Lady in the House
Copyright© 2008 by Michele Nylons
Chapter 14
Fantasy Sex Story: Chapter 14 - 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
I awoke in my cell the next morning unaware of the terrible fate that fallen upon my sister Angie. I knew that Steve had sent his henchman Danny to do something to her but I didn't know exactly what that evil bastard Steve was capable of.
I lay there shivering with dread hoping that he had just given Angie a warning, or at worst that he'd shown her the pictures that Steve had taken of me dressed as a woman being forced to fellate him. God, I hope those bastards hadn't hurt Angie, or even worse her daughter.
The prison was waking up and I could hear the clatter of cell doors opening and the underlying drone of prison life. The sounds of men pissing into steel toilet bowls, the muffled farts and the cries and curses of the inmates as they prepared for another day of boredom and brutality.
I forced myself to get up and shave and brush my teeth; I collected my soap and towel and waited for the guard to open my cell so I could take my shower. A burly guard looked through the peephole into my cell and then unlocked the door.
"Come on sugar; get your arse moving down to the shower block," he said sarcastically.
I wondered what he meant by calling me sugar. There was no doubt that Steve would have put some of the guards on his payroll. The warden was allowing him to run a prison brothel but even though Steve had plenty of inmate henchmen working for him, he would also need some of the guards. It was the same scheme that Eddie had used when he was running Chelmsford.
I went down to the shower block and scrubbed myself clean. I deliberately made no eye contact with any of the other inmates but I knew some of them were looking at me and whispering. It was obvious to everyone in the communal shower that my body had been fully shaved and I would undoubtedly have got some unwelcome attention by the 'bull dykes' except for the fact that word had obviously gotten around that I was one of Steve's 'girls'. No one in Chelmsford fucked with Steve or his 'property'.
Once safely locked back in my cell I was alone and found myself wondering exactly what had happened to Angie yesterday. The longer I was left alone in my cell the more I worried and imagined the worse. My cell door opened without warning and 'Iron Bar' Steve sauntered in and slammed the door closed. I scrunched myself up against the wall on my bunk, as far away from him as possible.
"Well if it isn't Mike, or should I say Michele. All refreshed after a good night's sleep?" he asked.
Steve was carrying a small tote bag, which he dumped on the floor before pitching himself down on the bunk. I tried to hunch myself further against the wall trying to stay as far away from him as possible.
"Oh what's the matter honey; you bashful? You don't look too bashful in this picture do you?" he teased and pulled out his highly illegal mobile phone and showed me that his screensaver was a picture of me dressed as a woman wearing full makeup fellating him.
"Look, these are the pictures your sister got to see yesterday," he smiled evilly at me.
Then he played with the menus on his phone and flicked through the pictures he had taken of me with his penis in my mouth. Although Steve was only semi-erect and I was being forced to participate, the pictures didn't appear that way. They portrayed me as a heavily made up tart fellating a well built, tattooed, con; there was nothing to indicate that I was anything but a willing participant.
"Take that filth out of here," I whimpered, pushing the phone away.
"Oh no Michele; you already knew about these pictures. I just wanted to show you how well they turned out."
"The real reason I'm here is to show these," he went on, fiddling with the phone in order to open a new picture folder.
"The quality ain't the best; Danny's a fucking hopeless photographer; he never gets the light right, and the composition is all fucked up ... but; you get a real feel for what the subject is feeling," he laughed and pushed the screen into my face.
I was horrified. There was a picture of my sister Angie! Steve flicked the buttons on the phone showing me a series of pictures of her sprawled in the corner of a filthy doorway, her pantyhose and knickers were down around her knees, her skirt and slip had been hiked up to reveal her privates. Angie's attractive, heavily madeup face was fixed in an expression of both fear and revulsion. Her jacket, blouse, skirt and legs were covered in ropes of sticky white semen. In the last two pictures Angie's face was contorted by a look of revulsion; the pictures showed a tumescent penis being rubbed over her semen-splattered face.
I lowered my head into my hands and started to sob. This was my entire fault. Because I hadn't been a willing transvestite prostitute and had not heeded Steve's warning not to resist my fate, my sister had been violated. I was heartbroken. My head was spinning; what could I possibly do fix this; or at least ensure that it never happened again?
"Ok. I'm sorry. I'll do whatever you tell me to do; I promise. Just don't go near my sister again. Please!" I begged.
"Oh no, little miss fucking smart-arse; I warned you what would happen if you fucked with me and I make no guarantees to you about anything. You fuck up again or try any of your sneaky shit and I'll unleash Danny again; besides he likes your sister, I'm not sure I can keep him off her. And as for your spunky little niece..." he finished, his face split with a depraved grin.
"I promise; I promise; I promise!" I pleaded.
"Well we'll see about that you sneaky cunt. Before you got transferred back here to Chelmsford you tried to cut a deal with the authorities for easy time in exchange for giving up your accomplices and it backfired on you right?"
