Published Sex Stories / transgender-stories

Nylon Mistress on Transgender Stories

Liza giggled as she sat back down on the sofa, a mischievous smile on her face.

"Whats so funny I asked?" wondering what had tickled her fancy. After all the only thing that had happened was that she'd just been to the toilet to relieve the pressure that the 3 or 4 glasses of wine that we'd both had must have been causing her.

"Come on what brought on the giggling fit?"

She stood up and came over to me. In what seemed like a strange move she turned side on to me and put her foot next to mine.

"Yep thats about right then, quite a bit bigger just like I thought" Then she laughed and sat back down again, her face glowing and two eyes that just said mischief.

"Umm is that a surprise? Of course my feet are
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bigger than yours!"

"No it's not really a surprise, what was the surprise was what I saw in your bedroom"

"What do you mean? Why were you in there?" I said, trepidation building in my body as the words came out of my mouth.

"Oh I didn't go in there initially, I just glanced in  as I was coming out of the bathroom, and I couldn't help noticing the pantyhose hanging over the side of the bed. Then my curiosity was piqued and I saw the lovely black Maryjanes on the floor below. Thats why I wanted to check what size you were. And as it happens you seem to be about the correct size to fit them. And what was even stranger was the shoes are exactly the same as these ones I'm wearing today. So...anything you might want to tell me?" and her voice trailed off as she laughed again.

"Umm well they belong to.." and she sharply cut me off "Don't give me a bullshit story, I know they're obviously yours..so what's the deal?"

I didnt know what to do, I was caught red-handed with no escape. My little secret had been uncovered and I could barely get a word out in explanation.

"Well...it's just that every now and then I...." and then my own voice caught as I tried to work out what to say. The evil look on her face was one of fun though, and I suppose the wine had made us both a bit more open to surprises so I blurted the truth out.

"Look, I've got a real fetish for some things. And as it happens pantyhose and heels are top of the list. I really get off on wearing them, I know its weird but I cant help it"

"Yeah OK I got no problem with that, but is it an accident that the shoes I saw match my own perfectly?"

"Well no...What REALLY gets me going is to wear something that someone I know wears. I love looking at what all the girls at work wear and trying to get my own.And I like yours especially. It takes a while to find out the right brand and everything, and then to get some that fit me, but when I do... well... And I knew you were coming today and I was hoping you'd wear those shoes so I sort of prepared by wearing mine for a while earlier. Oh god, you probably think I'm a real nutter"

She looked across at me and then stood up. "Well come on then, if you like to wear them that much we should match now. Come on, put em on and show me"

My heart was going a million miles an hour. I was terrified but excited at the same time. Liza was about to help me live my ultimate fantasy. Even as she dragged me into the bedroom my dick started to stiffen. Oh god, how was I going to hide it!

We sat on the bed and she told me to take my jeans off. I dropped them to the ground and then removed my socks.

"Ok put the pantyhose on for me" I did as I was told and she said "Oh dear, you even know how to put them on properly, you've obviously been doing this for some time. And by the looks of things you really do enjoy it too" as her eyes glanced downward toward the throbbing member that I could no longer hide.

"Come on, shoes next" and I reluctantly slid my feet into the heels and buckled them up.

She looked at me and said "You know ordinarily I wouldnt be interested in you, as you know, we're just friends. Maybe its the wine talking but this really turns me on I have to say." She leaned across and kissed me lightly on the lips.
"So, it seems a shame to waste this, what say we have a bit of fun then?"

I wasn't sure what she meant but then she rolled over and pulled me onto the bed. She positioned me face down and then removed all her own clothes except her own pantyhose and shoes. She slid on top of me and for the first time I felt the exquisite feel of nylon upon nylon as she moved her own legs in and out of mine. My god the feeling was incredible, it was everything I'd ever hoped it would be, and I was in heaven. Judging by the noise she was making it was something good for her as well. Every time she moved her leg a tingling sensation went through me and I was sure that I'd cum in record time.

"Do you want to swap around?" I heard her say?

"In what way?

"This time you can be the girlie" and I felt her rip a hole in my pantyhose and her finger started playing with my rear. Oh god this isn't what I'd planned, I'm not sure I want to go here. But she kept going and pretty soon I felt her slender finger invading my crack, and then slowly sliding inside my hole.
Is this what its like I asked myself? I know I'm not gay, but boy does this feel good. Liza kept it up for a while with her finger exploring everywhere inside my hole and I was going wild with delight.

"You got a vibe or a dildo?' she asked?

"Umm yeah in the bedside drawer" I figured she was going to let me play with her a bit now. I didn't think we'd actually fuck as such, I didn't think that she'd want that so the vibe request seemed reasonable. But I was wrong. Seconds later I felt a healthy squirt of lubricant on my ass and then the tip of the vibe was nesting in my ass crack

"Oh I'm not sure we should go down this road?"

"Don't be silly, if you're going to dress like a girlie you need to be fucked like one, I think you might just enjoy it" she said as she pushed the first part of the vibe in my hole.

Oh god it felt like a telephone pole it was so big, but I couldn't disagree that it was making me extremely horny and my dick had never been harder. She pushed more, and more and gradually the whole length was inside me. I'd never felt anything like this before and although it was uncomfortable, I wanted more all of a sudden.
Liza started to move it in and out in long slow strokes, gradually building up momentum. Almost involuntarily I started to respond and move with her rhythm. She would thrust and I would push back. It was feeling incredible and she knew I was enjoying it.
By this stage she'd moved into a reverse position so she was next to me and her pantyhosed legs and feet were next to my head as she concentrated on fucking my hole with the vibe.
I grabbed one of her feet and started to lick her leg, my tongue dancing over the nylon and occasionally onto the leather of her shoes. I was surprised to hear her moan, obviously she had some fetish in this area as well. I renewed my licking and slipped one of her shoes off and started to suck her toes through her hose. She momentarily stopped fucking me as she gasped with pleasure. Seems we both shared some enjoyment here.

"Are you ready yet?" she asked me in between moans

"I'm so close it doesn't matter, and if you slam that thing inside me one more time I'm gonna flood the bed soon"

She pulled the vibe out of my swollen ass and quickly rolled me over onto my back. She grabbed a spare pair of pantyhose out of my drawer and wrapped them around my swollen member and then placed her mouth over them as well. My cock went into her mouth surrounded by nylon... I was in heaven and living my ultimate fantasy, and I could believe it.

"Oh god I'm gonna cum...you gotta let me cum" I yelled.

She ripped a hole in my pantyhose and swivelled around and stuck her finger back in my ass hole. Then she positioned her own feet next to my cock. With barely a couple of strokes from her free hand my cock erupted and a torrent of cum shot forth from it. The sticky juice went all over her leg and shoes,and trickled down in between her toes. It was more than I'd ever cum in my entire life, I thought I'd never stop.

"Enjoy that did you?"

"Umm, yes, very much so" I gasped trying to catch my breath.

"Good, cos Its my turn now and I snuck a look in your closet and saw all those other shoes and we're going to try them all out tonight..."

And I knew that there was a LOT more still to come.....


Diamond

girlcock on Transgender Stories

She was a vision from behind. Her long curly hair fell down her back in golden-brown and raven ringlets to brush the tops of her black leather chaps. Her bottom was bare, thrust out of the tight leather leggings, round and full and firm. The bare skin was a deep, latte brown. High-heeled platform boots peeked out from beneath the bottom cuffs of the tight chaps that hugged her thighs and calves, outlining the muscles of her strong, long and slender legs.

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margin-top-alt: auto; mso-margin-bottom-alt: auto">But it was when she turned that I knew this was one I had to have, if I could. She faced my direction and nonchalantly leaned against the pillar, looking idly off at Club X’s dance floor. I could see now she wore a slave harness that been obscured by her long hair from behind. But when she turned to me I could see how the black leather straps framed her delicate breasts, making an “X” in her cleavage. In her navel she wore a large, dangling gem that shimmered in the club light as she moved her hips slowly with the rhythm of the music.

That was almost enough in itself. But there was more.

Over her loins she wore a leather jock. Its pouch was covered with black metal studs, like scales, and I could see the brass snaps around the edges. She could pull it off with a sweep of her hand. With all that gear I couldn’t tell how large her package really was, but I wanted nothing more than to find out.

I was already imagining the discovery as I slowly made my way over to her. But I was frightened almost speechless. I’m a fit good-looking guy, six-one if an inch, with blond hair and a healthy enough sun-glow, and I was not afraid of shemales. But she was something else. “Out of my league,” I thought.

I was dressed all in rubber; a latex “t” on top of a pair of  “Mr. M.” black rubber codpiece pants, which hugged my thighs and ass. I looked good and, inside, the rubber was beginning grow slippery inside with the first faint hints of perspiration, which made me feel good, too. I could feel my cock strain slightly against the rubber fabric of the pouch. The cock-rings I wore around the base and shaft cantilevered my cock outward a little, but mostly it was all me. The rubber felt good, slipping back and forth against the tip of my cock. 

She turned and looked at me as I approached. I sort of froze for a moment, trapped as in a basalisk stare. I almost tripped over my own feet. She noticed and laughed, her head dipping forward then back, making her hair shimmer in the light. Her full lips peeled back into a wide grin and she looked me up and down, taking me in, checking me out. She put a slender hand up to her chin and cocked her head to one side in mock assessment. After what seemed like forever, she finally raised her hand and gave me a coy “come here” gesture with her index finger.

I was relieved but still without something clever to say as I swaggered up to her, trying to look bold.

She leaned over so I could here her over the thump of the music and spoke into my ear.

“Busted!” was all she said.

Her breath against my ear thrilled me and I felt the goose bumps rise on my arms. She noticed and gently wrapped her hand around my bicep, caressing downward, and took my hand in hers. I trembled at her touch. She didn’t stop there, but with her other hand began caressing my rubber-covered chest lightly with her nails. She circled around my left pec until she found my nipple, which had grown hard, peeking though the slick fabric. I stiffened as she ran her nail across it. My cock jumped a little and, with a little thrill of ecstasy, I moaned as I felt a drop of pre-come shoot out of the tip of my cock. It lubricated the inside of the latex pouch so that every movement felt like a slick caress.

She leaned over and spoke into my ear again. “You didn’t shoot it already, did you?” I shook my head and tried to reply, but the music was too loud for a proper explanation. She read my face. “Shall we go somewhere quiet?” she shouted over the din, and without waiting for a reply, took my hand, turned, and led me toward the stairs behind the dance floor.

I was working up a good sweat now, so that each step was like a warm embrace inside my rubber sheath. My cock felt hot inside its slick pouch as we moved through the gyrating dancers. There were pretty boys in leather and rubber, S&M hunks in leather chaps and vests, cute little goth girls in corsets and white face powder. They eyed us with sidelong smiles as we brushed through them. A few of the boys brushed up against me, copping little feels here and there, on my thighs and ass. I didn’t mind. I loved their looks and their touches.

Upstairs we found a large, square room, dimly lit with red light. Lining the walls were several alcoves with bars on them. They weren’t cells. They were private play spaces Club X was famous for. The bars could be shut and locked from the inside, for a little privacy, or left open to invite others. Several were already occupied. We could see their dim shapes moving within and hear people sighing and panting with pleasure and, in a few, pain. Little crowds had gathered around some of the occupied alcoves in twos and threes. Some stroked themselves. One pair of boys in rubber cat suits and hoods stood watching and stroking each other, their cocks the only skin visible, almost glowing in the reddish light.

There’s nothing like the sight of a hard cock. I love it. I have since I was a boy. It gets me hot. Looking at those too boys all rubbered-up, their cocks out, each slowly stroking the other, sent a shiver through me and again I felt the little charge as I shot another little load of pre-come into my pouch. It felt so good I stopped and let out a little “uh!”

“Again?” she said. I could hear her ordinary voice now. It was soft but strong, neither gruff like a man’s nor high-pitched like a woman’s. She smiled, looking up me quizzically. I leaned over and spoke softly in her ear.

“It’s a little thing I can do,” I told her. “When I’m in rubber and in the right… frame of mind.  It’s like mini-orgasm. I get this intense thrill for a second or two and I shoot off a little clear pre-come.”

“Wow,” she said, raising her eyebrows and flashing a broad, white smile. “Sounds like a superpower to me!”

I laughed. I’d never thought of it that way. I liked the sound of it. I liked her. I loved that smile and the mischievous sense of humor behind it.

“My name’s Michael,” I said.

“You’re Superman to me,” she replied, with a giggle. “I’m Diamond.”

“A pleasure,” I said taking her hand and kissing it.

