Lady in the House – Reprise

By

Michele Nylons

Introduction

For those of you reading this story who have not read the previous ten instalments of ‘Lady In The House’, I suggest you find the stories and read them first before you continue. For those of you who have read the previous instalments, I have decided that the story conception is too good not to explore it further. I know that some of you were not satisfied with the ending; and to tell the truth, after reflection, neither was I. So I have reprised the story and I hope this effort is as good as my previous attempts at physically forced transvestite sex. There you have been warned, or hopefully titillated into proceeding.

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The Reprise

My name is Mike and I am standing outside my cell in G Block of the Chelmsford Correction Facility for Men. I am in my late forties and have had a very successful career as a highly paid accountant and money manager. This Facility is not new to me. I have served time here as an inmate previously. I was convicted of aggravated manslaughter for killing a young girl whilst drunk behind the wheel of an expensive car. I served my time and was released on bail after five years. What is unusual is that for most of my time in Chelmsford I lived a dual life. I was Mike the accountant and confidant of Eddie McManus who had me transformed into Michele, a transvestite prostitute who was forced to service other inmates and prison officials in the notorious E Block, kicking up my earnings to Eddie.

I was rescued, if you can call it that, by an inmate called Davey who kept me as his willing concubine for the remainder of my prison term. This might seem like a strange arrangement, but when the price of your life is servitude as the transvestite ‘wife’ of a prison inmate or constant violation by prison thugs, then you make take the path of least resistance and pain.

For the last ten years I have been seeing a psychiatrist who convinced me this was the case. After being released from prison I sought physiological counselling to deal with what had happened to me in Chelmsford. My psychiatrist and I worked together trying to mend the abuse, both physical and mental, that I had undergone during my prison term. We agreed that I had succumbed to the world of transvestism as a means of survival whilst I was in prison. That I was in fact a heterosexual male forced to do what I did only because I had no choice.

I have not dressed as a woman for over ten years. I did have urges to transform into Michele on occasion during my first few years of release, but I overcame them. I rebuilt my life, moved to a new city, and started my career over. I became successful and made lots of money. I reinvented myself and reacquired all the trappings of success. Big house, big car, big bank account and lots of beautiful women. I got too greedy. A year ago it became obvious to me that I was in too deep in some shady real estate deals involving the misappropriation of government funds.

I cut a deal with the investigative body that was breathing down my neck. I gave up everyone else involved in my shady scheme for a one year sentence in a low security prison. I would do easy time with white-collar crims. Colour TV, gymnasium, single cell, conjugal visits; it would be a walk in park. It all went to shit when they found out about my previous conviction; "sorry Mike but the deal’s off; the best we can do is two years hard time," they said. I took it. Then I found out that my hard time would be done in Chelmsford and the nightmares returned.

When I was driven into Chelmsford Prison eight months ago I was fifteen kilos overweight with a scruffy grey flecked beard and long greasy hair. I had deliberately let myself go so that I would not attract the attention of the predators that I knew lurked within the walls of this shit-hole; particularly the predators of cell block E; particularly Eddie McManus and his crew.

I kept a low profile but made extensive inquiries as to what was going on inside Chelmsford. I was relieved to be assigned to G block; there was no one on G block who had been there long enough to remember me. I was even more relieved to hear that Eddie had died over two years ago and that his empire no longer existed. E Block was now condemned and was boarded up, awaiting demolition. The corrupt and perverted Warden had been replaced and the whole prison had undergone radical reform. I tentatively inquired about transvestite prostitution in the prison and was greeted by bellows of laughter and disbelief. Sure, there were rumours that such things had happened in the dim deep past, but no one really believed them. How could an inmate, even an inmate as infamous as Eddie McManus, operate a string of transvestite prostitutes inside a maximum security prison!

