I’ve got something to admit to everyone who doesn’t know me from way back in the day.
I have, on multiple occasions, dressed up like a woman. Nope, that’s not a typo. I’ve been out in public, and seen by others, dressed like a woman.
The last time I walked on the pink side, believe it or not, I was doing the Lord’s work. I was on a mission trip to Pittsburgh, Pa., where I wore a pink dress, that when stuffed with balloons, looked quite shapely on me. I had makeup on my face, but no wig or something that would substitute for one. Lack of resources. It was a part of a skit where about ten of us were wearing the girls’ choir outfits and singing something I can’t recall. There were photos taken, but I sure don’t have any of them.
Looking back, it seems like I could be accused of conspiring to get more and more people in on the act, because the second time I dressed like a woman, there were only two of us doing it. I was part of a brainstorming session for our high school’s Project Graduation group, though I can’t figure out why, other than I knew the guys who were in charge. We needed ideas for a skit that we would perform in front of the entire senior class hyping our drug & alcohol-free post graduation party. Well, from not knowing how I got to the meeting in the first place, I ended up being one of the two guys dressed up, on stage, like the ‘Men On Film’ characters from the sketch comedy series “In Living Color.” Our skit wasn’t as baudy, but we really played up the gay accents, and got to make comments about a prize winner who had to come up on stage to claim his prize, and we ‘accidentally’ dropped his prize so he’d have to bend over to pick it up and give our characters a view of his backside. (On a side note, he never pounded me for that – he was a nice guy.) There was, at one point, video of this, because it was on the local news the next afternoon, but I hope there’s no pictures.
The first time was solo, and as I recall, I volunteered because nobody else, not even the girls in my group, were up to the task of Queen Guinevere. It was fifth grade, my first year at the school, and I was in an Olympics of the Mind group. Another group had some sort of challenge involved with reading Moby Dick. I know one of the kids in that group read the entire book, I don’t know about the others. Our challenge was themed on the Adventures of Camelot. We had to maneuver a maze shaped like the walkways around the top of a four-walled castle. But each person going through the maze was blindfolded, and guided by someone who could see, but couldn’t communicate with voice. Once a blindfolded person reached a checkpoint, they removed their blindfold and served as a guide for another person. Anyway, the main guide was Guinevere, and I was the only person who could do it. So, I dressed in my mother’s old purple robe, put a tiara on my head, and went out there dressed like a woman, with my classmates cackling the whole time. The girls were the worst about the heckling, and all I could do was grab their hair and threaten to slam them to the ground unless they shut up. That was about all my father would let me do to defend myself without beating me to a pulp. Why that is so is for another story….