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Crossdressing adventures

545 words | 6 |4.64
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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.

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6 Comments

  • Reply Erotic Writer 2024 ID:1cv0rsdefq3j

    Great story. I too love the soft feel of women’s panties against my hard cock and how sexy my bulging cock looks in them.

  • Reply Robert ID:vuft6ud1

    Nice story. You said you loved wearing your mother’s girdle. What type girdle did your mother wear? Did your friends sister wear a girdle. I wore my mom’s girdle as well. A very nice long leg panty girdle. I’ve been wearing panty girdles ever since. In fact I’m wearing one now. I’d love to experience sex with another girdle wearing guy.

  • Reply Twocrows ID:1e0dqswgqyh6

    i often go to the bath house wearing stockings and panties. i always get to suck cock and i am often fucked so good while wearing nice lacy things

  • Reply Throater13 ID:1cmry4ofem4o

    I love dressing up as a woman too. I love wearing sexy lingerie and sucking cock and getting fucked while I am dressed in female attire

    • James McKelvy ID:1cqkkcl18y0g

      It is so sexually thrilling to imagine myself as a girl having my breasts fondled and my clitoris rubbed and sucked, and I love the way that women’s underwear feels as it rubs against my genitals.

    • cilla ID:2w2ak3e3zra

      my lingerie changed my life now i love been fucked and bred . started at 7 when i found some panties at school must have dropped out of bag , tried on instant little cock hardon