Synopsis: Michele tried to use her feminine charms on the Warden at Chelmsford Prison. He rebuked her and sent her packing back to work in the prison brothel. Now Eddie has introduced her to a powerful friend of his called Davy..... Can Michele seduce Dave and persuade him to help her escape the brothel where she works as a transvestite prostitute?
entered the office only an hour ago. The Warden grabbed my arm in a vice-like grip and dragged me across the office. He opened the door and threw me outside like a piece of garbage; I tripped and fell to my knees on the hard polished floor tearing my beautiful pantyhose. I looked up to see 'Iron-bar' Steve smirking down at me. The Warden briefly disappeared back inside his office, then returned to the doorway and threw my shoe and my ripped skirt at me.
"Tell Eddie I've finished with this for now. She's one of his better whores, but she has too much of a mouth on her," Warden Stone barked at Steve and slammed the door shut.
Part IX
I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!!
The cravings of male sexual hunger within the confines of the four walls of Chelmsford Prison did not stop just because there were visiting days with the guards bribed to look the other way (or wantonly stare) whilst prisoners wives or girlfriends masturbated and fellated their partners in the visitors room. On completion of these visits the prisoners were seldom fully satisfied when they stuffed their sticky, deflating penises back into their grubby prison fatigues; they had the same appetites as men everywhere and wanted sex daily if they could get it.
In this rough world of imprisoned men where the inmates had only the slight chance of sex during visiting hours, I knew that when I was forced to dressed as a woman, I was enticing to these sexually deprived animals. The prisoners had only the fumbling wanks and sloppy fellatio provided by their wives and girlfriends as they dipped their hands and heads below the Formica topped tables during visiting hours.
The lack of normal heterosexual relations available to the inmates was the catalyst that allowed Eddie to make a fortune running his prison brothel with his string of transvestite prostitute inmates. Men starved of female companionship took their pleasure where they could; and there were also undoubtedly some prisoners and guards who preferred sex with transvestites regardless of the availability of women.
I was the latest addition to Eddie’s stable, and although being forced to crossdress and prostitute myself was repulsive to me, I knew from recent events that I was irresistible to the inmates and guards who found their pleasure this way. So why had the Warden been so contemptible to me after treating me so nicely at first? I had obviously overplayed my hand when I tried to make my proposal for a transfer out of Chelmsford. Stupid me! I decided that I had better come up with another solution to get out of this disgusting place. Perhaps blackmail might work where my charms had failed?
"Well Michele, you really managed to piss the Governor off somehow! Come on you naughty girl, lets get you back to your cell so you can get cleaned up and rested; you still have to work tonight," Steve said, lifting me to my feet.
He leant down and picked up my skirt and shoe from where the Warden had thrown them on the floor.
"Here sweetheart, put these on," he offered the items to me smiling.
I slid the patent leather black high-heeled sandal over my stockinged foot, my painted toenails visible through the torn reinforced toes of my pantyhose. The silver anklet around my left ankle was still there, sparkling as the light reflected off it. I slid the navy blue skirt up my legs and wiggled my pantied arse into it and tried to smooth it down my thighs. I leaned against Steve to steady myself whilst I dressed and I heard him gasp as he wantonly ogled me. The split in the side seam of the skirt exposed my sheer hosed legs right up to the top of my thigh, and I exposed a glimpse of white satin panty as I adjusted my translucent white nylon slip under my skirt. I felt Steve’s hard muscled bicep as my painted fingernails dug into his arm and remembered how dangerous this could be.
"Christ you look good Michele. With that torn skirt, laddered stockings and messed-up makeup you look like a stray waif who needs rescuing."
"And fucking," I heard him whisper to himself.
"Come on, we better get a move on," Steve pushed me through the door onto the stairwell landing.
He pushed me against the wall and pressed his full weight against me. I could feel his hot breath on my neck.
"Shhh! I think I hear someone on the stairs below us!"
"We’ll have to wait here and be quiet until the coast is clear," he whispered in my ear.
Steve pressed tighter against me, my back was pushed hard against the cold concrete wall. Steve was breathing into my ear his breath quickening.
