Confessions of a tgirl slut 7
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A few years ago I met up with a guy through a personals site. We had chatted off and on for months but he wasn't exactly local - about forty miles away - and for some reason or another we just hadn't made it happen. We got it together finally because his work was taking him past my place and so the date was made. And we really clicked. For a start he showed up on a massive motorcycle in full leathers and boots whereas I was in full pink sissy costume. I love a really heightened sense of difference between me and the man so here was what constitutes for me a sense of tough, dominant macho man and mincing sissy - a real polarisation. But being a first meeting it was exploratory. We were sizing one another up in a way.
I was relaxed, though, and so although the session was mostly vanilla - a long, deep-throating blow job almost to orgasm, immediately leading into a rough fuck with a fair amount of verbal abuse thrown in for good measure - it was as exciting as vanilla can be. So all in all it was an excellent start.
Yet, although we managed to stay in touch, we weren't able to meet again. He was posted abroad and two years passed. Then, out of the blue, I got a phone call from him to announce that he was back and that forty miles wasn't going to stand between us. As far as he was concerned, that first meeting was just a taster.
I never allow myself to be fucked on a first date but there was real chemistry between us and I had to go with the flow,' I said on the phone. And you were big and I was tight. I'll bet I'm even tighter now. But being fucked is special. I loved it and remember our session well.'
He laughed and replied, `Mmmmmmm but you still relaxed and took it all and before that you deep throated me like a true professional whore. It was a wonderful day and I still smile and wink up at your house as I pass. Next time make sure you are in your sissy dress again, with your frilliest sissy undies as I call and catch you all dressed up and make you my little cum slut and I'm also planning to tie you up and have my wicked way with you.'
`We can move on to a more kinky stage on your next visit. Bondage is great as is spanking, maid service, roleplay as punter and whore...you name it.'
`You won't believe how many fantasies I have,' he replied.
`Well, I love that kind of fantasy sex. Way back I did a lot of anonymous silent sex in places like Hampstead Heath and had amazing horny times. But the idea of doing it again with you is hot. Have you ever been dogging? I haven't done it but want to. They say there's a dogging place about half a mile from me.'
`Mmmmmm I will be your pimp and sell you to the other doggers for a fiver a time for a blow job and a tenner for a fuck so that you can realise what a cheap slut you are. So we'll go dogging with me as your pimp. You can keep the sissy stuff for home but when you are out and about with me I want you to look like what you will be that night - a cheap whore.''
The stuff of fantasy I thought to myself but he was as good as his word. The next time I heard from him was to tell me that he was showing up on Saturday evening and that we were going dogging. He told me to dress at my sluttiest and go over the top on my makeup as well.
Saturday arrived. I wasn't sure that it was not just all a fantasy and that if he showed, perhaps we would role play at home. But somehow, with him I wasn't so sure. Really, when I thought about it, I realised that he had, in fact, done all so far that he had said he would. Perhaps we were going dogging after all.
Anyway, I followed his instructions and dressed like a whore. Seamed black stockings held up by a 14 strap belt - in my excitement I managed to ladder one, pulling it on but I felt a cheap slut wouldn't care; strong, black lace corset, laced as tight as I could get it - though I knew he'd insist on making it even tighter; black bra holding up and pushing out the biggest set of tits I owned - 44 DD; black leather mini skirt, so short it did not hide the straps of the suspender belt; red satin blouse, stretched insanely tight against my huge bosom; black six inch heels.
Then to the makeup and I didn't hold back - first loads of foundation, laid on thick, then more blusher than I'd ever apply normally. The eyes - I laid on a lot of pink on the lids, above that, the sockets were startling white, beneath the eyes was a thick band of purple, and then a patch of glittery blue at the corners of the eye. To look more like a whore, I didn't do much in the way of blending - I wanted to give the impression of a whore going through the motions of beautifying herself in a casual and short cut manner. Thick eyeliner, loads of cheap mascara and then on to the lips. Coat after coat of brilliant gloss red, badly applied. Nails - also gloss red. The wig - I chose my biggest hair and back brushed it. A couple of large gold hoops for the ears, a number of cheap and vulgar bangles for the wrists and I was done.
I stood in front of the full length mirror and the image that confronted me made me gasp. I had thought that there was a chance that I might look a little classy - black is always a winner for class - but the makeup in itself dispelled any thought of that, plus the mini skirt left so little to the imagination. I wondered if I should wear panties or not but felt that they'd just be a hindrance. There was a danger of my male bits being seen and so I dithered about that for a moment but decided I'd leave it to my biker to make a decision. I definitely looked like a whore.