“But enough with the niceties” she said, and pulled me over into an open alcove. “Top or bottom?” she asked as she closed the barred door and set the latch.

“Both and neither, I guess,” I replied. I hadn’t ever been asked the question like that. “I don’t really play that way. I like to play and just see where it goes. You?”

She gently put her hands on her hips and looked me in the eye. She looked magnificent standing there. I could see the muscles move beneath the taut flesh of her arms. She was buff but delicate, strong but soft. She is perfect, I thought. 

“About the same,” she said at last. “But there’s one thing I know I want.”

“What?”

“I like my cock sucked by good looking boys in rubber.”

“Good.” A couldn’t help the grin that spread over my face. “I love to suck beautiful girl-cock while wearing rubber.”

As if directed by an invisible puppeteer we came together and embraced. My hands moved down the contours of her sides and leather bound hips, coming to rest on the hot flesh of her full, round ass. I caressed its curves as we kissed for the first time, our tongues searching each other’s mouths. She reached down and ran her nails up my rubber pouch the same way she had done to my chest. My cocked stiffened to meet her touch and for a third time I shuddered and groaned and let fly a little juice inside my pouch.

“Superman,” she whispered.

She reached back and took my hands away from her ass. Glancing behind her, she took a step back and sat on the edge of the upholstered platform that served as the cell’s play-bed. She leaned back and spread her leather-embraced legs wide, her leather- and metal-clad package thrust out.  She reached behind her, pulled and pillow from the bed and tossed it to her feet.

I took two steps forward and knelt down on it, between her legs. I caressed the leather chaps as I took in her fragrance -- leather and sweat and sex. I bent down and kissed the open space of her inner thigh, between the pouch and the tops of the chaps. I nibbled and licked playfully, and she began to moan. I ran my tongue along the underside of the studded pouch. Through it all I could feel her cock growing inside. I was pleasing her and I loved it.

I glanced behind me for a second. We had an audience of three or four standing on the other side the barred door. The two boys in rubber suits had wandered over and were stroking their cocks, watching and waiting. It thrilled me, flattered me.

 

I turned back and leather and steel pouch seemed to pulsate in front of me, inches in front of my face and lips. I reached up and slowly undid the snaps, one by one. I pulled the pouch away and her cock stood upright, freed at last from its little prison. It was gorgeous -- long, thick and full. Like me, Diamond wore cock rings around the base of her cock that further engorged her sex, making it so hard that the head of it gleamed purple and shiny. I noticed the thick gold ring that curled out of the tip and pierced her glands: a Prince Albert. Her balls were shaved, big and heavy. I cupped them gently in my hand and tugged. It must have sent a thrill through her because she arched her back and moaned.

I couldn’t stand it anymore. I had to have my mouth on it, to feel and taste it with my tongue. With my free hand I lifted it up. Like her balls, it felt heavy in my hand. I placed my tongue, broad and wet, right at the base, where the ball-sack met the shaft. I slowly eased my tongue upward, feeling every little nuance of its shape and texture, tasting its sharp tang. It was heaven. I eased my tongue up and down the underside of her shaft, licking the glands when I got to the top. She sighed and moaned with delight.

“That is so good,” she whispered. “You’re such a sweet little cock-licker.”

It’s true. I am a sweet little cock-licker and I don’t mind admitting it. I love cock, especially girl cock. Boys will do, but girl cock is the best.

I ran my tongue up the underside once more, put my lips around the head and put it in my mouth. I could feel the heavy gold ring on my tongue. When I flicked it back and forth she moaned, and jerked her hips. I pulled away and watched as a silver drop of pre-come oozed out of the tip.

I looked up into her brown eyes and smiled. “Now whose the superhero?” I said and licked the droplet off as it ran down the curve of the gold ring.

I went down again, holding the base of the shaft in one hand, opening my jaws wide and taking her deep. I let my tongue dance over the head and glands on the upstroke, licking the shaft on the way back down. I could tell she liked it. She kept moaning and whispering, “Sweet little cock sucker,” “Such a slut for cock,” “You love my cock, don’t you, little boy?” and “Worship it.” 

 

Suddenly she reached down and grabbed me, one hand under each arm. She pulled me up onto the bed with her, twisting her body so that I was now lying next to her. I looked into her eyes and she kissed me deeply, our hands running over each other bodies. Her touch was electric through the rubber.  

She reached down and all but ripped my pouch off, the metal snaps going “click-click-click” as she pulled it sharply away. As she did so, I could see the clear, sticky but viscous strings of pre-come stretched between my package and the pouch.  My cock was free at last from its luxurious cage. It was beautifully hard and full and it glistened with slippery, sticky pre-come. 

“What a lovely mess you make, Superman.” She smiled, holding the pouch up.  To my surprise -- and delight -- she brought the pouch to her face. Her tongue darted out and licked a little of the ooze out of it, letting it slide off her lips and down her chin. Then, her mouth glistening with my ooze, she tossed the pouch aside and leaned over me, bringing her face down close to mine. I licked her lips and chin and cheeks. I could taste myself on her lips and tongue. She kissed and licked my face in return. I loved the feeling of her warm, wet tongue, broad against my skin and lips. She reach down and gently gripped my cock, still juicy with my ooze. She stroked it slowly as she kissed and licked me. It thrilled me and I shuddered and yet another little wad of clear, slippery fluid shot out of my cock. It landed in the palm of her hand.

“Oh!” she said, with a start. She laughed. “That’s how it works. Nice trick.”

She licked the head of my cock twice and then took it deep.  She pulled on by balls like I’d pulled on hers, but harder, more forcefully. It hurt slightly, but it was a sweet pain. It felt great to have my sex man-handled by this gorgeous creature. It made me feel desired.

She moved down to lick and suck my smooth-shaved balls. She encircled the base of my sack with her thumb and forefinger, cupping my balls snuggly with the other. With her free hand she began stroking me, up and down, around and around. She knew what she was doing; she teased the head on up the upstroke, playing over the sensitive part beneath the head. I kept lubricating myself with little pre-come jisms, one after another.

I was almost there but didn’t want to go, yet. I wanted to make this last. I gently put my hands on her cheeks and lifted her head away from my cock. She slurped a bit as her lips came away from me, looked up and me and smiled.

“What’s up, Superman?” she asked. But I could tell she knew why I’d stopped her.

“It’s too good,” I said, “I’m not ready.”

“Good,” she said as she sat up, looking me in the eye. “I want to take you home.”

Half and hour later we were in her apartment in the Castro. I watched her take off her coat as I took off mine. Even that simple act seemed alive with sex. We had been kissing in the back of the cab. It had almost getting out of control when the driver cleared his throat loudly and gave us a sour look in the rearview mirror. Still I was pretty hot and when I saw her gorgeous round ass cheeks sticking out of the leather chaps again, it was almost too much. I gave another little squirt in my codpiece as I drew in a quick breath.  She turned when she heard me and gave me a knowing glance.

“Thank heaven there’s no kryptonite around, Superman,” she laughed. “Give me your coat.”

She hung it up in the hall closet and led me into the kitchen where she poured us each a vodka tonic. We went into the living room and she asked me to sit on the black leather sofa. The room was decorated in an ancient Greek motif, with black and orange vases, columns for end tables and so forth. One wall was papered in what looked like scenes from the ancient Olympics.

“I’ll be right back,” she said, “I want to slip into some play clothes.”

“Play clothes?” I thought as she turned and sauntered down the hall, her ass swaying deliciously back and forth. “If those are her street clothes then… ” I wondered how much wilder and better this could get.

While she was changing, I examined the wallpaper more closely. It was printed with the sort of nude hoplites, wrestlers, discus throwers, and gymnasts of the kind you see in Greek art. Then I noticed the men’s cocks. They weren’t the oddly small pricks usually found in Greek art, they were big, and most were either stiff or halfway there. I noticed too that some the characters were female, also unusual in Greek sports scenes. Then I saw about half these “women” had cocks. I got up close and looked at their faces. They all looked exactly like Diamond’s. I was floored.

“You like the wall paper?” I heard Diamonds voice behind me. It sounded slightly muffled.

“It’s you,” I said without looking away from it. I wanted to look at her, but I also wanted to savor the anticipation.

“I was the only model I had available,” she said.

“You painted this?” I asked, still staring at her profile on the wall.

“I design these things,” she said. “As you can see by looking at me I like Greek things.”

I turned and was floored once again. Diamond was head to toe in gleaming black rubber, her face was obscured by tight-fitting latex mask. One top of that she wore what looked like an ancient Greek helmet, also shiny black, complete with a black brush made of short rubber tubes. Her body was encased in a cat suit that fit like a second skin, so taught that in only creased at her elbows and knees. Around her waist was a tight bodice or corset, the front of which was molded to look like the “abs” on Greek armor. Her suit sported a snap-on codpiece, like my pants, and I could see the curves of her cock and balls against the rubber. She wore a pair of knee-high lace-up boots with platform heels. Diamond was a vision: a slick, shiny Amazon, oozing with sensuality. 

 

The only visible flesh was her eyes and mouth -- her lips looked so plump and juicy -- and the tips of her fingers. In her hand I saw she held a collar with a chain leash coiled in her fist. In the other she held something else, something leather.

“I love it,” was all I could say. It was the hottest thing I’d ever seen.

She swaggered over to me and told me to hold still as she buckled the collar around my neck. Then she knelt down and began strapping the leather articles around my knees. They were kneepads.

“You get to be bottom tonight,” she said. I didn’t argue. I hoped that meant sucking more cock. “On your knees.”

I went down on all fours and she lead me slowly down the hall and into the bedroom. The room was decorated in more of the same, but the illustrations were more explicit, with the figures fucking and sucking one another, beating one another with cats of nine tails and other things. Some of the figures were creatures from mythology – minotaurs, centaurs, satyrs and medusas, all sporting beautifully erect cocks. Over the bed was an oil portrait of Diamond herself, lying on her back on a bed, nude, her long, thick cock curving to one side over her belly. The bed was covered in black rubber sheets.

“Get up on your knees,” Diamond said. I did it and she turned and pulled a black rubber hood off the dresser behind her. She put it over my head and it stretched tight against my cheeks. She zipped up the back. I felt like a warm caress.

“I’m getting deliciously hot in here,” she commented. “I’ve got another layer on under this one.”

“I want your cock in my mouth,” I said. I needed it so bad.

“Soon enough,” she said. “Take off your boots.” They were off in a second.

She turned to the dresser again and I fell to my hands and knees. I began to lick the heels of her boots, gently, hoping she would let me go higher, to the prize I lusted after. Instead she jerked the chain a little, like she would a dog that won’t heel. Then she took a step toward the bed and began to pour out a clear, viscous liquid onto the rubber sheets from a large plastic bottle. Lube, I realized. She dripped it all over, squeezing the bottle to reach the far corners.

“Up” she command, pulling the chain high.

The bed was slippery and I slid into the middle.

“Roll in it, spread it all over you and the bed.” I began to slip around, spreading the slippery stuff on the bed with my hands, turning over to get it on my back. One handing still holding the leash, Diamond sprayed more on me until I was covered with slick slime from head to foot. It felt amazing through my rubber suit and I caressed myself, squirming around with the almost childish but still wildly sexual pleasure of it.

Diamond hooked my leash through a ring on the headboard. She took off her boots while I enjoyed myself, rubbing the slime over my body. She was even wearing rubber hose. She stepped up onto the bed and took off her helmet and tossed it aside. She stood over me, long muscular legs spread apart, her hands on her hips. She looked down at me.

“Who’s a little rubber slut?” she asked.

“I am,” I answered.

I looked up at her and could see her cock throb slightly inside the rubber casing. I wanted it so bad. She began pouring the slippery stuff all over herself.

“Caress me,” she said. “Rub it all over me.”

The rubber skin was hot to the touch. I caressed her, making her as slippery as me. She moaned and tilted her head up to the ceiling. I worked her ass and them moved my hand around to play with her cock through the rubber. She moaned again when I touched it and I could feel it flex. I love feeling a cock getting hard.  

“Yes,” she said. “That’s a good little slut.”

I loved it when she called me slut. I kept caressing her, feeling the rubber stretch tight as her cock grew hard. She rolled her hips back and forth, moving like a belly dancer to my rhythm.

Finally she pulled my hand away and knelt down on the bed. She put her arms around me and threw me down. She fell on top of me and began writhing around against my slick, slime-covered body, rubbing her codpiece against me and licking my mouth. I was magnificent. We writhed until we were both so hot we couldn’t bear it anymore.