"I can’t hear anything," I whispered.
"Shhh! If you can’t shut up I’ll have to shut you up!" he whispered hoarsely and pressed his lips against mine.
I felt the groan in the back of his throat and heat from his body. He kept his lips locked on mine and then I felt him slowly start to rub himself against me, his member thickening in his jeans and pushing against my lower body. Steve’s hands came up and pressed my arms tight against my body in a vice-like grip as he continued to kiss me and move against my body.
"Keep quiet; we can’t afford to be found here outside the Governor’s office; Eddie would kill me," he whispered hoarsely between kisses.
I tried to open my mouth to protest and he slid his tongue into my mouth and passionately tongue kissed me. I was resigned to my fate. What could I do? I was still shocked from the ravaging I had received from the Warden. Steve released one hand and slid his arm between our bodies, still kissing me and flattening me against the hard wall. He fumbled around; I knew what he was doing, and then I heard the rasp as he opened his zipper.
His hard penis leapt free from its denim prison and I felt the hard hot texture of it as it came to rest against the material of my skirt. Steve groaned again and repositioned his hands. His body now pushed me harder against wall; his right hand pushed on the back of my neck pulling my face and lips hard against his; his left hand slid up my right thigh, his callused fingers whispering against the nylon of my hose.
It was deathly quiet on the stairwell. All I could hear was Steve’s heavy breathing, the occasional groan in the back of his throat, the whispery murmur of his fingers stroking my pantyhose and the rustle of my skirt rubbing against my body as he pushed his cock against me and gyrated his hips. There was no sound of voices or footfalls.
I managed to briefly break the lock of his lips on mine and pleaded,
"There’s no one coming Steve; quick let’s get back to my cell while the coast is clear!"
"Shut the fuck up bitch!" he hissed, "There is one person coming soon and that’s me!" he confirmed his intention to take me in this cold bleak stairwell.
I squeezed my arms up between us and pushed against his shoulders in an attempt to fight him off. Steve just pulled my face back to his and carried on kissing me, thrusting his tongue over my lipstick-smeared lips and deep into my mouth. His hand on my thigh seized the hem of my skirt and wrenched it up; as he did so he adjusted his stance so that his hard hot penis pressed between my nylon encased thighs.
Steve groaned again and began to rub his engorged member in the crevice created by pantyhosed thighs. I locked my thighs together in a vain attempt to stop him. Steve now repositioned his hands and bought them both down to my buttocks, taking one buttock in each of his big strong hands, squeezing them through the material of my skirt. The hem at the front of my skirt remained ridden up so that his cock was nestled in the ‘Y’ shaped silken valley created by my hosed thighs and white satin panties. Steve now began to push his steel hard member in and out of this silken trap, his cock pressing further between my legs with each thrust. He was ‘dry humping me’ the dirty bastard!
I beat my fists against his hard muscled shoulders trying to discourage him, but it was useless. Steve now lifted my buttocks upwards and as he did so my body slid up the wall and my feet lifted off the floor; Christ he was strong! My high heels left the ground and as Steve continued to lift me up against the wall he pushed his body weight against me, forcibly opening my legs. As hard as I tried to press my legs closed, the force of his body and his strong arms proved no match for by feeble efforts as my fists drummed against his chest and shoulders.
Steve suddenly heaved me up and at the same time repositioned his grip under the tops of my thighs as he pushed me back against the wall with his bodyweight. My feet were now completely off the ground and my thighs spread further, unencumbered by my torn skirt. Steve pressed his groin into me and I felt his turgid penis throbbing against the satin gusset of my panties. He adjusted his position slightly and I felt his member begin to slide under the gusset of my panties and push against the sheer nylon crotch of my pantyhose.
Steve was panting with excitement and exertion; his hot breath was in my mouth and then on my cheeks as he kissed me hotly on my lips and face. He moaned,
"Michele; please………I’ll be gentle honey……..God you’re so lovely!"
What could I do? Resistance was futile and would probably only cause me pain.
