"So soon Mike? God you’ve got a recovery rate most girls would love. But you’re not putting that thing near me again with mom asleep in the next room. Its lucky we weren’t caught just before."

I pouted, "But sis, you turn me on" I said and reached out and stroked her nylon covered thigh. I could see up her shiny legs up her skirt to the wet nylon covering her pussy. Just knowing that it was my sperm there got me even more aroused.

"I know what I can do for you." She smiled "Boys love this." She stood up and left the room. I was so disappointed but she came straight back with sly grin on her face. "You like to look up my skirt and look at my pantyhose and panties, don’t you?" she said. My sister then hopped on the bed and sat directly in front of me. She spread her legs and her white A-line skirt rode up to reveal her silken nylon thighs and come soaked panty crotch that had become almost transparent now it was wet with my semen.

Then she reached down and opened my fly; my hard cock popped straight out. It was red and throbbing and had a smear of pre-come at the tip. "Now I know you’ll like this" she said and bought her hand out from behind her back. In her fist she had a pair of white nylon pantyhose, I recognised them immediately as mom’s, she wore them as part of her nurse’s uniform.

My sister reached out and slowly drew the sheer nylon of my mom’s pantyhose over my cock and pulled it taught just like putting on a stocking. I had done this many times to myself of course, but the feel of my sister’s hand against my nylon-encased cock was exquisite. "Oh yes sis" I moaned.

Eileen had long fingernails, painted slut red of course because she is one. Her long fingers slid lightly up and down my nylon-covered cock; they felt like satin butterflies. I started to moan softly and she took the other leg of the pantyhose, placed her hand inside and began so slowly stroke my balls at the same time. I groaned "Oh sis, that’s lovely. Please don’t stop"

"Why would I stop Mike? You obviously need the relief, it’s the least a girl can do for brother" she smirked and gripped my pantyhosed cock a little tighter and wanked it slowly. "Here is something for you to look at while I make you come" she said and quickly changed position so she was straddling my face. Her silken pantyhosed thighs were right beside my head and I rolled my head to one side and started to lick them.

The feeling of my sister wanking me off with my mom’s pantyhose and the feel of my sister's sheer nyloned legs and ass against my face and tongue sent me into nylon ecstasy. "Imagine they are mom’s thighs you’re rubbing your cock on" she whispered. "They’re her nylons, I took them from the laundry basket, you can probably just still smell her cunt on them"

My sister talking like that caused my cock to become turgid; I was terribly close to coming. "Here Mike, you can definitely smell mine" she laughed and lowered her pantyhose and nylon panty covered snatch on my face. It was lovely, even though my come had soaked the gusset of her nylons and panties, I could feel her hot pussy and taste her juice.

I started to lick my sister’s hot cunt through her nylon panties. I bit into her pantyhose making a small hole for tongue to fit through. I pushed my tongue against the nylon of her panty gusset and moved it back and forth. My sister responded by pushing herself down on my face, and my tongue stated to lap faster at her silken gusset.

We must have looked quiet a sight, my sister crouched over me with her skirt rucked up and her pantyhose legs astride my face and my face buried in her panty covered pussy. My hard cock covered with my mom’s white pantyhose, being wanked by her red fingernailed hand.

I felt the grip on my cock tighten through the sheer nylon, and Eileen’s pace quicken. She pushed her panty-cunt harder against my face and my tongue forced the gossamer thin nylon of her panties inside her whilst by chin was rubbing her clitty. I could feel her really start to wank my cock hard now and my sister sensed my orgasm approaching.

"Come in mom’s nylons Mike! Come on brother of mine, fill your mommies pantyhose with your creamy come!"

I pushed my tongue as far as I could get it inside my sister panty covered cunt and gripped her sheer nyloned thighs, I pushed up and felt her gush of fluid in the crotch of her panties. At the same time she gripped my nylon covered cock as tight as she could and wanked it furiously. "Come in mom’s nylons Mike, let your sister ease your tension, shoot for me brother"

It was too much, the feel of pantyhose thighs in my hands and her sheer panties on my face; the silken caress of my mom’s pantyhose on my cock being wanked by my sister; it was just too much.

I groaned and felt myself release. Come was boiling out of my cock and trapped in the nylon of mommies’ pantyhose. It lubricated the shaft of my cock as my sister continued to wank it. "GOOOOOOD!!!!" I groaned as wave after wave of pleasure exploded inside me. "OHHH sis, that’s just SOOOO good."

Just then the door flew open and there was our mom standing in the doorway, her skirt creased around her thighs; she had obviously just woke up from her nap. She looked in the room and saw her son lying on the bed, with his cock being wanked into her pantyhose by her daughter, who was sitting on her son’s face, her skirt rucked up to display her nyloned legs and panty ass and crotch.

"Just what the fuck do you two think your doing!" she shouted.

 

To be continued………………….

My sister Eileen was a trollop, no doubt about it. She was 17 and had inherited mom’s figure and long legs, she wore far too much makeup and her school uniform skirt was far too short. Eileen liked to flaunt the rules, she was always on detention for not conforming to the school dress code but she couldn’t care less.

She wore her skirt as short as she could get away with and instead of wearing the prescribed uniform brown ankle-socks; she wore sheer to the waist pantyhose. The boys loved her and she loved them. She didn’t care about her reputation, as she saw it, at the age of sixteen and in her last year at school, it was more important to be popular than to get an education. Eileen was known as the ‘town bike’ and on parents and teachers day at school, the same fathers that cast their eyes on my mom could not help also glancing at Eileen with the same longing.

Living in the same house as my mom and sister did have advantages. From as long as I could remember I have had a fetish for nylon stockings and pantyhose. Mom wore either white or beige pantyhose with her nurse’s uniform and my sister wore beige to school but sometimes black or other coloured pantyhose with her street clothes. Of course once they were damaged they were discarded, but they did not stay in the trash long before they became part of my collection.

Alone in my room I would enact my pantyhose fantasies. I would wear them, sniff them, and wank in them, all kinds of pantyhose perversion. I loved the sight, feel, and smell of nylons. I could get an erection just rubbing their silken material against my face, and could orgasm by just rubbing my cock against the silky fabric. Yes living with two ladies who wore pantyhose every day had its advantages.

It also had its disadvantages. In the evenings I was constantly surrounded by two sexy women wearing sheer pantyhose and short dresses and skirts. I think because I was a son and a brother to them that both mom and sis just didn’t take any notice me as a man. They both often sat around with their skirts hiked up or legs akimbo and were often in various states of undress in my presence. I was just Mike, the son and brother who was a nice guy, studied hard, had few friends, and kept to himself. I think they actually felt a bit sorry for me, a geeky loner who spent most of his time in his room.

But if only they knew what I got up to in there, with their discarded pantyhose and the odd pair of nylon panties I had stolen. I wore their pantyhose and panties. I knew the sweet yet musky sell of their vaginas intimately; I had put the same silky nylon gusset that had encased their pussies against my penis. In my fantasies my mom and sister would wank me off with their nylon-encased toes. If only they knew…………………..but one day they found out.

Mom had come home about seven thirty, dog-tired from a day at the hospital. She kicked off her white loafers and the pungent yet arousing smell of nylon encased feet that had spent all day in hot shoes hit my nose. She ruffled my hair and kissed my cheek.

"Mom is just going to lie down for a little while son," she said. "Please go and fix me an ice cold Coke". I went into the kitchen and fixed the Coke and returned to the living room to find mom asleep on the lounge.

She was lying on her side and her white nurse’s uniform dress had rucked up around her ass. She was wearing white pantyhose today and pulled on a pair of white nylon panties over them. The crotch of mom’s panties looked hot and stained from her long day at work.

This was not an unusual situation, mom often crashed on the lounge like this and I would steal furtive glances up her skirt until I could take it no more and retire to my room for relief. This evening however, I knew my sister had a hot date with some guy she had been trying to get to take her out for ages. She wouldn’t be home for ages. I had my chance to try something I had wanted to do for a long time.

I put the Coke on the table and sat on the far end of the lounge. The TV was on and deliberately make plenty of noise and movement, I had to be sure mom was sleeping deeply. She didn’t stir at all. I reached out and gently placed my hand on her calf. I caressed the sheer nylon and immediately felt myself get hard in my jeans.

I stroked mom’s nylon calf for a couple of minutes, it felt lovely but it was also my plan to see haw far I could go without waking her up. She remained dead to the world. I took a deep breath and slid my hand up her thigh, the nylon was stretched taught and shiny here and as I stroked mom’s thigh I felt a drop of pre-come drip out of the end of my penis. I reached down and slowly unzipped my fly.

My throbbing hard cock sprang out; it was red and engorged. I continued to caress mom’s pantyhosed thigh and slowly wank my cock. It was nice but I wanted to feel that sheer nylon on my cock; I wanted to touch my mom with it. I re-positioned myself and was now on my knees on the end of the lounge. If mom woke up now I would have no alibi, kneeling there with my cock out of my jeans. I bent down over mom and put my nose next to her nylon covered pussy, I breathed in the heady aroma of mom’s cunt though her panties and hose.

I gently stroked the sheer white nylon of her panty crotch and felt the heat mom’s pussy had generated. I dare not linger in this compromising position any longer; I sat back down on the lounge. Now I eased myself so I was hunched over mom’s legs. I placed my cock against my mother’s pantyhosed calf and began to rub it gently against the sheer nylon. The feeling was exquisite and I became lost in my fantasy come true. I was rubbing my hard cock against my mom’s nyloned leg finally one of my deepest desires had come true. I knew what I was doing was wrong but it felt so good.

Then the door flew open and my sister flew into the room "That cheap, no good asshole" she yelled, then…………… "What the fuck do you think you’re doing?" She hissed at me.

"I, I, I, Shhhhhhhhhh" I hissed back quickly shoving my cock back in my pants.

Mom stirred "What’s up!"

"Nothing mom, just go back to sleep ok," I soothed.

I was glaring at Eileen who was mesmerised with shock at what she had seen. I got up and grabbed my sister and shoved her out of the room, down the hall, and in to my room.

"You, you, you" she stammered "were touching mom with your thing." she was still shocked but now she seemed to be coming around.

"You, you, you………You dirty little bastard." she started to smirk.

"I knew you were a perv, all the time you spend in your room with the door locked. All the times I couldn’t find my pantyhose and panties. And all the times mom and I found those suspicious stains on the pantyhose and panties we had left to hang in the bathroom!"

"You fucking dirty perv!"

"Shut up" I hissed in her face. "Shut up! shut up! shut up!" I pushed her and she fell on my bed, she looked up at me and laughed

"Wait until I tell everyone about my brother the pantyhose pervert," she said vindictively.

She was lying where I had pushed her, propped on her elbows facing me. Her legs were apart and her short white A-line skirt was hiked up to the top of her thighs, her platform high heels swung just off the floor. Her bust heaved with anger and then laughter, straining her breasts against the pink cashmere sweater she was wearing.

Her legs were encased in the shiny gossamer of taupe pantyhose, I could tell they were the expensive, sheer to waist kind she wore for her best dates. With her sluttish makeup and flaming red hair I could understand why the boys all loved her, she was my sister but I felt my erection start to return just looking at her.

"You aren’t telling anyone about anything," I said.

"Like fuck I’m not," she laughed back. "Starting with mom. She will be really keen to know her son was dry humping her leg like some dog on heat I’ll bet"

"You will be lucky if she doesn’t throw you out," she sneered.

"Oh I don’t think you will!" I hissed at her and then I noticed the fear in her face, she knew she had pushed me too far. I knew I was caught dead to rights and the only way I could save myself from a life of blackmail from bitch sister was to make sure I could blackmail her back.

"Yeah, I don’t think you can tell anyone anything about my pantyhose fetish, especially as you are a willing participant." I sneered at my sister.

"What the fuck are you talking about," she just managed to get out when I fell on her. I pushed my face into hers and mashed my lips against hers. She struggled and I followed the movements of her head to keep my mouth over hers to keep her quiet. She was struggling beneath me but even though she was a well-built girl, I easily outweighed her. I reached down and opened fly and pulled out my cock, it was semi-erect.

Eileen could feel me moving on top of her and when she felt my half-hard cock on her pantyhosed thigh she really began to struggle. I began to harden as I felt the silky feel of my sister’s nyloned thighs rubbing my cock. I didn’t have to move because her struggling was making a nice rocking motion that kept my cock rubbing nicely on her hosed thighs.

My sister wasn’t dumb, she was no virgin and figured out what I was doing and stopped struggling. She pulled her head right back and breathed out softly

"But I’m your sister Mike, I’m your sister!"

"I know that. You are my cock teasing, slut sister, who lounges around the house showing off her assets just to tease me. If you suspected I had a pantyhose fetish, then you must have done all that on purpose!"

"But I’m still your sister, we can’t," she sobbed.

"Well I can," I said.

I reached between us and hiked up her skirt all the way over her hips, I positioned my now rock hard cock between her silky nyloned legs and against the gusset of the nylon panties she wore under her pantyhose. Then I began to move slowly back and forth, pushing my cock against her gossamer encased pussy. She had given up the struggle and was quietly sobbing, her head was resting against mine.

"Don’t Mike, please don’t, I’m your sister," she whispered.

"I don’t care," I whispered back. "I have wanted to do this for so long, I don’t care about the consequences." I whimpered and then gently kissed her.

She didn’t respond at first so I kept up the pressure lightly on her lips until I felt the first stirring’s in her. My cock, which was encased in the folds of her pussy but surrounded by the nylon of her panties and hose, suddenly felt sticky warmth against it. Although I was close, I knew I hadn’t come yet, so it could mean only one thing, my sister was getting wet.

Oh my God! I got even more excited now and started a rhythmic humping, that forced the head of my cock to push against where I though her clitty might be under the nylon of her hose and panties. I must have been close because I felt my sister squirm slightly and adjust her ass so that my cock moved a fraction to what must have been the right position for her.

Then I felt my sister start to hump me back, as I pressed my cock against her she pushed back against me. I was in heaven, dry humping my sister like this. I put my hands under her ass and squeezed her buttocks through her sheer hose and nylon panties. It felt wonderful. Then she amazed me! My sister lifted her legs up and rubbed them over my back.

She reached around and pulled my shirt out of my pants and rucked it up my back. I felt her pantyhose legs lock behind my back and rub the sensitive skin there, as she rocked in time with my thrusts. She was now rising up to meet my thrusts and kissing me passionately.

She was breathing hard and fast. The feel of her pantyhose encased legs rubbing my back, her nylon pantied ass in my hands, her soft lips kissing me, her sheer pantyhosed and nylon panty covered cunt pushing against my cock was exquisite and I felt myself about to release.

I pushed hard against my sister and felt the end of my cock push the fabric of her pantyhose and panties just inside her cunt. It was too much. I shuddered and felt streams and streams of my semen flood into her and soak the material of her panties and hose.

She shuddered back and gripped me with her tight nyloned legs and I felt her orgasm rage through her and her cunt spasm against my nylon covered cock.

We held each other that way for a few minutes, then she lay back and dropped her legs. She smiled up at me through her smeared makeup and said:

"We are in so much trouble now," and giggled.

 

To be continued.

I looked down again into Mom’s face and saw that she had stopped crying. Her smudged makeup made her look even sexier in my eyes. She has the sultry ‘used’ look I sometimes saw on the ‘Waif’ models in Sis’s magazines. Mom’s eyes locked on mine,

"Are you happy now Mike? Did you get what you wanted son?" she whispered.

"Is the satisfaction of your animal lust worth the ruination of our family?" she asked.

"Mom, you don’t understand," I whispered back.

"You and Eileen have been driving me sexually insane for so long it’s amazing I haven’t done this before. Sitting and lying around in your short skirts, your pantyhosed legs and sexy nylon panties on display; the makeup, the clothes, the nylons, the smell of you both, you drove me mad!" I exclaimed.

"Haven’t you ever wondered about the stains in your panties and nylons? Sis’s too!" I pleaded.

"Of course I knew it was you Mike, who else could it be? But what was I supposed to do, confront you? Hold mine and Eileen’s soiled pantyhose and panties to your face? Ask you to explain?"

"I knew that you would have no answer that made sense. I knew the embarrassment for you would be unbearable, so I decided to let you indulge your fetish and let you use our underwear for your pleasure. I though it might stop eventually, and I hoped your Sister wouldn’t notice. But I never expected this!"

"Get the fuck off me Mike! I’m your Mother for god’s sake!" she hissed.

"I can’t Mom," I whimpered.

"I know you will have to report this. If not to the police, then to your fucking shrink, who will convince you to report me to the police anyway." I said.

"So what are you going to do then Son," Mon spat at me. "Spend the rest of your life with me and Eileen held prisoner in this house. I don’t think so Mike; come on son let me get up," she pleaded.

"I don’t know what I’m going to do Mom," I said. "I really just fucking don’t know," I started to cry.

Then I heard a voice behind me say,

"Then there is only thing for it Mike, we will have to do to her what you did to me."

I turned around shocked. There was my sister Eileen. She was as usual dressed in her parody of the school uniform, the hem of her tunic way too far above her knees, her legs in sheer taupe pantyhose instead of ankle socks, her feet in low heeled court shoes, and with way too much makeup on for a seventeen year old schoolgirl.

"What the fuck, Sis, what are you doing here I stammered."

Mom tried to wriggle free at the sound of Eileen’s voice,

"Call for help Eileen, please, help me!" she pleaded.

"Shut up Mom please," Eileen said matter of factly. "I came home because I forgot my math homework, and I heard the struggle in here. I’ve been at the door the whole time. I saw what Mike did to you Mom, and I have listened to what you have both had to say."

"Then you understand Eileen," Mom pleaded again. "He did the same thing to you, forced himself on you, we have to stop him!" she demanded.

"Well unfortunately for you right now, that’s not how I see it Mom," my Sister said.

"I know if this gets out, the family is ruined. Mike goes to prison or a boys home; at the very least he is kicked out of our home, and I don’t know if I can take that with what has happened to Dad."

"I also know there is no way this can be kept secret if you tell anyone. My life will be worthless around town! Ok, so I’m not the homecoming virgin, I might be a slut but I don’t want to be forever known as the girl that fucks her brother!" she hurled at Mom.

The she grinned wickedly,

"Besides Mom, I have to tell you, I kind of like what Mike and I do. I like the power I have over him with just the flash of my knickers or a display of my pantyhosed thighs. And I have to say, I like what he does to me, sure it’s kinky, but it sure feels good!" she chuckled.

"Oh my God! Not you too!" Mom shrieked from beneath me, and commenced struggling in earnest to get free. I grabbed her wrists and pinned her down again.

"So anyway Mike, as I was saying," Eileen continued matter of factly, "there is only one thing to do. We have to do to her what you did to me. Make her like it!" Eileen said wickedly.

"So lets get started Mike," she smiled at me, "She just lay there before while you had your way, lets see if together we can warm her up!"

"No! No! Fucking No!" Mom started shouting and struggling again.

"Hold her Mike," Eileen ordered, "and shut her up for God’s sake." She added.

I used the easiest method to shut Mom up that came to hand, and that was to crush my lips against hers. I started kissing her with renewed fever whilst watching my Sister Eileen out the corner of my eye.

Eileen approached the bottom of the bed and grabbed Mom’s ankles and pushed them down on the bed to help hold her still. Then she surprised me by climbing on the bottom of the bed herself and she started to kiss and lick Mom’s ankles and calves; her lipstick smeared on Mom’s sheer nylons as she did.

"Hold her Mike!" she ordered, "this is going to get really exciting for us, but I think she will fight like a bitch for a while, at least until I can get her wet," Eileen said.

Eileen started to spin around on the bed easing my body to back along Mom’s body, whilst I kept my grip on Mom’s wrists. She ended up astride Mom with her head near Mom’s calves and her legs straddling Mom’s chest. I had moved back against the bed-head at the top of the bed and was now sitting with Mom’s head between my knees and all my weight on her wrists, facing Eileen’s back as she bent over Mom. Mom could hardly move at all, and again it looked like she was going to resign to her fate. Tears streamed out of her eyes again adding to the watery mascara that was smeared on her face. She whimpered softly,

"Please don’t children," and then became silent and limp.

Eileen now worked her way up Mom’s legs, kissing sucking and licking her diaphanous nyloned legs. I was so turned on, I felt my member once again engorge and it rode to attention, ready for action.

"Come on Mike," Eileen lifted her head, turned, and giggled, "you must get the idea. What about giving your Sister some of what she’s giving Mom?" she laughed, wiggling her ass at me.

Eileen’s skirt just covered her ass, the pleats of her school uniform tunic skirt enticingly close to me. I reached out and lifted my Sister’s skirt and was instantly aroused further. Her thighs were encased in the sheerest of gossamer taupe nylon, and then they disappeared into the flimsiest sheer nylon panties I had ever seen. They were nearly see through and I could see the gusset of her pantyhose moulded snugly against her cunt whilst the sheer nylon of the full cut panties caressed her ass cheeks.

I reached out and stroked the globes of my Sister’s ass checks, my hands stroking her firm buttocks through the flimsy nylon of her panties and hose. Eileen by now had her face buried between Mom’s thighs. Although Mom made no sound she was now trying desperately to close her legs, but it was too late, Eileen’s mouth was firmly clamped on her panty crotch. My Sister used her tongue to ease aside the silken gusset of Mom’s panty crotch and pushed her tongue, snake like, through the hole in Mom’s pantyhose, the same hole through which only a while ago I had raped my Mother with my rampant penis.

I was now so excited my cock was throbbing. Watching my Sister lick my Mom’s cunt through her hose and panties was more than my wildest fantasies could have imagined. I fell forward and buried my face in my Sister’s panty clad ass. I forced my tongue against the sheer nylon encasing her cuntal lips and began to lick. Eileen shuddered and pushed back against my face, I heard a stifled moan from between Mom’s legs where her head was buried lapping at Mom’s cunt. Then I head a sound I hardly believed. Mom gave out a long trembling sigh, and moaned,

"Oh God forgive me that feels so good!"

Mom’s hands went down to Eileen’s head, not to push it away but gently stroke her daughter as she licked her Mom’s cunny through the hole I had torn in her pantyhose. Eileen let go of Mom’s ankles and unbelievably Mom opened her legs further to allow her daughter better access to her cunt. Mom’s silken, nylon encased, legs opened and raised slightly off the bed, her high heels came to rest on the bottom of the bed as she pushed her ass, still clad in her nylon panties, up off the bed to allow her daughter better access to Mommies now sopping cunt. Eileen used her now free hands to push the gusset of Mom’s panties to one side of her cunt, and the other to tear the hole in Mom’s pantyhose even bigger so she could get her lips on Mom’s pussy and work her tongue around her clitty.

Mom was now groaning and moaning, lifting her ass in a steady rhythm to Eileen’s oral invasion of her cunt. I was now furiously licking my Sister’s cunt through her panties and hose but I wanted more. I bought my hand up and dragged the gusset of her nylon knickers across her ass exposing her cunt sheathed in the gauzy nylon of her pantyhose. I put a finger against the nylon and pushed. My finger disappeared inside her cunt sheathed in the nylon of her hose. I immediately realised what I was going to do; my greatest of all fetish fantasies.

I eased myself forward over my Mom who was now steadily groaning in ecstasy underneath me, and positioned my rock hard cock against my Sister’s cuntal lips. I eased forward and the gossamer thin nylon of her pantyhose began to give and to encase my cock as it slowly forced its way inside my Sister. The nylon of the pantyhose encasing my Sister’s lovely big ass began to stretch taught as my cock forced its way deeper into her, taking more of the luxurious silken material with it. The feeling was exquisite, my cock was being gripped by my Sister’s tight cunt and was surrounded by the most glorious soft sheer nylon at the same time. I slowly started to pump in and out of my Sister, one hand on her nyloned buttocks, the other pulling tight on her panty crotch, driving the damp nylon against her hard clit as I fucked her.

Mom was now almost incomprehensible with pleasure. She was groaning whimpering and crying as she maintained her steady thrusting of her ass up from the bed and against my Sister’s face buried in her crotch. This was just amazing, more than any fantasy I could imagine and I knew I couldn’t hold back my orgasm for much longer.

I imagined what we looked like. Mom on her back with her nurses uniform skirt pushed up around her waist, her nyloned legs spread, her ass bucking in the air to meet the tongue of her daughter who is straddling her dressed in her school uniform, her pleated skirt thrown over her waist to expose her pantyhosed thighs and pantied ass, as her cunt is being plundered by her brother, who has his cock driven deep inside her whist he is straddling the upper torso of his Mother.

Eileen was starting to grunt in time with my thrusts as the nylon of her hose was forced against her sensitive clitty. Added to her pleasure was the gusset of her sheer panties rubbing against the nylon hose as I gripped the panties like a horse-rider holding his reins in one hand. Mom was still moaning her pleasure, her grunts getting faster and louder. Then the most amazing thing happened; I felt a tongue on my balls. I looked down and saw that Mom had lifted her head slightly and was licking my balls as I thrusted in and out my sister. She opened her lipstick lips and gently licked and sucked them with her hot wet mouth.

It was all I needed to go over the top, my cock exploded and I pounded it in and out of my Sister, the force of my strokes making her ass cheeks shudder. I felt the hot semen shoot out of my cock, through the sheer nylon encasing it, soaking my Sister’s cunt and further lubricating the pantyhose surrounding my penis. I shot load after load until I was spent.

As my first load exploded deep in my Sister, I felt her cunt walls quiver as her own orgasm erupted. She bucked back against me to meet my thrusts and at the same time increased the frantic lapping at Mom’s cunt. She buried her head deeper inside Mom’s nyloned thighs and pushed her tongue hard against Mom’s clitty.

This had the effect of invoking a shuddering orgasm in Mom. Her whole body quivered and her heels drummed against the bed as she came. Mom’s lips clamped down on my balls and her tongue became frantic as it slobbered around my tight hard testicles.

We were all coming at once. Mother, Brother, Sister, the girls in their sheerest nylon pantyhose and panties, slutty makeup and uniforms. It was certainly a silken family trap!

 

To be continued………………………………………………………………….

We were all coming at once. Mother, Brother, Sister, the girls in their sheerest nylon pantyhose and panties, slutty makeup and uniforms. It was certainly a silken family trap……………………………

 

Part V

An hour later I was on my way to school. I couldn’t help thinking about the exquisite sexual fantasy that I had just lived, fucking my Sister and my Mom. I was semi-hard as I relived the last few hours of the morning. Mom had made me and Eileen go to school, she told us that we should behave as normal so no one would suspect what was going on in the privacy of our house. She gave us both late notes; some bullshit about a sick family member who we had gone to visit in hospital. Mom said we would have to talk about our family secret tonight and decide just how we were going to keep having our family fun and keep it a secret.

All day at school I fantasised about how I had fucked Mom. She, fully clothed with her tight white uniform skirt rucked around her ass as I slammed into her, past her torn hose and panties. By the time I left school at half three I was horny as hell. I knew Mom wouldn’t be home until six but I couldn’t wait, I walked the half dozen blocks to the hospital where she worked.

I sometimes went there to see Mom at work, I love staring at the pretty nurses in their tight white uniforms, silky pantyhose, and cute little hats. A few of the older nurses who knew Mom would often come over and say hello and ruffle my hair. If only they knew I wanted to throw them down on the nearest bed and fuck them in their crisp white uniforms. A nurse named Janet who I guessed to be in her mid 40s came over to me as I sat on the bench near Mom’s workstation at the end of the ward.

"Hi Mike," she said.

"Your Mom is occupied with a patient right now, the ward has been really busy today," Janet said as she rushed past.

"Wait in the Matron’s office out of the way and I’ll tell her you’re here."

I went into the Matrons small office that was next to long counter where Mom did her paperwork when she wasn’t busy in ward. I closed the door behind me and sat in an armchair that was pulled up to the desk. I looked around the office and lazily rubbed my semi-hard cock through my jeans. I wondered what the fuck I was doing here, but I was so horny for Mom. I could go home and probably fuck my sister Eileen, but I was hot for Mom after this morning’s session.

A small rubbish bin in the corner caught my attention. Hanging half out of the bin was the leg of a pair of pantyhose. I checked to make sure the door was closed then wondered over and removed the pantyhose from the bin. They were white, control top and I could see the ladder torn in one leg that was reason Matron had discarded them.

I lifted the gusset of the hose to my face and inhaled the smell of Matrons cunt. The smell was still strong, so the hose must have been discarded not that long ago. I walked over to locker in the corner and opened it. Inside were two white skirts with matching blouses on hangers. Matron was a stout woman looking at the size of them. I found nothing else there to excite me so I returned to the armchair.

I was so horny now that I had to do something about it. I eased my zipper down and freed my hard cock. I slid one leg the silky nylon pantyhose over my cock and started to gently stroke it.

Just then the door flew open and in came Mom. She looked flustered and had obviously been working hard.

"Jesus Mike, why are you here Son, cant whatever it is wait until after………………"

Then she stopped mid sentence as she saw what I was doing.

"For fuck sake Mike, if you get caught doing that here they’ll lock you up and fire me. Can’t you at least leave yourself alone until you get home?" Mom said sounding exasperated.

"Well no Mom," I said getting up out of the chair.

"I just can’t stop thinking about what we did today."

"Well Son, there is a time and place for that. What we did this morning and last night is illegal; so at least lets leave that behaviour at home," Mom said, sounding cross.

I took a step towards her; I would have looked a real sight with the stocking hanging off my cock if anyone walked in.

"Please Mom," I pleaded and put my arms around her. I crushed my lips against hers, tasting the lipstick as it smeared on my lips. I pulled her close to me and I felt her move against me as my hard cock pushed against her leg through her skirt. She rubbed her lower body against me, dry humping me through her skirt.

"Ok Mike, I’ll let you have something quick, but then you must leave ok?" Mom said, reaching behind herself to engage the lock on the door.

"Matron is gone for the day, but I can only spare a few minutes so it will have to be very quick Mike."

Mom eased herself out my grasp and went to the desk where she bent over. She reached back and lifted her skirt and pushed her lovely round ass towards me.

"Help yourself to Mommy Mike," she said seductively as she looked around me and smiled.

I needed no further invitation. I pulled the flimsy stockings off my cock and threw them back towards the bin where I had found them and stepped behind my mother. Her ass was raised towards me, the firm cheeks glimmering in the sheen of her pantyhose. I noticed that today she was just wearing a white nylon thong, the thin strand of silky white material running up the crack of her ass, visible through the nylon gusset of her hose.

"Come on Son, give Mommy a quickie, you started it, now hurry up and finish," she panted, and wiggled her ass at me.

I stepped between her parted legs, the rough material of my denim jeans whispering on the nylons that encased her legs. I reached out and placed one hand on each of the globes of her ass and pushed my cock into the crack. As I rubbed my cock up and down the crack of my Mother’s ass, my penis was stimulated by the feel of her pantyhose, Mom started to push back on me and gently rotate her ass.

"Mikey, you have to be quick Son," she panted again.

"I’m enjoying this as much you are now, but we might get caught if you don’t hurry."

I needed no further urging; I pushed a finger into the crotch of Mom’s pantyhose and popped it through the sheer nylon. Then I put both hands into the small hole I had made and tore the hole in the pantyhose covering Mom’s cunt until it was big enough for my purpose. I eased the thin strip of material covering her cunt to one side and slid myself inside my Mother until I was buried to the hilt.

"Oh Mom," I gasped.

"This feels so good."

"Oh do me Mike, do me son." Mom panted.

I started a steady thrusting, pushing my cock in and out of Mom’s cunt. Mom pushed back with each thrust, burying my cock deep inside her and rubbing her sweet nyloned ass against my balls. Mom was panting now.

"Do me Mike, give your Mom a good fucking, push that young cock of yours in and out of Mommies pussy," she chanted.

"Fuck me, fuck me, fuck meeeeeeeeeeeeeeeeeeeee," she hissed, and I felt her cunt spasm around my cock.

I was making my Mom come. Her tight cunt gripped my cock and she pushed back against me, forcing her clitty against me as I humped. My cock expanded and blew its load. A torrent of hot semen washed into my Mom’s cunt and she gasped and shuddered again.

I nearly fell over as I leaned over my her, grabbing her stockinged thighs and pulling her back on me, impaling my Mommy as I shot my sticky gism deep inside her.

Just then the door rattled,

"Jean? Jean? Are you in there," I heard one of the nurses saying. Mom answered,

"Just a minute Carol. I’ll be out soon. I’m changing my nylons because I caught them on Mister Simpson’s bed."

Mom was cool as cucumber; bent over the desk with my cock buried in her she told lies as easy as pie. I felt Mom squeeze her cuntal muscles and push my deflating penis out on her. She turned around and took a handkerchief from her pocket and took hold of my flaccid penis and wiped it. She zipped my fly and patted it then leaned forward and gently kissed my lips. She bought her finger up to her lips,

"Shhhh," she whispered. And began to wipe the hankie between her thighs, soaking up my come.

"Well Mister Simpson needs his five o’clock meds Jean, torn nylons or no torn nylons. Please hurry," nurse Carol said through the door.

"On my way Carol," Mom said and smoothed down her skirt. She pointed to the corner of the room that would be in the blind spot from the door and I tip toed over there. Mom opened the door,

"There, that’s better," she said motioning to her legs to Carol to continue the charade of the torn nylons. She quickly glanced my way and winked as Carol turned away. Mom quickly flicked the back of her skirt up exposing her gauzy nyloned thighs and ass, she tipped me another wink and walked off.

I waited for about two minutes and was about to leave when a large woman who I estimated to be in her mid forties entered the room. It had to be Matron!

"Who are you sonny," she asked in a not too friendly manner.

"I’m Mike. My Mom is a nurse here, Jean." I stammered. The room reeked of sex; she must have been able to smell it.

"Well what are you doing in my office Mike," she asked.

"I was doing my homework waiting for Mom," I lied. It was a stupid lie because I had no books with me. Matron looked at me quizzically and said,

"Well I have work to do Mike, best you wait for your Mom outside," she said.

"Ok Ma'am, I will." I said and squeezed past her towards the door. Up close she was quite pretty, as some larger women are. She had a round open face framed with red hair worn in a loose bob. Her eyes were huge and a deep blue. She too obviously believed like Mom, that more was better when it came to makeup because her eyes were painted and heavily mascaraed and her lips were a cherry red. She was just the sort of woman I fantasised about when I wanked.

I had to look down of course. Yes! Glimmering taupe pantyhose encased her legs that were large but well shaped. They were long and tapered out of her tight, dark blue, business suit skirt. I saw that she saw me looking at her legs and she smiled. She reached in the bin next to her desk,

"Here Mike," she smirked and handed the pantyhose that only minutes before had been stretched around my cock.

"You might as well keep them, by the look of the that little wet patch and the smell of semen, you were been busy with them before I came in," Matron said, a smile on her face.

"Maybe next time you visit I’ll let you take these off," she said pulling on the gossamer sheer nylons on her legs.

I was just flabbergasted and almost beyond speech.

"Thanks Ma’am, I would love to," I stammered and walked out the door my head spinning. I heard her laughing to herself as I walked away stuffing her pantyhose into my pocket.

"But I bet you are the sort of lad who would have more fun If I left them on," she chuckled after me.

"Just leave Eileen ok, I just can’t talk to you right now," Mom scowled. I had never seen her so angry.

My sister Eileen slunk out of the room and I heard her bedroom door close shortly after.

"And you, you, I don’t know what to call you Mike, I just can’t talk to you either right now, I’ll just lose it!"

Mom turned away and slammed the door as she left, but even then I couldn’t help looking at where my mom’s skirt had rucked up to display her silken thighs.

I rolled over and started to whimper. I felt disgusted with myself, but at the same time so sexually sated that I was exhausted. I fell asleep that way, my mind spinning with what I had just done with my sister and what the consequences may.

I awoke the next morning surprised to find myself still fully dressed, and a pair of come stained pantyhose beside me on the bed; mom’s pantyhose. Then the events of last night all came flooding back to me; oh my god, what had I done?

I snuck out of my room to shower, hoping like hell not run into my mom or sister; I was so confused and apprehensive, I just couldn’t face either of them. I made a plan to stay in my room until sis left for school and mom left for work, it would be better that way, more time to think.

The minutes seemed like hours until Eileen left for school, I watched at the window until I saw her leave. Even though I knew my sister and I had committed the gravest of sins, as my sister walked down the path, head down, my eyes could not help focussing on her sexy pantyhosed legs on display beneath her short skirt. I knew I had caused her a terrible dilemma that could break our already fractured family apart, yet I still fanaticised about our sexual encounters last night. I started rationalising to myself. We hadn’t really committed incest (yes I was now admitting to myself the nature of our sin), as I hadn’t actually entered her with my naked penis; we hadn’t ‘fucked’ in the true sense of the word, had we?

The dreaded knock came on bedroom door about fifteen minutes after Eileen had left for school. I was in a cold sweat, hoping my mother would at least give me the day to prepare for our encounter. I had fantasised about leaving home, running away, and never coming back to face my mom and have to explain my perversions. I just felt so ashamed and unable to explain the lust that had lead to last night’s abhorrent behaviour. But deep inside I was still seething with the ecstasy that I had experienced; the exquisite feel of my cock on my mom’s nyloned legs and the aftermath of sexual frenzy that I had experienced with my sister as she at first resisted, then capitulated to my base desires.

"Mike, It’s mom, we really need to talk," she called to me through the door.

"Mom, I’m just so sorry, I can’t talk to you, I’m such a bad son and a worthless brother," I croaked.

"Let me in Mike, we need to talk son," my mom insisted.

I dragged myself away from the chair by the window on leaden feet, dreading this encounter. I unlatched and open the door. Mom was dressed for work, her pristine white nurse’s uniform complemented by her white nylons and white nurse’s shoes. Although her shoes were ‘flats’, they somehow helped define her thighs and the calves that were on display below the hem of the skirt that came to just above her knees. I couldn’t help but admire her, she was stunning in my eyes, her makeup as usual was heavier than expected of someone in her profession, but it accentuated her sexiness, almost making her a caricature of the nurses seen in porno magazines and movies.

"Mom, I’m so sorry," I whispered as she entered.

"I just, I just," I couldn’t finish the sentence.

"We need to talk Mike," she half whispered, she started to cry and led me to the chair that was next to my study table.

I sat down and I felt all of my energy drain from me. I felt depleted of all energy and will. I was determined however to take full responsibility for my actions and tell mom everything. I would not let my sister take any blame for what I had done. Sure she had become a willing participant in our deviant encounter, but only after I had forced her.

Mom remained standing in front of me, and still my eyes drifted to her silken nyloned calves and then up to her thighs. I felt a further disgust directed at my wanton lust. I cleared my head and began:

"It was all my fault mom,"

"I forced Eileen to do what you saw. It’s all my fault and I won’t blame you if throw me out on the street."

"I let you down," I sobbed.

"Dad is in jail, I’m the ‘man of the house’ and now I fucked it all up by doing what I did to my sister."

"I’m so sorry," I sobbed.

"But it wasn’t just your sister was it?" mom stated in a firm voice.

"Eileen told me what she saw when she came home," she said.

"You were doing things to me while I was asleep, weren’t you?"

"Oh mom I’m so sorry," I whispered, "I, I, I, Just couldn’t help myself."

"Well son, can you explain to me why you did what you did?" mom asked sounding genuinely concerned.

I told her, I let it all out. I went on to explain my sexual desires and fetish. How, for as long as I could remember, I have had a fetish for nylon stockings and pantyhose. How once she and my sister had damaged and discarded their nylons I would retrieve them from the trash and alone in my room I would enact my pantyhose fantasies. How I would wear them, sniff them, and wank in them, all of my panty and pantyhose perversions. I told my mom that I could not resist the sight, feel, and smell of nylons.

I then told my mother how I felt being constantly surrounded by two sexy women wearing sheer pantyhose and short dresses or skirts. That when they sat around the house with their skirts hiked up or legs akimbo that I just had to retire to my room to take my pleasure with a pair of their discarded pantyhose or nylon panties that I had stolen from the wash-basket.

"Oh Mike, I’m so sorry, I didn’t realise you had these feelings for your sister and me. I’ll talk to Eileen tonight and explain it all. I don’t know what I’m going to do about what happened between you and her though; you know what you did was not only morally wrong, It was illegal."

"There is only one thing for it. It will have to be our family secret; you must never tell anyone, ever, ok?"

"Of course mom, I promise," I whispered.

"And Eileen will have to be convinced of the same. That only leaves me, and of course I’m not going to say anything. I will not have my family split up"

"So there Mike, we can just put this nasty episode behind us ok?"

My mom smiled sweetly and I realised how much I loved her. But even then, with al this going on my eyes drifted to the hem of her skirt and her silken thighs. My mom’s eyes followed mine and I knew she had seen what I was looking at. She frowned.

"Take a shower Mike, get ready for school. I’ve a phone call to make then I’ll drive you, ok son?" she smiled.

"Ok mom," I said, and bounded off the bed and down the hall to the bathroom.

Everything was going to be ok, I thought to myself. We just won’t talk about what happened last night and things will return back to normal. I stripped off and got under a warm shower. As I soaped my cock and balls a tingle started and I couldn’t help but stroke my hardening cock I was thinking about how I had climbed on my sister and dry fucked her through her pantyhose and panties.

I couldn’t help myself I still had my fetish. I turned off the water and climbed out the shower, drying myself on the towel. Then I went exploring in the washing basket. Bingo! I found the pantyhose mom had been wearing last night. I pulled them out of the basket and put them to my face. I felt the sheer nylon caress my face and smelt the faint aroma of my mother’s vagina in the crotch of the hose.

My cock was now hard and I lowered the pantyhose down to it. I opened the hose and pulled one leg over my cock and started to wank slowly. The feeling of the sheer nylon of my mother’s pantyhose on the nerve endings of my erect member was exquisite. I forced myself not to speed up the slow, deliberate, movements of my right hand wanking my hardon. With my left hand I gathered up the rest of the silky garment and began to slowly massage my balls. My thoughts now were of the earlier part of last night, how I had slid my cock up and down my mother’s silken calves, clad in these very silken sheer pantyhose.

Then I heard my mother’s voice, distant but loud enough to bring me out of my reverie. She was on the phone in her bedroom, I decided I better stop my wanton pleasure and get ready for school or mom would be suspicious. That wouldn’t do now that It looked like I was going to get away with what was virtually the rape of my sister, and certainly incest with both her and mom, (even though mom didn’t know what I had done to her).

I threw my discarded clothes into the wash basket on top of the pantyhose I had been wanking into. After years of masturbating with my mom’s and sister’s nylon panties and pantyhose, I knew how to replace the garments so that they would not be suspicious. Although my sister Eileen had said she had noticed come stains in hers. I would have to be careful in future I though. I may have agreed not to engage in incest but I had no intention of giving up my fetish.

I left the bathroom doing up my shave coat, a ratty robe I only wore to and from the bathroom for the sake of modesty. As I passed mother’s room I overheard her talking softly into the phone,

"He’s only 15 doctor but he’s maturing so fast. No I can’t tell you about it on the phone that’s why I want to make an appointment for me and him to see you as soon as possible!"

"Look you worked wonders with my depression when my husband went into prison, now I need you to help with a family crisis."

"No it’s mainly Mike and these depraved sexual urges he is having. I’ll explain it all to you before he goes in to see you, but you must keep it to yourself!"

"I know I have your word as my doctor, but what Mike’s been doing is pretty debauched. Ok then, we’ll be there in an hour, Mike thinks I’m taking him to school. Bye."

The fucking bitch! My mother the fucking bitch! My blood was boiling at this betrayal. I flung open the door just as my mom was hanging up. She was sitting on the bed next to the telephone on the nightstand. I stormed into the room and pushed her hard on her shoulders forcing her to fall back on the bed.

"You fucking bitch mom! You swore we would tell no one!"

She whimpered, I could see the fear in her face, "Mike its for the best. I have to get you some help if you are going to stay in same house with me and your sister."

"But you promised! We would all just say nothing, tell no one, and that would be it!"

"But Mike you need help!" she cried again.

Now I noticed how she had landed when I pushed her back on the bed. The hem of her white nurse’s uniform had ridden up and her legs were slightly parted. I could see her sexy sheer pantyhosed thighs tightly stretching the white cotton skirt. I felt my cock begin to harden and I looked into her face. Her makeup had started to smear because she was crying, the mascara darkening her eyes even more. My god she looked even sexier, sluttish in her pose, with her piled on makeup, dishevelled, and her skirt rucked up; she looked vulnerable. She looked fuckable !

"Oh I need help alright mom," I hissed.

"I need fucking help, the same kind of help sis gave me last night."

"So mommy are you going to help your son with this problem," I whispered harshly and opened my shave coat to reveal my hard throbbing cock to my mother.

"Mike! Son! No!" she screamed. "You can’t, please, cover yourself; I’m your mother for god sake!"

I was through talking; looking at her lying helpless on her bed only made me more aroused. As I leapt on her, my shave coat flew open, and I landed on top of her. I stretched her arms out and pinned her beneath me. I had landed directly on top of her with my legs between hers; my erect penis pushed against the cotton hem of her skirt and my face hovered over hers.

"Please Mike, stop this now, please have some respect for your mother," she whispered into my face only inches from hers.

Her breath was sweet, and looking into her sexy blue eyes and ruby lipsticked lips, I knew I couldn’t stop myself. I lowered my face onto hers and kissed her lips. She kept them tightly closed, but the taste of her lipstick and the feel of her fully clothed body against my almost naked body only inflamed my passions. I sighed and tried to force my tongue between her lips. My mother responded by squirming beneath me and wriggling to get free.

This was a disastrous mistake for my mother as her writhing caused her skirt to ride up further and my hard cock to come into contact with her pantyhosed thigh. I hung on to her, allowing her to move beneath me thus causing her nyloned leg to rub against my turgid penis. The feeling of her gossamer nylons on my cock was electrifying; along with the feel of her breasts inside her crisp white nurse’s uniform rubbing on my chest I was intoxicated with passion. The thought of finally consummating my deeply held secret passions for my mom in her uniform and pantyhose drove me to the peak of my desires.

"That’s it mommy, fight me if you want. You know my sister did at first, but she soon changed her mind," I whispered in her ear.

Then my mother realised what I was doing, holding on to her and allowing her struggle to inflame my passion. She lay still and looked me in the eyes.

"Well take what you want Mike. I won’t fight any more because I think that’s what you want. But remember you will have to live with consequences after," she whimpered.

I lowered my lips to hers and as they touched I whispered, "Fuck the consequences!"

I mashed my lips on hers and forced my tongue into her mouth. She didn’t respond but she didn’t fight either. Her lying prone and not offering any response at all only served to inflame me to greater passions. I put my hand between her legs and positioned my cock over her panty and pantyhose covered pussy and started to thrust slowly against her. I then eased my cock between the nylon gusset of her panties and the gossamer thin nylon of her sheer to the waist pantyhose covering her pussy. My cock was in a silken trap, caressed between her nylon panties and her hot cunt covered by her pantyhose.

I continued to kiss my mother as I humped her panty crotch, my cock was like a living thing, the sensation was so magnificent, better than anything I ever felt when masturbating, or even with my sister last night. I could feel the outline of my mom’s pussy lips through the hose and adjusted myself so my cock was between them. My precum was lubricating the nylon so I couldn’t tell if mom was aroused but she continued to lie there unresponsive.

I reached down with my hand and put a fingernail against the nylon covering her cunt and pushed until I felt the pantyhose tear. Still my mother didn’t move so I pushed forward with my hips. The tip of my cock forced its way through the hole in her pantyhose and was nestled in her pussy lips against the entrance to her cunt. I pushed forward again slowly but firmly and felt the head of my cock enter her. My mother grunted as my cock went inside her, but other than a flinch she made no effort to stop me. My mind was racing. I was fucking my mom! NO! I was raping my mom!

I pushed in further and found resistance. She was dry! It was obvious my mom was not going to capitulate and become a willing participant. I started a slow thrusting movement hardly moving my cock at all, just enough to get my precum lubricating my cock as I entered her further, millimetre by millimetre. We must have looked a sight, my mom lying on the bed her legs apart and her arms above her head held there by my free hand. Her skirt rucked up around her waist and her sheer nylon encased legs wide with me between them slowly humping and forcing my kisses on her, her heavy makeup smeared making her look like a whore.

Eventually I was fully inside her and my balls came to rest against the silken gusset of her panties that had been pushed aside to allow my entry. I was fighting off my orgasm; having to enter her slowly had helped. My precum had lubricated my mom’s cunt enough to enable my cock to fully penetrate her, but she was still very tight. My head was spinning with desire now and I knew the inevitable would happen soon, regardless of how slowly I fucked her.

I released the hold on her hands and lifted her silken pantyhosed legs up and around me. Mom didn’t fight; she hadn’t said a word other than the grunt as I entered her. She was just like a rag doll. Tears streamed slowly down her face and her eyes were closed. I shucked off the shave coat all the way so that I was fully naked and could feel the gauzy nylon of her pantyhose legs on my back and thighs. I pulled back my throbbing cock all the way and thrusted deeply into her, once, twice, three times. Each time I did, she grunted with the force of my thrusts. On the third thrust I pushed in as far as I could and rubbed my balls on her panty-ass and concentrated on the feel of her silken nylon legs against me. I exploded; torrents of come seemed to explode out my cock. The pleasure was so intense that it was almost painful.

I shuddered and groaned for what seemed like an eternity as I filled my mother with my hot seed. Eventually I came down from the plateaux of ecstasy and opened my eyes. I found myself looking at my mother’s icy blue eyes; they were devoid of emotion. She just stared up at me.

 

 

To be continued………………….

“Your mine sugar,” 

“Shake that arse for me baby,” and other demeaning harangues were yelled my way.  I was so scared about what would happen to someone like me in here.

One of the guards laughed “I’d get a big bad friend if I were you,”

His mate retorted “I’d get two big friends.”

I spent first night in Chelmsford alone in a cell, scared to death and didn’t sleep a wink.  The next day I was assigned a cell in the general population wing and my cellmate was ‘Big Bill Stevens’.  He gave me the some advice.

“Mike, you need a really, really big friend or two, otherwise those lads will eat you alive. Or should I say you will spend your life eating them!” he laughed.

Bill went on to explain prison life to me; how there were two types of inmates really; the hunters and the hunted.  With my small stature and my soft body, unused to any physical work, I was a sitting duck for the freaks.  I explained my background to Bill, about how I was a successful businessman who had the misfortune to drive home after consuming nearly a bottle of scotch.  About how I didn’t even remember hitting the girl.

“We all have our stories to tell,” said Bill, “and yours don’t mean shite in here.” He added callously.

“However,” said Bill, “there is another class of inmate.  The kind like you that has a lot of money on the outside; the kind that can buy protection; the kind that can get a get a guard or two in his hip pocket. Your kind.” He half laughed.

And that was it, the deal was struck. Big Bill Stevens became my minder.  With a liberal sprinkling of cash, which was provided by a bent guard to whom I set up a special account to access to my money outside, (and who took twenty five percent of every penny I had him withdraw); I was assigned to a larger more comfortable cell with Bill. We lived like kings; special food, special privileges, special packages from the outside containing booze, cigarettes, pornography, anything to make life more comfortable or anything that could be used for trade inside the nick.

I figured it was costing me more to live in jail than it was to live the high life outside, but I was locked up for five years with no hope of release, and without Bill as my minder, a few guards in my pocket, and the influence and protection of my money, life would be hell.

Then about three months ago, it all went to shit.  I found out there was another class of prisoner, a very special class of inmate who was so unique that there could be only one in each jail, the kind of inmate that ate the hunters just as easily as the hunted.  The kind of hard man that had nothing to lose, and was so hard the other kingpins in the nick paid him tribute and did his bidding without question.  The kind of inmate who didn’t need to bribe guards (although he kept them well paid anyway), because with one phone call to the outside he could have any guard’s family battered or worse.  The real boss of Chelmsford prison was not the Governor, It was Eddie McGuire, or actually, Mister McGuire to anyone but his closest confidants.

Eddie was in for life, but Eddie still ran one of the most successful criminal gangs on the outside.  Eddie wanted for nothing on the inside, the only thing he couldn’t have was freedom. And now Eddie had me!

Four month’s ago Eddie approached me and said he was impressed with how a faggot little man like me had set myself up.  He said he had no problems with the way I lived, as long as I bought my ‘special concessions’ from him, and as long as he got ten percent of any cash that I had smuggled inside.  From the look on Bill’s face I knew I had choice but to comply.  I figured it was just life in the nick and what the hell I had plenty of money working for me outside.

Then about a month after that I was sitting in the cell I shared with Bill wondering what was taking him so long to do the daily rounds of bribes and trading when I had an unexpected visitor.  One of Eddie’s minders came in to the cell and said,

“Bill won’t be back.  In fact he ain’t going anywhere any more.  When the fracas is over, you get your ass down to Eddie’s you little toerag.”

I wondered what the fuck he was on about, but next minute 2 prison officers came in and turfed me out. They searched the cell from top to bottom removing all my contraband and luxuries.

“You can go back in now arsehole.” One of the guards sneered. “Bill has had an accident and won’t be back.  You’re on your own until we re-assign you to another cell.  Sleep well sweetie!” The guard crooned and sauntered off.

I was scared shitless but knew better than to ignore the summons to Eddie’s cell.  I hurried down, minder-less for the first time since my arrival.  Eddie was waiting for me.  He was a slim man in his fifties, but sinewy with muscle.  I had heard he had choked more than one man to death with his bare hands.

Eddie wasted no time explaining the situation; Bill had been withholding some of the money I was supposed to pay Eddie.  Bill was now a permanent guest of the hospital and would never walk again.  Bill had fucked up big time.  And more importantly, Bill was my minder so I was responsible for his actions.  I tried to explain the situation; that I didn’t know Bill was skimming from the tribute I was supposed to pay.  Eddie quickly went on to explain that he didn’t give a fuck, that my girly ass belonged to him now.  I was going to become his accountant, his financial adviser, and I was going to pay him for the privilege of his protection.

I was moved into a cell next to Eddie that evening. What could I do? I had to have a minder otherwise I would be every hard man’s toy. I complied with Eddie’s wishes. I managed his funds and barter inside and I paid my tribute. After a couple of weeks I though I had nearly a better set up than before. Then some changes started to happen and at first I didn’t realise how drastically they would affect me.

Eddie had me organise some women’s clothing be bought in.  We had become sort of friendly; well as friendly as you could get as an underling; probably because a little chap like me was no threat to him.  He showed me some fashion magazines that he had bought in and pointed out some skirts, blouses, suits, and lingerie.  I have to say I was not suspicious at this stage, fashion mags in jail were poor mans porn that you didn’t have to hide them from the guards. I had also come to find out that some of the other effeminate inmates dressed as women and performed sexual favours for money. I also knew some of the more powerful prisoners had ‘wives’, crossdressed men who lived with them in their cells in homosexual relationships, either for protection or because they were just queer.  The guards turned a blind eye or took part of their take from the ‘working girls’; either way, I wasn’t really interested. 

I figured Eddie had me order in the clothing either to sell to the ‘working girls’ or he had his own ‘wife’ hidden away somewhere discrete in the jail.  I was really puzzled at how much interest he had me show in ordering the lingerie and shoes. He took special care in selecting sizes. Together we poured over the catalogues and I feigned interest as much as I could. I agreed with him that high heels looked lovely on a nice set of legs, but were hardly practical for a crossdressed inmate to get around the jail.

“You fucking nonce!” He laughed, his voice roughened from forty cigarettes a day. “She won’t be wearing them around the nick, just in my cell, and mainly on my cot.” He laughed again.

We spent ages looking at stockings and pantyhose.  He told me how much he loved nylons on a shapely leg and had me order in large quantities of fully-fashioned stockings and sheer to the waist pantyhose in many different shades.  I explained to Eddie that they would cost a fortune, as even the guards who were on the pad didn’t like prisoners having nylons because they were an ideal medium for suicide by hanging.  One or two inmates in the past had suicided by hanging themselves with a stocking.

“Just get on with the order, secretary!” he scowled.  “Just fucking pay the price! Just fucking do what your told!” 

I hated upsetting Eddie in any way as he scared me to death, and now I leapt to my feet to make the deal with the bent guards and pay their ridiculous prices for the smuggled in lingerie and other girly items.  Another thing I didn’t like was that for a week or so Eddie kept calling me his ‘secretary’ for some reason. I figured it related in some way to me being his accountant. 

