Part IV

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, 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.

He stroked my cheek as looked into my heavily made-up face, he pushed a finger into my mouth and I sucked on it seductively. Eddie stroked my jet-black hair following the mane to where it caressed my shoulders, the red highlights in my hair enhanced by my mauve eyeshadow and ruby red lips.

"Oh my fucking God you are beautiful!" Eddie whispered and lowered his lips to mine.

I tried to push my hand between us to arouse him further but he was rubbing his cock against my stocking thigh as he had done earlier in the evening. I pushed back against him, encouraging him, responding to his kisses with false passion, hoping I could make him ejaculate against me.

He moved on top of me again and to my horror I felt his strong hands pull my calves up again, bending my knees so he was between my legs with my heels flat on the bed. I tried to push myself down into the bed but he forced his hands under my buttocks and lifted my arse clear of the bed. In a swift movement he grabbed two of the pillows from the many that were scattered around my 'work bed' and positioned them under the small of my back. I knew what was coming next as he reached down to my stockinged calves and pushed upward so that my knees came up almost under my chin.

I was terrified about what was to come next but remembered the advice Carmel had given me. I kissed Eddie deeply, my arms locked around his back. I felt his hard cock punching at the thin gauzy nylon panties that were the only thing between Eddie's erection and my puckered anus. I broke the kiss and reached underneath the pillow under my head; my hand came in contact with a cold hard tube.

I pulled it out and glanced at the object in my hand; it was a tube of KY jelly. Eddie followed my gaze.

"Please," I whispered.

Eddie snatched the tube and flung it across the cell.

"No Michele, not the first time. I want your virgin arse without any lubricant except mine!"

With that Eddie clamped his lips over mine again and his tongue assaulted my mouth. I felt his grip tighten on my legs, pushing them hard against my body, forcing my pantied arse high in the air, supported by the pillows under the arch of my back. He thrust forward with his rock hard cock and I felt it tear through the flimsy nylon of my see-through panties and slam against my sphincter.

I wanted to scream but he clamped his mouth tightly against mine, kissing me hard but keeping his tongue out of my mouth for fear of me biting it. Eddie started to push hard against my puckered ring gripping my legs even tighter. I felt my sphincter stretch as Eddie's glans began to invade my arse; the slight lubrication from his pre-come easing the passage only slightly. I felt a pain that was almost unbearable as Eddie continued to push against me. He was still kissing me but grunting at the same time; his breath exploding in little gusts between my lips.

The head of Eddie's penis was now just inside the entrance to my back passage and my sphincter clamped tight around his shaft. There was now no lubrication whatsoever as Eddie commenced to rape me. He pushed into me slowly, forcing his engorged member deeper into me. The pain was excruciating and I began to cry. I couldn’t help it. The fear, the humiliation, the pain; it was too much.

Large tears ran down my cheeks leaving trails of mascara as I began to sob in earnest. Eddie released one hand and bought it up and slapped me hard against my face.

"Stop that fucking shit right now!" he demanded.

"You've been a good girl up until now Michele, so just take it. Take it!!!"

He replaced his hand on my limbs and continued pushing into me. I knew now that all I was going to get was more pain unless I relented and assisted Eddie in his rape. Passive compliance was doing nothing but causing me agony. I concentrated and forced myself to try and relax the muscles creating the resistance to Eddie's cock as it intruded deeper into me. It was hard to do but I was able to make my inner passage muscles relax and suddenly Eddie's cock slid about four inches into me.

More pain now as the thicker part of his member tried to force itself still deeper into me. Eddie was panting now and was supporting his weight on his forearms that held my legs locked to my body. He was looking down so he could see his penis disappearing through the hole he had forced in my panties as it buried itself into me. Then he looked at my beautiful face, the makeup running from my tears.

"Oh yeah, this is so good!" he groaned and gave a mighty thrust.

As I felt the thrust coming I forced myself to relax and Eddie's hard cock thrust in all the way, deep into my bowels. His scrotum bounced against the soft nylon covering my arse cheeks and as he ground his cock inside me his balls rubbed against my slinky nylon panties.

