Lady in the House - Cover

Lady in the House

Copyright© 2008 by Michele Nylons

Chapter 15

Fantasy Sex Story: Chapter 15 - Mike is a middle aged highly successful accountant who gets sent to jail for killing a young girl whilst drunk at the wheel of his car. He is taken in by Eddie McManus, who runs all of the rackets in Chelmsford Prison with the blessing of the warden. Eddie runs a string of inmates who are transvestite prostitutes. Little does Mike know that while he is currently Eddie's accountant and secretary, he is actually being groomed to become one of Eddie's "girls"

Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Ma   NonConsensual   Reluctant   Rape   Blackmail   TransGender   CrossDressing   Fiction   Rough   Humiliation   Harem   Oral Sex   Anal Sex   Masturbation   Petting   Foot Fetish   Leg Fetish   Violence   Transformation   Prostitution  

After the warden left my cell my mind was racing. Why were they bringing my sister here to visit? How was I going to remove my makeup and nailpolish? What was I going to do about my semen-stained clothing?

I heard the keys rattle in the lock of my cell door and Steve strolled in.

"Well Michele it look's like you are starting to behave. The warden seemed happy with his little visit," he smiled mischievously at me.

"Now we need to get you cleaned and dressed for Angie's visit so lets go," he opened his palm and gestured at my cell door.

"What? Go out into the main prison? Dressed like this?" I cried.

"Oh stop it you silly cunt; don't you think that every guy in the joint knows that you're one of my girls? Do you think any of them would dare touch my property without my permission?" he said.

"Besides, except for those guys with loss of privileges, everyone else is at work or in the exercise yard so no one is going to see you anyway!" he finished.

Steve got me to scoop up the makeup and accessories and put them in the tote bag that he bought to my cell this morning and then gripped my wrist and half dragged me out the cell. I clattered along on my high-heels behind him like a dog being dragged on a leash.

As I exited the cell the prison guard who was holding open my cell door whistled at me.

"Fuck off mate; you can't afford her. Come down to E Block tonight and I'll toss you something you can afford," Steve scowled.

We passed row after row of empty cells. Down this end of F block the less privileged prisoners shared open-barred cells and I was starting to feel a little better knowing that the block was clear of prisoners and I wouldn't be seen dressed as a woman. I was being too optimistic as it turned out. I heard a hiss from a darkened cell.

"Steve! Steve! Whatcha got there mate?"

Steve stopped and went over towards a darkened cell.

"Fuck me, if it ain't Bobby McTavish? What the fuck you doing in there Bob, why ain't you out in the yard with the boys?" he asked.

"Ah I fucked up at work the other day and punched some slimy fucking guard. They kicked me out of my private cell and threw me in this barred shithole and took away all my privileges. Lucky I didn't get solitary!" he griped.

"Too bad man; it sucks to be you," Steve said sympathetically to the con behind the darkened cell bars.

"Fuck she looks good Steve, how come you got her out here in general population during the day? They renovating E Block or something?" Bobby laughed.

"Special job for a special client," Steve winked, "I'd let you have some but we're kind of in a rush."

"Oh come on man; I'm fucking locked in here for the next three weeks; at least let me have a bit of a feel?" Bobby pleaded.

These thugs were talking about me as if I was just a piece of Steve's property; to be used, given away or traded as he saw fit! The reality is; it was true!

"Look Bobby; I am in hurry but I'll tell you what I'll do. You can have her against the bars for ten minutes while I cockatoo for you; then we're gone whether you've come or not ok?" Steve said.

I couldn't believe what they were proposing. This ugly muscled thug could do what he liked to me through the bars of his cell whilst Steve kept a lookout!

"Thanks Steve, I won't be long mate, I haven't had bit for ages," Bobby laughed and waved at me to approach the bars of his cell.

Steve growled in my ear: "Ok girl, you know what to do. We ain't got all day so get him off quick!" and pushed me over to the barred cell.

I set my resolve and pressed myself against the bars looking into the gloom of the cell. Bobby was a big man with hard muscles and strong wide shoulders. He was shirt-less and his heavily tattooed torso gleamed in the dark. He came up close to the bars of the cell and dropped his shorts.

I reached out through the bars to take hold of his phallus and he knocked my hand away.

"Oh no sugar; you touch my dick and I'll come in thirty seconds. I want my ten minutes worth," he smiled.

