Waiting for Halloween

Halloween 1983

Growing up, October 31, also known as “Halloween,” was my favorite holiday. To me, the candy was incidental; the costume was the attraction.

I never wore an off-the-rack costume. Rather, I assembled bits and pieces to create my costume. I was the Frankenstein monster, the Hunchback of Notre Dame, Alfred E. Neuman and a Pittsburgh Pirate (the year Mazeroski beat the Yankees in the World Series). Although I had girly inclinations, it never occurred to me to dress as a girl for Halloween – I mean, “Who does that?”

Turns out, lots of guys. 

One year, making the rounds of my relatives homes on Halloween, my aunts were all aflutter about the neighborhood boy who showed up en femme. I remembered that they were very impressed that he was wearing nylons and high heels. Wow – was I jealous!

A couple of years later, my best friend complained that he had shown up at my home to trick-or-treat and was disappointed that I was not home because he wanted me to see his costume. You guessed it: he was dressed as a girl. 

Next year, he tried to convince me to join him and dress en femme for Halloween. To guard my fragile male ego, I indicated that I had no interest in joining him, but in my heart, I was dying to do so.

It turned out that guys did dress as girls on Halloween. So after dressing surreptitiously in my mother’s and sister’s clothes for the better part of the 1960’s, I decided that Halloween 1969 would be my debut as a girl. 

I did not want to reveal how good my femulating skills had become during the previous years, so I toned down my costume and wore boy sneakers rather than Mom’s heels, boy underwear rather than my Mom’s bra and girdle, minimum makeup, a skirt, top, woolen cap and wiglet borrowed (without permission) from my sister’s wardrobe.

Mind you, I had no place to go. I was way too old to trick-or-treat, I had not been invited to any Halloween parties and I was too young to go bar-hopping. So I drove around town and visited some friends and relatives. And had the time of my life!

Next morning, I was back in the closet looking forward 12 months hoping that the next Halloween would offer an opportunity to crossdress among the civilians again. Most years, I was disappointed, but on a few occasions, I was invited to a Halloween party. And unlike my first Halloween out, I did not hold back. Instead, I used all my femulating skills to present myself as a woman. 

Attending those parties, I realized that over the years working hard in my closet, I had gotten pretty good at femulating because more than once when I showed up at a party, other guests wanted to know who was the woman not wearing a costume!

Attending one of those parties with my bride changed my life. Noting my femulating skills and having become familiar with my past Halloween “costumes,” she put two and two together and suggested I find and join a support group, which I did as quickly as possible. 

The support group provided opportunities to crossdress among the civilians on days that did not proceed All Saints’ Day. No longer did I have to depend on that one day in October hoping that someone, somewhere would invite me to a Halloween event. But don’t get me wrong – I have not abandoned October 31 and have dressed appropriately many times on the “Crossdressers’ Holiday.”

Wearing Nanette by Nanette Lepore
(I said yes to this dress and ordered it on sale from Rue La La.)

Yet another modern couple