I have a friend who is gay, he is 16, and we have been friends for 5 years now. We have always been a bit open about our sex lives with each other, I was always curious about his gay partners, and he was curious about my straight ones. I would find his type of guys attractive, and he would find my type of guys attractive as well.
He is also a crossdresser but it's in secret, but he does trust me with it and I have seen photos, I have even given him some of my clothing. He is on a lgbtq teen site and he has posted photos of himself, just not showing his face. He gets great reviews, lol
My confusion is this. We had sex together just a few weeks ago. He asked if he could which was a surprise, I never looked at him as a partner. He wanted to experiment and see what it was like, and he was honest about it and just wanted to try it. He didn't seem all that interested when we did it, and I was a bit uncomfortable with it as this is just a friendship and nothing more, but we did have fun and laugh about it.
We have been texting the last few days and he wants to do it again, but this time dressed as a girl. I haven't' really givin him an answer, been a bit quite about it, and now he has apologized and I feel like he is mad at himself for asking.
I think he wants to be trans, or maybe a secret trans. But why does we want to be having sex with a female now? And I am straight, I am not bi, but now I am having sex somebody who is gay and maybe trans, so am I now BI curious?
How should I talk with him about this? And should I give this a try? And do I have sex with him as a boy or do I have sex with him as a girl?
I am not being judgmental here, but I am lost on how to do this, but I am curious myself.