Chapter 1

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, Violent, Transformation, Prostitution, .

Desc: Fantasy Sex Story: Chapter 1 - 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"

How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended up in one the States high security prison?

Well it had a lot to do with a bottle of scotch, a fast car, and a dead little girl. The magistrate decided I was to be made an example of; five years for manslaughter, no parole. How did I end up 'belonging' to Eddie McManus, the Facility's most notorious inmate? I thought back to six months ago about when I arrived at the prison. It was obvious I was grist for the mill, the inmates jeered and cat called as I walked down the centre aisle past all the cells.

"Your mine sugar,"

"Shake that arse for me baby," and other demeaning harangues were yelled my way. I was so scared about what would happen to someone like me in here.

One of the guards laughed "I'd get a big bad friend if I were you,"

His mate retorted "I'd get two big friends."

I spent first night in Chelmsford alone in a cell, scared to death and didn't sleep a wink. The next day I was assigned a cell in the general population wing and my cellmate was 'Big Bill Stevens'. He gave me the some advice.

"Mike, you need a really, really big friend or two, otherwise those lads will eat you alive. Or should I say you will spend your life eating them!" he laughed.

Bill went on to explain prison life to me; how there were two types of inmates really; the hunters and the hunted. With my small stature and my soft body, unused to any physical work, I was a sitting duck for the freaks. I explained my background to Bill, about how I was a successful businessman who had the misfortune to drive home after consuming nearly a bottle of scotch. About how I didn't even remember hitting the girl.

"We all have our stories to tell," said Bill, "and yours don't mean shite in here." He added callously.

"However," said Bill, "there is another class of inmate. The kind like you that has a lot of money on the outside; the kind that can buy protection; the kind that can get a get a guard or two in his hip pocket. Your kind." He half laughed.

And that was it, the deal was struck. Big Bill Stevens became my minder. With a liberal sprinkling of cash, which was provided by a bent guard to whom I set up a special account to access to my money outside, (and who took twenty five percent of every penny I had him withdraw); I was assigned to a larger more comfortable cell with Bill. We lived like kings; special food, special privileges, special packages from the outside containing booze, cigarettes, pornography, anything to make life more comfortable or anything that could be used for trade inside the nick.

I figured it was costing me more to live in jail than it was to live the high life outside, but I was locked up for five years with no hope of release, and without Bill as my minder, a few guards in my pocket, and the influence and protection of my money, life would be hell.

Then about three months ago, it all went to shit. I found out there was another class of prisoner, a very special class of inmate who was so unique that there could be only one in each jail, the kind of inmate that ate the hunters just as easily as the hunted. The kind of hard man that had nothing to lose, and was so hard the other kingpins in the nick paid him tribute and did his bidding without question. The kind of inmate who didn't need to bribe guards (although he kept them well paid anyway), because with one phone call to the outside he could have any guard's family battered or worse. The real boss of Chelmsford prison was not the Governor, It was Eddie McManus, or actually, Mister McManus to anyone but his closest confidants.

Eddie was in for life, but Eddie still ran one of the most successful criminal gangs on the outside. Eddie wanted for nothing on the inside, the only thing he couldn't have was freedom. And now Eddie had me!

Four month's ago Eddie approached me and said he was impressed with how a faggot little man like me had set myself up. He said he had no problems with the way I lived, as long as I bought my 'special concessions' from him, and as long as he got ten percent of any cash that I had smuggled inside. From the look on Bill's face I knew I had choice but to comply. I figured it was just life in the nick and what the hell I had plenty of money working for me outside.

Then about a month after that I was sitting in the cell I shared with Bill wondering what was taking him so long to do the daily rounds of bribes and trading when I had an unexpected visitor. One of Eddie's minders came in to the cell and said,

"Bill won't be back. In fact he ain't going anywhere any more. When the fracas is over, you get your ass down to Eddie's you little toerag."

I wondered what the fuck he was on about, but next minute 2 prison officers came in and turfed me out. They searched the cell from top to bottom removing all my contraband and luxuries.

"You can go back in now arsehole." One of the guards sneered. "Bill has had an accident and won't be back. You're on your own until we re-assign you to another cell. Sleep well sweetie!" The guard crooned and sauntered off.

I was scared shitless but knew better than to ignore the summons to Eddie's cell. I hurried down, minder-less for the first time since my arrival. Eddie was waiting for me. He was a slim man in his fifties, but sinewy with muscle. I had heard he had choked more than one man to death with his bare hands.

Eddie wasted no time explaining the situation; Bill had been withholding some of the money I was supposed to pay Eddie. Bill was now a permanent guest of the hospital and would never walk again. Bill had fucked up big time. And more importantly, Bill was my minder so I was responsible for his actions. I tried to explain the situation; that I didn't know Bill was skimming from the tribute I was supposed to pay. Eddie quickly went on to explain that he didn't give a fuck; that my girly ass belonged to him now. I was going to become his accountant, his financial adviser, and I was going to pay him for the privilege of his protection.

