I went to a Halloween party one year, dressed like a woman, sort of. I didn't shave my moustache, as I didn't want anyone to REALLY think I was female, but otherwise, it was pretty convincing (I weighed 120-ish pounds, long hair, 34-24-34), so convincing that when I went into the boys' bathroom, guys walking in behind me got confused and embarrassed.

Anyway, there was a couples costume contest, so I teamed up with some dude who was dressed up as a macho Rambo type, and I was his slut. (I have a good sense of humor, and I'm comfortable with my masculinity, so doing this kind of thing is just funny to me, not embarrassing). In the line for the contest part was another female, and man, she was hot hot HOT. But...she didn't appear to be wearing a costume, so I asked her, what up, what's your costume? HE said, "I'm a man, I'm dressed as a woman, that's my costume." Holy crap, I couldn't believe it! I've never seen such a fine-looking man before, or since, didn't know they could be THAT convincing.

Me and the Rambo dude won the contest though, pretty much solely because of our sense of humor, not because our costumes were that great. But ever since that Halloween, when I see a particularly stunningly hot woman, I always wonder...is she REALLY a woman?