Okay, now that I think about it, it's really two questions. He's a guy friend that I've known since fifth grade. I'm not sure that we're what you call "close." We hang out. We drink. We play video games and make each other laugh. We act like idiots. We talk about relationships and stuff, too. But I still don't consider this close. Unless something major happened, I don't think I could ever cry in front of him or vice versa.
Okay, there's a bit of sketchy detail. Now, onto the questions. Since I count him as one of my best friends, I do have the desire to share this part of my life (the crossdressing) with him. However, my experience (from highschool--several years ago--mind you) is that he's not very good with secrets. There's a chance he already knows, as he's friends with my ex-girlfriend who knew. I want to tell him, but every time I get close, I back out for reasons I don't fully understand.
The other question is a bit more complicated. I'm worried that I won't be able to put words to it very well, and that I might inadvertently offend somebody. Not to stereotype, but he has the characteristics of someone who might be gay or transvestite. I have good reason to believe he's not gay, but he's skinny, and his manner of moving and gesturing is very effeminate. I guess what I'm beating around the bush saying is that he looks and dresses like someone who might be gay or somehow femme (and I'm aware that homosexuality and femininity are far removed from one another psychologically, but not necessarily in appearance).
This is not my entire reason for suspecting. However, I want to respect his privacy, and so I will not detail my other reason. And without it, I guess it's impossible to make a detailed analysis. Anyway...I kind of went off on a rant. I just want to tell him, but I'm scared that he might be the one wrong person to tell. He could also be a right person to tell, especially if he is like me, or something. Anyone have any advice?