I screamed, the pain was the most incredible thing I had ever felt. I tried to stop but one long agonising scream escaped me. Eddie lifted a hand and I knew he was going to belt me again. I did the only thing I could. I raised the leg that he no longer held and wrapped it around him; then I encouraged him to release the other leg so my that my legs were locked around his waist, the shiny high heels pointed to the ceiling.

I pulled his lips down to mine and thrust up to meet him and I slid my tongue into his mouth. I started to fuck Eddie McManus! At first the pain was so bad that I was sobbing into Eddie's mouth as we copulated. Eventually though, enough of his pre-seminal fluid had leaked so that it slightly lubricated my anus. Although it felt immensely uncomfortable I was able to bear the pain and concentrate on trying to get the rape over and done with.

I bucked against Eddie matching his thrusts and getting into his rhythm; I scrunched my panty ass against his scrotum as he slammed his cock home inside me and rubbed my stocking legs along his back to excite him further. My arms were locked around his back and we both kissed passionately between our gasps for breath as we rutted.

I felt Eddie quicken his pace and he plunged harder and faster, I worked hard to keep up with his rhythm and held his face in my hands and kissed him all over as my legs remained locked around his back. I eased my legs down slightly and dug my high heels into his sides to stimulate him further, I just wanted this to be over.

Then, just as Eddie was moaning and running his hands up and down my stocking legs; I guessed he was approaching his orgasm; a strange thing happened. During his thrusts I began to feel a pleasant warm feeling deep in my bowel. My penis was beginning to stir in the soft nylon of my panties, encouraged by the pressure of Eddie's body against mine as he fucked me. What the fuck was happening? Then I realised, I had read about this somewhere, stimulation of the prostate gland.

'I am not enjoying this! I am not enjoying this!! I AM NOT ENJOYING BEING RAPED!!!' I thought to myself in terror!

Eddie gave one huge lunge and pushed his cock fully inside me, he ground his balls against the silky fabric of my panties and madly stroked my stockinged thighs. He clamped his lips hard against mine and I felt his hot seed expel itself inside me. His cock convulsed and shuddered.

I had an uncontrollable reaction; my high heels drummed on Eddie's back as I lifted my arse up off the pillows to push as hard as I could against him. My tongue lashed around wildly in his mouth and I sucked his tongue deep into my mouth. My sphincter spasmed and my back passage convulsed against Eddie's ejaculating penis. My prostate pushed out rings of pleasure moving through my body in waves. I ejaculated into my panties; I wasn't even erect although my flaccid penis was pushed hard against Eddie's torso, the soft silky nylon of my panties caressing my soft member trapped between us.

We lay like that for what seemed like an eternity as our mutual orgasms subsided, gradually relaxing our fierce grip on each other and our kisses becoming more delicate and soft.

Eventually Eddie eased himself out of me and I felt the strangest feeling as my arse muscles remained relaxed and my sphincter dilated. I felt Eddie's spend leak from me and slowly seep from my arse into my torn panties. Eddie sat on the edge of the bed his member slowly deflating. He reached out and caressed my cheek with the back of his hand then bent and kissed me tenderly.

"That was lovely Michele," he whispered a genuine smile on his face.

I was still in shock at my response, trying to rationalise it. It was just my body reacting to a stimulus; 'I DID NOT ENJOY BEING RAPED!!!' I kept this mantra going over and over in my head.

Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread there when he had pressed his body against me.

I watched the terrible storm brood in his eyes as he reached out and smashed me across the face.

"You dirty Cunt!!!" he screamed, and pushed my face into his belly.

"You lick that disgusting mess off my body before you lose some teeth!" he bellowed, rubbing my face against his belly as I made a vein attempt to lick my own spend off his stomach.

He pushed me back on the bed, my makeup ruined, mixed with semen and tears and smeared all over my face.

"Now get yourself cleaned up and get changed you filthy whore; you're open for business!!!"

 

To be continued……………………………………………………………………………..