I moved my hands from his chest and wrapped them around his neck and slid my nyloned calves around his waist. Had anyone come up or down the stairwell they would have been greeted with the following sight:
A large muscular man embracing a petite businesswoman, bracing her up off the floor and against the cold brick wall, her arms locked in embrace around his bull neck whilst her legs were locked around his waist to help support her weight. Her painted toenails peeking through patent leather black high-heeled sandals, her sleek legs sheathed in laddered, diaphanous sheer black nylons, with dark reinforced cuban heels and toes, the seams of the nylons running up the backs of her legs.
She wore a navy blue suit. The skirt was ripped up one side and was snug at the waist and tight around her hips and bottom. A glimpse of translucent white nylon full slip was visible where her skirt was torn and where the front of her skirt had ridden up as she clutched herself to the muscular inmate who held her captive. A flimsy white nylon blouse peeked through her navy blue suit blazer designed to match her skirt.
An observer would then notice her pretty feminine face. She wore pinkish hued eye shadow, blended with light aqua to just under her eyebrows. Lashings of black eyeliner and mascara had been applied to her lids and lashes and had smudged around her eyes and had run down her cheeks from the tears she had recently shed. Her plum coloured lipstick was smeared around her lips from the frenzied kisses that had been forced upon her. Her hair was a black bob wig, and a pair of silver and diamond encrusted sapphire drop earrings hung from her ears, a matching pendant around her neck.
She looked defeated and submissive as the powerful thug supported her, pushing her against the wall as he thrust against her grunting and panting whilst he defiled her.
Steve was kissing me hard, his tongue assaulting my mouth. His rampant member slid back and forth, snug between the nylon of my pantyhosed crotch and the satin gusset of my panties. He picked up the pace and pushed his cock harder into the crevice between my buttocks. He settled into a steady rhythm as he dry fucked me, his pelvis thrusting back and forth as he pleasured himself. I just hung on and offered no resistance, allowing him to gratify his primal urges; I just wanted it over with. I responded to his kisses and pushed my arse against him to increase his pleasure and hasten his climax.
Suddenly Steve slammed me against the wall and thrust forward and upwards with all his strength. I felt the glans of his member push firmly against the nylon of my hose and then felt the thin gauzy material stretch and finally give. His rock hard penis nestled in the bud of my sphincter and began to shoot hot spurts of semen. The warm slick liquid lubricated my puckered bud and his member slid deep inside me, pulsing and spewing streams of his seed into my back passage. Steve’s tongue pulsated in my mouth and I responded as I felt an uncontrollable wave of please wash over me.
The head of Steve’s penis was pushing hard against my prostate, his vibrating rampant flesh shooting hot jets of come inside me causing me to orgasm spontaneously. I suddenly emptied my seed into my silky pantyhose and satin panties that encased my sex organs. Steve’s crotch pushed the filmy material against my scrotum, increasing the sensations as they shot through my body, amplified by feel of the sheer nylon hose on my legs and the silky full slip and blouse on my torso.
Steve thrust me hard against the wall as he emptied himself inside me; I groaned and forced myself against him. Steve shuddered and moaned, torrents of semen spewed from his member and dribbled out of me, pooling in my panties.
As our orgasms subsided Steve eased me slowly to the ground and as he did so his cock slid from inside me unleashing a further torrent of come into my undergarments. I tottered on my high heels and held on to him, the last of our kisses becoming softer and tender until I was standing there on shaking legs, my back against the wall for support. Steve adjusted himself and zipped up. He leaned forward and pressed a light butterfly kiss on my cheek.
"Come on honey lets get you back to your cell before Eddie comes looking for us," he whispered, and nuzzled my neck briefly.
As Steve led me dazed and confused up the stairwell and back to my cell I began to realise what had just happened. Again I felt repulsed by my uncontrollable sexual responses. I loathed myself for capitulating and even worse for taking pleasure in the sick, twisted sex life into which I had been enslaved.
