My high school did not have a womanless beauty pageant or a gender swap day like the schools that the lovely lads in lace above attended. The closest our school came to approved crossdressing is when the boy’s basketball team performed in 1920’s flapper drag for the annual school musical. Their femulation was nothing to write home (or here) about, but I was jealous nonetheless because given the opportunity, I knew my presentation would have been more authentic than the basketball men in dresses.
Men wearing earrings became a thing while I was in high school. I recall our principal warning the boys that if anyone showed up wearing an earring that boy would also begin wearing the Catholic school girl uniform that the distaff side of the student body wore.
I thought about borrowing a pair of my mother’s clip-ons and wearing them the next day, but I did not want to give the class bullies the satisfaction that they were correct in electing me “The Boy Most Likely to Change Sex.” So I just dreamed about wearing a navy blue jumper, white blouse, nylons and penny loafers to school instead of my boring sports jacket and trousers.
Instead of being a closet crossdresser, what if I was more open about my crossdressing back then? I am certain that my parents knew what I was doing when I was home alone and I like to think they would have supported me. And I’m sure that my mother, an excellent seamstress, would have sewn me confections that would have made the other girls jealous.
Living full-time as a woman would have been delicious, but not only did I miss the boat, but I was too scared to even buy a ticket for the journey. But back then, I did not know about womanless pageants and the like. I knew I wasn’t alone, but I did not think there were many others like me even though my best friend in grammar school practically came out to me as a crossdresser. What were the chances of that if crossdressing was as rare as I thought? Nevertheless I was not prepared to take the journey solo.
Today, looking at the thousands of the Internet images of girls like us, I wonder if there are any guys who haven’t crossdressed! There sure are a lot of us! There probably always were, but today we are more open about it, so it seems like there are more.
If I could to do it all over again... but I can’t, so why beat myself up about it. Instead, I will continue to be the best woman I can be or rather, the best old lady that I can be and enjoy my femininity as often as I can.
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| Wearing Boston Proper |
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| Kristin and Jean, 21st Century son and father |