He showed up on his motorbike in good time. He looked critically at me, made me parade up and down a bit. And liked what he saw. Though he did say, `Take that blouse off for a moment. The corset needs tightening.' With the help of a series of deep breaths, it was tightened more than I'd ever before experienced, giving me the most feminine outline I'd ever sported.
Just one finishing touch,' he said as he handed over a package. I opened it, put my hand in and pulled out a stainless steel chastity belt. You are a working girl tonight so this is not about your pleasure. Put it on and hand me the key.' Easier said than done as I was turned on by this level of being controlled and it took quite a bit of wrestling with my bits before they were locked away. `And no panties. I don't care if the chastity cage holding your clit is seen or not; I just got to let guys have easy access to your pussy.'
So the dogging session was a reality. We left the house and walked to his motorbike. It was a fine September evening, not exactly warm but not cold either. He handed me a leather biker's jacket which if anything, increased the whore look and I got onto the pillion seat. And off we went, my heart wildly racing at what might happen. I knew of the place but had never had the courage to go alone and especially not alone as a transvestite. I had no idea if the place was for heteros only, if gays went there, or what kind of action people got up to. But with my biker, I felt protected.
We were there in under five minutes. There was a carpark, with about ten cars, but no sign of any action. All was still and dark. I jumped off and he parked his bike to one side. Now I felt, shy, scared, worried about some hetero macho type getting turned off by discovering that the cheap whore was a transvestite.
`OK slut. Take the jacket off and walk to the other side of the car park. Then strike a few poses and walk back to me. And remember, I don't want any lady like walking - you walk like a whore.' He slapped my bum and off I went. I really swayed the hips as I moved and stuck a hand on my left hip. I was a walking cliche.
`Look into every car and smile,' he shouted after me.
All was in darkness. I wondered if anyone could possibly see me. Maybe they'd think my silhouette was that of a genetic woman. As I passed the first car, I could see a solitary figure behind the wheel - but I threw a dazzling smile as directed and passed on... Two cars, three cars... I felt more confident and I took to lingering just a little as I smiled and now suddenly cars began switching on their lights and now I felt I was walking across a spotlight lit stage. There was no hiding now.
I got to the far end of the car park and struck a few poses. I hoped they were slutty, sexual poses. Then I started the walk back. Car doors opened and a few guys got out and stood watching me go by. And then I was back with my biker.
Good slut,' he said. You've created a bit of interest here.'
`Are there no women here? It seems to be all blokes,' I said.
`Don't worry about that. It just increases your chances of action. Looks like you are the only attraction, at the moment.'
One of the guys was making his way towards us. Middle aged, running to fat. My heart sank.
`What's up,' he said as he reached us.
`Fancy a taste of this whore?' said the biker.
`She's a whore?'
`Yeah, doesn't she look like one?'
`Yeah, she does. What's the rate?'
`A fiver for a blow job, a tenner for a fuck.'
`Fucking hell, that's cheap! Are you serious?'
`'My business plan - make it cheap and you get more custom.'
The punter stuck his hand in his pocket and produced his wallet.
`I'll start with a blow job and see how it goes. Here's your money. Right, come along, darling.'
Not a word about me being a guy! Did he really think he was getting a real prostitute? The idea turned me on even more.
Putting an arm around my waist he led me to his car. He dropped his trousers, and pants, opened the passenger door and sat sideways with his feet outside on the ground. I knew what was expected of me and knelt on the tarmac. I was in no way attracted to this guy, would never have gone on a date with him but I was totally turned on and could feel my sissy clit, straining to get erect in its steel cage. My mind was a whirl of feelings and emotions and I was almost shaking with excitement. I really got to work on his cock, teasing and licking and sucking, the whole repertoire of cock sucking techniques coming into play. Lapping at the cock head and then plunging all the way down. Gently working on his balls, then finding the line from balls to arse. He was in the wrong position for being rimmed but I was so worked up by now that I would have gone for that too, even though his arse was fat and flabby. At times I could feel him close to cumming but when this happened he would push me away and I'd get my breath back before starting in again. But the inevitable happened and suddenly he froze, then shook, gasping and spluttering as he climaxed and his cum began to pump into my mouth and down my throat.
`Ah, God, no! I didn't want to shoot. I wanted to fuck you, slut. But you did a great job. Yeah, you're worth a fiver.''
