Have you/would you ever dress in drag?

[Comte Arnau]

Yes. It was a game for kids in which you had to put the clothes of one of the girls and the girls clothes from your wardrobe. I basically did it to spend the evening with one of the girls I liked. Can't even remember her face or name now, I was like nine or ten, but I remember the lipstick moment as one of the worse experiences in my life. Such repulsive substance on one's lips, eww...

[Fortis in Arduis]

Dunno if it counts but at my high school (I was 15) we had winter carnavals, and for it we competed against other 'houses' (kind of like harry potter... the students lived in seperate houses). One of the events was to put on short plays.
Because houses were seperated by gender, guys had to play female characters and vice versa.

For my house, we made fun of celebs (Celebrities was the 'theme' of the carnaval that year), and we had an american idol scene. I was Paula Abdul. So I guess that counts? It was very lulz all in all.

Any sort of male to female transpersonation requires one very special component, and that is BALLS!

[Sikeliot]

For some reason, men dressed as women convincing as female than women dressed as men look as male.

[Ghost Knight]

For some reason, men dressed as women convincing as female than women dressed as men look as male.

Look how convincing this man dressed up as a girl is:

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Not the one in blue

[Comte Arnau]

For some reason, men dressed as women convincing as female than women dressed as men look as male.

True. Just look at the guy behind. He's taken the bait.

[CelticViking]

School plays and parties for fun.

Groucho glasses