Uptown Girls

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Story of my dressing & first TV threesome.
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Young confused and so horny it hurt that's how I felt that evening and having no internet and living at home made meeting up with horny guys and girls difficult especially as my family had no idea I actually preferred a cock to pussy a man or a transvestite to a woman anytime if I could get one.

In the daytime things had been much easier for me as I was out of work taking a year out to find a career by choice I spent a lot of my days calling gay cruising lines looking for sex and succeeding the majority of the time and having hot horny fun in the family home while my mother worked and my brother was at school but now this wasn't an option. I was sat watching the normal boring evening television programmes and listening to the same old comments especially from my mother about going out and getting some interests or joining a social club, I mean really join a social club this was 1995 not 1965 and besides the area I lived in was not for the faint hearted after dark due to its rough characters who frequented the local bar across the street from the back of my house.

Week after week I heard the same old thing and after running into a old school friend at the jobcentre whilst I was trying not to get a job we got talking and as he lived on the same estate we decided as we were both now just about to turn 19 it was time to venture into the town centre for the first time for a few beers and hopefully to find some drunken girls for some fun. My friend Paul and me had history, we had known each other for years and he knew full well I was secretly not only bisexual but also a cross dresser with a liking for hard cocks in my arse as I had cornered him before and tried to get him to fuck me but he was so obviously straight and although he knew of my secrets he never did tell anyone so it was brushed over and forgotten about.

As we arranged to go out on the Friday evening he jokingly said to me I presume its shirt and jeans not stilettos and corsets, I had to chuckle as I knew he wasn't ever going to say anything but he had to remind me about my indiscretions from our past and he had every right to. That evening at home I got the same old questions about my day and whether I had found a job as yet or not which only resulted in me fetching a beer from the fridge and going back to my favourite armchair before the usual comments started to come out about why don't you go out and socialise instead of sitting around here all the time but this time I was going out and I was going to pull a complete slut and bring her back and make her scream all night long just to get my own back.

Friday soon came round but as usual I couldn't help myself and as I never got out of bed till near lunchtime I knew the house would be empty so getting up I put on my basque panties stockings and 4 inch heels with my cheap jet black long wig and some stolen makeup from my mums room, looking back I must have looked a right state but as I tottered downstairs in my heels I took the phone off the cradle in the hall and called the cruising line again. Soon I had left my description and told everyone I had a house to myself and needed fucking and within minutes I got a reply from a decent sounding guy from 5 minutes down the road from me who told me he adored Tgirls and would love to come fuck my tight cock hungry arse.

So far the day was just going exactly to plan as I gave the guy my address and phone number telling him never to call me apart from today to which he agreed and said I will see you in 10 minutes or so then hope you hungry for my big cock in your arse, as he arrived I near had a heart attack as I peered through the net curtains I suddenly recognized the guy who had come round to meet and fuck me. I now just hoped he wouldn't recognize me under the makeup and wig and with shaking legs I stumbled to open the front door for him and as he stepped in he playfully patted my butt before grabbing my arm and pulling me toward him and then it came, the thing I had feared he had recognized me and I'm not surprised as I used to hangout with his son when we went to school but he then said no bother I wont say nothing as long as you let me fuck you.

David was Paul's dad a stocky and somewhat scary guy well known for being not someone to mess with if you didn't want trouble, standing well over 6 foot tall with a muscular torso he was the kind of guy I loved being fucked by and now I wanted to know what his cock was like too. Wasting no time I fell to my knees as he pulled open his thick leather belt and pulling open the buttons on his jeans flies to show he had no boxers or briefs on at all as he pulled out a thick manly cock and ordered me to suck him hard before he gave me a taste of his belt, all I wanted was cock and wasted not one more second before stretching my made up lips round his thick bell end and easing his thick shaft into my mouth.