Suddenly, she stood up on the bed again, almost slipping and falling as she did so. She grabbed at her crotch and pulled the codpiece free. Her cock swayed there like a pipe dangling off the back of a utility truck. It was shiny with sweat and precome and looked so delicious.

“Suck it, little slut,” she said.

I practically lept on it. I took her balls in my hands and licked her all over. She grabbed her cock by the base and began slapping it against my cheek as I fought to get it in my mouth. It tasted salty and the skin was so creamy and soft stretched over the hardness. I licked up the sweat and precome and spread her juices over my face. Her musk was driving me mad.

All of a sudden she lurched and groaned loud. My cheeks were splashed with hot, creamy jism and I opened my mouth wide to catch the rest of it. I moaned with the pleasure myself as her second wad shot into my mouth. I savored it, rolling it around with my tongue before swallowing it. It tasted so satisfying and I sighed and jerked a little as I shot my own little teaser cum onto the rubber pouch.

I looked up at her she was smiling down at me through the mask, stroking her still-hard cock.

“Turn over,” she commanded. “On your hands and knees.”

I didn’t usually do what I knew she wanted but I had to obey. All I wanted was to please her, be her slut, a toy for her to slide her cock into and shoot her hot come inside of.  I felt her fumble with the zipper at the back of my pants. I felt cool air on my ass as she slid the zipper up and the rubber peeled away. It was refreshing.

She knelt behind me. I looked back over my shoulder to see her rub some lube from the bed onto her cock. I faced forward, closed my eyes, tried to relax and held my ass high. I felt the head of her cock, hard but pliant, explore my hole. It felt good.

She bagan to push it in and out gently, and slowly my asshole relaxed and began to expand, little by little, with each thrust. There was a flash of pain as she pushed the head all the way inside, but it quickly subsided into that dull but pleasurable ache. She pushed deeper and I moaned as her cock began to caress my prostate. It made me tingle all over.

When it was freely sliding in and out, Diamond ordered me on my back. She helped me turn so that she didn’t have to pull out. The sensation was thrilling, her cock turning inside me, against the walls of my ass.

“Jack off while I fuck you,” she said.

I reached down and set my hard cock free. It was slick with my juices and I began to stroke as I looked up at her rubber-clad face looking down at me, while her hips rolled back and forth. The look, the smell, the feel were the hottest sensations I’d ever experienced. Every part of my body, even inside, was alive, on fire with excitement. We both felt it and I stroked it faster and she plunged it into me and pulled it out. There was pain and pleasure and electricity all at once. We were both moaning, writhing, jerking. We couldn’t take our eyes of one another.

I felt the pressure build inside and I lifted my ass off the bed to tell her I was about to come. Just as the white jizz shot high out of my cock, she ripped her own from inside me and I saw the white, gooey stream shoot out the tip. I ignored the pain and watched her come splash against my torso, landing as high as my cheeks.  It was ecstasy.

Diamond stood motionless, drinking it in for moment, but then quickly leaned over and grabbed a towel off the nightstand and wiped off her cock. Then she knelt down and took my cock in her hand and began licking it off, running her thick, wet tongue all over it. I never had a chance to go soft. Her tongue felt so good. I loved watching it caress me.

She took it all in my mouth, fucking it with her face like schoolgirl fucks her date on prom night. I just lay there, moaning and sighing. She started stroking it with one hand while caressing pulls with the other, licking occasionally here and there. Again I lifted my hips as I felt the pressure build, and she stroked faster. Diamond opened her mouth wide over my cock as I came, shooting all over her lips and tongue and cheeks.  

Whores And Pimps - Part III

PantyhosePrincess on Transgender Stories

Whores and Pimps - Part III

 

By

 

Michele Nylons

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Michele pulled at her bonds, struggling and wriggling on the bed trying to break free for a few minutes until she realised that she was securely tied and had no way of escaping.  Ellie sauntered over to the bed and looked down at Michele,

 

“Well honey, looks like we have you just where we want you; I think we are going to start to really have some fun now,” she sneered.

 

Michele opened her mouth to scream and Ellie slapped her face hard.  Michele’s face was jerked to one side with the force of the blow and her eyes watered with the pain.

 

“Look bitch, you can try to scream all you like, but if you do I’m going to invite my friends here to smack you around a bit as a prelude to whatever else they’re going to do to you.  And once they’ve done that we can gag you if you still insist on making a fracas, although I’m sure they have better ways of stuffing your mouth, so shut the fuck up or wear the consequences,” Ellie threatened.

 

Realising that resistance was useless, Michele lay still and contemplated the circumstances in which she now found herself.  She had already seen Ellie and the fat cop who she had encountered earlier in the evening; she wondered who else comprised “we” Ellie had spoken of; she looked around to see who else was in the room.  There were three other men sitting at a table drinking.  Their chairs were turned towards the bed and they had obviously been entertained by the performance provided by Ellie fellating the cop while they waited for Michele to come around.

 

They were rough looking types, dressed in jeans and T-shirts; solidly built and appeared to be in their middle forties.  The men were talking amongst themselves in gruff voices; their language vile and littered with swearwords.  Their eyes glistened as they looked hungrily at Michele tied to the bed.

 

“I won’t worry too much about formal introductions Michele if you don’t mind.  You met my friend here from the local constabulary on your way to the party earlier in the evening, and I suppose it’s fair to say you’ve known him only briefly but certainly intimately,” Ellie smiled cruelly.

 

“These other three gentlemen are also aficionados of special ladies like ourselves; that is to say they have a penchant for attractive transvestites; and they particularly like a little bit of, shall we say, extremism when it comes to sexual encounters.”

 

“They are very close friends of mine, and over the years I’ve been able to sacrifice quiet a few ‘virgins’ to the altar of their desires; if I might wax poetic,” Ellie went on.

 

“Most of the girls I have lured into their clutches have left having eventually enjoyed the encounters; a few have not; but none have ever been a position to complain.  So I suggest you just relax and enjoy what I am about to allow you to experience; if nothing else you will at least leave this room enlightened as to what two transvestites and four hungry mature men can accomplish in the way of sating their appetites.” Ellie finished.

 

Ellie turned to the three men who had been eagerly watching and listening to her explain the situation to Michele, like a pride of lions watching their wounded prey.  Their eyes glittered in the darkened room as they feasted with wanton lust on the bound transvestite.  Michele’s miniskirt had ridden up when she had struggled at her bonds and her luscious nylon sheathed legs were exposed right up to the tops of her thighs and her red satin panties peeked from under the hem of her skirt.

 

“Gentlemen, meet Michele.  Michele, meet the gentlemen,” Ellie introduced them sarcastically.

 

“As for you, my law enforcing accomplice; you can sit over there on the lounge and I will keep you suitably amused whilst Michele and our three comrades entertain us.”  Ellie sauntered over to an overstuffed lounge which had been positioned beside the bed.

 

The three men rose as one and sauntered over to the bed and they looked down and surveyed Michele tied to the bed.  They stared at the middle aged whore; her black leather miniskirt rucked up around her waist from her struggles, her red lace garters clipped to her black stocking tops; legs spread wide and her ankles tied to the bed just above her black high-heeled sandals; her red painted toenails visible through the diaphanous nylon.  Michele’s leopard-skin print nylon blouse was opened at the top displaying her red satin brassiere.

 

Michele’s face was framed by her brunette wig the lighter tints highlighted in the lamplight, her heavily mascared eyes peeked from under her fringe, emphasised by her blue and pink eyeshadow. Her rouged cheeks and ruby red lipsticked lips were accentuated by her pale foundation and face powder.  Michele’s earrings and necklace glittered in the dim light.

 

One of the men noticed her anklet glittering and reached out and caressed her ankle and then slowly ran his hand up her leg to her stocking top, stopping briefly to play with her garter strap and then continued up her thigh until his hand rested on the front of her panties.

 

“She’s wearing pantyhose under her panties and stockings guys; looks like this whore will need to buy a new pair tomorrow,” he chuckled to the others.

 

Michele wriggled as she felt the man’s hands on her leg and panties.

 

“Hold still now honey; Michele is it?  My friend is going to untie your legs and if you give us any trouble; well Ellie has already explained what we will do,” he threatened.

 

Michele felt the bonds on her ankles loosen and then her ankles were free; she tried to close her legs but the man who had untied her legs now held them wide apart and pushed her ankles down on the bed. 

 

“Keep her like that Joe; if she moves or makes a sound belt her one,” said the man who had his hand on her thigh to the man holding her legs down.

 

Then he and the other man started to undress; they dropped their clothes where they stood and kicked them away into the centre of the room.  One of the naked men then relieved Joe of his task and Joe shucked out of his clothes so that all three of them were now naked.  Michele strained her neck up off the bed and saw the three men standing around the bed with their erections standing proud under their round bellies.  She started to cry and the man named Joe slapped her once across the face.

 

“Keep quiet bitch; last warning!  Next time you will get a proper belting,” he growled.

 

“Fuck she looks good,” said the man who had stroked her legs, “can I fuck her first?”

 

“I think that’s only fair Steve,” Joe replied, “I fucked the last trannie that Ellie got for us first.  You ok with that Bill?”

 

“Sure,” Bill answered, “I’d prefer a blow job before I fuck her anyway.”

 

Michele’s head was spinning; she knew that resistance was futile, maybe she could reason with them?

 

“Look, Bill, Joe, Steve; what about if you untie my wrists and just let me go?  I won’t tell anyone about this honest.  You’ve had your fun now so the joke’s over; come on guys let me go,” Michele Begged.

 

All three of the men standing over Michele, the fat cop, and Ellie laughed in unison.

 

“You silly cunt; we ain’t joking; and we ain’t letting you go; and I’ll let you into a little secret Michele; you won’t be telling anyone about what happens here tonight.”

 

“Are you really going to admit to being a transvestite?  And anyway who you going to tell; the police?  Our friend Bob over there is the police you dumb cunt!”

 

“And I gotta let you into a little secret; our real names aren’t Bill, Joe, Steve and Bob.  Sure you know Ellie is Eddie but Ellie saved you when you got drunk and passed out at the party.  She was your saviour and friend tonight in front of all those witnesses; do you really think anyone is going to believe that she took you up to her hotel room and gave you to four men to have their way with?  It’s just ludicrous!” Joe lectured Michele.

 

“Now shut the fuck up and you take what we give you and you won’t get hurt; like Ellie said you might even enjoy it,” he finished.

 

“I know how to shut her up,” Bill said and bent down and began to kiss Michele on her painted red lips.

 

Michele felt Bill’s tongue invade her mouth and attempted to move her head out of the way but it was useless, he continued to kiss her, the taste of whisky and cigarettes on his breath.  She felt one of the men; Joe she figured as Steve had hold of her legs, untie her wrist and grip it firmly.  He moved her hand down and then she felt her hand come into contact with his erect member and she tried to flinch it away.

 

“Don’t you fucking well make me hurt you bitch; you take what I give you and don’t even think of hurting me down there,” Joe growled.

 

Michele wrapped her fingers lightly around the rubbery fat cock and placidly held it there.  Joe held her wrist and began to slide his cock in and out of her loosely clenched fingers.  He looked down at his thickening member wrapped in Michele’s hand, her red painted fingernails accentuating her delicate fingers, and groaned. He swayed back and forth on his heels and fucked her hand.

 

“Oh yeah; wank that cock baby! Wank that cock!” he moaned.

 

Michele felt her other wrist being untied and when her right arm was freed it was placed over Bill’s shoulder and she left it there, limp, so that she held him in a faux embrace.  Bill sat on the bed as he continued to kiss Michele and he felt her start to respond.  Gently at first, she tentatively slipped her tongue into his mouth and then when he pressed his lips harder against her lipstick painted mouth, she kissed him back passionately.

 

Michele was becoming aroused despite the fact that she was being forced to participate in their debased game.  Bill’s kisses were deep and exciting; she responded despite her feeling of abhorrence and used her free arm to embrace him.  Instinctively her right hand clasped onto Joe’s cock and started to slowly masturbate him.  She felt her fingers slide along the sleek hard shaft and then over the spongy bulbous head; she manipulated the sensitive area at the bottom of glans and heard him sigh.

 

Bill lifted his face from hers and Michele reluctantly allowed him to escape her embrace.  He bent down and kissed her lightly on her lips and then both eyelids.

 

“God you are one pretty whore,” he whispered into her ear.