Then the fateful day happened. Today!

I could walk around the jail with immunity now that I was ‘one of Eddie’s’.  I had sometimes seen other inmates point to me and I overheard them referring to me as ‘Eddie’s new secretary’.

“Oh yes, I can see what he sees in her.” One ‘noncer’ said, which I found puzzling.

It was just after dinner when I returned to my cell to find one of the prison ‘wives’ waiting for me.  I had seen him before and knew him as Craig, one of Eddie’s underlings.  I only just recognised him though as he made a quite attractive and convincing woman.

“Fuck off you poofter!” I shouted at him, her, It!  “Don’t you know who I work for!”

“Oh I know darling,” she cooed at me. “ And Eddie said it’s time.  You’re coming with me honey.   I’m going to prepare you for him.”

“What the fuck are you talking about,” I said.

“Look honey, my name is Carmel and I work for Eddie.  And you’re coming with me and I’m going to show you how to transform yourself for Eddie.” Carmel said calmly.

“I still don’t know what the fuck you are talking about.” I said

“Well honey is you look over your shoulder you will see ‘Iron Bar’ Steve.  You can either be transformed by him or by me ok?” Carmel crooned.

I turned around, and sure enough, there was ‘Iron Bar’, Eddies enforcer. He was grinning at me and slapping a piece of steel pipe in the palm of his hand.  I made my decision and nodded to Carmel who led me out of my cell down into E Block.  E Block was pretty much deserted and I had heard rumours that it was a part of the prison used by prisoners and guards alike for activities the general population didn’t need to know about.

Carmel led me into one of the bathrooms in block and turned into the small room where a big old white bath sat.  It was full of steaming soapy water.

“Strip and get in sugar,” Carmel said.

I looked around saw all manner of soaps, shampoos, razors and such.

“Fuck off hag fag,” I sneered at Carmel.

“Steve, she wants you!” Carmel yelled out the door, and sure enough there was ‘Iron Bar’ with a smirk on his face, smacking his trusty pipe into the other palm. Carmel pushed her face right into mine.

“You don’t seem to understand do you Mike? You either do exactly as I say, which is what Eddie wants; or, I let Steve there take you for the last walk you’ll ever have!”

I now realised the severity of the situation but was still confused. Although enough to do exactly what Carmel said or I would have my legs broken in such a way they would never mend.  I shucked off my clothes and lowered myself into the bath.  Carmel threw me a loofah and said “Scrub!” So I did.  Then she sat on the edge of the bath and took one of the disposable razors from a pack.  I was not surprised that one of Eddie’s ‘girls’ would access to an item that anyone else in the prison population could never get.

Carmel lifted my leg and stated shaving it.  I tried to pull my leg away and she held it tight, gave me a stern look, then glanced towards the door where Steve was lounging outside. I surrendered.

“Watch how I do this hon,” Carmel said,  “you doing this shit yourself from now on.”

Then it dawned on me what was happening, the significance of the word ‘transform’; the reason Carmel was shaving my legs.  I felt numb.  I couldn’t comprehend why Eddie would do this to me.  I was in a trance as Carmel fished shaving my legs and then the soft down on my arms.  She shaved my face and rubbed moisturiser onto it.  Then she led me out of the bath and dried me off.  I was just like a mannequin that Carmel could move around and pose as she liked.  Carmel led me to the part of the bathroom that had about ten sinks and mirrors lined up along the wall. It wasn’t until later that I took notice that the usual stainless steel mirrors had been replaced with glass and that each of the mirrors had a bright light over it.  One of the sinks had a high stool set up in front of it and Carmel sat me on it.

“Now pay attention honey, you need to learn how to do this,” she said.

I noticed that on the shelf below the mirror was a large assortment of makeup.  Carmel took a damp sponge and applied generous amounts of foundation to my face, cooing at how lovely my skin was and that I didn’t need to use 'dermablend' or other such heavy-duty foundation.  After she had applied the foundation to my face and neck she picked up brush and applied a slightly lighter coloured powder to set my face.  She rouged my cheeks, accenting my high feminine cheekbones.  She fussed around my eyes applying liberal amounts of eyeshadow, eyeliner, and mascara. She then finished with another light dusting of powder. All the time Carmel was explaining to me how I would need to learn how to apply my own makeup. I was still too dazed to really accept what was happening. The final touch was the application of a bright red nail polish to my toe and fingernails.

Then Carmel reached under the sink and opened a cupboard.  She pulled out three wigs sitting on wig stands and I noticed there were a lot more in there.  Carmel looked at me seriously for awhile then selected a blonde bob and pilled it on my head.  She turned me towards the mirror and made some adjustments.  I was shocked as I looked at myself; I looked stunning.  I couldn’t believe the transformation to my face.  I looked like a sexy, mid thirties, over made-up, slut.

“You like?” Carmel smiled at me.

“I look like a fucking woman!” I shrieked.

“Well that’s the idea stupid,” Carmel Laughed. “Follow me.”

I followed her out of the bathroom, stark naked and with my face made up to look like a whore. ‘Iron Bar’ Steve followed at a menacing distance.  Carmel led me into a cell in a set of six on the next level up.  The five others around it were all deserted but the cots were made up with what looked like satin sheets and comforters.

“This is your workroom honey, hope you like it,” Carmel said as she led me inside the cell.

I couldn’t believe it, the oversized cot was made up with satin sheets and a full sized wardrobe was open and hanging there were the clothes that Eddie had made me help him pick out.  Four pairs of different coloured high heels were arranged on the bottom of the wardrobe and in the drawers that were pulled open was the lingerie Eddie had spent so much time selecting with me. Now I knew why! Carmel led me over to the bed and sat me down.

“Well I guess I better show you how to dress too,” she said.  “Eddie was quite specific about what you were to wear for him tonight.”

Carmel selected a pair of shiny, sheer to the waist taupe pantyhose and rolled them up my legs. She stood me up and showed me how to pull them tight around my arse.  The nylon felt cool and slippery on my legs, not unpleasant. I had always loved to run my hands up a nyloned thigh but had never imagined what it would be like to wears them.  I nearly died when Carmel put her hands inside the gusset of the hose and grabbed my cock and pushed back between my legs. The tight nylon held it snugly against my ass.

“There,” Carmel said, “lets get that little thing out of the way shall we?” she laughed.

I heard Steve laugh at the door and realised to my humiliation that he was watching the proceedings. Next Carmel pulled a pair of silky nylon peach coloured full cut panties from the drawer with a matching bra.

“Here,” she said, handing me the panties, “put these on while I get the breastforms”.

I didn’t know what the fuck she was talking about, Breastforms?  I slid into the panties, the silky nylon of the panties created little electric shocks of pleasure as they rubbed against the sheer nylons as they slid up my legs.  Carmel turned around and was holding two perfectly formed small breasts, one in each hand.  She put them down and put the bra on me then placed each of the plastic breasts in each cup.

“There is some adhesive in the dresser draw that has instructions on how to adhere the breastforms to your chest. You can learn to do that later.  The way I’m dressing you tonight it won’t matter you just need the shape.” Carmel said, sounding serious about subject totally alien to me.

I was still in shock as to what was happening to me when Carmel sat me down again and lifted my feet one by one and placed a back shiny high heel on each one.  She pulled out a little jewellery box from out of a draw in the base of the oversize cot. 

“For fuck sake keep this locked away from now on and never lend your jewellery to any of the other girls.” Carmel said very seriously.

‘My jewellery!’ ‘Other girls!’ ‘My workroom!’ What the fuck is happening to me I wanted to scream.  I kept my cool though, I realised I had no choice but to succumb to the ministrations of this freak man/women who was dressing me or have ‘Iron Bar’ Steve cripple me for life.  One I saw Eddie I knew I could convince him that he had his little joke and that I would make up for what ever mistake I had made as soon as I got back to work as his finance manager, back in the general population of the jail.

Carmel selected a simple gold ankle chain and fastened it around my slim ankle.  The gold twinkled in the light against the sheen of the sheer nylon. Carmel put two gold bands around my right wrist, and a simple but elegant, gold ladies watch on my left.  She placed another simple gold chain around my neck, for which hung a black onyx stone set in gold.  She clipped matching earrings to my ears.

“We’ll pierce your ears tomorrow hon,” she said humming away as she worked.

Like fuck you will, I though to myself.  Next Carmel had me stand and I teetered on the high heels, steadying myself by holding on to her. 

She smiled, “You’ll soon get used to them.”

I thought again, like fuck I would because after tonight I’ll never need to wear them.  Eddie will see this is a mistake. Carmel selected a satin waist-cincher that matched my bra and panties and pulled it tight around my waist.  My already un-masculine body was now positively effeminate.  My smooth long legs enhanced by the sheer hose, my arse had been pushed out slightly by the squeeze of the cincher, my false tits that just proportional to my small build, and my little waist. I looked like a well looked after thirty-year-old woman.

Next Carmel took a cream coloured silk blouse and pulled it up my arms and buttoned up the front.  It was open down to the second button and showed a hint of my peach bra.  Next she had me step into a peach nylon half slip, that again matched my bra and panties.  It too gave me little electric shocks of pleasure as it slid up my nyloned legs. Carmel reached into the wardrobe and pulled out a hanger on which there was a bark blue women’s business suit.  I remember Eddie picking it out of a catalogue and wondered at the time why his ‘working girls’ would need something so sophisticated.  But along with nurse’s uniforms and other fetish clothing I figured it was just to pander to some expensive punter’s peccadilloes.

Carmel had me step into the skirt and pulled it up my legs and fastened it around my waist. She straightened my blouse, ensuring it was tucked in and then surprised me as reached under the skirt and pulled the half-slip that had become rucked up when I donned the skirt.  I got another of those little electric shocks of pleasure form her hands straightening the slip and touching my stocking legs.  I looked down and was surprised to see a pair of sexy pantyhosed legs showing from below the hem of a navy blue skirt that was six inches above my knee.  Attached to those legs were a pair of sexy nylon encased feet, the red toenails showing though the gossamer nylon.  Around one slim ankle a gold bracelet reflected a glint of light.

Finally Carmel helped me into the matching jacket and led me over to a full-length mirror that was attached to the wardrobe door.  I was amazed! Staring back at me was a gorgeous woman in her mid thirties. Her bottle – blonde hair and over made-up face atop the cream blouse and navy blue power suit made her look sophisticated but strumpet like.  Carmel spun me around so I could see my side and rear.  My ass stuck out provocatively and stretched the material of the skirt taught against my arse. It was forced that way by the pull of cincher and stance I had to adopt to remain on feet in the high heels. The rear of the skirt had a small split that showed about another six inches of the back of my nyloned thighs.

Just then I saw hand reflected in the mirror as it grabbed my arse.  It was Steve.

“You look great,” he growled as he pawed my arse and legs.

“Get the fuck off her Steve or I’ll tell Eddie,” Carmel screamed smacking Steve’s hand away.

Steve retired to the door sheepishly.

“You know Eddie always gets them first!” she yelled after him.

Then the full light of the situation dawned on me.  As I looked at the reflection of the trampy woman in the business suit I realised she looked just like a caricature of the ‘sexy secretaries’ I had seen posing in porn magazines just before they stripped off their clothes, page by page.

Now I knew why Eddie had called me his secretary! Oh my god! He had been planning this for weeks, having me help him pick out clothes, obviously getting his ‘girls’ to find out my sizes for clothes and shoes.  And now I had no choice but to be Eddie’s ‘sexy secretary’ or suffer an agonising beating and the loss of my limbs!

“Mike, now you are Michele, you look beautiful. I hope you enjoy your first time as much as I did,” said Carmel as she slid past me and out the door.

And that is how I became to be dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail.

To be continued………………………………..

 

And so it was for the next six months. I engaged in all the nylon fetish sex I could possibly want. I had my Mom, my Sister, and Matron wrapped around my fingers. They enjoyed our sexcapades, sure, but beneath it all was the undercurrent of incest and forced sex; after all I had raped all of my now willing participants to begin with.

I had the company of my three nylon queens individually, Mom and Sis together, and occasionally all three of them together; and of course they always wore nice sexy outfits, often their respective uniforms, and always pantyhose or stockings and nylon panties; my fetish dominating our incestuous relationship.

Mom was at first quiet shocked when she found out Eileen and I had blackmailed Matron into our 'silken family trap', but quickly submitted to the new rules of my game. She eventually capitulated to a foursome when we invited Matron around home for dinner, followed by lashings of sex for desert. I had the pleasure of watching Mom and Matron sixty nine each other fully clothed, their heads buried under each other's skirts as they pleasured each other lying on the couch in the lounge whilst Sis stroked me off into a sheer stocking. I managed to fuck all three of them that night but was so tired I had to take the next day off school.

And then things took a strange turn that I never would have expected nor ever dreamed could happen.

It was a cool sunny winter afternoon when Mom came into the house excited.

"Look kids, we've been invited to fancy dress party by the girls on my shift at the Ward," she beamed.

"Not fucking likely!" I responded. "That sounds like girls fun to me."

"Oh come on Mike, it sounds like fun, it's a 'Whores and Pimps' night," she said.

"What's a 'Whores and Pimps' night?" Eileen asked.

"Well obviously the girls go to the party dressed as whores and the guys dress as pimps; you know the sort of thing," Mom explained.

"Well Mike, if me and Mom dress as whores, you know what that means don't you? Short skirts, high heels, sheer nylons, pretty panties, lots of slutty makeup, all the things you hate." Eileen teased.

"Now that you put it that way, it sounds like it could be fun, especially on the way home in the car after you girls have had all night to tease me, not to mention the other 'whores' who will be at the party. Ok, count me in," I said.

"Well its three o'clock now and we've to be there by seven, if you get showered and changed by five Mike, that leaves your Sister and I plenty of time to find suitable costumes and prepare ourselves for the evening. If you behave we might even give you something before we go," she winked.

"Well Mom, having an intimate knowledge of yours and Sis's wardrobe, neither of you will have problems dressing up as whores," I taunted.

"Hey!!!!!!" they both chimed in together; but it was too late I was of to my room to see what I could throw together for fancy dress.

'What the fuck does a pimp wear?' I wondered.

As I shaved, showered and dried myself off, I fantasised about the evening to come; lots of women and girls dressed up as whores. They were all bound to wear revealing clothing, miniskirts, hot pants, that sort of thing; and all whores wore nylons didn't they? I could hardly wait!

I wondered into the lounge room about six o'clock looking despondent. As a teenage lad I had no idea what a pimp wore and the best I could muster was a wrinkled suit that I had almost outgrown, and a cowboy hat.

Both the girls burst into laughter when I entered.

"Oh fuck Mike, you look like a dickhead," Eileen chortled.

"Hey, that’s not fair. He looks like a kid who hasn't a clue how to dress," Mom laughed in time with my Sister.

"Oh cut it out you two. It's easy for you, your costumes are just the sort of thing you wear for me around the house anyway, and I must say you both look like eminently fuckable whores," I retorted.

Mom was wearing her shortest black leather miniskirt, a black low cut short sleeved blouse, matching black patent leather, six inch high heeled 'fuck me' pumps, and sheer black seamed stockings. Her reinforced stocking tops were easily visible at the hem of the miniskirt and they were clasped into bright red garter straps that disappeared under her skirt and led up to her garter belt. The crotch of her matching gauzy red nylon panties was just visible whenever she made the slightest move and her identical red bra was on display for all to see, pushing up her tits and hardly covered at all by her blouse. Her flaming red hair was worn frizzed and big, framing her heavily made-up face; lashings of black mascara, mauve eyeshadow, blushed cheeks and ruby red lips. The outfit was completed with a gold necklace, gold bangles on her wrists, gold teardrop earings dangling from her ears, and a matching anklet glittered on her sheer stocking encased ankle. She looked just like an eighties whore!

My Sister was wearing white skin tight nylon bustier, her lovely adolescent tits on display. She had squeezed into the tightest hotpants I have ever seen. The taut red lycra hotpants were moulded to her ass and emphasised her pubic mound; there was no visible panty line meaning that the glossy taupe pantyhose that glittered on her long legs was the only underwear she was wearing. The ensemble was completed with white platform shoes. She wore her red hair in a similar style to Mom; her makeup was also identical, although her selection of jewellery was gaudy and ornamental. The single exception being the gold ankle bracelet, identical to Mom's, sparkling on her gossamer encased ankle. She looked like a seventies whore!

I was enamoured with my pair of whores from decades past and could hardly wait to get my hands on them.

"Well come on Mike, cant you do better than that for a costume, look at the effort me and Mom have put in," Eileen complained.

"Leave him alone," Mom replied, "Let me look in you wardrobe Mike and see if we can't find some thing more pimp like shall we?"

Mom led the way to my room and I couldn't take my eyes of her ass and legs. Her pert buttocks, encased in her sheer red panties peeked below the hem of her skirt, and her legs looked so long, accentuated by the seamed nylons and high-heeled pumps. We rummaged around in my wardrobe and found nothing suitable for me to wear. Returning to the lounge we I sat down next to Eileen and Mom went to the kitchen and returned with drinks. Mom figured that as been as we were all fucking each other and breaking the incest taboo, what difference would a little under age drinking make? Mom handed me my favourite drink, a rum and coke.

"Well I do have one idea Mike," she said coyly, a cheeky grin on her face, "but I'm not sure you would be up for it?"

"What?" I asked.

"Well……….what if you come along as a whore too!" she exclaimed.

"FUCK OFF!" I responded immediately; but then Eileen piped straight in,

"Great idea Mom, I bet we can make him look a proper trollop; come on Mike it'll be fun."

"No fucking way!" I again replied, "You are not dressing me in drag!"

"Come on," the girls chimed together.

"Think of it this way Mike," Eileen said smugly, "You are always getting into our pantyhose and knickers, now it will be our chance to get into yours."

I thought back to the time a few months ago, before I had 'tamed' my Mom and Sis: 'Alone in my room I would enact my pantyhose fantasies. I would wear them, sniff them, and wank in them, all kinds of pantyhose perversion. I loved the sight, feel, and smell of nylons. I could get an erection just rubbing their silken material against my face, and could orgasm by just rubbing my cock against the silky fabric. Yes living with two ladies who wore pantyhose every day had its advantages'.

I had loved the feel of nylon on my legs and balls, and this would be one way to experience that lovely feeling again, and maybe I could enact my ultimate fantasy after the party; fucking a girl in nylons while I was wearing them too! Maybe I should go along with their harebrained scheme to please my own appetites. Besides, the drink was starting to kick in, I felt relaxed and uninhibited.

"Ok," I found myself saying, "you can dress me like a whore, but you girls are really going to have to put out to repay me for this little party trick."

"Oh you will get repaid Mike," Mom said, "you will get repaid."

Eileen bought me another rum and coke, "Here Mike," she offered, "drink up, we're going to a party remember?"

"Ok Sis, you bet, these drinks are great."

I was really starting to feel woozy as I gulped at the second drink, I can usually hold my liquor pretty well, even for a teenager, but this evening it was going straight to my head. I vaguely remember being led to the bathroom and the girls running me a bath. They gave me another drink while they ministered to me.

"I have already had a shower," I said, my voice sounding like it was coming from a long way off.

"Silly, we're shaving your legs Mike, you can't be a sexy whore with hairy legs," Mom laughed.

"Fuck off, you can't do that," I tried to get up, but it was no use; I fell back in the tub and started giggling.

Eileen helped me drink my drink by holding it up to my mouth. The rest of the evening was blur. I can remember little episodes of clarity, the girls drying me, dressing me in lingerie, helping me into a skirt and blouse, Eileen holding my head still while Mom applied makeup and pulled a wig over my head, Eileen bending down and buckling shoes on my feet. Shoes that I couldn't stand up in when they finally got me to my feet. After that I don't remember a thing, the world became one big blur, then it was dark.

Darknes……………………………………………………………………………………………………………………………………

 

SNAP!!! I felt this tremendous rush as I breathed in the fumes from under my nose. Mom was standing in front of me waving a phial of something in my face, the vapours of which instantly sobered me up, and made me wide awake.

I knew something was terribly wrong. I was standing but my arms were extended above my head, my wrists clamped into what could only be cuffs. The weight of my body was suspended from my wrists and I struggled to take my weight on my feet. Then I realised that my feet were in some kind of strange shoes that made it hard for me to get my balance. Then I remembered my sister strapping me into a pair of Mom's high-heels. I also realised that my legs were held apart about a metre and no matter what I tried I couldn't close them.

Mom moved away from me and I looked down and was shocked. On my feet was indeed a pair of Mom's black high-heeled open toe pumps. I could see that my toenails were painted bright red through the opaque reinforced toe seam of the fully-fashioned smoky grey nylon stockings I was wearing. ( Similar to Matron's favourites I though somewhere in the recesses of my mind. ) I remembered vaguely about volunteering to dress in drag for a party, that explained the shoes and stockings; but I couldn't understand why there was a metre long stainless steel bar clamped above each ankle with a leather cuff holding my legs apart.

My eyes continued looking up my body. About mid thigh began the hem a black miniskirt made of some silky material, my other senses were awakening now and I could feel the luxurious feeling of the nylon stockings on my legs. The hem of the skirt sent little electric shocks along my thighs as the material stroked against my stockings. I was wearing a pink nylon blouse that felt so light and sexy against my back and chest; but I noticed I had false breasts and felt what could only be a bra around me. I followed the sleeves of the blouse up and saw my wrists clamped securely in the cuffs, my fingernails were painted red and my hands had been shaved; they looked positively feminine.

Ok, I figured out that the girls had dressed me as a woman for the party as I had agreed to, but why was I in captivity? I noticed some other things too, I was obviously wearing nylon panties, as I could feel the sensuous material against my balls and cock, and snug against my ass cheeks. I could discern a silken garment tight against and just over my panties, a suspender belt; I realised as I sensed the silken garters extending to the tops of my thighs. I could feel the little clips of the garter snaps on my thighs where they were attached to my stockings.

Mom stepped in front of me and held up a large mirror. I looked at her confused but she just held the mirror up to me. I saw a tawdry whore looking back at me. She was quite attractive in a cheap fuckable way. Framed in a blonde bob, was a face that had been heavily made up complete with lashings of mascara, eye shadow, rouge and lipstick. I realised it was me!

Mom smiled at me as saw the realisation on my face.

"Mike, we've turned you into Michele. Don't you like her?"

"Why?" I asked. "Why am I handcuffed like this Mom."

"Well Mike, er Michele, I spiked your drinks, being a Nurse I can get all kinds of drugs you know. Then your Sister and I shaved you all over and dressed you just like you are now. We applied that makeup and wig and then strung you up. Finally we put that restraining bar between your legs."

"Of course even me and Eileen had to have help to drag you down here to the basement and truss you up; so Matron helped."

Matron stepped into my sight. She was dressed in a black full body corset and waist cincher, her tits pushed up and out. From the bodice of her waist cincher, suspenders ran down her legs to her favourite smoky grey fully-fashioned nylon stockings. She had on a pair of the highest heels I had ever seen; black of course. She too was heavily made up.

"Hi Michele," she smiled at me and winked.

"But why?" I pleaded again.

"Because Mike, you need to be taught a lesson. Although we enjoy having sex with you and each other, and really get off on your nylon fetish, you did rape us!"

"What?!?" I asked amazed.

"All of us Mike, you forced yourself on all of us to begin with. So now you are going to see and feel what it's like to have someone force themselves on you. We have turned you into a girl; and now we are going to rape you!" Mom said viciously, her heavily made up face angry but so sexy.

"See! I knew you were the sort of lad who would have more fun if I left my nylons on," she said.

By the time I was in my teens I had a full-blown nylon fetish, by now women were wearing pantyhose instead of stockings but I still loved nylon encased legs. I had quite a collection of nylons most of which I got when Mom or my sister discarded theirs; I would wait until no one noticed then take them out of the bin. I was also wearing nylons a lot when no one was around or I was in bed and masturbated while wearing a pair of pantyhose and then placing a nylon on my cock. One of my favourite pastimes was visiting my Aunt Mary, she was a single mom who lived alone with two daughters, and they all wore pantyhose. While my sister was playing with the two girls I would rummage in their bins for discarded hose and rifle their laundry basket. Then one day I got caught.

I was 15 and Abegail, my eldest cousin was 18, and she was the one that caught me. The three girls had supposedly gone shopping with Aunt Mary, leaving me to my carnal pantyhose pleasures while they were gone. What I didn’t know was that Abby had left the others to return home, feigning a stomach upset. But I found out later that she suspected I was tampering with her lingerie and she intended to catch me. She told me later that she had noticed stains on her pantyhose when she washed them and as she was 18 and sexually active, she had good idea what those stains were. I was by this time, oblivious to the world, hiding in their bathroom wearing a pair of sheer pantyhose and stroking myself through the sheer nylon gusset. Abegail burst through the door and shouted "I knew it, you pervert, I knew you were wanking in my lingerie, you fucking little pervert". I was so scared and embarrassed; here I was standing in her bathroom wearing nothing but a pair of her pantyhose and a hard-on, which by now was quickly deflating. I lost control of my legs and sat down heavily on the toilet seat.

"You fucking Nancy boy" she said, "wait until I tell your mom, my mom, your sister, every fucking one that you’re a Nancy-boy, pantyhose wearing, pervert!" I was so scared and started begging her, "please Abby, don’t tell anyone, I’ll do anything you say, I’ll stop doing this, I promise!" I was a pathetic sight standing in front of her naked, grovelling to her. She was standing over me fully dressed, she was wearing a cute little purple mini-skirt, white blouse and platform heels (this was the 70s remember) and of course, beige pantyhose (beige and white were the mainstay of 70s hosiery). "You bet you’ll do anything ‘pantyboy’" she said, "You’ll do whatever I fucking well say or everyone will know about your little pantyhose perversion!" By now the initial shock had worn off and couldn’t help noticing her legs showing nicely below her mini, she had one foot forward and her hands on her hips in a dominating pose, she was a little chubby but had nice legs and a pretty face. Of course her standing like that with her silken hose covered legs at eye level had an obvious effect on my penis. Abby had never particularly liked me and had teased me a lot when I was younger, her being three years older she was always dominant, now she noticed my gradually stiffening penis. "You fucking freak, you can’t help yourself can you?" she said pointing at my nylon-covered appendage, "well now that horrible thing is sticking out, you humiliation starts now pantyboy". "Stand up pantyboy" she said, "lets see what that pathetic little dicky looks like". I knew Abby had had a few boyfriends and guessed she was no stranger to male anatomy, and I definitely knew she was certainly not going to miss the chance to humiliate as much as she could, but standing there, her tight sheer pantyhose encasing my lower body, and her being fully dressed somehow excited me.

I stood up and my now erect penis was pushing out the gusset of the hose, there was a small pool of clear pre-come forming at the end of my penis and soaking into the nylon. "Well you are the panty-boy, aren’t you, now I know why those stains were appearing my pantyhose every time you visited, you disgusting little pervert. Go on, show me what you do when your wearing my nylons." I stammered, "what do you mean?" "You know what I mean pantyboy, wank that disgusting little cock!" She started to laugh as I took my cock in my hand and started to stroke it through the nylon, "you really are pathetic you know" she said, "I’ll bet you’ve never even been with a girl before have you!" "No" I answered looking down at my pathetic nylon covered toes, tears were starting to form in my eyes and I didn’t want her to see me cry. She stepped forward and lifted my chin, "stop that you pathetic pantyboy, I don’t want you simmering away, now stroke that fucking cock! Show me what you do in my hose or the whole world will know!"

I put everything else out of my mind and just stared at the little purple mini and her thighs below the hem. I started to stroke my hosed member again. It started to feel nice and I could feel really myself engorge at the thrill of what I was doing, wanking off in front of Abby. I have to admit it was a fantasy I had had previously when I masturbated while wearing her pantyhose. I stroked it faster, rubbing the sleek nylon gusset against my turgid member and staring at her legs, imagining my cock rubbing against them. "You fucking pervert!" she hissed, "your really enjoying that aren’t you! Well I’ll put a stop to that!" She reached out and slapped my hand away from my cock. "Leave it alone pantyboy" she said, I looked down again at my toes, humiliated again. "Don’t look down, look at me! And leave that alone!" she said pointing to my hard cock poking out the front of her pantyhose. Its disgusting she said and all of a sudden reached out and grabbed it to make her point. It was too much, I was close to coming before, but the feel of a girl’s hand holding my cock while it was encased in sheer nylon was a sensory overload. I shuddered and groaned as I spent my seed. The ejaculation pulsed out of my throbbing penis and poured through the nylon gusset into Abby’s hand.

Abbey of course was disgusted and wiped her hand on my body, covering me with my own semen. "Now fuck off out of here pantyboy," she said, "and never touch my underwear ever again". I heard her mocking laughter as I ran down the hall the bedroom in which I was staying. To say I was terrified was an understatement; I was so scared she would tell everyone about my perversion. Days, then weeks passed and nothing happened. Whenever I met Abbey she would snigger at me but never bought up the day she caught me. I wondered why she had the ultimate degradation to inflict on me but didn’t. Then it dawned on me, she was older that me, she had humiliated me, she should have known better and more importantly, what she did to me was wrong.

It was then I hatched my plan. Next time we visited Aunt Mary, I confronted Abbey in her bedroom "what do you want pantyboy" she sneered. I told her what I had been thinking about what happened "well what the fuck you going to do about it pantyboy, you can’t tell anyone otherwise they will know you are a pervert". I was really angry now and answered "I am going to tell mom, she wont care about what I was doing, just what you did to me, your older and should know better, she will tell your mom for sure!" I could see she was starting to sweat, her bluff had been called. "Please don’t tell" she said, "I’m sorry, I take back what I did." Not good enough I said as my plan formulated further in my mind. "You have to be punished for humiliating me," I said. "Whhhhhhhhhat do u mean?" Abbey looked flabbergasted. "You have to make it up to me" I said, "or I just leave right now and tell mom and Aunt Mary what happened!" "Ok, ok, ok" she said cutting me off as I headed for the door, she closed the door and locked it. "What do you want from me?" she asked. "Well’ I said, "I know that you have had boy friends so I figure you must know all about sex." She looked shocked "so!" she said. "Well now your going to let me do some things to you that you have probably done before anyway, so you shouldn’t mind" I grinned evilly at her. "No fucking way!" she exclaimed. "Ok then" I said and started to unlock the door. "Alright!" she sighed disgustedly. "Sit on the bed and don’t say another word" I said, "now its time for to pay". She sat demurely on the edge of the bed. She was wearing another A-line mini, white this time, a pink blouse, platform shoes, and of course, my favourite beige pantyhose. I sat down beside her and placed my hand on her knee, the nylon felt silky against my fingers and immediately began to stiffen. I stroked her leg up and down from the top of her thigh to her ankle. She just sat there and stared up at the ceiling, enduring my molestation. She stiffened as I my hand went under her skirt and rested on her silky nylon panties. They were full cut sheer white nylon. Her hand went on mine and tried to push me away, "Mom" I yelled, but not loud enough for anyone outside the room to hear. She understood the threat and took her hand away. Now I stroked her through her panties, feeling the nylon of the panties rubbing on the nylon of her pantyhose gusset was making me extremely aroused. I noticed her breathing was deeper and quicker and her eyes were closed. I eased my hand down to my shorts and freed my erect member. I leaned over and began to rub it on her pantyhosed leg as I continued to stroke her panties. We were now both breathing deeply and heavily and I could feel her panties becoming moist to my touch. I was so excited, the first time I touched a girl there and she was enjoying it, even if she was being forced to do so. I gently pushed her back on the bed and climbed over her, she whimpered "nhhoo", but her heart wasn’t in it. I pushed her skirt up to her waist and lay on top of her. My throbbing penis was pushing against the nylon of her panties and as I began to grind it back and forth, I felt it rubbing against her panty and pantyhose covered pussy. Amazingly she began to push back against me, matching my thrusts with her own. I put my hand down and moved her panty crotch to one side and tried to push my member through the hose; "NO, NO, NO, NO!" she whispered in my ear, "you cant do that, you can’t fuck me". She reached down and placed my penis in the folds of her pussy, but still protected by the sheer nylon of her pantyhose, then she eased the silky gusset of her panties over the top of my penis. It was exquisite, my penis in a nylon trap, the sheer hose covering her pussy was pushing against the base of my penis and the silky gusset of her panties was pushing against the top of it as we thrust against each other. We ground against each other, panting and sighing, but I felt myself ready to come. She felt it as well and wrapped her nylon-encased legs around me and held me to her as she pushed her silky gusseted pussy against my penis. Then she kissed me thrusting her tongue deeply inside my mouth as I exploded against my cousin. I could feel my semen saturating her pantyhosed pussy and legs and soaking her panties. She was pushing against me so hard and she groaned "Goooooooooooodddd" into my mouth as she was kissing me and shuddering with her own orgasm.

I enjoyed Abbey’s pleasure many times over the next few months; she always kept her pantyhose on to prevent me from entering her. She explained that, as I wasn’t actually fucking her, in her mind, we were not really breaking a family taboo. We were exploring new ways to pleasure ourselves, she knew I loved the feel of nylon against my cock because she had caught me wearing her pantyhose. So it did not take long before I was wearing her pantyhose during our ‘sessions’. One day she had me wear a pair of her nylon panties over sheer to the waist pantyhose whilst she was dressed the same. The feeling of our highly aroused sexual organs rubbing together encased in folds of nylon from the panties, straining against the sheer nylon gussets of the pantyhose was wondrous.

But then as suddenly as our sexual encounters started they came to a screaming halt. It did not take too long for 18 year old Abegail to acquire a new boyfriend, a new jealous boyfriend. Besides the fact that she now hardly had any spare time at all when I visited, she explained to me that if we continued what we were doing she would be cheating on him. Also she said she believed what we doing was very close to incest; she could not continue our sessions any longer but had enjoyed what we had done in the past. She asked me not to be jealous of her boyfriend but to remember fondly our lovely encounters. Abbey gave me two pairs of her pantyhose and a pair of her sheerest panties as a ‘farewell present’.

My passion for nylons and nylon panties continued on through my teens and into my twenties. I still wore pantyhose and whenever possible nylon panties to bed and to masturbate. I liked to wrap a sheer stocking around my cock whenever I wanked. I managed to get myself girlfriends, (always girls that wore pantyhose often), lose my virginity, and on the odd occasion find a girl that would share my nylon fetish. A couple of my girlfriends let me fuck them while they still wore their stockings or pantyhose and one girlfriend I had when I was 25 would let me wear pantyhose as well.

One afternoon my girlfriend Eileen and I were in the bedroom of my flat lying on the bed. I had my hand under her skirt, stroking her pantyhosed thighs. My hand would wonder across her crotch, pushing against her nylon encased mound; she was moaning and pushing against my hand. "That feels so good" she whispered. "I know" I said, "I just love the feel of nylon against me too". She giggled, "go on then – get dressed, I know you want too". I quickly discarded my clothes and slipped on a pair of sheer pantyhose. Eileen was hip to my fetish by now and we had often fucked whilst both wearing hose. Her hand slipped up my nylon legs and lightly caressed my balls. I was in heaven as I maintained my pressure on her silken clad mound. I pushed her back on the bed; she looked magnificent, fully clothed with her red miniskirt hiked up around her waist, sheer taupe pantyhose, white nylon panties, and red high heels. I climbed on her and ground my hard member against her mound. My cock and balls encased in the fabric of my pantyhose was rubbing against her pussy covered in the sheer nylon of her pantyhose and panties. I reached down and with my fingernail I made a small hole in the front of my pantyhose and let my dick poke through. I now had my cock rubbing and pushing into her pussy. I could feel her outer pussy lips against my cock head through the nylon of her hose and panties. I again reached down and this time made a small hole in the gusset of her pantyhose. "Oh Dear! I ruin more nylons this way" she giggled and wrapped her sheer nyloned legs around by back as my penis pushed aside the fabric of her panties and slid into her. I was so excited and was already close to coming. "You really do love nylons don’t you darling" she whispered in my ear as she thrust up against me slowly. "Oh my God yes" I whimpered, on the verge of orgasm. "I have an idea," she said, and to my despair she eased me out of her glistening pussy. "What are you doing" I begged. "I’m so close." Again she giggled and to my surprise she reached over to the bedside table and dipped her hand into the drawer where I kept my pantyhose, stockings, and panties. She drew out a sheer nylon stocking and to my utter amazement and delight, slipped it over my hard penis. She slowly stroked my throbbing member through the nylon of the sheer stocking. "Christ I’m going to come!" I shouted. "Not yet" she whispered into my ear as she slid back under me and positioned my stocking encased member against the entry to her soaking pussy. She then pushed slowly but firmly against me, sliding the nylon covered cock into her cunt. I was in heaven. Her hot wet pussy was gripping my stocking covered cock like a silken glove. At the same time my pantyhosed balls and legs were rubbing against her pantyhosed legs and sheer pantied arse. I couldn’t hold it any longer; I exploded deep inside her. Needless to say I married Eileen.

I am a 20-year-old crossdresser. I have been dressing as a woman for five years without my family knowing. There is certainly no way I was going to tell my now 16-year-old brother Tom what I did for kicks. He had grown up rough, and unlike me, who enjoyed a serene, some would say sissy lifestyle, Tom couldn’t wait to join a street gang. While I locked myself in my room trying on makeup and sexy women’s clothes, my younger brother was playing football, sneaking beers, and committing petty crimes with his pals.

I had been sneaking out of the house dressed as woman for about 3 months now, and I always headed to the local park where I was guaranteed of picking up some rough trade; usually older men who would take me in the toilets for a quick blowjob or a quick fuck against the cubicle wall.

Tonight I had walked down to the local park and was sitting in my favourite dark corner, looking for punters who occasionally cruised the park looking for action. I was certainly dressed for action; red Lycra miniskirt, blue and black sequined top, sheer black nylon stockings, sheer red nylon panties, garter belt and black ‘fuck me’ high heels. I had put on my trademark ‘slutty make-up’ and my favourite blonde wig. I looked nothing like my male self, and was confident that I would not be recognised by anyone who knew me casually. I was having a chat with an older man I'd met before, the memories of an earlier visit we had made to the toilet block quite turning me on and hoping we were going to get it on.

Then I saw them, a street gang I had never seen around my ‘patch’ before, but I instantly recognised Tom amongst them. There were six of them and they were all young, fit and no doubt full of the beer they'd obviously been drinking that evening. But I hadn't come out looking for trouble that evening, that wasn't my scene at all, even so I knew I only had myself to blame for the fix I was in. I deliberately hung around this park because I knew Tom’s gang never came here and now my luck had run out.

Unfortunately the street gang now entered the park and my ‘older friend’ just turned and ran. The gang swaggered towards me. I knew I had a few options: identify myself to Tom and live in ridicule for the rest of my life, or chill out and hope they passed and left me alone. Possibly stupidly I lit a cigarette to still my nerves as they approached and instead of passing, the gang veered over to my seat, a voice asking,

"Can you spare a couple of cigs?"

These boys all appeared to be in their teens or early twenties and I knew from talking to Tom that they had a reputation for trouble. As I said, obviously they'd had more than a couple of beers apiece but they did not appear to be over the top pissed. Maybe they would take my smokes and move on. As they came closer I prayed they, and particularly Tom, would not recognise me in the dim light.

One was jet black; he looked the oldest, wearing white rugby style shorts and a black T. The youngest looking was also coloured, more a coffee colour, in his case wearing denim shorts and a polo shirt. The others were white but standing more in the shadow so I couldn't make them out so clearly at that time, but I knew one had to be Tom. I handed over a couple of cigarettes saying I couldn't spare any more and was told.

"No problem."

They stood around to light them and the thought had just crossed my mind that I wouldn't mind meeting one or two of them at a time down here if only they weren’t Tom’s friends Then the oldest asked, out of the blue,

"Do you suck cock u dirty Tranny?" I was taken aback, but it was obvious they recognised me for what I was, a crossdresser or transvestite if you like, and without really thinking I replied,

"It has been known."

There must have been some sort of pre-arrangement between them because the leader pushed a younger coloured boy toward me laughing and saying,

"Well let’s see you then. My friend here has been sporting a hard on all night and he says he will even stick it in a slutty looking tranny like you to get relief."

The young man pushed me to gently my knees, I knew resistance would be futile, my face was just level with his denim shorts, the front of which he was massaging slowly. Judging by the bulge in his shorts I hadn't heard a lie, he had been sporting a hard on all night. As he was pushed even closer he asked,

"Are you sure you don't mind honey?" and turned and laughed to his pals.

Normally I wouldn’t mind at all! It was what I'd come down here for, even though I'd not expected an audience. The other males would be no problem if they wanted to watch; it would just turn me on more. In reply I just licked my lipstick lips nervously.

That was all the encouragement he required and pulling down the zip on his shorts, he pulled out a nice looking weapon, already more than half hard. It was a nice size and shape, cut, about six inches long and the girth was in proportion, nicely coloured to match his skin tone.

He used his hand to move his cock tentatively to my red painted lips where his courage failed and I could see it just start to wilt. My instincts took over and I moved my head forward and grasped an inch or so between my lips, using my tongue to wash round the end. He gasped and he immediately became fully hard, his animal desire taking over as he moved forward, plunging the whole six inches down my throat without warning.

I managed to hold tight as he placed his hands on my head and started rocking back and forth. He must have been playing with it, or talking about it, most of the night as I was only just getting used to it when he pulled out, yelling "I'm cumming," and proceeded to jack off rapidly, shooting over my face, the semen running down on to my blouse. That seemed to decide it for the rest as they all moved forward and one of the white boys dropped his shorts to display a fully hard, slightly larger cut cock, which he poked out at my face.

I was hoping now that maybe all they would do was demand a blowjob each and go on their way. In the dark corner of the park maybe I could get away with that and then make some sort of excuse when Tom came to take his turn. As much as I loved sucking cock there was no way I was going to fellate my own brother.

Normally I do love a cut cock and would need no further bidding to wrap my lips around the cock in front of me and work it, but now I was scared. They were drunk, horny, and trouble. This seemed to settle it for them and I became aware the other lads all had their cocks out, rubbing them excitedly. An older coloured boy made his way forward and pointed his groin at my face.

"How about this then? You fucking tranny slut," he asked.

This when I realised I was in serious trouble. I gasped,

"My God! No!"

His cock was huge, it had to be a eight inches long and possibly two inches across.

"I can’t take that," I gasped.

"Well your going to," he growled.

Without further ado the lads pulled me up and hustled me over to the children's roundabout in the play area. That was all the leader said to me directly for some time, giving others instructions as to what they should do to me, how to place me, how to hold me. The roundabout was one of the old style, solid wood planks, well worn, with a small running board and four metal handles crossing over the top. It was located in an area of the park where the streetlights had been broken and whilst it gave them the privacy they wanted to go about their ravaging of me, I dismally hoped it would assist my disguise and help keep my true identity from Tom and his friends.

Under their leader’s instructions they soon had me spread out on my back between two of the roundabout handles, they pulled my panties to one side and exposed my puckered ass, my sheer stockinged legs where spread wide and my high heeled feet where lifted high in the air. The white boy who'd just fucked my face knelt behind me holding my head up and cushioning it somewhat from the bars. Some of the lads had stripped off their pants by now and it was obvious that they weren't going to leave me alone until they had all had their way with me. I tried to look around to see where Tom was, I just hoped he wouldn’t join in,

One of the boys climbed on the roundabout and knelt with his cock pointing at my face. He was quite dark, only about eighteen but already with a hairy manly chest. He just knelt there masturbating for a while and then I felt a pair of hands start to feel my arse, first gently and then with more vigour. One, then two fingers inserting themselves up my passage. I couldn't see who it was but I prayed it wasn’t Tom. As my arse muscles started to spasm as the fingers withdrew and a voice said "Now!" and I heard and felt someone spit on my ass-bud.

"Natural lubricant," a sleazy voice laughed. I recognised the feeling of what entered me next, a medium sized cock was pushed deep inside me, and it wasted no time, but started to attack me straight away. In, out, in, out. He was reaching my prostate without any problem. Even though I was being raped, I was going to cum soon if not very careful. I managed to mumble something along those lines in between loosing my breath each time I gasped he rammed his cock in and out of me. I just hoped it wasn’t Tom, ‘please god don’t let it be my brother fucking me,’ I prayed, even though I was now thoroughly enjoying the fucking I was receiving.

"Oh God, I’m going to come," I uttered, as the intense fucking I was receiving took me over the top.

"That's OK. So am I," laughed the lad kneeling over my face as he sped up the speed of his wrist and with a series of soft yells shot over my painted face and lipstick lips.

All this time the attack on my arse had continued. I heard,

"I'm cumming. God I’m cumming. Here we go!"

I was thankful the voice I heard was not Tom’s, but the attack intensified and with half a dozen sharp thrusts as I felt the cock in my arse shoot inside me. The boy that was raping my arse shuddered a couple of times and pulled out. Lying there catching my breath I was hardly aware as the lads changed places.

Now my head was being clenched more tightly, one lad was standing each side of me holding my now laddered, stocking clad legs back in position and a new weapon was rubbing against my panties that had slid back, and now covered the entrance to my arse. I looked up to see the leader with his huge cock in his hand pointed at my arse, from which his mate’s semen was leaking and staining the crotch of my panties. I started to struggle,

"No, I can't," I said.

"Yes you will, your arse is well and truly lubricated now" he snarled.

I struggled but someone grabbed my high-heeled feet and pulled my legs high over my head exposing my come-soaked panty-clad arse. The lad kneeling at my arse pulled the soaked, slinky fabric to one side and positioned his manhood at the puckered flower. Amazingly, the usual flush of expectation of a good fucking flowed over me and I felt myself relax against my own will. I know what I'd said, but there was no way I could take him. He had to be a ten inches and at least three inches across. A solid black ebony shaft. As his cock demanded access to my hole it seemed to glisten and gleam in the moonlight.

"Right?" was all he said.

"No!" I managed to reply.

It didn't matter. Whatever I said, it didn't matter. He was going to fuck me. He was going to rape me. No one was going to do a thing about it, including my brother who was oblivious to my fate. The other lads that were holding me in position were getting excited now. I could see hands moving, two bodies kneeled beside me, hard cocks were being readied for an assault on my body, but they were all watching the weapon that probed my entrance. He was slow; at least I'll give him that.

He stopped for a moment as soon as he forced it into my entrance, but only to allow me another gasp before starting again on a slow but inexorable voyage of discovery inside me. It never seemed to stop, a little push, stop, pull back, and push again. Each time a greater violation. He punched past my prostate almost without my being aware and still the exploration continued. Deeper than I'd ever been violated before. If I'd not been so excited and scared at the same time, and held so tightly, there wasn't any way I could have withstood the punishment.

I could hear myself letting out little yelps and groans whenever I had the breath, which wasn't very often. Each time I gasped in order to keep breathing, he forced his cock in again before I had time to fill my lungs. It felt as if that monster penis of his was splitting me apart. It wasn't a cock, it was a weapon he was using on me! It stopped. I managed to take a clean breath, open my eyes and look up. The leader was looking down on me his face covered in sweat from his exsertion in my arse.

"I've never had it in a tranny’s arse before. You are one tight bitch!" he laughed.

I was in pain, but such glorious pain. I'd never been so thoroughly possessed before. I knew he was raping me. No way could it be called regular sex. He might damage me but deep inside was a feeling that I wanted more. I just had to have more.

"Get on with it," was all I replied.

With an even bigger grin he pulled back slowly, and that was all my body needed to move on to a higher plane of sexual ecstasy. I must have been a quite a sight, my skirt rucked up, sheer nylons laddered, legs held spread, panties pushed to one side of my open arse that was impaled by a huge black cock.

The two lads who were holding my legs with one hand and their hard cocks with the other decided it was time to get in on the action. One crammed his engorged penis past my lipstick lips and into my mouth, the other was busy stroking his cock and alternately rubbing it on my cheek and in my hair. Someone grabbed hold of my cock and was squeezing it hard each time the unknown assailant rammed his cock in me. ‘Not my brother Tom, please,’ I hoped.

That seemed to be a general signal for the other lads and I felt other hands moving over my body, rubbing cocks on my stocking legs, wanking over my face, and then my hands were grabbed and wrapped around two more throbbing penises. Was everyone going to use me tonight? Which cock belonged to my brother? I was aware of the weapon up my arse as it started to swell and judder, and as it started to shoot I felt the cock in my mouth explode and come filled my throat. I had no choice but to swallow.

The two cocks that I had been forced to wank also ejected their loads, I felt the sticky come saturate my hands. The other lad rubbing his cock on my face shot a stream of come over my eyes, adding to the come already there expelled from the first boy who used me. My mascara was running down my face in a stream of hot semen. The lad who was dry humping my sheer stocking leg groaned at this sight and I felt his cock pulse against my stocking thigh and I then the warm wet feel of come through my laddered nylon encased calf. Finally the young black man that was raping my arse stopped; he withdrew his flaccid penis and looked over his shoulder, smiled an evil smile, and said,

"Here, you can have what’s left of this bitch now." I looked up in horror realised it was my brother Tom he was talking to.

"No, no more please, I can’t take it," I whimpered in attempt to put him off .

What could I do, If I exposed my real identity there was a good chance the gang would beat me up and Tom would know my secret and tell everyone. I decided to meekly accept whatever my brother decided to do to me, and hope he didn’t notice who I was under the smeared makeup and ripped women’s clothes.

My brother Tom took his place and lay on top of me.

He didn’t seem to care that my face was covered in come and that I was leaking sticky white semen from my arse. He leaned down and kissed my smudged lipstick lips. I felt his cock stiffen as he pressed against the nylon panties covering my penis. The lads holding my legs, having achieved their orgasms and having no further use for this ‘tranny slut’, had let go of my legs and were stuffing their sticky cocks back into their shorts as they dressed.

Tom reached down and placed his turgid penis against the bulge of my soft cock encased in my nylon panties, oblivious that his was older brother underneath him. He was humping it against my panty cock, obviously too aroused and too inexperienced to try to enter me, he had decided to come quickly against me. I thanked god that it looked like he was not going to fuck me or make me suck him. I had guessed that Tom was still a virgin, and his inexperience and excitement meant he wanted to quickly release his seed and move on.

I realised he was the last in the long procession of rapists that were using my body for their own pleasure, taking what they wanted by force, even though I would have given it gladly one at a time in if my brother wasn’t there. I decided that I could take no more, I was now fully aroused by my brother’s thrusting penis, even though I had been raped in every orifice, was covered in come, my make-up smeared, my nylons ruined, my clothes ripped. I decided to help Tom achieve his orgasm as quickly as possible before he changed his mind and wanted to fuck me properly or worse still he recognised me in the dim light.

I lifted my legs and wrapped them around my brother’s back as he dry humped me through my panties. I pushed up and met his thrusts as his cock pressed against mine through the sheer nylon of my panties. I lifted my head, covered in come and smeared make-up and pushed my lipstick smudged, recently raped mouth against his. I rammed my tongue down his throat and started to dry fuck him earnestly.

Tom’s inexperience was obvious and my brother started to squeal as his cock spasmed against mine, drenching my panties, soaking through to my now throbbing penis, which erupted in unison. I gripped my brother in my embrace tighter as our cocks continued to jet come against each other. Finally Tom lay still, and then pushed himself off me and joined the circle of rapists standing around me.

They were all laughing and looking down at me. There I was, my skirt hiked up, my penis slowly deflating, covered in semen, my clothes ruined. I was well and truly raped by the gang, which had included my brother. The leader of the street gang, the one who had raped my arse with his enormous cock, spoke.

"Come around here again you fag tranny bitch you’re going to get the same!"

He turned his back to me and started walking away with the rest of his gang slowly following laughing and jeering amongst themselves. Tom, my brother the rapist, who had used me last, suddenly broke away from the gang and ran back to me.

‘What now’, I thought. My younger brother knelt beside me, lifted my head and gave me a soft passionate kiss. He whispered in my ear,

"Thanks most exciting experience of my life Sis," he whispered.

I lay there and couldn’t believe what I had heard. He knew who I was! He called me ‘Sis’!

"Well I guess you are now my older sister now, instead of my older brother; tomorrow you can you can show me what a blow jobs feels like, either that or I can just tell Mom and Dad about your secret. See ya’ later Sis," he laughed.

His lips brushed mine again and he shot up and sprinted after his friends laughing out loud.

 

To be continued...........

 

Part III

Tom eased back and his long thick cock slid out of my ass; he slid my panties back into place, pulled my skirt back down, and patted my ass.

"Well done Sis," he laughed.

"I really need to empty the old ball sack, and your ass was just the place to do it. Now cook my fucking breakfast bitch!" he scolded; any form of tenderness gone from his voice.

I sheepishly turned back to my chores as I felt my brother's semen oozing from ass and mix with my own semen pooled in the crotch of my nylon panties as it start to cool off and congeal.

"Tom, can I please change my underwear?" I asked, using a pleading, subordinate tone.

"I don't think so Mike, I mean Michele. When you have served my breakfast we might go back upstairs to where you keep your girly clothes and pick out something more suitable for company; but for now you'll do fine as you are" Tom answered.

'Company, Oh my God, what is my brother thinking of getting up to next,' I thought to myself.

I decided to shut up and get on with Tom's breakfast. As I laid the plate before him, Tom slid his hand up my sheer stockinged leg and stoked my thigh. I didn't move, I decided to let Tom have everything his way for now; after all he held all the aces.

Tom continued to play with my stocking tops as shovelled food into his mouth with his other hand. Then his hand slid up to my soaked panties.

"Oh fuck Sis, you're sopping wet. I must have come a torrent in your ass, and you're soaked in the front too," he laughed as his hand slid around and stroked my cock through the nylon panty.

"Well I'm glad that you liked that I gave you a 'reach around' but for fuck sake all that come in your knickers is disgusting!" Tom laughed evilly and then removed his hand and wiped it on the front of my black miniskirt.

"You fucking arsehole!" I yelled and made to slap his face.

Tom was too quick for me and grabbed my hand in mid air as he stood up and pushed me back hard. I tottered back on my high heels and fell flat on my ass on the kitchen floor, winded. I must of looked a sight, my legs spread, skirt rucked up to expose my stocking tops and soaked white nylon panties, and my thick makeup starting to run as I tried to hold back tears.

"You fucking well are a girl Mike!" Tom spat contemptuously.

"Now get your fucking faggot, girly ass into the shower and clean yourself up. And don't think this is over, I've just started having fun. When you've cleaned my 'man fat' from your ass and made up your slutty face for me again, I'll help you pick out the wardrobe for this afternoon's entertainment. Now fuck off and let me finish my breakfast you freak!" my Brother said, dismissing me from the room.

I skittered up onto my heels and slunk off to the shower. I had never felt so humiliated. Even the raping I had received from the street gang last night had some semblance of respect and tenderness. My Brother Tom was treating me like a two-dollar whore this morning!

I removed my come stained panties, garters, stockings and skirt then gathered up the soiled clothing from last night's 'adventures' and put them in the washer while I showered. I spent at least half an hour washing myself and gave myself a quick enema to clean out my brother's come from inside me. I vaguely heard the phone ringing and Tom answering during this period, but paid scant attention.

After three-quarters of an hour I retrieved my now clean clothes from the washer and placed them in the dryer. I felt refreshed enough to go to my room and get dressed. As I entered Tom was sitting on the bed surrounded by a selection of my girl clothes he had obviously taken from my secret hiding place at the back of the wardrobe.

Tom had laid out my red Lycra miniskirt, a black sheer blouse, black nylon panties and matching bra, and a pair of my sheerest black seamed nylon stockings. On the floor were my high heeled, patent leather, open toe, sandals. My blonde wig was sitting on the dresser amongst the makeup scattered there from this morning.

"Get dressed, Sis," Tom ordered.

"And put on lots of that slutty makeup you wear, just like last night. And…fucking get a move on; we've got company coming."

"What are you on about Tom?"

"Who have we got coming?" I sounded alarmed.

Tom grabbed me and threw me on the bed.

"Just do what you're told 'big Sister', unless of course you want our family and the whole neighbourhood to know about you perversion!" Tom yelled into my face. He stormed out the room and left me to dress.