I was moved into a cell next to Eddie that evening. What could I do? I had to have a minder otherwise I would be every hard man's toy. I complied with Eddie's wishes. I managed his funds and barter inside and I paid my tribute. After a couple of weeks I though I had nearly a better set up than before. Then some changes started to happen and at first I didn't realise how drastically they would affect me.

Eddie had me organise some women's clothing be bought in. We had become sort of friendly; well as friendly as you could get as an underling; probably because a little chap like me was no threat to him. He showed me some fashion magazines that he had bought in and pointed out some skirts, blouses, suits, and lingerie. I have to say I was not suspicious at this stage, fashion mags in jail were poor mans porn that you didn't have to hide from the guards. I had also come to find out that some of the other effeminate inmates dressed as women and performed sexual favours for money. I also knew some of the more powerful prisoners had 'wives', crossdressed men who lived with them in their cells in homosexual relationships, either for protection or because they were just queer. The guards turned a blind eye or took part of their take from the 'working girls'; either way, I wasn't really interested.

I figured Eddie had me order in the clothing either to sell to the 'working girls' or he had his own 'wife' hidden away somewhere discretely in the jail. I was really puzzled at how much interest he had me show in ordering the lingerie and shoes. He took special care in selecting sizes. Together we poured over the catalogues and I feigned interest as much as I could. I agreed with him that high heels looked lovely on a nice set of legs, but were hardly practical for a crossdressed inmate to get around the jail.

"You fucking nonce!" He laughed, his voice roughened from forty cigarettes a day. "She won't be wearing them around the nick, just in my cell, and mainly on my cot." He laughed again.

We spent ages looking at stockings and pantyhose. He told me how much he loved nylons on a shapely leg and had me order in large quantities of fully-fashioned stockings and sheer to the waist pantyhose in many different shades. I explained to Eddie that they would cost a fortune, as even the guards who were on the pad didn't like prisoners having nylons because they were an ideal medium for suicide by hanging. One or two inmates in the past had suicided by hanging themselves with a stocking.

"Just get on with the order, secretary!" he scowled. "Just fucking pay the price! Just fucking do what your told!"

I hated upsetting Eddie in any way as he scared me to death, and now I leapt to my feet to make the deal with the bent guards and pay their ridiculous prices for the smuggled in lingerie and other girly items. Another thing I didn't like was that for a week or so Eddie kept calling me his 'secretary' for some reason. I figured it related in some way to me being his accountant.

Then the fateful day happened. Today!

I could walk around the jail with immunity now that I was 'one of Eddie's'. I had sometimes seen other inmates point to me and I overheard them referring to me as 'Eddie's new secretary'.

"Oh yes, I can see what he sees in her." One 'noncer' said, which I found puzzling.

It was just after dinner when I returned to my cell to find one of the prison 'wives' waiting for me. I had seen him before and knew him as Craig, one of Eddie's underlings. I only just recognised him though as he made a quite attractive and convincing woman.

"Fuck off you poofter!" I shouted at him, her, It! "Don't you know who I work for!"

"Oh I know darling," she cooed at me. " And Eddie said it's time. You're coming with me honey. I'm going to prepare you for him."

"What the fuck are you talking about," I said.

"Look honey, my name is Carmel and I work for Eddie. And you're coming with me and I'm going to show you how to transform yourself for Eddie." Carmel said calmly.

"I still don't know what the fuck you are talking about." I said

"Well honey is you look over your shoulder you will see 'Iron Bar' Steve. You can either be transformed by him or by me ok?" Carmel crooned.

I turned around, and sure enough, there was 'Iron Bar', Eddies enforcer. He was grinning at me and slapping a piece of steel pipe in the palm of his hand. I made my decision and nodded to Carmel who led me out of my cell down into E Block. E Block was pretty much deserted and I had heard rumours that it was a part of the prison used by prisoners and guards alike for activities the general population didn't need to know about.

Carmel led me into one of the bathrooms in the block and then she turned me into a small room where a big old white bath sat. It was full of steaming soapy water.

"Strip and get in sugar," Carmel said.

I looked around saw all manner of soaps, shampoos, razors and such.

"Fuck off hag fag," I sneered at Carmel.

"Steve, she wants you!" Carmel yelled out the door, and sure enough there was 'Iron Bar' with a smirk on his face, smacking his trusty pipe into the other palm. Carmel pushed her face right into mine.

"You don't seem to understand do you Mike? You either do exactly as I say, which is what Eddie wants; or, I let Steve there take you for the last walk you'll ever have!"

