Crossdressing adventures Sex Stories Cool – Y2Stories.Com

Crossdressing boys experiment with each other

My cousin and I were 14 and 13 respectively when we first began to experiment with crossdressing. Terry had two older sisters, and one day when we were at his house by ourselves, we were in his sisters’ bedroom, and there were panties and bras lying all over the beds and floor. In a joking way we picked some of them up and began holding them in front of our bodies and talking in high voices like girls. The next thing I knew, he dared me to put on his sister’s bra and panties, and since the idea secretly turned me on, I did it. I stripped out of my jeans and T-shirt, and slipped into his sister’s satin panties, and put on and adjusted her bra. The feel of those panties on a 14 year old boy’s cock had me instantly hard…a fact that was not unnoticed by Terry. I then dared him to do the same, and he did. Here we both were in his sisters’ bedroom wearing their underwear, and both of us had huge hard-ons that would cut glass they were so hard. Looking at his erection in those yellow panties was really getting me hot, and I said, “You know what that makes me want to do?” Yes,” he replied. “You want to jack off!” Although we had never discussed it and certainly never done it in front of each other, we each pulled out our hard cocks and began to stroke them. Terry left the room for a moment and came back with a bottle of hand lotion, and we both got busy jerking our erections. As I stared at his hand moving back and forth on his dick, I was getting more and more turned on. I was imagining for just a moment what it would be like to be a girl and have that hard dick sliding into my wet pussy. Those thoughts put me over the edge and I began to spurt my hot cum all over the place. Seeing me shooting my wad was all it took to put Terry over the edge, and about 30 seconds later, he was spurting just as hard as I had. Well that initial introduction led to us experimenting with crossdressing whenever we had the opportunity. If my family wasn’t home we would dress up in my mother’s underwear (I loved wearing a girdle), and if his family wasn’t home we would wear his sister’s stuff. In no time at all we had progressed to stroking each other’s hard dicks, and before very long we had begun to experiment with performing oral sex on each other while dressed as girls. It wasn’t until about two years later that I took the first cock in my boi pussy, and it wasn’t with my cousin Terry. An older man took my virginity, and after the first time, I knew that I would always want to be a girl. I have continued to crossdress throughout my life, and I still find being a sissy sexually exciting. I am much bigger and heavier now than I was at 14, and I could never pass as a woman, but I still am able to find other men who enjoy crossdressing and having sex while dressed up as females.