He reached out through the bars and put one hand on my waist and the other behind my head and pulled me up against the bars. He bought his face to mine and kissed me. I kissed him back and our tongues entwined. His long hard cock was sticking through the bars and rubbing against my already stained pencil-skirt.

I reached down and lifted the hem of my skirt so that his cock was enfolded in my satin slip and closed my stockinged legs on his penis. Bobby's cock was now locked between my legs, enshrouded in my slip and nylon stockings. He groaned in my mouth and kissed me harder as I slowly rocked back and forth on my high-heels, masturbating him with my sheer nyloned legs.

This was easy! This con had been without sex for so long that he was putty in my hands; or in this case legs. Bobby slid his hand down my waist and onto my buttocks and held my groin hard against the barred cell as he rocked back and forth in time with me, sliding his hard hot member between by thighs. He kissed me passionately his tongue exploring my mouth between groans of pleasure.

Suddenly he pulled my body hard up against the bars and shuddered and grunted and I felt a hot stream of viscous liquid saturate my stocking tops. Bobby bucked and humped at my legs as he grunted and groaned until he was sated. When he had finished climaxing, he took a handful of my black satin slip and wiped his slowly deflating cock on it. His spend left silver trails on the black satin. He sighed and pushed me away from the bars.

"Fucking not bad Steve, when I get off loss of privileges I'm coming down to E block to get better acquainted with this one," Bobby said.

"What's your name honey?" he asked.

"Michele," I replied demurely pulling down the hem and straightening my skirt.

"Well Bobby is going to spend some time with you as soon as he can honey," he looked over at Steve.

"Thanks mate; see you later hey?"

"No worries Bobby, hang in there pal," Steve replied and grabbed my wrist again.

"Come on Michele; get a fucking wriggle on, we got a schedule to keep if you want to look nice for Angie," he grinned and carried on dragging me down the lower corridor of F block.

I felt Bobby's semen cooling and trickling down my stockings. But more troubling for me was that I could feel my semi-erect penis pushing uncomfortably at the front panel of my nylon panties. What was I becoming? Was I was reverting back to the Michele Nylons; prison whore?

Eventually we came to the door that led out of F block to E block. E block looked dilapidated and unused in the pale mid-morning light; fenced in, the 'No Entry — Condemned' sign over the gate gave the place a felling of foreboding.

"We're getting the old tunnel between F and E blocks opened up again Michele so as the punters won't have such a hard time getting to the brothel," Steve said as he pulled me across the deserted forecourt the block.

"Sort of like I had your old tunnel opened up," he laughed viciously.

"But seriously; now that the work gangs have completed renovating the workrooms, bathroom and reception, we can start doing some real business. The Governor insists on complete secrecy so we needed to get the old tunnel that Eddie built reopened," he explained.

I knew Steve's plan now. Not only was he going to reopen his old boss, Eddie McManus' brothel, but he and the Warden would have any outsider think that E block was just a condemned rotting hulk, whilst inside parts of it had been renovated and converted to a brothel for the inmates and guards.

"This is the last time you'll come to E block through the front door Michele; but don't worry you'll be spending lots of time here," he sniggered and slammed the main door to block shut behind us.

E Block was still as dark, cold, damp and deadly quiet as it was when I came here a couple of days ago. Eddie led me past the old disused cafeteria where the rusty tools, forgotten by time, still lay in a pile. We continued down to the part of the block that constituted the brothel. Steve opened a dirty, grime encrusted door and I was amazed at the sight that greeted me. Steve and his guys had been busy!

The door opened into a carpeted elegantly furnished exquisitely wallpapered reception room. The room was finished in colours of cerise and gold and was the antithesis of the rest of the block. A receptionist's desk was positioned adjacent to the entry; and to one side of the desk a gold trimmed door was let into the wall; a door that I knew led to the workrooms.

Carmel was sitting at the desk going over some paperwork. She was wearing a bone suit, the hem of the skirt just above her knees, a cerulean silk blouse, taupe hosiery and white high-heeled pumps. She was heavily madeup and wore a blonde wig, styled high on her head. Gold jewellery glittered in her ears, at her throat and on her fingers. The Madame of the house was in attendance.

"Carmel! Get Michele cleaned and dressed ready for the visit. Have her ready by three o'clock!" Steve ordered and left the room.

Carmel and I both glanced at the ornate wall-clock; it read 1:37pm.

"Come on Michele, we don't have much time and Steve has left me with strict instructions on how you are to be prepared," Carmel said and took my wrist and led me over to the gold trimmed door.

