Chapter 4

Fifteen minutes later I was back in the cell Carmel had described as my 'work room'. She had cleaned me up in the shower and led me back here, dressed me, and was now putting the finishing touches to my makeup.

I was in daze; Eddie coming against my crotch and thighs was one thing, but 'Iron-bar' Steve's brutal rape of my mouth and then the humiliation of him ejaculating over my face had left me blank and bewildered. I had followed Carmel like a drone and let her take care of me and prepare me for my next encounter with Eddie. Now she was getting angry.

"Oh for fuck sake pay attention hun; I can't be doing your makeup for you every day, from tomorrow on your on your own!" she scolded.

She had selected my clothes and dressed me again but had to constantly remind me to watch what she was doing as I would need to dress myself in future. She dressed me like a whore!

After making up my face with heavy foundation, powder and blush, she had applied three different hues of eyeshadow ranging from frosty pink to mauve purple on my eyelids, working up to my plucked brows which she had highlighted. She applied lashings of mascara to my full lashes and finished with ruby red lipstick. She put on three coats and made me bite down on a tissue between each application to set the lipstick.

"This will stay on even during the most serious blow job she laughed," when she was done.

Next she had me put on a red nylon and lace garter belt. (Again I had vague recollections of helping Eddie select this item amongst the range of lingerie he ordered for his 'working-girls', as he referred to his transvestite prostitutes, who created a large part of income in the jail.) Carmel attached black, sheer, fully-fashioned nylons to the garter clips. As she smoothed them up my legs the electric spark of nylon on my legs bought me out of my daze long enough to admire my well-formed legs in the reinforced heel and toe nylons; the back-seam ran up to the gauzy reinforced stocking top cinched in the garter clip.

Again she fastened a gold chain around my slim ankle and had me step into a pair of shiny black, patent leather, open-toe sandals which had to be the highest heels I had ever seen. When I remarked I would never be able to walk in them Carmel laughed and said,

"What the fuck makes you thing Eddie even wants you on your feet tonight sugar; you'll be just fine on your back!"

Carmel pulled a pair of black see-through nylon panties up my legs and gave my arse a squeeze as she adjusted them on my hips with their high cut sides showing my upper thighs. She pushed my flaccid penis between my legs and hid it away, tucked under the gusset of my panties. She had me put on a red lacy bra to match the garter belt, again showing me how to adjust the breastforms just right. Over this ensemble she helped me into a purple cape of shimmering satin with long flowing sleeves, it buttoned only at my neck and came down to mid calf. She touched up my red nail polish and led me on shaky heels to the mirror.

Carmel had arranged on my head a long black wig with red highlights. My hair was dead straight, "Morticia Addams" style, and as I looked in the mirror I looked like some cheap Goth whore. The cape was open at the front displaying my lingerie clad body and the ultra-high heels caused my arse to push out and forced me to adjust my posture like a street walker strutting her stuff.

Carmel led me over to the bed and sat down next to me.

"Now Michele, you know what's coming so I won't pretend like its going to be nice the first time it happens. My advice is to get Eddie good and randy; the more excited he is, the sooner he will come hun."

"Under the pillow there is a tube of lubricant, if you get the chance use it; it will make things a lot easier on you babe."

"Now I know you don't believe all this is happening to you, but it is. There is nothing you can do about it; the only other alternative is not worth thinking about; you don't wanna spend the rest of your life in a wheelchair doing Eddie's books."

"Believe me Michele you will either grow to like this life; or you will grow to tolerate it, but there ain't nothing else in your future while you are in this prison."

Carmel left me with these fateful words while I sat and waited for Eddie McManus, the most ruthless man in Chelmsford prison. The man who had only an hour before forced himself against me and orgasmed against my body, then gave me to his underling who orally raped me and ejaculated over my face. The man who was about to sodomise me, then put me to work as a transvestite prostitute for use by the scum, the guards, or anyone who could afford the price.

I made a futile effort to try and work out in my mind how often Eddies 'girls' were used. As his 'secretary' and bookkeeper I knew how much profit he made from his crossdressed whores but had no idea how many he had or how much they charged. It was a useless exercise but it kept my mind off the inevitable fate about to befall me.

I felt a hand slide up my thigh and I jumped about a metre in the air.