I eventually relaxed and decided to do easy time. I volunteered to assist in the prison education scheme, training inmates in the basics of bookkeeping and accountancy. I went to the gym every day and slimmed myself down, I shaved my beard and started looking after myself. I kept myself to myself outside of the classrooms and cafeteria meal times. I was a model prisoner, quiet, well behaved and compliant. I was stupid! I became complacent. I paid the penalty. And so eight months later I returned to my cell to find my few belongings packed up in a cardboard box and a surly prison officer standing at the door thrusting a piece of paper at me. I took the document and read it. It was an order transferring me to F Block. F Block was where the worst criminals were housed, murderers, rapists and perverts.

"Why," I asked, my voice trembling.

"Well it would appear the Governor’s brother has just been indicted for fraudulently using government funds," the guard answered.

"And it would appear that your testimony was crucial to the inditement. Suck’s to be you hey Mikey; no more easy time. F Block ain’t what it used to be in the old days they say; but it ain’t a walk in the park either," he sniggered.

"And it’s right next door to E Block; you know all about E Block don’t you?" the guard went on.

"What are you talking about; E Block’s condemned," I stammered.

"Never mind, I’m just fucking with your mind; pick up your shit and let’s go," he ordered.

I settled into my cramped and mouldy cell in F Block. The single cells here were old brick and tile with full-length solid steel doors with a peep hole at eye level and a trap at the bottom to pass food trays and reading matter through during locked downs. I again settled down into the routine of head counts, meals, showers, sleep, more head counts and boredom. No extra curricular activities here; just hard time. Three times a week we were allowed out into the exercise yard. I kept to myself and watched the passing parade of quiet withdrawn men doing hard time. Often there was violence; fights over who knew what, but I stayed away and made no friends.

After another three months in F Block I was nearly a year into my stretch and dreaming of release or maybe even probation. Then one day my door was thrown open and a guard yelled at me.

"Come on out lazy bones; work detail!"

"Work detail. I thought we didn’t get the privilege of work on F Block?" I asked.

"You ain’t workin’ on F Block smart-arse; you’re workin’ on E Block!" he replied sarcastically.

"New Guv’ner that’s taken over; want’s that shit-hole knocked down. But first he want’s anything of value stripped out of it. You and a few other short timers will be spending your time removing all the plumbing, pipe-work and electrical wiring. Anything that’s worth a bob is coming out. So get fucking moving," he scowled.

As I walked over to E Block I felt a sense of foreboding; all of my fears returned. I concentrated on what I had learned in therapy and rationalised the situation. Eddie McManus was dead, E Block was deserted; I will be there with a work detail supervised by prison guards. There are only the ghosts of the past in E Block of Chelmsford Prison. I remembered the ghosts as the work detail clambered through the iron gate set into the fence surrounding the dark hulking building. A sign in large red lettering hung above the gate: ‘No Entry – Condemned,’ it read.

The ghosts marched across my mind: ‘Iron Bar’ Steve who was Eddie’s enforcer; Carmel the make-over artist who had turned me into Michele; and her chubby friend Charlotte who had worked alongside me in the transvestite brothel. I actually had a fleeting fond remembrance of Mabel; the old transvestite ‘house keeper’ who kept our ‘work rooms’ clean, our makeup topped up, and who took our feminine apparel to be clean and pressed. Then I remembered the string of brutal men who had used me and any fond remembrances disappeared in a cloud of bitterness. Those bastards had degraded me; forced me into a life of transvestite prostitution. I had endured it and survived. Anyway they were only memories; E Block was dead and empty; fuck the ghosts!

Inside E Block was dark, cold, damp and deadly quiet. The guard led us into the old cafeteria where an assortment of rusty tools lay in a pile. The other inmates didn’t even bother picking up any of the old tools, they moved off in groups to already assigned workplaces. I stood there pale and shivering until the guard turned to me.

"You get to start ripping the fittings out of the bathroom," the surly guard grunted and pointed at me.

I was still shivering when I forced myself to respond.

"Can I work somewhere else; what about the guards offices, I can rip out the wiring. Copper wiring is worth a lot of money." I asked.

