Well, I can't judge because I don't know the person in question. You should ask him. Like Joker said, cross-dressing doesn't equal being trans*, also, trans* is an umbrella term, there is so much more he could be. - The way he acts and dresses could have nothing to do with
LGBT, if I was a guy, I don't think I'd mind dressing femme, but then again, right now I'm a girl, so I wouldn't know what it's like for a bio boy.
-I agree with Joker, ask him, and don't seem too judge mental on it, it could be a touchy subject.
(With the boob thing, there are things that can give a guy a woman's shape, and vice versa. ^^)