I knew I had no choice but to comply as I plied on my makeup, making my self look like a cheap whore with heavily mascaraed eyes, ruby red lips, and rouged cheeks. I fitted the wig, slid into the bra and panty set, pulled my matching black garter belt over my panties and squeezed into the tight red mini. I eased the slinky nylon blouse over my shoulders and bent down to glide the diaphanous, black nylons up my legs and attached them to the garters. I buckled the high heels and bent down to straighten the seams of my stockings.

As I was I stood up and turned my back to the mirror to check my stocking seams were straight, the door had opened silently.

"My fucking oath Tom, she looks even better than last night, I can't wait to get my hands on her!" a voice I remembered from last night exclaimed.

I turned around and saw a jet-black youth that I identified as being the leader of the gang that had forced their way on me last night in the park.

"Well don't wait Tone," by Brother Tom, said matter of factly.

"Help yourself. Tony, this is my Sister Michele; Michele this is Tony. But what the fuck, you two met on a more than personal level last night didn't you. So, no need for formal introductions," he laughed.

"Go for it Tone!"

The black, heavily muscled youth sprang forward and wrapped me in his huge arms. He pulled me forward and I collapsed against him. He looked me in the eyes and then pulled my face towards his.

"Hello Michele," he whispered.

"Remember me?"

Just before his lips crushed mine I tried to scream.

"Nooooooooo!"

But his lips mashed against mine and my scream was stifled. Tony forced his tongue into my mouth and began to rape my mouth. He pulled me hard against him and I felt the growing bulge in his jeans as he kissed me. Tony's right hand released its grip from around me and went to my ass and began squeezing my cheeks through my skirt and panties. He rubbed first one cheek of my ass then the other as he continued to French kiss me.

I tried to struggle, but his grip was too tight and all I succeeded in doing was moving my lower body against him and arousing him further. His cock now felt like an iron bar against me. Tony's hand now reached under my skirt and started to caress my stockinged thighs. I was so breathless I thought I would pass out.

"Oh fuck yes, Michele," Tony whispered as his lips left mine briefly.

"God you are one sexy little girly-boy!"

He then proceeded to kiss me again and steadily force me back towards the bed. I had no control over the situation and as my legs came into contact with the end of my bed I fell backwards with Tony on top of me. He reached under my arms and dragged me up the bed so I was prone underneath him; all the time his lips were locked on mine. The only thing I could think to do was slam my legs shut in protest.

Tony broke the kiss and as I lay there panting he straddled me. He was sweating and breathing hard himself. He tore off his T-shirt and unbuckled his belt; he pushed his jeans down and lifted each leg to shed himself of the garment. He wore no underwear and I caught sight of his huge erect organ. It looked even bigger than the monster he had forced into me last night.

I prayed that this would end soon. Maybe Mom and Dad would come home, maybe Tom would take pity on me, maybe the world would end; what chance did I have?

Tony now lay on top of me, taking his weight on his elbows and began a series of passionate kisses. His hands roamed over my body, stroking and caressing. Eventually one hand reached under my skirt and began to stroke my thighs again. I felt him squirm on top of me and realised what he was doing. Tony was working his cock between my locked, stocking encased thighs. He started a slow steady rhythm as he dry humped my thighs, his cock trapped between them.

I felt him get further excited now and his kisses became even more passionate as his rock hard cock continued its steady fucking motion between my nyloned legs. I made a mistake. I opened my legs slightly to try and thwart his pleasure, and Tony immediately seized the opportunity. He dropped one leg between mine and forced them further apart. He pushed up with his hips and his iron hard cock came into contact with mine through the gauzy nylon of my panties. Tony immediately began dry fucking me through my panties, his hard member pressed against mine, only the thin translucent nylon between them.

I couldn't help myself. My cock began to harden and I started to push up to meet his thrusts. I responded to his kisses, driving my tongue deep into his mouth and mashing my lipsticked lips against his. The feeling of our cocks rubbing together with only the thin nylon panty between them was exquisite. Again I had gone from being the victim of a rape to willing participant, only because of my inability to control my arousal.

I was enjoying the dry fucking so much that I pushed my heels into the bed to force my crotch higher and harder to meet Tony's thrusts. I locked my arms around him and began to groan. I then felt the bed shift as a weight was added just near my head. I turned to the right and opened eyes and saw my brother's engorged member level with my face. I guess it was just instinct, but I opened my mouth and sucked the proffered appendage into my mouth, my lipstick leaving a red trail along the shaft as it slid over my lips.

I began to move my tongue around the throbbing head of Tom's cock, licking under the glands whilst keeping it trapped in my mouth, my lips clamped on the shaft. I heard my brother groan.

"Oh Sis, yeah sweets, that what I wanted."

Tony stopped thrusting against me and I writhed on the bed to indicate my disappointment, but he was only adjusting his position. He put his knees between mine and grabbed my silky, stockinged calves and lifted my legs up and locked them under his arms. I felt his cock prodding against the leg opening of my knickers and then felt it slide inside my panties and rest against my ass bud.

I was now getting exceptionally randy and began a steady long slow blowjob on my brother Tom. I kept his shaft clamped between my lips and moved my head up and down his shaft as my tongue continued to lash his tender glans. My own cock was rock hard and the tip had forced its way out of my panty waistband and was so sensitive, the friction of it rubbing on my skirt was painful. I reached down and pulled up my lycra skirt around my waist, fully exposing my panty clad ass and balls, my glans were now exposed and my cock was pushed flat against my stomach by the waistband of my panties.

Tony started to push forward with his hips, and his penis, lubricated by our 'cock-kissing' session, slid slowly into my ass. I relaxed my inner muscles and allowed him to enter me until his balls rested snugly against my ass cheeks. Tony then lifted my legs higher and placed my high-heeled feet over his shoulders, he was kissing my stocking legs, bending forward and moving his kisses up my legs as his cock started its outstroke.

I clenched my lower muscles tight and my ass gripped his cock as it started a steady in and out rhythm, on the in stroke his body rubbed against my cock adding to my pleasure. I was sucking Tom's cock to the same rhythm, his cock being swallowed deep into my throat as Tony's shaft pumped into my ass.

"Oh fuck Sis, this is just so good! Suck that cock honey!" my brother groaned.

"And take me deep inside you sugar," breathed Tony.

The pace gradually increased as Tony started to fuck me hard. He was no longer gentle, but was pounding his hard, fat cock in and out of me faster and harder, his balls slamming into my panty ass and grinding himself against me at the top of his in stroke. Tom was keeping pace and was now holding my head as he fucked my mouth, I was breathing heavily through my nose trying not to choke when his cock was fully inserted into my mouth, his balls banging against my chin.

And me, the poor little girl being raped? I was enjoying every second! I was sucking and licking my brother's cock, and rising to meet Tony's thrusts as I concentrated on squeezing his cock tight inside me.

The pace was now at a crescendo and both of the boys where groaning as they approached orgasm.

"Ohhhhhhhh fuuuuuuuuck honey I'm gonna' come, I can feel it," groaned Tony.

"Ohhhhhhhh me too!" screamed Tom.

"Take it! Take it! Take it, sugar!" Screamed Tom, as I felt him push forward with a mighty thrust. He buried his face in my nyloned thigh and kissed me there as his cock started to spasm deep in my ass. He was pushing his cock into me as deep as he could, and grinding his balls against my panty ass to increase the sensation of his orgasm. I felt my ass flood with hot semen.

At the same time Tony groaned,

"Here Michele, take my load!" And he too pushed his cock deep inside my mouth down to the back of my throat, his hands forcing my head hard against his crotch. Hot salty sperm started to boil from his throbbing penis and fill my mouth. As much I sucked I couldn't swallow it all and I pulled my head back. Tom pulled his cock from my mouth and rubbed it all over my face as the last of his seed ejaculated over my face. The hot, sticky come was in my eyes, my hair, and all over my cheeks. My makeup was running as semen was smeared all over my face by my Brother's hot, jerking cock.

I felt the last spasms of Tony's orgasm deep in my ass, and my bother's hand squeeze my cock and stroke it in a tight grip. I ejaculated against my belly; I felt the hot come pool there as my dick throbbed in my brother's hand.

When I arrived home I raced up to my Sister's room, I was in luck, she was home. I entered her room to find her propped on the bed with a set of headphones on her head, listening to her music. I plopped myself on the bed beside her and of course, immediately began to stroke her pantyhose encased leg.

"Hi Sis," I smiled as I slid my hand up and down her gossamer nyloned thigh.

"Hi Mike," she smiled back, removing her headphones.

"Trust you to go straight for my legs; without even the slightest invitation or provocation," she laughed.

"You just have to be in the same room and wearing nylons Sis, you know I can't resist," I responded, smirking what I hoped was my cutest smile.

"Well, you will never guess what happened to me today?" I inquired.

"Well, no Mike I can't; but judging by the big smile on your face, the hard-on in your pants, and the way you are pawing my thighs, I guess it had something to with sex," she teased.

"Well Sis, the hard-on is in no small part due to my playing with your sexy legs, but largely due to my adventures this afternoon."

I then went on to tell Eileen about the fantastic fuck I had had with Mom in the Matron's office at the hospital. I also told her about playing with Matron's stockings before I fucked Mom, and about how Matron had come in to her office later and basically propositioned me. I then started to explain to her my plan to get Matron involved in our sex games.

Before I could go on further she stopped me.

"Mike, that story where you bent Mom over the desk and fucked her has got to one of the hottest stories I have ever heard; slide your hand up my skirt and see what you've done to me."

Who was I to turn down such a request? I slid my hand along my Sister's slinky nyloned thigh and under her little pleated tartan skirt. I savoured the feel of her nylons on my fingertips, and the light material of the hem of her skirt sliding along the back of my hand as it disappeared into the lovely playground that my Sister was encouraging me to explore.

As my hand encountered the top of her leg I slid it slowly across her silky pantied crotch. I could feel the heat, and as my fingers ventured down between her legs, I felt the damp wetness there.

"Oh Mike," she whispered,

"Please, please, please," my Sister begged.

I pushed two of my fingers into her slit, rubbing the nylon of her hose and panties against her labia. I pressed harder against where I guessed her clitty might be beneath her underwear and was immediately rewarded with a sob of pleasure.

"Oh god yes Mike, there, that’s it."

I massaged her cuntal area slowly but firmly and felt my Sister's panties become soaked with her juices. She squirmed and rose herself up off the bed to meet my ministrations. Her back and legs arched as she rose her torso up, taking her body weight on her feet and shoulders, her skirt fell back revealing dark green nylon panties covering gauzy sheer-to-the-waist pantyhose. What a magnificent sight I though as I continued to stoke her hot pussy through the layers on nylon.

After a few minutes of making Eileen squirm in sexual bliss, I decided that I needed to attend to the now raging hardon that was bulging in my jeans. Without ceasing attending to my Sister, I removed my clothes and manoeuvred myself between her spread legs. I lightly rubbed my engorged member against my Sister's nylon encased thigh and quickly got into the same rhythm as the stroking I was applying to her cunt.

The feel of her delicate nyloned leg against my cock was scintillating, I could never get too much of the wonderful feeling of my penis against nylon. As I started to press my cock harder on her leg, I too started to pant.

"Oh yes Sis, I love this, absolutely love it!"

"Don't stop Mike, I'm close, please, put him in me, put Him in ME!"

I knew what she meant, and my Sister begging to be fucked was a request not to be denied. I reached my hand inside her panties and seized a handful of gauzy nylon and ripped open the gusset of her pantyhose.

"Oh Mike, yes, put him in NOW!" Eileen screamed.

I reached behind Eileen and grabbed the two pillows that rested on her headboard and pushed them under her arched back. I pulled on the gusset of her pretty green panties and eased it to one side. I kneed myself forward and positioned the head of my cock inside my Sister's swollen labia and let go of the gusset of her panties. The soaked panty material eased back across her crotch and came to rest against the side of my penis.

Eileen felt my glans nestled in her cuntal lips and she slowly began to ease herself forward, impaling herself on my turgid, throbbing cock. As my Sister slid herself onto my cock, I reached forward and grabbed her waist just where the waistband of her pantyhose peeked over the top of her panties. I took a firm grip and started to push her down onto my member, slow and hard until I was buried into her right up to the hilt.

As our pelvises butted together we both grunted,

"Ough!"

I moved my hands down my Sister's sleek hosed legs and lifted her claves up and around my waist. I felt her legs lock behind me and she gripped me against her, the sheer nylons sending shooting sensations of delight where they brushed against me. She used the grip she had on me to commence a slow steady fuck; easing my cockhead out of her until the crown of my glans was touching her inner labia, then pulling me back into her until our crotches were smashed together.

Eillen's juices were flowing faster as my penis eased in and out of her, her soaked panty slid along my shaft, heightening the sensations shooting through my body. She started to chant in time to our now steadily increasing thrusts,

"Fuck! Fuck! FucK! FucK! FuCK! FuCK! FUCK! FUCK!……………….FUCK MMMMMMMMMEEEeeee!!!!!!!!"

"Oh Mike fuck me honey, please, please, please!" she sobbed as the tempo increased.

My body felt like it had some sort of electric sexual energy flowing through it due to the sensations of my Sister's cunt gripping my cock, her pantyhosed legs rubbing back and forth as we humped, and the nylon panty teasing the shaft of my cock as it thrust in and out of her.

Our orgasms were fast approaching and Eileen sensed it too. She locked her long legs around me even harder, clutching me in her grip and slamming me against her, grinding her cunt against my pelvis and causing exquisite friction to scour her clit. Her silken legs spasmed and convulsed against me and her cunt quivered and pulsed in orgasm. My cock burst forth stream after stream of hot semen inside her as it pulsed and throbbed in concert with her climax.

"Sis, Oh Sis! I love you, I love it!" I groaned as she sucked the energy from my body.

"Oh Mike, you drive me wild, Brother of mine. I love you too!"

We both came down very slowly from our mutual climax, shuddering and groaning as the last of orgasms drained from us. Eileen's, legs slid down my side and came to rest splayed apart with me between them. I slowly allowed myself to fall forward on top of her as she released me from her grip. I started kissing her gently, planting lots of little kisses on her lips and stroking her hair and caressing her face as I kissed her. We lay like that for a while, kissing and caressing as my cock slowly deflated inside her and eventually plopped our of her puffed-up pussy lips and came to rest on her panty crotch as the silky material slid back into place, my cock no longer keeping it to one side of her entrance.

"Mmmm Sis, I could lay here for hours and do this," I whispered into her ear.

"Liar," she giggled.

"You'd get hard again eventually and want to do it all over again!"

"And so would I, so get off me you naughty boy and tell me about your plan for Matron!"

I eased myself from on top of my sister and lay close beside her, lazily stroking her thighs and buttocks and occasionally stealing a kiss as I explained my plan to trap Matron. Eileen asked questions and offered suggestions as I outlined my plan. She giggled occasionally and conspired with me to concoct what hopefully would be another 'silken trap'; this time for Matron.

We decided to strike while the iron is hot and hatch our plan for the next day.

That night Mom came home exhausted and after a quick dinner she gave us both passionate kisses goodnight and went to bed; I was to find out later, that on the way she left her discarded nylons hanging from my bedroom doorknob; a nice trophy for my collection.

The next afternoon I met Eileen at home, we both skipped school after lunch to prepare our trap. Eileen dressed in a black leather mini, white low cut blouse, tan pantyhose and red high heels. She flipped up her skirt and revealed a pair of black, lacy open crotch panties. I loved the look of those open crotch panties covering her pantyhosed pussy.

"Down boy," she laughed as I made a half-hearted lunge for her.

With her usual lashings of makeup and red hair worn in an eighties frizz she looked more like a hooker than a schoolgirl.

I then made a call to the hospital and asked for the Matron supervising Mom's ward; I was in luck, she answered.

"Matron Phillips," a husky professional voice answered.

"Hello Matron, it's Mike here, I spoke to you yesterday afternoon in your office?"

"Hello Mike, what can I do for you, do you want to speak to your Mother?" she asked.

"Oh no Matron! I want to talk to you about my Mother. Its personal, and I wondered if I could see you alone in your office?"

"Well that is really an odd request Mike, I really don't normally see family members of my staff, especially alone." She responded.

"Please Matron, I really have to talk to someone about Mom; it's really important." I begged.

"Ok then Mike, if you insist, be here at two PM then; I'll make sure your Mother is busy in the ward so she won't know you are here," she capitulated.

"Thank you so much Matron," I responded, trying to sound relieved.

'We're on!" I winked at Eileen………………

At two PM sharp we were outside Matron's office. True to her word, Mom was not in sight, in fact the nurses station was empty; no one had seen us enter the ward.

"Come," Matron responded to my knock.

'I hope to,' I thought to myself as Eileen and I entered her office.

"Mike, I didn't know you were bringing anyone else; is this your Sister?" Matron asked looking a little surprised.

"Yes Matron; meet my older Sister Eileen," I responded.

"Pleased to meet you Eileen. You look a lot older than your Mother says you are; eighteen isn't it?" Matron enquired.

I noticed Matron cast an evaluating look up and down my Sister's body. Her gaze rested on Eileen's lovely sheer hosed legs framed below the micro mini, then she took a long casual once-over up the rest of her, coming to rest on Eileen's heavily made up baby blue eyes and flaming red hair.

"Yes, eighteen Matron," Eileen responded, casting her own long deliberate appraisal back at Matron.

Matron was wearing the same tight, dark blue, business suit skirt and white blouse set she wore yesterday, except today she also had on a matching navy jacket. Black high-heeled pumps and dark hose completed the ensemble. Her application of makeup again leaned to the heavy side, dark blue eyeshadow and plum red lips; her glossy red hair, styled in a bob in contrast to Eileen's frizzy mane.

'Two redheads to play with, hope they are both as fiery as their hair,' I thought smugly.

"Well sit children." Matron motioned towards two seats in front of her desk.

Matron came around the large desk and sat on the corner, her skirt riding up and displaying an ample thigh encased in smoky grey hosiery. I couldn't help but look, and Matron saw my glance and smiled smugly.

"So what's so important about your Mom that you have to see me without her presence?" she came to the point.

"Well it's like this Matron, it’s a hard subject to talk about so I guess I'll just say it straight out. Mom is having sex with me," I blurted out.

Matron looked at me with disbelief and shock.

"I don't believe you, Jean, I mean your Mother couldn't possibly…….." she trailed off.

"Yes Matron, I can see what you're thinking about; yesterday afternoon, this office reeked of sex, I bet you could smell it," I countered.

"You handed me your pantyhose remember, you hinted that I had wanked in them, but I can tell by the look on your face you now realise that there was also the smell of pussy in here too," I added.

Matron now turned a deep crimson.

"Mike, I, er, the pantyhose, I didn't know. Oh my god…er; anyway we shouldn't talk about this in front of your Sister, and don't use those rude words" she stammered.

"Oh Eileen knows everything Matron, in fact Mom is having sex with her too, isn't she Sis?"

"Yes Matron, me too," Eileen responded quickly, smiling sweetly.

"But Mike, why, why, are you telling me about all this. It's terrible, it's illegal, it's disgusting!" Matron asserted.

"Well because after my Mom forced me to have sex with her in your office yesterday, you found me in a state of distress and the best you could do was try to seduce me yourself! Even after I asked you for help, the best you could do was try to take advantage of me!" I hissed at her.

"But Mike, that is such a blatant lie. You know it is!" she pleaded.

"Well explain that to the police when I tell them that story, or maybe I'll just tell just the hospital management. Either way it'll be hard to explain how I came to have your pantyhose in my possession, which will undoubtably have your vaginal secretions and certainly my semen in them."

"I'm no expert, but I've seen enough cop shows to know how forensics work. And of course my Sister here will back me up at how distressed I was when arrived home yesterday, wont you Sis?" I smirked.

"Of course honey, I mean Brother of mine; of course I will," Eileen smirked right back.

"I don't believe this, why Mike? Why are you are you doing this to me?" Matron pleaded, tears forming in her eyes.

"Well Matron, its because I am now an expert in getting what I want, and well, I want some of this, you see," I whispered as I leaned forward and placed my hand on her thigh.

This was Eileen's cue; she rose out of her chair and sat close to Matron on the desk. She placed an arm around Matron's broad shoulders.

"And you see Matron, I'm here to see that Mike gets what he wants," she whispered into Matron's ear.

"What are you doing?" Matron begged of us.

"Well I'm taking you up on your offer Matron, you were right when you said, ' But I bet you are the sort of lad who would have more fun If I left them on,' I said as I slid my hand further up her thigh and under her skirt.

At the same time my Sister turned and reached out with her other hand and undid Matron's jacket. Matron couldn't fight both of us off, but she tried to wriggle her legs and at the same time remove Eileen's hands, which were now unbuttoning her blouse.

"Now Matron," I said, "either cooperate or we tell our little story to the management or the police," I threatened.

Matron stopped wriggling and sat still, defeated.

My hand continued to explore under Matron's suit skirt, sliding up her nylons, then encountered a stocking top and garter.

"Oh yummy Matron, I've always dreamed of fucking an older women in stockings," I said stroking the plump flesh above her stocking tops.

I rose out of my chair and stood between Matron's, chubby, but shapely legs and commenced stroking them. I noticed now the smoky grey stockings had a black seam running up the back of them; I loved the feel of them, so sexy! I lifted Matrons skirt and looked underneath, slapping Matron's hand out of the way as she tried to stop me. She was wearing huge dark grey nylon panties, then I realised they were cami-knickers, silky nylon shorts with frilly lace around the legs and waistband. I kept stroking Matrons stockinged leg with one hand and started stroking her panty crotch with the other. I felt Matron stiffen as my hand went to her nylon covered cunt. I heard Matron give a muffled grunt and looked up, I took my eyes away from her splayed stocking encased legs and knickered ass to see what was happening.

Eileen had been busy too; she had Matron's blouse open and her hand inside Matron's matching grey nylon brassier, and was stroking her tit. My Sister started kissing Matron passionately; I could see her working her tongue. Matron was a big lady but still no match for Eileen who was holding her in place as she struggled.

I opened my fly and eased out my stiffening member, rubbing it on Matron's smoky, nyloned thigh and experienced that familiar exquisite feel of diaphanous nylon against my cockhead, making it tingle with delight. A snail's trail of pre-come glistened on her leg. Matron tried to struggle again and I held her legs tightly.

"Submit Matron, or you know what happens," I threatened yet again.

She relaxed again and gave a resigned shrug. Sis was smiling at me and said, "Look Mike, I think she's starting to like our attention."

Eileen had Matron's tits fully exposed and her large knobby nipples were swollen and a bright pink colour.

"Well I guess it's a matter of when rape is inevitable……….." Matron whispered.

"It is," I chuckled and recommenced dry humping her leg.

I worked my way forward between her legs and my cock came in contact with her stocking top. I rubbed it there whilst my hand slid down from under her cami-knickers to caress the expanse of flesh above her stocking. It was a very new and rewarding experience for me to play with legs encased in fully-fashioned stockings instead of pantyhose.

My sister was now kissing Matron in a series of long slow kisses and Matron was responding, not overtly but you could tell she was coming around and giving in to her growing sexual excitement. The sight of these two heavily made-up redheads kissing and fondling was exciting me further and I kneaded Matrons plump thighs harder and humped her stockinged leg with long slow strokes.

I moved my hand under Matrons cami-knickers and stroked the outside of her pussy. It was so hairy and felt huge, unlike the tight little slit my Sister has, and Mom's was also small compared to the puffy fat mound I was now stroking. I poked a finger inside the flabby outer cuntal lips and felt a warm moist cave, the inner lips nearly as large as her labia majora; Matron stiffened slightly and then relaxed, her legs opening further.

I eased two fingers inside her cunt and positioned my thumb over her clit, it was hard and felt huge compared to my Mom's and Sister's; the inside of her hot wet cunt was loose and I eased my two remaining fingers inside her with no resistance. My cock was still humping at her leg and Sis was still kissing her and stroking her nipples; Matron had raised her hand and her red nail-polished fingers gently held my Sisters head and stroked her hair. The bitch was really hot for it now!

Eileen was now lying across the desk and leaning over Matron as she played with her tits and kissed her. She shifted position and crawled right up on to the desk and straddled Matrons waist. This caused my Sister's skirt to ride up and expose her lovely pantyhosed thighs and pantied ass to me. With my free hand I started stroking my Sister's mound through the nylon of her hose and panty crotch, feeling the heat and wetness there.

She allowed me to do this for a minute or two and then reached back and with her polished fingernail, slit open the crotch of her pantyhose in a neat ripping sound. She spread the lacy opening of her open crotch panties, exposing her sex, and started to work her body up Matrons torso until her cunt was positioned over Matrons face. As my Sister slowly lowered herself I saw Matron's tongue reach out to meet the delicious cunt descending on her. The smell of hot cunt was tangible.

I positioned my now rock hard cock against Matron's fat puffy cunt, I had opened the leg of her cami-knickers and pulled my hand out of her cunt with an audible 'plop'. I pushed forward and it was like entering a hot buttery cave as Matrons labia opened and my cock slid effortlessly inside her. Matron's legs rose up and locked around me, I pulled off my shirt and dropped my pants so I could feel those silky grey seamed stockings against my body. Matron gripped me and commenced pulling and pushing my body back and forth in a slow rhythm as I fucked her.

The feel of Matron's cunt was so different to Mom's and Sis's. It was loose and wet instead of the tight little pussies I had become accustomed to. My cock loved the different sensations of the slack, hot folds of Matrons gaping maw. Her labia wrapped around the base of my cock as my crotch slammed into her. Matron was controlling our fucking, gripping me tight with her stockinged legs, forcing me to slow down my thrusting to long, slow, deep strokes.

Sis was now groaning and I could see she was pushing her cunt up and down on Matron's face, increasing the speed of her cuniligal face fuck. I could hear Matron's muffled groans and my Sister began to whimper.

"OOOOHHhhhhh! OOOhhhhhh!"

It was obvious Eileen was close to orgasm as she rocked harder and faster on Matron's face. Suddenly she arched her back and pressed herself down on Matron's face.

"Cooommmmminggg!!" Eileen moaned, pushing a hand into her mouth to stifled a scream.

Then Eileen fell forward, her body shuddering as the last of her climax shook her body. She rested like that recovering for a couple of minutes as I enjoyed the sight of her straddling Matron and coming down from her high. I tried to increase the intensity of my coupling with Matron. She would have nothing of it and continued to keep me locked in the vice grip of her big muscular legs, ensuring a slow steady rhythm.

My sister dismounted Matron's face as a rider would a horse and she rolled to one side panting, her skirt still hiked up and her long pantyhosed legs spread. Now I really wanted to increase my sexual pleasure and give Matron a hard fast fuck. I gripped her stockinged thighs, and using all my strength, I pulled Matron's legs apart. I eased back and my cock fell out of her plump pussy with a slapping sound. Matron started to panic until she felt me start to twist her body and realised I was trying to turn her over.

Matron assisted me and rolled over so she was face down on the desk. I pulled her back towards me until her heels found the floor so she was bent over the desk. She looked delicious, bent over in her high heels with her seamed stocking encased legs stretched taught. I ran a hand up her silken shanks and clutched the hem of her skirt, which had fallen back over her rotund ass. I pulled the hem up and tucked it into the waistband of her skirt, exposing her panty-encased ass-checks. I pulled her cami-knickers down around her ankles and pushed forward so that the crown of my glans was just inside her gaping maw, then I pushed forward with all my might.

My cock slid into her slick wet folds and her labia greedily wrapped around the base of my cock again as I entered her fully, my crotch slapping against her soft round white ass. I then grabbed hold of the garter straps that held up her stockings and used them as reins as I commenced a hard fast fuck, pounding in and out of her sloppy cunt.

"You naughty boy!" Matron whooped.

"You, naughty, naughty, naughty, boy!!!"

"Naughty am I Matron?" I howled, "I'll show you naughty!"

I commenced a frantic in and out fucking motion that was accompanied the sucking sounds of her pussy as I pounded into her. My balls and crotch were soaked and her thighs and ass glistened with her love juices. Then it happened! I pulled back too far and my cock fell out her, in my haste to slam it back into her, the head rammed into the slick membrane of skin that separates her cunt from her ass. The force of my thrust and the slippery juices forced my cock to move upwards and plunge into her ass. It took me a second to realise what had happened, but then I realised I was having my first anal sex experience. My cock was buried to the hilt in her warm tight chamber, there was a slight resistance to my thrusts and a tight pulsing and squeezing on my cock coming from the walls of her dark hole.

"AAAGGGHHhhh!" Matron moaned.

"You naughty boy!!" Matron screeched.

"You are a very, very, very, NAUGHTY BOY!!!" she screeched.

As I recommenced my hard and fast fucking motion, this time in Matron's ass, I realised the bitch was enjoying it.

"Take it Matron!" I whooped.

"Take it deep in your asshole!" I whooped again as I fucked in and out of her tight hole, her ass spasmed around my cock and I drove it deeper, and deeper as her fat ass wobbled and swayed under the anal attack.

"Oh you are a naughty boy Mikey!" she gasped, almost out of breath,

"I'm commmming" I hissed and pushed my pulsating hard cock deep inside her.

I felt my member drive in as far it would go and her ass muscles grip and spasm all around it. Her fat white ass was shoved flat against my crotch and her stocking legs were forced hard against the desk. My cock exploded a torrent of semen in long juddering jets and I felt the hot jism wash around the head of my penis which had created a dam in her ass tunnel. I pulled on the reins of her garters and moaned.

"OOOOOHHHHhhhhh!!!"

Matron was quivering against me, I couldn't believe she was coming; having an anal orgasm as I raped her.

We both slowly came back to earth from our shattering orgasms and Matron went limp, whimpering in the last throes of her climax. I eased back and my now deflating penis popped out of Matron's asshole; my semen began to mix with her cunt juices and ran down through the folds of her pussy and on to her smoky grey nylons, staining them with our combined come. She turned around and pulled herself upright off the desk, her heavy makeup ruined by the face fucking she had given my Sister and by the exertion of our frantic fuck. I could smell my Sisters cunt on her breath as she wrapped her arms around me and pulled my face to hers and gave a hard sloppy kiss, thrusting her tongue deep into my mouth. She pulled back and smiled at me.

"See! I knew you were the sort of lad who would have more fun if I left my nylons on," she said.

 

To be Continued………………………………….

"Here Mike," she smirked and handed the pantyhose that only minutes before had been stretched around my cock.

"You might as well keep them, by the look of the that little wet patch and the smell of semen, you were been busy with them before I came in," Matron said, a smile on her face.

"Maybe next time you visit I’ll let you take these off," she said pulling on the gossamer sheer nylons on her legs.

I was just flabbergasted and almost beyond speech.

"Thanks Ma’am, I would love to," I stammered and walked out the door my head spinning. I heard her laughing to herself as I walked away stuffing her pantyhose into my pocket.

"But I bet you are the sort of lad who would have more fun If I left them on," she chuckled after me.

 Part VI

"Thanks most exciting experience of my life Sis," he whispered.

I lay there and couldn’t believe what I had heard. He knew who I was! He called me ‘Sis’!

"Well I guess you are now my older sister now, instead of my older brother; tomorrow you can you can show me what a blow jobs feels like, either that or I can just tell Mom and Dad about your secret. See ya’ later Sis," he laughed.

His lips brushed mine again and he shot up and sprinted after his friends laughing out loud.

As I lay there used and abused I wondered what my future held now that Tom knew my secret. I picked myself up and staggered home, limping to the bathroom to remove my female garb, my underwear tattered torn and come soaked. I ran a shower to remove my smeared makeup and the dirt and come from my body. I checked myself for bruising and cuts and found that I had not come out too worse for wear.

I grabbed my clothes and retired to my bedroom where I sorted through them, discarding the ripped and stained intimate items and locking away my skirt, top, and salvageable underwear to be washed later (when no one was home of course).

I lay on the bed smoking, reliving the events of the night. If hadn’t been for my Brother being there I wouldn’t really have minded what happened to me. In fact, as I thought about how I had been used by the gang, incredulously, I began to get an erection. It quickly deflated as I wondered what Tom was going to do with his new found knowledge.

Would he tell my parents, my friends, and our neighbours; or would he torture me with guilt? I drifted off thinking of scenarios where my Brother blackmailed and tortured me now that he knew I was a crossdresser.

The next day was Saturday and I stayed in bed late. My parents left early for a weekend away on holiday at the coast. I was dreading seeing Tom again after what had happened last night. I kept running scenarios through my mind, what would Tom do next? I did not have too wait long.

"Morning Sis," Tom said cheerfully as he barged into my room.

"Well! I knew you were a bit of poof but I never suspected you liked to dress up as a woman, and quite a sexy little tart you are, if I do say so," he laughed.

"Don’t please Tom," I begged.

"Please don’t tease me this way. You know about my secret life and that’s bad enough, but don’t treat me like shit; I am your elder brother after all," I implored.

"Oh no you are not! You are now my elder sister; that’s how we’re going to play it from now on! And you are going to be a very obedient older sister or your secret is out and you might as well move to the moon because no one will want to know you here," he said.

"Oh my God, no, please Tom, don’t do this," I begged.

But he was not listening. He began rummaging through my wardrobe.

"So where do you keep your girly gear then Sis?" he laughed pulling my clothes all over the place.

"If you mean the clothes that I wear when I am Michele, then they are in behind the back of the wardrobe, there’s a false back."

"You sneaky little trollop," he laughed again as he pulled the false back away from the wardrobe and examined my feminine clothes hung there in the small space I had built there. Three pair of high heels were arranged on the floor and a small chest of drawers held my lingerie, makeup, and jewellery. A blonde and brunette wig sat side by side on wig-stands, on top.

"Well get up Sis, Michele is it? Get up, get dressed, and cook my fucking breakfast then," ordered Tom.

I got out of bed and figured, ‘Here we go, I’m going to have to do whatever he wants while he holds my secret life as a blackmail tool.’ I reached for my jeans and a T-shirt that were thrown over the back of a chair.

"No, no, no Sis!" he bellowed.

"I want you dressed like you were last night, as a girl, you are going to be my slave sister all weekend, and then, if you treat me nice, maybe I’ll consider whether to tell Mom and Dad about your peccadillo for ladies clothing," he laughed.

"These should be nice," he said and threw a black miniskirt and white satin blouse at me from off a coat hanger. 




"And I like these too," he smiled as he tossed me a pair of white full brief nylon panties, garter belt, and matching bra that he had pulled from a drawer. He rummaged further.




"And you have to wear these," he smirked holding out a pair of sheer, fully-fashioned, taupe, nylon stockings.




"I just love girls in stockings," he smirked.




"That brown hair and those black shoes you had on last night should do the trick," he said.




"If you mean the brunette bob and the black high heel sandals, you are showing some taste for a blackmailing son of bitch!" I countered.




"Now, now Sis, lets not start the day on a bad note. Just get fucking showered, dressed and put on plenty of makeup so you can look pretty for your brother. And cut the shit, or I might get angry," Tom growled walking out the door.




"See you downstairs in the kitchen in about half an hour shall I? I’ll give you my breakfast order then!" was Tom’s parting shot as he went out of my bedroom.




What the fuck could I do? I decided to comply and see where things would go from here. I dragged myself off to the shower to prepare for my day’s torture at the hands of my younger brother…………..




Three quarters of an hour later I opened the kitchen door and sidled in. Tom was sitting at the kitchen table dressed in his boxers and a t-shirt.




"Fuck me Sis!" Tom exclaimed. "You are one fucking sexy bitch!"




I stood there in my black mini, the skirt finishing about eight inches above my knees, just covering the dark welt of stocking top on the sheer taupe stockings clinging to my legs. The black back-seams of my stockings led perfectly straight down the back of my legs to the darker, fully fashioned reinforced heel and toes displayed by my shiny, black, high heeled sandals. A thin plain gold ankle bracelet glittered at my right ankle.




The white satin blouse was buttoned up to my neck, adorned by a matching gold necklace to match the ankle bracelet, bangles at my wrists and plain gold earings dangling from my ears. The brunette bob framed my heavily made up face. What wasn’t visible were the silky nylon full brief panties and matching garter belt and bra underneath. I looked like the sort of girl you might see standing on a street corner of a red light district.




"So, Michele or is it Sis? Come over here Michele and lets get a good look at you," Tom said, his eyes roaming all over me.




I walked over to him, the high heels and tight mini forcing me to sashay provocatively. I halted just in front of my younger brother, my head bowed. He stood up, reached out and lifted my chin; he looked into my heavily mascaraed eyes,




"My God, Sis. I didn’t realise how sexy you looked last night. If I didn’t know it was my older brother under that makeup and in those clothes I’d swear you were just some foxy tart I met in a pub."




Bob reached out and pulled me to him, he kissed me roughly, forcing his tongue into my mouth. I tried to pull back but he held me tight. I felt his cock harden in his shorts as he pushed against me. I tried to move side-on so his penis was not in contact with mine through our clothes. He started rubbing his erection against my leg, dry humping me, his brother.




"Please Tom," I whimpered, "Don’t do this."




He released me and pushed me back holding me at arms reach.




"Oh no Sis, don’t come on all coy now deary, you weren’t coy last night when you were sucking and fucking my mates now, were you Michele?" he said sarcastically.




"Anyway Sis, you are probably right about one thing, I don’t want to get you diverted from cooking my breakfast do I?" he chuckled.




"Plenty of time for that sort of fun after I’m fed. Now get going Sis, two eggs over easy; just like you were last night if I remember," he chuckled at the joke made at my expense.




"Crisp bacon, toast and coffee please Sis. Chop chop, I’m hungry."




I felt so humiliated, but I was relieved to be out of his reach. At least while I was cooking it gave me time to think about some way of getting out of this dilemma. 




I put bacon in a pan on the stove and retrieved eggs, milk, margarine, and coffee from the fridge. Then I made what was to be disastrous error of judgement. Instead of kneeling down, ladylike, to get the coffeepot out of the bottom cupboard, I bent over at the waist and started muddling amongst the pots and pans in there searching for the coffeepot.




Tom was greeted with the view of my miniskirt stretched tight against my ass as I bent over. My skirt rode up to reveal the garters attached to the dark band at the top of my diaphanous stockings, the seams leading down to my high heels which were splayed slightly apart. A glimpse of sheer white nylon panty was just visible from under the hem of my skirt. Then I heard Tom groan and utter,




"Fuck breakfast! That view is just too much for me to take in and sit still!"




I heard his chair screech as he pushed it back and he made his way quickly over to me.




"Fuck Sis, I just have to have you," he groaned and I felt his full weight behind me.




He pushed my upper body down so I was bent over the counter top and I felt him fumbling behind me, breathing hard and grunting. I tried to push myself up off the counter and I felt a sharp jab in my side as he punched me.




"Don’t fuck around Sis," he snapped, "this can be easy or hard for you, but I’m taking what I want right now!"




I was winded and in pain and knew I was defeated. I stopped resisting and stood still, bent over the counter. My brother kicked my heels further apart and then I felt him move between my legs. He fumbled again, then in shock I felt his hard penis through my nylon panties pushing against my ass.




"Oh this is so good," he sighed as I felt his hand back there behind me trying to manoeuvre his erection into position.




His cock slid against my stocking thigh and he slowly rubbed it there as he pulled my panties over to one side of ass cheeks to expose my puckered ass bud. Tom reached out and I saw his hand dip into an open tub of margarine sitting on the counter next to my head. 




‘Christ,’ I thought, ‘I know what the bastard is about to do.’ Then I felt him rub the cold slippery margarine between my buttocks. Tom eased himself back and placed his hands on my hips, gripping onto my garter belt under my skirt. Then I felt his cock at the entrance to my ass. He just eased forward in one long slow thrust.




"OOOhhhh!" I groaned as I felt his long thick shaft slide slowly into my ass, filling it, the head of his penis pushing up against my prostate.




"OOOhhh!" my brother groaned as his greasy, slick, cock slid easily, deep into me and he felt my ass grip his penis like a velvet glove.




I felt my cock immediately stiffen inside my panties as he started to fuck me with long slow strokes. I couldn’t help but feel sexy all over as I accepted my brother’s invasion of my ass. The stimulation on all the sensitive nerves deep in there, the pressure on my prostate, and the magnificent feeling of being filled with cock, all combined to drive me into ecstasy. 




I pushed back to meet his slow easy thrusts and I felt him release one hand from my hip.




"Oh Sis," he moaned, "this is so good, I can’t hold it in much longer."




I knew what he meant, he was close to coming, and so was I. I pushed back harder as his long slow thrusts grew more intense, he was pushing his pelvis hard against my soft ass cheeks on the in stroke and pulling back so just the head of his cock was just inside my sphincter on the out stroke. I matched his rhythm and then I felt his free hand grip my hard cock through my panties. He didn’t wank it, he just squeezed my cock in time with his thrusts.




It was too much for me and I started to squirt hot semen, drenching my panties as he squeezed me harder. Tom grunted and pushed himself into me as far as he could, I was pushed hard against the kitchen counter as my brother’s throbbing cock exploded deep in my ass. I felt the head of his penis pulsate against my prostate as he shot stream after stream of hot semen deep inside me. I continued to eject jets of come as his hand squeezed my penis harder through my silky nylon panties.




I moaned and squirmed my ass back against him to drain the last droplets of come from him. He groaned and collapsed against me, sated.




"OOOOOhhhhhh Sis, that was just so fucking good," my brother whispered in my ear and kissed my earlobe.




To be continued

Part IV

Fifteen minutes later I was back in the cell Carmel had described as my 'work room'. She had cleaned me up in the shower and led me back here, dressed me, and was now putting the finishing touches to my makeup.

I was in daze; Eddie coming against my crotch and thighs was one thing, but 'Iron-bar' Steve's brutal rape of my mouth and then the humiliation of him ejaculating over my face had left me blank and bewildered. I had followed Carmel like a drone and let her take care of me and prepare me for my next encounter with Eddie. Now she was getting angry.

"Oh for fuck sake pay attention hun; I can't be doing your makeup for you every day, from tomorrow on your on your own!" she scolded.

She had selected my clothes and dressed me again but had to constantly remind me to watch what she was doing as I would need to dress myself in future. She dressed me like a whore!

After making up my face with heavy foundation, powder and blush, she had applied three different hues of eyeshadow ranging from frosty pink to mauve purple on my eyelids, working up to my plucked brows which she had highlighted. She applied lashings of mascara to my full lashes and finished with ruby red lipstick. She put on three coats and made me bite down on a tissue between each application to set the lipstick.

"This will stay on even during the most serious blow job she laughed," when she was done.

Next she had me put on a red nylon and lace garter belt. (Again I had vague recollections of helping Eddie select this item amongst the range of lingerie he ordered for his 'working-girls', as he referred to his transvestite prostitutes, who created a large part of income in the jail.) Carmel attached black, sheer, fully-fashioned nylons to the garter clips. As she smoothed them up my legs the electric spark of nylon on my legs bought me out of my daze long enough to admire my well-formed legs in the reinforced heel and toe nylons; the back-seam ran up to the gauzy reinforced stocking top cinched in the garter clip.

Again she fastened a gold chain around my slim ankle and had me step into a pair of shiny black, patent leather, open-toe sandals which had to be the highest heels I had ever seen. When I remarked I would never be able to walk in them Carmel laughed and said,

"What the fuck makes you thing Eddie even wants you on your feet tonight sugar; you'll be just fine on your back!"

Carmel pulled a pair of black see-through nylon panties up my legs and gave my arse a squeeze as she adjusted them on my hips with their high cut sides showing my upper thighs. She pushed my flaccid penis between my legs and hid it away, tucked under the gusset of my panties. She had me put on a red lacy bra to match the garter belt, again showing me how to adjust the breastforms just right. Over this ensemble she helped me into a purple cape of shimmering satin with long flowing sleeves, it buttoned only at my neck and came down to mid calf. She touched up my red nail polish and led me on shaky heels to the mirror.

Carmel had arranged on my head a long black wig with red highlights. My hair was dead straight, "Morticia Addams" style, and as I looked in the mirror I looked like some cheap Goth whore. The cape was open at the front displaying my lingerie clad body and the ultra-high heels caused my arse to push out and forced me to adjust my posture like a street walker strutting her stuff.

Carmel led me over to the bed and sat down next to me.

"Now Michele, you know what's coming so I won't pretend like its going to be nice the first time it happens. My advice is to get Eddie good and randy; the more excited he is, the sooner he will come hun."

"Under the pillow there is a tube of lubricant, if you get the chance use it; it will make things a lot easier on you babe."

"Now I know you don't believe all this is happening to you, but it is. There is nothing you can do about it; the only other alternative is not worth thinking about; you don’t wanna spend the rest of your life in a wheelchair doing Eddie's books."

"Believe me Michele you will either grow to like this life; or you will grow to tolerate it, but there ain't nothing else in your future while you are in this prison."

Carmel left me with these fateful words while I sat and waited for Eddie McManus, the most ruthless man in Chelmsford prison. The man who had only an hour before forced himself against me and orgasmed against my body, then gave me to his underling who orally raped me and ejaculated over my face. The man who was about to sodomise me, then put me to work as a transvestite prostitute for use by the scum, the guards, or anyone who could afford the price.

I made a futile effort to try and work out in my mind how often Eddies 'girls' were used. As his 'secretary' and bookkeeper I knew how much profit he made from his crossdressed whores but had no idea how many he had or how much they charged. It was a useless exercise but it kept my mind off the inevitable fate about to befall me.

I felt a hand slide up my thigh and I jumped about a metre in the air.

"Fuck!" I cried in hoarse whisper.

"Well yes please honey; you sure look like you need it 'Secretary bird', you're dressed just like that’s what you need; a good fucking!" Eddie laughed.

"Oh sorry Eddie, I didn't realise you had come in." I offered in a conciliatory tone.

"Oh fuck the small talk Michele, I've got my second wind now; I just loved watching what Steve did to you in the shower block; it's got me hot as hell!"

"You…….. you saw!!!" I whispered.

"Oh yes honey, I saw. Your plump red lips looked really good clamped around Steve's big cock; you've just got to learn to swallow girl, then you won't get that yucky mess on your face."

"Of course some of your future customers like to see a pretty girl with come on her face, its adds to their pleasure and puts snotty 'Secretaries' in their place. Imagine how many of your new customers are going to be guys that you treated without the courtesy and respect they have come to expect. When you were my number one confidant you had my protection, but now you are just another prostitute. I think some of them will pay nicely to see you humiliated." Eddie stated matter of factly; cruelly!

"Anyway enough small talk," Eddie pulled me to him roughly.

I was prepared this time, rather than fight him or become pliant in his arms I responded. As his tongue invaded my mouth I pushed mine into his and commenced a passionate kiss. I made my mind go blank and remembered what Carmel had advised me, 'get him aroused and he will come sooner'.

Eddie's hand went straight to my thigh and he stroked the cool sleek satin cape over my stockinged thigh. He obviously liked the feeling because he stated to grunt as he continued to kiss me. He pushed me back on the bed and straddled me, all the time keeping his lips locked on mine as he grunted and snuffled like a pig. Eddie was now running his hand up and down my stocking legs working his way from my ankles up to my thigh as he pulled my legs up and bent my knees so that my enormous heels were flat on the bed pulled up close to my buttocks.

Eddie now ran his ran over my panties and reached into the gusset and found my flaccid penis tucked away. He pulled it free and rubbed his hand over it through the gossamer of the light clingy nylon. I shuddered.

"Oh don't be shy Michele; some men won't even kiss you before they fuck you in here; at least I'm giving you some foreplay," Eddie chuckled then again attacked my mouth with his.

He took my hand and bought it up to his shorts, he was only wearing his smoking jacket over them, the light pants he had been wearing earlier had obviously been discarded. He put my hand against the front of his jockey shorts and I felt the heated bulge of his package. I remembered how Steve had reacted when I masturbated him; the first time I had touched another man's penis, and I used the same technique on Eddie.

I dragged the back of my hand over the bulge so that my fingernails dragged agonisingly slow over his tumescent erection. Then I feathered my fingers back down his member, softly fluttering them against the rigid pole. Eddie groaned and broke the kiss so he could look down at my painted red nails running up and down across his sac and his rampant member which was straining against the light material of his shorts.

I now made a clinical decision to increase the tempo of this foreplay to excite Eddie further so that when he eventually sodomised me he would hopefully be ready to climax quickly. Maybe if I was lucky I could just get him to come against me again before he could rape me!

I reached into Eddie's shorts and gently stroked his scrotal sac using my fingernails to lightly scrape against the puckered sensitive skin. Eddie groaned and began to kiss me passionately again and with my free hand I stroked his face and ran my fingers through his hair. I circled the girth of his erect member and started a slow feathery stroking motion up and down the shaft; as I came to his glans I flicked a finger over the spongy mass of his knob.

Eddie adjusted himself over me and shucked off his jacket, pulled down his jockey shorts and discarded them. He was now naked and stretched over me, his rampant penis sticking out proudly hard against his belly. Eddie lowered himself on top of me, pushing my legs down so I was suppliant; lying beneath him with my legs splayed apart.

Eddie lifted himself up on his elbows and gazed along my body. He took in the shiny black ultra-high heeled open-toe sandals on my feet with the fully-fashioned heel and toe of my nylons exposed. He caught a glint of light off the gold chain on my ankle and ran a hand under my leg to follow the seam of my stocking to the decorative stocking tops on my thighs. His hand followed the garter strap up to the red lacy garter belt and across the sheer black nylon see through panties where he gently stroked my still flaccid penis. His hand continued upward to dwell briefly on my red lacy bra then continued up, following his gaze to my face.

He stroked my cheek as looked into my heavily made-up face, he pushed a finger into my mouth and I sucked on it seductively. Eddie stroked my jet-black hair following the mane to where it caressed my shoulders, the red highlights in my hair enhanced by my mauve eyeshadow and ruby red lips.

"Oh my fucking God you are beautiful!" Eddie whispered and lowered his lips to mine.

I tried to push my hand between us to arouse him further but he was rubbing his cock against my stocking thigh as he had done earlier in the evening. I pushed back against him, encouraging him, responding to his kisses with false passion, hoping I could make him ejaculate against me.

He moved on top of me again and to my horror I felt his strong hands pull my calves up again, bending my knees so he was between my legs with my heels flat on the bed. I tried to push myself down into the bed but he forced his hands under my buttocks and lifted my arse clear of the bed. In a swift movement he grabbed two of the pillows from the many that were scattered around my 'work bed' and positioned them under the small of my back. I knew what was coming next as he reached down to my stockinged calves and pushed upward so that my knees came up almost under my chin.

I was terrified about what was to come next but remembered the advice Carmel had given me. I kissed Eddie deeply, my arms locked around his back. I felt his hard cock punching at the thin gauzy nylon panties that were the only thing between Eddie's erection and my puckered anus. I broke the kiss and reached underneath the pillow under my head; my hand came in contact with a cold hard tube.

I pulled it out and glanced at the object in my hand; it was a tube of KY jelly. Eddie followed my gaze.

"Please," I whispered.

Eddie snatched the tube and flung it across the cell.

"No Michele, not the first time. I want your virgin arse without any lubricant except mine!"

With that Eddie clamped his lips over mine again and his tongue assaulted my mouth. I felt his grip tighten on my legs, pushing them hard against my body, forcing my pantied arse high in the air, supported by the pillows under the arch of my back. He thrust forward with his rock hard cock and I felt it tear through the flimsy nylon of my see-through panties and slam against my sphincter.

I wanted to scream but he clamped his mouth tightly against mine, kissing me hard but keeping his tongue out of my mouth for fear of me biting it. Eddie started to push hard against my puckered ring gripping my legs even tighter. I felt my sphincter stretch as Eddie's glans began to invade my arse; the slight lubrication from his pre-come easing the passage only slightly. I felt a pain that was almost unbearable as Eddie continued to push against me. He was still kissing me but grunting at the same time; his breath exploding in little gusts between my lips.

The head of Eddie's penis was now just inside the entrance to my back passage and my sphincter clamped tight around his shaft. There was now no lubrication whatsoever as Eddie commenced to rape me. He pushed into me slowly, forcing his engorged member deeper into me. The pain was excruciating and I began to cry. I couldn’t help it. The fear, the humiliation, the pain; it was too much.

Large tears ran down my cheeks leaving trails of mascara as I began to sob in earnest. Eddie released one hand and bought it up and slapped me hard against my face.

"Stop that fucking shit right now!" he demanded.

"You've been a good girl up until now Michele, so just take it. Take it!!!"

He replaced his hand on my limbs and continued pushing into me. I knew now that all I was going to get was more pain unless I relented and assisted Eddie in his rape. Passive compliance was doing nothing but causing me agony. I concentrated and forced myself to try and relax the muscles creating the resistance to Eddie's cock as it intruded deeper into me. It was hard to do but I was able to make my inner passage muscles relax and suddenly Eddie's cock slid about four inches into me.

More pain now as the thicker part of his member tried to force itself still deeper into me. Eddie was panting now and was supporting his weight on his forearms that held my legs locked to my body. He was looking down so he could see his penis disappearing through the hole he had forced in my panties as it buried itself into me. Then he looked at my beautiful face, the makeup running from my tears.

"Oh yeah, this is so good!" he groaned and gave a mighty thrust.

As I felt the thrust coming I forced myself to relax and Eddie's hard cock thrust in all the way, deep into my bowels. His scrotum bounced against the soft nylon covering my arse cheeks and as he ground his cock inside me his balls rubbed against my slinky nylon panties.

I screamed, the pain was the most incredible thing I had ever felt. I tried to stop but one long agonising scream escaped me. Eddie lifted a hand and I knew he was going to belt me again. I did the only thing I could. I raised the leg that he no longer held and wrapped it around him; then I encouraged him to release the other leg so my that my legs were locked around his waist, the shiny high heels pointed to the ceiling.

I pulled his lips down to mine and thrust up to meet him and I slid my tongue into his mouth. I started to fuck Eddie McManus! At first the pain was so bad that I was sobbing into Eddie's mouth as we copulated. Eventually though, enough of his pre-seminal fluid had leaked so that it slightly lubricated my anus. Although it felt immensely uncomfortable I was able to bear the pain and concentrate on trying to get the rape over and done with.

I bucked against Eddie matching his thrusts and getting into his rhythm; I scrunched my panty ass against his scrotum as he slammed his cock home inside me and rubbed my stocking legs along his back to excite him further. My arms were locked around his back and we both kissed passionately between our gasps for breath as we rutted.

I felt Eddie quicken his pace and he plunged harder and faster, I worked hard to keep up with his rhythm and held his face in my hands and kissed him all over as my legs remained locked around his back. I eased my legs down slightly and dug my high heels into his sides to stimulate him further, I just wanted this to be over.

Then, just as Eddie was moaning and running his hands up and down my stocking legs; I guessed he was approaching his orgasm; a strange thing happened. During his thrusts I began to feel a pleasant warm feeling deep in my bowel. My penis was beginning to stir in the soft nylon of my panties, encouraged by the pressure of Eddie's body against mine as he fucked me. What the fuck was happening? Then I realised, I had read about this somewhere, stimulation of the prostate gland.

'I am not enjoying this! I am not enjoying this!! I AM NOT ENJOYING BEING RAPED!!!' I thought to myself in terror!

Eddie gave one huge lunge and pushed his cock fully inside me, he ground his balls against the silky fabric of my panties and madly stroked my stockinged thighs. He clamped his lips hard against mine and I felt his hot seed expel itself inside me. His cock convulsed and shuddered.

I had an uncontrollable reaction; my high heels drummed on Eddie's back as I lifted my arse up off the pillows to push as hard as I could against him. My tongue lashed around wildly in his mouth and I sucked his tongue deep into my mouth. My sphincter spasmed and my back passage convulsed against Eddie's ejaculating penis. My prostate pushed out rings of pleasure moving through my body in waves. I ejaculated into my panties; I wasn't even erect although my flaccid penis was pushed hard against Eddie's torso, the soft silky nylon of my panties caressing my soft member trapped between us.

We lay like that for what seemed like an eternity as our mutual orgasms subsided, gradually relaxing our fierce grip on each other and our kisses becoming more delicate and soft.

Eventually Eddie eased himself out of me and I felt the strangest feeling as my arse muscles remained relaxed and my sphincter dilated. I felt Eddie's spend leak from me and slowly seep from my arse into my torn panties. Eddie sat on the edge of the bed his member slowly deflating. He reached out and caressed my cheek with the back of his hand then bent and kissed me tenderly.

"That was lovely Michele," he whispered a genuine smile on his face.

