my first *serious* gf in high school -- i expressed my curiosity about dressing to her and she said, "lets do it!" so one afternoon when her house was empty, she gave me the "whole 9 yards" in her words. i had longish hair then, so she styled it. i can't remember if i was remotely convincing, but it was awesome. we did it again for halloween once (used a wig -- more of a funny look), then we even put together an outfit (she helped me shop for it) for my first time out in college. i went to an atm, a gas station and mcdonalds drive in (she drove). the funny thing is, after we broke up, i saw her wearing the dress from my outing! she looked better in it. : ) she was such a fabulous woman -- those were amazing times.
my wife dressed me up 2x for halloween. both were amazing. had a wig the second time and thought i passed just a little. i shaved my legs both times, and got some strange attention from guys that i knew. one kept wanting to put his hand on my leg (bare legs the first time), and i'm not so sure it was all a joke. the second time i wore black hose, and the host of the party kept commenting. helps me understand the female experience a bit.
probably won't ever happen again. after the last halloween, i think my wife realized i enjoyed it too much and said never again. who knows, maybe in another 5-10 years she'll soften. ;-)
sorry for so much detail! just fun to reminisce.
ps -- and the one that probably started it all -- my sister dressed me up in her clothes when i was about 6. : )