"Fuck off! What do you think this is; a fucking holiday? Get those fucking tools and get your arse down to the communal bathroom. I’ve been told you know the way," he sniggered.

What did that mean? I was starting to panic. The fear returning, knowing I was going back to the place where my nightmare on E Block had begun.

"What do you mean you’ve been told I know the way?" I snapped at the guard.

"Get fucking going or you’ll feel my fucking boot in yer arse," he growled

I picked up a wrench and crow bar and skulked off to the bathroom.

The bathroom was a large white tiled communal shower and bath area. I looked at the big old bath where Carmel had shaved and scrubbed me before she transformed me into a transvestite for the first time. The ten sinks, over which Eddie had illegally replaced the stainless steel with glass mirrors, were still there. The sinks were rusty and most of the mirrors broken, the shards of glass removed so that inmates couldn’t use them as weapons I supposed. I shivered again and went and stood in front of one of the two remaining mirrors. It was covered in grime and years of dust. I rubbed at the mirror and created a swath of clear glass that reflected my own face back at me.

I was ten years older than the last time I had looked in this mirror. My face was now thinner if anything, and there were flecks of grey in my hair but despite letting myself go before I came back to Chelmsford, the months of gymnasium training and ten years of professional health treatments prior to my incarceration kept me looking pretty good. For a guy in his forties I looked pretty good, I grinned to myself.

The grin froze on my face and then turned into a silent scream. Another face was reflected in the mirror. It was Iron-Bar Steve; grinning his hateful smirk which I had hoped never to see again.

"Hello Mike; or should I say Michele?" he sneered.

I turned around shocked. Steve was ten years older but just as menacing. He was tall and rangy and his grey hair was pulled back into a ponytail. He wore prison issue jeans but he was also wearing none-issue polished black ‘biker boots’ and an Hawaiian shirt, open to the throat where a gold chain and locket was visible.

"What the fuck……who……….what the fuck are you doing here?" I stammered.

I just stared into his face dumbfounded.

"Eddies dead; long gone, and I took his place," he said

"I run Chelmsford now. Every fucking thing that makes a buck in this shit-hole is run by me; and I’m always looking for a way to make more," he went on.

I looked at him perplexed, not knowing what to do or say. And then I nearly fainted; from behind the mirrored wall I heard the distinct sound of high-heels clicking on floor tiles. From around the corner of the sink units walked Carmel.

"Well hi honey," she cooed, "Welcome back. You ready to go to work?"

Carmel was wearing a grey suit, the skirt just above her knees, she wore her jacket over a white silk blouse; the outfit complete with tan hosiery and black high-heeled court shoes. Her makeup was heavy but professional and she wore a jet-black wig of shoulder length hair. Gold jewellery glittered in her ears, at her throat and on her fingers. She looked like a gaudy, over-madeup, secretary or hostess.

I turned and tried to run but Steve grabbed me and pulled me back. He slammed me against the sink bench and I collapsed winded. He picked me up and slammed me against the bench again and this time I passed out.

When I woke up I was tied to a chair, still inside the E Block bathroom. Steve was standing in front of me; Carmel stood off to one side smoking a cigarette.

"So as I was saying," Steve went on as if nothing had happened, "I’m back into the girl for hire business."

"The new warden had a change of heart. We’re running Chelmsford like it used to be run in the good old days; like, you know, about ten tears ago?"

"It’s hard to believe it’s been ten years," he sighed, "so many changes."

"So anyway; I decided to reopen the E Block brothel. I’ve got Eddie’s old suppliers back on line and along with the other swag we smuggle in, they provide all the necessary items my girls need. Clothes, makeup, shoes, lingerie; the fucking lot."

"But, I don’t understand; E Block is closed, derelict, about to be demolished," I stammered.

"That’s just a front you dopey cunt," Steve went on.

"The work details aren’t demolishing the joint; they’ve actually refitted the cells back into ‘workrooms’. You remember the workrooms right?"