He was so huge I struggled to manage his thick cock as he took the back of my head and began to face fuck me as I gagged for breath and eventually managed to get a rhythm so I could breathe as he pulled back but soon I found his huge cock entering my throat and cutting off my supply of air completely as he pounded my face, soon I could take no more as I gently pushed him back and managed to get him to take his cock from my mouth but as soon as I could breathe again David said now bend over you fucking little tart I'm going to fuck your tight little arse pussy now, normally I loved being fucked but David was huge his bell end was thick and bulbous and he was at least 9 inches long.

Thinking I was going to be clever I knelt sucking at his bell end and balls but soon he grew bored and said come on you want fucking, I know you want it and Paul told me you're a queer but I'm not going to tell no one if you let me fuck that tight fuck hole and I know you wont say nothing cause you know what will happen if you do. I knew only to well what would have happened if people found out that one I was gay and two David liked shagging trannies the second being a painful experience and a spell in hospital if I was lucky.

I now had to do it so I said to David wait a minute for me and I rushed upstairs and rustled through my bedside drawer and found my lube, normally I didn't worry too much as I had already greased up my fuck hole before he arrived but to take that monster of a cock I was going to need more a lot more. While I was in my room I decided I needed more to relax me so I quickly found a half smoked marijuana joint from the night before and quickly took 3 or 4 long drags on it making me very relaxed and a bit stoned to be honest but now I felt ready.

Tottering to the top of the stairs on my 4 inch high heels I decided I was going to fuck in my mothers room this time on her queen size double bed but before I did I took my duvet and threw it over her bedding so I didn't get lube or cum all over her sheets, calling David up he was now naked as he walked up the stairs and still rock hard as his huge 9 inches rocked between his thighs as he took the stairs and followed me into my mothers room. As I laid myself onto the bed David very quickly took my ankles and forcefully pulled me onto the end of the bed before telling me to flip over and push my fuck hole in the air for him to fill with spunk.

I was now quite relaxed but even so the feeling of someone pushing almost a tennis ball into your anus will make you squirm a little and as I did David grabbed my thighs as he forced his huge bell end into my arse making me scream as I felt him almost tearing me in half as I felt his thick long shaft being driven roughly into my now sore anus, inch by inch he forced into me until he reached his balls and then he told me in no uncertain terms now I'm going to fucking screw you hard bitch and with that he took a tight grip of my hips and began to squeeze his huge cock in and out of my bleeding and raw arsehole pounding my anus again and again harder and harder with each time he drove his huge prick into me making me actually cry out in pain as he fucked me and showed me no mercy or affection what so ever.

I knew full well I was in trouble and as he continued pounding me I almost passed out with the pain but just as I felt there was no way I could take any more I heard David grunt and felt him flooding my bleeding arsehole with hot spunk but he still continued to drive his semi hard cock into me driving his spunk deep into my arse. I felt the only way to stop him was to say I had enjoyed our fuck so as he pulled from me I sat and felt that he had destroyed my anus but he had no plan to finish there as he bent down and kissed my lips before standing and forcing his cock now dripping in blood and spunk into my mouth and ordering me to lick him clean, I attentively lapped at his spunky cock tasting a mixture of shit cum and blood from his bell end but he decided I wasn't doing a good enough job as he shoved his thick cock down my throat again gagging me and making me vomit this time to which he slapped me hard round the head knocking me back onto the bed completely fucked physically and mentally.

When I came to David had left but had stuffed a ten pound note into my cleavage with silence written on it so not only had he pretty much assaulted me but he had paid for my silence as well, getting into the shower I slowly washed off much of my body before I reached my butt but as I started to rub at my anus with my shower gel I saw trails of blood in the water and knew my time as a tgirl was over and I probably would never been able to have anal sex again. Then it sprang back into my mind that it was Friday and I was going out with Paul tonight for a beer in town, stepping from the shower I dried myself and made myself as comfortable as possible after my severe fucking I had just taken.