I now realised the severity of the situation but was still confused. Although not confused enough to understand I had to do exactly what Carmel said or I would have my legs broken in such a way they would never mend. I shucked off my clothes and lowered myself into the bath. Carmel threw me a loofah and said "Scrub!" So I did. Then she sat on the edge of the bath and took one of the disposable razors from a pack. I was not surprised that one of Eddie's 'girls' would access to an item that anyone else in the prison population could never get.

Carmel lifted my leg and stated shaving it. I tried to pull my leg away and she held it tight, gave me a stern look, then glanced towards the door where Steve was lounging outside. I surrendered.

"Watch how I do this hon," Carmel said, "you're doing this shit yourself from now on."

Then it dawned on me what was happening, the significance of the word 'transform'; the reason Carmel was shaving my legs. I felt numb. I couldn't comprehend why Eddie would do this to me. I was in a trance as Carmel fished shaving my legs and then the soft down on my arms. She shaved my face and rubbed moisturiser onto it. Then she led me out of the bath and dried me off. I was just like a mannequin that Carmel could move around and pose as she liked. Carmel led me to the part of the bathroom that had about ten sinks and mirrors lined up along the wall. It wasn't until later that I took notice that the usual stainless steel mirrors had been replaced with glass and that each of the mirrors had a bright light over it. One of the sinks had a high stool set up in front of it and Carmel sat me on it.

"Now pay attention honey, you need to learn how to do this," she said.

I noticed that on the shelf, below the mirror, was a large assortment of makeup. Carmel took a damp sponge and applied generous amounts of foundation to my face, cooing at how lovely my skin was and that I didn't need to use 'dermablend' or other such heavy-duty foundation. After she had applied the foundation to my face and neck she picked up a brush and applied a slightly lighter coloured powder to set my face. She rouged my cheeks, accenting my high feminine cheekbones. She fussed around my eyes applying liberal amounts of eyeshadow, eyeliner, and mascara. She then finished with another light dusting of powder and a plum red lipstick to my pouty lips. All the time Carmel was explaining to me how I would need to learn how to apply my own makeup. I was still too dazed to really accept what was happening. The final touch was the application of a bright red nail polish to my toenails and fingernails.

Then Carmel reached under the sink and opened a cupboard. She pulled out three wigs sitting on wig stands and I noticed there were a lot more in there. Carmel looked at me seriously for awhile then selected a blonde bob and piled it on my head. She turned me towards the mirror and made some adjustments. I was shocked as I looked at myself; I looked stunning. I couldn't believe the transformation to my face. I looked like a sexy, mid thirties, over made-up, slut.

"You like?" Carmel smiled at me.

"I look like a fucking woman!" I shrieked.

"Well that's the idea stupid," Carmel Laughed. "Follow me."

I followed her out of the bathroom, stark naked and with my face made up to look like a whore. 'Iron Bar' Steve followed at a menacing distance. Carmel led me into a cell in a set of six on the next level up. The five others around it were all deserted but the oversize cots were made up with what looked like satin sheets and comforters.

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

I couldn't believe it, the oversized cot was made up with satin sheets and there was a full sized wardrobe. Hanging inside were the clothes that Eddie had made me help him pick out. Four pairs of different coloured high heels were arranged on the bottom of the wardrobe and in the drawers that had been pulled open, was the lingerie Eddie had spent so much time selecting with me. Now I knew why! Carmel led me over to the bed and sat me down.

"Well I guess I better show you how to dress too," she said. "Eddie was quite specific about what you were to wear for him tonight."

Carmel selected a pair of glossy, sheer to the waist taupe pantyhose and rolled them up my legs. She stood me up and showed me how to pull them tight around my arse. The nylon felt cool and slippery on my legs, not unpleasant. I had always loved to run my hands up a nyloned thigh but had never imagined what it would be like to wear them. I nearly died when Carmel put her hands inside the gusset of the hose and grabbed my cock and pushed back between my legs. The tight nylon held it snugly between my legs.

"There," Carmel said, "lets get that little thing out of the way shall we?" she laughed.

I heard Steve laugh at the door and realised to my humiliation that he was watching the proceedings. Next Carmel pulled a pair of silky nylon peach coloured, full cut panties from the drawer with a matching bra.

"Here," she said, handing me the panties, "put these on while I get the breastforms".

I didn't know what the fuck she was talking about, Breastforms? I slid into the panties, the silky nylon of the panties created little electric shocks of pleasure as they rubbed against the sheer nylons as they slid up my legs. Carmel turned around and was holding two perfectly formed small breasts, one in each hand. She put them down and put the bra on me then placed each of the plastic breasts in each cup.