I was still in shock at my response, trying to rationalise it. It was just my body reacting to a stimulus; 'I DID NOT ENJOY BEING RAPED!!!' I kept this mantra going over and over in my head.

Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread there when he had pressed his body against me.

I watched the terrible storm brood in his eyes as he reached out and smashed me across the face.

"You dirty Cunt!!!" he screamed, and pushed my face into his belly.

"You lick that disgusting mess off my body before you lose some teeth!" he bellowed, rubbing my face against his belly as I made a vein attempt to lick my own spend off his stomach.

He pushed me back on the bed, my makeup ruined, mixed with semen and tears and smeared all over my face.

"Now get yourself cleaned up and get changed you filthy whore; you're open for business!!!"

 

To be continued……………………………………………………………………………..

Eddie's hands slid up my body to my shoulders and he gently eased me back and lowered me to my feet. He looked down, pulled up my half-slip and smoothed down my dark blue skirt, the hem coming to rest against my sticky thighs. Then he did something that summarised in my mind how used I felt; he took a handful of my skirt and wiped his slowly deflating penis on it; the globs of semen and silvery seminal fluid staining the dark material as he cleaned himself on me.

"Not bad Michele," he chuckled, "Now clean yourself up sweetheart, you look a complete fucking Mess."

 

Part III

 

Carmel appeared as if from nowhere and took me by the hand. I was so shocked at what had happened that I just followed her instinctively, as I passed Eddie, clattering on my high heels, he reached out and spanked my arse.

"Have her ready in half an hour Carmel, I haven't finished with her tonight; not by a long shot."

"Oh, and tell Steve he can use for ten but he's not to fuck her, ok." Eddie bellowed down the corridor.

"Of course Eddie, you want the secretary thing again or you want her ready for bed?" Carmel asked.

"I think I'll have her fully dressed again; stockings this time though, I don't want to have to rip any more pantyhose to get what I want ok!" Eddie answered.

"Sure honey, I know what you like, she'll be ready for you in half an hour."

"And don't forget to tell Steve he can't fuck her, I don’t want slops."

"Of course Eddie," Carmel smiled sweetly at Eddie, "Now come along Michele lets get you cleaned up honey," Carmel whispered dragging me down the corridor towards the bathroom on E Block.

"What's he on about?" I asked Carmel as we went into the bathroom and she led me to the sinks.

"Eddie is going to use you until you bore him, then you are going to be just one of us girls; a common prostitute hawking your pretty arse for Eddie; making him money and occasionally making him come." She sneered at me.

"Just get used to it; learn to like it!"

"Learn to like it!" I scoffed.

"Learn to like being dressed as woman and used by these poofters in this jail; you're fucking joking! I hurled at her.

Then I felt an enormous slap across my backside; the pain was excruciating.

"Oh god!" I moaned.

"No not god, just little old iron-bar Steve. Fucking hurts don't it; my steel bar crashing against your arse like that?"

"So you think I'm a 'poofter'; well I've got a another steel bar right here in my jeans honey and you've got about ten minutes to take care of it!"

It was Eddie's enforcer Steve, undoubtably he had heard Eddie say he could use me briefly and was wasting no time coming to claim his prize. I realised at once that fighting him would be futile and decided to let him take what he wanted. I had heard Eddie say he couldn't fuck me so I figured the best defence was attack. If I excited him enough maybe I could get him to orgasm against me just like Eddie had done. That was humiliating enough but I didn't want to consider any alternative.

I turned around and forced myself to move towards Steve and embrace him. I rubbed one nyloned thigh against his leg and reached up and kissed him. His breath was atrocious, I forced myself not to gag and pushed my tongue into his mouth and gave him a long kiss.

"Steve honey, you don't have to use that bar on me; lets just take care of the bar I can feel throbbing in the front of your jeans," I whimpered in what I hoped was a sexy parody of a seductive female.

"Oh but you don't understand Michele," he sneered, "its more fun to take what I want!"

Steve pulled me roughly to him and locked his lips on mine. At the same time his hand went to my skirt and yanked it up around my waist. He twisted his hands in the nylon of my slip and yanked it down around my knees and ground his body against mine. I felt his hard member pushing against me though the rough denim of his jeans.

Then Steve pushed me away to arm's length.

"Drop the skirt bitch'" he hissed.

"What?" I answered not understanding quite what was going on.

'SLAP'!

My head exploded with the force of the slap to my face; I thought my head had been knocked off.

"Don't you fucking mark her!" Carmel warned Steve.

"Well you tell that bitch, I ain't half as nice as Eddie so she better just take what's coming ok," Steve hissed at Carmel.

"Ok Steve, I think she gets it!" Carmel retorted.

"Well let's just make sure," Steve answered and then punched me in the stomach. I doubled over in pain completely winded.

"Right I'm wasting time, no more talk; just action. I tell you what to do and you do it bitch ok?"

I nodded as best I could, my face was on fire from the slap and I still couldn't breath.

"Skirt!" Steve demanded.

I put my hands to the waistband of my skirt and tugged it down around my ankles then stepped out of it along with my slip.

"Now my jeans!"

I stepped forward and tugged at Steve's belt.

"On you your fucking knees you stupid cunt!" Steve bellowed and brutally pushed me down.

Now my face was level with Steve's crotch and I reached out and undid his belt. I noticed again my manicured painted nails as I eased the zip of his fly down and snapped the button at the top of his jeans. As I eased the jeans down his legs a fetid aroma assaulted my nose and I noticed his putrid underwear.

"Stand!" Steve ordered.

I stood, tottering on my heels trying to recover my breath. Steve grabbed me and forced himself against me pushing his tongue deep into my mouth and pushing his hips against me. Carmel looked on at Michele; this attractive petite woman in heavy ruined makeup, dressed in her blouse and jacket but without her skirt, wearing torn and laddered hose and panties was teetering on her stylish black pumps as this jailhouse hooligan with fetid breath and stained boxers ravaged her.

I felt Steve reach between up and knew what he was up to. He was freeing his penis from his underwear as Eddie had done. I was still determined to get this over with as soon as possible and seized the initiative. As soon as I felt Steve's erect member against me I reached down and gently held it. I had never held another man's penis before and it felt tactile and spongy, I could feel the thick veins running along it. It also felt slick and warm. I commenced a slow stroking motion, easing my hand along the shaft and circling the enormous head. The cock was so thick that I couldn't grip its full girth in my hand.

Steve groaned, "Oh yeah bitch, you know what daddy likes."

He pushed me back slightly so he could see my painted nails trailing along his shaft as I wanked him. A thin thread of shimmering clear pre-come ran from the purple head of his penis across to my gauzy nyloned thigh. Steve reached out and rubbed my pantyhose thighs and then worked his way up to my panties. I stiffened as I felt his hand go inside my panties and begin to fumble about. I forced myself to relax otherwise I knew Steve would belt me again. Steve eventually found my thin soft cock nestled in the crotch of the sheer nylon panties and he began to free it from its little nylon prison.

I concentrated on slowly masturbating him to the best of my first-time ability. I gripped his member tightly and slowly squeezing and stroking as I worked my hand up and down his penis. He must be enjoying it I though, because he was just staring at my hand wanking him while one of his hands stroked my nyloned thighs and pantied crotch. As his other hand had finally freed my member, he began to squeeze it harder and harder. I just concentrated on getting this over with as soon as possible, the feel of his hand on my penis was vile.

I decided to move things along and pushed myself against him stroking his cock with firmer faster strokes. I lifted my head and kissed him, gently sliding my tongue along his gums and exploring his mouth, blocking out the awful taste of his breath. I guided his member against my pantyhosed thigh and rubbed it there, the underside of his cock with all those nerve endings rasping against the diaphanous nylon as my painted fingernails gently raked the top of his turgid cock.

I began to pump my leg up and down so that he was dry fucking me, similar to what Eddie had done. With my fingers stroking and squeezing in time with my humping leg I was hoping he would soon climax. He was groaning now and breathing heavy; his fetid breath puffing in my mouth. Combined with the meaty stench coming from his crotch I was ready to gag but kept control and tried harder to please him, kissing him deeper and stroking him harder.

Then he suddenly grabbed me by the shoulders and threw me back away from him. I stumbled back on my heels and my back crashed into one of the sinks, winding me again.

"Oh no you fucking bitch! You fucking cunt! I know what you're up to!" Steve roared.

"You're trying to get to come like this ain't you?"

"Well I ain't going to come in Eddie's leftovers. Get back here!"

I moved forward towards Steve warily. This parody of a secretary in a blonde wig, come-soaked and torn hose and panties, tottering on shiny black heels, dressed from the waist up in blouse and business jacket. What a sight!

Steve reached out and put his hands on my shoulders and pulled me to him. He kissed me deeply, forcing his tongue deep in my mouth. Then he eased his hands up to my shoulders and commenced to push me down.

'Oh God! I know what he wants,' I thought.

I dropped to my knees on the cold tiled bathroom floor and stared eye level at Steve's disgusting throbbing penis. He grabbed my head in both hands and pushed it forward so that the head of his cock was between my lipstick lips. He kept pushing but I couldn't open my mouth. The smell coming from his loins was fetid and I was sure that monstrous member would make me gag and vomit..

SLAP! I saw stars and the ringing in my ears blocked all other sounds. I started to cry and as I did Steve grabbed my head in both his hands and pushed his hard, throbbing cock into my mouth.

"You take this bitch, and don't bite or you're fucking dead!" Steve fumed.

He pushed the filthy thing into my mouth until he felt me start to gag and then commenced raping my face. That's the only way I can describe what he was doing to me. He held my head and raped it! He thrust his filthy, foul tasting, pulsing, penis in and out of my mouth. Besides the cheesy rancid taste there was also a sweet salty taste that I knew to be pre-come. My gag reflex was suppressed as long as he didn't drive his cock too deep into my throat, but it was so huge I couldn't breath.

Then I sensed Carmen beside me.

"Breath through you nose hun, breath your nose. He won't be long, I can tell he's nearly there."

Steve tightened his grip on my head and slammed me back and forth against his cock. He pulled me back until just my lips circled his plum coloured knob; then drove me against him as he thrust forward, forcing his turgid meat into my mouth. As a reflex I moved my tongue around the shaft and sensed his enjoyment. I was hoping he would come soon as every time his cockhead hit the back of my throat I had to gag. Then I realised the sick bastard was getting pleasure out of my gagging. Now he increased his attack on my virgin mouth and I tasted more and more of his pre-seminal fluid. He was groaning and panting.

"Yeah bitch, I'm coming whore, take this!"

He slammed forward hard and pushed my face into his groin and held it with two hands at the back of my head. His penis throbbed and erupted in my mouth and I felt the hot salty taste of his seed as it exploded from his glans. I started to gag and tried to force myself free as his semen flooded my mouth and slid down my throat.

"Take it bitch, take it!" Steve howled in his orgasm.

"OH Yeah baby, on your face yes! On your face!"

Steve pulled my face out his groin and held it close to his crotch with one hand; with the other he rubbed his still ejaculating penis all over my face. His ejaculate shot across my cheeks and landed on my eyelashes, a string of hot semen running across my face. Another spurt shot against my lips and up my nose. I felt stream after stream of semen scald my face and start to run down my neck. The thick gobbets of milky come smeared my cheeks, nose and lips. Looking out my eyes I could hardly see because of the ropes of hot come across my eyelids and lashes.

Steve's orgasm started to subside and he continued to rub his cock all over my face. He smeared his spend all over me, it combined with my lipstick and makeup to make a hot sticky film that covered my face. Steve stepped back and looked down at me, on my knees, may face covered in come, my clothes a mess and makeup mixed with semen, caking my face.

He reached out and grabbed a hand-full of my blonde hair and wiped his cock clean in it.

"Get this useless bitch cleaned up and dressed for Eddie; her night's only just started!" Steve sneered at Carmen as he turned his back and walked away zipping up his fly.

 

To be continued……………………………………………………………………………..

"Mike, now you are Michele, you look beautiful! I hope you enjoy your first time as much as I did," said Carmel as she slid past me and out the door.

And that is how I became to be dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail.

 

Part II

 

"She's all yours Eddie. She looks beautiful." I heard Carmel say as 'she' disappeared down the corridor, her high heels clicking on the tiled floor.

Eddie appeared at the door to the cell, he stepped inside and closed the door behind him.

"So what do you think of the little nest I have here for you 'secretary bird'," he asked sarcastically.

"Eddie, what's going on, what's all this about," I implored.

"Well if you haven't figured it out by now hun, you are a lot dumber than I thought. I needed a secretary, but not just to be my accountant, I need a 'Girl Friday' who can help run my business and take dictation; emphasis on the DICK," he smirked.

"I recognised your potential early, so now I have made you into Michele, my secretary, confidant, and soon to be my personal assistant. Very fucking personal if you know what I mean!"

Eddie stepped towards me. He was dressed in a pair of light tan linen pants, a smoking jacket, and expensive looking moccasin slippers adorned his feet.

"You look beautiful hun, just what I was hoping for; come here," he whispered hoarsely and reached out to pull me to him.

I immediately tried to step back out of his reach but he gripped my forearm and pulled me forward. As he did his other hand came up and slapped me soundly across the face. It was what the inmates referred to as a 'bitch slap', and it really stung. My eyes started to water.

Eddie took a handkerchief out of his pocket and put it to my teary eyes.

"Now Michele, don't cry; I would hate to ruin all the hard work that Carmel did with your makeup," he said.

"Just behave yourself and there will be no more pain."

He lifted my chin and looked deeply into my eyes.

"God your just fucking beautiful," he whispered and put his arms around me.

Eddie embraced me, locking his strong arms around me. His faced moved forward and I sensed he was about to kiss me. My involuntary action was to move back. His right hand came up again and was held out flat near my face, ready to slap me again. I forced myself to stay still.

He enclosed me in his arms again and this time his lips came down on mine. It was the strangest feeling, I could feel the slight rasp of afternoon shadow on his face, smell the faint scent of his aftershave and the press of his thick lips against mine. He pushed his tongue into my mouth and I could taste my lipstick mingled with his mouthwash. His tongue started to explore my mouth and he pulled me even closer.

I forced myself not to back away, rather I became limp. I knew there was no way out of my current predicament without extreme pain and punishment. Even then Eddie would take what he wanted from me. I tried to clear my head and just endure what was happening to me without further antagonising him.

Eddie was now kissing me passionately, his lips pressed hard against mine, his tongue exploring under mine then slowly working its way around my mouth, flicking and probing. His body was hard against me and I felt a hand slide down my back and come to rest on my buttock. He rubbed his hand there, the material of my dress and half-slip whispered against the smooth nylon of my panties and hose.

"Mmmm," Eddie whimpered, his lips still against mine.

He lifted his face and looked at me again. I realised he was not looking at another man, but a gorgeous woman in her mid thirties, her hair styled in a bottle – blonde bob and wearing thick makeup, rouged cheeks and plum red pouting lips.

"God I just have to have you hun, my lovely little secretary bird; this is just how I imagined it would be!"

Eddie started kissing me again and I felt his other hand slide down so that he had both of my buttocks in his grip. I felt him lift up the hem of my business suit skirt and caress the material of my half-slip. His hands worked in a circular motion in time with his tongue, rubbing the silky slip against my tight pantied buttocks. I was so shocked that it took me a while to realise that he was also gyrating his hips against mine; pulling my lower half against his as his passion intensified.

I commanded myself not to move, to just take what was coming; it couldn't be worse than a beating or broken legs!

Then I felt it, I went from being a limp rag doll and tensed up, almost pulling myself away. Using the utmost self-control I forced myself to go limp again in his arms and allow him to ply my body against his. What I felt was a long iron bar that could only be an erection pushing against my stomach. I could feel it though the material of his slacks and my skirt.

Eddie was gyrating against me now, his tongue working feverishly in my mouth, his lips crushing mine. The hands on my ass gripped my buttocks and pushed my lower body harder against him. He was 'dry humping' me I realised; pushing his erect member against me through our clothes. I heard and felt a deep humming from his throat and he was breathing heavily in and out of his nose as he continued to kiss me deeply.

Eddie suddenly stopped pushing on my buttocks and I felt a hand leave my ass, glide across my hip then move between us. He fumbled there, his hand between my navy blue skirt and his loose tan linen pants. My god I knew what he was doing! And then I felt the fruits of his efforts down there.

Eddie had freed his erect penis from the confines of his pants and it was now like a hard iron bar between us. His hand flew back to my ass and he again rucked up my skirt and used both hands to caress my buttocks through the slip as he pulled me back against him.

He ground himself against me, his cock hard against my lower abdomen. I could feel the girth of it though the layers of skirt, slip, panties and pantyhose. I concentrated harder on not panicking and just allowing Eddie to do as he wanted; surely this would be over soon.

Eddies kisses had now become a hard insistent invasion of my mouth; every few seconds he had to break to take a breath; I could feel my lipstick smeared over my lips and over my teeth. During these little gasps for breath he would pant,

"Yes! oh yes baby! so good! so good!!!"

"Gotta do it soon! gotta do it soon!!!"

Eddie again removed a hand and fumbled around down there between us. This time I felt him lift my skirt up completely so it was rucked up around my waist. He lifted me up and forced me to my toes, my heels left the ground and I fell further against him, my face now level with his as I balanced in the awkward high heels that I had never worn before. Eddie struggled with his erection and I felt him push it down then release it so it sprag forward whilst at the same time he pushed our lower extremities together.

His cock was now wedged between my legs, hard against my crotch and encased in the silky sheer material of my half-slip.

"Oh my god!" Eddie groaned and began his hard circular humping against me yet again.

He got into rhythm, dry fucking me in time to his feverish kisses; slowly circling his manhood he had trapped between us. Eddie tugged hard on my slip and I felt it start to drag down my thighs until it was around the tops of my knees. Now I could feel his turgid penis trapped between my pantied crotch and gossamer hosed thighs. Eddie was pushing up now as he thrusted, fucking the silken trap made by my pantyhosed thighs and nylon pantied crotch. I could feel the head of his penis rubbing itself along mine through my panties. My penis was still held in place tight between my legs by the gusset of my pantyhose.

Eddie had just what he wished for I guess. His slutty secretary forced to stand tiptoe in shiny black heels, her silken pantyhosed legs circled by her pretty peach half-slip just above her knees. Her dress rucked around her waist, her blonde bobbed hair framing a heavily made-up face that was locked to his in a powerful stream of kisses.

The big strong man held his sweet secretary in his tight embrace, sliding his tumescent member between her thighs, the gossamer of her hose and silken sheen of her panties serving to provide little electric shocks of pleasure through his body.

I felt Eddie quicken his pace and his cock begin to throb. He pushed against me harder and he held me so tight I though he would squeeze the breath out of me. His tongue was now a wild wet animal, thrashing in my mouth, fluttering and exploring every crevice.

Both his hands gripped my buttocks squeezing them roughly through the gauzy nylon panties and pushing me forward and back to the rhythm of his thrusts. Then he groaned and gripped my ass so tight that I felt the nylon panties tear and his fingers burst through and bury themselves into the gusset of my pantyhose. He forced me against him as hard as could and I felt his penis begin to pulse and throb.

Hot wet fluid suddenly soaked the tops of my thighs and the crotch of my panties. I felt stream after stream of his creamy seed shoot against my silken hosed thighs and being to slowly run down my legs. My crotch was soaked with hot sticky liquid and as I struggled to breathe I could smell the salty, slightly swampy smell that is associated with fresh semen.

Eddie had ejaculated against me. He slowed down his thrusts and slightly eased his grip on me. His spend had now invaded the layers of panty and hose and I could feel it warm and milky against my penis.

Eddie's hands slid up my body to my shoulders and he gently eased me back and lowered me to my feet. He looked down, pulled up my half-slip and smoothed down my dark blue skirt, the hem coming to rest against my sticky thighs. Then he did something that summarised in my mind how used I felt; he took a handful of my skirt and wiped his slowly deflating penis on it; the globs of semen and silvery seminal fluid staining the dark material as he cleaned himself on me.

"Not bad Michele," he chuckled, "Now clean yourself up sweetheart, you look a complete fucking Mess."

 

 

To be continued………………………………..

 

 

"I expect you’ll be very busy indeed," Eddie’s laughter faded as he disappeared down the corridor between the cells.

I cringed at the thought of another night in this caged prison brothel, forced to service some of the roughest men I had ever met. At the same time I was feeling confused as to how quickly I had acquired female mannerisms; how I had become aroused by wearing the lingerie, makeup, wigs, and heels that Eddie forced me to wear. I was also amazed at how, after only a brief introduction, I was developing the skills of the feminine art in applying makeup.

I was more disturbed however, by how I had responded to the sexual attentions of some of the punters and the ministrations of my crossdressed sisters. I could not deny that, despite the fact that during this torrid night I had been repeatedly orally and anally raped, I had experienced two of the most intense orgasms of my life this evening. I decided that I was just too dog-tired to think about it; I needed to sleep. I was even too tired to be angry with Charlotte and Carmel, who although they had obviously enjoyed the sexual encounter we had just experienced together, had obviously been put up to it by Eddie so that he could enjoy the ‘all girl’ show.

The two vixens in question, (who had just introduced me to my first transvestite lesbian experience), slunk out of my workroom cell. They both glanced back and blew me a kiss.

"Nightie-night sweetie," they giggled in chorus, the sound of their laughter and the clattering of their high heels diminishing as they moved on down the corridor.

Mabel came in and dumped my prison fatigues on the bed and pointed to the door with the words,

"Out! Shower. Get changed!"

I got the message and slipped out of my feminine attire and deposited it in the laundry bin in the corner of the cell. My heels and breast-forms went inside the large wardrobe. I removed my wig and put it on a vacant wig-stand then took the towel Mabel proffered, cinched it around my waist, and headed once again down the passageway between the cells carrying my fatigues to the shower block.

The overhead lights suddenly clattered on revealing the workroom cells on either side of the passageway. Through the open bars I stared at the oversized double beds, rumpled satin sheets, large armoires and dressers with makeup mirrors, totally incongruous in this disused prison wing. The workroom cells were like islands of perfumed femininity amid a sea of stink created by caged men.

Mabel poked her head out of my cell and barked orders to a couple of prisoners who I recognised as weaker individuals who had ‘no muscle’ and therefore had shitty jobs working in the prison laundry. They were stripping the beds and dumping sheets and pillowcases into large wheeled washing carts. They were also emptying the laundry bins from each cell into individual oversized prison laundry bags; I noticed the laundry bags were each labelled with the cell numbers and the feminine names of the ‘working girl’ that used each cell. As I passed one of the laundry hands I saw him bring a pair of soiled panties to his face and rub the bulge in the front of his denim jeans. I scurried past disgusted.

The laundry was a big money maker for the prison. It catered for the needs of the prisoners, the guards, and also took in work from nearby hotels and a hospital. Eddie controlled the prison laundry, as he did just about everything in Chelmsford prison. Obviously also had the laundry workers working overnight to wash and dry the bedclothes and clothing that belonged to his ‘working girls’. To make his prison prostitution operation work he must also have the laundry dry cleaning service clean the ‘girls’ skirts, blouses, jackets and other items of clothing.

The cleaning of feminine clothing had to be being done overnight as I had made many trips to the prison laundry during the day whilst working as Eddies accountant and I had never seen any items of female attire in there. I knew Eddie made a considerable amount of money from the laundry; and of course, he was paying off someone high in the prison authority so that he could run the laundry business. As his accountant I knew he would also be charging the ‘girls’ for the laundry service; Eddie made money off everything, he gave nothing away.

When I got to the shower block I ran the water as hot as I could get it and soaked myself for half an hour in the shower trying to wash away the shame and humiliation of the last few hours. I scrubbed my face repeatedly to remove the caked on makeup. The blush, lipstick and eye shadow came off easily but I had to scrub at my face continually with the washcloth until it came away bearing no traces of foundation or mascara. I poured nail polish remover onto a cloth and cleaned the red nail polish from my fingernails.

I moved to the mirror and was glad to see that I looked like a man again; but then I noticed that some mascara was still clumped here and there on my eyelashes and little clots of eyeliner were smudged in the corners of my eyes. I picked up a bottle of moisturising cleanser from the shelf under the sink and removed the last traces of ‘Michele’ from my body.

I winced as I pulled on my denim prison uniform fatigues and felt the scratch of stiff cotton on my body instead of the luxurious feel of satin, silk and nylon. ‘Stop it!’ I told myself as I found myself wishing I could exchange the scratchy denim and cotton work-wear for the soft feel of feminine garments; ‘this is how you are supposed to be dressed Mike; as a man!’

I made my way back to my accommodation cellblock without further incident. I was amazed to find my cell unlocked and unguarded. Fucking Eddie ran the whole prison I was sure if it! I let myself into the relative privacy of my own cell. With only a peephole in the door for the guard to look through instead of the open bars of the workroom cells in E Block it was as private as one could get in prison. As my head hit the pillow my mind was spinning with what had happened to me, how drastically my life had changed in one day. The last thing I noticed through teary eyes before I fell into a deep sleep was the clock on the wall ticking over to 2:30am.

I awoke the next morning and looked straight at the clock; it was 9:30am. Eddie must have arranged it with the guard on my wing to let me sleep in. I was tired and sore from the events of the previous evening and the early hours of this morning, I just couldn’t believe what had happened to me. I seemed normal enough (or as normal as one could be when you are a guest in Chelmsford prison); just Mike. Mike brushing his teeth, Mike combing his hair, Mike changing into clean fatigues. Mike drinking coffee alone in the deserted cafeteria. There was no sign of Michele or her feminine ways; Christ I wished it were all just a bad dream!

I looked down at my hands holding the coffee cup and noticed that there were little crescents of red nail polish under the cuticles of some of my fingernails. "Fuck!!!" I exclaimed. Then I heard the voice I feared most; Eddie had snuck up on me and whispered in my ear,

"Come on Secretary you’ve got a lot of work to do. Just because I’ve found you some after-hours employment, doesn’t mean you can neglect your day job," he snickered.

I followed him and took up my usual post working on Eddie’s books as I had done every day for the last few months. I couldn’t bear to bring up with him the events of last night or even look him in the eye. What I did do though was to pay particular attention to those parts of Eddie’s business that had now come to directly effect me. Because Mabel ran the books relating to the prostitution ring, I had never really paid them too much attention before, except to check the bottom line for profit against loss; today I paid them special attention.

how Eddie’s prison business works and how Mike/Michele ended up becoming Eddie’s accountant and ‘secretary’.

A note for those of you who haven’t read Part I of this story; you probably need to read it now to understand

It was all there, the amount each punter paid Mabel for a ‘session’ with each ‘girl’ (there were various codes that I didn’t really understand but as some sessions cost more than others, I could only deduce those punters wanted ‘special services’ and paid accordingly). Here was listed the earnings made by each of Eddie’s transvestite hookers against the costs involved in running his secret prison brothel. Payments were listed to Mabel, the guards (although a lot of the guards seemed to take their payment in ‘trade’), and the inmate ‘minders’ Eddie employed (I shuddered as I though about how ‘Iron-bar Steve’, his most vicious minder, had used me).

The costs of female attire, lingerie, cosmetics, perfumes, wigs, shoes and other accessories were carefully recorded against each girl’s name and deducted from her earnings. It appeared that despite these costs, and even after Eddie had taken the larger part of the profit for himself, the girls still made a substantial amount of money. By prison terms they were rich; in fact they probably made more money than your average streetwalker did on the outside.

Then I looked up the ledger entries Mabel had made against me, ‘Michele’; I was astounded at how much money Eddie had made from me last night, even though only a couple of my ‘tricks’ were paying customers. Then I looked in the debit column at how much money I owed Eddie; I was flabbergasted. I owed him thousands of dollars for the clothing and accessories he had purchased for me!

"What the fuck Eddie?" I turned around and shook the ledger book at him.

"This is bullshit! I’m a rich man outside but it will cost me double the money I owe you in bribes to have that much smuggled in!"

"I suppose I have no fucking choice, It would take me weeks to pay this off earning the money you expect me to make in your filthy whorehouse!"

I couldn’t believe that in my outrage I was shouting at Eddie like this.

"Oh no Secretary bird; months at least; probably a year to clear that debt!" he laughed.

"What the fuck?" I stammered.

Eddie reached out and grabbed my slender throat,

"You can only pay for the goods and services I provide for you with the services you provide to me!"

"What the fuck does that mean?" I asked. "Why can’t I just pay you out from money I have on the outside?"

"All of your clothes, makeup, wigs, nylons and those nice frilly things I have you wear, you have to pay for out of the money you make in the workroom. That’s the deal. How do you think I keep my little harem working for me?" he responded.

"And of course you will always need more of those lovely things, because, as you can imagine, they tend to get worn out quickly and suffer more than their fair share of wear and tear during the working day; or should I say working evening," he laughed.

"And I can’t have my punters complaining that my girls dress like shit now can I?" he mocked.

"Besides; look on the bright side, you get to keep everything you pay for and I’ll let you keep any tips; pardon the pun," he laughed.

"In a few weeks, once you get to like the work, you will be asking for more and more clothing, lingerie, and girly luxuries, all my girls do," he finished.

"Girls?" I stammered.

"Girls! Girls! Fucking GIRLS!!!!!"

"They’re crossdressers you dolt! They’re men! Men! MEN!!!"

"And so the fuck am I! I’m a fucking MAN not a GIRL!!!!!"

Whack! Everything went black.

I woke up on my bunk in my cell my head throbbing.

"Christ!" I groaned.

Eddie had obviously belted me during my outburst and knocked me out. I raised myself off my bunk and looked in the mirror. No visible damage done; just a bump on the back of my head. Eddie was too smart to mark his latest money-spinner.

I noticed my cell door was closed and on further inspection locked. Then I noticed a suit-bag hanging on the end of the double-bunk. On the disused top-bunk was a pair of black high-heeled open toe sandals, a makeup case, a pair of expensive Italian pantyhose still in their wrapping and some boxes that when opened contained white satin lingerie. A wig composed of a shiny black bob, with discrete cerise highlights was perched on a wig-stand. I recognised it as one of the wigs Carmel had had me wear last night. The wig had been cleaned, combed and styled; the harsh prison light bulb picked up the highlights in the hair.

I walked over to the suit-bag and noticed a note pinned to it. It read:

‘Get dressed. Be ready by 1pm and make sure you look good for a special friend of mine. Steve will pick you up.

Or don’t get dressed, your choice!

If you’re not dressed when Steve gets there you won’t need to get dressed in anything but hospital pyjamas for at least a month!

Love Eddie

XXX’

Resignation came crashing down on me yet again; I would not be able to get out of Eddie’s clutches until I was released from Chelmsford…or… a glimmer of hope formed in my mind…transferred!!! That was it! I would get a transfer! I had plenty of money outside; sure it cost me double every time I tried to get any of my money smuggled in, but if Eddie could bribe the guards, surely I could too! All I needed to do was to find out the right person to bribe. I made a resolution right there and then. I would withstand whatever depravity I had to until I could arrange a transfer to another prison. With this resolve firmly in my mind I started to get dressed into the clothing that had been bought into my cell whilst I was unconscious (probably delivered by Mabel in her male alter ego: the washed up trustee lifer).

I shucked out of my prison fatigues and stood naked in the centre of my cell. Short, slim and well proportioned with all of my body hair removed my body did not look especially feminine; but it was more womanly compared to most of the inmates in here who were either bodybuilders or had resigned themselves to lives of flabby inactivity. Maybe I could fatten myself up so that I wouldn’t be attractive to men? Then I remembered Charlotte, the chubby whore from last night, being fat had not worked for her, it had just made her more attractive to men who liked larger women (BBW’s as they were referred to in men’s magazines).

I opened the large makeup case and investigated the contents. It contained plenty of makeup, a small bottle of perfume and some jewellery in the upper compartment tray. I removed the upper tray to discover that in the bottom compartment was a pair of breastforms. The two silicone tits looked forlornly up at me from the bottom of the case. Breastforms! This time yesterday I wouldn’t have had a clue that the fucking things even existed. I selected the ruby red nail polish out of the makeup case and sat down on my bunk and painted my toe and fingernails contemplating the future. Eddie obviously had a special trick lined up for me this afternoon; what he didn’t know was the trick I was going to play on him; if I could just find out who I needed to bribe to get out of this nightmare.

I laid out the makeup on the shelf in front of the mirror over the sink and started the transformation from Mike to Michele.

I applied a layer of heavy foundation from my hairline all the way down to the bottom of my neck. Next I applied a second layer of Revlon foundation that matched my natural skin tone and then set the foundation with a lighter shade of face powder. I rouged my cheeks to highlight my sharp cheekbones, applied another light dusting of powder, and then went to work on my eyes.

My eyebrows were thin anyway and just required a light touch of pencil to form the arches. I applied a pinkish hued eye shadow to my eyelids and then blended a light aqua from there to just under my eyebrows. With a fine brush I applied black eyeliner in a thin line on my eyelids as close to my eyelashes as possible, top and bottom. I took the line right into the corners of my eyes as I had been taught. I applied lashings of black mascara to my eyelashes, only having to clean up a few little flecks that dropped onto my face. Next, three coats of the same plum coloured lipstick that I had worn last night, carefully applied inside the matching lip-liner. I pulled the black bob onto my head and adjusted the wig so that it sat correctly. I clipped a pair of silver and diamond encrusted sapphire drops to my ears and a matching pendant around my neck to finish the effect. I looked gorgeous; Carmel would have been proud of my efforts I thought to myself.

Now, to the foundation garments! I unwrapped the expensive looking Italian pantyhose. The diaphanous sheer black nylons were fully fashioned with dark reinforced cuban heels and toes; a neat black seam ran up the back of the legs to the top of the waistband. The gusset was as sheer as the rest of the hose with no joining seams or cotton insert that is usually found in the crotch area of most pantyhose. The nylons were decorated with tiny little rhinestones just above the heels.

I sat on the edge of the bottom bunk and slipped on the sensuous hose being careful not to snag them. My legs looked stunning, the little rhinestones made the pattern on the outside of each of my calves, the cuban heels tapered into the back-seam. I adjusted the seams to run perfectly centred up the backs of my legs. As I smoothed the hose little sparks of delight flew up my legs and I felt myself begin to stiffen. Before I could become further aroused I pushed my penis between my legs and held it there with the tight nylon gusset. These hose must be really expensive I mused.

Next I slid the white satin panties up my legs sending more little darts of pleasure into my body as they rubbed on the nylons. I stood and pulled the panties into place around my bottom and crotch. They were pure white, sleek and discretely laced around the waistband and leg openings. The full cut white panties stood out dramatically against the black nylon pantyhose; the seat of the full-cut panties encased the globes of my buttocks perfectly and the front panel was tight against my crotch with just my little package spoiling the effect.

I removed the breastforms from the makeup case and stood before the mirror and put them in place. I had applied a liberal amount of artist’s gum to my chest and the back of the breastforms as directed by the label on the tube I had found in the case. The directions on the gum promised to hold them in place ‘for hours on end’; they certainly felt secure. I just hoped the fucking things weren’t glued there permanently.

I put on the white satin bra next. Still a novice, this proved to be the hardest garment to get into. In the end I clipped the catches at the back of the bra together and pulled it on like you would a T-shirt, arms in first then pulled the back strap over my head. I wrestled the garment into position and smoothed out the sleek satin cups over my false breasts and untangled the straps over my shoulders and around my back. It was a lovely fit, perfectly matching the satin panties with a lace trim along the top of the breastcups with a single pale pink satin rose nestled between them.

The last item of lingerie in the packages was a full slip of the sheerest translucent white nylon. I slipped the item over my head and pulled it down so that the bodice fit snugly against my torso; the slip flared at the waist and finished mid thigh. The hem was trimmed with lace matching my bra and panties. The gossamer thin garment felt luxurious and when the material stroked against my nyloned thighs little explosions of pleasure ran up my legs.

I stepped into the patent leather black high-heeled sandals, my painted toenails visible through the reinforced toes of my stockings, the pretty cuban heels accented by the ankle straps of the shoes. I bent down and fastened a silver anklet around my left ankle; the chain sparkling as the light reflected off it accentuating the miniature rhinestones on my sleek hosed calves.

I stood up and unzipped the suit-bag. Inside was a navy blue suit and sheer white nylon blouse. I slipped into the blouse, the cool feel of the nylon sleeves sliding up my arms, the light material whispering against the full slip as I buttoned the garment. I stepped into the skirt; it was snug at the waist and tight around my hips and bottom, the hem coming to just above my knees. I pulled on the wide lapelled jacket and my transformation was complete.

I looked in the mirror stepping back so I could see as much of my reflection as possible. I was no longer Mike, the weak willed accountant; I was Michele, a power dressed executive; a ‘fem fatale’ in a business suit. I sprayed liberal amounts of perfume on my neck, behind my ears and then as Carmel had showed me, under my skirt.

I was about to sit down when my cell door slammed open. ‘Iron Bar’ Steve stood there in the company of one of the guards.

"Oh fuck me Steve she’s fucking gorgeous; I’d love to shag her bent over the bunk dressed just like that!" the dimwitted guard exclaimed.

"Fuck off stupid, you couldn’t afford a fucking hand job off her, she’s out of your league," Steve responded.

‘How chivalrous,’ I thought to myself, ‘A brain-dead thug defending the honour of a crossdressed inmate prostitute to a corrupt prison guard!’ I couldn’t help but smile at the irony of the situation.

"Oh you won’t be smiling for long honey," laughed Steve, "Eddie’s special friend doesn’t like jokes from fag inmates one little bit."

"Who are you calling a fag Stevie? You couldn’t get enough of me last night could you?" I clipped sarcastically.

Steve raised his hand but I stood defiantly in the doorway of the cell. I knew that Steve dare not touch me at the moment as I was all prettied up for some special punter. It was good to actually feel a slight empowerment for once. I sashayed though the cell door deliberately taunting Steve but I paid the price as I passed him; he reached out and squeezed my pantied buttocks through my skirt.

"Don’t touch the merchandise Steve," I taunted again, turning my pretty face to his and pouting at him.

"Oh don’t worry Michele, I’m just here to escort you to your special date, but you will be well used merchandise when you return," he laughed.

I looked around the cellblock and noticed it was empty. All of the prisoners were at work of course, but I couldn’t see any guards either, other than the dimwit who had unlocked my cell and was now making his way back to the guard’s office at the end of the block.

"Oh don’t worry honey, you’re getting the red carpet treatment, no one is going to see where your going except for a select few in the know," Steve said, tapping the side of nose..

Steve led me through a series of doors and deserted corridors. I never saw another soul; the doors opened electronically when Steve swiped a keycard though each of the card reading devices fitted next to the door-locks. ‘Who the fuck is Eddie’s special friend?’ I thought, ‘He must have some clout to be able have a crossdressed prisoner led halfway through the jail without anyone seeing it happening.’ ‘And who the fuck gives prisoners like this maniac escorting me the keys to the jail; this was just fucking insane!’

We finally arrived at a set of fire stairs, the door to which Steve opened with a swipe of his card. He led me up three flights of stairs, me tottering on the high-heels I was still unaccustomed to wearing. He opened the door at the top of the last flight and held me back as he scanned the corridor for a few seconds.

"Ok, quickly now," he said grabbing my wrist and pulling me into the corridor behind him.

"This is his private entrance; I’ll pick you up from here in hour. Behave ok!" Steve whispered in my ear, kissed me gently on the earlobe, and pushed me through an unlocked wood paneled door and slammed it shut behind me.

I half fell through the door and as I glanced up I could just make out the name embossed on the door; in faded gold leaf lettering it said WARDEN.

Warden Stone was a large man and as I fell though the door he caught me in his strong arms.

"You must be Michele," he smiled, gazing directly into my eyes.

"Here take a seat," he insisted leading me to a large leather divan set against one wall of the large office.

I was mesmerised; I knew that things were obviously way out of the ordinary in this fucked up jail. What with Eddie running every legal and illegal activity he could, including a lucrative brothel staffed by crossdressed feminised prisoners, corrupt guards and inmates running around with the keys to the doors; it was just farcical. The lunatics were literally running the asylum. But this! The Governor admitting a crossdressed prostitute, delivered by a messenger from the hardest criminal in the jail, into his private office; this was beyond comprehension!

But then again; in some fucked up way it made sense. How could Eddie possibly get away with what he did in here without the blessing of the Governor. In fact it made even more sense as I quickly caught on to the enormity of the situation; this was where Eddie’s largest payments went to; the Warden, they were obviously partners. The Warden ran the jail but Eddie ran everything inside the jail and the Governor got his cut; including the fringe benefit of access to Eddie’s working girls whenever he wanted. How else could all this be explained?

At the same instant another lightning bolt struck me; I was now with most powerful man in Chelmsford prison, if anyone could get me a transfer out of here it was him! I decided right then and there that I was going to be very nice to the Governor; no matter how disgusting his needs were, I was going to tend to every one of them willingly. After all, this could be my only shot at getting out of this nightmare. ‘So Mr Stone,’ I thought to myself ‘You’re about to have the wickedest hour you ever spent with one of Eddie’s whores!’ I mustered my resolve and made my move.

"Why thank you Warden Stone," I offered him by biggest smile and sat down, crossing my legs in a ladylike fashion so that the hem of my skirt rode up to mid thigh.

I noticed his eyes open wide and heard a sharp intake of breath as he heard the soft rasp of my nylons rubbing together and stared at my thighs encased in their gauzy nylon sheaths.

"Stanley please," he smiled back.

"And you are Michele I’m told," he went on.

"Well Michele let me paint a picture for you; I’m sure you are not naïve and understand why you are here. But there is no need for this to be unpleasant for you; I assure you that I can behave like a gentleman, and this scant hour we have together can be a welcome break for you from the filth and depravity you experience very day in my prison."

"So Michele, shall we spend a nice relaxing hour together?" he asked expectantly.

"Why Warden, I mean Stanley; if you are the gentlemen you already appear to be I’m sure I can behave like the lady you want me to be. Perhaps we can even accommodate each other in other ways if you would like to discuss a proposal I have for you?" I responded maintaining my painted smile.

Warden Stone’s face clouded over at my proposal; I had gone too far too early; I went into damage control.

"But of course that’s for later, please sit with me," I patted the leather couch next to me and batted my lashes like a good little coquette.

Stanley smiled again and managed to drag his gaze away from my legs to my eyes.

"Lovely, but please, allow me to get you a drink; scotch?"

"Please," I smiled back and he turned to an expensive looking oak cabinet to pour the drinks.

‘I might as well make the most of this,’ I though to myself as I glanced around the Warden’s impressive office. As one would expect it held all the trappings of power; a large desk, chunky furniture, the wall adorned with certificates, trophies and pictures of the Warden with other powerful men. On his desk I noticed a picture of the Warden and his family. His wife appeared mousy and his daughter was a skinny teenager with dank hair; they were smiling painfully for a picture obviously posed to project family harmony. I wondered what his mousy wife would think if she knew that Stanley’s peccadilloes ran to intimate encounters with crossdressed prison inmates?

Stanley returned to the large sofa, stopping off to turn out the overhead lights and check that the door to his outer office was locked and the shades lowered. He set the drinks down on side table and adjusted the one remaining lamp to a diffused glow. ‘Very cosy,’ I thought to myself; ‘I bet his receptionist is on an errand for an hour or so.’ I wondered how often he did this?

The Warden handed me my drink and indicated the vacant place beside me on the sofa,

"May I Michele?" he asked smiling.

"Of course Stanley," I smiled, again patting the seat beside me.

Stanley sat down heavily beside me and the cushion gave way under his weight so that I leant in towards him slightly, the golden liquid and my red fingernails glimmered in the diffused lamplight as I raised my glass to him.

"Cheers," I whispered and drank heavily from my glass.

"Cheers," he responded, downing the spirit in one huge gulp.

Stanley had to be over a hundred and thirty kilos and close to two meters tall; well proportioned but large; I noticed the beginnings of a paunch hanging over his belt as his suit jacket opened. ‘Ok this is it,’ I decided; ‘lets get this façade over with!’

I reached out and took his empty glass from him and placed it on the side table beside mine, a crescent of lipstick decorated the rim of my glass.

I turned to face the Warden and reached out to him, gently taking his head in my hands, I pulled his face towards mine seductively opening my lips slightly. Stanley groaned and pressed his lips lightly against mine. He kissed me softly, with his mouth closed; then he reached out and put his strong arms around me and eased me against him as he smothered my face with feather soft kisses. He kissed me all over my face; my lips, my cheeks, my forehead, and placed little butterfly kisses on my lightly closed eyelids.

"You are so beautiful," he whispered in my ear, gently nuzzling my earlobe.

My hands were now on his powerful shoulders and we embraced each other for a few minutes; softly kissing each other, I felt the heat slowly growing in him as he became aroused.

I felt his hand slide down my body and come to rest on my knee; he softly massaged my leg, slowly working his hand higher, lightly stroking the inside of my stockinged thigh. His breath was becoming heavy now but he made no attempt to force himself on me; his mouth remained closed as he tenderly rained down soft kisses on my mouth and face.

I reached out with one hand and placed it on his thigh feeling the hard muscle through the material of his trousers; the back of my hand brushed briefly against his tumescent member; he gasped.

"Oh Michele; you naughty girl!" he whispered, his hand sliding under my skirt came into contact with my slip.

The Warden wrapped his hand in the silken material and began to slowly glide the slip up and down my thigh. The feeling of the delicate fabric rubbing on my pantyhose was exquisite; my member began to awaken in the silken gusset of my hose; my tight white panties holding it in place as it slowly thickened and elongated.

I moved my hand across the bulge growing in the Warden’s trousers and found the zipper on his fly. He removed his hand from under my skirt and gently moved my hand away.

"No Michele, I want to taste all of your sweet treasures before we consummate our little interlude," he said and took hold of my upper arms in a tight grip.

‘Quite the wordsmith,’ I though to myself; ‘I wonder what sweet treasures he intends to enjoy?’

Stanley kissed me fully on the lips, pressing his torso hard against me, slowly sliding his tongue into my mouth; I tasted my own lipstick on his tongue as he gently explored my mouth. Then he pulled his face away from mine and eased me back against the padded armrest of the divan. I guessed that now he would want more than just kisses and caresses and as he adjusted his position on the sofa I made to remove my suit jacket.

"Oh please no Michele; I want you dressed just as you are. I love a woman who can pull off the whole power-dress performance thing and still look feminine and sexy."

"Do you like the lingerie? I had Eddie acquire it for you just for this occasion; and those nylons, God, I could eat you up in those. In fact I think I just might," he chuckled.

I relaxed back against the padded armrest and Stanley bent down and lifted my legs so that I was lying lengthways on the divan. I was lying with my back supported by the padded armrest and my legs across Stanley’s lap.

"That’s better," he smiled and began to stroke my legs with his hands.

"Oh that feels so sensuous, and I just love those little rhinestones sprinkled on your stockings," he said.

He bent his head and raised one of my legs to his mouth and commenced planting sweet little kisses all up and down my calf. He moved his lips slowly up and down my lower limb and then licked the back seam of my stocking all the way down to my high-heeled sandal. He kissed my feet, and pushed his tongue into the darker reinforced extremity of my hose and sucked on my painted toes through my open toe sandals. I must say it felt quite erotic.

Stanley used his free hand to stroke my other leg sliding his fingers far up under my skirt, stroking up and down my leg slowly and sensuously.

"Mmmmm let me see," he groaned and lifted his face from my feet.

He opened my legs slightly and raised my skirt up around my waist. He gazed upon me lying there with my stockinged legs in his lap with the hem of my slip coming halfway down my thighs, the pure white nylon slip in contrast with the dark hosiery.

"Lovely," he said, and began to kiss me up and down my legs again.

This time he buried his head under my slip and continued up my legs right to the top of my thighs. He kissed the front panel of my satin panties whilst stroking my legs. After a minute or so of placing soft kisses on my panties and thighs he made his way back down my legs and began to suck on my nylon sheathed toes again. His hands were now sliding the soft material of my slip up and down my thighs creating wonderful sensations through my body. My member was stiffening further and was becoming uncomfortable being held in place under my crotch by my pantyhose and tight panties.

Stanley was now licking my shiny black patent leather sandals, holding both my feet in place by the spikes of my heels. As he worshipped my feet and gazed up my legs, his eyes glazed over with lust; then he started sucking on the spiky high-heels, taking them into his mouth and lovingly caressing them with his tongue; first one then the other; as if fellating my heels.

He was panting and groaning as he worshipped my legs and feet. Then he moved one hand down to his fly and pulled on the zipper. His hand disappeared inside and rummaged around eventually freeing his erection; it protruded stiffly from his trousers, red, angry and engorged.

Stanley lifted my feet and re-positioned them one on either side of his hard cock and slowly started to fuck my feet. I realised what he was doing and assisted him. I slowly started to masturbate him with my feet, slowly lifting them up and down, letting my soft stocking foot caress the head of his penis and then the patent leather of my shoes.

Stanley threw his head back against the cushioned divan and let me foot fuck him. He renewed his carnal attack on my legs as I wanked him with my feet. I trapped his member my feet and stroked hard. He moaned and writhed in ecstasy.

Then he looked at me again and gently moved my feet out of his crotch. He stood up and re-positioned himself on the divan so that he was kneeling between my spread legs. With trepidation I thought, ‘Here he goes; he’s going to fuck me.’ But he didn’t. Stanley closed my legs and lifted my feet up to his mouth and began to worship them with his lips and tongue again. I was lying down full length on the divan now with just my head pillowed on the armrest, my skirt and slip rucked up around my waist with my legs lifted up whilst Stanley took oral pleasure on my feet and calves. Now I knew what ‘sweet treasures’ the Warden wanted to taste; he was a foot fetish. ‘Well at least I might leave here without having to gratify him in some other disgusting way,’ I thought to myself.

Stanley was now in a frenzy, lapping and sucking at my shoes, toes, and feet; he was panting, his face red and sweating. Stanley actually looked quite pathetic dressed in his full suit with just his stiff penis poking out his trousers as he paid homage to my peds. He stopped briefly and quickly fumbled at his waist, undoing his belt and pushing his pants down around his thighs. Then he gripped my ankles, lowered my legs and pushed my feet together. He pulled my feet between his legs so that his cock lay in the silken valley created by my calves. Then he started to fuck my legs.

He rubbed against me faster and faster and I could feel the friction of his hard cock against my nylons. Stanley groaned and whimpered. His gaze alternated between my face and my pantied crotch as he pushed his cock against me harder and faster.

I decided that I would assist him with his fantasy and placed two slender, red-nailed fingers on the gusset of my pure white satin panties and began to stroke. Stanley reacted immediately.

"Oh yes Michele! You naughty, naughty girl!"

"You are such a pretty girl, but such a naughty girl," he chanted.

"Oh Michele, you naughty nyloned princess I’m going to come; I’m going to come all over your pretty toes and feet; would you like that?" he begged.

"Yes Stanley please; please come all over me!" I role-played for him as he approached his climax.

He shifted his grip to my ankles again and pulled my feet up to his quivering member. I knew exactly what he wanted and began to masturbate him hard and fast between my feet; pushing back and forth with my legs so that my high-heels and stockinged feet ran up and down the length of his shaft. At the same time I furiously rubbed the front of my panties; a parody of a woman pleasuring herself.

"Come for me Stanley; come on honey, come for Michele baby," I cooed.

Stanley’s face screwed up and went bright red as a shattering orgasm washed over him. Ropes of creamy semen jetted from his penis splashing up my legs. Spatters of his spend formed sticky white pools on my calves and feet; they glistened in stark contrast on my black stockings. My diaphanous black hose became darker still in the places where Stanley’s semen soaked into the nylon.

A silvery thread of Stanley’s ejaculate hung down from the heel of one my shoes forming a sticky necklace between my foot and his deflating penis.

"Oh Michele, that was wonderful," Stanley gasped and collapsed on top of me.

His weight nearly knocked the breath out of me as he started to cover me my face with soft kisses again. I pushed lightly against him until he took the hint and rolled off me so we were lying side by side. Stanley pulled me close against him, one arm over my body caressing my buttocks, slowly stroking the sheer nylon slip against my panties. His kisses grew harder and his tongue now invaded my mouth; I could hardly breath. I managed to pull my face away from his.

"I’m glad you liked that Stanley; was that how you wanted to take me?" I whispered in his ear.

"Oh yes Michele, but that was just an entrée sweetheart; I recover very quickly," he whispered back.

"Perhaps a drink Stanley, before we play some more?" I asked.

I was getting confident now; the Warden was obviously a submissive, I had read that powerful men often liked to take on a submissive role during sex play. I decided to test my theory.

"Come on Stanley, pour me another scotch and we can discuss a proposal I have for you. If you are a good boy and treat me nice I might let you have some more," I teased.

I was not prepared for what happened next; I had hopelessly misjudged the situation.

The Warden used his powerful build to roll me onto my back and pull himself up so he straddled my waist. One huge hand came across and swiped me on the side of my face, stinging and numbing me.

"Oh I don’t think you realise the situation here bitch! I’m the fucking Warden of this jail and you’re just another slag who Eddie provided for me to use as I see fit."

"Don’t try and offer me proposals! I make the fucking proposals here!" he screamed at me.

"Now here’s a fucking proposal; lift your fucking trollop arse up off my lounge," he yelled.

Warden Stone stood up and dragged me off the divan and shook me like a rag doll. I was terrified; the man had turned from being a gentleman to a demon in the space of seconds.

"Here’s another fucking proposal," he barked and shoved me hard towards his desk.

I tottered on my heels and reeled over towards the desk; one of my shoes flew off and my stockinged foot slid on the polished floor. I reached out trying to grab the desk for support but I collapsed on the floor beside the desk, legs akimbo.

"And here’s my final proposal," the Warden bellowed and moved in, pulling me up off the floor and bending me over the huge oak desk.

One bear-like hand grabbed my skirt and tore it from my body; the side seam splitting with a loud rip. The Warden pushed me down harder on the desk, he put one hand on the back of my neck and mashed my painted face onto the hard surface of the desk. With his free hand he pulled my slip up and over my back and I realised how exposed I was in this position. I was bent over the desk with my skirt ripped off, my slip hiked up, tottering on one heel, my satin pantied buttocks raised and exposed.

Warden Stone let go of my neck briefly but it was no relief; I was horrified by what he did next. He put both hands on my hips and yanked my panties and pantyhose down in one swift movement. They tangled in a bunch at the top of my thighs.

"No! Please, Stanley don’t do this," I whimpered.

"What you mean this, you cocksucking whore," he taunted and I felt him position himself behind me, his swollen penis probing at my buttocks.

"No! No! Please!" I begged.

"Well what do you think of my proposal Michele?" he grunted and pushed forward with all his weight.

"Ohhhhhhh god no!" I moaned as his member slid all the way up inside me.

I felt as though I had been split open. It was so tight and he was in me so deep that I could feel his groin hard against my bottom. Then he raped me. He just fucked me like a whore. Bent over the desk I could offer no resistance as Warden Stone commenced thrusting in and out of me. I don’t know how long he ploughed himself into me; at least ten minutes; he obviously had plenty of staying power having just recovered from an orgasm only minutes ago.

He grunted and groaned, calling me filthy names and slapping my buttocks as he fucked me hard and fast. His cock pistoned in and out of me and his groin slammed against my buttocks. I forced myself to relax my sphincter but the pain was still excruciating. Eventually the lubrication from his pre-seminal fluid eased some of the pain as his invading member continued to rape me.

Eventually he bellowed, grunted and puffed and suddenly I felt the hot ooze of semen inside me. The Warden wasted no time and pulled himself out of me immediately. He yanked my panties and pantyhose up over my buttocks and I felt him wipe his penis clean on my buttock; his warm spend left a wet patch on the cheek of my bottom. I remained bent over the desk, silent and humiliated, feeling vile and debased as the Warden pulled up his pants and shoved the tails of his shirt into the waistband of his trousers.

There was a gentle rapping at the wood paneled door through which I had entered the office only an hour ago. The Warden grabbed my arm in a vice-like grip and dragged me across the office. He opened the door and threw me outside like a piece of garbage; I tripped and fell to my knees on the hard polished floor tearing my beautiful pantyhose. I looked up to see ‘Iron-bar’ Steve smirking down at me. The Warden briefly disappeared back inside his office, then returned to the doorway and threw my shoe and my ripped skirt at me.