 

Michele became more excited and felt her own cock hardening inside her satin panties.  Bill shifted position so that he was kneeling on the bed, his groin next to Michele’s head.  She offered scant resistance when he turned her head towards his erect member and rubbed it on her lips.  Michele opened her lips and skimmed her tongue across the head of Bill’s penis.  Bill pushed forward and his glans slid over her lips and into her warm wet mouth; he rocked back and forward and pushed his cock in and out of her mouth; fucking Michele’s oral cavity as her lipsticked lips clamped on his shaft and her tongue lashed at his cock-head.

 

Michele couldn’t help herself; she was enjoying playing the role of a whore; sucking Bill’s cock whilst she stroked Joe’s cock with long slow strokes.  She enjoyed the feeling and taste of the hard member in her mouth, unlike the fat stubby cock of the cop, this cock was long, sleek and the secretions that leaked from the eye of the penis were sweet.  The cock in her hand was also long, but thick and veiny; she loved the silky feel of the skin of the shaft contrasting with the spongy feel of the head.

 

Then she felt Steve’s hand under her skirt start to stroke her own cock through the layers of her satin panties and pantyhose.  As the satin of her panties rubbed against her nylon encased cock it sent small shocks of pleasure shooting through her.  Then she felt Steve move onto the bed between her legs as he continued to stimulate her through her underwear.  She was startled when she felt Steve’s other hand push aside the crotch of her panties and a finger probe at her anus through the nylon gusset of her pantyhose.  She wriggled a little but she found the finger stimulating.

 

Michele could not believe that she was becoming an active participant in her own rape; she was enjoying it, she couldn’t stop the raging desire that coursed through her.  She sucked on Bill’s cock and used her free hand to stroke the shaft as she slobbered over the head of his cock, alternately kissing, licking and sucking at the fat cock-head.  Her other hand slid up and down Joe’s member, varying between squeezing it and then running her red painted fingernails gently up and down the shaft and under his balls.

 

Steve was mesmerised by Michele’s nylon sheathed legs; he manipulated and caressed Michele’s hardening cock through her knickers and with his other hand he stroked her stockinged calves and thighs. Steve straddled Michele’s right leg and began to hump her thigh.  Then he lifted her leg and worked his cock into the silky furrow behind her knee; he groaned revelling in the soft sensations in his cock as he slowly worked his penis in the gossamer nyloned crevasse behind her knee and thigh.

 

Steve slid his cock further up Michele’s thigh until he could force it under her stocking top so that it was trapped in the silken diaphanous tunnel between her stocking and her pantyhose encased thigh.  He fucked the gauzy chasm leaving a silver trail of pre-seminal fluid soaking into her nylons as his cock throbbed and released sticky beads of pre-come.

Michele could feel Steve’s hard penis sliding up and down her leg and was surprised to find that the sensation was highly arousing.  When he slid his cock into the silken trap behind her bent knee she clenched her knee so that his penis was clamped between the sensitive nylon sheathed skin of her calf and thigh; she moved her leg from side to side and felt Steve’s hot cock secrete warm moist droplets of sticky pre-come which was absorbed into her stockings and pantyhose.

 

When Steve moved his cock up her leg and started to fuck her thigh with his cock between her stocking and pantyhose she pushed her leg up into his groin so that her pantyhosed thigh rubbed against his scrotum, sending delightful stabs of pleasure through his balls.

 

Michele wanked at Joe’s cock; squeezing the shaft as she worked her fingers up and down his manhood; when she came to the end of his shaft she worked her fingers in circular motion around the glans and then grasped at the shaft and slid her hand back down the length of the engorged member.  She sucked and slavered at Bill’s cock, occasionally allowing his member to come right out of her mouth and then she licked the entire length of his phallus and gently nibbled at the head whilst flicking her tongue under the sensitive skin where the glans joined the shaft.

 

Joe was rocking back and forth on his heels, fucking Michele’s hand as she wanked him.  He looked into her pretty made up face and her rouged cheeks and mascared eyes, fringed by her silky hair aroused him; but what stimulated him the most was the way she worked her ruby red lipsticked lips up, down and over Bill’s cock.  For a girl who was terrified of what was about to happen to her twenty minutes ago, she had certainly changed her tune; she really was a whore.

 

Joe cast his eyes down Michele’s body, he reached out and caressed her belly through her nylon blouse and scanned down to her groin where her miniskirt had been pulled up and was rucked up around her waist exposing her garter belt and red satin panties.  Steve was slowly massaging Michele’s cock through her panties and his other hand was pressing down on her magnificent black stocked leg; his cock jammed between her stocking top and her pantyhosed thigh as he rocked back and forth and fucked the gossamer tunnel.

 

Steve was in ecstasy, but he forced himself to remove his cock from the silken trap of Michele’s thigh and moved back down the bed so that he was between her spread legs.  He moved up between them and pushed his cock down onto her panties to replace his hand which had been stroking Michele’s cock through her satin knickers.  He pressed down and began to slide back and forth, fucking Michele’s silken encased cock with his own.  The feeling was electrifying as his shaft felt hers start to throb through her tight pantyhose gusset and the satin panel in front of her panties.

 

Michele felt Steve’s manhood rub against her own as he dry fucked her through her knickers and hose; the taut nylon on her cock sending sensations all through her member.  She bucked and lifted her crotch to meet Steve’s thrusts and gyrated her hips to enhance the sensations shooting through her groin.  Then she was a little disappointed when she felt Steve move on top of her and his cock slid down her shiny satin panties and eased under the gusset; she felt the head of his cock nestle in the crack of her arse and begin to push against her arse bud, forcing the nylon of her pantyhose into the puckered hole.

 

Steve was gasping with pleasure as his cock rubbed against Michele’s nylon sheathed, engorged member.  He could easily come this way and enjoy every second; but he wanted to fuck the lovely transvestite who lay beneath him sucking the cock of his friend and masturbating the other.  He pulled back and shuddered as the glans of his penis rubbed feather lightly along Michele’s panties; he pushed forward as the knob of his cock nestled against the elasticised crotch of her panties and then forced his hard cock under her panty crotch and against her pantyhosed arse. He manipulated his crotch and wriggled his cock in the silken pantyhosed valley of Michele’s arse crack until he felt the head of his penis nestle in the bud of her back passage.

 

Steve pushed forward and felt the nylon pantyhose gusset begin to give; he pushed harder and his cock broke through the gossamer prison and wedged into Michele’s anal bud.  His cock was wet and lubricated from his pre-seminal secretions and he continued to push forward and felt his cock stretch Michele’s sphincter and finally the head of his penis penetrated Michele’s virgin passage.

 

Michele felt Steve’s cock begin to slide inside her; at first it was uncomfortable but she forced herself to relax and then the sensation of being slowly filled with hard cock began to excite her.  To Michele’s own amazement she actually started to push her groin against Steve to force his cock further and deeper inside her.  She felt her passage open as his manhood filled her and then she felt Steve’s groin hard against hers; he was all the way in.  Michele heard Steve groan and she lifted her stockinged legs up and wrapped her high heels around his waist and began to buck underneath him.  Steve held on and Michele began to fuck him, raising her buttocks off the bed in time with his thrusts in a slow steady rhythm.

 

Michele had now actually become the whore that she had only pretended to be at the start of the evening.  She was not only dressed as a whore; she was behaving like a whore.  She had already sucked her first cock before she got to the party, she had had lesbian sex with Jill on the balcony; now she was having forced sex with three middle aged men; and she was loving it!  ‘Yes’, Michele thought to herself, ‘I am a whore and I adore being a whore; what have I missed out on all these years?’

 

The three men and Michele began to concentrate on inducing their orgasms.  Steve was now slamming his cock in and out of Michele’s back passage and she was bucking under him; raising her buttocks off the bed to meet his thrusts.  She could feel his pulsating cock stretching her back passage and pushing against her prostate, sending waves of sexual sensations through her body; she wiggled her arse and clenched and unclenched her sphincter to increase Steve’s pleasure and enhance her own gratification.

 

Bill’s cock was pulsing in her mouth and she felt his orgasm approach as he pushed his cock in and out of her lipsticked mouth, holding her head as he fucked her face.  He groaned as Michele slavered at his erect manhood, running her tongue over the head and shaft as she felt the vibrating piece of flesh begin to convulse.

 

Joe was rocking on his heels fucking her hand in time to Michele’s hard strokes as she masturbated him.  He looked at her ruby red fingernails and the glittering jewellery on her fingers and wrists and felt his own climax build.  Michele could feel Joe’s cock start to shudder in her fingers and she gripped it hard and wanked at the erect piece of manhood; increasing the pace as she felt the cock quiver and shake in her hand.

 

Steve’s cock erupted deep inside her and Michele felt the splash of his seed flood  her passage; Steve’s cock was buried deep inside her, in her right up to the hilt, and she pushed up to meet Steve’s groin and felt his erection quiver against her prostate gland as she filled her panties with her own hot wet emission.

 

Bob’s cock exploded in her mouth at the same time and her mouth was inundated with salty hot come; she gulped it down as fast as she could but still some of the viscous white fluid escaped her mouth and ran down her chin.  Joe saw this and groaned as own penis spewed forth jet after jet of hot semen all over Michele’s hand, and arm.  Jets of his spend shot through the air and splashed on her blouse; the gobs of white ejaculate contrasting against the leopard-skin nylon.

 

Michele was writhing in ecstasy as the three cocks filled her and covered her with hot come.  Her arse was convulsing as Steve plunged his last few thrusts deep inside her, draining the last of his issue.  Her mouth was filled with Bob’s semen and he pulled his cock out of her mouth and let the last few jets of his release splash over her pretty, heavily made up face; a string of semen flew out of his cock and glistened in her hair.

 

Joe’s penis had shot stream after stream of semen over Michele and the globs of glistening semen on her blouse was joined by a thick viscous stream of come which had splashed over her rucked up skirt.

 

Michele lay there quivering in orgasmic bliss as her own climax subsided; her hot fluid filled her panties as she tasted Bob’s come in her mouth and felt his hot seed on her face.  She was covered in semen inside and out; she felt sated; satisfied like she had never been before.  Michele had become a Transvestite whore and she loved it!

 

……………………………………..To be continued.

Natasha gets a surprise

Nylon Mistress on Transgender Stories

"My God, what are you doing' cried Natasha as she walked into the room?

The sight that must have greeted her was indeed a strange one as she looked at me lying on the sofa with a pair of tan pantyhose pulled most of the way up my legs, a black bra around my top, and a black pair of her heels jammed onto my feet.

See the thing was that she'd asked me over to help get a new DVD player going for her. Her husband was away interstate for a few days and she wanted to watch some movies, so I offered to help. I'd started the job and she'd just nipped out to the supermarket leaving me to it.
But she'd got near the supermarket and realised her purse was still at home and had come back to get it. I'd got the player working quick
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ly and the noise from the TV drowned out her return. And because I thought I had some time to spare, I'd decided to indulge my passion a little, never for a moment thinking that she'd be back so soon. And so, here we were...

"Oh no, Oh God, I'm sorry..I..umm Oh No" was all I could say. Didn't make a lot of sense I know, but I didn't know what to say. I'd been well and truly caught and I thought I was in big trouble.

"C'mon" she said "This had better be good, and think yourself lucky I don't throw you out in the street looking like you do right now!"

I stammered and stuttered a few times, my head filling with a million different reasons, but in the end I knew that none of it would make any sense. I decided to play the only card I really had. I decided to confess.

"Look, I have to admit, that like most guys, I have my slightly perverted side.We all have little things that excite us, and in my case I have a bit of a 'thing' for pantyhose and high heels. Always have had as long as I can remember. And of course I see you a lot and I cant help but take notice of what you're wearing, especially when it comes to what turns me on"

"Ahh" she interjected "That would explain why apart from all the girls, you were the only guy who ever commented on when I was wearing new stuff, especially shoes then" she said, with finally a hint of a smile coming to her face. And she sat down on the sofa beside me.

I felt ludicrous now, my previously hard cock had sunk down to nothing but I was still just sitting in front of her looking what must have been a real sight.

I continued...

"Anyway, I knew it was wrong, but with you away I couldn't resist taking a look in your wardrobe. At first it was just a look, but then the desire to try them on overtook me. And I suppose I just lost myself in the moment and well....here we are"

" I assume you think I'm some sort of ultra-strange pervert now, and maybe I am. But you're an attractive girl and combine that with the attraction I felt to your 'things' well I couldn't help myself. I'll just take this stuff off and go...." and I leant over to start taking the heels off.

As I did she pulled my hands away and pulled my down-turned face back up.