As I dressed and tidied up my mothers bedroom the phone rang beside her bed and I recognized the number as Paul's home phone number as like me he had no mobile but was it him or was it David? Cautiously I answered the phone and to my relief it was Paul but to my disbelief he said my old man is going to drop us in town as he is going down the club tonight, normally that would have been fine but after he had just fucked me senseless and left me in pain I knew the only reason he had agreed to drive us to town was to guarantee my silence I told Paul yeah that's cool mate saves us the bus fare and all the hassle don't it? He quickly agreed and said he's offered to run us home to but I told him we would probably be on the pull tonight.

That was originally our plan to go get drunk and find some drunken sluttish girls to fuck by the end of the night but I was now not sure if my cock or anything down there was capable of working full stop, the evening soon came and as I heard a horn outside the house I knew it was Paul and David and I chucked on my jacket and shot out the door trying to avoid my mother as a nurse she would spot anything and as I was walking like I had been horse riding all day she would ask questions. Jumping into the back of the car Paul said jokingly you went for the jeans and shirt then and jokingly I replied you want me to go change, to my surprise Paul said go on then I dare you before retracting his comment.

I was in shock as I sat in the back of the car and heard those words come from Paul and looking into the rear view mirror I could see David's eyes watching my every move but as I went to open the door David pulled away and I could tell from the look he flashed as he turned to look at me I had said enough so I sat quiet until we reached the town centre, as the car came to a stop Paul jumped out but as I opened the door David quietly said go on then slut if you don't pull I will fuck you again and if my boy gets in trouble I will be holding you responsible too and that means I will really fuck you but remember one word and, but as he went to finish I jumped out of the car and slammed the door making sure I got to the entrance to the bar and past the bouncers quick as I could and not looking back.

I was so sore from the fuck I had earlier on I struggled from bar to bar and told Paul I had a mountain biking accident in the day and he seemed to take my excuse for limping around as truth, soon though we found a bar with huge leather sofa's and cheap drinks which seemed like heaven to me as I sat and sunk pint after pint but little did either of us know we had somehow in our drunken state ventured onto the borders of the towns gay area. It didn't seem to bother Paul if he even noticed as he had pulled a drunken little blonde girl he was all over, I so far had less luck but as the night went on I decided to go get some more beers in and some stupid bottle of something for the girl Paul had with him now but as I stood at the bar a gorgeous raven haired curvy woman caught my eye but then disappeared again into the crowds.

Taking the drinks back to the table I said to Paul I'm going to have a browse round the bar mate I will be back in a bit, as I wandered off all I could hear was the music being pumped into the bar and as I walked round I saw a set of stairs to a basement bar. Thinking why the hell not I decided to investigate further and as I reached the bottom of the stairs and stumbled slightly on the flag stone floors I saw her again this time she was at the bar with another girl, a sexy leggy looking blonde now blondes have never been my thing but she looked amazing but I knew I had to chat to the raven haired beauty first and decided the best way is to get another drink so quickly downed my pint I had in my hand and made my way to the bar.

The barman obviously had seen me checking out the two girls and as I ordered a drink he lent over the bar a little and said the dark one is Vicki the blonde is Emma in case that helps but as he told me Vicki heard him and told him to disappear as I paid for my beer. I just didn't know how to react so I said hi I'm Marc and got well you know my name now don't you and with that she turned her back on me and continued her conversation with the other girl sat with her Emma I recalled her name was but as us lads do I was not going to give up that easy as I took the back of Vicki's chair turning her to face me and as she did I said I'm sorry girl but I just had to tell you I haven't seen any girl as hot as you in town ever. I guess I must have broken the ice as she said well buy me a drink and maybe we can chat a little as Emma is leaving soon anyway.

Being slightly the worse for wear from the alcohol and pain killers I had taken earlier on I still had a feeling these girls were different in fact I was pretty sure they were the kind of girls I had been looking for over the past few years, both of them were very convincing and Vicki was stunning in a tight black dress with long legs and high heels with her long black hair flowing half way down her back making her look amazing. Emma was just as stunning but was the opposite of Vicki, she was a bit more heavily set but still very attractive in stilettos with a satin skirt and a tight blouse showing off her obviously fake large cleavage which met the tips of her long blonde flowing hair. I was spoilt for choice but knew which of them I wanted to take home but as we sat together Emma began flirting with me and running her long nails up and down my thigh as Vicki sat watching as I attempted to make it clear that I fancied her and Emma would be second choice if she turned me down.

