As soon as fall weather begins to sneak into our climate here in Southwestern Ohio, I'm sure the thoughts of crossdressers and or transgender women still in their closets turns to Halloween.
Back in the day, I had my share of Halloween's when I basically came out to my friends and acquaintances at the least as a cross dresser. Over the years, I have been able to share sort of a "best of" series of posts on my experiences.
Because of my job in the restaurant business, I was unable to "dress up" for Halloween but I normally found other outlets. One memorable one was when a couple friends, my wife and I went to a restored Victorian style theater in Columbus, Ohio. They were showing the original silent version of the "Phantom of the Opera" complete with an accompaniment by the restored theater organ. The costumes were amazing!
I wore a mini dress with heels, shaved legs and blonde wig. The idea was wonderful until I had to negotiate a long walk in those heels!
Also, shaved legs represented sort of a demarcation point between being a casual cross dresser and someone who is much more serious. I actually wore the same outfit to my own bar's Halloween party and earned the nickname "legs". I wish I could actually find the picture of me which surfaced quickly, but it unfortunately is long gone, it seems.
Two of my female friends went as far as saying I made a better looking woman than a man, which would turn out to have far reaching implications, good and bad. From that point forward I started to "invent" reasons to cross dress in front of certain friends and secretly fantasized about having a "girls night out" with some of them.
As it turned out, I would have to wait some 35 years for my first night out with cis women.
So Halloween to me will always be a cherished time which continues to this day. Last year, my flowing witches costume attracted an "admirer" at our "Witches Ball" and I hope this year will be as fun too.
Advice? Halloween is a slippery slope. If you want to gently take the risk to out yourself, do it.
But if you do, take the chance to enjoy the experience!