Yes, some people can remember that far back. I am the youngest, a surprise baby, of a family of three older sisters and a brother. I was born in early 1949 and spent my younger days admiring my sisters, mother, girl classmates, and the girls in my neighborhood on Long Island, NY with their amazing full dresses and skirts. I attended a Catholic Grade School that did not require uniforms. Boys had to wear dress slacks, white shirts and either a long tie or bow tie Down Dating tips. Oxford shoes only, no sneakers. The girls had to wear dresses or skirts and blouses. There was no rule about skirts being too short because they were all knee length or longer anyway. Mini skirts had not become the fashion yet.
In 1956 my family moved from a cramped 1 and 1/2 bedroom apartment (remember there were seven in the family) to a three bedroom Cape Cod style house with a full basement. I was seven and that was when I was left alone without a babysitter for the first time and immediately took advantage of my sisters’ and even my Mom’s closet and dresser drawers. My life started on the path of a crossdresser that, after 64 years, I am still happily traveling. But I was alone, as a boy, and I knew it. Society frowned on any male, young or old who would want to dress feminine unless it was a parody of one, like what Milton Berle or other comics of the 50’s did.
At thirteen a boy was on the threshold of being a man in those days
Fast forward to the fall of 1962. I am now in another Catholic school, but now it is a boys High School. It was a college Prep School in Brooklyn, N.Y. We were required, from freshman year on, to use the famed 5th Avenue New York City Public Library to do research for any papers we were assigned to do. I was now thirteen and still feeling like I was the only boy in the world who wanted to dress like a girl. The weight of carrying this secret was truly heavy on my soul. Things were very different back then compared to now. Imagine letting a thirteen year old commute 2 hours each way to school and back home, via bus and subway today? Then add to that, commuting into Manhattan to that phenomenal World Class NYC Library on the corner of 5th Avenue and 42nd Street on Saturdays to do more studies. No parental monitoring. Amazing times to grow up in.
But one day, I wandered down 42nd Street toward Broadway and Times Square
It was on one of those Saturdays that I finally found out that I was not alone. You could leave your books and papers where you were sitting in the amazing Reading Room at the Library and return an hour later without a page being disturbed. I would eat my brown bagged lunch in Bryant Park behind the library. Everything seemed new and amazing to me. But when I got to Broadway and looked down the street toward the Hudson River, it was like I was looking into the gates of Hell. After all, I was a thirteen year old Catholic boy. I could see movie marques hanging over the sidewalk for what seemed like forever. And they all had XXX next to the titles of the movies. Coupled with the signs that announced ADULT BOOKS all over the place, I thought I had just committed enough sins, just looking down the street, to go straight to hell.