"Tell Eddie I’ve finished with this for now. She’s one of his better whores, but she has too much of a mouth on her," Warden Stone barked at Steve and slammed the door shut.

 

 

 

 

The Predator walked over to one of the stalls and grabbed a handful of toilet paper from the dispenser and then strolled over to the ottoman.  He looked at the transvestite whore lying there, her lovely blonde bob and white nylon blouse were covered in the biker’s semen, her stockinged thighs spread wide crudely displaying her red nylon panties soaked in her own emission and that of the biker who had fucked her. With her leather mini bunched around her waist and her red high heels wide apart resting on the ottoman, she looked fucked and contented.  He handed her the bunched up toilet paper, “Clean yourself up,” he growled.

The Predator watched the transvestite as she sat up and adjusted her underwear; she stood up and moved over to the mirror and used the paper and some tap water to clean most of the semen off her hair and clothing; she went into one of stalls for a few minutes and then he heard a flush.  He was thinking to himself that he had very much underestimated this transvestite bitch; she had handled all of the circumstances that he had put her in to and was gaining the upper hand with each situation. A plan formulated in the back of his mind.  Would she go for it?  There was only one way to find out.

The Predator held his hand out to the dishevelled woman and when she took it he led her back to the ottoman and indicated for her to sit.  She sat down and he sat beside her and looked at her face; still pretty despite the messy makeup and unkempt hair.  He slid a hand over her stockinged thigh and looked her in the eyes, “Michele is it?  Well Michele, we are leaving here now and I’m taking you home. On the way we are going to have a chat and I’m going to make you an offer that I want you to consider; either way, given what has happened tonight I don’t think you want to go the authorities and tell them what happened; otherwise your friends and family would have to know about your double life.  Just think my proposition over let me know one way or the other.” 

The Predator kissed her gently on the lips and helped her to her feet; he handed her her purse and took her by the arm and escorted her out of the ladies room into the dark bar.  He walked Michele past the booth where Red still sat nursing a drink, “Bye Red,” he muttered as they walked past.  As they made their way to the door of the bar the bikers standing around the pool table all applauded and yelled out cat calls.  The Predator led her out into the cool night air and over to his car; he opened the door for her and as she went to get in the car he pulled her to him and kissed her.  She responded and wrapped her arms around him holding him tight.  He gently disengaged himself and helped her into the car and they drove away into the night.

Three weeks later……………………………..

The Predator looked at the middle aged woman spread eagled on the huge four poster bed.  She was tied hand and foot to the bed by the stockings he had taken from her dresser.  She was just to his taste; her heavily made up face was framed by her permed red hair.  He studied her for a minute.  Her pale skin was sprinkled with freckles just visible under the layers of foundation, face powder and rouge.  Her eyes were pale blue framed by her dark mascara and eyeliner and her bright red lipsticked lips quivered in fear.

The Predator cast his eyes along her body.  She wore a red satin evening gown; now slit open from her breasts to the hem at the bottom of the dress.  The gown had been pulled open exposing the black nylon full slip that she wore underneath; this garment too had been slit from top to hem exposing her red satin half-cup brassiere and matching directoire knickers.  Just above the waistband of her knickers the lace top of a black suspender belt was visible; the garter straps peeking out from the legs of her knickers were attached to high sheen taupe stockings; the stocking tops were dark brown and pulled taught where the suspenders were attached by their glistening silver clips.  Her shoes were red suede high heeled pumps.

The Predator thought she looked like a sacrifice on an alter; the bizarre image was like some gothic tale; with her red satin gown and black full slip spread open beside her; he imagined she looked like a vampire queen, spread eagled and awaiting the stake.

The Predator moved over to the side of the bed and gently, light as a feather, ran the point of the silver steel blade of his knife along her body; starting from between her breasts, along the curve of her belly and down to her sex.  As she moaned he savoured her fear.  The Predator placed his other hand over the crotch of her satin directoire knickers and pushed the silky material into her cleft, “Like I said, honey; don’t cry out and no one gets hurt,” he whispered.

Michele was dressed in a full-body black leather corset; her new breastforms filled the cups so that the leather pulled taught across her breasts.  She wore black satin full cut panties, the crotch just visible below the bottom of the corset.  Suspender straps ran from the corset underneath her panties and were attached to diaphanous black nylons with dark reinforced cuban heels and stocking-tops; tiny diamantes decorated the satiny stocking-tops and the cuban heels; a black seam ran up the back of the stockings.   These were the same stockings the Predator had made her wear to the biker bar three weeks ago; she knew he loved them.  Her feet were shod in black patent leather high heeled sandals; her painted red toenails just visible through the reinforced toes of her nylons.

Michele had carefully matched her makeup to her attire; which reflected her mood this evening.  Earlier in the evening she had sat in front of her makeup mirror and contemplated how she wanted to look.    The theme was dark; black actually, and she was so excited that she had to be extra careful when applying her makeup.  She applied two thick but even coats of pale foundation to her face and neck.  Then she painted jet black kohl to her upper and lower eyelids, starting in the very corner of her each eye, working outwards applying three thick coats so that her eyes looked like an Egyptian goddess.  She carefully brushed dark purple eyeshadow onto her eyelids applying several coats to get the desired effect; she smudged the dark makeup with a finger feathering it out and up so that it faded just below her eyebrows and extended right to the outer edges of her eyes.

Michele next applied a dusting of red rouge to her cheeks; running it diagonally across her cheek-line and feathering it up to almost meet with her eyeshadow.  She applied a coat of pale face powder next, setting the foundation and rouge.  Then she carefully removed the plump black false eyelashes from their little plastic container. She fiddled around until they were set perfectly and indistinguishable from her own upper eyelashes.  Her lashes were now long, plump and dark.  She heavily mascared her lower eyelashes and then reached for her lipstick.  She applied blood red lipstick to her lips using the base coat applicator and then set her lipstick with the clear top coat.  As she did this she was pleased to see her bright red nail polish matched the lipstick perfectly.

Michele applied another coat of pale face powder and reached for the wig she had selected earlier.  The wig was a jet-black short bob; she adjusted it in place and fiddled with the fringe so that it was in a perfectly straight line across her forehead coming down to just over her eyebrows.  She gave it a final combing; the sides of her hair extended along her cheeks and angled up; the hair at the back of the wig ran high across the back of her neck displaying her delicate white skin.  To emphasise her neck she clipped on a diamante set silver necklace which had three strings of diamantes drops connected to the main necklace hanging down to the top of her breasts.  She clipped on matching earrings which dropped almost to her shoulders.

Michele wore a huge red ruby ring set in silver on the ring finger of her right hand and a huge yellow diamond with matching setting on her left.  On all of her other fingers she wore silver rings of various designs.  Around her slim, black-nylon clad ankles she wore silver anklets.  She stood up and slinked over to her full-length mirror and looked at herself, her eyes wondering up and down, adjusting little things here and there. She uttered one word; “Perfect.”  Then she sprayed herself liberally with her favourite perfume, ‘Poison’, pulled on a trench coat and went down stairs to wait for the Predator who would soon be here to take her out on her first adventure with him.

Michele now stood on the other side of the huge four poster bed and looked down at her captive.  He was tied to the bed in the same fashion as his wife; lashed to the frame of the bed by nylon stockings.  He was wearing a black dinner suit but the jacket had been discarded before the man was restrained on the bed.  His crisp white formal shirt was unbuttoned; the tails untucked from his trousers and the shirt wide open displaying his dark hairy chest.  His black dress trousers had been pulled down to his ankles so that only his white satin boxer shorts covered his manhood.  He was about fifty but still trim and handsome; his deep blue eyes were set off by his black curly hair.  His face was chiselled and his cheeks well defined.

Michele ran a sharp red fingernail down his body, starting at his throat and ending just below his belly button where the waistband of his boxer shorts lay tight across his abdomen.  The man groaned; “You won’t get away with this you bitch!” Michele responded by gently fondling his package through the satin shorts and whispering, “Shush honey; you heard what my partner said; don’t cry out and no one gets hurt!”  She was pleased to feel the man was adequately endowed and could hardly wait for the fun to begin.  Her own genitals ware restrained by a gaff and as her excitement mounted it was becoming decidedly uncomfortable.

The Predator was naked; his rampant penis stuck out in front of him, tumescent, pink and swollen, a long rope of clear pre-seminal fluid hung from the eye of his glans.  He climbed onto the bed and straddled the woman who was lashed there spread eagled.  He rubbed his cock over her satin encased tits and groaned as the silky material stimulated the nerves in his hard member.  The woman squirmed beneath him but all her movements did was to excite him further.  He grasped the bed head and lifted himself up and forward until his cock was over the woman’s face and then lowered his crotch until his erect penis rested on her cheek.  He rubbed his cock all over her face and was delighted when a single tear escaped her eye and ran down her cheek.

Michele watched the Predator climb on the bed and knew that the fun was about to start.  She saw the look of anger in the eyes of the woman’s husband.  She sat on the bed beside the man and lowered her face to his and pressed her mouth down on his thick sensuous lips.  He tried to move his head away and she gripped his testicles through his shorts and squeezed.  He got the message and lay still; he knew there was nothing he could do.  The Predator had done all the talking when they had overpowered the couple as they had just finished dressing to go out for the evening.  The threats the Predator had made, particularly against the woman, had forced the couple to capitulate.  They knew their best option was to be compliant and then hope that the man and woman who had broken into their house would leave them unharmed once they had had their way with them.

Michele probed her tongue inside the man’s lips and forced it into his mouth; she swirled it around and savoured his sweet fresh breath.  She eased her grip on his testes and snaked her hand inside his shorts and took his thick flaccid member in her hand.  She kissed him harder and slowly started to stroke his penis.  She heard him gasp and then she felt his cock begin to harden in her fingers.  Michele smiled even as she continued to kiss him; she thought to herself that men were just so easy to control.

The Predator looked across at Michele kissing the helpless man on the bed and smiled when he saw her hand disappear inside his shorts.  He sniggered when he saw that she was goading an erection out of the man.  He moved his body down onto the woman so that he was lying on top of her, his face hovering over hers, “Look,” he said, “your husband can’t help himself; he’s enjoying it!”  The woman strained and turned her head and saw the attractive black clad woman kissing her husband; she looked down and was horrified to see the bitch had her hand inside her husband’s shorts and was stroking him.  She was more horrified when she saw the woman ease her husband’s erect member out of the fly of his shorts and stroke his hard cock, her bright red fingernails snaking up and down his tumescent member.

Michele was now stroking the hard cock in her left hand; she slid her fingers up and down the spongy mass of sinew and veins and felt it thicken and engorge.  She kissed the man passionately and he groaned and started to respond to her kisses, the tip of his tongue exploring hers.  Michele pressed her body against his and slid one sleek nyloned leg over his and began to rub her black nyloned leg up and down; he writhed and began to push up with his abdomen so that his cock was actually fucking her hands.  She loosened her fingers so that his cock was held in a feather like grasp; barely touching the skin of his penis.  She felt him buck and bounce as he tried to get more friction on his manhood.  Michele’s smile widened.

The Predator watched as the woman looked on horrified at the reaction of her husband to the ministrations of the whore who was rubbing her stockinged thigh along her husband’s leg.  She saw him attempting to fuck the trollop’s hand and heard his heavy breathing in between the long wet kisses.  More tears escaped her.  The Predator lowered his face to the woman and began to spray soft kisses on her pale skin; he gently lapped up her tears with his lips.  He ran his hand down her belly and tenderly cupped her sex through her directoire knickers and began to work the soft gossamer material of the knickers into her cleft.  The woman stiffened beneath him and then began to struggle. He forced his lips down on hers and pushed a finger into the folds of her labia and began to softly stroke her clitoris.

Michele looked across at the Predator as he began to stimulate the woman’s sex and force his mouth over hers.  She lifted her face away from the woman’s husband and whispered in his ear, “Look.”  The man turned his head to the side and was greeted by the sight of his wife struggling under the monster who had invaded their house.  To his disgust he saw his wife stop struggling and begin to move her hips in a circular motion in time with the man’s hand which was buried in his wife’s knickers.  While his attention was elsewhere Michele turned around on the bed and lowered her face the husband’s erect shaft and slurped the stiff member into her mouth, smoothing her lips all the way along the shaft until her lips were at the base of his cock; she lashed her tongue around the bulbous glans.  The man moaned and pushed his hips up off the bed and began to fuck her mouth as she moved up and down on his rampant cock.

The Predator looked across at Michele and saw her fellating the woman’s husband.  The man was face fucking Michele and he had look of extreme pleasure on his face.  The woman beneath him was now squirming and bucking as he manipulated her clitty through her knickers; he took his hand away and heard her mumble her disappointment into his mouth as he kissed her.  He didn’t disappoint her for long; he adjusted his position on top of her so that his hard cock was buried in the fissure of her open labia and began to dry fuck her through her satin knickers.  She bucked up against him and he moaned at the intense sensations shooting through his cock caused by the sleek material of her knickers rubbing against his erection.

Michele was sucking the husband’s cock in a steady rhythm, grasping the sinewy cock between her lips and whisking her tongue along and over his glans.  She could taste his secretions and his humping motion lifted his arse clear of the bed as he bucked under her.  She glanced across to see the Predator slide his cock between the wife’s legs and knew that soon this little drama would come to its climax.  Michele eased her face away for the man and this time she actually heard him grumble in disapproval.  She eased a hand inside her panties and untied the gaff so that her aching member could be free and then she lifted herself up over the man so that her stockinged thighs straddled his.  Michele raised her arse up and eased the gusset of her black nylon panties to one side and lowered herself slowly so that the tip of the man’s cock nestled up against her sphincter.  Michele lowered herself and gasped at exactly the same time as the man when his thick bulbous glans slid inside her.

The Predator saw Michele mount the husband and position his cock underneath her; he pushed the woman’s face to the right so she could see what her husband was doing.  The woman gasped, and as she did the Predator quickly repositioned his cock under leg of the woman’s directoire knickers and pushed his hard cock into her tight slick cunt.  The woman bucked and rolled beneath him and he hung on to her and enjoyed the ride.  He didn’t know if she was trying to buck him off or was trying to fuck him and he didn’t care; her firm vaginal walls were stretched around his rampant penis and all he could feel was the intense pleasure shooting out from his groin.  The woman beneath him began to set a measured tempo with her thrusts and it was obvious now that she was enjoying what she was getting; forced or not.  The Predator adjusted his position so that the base of his cock pushed against the woman’s clitoris and his balls rubbed against her gossamer smooth directoire knickers.  He started to fuck her hard and fast feeling his orgasm building.

Michele eased herself down further so that the man’s cock slid slowly further inside her.  She had lubricated her back passage in the bathroom before she had joined the Predator at the bedside and now she was glad she had.  The cock filled her anus and she had to take it easy and ride with the man beneath her to stop him lunging up and stabbing her arse with his cock.  She took control and eventually she was filled up with hot throbbing cock.  She sat down hard on the man to stop him from fucking her; she just sat there and enjoyed the feel of hot cock filling her arse.  Michele stated to gyrate as she clenched and unclenched her internal muscles to stimulate the cock buried inside her.  Then she started to slowly ease herself up and down on the rampant member, eventually loosening up enough so that she could increase the tempo.  The man beneath her sensed this and matched her with his thrusts; as she lowered herself down, he thrust up; the head of his cock pressed against her postrate and she felt her own orgasm build.  Michele bucked faster up and down on the cock and felt it slide in and out of her and stimulate the hundreds of nerves along the walls of her arse.  She was close to coming.

The Predator fucked the housewife with long hard strokes and lowered his face to hers and was greeted by sloppy wet kisses as the woman bucked beneath him.  Her cunt was spasming around his cock and he sensed she was about to come; he thrust faster and harder and was rewarded with her hot juices flowing around his hard cock.  He crushed his lips against hers and plunged his tongue into her mouth; he ground his groin against hers and she pushed back hard against him and her cunt convulsed as she orgasmed.  The Predator’s cock spasmed and twitched as it shot load after load of hot semen deep into the woman.  The housewife pushed back against him and shuddered as her orgasm racked her; she gasped around his tongue but continued to mash her lips against his, there tongues intertwined and teeth crashing together so intense was their climax.

Michele pushed down hard on the cock buried deep in her arse and felt it convulse.  The man’s member shuddered deep inside her and as it spasmed she felt jets of hot fluid fill her back passage.  His knob was pushed hard against her postrate and she felt her release.  Her issue shot from her semi-hard cock and filled the front of her panties.  Michele slammed her arse up and down on the rock hard cock that was spewing semen deep inside her.  She screamed and moaned and shook her head; the sensation was so exquisite.  Eventually her climax subsided and she came to rest straddling the man who lay there moaning beneath her, his cock pulsing in the last throes of his orgasm.  Michele lowered her head and gave the man a sloppy wet kiss and then leaned back and looked across at the Predator.

The Predator looked across at Michele as she raised herself from the hot wet kiss that she was giving the husband.  He saw her straighten up, the man’s cock still buried in her arse as she straddled him.  She smiled at him and leaned across; the Predator lifted himself from the housewife and Michele and the Predator kissed each other passionately across the bodies of their victims who lay lashed to their marital bed; the Predators cock was becoming flaccid inside the woman, and Michele’s back passage was contracting around the wilting cock buried inside her.  The wife looked across at her husband and whispered, “We can never tell anyone about this,” Her husband responded, “Never.”

Michele and the Predator smiled at each other.

The End

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Mike Stephens was eighteen years old; he lay in his bed slowly improving his erection as he listened to his mother clattering around the adjoining bedroom getting ready for work. He, his mother and his sister lived in a small house in a quiet suburb where he attended high school; his mother commuted to the city where she worked as a legal secretary six days a week. He had never known his father and his mother doted on him; he was a mommy's boy with few friends.

Mike reached under his bed and searched around until his fingers encountered the scrap of satin he was looking for. He pulled the piece of fabric from under his bed and bought it to his face. It was a pair of his mother's red satin panties; they were crusty with dried semen but they still held a scintilla of the aroma of his mother's sex; he put them to his face and scrambled around again under the bed until he found the other object he looking for. It was a pair of sheer-to-the-waist pantyhose; he sighed as he slid his cock inside one of the legs of the pantyhose and caressed the silky garment against his sensitive glans.

Suddenly his bedroom door flew open and Mike's twin sister stormed into the room. She stopped suddenly and stared at her brother lying naked on the bed with his mother's panties on his face and his penis encased in a pair of her pantyhose. She quickly reached behind her, slammed the door closed and locked it.

"For fuck sake Mike; how many times do I have to tell you to lock your fucking bedroom door when you're at it!" she laughed.

"If Mom caught you she'd have a blue fit!"

"Never mind about that Shelley; come and give me a hand with this will ya," Mike smiled back at his sister.

Michele Stephens, or Shelley to her friends, was dressed in her school uniform: pleated navy-blue shirt, the hem of which rested mid-thigh, white blouse, school tie, navy-blue blazer and black court shoes with a two-inch wedge heel. She wore expensive taupe sheer-to-the-waist pantyhose (the same brand Mike had draped over his cock) and white nylon bikini panties and matching bra. Her face was heavily made up with lashings of mascara, eyeliner and eyeshadow; ruby-red lipstick and rouged cheeks. Bangles and bracelets glittered at her wrists, matching earrings dangled from her earlobes. Her long manicured fingernails were painted the same ruby red as her lips.

She was forever getting into trouble at school for flaunting the school dress code but as she was a straight A-student, and behaved herself she was given latitude and treated leniently. It also helped that most of the male teachers secretly had the hots for her.

Michele Stephens was an expert prick-tease. She deliberately dressed the way she did to get the male teachers and boy students randy for her. She flashed her legs and knickers whenever she got the chance and during the summer months she opened her blouse to show off her budding titties.

She had no intention of letting any of the males who lusted after her getting any further than a grope and maybe a little foreplay; she fully intended to keep her virginity for the right man, who, provided he had the right prospects, she would marry and let him deflower her on their wedding night.

Not that she didn't like sex. About a year ago she had caught him masturbating into her panties in the bathroom. She had found dried semen stains on her underwear and pantyhose previously to this incident and she was intelligent enough to know that the culprit could only be her brother. She didn't ridicule or blackmail her brother; she made a deal with him instead.

She would give him her discarded nylons and panties for him to use for his masturbatory fantasies so long as they kept the secret to themselves. A few weeks later, after constant begging and whining she had finally agreed to masturbate her brother. She set the ground rules, which they both agreed to. There would be absolutely no penetration! She would not fellate him nor would he get to perform cunnilingus on her. There would be no kissing. In fact; they would never touch each other intimately flesh to flesh.

She would masturbate him only if he had a nylon stocking or a pair of panties covering his penis and he would masturbate her but only through the fabric of her underwear. This way they justified it to themselves that they were not committing incest; they were simply gratifying each other.

"You've only got a couple of minutes before you have to get up for school and Mom's in the next room," Shelley grinned mischievously at her brother.

Shelley was getting a little wet watching her brother stroke his long thick cock and she decided that she could risk spending a few minutes in his room before school. She sauntered over to his bed and took his tumescent penis in her hand and began to stoke it lightly with her fingers; she ran a red fingernail around the corona of his glans and giggled as his whole body shuddered. The stocking wrapped around Mike's phallus was wet with pre-seminal fluid where it stretched over his glans.

"Well come on bother; don't be one way about this," Shelley said and took her brother's hand and placed it under her skirt.

Mike slid his hand up his sister's pantyhosed thighs, relishing the feel of the sleek nylon on her coltish legs.

"Don't fucking ladder my nylons," she half-heartedly berated him shifting his hand from her thigh to her pubic mound.

She opened her stance so that her brother could get uninterrupted access to her pubis. Mike slid a finger along the crotch of Shelley's nylon panties; he could hear the faint hiss of her panties rubbing against the gusset of her pantyhose. Shelley always wore her panties over her pantyhose. He slid his finger inside her labia and felt the wetness of her sex. He expertly found her clitty and began to grind his finger against it through the fabric of her hose and knickers.

"OOOhhhhh!!!" Michele groaned and gripped her brother's penis and began to wank it fervently.

"OOOhhhhh!!! Yes Sis!!!!"

"Have we got time for a pony-ride?" he asked mischievously

Shelley's heavily-made up eyes glittered with lust.

"You naughty boy! Ok; but let's make it quick!" Shelly said, pulling the pre-cum stained stocking off her brother's penis.

Shelly crawled onto her brother's bed, hiked up her skirt, straddled Mike's naked body and lowered her panty encased crotch onto her brother's rampant penis. She began to rock back and forward, enveloping Mike's erection in the folds of her labia through the material of her panties and hose.

Shelly and Mike had invented the 'pony-ride' as a means of mutual masturbation that did not involve any penetration or flesh to flesh contact. It was their favourite pastime but quite dangerous as they could be caught more easily than if they just stroked each other.

Shelly mashed her pubis against her brother's hard cock until she felt his glans nestle against her clitty and then she began to quickly rock backwards and forwards to stimulate herself. Mike held his sister by the waist and pulled her body down on his rampant penis and groaned as he felt his orgasm wrack his body. He flooded his sister's panties with hot semen and Shelly could feel her panties and the gusset of her pantyhose soak up brother's juices as her own orgasm exploded.

Mike ran his hands along Shelly's smooth thighs as he pushed up with his groin forcing his cock inside the folds of his sister's sperm soaked cunt; only the fabric of her panties prevented him from penetrating her virgin pussy. Shelly wriggled her hips causing her brother's cock to stimulate her engorged clitty; she bought a hand up to her mouth and bit it to suppress a scream of pleasure. She didn't want her mother, in the adjoining bedroom, to hear them.

In the next room Mrs Michele Stephens, Michele and Mike's mother, was finishing getting dressed for work. She slid her feet into a pair of sheer-to-the-waist pantyhose and pulled them up her long, well-defined legs; she eased out the wrinkles and pulled them tight and snug over her full-cut satin panties. She pulled down the hem of her dark business suit skirt so that it rested just above her knees and straightened it. She slid her feet into a pair of black high-heel pumps and checked her makeup a final time in the vanity mirror.

Michele was in her mid forties and a little plump but still attractive. She wore her hair in a bob; she coloured it brunette and had put discreet crimson highlights through it. Like her daughter she wore very heavy makeup; black mascara and eyeliner, blue and pink eyeshadow, rouged cheeks and plum-red lipstick, one shade darker that her daughter's. Her nails were long and painted to match her lipstick and she wore silver drop earrings and a matching necklace and bracelets. She picked up another silver bracelet and clipped it around her ankle.

She pulled the suit jacket over the mauve silk blouse that she had chosen to wear to work today and looked at herself in the full-length mirror. She was aware that she had great legs and large breasts but she was a little dismayed at the slight paunch at her belly.

"Eat less; exercise more!" she berated herself and smiled.

She knew that she was still attractive; most of the single men at the office, and some of the married ones as well, had hit on her. Michele rejected their advances; she had not entered into a sexual relationship since her husband had left her fifteen years ago. With Her children would graduate this year and it wouldn’t be long before she was an 'empty-nester' and she could stop working all hours god sends to support her kids and then she could go looking for a good man.

She sighed; smoothed her skirt again, picked up her handbag and exited her bedroom. She ran into her daughter who was just coming out of Mike's bedroom.

"Is your brother up yet?" she smiled at her daughter.

"Oh yes; he's up Mom," Shelly giggled and turned on her heels and skipped down the corridor to her own room.

Michele shook her head, totally unaware of her daughter's double entendre; 'at least they get on together and don't fight' she thought to herself. Just as Shelly disappeared inside her room Michele noticed that the back of her daughter's uniform skirt was caught in the waistband of her bikini panties. She bet Mike would tease her about that later. She knocked softly on her son's bedroom door.

"Get up sleepyhead; time for school," she called through the closed door.

Mike finished wiping his cock with his mother's panties and got out of bed. He waited a few minutes for his erection to subside and then padded down the corridor to the bathroom. After he peed he rummaged around in the laundry basket but was disappointed to find that neither his mother nor his sister had left any soiled underwear in there for him.

In her bedroom Shelly changed out of her semen stained panties and pantyhose and pulled on a clean pair of taupe pantyhose and a pair of satin bikini panties over her hose. She noticed that the rear of her skirt had been caught in the waistband of her panties and she silently rebuked herself. She hoped her mother didn't suspect what she and her brother had been up to.

Fifteen minutes later mother, daughter and son were finishing a hurried breakfast and getting ready to leave the house. It was then that the three criminals burst into the house.

Dave and Leon were brothers and they had escaped from prison the previous evening along with their friend Sol. They had been evading the police all night and had finally hidden in the backyard of the suburban house that they had just broken into. Their plan was to get some food and hold up until dark and then steal money and a car from the occupants and get as far away as possible. The plan was amended as soon as the criminals laid their eyes on the two Micheles.

The escapees had been locked up for over three years and when they saw the mother and daughter they knew that they just had to have them whatever the consequences.

Dave and Leon stormed into the kitchen while Sol double-locked the doors to the house and pulled all the curtains closed. He then checked all of the rooms in the house to make sure that no one else was at home. Mother and daughter were about to scream in unison when Leon grabbed a carving knife off the counter and held it to Mike's throat.

"Anyone makes a noise and the boy gets it!" he hissed.

Michele and Shelly both stifled their screams and closed their mouths.

"Anyone else at home?" Leon asked.

All three captives silently shook their heads.

Leon dragged Mike into the darkened lounge and Dave pushed Michele and Shelly after them. Sol joined them and closed the lounge room door and switched on the lights. Sol had found a hank of clothesline whilst he had searched the house and he tied the teenage boy to a wooden chair. He's found Shelly's discarded pantyhose on the floor of her bedroom and he stuffed them into Mike's mouth to gag him.

Sol wasted no time and grabbed hold of Shelly and threw her on the couch. Her skirt hiked up exposing her white satin panties and the sheer gusset of her pantyhose.

Leon held the knife under Mike's chin.

"Anyone resists and the boy gets his throat cut," he threatened.

Sol dropped his pants and his huge cock bobbed in the air in front of Shelly's shocked face. Michele moaned.

"Please don't; not my daughter, please!" she begged.

"Shut the fuck up!" Dave said and pushed her over towards a large overstuffed armchair.

Shelly opened her mouth to scream and Sol grabbed her head and forced his cock into her open mouth.

"If you bite it; I'll cut your brother's cock off!" he growled.

In a reflex action Shelly closed her mouth over the long hard cock and Sol held her head still as he fucked her face. Shelly was surprised that the man's phallus didn't taste as disgusting as she though it would. It was spongy and the fluid that was leaking from the eye of the glans was actually a little sweet. If fellating this man would save her brother's life so be it! She began to suck on Sol's engorged penis and lick his glans with her tongue. She bought up a hand gently stroked his balls.

Sol let go of the teenage girl's head and let her suck on his cock. She was sitting in the chair with her legs spread wide giving him a great view up her skirt. He admired her legs and the mound of her pubis. He knew that he was going to come soon but it didn't matter; they had all day, and he was definitely going to get a piece of this girl's pussy before he left.

Dave threw Michele onto the armchair and pulled her into a kneeling position with her back to him; without any ceremony he pushed her forward so that she had to hold onto the back of the chair to maintain her balance. He kicked her legs open and lifted her skirt and positioned himself between her legs. Michele was sobbing but he payed no attention as he unzipped his fly and began to rub his erect phallus on her buttocks and thighs.

Michele cringed when she felt the man's penis rubbing against her rear; it had been over fifteen years since she had let a man put his sex organs near hers but she knew exactly what this man was doing. She knew that to offer resistance would only endanger the lives of her son and daughter. Although she couldn't see it happening; she was aware that the other man was assaulting Shelly. Maybe if she complied they would leave her daughter alone and concentrate on her? She knew this was a vain hope but she was prepared to do anything to save her children.

Dave was in rush to fuck the podgy but attractive woman he had bent over in front of him; he hadn't had sex with a woman for so long and the way the woman was dressed in her business suit with her heavy makeup and perfume was very arousing. She looked and dressed very similar to one of the prison's psychologists; whom the inmates often fantasised about when they masturbated. He was sure the bitch dressed that way just to get the inmates excited.

Dave tore open the gusset of Michele's pantyhose and pushed his cock inside the hole and rubbed it against her satin panties relishing the feel of the slinky garment against his throbbing penis. He grabbed the woman by the hips and slid his cock inside the leg opening of her knickers and pushed the glans of his penis inside the lips of her labia. He pushed forward whilst pulling the woman's buttocks back against him and slowly impaled her on his cock.

Michele gasped as the man's engorged phallus pushed its way inside her and filled her vagina; she had forgotten what it was like to have a man's cock inside her body but she was glad that the man was leaking copious amounts of pre-seminal fluid otherwise the discomfort she felt would be downright agony. She felt the man grip her hips and slowly being to fuck her with long slow strokes.

Michele's body responded to the stimulus and she began to ooze vaginal secretions which eased the passage of the man's cock as it thrust in and out of her vagina. She shuddered with an amalgamation of disgust and arousal as she realised that despite the situation, long dormant feelings of sexual excitement were emanating from her sex and through her body. She groaned and pushed back against the man who was forcefully taking her. She hoped her son and daughter realised she was capitulating only to save them from the brigands who had invaded her house.

Meanwhile Shelly was suckling on Sol's cock; she had learned how to regulate her breathing as she bobbed her head up and down on his cock. Although she didn't like what the man was forcing her to she did wonder why the girls at school made such a fuss about fellating their boyfriend's; saying it was disgusting and that they only did it to keep their boyfriend's happy. There really wasn't much to it once you got the breathing right: clamp your lips on the shaft and bob your head back and forth whilst your tongue licked and slavered at the man's glans. To Shelly it was not really different to masturbating her brother except the man's cock was in her mouth and not her hand.

Shelly was happy to suck as many cocks as she had to, to keep her family safe; as long as they didn't fuck her she could live with the indignity. She was vaguely aware that her mother was being assaulted on the chair across from her; she could hear the slapping noises as the man pounded his cock in and out of her mother's cunt and his groin slapped against her mother's buttocks, but she realised her mother was not resisting only to save her and her brother from danger.

Shelly stroked Sol's scrotum in order to encourage his orgasm; she had never done this for her brother and the hairy sack with the two firm testes felt strange. She knew that boys likes girls to do this and she was also aware that if she yanked or squeezed the man's scrotum she could cause him excruciating pain and she would have done so except for her responsibility for the safety of her brother. So Shelly concentrated on fellating the escapee so that she could get the ordeal over with as soon as possible.

Shelly felt Sol's long hard cock begin to pulse in her mouth and his hands flew to her head and pushed her face into his groin; she knew what was about to happen, she had bought her brother to orgasm plenty of times and knew that this man's cock was about to disgorge his load of semen. She could feel the man's scrotum contract as she gently caressed it and then his cock began to convulse. Shelly prepared herself for the flood of semen that was about to fill her mouth but she did not anticipate the volume.

Sol moaned as he erupted into the young girl's mouth; she was still stroking his scrotal sack and her lips and tongue slavered at his shaft and head; he held her head in his hands and fucked her face.

"OHHHHhhhhh!!! Yeah baby! Take my load! TAKE MY LOAD!!!" he shouted.

Despite her best efforts to swallow the warm musky fluids that filled her mouth; Shelly still let some of the viscous fluid escape her lips and dribble down her chin. She began to gag and gasp but the man held her head firmly and she had to force herself to control her breathing so that she didn't coke. Rivulets of spunk ran from her nostrils as Sol's load backed up in her mouth and sinuses. Shelly swallowed as much as the semen as she could and finally gained control of her gag reflex. She slathered the man's cock and shifted her hand to his shaft and drained him of the last of his spend.

Sol's knees nearly buckled with the intensity of his orgasm and he let go of the girl's face and let her drain him; her pretty face was covered in semen; dribbles of the white creamy fluid ran from her nostrils and the corners of her mouth.

Shelly licked the man's penis clean and then spat the slowly deflating member out of her mouth; she swallowed the last of his ejaculate and then licked the dribble from her lips and wiped her face with her sleeve. The sleeve of her navy-blue school blazer was stained with silvery threads of drying semen. Shelly felt degraded but at the same time a little proud that she had performed so well and saved the lives of her mother and brother.

Michele heard the man who was forcing her daughter to fellate him moan in pleasure as he orgasmed. She realised her daughter had lost her innocence and had been degraded and sexually assaulted but least the criminals were not physically hurting her or her family other than the acts of sexual assault. She was now panting with long repressed lust as her well-lubricated vagina stretched around the long thick cock that was now slamming in and out of her. The walls of her vagina squeezed and convulsed in cadence with Dave's thrusts.

Dave was aware that woman was enjoying being fucked and he shifted his hands down to the top of her legs so that he could stroke and caress her pantyhose encased thighs and buttocks. He ground himself against her soft buttocks enjoying the feel of his scrotum rubbing on her satin panty clad arse. He could feel his orgasm rushing through him and squeezed the woman's thighs in a vice-like grip and pounded his spasming cock in and out of her quivering cunt.

Michele groaned in coerced pleasure as an orgasm shook her. It was her first coital invoked orgasm for many years and she had forgotten how intense the pleasure was. As Dave's hot semen filled her wet cunt wave after wave of sexual pleasure rippled through her body.

"Oh God forgive me that feels so good!" she moaned.

"Ohhhh yeah; so good!" Dave replied in unison as he drained himself inside the mature woman who bucked and writhed against his gushing cock.

Dave pulled the woman's soft buttocks into his groin and let his cock quiver and pulse inside her; he could feel her tight quim undulate around his shaft as she rode her climax along with his. Rivulets of his semen oozed from her cunt and soaked into her panties and pantyhose. He grasped the woman's body and quickly spun her around so that she lay beneath him; he knelt between her legs and slammed his cock back into her sopping cunt as he ejaculated the last of his spend deep inside her.

When Dave quickly pulled out of her and then spun her around, Michele instinctively raised her legs and drew him back into her. His pubis now ground against her clitty intensifying the last throes of her orgasm. She drummed her heels on his back and thrust her groin up to meet his and her nails raked at his shirt; she put her arms around his neck and pulled his face to hers. Dave bent down and kissed her, driving his tongue into her sweet wet mouth. She responded and slathered at his tongue. Dave tasted the sweetness of her mouth and scent of her perfume; he relished the feel of her hose-clad thighs on his body.

Michele realised that she behaving like a wanton slut in front of her children but couldn't control herself. The last of her orgasm wracked her body and she slowly recovered her composure. The man on top of her lay exhausted and spent as she rested her legs on his back and removed her arms from around his neck. He kissed her and then disentangled himself from her prone body; his cock slid out of her steaming cunt with audible plop and rivulets of semen gushed from her sex further soaking her panties and hose.

Dave knelt between Michele's legs gasping for breath; he wiped his cock on her skirt, gobbets of his semen glistening on the dark fabric. He got to his feet and put his cock away and zipped his fly.

Sol pulled up his pants; he stood in front of the teenage girl who silently sobbed as she sat on the couch and pulled down her skirt. Shelly's sobbing was a consequence of shame and guilt rather than any feelings of outrage. She wanted her mother and brother to think that she had been an unwilling participant in forced fellatio rather than a provocateur.

During the ravishing of the mother and daughter by his brother and friend, Leon had taken great delight in watching the action. He was now sporting a huge erection and was keen to use it. Remarkably, he noticed that the teenage boy tied to the chair was also exhibiting a large bulge in his pants.

As Sol and Dave dressed themselves and the two Michele's guiltily sat in silence adjusting their clothing Leon had an evil though.

"Hey guys; check this out! The young fellow here has a hard on!" he sniggered.

"I'll be buggered; the young buck's got the hots for mommy and sister!" Sol laughed.

"Well why don't we grant him his wish," Dave sniggered, and began to untie the youth.

Mike Stephens shook his head in horror at what the criminals were proposing; it was one thing to share the occasional 'pony-ride' with his sister; but to be forced to perform sex acts with his family in front of these thugs was utterly degrading. The problem was that he was utterly turned on; the sight of his mother enjoying being fucked by the escapee and his sister milking the other brute with her mouth had excited more than anything he had ever seen.

Mother and daughter paled at the suggestion that they should engage in sexual activity with Mike, forced or otherwise. Shelly had masturbated her brother plenty of times but no one knew about it except the two of them. Both women cowered down into their seats and began to sob.

"Well I'll tell you what; I hope he's hot for mommy because I want the girl next!" Lean snarled and stalked over to where Shelly sat quivering in fear on the couch.

Dave held the knife to the teenage boy's throat.

"Drop your pants kid!" he threatened.

Mike had no choice but to comply and shucked out of his school uniform pants; his erection bulged in his Y-fronts.

Shelly tried to scream as Leon approached her unbuckling his pants but she realised that this would only cause more violence. She set her resolve and opened her mouth as the man approached her expecting that he would force her to fellate him as the man named Sol had.

"Fuck that; I want some pussy!" Leon growled, and before Shelly could react he grabbed her ankles and lifted her legs up high in the air.

Shelly screamed in unison with her mother and Dave reacted by bringing the knife back to the teenage boy's throat.

"Shut the fuck up!" he snarled and both women stifled their protests.

Leon spun Shelly around so that she lying on the couch with her legs high in the air and her skirt rucked around her waist. She began to quietly sob as Leon ran a hand up and down her silken legs. He loved the feel of her silky hose and pulled one her calves to his groin and rubbed his cock on her ankle and leg leaving silvery trails of pre-seminal fluid on her stockings.

Despite the absurdity of the situation Mikes cock began to quiver in excitement as he watched what the man was doing to his sister.

"The boy wants some," Dave leered.

"You a virgin?" he hissed in Mike's ear.

Mike nodded in response.

"Well I believe it's only fair that mommy help you out and be the first," Dave laughed.

Both Michele and her son balked but when Dave frog-marched the boy over to where his mother sat on the overstuffed chair she realised that the men were dead serious.

"You fuck him or I do," Dave whispered.

"During my time inside I got quite a taste for young arse; so you decide!"

Michele knew that what the men wanted her to do was the ultimate taboo but she was not going to let this man bugger her only son.

"Mike; I'm going to do what these men want, but remember I'm only doing it to save you from an even more revolting and debasing act," Michele whispered; her heavily made-up face showing her deep concern.

Mike nodded and hung his head but secretly, in the deep dark recesses of his mind, he was extremely aroused at the thought of fucking his mother.

Meanwhile Leon had climbed on the couch and was furiously rubbing his cock against Shelly's nylon-encased thighs. He then lowered himself so that his cock was rubbing against the gusset of her panties; Shelly's labia opened in response to the stimulation and Leon was excited as he felt the folds of the teenage girl's open like a flower and envelop his cock through the layers of nylon panty and hose.

Shelly blushed as she realised her body was reacting the same as when her brother mounted her for a 'pony-ride' and her sex began to moisten. Leon dry humped the girl and was delighted when he sensed her vaginal juices were soaking into her underwear.

Dave stood behind Mike brandishing the knife menacingly and Michele realised it was time to commit the most heinous of sins but she had no choice.

"Stand still Mike and just let mommy do what she has to ok?" she whispered and Mike nodded his consent.

Michele reached out and took her son's erect penis in her hand; she lightly raked her painted fingernails along the shaft and watched him shudder as waves of pleasure swept over him. Mike groaned and his mother gripped his tumescent penis and began to stroke him earnestly.

"Oh god mom; I'm sorry but that feels so good!" Mike moaned.

"Fuck this!" Dave growled, "You're trying to get him off with a wank. You better fuck him right now you bitch!"

Michele was dismayed that her plan had been discovered. She had hoped to bring her son to orgasm by masturbation and forgo the indignity of having have sex with him. Michele resigned herself to her fate.

"Ok Mike I'm going to scrunch back on the chair and I want you to kneel on the floor between my legs ok?" Michele whispered to her son.

Mike nodded and when his mother lay back and lifted her skirt he smiled inwardly to himself. He kneeled between her legs and put his cock on her sex and began to hump his mother through her panties. Michele lifted her legs and enveloped her teenage son and pulled him to her body. She could feel his hard cock through her panties and, God help her, if she didn't start to secrete vaginal juices again.

Mike began to frantically hump his mother, feeling the folds of her sex around his cock just like his sister's had been this morning. He grunted and panted as he dry humped his mother and she held him locked to her body by her strong thighs and calves. The feel of her gossamer nylons on his bare skin was highly arousing and if he hadn't blown a load earlier this morning into his sister's underwear he would almost certainly have come by now.

"Fuck this I want to see some penetration!" Dave snarled, waving the knife around.

Michele tentatively reached down and took her son's penis in her hand.

"Ok Mike; we have to do this because these men are making us do it; be brave," she smiled into her son's face trying to ease his guilt.

She guided her son's erection through the layers of satin and nylon until his glans nestled in the crease of her labia. Her cunt still wet from the fucking she had just received opened easily and her son's penis slid inside her right up to the hilt. Mike couldn't continue the charade any longer and began to rut away between his mother's legs. He crushed his lips against hers and slid his tongue into her mouth, savouring the taste of her lipstick and the smell of her perfume.

Michele was shocked by her son's actions but she rationalised it as the act of a frightened boy. She lifted her legs up and locked her high-heels behind her son's back and fucked him back; kissing him with heat and fervour. She figured that she should make him come quickly to get the degrading act over with as soon as possible.

Mike took his mother's response as consent and tore open her satin blouse and plucked her large soft white breast from the cups of her satin bra. He tweaked a raspberry-coloured nipple between his fingers and then suckled the other one, gnawing and slobbering at her breast.

Michele was genuinely shocked; the little bugger was taking liberties and obviously enjoying himself. There was nothing she could do now however and decided that her son was going to have some explaining to do if they survived the day. She resigned herself to the situation; she was acutely aware that her son had a rather magnificent long thick cock that was stimulating her rather agreeably. She lifted his face from her breast and back to her mouth and kissed him passionately as she bucked away underneath him.

Mike moved his hands down to his mother's thighs and stroked them; revelling in the feel of her soft warm skin sheathed in the diaphanous nylons. He slid his hands under her buttocks and squeezed them through her panties as he bucked and fucked and humped his mother, feeling an intense orgasm building up.

Michele let her son fuck her and his cock stimulated her vagina whilst his pubis ground into her stimulating her clitoris; she hung on to him with her legs locked around his waist and arms around his neck. She rode him as he rode her. Mother and son rutted like animals as they simultaneously orgasmed.

"OHHHhhhh Mommy that is just so goooooooooood!!!" Mike squealed as his cock pulsed and sprayed jets of hot semen deep inside his mother.

"Oh baby; yessssssssss!!!" Michele hissed in her son's ear as she felt him flood her cunt with hot spunk and her vaginal walls spasmed and milked him as she came.

"Oh fucking great; what a turn-on!" Sol cheered mother and son on.

Sol had kicked off his pants and was stroking his cock as he watched mother and son fuck each other with obvious relish whilst Leon ravaged her daughter in the same room.

He pulled Mike off his mother and the last of Mike's emission sprayed over his mother's legs. Sol quickly replaced Mike between his mother's legs and began to fuck the plump woman with vigour. Michele wrapped her legs around him and fucked him back; as her orgasm continued to pulsate through her body. She viciously pulled his face down to hers and smashed her lips against his as she humped at the newly inserted cock.

Dave laughed and tied Mike back into to the chair; his cock slowly deflating and leaking drops of semen on the floor. Then he turned around to see what Leon was up to; he was horny as hell again and wanted to get himself a piece of either the mother or daughter.

Leon was writhing away on top of the struggling teenage girl; he'd tore off her panties and torn open the crotch of her pantyhose and his cock was jammed against the girl's virgin pussy.

Shelly's cunt was slick with juices from her own secretions and Leon's pre-seminal fluid and as Leon pushed his iron-hard cock slowly into the teenage virgin he deflowered her, slowly tearing her hymen. Shelly was surprised that she felt so little pain but what she didn't know was that all that 'pony-riding' with her brother had been tearing and stretching her hymen little by little over the last few months so very little of her hymen remained when Leon penetrated her.

When she experienced a cock inside her for the first time in her life Shelly wondered why she had ever decided to save her virginity for marriage. The feeling of the penis inside her was quite satisfying and when Leon's pubis slammed against hers and he began to hump away at her, his pubis stimulated her swollen clitty and she found herself enjoying being fucked for the first time. Shelly was pragmatic enough to realise that now that her virginity had been taken from her and the three men intended to repeatedly take her and her mother she might as well capitulate.

She looked over Leon's shoulder and saw that Sol had replaced her brother between her mother's legs and was rutting away excitedly while her mother bucked and humped underneath him, her legs locked around him and her heels drummed on his back as her orgasm continued to rage through her. Shelly copied her mother's actions and lifted her legs up allowing Leon to fully penetrate her.

Leon was a little surprised when the teenage girl lifted her legs to allow him better access to her pussy but ever the opportunist he took hold of her ankles and lifted them over his shoulders, he kissed her nylon-sheathed calves as his engorged penis slid in and out of her tight virginal pussy and then lowered his face to hers and was rewarded with a series of deep sloppy kisses.

Dave was now the only escapee not getting any action and he was horny as hell; he moved over to the armchair and took hold Michele's hand and put it on his cock. She instinctively took hold of his penis and began to stroke him but he was not satisfied with that. He took hold of her hair and pulled her face away from Sol's and proffered his engorged penis to the plump mature woman who was being ravished by his jailhouse pal. Michele accepted the offering and her lipstick smeared his glans and shaft as she swallowed the proffered appendage.

Sol was a little disappointed that the woman was no longer kissing him; but watching her fellate Dave added to his excitement and he felt another orgasm building. He exploded inside the woman and felt her cunt spasm around his cock as she came with him. She slathered and sucked at Dave's cock and he too erupted, filling her mouth with his seed.

Leon and Shelly were concentrating on their own desires as they both approached orgasm; Shelly was very excited, she had experienced clitoral orgasms before but having her cunt filled with hard cock added a new dimension to the sexual delight she was experiencing. Her cunt was sopping wet with vaginal juices and when the man rutting at her body exploded inside her, her own orgasm was invoked. She writhed and moaned as the most terrific orgasm she had ever experienced shook her body.

Leon howled as his cock convulsed inside the young girl; her pussy milked him of his seed and he pounded away at her as her body writhed beneath him and her cunt quivered and shuddered in the throes of her climax.

Mother and daughter abandoned any pretence of reluctance and gave way to their carnal desires as the three home invaders repeatedly ravaged them both over the remaining hours of daylight. Michael was cut loose from the chair and allowed to fuck his sister later that afternoon as the three escapees looked on whilst forcing Michele to watch. Michele's suspicion was raised as she watched her son and daughter fuck each other with unrepressed enthusiasm and her mind drifted back to when she saw Shelly leaving her brother's bedroom this morning with her skirt stuck in the back of her panties.

By the time the criminals left the Stephens' house mother and daughter were dressed only in their lingerie and high-heels, their pantyhose torn to tatters, their knickers ripped open at the crotch, their makeup smeared over their faces and their faces, bodies and hair sticky with drying semen.

The three escapees were disappointed to find that Michele Stephens did not own a car so they stole one from off the street. They also found only a small amount of cash in the house. Michele Stephens' promised the escapees that that they would not report the home invasion; they did not want to have to explain to the authorities how they had capitulated to hours of torrid sex and incest. She made her children swear their secrecy as well.

Michele Stephens went to the pharmacy and bought 'morning-after pill' contraceptives for herself and Shelly. She then put herself and her daughter on the contraceptive pill. Shelly Stephens, deflowered and awakened to the delights of sexual intercourse, began to fuck her brother on regular basis and gained a reputation as a school tart. Strangely enough she still graduated as a straight-A student and some whispered that this might be due certain favours she bestowed on some of the teachers.

Michele Stephens' career as a legal secretary also took off over the following months and it was rumoured that she fucked her way up the corporate ladder. By the time her son graduated high school, she owned a late model SUV, had paid off her house, and had a substantial amount of money in her savings account. A mysterious stranger was seen by the neighbours to frequently visit her late at night and it has been said by some that the stranger bore a distinctive resemblance to an escaped prisoner named Sol; but rumours and innuendo are rife when an attractive mature woman lives on her own.

"Yep, you are one fucking hot nurse alright; maybe next time you can play Nun!"

I heard his laughter fading as he walked down the passageway past the other cells to what I presumed to be the waiting room. The waiting room where undoubtedly there were more customers waiting. I closed my eyes as the tears ran slowly down my cheeks.

 

Part VI

I reached across and pressed the orange button to switch on the amber light indicating to Mabel that I was not yet ready for another visitor. I noticed the blue light was lit, indicating that I had another 'customer', or as Carmel would say "a punter" waiting.

I looked across and saw Carmel kissing the huge Negro who had previously been fiercely sodomising her. He pushed a handful of notes down her bra, spanked her playfully on the arse, and strolled out the cell. I quickly hid my face so that we would not make eye contact; I did not want him for a customer; not from what I saw of him when he was violently fucking Carmel.

I walked up to the cell bars and whispered to Carmel across the passageway, I could hear grunts and sighs as the other 'working girls' serviced their clients in the other four cells,

"Carmel, Carmel!"

"Hi Michele, see what Leon gave me?" She smiled pulling out a handful of notes from her bra;

"He is always a big tipper; and he has a big tip down there too!" she laughed at her own pun.

I had no time for this; I had important questions to ask. Carmel ignited the obligatory menthol cigarette.

"What do I do now; I pressed the orange button but the blue light is still on. Do I make the punter wait until I'm cleaned up or what?"

"Oh my God; Carmel, I want this to stop. I have just been sodomised so hard my back passage is bleeding!"

I started to sob again.

"Cut that shit out Michele; you need to harden-up girl or you won't survive!"

"Talk to Mabel on the intercom, sometimes the punters don't care too much how you look, especially if they just want a 'quickie'."

Again I was amazed at how quickly these perverts had degraded me down to their level. I was thinking of these crossdressed prison prostitutes as 'girls' and the men who raped me for money as 'punters'; plus I even understood what she meant by a 'quickie', it wasn't rocket science after all!"

I pressed the talk button,

"Mabel I'm not cleaned and dressed yet," I whispered in my best imitation of a feminine voice.

I hoped she would have some sympathy for me now that I was capitulating in this perverted parody of forced feminisation and prostitution.

"Don't bovver Michele; he's on his way. He just wants a quickie and this is a freebie so you better make it quick; time is money!"

What the fuck did she mean: 'Freebie'? I was about to find out.

The unmistakable navy blue uniform of a prison guard came into view. He was a fat man with a florid complexion, he was sweating heavily with the exertion of carrying around such a large gut.

I had sat back down on the bed and evened out my white nurse's uniform skirt, the semen and bloodstains were not too visible, but I knew they were there. My white pantyhose had laddered down one leg from the hole that my last customer had ripped in the gusset.

I did not recognise the fat guard but I knew he must be in charge of one of the other wings as he wore Sargent's stipes on his sleeve. He came straight into the cell, sweating and puffing, and without saying a word unzipped his fly.

I looked up in stunned amazement as he walked up to the bed, reached out a hand around the back of my head, and with his other hand, pushed his semi tumescent, uncircumcised penis into my mouth.

I started to gag immediately because the taste was so foul. It tasted of stale urine, and a cheesy taste that could only be the built up detritus of bodily secretions that had coagulated and fermented under his foreskin. It was the most disgusting taste I had ever tasted and my gagging increased.

The guard pulled his cock out of my mouth, pushed my head back and tilted it up to look at him; his fat face was snarling and vicious. He slapped me once across the face. He didn't say anything; he just wagged his finger in my face. The slap wasn't even that hard, it was just the surprise and his continued silence that stunned me.

He took his semi-hard cock into his hand again and pushed it against my lips. I knew enough by now to realise that my only salvation was to make him come as quickly as possible. I opened my mouth and pushed out my tongue. I deliberately licked at the lipstick on my lips to try and mask the fetid taste of the guard's penis. I then started to lick all around his knob that was half exposed out of the wrinkled foreskin.

I bought up my hand with the intention of masturbating the guard while I slobbered on his glans with my tongue and lips so he would ejaculate over my body rather than in my mouth. The guard would have nothing of it and slapped my hand away; he again grabbed my head and forced his cock between my lips and into my mouth.

He was still silent except for his heavy breathing and grunting. The smell of stale sweat wafted from his filthy body. He bought his other hand up now and cradled my head between both hands, the dirty fingers enmeshed in my hair behind my ears. Then he raped my mouth. There is no other way to describe it.

His penis became engorged and hard, the glans were now fully exposed as his foreskin pulled back from the bulbous knob. The foul taste of his cock was now so rancid I thought I might gag again so I did the best thing I could under the circumstances and worked up as much saliva as I could to wash his knob clean with my tongue. I worked up more spit and continued to slaver his cock with my tongue; this had the effect of cleaning his cock and cleaning out my mouth as I swallowed the foul mess that had coagulated under his foreskin.

These actions also obviously increased the guard's pleasure as he now increased his tempo, thrusting his erect member in and out of my mouth. He pulled his cockhead out as far as my lips and then rammed it home as far as it would go. Luckily his cock was not very big and I had no problems accommodating him, it was just so hard to breathe with it jack-hammering in and out of my mouth.

On the in-stroke he pulled my head forward to that my nose was buried in his fat gut overhanging his loins. He forced my head onto his penis so hard that my teeth rattled on the metal zipper of his fly. He was sweating so much that I could feel drops of his disgusting perspiration dripping off his jowls and on to my head.

He continued to grunt like a pig as he fucked my face; his now rock hard cock with its spongy head tasted salty as precum started to leak from the eye of his glans. He pushed it in and out faster and harder, pulling it out nearly all the way then slamming it home so that my face was buried in his crotch.

Then he pushed my face into his crotch as hard as he could and held it there. I couldn't breath! I felt my gag reflex returning as I struggled to get oxygen into my mouth or nose. I reached out and tried to push myself back from him but his vice-like grip was too strong; he pushed my face harder into his crotch.

I couldn't help it, I stated to gag, my mouth convulsing and my tongue flailing around in my mouth. At the same time my fists were drumming against his thighs as I tried to push myself away. That was when he stated laugh! He also said the only word he ever spoke,

"Good!"

He held my face hard against him and as I started to blackout I felt his penis convulse in my mouth. Stream after stream of creamy, salty, hot semen shot into the back of my mouth. As the guard's cock continued to eject its foul jets of spunk he continued to laugh. He was laughing as he orgasmed.