"Fuck!" I cried in hoarse whisper.

"Well yes please honey; you sure look like you need it 'Secretary bird', you're dressed just like that's what you need; a good fucking!" Eddie laughed.

"Oh sorry Eddie, I didn't realise you had come in." I offered in a conciliatory tone.

"Oh fuck the small talk Michele, I've got my second wind now; I just loved watching what Steve did to you in the shower block; it's got me hot as hell!"

"You ... you saw!!!" I whispered.

"Oh yes honey, I saw. Your plump red lips looked really good clamped around Steve's big cock; you've just got to learn to swallow girl, then you won't get that yucky mess on your face."

"Of course some of your future customers like to see a pretty girl with come on her face, its adds to their pleasure and puts snotty 'Secretaries' in their place. Imagine how many of your new customers are going to be guys that you treated without the courtesy and respect they have come to expect. When you were my number one confidant you had my protection, but now you are just another prostitute. I think some of them will pay nicely to see you humiliated." Eddie stated matter of factly; cruelly!

"Anyway enough small talk," Eddie pulled me to him roughly.

I was prepared this time, rather than fight him or become pliant in his arms I responded. As his tongue invaded my mouth I pushed mine into his and commenced a passionate kiss. I made my mind go blank and remembered what Carmel had advised me, 'get him aroused and he will come sooner'.

Eddie's hand went straight to my thigh and he stroked the cool sleek satin cape over my stockinged thigh. He obviously liked the feeling because he stated to grunt as he continued to kiss me. He pushed me back on the bed and straddled me, all the time keeping his lips locked on mine as he grunted and snuffled like a pig. Eddie was now running his hand up and down my stocking legs working his way from my ankles up to my thigh as he pulled my legs up and bent my knees so that my enormous heels were flat on the bed pulled up close to my buttocks.

Eddie now ran his ran over my panties and reached into the gusset and found my flaccid penis tucked away. He pulled it free and rubbed his hand over it through the gossamer of the light clingy nylon. I shuddered.

"Oh don't be shy Michele; some men won't even kiss you before they fuck you in here; at least I'm giving you some foreplay," Eddie chuckled then again attacked my mouth with his.

He took my hand and bought it up to his shorts, he was only wearing his smoking jacket over them, the light pants he had been wearing earlier had obviously been discarded. He put my hand against the front of his jockey shorts and I felt the heated bulge of his package. I remembered how Steve had reacted when I masturbated him; the first time I had touched another man's penis, and I used the same technique on Eddie.

I dragged the back of my hand over the bulge so that my fingernails dragged agonisingly slow over his tumescent erection. Then I feathered my fingers back down his member, softly fluttering them against the rigid pole. Eddie groaned and broke the kiss so he could look down at my painted red nails running up and down across his sac and his rampant member which was straining against the light material of his shorts.

I now made a clinical decision to increase the tempo of this foreplay to excite Eddie further so that when he eventually sodomised me he would hopefully be ready to climax quickly. Maybe if I was lucky I could just get him to come against me again before he could rape me!

I reached into Eddie's shorts and gently stroked his scrotal sac using my fingernails to lightly scrape against the puckered sensitive skin. Eddie groaned and began to kiss me passionately again and with my free hand I stroked his face and ran my fingers through his hair. I circled the girth of his erect member and started a slow feathery stroking motion up and down the shaft; as I came to his glans I flicked a finger over the spongy mass of his knob.

Eddie adjusted himself over me and shucked off his jacket and pulled down his jockey shorts and discarded them. He was now naked and stretched over me, his rampant penis sticking out proudly hard against his belly. Eddie lowered himself on top of me, pushing my legs down so I was suppliant; lying beneath him with my legs splayed apart.

Eddie lifted himself up on his elbows and gazed along my body. He took in the shiny black ultra-high heeled open-toe sandals on my feet with the fully-fashioned heel and toe of my nylons exposed. He caught a glint of light off the gold chain on my ankle and ran a hand under my leg to follow the seam of my stocking to the decorative stocking tops on my thighs. His hand followed the garter strap up to the red lacy garter belt and across the sheer black nylon see through panties where he gently stroked my still flaccid penis. His hand continued upward to dwell briefly on my red lacy bra then continued up, following his gaze to my face.