I never participated in such an event. But, I was part of a large club in college where the idea of a crossdressing party around Halloween was floated. My interest was seriously sparked and I probably let on too much how interested I was, enough so that a young lady of our group commented on it. I immediately shut up about the party, never said a word about it again. The party didn't happen.
Our High School Varsity Club had an annual dress like a girl event where all new members had to come to school fully dressed for the entire day. One particular year I remember that one of the track guys came and my god, he was stunning. He was smaller and a little effeminate but he passed 100% as a woman. His movements and mannerisms... Looking back on that day you cold tell that he had done this before. The year I would have been eligible to participate, it was dropped from the requirements. sigh....
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