Where it happened: Boston, Massachussets
Langauge: English
Sex: Male
Rating: 2
Category: Straight
I was 16 years old and I was with my family in Boston (the really nice part of the City). We were there because a friend of our family was getting married. So off we went. At the party I met two guys younger than me. One was a chubby Brittish teenager, the other was 12 years old and from Chicago. HIs name was Thomas. I fell in love with that boy right away. I’m a guy, you know and I’m straight, but that guy was so gorgeous. He was tall for his age, and had a slim figure with a beautifull round face that framed a set of wide, pulsating lips. That night we had this barbeque at a friends place, and my whole family was there. We were off playing around with the other kids in the shrubs at the back. Then we played this wrestling game, sort of like tag. Thomas and I wound up on the lawn in a secluded area where no one could see us. While he was on the ground I placed my hand on his shirt and slowly I put my hand up his back. He seemed not to mind, so I put my hands in his pants. Then he leaned up and kissed me on the mouth. It felt so good. We lay on th lawn holding each other and kissing for a few minutes untill we heard someone looking for us.
The next day my family and his went to the aquarium and we stayed behind. He called my room to say he had a surprise for me. He came to my room and I oppend it. I could not believe my eyes. He was dressed in a short kilt and a tight fitting white tanktop. He had on old fashioned black fishnet stockings and high heeled black shoes. He’d polished his nails a beautiful shade of red and was waering a lot of makeup. I looked at this gorgeous boy stanging infron of me. Get in I said. Someone might see you.
Don’t worry he said. They know why I stayed behind. Come on, lets go for a walk.
We walked hand in hand down the streets of Bostson. Everyone wasstaring at us. They couldn’t believe what a gorgeos girl I had. If only they all knew.
We went back to the hotel and up to my room. I waited while he stripped off his panties and shirt. The we got into bed, me in my shorts, and him in his tights and stilletoe heels. We kissed passionately, and he stroked my penis with his long, gracefull red nails. My cock was ahrd, I tell you. I vould have done push ups on it. Under
the covers we went. He lay on his chest and told me to make love to him. I was afraid I’d hurt him but he told me he did it all the time. He was right. His but was tight and wet. It felt so tight and warm around my dick that I came right away, and so did he. He had an orgasm in his butt! We rolled around giggling and playing with each others cock and balls.
I still wasn’t sure what to make of all this. Here I was, a 16 year old girl-chasing male fucking an effeminate 12 year old boy. Who cared, I was so much in love that I cared only abbout that gorgeous face between my legs, playfully tickling my penis.
He left to meet his parents who’d just got back. I came down(after washing the lipstick off my face) to find him down there, in his dress and shoes. Apparently his family didn’t seem to mind. He sat next to me on the sofa for a while. Only me and his folks knew that this lovely girl was a boy in a dress.
After his parents had gone, he and his sister said they were going upstairs to do their nails. They invited me up, so I said I’d join them later. When I arrived he was polishing his sister’s nails, and she didn’t have a shirt or bra on. When she’d finished, she went over to the suitcases and pulled out some girls clothes and threw them to me. I asked her what they were for, and she told me she’d gotten them in my size. Come on, she said, what do you think we went out for. Do you think I realy went to the aquarium. I stripped then and there and put on the panties and stockings. They had strps that hook to your panties, and th whole rig felt great. I never thought it was this much fun to dress in drag. I sat down and the put nail polish on my nails. While I waited for them to dry his sister stripped and oiled her pussy. She realy did have a great body. She was about my age, maybe 15.
We got into bed and I placed my red-nailed hands on her tits and slid my cock into her hole. This wonder full feeling came over me and I realised this guy had his cock in my ass. It felt wonderfull. We all came at the same time. Then we continued our little orgy for hours. The next day I went back to Jersey and they went back to Chicago.
This day will be in my mind forebver. I’ve had lots of beautifull girlfriends since, but Thomas will be in my memory forever. I’d like to see the next guy who’s cock he sucks, and tell him what a lucky guy he is.
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