Again I was being spoken about as if I was piece of property, which I guess I had now resigned myself to be true. I was Steve's transvestite whore; to be used, traded and abused as he saw fit. The only thing I could do was to minimise any pain to my sister and myself.

"Ok Carmel; let's go and get ready then," I said snatching my hand free and walking through the door to the passageway that led down the centre of the workrooms.

The boys had been busy in here too and the smell of fresh paint still hung in the air. Twelve cells had had the walls of the adjacent cell knocked out so that there were now six barred workrooms; three cells on each side of the room facing each other. Each cell had been freshly painted in colours of deep red, gold and black. The oversize cots had been replaced with queen-size beds made up with satin sheets, comforters and piled high with pillows to match the décor.

Each workroom had a large wardrobe and dressing table fitted against one wall. Large well-lighted cosmetics mirrors were fitted over the dressing tables and well-padded elegant stools were provided to sit comfortably at the dressing tables. The floors were carpeted to match the décor and the lighting was subtle and discrete. Each room also had a small sink and vanity. There would be no doubt to any first time visitor what these rooms were to be used for.

The cell walls of the workrooms opened on to the corridor that ran down the centre of the room, the bars on the cells were painted flat black; and maroon coloured heavy silk curtains were pulled back from the barred walls, ready to be closed when privacy was required. The curtains provided privacy, but the muffled sounds of copulation would still resonate through the workrooms. It was designed that way of course; everything here was designed so that the punters could forget their cold hard vicious prison lives and emerge themselves in a fantasy world of debauchery. The irony was that façade of the workrooms was as false as the façade of the girls that worked in them. The girls were men! Transvestite prostitutes; some of them who worked for the money even liked what they did and others like me were blackmailed and bullied into servitude.

"Steve's been spending some money Carmel," I said, "How many girls has he got on the books now?"

During my last stretch in Chelmsford Prison I had been Eddie McManus's accountant and bookkeeper so I knew the background to Steve's empire which he had inherited when Eddie passed on. The new Governor had given Steve the approval to reopen the brothel, which had done a roaring trade when Eddie ran Chelmsford. Steve was obviously determined to make the most of his investment.

"We've got eight including you Michele and Steve's got his eye on a new kid in B Block who he thinks might be a poofter so hopefully the kid won't take to much persuading," Carmel replied.

"Remember chubby old Charlotte? She's back inside again and she was one of the first girls we recruited. She's still chubby and we're all getting older hun; but she still pulls the punters."

"Old Mabel who used to clean up and look after the wardrobes and cosmetics has passed on; but I've got an old noncer who likes to crossdress. She'd be no good as a working girl but she's taken on Mabel's old job and she does a few freebies in her cell on the block."

"Steve tolerates it because he pays her fuck all," she laughed.

"Yep, Steve has put a lot of money into renovating this place over the last couple of days. He got all the gear bought two days ago and the work gangs worked non-stop to get it finished."

"Now he's looking for a return on his investment and the tunnel between E and F block will be reopened tonight so we're going to be busy," she finished.

We reached the other end of the passageway and Carmel opened the door. The bathroom had been renovated too. The place gleamed with new white tiles, sinks and showers. A row of toilets ran along one wall, and ten lockers with ten large laundry hampers beside them ran along the other wall. Each locker and hamper had a nameplate on it. Mine was third along, next to Charlotte's.

"You know the deal honey. Steve fronts your clothes, lingerie, shoes, cosmetics and so forth and when you've paid for the initial issue, you get to order what you like on the tick and then you pay that off." Carmel explained.

"Regardless, Steve takes half of what you make up front. You never see the money. I handle all the cash and records and give them to Steve's accountant."

"I know how the scam works Carmel. I used to be the accountant!" I spat at her.

"Well honey; you're just a working girl now like the rest of us. Steve don't need any more accountants," she replied sarcastically.

"Sorry Carmel, I shouldn't take it out on you," I apologised.

"It's just that I'm so nervous about having to face my sister this afternoon. I know Steve's forcing me to see her while I'm dressed is his way enforcing my services but he must realise that I'm broken by now?" I started to cry.

"Look honey; that bastard told me what he had Danny do to your sister. He's a fucking evil cunt but while we're here in fucking Chelmsford he owns us. Just get the visit over with and get on with your life," she said.

"I know it sounds trite; but we just have to make the most of it." She finished.

