This story is for persons of eighteen years or over. All comments, good or bad are welcome and all will be answered.
Chapter One
`Why were you dressed as a woman when you were arrested?' the solicitor who had been assigned to me asked.
`I was on my way to work and stopped in the pub for a drink,' I replied.
`Work? Dressed as a woman? Why?' that same old question, why. It cropped up many times and there were very few times that I could answer the question. I gave a sigh.
`I work in a transvestite night club as a female impersonator. Does that answer your question?' I asked.
`Not really. I would have thought that you would have been dressed in, ah, trousers and the like and changed when you got to work,' he said.
I haven't any, ah, trousers and the like,' I said sarcastically. All of my wardrobe consists of women's clothes.'
`Why?'
`Oh for Christ's sake! Because I like dressing up as a woman!'
`Mr Trent, or can I call you Jack?' he asked.
`Jackie. Everybody who knows me calls me by that name. I'm even billed under the name.'
`Okay. Jackie. I've been assigned by the court to defend you and so I must know something of your background and exactly what happened in that pub. The charge is affray, assault, damage to property, assaulting two police officers and resisting arrest as well as abusive language. How will you plead?'
`Not guilty of course! I was only defending myself. She started it!' I said.
`But you put her into hospital as well as one of the police officers,' he said.
Serves them both right. Her for starting it and him for grabbing me like he did, look!' I pulled up the torn sleeve of my dress and showed him the purple bruise marks on my upper arm, the imprints of fingers clearly to be seen. He shouldn't have gripped me so hard. I didn't know it was a copper when I swung round and hit him. I was only defending myself.'
`The other woman suffered a broken nose and cuts to her face from the glass you smashed into her face.' I gave a snort at this.
`Other woman my arse! That was Maurice Goodchild, also known as Maureen. A blowsy queen that shouldn't be out on the streets at her age.'
`Maurice Goodchild?' he asked looking quite surprised at this news.
`Yes. I didn't know it was her tom I was chatting up while she was out in the cottages,' I said.
`Cottages?' he queried.
Toilets to you,' I replied. He was sitting by himself and I thought he was good looking enough to have a chat with and so I sat down to talk. Next minute I was hit on the shoulder by Maureen who started screaming at me and she went and tore my sleeve so I hit her with my beer glass. I didn't know I had it in my hand, I thought I was using my fist. I know the glass broke in my hand and I could see blood coming from her nose but I wasn't going to give her a chance of hitting me back so I jumped on her.'
`Smashing two tables and a chair in the process,' my solicitor said.
`It was as much her fault as mine as well as her tom for he jumped on my back. It was him that caused us to crash into the other tables.'
`What's Tom's last name, we may have to call him as a witness?' he asked.
Tom?' I snorted. That's not his name! That's the name given to a man that picks up the likes of her. What his real name is I've no idea, I've never seen the man before.'
Okay,' he said. So you started to chat him up, why?'
`Well if he was agreeable, we would have gone out to the cottages,' I said.
`Why?'
`What planet are you on? To have him fuck me of course.'
`Oh! You mean you were actually soliciting then?'
`Am I being charge with that too?' I asked.
`No.'
`Then yes, I was. Isn't that what you do being a solicitor? Getting clients so that you can fuck them?' I asked with a smile.
Not quite,' he said, having to laugh at the suggestion which made him almost human. That has already happened to them and we try to help them as best we can, like you.'
`I never got round to being fucked before the fight started,' I said.
`But you're fucked now unless I can get you off.'
As he said, he didn't get me off and so I was fucked. I was found guilty and sentenced to three months prison. I don't suppose my turning up in court wearing a dress helped my case, but I was going to either win or go down with my colours nailed to the mast. My solicitor did the best he could but it was my kicking the second copper in the balls as I was being held that turned it against me.
I got a lot of sneers from the guards as I was dumped in Wandsworth Prison later that day. I won't go into all the names I was called by the guards in there as I had to strip off my clothes for a shower before being given my prison clothes to wear. I was escorted into C Block and up on the second tier, a cell door was opened and I was told to go in.
`Well bless me if it isn't Jackie Trent,' the lag on the upper bunk said as I went inside and heard the cell door clang behind me.
Hallo Bert,' I said. Never thought that I'd meet you in here?' Bert Wilson was a pickpocket, though I think he was beginning to suffer from arthritis for he seemed to get caught more often now he was getting older. I knew him from the outside and he'd been into my club a few times.