"I’ve already got enough girls working for me to get started. Noncers and homos that were blowing and fucking inmates for fun or chump change. A couple of them have gladly made the switch to becoming transvestite whores. And the others; well I made them an offer they couldn’t refuse," he chuckled.

"And when one of them that still refused. Well……………..he don’t walk so good any more; nor does his wife on the outside either!"

"Carmel here was recruited to take on Mabel’s old job; you know the Madame and organiser. She’s getting a bit long in the tooth, but she still looks a stunner when she’s dressed," he smirked and patted Carmel’s pert behind and then slid his hand up her sleek thigh.

He took his hand from under Carmel’s skirt and went on.

"But, I can always another mature strumpet. Which brings me to why you are here," he said.

"You looked like shit when you first arrived back at Chelmsford; I had a few of my guys check you out and they said you looked like a fat hairy bear; no way you could be transformed into a transvestite."

"But we kept our eye on you, and now, well…….a good all over shave, some makeup, the right wig and clothes, you will be back to your old stunning self. A little older sure, but some of my punters like the more mature and experienced type," he finished and smiled an evil smile at me.

"You’re fucking crazy Steve," I snapped back, "I hated being a transvestite and doing those disgusting things. I only did them because Eddie forced me to. What the fuck makes you think I would ever consider doing that again," I spat at him.

"Fuck you! I’d rather die!" I screamed.

"Well you see, you aren’t going to get that luxury; you work for me, just like you did for Eddie, or you spend your remaining time in Chelmsford in purgatory," Steve relied evilly.

"You will be beaten every week. Not enough to put you in hospital and away from my grasp but enough to keep you in constant agony."

"Also, my contacts on the outside are going to get to your sister Angie. They won’t kill here straight away; they will have a few hours of fun with her first. And they really know how to have fun," he smirked.

"And of course if your niece happens to be with Angie when they take her? Well, boys will be boys," he laughed and held up a picture. It was a picture of my sister Angie with her fourteen-year-old daughter taken outside of their house.

I paled and nearly passed out again.

"You wouldn’t; you couldn’t!" I screamed.

Steve slapped me across the face and pushed the photograph into my face.

"I bet they will both scream a lot more than you just did before they are finally disposed of," Steve said flatly, and sat down on the edge of the bench and lit a cigarette.

"You get one chance to say yes or no; I will have your answer now."

Steve pulled a slim cellular phone from his pocket, it is of course highly illegal for inmates to have cell-phones of course, and punched a button.

"Danny, yeah it’s me. You ready to go on the thing. Yeah that’s it. The daughter’s with her? Good. Well stand by and I’ll call you in two," he talked into the phone.

"Well that’s it Mike, you got two minutes to give me an answer!" he sneered at me.

I was horrified. I either agreed to undergo at least a year of being a transvestite prostitute, or this heathen would have my sister and niece raped and murdered. What choice did I have? I sat there tied to the chair and cried; tears streaming down my face. I couldn’t talk, I couldn’t do anything other than sob. The horror of the choice I had to make was almost beyond comprehension.

Steve flicked open his phone again and hit a button.

"Hey Danny; enjoy. I want pictures; you know before and after shots," the sick bastard said.

"No! No! No!……I’ll do it!…… I’ll do it!" I cried

"Hold on Danny; the job’s off. Well I’m sure you can find someone else to meet your needs; just not those two. I still want you to keep an eye on them though, I might change my mind." Steve snapped the phone shut.

"You get the picture Mike?" he barked.

"And don’t bother trying to call and tell your sister to pack up and fuck off to wherever because my main man Danny will have her under surveillance. Not all of the time of course; but you will never know when."

"So. Now; where were we? That’s right you had just consented to working for me."

"Carmel here will assist you to make your transformation back into Michele."

"And look on the bright side; it’s not like I’m asking you to do something that you have never done before is it? From what I remember of that day on the stairwell outside the Guvnor’s office you were quite good at what I want you to did!" I slumped in the chair defeated and watched as Steve turned his back to me sauntered off.

"Ok Carmel; get that sorted! I want the place open for business after supper" he yelled back over his shoulder and left me alone with Carmel, the transvestite Madame.