At last he released the tight grip on my head and allowed me to take a breath through my nose. As soon as I did he pushed my face back into his crotch. As my mouth filled up with his sickly seed I had no choice but to swallow. If I didn't I would choke. His ejaculation seemed to go on forever and try as I might I could not swallow all his come. It welled up in the back of my throat as his cock continued to throb and convulse. I coughed and felt his slimy emissions force its way up the back of my throat and then run out of my nostrils. I felt disgusted.

Then the guard pushed me away. I fell on the bed gagging, sobbing and coughing; trying to breathe. He reached down and grabbed my hair and pulled my face up again so I was looking at him from level with his waist. His face was bright red, florid and sweaty. His jowls dripped sweat down his shirt. Without a word he rubbed his now deflating penis all over my face mixing his semen with my tears and my makeup. Then he put his cock inside his pants, zipped up and walked away. I had never felt so humiliated in my life.

 

I lay on the bed sobbing. I looked up through the tears, makeup and semen in my eyes and noticed that the blue light on the intercom was mercifully extinguished. I reached out slapped the switch to turn on the orange busy light. The intercom suddenly crackled and I heard Mabel, the crossdressed old con who was our 'madam'.

"Take half an hour hun, it's gone quiet for now and it's getting late; get cleaned up and give me a call."

I half groaned into the intercom,

"Sure."

I wanted to just lay on the cot and cry myself to sleep but I knew that Carmel was right, I had to harden up if I was to survive. I had to find out as much as I could about this sick operation so that I could tell someone in authority so they would get me out of this nightmare.

I stood and stripped off my stained nurse's uniform, slid out of my high heels and pulled down the tattered pantyhose. I threw the hose in the bin, stripped off my remaining underwear and placed it with the uniform in the washing basket that was tucked away in the corner. I noticed the little ridiculous nurses cap on the floor and picked that up on the way. I pulled off my wig and put on the satin robe. All of these movements caused me significant pain. My head ached from the slapping I had received, my back passage felt like someone had put a red hot poker up there, and I was now immensely tired. I had no watch but guessed it was after 3:00am.

I padded out of my cell with my makeup case in hand and made my way down the dim passageway. I deliberately tried not to look in the other darkened cells but in the subdued red lighting I could see Carmel was kneeling on her cell floor and fellating a con who was sitting on her bed. His head was propped back on a mountain of fluffy pillows, his eyes closed as he enjoyed her ministrations.

As I passed the end cell on the right I heard muffled yelps and couldn't help but peek. I saw a fat crossdressed 'working girl' dressed in a French maid's outfit, baby-doll blonde wig and heavy makeup; a skinny little con was riding her doggy style on the bed. He had her black satin maid's skirt rucked up over her back and her black satin panties hung from one fat, black-stockinged ankle as he humped her and smacked her plump white ass as he did. She yelped every time he smacked her, but she seemed to be smiling and pushing back to meet his thrusts. If my life weren't so tragic I would have found the sight immensely funny I suppose.

I continued on to the shower-block and let the scalding hot water wash away my makeup, tears, and the semen from two different men. I was so close to crying again but held back. I heard the shower next door suddenly splash into life.

"Hello?" I asked with a trembling voice.

"Hi hun," I heard the response as a male falsetto.

"I'm Charlotte. No Charlotte the Harlot jokes please!" she laughed.

"Welcome to E Block Michele," came the voice over the shower cubicle.

"You know who I am then?" I asked.

"Oh of course hun, it's always the talk of the nick when a new girl starts working for Eddie."

I turned off the water and towelled myself dry thinking about what Charlotte had said: 'talk of the nick'?

Charlotte emerged from the shower with a huge silk bathrobe wrapped around her generous proportions. She was the French maid I had seen on my way out of the cellblock. She made her way over to the line of stainless steel mirrors and began to apply makeup to her plump but pretty face.

"What do you mean by 'talk of the nick'?" I asked taking a seat beside her and applying foundation to my face.

"Well Carmel should have told you everything; didn't she?"

I went on to explain to Charlotte what Carmel had told me and also what I had figured out for myself. I made no mention of my plan to escape this hellhole; Charlotte like Carmel seemed to accept the situation and even seemed to like what was happening to her.

"Well you seem to have it figured out pretty well hun. Eddie owns us girls, Steve is the muscle, Mabel is the Madame; and up until yesterday darling, you used to be the accountant and secretary."

"I suppose you still are Eddie's secretary," she said sarcastically.

"Lots of us girls started out working for Eddie in other roles; as runners, dealers, or small time worker bees. Eddie seems to have the knack of knowing which cons will look like sexy women when they're crossdressed; feminised if you will."

"Some of the prospects are so obvious because they are 'femme' when they arrive in the nick; some convert to homosexuality as part of prison life and Eddie feminises them as willing subjects, and some like you are forced into it."

"To be honest I think Eddie likes it better when he has to force them," she smiled, smoothing on a second coat of bright red lipstick.

"How many of us are there? Crossdressed prostitutes I mean?" I asked incredulous.

"Oh not that many; about a dozen or so at any one time, but only six of us work in the workrooms."

"Some take up full time with cons who can afford to pay Eddie enough to keep them; some are just let go when Eddie has made enough from them or they break down and are sent to the psycho ward."

"Take Carmel for instance, she still works for Eddie even though she has a prison 'husband', she does it because she likes the money, she likes the gifts from Eddie, but mostly she likes the life."

"Then there is Mabel who did this for so long that she got too old to work the cells so she's Eddie's hostess, Madame, whatever; but will still give a con great time if doesn't mind mutton instead of lamb if you know what I mean?" Charlotte winked and concentrated on applying another thick coat of mascara.

"But what about the Warden? I know lots of the guards are corrupt from my time here already, but how the fuck does Eddie get to run a stable of crossdressed prostitutes out of a prison wing? I know it's this is a small disused block, but fuck me its prison property!!!!"

"Oh my god Michele for some one who is so smart you are so dumb!"

"Who the fuck do you think is Eddie's partner? It’s the Governor you fucking idiot!"

I let that settle in. So it was going to be no use going to the prison authorities with my complaints; I would just have to figure a way to use my money and outside influence to go higher up the chain of authority to rescue me.

I looked at myself in the mirror; it amazed me how quickly I had got the hang of applying makeup. I had on thick coat of foundation and powder, rouged cheeks, heavily lined and mascaraed eyes, mauve over pink eye shadow, and my dark ruby red lips. I sure knew how to look like a slut after only one night!

Charlotte's makeup was even heavier than mine, and her plump bright red lips and chubby face, gave her a slutty girly look. She picked up her makeup case and stood to leave,

"Did Carmel tell you not to leave anything in here? Those other bitches will steal your knickers while you're still wearing them if they can get away with it!" she laughed.

I fell into step beside her,

"But what did you mean by me being 'talk of the nick'" I asked again.

"Oh whenever a new girl starts the punters are always interested. Eddie can charge them more because you are new, undamaged goods, but of course he has throw the senior guards a few 'freebies' to keep them on side."

"He will probably limit the amount of punters you see for the first few nights, but after that you will be the most popular girl at the ball!" she laughed.

"You like this don't you; this life?" I asked trying to keep the disgust out my voice.

"Oh Michele, I didn't like it at first, but now I love it! I work all night and sleep all day and Eddie gives me anything I want!"

"I hated it so much when I first started that I though if I got fat none of the punters would want me. I was already a bit plump so I put on another 10 kilos; guess what? Some of the punters just love us larger girls!" she giggled.

"After six months of hating myself I started to realise I liked it. I bet you have already had a few twinges in the clitty whilst those naughty men have had their way with you?" she chuckled.

"See ya," she whispered as we came adjacent to her workroom cell and slipped though the door.

I though to myself: 'How can she know? Twinges! Twinges!! I have had an orgasm for god's sake!!!' My god I hope I never get to like this wretched existence like the other wretched girls!

I entered my cell and sat on the bed. It appeared none of the other girls had punters either for now as they were either adjusting their makeup in their wardrobe mirrors or changing into robes to go to the shower and bath block. Through the bars I saw Carmel lounging on her large work cot surrounded by her mountain of satin pillows; she had the obligatory menthol cigarette and was reading a fashion magazine by the dim red light of her lamp.

To my disappointment it looked like this night's training had paid off; I knew exactly what to do next! I had been brainwashed to some extent. Without further thought I selected a brunette shoulder length wig and adjusted it in place. I opened the drawer and took out a set of matching white satin full cut panties, bra, and garter belt. I put the bra in place and tucked the breastforms into the cups. I selected a pair of diaphanous skin toned stockings that were embellished by black seams and black, reinforced heel and toes. I slipped into the garter belt, sat on the bed and slid the exquisite cool nylons onto my legs, fastening them to the garter clips. I smoothed each stocking out along my legs and adjusted the seams so they lay in the centre of the back of my legs.

I sat there stroking my legs, feeling the luxury of the expensive nylons sending little electric waves of pleasure though my body. I don't know how long I had been caressing my nyloned legs when I snapped out of the reverie.

"I will not surrender to this perversion!" I told myself.

I slipped the sleek white nylon panties up my legs and stood to adjust them in place, the little electric shocks from the swish of the nylon on nylon as they slid up my legs caused my penis to spasm involuntarily. I concentrated and pushed my wrinkled penis into the snug silken gusset of the full cut panties.

I walked to the robe and selected a white leather miniskirt and peach satin blouse. The satin of the blouse on my bare skin was again cool and luxurious; I had trouble with the buttons because they were on the wrong side. I sat on the bed again and put on the strappy white high-heeled open toe sandals that I had selected. The reinforced heels and toes of my nylons made a sexy display. I stood up and stepped into the white leather mini and hitched it up, tucking the blouse into the waistband and zipping the skirt at the side.

I went to my jewellery box and selected a small plain gold bracelet, which I fastened around my ankle. It glowed in the dim light, set off by the contrast of my silky flesh toned stockings, reinforced nylon stocking heels and the white leather ankle straps of my high heels.

I selected a simple gold chain for my neck and plain gold drop earrings. I slipped two gold and emerald rings onto my fingers. I noted my ruby red fingernail nail polish was chipped, but in this light who cared. I wondered how much, if any, of this jewellery was real.

I looked at myself in the full-length mirror. I saw a mature, sexy woman with brunette shoulder-length hair, wearing heavy makeup and a lovely peach satin blouse. Her jewellery was exquisite, the emerald rings on her finger contrasting with her red polished fingernails, the simple gold neck chain resting where the hint of her breasts began to rise in the satin blouse.

Her tight white leather skirt stretched across her tiny little pot belly and clung to her well formed thighs, the hem resting against her sheer nyloned thighs, displaying just a hint of dark nylon stocking tops. Following her well-formed legs down, they are encased in gossamer thin, flesh toned, nylon stockings with sexy black back-seams. The black reinforced heels and toes of her stockings peeked through the high-heeled sandals, a glimpse of red nail-polished toes just visible through the nylon. The strappy white high heel sandals pushed her feet up at the heels so that her toned calves glittered in their nylon casing, the gold anklet smoulders in the red light.

I reach out and apply a coat of powder to my lower neck and decolletage where it disappears into the satin blouse. The final touch. I look gorgeous, sophisticated but highly desirable. I look eminently fuckable!!!

I turn around and Carmel and Charlotte are in the corridor leaning on the bars of my cell and looking in; cigarette smoke drifts past Carmel's heavily made-up face and creates a halo around the jet-black hair she is wearing teased high on her head and descending past her shoulders. Her heavy Goth makeup, red lips and pale skin make her look like the caricature of a vampire in the movies. This image is reinforced by the skin-tight, black satin sleeveless dress that clings to her body and descends to her ankles. The dress is split up to the waist and one leg encased in sheer black nylon is on display to up to her thigh.

'Sheer to the waist pantyhose,' I thought to myself, then: 'Stop thinking like that; you are not a woman!'

Carmel's outfit is completed with black, satin, opera length gloves, patent leather spiked high heels and a profuseness of silver jewellery. She has a huge silver cross around her neck, long silver ear drops and silver bangles on both wrists.

Charlotte has gone punk and even though she is a big girl she carries it off somehow. The heavy makeup she applied in the shower block has been enhanced even further with more black eyeliner surrounding both of her bright blue eyes. She has extended the dark pink blush from her cheeks to the corner of her eyes and added a powder blue blush to it as a contrast. Her bright red full lips have been glossed and she has added glitter to the abundant multi-coloured eyeshadow that extends from her eyelids up to her eyebrows. Her plump pretty face is framed in a shocking, frizzy, bottle blonde wig that has pink and blue streaks running though it.

She wears a black sequined top that is slashed and torn, her red lacy bra visible in some places through the tears. Written across the front of the ripped garment in silver sequins are the words: "Fuck Slut". She is wearing a red Lycra mini that barely covers her crotch; the waistband bulges around her big belly. She is wearing ripped black fishnet stockings attached to red garters that match her bra. The fishnet stockings stop halfway up her fat thighs and I can see she is wearing shiny taupe dance tights underneath as a foundation garment; the heavy lycra shimmering in the dim red light. Her feet are clad in the tallest high-heeled pumps that I have ever seen; the heels have to be ten inches high. Charlotte has finished the outfit with outrageous jewellery. She has four gold studs in each earlobe, so many gold chains around her neck that I can't count them, and as many bangles on both wrists. Ornate safety pins decorate her torn blouse and micro mini. A gold chain runs from one earring to a gold stud in her nose.

"You look gorgeous Michele," Carmel whispers through the bars.

I wondered if she had read my mind when I was standing in front of the mirror admiring myself.

"Well, I have to say you girls are looking something special. Special fetish requests from the punters?" I enquired.

"Well no Michele; there are no more punters tonight; we're closed for business." Carmel responded lighting yet another menthol cigarette and blowing a cloud of blue smoke towards me.

"Thank fuck for that," I breathed with a sigh of relief.

"Now I can get out of these stupid fucking women's clothes and get back to my own cell!" I said, relived that the evening had come to an end.

Carmel and Charlotte stepped into my workroom cell, silently closed the door, and leaned back menacingly against the bars,

"Oh no Michele, you don't understand! We've finished with punters tonight, but WE haven't finished with you!!!"

 

To be continued……………………………………………….

"Now I can get out of these stupid fucking women's clothes and get back to my own cell!" I said, relived that the evening had come to an end.

Carmel and Charlotte stepped into my workroom cell, silently closed the door, and leaned back menacingly against the bars,

"Oh no Michele, you don't understand! We've finished with punters tonight, but WE haven't finished with you!!!"

 

Part VII

'Oh no!' I think to myself, 'all the degradation I have had to put with over the last seemingly endless hours, and now, just when I think it's over, these two have come for their pound of flesh!'

I look at the two transvestite hookers who have ominously just stepped into my cell, one is a seductive 'Vampira', the other a sexy slut punk, the shock and bewilderment is obvious on my face and for umpteenth time tonight I started to cry.

"Ok girls; please just get it over with as quickly as possible, and please don't hurt me, I'll do whatever you want but I don't want to get hurt any more," I implore, hoping they will take what they want quickly and then let me go.

"Oh Michele sweetheart," Carmel sighs moving towards me with her arms open, "you poor, silly sweet thing; we aren't here to hurt you; we're here to comfort you after your first night at work. Look!" she says, pointing at Charlotte.

Charlotte is smiling and holding up a bottle of whisky, which she been concealing behind her back.

"Come on hun, lets sit down and have a drink," she smiles and leads me to the bed removing her black satin opera gloves and dropping them to the floor.

I sit down with relief and cross my legs. The swish of my nyloned thighs rubbing together sends a little jolt of pleasure through my body. Carmel sits beside me and offers me one of her menthol's whilst Charlotte pours large measures of whisky into three tumblers she has found somewhere in one of the cupboards in my workroom.

I extend my trembling fingers, my fingernails glint a dull red in the subdued light, I take the proffered menthol and bring it to my lips. Carmel extends her bright red fingernailed hand and flicks the bic lighter into life; I drag back on the cool menthol cigarette and blow out a plume of smoke towards the ceiling. I look down and am surprised to see the filter of my cigarette is ringed with lipstick. I laugh to myself at the red, lippy stained cigarette butt and flick a lock of hair out of my eyes.

Crossed legs, lipsticked cigarette butts, flicking my hair! I have adopted all these female mannerisms in such a small time; 'It's as if I was born to this!' I think to myself.

'No!!! Never!!! I won't give in to this sick life!' I force myself to say in my mind, 'I'm a man, a man, a MAN!!!!!

I bring my head up and my face is level with Charlotte's chubby knees. Her ripped black fishnet stockings are indeed being worn over shiny taupe tights as I suspected. My eyes move up her thick but shapely legs, past the tiny tight Lycra mini stretched taught on her thighs, past her slashed T-shirt with the words "Fuck Slut" printed on it in silver sequins. She is proffering me a tumbler of whisky, and, as I reach out to take it I look up into her plump pretty face and whisper,

"Thank you."

"Your welcome honey," she smiles back, her heavily made up face and punk bottle-blonde, pink and blue streaked wig make her look sexy in a 'street whore' kind of way. Her heavily eye-shadowed and mascaraed eyes gleam in the darkened cell.

Charlotte pulls up a chair and sits directly in front of me offering a drink to Carmel and accepting a lighted cigarette in return. I take a pull on the tumbler and the fiery liquid burns my throat as I swallow it; I take another hard pull on the menthol and erupt into coughing fit. The coughing continues as my throat, sore from the abuse it has taken from the 'punters', spasms from the irritation of the smoke and strong liquor.

"There, there," offers Carmel as she takes the drink and cigarette from my hands and hands them off to Charlotte who places the cigarette in an ashtray and the drink on the bedside table.

Camel pulls my head to her shoulder and gently strokes my back as the coughing fit slowly subsides. I can smell her perfume, I recognise the brand as 'Poison,' and my head nestles in the crook of her neck. My arms instinctively wrap around her and I return the hug. I hug her gently as I start to sob into her neck and she continues to stroke my back and slowly rocks me back and forth in the light embrace. She whispers in my ear,

"It's alright Michele; It's alright honey."

I start to drift off as my senses experience the wonder of this sensuous embrace. My satin blouse slides stimulatingly over Carmel's tight, body hugging black satin dress and I can feel the heat of her body even though her breastforms. Our knees are lightly touching, the diaphanous nylons delicately stroking each other, her black pantyhosed leg peeking through the split in her dress and my silk stocking thighs become further exposed as my skirt rides up as we continue to embrace.

In my reverie, I feel the beautiful soft butterfly of Carmel's breath as she exhales sweetly in my ear and whispers,

"There, there, honey; it's all better now; Carmel's here sweetie, Carmel's here."

I raise my head and look into her heavily made-up eyes; my gaze roams over her red lips and pale skin as my right hand moves up and gently strokes her cheek, my ruby-red nails in stark contrast to her pale Goth makeup. My hand continues up to her lustrous black wig and entwines itself in the silky softness of the fine hair. I gently pull her face to mine and our lips brush; I slip my tongue across her lips and taste her lipstick.

Carmel looks into my eyes deeply and reciprocates; her hand slides into my hair and she pulls me forward until our lips softly meet; her tongue cautiously extends and brushes my lips. Then, at the same time, we open our mouths and mash our lips together, our tongues entwine and our bodies push against each other, satin and nylon come together to create an exquisite rasping sensation that causes my little penis to awaken in its silken panty prison.

The strangest feeling envelops me, our caress is so soft and gentle, feminine, comforting and at the same time sexual. My head is spinning with the new sensations that course through my body; after the brutal treatment I have received over the last pitiful hours the tenderness that Carmel is bestowing upon me has me entranced.

Carmel eases me back on the bed until my head comes to rest on my pillow; our kiss is not broken and a sense of urgency seeps into our embrace. Carmel strokes my face and showers my lips, cheeks and eyelids with soft loving kisses; my head spins in a heady sensation of soft feminine yearning. She adjusts herself so that she is half on the bed, her legs straddling mine as her silken, nylon clad knee rubs softly against my stockinged thighs.

My penis has now freed itself from between my legs and is rampant in the front of my panties. Carmel sighs sweetly in my ear as she softly kisses my lobe, her perfume mingling with mine to create a dizzy cloud that further heightens my senses.

"Michele, honey; you are so lovely," she whispers.

Her hand slides up my inner thigh and my penis pulses, the light rasp of her nails on my stockings sends waves of pleasure through my body. I pull her body harder against me and pull her soft lips against mine, our tongues intertwining in a sweet symphony. Carmel's hand slides under my skirt and I gasp as she tenderly strokes my erect member through my silky soft nylon panties.

I suddenly realise what I am doing!

"No! Stop! This isn't right!" I cry as I push Carmel's body away from me.

Carmel lowers her face to mine again and tries to kiss me but I squirm and turn my head away.

"Fuck off you pervert!" I sob.

"This is sick; I won't be like you! I won't submit to this twisted, sick existence that you and your perverted friends seem to enjoy. Get off me you fucking transvestite hag!"

Carmel pushes herself over me so that she is straddling my waist, the split in her skirt is wide open and the garment has ridden up around her waist. She grabs my wrists and pushes my hands back behind my head locking them there. She looks into my eyes with a cruel sneer on her face, her pale makeup making her look much more like a vampire because of her pale skin, red lips and dark made-up eyes; her teeth glint evilly in the lamplight.

"Well 'Little Miss I'm too good for you', I guess we have tried being nice. Obviously you only understand pleasure when it's forced upon you. We know you have really enjoyed the night's proceedings; Eddie told me you came when he fucked you and that bulge there in your knickers is a dead give-away." She sneered.

"Charlotte, plan B," she laughed.

I am pinned down with Carmel straddling me, forcing my hands back against the bed-head I twist my head to the left to see what Charlotte is up to. She rummages in the drawers of my dresser, gives a triumphant yelp, and comes over towards the bed with a pair of stockings in her hands. Before I have a chance to move she has lashed my left wrist to the iron bedpost and has started working my right.

I fight and buck trying to dislodge Carmel and pull my arm free from her grasp, but I am spent from the evening's ravaging and eventually I give up. Charlotte lashes my right wrist to the other iron post with the remaining stocking. Again I am forced to succumb to my captors.

"There now that's better; our spoilt brat has been tamed," gibes Charlotte.

"Now Michele, I'm going to tie your ankles to the bed just like your wrists and if you struggle Carmel is going to belt you; aren't you dear?"

"Oh please struggle honey, there's nothing more I'd like than to belt you one across your smug, pretty face." Carmel replies.

'Why are they being so cruel' I think to myself, bewildered. 'They had so been so nice earlier on!'

I submit while Charlotte finds another pair of my hose and lashes my ankles to the bed-base; she has to tie one end of the stockings to the steel bedpost and the other to my ankles because my feet do not reach right to the end of the bed. This allows me some small movement in my legs due to the stretchiness of the nylon stockings.

"Now; lets get started shall we?" smirks Carmel to Charlotte.

Carmel lowers her heavily made-up face to mine once again. I struggle and turn my face to one side to evade her kiss. Whack!!! Carmel slaps my face with her open hand.

"Come on Michele, you liked this before, now stop playing coy," she smirks.

Carmel lowers her lips to mine as I force myself to hold still while she does to me what she wants. Her soft lipsticked lips gently press themselves against mine, my lipstick smears and mingles with hers as she pushes harder and her lips crush themselves on mine.

Carmel's tongue pushes between my lips and slowly slides over my teeth. I capitulate and open my mouth and run my tongue against hers and taste her sweet mouth. My penis hardens again and rustles against my nylon panties. Then I feel a cool hand slide up my stockinged leg and under my skirt; it strokes the top of my thigh and slowly the fingernails scrape up the bare skin where my stockings end and up to the bulge in my silken full-cut panties. The nails slowly scrape across my nylon-encased cock and I sigh into Carmel's mouth and push my lips harder against hers. I surrender; the stimulation is too much.

I realise that Charlotte has moved down the bed and it is her ministrating to my engorged penis. The feeling of Carmel's soft lips against mine, her silken body straddling me as she forces her kisses on me, and the slow torture of Charlotte's fingernails against my panty-clad member are too much to fight against; I push against my bonds lifting my face to reciprocate Carmel's kisses and raise my skirted ass up off the bed to encourage Charlotte's caresses.

"Oh the bitch likes this after all; maybe all she needed was a little persuasion," Charlotte giggles.

"Let's try some more persuasion and see what happens," she laughs.

I feel my skirt being rucked up and bunched up around my waist. I can't help but assist by raising my ass off the bed; Charlotte now has my hard cock firmly gripped in her hand through my sheer nylon panties and is slowly working her fist up and down it; the feeling is delightful. Carmel has adjusted herself so she is lying on top of me, her upper body encased in her skin-tight silky dress is pushing against my satin blouse crating little butterflies of sensation. One hosed leg slides up and down my stockinged leg driving me wild with lust.

Charlotte's hand reaches inside my panties and frees my erect member pulling it out of the waistband; she strokes it gently now, slowly up and down, dragging her fingernails over the sensitive glans at the top of the up-stroke. I groan again.

"Oh Carmel! Oh Charlotte! You naughty girls!" I whisper into Carmel's mouth as she continues to kiss me deeply.

She is now stroking my face and pulls her face away from mine briefly; she looks in my heavily made-up eyes and whispers back,

"I knew you would like this; I'm going to make this special for you Michele."

Carmel then lowers her luscious lips to mine and we continue our passionate kiss. Then I feel Charlotte's hot breath on my thighs, she is kissing my stocking tops as she slowly wanks me with one hand and caresses my panty-clad balls with the other. Her kisses move up my thighs and across my nyloned balls and then I feel her hot wet mouth engulf me.

I groan again and rise my ass up off the bed in acceptance of Charlotte's oral worship of my shaft. My tongue is wildly exploring Carmel's mouth and I strain against my bonds to kiss her harder. Charlotte is working her mouth up and down up erect member, her tongue fluttering against the glans. I am close to coming. Carmel pulls her face away from mine briefly and whispers,

"Look!"

I raise my head as much as my bonds will allow and look down my body as Carmel slides over to one side so as not to obstruct my view. Looking down I see my legs spread; my ankles tied with the stockings which are lashed to the bedposts. I see my slender legs encased in silky flesh toned stockings, the reinforced nylon stocking heels visible in my strappy white high heels. My white leather miniskirt is bunched up around my waist and there is Charlotte's head buried in my groin.

Charlotte lifts her head slightly and turns to look up at me; she is beautiful for a plump girl. Her face is framed by the shocking, frizzy, bottle blonde wig with pink and blue streaks running though it, her heavy makeup with black eyeliner, dark pink and powder blue blush, and glittery multi-coloured eyeshadow. Her glossy bright red full lips grip the shaft of my penis.

"See," giggles Carmel, "I told you we came to comfort you."

Carmel now straddles me again and as our nylons rub my cock spasms in Charlottes mouth.

"She's ready for you Carm," Charlotte declares removing her head from groin, "and you better be quick!"

I wonder what she means……………..

Then it dawns on me as Carmel adjusts her position over me, she reaches under her dress and I hear a ripping sound as she tears the gusset seam of her pantyhose with a fingernail.

"Just relax honey," she whispers and kisses me briefly.

Then she adjusts herself again so that she is sitting over me with her lovely ass over my erect penis. She hitches up her dress. With one hand she pulls aside her panties and torn pantyhose gusset whilst with the other she grips my penis and positions it against her puckered anus.

Carmel slowly lowers herself onto me and I slide into her all the way. She pushes down and her panty-clad ass cheeks rest on my thighs; the nylon of her panties and torn hose rub against my shaft and balls as she slowly starts to ride me, putting her hands on the bed behind her to support her weight as she fucks my rock hard clitty.

Charlotte moves up to the top of the bed and begins to kiss me slowly, her tongue throbbing in my mouth as my penis throbs deep in Carmel's ass. My cock feels so snug and tight as Carmel rides me, her sleek back passage spasming against my invading member. Carmel is groaning and moaning,

"Oh Michele, fuck me!"

"Michele Fuck Me!"

"Michele………FUCK ME!!!!!"

I am delirious with passion, my clitty is trapped deep inside Carmel and as she rides me I push up to meet her as she slams her pantied ass against my groin. My silky lingerie is sending little explosions into my groin where it comes into contact with Carmel as she bucks over me, the rustle of silk, and nylon and satin becomes the background music to our groans and sighs as we approach orgasm.

I open my eyes because has Charlotte stopped kissing me, I am disappointed because her lipstick kisses were adding so much to my stimulation. I turn my head to see that Charlotte has freed her short stubby cock from her panties and is viciously wanking it. She looks down into my eyes and I see the pleading there.

"Please?" she whispers.

"Ok," I whisper in capitulation.

Charlotte kneels on the side of the bed, her stubby clitty sticking out from her groin, her sleek dance tights are pulled down and her fishnet stockings strain on the red garters where she has roughly adjusted her underwear to allow access to her angry little cock. She has pulled off her Lycra mini and dropped it around her high-heeled feet.

I can't move my head too far because of my bonds but I turn my head to one side and greedily suck Charlotte's hard fat clitty into my mouth. It tastes salty but clean and I immediately begin to suck it and slide my tongue all over it. The sight of my fellatio act must have aroused Carmel further because she is now bent forward over me and is slamming her ass up and down on my cock in a frenzy. My penis is now throbbing with excitement and I can feel my orgasm build as Carmel's hot ass pulses against my cock and drives itself up and down my shaft.

Charlotte is now groaning in time with Carmel as I suck and lick her fat little hard clitty-cock. I can feel it begin to spasm.

"Fuck me Michele!" Groans Carmel.

"Suck me Michele!" Groans Charlotte.

And I do! I fuck and suck and I come! My penis explodes deep in Carmel's ass and I rise up to thrust it in as far in as it will go. Carmel responds and pushes down grinding her pantyhosed ass against my panty-clad balls as I unload steam after stream of hot semen deep in her back passage. At the same time Charlotte grips my head and pulls my face into her groin as she jets huge globs of her seed into my mouth.

The experience an orgasm like nothing I have ever felt. My cock is exploding with the friction and pulsing of Carmel's tight ass; my balls are electrified by the sensation of Carmel's panty and hosed ass rubbing against their silky nylon panty prison; my mouth and lips are on fire as I suck and swallow Charlotte's hot seed, the feel of her stubby member invading my mouth is beautiful; and all over my body, the silky satin feel of my lingerie, skirt, blouse and stockings is amplifying the electric pulses of the most fantastic orgasm of my life.

After about three minute of intense pleasure, Charlotte removes her flaccid penis from my mouth; a trickle of her spend drops onto my chin as she tucks her angry little weapon back into the gusset of her sheer dance tights. Carmel eases herself off me, giggling as my cock plops out her ass. She stands next to the bed and adjusts her clitty inside her hose and panties and smooths down her black satin sheath dress. It's only then I notice the semen stains on her underwear and realise she has ejaculated whilst I was fucking her.

I lie there, my hands and feet tied, my skirt hiked around my waist; nyloned legs spread, my slowly deflating penis sticking out of the waistband my sheer panties. My makeup is smeared and wig tousled due to the passionate struggle I have just endured and enjoyed. The single drop of Charlotte's semen glistens on my chin.

"That was wonderful!" whispers Charlotte.

"Wonderful!" whispers Carmel.

"Wonderful!" I whisper.

"Fucking wonderful ladies; I really enjoyed the show. Now who the fuck gave you permission to play those sort of games!"

Oh my God! It's Eddie. He's looking though the bars of my workroom cell pushing his sticky, gnarled cock back into his pants. A pool of semen glistens at his feet in the low light.

"Now; how the fuck am I going to punish you girls for using something that I own and that everyone else has to pay for to use!"

"YOU!!!!!" he screamed pointing his shaking finger at the three of us.

 

 

To be continued……………………………………………….

Her spreading tummy was held in place with a full girdle with attached suspenders. Her ever expanding, slightly saggy breasts could be controlled and displayed to advantage with the right bra. Her face just needed more makeup than she used to use when she was younger, so she wore lashings of it. Finally her hair was always perfect, no demure bob or modest perm for our Pamela; she wore her hair big, high and sassy. ‘Mutton dressed as lamb,’ her Mom would have called her; but that was Pamela’s look. Her regular punters loved it.

Pamela had been a prostitute all her working life. She had held the odd regular job here and there, but always came back to the game. From the moment she had turned fifteen when she noticed the boys furtive glances at her breasts and her uncle Bill’s awkward but repeated attempts to look up her skirt and the lump in his pants when he hugged her (which he tended to do way too often and for far too long for propriety); she knew that she had something men wanted. It didn’t take her long to figure out that they would pay for it too. She fell into prostitution the way some of her girlfriends fell into jobs such as hairdressing or as shop assistants; it was just the job that best suited her.

Pamela had started working at her aunt Doreen’s modest establishment when she turned sixteen. Her mom had raised no objection. To supplement her meagre wage, every now and then her mom had taken in the odd lodger who sometimes paid extra for the privilege of sharing her mother’s bed. Her dad had run away when she was still in nappies and she didn’t remember him. Pamela dutifully gave half of everything she earned to her mom.

At Aunt Doreen’s she had learned the ropes so to speak. At first most of her customers were men who wanted a younger, prettier girl than their wife or current girlfriend. As she grew older she got the men who wanted an experienced woman who would do all the things for them in the bedroom that their wives and girlfriends wouldn’t do.

Pamela would do almost anything within reason providing the punter paid her enough. She had done some kinky things in her time, everything from mundane requests for fellatio to dressing punters in frilly knickers and spanking their bums. In fact light bondage and discipline work was her forte and she often took down punters into the special ‘dungeon’ room in the basement. However she would have nothing to do with the heavier, perverted stuff that was sometimes requested.

She refused any requests for sodomy, role-playing involving rape or incest, heavy sado-masochism; and as for anything involving pissing and other dirty acts; who were these perverts anyway? Go to Germany for fuck sake! The Germans seemed to make all the 'adult' movies involving those revolting acts.

In her mid thirties Pamela’s mother had died and she had finally moved out of her mom’s old home and at the same time moved out of Doreen’s establishment. She set herself up in a nice little flat and only saw her regular customers or those punters who came to her recommended by trusted friends. In her late thirties and her early forties her regulars had dwindled away to almost nothing. They had moved on, found younger women, or just stopped paying for sex. Older and bolder but still attractive enough to pull the punters she had started working the streets.

She could get a legitimate job and with the added income from her few remaining regular customers she could probably make a decent living working at one; but Pamela was prostitute; that’s what she did best, so that’s what she did.

Life on the streets was harder, but Pamela was no mug. If a punter was nice and looked like he had enough money she took him home for a 'full service'. If the punter only wanted a quickie, was half pissed, or didn’t have the money for a full service she would blow him or have him fuck her standing up in the doorway. The doorway in the dark disused alley had become her workroom. She would stand on the main road displaying her wares and until she hooked a short timer, then she would lead him down the alley and into the doorway to complete the transaction. The better clientele had a short walk to her flat.

Pamela, like all prostitutes, had had her share of bad experiences. Safe in Aunt Doreen’s brothel there was always help at hand and the worst that had happened had been the odd abusive punter when she’d turned down a request for perverted sex. In her flat she only serviced regulars; but on the street it was different; she had had to deal with all sorts.

Occasionally a punter would try to get a freebie, but she soon learned to take the money as soon as she entered the alley and before her and the punter got to the doorway. Sometimes if the customer was too pissed or couldn’t come for some reason they demanded their money back. Once a punter had slapped her face and called her a whore before running off into the night, but mostly Pamela could handle any situation.

On this cold wet night Pamela’s life was about to change forever. Tonight she had invited the wrong punter down into the alley.

Pamela had been about to give up for the night when a punter approached her where she stood at the entrance to the alley. She had watched him walk past two or three other working girls who were huddled in their usual positions on the street. He looked them over and continued on until he came face to face with Pamela. He looked her up and down, surveying her from top to bottom.

Pamela was dressed in a white silk blouse under a short red leather jacket, a black leather miniskirt came to mid thigh, black seamed stockings, and matching red high heels completed the ensemble. Her hair was teased, and framed her mature but attractive face. She was heavily made up with lashings of eye shadow, mascara and eyeliner to accent her pretty blue eyes, her cheeks were heavily rouged and she wore bright red lipstick. The punters liked their girls to look 'slutty'; it added to their fantasies she thought.

"Now you’re my type of girl," the man breathed whisky on her.

Pamela appraised the punter. Dark business suit, mid forties, just going to fat, heavy but handsome, a little drunk but sensible. He would do for her last quickie before she went home.

"Glad you like what see darling; it’s sixty for short time ok," Pamela made her pitch.

"Fucking expensive for an old pro like you ain’t it?" was his response but he stayed put and continued to gaze up and down Pamela’s body.

‘The ones with plenty of money always argued about the price,’ she thought.

"Look it’s sixty; short time in the alley. Take it or leave it; I’d as rather go home anyway!" Pamela snapped back.

"Ok! Ok darlin’; I’m hot to trot and your just my type, lets have you then," another cloud of whisky enveloped Pamela.

"Follow me, what’s your name?" she lead him just inside the alley.

"Mike," he replied.

"Let’s have the money Mike; then you get your honey ok?" Pamela gave him her best false smile.

Mike fumbled for his wallet and handed over the sixty. Pamela saw the wad of cash he had in his wallet and thought ‘Cheap fucker’.

Pamela took Mike’s hand and as she led him into the gloom of the alley, as they walked into the gloom Mike placed his hand on Pamela’s bottom and pinched; she brushed it away irritably.

"Hold your horses lover; here we are," she whispered as they entered her doorway.

The doorway was recessed far back into the disused building and no one was able to see them unless they came all the way down the alley. Pamela had never been disturbed here yet; then why would she? The building was disused.

Mike turned Pamela to face him and eased her back against the door; he pushed himself against her and tried to kiss her. She pushed him back and turned her face away from him.

"No lover; no kissing Ok? I don’t do that with punters."

"What do I get for my sixty then?" Mike asked his face puffed up and reddening.

"You get oral relief, and if you want you can shag me Ok?" Pamela offered her standard services.

"Can I fuck you in the arse then?" her customer went on insistently.

"Look sweetie you can have what I just offered; if that’s not to your liking take your money and fuck off; it's fucking cold and I’m tired!" Pamela laid down the law. What she didn’t need was the last customer of the night to be a difficult bastard.

"You slags are all the same," Mike cursed; "you come on all dolled up to get a guy horny then you won’t play the game properly. How can I shag you without a bit of a kiss and cuddle first hey?" Mike insisted, his voice getting angrier.

"Look I’m no slag and if you don’t behave you’ll get nothing ok?" Pamela had had enough.

"Alright, alright, give us a suck then sweetheart." Mike capitulated.

‘Thank fuck for that’ though Pamela ‘let’s get this over with and get home to bed.’

Pamela dropped to her knees, placing them on an old cushion she had bought to the alley not long after she first established the doorway as her 'workroom'. She had laddered her stockings kneeling on the bare brick floor the first night she worked here. Her face was level with the punter’s crotch and she reached up and unzipped his fly. Mike looked down at the overly made-up whore as her red fingernails slid down his zip and reached inside his trousers.

Pamela’s fingers freed Mike’s already thickening member from his underwear and pulled it out of his flies. ‘At least he’s nearly hard; he shouldn’t be too long coming,’ she thought; ‘not a bad sized one either,’ she couldn’t help thinking.

Mike watched as Pamela slowly stroked him until he was fully erect and then sighed as she bobbed her head down and took him in her mouth. His perfect fantasy was playing out perfectly in the dim gloom. A lovely older woman dressed as a tart was kneeling before him suppliant to his carnal needs. Mike looked at her heavily made-up face and pretty eyes as she looked up at him. Kneeling as she was, he got a great view of her large arse encased in the black leather mini and her seamed stockinged legs; he loved her red high heels, so whorish.

Pamela saw that Mike was staring at her face and body as she fellated him; she knew that punters liked to do that and she made a point of looking up into his face; she knew that really got them aroused. Hopefully this dickhead would come quickly she thought. Then she felt his hands on either side of her head. He held her in a vicious grip and began to brutally fuck her face. She couldn’t move her face away from his crotch and she was gagging on his cock as it forced its way all the way to the back of her throat.

Pamela started to pummel Mike with her hands as she gagged on his penis. Mike just held her tighter and continued to enjoy fucking her mouth.

"You love this don’t you, you whore. Don’t pretend you don’t. You’re all the same, you say you won’t do this and you won’t do that, but what you really want is good hard dirty fucking don’t you?" Mike was raving now.

"No kissing! No anal! Who the fuck do you think you are; I’ve paid my money and I’ll take what I want," Mike hissed as he held Pamela’s head in a vice-like grip and fucked her mouth.

Pamela had no choice, she couldn’t breath and Mike's cock was choking her, so she bit down on it. Mike screamed and pushed her away; Pamela lay sprawled in the doorway flat on her behind, her legs spread, her skirt rode up to reveal her stocking tops and red nylon panties.

Mike quickly recovered from the nip he had taken on his penis and looked at Pamela fallen flat on her arse before him. He looked up her skirt and his cock began to harden again; he looked at her heavily made up face and knew he hadn’t taken all he wanted from this whore.

"Fuck off!" Pamela shouted at him, "Fuck off and leave me alone!" she begged, hoping her cries would be heard by someone passing the alley. She knew her hopes were forlorn.

Mike moved in to take what he wanted. He reached down and slapped the whore hard across the face bringing tears to her eyes, she sobbed and her makeup started to run; her crying only served to arouse him further.

"Please, please don’t," Pamela pleaded, knowing she was in deep trouble.

"Yeah, that’s it bitch; you say please! You say please and I might be nice but don’t worry Mike knows what you need," he growled.

Mike dropped down between Pamela’s spread legs and reached up under her skirt and grabbed her panties. He tugged and pulled on the flimsy nylon garment until they tore free from her body. Mike bought the sheer panties up to his face and smelled the crotch; then he wrapped them around his tumescent member and gave it a few stokes.

"Nice knickers bitch; they're lovely."

Then he reached out and stuffed them in Pamela’s mouth. She tried to move her head from side to side but he slapped her again and pushed them deeper into her mouth, effectively gagging her. Then he grabbed her ankles and pulled her forward so that her spread legs straddled either side of his body; Pamela fell back hitting her head on the ground.

Mike had Pamela positioned prone in front of him with his throbbing cock inches from the entrance to her vagina. He pushed forward and thrust himself inside; right up to the hilt; Pamela groaned through the gag.

Pamela was dazed from the slaps she had received and from hitting her head on the pavement but when Mike lifted her legs around him she knew what was coming next. She braced as she felt Mike's huge member push past her labia and rudely thrust deep inside her. As a prostitute she had obviously succumbed to hundreds of erect penises inside her before, some a lot bigger than this; but this was different, she was being raped and she felt defiled.

Mike started to fuck Pamela with slow hard strokes enjoying her tight vaginal walls around his cock and loving the feel of her silken stockinged legs against his body. He was pleasuring himself at the expense of this whore. ‘What was it she said? No kissing right?’ he thought, then leaned forward and breathed his whisky breath into her face.

"I’m taking out the gag but if you scream I’ll knock you out you fucking bitch!" Mike panted as he continued to fuck her.

He leaned down over her and pulled her legs up around him in the missionary position and positioned his face in front of hers and took the panties in his teeth pulling the panty gag out of her mouth. Pamela gasped for fresh air but not for long as Mike started kissing her in a frenzy. He pounded his cock in and out of her in time with his tongue as it slid around her mouth. His hands ran up and down her stockinged thighs, laddering her expensive diaphanous stockings with his nails.

Pamela didn’t know what was worse, having her panties shoved in her mouth as a gag or Mike’s fetid breath and slimy tongue as he kissed her. His fingers were scratching her legs and tearing her stockings to ribbons. His penis continued to slide slowly in and out of her, she almost wished he would speed up the fucking and get it over with. ‘Maybe that was it?’ she thought.

Mike noticed a subtle change; Pamela was no longer struggling; in fact she was returning his kisses. Her arms had moved up to embrace him and she was rising her arse up against him to meet his thrusts. She was fucking him back!!!

"You fucking slut whores, you’re all the same, you just can’t get enough dick can you?" Mike groaned.

Pamela continued to play her game, ‘Get this guy off and then get to the police,’ that was the plan now!

"Yes Mike; give it to me honey; you know I need it," Pamela lied, convincingly she hoped, whispering into Mike’s ear.

Mike was lost in the pleasure of fucking this whore when a little alarm bell went off in his head.

"You fucking bitch! I know what you’re fucking doing! You need it hey? Well let’s see how bad you need it baby!"

With that Mike pulled himself off Pamela and looked down at her. Her coat was opened and he had managed to tear open her blouse revealing her large white breasts. Her skirt was dirty and rucked right up around her waist to reveal her red garter belt which were attached to her sheer black nylons now in tatters on her bleeding thighs. Mike groaned with pleasure at this picture of a woman ravished.

Mike reached down and grabbed Pamela by the hair and pulled her to her feet. He spun her around and slammed her face first against the door.

"So you need it do you whore! Well here it is!"

Mike kicked Pamela’s legs apart and positioned himself behind her. He pushed his now rock hard penis between her fleshy buttocks and rubbed it up against her fleshy labia to coat it with her cunt juices then pulled back and started to force it into her back passage.

Pamela couldn’t believe the excruciating pain she was feeling as Mike invaded her with his weapon. She tried to relax her sphincter but Mike just kept pushing himself slowly and steadily inside her. She thought that she felt herself tear and she screamed again at the intense pain.

Mike was passed caring about her screaming; he was living his ultimate fantasy raping this fat cow.

"Yeah baby that’s it; take it for Mikey; take that cock!" he chanted over and over.

Eventually he forced himself inside her as far as he could get, his crotch hard against her soft fat buttocks. Then he thrust in and out as slowly as he could, but he couldn’t hold back; the pleasure was just too much. He pushed forward and buried himself to the hilt in Pamela’s arse and exploded. Stream after stream of hot semen shot from his cock deep inside Pamela’s arse. Mike grabbed Pamela’s face and twisted it around so he could kiss and lick her as he shot his load.

Pamela was now numb with pain. She was barely conscious and only just aware of Mike anally raping her. The only thing keeping her on her feet was the pressure of Mike behind her as he fucked her and her will power to stay conscious. Then she felt him take a mighty lunge and bury himself even deeper inside her and she felt her insides tear again, the hot flood of Mike’s semen increased the pain of the wound. Then the sick fuck was kissing her. This maniac was kissing her whilst he raped her.

Mike collapsed against the prostitute as his orgasm subsided. He eased himself out of her and reached down and picked up the shredded red nylon panties off the ground. He wiped his deflating penis on them and spun Pamela around to face him. Her face was a mess, her makeup spread all over it. She just stood there in a daze.

Mike kissed her gently on the lips then pushed the come soaked nylon panties into her mouth, leaving half of the flimsy garment hanging out.

"Don’t forget your knickers," he laughed.

"Thanks for the fuck; keep the money bitch," he mocked as he disappeared up the dark alley.

Before she passed out Pamela made a vow: ‘This Bitch is going to get revenge!’

It took Pamela three months to recover from her ordeal. Somehow that night she made it home to her flat and called her Auntie Doreen who came straight around. Doreen didn’t ask her niece what had happened, she didn’t have to; it was obvious. Pamela never told her Aunt the details of what happened, she was too humiliated. Pamela’s wounds, internally and externally, healed quite quickly; it was her mind that took the time. She eventually regained her self-confidence and was capable of leaving her flat to shop and so on, but she needed to work; and there was only one thing she knew that she was good at. It was Pamela’s resolve for revenge that kept her going and got her through.

‘This bitch is going to bite back; one day I will find him and he will pay for what he did to me,’ became her mantra.

Pamela discussed going back on the game with Aunt Doreen who refused to entertain the idea of her niece working the streets again.

"I’m in my fifties now love, come back and work at my place, it won’t be long before you can take it over, I’m getting to old for this game anyway," she implored.

And so it was. Pamela went back to servicing punters at Aunt Doreen’s brothel. There was security there, both in the numbers of girls on a shift at any one time, and from Doreen’s live in boyfriend Steve. His nickname was "Iron Bar Steve" and he had once done a stint in Chelmsford prison where he worked as a 'hard man' for Eddie McManus who was the hardest man there and ran the jail from the inside. Steve was the bouncer at Doreen’s establishment and he kept the punters in line if they played up. Steve had been living with Doreen for nearly twenty years (except for his stint in Chelmsford); he was only in his forties, nearly ten years younger than Doreen but they loved each other, and Doreen confided one night after a few gin and tonics, that she still kept Steve more than happy in bed. In fact, she implied, they both enjoyed a very exciting and varied sex life.

Six months after she started working again Pamela got her chance for revenge. She was walking past one of the rooms in the brothel when she heard the unmistakable voice of her rapist coming through the door. It was Mike! He was ranting at Susan; the poor girl had him in room number two as a customer.

"You’re all the same you slags, dressed up in your sexy gear leading a guy on and then won’t do what he wants. Bitches! Fucking bitches! Now get over here and suck my cock!" he ranted.

It was him alright! The memories of the evening Mike had raped her in their alley came storming back.

Pamela’s heart began to race and she ran down the corridor to Doreen’s office.

"It’s him; the bastard who raped me. He’s here, he’s in room two with Susan!"

"Are you sure? Mike’s been a coming here for years off and on, he’s a bit rough but I never took him for a rapist?" Doreen asked, a concerned look on her heavily made up face.

Pamela broke down and fell into her Aunt Doreen’s arms sobbing, she told her every detail of what that man had done to her on that cold wet night. Doreen poured them both a stiff drink and they began to plot Pamela’s revenge.

"Revenge is dish best eaten cold," quoted Doreen, "Let's make the punishment fit the crime," she added.

Doreen and Pamela waited a week; during this time they planned Pamela's revenge and acquired the necessary items to ensure the punishment fit the crime. Mike was obviously a vicious woman hater; his litany of 'Bitches dressed up in sexy gear who won't do just what he wants,' was to become the basis of their planned revenge; a theme if you like.

During this time Doreen enlisted Steve's help; he was instrumental to their plan. Of course when Doreen told Steve what Mike had done to Pamela, Steve just wanted to smash his head in "I'll castrate the bastard!" he said; but Doreen went on to explain how her and Pamela's plan was so much better. And so, the trap was set.

Mike made his called the brothel about a week later and asked to see the sexiest girl available. Doreen took the call,

"Mike, you have been such a valuable and reliable customer over the years that I've booked you in for a special treat. My prettiest girl and I'll let you have an hour with her for the cost of your normal half-hour session."

"About fucking time you gave me something; I've been coming to your shit-hole knocking shop for years now and I have to tell you I never had anything for nothing and your slags always lead me on; they never give me what I want," Mike growled down the phone.

"Oh don't worry Mike; we'll make it up to you this time honey; you will get everything you deserve," Doreen sweetly answered.

"See you at six then honey; bye." Doreen hung up the phone then commenced dialling Pamela and Steve.

Mike arrived at Doreen's establishment at 6:00pm sharp looking forward to his special deal.

Doreen met Mike at the door and escorted him directly to the basement dungeon room. Doreen had dressed up specifically for the evening and although nearly sixty she looked very sexy in a whorish way. She was wearing a tight black leather mini, a white silk long-sleeved blouse, black stockings and shiny black patent leather high heels. Underneath she was wearing red silk camiknickers over a red satin garter-belt and a matching bra was visible under her sheer blouse. She wore lashings of makeup and her blonde hair was piled high on her head. She looked exactly what she was; an old prostitute.

"I hope I'm getting something better than you Dor'; you look real sexy but fuck your old enough to be me mum," Mike whinged as they entered the dungeon.

"Oh don't worry Mike, you're going to get exactly what you deserve!" Doreen flicked back across her shoulder.

As Mike passed through the door he noticed another sexily dressed older prostitute sitting on the bed in the centre of the room. Then he recognised her! My god it was the whore he had raped in the alley; then he felt a little sting on his neck and then nothing but blackness. Mike awoke some time later but he didn't know where he was.

He looked around groggily and realised that he was still in the basement of the brothel but he knew something was seriously wrong. Something just wasn't right, he couldn't move for a start and his clothes just didn't feel right on his body. The he realised he was bound to a chair. Both his legs were bound to the legs of the chair and his wrists were bound to the arms. Positioned in front of him was a full-length mirror; he couldn't believe what he saw in it.

Reflected back at him was a plump, overly made up whore. Mike looked her up and down. She had a blonde bob, her eyes were heavily made up with mauve and blue eyeshadow; black eyeliner outlined her heavily mascaraed lashes. Her foundation and face powder had been thickly applied; her rouge was just as heavy and bright red lipstick completed her whore's painted face. She wore a large gold choker necklace and matching drop earrings.

Next he noticed her clothes. She wore a long-sleeved blouse of sheer nylon; he could see a black brassiere through the sheer material. The garment had ruffles at the front of the decolletage that came all the way up to her neck so that no cleavage was visible, although she had huge tits straining at the front of the blouse. Where the cuffs ended, her wrists were tied to the arms of the chair but he could see her red painted whore's fingernails.

She wore a red lycra miniskirt that just covered the very tops of her thighs; because she was lashed into the chair it bulged a little at the waist around her potbelly. Her legs were encased in sheer taupe stockings that glistened in the overhead light; on her feet were bright red high-heels. He could see her stocking tops where her skirt was hitched up around her thighs and he saw the silver glitter of her garter snaps at the end of the black suspenders that lead under the mini to the suspender belt. Her thighs were slightly opened and he glimpsed the gusset of a pair of black satin panties.

Each of her slim nyloned ankles was firmly bound to a leg of the chair in which she sat. Then it dawned on him; he was looking at himself!

Then he started to realise the strange feeling of the clothes on his body. The sheer hose on his legs were light and sexy; they felt like gossamer silk sheathing his legs. His cock and balls were encased in the softest of satin panties; they gently caressed his sex organs and the cheeks of his bottom. The skirt felt strange but sexy as the tight lycra spandex squeezed his potbelly and thighs. The blouse was made out of the sheerest of gauzy material that he had ever experienced and it lightly caressed his upper body. He could feel the bra underneath the blouse snug against him, a light padding material was obviously being used to fill out the bra cups to create the huge false tits.

He could also feel and taste the makeup on his face. The lipstick tasted sweet and slightly greasy but pleasant; just like it tasted when he kissed a woman. But the most disturbing thing, besides waking up to find himself dressed as a whore, was that he could feel his penis starting to harden in his panties. He wasn't sure if he aroused because he was attracted to the cuddly crossdressed whore he saw in the mirror (she was certainly dressed just the way he liked his women to dress) or because of the sweet caress of the lingerie and female clothing on his body.

But why was he dressed like a crossdressed whore; and more importantly why was he lashed into this chair? Both questions were about to be answered.

"Well don't you look pretty Mike," he heard a woman's voice coming from behind him; it was dripping with sarcasm.

Then Pamela stepped forward and came into his field of view. Although it had been a while, Mike recognised her immediately; it was the prostitute he had raped in the alley.

"What the fuck are you doing here. I fucked you once and you weren't up to much love; give up the game before your cunt falls into your arse!" he snapped at her contemptuously.

Whack! His head snapped to one side as she slapped him upside of his face. Then though teary eyes he saw Doreen walk in front him; she looked sexy. She had disposed of her miniskirt and blouse and was standing there in her red silk camiknickers, matching bra and a red satin garter-belt holding up her sheer black stockings; shiny black patent leather high heels completed the ensemble. Her heavy makeup had been touched up. Dressed only in her lingerie as she was, she looked quite dominating.

"Well fuck me Doreen, you don't look too shabby for a wrinkled old cunt!" Mike snapped again.

Whack! Whack! This time it was Doreen who slapped his face; she stumbled on her heels she hit him so hard.

Mike shook his head and this time took a good long look at Pamela; she looked very different tonight. She was wearing a black corset and waist cincher. It looked to be made of a satin material and although Pamela was plump it cinched in her waist, emphasising her large breasts and buttocks. Suspender straps ran from the garment down her plump thighs and were attached to black seamed nylon stockings. Her feet were shod in the highest of high heels he had ever seen. The ensemble was completed with bright red nylon panties.

