Originally Posted by
ThePreserver
Back in school, us Student Council members had a thing where you could "auction" people for a day, and force them to wear stuff, carry their books, etc. Naturally, all of us gentlemen were forced to cross-dress, and let me just say, I'm not very much used to wearing something as short as a skirt. My shortest shorts are knee-length, and they had me wear a very short skirt. When I sat down I had to cross my legs so no one would see anything.
It was... interesting, pretty breezy up there (I had boxers on underneath). I dress for comfort/utility as often as possible, so cross-dressing wouldn't really do anything for me. Although wearing women's underwear, I could probably see myself doing that.
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