"Look, don't worry. I had always noticed that you took more notice of me than maybe you should have, but now I understand a little more. It's no big deal, and to be honest it actually turns me on a little"

With that she leant over and kissed me lightly on the forehead and then leant over me further and began to pull the pantyhose up over my flaccid cock and up onto my waist. I was shocked and slightly taken aback but my cock responded instantly and began to harden as the nylon touched it again.

She stood up herself and pulled me up after her. She wrapped her arms around me and kissed me deeply and ground herself into me. My cock was now rock-hard again and she pushed harder into it.

"Wait here, it's time for a surprise" and she walked off.

My head was spinning now, what was going to happen? I expected some retribution, not reward.

A few minutes later she emerged from the bedroom that I'd hurriedly rifled through earlier. She was stunning. She was covered in a one-piece black body stocking with a halter neck, and shimmering silver highlights. On her feet, black patent boots, with a good 6" stiletto heel and a pointy toe.
Her breasts were trying to burst through the gossamer sheer fabric and even from a distance I could see the gaping hole between her legs of the crotchless outfit.

She walked over and pushed me onto the sofa

"I know this is wrong for both of us, and you need to understand that this is STRICTLY a one-off thing. But, I desperately want to fuck you right now. I want to have some fun, because this is something we may never get a chance to do again. You don't need to worry, this is our secret. I might ask you to do some things that you might not like even, but today is a time for experiments. So, just go with me and enjoy..." and I couldn't help but notice the wicked smile on her face.

I never got a chance to reply as the next thing I felt was her on top of me and her open legs ground the soft hairs of her vagina into my face. I didnt need prompting then and quickly set about eating every inch of her soaking wet pussy. She certainly wasn't lying about being turned on by the ocassion that was for sure.
But she wasn't leaving me alone either, and I could feel her tongue running up and down the length of my cock again and again, the whole while caressing it through the nlon of the pantyhose.
Every now and then she'd use her hand to pull my cock out a little and I could feel the head of it disappear into her mouth. If this wasn't heaven it was as close as I was every going to get to it that was for sure.

She moved further down my body and began to kiss my legs through the pantyhose and I did the same to her. I loved the feeling of the two bodies clad in nylon rubbing against each other. To be honest it was all I could do from cumming on the spot and it was probably good timing from her that she stopped sucking my cock and moved on.

We echoed each others movement, stroke for stroke, kiss for kiss. Then she got down to my feet and removed one of her heels from it.
"Hmm a little tight but otherwise a good fit really. Aren't you a lucky boy" and then proceeded to suck each toe individually through the pantyhose.

If you'd asked me before whether I would have liked that I would have said no, but as she was doing it to me it was sending wave after wave of pleasure right through me. It was like nothing I'd ever felt before, and she knew it..

"OK, I think you're well and truly worked up now my boy, time for Natasha to do something that I've always wanted to do but couldn't"

She looked back at me, stood up and then flipped me over onto my stomach. To be frank she could have done or asked for anything and I would have agreed at that time.

I felt her rip the pantyhose under my balls and then tore a great hole right through the front and the rear. Then I was shocked to feel a big cold gooey sensation in between my ass cheeks, running down over my cock and balls. I whipped my head around and saw her strapping on a dildo. Leather straps ran around her waist and one underneath and the rubber member just stuck out in front of her, the head glistening with lubricant. Luckily it wasn't huge but it also wasn't what I really wanted either!

"Umm hang on, I'm not really into this sort of thing, I mean I'm not gay or..."

"Quiet" she said "I told you that there might be some buttons pushed today, I've let you indulge in what you want, this is what Natasha wants" and she put the head of the dildo between my cheeks as she straddled me.

I knew it was pointless to protest much further now and I didnt really have much of an option anyway as I felt the pointy head ease into the first part of my asshole. My eyes must have been like saucers I think as she eased the dildo in.

"Mmm enjoying it so far are we?" and I'm sure I detected a hint of sarcasm in her voice almost

Before I had a chance to reply she pushed it in further. And even though it wasn't all that enjoyable, my twitching cock was getting even harder, so somewhere deep inside she was certainly creating feelings in me that I hadn't had before.

I tried to relax a bit and as soon as I did the pain went away and the whole rubber member slid in.

"Thats it my boy let me fuck your hot little boy ass"

I couldnt believe it, I'd never heard her use words like that before. Certainly this experience was obviously opening some new ground for both of us. She began to slowly fuck my ass.  Each stroke was long and measured like she could almost feel it herself through the rubber. I had to admit that the sensation was now becoming quite pleasant for me too as the dildo seemed to be hitting spots inside my ass that were really responding.

She kept on fucking me and then abruptly pulled out. My hole felt empty and alone and I wanted it back in.

"Please Natasha, fuck me some more" I pleaded.

"No, its time for you to suck mommy's cock" and she giggled.

I knelt in front of her and took it into my mouth. I knew she couldnt actually feel anything, but she seemed to really enjoy the fact that she  was the cock-sucking recipient for once. After a while of slurping on the rubber meat I started to work my way around the sides a little and onto her flesh. She was beginning to moan softly again so I decided it was my turn for a bit of control again.
I undid the clasps on the straps and let the dildo fall to the floor. With ome movement I pushed her over the sofa and opened her legs. I knelt between them and slammed my cock all the way in.

"Ohh yes...thats what I want" and she shuddered.

I couldnt believe how worked up she was and I just rammed into her again and again. No finesse now, just raw hard fucking and she was responding to it big time. Finally one stroke took her over the edge and she shook violently all over and her pussy clamped hard on my cock as she decended into her orgasm. She must have had 2 or 3 in a row as I felt her grip me tight over and over and just a low moan coming from her mouth until she finally stopped moving.

I stood up and looked down at her. Her face had a slight smile and her luscious body was still shimmering in its body stocking and down on her legs those nasty patent boots were looking as good as ever.
She looked back up at me and her hands went to her boots. She slipped them off and then wrapped her feet around my cock.

"I think I know what you need now" and began to jerk me off with her feet.

And she was so right. With each stroke my cock got harder and harder and the feelings that she was bringing up were just divine.

"Do you want to cum baby? Do you like this?"

What a stupid question, of course I wanted to cum, and it grew ever closer. Finally I could hold back no more and a scream emerged from deep within me as felt the first spurts of cum shoot out of my cock. They arced up over her legs, some staying there, some going further and splashing on her breasts and face. Long streams of sticky white cum, again and again. I noticed her lean over and she'd grabbed one of the heels that I'd been wearing just minutes before, and positioned it in front of my cock, and some of the cum shot over it and then down into the other one lying on the floor.
Then when I'd finally shot the last spurt whe let me go, and I collapsed onto the sofa next to her. Her legs and feet were covered in my cum and some still peppered he face and breasts.

I looked down at the shoes and they too had a good coating too. I'd never shot that amount ever before and I was amazed myself.

She leaned over and kissed me deeply again and some of the cum rubbed off onto my own face as well.

"OK, that was a lot of fun...and I think you nearly drowned me!" she laughed and wiped some of the cum away

"Hmm , these are a little wet too aren't they, you naughty boy" and then she held up holding the dripping high heels over herself dripping more cum on her legs again"

"Tell you what, you deserve a present." and she stood up and wriggled out of her body stocking standing naked in front of me

She handed me the heels and the body stocking

"These are yours now, oh, and you can keep the other stuff that you're wearing too. Next time you feel the need, you can pleasure yourself, and think of me at the same time"

"Oh but I can't do that..."

"Don't be silly" she said "I know that it all turns you on, and its OK with me. Now I can tease you a little too, Ha!"

She held me close to her again, kissed me once more, and then pulled away.

"It was a once off remember, but that doesnt mean that I wont remember it...." and she turned and walked into the shower.

I sat down on the sofa and slowly removed my pantyhose and then got dressed. I wouldnt forget it either.

The Day After

girlcasy_cd on Transgender Stories

I explained in my previous story, which to really understand me you really have to read “My life as a girl” besides I am picking up where I left off but if you don’t want to take the time to read it, I am what they call an intersexual. A term you should look up or go back to the other article to understand. In short, I have the body of a girl with extreamly small male organs that disappear inside my groin. It has taken me a few years to come to grip with my feelings and body. By relating these experiences my hope is to help others with the same problem and to come to grips with their gender related issues.

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I went to bed that night and relived the events of the evening over and over in my head.  It was like a dream.  I had actually passed myself off for Julie!  Every thing inside me told me I could but there is a lot of difference between thinking and doing and I had done it. The only one that knew was my sister. Everyone else, Mom, Dad, my little sisters, Karen and Holly and even Brian thought I was Julie!

 

The next morning it was hectic in the house. I put on latex gloves to hide the fingernail polish. Dad and Mom left early for work. My attention was consumed in getting Karen and Holly dressed and off to school. Julie came in the kitchen and hugged me telling me again how much she enjoyed last night. She then left for school.

 

When everyone had left the house I went upstairs and stripped off my clothes and showered, washing Brian’s dried cum out of my hair and off my body. After drying off I picked up the clothes Julie had left laid out on my bed. I laughed to myself at the thought that she laid out what clothes she wanted me to wear. I dressed and went into Julie’s room and sat down and blow-dried and styled my hair and began to put on my makeup. My conversation with Julie was running through my mind as I slowly and meticulously applied it.

 

 

 

I was angry with her. “ Why the hell did you call Brian? And why did you tell him you wanted to suck his cock really intending for me to give him the blowjob?” I demanded after the door to her room was closed.

 

“ Because it was going so well with Dad and Mom. You had them fooled and I began to see how you could help me out of another situation.” Julie said looking me straight in the eyes, “ Tomorrow Brian will have told everyone at school that I sucked his cock!”

 

“ Why the hell would you want him to tell everyone?” I blurted out.

 

“ Because I really didn’t want to do it! I think its sick and degrading to let a guy dominate me that way, on my knees before him. Besides I am more attracted to girls and now they will think I am straight because you gave Brian a blowjob. The guys were already starting to tease me about being a lesbian. Even the girls were starting to act funny around me even though I haven’t acted on my feelings, besides you should know what the girls go through, especially if you are going to take my place at school.”

 

I was probably as shocked at her confession as she probably was when she saw me dressed like her. I was speechless. Julie had told me that some were teasing her but I had no idea!

 

We both had secrets that we had kept from each other. My anger had faded.

 

“ Besides it looked like to me that you were enjoying him sucking on your nipples and it was so sexy watching you suck his cock.” Julie added.

 

“ What? How did you see what went on?”

 

“ Well when you left the house, I followed and stood behind a tree not ten feet from where you were in the park and with the full moon out, it was as if it was broad daylight. The moonlight lit your bodies up. Anyone who would have even driven down the street would have seen you two. It was so public, so hot!”

 

I didn’t know what to say so I turned and opened the door and went to my room, stripped off her clothes and climbed into bed not even caring about Brian’s cum all over me.

 

 

 

I completed my makeup, stood up and walked to the full-length mirror in the corner of the room, examining every angle making sure everything was in order. I had plans for the day and needed to put things in place.

 

I went about my daily chores, making all the beds, picking up Karen and Holly’s room, putting their dirty clothes in the hamper, vacuuming the carpet both upstairs and down. I scrubbed the bathrooms and mopped the floors in each. Then mopped the kitchen floor. Dad still hadn’t fixed the lawnmower yet so the lawn would have to wait till the Saturday.

 

By 11 o’clock I was done. Now I had the rest of the day to do whatever I wanted. Mom and Dad wouldn’t be home till after midnight tonight. They were going to attend a company dinner. Julie was going to be out late because of the football game and dance afterwards. My little sisters were going to Grandpa and Grandma’s after school and Mom and Dad would be picking them up on their way home tonight. So I had at least 12 to 13 hours to do whatever I wanted!

 

I picked up my purse and locked the door and headed for the mall walking past the park on the way. I stopped for a moment to watch some moms with their children playing in the spot where hours ago I was on my knees sucking Brian’s cock. I couldn’t help but smile as the scene flashed through my mind and thinking of Julie standing by the tree nearby.

 

He called me his bitch and last night I was just that. His bitch sucking his big cock. I wondered how things went for Julie at school and how her date with Brian would go tonight. I decided to go and sit and watch the kids play and so went to the very bench we were at and sat down. One of the moms came up and introduced herself to me.

 

“Hi I’m Samantha but my friends call me Sam.” She said as she sat down next to me.

 

“Hi I’m Julie.” I said back.

 

“If you don’t mind me asking how come you’re not in school?” she asked.

 

“I’m doing home schooling. I am just running some errands for my parents” I said casually.

