Halloween is like candy on Trick or Treat Night, you do never know what you are going to get.
This Halloween experience goes way back to the early 80's when needless to say I was much younger, slimmer and prettier. I had just married my second wife and talked her into moving to the New York City area sight unseen from Ohio to start a new job with another restaurant chain.
We were settled in and unsettled at the same time when Halloween rolled around. Our relationship at the time was real rocky due to the fact I was still riding the "ego coaster" from basically having to prove I wasn't a genetic female to get into a "transvestite mixer" weeks before. I literally was torn in half by gender issues which made me an absolute bastard to live with. So, by the time Halloween rolled around, she basically kicked me out for the evening, slutted out and all.
As it turned out I was invited to go out with an assistant manager of mine and her friends. So why not? Mini dress, shaved legs, long blond wig and all, I showed up at the house where we were all supposed to meet. As I made my "grand entrance" of course the room got quiet. Who knows what they really thought until I said "Hi" in my very male voice. Then, it was my turn to be quiet as the three other women just happened to be dressed like me (and almost as tall) got up to leave. Just for a second I thought I had died and went to cross dresser heaven and all this time it was in Yonkers, New York? Yay!
The place we were going was only about a block away so we walked it. I remember the clicking of all of our heels on the pavement as we crossed in front of cars in an intersection in front of the bar like it was yesterday. Quickly I lost any apprehension of how I was dressed and did my best to throw my shoulders back and blend with the other three. The Aerosmith song "Walk this way" comes to mind! Looking back on it now though, the evening was one of the first ones where the rush of the clothes, wig and shaved legs faded quickly. I think I knew but didn't really want to acknowledge how natural I felt.
Once we got in the bar, the other three were quickly the hit of the evening and I tried to quietly grab a spot at the table, order a drink and enjoy the situation I unknowingly found myself in. I didn't labor under any ideas no one knew I was a guy but I did turn down two requests to dance.
All too soon, the "bewitching hour" was upon me and it was time to leave. The good news was the evening was incredible beyond all expectations. The bad news was once again I didn't do my relationship any favors. For you long term "Cyrsti's Condo" visitors you may remember the comment "be man enough to be a woman" from my wife which finally taught me a lesson. Did I want to move past looking like a woman to experiencing life as one?
As you have probably guessed then I had no easy answer to my gender questions and there were many lessons to come. The story has a happy ending though as my wife and I were married for 25 years after that evening, until she passed away some time ago. She became more of a feminine role model to me than probably she ever knew.
Life is nothing if not just moments in time. Some better than others and the Halloween party that night exceeded all my expectations-even when my boss came up to me the next week and smiled slyly when he asked about my costume!