`Why are you here?' he asked sitting up and letting his legs dangle down.
You know Maureen Goodchild?' I asked and he nodded. Well I gave her a new nose job and ruined a copper's love life, putting them both in hospital. They gave me three months.'
`Well this is going to upset your love life too then,' he chuckled.
`Not really for this is a men's prison and there must be quite a few who are quite randy. As I'm in here with you Bert, would you like to be the first?'
`I've got no money Jackie,' he said a little disconcertedly.
`As we're going to be cell mates, it's free for you,' I said and saw his face light up in a smile which broadened even more as I stroked the front of his trousers and felt that he'd suddenly risen up.
Oh Jackie,' he said as he slid off the top bunk and landed down next to me. Can I kiss you too?'
Of course,' I said with a laugh as I undid my trouser buttons. He grabbed me with his arms and gave me a good smacking kiss on the lips as I dropped my trousers and turned round and leaned down onto the lower bunk. Like me, he didn't give a hoot as to what the other cells on the other side of the block could see as I heard his trousers come down and felt the tip of his of erection press against my rear. Push in and fuck me Bert. It's been two weeks since my last cock.'
I gave out a big sigh as I felt him push and enter my backside. It was lovely to have a cock back inside me again and revelled in his movements as he shafted me, almost drooling as he held my hips firm as he fucked me. He'd been without anything like this for a long time for he was soon holding me tight as he came, bucking his hips and I felt his seed spatter my insides and welcomed the soothing massage he was giving me.
It was over too soon and gave out a mew as he pulled out and staggered to the metal basin to wash his cock before putting it away. I'd pulled my trousers up and got onto the lower bunk and sighed at just having had a lovely fuck. When he'd finished, he turned and got onto the bunk with me and gave me a kiss.
`Thanks Jackie, you don't know how much I needed that,' he said as he kissed me again.
Any time, Bert, anytime. I'm not going anywhere for the next three months,' I said, reliving the pleasure of having a hard penis rouse my insides again. Who's the Baron?' I asked, that being the term for the prisoner who was the top dog of the place.
`Eddie Forbes,' he replied. He didn't have to enlarge on that for I knew who it was. He was a bank robber and was serving twelve years of which he'd already served four. I knew him by sight though not to talk to and I looked out for him when we went down to the mess hall for dinner. I queued up with the others until our supper was dumped on my metal tray and then looked for where this Eddie Forbes was sitting. I saw his table and walked over with my tray and though the table was full, I stopped by him.
`Can I sit down here?' I asked. There were some scowls from the others seated but not from Eddie. He looked me up and down and it least it was with frankness and not as if he was looking at a heap of shit.
Certainly Jackie,' he said. Shift!' he demanded of the men that were sitting opposite him and so they started to shuffle their backsides along the bench and the guy at the end had to get up and with a scowl at me, moved onto another table as room was made for me opposite Eddie.
`So what does our catamite Jackie want of me?' he queried as I sat opposite him and began to eat from my tray. I smiled at him.
Your cock and protection in either order,' I said, looking him in the eye. I'm willing to look after you if you'll look after me. There's too many pederasts in this place for my liking. I'd rather have you than any number of the others.'
`As I understand you've already had Bert Wilson,' he said with a smile.
`He's my cell mate. He was hospitable in his welcome to his humble abode and I returned his hospitality by welcoming into mine.' He laughed at this as he continued his meal and looked at me with a speculative eye.
`So you are offering yourself to me in return for protection?'
Unreservedly except for letting Bert ease himself now and again,' I said with a smile. Other than him, I will be yours to command, plus that I sit here opposite you for all my meals during my three months here.' I wondered if I'd gone too far for he didn't answer me for several minutes as he continued eating his meal. In fact he didn't say anything till he'd finished eating and pushed his empty tray along to the man sitting next to him.
`Be in my cell in half an hour,' he said as he got up. Leaving his tray for this other man to take away for him. Got you, I said to myself and so I knew that I was now safe from rape whilst inside for it was better to choose the man who was going to fuck you than have half a dozen or more suddenly attack you and force themselves inside and possibly cause some internal problems.
I finished my meal and after putting my empty tray with the others, left the dining hall and went up to my cell and stripped off and washed myself at the basin as Bert came in.
`So you're going with Eddie Forbes then,' he said in a flat voice to me.
