Shool teen crossdresser first time sex

I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my new bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I was besides myself I could not believe how hot that was and how fucking much I wanted to suck a big cock and feel it explode all over my face, in my mouth.

I’d had been stealing my s****rs clothes for years and jacking off in my room dreaming of the day a man would finally fuck my face and give me his sweet, sweet cum. giving myself self facials and needing to jack off five times a day, fuck I was horny.

Finally on a quiet morning in spring I found myself all alone in the house, my friend James had come over, he would do it a lot and we would listen to records, look at girly magazines and from time to time jack off together. we had never touched each other but god how I wanted it, he was smooth, had a nice sort of fem body and a hard 7” that I would fantasize about when we looked at porn together.

That day we were looking at some mags and I said “don’t you think that girls lingerie is sexy” all he said was yes referring to the slutty blonde in white garters, stocking and push up bra.

Next I asked “have you ever wore girls panties?” he paused for a second gave me a confused look and said “fuck no” couple of minutes went by and I asked “have you ever thought about it?” he looked down at the magazine and in a barely audible whimper said “well....uhm...yeah” I smiled and gathering up some courage I said. “you know I do it all the time” he quickly looked up and said with wide eyed amazement “really?, you do? do you like it” I smiled “I love it” and we both fell silent a bit awkward moment but you could feel the tension rising up.