Steve dropped me off at my cell and made me strip. He took away my female attire and led me to the showers. He stood guard while I washed off my makeup and showered in the empty cellblock ablutions, the other cellblock inmates were at work but he was taking no chances that anyone might decide to have some fun with one Eddie’s ‘girls’ out of business hours. I have to say I felt better knowing that Steve was there to watch my back whilst I was in there alone. Steve didn’t say much to me at all after I had taken off my female clothing and washed off my makeup; it was as though he had no time for Mike, he just lusted after ‘Michele’.
I spent the last part of the day alone in my cell contemplating how I was going to get out of the mess I was in. I watched the clock, dreading the passing of time as the minutes advanced into hours. ‘Iron Bar’ Steve finally knocked on my cell door and entered,
"Time for work; let’s go," he said.
Steve led me back to E Block, the deserted wing that Eddie had set up as his brothel. He handed me over to Mabel who told me to strip. She inspected me all over as I just stood there meekly letting her prod, poke and stroke me.
"You need a good shaving girl," she clucked, and led me down to E block’s shower rooms.
She had me sit on a stool and shaved the light stubble from my face and then proceeded to remove any remaining hair from my arms, legs and chest. She then rubbed moisturiser all over my body and dressed me in a light blue satin kimono.
"Come on love, you can get ready for work in your workroom," she muttered leading me out into the corridor to my workroom cell.
‘Ready for Work! Workroom! Who the fuck was she kidding,’ I thought to myself. ‘What she really meant was go and make yourself into a woman so the sick bastards in this hellhole can violate you!’
As I passed down the corridor two of the cells had low red lamplight emitting from the flimsy curtains which had been pulled across the bars at the front of the cells. I heard muffled grunts and groans, and as I passed the first cell I heard the slapping sound of flesh against flesh. I could just make out the silhouette of what appeared to be a woman bending over a chair as a large man stood behind her pounding himself against her buttocks.
I could just make out that her panties were pooled around her ankles above ridiculously tall high-heels. As the large man plunged forward into her she shuddered and tottered on her heels, she held on to the back of the chair and the legs of the chair made a scraping noise each time she was pushed forward slightly with each thrust. The man appeared to be fully clothed and grunted like a pig with each lunge of his body; he held on to her tight at the waist. The woman, actually a crossdressed whore, gasped as each thrust rammed his groin against her buttocks with a loud slap.
I couldn’t see anything in the second cell; I could just hear the slurping sounds associated with a well-trained fellatrix at work and the murmurs of a man being satisfied.
"Just Carmel and Charlotte servicing a couple of guards before we open for business," Mabel said as we passed by on the way to my workroom cell.
"Eddie gives the guards a freebie and they keep watch for him and keep out the rabble. Business is business in Chelmsford prison honey; we all have to pay our way," she sniggered.
She led me to the cell door and I noticed that heavy curtains had been rigged on a rod above the cell bars that opened on to the corridor. They were pulled back at the moment but they did not bode well for me this evening I guessed. Mabel pushed me through the door and walked over to the armoire. She rummaged around and pulled out what appeared to be a schoolgirl’s uniform.
"You’ve got a ‘special’ first up love; get dressed, Eddie’s bringing a friend in half an hour."
"He wants to play ‘Naughty Schoolgirl.’"
Mabel rummaged around in the drawers and selected lingerie that she threw onto the oversize cot. She looked at the assortment of wigs and selected a blonde, shoulder length wig.
"Shame we haven’t got time to make up some pigtail braids on that wig, but he’s not really that fussed on authenticity if you know what I mean; it’s more of a costume dress-up thing with him," she shrugged.
"Well come on love, get a fucking move on!" she ordered and pottered out of the cell to go about her duties.
"Fucking old tranny fag-hag!" I hissed to the empty cell after she had left.
I knew the routine well enough by now and resigned myself to getting dressed; failing to comply with Eddie’s orders would only result in a beating.
I sorted through the lingerie on my cot and laid it out so I could dress with a minimum of fuss. First I slipped a red satin garter belt around my waist and clipped it together at my belly button. I twisted it around so it faced the right way, smoothed out the satin panel at the front and straightened out the three red garter straps connected to each side of the belt.
