The absolute best time I had in a prom dress (being a male, also my first time) was attending the Rocky Horror Picture Show put on by the Barnstormers.
There was, of course, much preparation involved in this. Probably 6 shots of Bacardi, some Pepsi, some Sierra Mist, and then I started in on the cross-dressing. Also required was one sports bra which looked like an orange headband for an elf. This went over my fake breasts, and by that, I mean itchy paper towels. Ouch! And to top it all off, a nice wig.
All while getting dressed, I was drinking aforementioned booze in front of RAs. One of them was also in drag. The other could not stop laughing at us.
Once we got to the show, all hell broke loose. I got called in to help out on a variety of techie responsibilities, which should have been resolved more than 24 hours before. So I got more drunk and more angry, and ended up sitting with the RAs. Well, ok, humping the one in drag. But it was Rocky, right, so anything goes?
Yeah, anything went. And I for one, hit up the everclear.Blackout!
I tried to start a fight with the director. I told Dr. Scott my entire medical history and yelled at him when he was not paying attention.
Changed with much ado, and then with a little help made it back to my dorm without causing a ruckus.
The moral of the story: you know a girl trusts you when she lets you get shitfaced in her prom dress and one of her sports bras.