Yes Bert,' I said as I dried myself, but I made it quite clear that though I'm going under his protection, you will still be able to have me when we're alone in this cell.' That made his face light up having thought that with me now being Eddie's piece of meat, he wouldn't get a sniff or taste. See you before lights out,' I said as I left the cell and went along to that of Eddies. One of his other minions was inside with him when I walked in.
Fuck off,' he said to his cell mate, and just keep watch.' The other man got up without a word and left the two of us alone. I moved into Eddie and ran my hand inside his shirt.
How do you want me?' I asked. Mouth or rear?'
`Let's see how good you are in giving head,' he said as he got onto the lower bunk and laid himself out. I went down onto my knees and undid his flies and pulled out his throbbing erection and held it upright in my hand. It was good to hold such a weapon again and look at, already starting to drool for I had been told that I was quite good in giving head. His was no bigger than most men and it was great to hold the hardness of a throbbing cock and feel his pulse rate through the fine skin that sheathed this muscle.
I gave it a few rubs first, feeling the strength of it before opening my mouth and lowering my head to take him inside. He was hot and my own cock rose up as I ran my tongue round the half exposed head from its foreskin and gave out a big sigh through my nose as I began to suck on him as I worked his shaft with my hand. I was also able to get my erection out of my own hated trousers as I worked on his and jerked myself off as I strove to give him complete satisfaction in this way.
He gave out a grunt and began to buck his hips slightly as he began to come and come he did in quite a quantity that I took into my mouth as I came myself, shooting my load under the bunk as my mouth filled with his sperm. I held it there till he'd finished before swallowing the lot and carried on moving my hand as I squeezed the last drops out of the eye that I licked off.
That was very good Jackie,' he said as I got his deflating prick back into his trousers before putting mine away. Tomorrow you'll work down in the laundry with me,' he said and then he got up from the bunk and gave me a kiss on the cheek. `Down there we'll have the other end,' he said with a smile and pushed me out of his cell and beckoned in the other man. I went off back to my own and Bert wanted to know all the details as our cell door closed along with the others. I not only told him what I did, but showed him too and he was over the moon with this.
Next day after breakfast, I was taken to the laundry by a guard and handed over to the warder in charge there. He just told me to see Eddie as to what my duties would be which turned out to be quite light. It wasn't long before he got me into a corner and told me to drop my trousers. This I did and then leaned over a basket trolley of washing and had the thrill of being fucked up the arse again. I needed it and would have taken more if he'd offered me to his mates, but he didn't.
So for those three months he either fucked me or I sucked on his cock though not always in the same order but at least twice a day he had me. Bert didn't go without either. There was the odd man I was given to by Eddie as part of a favour to which I had no objections for any cock that was up and rampant was acceptable to me to please me as well as the giver.
I was nearly in tears on my last day there as I was fucked by Eddie who, because of who he was, had kept other predators away from me. He'd stroked my bare bum and told me that he was going to miss having me as he stuck his prick in between the cheeks and gave me a good rogering. This was straight after breakfast for half an hour later I was taken through to where I was given back my own clothes, the warder handing them to me with a look of distaste on his face at having to handle these women's things.
How nice it was to finally get rid of those hateful trousers and pull on a pair of stockings once again. The wearing of these soft clothes was what I had missed most these past three months, well, except for my gin and tonics too. I was left in a small room on my own to get dressed and being as perverse as I normally am, roused myself up to an erection and jerked myself off into my panties and left them inside the trousers for one of the warders to find later. Of the small amount of money I had been given for working in the laundry, I gave to Bert except for enough for me to get a taxi to the bank. Fortunately, my landlord where I lived was good and knew that I would pay my back rent when released.
This I did and I also got a right bollocking from the club manager when I turned up to see if I still had a job.
`Why the hell did you have to pick that night to have a fight and get arrested. A full club and our supposed star doesn't show up. Why?' he screamed at me. There was that word being thrown at me again. Why! Why was I always being asked this? See, they've even got me using that bloody word. How the hell can you really explain what you'll ever do in every situation that you encounter? You can't. Anyway, even though I wanted to scream this back to him, I didn't for I still needed the work and so I mumbled out an apology and bit my tongue in case I said something that I would later regret.
It seemed to pay off for when he ran out of breath and words to describe my behaviour, he said that I could start that evening but I had lost top billing and I would have to do better than his new star to take back the top spot. Mind you, it wasn't the money that he paid that kept us all there, it was what we made out in the cottages which was more than double than what he paid us. I suppose that's why he never said anything about us using his club as an unofficial male brothel for we were if the truth be really known and acknowledged, whores, for we sold our mouths and ring pieces to who ever had the money to fuck us in either orifice.