Next I slipped into the nearly nude sheer nylon stockings Mabel had selected. I pulled each one up my freshly shaven legs and attached my suspender belt to the reinforced lace panels at the top of each stocking with the three garter straps. As I smoothed out the wrinkles in the delicate nylon along my legs little sparks of sensuality ran through me. I shrugged the sensation off and continued to dress.
Next I stepped into a pair of boy-leg lace paneled knickers. They were gray nylon with a white lace insert at the front and around each leg opening. The lace trim matched the lacing on my stocking tops. I shrugged into red satin full-cup bra which matched the garter belt. I walked over to the makeup table and opened the drawer that contained my breastforms and pushed them inside the bra cups. No time for adhesive if Eddie was due in twenty minutes. I adjusted the bra and breastforms so that they appeared as natural as possible.
Eddie obviously did not care too much for authenticity; Mabel has selected a pair of patent leather black high-heeled court shoes. They slid easily onto my stockinged feet and as I stood I was relieved to find out that it was a lot easier to balance on these wedge heels than the tapered spiked heels that I had been forced to wear up to now.
I sat at the makeup table and adjusted the lamp so that I had good light to apply my makeup. It still amazed me how quickly I had become adept at the feminine art of applying makeup!
First I applied the foundation and powder. My eyes I decided, would be in dark shades so I applied dark gray eye shadow and black eye liner. I underscored the eyeliner on my lower lids with a thin dark blue line for contrast. I applied lashings of mascara so that my lashes were almost caked with a thick black coating. I lightly applied a dark shade to my eyebrows with the eyebrow pencil and completed the look with a light pink shade of blush on my cheeks and only a slightly darker shade of pink lipstick. I decided to experiment this time and applied a coat of lip-gloss. I pulled on and adjusted my wig; just the look I wanted; I looked like a naughty schoolgirl with the lighter shades of makeup I had applied but with my dark eyes contrasting wonderfully.
Next I put on the long-sleeved cotton blouse, being careful to keep the pristine white garment free of makeup. I buttoned up the blouse, still finding trouble with the way women’s clothing buttoned on the opposite side. I pulled the school uniform tunic over my head and adjusted it. It was a dark blue and green tartan. The dark colour emphasised my pale face and dark eyes. The bodice was tight against my torso; the skirts were pleated and came to just above my knees. Then I had an idea; the finishing touch!
I rummaged around in the drawers until I found what I was looking for. I sat on the edge of the bed and kicked off my court shoes. I pulled on a pair of white cotton anklets over my stockinged feet and then stepped back into the black patent leather court shoes. I looked fantastic! I left my ears unadorned but slipped a simple gold chain necklace around my neck.
I sat back down on the bed and started applying two coats of pale pink nailpolish to my nails. While I was doing this I had time to think and realised what I had done. ‘My God! What the fuck was I doing!’
Not only was I capitulating with the crazy bastards who forced me to become a crossdressed prostitute; I was dressing like a woman as if it was a natural thing to do! I was working at looking good and even being innovative to achieve the ‘look’. Fucking white anklets; what the fuck was I thinking of!!!! Had these sick fucks brainwashed me?
I was about to get up and do; I don’t know what; remove my makeup and clothes? rebel? scream? then I heard the unmistakable sound of Eddie’s voice as he approached.
"Oh fuck yeah Dave, you will love my latest acquisition! She’s got an arse to die for; and with only a little bit of training she already knows how to suck cock like she was born to it."
"I don’t trust the cunt though; she’s too fucking smart by half," he added.
"Smart mouth on her; and you can tell she’s planning something. You have to remember this twat ain’t like Charlotte and the other dumb cunts in my stable; he was a businessman, pretty smart and well to do on the outside until he got done for running some kid over while drunk."
"She still thinks there’s a way out of her job here, and I’m sure she’s got ideas about getting outside or transferring to somewhere else, so be careful if you take a fancy to her; she might try it on, like I said, she’s just too fucking smart!"
Eddie was obviously discussing me with the punter he was escorting to my cell. So Eddie knew I had plans to try and get out of the fucked up predicament I was in. So what! If I got my chance you can bet I’d be gone in a flash!
