Stag Night Tranny Gang Bang
I really still don't know why, to this day, i said i would go with Ross to the Stag night. It was probably one of my more stupid decisions in life!!
I'd met Ross a couple of times before, mostly at the S Club in Merton. Ross was about twenty three, really good looking, and loved the whole cross dressing scene but didn't dress himself and described himself as an ardent 'admirer'. He'd approached me at the bar one night and we'd got talking. Although I was much much older than him it only seemed to encourage him even more. The first night that we met I'd been wearing a really short black leather mini skirt, a silver see-thro top and really high black boots. He was all over me, telling me how gorgeously sexy i was and how he wanted me. We'd gone back to my flat, and, yes, he'd fucked me. I suppose I'm a bit easy when sex becomes involved. In a short time I had become his 'bit of tranny on the side' and he would often phone to ask if it was okay to come around and I'd invariably say yes and have to rush like crazy to clean out and lubricate my clitty, apply my make-up and slip into something sexy. Sometimes he'd turn up late, after taking his girlfriend home or out drinking with his mates, and fuck me quite roughly, but i didn't mind as i always felt good, sexy, feminine and full after he'd left.
Anyway one night he'd come around and after he'd filled me with his delicious cum we got talking over a glass of wine. It was a big thing between us that i had to be dressed en fem and always dress like a prostitute, you know black or red undies, high heels, stockings etc, and we often talked about previous sexual encounters we'd both had, tranny and female!! One night i told him that one of my fantasies was being fucked by lots of guys, sort of a gang bang. Ross eyes lit up and i could see his brain working overtime. "I think, if you're up for it, i might be able to make that particular dream come true" Apparently the following Friday night Ross was going to his best mates stag night and they had talked about getting a prostitute in for the evening. What did i think about coming along too and sharing the load? There were lots of questions! Did his friends know that he was regularly fucking a tranny and that i was much older than him and his mates? Wouldn't he be embarrassed? What if his mates wanted the prostitute and not me? No, he said, he was proud of me and that i would make most girls envious. Anyway a lot of his mates knew about me and some were quite jealous and often mentioned about what sex was like with me. To start with i was totally against it but Ross was very persuasive and after milking me off (he usually only milked me when i was good and i very rarely cummed when he fucked me as i usually finished myself off later) i said i would think about it.
Well i mulled it over in my mind and the next evening when Ross came around i agreed. There were to be certain conditions. Condoms must be worn, it was to stop when i felt I'd had enough and Ross was to stay with me all the time. It was all agreed and Ross said that he would pick me up at about 8.00 on Friday night. I was to definitely to dress as sexy and whorey as possible.
Well Friday arrived and on time Ross was at the door. I'd decided to wear my blonde hair, a black basque, my shortest red pvc mini, very sheer black stockings and my highest black heels. I must say that i felt a million dollars and the look on Ross face when i came to the door told me everything and that I'd hit the mark. " You look absolutely stunning darling. Don't worry about a thing. I'll me there for you the whole evening".
We were soon at the clubhouse which had been hired for the evening. Ross e****ted me in and we went straight to the bar. I could feel all the guys eyes following my every move. Soon though i was made to feel really at home as several guys came over and offered to by me a drink. I suppose that there were about thirty guys there, mostly in there twenties with a couple more, say ten years older. After about half an hour the prostitute arrived. She was dressed perhaps more conservatively than me but still looked the business. We were introduced and had a quick chat, mostly if i remember about the strength of the Durex's she was using, but she seemed quite keen to get down to business. Garry, who seemed to be organising the evening, ushered us over to two small rooms at the end of the bar area. Tracey, the prostitute, was show into one of the rooms and i was show into the other. Ross came in with me. "What do you think Ross? Do you think they'll want me?" " Of course they will! Couldn't you see the looks on there faces when you came in the bar! You'll be just great. Just relax and enjoy yourself. You know it's something you've always wanted." Someone, Garry i expect, had arranged of a small couch to be placed in the room. It was the sort of couch that you get in doctors surgeries and covered in green pvc. Ross locked the door, took off my thong and arranged me over the couch. I gave him the large tub of KY jelly and after warming his hand on the radiator very gently eased some into my clitty. First one finger, then two and finally three fingers. He then pulled out his rampant cock and with one swift movement entered me. It felt absolutely wonderful. He was so strong and knew just when to thrust and fill me completely. "Your ass is absolutely perfect this evening. Its really sweet! I had to have you first darling. I hope you don't mind as I think the world of you Joanna". Ross shafted me for three or four minutes and then took out his cock without spunking. " I'll save my juice for later darling. I'll try to be the last, if i can hold on that long!!"
