Dating a Teen Crossdresser

What I Learned from Dating a Teen Crossdresser


I never wondered what it would be like to date a teen crossdresser until I actually met and started dating one. From outward appearance, you’d never know he was a crossdresser. There aren’t really signs or behaviors that give that away. It’s a very intimate and private thing that he wouldn’t share with just anyone, and that’s why I felt so lucky that I got invited into that part of his life. He trusted me, because I had an open mind, and I learned a lot about love, sex and relationships in the time I spent with him.

What I learned

It’s not like it was the situation in which he was caught crossdressing. Once we started getting sexually involved, he slowly find out what my sexual preferences were and just how adventurous i was, and if I was ready to at least see him in a different light. Once he knew he was safe, he brought out his alter ego, Vanessa, who was so exciting and so different than my boyfriend. I was almost dating two people, and the best part was I could have both in bed. I learned that he was more fun as Vanessa than as himself and that alter egos do exist and they are exciting!

Crossdressing does not have to be scary. Even though I was at first intimidated about what that could mean about his gender, crossdressing does not mean a man is gay or is not interested in women. Watching him transform into a woman in front of my eyes was not only fascinating but in a strange way erotic.

Crossdressing for teens is something very new, and starts off as experimentation and a performance. He is learning more about himself as he performs his alter ego, which does not have an impact on his sexuality. So he can be dressed as a woman, but still be a man having sex with me. It’s a very dramatic performance, and emphasizes what they like about being feminine or the female sex. The shape of one’s genitals should not determine everything they do in life, from career choices to cognitive abilities.

He realy knows how to crossdress and it’s really sexy. It’s hard to explain but when you see someone you are sexually aroused by normally and then you see him in sexy panties, it’s hard to describe but it heightens their masculinity. The foil is so dramatic your eyes don’t know how to pair the two things together and that dissonance is arousing if not totally exciting.

Crossdressers are vulnerable and are putting it all out there by living out their alter ego. Even though we are a heterosexual couple, just walking around town at night, not knowing who might recognize him and get angry and attack is scary. So, being caring and understanding and be smart about where you go out as a couple is important.

I’ve learned so much from my teen crossdresser boyfriend and he has enlightened me so much about my own gender and sexuality and how artificial ‘norms’ are. So, if you get the chance to date a crossdresser, don’t pass it up. It will change your (sex) life for the better.

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