Chapter 17

After putting this story to bed in July 2005 and then reviving it again in March 2007, I have finally run out of ideas for our intrepid transvestite prison prostitute. That said; after you read on and see how I have concluded the series, you could argue that there is plenty more to explore in this story; especially the development of the characters of Michele's sister Angie and her niece. But, I have other stories to write and I think it's time for this saga to end. But you never know...

"Well honey; that was wonderful but we still have to work," Carmel said, and arranged her clothing before leaving my workroom cell.

I head the clicking of her high heels receding down the corridor dividing the workroom cells.

I cleaned up and sat down to wait for my next punter. My life had come the full circle and I was resigned to my future as a transvestite prison prostitute; being forced to service punters for "Iron Bar' Steve in MH Correctional Establishment Chelmsford. Steve had hold over me by using blackmail and the threatening to hurt my sister Angie and her daughter.

And what was the story with Angie? During the conjugal visit that Steve had arranged I had no choice but to fellate Danny in front of her; but she had willingly sucked Steve off and orgasmed herself when he came. I guess she has the same desires as anyone; after all, how many times I had I orgasmed whilst being taken against my will. Which reminded my of those four filthy prison guards who had used me and then pissed on me; god I hated them and I hoped that some form of revenge would be forthcoming. Then I heard muffled male voices in the corridor and mentally prepared myself for work.

It was about a month later that Steve came to visit me one evening in my workroom. I had settled into the routine of forced prostitution and was seeing about four customers a night and more on the weekends. I did very little during the day; Steve's 'special girls' got special treatment from the guards, we didn't have to work and we got preferential treatment and better food than the ordinary prisoners. There was some resentment from the other inmates; but what could they do about it? Steve and his henchmen ran Chelmsford Prison with the help of the guards on the payroll and with the consent of the warden. Besides, a lot of the prisoners saved up their cash so that they could visit Steve's prison brothel and enjoy some time his troupe of transvestite prostitutes.

It had got to the stage where if I liked a punter I would allow myself to become aroused during the sex and sometimes even orgasm. Some of the punters liked to play with the girls' cocks but a lot of them liked to think of us as real women and didn't want to even see our male sex organs. They never got violent though, Steve wouldn't allow his merchandise to be damaged.

And that was why, it turned out, that Steve came to visit me.

"Hi Michele," he smiled as he entered my workroom cell.

I was dressed in a red leather miniskirt with a kick pleat in back, white satin blouse and red high heeled pumps. I was wearing lashings of makeup and lots of trashy jewellery with my red painted fingernails and jet black bob wig I looked like a proper trollop. Under my skirt and blouse I wore a red satin brassiere and suspender belt, sheer white nylon panties and black, fully-fashioned silk stockings. I was earning Steve plenty of money, and as our clothing allowance was proportional to the amount of money we bought in, I could afford the best clothing and lingerie available. I even looked forward to getting my weekly clothing catalogue from Carmel. We would sit together, sometimes with anther working girl named Charlotte, and we would select sexy fetish clothing from the catalogue and then it would be ordered in for us. Carmel and I also managed to get together for the occasional hot transbian sex session which I enjoyed a great deal.

It was different making love with another transvestite than it was with the punters. Most of the punters were rough and only concerned with getting gratified, whereas when Carmel and I had sex we took our time and were gentle with each other. We had discussed asking Charlotte to join us, after all during my last incarceration in Chelmsford, Carmel and Charlotte had forced me to participate in a threesome, so it would not be a new experience for us, except that this time I would be a willing participant.

"Hi Steve," I smiled back.

Steve came over and took me in his arms and kissed me passionately his hand roaming under my shirt, caressing my stocking tops and then squeezing my buttocks.

"You're still a stunner for an old broad," he laughed as he sat down on the bed and patted the duvet beside him.

I sat down next to him, his manly sweaty odour contrasting with my favourite Poison perfume. He stoked my knee and allowed his hand to wander up my thigh and then removed his hand from my legs and looked at me seriously.

"I have something to show you that you are going to like," he said.

"You need to realise that what I'm about to show is not personal; it's business."

I nodded, "Ok; now I'm intrigued," I answered.

Steve pulled his Blackberry from his pocket and showed me the screen while he scrolled through a picture library. The images were brutal. They were pictures of the Bill, Harold and the other two prison guards who had sexually assaulted me and then urinated on me. All of the guards had been beaten had had black eyes, bloody noses and missing teeth.

"And they all got suspended from work too," he smiled evilly.

"Fuck them!" I whispered, "They got what they deserved."

My mind drifted back to the dark and dirty room in F Block where I lay on my side in the foetal position, my legs curled up against my body, my face hidden in my hands, sobbing with humiliation covered in their semen and urine.

"Now that should teach this bitch who is running this prison!" Harold, the leader of the guards, had growled at me.

"Tell Steve that Bill said hello, and thanks for the loan of one his girls; tell him he knows where to find me if has any problems with me using his property without permission," the other guard. had said.

Steve obviously did have problems with the guards using his property and had meted out a vicious punishment. Although the images of the beaten guards were brutal, I couldn't help but allow myself to smile.

"I told you Michele; it's business not personal," Steve said.

"I can't have the guards and inmates thinking they can take anything from me without recrimination," he went on.

"But if those pictures make you happy; so be it. Maybe you could find some way to thank me appropriately," he smiled.

"But you better be quick because I've got other business to attend to."

I stood up and walked over to cell door and closed it and then pulled the curtains closed across the cell bars. I turned around and smiled seductively at Steve.

"Well honey; a girl has gotta reward the man who defends her honour."

"And if you need a quickie who am I to say no."

I reached out and holding onto the vertical cell bars I bent over. My skirt rode up exposing my stocking tops and gauzy nylon panties.

"Come and get it," I moaned seductively and wriggled my buttocks invitingly.

"Oh fuck Michele; you have become such a slut!" Steve chortled, and I heard the bed springs creak as he stood up.

Steve walked across the cell, stopping at my dressing table to pick up a tube of K-Y Jelly and then positioned himself behind me. I heard the unmistakeable sound of a zipper being opened and then the rustle of material as he dropped his pants. Steve stood close behind me stroking my buttocks and stocking tops. I reached around behind me and my fingers brushed along the firm flesh of Steve's erect penis and traced the veins along its length; when I reached the tip, I ran my fingers gently along the glans and frenulum.

I reached beneath Steve's crotch with my other hand and gently tickled his scrotum, while my other hand gently petted the top of his cock. Steve growled as I closed a hand around his shaft, and stroked the length of it while my other hand continued to massage his scrotum. After a few back and forth strokes, I fluttered my fingers against his glans and gently scraped a fingernail against his frenulum. Steve moaned, shuddering and twitching. I didn't want him to climax yet so I shortened my stroke and concentrated on his shaft, avoiding the sensitive glans on most of my strokes. Every few strokes though, I gave his glans a soft squeeze. It was driving Steve crazy and I could hear him panting.

"Oh fuck Michele; I'd like to let you do this all day but I really gotta go soon; here rub this in," Steve sighed and I felt him squeeze a dollop of cool lubricant on his shaft.

I thoroughly coated Steve's rampant cock with lubricant, and wiggled my pantied buttocks again. Over the last weeks I had been taken anally repeatedly and I had acquired the ability to relax my sphincter and anal muscles; but I knew the key to keeping pain to a minimum during anal penetration was to use plenty of lubricant.