Chapter 5

Carmel rushed into the cell, or as she called it, my 'workroom';

"Come on Michele, the night's only just begun! The waiting room is full of punters, and because you are the new girl, you're top of the menu!" she said, busily fussing around me and helping me to my feet.

I allowed myself to be pulled up off the bed, and stood in front of Carmel (who until today I had only known as Craig).

"Look what he did to me!" I cried; "Look what that disgusting man did to me!"

"Oh shut the fuck up," Carmel crowed. "You'll get worse and you'll get better Michele; that's the life of a working girl here in Chelmsford!" the crossdressed freak standing in front of me explained matter of factly.

"That's just it!" I cried.

"I'm not a girl! I'm not Michele; my name is Mike and I'm a businessman not a woman! And you are not Carmel; some kind of bawdyhouse Madam; as you like to pretend! You're Craig! A guy in a dress, pretending to be a girl! You're just a sad, pathetic, transvestite prostitute living in some made up dream world inside this prison!"

"I'm a big name outside!" I cried.

"A 'Face'! As you jailhouse scum are want to say! I have money, friends, influence" I cried.

Carmel laughed out loud and slapped me hard across the face. I felt the sting though my tears.

"No honey! You have it all wrong! You're inside Chelmsford prison honey and you are whatever Eddie want's you to be!"

"You're Michele! You're Eddie's property; and you have about five minutes to get ready because customers are waiting!"

"Now pay attention, you really are on your own after I clean you up; a girl's got to make her own living too you know, I can't spend all night showing you how to put on makeup and how to dress" Carmel sneered.

She led me back past the five other cells that made up this section of E block. Low light leaked through the bars of the other cells; red shaded bedside lamps had been lit. I saw other 'working girls'; transvestite prostitutes, putting the final touches to their makeup, adjusting the seams on their stockings, or arranging their wigs. They sat on their oversize cots that had been made up with satin sheets; bold colours, black, red, and blue were predominant. One or two of them looked up with their painted faces and smiled at me; but there was no sympathy in their smiles; they were the types of smile that predators gave their prey just before they pounced for the kill. Four of the cells were occupied by Eddie's 'girls', leaving my 'workroom' and the cell across the passageway vacant. It dawned on me as I clattered along on my impossibly high-heels that the vacant cell directly across from me must be Carmel's 'workroom'.

We arrived at the bathroom at the end of E block again and Carmel helped me undress and sat me down in front of the highly polished stainless steel mirror. I washed my face clean and stared at the makeup arranged on the shelf below the small sink.

Carmel said, "Ok Michele; you've done this enough times tonight with my help; it's time you went solo."

Carmel lit a menthol cigarette and sat down on a stool beside me, preening herself in the mirror. She made minor adjustments to her own makeup as she sat there and smoked.

It was amazing how much I had learned in such a small amount of time. I took a damp sponge and applied generous amounts of foundation to my face and neck finishing with a slightly lighter coloured powder to set my face. I rouged my cheeks, eventually getting the hang of how to accent my high feminine cheekbones. Carmel had to instruct me again how to apply the rouge after my first attempt made me look like some kind of circus clown with rosy red cheeks. I then applied liberal amounts of eyeshadow, eyeliner, and mascara with minimal assistance from Carmel.

"You're getting the hang of it honey, although you do look like a bit of a panda, but you will become very good at it soon," said Carmel laughing at my efforts with the mascara applicator.

"Besides, the punters like us heavily made-up, it's not like were supposed to be their wives or Moms," She laughed wickedly and applied another coat of mascara to her own heavily made-up eyes.

I finished with another light dusting of powder and applied two coats of plum red lipstick to my pouty lips. Putting on the lipstick I had discovered, was the easiest part. I applied a touch-up coat of bright red nail polish to my toenails and fingernails where they had been chipped. I checked myself out in the mirror with a self-satisfied smirk. Not bad for my first solo effort I thought.

"Wonderful Michele; you are getting the hang of it now," Carmel cooed like I was a good pupil who had learned her lessons well.