 

“Oh ok. I didn’t mean to be nosy but it’s just unusual for a young girl to be here during the day. Although I have seen you walk by before.” She paused and looked over at her child playing on the swing. “You must live close by, I live right over in the blue house over there. Do you have brothers and sisters dear?”

 

“Yes.” I said, adding, “ Two younger sisters and a twin brother.”

 

“Are they home schooled as well?” She asked.

 

“No, just me.” I said.

 

“Hey could you baby-sit during the day sometime? Sometimes I am looking for someone to watch Michael while I run errands and if you think you would be interested can I call you? I’ll pay you good.”

 

“Let me think about it and talk it over with my parents. I know where you live and will let you know. Ok?”

 

“That would be great, thanks.”

 

“Well I have to go, it was nice meeting you Sam.” I said and getting up I walked down the street and turned heading for the mall.

 

When I reached the mall, I purchased my own makeup and fingernail polishes so that I wouldn’t have to use my sisters. Afterwards I went into one of the restraunts and sat down and ordered a salad.

 

When I finished it I then walked slowly home enjoying the warm sunny day with the breeze blowing my skirt. The air felt good on my bare legs. I stopped to rent a video from the adult section in the back room of the store. The guy at the video store reminded me that I needed to be 18 to rent the movies from the back but after giving him a flirtasous smile and leaning over the counter to show some cleavage smiled back at me said,

 

“ Its on the house. Just bring it back and let me know what you scenes you enjoyed.” He said smiling back at me.

 

“Ok.” I said blushing.

 

By the time I reached home it was about three o’clock and in a couple hours my friends would be out of school and would be stopping by to hang out. It was our regular ritual. Wayne, Bill and Mike and myself would usually smoke a few joints and sometimes Wayne would have a bottle of alcohol that he took from his dad’s bar in his den. We would put some music on in the garage and get really buzzed and doing tricks on our skateboards in the driveway or down the street.

 

I couldn’t count the number of times they talked about Julie and how she was really hot! When they would talk about her I could see the bulges in their pants grow. At times they even joked about getting hard thinking about her and then rub their cocks through their jeans to show their manhood and we would all laugh.

 

They were the geek type with their glasses and not so handsome looks and bad hairstyles. They hung out with the other geeks at school and I knew they weren’t very good with the girls but liked to talk big like most of us.

 

I had fantasized about seeing their cocks but being a guy I would never dare let it be known for fear of loosing my only friends besides I was struggling to understand my feelings.

 

After sucking Brian’s cock last night and everyone thinking I was Julie. I couldn’t stop thinking about their cocks and how it would be suck theirs.

 

Tonight it would be Julie entertaining Wayne and giving him a present he would never forget! I picked up the phone and called Bills cell phone and left a message for him not to come over tonight. That I was doing something with Wayne for his birthday and although I wish I could include them it wasn’t possible.

 

I then called Mikes cell phone and left the same message.

 

Tonight both our fantasies were going to come true.

 

I went to the kitchen and took out the refrigerator a large smoked sausage. Time to do some research. I went into the family room and put the video in and turned it on. It was all about different girls sucking cock and the guys eating their pussy’s.

 

I watched intently trying to learn the different techniques the girls used. I realized last night that I need to know more about how to suck a cock.

To give them the most pleasure I possible could.

 

I continued watching the movie over and over imagining myself sucking the cocks, imitating what they did while sucking on the sausage. With each scene I was beginning to get more excited about this evening.

 

I removed the videotape, put the sausage back in the fridge and went upstairs and hid it in my closet behind some clothes. Wayne would be over soon and I certainly didn’t want to forget the tape in the VCR. The last thing I needed was to have Mom or Dad or anyone for that matter turn on that movie.

 

I looked myself over in the mirror checking my makeup and outfit and reapplied my lipstick.

 

“Humm, perfect.” I thought out loud.

 

I heard the garage door open up and looked out the window. It was Wayne. He went in and then I heard the music coming out. I stood in the window watching for several minutes. I couldn’t believe how nervous I was. I was shaking.

 

I kept thinking about last night and how even Mom and Dad couldn’t tell Julie and I apart.

 

I went down stairs and went out the back door, down the sidewalk to the garage and looked in. Wayne was at the counter with his back to me mixing some drinks. Next to the bottle of vodka there were several joints.

 

Oh-Yeah this was going to be a good night. Everything I need was there to sooth my nerves.

 

Suddenly his cell phone rang.

 

“What’s up Bill?” I heard him say. “Yeah, I’m here now.”

Then there was silence as he listened. I sat down on the bench that was at the side of the driveway. I had a perfect view of Wayne.

 

“No way man!” Then silence on Wayne’s part again.

 

“Ok. Well be cool.”

 

“Yeah Kacy and I will just have to party without you.”                

 

“Yeah its cool. You guys are coming over to my house Sunday right? Remember it’s my birthday and I my folks said I could have some friends over for dinner and I thought we could all just hang out afterwards. I got a new video game, its really cool!”

 

“Great! Yeah man, it will be the four of us. Well hope it all works out. Talk to you later.” Concluding his conversation putting the phone down.

 

Everything was going according to plan.

 

I got up and walked into the garage “Hi Wayne. How’s things going?”

 

Wayne wheeled around as if to try to hide the stuff on the bench. “ Hi Julie!” he blurted out, his voice highlighting his nervousness.

 

“Hey, eh, Kacy isn’t going to be home tonight. He wanted me to tell you.” I said.

 

“Oh ok. I guess I’ll just head home then after I close up. Thanks Julie.”

 

I walked over to him and looked behind him at the drinks and pot, “What this? Do you mind if I hang out with you a bit? Maybe we could smoke one of these together. If you don’t mind that is?” I said reaching around and picking up a joint and putting it to my lips.

 

“Ah, well, Ah yeah, sure, that would be cool.” He said with a puzzled look on his face.

 

“Kacy told the other guys not to come over.” I said. The puzzled look remaining on his face.

 

I reached over and stuck my hand in his front pants pocket to get the lighter. I wrapped my fingers around it and felt movement in his crotch. I moved my fingers around more and looked him in the eyes as I felt his cock through the material.

 

“ Mind if I use your lighter?” I said slowly almost in a whisper.

 

Wayne was frozen stiff! Not sure what to do or say.

 

I pulled the lighter slowly out of his pocket rubbing my fingers along his cock and putting it in his hand.

 

“Will you light if for me?” I said not breaking eye contact with him.

 

“Oh, sure. I’m sorry!”  He said and raised the lighter and flicked it to life. I broke eye contact and put the tip of the joint in the flame and took a long drag on it and holding it in then handed it to him.

 

I then picked up one of the drinks on the counter and walked slowly and seductively outside to the bench where I was sitting before. I could feel Wayne’s eyes watching my every move. He followed carrying his drink and the joint. I sat down and crossed my legs. My short skirt riding high up my thigh revealing practically all of my legs.

 

Patting the space next to me I said, “Come on sit down, I won’t bite. It’s a really nice afternoon and I love sitting in the Sun.” Then putting the drink to my lips, took a deliberately long slow drink of the liquid in the glass. Wow it was mixed strong, practically all vodka with just enough orange juice to add color to it.

 

Wayne sat down and I could tell he was really nervous about being so close to me. It was kinda funny and that I had to laugh, He had no idea why I was laughed. Wayne and I had sat on this bench many times getting stoned and he was never nervous when I was his friend Kacy, just one of the guys!

 

He took another hit off the joint and reached out to hand it to me, his hands visibly shaking. I touched his hand pausing for a moment before taking the joint, licking my lips slowly, then I put it to my lips and took a deep drag and held my breath holding the smoke in my lungs.

 

I put my head back against the chimney behind the bench and looked up at the clouds floating bye in the late afternoon sky knowing that as I did, my breasts would be straining against my low cut blouse. I intentionally didn’t wear a bra today and even though I was looking up I could feel my nipples pushing on the fabric.

 

“Ummm” I said releasing the smoke slowly, “ Wow that’s some good pot. Is it laced with something?” Then rolling my head over towards Wayne catching him staring at my chest and legs.

 

He suddenly realized that I was looking at him and he jerked his gaze away, grabbed my glass and stood up not answering my question.

 

“Let me refill your drink.” He announced and scurried off to the garage. I watched him as he went to the counter and poured the liquid from the bottle into my glass. Funny he didn’t put anything else in it, just vodka. I took another drag on the joint and leaned my head back and waited for him to return.

 

“Here you go,” he said sitting down again. I leaned forward and released the smoke from my lungs and took the drink and put it down on the patio stone next to the bench.

 

I was really starting to catch a buzz between the strong drink and the weed. I took another deep hit and decided to get things moving. It was obvious he wasn’t going to make a move.

 

I leaned over and grabbed his head and pulled it down to me and planted my lips on his kissing him softly. When he started kissing me back I began to blow the smoke into his lungs. I let go of his head breaking off the kiss leaning back on the bench.

 

He then blew the smoke out and looked at me with a real puzzled look on his face.

 

“What?” I asked.

 

“I just don’t get it. You’re the most beautiful girl in school, a cheerleader on top of it and you have never, ever, come down to hang out with us before. In fact at school you don’t even know I exist. And now here you are getting stoned and you just kissed me? What’s the deal here? Are you setting me up for some kind of joke or something? And why did Kacy tell the others not to come over?” Wayne stammered out with his voice breaking.

 

“Look, Kacy told me its your birthday Sunday and he wanted me to give you a his present but not with everyone around.” I said staring him in the eyes.

 

“W h a t ‘s the present?” he asked looking away.

 

“Well, Kacy wants me to suck your cock” I said as I put my hand on his upper thigh. His cock was definitely growing.

 

“What?” he managed to get out not believing what he had just heard.

 

I got up and dropped the cushion I had been sitting on down on the patio stones in front of him and kneeled down. “Well he told me how you guys talk about me and this is his gift to you so just enjoy it. Eh, the thing is, you can’t tell anyone. Do you understand that?”

 

I took another drag on the joint and handed it to him. I then reached up and unbuckled his belt. Unbuttoning his pants and slowly unzipping his pants as I blew out the smoke from my lungs letting my fingers trace his cock.

 

I grabbed his pants at the waist and looked up into his eyes and said, “ I need a little help here!”

 

With out a word he raised his body off the seat and allowed me to pull his pants down. His cock springing straight up. It was larger than I had imagined. Then bent untying his shoes pulling each one off, then the socks followed by his pants all the while I didn’t take my eyes off his seven or eight inch cock.

 

When he was naked from the waist down I stood up and unbuttoned my blouse swaying to the music and dropped it on top of his pants. “Do you mind if I get comfortable?”

 

My breasts being exposed to the late afternoon air and his eyes, made my nipples stick straight out from the mounds of my breasts. I knelt down between his legs and picked up my drink, standing up slowly allowing my chest to brush against his cock and balls and inner thighs. Picking up his hand I placed them on my breast. He squeezed it really hard just as I took a drink from my glass. I swallowed hard.

 

“ Ouch! Hey easy there big boy. Gentle is better!”  And then took another drink of the really strong drink. This time he gently squeezed my breasts and I leaned forward and put one of my nipples to his lips. I could feel his cock and balls up against my legs so I moved them back and forth.

 

“Ummm , Yes that’s the way, you big stud. Ummmm that feel so good.” I said as he sucked gently on my nipple. This is the second time a guy had sucked on my nipples and I was still amazed at how sensitive they were.

 

“Umm now lightly use your teeth to nibble on it, oh yeah that’s the way!” I moaned as he lightly took it between his teeth.

 

After about five wonderful minutes I backed away from him pulling my nipple out missing his mouth on them instantly.

 

“Awwwwwwe.” I said pouting, the disappointment being obvious in my voice.

 

I handed him my empty glass and then reached up and cupped each of my own breasts and pinching my own nipples played with them rubbing his saliva around in front of him. His eyes taking in every move I made. I moved seductively to the music that drifted out of the garage and then leaned forward kissing him.

 

Kneeling down before him, I placed his manhood against my naked chest reached up and unbuttoned his shirt allowing my hands to fondle his chest. I bent down and nibbled on his nipples and then pinching them, rolling them between my thumbs and finger making then hard.

 

“UMMMM,” Wayne sighed.

 

Turning my focus to his cock I lightly dragged my red painted fingernails down his chest and stomach to his cock grabbing his hard cock rubbing it over the soft flesh of my breasts and hard nipples.

 

“Oh god Julie, that feels sooooo good!”

 

I moaned with pleasure feeling his soft, hard  flesh as I played with my nipples. “Ohhhhh yeah.” I whipped my head back throwing my hair behind me and licking my lips slowly, “Ohhhhhhh.” I whispered softly leaning my head back.