I took my chance as Emma announced she had to go to freshen up and left me sat with Vicki who didn't waste anytime in asking do you fancy Emma? I had to tell her straight I thought she was very nice but I actually fancied her to which she did not hesitate in leaning into my side and sliding her long fingernails over my groin sending shivers of excitement through me making me lose some control as I started to get hard. Vicki obviously liked what I had and as she lent into my side she told me quite clearly you can fuck us both with that if you want us, of course I did but really I could never take a Tgirl home let alone two but to my surprise Vicki said must have read my mind as she said I only live just down the road if you would be a gentleman and escort me home then maybe we can play together.

Now I knew Vicki wanted a good fucking and as Emma came back she pushed up against my other side and as she got comfortable she saw Vicki's hand caressing my now hard cock through my jeans and whispered into my ear so you fancy both of us? I had never fucked a Tgirl and now I had chance to have two together on the same night in a private flat nearby and there was no way I was going to turn them down but I soon remembered I had left Paul with the girl he had met upstairs so I made my excuses telling both the girls to give me 5 minutes and I would be back for them. Rushing back up the stairs I headed across the bar to see Paul and the girl he had met heading for the door and pushing my way through the crowds I managed to catch him, as I tapped Paul's shoulder he turned and said thought you had gone off with some slut so I filled him in on the two girls I had to play with but didn't tell him they were both trans girls he just shook my hand and said you lucky boy huh I'm off to fuck this little tart and with that he and the girl with him staggered off down the street.

I stood outside for a moment and watched Paul and the girl he had with him get into a nearby taxi cab and as I took a breath of the cold night air the alcohol really took its effect making me feel even more drunk than I was already, I decided though I needed to go back to Emma and Vicki but as I reached the top of the stairs the girls were coming upstairs to find me. As they reached the top of the stairs their height suddenly made me feel short as both were in very high heels but they did look amazing and I knew only to well I was going to get to fuck one of them at least if not both of them. I really did suddenly feel like a midget between them as I had one of each arm as we left the bar and made our way up the street, all I remembered was Vicki saying she lived close by but as we turned the corner into a dimly lit back street I didn't feel safe in the slightest but fortunately we only went on for a metre or so before Vicki pulled out her keys and unlocked a door you would hardly notice if you did not know it was there.

As I stepped in behind Vicki I couldn't help myself and patted her tight bum as we made our way up a narrow staircase to her flat which was above a adult shop selling porn DVD's and the like, reaching the top of the stairs Vicki once again unlocked another door and led me into her flat and into the warm telling me to take a seat and relax but I was so nervous I began to physically shake. Emma placed herself by my side and noticed my nerves setting in but she had a way about her and as she sat by my side slowly rubbing at my groin I started to relax and as I turned to face her she stood and dropped her skirt and pulled off her blouse to show off the most beautiful lace basque and panties with lace topped stockings and her girly cock pushing at her panties.

In what seemed like seconds Emma had my jeans down round my ankles and had pulled my briefs down to release my own cock as she slid down between my legs and began to suck me gently and slowly deep into her mouth past her beautifully made up lips making me exceptionally hard as she lapped at my bell end, soon Emma had all 8 ½ inches of my throbbing cock deep in her mouth and as she got up and climbed onto my lap facing me she slid her obviously experienced tongue into my mouth and as we kissed first gently then becoming more passionate as I felt her cock stiff against my own. I couldn't believe my luck it was obvious I was definitely going to get to fuck Emma but Vicki had been gone for what seemed like ages until I heard the sound of her stilettos crossing the room and as I looked over she was all made up still but now in tight fitting thigh high boots with at least a 5 inch heel a tiny pair of panties and a tight corset pulling her body in tightly making her look completely feminine and what most mean would dream of having any girl that looked that good.

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