"As you know, because of your testimony the Governor's brother got caught with his fingers in the government cookie jar and went down for it. That's why you ended up back here isn't it," he finished.
I looked up meekly and nodded.
"Well it seems the Governor wants to pay a visit to the cunt who got his brother banged up and who is also responsible for him getting demoted to looking after this rat hole of a jail instead of being in charge of a nice cushy reform facility."
"So now; it's not like the Governor can waltz on down to E Block where he can be seen by all the inmates and guards now is it? I mean he's the boss and needs to keep a degree of separation from the rabble."
"As you remember, from a previous experience, Eddie used to deliver some of the girls to the Governor's office, but this guy is the epitome of discretion."
"However he is determined to see you; and in particular he want's to see what I've done to you. So in that bag there are a few items to help you change from Mike to Michele."
"So get fucking going sweetheart; you got a VIP visitor coming to see you in an hour. Now we'll see if you can do what your fucking-well told!" Steve spat at me and stood up.
As he went out the door he looked back and smiled.
"By the way; my sources tell me that you are to have a visitor later this afternoon."
"It's your sister!"
"Now get fucking dressed," he smirked, and slammed the cell door behind him on the way out.
The last time I was in Chelmsford I had been one of the girls that Eddie had delivered to one of the previous wardens. I had stupidly tried to win over the Governor using my sexual guile and it had backfired on me completely. I was determined I wouldn't try any of the same tricks this time; I couldn't afford to play with the wellbeing of my sister and niece.
I opened the bag that Steve had delivered and was not really surprised by its contents; female attire, breastforms, a wig, cosmetics, lingerie, perfume and the obligatory pair of high-heels. Resigned, I emptied the bag its contents and laid them out on my cot.
I knew that I wouldn't be disturbed until the warden arrived and was grateful to have a completely walled-in cell with a solid steel door; the thought of dressing whilst other inmates and guards watched me through a barred cell was something I didn't even want to contemplate.
I arranged the cosmetics on the small shelf over my sink and stood in front of the mirror to start what was again becoming a familiar ritual. I put a layer of foundation on my face and applied powder to set it. I rouged my cheeks and applied plenty of black eyeliner and heavy mascara. I carefully put on my aqua eyeshadow and put a second coat of pink eyeshadow to highlight it. I put on the two-coat plumb coloured lipstick, colouring my lips fist then setting the lipstick with the clear, glossy topcoat. Lastly I gave my face a fine dusting of finishing powder being careful to keep it off my mascara. There; the perfect whore's face, made up to perfection. I guessed that Carmel had packed the bag because the makeup was exactly the style she would have had me wear in my E Block workroom.
Satisfied with my makeup I stepped into a black satin-lined suspender belt, the black garter straps dangled down and tickled the tops of my thighs. I then squeezed into a matching satin brassiere. I pushed the silicon breastforms into the cups of the bra and arranged them to look as natural as possible and then sat down on the cot.
I slipped a pair of fully-fashioned nylon stockings up my legs and adjusted the back-seams so they were straight and fixed them to the silver clips on my suspender straps. A familiar feelings of subtle stimulation shuddered through my body as the gossamer nylons slid up my shaved legs. The feelings intensified as I pulled a pair of black nylon full-cut panties up my legs and smoothed them around my buttocks and over the suspender belt. I suppressed the feelings and concentrated on getting dressed.
I stepped into a black satin full-slip, my body tingling at the feel of the slip on my bare skin and the whisper of the lace hem on my stockinged thighs. I stepped into a navy-blue pin-striped pencil skirt, closed the zipper on the side and adjusted it around my waist and pulled the hem down over the hem of my slip. The skirt was tight around my buttocks and thighs and had a split in the side up to mid-thigh; the hem stopped six inches from my knees. If the skirt wasn't so tight and didn't have the side-split it would almost be modest.
Next I buttoned myself into pure white, long-sleeved, satin blouse and tucked into the waistband of my skirt. I sat on the cot and stepped into the eight inch black patent leather pumps that had been provided for me. I opened a little felt drawstring bag and as I guessed it contained jewellery. I slipped a gold anklet on my right ankle and admired the way the fine gold chain glittered against my black sheer nylons. I clipped on a pair of gold drop earrings and put the gold ladies watch and gold bangles on my wrists and fumbled around until I had closed the clasp on the gold chain necklace around my neck.
I stood up and looked in the mirror as I fitted the jet-black wig. The fringe rested on my eyebrows and the bob sat on shoulders. I combed out the wig and noticed it had subtle red highlights through it. Lastly I put on a navy-blue pin-striped jacket which matched my skirt. It too was tight and clinched at the waist; the sleeves short enough to show some white blouse cuffs and my gold accessories.