Mind you, I didn't do myself any favours that evening when I went into the dressing room.
Jackie!' was screamed out as I entered the cramped dressing room by Sally, we always used our female names both in and out of the club. She was a few months younger than me and not as good looking as myself or sung better. She was up from her seat, second from the end and hurled herself at me, smearing her make-up as she kissed me. We thought you'd gone forever!' she cried as she embraced me. You'll have to tell us all about it. Shift you lot,' she cried out to the others. Move down and let Jackie have her place.' There were disgruntled noises from the other four as Sally began pushing them back towards the entrance. The end seat was always for the newcomer because you got knocked about every time one of the others went out or came into our confined space.
Then I noticed that the girl that was moving to this end seat, was wearing one of my dresses.
`That's my dress you're wearing,' I cried out.
`So what? You weren't here,' was the reply which got my rag and so I decked her, blotting my copy book. As she shook her head on the floor, I got my dress up over her body and heaved her up as I pulled it off of her.
`Nobody wears my clothes, ever,' I shouted at her and got some small satisfaction at seeing a trace of blood at her lip that she licked at as she looked up at me. There was fright in her eyes and I knew that they'd heard of Maureen and of how she finished up in hospital. The other girls had turned round to concentrate on the own reflections in the fly speckled mirror than look me in the eye at this sudden attack.
Sally had moved her make-up down to the third seat for me to have the second seat and I looked at the one that had taken my first seat and saw that she had a smug grin on her face.
You can take that supercilious smile off your face,' I said to her, before I knock it off. Enjoy that seat while you can for you won't be in it much longer now that I'm back.' The grin disappeared and to give her credit, kept her mouth shut and turned back to the mirror to continue to see to her make-up.
`Any chance of a drink Sally? I've wound myself up too much,' I asked of her.
`Sure. Jean! Go and get a large gin and tonic for Jackie please,' she asked and the one that was second from the end got and went out and returned a couple of minutes later with a nice big glass full.
`Thank you Jean,' I said to the young thing that passed me the glass. Christ! I must be getting old when I'm thinking of these others as young things and I was only twenty years old myself. It seemed as though I'd been doing this for donkey's years and I stifled the thoughts of how I came to be where I was though it was brought home to me a few days later which we will come to in a moment.
With us six girls we had to go out on stage and sing three songs each, the girl nearest the door started the evening off, the one that I'd clocked. This gave me time to see that my face was as perfect as I could make it before I followed Sally's turn on the stage.
I got a lovely welcome from the regulars with shouts of, Nice to see you back Jackie,' to which I shouted in return, that he saw my back more often than my front, which brought out a laugh with the others knowing that he fucked me quite often out in the cottages. We're rooting for you,' to which I replied that he always had a root for all of the girls that brought out more laughter. Give us your best!' that only had one answer, That's for you to pay for out the back,' I replied to more laughter and then went on and sang my three songs to finish with a tumultuous applause.
`Top that,' I said to the current queen bee as we passed on the stage and had the satisfaction that she didn't.
As we normally did when coming off stage, circulated round the club to encourage the punters to buy us drinks at the exorbitant prices that were charged. As well as this, we were also selling ourselves and within a couple of minutes I was out in the cottages with one of them who almost slavered at the mouth when I said yes to his query. We didn't wear panties and the back of my dress was soon lifted as I bent over and had him push his throbbing cock up inside to fuck me. It cost him thirty quid to do that and I loved both the money and having a large prick again servicing me. I had another three fuck me before I had to return to the dressing room to check my make-up having just earned what I was paid for the whole week of singing.
After my next bout on the stage, I had two face fucks, having the man's cock in my mouth and taking his semen in and swallowing it and then telling him how lovely he tasted, though this only cost them fifteen quid for this service. The other two men I had fucked me nicely thank you.
I kept getting told that it was nice for them to have me back singing again which bolstered my ego no end and I had another four men to round of the night which was a financial success for me compared to giving it away for free in prison.
Such was the welcome I had been getting that night and for the rest of the week, our queen bee left and I was then back into the top seat and got top billing for the word went round that I was back and the place was full, as I was with cock every night both front and rear and loved every minute of it.
I had a shock during the next week for I had a social worker and her colleague call at the place I lived. I hadn't quite listened to what the judge had said when he'd sentenced me to three months inside, that I was to receive counselling because of my penchant to wearing female attire at all times whilst being of the male species.