Naturally, not me, but a "friend"...
A mate of mine who's now in his fourth year claims that the first time he had sex (or at least, the first time he had sex with his current girlfriend) he was in drag. Full drag. Make-up and all. As a schoolgirl.

I'm assured he had most of it off by the time they got around to the deed, but it does beg the question of whether or not she would still have bedded him had he not been dressed as a woman. So you've got to ask yourself... would you cross-dress for sex? Even if she only wanted you for how good you look in a skirt? (Of course, it's about the only way to actually be involved in some hot lesbian action, I suppose)

EDIT: One I forgot, reminded by the Rocky Horror post below. Fancy dress party, most of us are going as random things (I was a Union soldier from the American Civil War, I think). Anyhow, one of my friends decides to go as a prostitute. But not only does he get the tights, miniskirt, wig and boob tube, but also shaves his legs and gets high heels. It was bad enough when he went around trying to wrap his legs around everybody (including the father of the girl whose party it was). It was worse when he got himself so drunk, that on the way back home, in the back seat, with me sitting next to him, his stomach decides that it wants to cleanse itself, all over the driver, all over the back seat. God knows how I managed to avoid getting any on me.

We all jump out the car, outside some houses, with the driver (dressed as a Mafioso) screaming "What the Funk! Funking hell! Aww, funking hell!" for a good 10 minutes, waking up the dogs in the houses (Sean of the Dead censoring in effect there, btw). Anyhow, we get back in the car after more puking on the pavement, except the driver refuses to wear his seatbelt, as it's covered in vomit.

So we drive back, with a horrible alarm ringing in our ears (one of those clever cars which tells you that you're being irresponsible and not wearing your belt), the prostitute still spewing slightly, the two sober people in the car gagging from te smell. The filthy ho had also managed to puke up between his legs, so that it all squished into the tights and up his skirt.

We get back to the prostitute's house, but his parents are out for the weekend. I ring my dad (who was a policeman) to find out what to do with a catatonic prostitute covered in vomit. We grab a sheet, throw it over a leather sofa, get th drunken arse onto it, cover him up, leave him a cup of water etc. The absolute worst bit of the night was seeing half his face (and the wig) caked in drying vomit, and the feeling of pity at him having to wake up to the aftermath of Aliens.
(arcro1, Fri 16 Mar 2007, 12:31, Reply)