 

Setting back on my heals, I used my fingernails to lightly trace the line on the underside of his cock until they reached the sack holding his swollen balls.

 

“Awe Yeah. God I can’t believe this is happening.” The words escaping from his lips.

 

I leaned forward and put my bright red lips on the tip of his manhood planting a soft kiss then opening my mouth slightly I stuck my tongue out and licked the hole at the end.

 

“Goddd Yesssss.” His word trailed off to a soft hiss.

 

His cock leaped I could taste the flavor of his sweet pre-cum leak out. Grasping the base of his cock with one hand I pulled down on it stretching the skintighter making the head swell more. With my tongue I licked all around the ridge at the base of the head. With the other hand I cupped his balls gently massaging them.

 

“OHHHH that feels so good!” he moaned almost in a whisper.

 

I looked up at his face. His head was back and eyes were closed. Wayne’s hands were gripping the bench to steady himself.

 

I licked down the same path my fingernails had traveled only a moment ago and holding his balls up to my mouth licking each one, then sucking them one at a time into my mouth using my tongue moving them around in my mouth then pulling them out while still sucking until they reached their limit and plopped down. I then traveled back up to the tip licking as if licking an ice cream cone.

 

“Ummmm, Oh God Julie your red lips are sooooo hot on my cock.”

 

I looked up into his eyes as he stared back down at me. His eyes were glassed over from the pot, booze and pleasure. I let saliva drip from my mouth onto his cock and rubbing it in pumping up and down slowly on the shaft.

 

I brought my mouth back to the head and this time I took it into my mouth until my teeth were just over the ridge and lightly bit down, sucking deeply on it while I moved my tongue back and forth on the underneath side.

 

His breathing was getting heavy as he tried to speak. “Yeah that’s it, please suck on it.”

 

I released my teeth and pulled it back out of my mouth and then sucked it deeper. I repeated the motion fucking his hard pole with my mouth each time moving my lips farther down until his cock hit the back of my mouth.

 

“UMMM, UMMMM” I moaned through my nose as I worked his pole with my tongue and mouth.

 

“Oh god, don’t stop!  Please.” He pleaded.

 

Wayne stretched his legs out straight and tensed up from the sensations my mouth was giving him. I lowered my head farther allowing his cock to push into my throat. I continued to fuck my mouth and throat.

 

“Holy Shit that feels sooooo good.” He moaned.

 

At last my nose was pressed into his pubic hair giving me a whiff of his sweaty body odor and my chin against his balls.  I held him deep in my throat for a moment enjoying his masculine smell and then as I pulled my mouth back up sucking until he came all the way out of my mouth making a slurping sound.  

 

“Ummm stud, you have a fucking huge cock. I just want to eat it up.” I whispered talking dirty in a seductive voice as I moved my fingernails down his inner thighs and legs.

 

“Oh god do!” he responded.

 

I grabbed it again and felt his butt cheeks tighten his cock swelling up even more as I licked around the crown of the head. I knew he was going to cum soon. I pumped up and down on his dick.

 

“OH GOD I AM GOING TO CUM! OH SHIT I DON’T WANT IT TO END!” Wayne moaned.

 

I sucked the head back in my mouth and continued to jack him off. I released his cock out of my hand and reached up to his bare chest with both hands bracing myself, digging my fingernails in. I could feel the flesh give way under my nails.

 

“ OUCH! OH SHIT I AM GOING TO SHOOT MY LOAD!” he practically shouted.

 

I kept my nails dug in his chest. I had him on the edge and now I was going to take him over the top.

 

I sucked more moving my head in circular motions around his cock.

 

“HOLY SHIT HERE IT COMES! OHHHHHHHH GOD! YESSSSSS! GOD YESSSS! YOUR MOUTH IS SO FUCKING HOT” Wayne shouted in deep heavy breaths.

 

 I dragged my nails down his chest making him erupt sending his hot musky juices into my mouth.

 

Screaming out “OWWWWWWWWW, OHHHHHHHHHHHHHH SHIIIIIIIIIT!

 

I swallowed, and then I released his cock from my mouth only to grab it with my hand. I pumped his shaft up and down until it stopped. His cum dripping down my face, nose and chin I swallowed the cum in my mouth then began licking the tip of his cock enjoying my friends man juice.

 

I looked up into his sweat-drenched face. His eyes were closed as if he had passed out. His chest was heaving up and down as he tried to catch his breath. Ten red scratches ran down his chest to his stomach from my fingernails.

 

I sucked his cock in one more time sucking off any cum that remained. Then pulling my mouth off his cock as it began to shrink. Standing up wiping the cum off my face with my fingers watching his face. He opened his eyes and I began rubbing his cum all over my breasts, playing with my nipples. Pinching my nipples one last time. I bent down and picked up my blouse.

 

“Kacy says Happy birthday!” I said in a soft voice as he sat there naked from the waist down and bare chest exposed.

 

“Julie, that was the most incredible present anyone could have ever given me. Thank you!”

 

“Don’t thank me. I did it for my brother. Goodnight.” I said then staggered topless to the house leaving him to get dressed and pick things up.

 

Once in the house I went to my room and gazed in the mirror. I had cum smeared all over my face and chest. I could feel it pulling on my skin as it was drying up. I laid back on my back on my bed and closed my eyes. The room was spinning and so was my feelings. Tears flowed out of my eyes out of happiness. 

 

After a few minutes I opened my eyes and dried my tears with the back of my hands and looked at the clock. Nine o’clock it read, so I finished undressing and put my robe on and stumbled downstairs to get something to eat. I was so hungry. I heated up some left overs from the night before and sat down and ate.

 

Grabbing a bag of chips I went back upstairs and laid back on my bed. The whole room was spinning out of control. All I could think about was how I pleased my best friend Wayne.

Removing my robe I crawled under the covers, closed my eyes and soon faded away.

SarahJaneyy on Transgender Stories

It was early in the morning and as usual I woke up before I had to get up. I walked into the bathroom and turned on the light instantly closing my eyes because the light was too bright. I undressed and got into the shower taking no longer then sixteen minutes. I got out and headed back into my room, and stood infront of the mirror. I was a 5'1 blonde with short hair and 36B sized breasts. I was rather beautiful and girls were usually envious of me. I ran my hands over my breasts and moved them down across my stomach at to my hips. I moved my left hand and slid it down to the area where usually a vagina would be but for me there was a relaxed groin. I appeared as a girl, but had sex organs of a man. It didn't really bother me, it made

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me different from everyone else, and I seemed to get more pleasure out of sex then my friends did. At this point no one knew about my secret, which meant I was a virgin. "shit" I said aloud as I moved swiftly over to my closet and grabbed down a pair of jeans and a black 'Bullet for my Valentine' shirt. I was running late, and I still had to pick up my friend McKenzi for school. I quickly got dressed, brushed out my hair, and headed out to the kitchen to grab my backpack. I swung it over my shoulder quickly and walked out to my car. I picked her up and got to school right on time.

I had gotten through the first three hours with no problem, but when I got to my fourth hour my heart started to race. See my fourth hour teacher Ms. Winters was one of the hottest girls I had seen on the planet, she had a nice rack and a nice ass. I usually had to hold myself back otherwise my secret would be out and everyone would know. I sat down in my desk which was right next to Kenzie's and prepared for the class to start. Right on the dot Ms. Winters walked in but today she was wearing a low-cut shirt and a rather tiny skirt. I could feel my dick slowly start to grow in my thong and jeans. Kenzi looked over to see what was wrong because I had a worried look on my face. She looked down and saw something she didn't expect "Ermmm Sarah.. what's that?" she asked pointing to the bulge in my pants. "Nothing!" I said loudly and got up and walked quickly out of the class. Luckily no one saw me but Kenzi and the teacher. I headed to the bathroom and headed into a stall to wait out my boner. They didn't last that long usually. "Sarah..?" I heard a voice call outside of my stall. "We need to talk" I said quietly. I headed out of the stall to find a curious Kenzie. "What did you see..?" I asked frightened. "Well.. I saw something in your pants... what are you? I mean are you a boy or a girl?" "A girl!" I answered immidetly. "Then why do you have a penis?" she asked hessitantly. "I was born with it, want to see? I can prove I was" she nodded and I grabbed her hand and lead her into the handicapped stall (that could fit seven people in it). I slowly undid my pants, and pulled down my thong revealing my dick. Relaxed it was a good six inches and erected it was around 9. "Oh my god!" she said stunned. "Can I touch it?" she asked with a grin on her face. That got me really excited and I nodded quickly. She approached me slowly and reached her hand down towards my dick which was starting to grow.

"You like me touching it?" she asked seductivly. "Yes.. yes I do!" I replied. "feel free to do more" I said in hopes of her doing so. Which of course she did. She kneeled down and wrapped both of her hands around it. "Mmm" I moaned softly. "Suck that dick" I said with a grin. She wrapped her warm mouth around my fully erected dick and slowly she started to take it all in her mouth. "Oh god!" I moaned loudly. "Suck it.. harder suck it you dirty hoe!" she countinued to suck it quicker and harder. It being my first time I was extremely horny and very excited so I reached the point of no return quicker then when I masturbated. "Oh shittt! I'm gonna come!!" I shot my load into her mouth and suprisingly she took it all in and swallowed it.

Thankfully no one heard us. Now our friendship is very different.. and we've done it many other times.

;]

The Shoe Store

Lmildcd on Transgender Stories

The Shoe Store

By

L

 

            Adam hated working Wednesdays. He works the entire day from

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opening to closing every Wednesday. His manger always takes Wednesday off. This was mostly a boring day for Adam. A few women came in the store before lunch which was a disappointment for Adam. Adam is a bit of a pervert. He likes to take a peak up a woman’s dress or skirt while he is putting on shoes for them. The morning customers all were wearing slacks.

 

            A woman came into the store a little after lunch time. She was wearing a halter top with a short skirt, stockings and heels.  Adam went over to her and asked if he could show her anything. She said she needed a new pair of shoes for a party she was going to attend this coming Saturday. She wanted to see shoes with a four inch heel in Silver size 11M. Adam went to the back and came back with four pairs of shoes. He decided to take a peek up the woman’s skirt while he was fitting her with the fourth pair of shoes. He noticed that she was wearing thigh high stockings, but she wasn’t wearing any panties. She caught him looking up her skirt. She just lightly tapped him on his head and asked him if he liked what he saw. Adam just simply nodded in the affirmative with a sly grin on his face. She said, “I’m Nyssa and I’ll come back at closing to give you a full view.” She left after purchasing one pair of shoes. Adam returned the other pairs to the back wondering if Nyssa would indeed come back.

 

            The rest of the day was like the beginning. All the women came in dressed in slacks. Adam kept wondering if Nyssa would come back.

 

            It was closing time. Adam had closed out the register and put the money in the safe. He then let his night clerk out the door. He locked the door and then did is final check. He heard a slight tap at the door. It was Nyssa with a small tote bag. She came back as promised. He let her inside. She asked if there was somewhere in the store that would be private. He nodded in the affirmative, and led her to the office in the back after relocking the door.

 

            As soon as they entered the office, Nyssa spun Adam around and gave him a passionate kiss, and then whispered in his ear, “We are going to have some fun.” Nyssa leaned against the desk and removed her halter top exposing her medium sized breasts while Adam was getting over the initial shock. She said, “Suck my nipples.” Adam attacked her nipples like a hungry infant. She said, “Gently baby gently.” He slowed down. He then started swirling his tongue around her nipples. “Oh baby that’s good, “she moaned. She then reached under her skirt and started playing with herself.

 

            “Ok baby stop sucking my nipples. I want you to get undressed for me, “she said after she stopped playing with her self. Adam did as he was told. Nyssa noticed that Adam’s cock was a little hard. She grabbed it and started gently stroking it. Adam started to moan with pleasure. She kept up the gentle motion until she felt a little leakage. She stopped and said, “I don’t want you to cum just yet. Sit on the desk while I put on a little show for you.” She started to dance and started to strip out of her skirt.

 

            Nyssa slowly inched her skirt downward. Adam’s eyes followed her every movement. Eventually, her skirt was low enough to reveal a slightly erect cock. “I told you that I was going to give you a full view,” she said in a low sexy voice. Nyssa continued dancing until she was completely out of her skirt. She then stroked her cock until it became half erect. Adam’s eyes were fixed on her cock. She guided his head to look into his eyes and said, “now the real fun is about to begin.”