"There is some adhesive in the dresser draw that has instructions on how to adhere the breastforms to your chest. You can learn to do that later. The way I'm dressing you tonight it won't matter, you just need the shape." Carmel said, sounding serious about a subject totally alien to me.

I was still in shock as to what was happening to me when Carmel sat me down again and lifted my feet one by one and placed a black, shiny, high heel on each one. She pulled out a little jewellery box from out of a draw in the base of the oversize cot.

"For fuck sake keep this locked away from now on, and never lend your jewellery to any of the other girls." Carmel said very seriously.

'My jewellery!' 'Other girls!' 'My workroom!' What the fuck is happening to me I wanted to scream. I kept my cool though, I realised I had no choice but to succumb to the ministrations of this freak man/women who was dressing me or have 'Iron Bar' Steve cripple me for life. Once I saw Eddie I knew I could convince him that he had his little joke and that I would make up for what ever mistake I had made as soon as I got back to work as his finance manager, back in the general population of the jail.

Carmel selected a simple gold ankle chain and fastened it around my slim ankle. The gold twinkled in the light against the sheen of the sheer nylon. Carmel put two gold bands around my left wrist, and a simple but elegant, gold ladies watch on my right. She placed another simple gold chain around my neck, from which hung a black onyx stone set in gold. She clipped matching earrings to my ears.

"We'll pierce your ears tomorrow hon," she said humming away as she worked.

Like fuck you will, I though to myself. Next Carmel had me stand and I teetered on the high heels, steadying myself by holding on to her.

She smiled, "You'll soon get used to them."

I thought again, like fuck I would, because after tonight I'll never need to wear them. Eddie will see this is a mistake. Carmel selected a satin waist-cincher that matched my bra and panties and pulled it tight around my waist. My already un-masculine body was now positively effeminate. My long legs were enhanced by the gossamer hose, my arse had been pushed out slightly by the squeeze of the cincher, my false tits were just proportional to my small build, and my little waist. I looked like a well looked after thirty-year-old woman.

Next Carmel took a cream coloured silk blouse and pulled it up my arms and buttoned up the front. It was open down to the second button and showed a hint of my peach bra. Next she had me step into a peach nylon half-slip that again matched my bra and panties. It too gave me little electric shocks of pleasure as it slid up my nyloned legs. Carmel reached into the wardrobe and pulled out a hanger on which there was a bark blue women's business suit. I remember Eddie picking it out of a catalogue and wondered at the time why his 'working girls' would need something so sophisticated. But along with nurse's uniforms and other fetish clothing I figured it was just to pander to some expensive punter's peccadilloes.

Carmel had me step into the skirt and pulled it up my legs and fastened it around my waist. She straightened my blouse, ensuring it was tucked in and then surprised me as she reached under the skirt and pulled down the half-slip that had become rucked up when I donned the skirt. I got another of those little electric shocks of pleasure from her hands straightening the slip and touching my stocking legs. I looked down and was surprised to see a pair of sexy pantyhosed legs showing from below the hem of a navy blue skirt the hem of which lay six inches above my knee. Attached to those legs were a pair of sexy nylon encased feet, the red toenails showing though the gossamer nylon. Around one slim ankle a gold bracelet reflected a glint of light.

Finally Carmel helped me into the matching jacket and led me over to a full-length mirror that was attached to the wardrobe door. I was amazed! Staring back at me was a gorgeous woman in her mid thirties. Her bottle — blonde hair and over madeup face atop the cream blouse and navy blue power suit made her look sophisticated, but strumpet like. Carmel spun me around so I could see my side and rear. My ass stuck out provocatively and stretched the material of the skirt taught against my arse. It was forced that way by the pull of cincher and the stance I had to adopt to remain on feet in the high heels. The rear of the skirt had a small split that showed about another six inches of the back of my nyloned thighs.

Just then I saw hand reflected in the mirror as it grabbed my arse. It was Steve.

"You look great," he growled as he pawed my arse and legs.

"Get the fuck off her Steve or I'll tell Eddie," Carmel screamed smacking Steve's hand away.

Steve retired to the door sheepishly.

"You know Eddie always gets them first!" she yelled after him.

Then the full light of the situation dawned on me. As I looked at the reflection of the trampy woman in the business suit I realised she looked just like a caricature of the 'sexy secretaries' I had seen posing in porn magazines just before they stripped off their clothes, page by page.

Now I knew why Eddie had called me his secretary! Oh my god! He had been planning this for weeks, having me help him pick out clothes, obviously getting his 'girls' to find out my sizes for clothes and shoes. And now I had no choice but to be Eddie's 'sexy secretary' or suffer an agonising beating and the loss of my limbs!

"Mike, now you are Michele, you look beautiful! I hope you enjoy your first time as much as I did," said Carmel as she slid past me and out the door.

And that is how I became to be dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail.

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