I looked like a businesswoman or high-class secretary who had the dress sense of a trollop. I would look quite presentable in any boardroom if the skirt wasn't so tight and split at the side, if the jacket wasn't so figure hugging, if my heels weren't so high, if my hosiery wasn't so lewd, if my makeup wasn't so heavy. If! If! If! If! If!
There was no doubt Carmel had carefully selected my attire; in fact I hazarded a guess that someone (the Warden?) had specifically asked for a certain look. I kicked of my heels and climbed carefully onto my cot so that I could see of much of myself as possible in the small wall mirror.
Then it dawned on me! I know who I looked like!
I was dressed in the spitting image of my sister Angie!!!
Could it be coincidence? I thought not. There are no such things as fucking coincidences in the dark underworld of Chelmsford prison. I guessed I would find out soon enough; I set my resolve not to upset the Warden or Steve today. I was terrified at the though of having to face Angie this afternoon when she came to visit. How could I explain to her that it was my fault that she had been raped? But, I needed to see her so that we could work some sort of plan to get her away from the clutches of Steve's outside henchmen.
A small bottle of "Poison" perfume had been included with the cosmetics and I spayed generous amounts on my neck and décolletage then a quick squirt under my skirt on the top of my thighs. An old girl like me remembers her old tricks I guess almost smiling at the helplessness of my situation.
'Carmel; you might be prison brothel madam and fag-hag but sometimes your blood's worth bottling!' I thought to myself as I saw a tell-tale rectangular bulge in one of the pockets of the carry-bag. I unzipped the pocket and smiled with pathetic glee when I reached in and pulled out a packet of Marlboro's. I had taken up all of the previous bad habits that I had developed since leaving Chelmsford the last time, I might as well take up a bad habit I enjoyed I thought, and lit a cigarette.
I sat back down on the cot to await the Warden. I stepped back into my pumps and started painting my nails as I whiled away the time. I tried to think of anything but what had happened to my sister. I chain smoked cigarettes while I carefully put on two coats of plumb-red nailpolish.
At some stage during my reverie I realised I had no way of removing my makeup and nailpolish when the Warden had finished his visit unless Steve was going to bring me some makeup cleanser and nailpolish remover. 'What the fuck!' I thought; 'removing my makeup is the least of worries.'
I was suddenly shocked out of my trance by the rattle of keys in my cell door; and then it slowly opened.
"Come back in half an hour! Unless there is an emergency I am NOT to be disturbed understand!" a harsh voice commanded from outside my cell door.
"Yes Guv' nor!" an anonymous guard grovelled his reply.
The Warden stepped into my cell and the door slammed shut behind him and the lock rattled shut. The Warden was a slim man in his early fifties. He looked dignified with his greying collar-length hair and smart dark suit. His immaculate white shirt was accentuated by his tanned complexion. He was handsome but grave. He reminded me of the movie actor Sam Elliot; he had the same deep gravely voice when he spoke.
"Cover the peephole!" he commanded pulling a small roll of masking tape from his pocket and tossing it at me.
As I clattered over to the cell door I was thought that I glad that I didn't have to walk around all day in these eight-inch heels and tight pencil skirt. It had to take short steps as the skirt restricted my stride and the heels made me concentrate to keep my balance. I knew that the effect of my high-heels and tight skirt on my gait was causing my ample bottom to sway too and fro, swinging seductively as I walked. I stuck a couple of pieces of the masking tape over the spy-hole in my cell door and wondered if the Governor had a predilection for transvestites. I didn't know, but I knew that he was wily and prison savvy by what he said next.
"I don't give a fuck who sees you dressed like that or what they see you doing, but I'm not going to give my guards or that sneaky fuck 'Iron Bar' Steve the chance to blackmail me by taking any pictures through that peephole."
"I didn't get to be the Governor of one of Her Majesty's finest penal institutions by being stupid."
"Which brings to my why I'm here," he went on.
"You have caused me and my brother a considerable amount of trouble haven't you?" he said.
"I'm so sorry Governor, I..."
"Shut the fuck up you dumb cunt; the question was rhetorical!" he cut me off.
"My brother's inside and I'm stuck here because of the evidence you gave to certain authorities hoping to get some shortened easy time."
"Well I've put a fucking end to that; haven't I?" he snarled.
I knew better than to try to answer and stood there with my head bowed.
"But turning you over to Steve and his sleazy deviate cohorts is only part of your punishment. Sure it's your enduring humiliation and pain by being forced to be a transvestite prison prostitute that gives me the most satisfaction; but this is personal so I'm going to have to have to have some personal revenge you understand?" he explained clinically.
I bowed my head lower looking down at my pumps.
"I expect you to answer this time," he growled.
"I'm so sorry Warden, I didn't mean for all this to happen. I was just trying to..."
"Oh shut the fuck up! I don't know why I bothered to let you talk," he barked.
"Don't talk anymore unless I command it ok?"
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