Then it dawned on me what Eddie had said, ‘so be careful if you take a fancy to her’.
‘Maybe that meant my first customer of the night might be a man of influence and power,’ I thought.
‘Maybe I could use him to my advantage? Better be careful though; I had fucked up royally when I tried it on with the Warden; best find out all I can about this guy before I try to use my newfound charms on him,’ I considered.
"Well hello Michele; don’t you look lovely this evening," Eddie said with an evil smirk on face as he stepped into my workroom cell.
A tall good looking man dressed in prison fatigues walked in behind Eddie and came to a complete stop in the cell doorway and looked me up and down where I sat on the edge of the bed.
"Christ Eddie she’s a stunner all right; you weren’t exaggerating on bit. Hi sweetie," he said pleasantly, walking all the way into the cell.
"Say hi to my best friend David, Michele; don’t be rude!" Eddie smiled my way.
"Hi David," I said in my best attempt at a coquettish voice.
"Davy here is a very special friend of mine Michele, and I promised him that you would treat him very nice this evening; so you do that for me and maybe I’ll be nice to you later ok?" Eddie said in a voice that left no doubt that if I wasn’t nice to Eddie’s friend I would be very sorry.
"Of course I will Eddie," I answered meekly.
"So Davy, will she do; is the get-up ok?" Eddie asked.
David had been looking me up and down ever since he arrived in the cell; he hadn’t taken his eyes off me.
"Yes Eddie she’s perfect, and I bet she can be a very naughty school girl too," David chuckled.
"Yes; and speaking of being naughty; Davy why don’t you go and see Mabel and bring yourself back a bottle of something to drink while I have a little chat with Michele. Just give us five ok?"
There was no doubt that although Eddie was treating David with more respect than I had ever seen him treat anyone else, Eddie was still the one giving the orders.
"Sure; is scotch ok Michele?" David asked my way.
"Fine," I answered.
David ducked out the cell and I heard his footsteps disappear down the corridor. As soon as David left the cell Eddie strode over to me and held out his hands.
"Stand up sweetheart and give us a good look at you," Eddie said.
I allowed Eddie to assist me to my feet. He looked me up and down and smiled.
"Wonderful," he said. Then with lightning-quick speed he punched me in the stomach.
"You fucking cunt! What the fuck do you think you were playing at with the Warden? Me and you are going to have a little chat later and I’m going to remind you how things work around here!" Eddie barked.
I collapsed on to the bed, the wind completely taken out of me. I doubled over in pain as I tried to breathe. I felt like I was dying, I couldn’t get any air in my lungs.
"Don’t you start crying and ruin your face you fucking cunt bitch," Eddie snarled.
"You fucking soak up that pain and get yourself ready. David is my best friend in this shit-hole and I promised him you would treat him special, so you just get your pretty arse off that bed, breathe deep, and be ready when he gets back here."
I forced myself to stand and eventually I could breathe in shallow breaths but the pain in my stomach was excruciating. Even so I realised that I was lucky that Eddie had bought his best friend to see me otherwise he may not have cared about marking my face with his fists. I stood there looking down getting my breath back.
Eddie lifted my face to his,
"You try any of your fucking smart moves with Davy, Michele and I’ll put you in hospital you bitch. I’ll accept the loss of earnings while you recover; besides some cons in here like being sucked off by bitches with no teeth; slides in nice and easy so they say, so you fucking well behave," Eddie threatened.
He released my face just as David walked back through the door with a bottle of scotch in his hand.
"I’ll leave you two kids alone to get acquainted ok?" Eddie sniggered.
He pulled the heavy curtains across the bars to my cell, slipped through them and slammed the door shut.
"Don’t disturb them for a couple of hours Mabel," I heard Eddie yell at her as he walked off.
I was alone in the dimly lit cell with David; we had complete privacy. David looked me up and down again.
"Drink Michele?" he asked, a smile breaking out on his handsome face.
"Please," I smiled back suppressing a grimace of pain from where Eddie had punched me.
