Twice I've dressed in women's clothing.
One year, for our squadron Christmas party, it was just a few years after the Berlin Wall came down and we were working more closely with Russia, we on the party planning committee "leaked" that we had gotten a Russian ballet troupe to come, as special guests, to put on a holiday show.
At the time, our air base was in the news, because we were part of a program flying grain over to Russia, to help them out, so we tied it to that, that they were saying thanks for that.
Needless to say, there were no Russians coming. During the big night, the curtain opened to reveal...seven of us guys, dressed in tutus and wearing gaudy makeup, and we all had balloons under our body suits for our chests.
We did a short program of the absolute worst ballet you've ever seen, culminating in some of us chest-bumping, resulting in burst balloons. It was hilarious.
No one, not even my wife, knew that I was in on it and one of the dancers!