"At least I have my own locker and clothes hamper; that's an improvement on the last time I worked here," I smiled wanly.

I went over to locker, kicked off my heels and shrugged myself out of my semen stained clothing and put my wig on a wig-stand beside my locker. I wrapped a bath-towel around my naked body. I looked in the mirror amused at the makeup-smeared man who stared back at me.

"Joan will take care of your clothes and shoes and brush out your wig and then return them back to your workroom. Your prison fatigues are hanging in the locker for later," Carmel said as she sat on a bench and lit a cigarette.

I walked over and took a drag off Carmel's cigarette, smiling again at my painted fingernails.

"Joan?" I asked.

"She's the noncer that I've got doing Mabel's old job. I call her the room attendant and she seems to like the title," Carmel replied an amused look on her face.

"Come on Michele; we ain't got long," Carmel appealed to me, "you know the drill girl, so get on with it!"

I used one of the toilet stalls and evacuated my bowels. It was bad enough knowing that I was going to be repeatedly taken anally, without suffering the embarrassment of being dirty down there when it happened. I brushed my teeth and used mouthwash.

I shaved closely again and took a long hot shower; scrubbing at my face to remove the makeup. Each of the shower stalls was fitted with an enema kit and a large container of lubricant fitted with a disposable applicator. I used the enema kit and when I was thoroughly clean down there I generously lubricated myself internally. I smiled grimly to myself as I thought back to the notion I had in the reception room about minimising pain to myself.

I dried off and went over to my locker and put on the satin robe and slippers that had been provided for me.

"I feel silly. A mature naked man wearing a woman's robe and slippers walking around with polished fingernails," I said to Carmel.

"Well we know how to fix that don't we sugar; lets go and get you madeup and dressed," she smiled and patted me on the bum.

"You getting cheeky with me?" I laughed.

"I remember when me and Charlotte got more than a little cheeky with you honey last time you were here; I'm still up for the odd transbian interlude if you're lucky," she smiled back at me and winked seductively.

"Now get a fucking move on!" she smacked my arse and led me back into the workrooms.

"Here we are honey; you know how Steve likes your makeup and he want's you in the brunette bob and the charcoal grey suit there," she pointed to a ladies business suit hanging up on the outside the robe.

"Shoes are next to bed and I laid out your lingerie. Steve was very particular about what you are to wear so please don't fuck about," she whined.

"Well whatever Steve wants; Steve gets," I said sarcastically.

"You know that girl," Carmel said and wandered out of my workroom, her high-heels clacking on the newly tiled passageway floor.

I sat in front of the makeup mirror, my cosmetics were neatly arranged on the dressing table. There was quite an assortment and most of them were brand new; still in their wrappers, but I recognised the cosmetics that Steve had bought to my cell that I had used this morning. Someone had put them back in my workroom. Just as well as I now had to pay for all of my own cosmetics.

A pair of breastforms was arranged on a tray along with the medical adhesive tape to affix them. I carefully affixed them in place. It had been a long time since I had done this so I took my time smoking a cigarette as I did it. I butted out my cigarette and touched up my fingernail polish and decided I had time to do my toenails as well.

I applied a heavy layer of foundation on my face and set it with face powder. I rouged my cheeks and applied plenty of black eyeliner and heavy mascara. I carefully applied the same aqua and pink eyeshadow that I had used this morning and applied the same Raging Ruby Max Factor, Lasting Colour Lipstick. I gave my face a fine dusting of finishing powder, being careful to keep it off my mascara.

I selected the brown bob from the assortment of wigs sitting on their stands inside my wardrobe. There was also a small selection of skirts, blouses suits and costumes hanging up in the wardrobe as well as four pairs of high heels. I knew that the drawers would be packed with lingerie. I didn't have time to look at everything in the wardrobe; and more importantly I knew how I was going to have to pay for it all.

I brushed the brunette bob, admiring the subtle gold streaks that had been dyed into it. I set the wig on my head and adjusted it. The fringe came to my brows and the mane sat lightly on my shoulders.

I walked over to the bed and looked at the lingerie that Carmel had laid out for me. I stepped into a white lace suspender belt fitted with three garter straps for each leg. I then squeezed into a matching white lace brassiere. I sat down on the bed, noting how soft and comfortable it felt and slipped a pair of taupe nylon stockings up my legs and adjusted the back-seams so they were straight, and fixed the darker welts of the nylons to my suspender straps. My red painted toenails were visible through the sandal-toe-reinforced stockings.

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