Then I took stock of the situation. I had been concentrating on applying my makeup and was amazingly, feeling a shimmer of pride in my efforts! What the fuck was wrong with me! I had also referred to myself as 'SHE' in a number of my thoughts and more disturbingly had subconsciously thought of: 'MY makeup!' 'MY clothes!' and 'MY shoes!' What the fuck was happening to me! Was I turning into some kind of willing participant in this sick, fucked world that Eddie had created inside this prison!

I bought myself back to reality by concentrating on the debauchery I had suffered over the last couple of hours. I had been sodomised and orally raped; my back passage was still sore from Eddie's invading penis. I could still taste the swampy, salty, taste of 'Iron Bar' Steve's secretions which he had deposited in my unwilling mouth; and my ribs and stomach muscles still ached from the pummelling I had received from Eddie during the evening.

I looked in the mirror again and saw what I really was; a small, insignificant male prisoner forced to wear makeup and jewellery. A parody of a woman! A man compelled to dress up in women's clothes so that sick, twisted prisoners could take their carnal pleasures and somehow justify to themselves they were not gay because they took their gratification from a man who is dressed as a woman.

Carmel helped me into a satin robe and then scooped all of the makeup off the shelf and into a small makeup case. She took the wigs with their stands and loaded them into my arms she grabbed my discarded clothing and shoved it with my high-heels into my arms on top of the wigs. Holding the makeup case in one hand she took my hand and started to drag me out of the bathroom.

"Ok Michele, from now on this place is just for you to clean up, shower and shave. Don't leave any clothes, makeup or jewellery here or the other girls will nick it as soon as you take your eyes off it; and then you will have to pay for it to be replaced."

"Everything you need is in your workroom and only you, Eddie, and Mabel have a key."

"Who the fuck is Mabel?" I asked.

"She's an old lifer who likes to crossdress. She's really too old to shag, but some of the cons occasionally give her one when they are short of money. She's Eddie's minder for his stable of working girls. Steve is the muscle, and Mabel is the housemaid is the best way to explain it I suppose."

"Mabel comes around during the day and changes the sheets and washes our clothes. She'll replace your makeup and tend to your wigs. She also takes orders for new clothes, lingerie, and any special costumes when you need them; all done for a small fee, and all done with a smile, she likes to be around us girls," Carmel beamed. "She also takes our bookings and manages the punters in the waiting room."

"What the fuck are you talking about?" I asked Carmel, bemused.

"Look Michele I really don't have time for this; you used to be Eddie's bookkeeper so you should have it figured out by now. Half of every fee we get off a punter goes to Eddie ok. You will probably have to work for nothing for about three months to pay for the clothes and other stuff Eddie has bought you to get you started with. Once you start making money Eddie keeps it for you on a tab; Mabel will deduct your expenses and such and will also give you cash or goods when you need them."

I realised what Carmel was explaining to me of course. As Eddie's prison accountant I had indeed managed his books and was aware that he had someone else look after his 'working girls' and put money into and out of that part of the account; but all I ever saw were the profits. It never occurred to me how complicated this side of his business was.

"Hang on a minute; what the fuck are you are talking about? Expenses? Goods?" I asked.

"Jesus Michele! You just don't get it do you?"

"Everything is a business to Eddie. The clothes, makeup, wigs and so forth you have to pay for. You also pay to have your clothes washed and 'workroom cleaned'. You also pay when you order in more clothes, wigs, lingerie, shoes and stuff. Mabel will bring around the catalogue and an order form for you."

I mind flew back to the times I spent with Eddie as he made me order in women's clothes, nylons, makeup and so forth for his stable of working girls; but I never thought I would be wearing any of it!

"Sometimes if Eddie sees something he really wants to have you wear he'll buy it for you as a present," she smiled.

We had arrived back at my cell; my workroom, as it I now realised it to be. Carmel pushed me through the door.

"Ok hun, its ShowTime; put those dirty clothes in the laundry basket, put your wigs and makeup in the wardrobe and get dressed. Try that long black wig hun, it will suit your makeup. As you can see Mabel has laid out your outfit for your first customer, it must be a special request, that's always good because the punter has to pay more for fetish stuff."

With that Carmel went through the door of her own cell, sat on the bed and lit another menthol. She punched a button on an intercom located on a nightstand next to her bed and spoke into it.