"Ok hun; let’s get you prepared. You remember how?" Carmel asked in friendly tone.

My head was still spinning and I could barely compose myself.

"Not really. I haven’t dressed for ten years," I whispered.

"Really! You never; you know? Got the urge after you left here?" she asked.

"No," I lied, "I have never had the urge to dress like a woman ever since I left this scum-bucket of a place. I’m a man, and I’ve only had manly thoughts," I snapped back at her.

"Sure hun, whatever. Anyway let’s start; I’m sure it’s just like riding a bike, you never really forget," Carmel finished with smile.

Carmel untied me and led me into the small room where the big old white bath still sat after all there years. It was full of steaming soapy water. She helped me to strip and get into the warm water. Carmel lifted my leg and started shaving it, and then she put the razor in my hand.

"It will go quicker if we work together here hun," she said, and took another razor and began to shave my back.

After forty-five minutes of fiddling with half a dozen disposable razors my body was completely shaven. Carmel shaved my face and neck with a fresh razor and helped me out of the bath and dried me. She applied hair remover around my anus, genitals, and crotch and in the crack of my buttocks and a few minutes later she washed it off and dried me again.

"There we are Michele, all that horrible hair is gone," she said sweetly.

I looked up at her, dejected and resigned to my fate. Then I realised I had responded to being called Michele.

Carmel wrapped me in silk kimono and led me upstairs to the next level. We walked down a corridor with three cells on each side. The cells were all deserted but for the oversize cots which were made up with satin sheets and comforters. In each cell there were full size wardrobes, lighted makeup mirrors hung over vanity dressing tables littered with makeup, perfume and different shaped and coloured wigs sitting on wig-stands. I knew that the inside the wardrobes would be filled with sexy feminine attire and pairs of high-heels, the drawers crammed with lingerie. I remembered this place from all those years ago. The ‘workrooms’ Eddie and his cohorts called them. I couldn’t believe I was back here in this nightmare again.

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

"Like it! Like it! Are you fucking crazy Carmel! How the fuck can I like the fact that I am about to dress me up like a woman so that strangers can abuse me sexually!" I screamed.

"Well hun, you didn’t like it at first the last time you were in Chelmsford if I remember rightly; but after a while; well I remember that time with me and Charlotte, and you spent all that time married to Davey before you got parole," she said matter of factly.

"You dumb cunt I had no choice! I had to do what I had to do to survive!" I screamed again.

"You just keep singing that song hun. Whatever gets you through the night and all that. But it ain’t the way I remember it. Anyway, Steve said as soon as you show any signs of reluctance to just show you this. But I think I’ll just stick it here on the mirror where you can see it all the time," she said, and stuck the picture of my sister Angie and my niece to the top right-hand corner of the mirror.

"Now I had to estimate your size but I figure a mixture of twelves and fourteens will do. You ain’t fat but you’re a big girl and I got you tens and elevens for your shoes. I know they’re right because we’re the same size as I remember," she went on.

She went over to wardrobe and opened the doors. She rummaged around and picked out various items of clothing and laid them out on the bed. She placed a pair of black stappy high-heels on the floor near the bed and then selected various items of jewellery and put them on the dresser. She pointed to a brunette wig which had lighter highlights streaked through it.

"Wear this wig with those clothes and shoes I have laid out for you. You should be ok with your makeup; like I said it’s like riding a bike – you never forget how. But I’ll drop in on you in about forty-five minutes." She said.

"Now look Michele. You better wake the fuck up and get with the program! One of Steve’s other prospects refused to cooperate and now he walks with a cane and so does his wife."

"I’m hoping this is going to be easy for you because you’ve done it before, but if you make it hard it won’t end well." Carmel finished.

"See ya soon hun; were open for business in about an hour so get cracking!" Carmel strutted out of the cell, her high-heels clicking on the tiled floor of the corridor.

I pulled the chair up in front of the dressing table and put my head in my hands and started to cry. I heard a voice through the bars of the cell.

