Chapter 1

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!"