David half-filled two glasses with hefty shots of the dark amber liquid and handed me one.
"Michele you are one pretty lady if I may be so bold. And that schoolgirl outfit is just as kinky as hell," he said grinning at me with the confidence the way only men secure in their good looks seem to be able to do.
He suddenly came over serious.
"Don’t get me wrong; I’m no noncer or anything. I like to take my fun with adults not juveniles; it’s just that I love trannies when they get dressed up in sexy costumes like that."
"Oh fuck I’ve done it again; I’m sorry I didn’t mean anything derogatory calling you a tranny."
"Shit, I’m behaving like it’s my first date; let me start over."
We both looked at each other and suddenly burst out laughing. It was honest laughter bought about by David’s embarrassment and stumbling apology. He was very handsome indeed; tall and slim with black wavy hair, deep blue eyes with laugh lines at the corners, white teeth and full sensuous lips. He was deeply tanned and obviously made the most of his allocated time in the exercise yard.
"Alright. Michele, I’m David but please call me Davy."
He took a big gulp of scotch and continued.
"I’m what you might call a business associate of Eddie’s; let’s just say I do him favours and he does me favours."
"I’m fourty something, single, bisexual and disease free," he laughed again.
"And oh; to be honest I do have penchant for transvestite hookers dressed up as school girls," he finished, laughing again in his easy way.
He had managed to put me at ease and I could see how he could easily win over any woman that took his fancy; or man for that matter, he did say he was bisexual after all!
"Hi Davy, I’m Michele and a woman never tells her age," I smiled back at him, taking a sip of the single malt.
"As for the rest……..", I started but Davy interrupted.
"I know the rest honey," David said, "and don’t worry I’m not here to force you to do anything you don’t want to do. Please sit."
I sat down and as I did I winced in pain as it flared up where Eddie had punched me.
"The prick! He hit you didn’t he; while I was gone getting the scotch, the bastard hit you," Davy said and sat down beside me and took my hand.
"If it had anything to do with me I’m sorry Michele; I don’t know how anyone could be cruel to you."
I was taken aback, but wary. So many times since I had been forced to crossdress men had started out being nice to me and had then turned vicious.
"No it was my own fault," I answered, "I did something stupid and paid the price."
"Well I don’t believe that a lovely creature such as you could do anything wrong; and anyway the most you would ever get from me is a light spanking on your tidy bottom," he started laughing again and I couldn’t help but laugh with him.
We both looked down into our drinks and took a sip as the laughter died down into an awkward silence.
Davy put down his scotch and turned towards me, he reached and gently turned my face to his.
"Look Michele, I do know your situation; Eddie told me the whole story. I know you are being forced to this against your will; and as I much as I would love to make love to you I an not going to force you to do anything that you don’t want to do."
"Don’t get the wrong Idea, I often come to Eddie’s stable and go with the girls here; I do love making love to transvestites; but most of the girls here are willing to do what they do, even if they were initially forced or blackmailed into it by Eddie."
"But I have never forced myself on another person and don’t intend to start now," he finished.
I was quite taken aback, Davy seemed to be the most genuine and gentle man I had met since I got into this mess; and he was just stunningly handsome. I figured that if I was going to have to pleasure punters all night, I might as well pleasure someone who is kind, handsome and obviously has some sort of influence in this place.
I had badly miscalculated with the Warden; I decided I would put my efforts into making Davy happy and play him along until the time is right to use his influence somehow to help me get out of this jam. Tonight I was his.
I reached out with my long feminine fingers with their pink painted nails and stroked his face.
"Davy you are the nicest man I have met in this place; how can I not like you?" I smiled and gently pulled his face to mine.
I kissed him on the lips and slid my tongue inside his mouth and ran it along the top of his gums; women had done this to me before and it drove me wild. Davy responded and took me in his arms. I allowed him to pull me against him as he held me tightly but tenderly. He didn’t try anything else for over five minutes; he was just contented to kiss. We kissed deeply and passionately, and besides the smoky taste of the scotch, his breath was as sweet as a baby’s. I was becoming genuinely aroused; it was not just lust invoked by an instinctive response to stimulation, but a slow sensual awakening of my pleasure centers.