"You don’t have time for that Michele; if you can’t get it together, look at the picture on the mirror and get the fuck on with what you know you have to do!" It was Carmel shouting down the corridor.

I heard muffled snippets of conversation and other noises coming from some of the other cells; girls turning up to get transformed and ready for work. I stood up and closed the full-length curtains across the front of my cell; the sheer material covering the bars from top to bottom. I went back and sat at the dresser, sighed and looked down at the makeup. Carmel was right; even after all this time I knew what to do. I looked down at all of the packages, brand new, still in their cellophane wrappings. I selected what I needed and opened the packages and laid them out in the order I would use them.

I applied generous amounts of foundation to my face and then a similar coloured face powder to set the makeup foundation. I remembered that if I didn’t get my eyeliner right the first time it was always a pain to clean off all the makeup around my eyes to start again so I did my eyeliner next; black kohl all along the edges of my upper and lower lids. I brushed on liberal amounts of eyeshadow, aqua on my eyelids and pink around the rest of my upper eyes right up to my brows and out to the edge of my eye socket. I brushed on three coats of black mascara and rouged my cheeks, accenting my high distinct cheekbones.

I picked out a ruby red two-part, long-lasting lipstick and painted my lips with the base coat. While that set I painted my fingernails and toenails with nail polish to match my lipstick; I applied the two coats very carefully as I was out of practice. I then dusted my face all over with glossy finishing powder. I picked up the wig and adjusted the brunette bob so that the fringe came to just above my eyebrows and then brushed it out over my ears and around the back and nape of my neck. To set my lipstick I applied the final clear coat carefully over my ruby red lips. I smacked them together and looked at my face in the mirror.

I couldn’t believe it; Michele was back! A lot older sure; but just as sexy. The familiar routine of carefully applying makeup, and the taste, texture and feel of the makeup all came flooding back. I wanted to cry again but I knew I couldn’t. It would only fuck up my makeup and I didn’t have time to do it again, it had already taken me twice as long to do as it used to.

I walked over and sat on the bed and pulled on the white satin brassiere that Carmel had been laid out for me. I positioned two life-like silicon breastforms inside the cups and adjusted the fit. Next I slipped into a black satin garter-belt, the six long suspenders hanging from it. I clipped it at my waist and spun it around so it sat nicely in position with the clasps at my back. I opened the package of stockings, black nylon, fully fashioned with the reinforced heel and toe, back-seams and gauzy stocking-tops. I slid each of the gossamer stockings up my newly shaved legs, clipped them to the suspenders and adjusted the seams. A shiver of pleasure tried to emerge from my memory but I forced it down.

I stepped into the white full-cut silky nylon panties that matched my bra; familiar little shocks of pleasure ran through me as the panties rustled against my nylon stockings and again I suppressed them. I reached for the mauve silk blouse, put my arms into the sleeves and buttoned it up, struggling with the buttons because they are on the opposite side to a man’s shirt and I hadn’t worn a blouse for so long. I stepped into the navy blue rayon pencil skirt and pulled it up and closed up the zip on the side. I adjusted the waist and smoothed out the skirt, it clung to my thighs and the hem came to about mid-thigh. It showed a lot of leg, and the form fitting pencil shape showed off my buttocks. I sat down and put on my high heel sandals, the gold buckles glittering against my dark nylon stockings; my painted toenails visible through the reinforced toes.

I stood and walked over to the dresser and clipped on the silver drop earrings and fastened a matching pendant necklace around my neck. I pushed a couple of silver bangles on each wrist, and two rings on the first and third fingers of each hand; the rings emphasised my red painted fingernails. I sprayed a liberal amount of ‘Poison’ (my favourite perfume) on my neck, my decolletage, and a couple of squirts under my skirt.

There I was finished. I stood up and looked in the mirror. God it was uncanny! I looked just like the old Michele used to look. Sure I was eleven years older but I still looked quite attractive. Then I heard my cell door clatter open and the privacy curtain was wisped back. Carmel entered my workroom.

