In grade 10, my history class was given a list of topics from which we could pick for our main project for the semester. One of them was "The Role of Women in Canadian History". My friend Jamie and I, for some now inexplicable reason, got all excited at the prospect of dressing up like women for our presentation. So, we borrowed somehwat old-style dresses from friends of ours, and we had another friend go out on the lunch hour of the day of our presentation to pick up some pantyhose for us to wear.
She got white ones. Probably because she wanted to hang us out to dry. Our leg hairs were clearly visible through them, and I don't know if that's more our fault or hers. :p
The other time that immediately comes to mind was three or four years ago. It was Hallowe'en. My girlfriend and I were invited to one of those pimp'n'ho parties that were the style then. Her feminist sensibilities were troubled, but we wanted to go to see some of the people, so we decided that she'd be the pimp, and I'd be the ho. I wore a nylon dress through which my nipples would've been clearly visible, if not for the bra that I decided to put on for the occasion.
I also wore makeup that night.
The host opened the door, looked at us, and just said, "Aw, Jesus Christ! Get in here out from the steet..."
It was bloody cold walking over to his place that night.