I rose to my feet and turned and was amazed to see a group of about five men standing in a circle. Some had their cocks out and were wanking. I looked about to see my biker but before I could locate him a tall, youngish guy took me by the hand and said, I'm next. I've already paid. I'm gonna fuck you.' He led me to his car and on the way I was thinking to myself, But this one will soon find out I'm a guy. He'll be looking for a cunt.'
As if reading my mind he said, `I know you're a tranny but a hole's a hole and the wife would never give me anal. I want to see if tranny cunt is as tight as they say it is. Right, on your knees in the back seat. OK now move your slut cunt closer to the door. That's it, slut.' I felt him lube me up. Quite roughly. He was in a hurry to get started and wasn't too worried about preliminaries. I felt his cock finding my hole. How big was he? How thick was he? These thoughts shot through my mind as, having located the spot, he wasted no time in thrusting into my sissy cunt in one sudden, savage movement. I bit my lip to keep from crying out.
`Oh, fuck yeah, you've a tight hole. Clamp your cunt tighter, whore. That's it. Yeah, you do what you're told. I like that. I fucking love that. Don't put your rates up cos I want to fuck your cunt regular like.'
He was a stud, no doubt about that. He knew what he was doing. I began to relax after the initial shock and soon I was thrusting back to meet his deep penetration. He was so excited I thought he'd shoot in an instant but he wanted his money's worth and every so often he'd draw back and rest before going back to vigorous thrusting. I knew we had an audience. There were low moans from the assembled guys. I played up to them even though I couldn't see them by moaning myself in an excess of sexual pleasure. Even in my trance-like state, I could hear their words of encouragement. Take it deep, whore.' Fucking slut' and even `Fucking tranny slut'.
Well to cut it all short, I gave six blowjobs and was fucked three times that evening. In the space of two hours. And although it was exciting, by the end of it I was really suffering. Time to go home. I never did find out if any one else showed up or whether I remained the sole attraction. I must remember to ask the biker when I next see him. But I was too exhausted to say anything. I was also a fool to think the evening was over. It was now two in the morning and there I was with a sore mouth, a sore pussy and a belly full of cum, thinking only of sleep but no sooner were we in the house than he led me to the kitchen and bent me over the kitchen table, took his leather belt from his trousers and said, `Whore, you only made sixty quid this evening so you're getting a beating to remind you to work harder.' And he laid into my bum cheeks, not too hard but enough to make me cry out at the last strokes.
When he had finished striping my buttocks with his belt, he told me to lie there and I did, sobbing a little at the burning in my bum from the rough fucking and on my bum from the strokes of the belt, but watching him to see what he next had in store for me. I saw him fix a dildo to a hard wooden chair.
'Right, come here,' he said. I got up and came over to him as he lubed up the dildo. `Now sit down.' I was too tired to resist and in any case, the whole scenario had become almost surreal. I was zombie like in my obedience.
My pussy was still gaping from all the fucking so the rubber cock slid into me easily though I did cry out as my stinging buttocks rested on the chair. I weakly begged him to stop but he ignored my pleas as he tied my wrists behind the back of the chair and my ankles to the legs. He stripped off in front of me, his big swollen cock stiffening as he moved in on me as he wanked, rubbing it around my face and slapping me with it.
He reached inside my bra, pushed the breast forms aside and pinched my nipples, squeezing hard, smiling as my mouth opened in a silent scream. He eased his cock into my open mouth, straight down my throat making me gag as he throat fucked me. Luckily for me, he didn't last long and he shot his load deep in my throat, denying me even the taste of my Master's cum. Then he knelt in front of me, produced the key and unlocked the chastity cage and pulled out my limp clitty. I hated him doing this to me but, despite all the abuse and discomfort I'd been through, my little clitty stiffened as my Master stroked it and wanked it till it spurted its pathetic little gurly load into his palm which he then brought up to my mouth for me to lick it clean and swallow my own cum.
Then he made me open my mouth and he pushed a ball gag into my mouth and strapped it around my head. He produced his phone and snapped me a few times. `I've got a photo record of the whole night's events so this is just the finish.' (These final photos show me at my least pretty - mascara running down, lipstick smudged, tights in a terrible state, hair looking like I had been dragged through a hedge backwards - yet they are my favourite photos.)
He kissed me on the forehead and said, `Good night, my little sissy cum slut. Sleep, if you can'.
And he went to bed, leaving me there till the morning.