Davy eased me down onto the bed, never breaking the kiss. We ended up lying side by side our lips locked. After what seemed like an eternity of passionate kissing I was ready for more; my senses were actually screaming for further stimulation. My cock was straining against the lace panel of my boy-leg knickers, the lace stimulating my member. I pulled myself closer to Davy and lifted my leg up and over his body, the pleated tunic rode up my thigh and exposed the matching lace stocking tops of my nude nylon stockings.
Davy got the hint and started to stroke my legs and thighs, his hand sliding slowly and gently along the nylon. I kissed him deeply and growled in the back of my throat as the sensation caused by Davy’s hands stroking my nyloned leg aroused me further. I started rubbing my crotch against his hard body in attempt to further stimulate my penis. Davy sensed what I was doing and gently eased me away from him slightly; I couldn’t contain my disappointment.
But Davy didn’t miss a beat, as soon as our bodies were separated far enough, he slid the hand that was stroking my leg under my skirt and went straight to my penis. He gripped it lightly through the lace panel of my knickers and began to slowly stroke it.
I groaned and Davy responded by sending his tongue into a frenzy in my mouth; it rolled around my tongue and tickled my cheeks and gums; he was an excellent kisser. At the same time he increased the speed of his hand stroking my turgid knicker-wrapped member. I knew that I couldn’t hold on to my orgasm much longer and tried to pull away; I realised that Davy had seduced me to the point where I would let him do anything. I had allowed the tables to be turned; I was supposed to seduce him into my power, not me into his!
I was too far gone, I made a feeble attempt to extricate myself and gave up immediately as Davy tried to hold me where I was, lying beside him. We were joined at the mouth, out torsos pressed tightly together as we continued our passionate kiss. I was twisted at the waist so that my legs lay open on the bed. My legs were now spread wide, my skirt up around my thighs, the sheer nude hose on my legs running down to the cute cotton socks and the patent leather black high-heeled court shoes.
Under my skirt Davy’s hand was now stroking me hard and fast through my knickers; I began to buck and writhe as my orgasm approached. My orgasm rocketed through me; I felt it through my own body. My senses were heightened to the pitch where I could feel, taste and smell everything intensified one hundred fold.
I could taste my lipstick mixed with Davy’s sweet breath and the musky scotch we had drank. I could feel his tongue jack-hammering in my mouth, my long sleek nylon encased legs were sending those little electric shocks of pleasure I had become to love so much. I could feel the satin bra and suspender set, smooth against my bare skin, and the gray nylon knickers rubbing against my buttocks and scrotum as Davy gripped my cock in the front panel of the knickers and strocked me furiously.
I could smell the sweet perfume I was wearing and Davy’s masculine after-shave, mixing with the musky hint of sweat as we both became further excited. Then I could smell the slightly starchy smell of my semen as I spent into my knickers.
My climax shot through me, and I shuddered and groaned. Davy continued to stroke me, milking my seed into my knickers, the semen lubricating the lace and increasing the intensity of my orgasm. As the last of my emission dribbled into my knickers Davy released his grip on my erection and slid his hand under my silky buttocks and turned my lower body towards him, his hand on my ass pulling me close against him. I lifted my leg again, rubbing my stocking leg against his muscular thigh, milking the last sensations that I could out of my subsiding orgasm.
Davy held me like that, our bodies side by side, for about five minutes; never braking our kiss, my lips were almost numb. Then he stopped kissing me and looked into my heavily made-up dark eyes and said,
"You like?"
"You bet," I responded smiling into his handsome face.
Now that we had stopped kissing I pulled myself free of our embrace briefly and Davy frowned; but not for long as I readjusted our position on the bed. I pushed Davy onto his back and I straddled his waist, my pleated schoolgirl skirt spread over his middle. I leaned down and kissed him briefly on the lips and then pulled back so I was sitting upright. I looked down into his beautiful deep blue eyes and said,
"Now, what can this naughty schoolgirl do for you?"
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To be continued………………….
