Cross Dressing Boy

Q: So how long have you been cross dressing?
A: Oh, about all my life, really. My mom used to dress me up as a little girl when I was young and take me out. I think she had really wanted a daughter and when I came along....it was just easier to pretend. It was a shock to get to school and find out all the other boys didn't wear frilly dresses or white tights with saddle shoes and bows! LOL.

Q: It didn't bother you?
A: Oh, no! I loved it! I loved feeling pretty and also the sensation of silk and soft fabric against my skin. Even when I had to dress like a "normal" boy my age, I still wore girl's underwear under my jeans. I had to be careful in gym class though, I didn't want to let any of the others see that I was wearing little blue or pink panties when we all changed in the locker room! THAT would of been kind of hard to live with - the teasing, I mean, not the panties!

Q: Did you ever go out cross dressed at any time in high school?
A: Not until my junior year, then I decided "fuck it, this is who I am and if I'm cool with it, everyone else can like it or piss off!" I had already discovered I was bisexual, so if they called me a fag or sissy, I could give a flying fuck!

Q: And did they?
A: No, actually all my friends were very cool about it. Most of them we also bisexual or open to experimenting with boys so it was no big shocker to anyone. I even dated the head of the football team for a while and he wanted to take me to the prom, but his parents absolutely flipped out and said NO WAY. We ended up breaking up over it because I thought he should of shown a little more backbone and told them to get a life.

Q: You wore female clothing when you guys went out?
A: Yes, I used to get such a thrill bounding down the steps to jump into his car dressed in my black velvet blouse, shortest skirt and stiletto heels. We would usually have to stop somewhere and make out for a while before we GOT to the party or movie, hehe. He was a real stud, I used to cock tease him without mercy! LOL! Poor guy!

Q: Sounds exciting. Where was the riskiest place you guys ever "did it"?
A: Probably the time I blew him on the couch in his living room while his parents were upstairs watching television! We were kissing and making out and I just couldn't keep my hands off his big beautiful cock. If his old man had come down stairs and found his star quarterback son getting a hummer from a cross dressing boy in a pink mini-skirt he would of had a fucking heart attack!

Q: Shame you two broke up. Are you dating anyone now?
A: Not really. I've been seeing a couple boys I met at transvestite clubs downtown, but nothing too serious. I do have a girlfriend though. She's a real sweetie who likes to shop with me and we dress each other up and go out clubbing. She's cool with me being bi, she's into Goth so she's been with girls before too. I guess you could say we're a modern progressive bisexual cross dressing couple! LOL!