Jean, hello! Thanks for responding to me.
How did I broach the subject? I think I found photos of the Halloween party I attended with him as youths where he dressed up in a short dress. We were both incredibly excited by it back then and hold fond memories of it. I think I asked him to dress up again casually. I have a wig in my room, and he just put it on later on on his own, pretended to be very femme. I wanted to put makeup on him and other things but was so shy. I admitted it, and he told me he would have been happy to do it. Still, I never know when to bring it up. How to interrupt "boy time". I see him pick up my bras and put them on against himself.
I think this can be a private thing...although I would be happy to take him out on special occasions when he feels comfortable.
Baby steps, indeed. I have to be a bit more bold still and ask him when I would like to dress him up.