"Michele, you look stunning!" she said.

She walked over and stood beside me looking into the full-length mirror.

"I tell you what honey; the guys in this hole don’t deserve two good looking sheilas like us. We make quite an attractive pair of strumpets" she giggled

"Are you fucking crazy!" I yelled in her face.

"Good looking pair of sheilas??? Attractive strumpets??? We’re fucking men you moron. We are two middle-aged guys dressed up as women! And soon some repulsive criminal is going to come in here and expect me satisfy him sexually while he pretends that I’m a woman!" I screamed.

"Well Michele you can fight this all you like but you know how it works; you’ve been here before. I you don’t like what’s happening; you just have to pretend you do."

"You know some of the punters like it when you get off; and, well some of them really like it if they have to force you a bit; but you know how it works. So I’ll send in your first customer shall I?" she finished.

"You fucking dozy cunt Carmel. You’re talking to me like I have just returned to an old job from the past that I used to like!" I replied.

"I fucking hated being a transvestite and the thought of having to go through all that filth and depravity again disgusts me!"

"Oh no Michele; you don’t get away with that. I know you enjoyed most of your time in here as a transvestite so don’t deny it. You can quote all of the psychiatric self justification you want but I was here and I remember what happened," she went on.

"Yeah you were forced to do what you did, same as you are being forced now. But don’t hand me that ‘I didn’t like any of it bullshit!’"

"Anyway I don’t have time to justify either of our pasts or present circumstances; we just have to live with them."

"First punter; five minutes, be ready!" she finished and closed the curtain and walked out.

I sat down on my bed and was about to cry when I caught a glimpse of my sister’s photo stuck in the corner of my mirror. I swallowed by pride, set my resolve and lifted my head to the curtain to await whoever walked through it.

A couple of minutes later my workroom door opened and the curtain was pulled back. In walked Carmel with a young man in his early twenties dressed in regulation prison fatigues. He looked around sheepishly and then Carmel took his hand and led him over in front of me.

"Michele this is Brendan; it’s his first time doing this sort of thing so I thought I would give him to one of my more experienced girls ok?" she smiled sweetly at both us and then winked at me.

"Brendan, Michele is the best I have. She’s just come out of retirement and that makes you both special; she will be your first Tranny and you will be her first man for some time. Enjoy kids. Don’t forget Brendan, you only paid for short time; I’ll be back to get you in half an hour." Carmel finished and exited closing the curtains and door behind her.

"I, I, I, err, I’m really nervous," Brendan stammered.

"But you look lovely. You look like one of those older women who used to come around to see me mum. They were like you; heavy makeup, tight skirts, nylon stockings and fuck me high-heels. I used to wank meself crazy thinking about them," he blushed.

"Well if you are nervous and this is your first time, maybe you just want to sit on the bed and talk," I cooed, hoping I could get Brendan to waste his half hour talking.

He was having none of it.

"Fuck that! I want to get me money’s worth! You’re a whore and I want right now sex, I don’t care if you have a cock as long as I don’t have to touch it. I haven’t had any sex for six months so I’m going to enjoy this; it’s cost me all me savings," he said and reached out and pulled me to him.

Brendan locked me in his arms and his lips came down hard on mine. He pushed his body against mine, dry humping and moaning and groaning. As his tongue pushed into my mouth the old familiar taste of lipstick and makeup rekindled memories long repressed. His tongue started to explore my mouth and he hugged me harder and I could feel his erection growing in his denim jeans.

"Oh fuck yeah; this is so good. Let me take it out before I come in me pants," he grunted and eased himself away a little from me.

Brendan fumbled around with his flies and I heard the sound of his zipper being yanked down. He took my hand and nervously placed it inside his trousers; my painted fingernails scraped against smooth hard skin. It was the first penis besides my own that I had touched in over ten years. My fingers automatically took the swollen phallus in a loose grip and eased it out of Brendan’s jeans.