"Ok Mabel, send him in," she sang.

Carmel rushed across to my cell and pointed to an identical intercom on my bedside table.

"Oh, I forgot to tell you how this works. Its simple hun," she explained, "when the blue light is on you have a punter waiting. Press that button to talk to Mabel in the waiting room. Press that orange button to indicate you are busy, cleaning up whatever, and that red button there is the panic button."

"Press the panic button and 'Iron-Bar' Steve will be here in seconds. But only press it if you have genuine emergency," she advised me, slipped me a wink, and skipped out of my cell to the sound of approaching footfalls.

Genuine emergency! GENUINE FUCKING EMERGENCY!!!!

What could be more of a genuine emergency than being forced into being a transvestite prostitute in a fucking jail!!!!

I sat on the bed and controlled the urge to cry. I knew it wouldn't help; all I could do was to get through tonight and then figure out a plan to get of the indescribable mess I was in.

I looked down at the clothes arranged on the black silky sheets. A 'special request' Carmel had said; what the fuck? Resignedly I started to dress.

First I open the package of hosiery. It contained a pair of white, sheer to the waist pantyhose. As I slid the sheer nylon up my legs those little electric sparks of delight again ran through me. I hated myself for enjoying the sensation of it! The sheer waistband was snug around my tummy and I tucked my deflated little penis between my legs to be held there by the gossamer nylon gusset of the pantyhose. Next I slid a pair white full brief satin panties up my legs and pulled them snug around my bum and groin. The rasp of the silky panty material against my sheer hose was so sensual that I felt my little cock pulse.

I slid the matching white satin bra around my chest and went to the drawer where I knew my breastforms where kept and placed them neatly into the bra cups. 'My breastforms' ... what the fuck had happened to me!

I concentrated on getting dressed and tried not to think about the exquisite feel of the nylon and satin on my skin. A pair of plain white high-heeled pumps was at the foot of the bed and I slid my feet into them and stood up. A single pristine white cotton tunic was laid out on the bed so I stepped into it and pulled it up my body. As I started to do up the buttons on the front of the tunic I realised what it was. A nurses uniform; 'Special Request' in-fucking-deed!!!

As recommended by Carmel, I placed the long, raven haired wig on my head, adjusting it in the mirror on the wardrobe door. I picked up the little white nurse's cap with the Red Cross on it and placed it on top of my head. I looked stunning!

In the full-length mirror was the image of gorgeous nurse in a crisp white tunic buttoned to her throat. Her long legs shimmered in gauzy white nylons below the knee-length hem of her skirt. Her legs terminated in the pristine white high-heeled pumps. The nurse lost all credibility however when you looked at her face. She was so heavily made up; with lashings of mascara and plump red full lips framed by her glossy black mane. The little white cap with its Red Cross added to the image; the girl in the mirror looked like a tramp in a nurses uniform; the same sort of fetish clothing worn by the girls in men's magazines that I liked to masturbate over.

I looked down at the bedside table and noticed the little blue light flashing. My trembling hand extended a red-painted manicured, finger-nail and pushed the button.

"Send him in," I whispered hoarsely.

Oh my God; what was I doing? The only thing I could I realised; do what I was told or have my legs and face broken. It was only for one night and soon it would be over. I would escape; I would tell the Warden, my lawyer; someone who could get me out of the obscene mess I was in!

I sat on the bed and waited. My eyes drifted to the cell across the way and I saw Carmel. She was standing up in her cell, bent over and holding on to bars of her cell for support; her painted red fingernails digging into the palms of her hands as she tightly gripped the iron bars. Her skirt was rucked up over her back, her pure white arse raised suppliantly into the air. Positioned behind her a large black man was pounding himself in and out of her. As he slammed into her he grunted and pulled her soft white arse back against him so he could drive himself in her as far as he could go. Carmel's heavily made-up face looked idyllic as she concentrated on maintaining the rhythm whilst she was anally pummelled. She opened her eyes and looked at me through the bars, she smiled at me, winked and then closed her eyes again as she rocked back and forth on her high heels, her sheer stockinged legs glittering in the low red lamplight.