I could hear voices and laughter outside and Ross unlocked the door. "One at a time now lads". Ross ushered in a strapping young lad, checked he was wearing a Durex and introduced him to me as Tom. Tom couldn't wait and already had his cock in his hand and was quickly into me. He was soon fucking me with a sweet rhythm. "I've never fucked a tranny before. I can see why you fancy her Ross" addressing Ross who was stood watching by the door. "You just make sure she enjoys you and give her a good shafting!" Tom wasn't going to last long. I could feel his cock throbbing deep inside me and after another couple of thrusts i felt his cock explode. He collapsed over my back and withdrew his cock. He quickly removed the Durex, pulled up his jeans, gave a gentle pat on by butty and left the room.
The next lad in was black and a real hulk of a guy. Ross, as before checked him over and introduced him as the local football teams centre forward. I was smiling at Ross as the black guy pulled out his cock. The look on Ross face suddenly changed. I quickly looked around and could understand why. He was huge. Luckily it wasn't so much the girth but the length which must have been at least 12" long. " You okay Joanna? He's a bit big!" I nodded to Ross that i was okay and i soon felt the knob end probing my clitty. I winced a bit as he pushed against me and the couch. My fingers gripped at the pvc. Ross moved over to me and held my hand momentarily before leaning back over me and gently pulling my cheeks apart as the big centre forward pushed harder into me. Soon he was in and i was truly aware of just how big and strong his cock was. Christ he was a good fuck. He certainly knew how to use it!! He must have rode me for a good eight to ten minutes before giving up the fight and letting his spunk shoot into the Durex. There must have been loads of spunk as i could quite clearly feel the rubber filling within me.
I could hear through the walls of the room the prostitute taking the rest of the guys in the other room. Some guy must have been really big as i heard her scream out once in pain as he obviously ripped into her. I was lucky i didn't have him splitting my ass and i was so glad that Ross was in the room looking after me. The next four or five guys were what i would call normal. It was very nice and i think each one enjoyed me but after the black guy I'm afraid that their cocks hardly touched the sides. I did ask Ross how the queue was and whether i was doing more business than the girl in the next room. He said that the queue for me was longer to start with but as the prostitute was bringing them of quicker some of the guys at the back were moving over to her queue.
Soon the last guy had spunked up me. Ross locked the door and came over to me. "I can't begin to tell you Joanna how proud i am of you." He pulled out his cock "I just don't know how i didn't spunk tonight. When that big black guy fucked you i really thought i was going to cum!". I felt so pleased he'd saved himself. "Give it to me now darling." Ross fucked me with feelings that I'd never experienced before from him. He was the best fuck, by far, of the night and when i felt his hot creamy white spunk fill me and start to trickle down my thighs all my fantasies and dreams had been realised that night. I was in heaven! Ross then turned me over and laid me out on the couch. He took my cock in his mouth, which he'd never done before, and commenced to give me, probably, the best blow job i had ever received. Unfortunately i didn't take me long to spunk and i started writhing over the couch in pleasure. I spunked loads and soon my milk was running down the side of Ross's mouth. There was obviously quite a lot as Ross told me later that he'd swallowed most of it and like the true boyfriend that he is told me that it tasted wonderful. Ross helped to clean me up and wiped up the spunk that had dribbled onto the floor and the couch from the other guys. I done my hair and tided up my make-up.
When we eventually came out the room all the guys applauded us. Garry stepped forward. "Thank you so much Joanna. You were fantastic. All the guys that had you were convinced that you were the better fuck. In fact one guy, Scott over there in the corner (big cheer), tried both of you and the prostitute and he certainly thought you were the better fuck". Ross looked at me and smiled knowingly. "We had to pay the prostitute £300 but although Ross had told us you didn't want paying we all clubbed together and this is for you. Buy yourself a new dress or what ever you trannies do".
Ross took me home and he fucked me again. Perhaps it wasn't so stupid after all! And i was £350 richer!!!!!