Pamela had on her usual lashings of makeup, this time very dark and Goth like. Black eyeshadow, eyeliner, mascara, pale foundation and powder, but bright blush and bright red lipstick and matching fingernail polish. She wore a black wig and her hair was worn high almost like a beehive. She looked every bit the dominatrix.

"What the fuck do you old whores think you're doing! When I get out of this chair I'm going to slap you both until you bleed, then fuck you senseless, just like I did to you that night in the alley you silly old trollop!" he spat at Pamela.

Whack! This time the blow was so hard that the chair fell over with Mike strapped in it; it was no slap it was a full-blooded punch delivered into his right side.

Someone with great strength lifted Mike upright, still strapped in the chair. Now he was scared. Then Steve walked into view and he got really scared.

"What the fuck is this about? What's happened to me? Why am I dressed this way? Why am I tied to this chair?" Mike pleaded through the pain in his side where he had been punched.

"Well Michele," Steve began.

"NO! NO! Fucking NO! My name is Mike!" the crossdressed slut tied to the chair cried out.

"Well you see Michele," Steve went on as if Mike had not said a word, "I have decided to name you that because you remind me of a girl I knew in Chelmsford Prison. She wasn't really a girl of course but she was prettier than you and a lot better behaved once we tamed her."

"So I've named you Michele, and the girls here agree it's a good name; and of course they also agree that you need to be tamed. In fact this was their idea; mostly Pamela's, but then again you raped her you cold blooded cunt, it's only fair that she choose your punishment!" Steve went on.

"You can't! You can't!" Mike/Michele tried to go on but Steve shut him/her up with a 'bitch slap' across the face.

"Just shut the fuck up and listen. Your punishment has been designed to match your crimes."

"You continually complain that the girls get dressed up all sexy and then lead you on; that is, won't give in to your perverted whims, so you knock them around and abuse them."

"But most disgusting of all, you raped Pamela and left her on the ground in that cold dark alley. Now you are going to get the same treatment," Steve said matter of factly.

"Oh n…" Michele tried to interrupt and received another bitch slap.

"So we lured you here, drugged you as you walked into the dungeon for your 'freebie', shaved your legs, and turned you into a woman. Dor and Pam have done a miracle and turned Mike into Michele!"

"It took some doing, shaving, dressing and making you up while you were unconscious but the girls said it was pleasant work knowing what they were going to do to you eventually." Steve finished.

"Oh it was disgusting touching you after what you did to me," Pamela said, "but it will be worth it!"

"Now you look exactly like what you have always despised and abused; a fat old whore dressed up sexy and ready to work!"

"And now we are going to give you what you gave me; pain, humiliation and abuse! You can cry and scream all you like; this room is soundproof."

"We are going to rape you!" Pamela finished.

Mike realised now what had happened to him and how much trouble he was in. He started to whimper.

"Oh shut the fuck up Michele; shall I shut her up for you Pam?" Steve asked Pamela.

"Any way you like!" Pamela shot back.

Steve pushed the mirror out of the way and stood in front of Michele. He could see the tears in her eyes and her mascara starting to run down her pretty cheeks.

"Fuck you! You get the same sympathy you showed Pamela," Steve spat at her.

Steve unzipped his fly and extracted his semi hard member. Another 'Michele' in another time and place (a few years ago in Chelmsford Prison) had described his cock as monstrous the first time he hade her suck it, and the description was apt. It was only seven inches long but it had a massive girth and ended in a gnarled purple knob; thick red and blue veins stood out all along the length of the monstrosity.

Steve reached out and grabbed Michele's head in both of his strong hands. Michele looked up, she had a pleading look in her eyes but Steve would have none of it. He released one hand and placed it on his semi erect penis and began to rub it all over her face. Michele was horrified; the feeling of the slimy member being rubbed on her cheek, over her chin and even in her eye socket was sickening. She opened her mouth to protest and Steve took the opportunity and pushed his now erect cock over her lipsticked lips and into her mouth.

Pamela and Doreen looked at the man they had turned into Michele being abused and degraded by Steve. Doreen was not concerned that Steve enjoyed forcing himself on the crossdressed whore, he had told her of his adventures in Chelmsford; and besides they had a very kinky sex life and allowed each other to take multiple partners anyway.

Pamela and Doreen looked at each other and smiled; this bastard was getting exactly what he deserved; a dose of his own medicine.

"Stick it to her Steve," Pamela goaded Steve on as he forced his turgid member into Michele's unwilling mouth.

Steve smacked Michele across the face again drawing blood from a small cut inside her mouth.

"You take this bitch or else I will break your fucking jaw!" he swore.

Michele could only capitulate, she opened her lips and felt the hard spongy mass of Steve's cock enter her mouth. She tasted her own lipstick, the salty taste of her own blood and another slightly salty sweet taste that could only be Steve's pre-seminal fluid leaking from the eye of his cock. Michele gagged as Steve forced his cock into her painted mouth right up to the hilt, his balls resting on her powdered chin. He groaned.

"Take that you slut!"

Pamela now had her first taste of her revenge as she watched Steve's cock disappear fully inside Michele's mouth.

"Yeah, take that you fucking whore! How does it feel you dumb cunt! Take that cock you fucking rapist shit, I hope it fucking chokes you!" She spat at Michele.

As Pamela and Doreen started to savour their revenge, Michele felt utter humiliation. Steve began to fuck her mouth; his hard member pistoning in out of her lips as Steve held her head steady and stood between her splayed legs fucking her face. Michele felt the hard cock sliding between her lips, over her tongue and slamming into the back of her throat. 'My god, how do these girls willingly give head,' she thought as her mouth was raped and she gasped for breath.

Then Michele couldn't believe what happened next, she felt a hand caressing her nyloned thigh. The hand was stroking up and down from her knees to the very tops of her thigh and sometimes disappearing under her skirt and stroking her pantied crotch. It was Doreen! Michele looked down and saw the old hooker was kneeling beside her chair, Doreen's hand was under Michele's skirt stroking and rubbing the sleek material of her stockings and panties.

Michele found what happened next even harder to believe; she started to become aroused, her penis hardening in her panties. Steve continued to drive his cock in and out of her painted mouth and was quickening his pace. Michele felt Steve's penis become rock hard and start to throb; she knew what that meant, Steve was building to his orgasm. Oh Christ, she was about to get a mouthful of semen. But what the fuck was Doreen playing at?

Doreen had now lifted Michele's skirt and was rubbing Michele's penis through her silky satin panties. Michele had started to harden and Doreen grasped her penis and started to wank her. A small telltale wet spot appeared in Michele's panties; she was enjoying the forced masturbation even while Steve was raping her mouth.

Michele had now got used to Steve's member thrusting in and out of her mouth. Although she was not enjoying what Steve was doing to her, she had come to tolerate it. She couldn't understand how she could be so sexually aroused though. Doreen was stroking her hard cock through her panties and she was getting harder and responding to the luxurious stimulation of the satin panties being rubbed against her member. Michele actually started to buck in the chair thrusting her pelvis in time with Doreen's strokes. This also caused her head to bob up and down, inadvertently providing stimulation to Steve's hard cock in her mouth; he could also feel her tongue starting to work around his cock lashing at the sensitive underside of his penis.

Michele was now concentrating on the feeling of Doreen's ministrations to her sensitive penis. Doreen had now slid her hand inside Michele's panties and as the painted fingernails of one hand raked her scrotum through the satin panties, the other was wrapped tightly around Michele's shaft and was viciously wanking the hard member. She was half choking on Steve's penis and was working her tongue around it to try and squeeze more air into her lungs as Steve pulled back enough to let her breath.

Steve took Michele's bobbing and bucking as capitulation; her movements were certainly increasing his pleasure so he slowly released his grip on her head. Michele was now sucking in time with Doreen's wanking and she hadn't even realised it. She felt Steve's cock stiffen and convulse in her mouth and suddenly realised he was about to ejaculate.

'Oh my God,' Michele thought. 'This cunt is going to come in my mouth and I'm fucking encouraging him. What the fuck am I doing?'

Pamela was standing back watching the first part of her plan come together. Mike sat there dressed as Michele tied to the chair. Steve stood between her stockinged legs his thick cock sticking out of his jeans, Michele's lipsticked lips sucked on his cock as he thrust in and out of her mouth. Doreen kneeled to one side of the chair with her hands in Michele's lap. Michele's penis was sticking up proud out of the waistband of her black satin panties as Doreen wanked it furiously with one hand and stroked her scrotum through the panties with the other. Michele's miniskirt had been rucked up around her waist and as she bobbed and gagged on Steve's cock she looked just like the whores she had abused. Heavily made up, short skirt, stocking and high heels; sucking a cock just to get it over with; she had in fact become one of the whores she hated and used and abused.

Pamela smiled as Steve groaned; she knew what was coming.

Michele felt her own climax building; the frenetic wanking Doreen was giving her cock coupled with the strange but luscious sensation of the silky satin and nylon lingerie was just too much pleasure for her to bear; she needed release. At the same time she knew that Steve was about to ejaculate a disgusting mess in her mouth but there was nothing she could do about that; her orgasm had taken control of the situation and she felt it build and start to explode through her womanly body. Her cock-clitty started to spurt.

At the same time she heard Steve groan and felt his cock convulse in her mouth. Stream after stream of thick, ropy, semen filled her mouth. At the same time Steve grabbed the back of her head and pushed her face hard into his groin; she couldn't breath because he held her so hard against him and the flood of semen that filled her mouth. Michele started gag and retch on the semen flooding her mouth; she swallowed what she could but streams of the viscous fluid poured out of her nose because she couldn't swallow it fast enough. Also her own orgasm had just commenced and she started convulsing as the first jet of her own spend erupted from her penis; which was being wanked furiously by Doreen.

"Now!" screamed Pamela.

And Michele suddenly felt the most excruciating pain ever. As the first stream of ejaculate left Michele's clitty Doreen heard Pamela's cry and with her other hand she squeezed Michele's scrotum as hard as she could; at the same time she viciously twisted and squeezed her penis. Michele's orgasm came to an abrupt halt and she nearly passed out with the pain.

In the space of one second Michele had gone from the ecstasy of orgasm to the most cataclysmic pain she had ever experienced. Her cock and balls felt like they were on fire; the pain made her gag and she fought back the urge to vomit. She knew that would be fatal as Steve was still in the throes of his own orgasm and the last streams of his semen were shooting into her mouth. She tried to swallow the salty mess but her gag reflex was making her choke. Steve's sperm was flooding her sinus and running out of her nose making it impossible for her to breathe; she was sure she would die.

On the other hand Steve used Michele's choking and shuddering to increase the pleasure of his own orgasm; he pressed Michele's head harder into his crotch and as the last of his discharge pulsed out of him, he shuddered with the intensity of his orgasm. When he had finished he pulled his semi-hard member from Michele's mouth and rubbed his semen all over her face with his cock; her makeup mixed with his semen and her tears. She looked like a mess as she gasped for breath, choking and crying.

Pamela just smiled.

"So Mike, how does it feel to raped, you fucking prick!"

"Come on don't cry shit-head; you asked for it. I'll quote you if you like: ""You’re all the same you slags, dressed up in your sexy gear leading a guy on and then won’t do what he wants. Bitches! Fucking bitches! Now get over here and suck my cock!" "

"Isn't that one of your favourite rants; well now you know how it feels!"

"See Mike, or shall we say Michele, you asked for it. You just sat there all dressed up like a whore and in the end Steve had to take what he wanted. Sure, just like me you capitulated and tried to get Steve off; especially when Auntie Doreen started stroking you. But now you realise rape really is a violent act and there is no pleasure to be had by the person being raped!" Pamela finished.

"I'm so sorry," Mike/Michele shuddered, trying to breath deeply to combat the excruciating pain in her groin.

She was crying and gasping for breath. Tears streamed down her face, her mascara running and her lipstick smeared all over her face. The makeup was mixed in with Steve's spend and as she felt the sticky mess start to dry on her face she felt degraded and ashamed.

"I'm sorry; please let me go now. I've learned my lesson and I'll never abuse another woman I promise," Michele sobbed.

Pamela replied from across the room, her voice slowly getting louder as she approached Michele from behind.

"I don't think you have learned your lesson Mike. In fact I think you are far from it; but I'm going to take part in your final punishment personally; to make sure you know just how much I hate you"

"After all it's only fair that I get to do that; you raped me remember?"

"I'm the Bitch you left raped and broken on the filthy ground in that alley with her panties stuffed in her mouth; you remember? You told me; and again I quote: "Thanks for the fuck; keep the money bitch,""

"Well this Bitch bites back Mike! I spent the money you threw on the ground beside me to buy you a present in fact. Now open those come caked eyes and see what the Bitch bought for you!" Pamela exclaimed and walked around the to the front of Michele.

Michele looked up and horror filled her; she screamed…….."NNNNNOOOOOooooo!!!!!!"

"But Michele; I'm dressed just how you like your whores look!" Pamela teased.

What Michele saw when she opened her eyes was Pamela, still in her black corset and waist cincher; the suspender straps running from the garment down her plump thighs and attached to black seamed nylon stockings had now been adjusted slightly. The suspenders had been adjusted because protruding from the crotch of Pamela's bright red nylon panties was a huge black strap-on cock. Pamela rocked on her high heels and made the black rubber penis wobble inches from Michele's face.

"Remember what you did to me honey; well it's time for revenge; Steve, Auntie Dor, come and give Michele an attitude adjustment. You know what I mean; put her in an attitude that will allow me to use this on her," she smiled cruelly looking Michele right in the eyes.

Steve was standing to one side pushing his now flaccid cock back into his jeans. He zipped up and sauntered over.

"NO! NO! NO! NO! NO! NO! NO! NO! NO! NO! Pulleeeese don't" Michele begged and tried to tear herself free of the bonds holding her in the chair.

"Oh fuck this!" said Steve and punched Michele in the face, knocking her out.

Michele woke up to the stink of chemicals; then she realised that Steve was waving smelling salts under her nose. At first she couldn't figure out what was going on; in fact she thought she was still Mike having a bad dream. Then it all came flooding back as she started to feel the throbbing pain in her balls and the ache in her jaw from Steve's punch.

She realised now that she had been let out of the chair in which she had been bound but was now in worse trouble. She was locked in a set of stocks that Doreen kept in an alcove corner of her basement dungeon. Mirrors surrounded all three walls of the alcove, front and both sides, so she could she exactly what was going on. What she saw terrified her.

She still wore the long-sleeved sheer nylon blouse and the black brassiere was still visible through the gauzy material. Now where the cuffs of the blouse ended, her wrists were thrust through the holes in the extremities of the stocks, her red painted whore's fingernails stood out against the black wood of the contraption as she tried in vein to pull her hands through.

The red lycra miniskirt she wore just covered the very tops of her thighs. Her legs, encased in the sheer taupe stockings held up by the black suspenders, continued to glisten in the harsh overhead light; they were spread apart by a stainless steel spreader bar attached to her slim nyloned ankles and she could only just balance on her bright red high-heels. Michele realised she could hardly move at all. She could just swivel her head up and down and from side to side to look in the mirrors, her wrists and ankles were firmly secured. Then she realised something else; she was not wearing any underpants. Michele looked up and saw Doreen, who was positioned just to one side of Steve. Doreen was holding the black satin panties she had been wearing earlier and swinging them around her fingers.

She looked to the mirror in front of her and noticed her face had been cleaned and her makeup had been reapplied. The blonde bob was still in place, her eyes were heavily made up with mauve and blue eyeshadow; black eyeliner outlined her heavily mascaraed lashes. Her foundation and face powder had been thickly reapplied and with heavy rouge and bright red lipstick she was again the whore 'Michele'.

Then Michele remembered the last thing she had seen before Steve knocked her out; where was Pamela?

"Ok Pam, she's awake," Doreen called out.

"Well I guess it's time for the whore to pay her dues then; after all she's all dressed up and asking for it just like they all do; hey Michele?" Pamela teased as she approached from behind Michele. Michele looked in the mirror and saw Pamela approaching from the rear.

Michele saw the huge black rubber cock attached to Pamela and began to cry; she realised how vulnerable she was locked into the stocks with the spreader bar holding her feet far apart.

"Please, please don’t," Michele pleaded, knowing she was in deep trouble.

"Yeah, that’s it bitch; you say please! You say please and I might be nice, don’t worry Pamela knows what you need," she growled.

"Sound familiar Michele? We are saying to each other the same words that we said to each other on that night you raped me in the alley; except this time our roles are reversed!"

"Ok Doreen; gag the cunt!" Pamela ordered.

Doreen stepped forward and shoved Michele's black satin panties in her mouth. As she tried to spit them out Doreen pushed them in further until Michele was effectively gagged.

"Now," Pamela whispered into Michele's ear, "the Bitch bites back!"

Steve and Doreen both sat down on a couple of chairs that Steve had dragged over and began to watch the show.

"As I said to Pam; revenge is a dish best served cold, and we have certainly planned this to perfection," Doreen whispered into Steve's ear and gave his muscular thigh a squeeze.

Michele watched in fear as Pamela clicked across the floor on her high heels and positioned herself behind her. She couldn't see much, other than Pamela moving in directly between her spread legs. Then she felt her miniskirt being lifted up and felt a cold wet substance being squirted between the cheeks of her arse. She just had time to realise that Pamela had lubricated her arsehole when she felt the hard rubber cock intrude inside her sphincter.

Michele wanted to scream with pain but the panties stuffed in her mouth prevented her from doing so. She heard Pamela grunt and heard the click of her heels as she rose up and down on the balls of her feet as she began to force the cold hard weapon deep in her arse. She thought the squeezing Doreen had given her balls had been the worst pain she had ever felt but this was far worse.

"Give it to the whore!" Steve goaded.

"Fuck that cock hungry slut!" Doreen provoked Pamela to push harder.

"OHHGGGHH!!!" Pamela grunted as she forced her groin forward and pushed the rubber strap-on dildo as far as she could up Michele's arse. Then she reached down and flicked a switch on the base of the strap-on and it began to fiercely vibrate.

Michele felt her insides tear as the huge intrusive dildo ravaged her back passage. She wanted to scream but her panty gag prevented her from crying out. She started to cry again in pain and humiliation; her makeup running in rivulets downs her cheeks. It was bad enough that she was being raped; but to have Steve and Doreen watch and gloat was so degrading.

"Oh look Pam; she's doing the panda thing again!" Doreen exclaimed, "After all the trouble I that went too to fix up her makeup; the inconsiderate bitch!"

"Does it hurt your 'botty' Michele?" Steve laughed solicitously, "Don't you like a hard cock in your arse as much as you liked my cock in your mouth?"

Michele jerked and convulsed as she felt Pamela flick the switch that made the dildo vibrate in her behind. The pain was now almost unbearable and she thought she would pass out. Her back passage felt swollen and she knew that something in there was torn. When she thought it couldn't get any worse Pamela began to violently fuck her arse.

Pamela pounded the big black vibrating strap on dildo in and out of Michele's arse. The vibrating phallus pressing into Pamela's crotch through her nylon panties started to arouse her. She settled into a steady rhythm and concentrated on bringing herself off. She thrust in and out as hard as she could, both to punish Michele and to increase her own pleasure. Pamela started to spit obscenities at Michele.

"Yes Michele; take it honey; you know you need it," Pamela snarled into Michele’s ear.

"Come on honey you need it don't you? Well let’s see how bad you need it baby!"

"Remember those words you cunt; you said them to me while you raped me!

"You need it do you whore? Well here it is!" Pamela exclaimed and began to frantically rape Michele.

The thrusting and vibrating rubber cock was quickly bringing Pamela to orgasm. She had not expected this but she thought it only appropriate that as Mike had come when he raped her; she should come while she raped him.

Michele was now in agony as the hard rubber cock continued to violate her bowels; a slight pleasant tingle had started to grow in her prostate but the pain she felt overrode any pleasure she may be getting tenfold. She squirmed round and tried to move her arse away from her rapist but she couldn't move. All she could do was move her head and as she looked up into the mirror what she saw repulsed her.

Michele was standing spreadeagled tottering on her high heels, her long sleek stockinged legs forced apart by the spreader bar and her skirt was rucked up. Positioned between her sexy legs was a heavily made up chubby Goth vixen dressed in black lingerie, her sleek black seamed stockinged legs bent slightly as she balanced on her heels and fucked a hard black rubber cock in and out of her soft white arse. She was cursing and groaning.

"Take this you fucking bitch! I'm raping you back you cunt! I'm fucking your skag arse you whore!"

"And I'm commmmmmmming!!!!!!!!!!!"

Steve had been watching Pamela rape Michele and of course the inevitable happened; he became aroused and erect. He opened his fly and freed his hard chubby member and took Doreen's painted fingernailed hand and placed it around the turgid tool. Doreen began to absent-mindedly stroke Steve's cock; she was intrigued by what was happening before her eyes.

"My fucking god Steve, Pamela's actually enjoying raping that poor cunt!" she gasped.

"And I'm enjoying watching her too," Steve smiled as he hatched his own little plan in his head.

Then he saw Pamela begin to thrust in and out of Michele as hard and fast as she could and heard the obscenities she was screaming at Michele and he knew she was about to come. He made his own move and jumped out of his chair and moved it in front of Michele where she was locked in the stocks. He jumped up on the chair, his hard cock jiggling in the air as he held on to the stocks with one hand to keep his balance. Then with his other hand he began to furiously wank his cock in front of Michele's face. He looked down at her.

Michele was now silently sobbing; tears streamed down her cheeks as she weeped muffled cries into the satin panty gag that had been thrust in her mouth. She looked up and tried to implore Steve with her eyes but all she saw was his cock inches from her face as he stroked it and groaned with pleasure. His eyes were locked on hers but they displayed no pity, only lust. Michele's back passage was on fire; she could tell by the increased tempo of the ruthless fucking and by Pamela's grunts and groans that she was about to come. She just wished she would hurry before she exploded in pain. The monster cock was ravaging her insides and the crude vibrations only amplified the pain.

Then Michele felt Pamela drive the intrusive monster right up her, as far as it would go and push for all she was worth. Pamela was coming. Michele grunted in pain into the gag and screwed up her eyes. Then she felt the hot ropes of Steve's semen as he ejaculated in her face. She made the mistake of opening her eyes in surprise and a spurt of warm salty semen flew across her face and into her eyes. It stuck to her face and then dribbled down from her eyelashes and some of the viscous fluid went into her right eye and started to burn. Steve was moaning in ecstasy.

"Take that you fucking rapist whore! Take my spunk you fucking cowardly crossdressed hag!" Steve cried as came.

Pamela was pushing her groin into Michele's buttocks as hard as she could. The vibrating phallus was sending waves of pleasure through her pantied crotch as she pushed hard against Michele's arse to force the base of the vibrating rubber cock against her clitoris. She spasmed and bucked as her orgasm consumed her. Her stockinged legs rubbed against Michele's nyloned thighs, adding to the gathering circles of pleasure that raced up and down her body as she climaxed.

Her orgasm slowly subsided and she fell forward so that she was resting against Michele's imprisoned body. When she gained control of herself she pulled back viciously ripping the still vibrating cock from Michele's arse. A flood of lubricant, blood and other matter began to run down Michele's thigh and stain the top of her stocking. Pamela moved around to the front of Michele, the obscene strap-on phallus still pushed out in front of her like a lewd putrid figurehead.

Steve stepped down off the chair and pushed it back; his tumescent member hung out of his fly, the last drops of semen dripping from the gnarled knob.

Michele opened her one good eye, tears makeup and semen streamed down her face, the other remained closed due to Steve's semen still stinging her there. She was sobbing into the panty gag and obviously in tremendous pain. Pamela moved in and stood beside Steve.

"Was that good for you too bitch?" she asked sarcastically and ripped Michele's panties from her mouth.

Michele sobbed and moaned.

"Please………….no more!" she begged.

"Oh shut the fuck up!" Pamela spat back mercilessly. She took the black satin panties and wiped the last drops of semen from Steve's cock, cleaned the fetid mess of lubricant, blood and faecal matter from the strap on cock still attached to her crotch, and shoved the panties back into Michele's mouth.

She turned around to her Auntie Doreen and said,

"I think I've finished with this bitch for now!"

 

The End

Part V

 

Carmel rushed into the cell, or as she called it, my 'workroom';

"Come on Michele, the night's only just begun! The waiting room is full of punters, and because you are the new girl, you're top of the menu!" she said, busily fussing around me and helping me to my feet.

I allowed myself to be pulled up off the bed, and stood in front of Carmel (who until today I had only known as Craig).

"Look what he did to me!" I cried; "Look what that disgusting man did to me!"

"Oh shut the fuck up," Carmel crowed. "You'll get worse and you'll get better Michele; that's the life of a working girl here in Chelmsford!" the crossdressed freak standing in front of me explained matter of factly.

"That's just it!" I cried.

"I'm not a girl! I'm not Michele; my name is Mike and I'm a businessman not a woman! And you are not Carmel; some kind of bawdyhouse Madam; as you like to pretend! You're Craig! A guy in a dress, pretending to be a girl! You're just a sad, pathetic, transvestite prostitute living in some made up dream world inside this prison!"

"I'm a big name outside!" I cried.

"A 'Face'! As you jailhouse scum are want to say! I have money, friends, influence" I cried.

Carmel laughed out loud and slapped me hard across the face. I felt the sting though my tears.

"No honey! You have it all wrong! You're inside Chelmsford prison honey and you are whatever Eddie want's you to be!"

"You're Michele! You're Eddie's property; and you have about five minutes to get ready because customers are waiting!"

"Now pay attention, you really are on your own after I clean you up; a girl's got to make her own living too you know, I can't spend all night showing you how to put on makeup and how to dress" Carmel sneered.

She led me back past the five other cells that made up this section of E block. Low light leaked through the bars of the other cells; red shaded bedside lamps had been lit. I saw other 'working girls'; transvestite prostitutes, putting the final touches to their makeup, adjusting the seams on their stockings, or arranging their wigs. They sat on their oversize cots that had been made up with satin sheets; bold colours, black, red, and blue were predominant. One or two of them looked up with their painted faces and smiled at me; but there was no sympathy in their smiles; they were the types of smile that predators gave their prey just before they pounced for the kill. Four of the cells were occupied by Eddie's 'girls', leaving my 'workroom' and the cell across the passageway vacant. It dawned on me as I clattered along on my impossibly high-heels that the vacant cell directly across from me must be Carmel's 'workroom'.

We arrived at the bathroom at the end of E block again and Carmel helped me undress and sat me down in front of the highly polished stainless steel mirror. I washed my face clean and stared at the makeup arranged on the shelf below the small sink.

Carmel said, "Ok Michele; you’ve done this enough times tonight with my help; it's time you went solo."

Carmel lit a menthol cigarette and sat down on a stool beside me, preening herself in the mirror. She made minor adjustments to her own makeup as she sat there and smoked.

It was amazing how much I had learned in such a small amount of time. I took a damp sponge and applied generous amounts of foundation to my face and neck finishing with a slightly lighter coloured powder to set my face. I rouged my cheeks, eventually getting the hang of how to accent my high feminine cheekbones. Carmel had to instruct me again how to apply the rouge after my first attempt made me look like some kind of circus clown with rosy red cheeks. I then applied liberal amounts of eyeshadow, eyeliner, and mascara with minimal assistance from Carmel.

"You're getting the hang of it honey, although you do look like a bit of a panda, but you will become very good at it soon," said Carmel laughing at my efforts with the mascara applicator.

"Besides, the punters like us heavily made-up, it's not like were supposed to be their wives or Moms," She laughed wickedly and applied another coat of mascara to her own heavily made-up eyes.

I finished with another light dusting of powder and applied two coats of plum red lipstick to my pouty lips. Putting on the lipstick I had discovered, was the easiest part. I applied a touch-up coat of bright red nail polish to my toenails and fingernails where they had been chipped. I checked myself out in the mirror with a self-satisfied smirk. Not bad for my first solo effort I thought.

"Wonderful Michele; you are getting the hang of it now," Carmel cooed like I was a good pupil who had learned her lessons well.

Then I took stock of the situation. I had been concentrating on applying my makeup and was amazingly, feeling a shimmer of pride in my efforts! What the fuck was wrong with me! I had also referred to myself as 'SHE' in a number of my thoughts and more disturbingly had subconsciously thought of: 'MY makeup!' 'MY clothes!' and 'MY shoes!' What the fuck was happening to me! Was I turning into some kind of willing participant in this sick, fucked world that Eddie had created inside this prison!

I bought myself back to reality by concentrating on the debauchery I had suffered over the last couple of hours. I had been sodomised and orally raped; my back passage was still sore from Eddie's invading penis. I could still taste the swampy, salty, taste of 'Iron Bar' Steve's secretions which he had deposited in my unwilling mouth; and my ribs and stomach muscles still ached from the pummelling I had received from Eddie during the evening.

I looked in the mirror again and saw what I really was; a small, insignificant male prisoner forced to wear makeup and jewellery. A parody of a woman! A man compelled to dress up in women's clothes so that sick, twisted prisoners could take their carnal pleasures and somehow justify to themselves they were not gay because they took their gratification from a man who is dressed as a woman.

Carmel helped me into a satin robe and then scooped all of the makeup off the shelf and into a small makeup case. She took the wigs with their stands and loaded them into my arms she grabbed my discarded clothing and shoved it with my high-heels into my arms on top of the wigs. Holding the makeup case in one hand she took my hand and started to drag me out of the bathroom.

"Ok Michele, from now on this place is just for you to clean up, shower and shave. Don't leave any clothes, makeup or jewellery here or the other girls will nick it as soon as you take your eyes off it; and then you will have to pay for it to be replaced."

"Everything you need is in your workroom and only you, Eddie, and Mabel have a key."

"Who the fuck is Mabel?" I asked.

"She's an old lifer who likes to crossdress. She's really too old to shag, but some of the cons occasionally give her one when they are short of money. She's Eddie's minder for his stable of working girls. Steve is the muscle, and Mabel is the housemaid is the best way to explain it I suppose."

"Mabel comes around during the day and changes the sheets and washes our clothes. She'll replace your makeup and tend to your wigs. She also takes orders for new clothes, lingerie, and any special costumes when you need them; all done for a small fee, and all done with a smile, she likes to be around us girls," Carmel beamed. "She also takes our bookings and manages the punters in the waiting room."

"What the fuck are you talking about?" I asked Carmel, bemused.

"Look Michele I really don't have time for this; you used to be Eddie's bookkeeper so you should have it figured out by now. Half of every fee we get off a punter goes to Eddie ok. You will probably have to work for nothing for about three months to pay for the clothes and other stuff Eddie has bought you to get you started with. Once you start making money Eddie keeps it for you on a tab; Mabel will deduct your expenses and such and will also give you cash or goods when you need them."

I realised what Carmel was explaining to me of course. As Eddie's prison accountant I had indeed managed his books and was aware that he had someone else look after his 'working girls' and put money into and out of that part of the account; but all I ever saw were the profits. It never occurred to me how complicated this side of his business was.

"Hang on a minute; what the fuck are you are talking about? Expenses? Goods?" I asked.

"Jesus Michele! You just don't get it do you?"

"Everything is a business to Eddie. The clothes, makeup, wigs and so forth you have to pay for. You also pay to have your clothes washed and 'workroom cleaned'. You also pay when you order in more clothes, wigs, lingerie, shoes and stuff. Mabel will bring around the catalogue and an order form for you."

I mind flew back to the times I spent with Eddie as he made me order in women's clothes, nylons, makeup and so forth for his stable of working girls; but I never thought I would be wearing any of it!

"Sometimes if Eddie sees something he really wants to have you wear he'll buy it for you as a present," she smiled.

We had arrived back at my cell; my workroom as it I now realised it to be. Carmel pushed me through the door.

"Ok hun, its ShowTime; put those dirty clothes in the laundry basket, put your wigs and makeup in the wardrobe and get dressed. Try that long black wig hun, it will suit your makeup. As you can see Mabel has laid out your outfit for your first customer, it must be a special request, that's always good because have to pay more."

With that Carmel went through the door of her own cell, sat on the bed and lit another menthol. She punched a button on an intercom located on a nightstand next to her bed and spoke into it.

"Ok Mabel, send him in," she sang.

Carmel rushed across to my cell and pointed to an identical intercom on my bedside table.

"Oh, I forgot to tell you how this works. Its simple hun," she explained, "when the blue light is on you have a punter waiting. Press that button to talk to Mabel in the waiting room. Press that orange button to indicate you are busy, cleaning up whatever, and that red button there is the panic button."

"Press the panic button and 'Iron-Bar' Steve will be here in seconds. But only press it if you have genuine emergency," she advised me, slipped me a wink, and skipped out of my cell to the sound of approaching footfalls.

Genuine emergency! GENUINE FUCKING EMERGENCY!!!!

What could be more of a genuine emergency than being forced into being a transvestite prostitute in a fucking jail!!!!

I sat on the bed and controlled the urge to cry. I knew it wouldn't help; all I could do was to get through tonight and then figure out a plan to get of the indescribable mess I was in.

I looked down at the clothes arranged on the black silky sheets. A 'special request' Carmel had said; what the fuck? Resignedly I started to dress.

First I open the package of hosiery. It contained a pair of white, sheer to the waist pantyhose. As I slid the sheer nylon up my legs those little electric sparks of delight again ran through me. I hated myself for enjoying the sensation of it! The sheer waistband was snug around my tummy and I tucked my deflated little penis between my legs to be held there by the gossamer nylon gusset of the pantyhose. Next I slid a pair white full brief satin panties up my legs and pulled them snug around my bum and groin. The rasp of the silky panty material against my sheer hose was so sensual that I felt my little cock pulse.

I slid the matching white satin bra around my chest and went to the drawer where I knew my breastforms where kept and placed them neatly into the bra cups. 'My breastforms'…………what the fuck had happened to me!

I concentrated on getting dressed and tried not to think about the exquisite feel of the nylon and satin on my skin. A pair of plain white high-heeled pumps was at the foot of the bed and I slid my feet into them and stood up. A single pristine white cotton tunic was laid out on the bed so I stepped into it and pulled it up my body. As I started to do up the buttons on the front of the tunic I realised what it was. A nurses uniform; 'Special Request' in-fucking-deed!!!

As recommended by Carmel, I placed the long, raven haired wig on my head, adjusting it in the mirror on the wardrobe door. I picked up the little white nurse's cap with the Red Cross on it and placed it on top of my head. I looked stunning!

In the full-length mirror was the image of gorgeous nurse in a crisp white tunic buttoned to her throat. Her long legs shimmered in gauzy white nylons below the knee-length hem of her skirt. Her legs terminated in the pristine white high-heeled pumps. The nurse lost all credibility however when you looked at her face. She was so heavily made up; with lashings of mascara and plump red full lips framed by her glossy black mane. The little white cap with its Red Cross added to the image; the girl in the mirror looked like a tramp in a nurses uniform; the same sort of fetish clothing worn by the girls in men's magazines that I liked to masturbate over.

I looked down at the bedside table and noticed the little blue light flashing. My trembling hand extended a red-painted manicured, finger-nail and pushed the button.

"Send him in," I whispered hoarsely.

Oh my God; what was I doing? The only thing I could I realised; do what I was told or have my legs and face broken. It was only for one night and soon it would be over. I would escape; I would tell the Warden, my lawyer; someone who could get me out of the obscene mess I was in!

I sat on the bed and waited. My eyes drifted to the cell across the way and I saw Carmel. She was standing up in her cell, bent over and holding on to bars of her cell for support; her painted red fingernails digging into the palm of her hand as she tightly gripped the iron bars. Her skirt was rucked up over her back, her pure white arse raised suppliantly into the air. Positioned behind her a large black man was pounding himself in and out of her. As he slammed into her he grunted and pulled her soft white arse back against him so he could drive himself in her as far as he could go. Carmel's heavily made-up face looked idyllic as she concentrated on maintaining the rhythm whilst she was anally pummelled. She open her eyes and looked at me through the bars, she smiled at me, winked and then closed her eyes again as she rocked back and forth on her high heels, her sheer stockinged legs glittering in the low red lamplight.

I head heavy footfalls approaching my cell and realised it was my first customer. I silently prayed.

A shadow fell across the doorway to my cell and the footfalls ceased. I looked up under the dark fringe of my hair; the heavy mascara and eyeshadow causing my eyes to reflect like two deep blue pools. My eyes met with a large man in his late forties. His thick arms heavily tattooed, burly chest and huge pot belly were barely contained by his faded blue singlet; faded denim jeans hung beneath his large belly and his shoes were prison issue boots, scuffed and poorly repaired.

I recognised him immediately; it was Harry Watson; or 'Doc' Watson as he was called by all who knew him. He was one of Eddie's 'enforcers'; a good mate of Iron-Bar Steve and just as ruthless.

Harry stepped into the cell and held out his rough dirty hand to me. I took it in mine and stood up, shaking in fear with what was about to happen. Harry looked me over slowly with hungry eyes. He looked down at my white high-heeled pumps and followed my shapely; nylon encased legs to where they disappeared inside the hem of my nurse's tunic. The white pantyhose shimmered in the low scarlet light cast by the bedside lamp. His eyes continued up my crisp white uniform, resting for a few seconds on my large false breasts, straining the buttons of the tunic. He then continued his gaze up to my face, his eyes engorging themselves on my full plum-red lips, my heavily mascaraed eyes, my rouged cheekbones framed by the jet-black mane of my hair. Finally he looked at the little nurse's cap with its silly Red Cross perched on my head.

"Fuck, you are worth every penny I've paid; now the Doctor want's his nurse!" he groaned and pulled me to him.

His foul tongue thrust into my mouth as he crushed his lips against mine. He groaned and his hand went straight under my skirt and began to brutally squeeze my buttocks through the silky satin panties and sheer hose. Harry pulled me close and as his rancid breath panted into my mouth, I felt his rock hard penis pushing against me though the fabric of his jeans and my skirt. He pushed me away from him releasing his grip and looked me up and down again with wanton lust.

"Lift yer skirt!" he demanded.

"Whaaat?" I stammered, dazed and confused.

Slap! Harry's hand snaked out and backhanded me across my cheek.

"Lift yer fucking skirt Nursey or I'll tear the fucking thing off you!" he shouted.

I looked down at his feet and took the hem of my pristine white cotton skirt in both hands and slowly raised it up my thighs. Harry's eyes followed the hem and opened wide as my firm thighs, encased in gossamer white nylon, slowly came into view. He gasped as the first glimpse of white satin panty was exposed and couldn't help him self; he reached out and stroked his hand up and down by thighs; his rough hand slithering over the gossamer nylon.

"Oh fuck, you're just what I asked for; I can't wait any longer Nursey or I'll come in me pants!"

With that he grabbed me roughly and spun me around so I was facing the bed. He pushed down on my shoulders and I fell forward doubled over so I that was tottering on my heels with my weight supported by my outstretched hands on the bedside table. I heard a ripping sound that could only be the zipper of his fly being pulled down. Inside I screamed and prayed, hoping what I knew was coming next wouldn't happen.

I felt Harry lift my skirt up and push it over my back so that my silky arse was exposed and thrust up at him as I gripped the nightstand to keep my balance. Then I felt a hot iron bar pushed against my pantied ass it rubbed all over my satin encased buttocks. I realised it was Harry's erect penis. Then I felt his erection slide under the silken gusset of my panties and wedge itself in the crack of my arse.

Instinctively I tried to move forward and away from the invading member but Harry gripped my waist, cruelly digging his hands into me as he held me steady.

"Oh no you don't Nursey; hold still while the doctor tends to you," he hissed.

I could feel his hard cock rubbing against the thin gauzy nylon of my pantyhose as it pushed the silky material into the crevice of my arse crack. Then I felt Harry reposition his member so the head was nestled in the rosebud of my sphincter. Now the thin layer of pantyhose was the only protection between my anal canal and his hot throbbing cock. I felt harry pull the gusset of my panties across my buttocks so that he had an unobstructed view of his penis poised at my rear entrance; his erect member pushing the nylon of my pantyhose tight against my sphincter. He said one word.

"Lube!"

"Whaat?" I stammered again.

"Lube! Or you can take it dry, but I think you will appreciate some lube Nursey!"

I knew what he meant then, and although horrified I remembered the torture of Eddie's rampant member invading my unlubricated anus. I reached under the pillow with one hand and searched for the tube Carmel had put there previously this evening. I grasped it and thrust it out behind me, rocking precariously on my high-heels as I held onto the nightstand with only one hand.

"No, you do it Nursey," Harry laughed.

He took the tube of KY jelly and squeezed a big blob of the cool slippery liquid into my hand.

"You do it! And be nice and gentle I don't want to come before I get it in yer!"

I awkwardly reached behind me and felt around until my hand came into contact with Harry's hot engorged pole. It was rock hard and as I put my small hand around it, it felt enormous and menacing as it throbbed in my hand. Harry looked down to see me standing legs wide apart on high-heeled feet, my legs encased in diaphanous white nylon and my white satin panties pushed to one side of my arse. He watched as my long delicate fingers, their red painted nails glimmering with the shine of the lubricant, slid feather-like up and down his hard cock, coating it with a generous amount of KY jelly.

I looked to one side and saw that I had left the wardrobe door open and I could see Harry and myself in the full length mirror. I looked just like a pretty nurse, a slutty nurse with a ridiculous cap perched on her head, bent over, pretty and pathetic as I reached back behind me and slowly smeared lubricant up and down Harry's penis. This nurse was about to be raped! Then I looked up and saw that Harry was looking at the same image and that he had a huge grin on his face.

"Oh Nursey, you're going to get it now!" he groaned.

His hands gripped my hips tighter and I felt his now lubricated glans press hard against my sphincter. But there was something preventing his entry; the nylon of my pantyhose! He hadn't pulled my pantyhose down or torn a hole in them!

"Pantyhose!" I gasped.

"Yes, I love them!" exclaimed Harry and gave an enormous thrust with his hips.

Christ! I felt the head of his penis slide inside my tight hole, the lube assisted but the nylon gusset of my sheer to the waist hose was also pushed inside me. The pain of having Harry's hard cock was bad enough but the nylon wrapped around the head of his cock was like sandpaper on the walls of my rectum.

"Oh God!" I groaned in agony and looked at my reflection in the mirror.

I was impaled on the head of Harry's cock as I stood with my legs spread, skirt hitched up and Harry's huge gut hanging over me as he thrust harder. I could see his eyes closed in concentration and ecstasy as he stuffed more of his tumescent member inside me. I felt my pantyhose grow tight around my buttocks and between my groin as harry forced more of the sheer fabric inside me, wrapped around his hard cock. He was groaning and gripping me so hard that the pain was almost more than I could bear; I felt a searing heat as my insides were invaded.

Suddenly I felt the flimsy nylon pantyhose give and Harry's well lubricated shaft drove itself all the way inside me as the resistance of the nylon parted. It was so big and in me so deep that it knocked the wind out of me and rocked me on my heels. I felt Harry's flabby thighs against mine, his jeans whispering on my nyloned legs as he ground into me. His large gut now rested firmly against my lower back and my hands gave way as his full weight was pressed against me.

"Don't fall over Nursey," he laughed, "I'm just about to start the ride!"

With that he pulled me up and back against him so that I was standing. I was rocking on my heels but Harry held me firm and spun me around so I was pressed hard against the mirror. My skirt had fallen down and was covering our intimate parts where Harry and had me impaled on him. He pushed me harder against the mirror and I smelt his rancid breath as he started to kiss my neck. One hand held me locked against the mirrored wardrobe as I felt the other fumble around at the front of my skirt. His hand went under the hem and began to stroke my pantyhosed thighs as Harry started to slowly rape my back passage.

It was not as excruciating as when Eddie raped me without the lubricant, but Harry's cock was a lot thicker and I felt so full of him that I would explode. Harry started to thrust slowly in and out of me, hardly moving his cock more than an inch in and out; he was panting as he slobbered at my neck, kissing and licking me with his foul mouth.

Harry's hand stroked my thighs and groin as he slowly fucked me, he obviously delighted in the feel of the slinky nylon and satin on his skin because he had shucked down his pants and was pushing his crotch hard against my pantyhosed arse on the in stroke. Harry now began to fuck me harder and faster, he breath in great explosions as he established a had and fast rhythm.

"Open your eyes bitch!" he gasped against me, "look!"

I opened my eyes and was humiliated by what I saw reflected in the mirror. Harry was thrusting against me, his jeans around his ankles and his sweaty body moulded to my back; his hand was under the front my skirt ferreting around, pawing and stroking. Harry's ugly face was beside mine and he slobbered at my neck. He was thrusting in and out pivoting his waist to get all of himself inside me, rubbing his balls on my nylon covered ass at the top of his in-stroke.

My back passage was filled and it ached with the size of the invading member that slid in and out of me, but oh god no! I could feel the spongy hard mass of Harry's glans as they pushed on my prostate; I couldn't believe it but again I felt the first ripple of sexual pleasure. I was not about to give this pig the idea that I was becoming aroused so I decided to end this rape as soon as possible.

I leant forward more so that my buttocks pushed out further and scrunched my hips from side to side to increase Harry's pleasure and ensure my nylon encased cheeks rubbed against him, as he obviously loved the feel of that. I turned my head sideways so that harry could stretch his fat neck out and kiss my pouty lips; I gagged on his breath but concentrated on trying to get Harry to come.

Harry now stepped back slightly and pulled me with him so that I was again bent over with my legs spread. Harry now started to pound himself heavily in and out of me. I though that he would do some serious damage to my insides if he didn't stop soon; the pain was enormous, but I still had the tingle of excitement every time his cock rubbed my prostate. Harry fucked me harder and harder and was really grunting and panting now. He gripped my hips and pulled me back hard against him as he thrust forward and held me rock steady as he pulled back. He was now jackhammering himself in and out of me, groaning and cursing.

"Fucking bitch! Fucking Whore! Fucking take this you cunt!" he screamed.

He pushed in hard and ground his balls against my nyloned cheeks as he shuddered. His grip on my waist was like iron. I felt his cock start to convulse inside me as it shuddered and secreted his hot spend. Harry's cock actually expanded and I felt the walls of my back passage begin to tear as Harry came deep inside me. I felt jet after jet of hot seed stream into me as Harry stated to rock slowly back and forth again. Harry's semen further lubricated his cock and some of the pain went away. Harry was still hissing obscenities as he completed his climax. I felt his spend drip from my sphincter and run down my nyloned legs.

Harry pushed me forward and thrust back so that his cock slid out of me, a torrent of his semen joined the trickle running down the inside of my legs. I couldn't believe how much semen he had shot into me.

I couldn't move, I was bent over, my back aching, my legs locked apart and my back passage throbbing in agony. Harry pushed me sideways and I landed on the bed, sitting up, my legs spread and skirt hiked up.

Harry leant over me and kissed me full on the lips.

"That was worth every penny; you are one hot nurse," he laughed.

Harry grabbed a handful of my clean white skirt and wiped his cock on it. The silvery gleam of semen and KY jelly stained the fabric; there was also a faint trace of blood.

Harry hitched up his pants and made for the door, tightening his belt; he looked back at the dishevelled, raped, nurse sitting legs akimbo on the bed, a look of shock on her face and her tunic stained with semen and blood,

"Yep, you are one fucking hot nurse alright; maybe next time you can play Nun!"

I heard his laughter fading as he walked down the passageway past the other cells to what I presumed to be the waiting room. The waiting room where undoubtedly there were more customers waiting. I closed my eyes as the tears ran slowly down my cheeks.

 

 

 

 

To be continued……………………………………………………………………………..

"You are one very naughty school girl," Davey groaned, and closed his eyes and relaxed, content to let Michele have control of the situation.

Michele found this empowering. Most of the men she had had sex with in Chelmsford had forced themselves on her or forced her into capitulating. Even when she had been playing a dominant role with the Warden she was not really in control. Davey was showing her the utmost trust by just lying there and allowing her to take charge of situation. She found she genuinely wanted to please him.

Michele stroked and caressed Davey’s engorged member, sometimes slow and gentle, sometimes hard and fast. Davey expressed his appreciation with a contented smile on his face and with occasional moans of pleasure. He reached out and caressed her face with his fingers. Michele drew one of his fingers into her mouth and sucked on it; twisting her tongue around the digit.

Davey put his hand under Michele’s chin and gently bought her face to his. He looked longingly into her eyes and said,

"You are truly beautiful Michele," and then bought her mouth to his and kissed her tenderly.

The smokiness of the scotch they had drunk earlier had mixed with his sweet breath and she responded to his kiss. She kissed him harder and her hand started pumping his long hard cock in a steady rhythm.

Davey groaned again in the back of his throat and Michele gently lifted her lips from his. He sighed his disappointment; but not for long. Michele slid her stockinged knees along the floor so that she was positioned adjacent to his crotch. She lowered her head and kissed his cock. She kissed it all over leaving telltale smudges of lipstick on the shaft and head. She rubbed it against her cheek and placed the glans against her eye and batted her eyelashes teasing him with ‘butterfly’ kisses.

Michele was totally in control of the situation and was actually enjoying what she was doing to Davey. Not only did she feel empowered, she felt aroused; for the first time since she had been forced into becoming a transvestite she totally loved being a woman and pleasing her man.

She bought her mouth down to Davey’s scrotum and kissed and licked his balls, feeling him tense up and sigh at this new attack on his senses. Then she licked all along the length of his penis and finally took his member inside her mouth. She ran her tongue all over his glans as she commenced to gently suck and move her head up and down.

"Oh Michele you are wonderful," Davey whimpered.

"But take it easy I’m so close," he half complained.

Michele had no plans to take it easy; she was in control and wanted to make Davey climax. In her head she imagined him coming; then they would cuddle and caress until they were both sufficiently aroused and he would make love to her like a woman. She could hardly believe her own feelings but she wanted Davey to fuck her. My god she was changing! She examined her feelings and found that yes; she loved being a woman with Davey and she wanted Davey to want her. She didn’t try to analyse her feelings any further; she was too confused, she got on with her most immediate pressing need; to please Davey.

Michele clamped her lips around Davy’s now throbbing member and sucked hard and bobbed her head up and down as fast as she could. Davey started to convulse and Michele tasted the first beads of pre-seminal fluid and then the hot jets of his seed as his penis convulsed and shot streams of warm salty sperm into her mouth.

Michele kept up her hard and fast fellatio, swallowing his issue as it filled her mouth. In response to Davey’s climax she felt her own clitty harden in the silken purse of her panties. Slowly Davey started to relax as his orgasm subsided and Michele felt his organ begin to slowly deflate in her mouth. She took it out and rained kisses all over the cute member as it shrank back into flaccidity.

Davey reached out and gently assisted Michele up onto the bed so that she was lying beside him. He gently stroked her hair and softly kissed her.

"I think I’m falling for you Michele," he whispered in her ear.

"I think I’m falling for you to Davey," she whispered back and snuggled up closer to him.

They caressed and chatted easily with each other for a while until eventually they fell asleep in each others arms; like lovers.

Then – Crash! The door to the cell flew open and Eddie strode into the cell. Michele and Davey sprang to their feet; Davey taking a step forward in a defensive position to protect Michele.

"Just look at these two lovebirds would ya!" Eddie sneered sarcastically and reached for the scotch, gulping down a swallow.

"Fuck me Davey, I warned you about this bitch!" Eddie whinged.

"She’s fucking trouble mate; I don’t care what she’s done or said to make you all gooey over her. She’s more fucking trouble than she’s worth."

"If I could sell the bitch for a profit I’d get rid of her, but I ain’t even made the money I invested in her," Eddie went on, waving his hand at Michele as if she was just a commodity not worthy of consideration.

"She’s wonderful Eddie," Davey shot back.

"You just don’t appreciate a precious jewel when it’s staring you in the face," Davey continued.

"And I want her!" Davey demanded in a menacing tone.

Michele was stunned; she couldn’t believe what she was hearing. Was Eddie’s best friend and business partner prepared to take on Eddie over her? She felt flattered but at the same time confused.

"If she wants me that is?" Davey looked deep into Michele’s eyes with a questioning look.

Michele was now totally confused. She knew that prisoners kept transvestite inmates as ‘wives’; in fact some of Eddie’s ‘girls’ were ‘married’ to inmates but continued to work in the brothel to provide money for their ‘husbands’. The more privileged inmates, the ones who really ran the jail, had full time transvestite partners; wives, who ‘stayed at home’ and lived with them in their cells.

"You’re fucking joking aren’t you Davey? You ain’t going to let this big arsed bitch get in the way of our friendship are you?" Eddie sounded astounded.

"No I’m not Eddie," Davey replied, "If she wants to move in with me I’ll see you right, but she stays with me; exclusively!"

"But only if that’s what she wants to do," Davey added this time turning to Michele and taking her hands in his and looking deep into her eyes.

Michele felt completely feminine; at that moment the remnants of her male alter-ego ‘Mike’ disappeared. She was a woman who wanted the man standing before her. She tried rationalising her feelings; being Davey’s concubine was a better prospect than being forced to work in the prison brothel; but deep inside she knew it was more than that. She had become Michele; she was Michele, and she wanted to be Michele all the time, and to be with Davey.

"Yes Davey," Michele’s whisper was barely audible, "take me home please; take me away from this place."

"Oh you fucking dopes," Eddie laughed.

"She is going to cost you heaps Davey," he warned; "You’re not getting her off me for nothing!" he insisted.

"Eddie you’re my best mate in this place and we go back a lot of years; we scratch each others backs and work the joint for a share of the profits; but if you keep talking about Michele like that in front of her I’ll fucking well smack you!" Davey retorted angrily.

Eddie laughed, "Ok, ok, don’t get your knickers in a twist! She’s yours; we’ll settle the price later."

"Michele, go and see Charlotte and Mabel and get them to move your things out of here into Davey’s cell in A block; I’ll clear the move with the warden tomorrow." Eddie said.

"And as wedding present you can keep the clothes, wigs, shoes and the rest of the stuff I bought you free of charge. I hope you will both be very happy," Eddie said half sarcastically.

"Now run along girl; me and Davey have business to discuss," he ordered.

Davey reached out and kissed Michele gently on the lips, "Don’t worry about him honey," he smiled; "get out of here and I’ll meet you in my cell in a couple of hours."

Michele walked out of her workroom for the last time that evening and didn’t bother to look back. She found Mabel and told her Eddie’s instructions. Mabel didn’t believe her at first and ran down to Michele’s workroom to see Eddie. She came back flabbergasted.

"Well I’ll be fucked," she said, "Good on you girl; now get out of here and me and Charlotte will bring your things down to A block," she smiled good naturedly.

When Davey finally completed his business with Eddie that evening he was considerably out of pocket. Michele had cost him plenty but he smiled as he walked back to his cell, two minders at his side, she was worth every penny. Besides he would soon make his money back with his other business dealings with Eddie; they both made more money than they could spend in this shithole. The only thing his money couldn’t buy was freedom; he had many years left to serve; but at least he would be happy and contented with Michele by his side.

Davey arrived at his cell just after midnight. His cell was actually three cells combined into a living area with all the modern furniture and electrical gadgets you could want, and a large bedroom with an enormous bed set against one wall. As he closed the door to his cell he noticed all the lights were out and the place was completely dark except for the flicker of candlelight coming from his bedroom. Davey stripped naked, kicked his clothes aside and strode towards the bedroom.

Michele was lying on the bed; surrounded by deep red satin sheets, her head resting on a mountain of white satin pillows. She was exquisite! Her hair was a sea of raven curls hanging down to her shoulders and her dark, heavily made-up eyes shone brightly beneath the fringe. Her full mouth a ripe red plum waiting to be kissed, and her rouged cheeks emphasised her sharp cheekbones and the elegant lines of her pretty face.

She wore a full length white silk nightgown thrown open and spread out on the bed like angel’s wings. A matching white bustier adorned her body, the garter straps clipped to white nylon stockings. He could just make out the triangle of white satin panties between her legs which were slightly spread apart; her feet were shod in white open-toe high-heeled sandals, her toes peeking out of the high-heels, her white stockings gossamer thin and stretched taught over her red painted toenails. She wore a pearl choker necklace, matching earrings and bracelets. She held out a hand and beckoned.

Davey strode towards the bed, his manhood erect before him, a rope of gleaming, clear pre-seminal fluid leaked from the eye, and Michele reached out and took him in a firm grip and pulled him onto the bed. She opened her legs wide and he knelt between them; neither of them saying a word. He bent down and kissed her passionately on the lips and she responded and moaned deep down in the back of her throat.

