In the early 1960s, I was on the cusp. I was a feminine boy, but I had never dressed. Except for comics on television and actors in films, males dressing as females was unheard of in my little world. Dressing as a female myself never even crossed my mind… until one Halloween.
I recall visiting my aunts' house on Halloween dressed as the Frankenstein Monster. My aunts were all aflutter about a neighborhood boy who had visited them earlier that evening dressed as a girl. He even wore stockings and high heels! Suddenly, dressing as a female myself crossed my mind.
Another Halloween, Billy, my best friend in grammar school urged me to join him trick-or-treating that year. He told me that he dressed as a girl the previous Halloween, planned to dress as a girl again this Halloween and suggested that I dress as a girl, too. I was intrigued, but as feminine as I was, I was not ready to dress as a female because I feared what people would think if I did dress up. (By the way, after adding a lot of twos and twos together, I am certain that Billy was transgender.)
About this time, I was exposed to female impersonators.
My father bought the New York Daily News every day and I noticed that at the end of the week, probably in the Thursday or Friday edition of the News, there would be a thumbnail-sized ad in the back pages of the paper that caught my eye. The ad always consisted of a photo of a gorgeous showgirl and was captioned "Who's No Lady?"
The gorgeous showgirl was no lady, but a female impersonator and the ad was for the Club 82 in New York City, a nightclub that featured female impersonators. I was amazed that males could look like the showgirls featured in those ads. I was so fascinated with the transformation that I began cutting out the ads from the newspaper and collecting them with a paperclip.
Then home alone one day, I started on a voyage that has never ended. I went to my parents' bedroom, found a pair of my my mother's nylon stockings and tried them on. This was so long ago that the stockings had seams (all stockings had seams back then) and my legs were still hairless.
After I slipped on the stockings, I opened my mother's closet to see how my legs looked in the full-length mirror hanging on the inside of the closet door. My legs still looked like my own legs except now they were covered by nylon.
Then it occurred to me that my mother's shoe collection was at my disposal inside the closet. I slipped on a pair of her high heel pumps and examined myself in the mirror again. My legs were no longer boys' legs encased in nylon; they had been transformed into a pair of shapely legs that any woman would die for!
After that eye-opener, I experimented with my mother's girdles, bras, dresses, hats, gloves, lipstick, rouge, etc. and got caught up in a snowball that has never stopped growing.
Wearing Boston Proper (Source: Boston Proper) |