 

            Nyssa reached into her tote back and brought out a rubber glove and a container of lube. “I need your asshole well lubed for what have I mind. Be a good boy and turn around and lean on the desk for me,” she told Adam. She put on the glove while he was turning around. She lubed up the middle finger of the glove. She slowly penetrated his asshole with her finger. He moaned while her finger went deeper inside. Nyssa started moving her finger back and forth once it was in all the way. She even twirled it around a few times. She kept this up for a few minutes. Both of their cocks grew harder.

 

            Nyssa said, “I think you are ready for the next stage” as she removed her finger, and then the glove. She reached into her bag and removed a seven inch dildo. She lubed up the dildo and she stroked it to get it coated with the lube. She inserted it into Adam’s asshole and he moaned again in pleasure. Nyssa pushed the dildo in as far as Adam could take it. She used the same technique as she did with her finger. She started slowly and gradually went to a faster pace. Adam continued to moan in pleasure as the dildo kept going in and out of his ass. Nyssa kept shoving the dildo in and out of his ass until she had a complete hard on.

 

Nyssa said, “I think you are ready for the final stage” as she removed the dildo. She reached into her bag for a condom. “I like to be safe,” she said while putting on the condom. She inserted her dick into Adam’s asshole. He let out his loudest moan. She pushed it in as far as Adam could take it. He continued to moan. Nyssa started thrusting her cock slowly at first. Adam started moaning louder still when Nyssa quickened her thrust. Nyssa continued her thrust at a faster pace and then Adam cried out, “My cock feels like its going to explode. I need to cum.” Nyssa replied, “I’ll take care of it as soon as I finish.” Nyssa continued to pound Adam’s ass until she shot a forceful load.

 

“I do enjoy fucking a young man’s ass, “she said as she slowly removed her cock. She peeled of the condom and tossed it into a nearby wastebasket, and then said, “Now let me think. What am I going to do with that hard on of yours? I know what I could do if we were at my place. I’m not going to let you suffer until I get you there. Turn around.” Adam did as he was told and she grabbed his cock. “My you do have a hard one”, she said. Nyssa always liked seeing a hard cock on a man after she fucked him. She started stroking his cock. “Please make me cum,” he begged. She replied, “Since you asked nicely and have been a good boy, I am going to jerk you off. Sit on the edge of the desk.” Adam complied. Nyssa reached into her bag for another condom. She said, “This is so that we won’t have any mess to clean up” as she was putting the condom on Adams hard dick. She started with slow strokes. Adam began to moan again. She stroked faster and Adam’s moans once again became loud. All of a sudden Adam yelled,”I’m Cumming!” Nyssa could see the condom filling up with his hot juice. She gave Adam a few hard strokes to squeeze out the remaining cum. She peeled off the condom once Adam’s cock started going limp. The condom joined the other one in the wastebasket.

 

They both got redressed after they rested for a few minutes. Adam led her out of the office and then let her out of the store. Nyssa gave him a quick peck on his cheek and a slight grab on his ass. She whispered in his ear, “Maybe I’ll come by again and take you to my place.” She left and proceeded to her car. Adam waved goodbye as she drove away, and she blew him a kiss. Adam relocked the door. This was one night he will not forget.

 

Adam finally lived out a fantasy of his. He always wanted to have sex with a she male every since he bought a she male video. Adam bought a video once based on the title. He did not know what the movie was about. The movie had scenes of she males fucking men, and she males fucking women. Adam became turned on while watching this video. This was his favorite movie to jerk off with.

 

Adam left the store after he gathered his belongings. He wondered if Nyssa will ever come back once he got in his car. Adam was happy. He lived out a fantasy or is it possible that his life has changed?

Hose and Heels in the Bedroom

Jolly1 on Transgender Stories

Liza giggled as she sat back down on the sofa, a mischeivous smile on her face.

"Whats so funny I asked?" wondering what had tickled her fancy. After all the only thing that had happened was that she'd just been to the toilet to relieve the pressure that the 3 or 4 glasses of wine that we'd both had must have been causing her.

"Come on what brought on the giggling fit?"

She stood up and came over to me. In what seemed like a strange move she turned side on to me and put her foot next to mine.

"Yep thats about right then, quite a bit bigger just like I thought" Then she laughed and sat back down again, her face glowing and two eyes that just said mischief.

"Umm i

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s that a surprise? Of course my feet are bigger than yours!"

"No it's not really a surprise, what was the surprise was what I saw in your bedroom"

"What do you mean? Why were you in there?" I said, trepidation building in my body as the words came out of my mouth.

"Oh I didnt go in there initially, I just glanced in  as I was coming out of the bathroom, and I couldnt help noticing the pantyhose hanging over the side of the bed. Then my curiousity was piqued and I saw the lovely black Maryjanes on the floor below. Thats why I wanted to check what size you were. And as it happens you seem to be about the correct size to fit them. And what was even stranger was the shoes are exactly the same as these ones I'm wearing today. So...anything you might want to tell me?" and her voice trailed off as she laughed again.

"Umm well they belong to.." and she sharply cut me off "Don't give me a bullshit story, I know they're obviously yours..so what's the deal?"

I didnt know what to do, I was caught red-handed with no escape. My little secret had been uncovered and I could barely get a word out in explanation.

"Well...it's just that every now and then I...." and then my own voice caught as I tried to work out what to say. The evil look on her face was one of fun though, and I suppose the wine had made us both a bit more open to surprises so I blurted the truth out.

"Look, I've got a real fetish for some things. And as it happens pantyhose and heels are top of the list. I really get off on wearing them, I know its weird but I cant help it"

"Yeah OK I got no problem with that, but is it an accident that the shoes I saw match my own perfectly?"

"Well no...What REALLY gets me going is to wear something that someone I know wears. I love looking at what all the girls at work wear and trying to get my own.And I like yours especially. It takes a while to find out the right brand and everything, and then to get some that fit me, but when I do... well... And I knew you were coming today and I was hoping you'd wear those shoes so I sort of prepared by wearing mine for a while earlier. Oh god, you probably think I'm a real nutter"

She looked across at me and then stood up. "Well come on then, if you like to wear them that much we should match now. Come on, put em on and show me"

My heart was going a million miles an hour. I was terrified but excited at the same time. Liza was about to help me live my ultimate fantasy. Even as she dragged me into the bedroom my dick started to stiffen. Oh god, how was I going to hide it!

We sat on the bed and she told me to take my jeans off. I dropped them to the ground and then removed my socks.

"Ok put the pantyhose on for me" I did as I was told and she said "Oh dear, you even know how to put them on properly, you've obviously been doing this for some time. And by the looks of things you really do enjoy it too" as her eyes glanced downward toward the throbbing member that I could no longer hide.

"Come on, shoes next" and I reluctantly slid my feet into the heels and buckled them up.

She looked at me and said "You know ordinarily I wouldnt be interested in you, as you know, we're just friends. Maybe its the wine talking but this really turns me on I have to say." She leaned across and kissed me lightly on the lips.
"So, it seems a shame to waste this, what say we have a bit of fun then?"

I wasn't sure what she meant but then she rolled over and pulled me onto the bed. She positioned me face down and then removed all her own clothes except her own pantyhose and shoes. She slid on top of me and for the first time I felt the exquisite feel of nylon upon nylon as she moved her own legs in and out of mine. My god the feeling was incredible, it was everything I'd ever hoped it would be, and I was in heaven. Judging by the noise she was making it was something good for her as well. Every time she moved her leg a tingling sensation went through me and I was sure that I'd cum in record time.

"Do you want to swap around?" I heard her say?

"In what way?

"This time you can be the girlie" and I felt her rip a hole in my pantyhose and her finger started playing with my rear. Oh god this isnt what I'd planned, I'm not sure I want to go here. But she kept going and pretty soon I felt her slender finger invading my crack, and then slowly sliding inside my hole.
Is this what its like I asked myself? I know I'm not gay, but boy does this feel good. Liza kept it up for a while with her finger exploring everywhere inside my hole and I was going wild with delight.

"You got a vibe or a dildo?' she asked?

"Umm yeah in the bedside drawer" I figured she was going to let me play with her a bit now. I didnt think we'd actually fuck as such, I didnt think that she'd want that so the vibe request seemed reasonable. But I was wrong. Seconds later I felt a healthy squirt of lubricant on my ass and then the tip of the vibe was nesting in my ass crack

"Oh I'm not sure we should go down this road?"

"Don't be silly, if you're going to dress like a girlie you need to be fucked like one, I think you might just enjoy it" she said as she pushed the first part of the vibe in my hole.

Oh god it felt like a telehone pole it was so big, but I couldn't disagree that it was making me extremely horny and my dick had never been harder. She pushed more, and more and gradually the whole length was inside me. I'd never felt anything like this before and although it was uncomfortable, I wanted more all of a sudden.
Liza started to move it in and out in long slow strokes, gradually building up momentum. Almost involuntarily I started to respond and move with her rhythm. She would thrust and I would push back. It was feeling incredible and she knew I was enjoying it.
By this stage she'd moved into a reverse position so she was next to me and her pantyhosed legs and fet were next to my head as she concentrated on fucking my hole with the vibe.
I grabbed one of her feet and started to lick her leg, my tongue dancing over the nylon and ocassionally onto the leather of her shoes. I was surprised to hear her moan, obviously she had some fetish in this area as well. I renewed my licking and slipped one of her shoes off and started to suck her toes through her hose. She momentarily stopped fucking me as she gasped with pleasure. Seems we both shared some enjoyment here.

"Are you ready yet?" she asked me in between moans

"I'm so close it doesnt matter, and if you slam that thing inside me one more time I'm gonna flood the bed soon"

She pulled the vibe out of my swollen ass and quickly rolled me over onto my back. She grabbed a spare pair of pantyhose out of my drawer and wrapped them around my swollen member and then placed her mouth over them as well. My cock went into her mouth surrounded by nylon... I was in heaven and living my ultimate fantasy, and I could believe it.

"Oh god I'm gonna cum...you gotta let me cum" I yelled.

She ripped a hole in my pantyhose and swivelled around and stuck her finger back in my ass hole. Then she positioned her own feet next to my cock. With barely a couple of strokes from her free hand my cock erupted and a torrent of cum shot forth from it. The sticky juice went all over her leg and shoes,and trickled down in between her toes. It was more than I'd ever cum in my entire life, I thought I'd never stop.

"Enjoy that did you?"

"Umm, yes, very much so" I gasped trying to catch my breath.

"Good, cos Its my turn now and I snuck a look in your closet and saw all those other shoes and we're going to try them all out tonight..."

And I knew that there was a LOT more still to come.....

 

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A Crossdressers Tale

AverageRon on Transgender Stories

Hi, my name is Ron. This is a story about the first time I dressed for a guy. I was off work that day. My wife was at work & my daughter was in school. I was bored and got online for for something to do. I have a yahoo screen name letting people know I'm a CD and bi. Well, this guy I've been talikng to for awhile was on and i figured "What The Hell, inite him over." His name was Tony. He was older in his 50's, But looked great from what i could tell from his webcam. Tony asked me if i would dress for him. I told him i was nervous but i would try. So i went up and got in the shower and shaved my body. Then went into my room and put on my thigh highs and garter. I then put on a little school girl outfit i had. A plaid mini-skirt and white blouse. I also wore 3" heels.
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When Tony got there i answer the door fully dressed as a woman. I was so nervous but excited at the same time. Tony came in and sat on the couch, I sat next to him. He started telling me how nice i looked and what graet legs i had. I leanwed over and kissed him. Next thing i know he has his cock out, It was about seven inches. It looked so good i had to taste it. I slowly licked up and down his shaft. Then i took it in my mouth. Tony grabbed the back of my head and strated fucking my mouth. After i finnished sucking him he lifted my skirt and pulled my panties down. Then he started giving the best head i had ever recieved. Then he asked if i had any lube. I was ready and reached over on the end stand and handed him a tube of K-Y. He squirted some on my asshole then rubbed some on his cock. He put legs on his shoulders and leaned down and kissed me. While he was kissing me he slowly slid his cock in my ass. It hurt like hell at first, but he was so gentle and waited till the pain subsided. And slowly strated pumping in and out of my ass. he picked up the pace till he was slmming me hard. I felt his balls slapping me, it felt so wonderful. I was in heaven. I was pumping my own cock with my hand and came on my belly. After tony saw that He took his cock out of my ass and came on my belly too. Then we cuddled for awhile. It was my first time but sure wasn't my last. Now i feel like a slut because i fuck guy all the time.
I hope you enjoyed this story as much as i enjoyed reliving it. E-mail me at average_ron@yahoo.com