She still held his manhood in a firm grip as she slid herself underneath him and eased her panties aside with one hand and positioned his member at the entrance to her special place. She lifted her white nyloned legs up high and bought her calves up around Davey’s lower back so that her high-heels were high in the air and almost touching. Michele pulled up her lower body and at the same time guided Davey’s beautiful hard slick member inside her. They never stopped kissing. Michele rose up and locked her heels behind his back as Davey thrust forward so that she could force all of him inside her. They rode the waves of mutual pleasure slowly; Davey taking his time so that Michele’s orgasm would come at the same time as his.

He released streams of his hot seed deep inside her and she responded by rising up and holding him tightly against her as she emptied her own emission into her white satin panties. Michele could feel Davey’s hot spend lubricating his throbbing glans as it stimulated the sensitive organ deep inside her. Davey could feel Michele’s secretions saturating her panties, soaking through, warm and sticky against his lower belly. Their lips had never parted throughout their lovemaking. Davey begrudgingly drew his face away from Michele’s just far enough so that he could look adoringly into her pretty blue eyes.

"I love you Michele," he whispered.

"I love you too Davey," she whispered back. Michele smiled.

 

The End

The predator had defiled five women so far, all sophisticated, attractive and well dressed ladies in their forties or early fifties. He made a point of that; that they be dressed attractively. He had been known to make his victims get out of bed and apply makeup and dress in their finest lingerie and eveningwear before he spent his time playing his sordid games with them. Some victims reported that he made them parade before him wearing differing ensembles until he was satisfied with how they looked before he ravished them.

The predator had arrived at his current destination by sheer luck. He usually followed his intended victim for a few days, and then planned his attack when he was sure that the victim was alone in her home. Tonight he was returning from a bar and decided to cruise a well-to-do neighbourhood just to see if there was anything special that might be worth following up. He was slightly drunk and stopped his car next to an alleyway separating two townhouses so that he could relieve himself. He ducked into the darkened alley to urinate when he noticed the shadow on blind. The silhouette on the blind was unmistakeable to a predator of his kind; a woman either dressing or undressing; her movements and mannerisms playing out like a shadow-puppet on a movie screen. He couldn’t help himself; he had to see what might be on offer here. When he had splashed the last of the hot stream of his urine against the wall he climbed up onto a garbage bin hoping he would be able to see more through the window.

The predator was in luck and managed to secure a position where he could see through a chink in the blind where it had not been fully extended. The view provided by the chink took in half of a woman’s bedroom. He could see most of the bed, scattered with lingerie and women’s clothing lying in a heap, the coat-hangers still attached to the skirts, blouses and jackets. There had to be at least six outfits lying on the bed surrounded by the small piles of assorted lingerie. He could see a dressing table littered with makeup, perfume bottles, jewellery boxes and the sundry items that women seemed to be unable to do without in their endeavours to look attractive. A wine glass, half full of red wine was set to one side. A small shelf above the dressing table held three wig stands. A blonde bob sat on one wig stand and a black long haired wig sat on the second; the third wig stand was bare.

The predator was pleased to see that this woman had such good taste in clothing and obviously looked after herself. The mountains of lingerie, makeup, jewellery and the wigs bespoke of a woman who was most attentive to her appearance – the sort of woman he fantasised about.

The predator allowed his eyes to consume the sight before him. The woman presented herself sideways to him, sitting in front of the mirror at the dressing table making final adjustments to her appearance. She looked to be in her early forties, solid but not fat, and dressed just to his taste. His eyes started with her face and worked their way down her body. Straight brunette hair hung just to her shoulders, the fringe framing her heavily made-up eyes; her cheeks were rouged, her lips full and painted plum red. A glint of light betrayed the simple sparkling earrings that undoubtedly matched the diamante necklace around her neck. She was wearing a black nylon full-slip, the rise of her small breasts emphasised by the tight bodice, the laced hem of the slip resting on her sleek nyloned thighs just above her knees.

The predator liked the way her taupe stockings glistened in the lights from the makeup mirror. Her hands slid down one leg, her fingernails painted a matching plum red to her lipstick, and adjusted her stocking; pulling the sleek nylon taught on her shapely leg and momentarily disappearing under the hem of her slip as she adjusted the clip on a garter strap. The predator shuddered. His eyes continued down her leg and lingered on the black, patent leather, open toe high-heels and he caught a glimpse of her painted toenails on display, encased in the gossamer of her sheer stocking, as she waggled her foot back and forth back as the admiring her own pretty foot. She stood, and then advanced towards the bed presenting herself front-on to the predator.

The predator took in the whole visage of the woman that he had now determined was to be his next victim. Mature, attractive, heavily made-up, tall and well built; she was just to his taste. If he had not spent the evening in the bar and was in a sober frame of mind he might have been more cautious, but the sight she unknowingly presented to the predator sealed the woman’s fate. The predator slid silently off the garbage bin on which he had been standing and made his way back to his car. He scanned the street and saw no one. Most of the lights in the adjoining townhouses were out and the street was quiet. He checked his watch: 11:30pm, perfect he thought, and reached into the back seat and took out his burglary tools. Fuck the risk! He had to have her. Now!

Michele sat before the makeup mirror twirling the wine glass in her fingers watching the light sparkle in the red Shiraz. The dark red wine matched the colour of her fingernails and she briefly giggled to herself at the complement. She was slightly drunk from the half-bottle of wine she had already consumed and she set the wine glass down carefully and began to add the final touches to her makeup.

Michele was actually Michael, a divorcee in his mid forties who lived alone and had come to transvestism late in life after suppressing an urge to crossdress for most of his adult years. Like most crossdressers he had urges to dress-up and become a woman for short periods of time and often dressed in his wife’s underwear when she was away. After an amicable divorce some five years earlier, Michael now transformed into Michele whenever it pleased him to do so. Living alone and having the privacy to dress when it suited him, he had developed the persona of Michele over a period of years.

Michele’s male alter ego had fought a battle with his weight for most of his life and he had allowed himself to balloon out during the later part of his marriage. When the opportunity to fully crossdress whenever he felt like it presented itself, Michael decided he didn’t want to look like a middle-aged frump. He dieted and exercised until he could eventually fit into a size 16 and some times even a 14; a great effort given his large frame, and he now carried very little fat.

Michele had acquired an extensive wardrobe, first at opportunity shops and later at larger specialty shops; insisting to the shopkeepers that he was buying the clothes as presents for his wife. Lingerie was easy to buy as it is never considered unusual for men to buy nice underwear for their wives or lovers.

Michele bought his first pair of women’s shoes from an opportunity shop and once he knew his woman’s shoe size he purchased many styles of high-heeled pumps and sandals; again insisting to inquisitive shop assistants that they were presents for his wife. He sometimes had the boxes gift-wrapped to maintain the façade.

Michele had dabbled with his wife’s makeup with various degrees of success and failure during the years of his marriage and easily obtained all the makeup he needed by purchasing a couple of complete makeup kits ("its for my niece’s birthday; she’s just turned thirteen") and then simply added to his makeup collection by throwing any item he desired in with the week’s groceries; no one ever questioned him at the checkout; husbands just picked up whatever their wives had written on the shopping list after all.

Michele could purchase women’s jewellery easily of course, but his biggest problem was how to get his hands on some nice wigs. The problem was solved when he was sent to a large city interstate on a business trip where he visited the part of town frequented by the gay community. Here a sympathetic old lady in a wig shop who was used to dealing with ‘his kind’ helped him pick out and try on three different styles and hair colourings. He purchased the wigs and then went into another ‘specialty shop’ where he bought breastforms in two sizes.

Michele loved being Michele; Michael transformed into her at every opportunity and spent most evenings and weekends dressed and fully made-up. More and more often though he had been fantasising about taking his transvestism a step further; whenever he was dressed as Michele he became aroused, he always had, but for the last year or so he had fantasised about being with a man. He did not consider himself gay; in fact when he wasn’t Michele his sexual fantasies revolved around women; but when he was Michele he wanted to be with a man or to have a ‘lesbian’ encounter with another transvestite.

Michele was terrified that her secret life would be exposed. When dressed she kept the doors locked, the shades closed and never answered the door. Although she had become adept at applying makeup and dressing en-femme, and she believed that she made quite an attractive mature woman, she would never dream of going out dressed as Michele. She contented himself with reading books and looking at magazines and movies where transvestites had hot sexual encounters with each other and with male admirers. Although masturbation bought relief, Michele longed for ‘the real thing.’ She was thinking a lot lately of either placing a discreet ad in some of the sex shops she visited or advertising her availability in a contact magazine or in some of the internet chat rooms she frequented.

Michele was not aware that she was about to have her first encounter tonight, nor that the Predator would be her first man. The Predator was not aware that the woman he lusted after, as he spied on her through her bedroom window, was in fact Michele; a transvestite.

Michele had opened a nice half-bottle of Shiraz earlier in the evening and then poured herself a warm bath. She painted her toe and fingernails and allowed them to dry and then poured herself a glass of wine and stepped into the steaming, scented water. She spent a luxurious hour soaking, during which she had shaven her legs and chest and closely shaven her face. She had also drunk three glasses of wine.

Michele towelled herself off and carried a full glass of wine from the ensuite bathroom into her bedroom where she sat at her dressing table and looked at herself critically in the mirror. She was showing her age but was still respectable and with the magic of makeup would soon be transformed into a presentable, if slightly sluttish, middle-aged woman. She giggled to herself and realised she was slightly drunk.

Michele went through the labour of applying her foundation; she had a product from Max Factor which closely matched her skin colour but covered up the few scars and blemishes that she had acquired during in her life. Next she liberally coated her face and neck with face powder one shade darker than her foundation; she now had the blank canvass she liked to achieve prior to applying the rest of her makeup. She loved this next part; the application of colours and shading which changed the whole look of her face from bland maleness to feminine fox. She giggled again and took a gulp of wine before continuing.

Michele applied her eyeliner next. All the books and magazines in which she had read makeup tips said you should do this later but Michele had learned that this was the hardest part of applying makeup and if she screwed it up (which she often did, especially after drinking), she could wipe the eyeliner away, apply more foundation and start again without ruining her eye-shadow and mascara. The eyeliner was applied liberally to her upper and lower eyelids, from the inner corner of her eyes to the outer corners, gradually thickening the line as she went. Having achieved the desired result she looked for a suitable palette of colours for her eye-shadow.

Michele selected a pale blue which she applied to her eyelids and then blended it into a shade of dark pink which she brushed onto the upper part of her eye sockets and right up to her eyebrows. She wished she could shape her brows but that would be too noticeable to her workmates, family and friends so she just kept her brows neatly plucked. Next she rouged her cheeks to define the lines of her cheekbones. She used more rouge and eye-shadow than is the fashion nowadays but she preferred the more colourful makeup styles of the eighties over the current subdued ‘less is more’ look.

Michele next applied a light coating of ‘skin-glow’ face powder all over her face and neck to set the makeup she had already applied and to give her face a subtle radiance. She carefully brushed lashings of mascara onto her lower and upper eyelashes. She knew from painful experience that if she put too much mascara on her lashes that it would congeal and look unsightly; even worse it could end up ruining her eye-shadow or face makeup if globs of the mascara came loose from her lashes. She did like to wear lots of mascara though and found a Maybelline product that did not clot and was easy to apply.

Michele took her time putting on her lipstick. Having completed the rest of her face she didn’t want to ruin the effect with a sloppy job. She took time to line her thin lips just outside her lip-line so that her lips would seem fuller; she also knew that the wine she had drunk was having its effect and realised that caution here would save her tears of frustration if she slipped and made a mess of her lipstick. The colour was a deep plum red and matched the nail polish that she had painstakingly painted on her toe and fingernails prior to her bath.

Michele reached up and studied the three wigs sitting on their stands. ‘The brunette,’ she thought to herself and lifted the wig from its stand. She brushed the wig with the special brush that she been advised to purchase by the nice old lady who had sold her her wigs. She started her brush-stokes at the extremities of the hair and worked her way up to the crown, admiring the sheen of the artificial hair. She positioned the wig on her head and adjusted it so that her fringe was straight and hung level with her eyebrows.

Michele looked in the mirror and admired her transformation. ‘I look quite attractive’ she thought; ‘I bet Michael would like to fuck me’ (she giggled to herself at the absurdity) and reached for her wine glass.

Michele went to the closet located on the right-hand side of the bedroom; Michele’s closet. The closet on the left was Michael’s closet and contained his suits, shirts, ties and boring male underwear, socks and shoes. Michele’s closet contained the soft, luxurious, feminine attire that so excited her. She rummaged through the lingerie draws and threw a pile on the bed; next she took down half a dozen ensembles and threw them in the centre of the bed amid the strewn underwear. It looked like a messy, awkward way to select an outfit but it worked for her. She would often get nearly fully dressed and then change her mind and she had found over the years the best method for her was to take a selection of clothing and throw it on the bed and then once she had finished dressing, put away whatever clothing she had decided not to wear.

The predator at this time was just leaving the bar having been unsuccessful in locating a suitable woman as his prospective next victim. He had drunk more than usual, and frustrated at not finding his next target, stumbled to his car and took off towards the better part of town to prowl for a fitting quarry to stalk.

Michele tore open a packet of cheap flesh-toned sheer to the waist pantyhose. She wore pantyhose as a foundation garment to help flatten her tummy, hold her male genitalia out of the way between her legs, and to help cover the small nicks and varicose veins on her forty-year-old thighs and ankles. She felt a small tingle of excitement as she smoothed the pantyhose up her legs and over her tummy and buttocks. She carefully manipulated the sheer toes around her painted nails ensuring she didn’t ladder the cheap hose.

Michele selected a pair of red nylon full-cut panties from the midden of lingerie on her bed. She stepped into them and slid them up her nyloned thighs, savouring the rustling sound of nylon on nylon. She adjusted the waistband on her hips so that the cute little lace bow was centrally located below her belly button. Michele could not understand the modern woman’s obsession with thong panties; they were uncomfortable and unflattering on women of her solid build. Besides she liked the way the tight nylon panties caressed her buttocks.

Michele next chose a black satin garter belt; her mother had called them ‘suspenders’ she remembered. She clipped the garment together and stepped into it carefully pulling it up her hosed legs and over her panties so that it sat snugly around the bottom of her waist. She carefully adjusted the garter straps ensuring they did not snag her pantyhose.

Michele decided on a matching black satin bra, again clipping the fastenings at the back of the bra together before donning the garment. She giggled yet again when she thought about all the troubles she had had as a young adolescent Michael attempting to undo his girlfriend’s bra so that he could caress her budding teenage breasts. She took another sip of wine and pulled the garment over her head, adjusting it on her chest in the mirror and straightening the straps on her shoulders. She had breastforms if she wanted to use them but this bra was slightly padded and with her ‘man boobs’ gave her a pleasing if subtle cleavage without being overly busty (although sometimes, when she was in the mood, she liked to stuff her bra with the largest set of breastforms she had and parade around like Mae West).

Michele dithered over which stockings to wear; it would depend greatly on which ensemble she finally decided upon. Should she wear black, grey, taupe, flesh-toned; fully fashioned, Cuban heeled or sheer toe? She had so many pairs! She settled on a pair of high sheen taupe lace tops. She loved the way they emphasised her shapely legs, and with the flesh toned pantyhose underneath the stockings, her legs would look magnificent. Michele thought her legs were the best part of her body. She slid the stockings on and connected the clips on the garter straps to the lacy stocking tops. She reached for her jewellery box and selected faux diamond earrings and a matching pendant necklace. As she clipped the earrings to her ears she lamented the dearth of good quality clip-on earrings. She dare not pierce both her earlobes as it would be too noticeable to others.

Michele went back to her closet and selected a pair of black, patent leather, open toe high-heels and placed them beside the chair next to her dresser. She chose a black nylon full-slip from the mess of lingerie on the bed and pulled it over her head being careful not to ruin her makeup or hair. She smoothed the garment to her body, the tight bodice clinging to her breasts and hips and the skirt flaring around her thighs, occasionally sticking to her stockinged legs because of the static electricity. She loved the feel of the lacy hem; like butterfly wings brushing on her thighs.

Michele sat down in front of the dressing table and slipped her feet into her high-heels; although a size eleven her feet were not grotesque because they matched the proportions of her body. After all she was a small size eight in men’s shoes and her feet were considered quite small for a man. She turned her chair sideways to the dresser so that she could adjust her stockings; she pulled the sleek nylon taught on her shapely leg and her hand disappeared under the hem of her slip as she adjusted the clip on a garter strap. She waggled her right foot from side to side, admiring her own pretty feet in the high-heels and appreciating the gleam of the lights on her high sheen stockings. Little did she know that she was not the only one admiring her legs and feet!

Michele stood and advanced towards the bed to select an ensemble for the evening. She finally decided on a white ‘Carla Zampatti’ A-line skirt and a mauve satin long-sleeved blouse she had purchased from Supré. She always wore long sleeved blouses or jackets because although she kept her fingers and the backs of her hands free of hair, she could only lightly shave her arms with a beard trimmer. Her tanned arms had only a light sprinkling of fair hair but she felt that fully shaving them would be too noticeable when she wore T-shirts and Polo’s when she was Michael.

Michele donned the blouse, fumbling with the buttons; she was still not used to them being on the opposite side to men’s shirts. Then she stepped into the skirt and pulled it up around her waist, tucking the blouse into the skirt and closing the zipper at her waist. She went back to her dresser and mooched through the jewellery box and decided upon two matching silver bracelets for her left wrist and a silver amulet set with a large black opal for the right. She slipped a matching opal ring set in silver on the ring finger of her right hand and a diamante ring set in white gold on her left ring finger.

Michele pushed her hands out before her and admired the effect of the jewellery against her slim wrists and her plum-red painted fingernails; she had taste she thought, but she still projected that slightly sluttish style she favoured. She looked at herself in the mirror and was pleased with the result. She twirled around and admired her ample but well-proportioned bottom; the A-line skirt was a snug fit. She drained her wine glass and tottered on her high-heels as she started from the bedroom to the kitchen to open another bottle of wine. She was drinking a lot lately; but what did she care? As long as she kept her weight in check; it’s not as if she had a boyfriend to keep sober for. She sauntered down the hallway towards the kitchen, her heels clicking on the slate tiles as she did her best vamp imitation, swinging her buxom sexy bottom from side to side and giggled to herself again.

The predator had let himself in easily through the kitchen window whilst Michele was making the final adjustments to her clothing in the bedroom. The kitchen window looked out over a small garden, dark at night, and well hidden from the main road; the lock was cheap and easily defeated. The predator was silent as he climbed through the window and dropped soundlessly to the tiled floor; he’d had plenty of practice after all. He heard the clatter of high heels on the tiles and a little giggle from the hallway. ‘Oh this bitch would not be giggling for long!’ he thought, as he hid behind the opened door that led into the kitchen from the hallway.

The predator quietly lowered the bag containing his burglary kit to the floor and reached inside it to take out a gag and a pair of handcuffs. He didn’t like using the gag on his victims because it ruined their lipstick and distended their faces. He liked to look into their pretty faces while he did things to them, and once they learned resistance was futile (and they all learned that lesson pretty quickly) he liked to kiss them. The woman who had excited him enough to risk what he was about to do had affected him strongly; he wanted to take her as soon as possible, his member was so hard that it was uncomfortable in his pants. He would take her quickly in the kitchen and then they could retire to her bedroom for the rest of the evening’s entertainment. he thought to himself.

The predator heard her high-heels getting louder now as she approached the kitchen door and his drunken mind reflected on his last glimpse of her before he had jumped down off the perch outside her bedroom window. Her heavy makeup, the black nylon slip in contrast to her sheer taupe stockings (he preferred women who wore stockings instead of pantyhose), and those shiny black open-toe high heels. He would take her fully clothed, right here in the kitchen; he would take her in such a way that she would know he was in charge and that resistance was futile. He would take her in a way that a woman of her breeding had probably never experienced before.

Michele walked into the darkened kitchen and headed straight for the wine rack above the breakfast bar. She didn’t bother turning on the light as the light spilling in from the hallway was ample for the task; besides she hadn’t closed the curtains in here and even though her kitchen window was not in open sight of the road she was still paranoid about anyone seeing her dressed en-femme. She was thinking of whether to open a bottle of Shiraz or merlot when she felt herself being pushed heavily from behind and she collided heavily with the kitchen table.

The predator pounced on her when she was halfway across the room. He used his weight and strength to propel her towards the kitchen table. She was a big woman and he was taking no chances; as she crashed into the table he pushed her shoulders down and pulled her hands up behind her back and clamped the handcuffs on her wrists. He lifted his knee and slammed it into her well proportioned behind to hold her against the table and pulled up on her cuffed wrists. As expected, she pushed her upper body upwards and back in an effort to escape, but this only assisted him. As she rose up and gasped, a prelude to either to a scream or cry for help, he pulled the ball bag over head and into her mouth, securing the straps tightly around her neck. He now had her where he wanted her.

The predator pushed down on her shoulders so that she was bent over the kitchen table. In the dim light he could now see her mauve satin blouse and the white A-line skirt; subconsciously he approved of her style, he loved it when they dressed nicely for him. He wasted no time. The predator kicked her heels apart so that her legs were spread as far as the tight skirt would allow and released one of his hands from her cuffed wrists and undid his flies and released his erect organ.

The predator was extremely aroused and he could smell the stale alcohol on his own breath as he panted in excitement. He reached under the woman’s skirt with his free hand and grasped the waistband of her panties and yanked them down. He was puzzled when her panties came to an abrupt halt at the top of her thighs and then he realised that she was wearing her garter belt over her panties and because of this her panties could be lowered no further without releasing the clips on the garter straps attached to her stocking tops. It didn’t matter, her panties were down far enough for him to carry out his intentions.

The predator stepped in close between her splayed high-heeled feet; his crotch close to her buttocks, one hand gripping her handcuffed wrists and pushing her body down hard on the kitchen table, the other hand under her skirt pulling her panties down so that they bunched around her thighs. He bought his free hand out from under her skirt and spat in the palm of it; then he spread the glistening spit over his tumescent penis, ensuring his glans was completely lubricated.

The predator lifted the woman’s skirt up and thrust forward. His cock came up against a membrane of sheer nylon, and for a moment he couldn’t figure out what had happened. Was the silly bitch wearing two pairs of panties? Then he figured out what was preventing him from reaching the object of his desire; it was the gusset of the woman’s pantyhose. The dumb cunt was wearing pantyhose under her stockings! Why the fuck would she do that?

The predator took no time to try to answer these questions, he was now so stimulated that he was close to climax. He pushed forward with his hips and felt his member force the nylon membrane of the pantyhose into the crease between the woman’s buttocks. He pushed harder still and felt his glans nestle into the woman’s anal bud, her silken hose wrapped around the sensitive head of his penis stimulating it into bringing forth a trickle of pre-seminal fluid; the clear liquid combining with his spittle to further lubricate his member. He grunted and pushed forward with all his bodyweight and actually felt the heavy table move an inch or two as he thrusted.

The predator felt his iron hard cock tear through the gossamer thin pantyhose gusset and then slam against the woman’s tight sphincter. His cock paused briefly at her resisting puckered entrance, then his weight and the lubricant did their job and his shaft slid slowly and steadily inside the woman’s tight back passage. The Predator’s crotch slammed hard against the woman’s soft round buttocks and his scrotum rested in the silken purse of her bunched panties stimulating him to extremis. He ground his crotch in a circular motion against the woman’s lovely soft arse and pulled her back hard against him and unloaded stream after stream of hot semen into her tight channel.

The predator howled and shuddered as his orgasm shook through his body; he ground his hips harder against her and stimulated his scrotal sac by rubbing it against the silken gusset of her pantyhose. His climax over, he pushed the woman forward and pulled back from her. He watched in awe as a trickle of semen seeped out of her and ran down her thighs, staining her stocking tops and pooling in the crotch of her panties. He had only just started with this bitch; he was going to have some fun tonight!

Michele lost all thoughts of red wine as she was propelled forward and slammed hard against the heavy wooden kitchen table. She was confused as to what was happening; her thought processes slow and fuzzy because of the wine she had drunk. She realised a stranger was in her house and that she was being pushed down across her own kitchen table but couldn’t figure out why. For one second she stupidly panicked at the thought that someone had found her dressed as a woman; and then a split second later she realised that she had a lot more to worry about than the exposure of her transvestism. She realised she was in serious trouble when she felt the handcuffs clamp on her wrists.

Michele’s fighting instinct took over and she used all her strength to lift her body up off the table so that she could yell a protest to the man who was assaulting her. She understood now that the perpetrator believed he was dealing with a woman; if she could just let him know that he had handcuffed a man, not a woman, maybe the intruder would let her go, or at least think twice about what he was about to do. Maybe she could negotiate with the trespasser; offer him money, her car, anything to get him out of her house without any further indignity.

Michele never got a chance to say a word; as soon as she opened her mouth the rubber ball gag was pushed into it. She started to hyperventilate, being forced to breathe in and out through her nose; then her chest was slammed downwards on top of the kitchen table and she couldn’t move. She stumbled as her heels were kicked apart and her legs spread to the full extremity allowed by her tight skirt. The home invader held her tightly against the table so that she wouldn’t fall, and then terror struck her she felt his hand reach under her skirt.

Michele was horrified at the prospect of what was about to happen to her. A glimmer of hope surfaced; he would realise she was not a woman and let her go, surely! Then she felt him yank her panties down and was actually relieved when her panties entangled in her garter straps and would go no further. As soon as the pervert reached under her to touch what he thought would be female genitalia he would be in for a terrible shock. He would be shocked by what he found there and would stop what he was doing. He would be disgusted to find out that she was a transvestite and may even beat her, but at least he would stop this perverted attack.

Michele’s glimmer of hope faded when she heard his flies unzip and the sound of him spitting into his hand. She was about to attempt one last struggle when her attacker’s full weight pressed against her backside pinning her to the table. She screamed to herself in her head as she felt her skirt being raised and the gusset of her pantyhose stretch as her attacker’s penis nestled in the bud of the entrance to her back passage. The fool didn’t realise she wasn’t a woman! He thought she was the lady of the house and he intended to defile her in this despicable manner to gratify his primal urges! Then she felt her attacker’s hard hot member tear through her pantyhose and begin to invade her.

Michele screamed into the gag at the intense pain as the hot cock forced its way inside her. No sound would issue forth around the gag but that silent scream would live in her memory for a long time. The man’s member slid slowly but inevitably deeper and deeper inside her; surprisingly after the initial shock and intense pain she felt as he had entered her, the feel of the invader’s lubricated penis became less painful; it just felt uncomfortable and filling.

Michele felt the intruder’s crotch press hard against her soft buttocks and realised with some relief that he was now fully inside her. She felt him pull her soft bum back hard against him and the gyrations of his hips as he worked his turgid member around inside her tight passage. Then she felt the hot gush of his semen as he spent himself deep inside her; she heard his groan and could smell the stale alcohol on his breath as he bayed and howled with his climax.

Michele was absolutely astonished at what happened next. As her defiler’s glans pulsated and throbbed against her sensitive prostrate, washing it with his hot seed, she felt a stab of exquisite sexual pleasure pulse through her lower regions and she simultaneously stiffened and ejaculated into the crotch of her pantyhose. She couldn’t suppress the pleasure she felt even though she felt utterly debased. She collapsed against the kitchen table as her orgasm subsided and she felt her attacker pull himself slowly out of her and was surprised that it did not hurt but in fact was mildly pleasurable.

Michele could feel that the tight bud of her back passage was left slightly open after the ravaging it had taken and she felt her attacker’s warm sperm run out of her and down her thighs where it pooled in her panties and stained her stocking tops. The front gusset of her pantyhose was soaked with her own spend whilst her attacker’s semen ran down her thighs into her bunched up panties. Her head was spinning with the realisation of what had just happened to her; then she began to wonder what would happen next.

To be continued…………………………………

The Predator pulled the woman up by her handcuffed wrists and heard her grunt into the ball-gag as she tottered on her high-heels. He pushed her down the corridor to where he knew her bedroom was located at the rear or the house. He couldn't help but become excited again as he looked at her round bottom and shapely nylon encased legs as she staggered ahead of him down the hall; he started to think what he was going to do next and started to stiffen in his jeans. When he got to the bedroom door he pushed her hard so that the bitch was propelled forward and fell face down on to the bed.

The Predator looked excitedly at the woman sprawled before him on her bed; her white A-line skirt had ridden up revealing the crotch of her full-cut red nylon panties and the lacy tops of her taupe high-sheen stockings, the tops of her thighs were framed magnificently by the black lace of the nylon full-slip. He opened his fly and coaxed his member to a full erection. God he loved this!

Michele lay sprawled on her bed; feeling completely exposed and helpless. She could feel his sticky come still dribbling from her back passage and she felt so degraded lying there with her skirt riding up revealing her red nylon panties and the lacy stocking tops; she wished she had never experimented with crossdressing; it was her fault, she should be ashamed of herself. She was even more ashamed that she had orgasmed when the predator had sodomised her; "my God, when would this end," she thought. Then she heard the unmistakable sound of a zipper opening and looked up to see the man open his fly and stroke his member until it was rock hard. Michele groaned into her gag and wondered what was going to happen next; how could this animal become aroused again so fast!

The Predator jumped onto the bed beside the woman; his hard member wobbling out in front him. He undid his belt and shucked down his jeans and underwear and kicked off his shoes when his clothing bunched at his ankles then he pulled off his socks so that he was naked from the waist down. The woman lay still on the bed breathing heavily through her nose because of the ball gag in her mouth. He worked his way into the middle of the bed so that his crotch was level with the woman's face. He reached out and turned her head so that she was facing his erect penis, it bobbed up and down in front of her pretty face. This was the part he really loved, but it was also the most dangerous! He warned the woman that he was about to take the ball gag out of her mouth and if she cried out or attempted to bite he would beat her until she begged him to stop. To prove his point he slapped her once across the face. He looked into her pretty heavily made-up eyes and saw the beginnings of a single tear; then the tear ran down her face leaving a small streak of mascara. The Predator figured she had got the message and reached behind her head and released the gag.

Michele screamed inside as the man jumped onto the bed; his erection wobbling out in front him and removed his clothing from the waist down. It would have been a comical sight in any other circumstances; the man struggling out of his jeans as his cock bounced up and down in front of him; but Michele was starting to realise what was going to happen next as the man moved forward and his erection approached her face. She could smell her musk on his manhood from when he had fucked her arse and she saw a bead of clear pre-seminal fluid form at the eye of his glans. Michele could not really understand the warning he issued but when he slapped her face she understood his intent. Her face stung and her head was reeling as the man reached behind her head and ripped off the ball gag; she gasped as the gag was released and managed to say one word: "Please!" before the beast pushed his cock into her mouth and grabbed the sides of her face and held her there while he fucked her face.

The Predator had done this to all of his victims and always loved the shocked expression on their faces as his cock invaded their mouths. The woman was so stunned that she didn't even think of biting; instead her lips clamped over his shaft and her tongue began slaver around the head of his penis as she tried to eject his member without biting it. The Predator started to fuck her face; his powerful hands held her face steady as he pushed his cock back and forth between her lipsticked lips. She could do nothing, trussed as she was, except capitulate.

The Predator looked down and was aroused and excited by the sight in front of him. The woman was heavily made-up (which he loved); her pretty face was framed by her brunette hair which hung to her shoulders and fringed her brows, her eyes were outlined in back eyeliner and her lashes heavily mascared. Pale blue eye shadow blending to a shade of dark pink coloured her sparkling eyes, her cheeks were heavily rouged, defining the lines of her cheekbones, her lips were coated in with a deep plum red lipstick; and sticking out of her matronly but attractive face was his pink, hard cock. He looked down her body at her arse and legs and then slid his eyes back up again to the woman's face and began to fuck her mouth harder.

Michele was still stunned from the slap as the rubbery flesh invaded her mouth and her first reaction was to eject the foul tasting monster. She was conscious of the fact that if she bit the invading penis she would suffer badly, so she clamped her lips over the man's shaft and tried to eject it. Michele pushed her tongue onto head of his penis and tasted a male cock for the first time. It was not what she expected; it was not salty as she had read it described so many times, but more of a creamy floury taste with an undercurrent of musk. She could also taste her own lipstick and perfume, and god help her if she didn't feel a stirring in her panties as her own member began to stiffen. Then she felt the man start to push his cock in and out of her mouth, groaning with pleasure. Michele realised that her attempts to expel his member were in fact arousing the man further; her tongue slathering along his glands and her lips tight against the taut sleek skin of his shaft were in no way effective in ejecting the invading penis, they were having the opposite effect. Michele decided that there was no way she was going to be able to repel his attack and decided that she would try to excite the man as much as possible so that he would get this barbaric act over with as soon as possible. As the Predator started to fuck her face; his powerful hands holding her face steady, she started to suck on the intruding member and work her tongue over his glans as her lipsticked lips moved up and down the shaft.

The Predator used long slow strokes so that the woman could breathe through her nose in time with his thrusts; he didn't want her gagging. Her soft lips and tongue were proving extremely arousing on the delicate nerves of his manhood. He loved it when he pulled back and the flange of his glans was between her lips and then the slippery feel of her wet tongue slavering his cock as he thrust into her face. If he didn't know better he would think the bitch was encouraging him.

The Predator felt his orgasm begin as his scrotum contracted and his penis started to convulse. Waves of pleasure shot though him as he felt his semen churn out of his scrotal sac and begin to shoot along the channel inside his cock, searching for release through the opening in the eye of his glans; the hot load spurned on by the blood engorged spongy walls of his shaft contracting and convulsing. The Predator held the woman's face hard and steady; he allowed the first few squirts of his ejaculate to stream into her hot wet mouth and then he pulled his cock back and out of her mouth; the head of his cock plopping out over her lips as the first jet of hot sticky semen ejaculated out of the eye of his convulsing cock.

Michele sucked and licked the invading penis as it raped her mouth; she was increasingly aware of the gossamer feel of her silky lingerie and stockings, the taste of her own lipstick and the light caress of her hair on her face. She could not help but become further aroused; the fact that she was cuffed and vulnerable added to her pleasure and allowed her to find an excuse for her debased reaction to this invasion of her sanctity; after all what could she do? All she could do, she rationalised, was to capitulate and to try to bring this brutal action to a swift end. Then Michele realised what was happening as the man quickened his pace and she felt his organ begin to contract and convulse. Her mouth filled with warm yeasty semen; it didn't seem to spurt out of his cock as she expected it would, it seemed more to just suddenly appear in her mouth. Michele couldn't escape the eroticism of giving her first fellatio, even if it was against her will; she felt herself ejaculate into her panties again, the warm flood of her own ejaculate soaking her panties and pantyhose as she swallowed his seed. Then the man pulled back suddenly and his cock plopped out of her mouth and she felt streams of hot sticky semen start to splash onto her face.

The Predator moaned with pleasure as stream after stream of white, warm fluid shot all over the woman's face; he rubbed his cock on her cheeks, her lips and her nose; coming all over her. A long rope of semen ran from the woman's brow, across her eye and onto her nose; as his cock rubbed against her face the semen mixed with her makeup and began to make a colour palate of semen, makeup and lipstick all over her eyes, cheeks and lips. He forced his cock back into her mouth as the last convulsions of his orgasm consumed him.

The Predator sighed as the last of his issue spent into her lipsticked smeared mouth; he stared into her scared, pretty eyes, now panda-like with the mixture of semen, mascara and eyeliner smudged all around them. God he loved to do this to these stuck up matrons. He pulled his cock out of her mouth and rubbed it all over her face again, the sperm and makeup now mixing with her tears. He let go of her face as she began to sob and rolled her over so that she was on her back, face up so that she could watch his final degrading act. He moved down the bed and grabbed a handful of her pristine white skirt and wiped the congealed mess of come and makeup off his cock with it. Her skirt was stained black and red by her makeup and silvery gobs of sperm were mixed in with the mess. "That'll stain," he laughed wickedly at the stuck up matron lying handcuffed on the bed before him.

The Predator finished wiping the mess on her skirt that was now rucked around her waist, and then he noticed the stain in the front of her red nylon panties. He knew that the spend from when he had fucked her had stained her underwear, he had seen the results of his orgasm on her buttocks and thighs; but he hadn't touched her cunt yet; he was saving that for later; so why was there wet semen all over the front of her panties? Then he saw the bulge there straining against the nylon pantyhose and panty gusset and slowly but surely he realised what it was! This fucking woman had a cock!!! What the fuck????????????

To be continued...

Like most crossdressers, for most of my adult life I have had the urge to dress-up as a woman for short periods of time, and I often used to dress in my wife's underwear when she was away on business. Since the divorce some two years ago, me, Michael, the respectable businessman, likes to transform into Michele, the sexy secretary (or naughty nurse; or whatever takes my fancy at the time) whenever it pleases me to do so. Living alone, and having the privacy to dress when it suits me, I have spent many hours developing the persona of Michele over the last two years. Of course I have to keep my secret life secret; and even though I have a strong desire to do so, I have never ventured out dressed as Michele.

I have acquired an extensive wardrobe, first at opportunity shops and then later at women’s clothing shops, insisting to the shopkeepers that I am buying the clothes as presents for my wife. Lingerie is easy to buy, as it is never considered unusual for a man to buy nice underwear for his wife or lover.

I bought my first pair of women's shoes from an opportunity shop, and once I had figured out my size in women’s shoes, I went ahead and purchased many styles of high-heeled pumps and sandals; again insisting to inquisitive shop assistants that they were presents for my wife. I sometimes even had the boxes gift-wrapped to maintain the façade.

I have experimented with wearing my wife's makeup with various degrees of success and failure during the years of my marriage. After she left me I obtained all the makeup I needed easily by purchasing a couple of complete makeup kits ("its for my niece's birthday; she's just turned thirteen" I told the shop assistant). I have added more cosmetics to this makeup collection by throwing any cosmetic item I desire in with the week's groceries when I’m out shopping. No one ever questions me at the checkout; husbands just pick up whatever their wives have written down for them on the shopping list after all.

It is easy to purchase women's jewellery of course, but my biggest problem was how to get my hands on some nice wigs. The problem was solved when I was sent by my firm interstate to Sydney on a business trip. I went to Paddy’s Market and there a sympathetic lady in a market stall that sold women’s wigs helped me pick out and try on three different wigs of varying styles and hair colourings. I purchased the wigs and then went up to Oxford Street where I went into a ‘specialty shop' and bought two pairs of breastforms in different sizes.

I love being Michele; I transform into her at every opportunity I get, and I spend most evenings and weekends dressed and fully made-up. I do not consider myself gay; in fact when I’m not dressed as Michele my sexual fantasies revolved around women; but when I’m dressed as Michele I often fantasise about being with a man or having a ‘lesbian' encounter with another transvestite.

I am terrified that my secret life will be exposed. When I am dressed I keep all of the doors locked, the shades closed and of course I never answer the door. Although I have become adept at applying makeup and dressing en-femme, and I believe that I make quite an attractive mature woman, I would never dream of going out dressed as Michele.

I read books and look at magazines and movies where transvestites have hot sexual encounters with each other and with male admirers. My favourite place to live out my fantasies is the Internet. I troll the chatrooms and cyber-space meeting places and I sometimes perform on webcam with other TVs and admires. I have been thinking a lot lately of either placing a discreet ad in a sex shop or advertising my availability in a contact magazine.

I check the time once more on the antique clock, and through the gloom I see that it is eight oh five. Now that I have finished working on my legal brief and the house has been made secure, I move towards my bedroom; my breathing quickening in anticipation. It’s time to transform into Michele and have some fun!

I strip off my clothes, shave my face closely and then take a long hot shower. I run my hands all over my chest, arms, legs and buttocks and am pleased to find them stubble-free. I fully shaved my body only two days previously and I used a hair-removal cream to remove all of the hair from the crevice of my behind and my scrotal sac. I can’t go to the beach like this, it would look suspicious being fully shaved. I also have to be careful at work, but working in a busy office where good grooming is expected, it is not unusual for a man to have the hairless ‘Metro’ look. The joke is that when my male work colleagues discuss fashion and the styles of the latest suits; I secretly wish I were dressed in the secretaries’ clothes rather than the latest business suit.

I dry myself off and sit at the dresser. I take my time applying foundation; it closely matches my skin colour and covers up the few blemishes that mark my face. I liberally coat my face and neck with face powder, one shade darker than my foundation; I now have the blank canvas on which to apply the rest of my cosmetics.

I apply eyeliner next, from the inner corner of my eyes to the outer corners, gradually thickening the line as I go. When I have thick black line running along the edge of my eyelashes I reach for my eyeshadow.

I select a pale blue which I apply to my eyelids and then blend it with a shade of dark pink which I brush onto the upper part of my eye sockets and right up to my eyebrows. Then I rouge my cheeks, defining my cheekbones. I like to use more eyeliner, rouge and eyeshadow than is the fashion nowadays. I like to imitate the makeup styles of the eighties rather than the current demure ‘less is more' look.

I apply a light coating of ‘skin-glow' face powder all over my face and neck to set the makeup and to give my face a subtle radiance. I carefully brush lashings of mascara onto my lower and upper eyelashes. I like to wear lots of mascara and have acquired a Maybelline product that does not clot and is relatively easy to apply.

I take my time applying my favourite Max Factor ‘Lasting Colour’ lipstick to my lips. I apply the base coat carefully just outside of my lip-line so that my lips appear fuller. I let the base coat set for a minute and then apply the clear topcoat over the ‘Raging Ruby’ lipstick and purse my lips.

I light a cigarette and concentrate while I paint plum red nail polish on my finger and toenails. Putting on two coats takes a few minutes but the effect is worth it. I keep my nails quite long and manicured; but this is another ‘Metro-sexual’ fad that is common among the men that I associate with at work and it does not attract attention. I stub out my cigarette and consider getting a drink. No, I decide I want to finish dressing first.

I study the three wigs sitting on their stands. I have a blonde shoulder-length, a black bob with cerulean highlights through it and my favourite brunette, with cerise highlights. I select the brunette and carefully lift it from the stand and brush it with my special wig brush. I admire the sheen of the artificial hair as I position the wig on my head and adjust it so that the fringe is straight and level with my eyebrows.

I open the bottom drawer in the dresser and there are my two pairs of breastforms. I take the smallest pair as I want a certain look tonight; more sophisticated then the bawdy size forty-two’s would permit. I affix them to my shaved chest with medical adhesive tape and cosmetic gum.

I open another drawer in the dresser and select a packet of flesh-toned sheer-to-the-waist pantyhose. I like to wear pantyhose as a foundation garment to help flatten my tummy, and to cover the small nicks and varicose veins on my forty-year-old thighs and ankles. I feel the first small tingle of excitement as I smooth the pantyhose up my legs and over my tummy and buttocks. I carefully arrange the toes of the hosiery around my painted toenails so that I don’t ladder them.

I stand up and walk over to my armoire. The armoire is an extravagance that I bought the week after my wife moved out and it is now filled with all of my female attire. For some reason I can’t mix my female clothing in with my male clothes. The built-in-robe that holds my boring business suits, shirts and dress shoes holds no interest for me tonight. Tonight I am totally absorbed with my armoire and the girly treasures contained inside its oak doors.

First I select some lingerie from a deep wooden drawer; the lingerie has acquired the delicate fragrance of the camphorwood drawer and I bring it to face and feel the sensuous satin on my skin and inhale the feint perfume. I place the lingerie I have selected to wear on my bed. My bed is a king-size four-poster with scarlet satin sheets and a black chintz comforter; another extravagance that I indulged in when the bitch left me.

I sit down on the bed and my pantyhose hiss as they rub on the comforter; little electric sparks shoot through my legs and my penis begins to swell inside the nylon sheath of my pantyhose. I push it between my legs and allow it to deflate so that I can continue dressing without an unsightly lump in my crotch.

I step into a white lace suspender belt that is fitted with three garter straps on each leg and then put on a matching white lace brassiere, adjusting my breastforms so that they fill the cups. I sit back down on the bed and slip a pair of taupe nylon stockings up my legs and adjust the dark back-seams so they were straight. I fix the dark welts of the stocking-tops to my suspender straps. My legs have a lovely sheen as they glisten in the lamplight; stockings worn over pantyhose give my legs a gossamer-like appearance and my red painted toenails peek through the sandal-toe-reinforced stockings. I run my hands up and down my legs enjoying the sensuous feel of the nylon but have to stop myself when my penis begins to rouse again.

I pull a pair of white satin full-cut panties up my legs and smooth them around my buttocks and over the suspender belt and then step into a peach coloured satin half-slip. The lace hem of the half-slip flutters against my stocking tops. The scintillating feel of the lingerie on my body arouses me further and I have to reach inside my panties and hose and adjust myself.

I walk back to the armoire and select a navy blue women’s business suit and lay it out on the bed. I step into the skirt and admire the single pleat at the front and the split side. It looks both professional and sexy, but it couldn’t really pass as a business suit because the hem only just covers my stocking-tops. I bought the suit off the rack at Carla Zampatti in Sydney and had the skirt adjusted at a tailor in Oxford Street who is probably the only man in Sydney that would dare to cut a hem that short on woman’s business suit. Of course he is used to the sort of clientele who make such requests.

I button myself into a peach coloured, long-sleeved, satin blouse and tuck it into the waistband of my skirt and close the zipper. I adjust the waistband of my skirt, and adjust the hem down over my slip. The skirt is tight around my buttocks and thighs and the hem sits high up on my legs.

"But why?" I pleaded again.

"Because Mike, you need to be taught a lesson. Although we enjoy having sex with you and each other, and really get off on your nylon fetish, you did rape us!"

"What?!?" I asked amazed.

"All of us Mike, you forced yourself on all of us to begin with. So now you are going to see and feel what it's like to have someone force themselves on you. We have turned you into a girl; and now we are going to rape you!" Mom said viciously, her heavily made up face angry but so sexy.

 

 

"Remember Mike, you forced yourself on me first," said my Sister Eileen.

"You dry fucked me fully clothed after I caught you playing with Mom's pantyhosed legs while she slept."

My mind went back the that first fateful evening, I remember my Sister pleading as I lay on top of her:

"And me Mike, you raped me too. I know that you will argue that I now love every second we spend in bed together, but the first time was Rape!" cried my Mother.

I remembered the first time I had taken Mom. She was setting me up to take me to some shrink because she had found out about Sis and me. It's true I forced myself on her; I remembered her eyes when I fucked her, so icy:

"And with me Mike; you even had your Sister, assist you into blackmailing me to having sex with you. Yes it's true that I had given you the 'come on' and would gladly have let you have what you took; but you did essentially rape me," quipped in Matron, the last of my three nyloned goddesses.

I remember that Matron had flirted with me and that was one reason I was determined to have her, but I did force myself on her to get my way; with Eileen's help as I remember it:

I was smiling to myself as I remembered taking each of my girls, my Mother, my Sister, and finally, Matron; my Mother's boss. They had all been willing participants for the last few months, so why now was I handcuffed to the ceiling with a space bar between my legs.

"So what are you going to do then?" I asked, a little worried about my vulnerability.

Matron turned around now; up until now she had her back to me and was fiddling with something. As I had noticed before; she was dressed in a black full body corset and waist cincher, her tits pushed up and out. From the bodice of her waist cincher, suspenders ran down her legs to her favourite smoky grey fully-fashioned nylon stockings. She had on a pair of the highest heels I had ever seen; black of course. She was heavily made up. But, more importantly; she now had a huge rubber cock growing out of her crotch!

"Why Michele we are going to rape you of course!" she laughed.

"No, no, no! You keep that fucking thing away from me! You girls let me down and get me out of these women's clothes and makeup, right fucking now!!!" I screamed and struggled uselessly against my restraints.

"Or what Mike; you'll tell someone about this? The full story about how you have a raving fetish that has been your only excuse to commit incest with me and your Sister?" Mom hissed scornfully at me.

"Or that you not only forced me to perpetuate your incestual, nylon fetish games; but cajoled me into helping you rape the Matron!" spat my Sister Eileen.

"Oh no Mike, we made you into Michele, so now you can feel the same sense of helplessness that we felt when you initially forced yourself upon us. I'm sure you'll get to like it Michele, just like we did!" Matron finished.

"So now honey, as an old saying goes: 'when rape is inevitable, lay back and enjoy it!' Obviously some stupid MAN thought of that, but in this case it's apt I think; although you can't really lie down now can you?" taunted Matron laughing.

Matron reached for a tube of lubricant that was lying on the bench and commenced to liberally coat the monster black cock strapped to her pelvic area with the greasy liniment. My eyes shot open wide at the size of the rubber penis protruding from her loins. It had to be eight inches long and Matron was having problems getting one hand around its girth.

"Don't worry Michele, we'll provide you with foreplay so that you're nice and lubricated when it enters you." Mocked my Sister, pointing at Matron's huge false cock.

"Oh that's right; men don't get wet down there do they? Never mind well see if we can take your mind off the your forthcoming ravaging anyway," Eileen taunted me further.

With that, my Sister came right up to me, face to face, and put her arms around me. It felt strange being in women's clothing as she held me, but the feeling of the slinky skirt against my nyloned legs was arousing and the feel of my Sister's body pressed against me excited me even more. She looked into my eyes and whispered,

"God! You are quiet pretty Michele!" and mashed her lips against mine. My lipstick lips on hers provided a unique and wonderful taste and as she pushed her tongue into my mouth I felt my penis beginning to stir in my nylon panties.

Eileen continued to kiss me and rub her body against mine, her beasts rubbing against my false breasts and her nylon bustier rasped against my blouse, creating erotic sensations that I had never felt before. My Sister's hand dropped from the embrace and came to rest on my right knee. I felt her stroking me there through the diaphanous nylon stocking, then she slowly worked her hand up my leg. It was the strangest experience; my legs splayed and held in place by the chrome bar clasped to my ankles, and my Sister sliding her hand up under my skirt and along my stocking thigh. She was still kissing me deeply and the taste of lipstick was delicious in my mouth. My Sister ran her hand up the a garter strap, lingering to tickle the bare skin at the top of my thigh where the stocking ended, and then her hand slid slowly upwards and gently cupped my balls through the gauzy nylon of my panties. I began to thrust against her hand, enjoying the sensations of nylon against my cock.

She then removed her hand and placed it back on my shoulder, she pulled her face back a few inches and looked at me,

"Better stop that; we wouldn't want Michele coming before we are ready for her to come, hey Mom?" she said looking deeply into my eyes.

"No honey, not until we are all ready," I heard Mom's reply close by and to the left.

I looked over and she was right there close to Eileen, they looked so hot; my Sister in her tight nylon bustier, taut red Lycra hotpants, and glossy taupe pantyhose. My Mom dressed in her black leather miniskirt, low cut blouse, six inch 'fuck me' pumps, and sheer black seamed stockings. Eileen started kissing me again, pulling me to her against the strain of my hands cuffed high overhead. My wrists were starting to hurt but my Sister's sensual attack was taking my mind off the pain. I felt Eileen move slightly and opened my eyes to see what happening. Mom was on her knees beside me, and as I looked she commenced to stroke my spread legs. She ran her hands up and down my smoky grey stockings creating little electric shocks along my legs. I was looking at the black seams running down the back of her claves to her shiny black pumps when Sis commenced kissing me again in earnest.

Eileen's hands had now moved inside my blouse and she was stroking my false tis through my lacy bra. She also ran her hands all over my chest, which felt wonderful now that it was hairless. Mom's hands had worked their way under my dress and stroked my stocking thighs, then she too moved over the brief expanse of flesh between stocking and panty and lay her hands on my sex organs. As her right hand caressed my balls through the gauzy nylon of my panties, her other hand stroked my hardening member through the tight nylon panty material.

"Let me look," I mumbled into Eileen's mouth through our passionate kissing.

My Sister eased back slightly and looked herself at our Mother on her knees, dressed as whore whilst stroking this trussed up whore's legs and panty covered cock. As we both watched, her head went under my skirt and I felt the exquisite savour of my mother's hot lips and tongue on my erect member as she worked on it through my nylon panties.

Mom reached out and grabbed both sides of the hem of my skirt and in one quick movement, pushed it up around my waist. I looked down and saw my Mother between my legs which were encased in fully-fashioned smoky grey nylon stockings, I could see that my toenails were painted bright red through the opaque reinforced toe seam. On my feet, a pair of Mom's black high-heeled, open toe, pumps. My Mom was on her knees, close to the metre long stainless steel bar that held my legs apart. Her heavily made up face was buried between my thighs as she sucked my now fully erect penis through a pair of the flimsiest white nylon panties I had ever seen; the straps from a matching garter clung to my thighs and ran down to my stocking tops.

"See Michele; your Mommy loves you," my Sister whispered in my ear.

"And I love you too," she whispered again and pressed her face into mine to commence another passionate kissing session.

I felt my Mom ease aside my panties and take my penis between her lips and gently and slowly begin to suck it into her mouth as she slid her tongue around the sensitive glans. The feel of the sensuous clothes I was wearing, the nylon stockings, the panties, and the strange yet exotic taste of makeup as my Sister kissed my lipstick into my mouth was arousing beyond anything I had ever felt before. My Mother was now sucking me in earnest, she had tucked the front of my skirt into the top of the waistband and her hands ran crazily up and down my stocking legs. Every now and then she would grab the bar between my ankles and push her mouth hard up against my groin, taking my member deep in her throat. My Sister continued to passionately kiss me and run her hand over the outside and inside of blouse, caressing the sleek nylon against my chest. I was close coming.

Then as if by some prearranged signal (which I'm sure it was), my Mom grabbed my calves and locked my heels solidly on the floor. At the same time my Sister put her arms around me and held me as tight as she could as her mouth crushed against me and her tongue went wild in my mouth. I became briefly aware of a presence behind me and my skirt being lifted from the back. Then I feel my panties being pulled down and a fumbling, as a cold, rubber object is nestled between the bare cheeks of my arse.

My God! Its Matron; I had forget all about her.

With that Matron thrusts and I feel my back passage ripped apart as the rubber cock enters me. I squeal with pain as the hard prick fills me and I feel the worst pain I have ever felt. I am held by my Mom and Sister and can't move in any way, my Sister continues to kiss me as she whispers between the kisses,

"It's ok Michele, relax, take it!"

Then Matron whispers in my ear as well, I can feel her body against my back as she wriggles and thrusts, forcing her rubber strap-on cock into me.

"Shut up bitch! Now you know how it feels," as she commences thrusting in and out of me.

On each forward thrust Matron's cock drives deeper into my ass. Because of the pain I have tears of mascara running down my cheeks but my cock remains hard as Mom continues to suck in rhythm with Matron's thrusting. My Sister continues to kiss and caress me as my Mother strokes my stocking legs running her hands in spidery waves up and down my calves and thighs.

I quickly realise that trying to squeeze Matron's cock out of my arse is only hurting me more. Matron is panting now and I can feel her hot breath on my neck. I force myself to relax the muscles in my arse, a strange thing happens; as the cock-head of Matron's hard rubber penis rubs against my prostate, I feel a warm tingle of pleasure. The please is amplified by the sweet lips of my Mother, who is gently sucking my cock now that she has realised I'm no longer struggling. My Sisters kisses are sweet and I respond and offer my tongue back to her and taste her luscious lipsticked mouth.

I start to get into the same motion as Matron, pushing back on her as she thrusts, pulling back away when she pulls back on the backstroke. Matron quickens her pace whilst at the same time Mommy sucks harder on my now pulsing penis. My Sister Eileen sucks my tongue deep into her mouth and pulls me hard against her, her breasts pushed hard against mine, Mom sucks my penis deep into her hot wet mouth and sucks hard and ravishes the glans of my penis with her tongue. Matron is fucking me hard and fast and then as she senses my climax, Matron drives her hard rubber cock deep in my arse and gyrates her hips.

My orgasm is so intense I think I might faint. My cock convulses in my Mother's mouth as streams of semen eject from my pulsing, turgid member; my arse spasms from the pressure of the hard cock stimulating my prostate; and my mouth tastes the sweet zest of my Sister's fragrant mouth. I love the feel of the silky clothing caressing my body, the sleek stockings on my legs, the sheer panties still clinging to my scrotal sac, the blouse gently nuzzling my chest and back. I push myself up on my tiptoes as my high heels rise inches off the ground as my climax drives me over the top.

I am spent, all resistance gone; I am entangled in a silken family trap!

THE END