He was shivering and shaking so hard that I knew I could make him come in seconds and that’s what I decided I would do. If I could get away with making this guy climax without using my mouth or even worse by bottom, then I was going to do it.

"So you liked that mommies friends wore short skirts, nylons and high heels did you?" I teased, as I slowly stoked Brendan’s hard cock.

"Oh yeah, I love the way you are dressed even if you are a guy," he whispered.

"Well you certainly know how to make a girl feel good," I chuckled.

"Oh fuck this talking; come here you sexy bitch," he groaned and pulled me against him again.

Brendan’s hands went straight to my buttocks and I felt him lift my skirt up completely so that it rode up around my waist. He kissed me hard and his tongue explored my mouth, panting muffled moans of pleasure. He was playing into my hands and I responded to his kisses and twined my tongue around his and started to squeeze and stroke his rock hard cock.

Brendan pushed me back and lowered me onto the bed without breaking our embrace, his hands running up and down my nyloned thighs and across my smooth nylon panties. I guided his erection against my leg so that his glans rasped against my stocking-top whilst my hand stroked his shaft. He was shivering and whimpering and I knew he was close to orgasm; I wanted him to come soon before he figured out what I was up to.

His hands moved back under me and he caressed my buttocks squeezing and massaging them through my silky panties and he pushed his body against me and I felt his penis begin to pulse and throb. He was now panting uncontrollably, his hands squeezing and kneading my buttocks, his crotch pushing hard with the rhythm of my strokes as I masturbated him. He forced the tip of his penis harder against my thigh so that my gossamer stocking excited him further. I knew this young man was living out the fantasy of getting his rocks off with one of his mommy’s middle-aged girlfriends.

I squeezed and massaged Brendan’s penis and then released my grip on his member and pushed my body up to meet his thrusts so that his cock was humping my thigh. He quickly moved his hands under my back and gripped my shoulders and began to dry fuck me. I clamped my legs together so that his manhood was trapped between my sheer stockinged thighs and wrapped my arms around him and humped him back. I wanted this young man to climax and then get off me so this could all be over with as soon as possible.

Brendan quivered and shook and hot streams of semen suddenly drenched my thighs; I felt the hot seed against my skin as it seeped through my hose. Jet after jet of Brendan’s spend soaked into my stockings as he ejaculated against my thighs. I gagged but forced myself to keep control and tense my thighs around his erupting penis and push up against him; kissing him deeply as he gasped into my mouth in the throes of orgasm.

He slowly came down from his climax and then relaxed and lay still on top of me; his passion spent. After a minute he pushed himself off me and stood with his back to me as he put away his deflating penis and zipped up his jeans. He seemed almost embarrassed about what had just happened.

I held up my skirt as I stood up so that none of his semen would stain it. Keeping my skirt rucked up around my waist, I clattered across the cell to my dressing table and took a handful of tissues and wiped away the long ropes of Brendan’s cooling semen from my thighs. The silence was awkward and I wanted him to go.

"I know what you did," Brendan whispered.

"What?" I replied.

"I know what did. You asked me about my fetish for older women in stockings and makeup and that, and then you got me off so that you didn’t have to suck me or anything," he said petulantly.

"Well next time I’m getting a suck at least; maybe more," he whined.

"Yep next time I’m getting my full money’s worth," Brendan grumbled as he flung back the curtain and clattered out of my workroom cell.

I was relieved. I had seen off my first punter having only to live with the indignity of having to masturbate him and make him come over my legs. But I was still ashamed of myself. I felt distressed and alarmed that the seductive skills that I had learned here in Chelmsford so long ago had returned so quickly and easily. I had quickly regressed back into a transvestite hooker. I looked at the photo of my sister and niece attached to mirror and rationalised that I had only done what I had to do to ensure their well being.

But as I stood there in my come stained stockings holding my skirt up around my waist with the pungent aroma of perfume and hot semen in the air, I wondered how I was going to justify to myself the stiff erection bulging out the front of my panties.

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To be continued………………………………..

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