It is Fall and Time for Halloween

 

I have heard Halloween is the national holiday for cross dressers everywhere.

I know it was for me as I could not wait for the trees to change colors and the temperatures to dip so I could plan my "costume" for the season. I was fortunate when I began to learn so many feminine basics thanks to my Halloween experiences. Such as, the first night I went out with friends to a late night showing of a silent movie in a beautiful restored theater in Columbus, Ohio. The primary lesson I learned was to either get a close parking spot or wear comfortable footwear as my heels began to bother me very shortly into the evening. Regardless, I had a great time in my short mini dress and I was disappointed when I did not see anyone else cross dressed (that I know of) and the night went by so quickly. My friends we went with did not even mention my shaved legs. I remember thinking it was going to be a very long year before I again could challenge the world as my feminine self.

Back then, my self was very under developed. The mirror still had a hold of me and I really had very little knowledge of where I truly wanted to go as I researched the gender world. Would the mirror be my home or could I succeed as a novice transgender woman. In it's own very important way, Halloween helped to point me in the right direction. The first parties I went to, I simply tried to dress sexy as my "costume" and took the easy way out. I was seeking validation as a woman  essentially by doing a form of drag, which never worked for me. For the most part, I was left alone by other men and women. It took me several parties to understand what I was doing wrong. 

From there on out, I started to attempt to tone down my "costume." For example, one year early on in my transition I wore all black. Starting with black flats, black tights and sweater. I paired it all with my short black skirt, long blond wig and topped it off with a black beret hat. I tried it all out at one of the big dance clubs Halloween party in town and was enjoying myself immensely until a person in a mask came up to me and said I know who you are. Initially I was a mixture of being scared and devastated some one could see through my "costume" so easily I did manage to laugh and say who was I and the person said I looked just like my Mom. Then I realized who he was and he went on his way. It turned out I grew up near him in the rural neighborhood where I lived. Even with all of that I had a great time and was saddened that Halloween only came around once a year.

It turned out there were many other lessons to learn from the cross dressers national holiday as I was going to find out. One of the biggest ones was when I realized how rare it was to find another possible "non civilian cross dresser" in their own "costume." Again, I was feeling alone in the world. Another one was there was no way I could wait another year to venture out into the world as my authentic femininized self. At the same time of my Halloween adventures, the internet became a part of my life and I was able to research terms such as transgender to see if they fit me. I found there was so much more to learn. 

There were more Halloween parties where I continued to learn from too. I haven't forgotten my pledge to share them also since for the most part, they had such a profound effect on my life as a novice transgender woman. 

Witches Come Together

 

Witches Ball Photo from the
Jessie Hart Archives...

Not so long ago, I was part of a group of Wiccans who put together sizeable parties every Halloween called "Witches Balls."

At it's peak, over five hundred people attended in a very appropriate huge vintage venue across the Ohio River from Cincinnati. Liz and I had plenty of experiences with the event because we went on several dates there before we were involved with organizing it. One of my fondest memories came when the Johnny Depp/Jack Sparrow impersonator flirted with me one year when the party was featuring pirates and also belly dancers. I also enjoyed watching the sexy gyrations of the dancers as I was given a chance to sit down with Liz and kick off my heels and watch. As much as I was enjoying wearing the heels, I was still paying the price for wearing them too long. 

Of course, since it was Halloween, costumes were an intricate part of the event and I was always on the outlook for the occasional cross dresser whose look was just a little too good. As close as I ever came was when I ran into a Facebook acquaintance who is also transgender who was selling her jewelry at the party. Overall, I was surprised I never was able to see anyone else who dressed as a woman for the evening. One thing for sure, I didn't need anyone else's approval  and I had a great time. 

Sadly, the larger witches ball's have become a thing of the past around Cincinnati and now are only held in smaller venues such as bars or taverns. So Halloween has increasingly become another rather boring day. However, I will be forever in debt of Halloweens past as they opened doors for me to express my true self long before I ever thought it was possible. We don't even have enough young trick or treaters stop by to see if any of the young boys are still dressing as cheerleaders. 

I do miss also the huge volunteer organizational effort it took to enable the events to happen at all. The feel good portion of the whole affair happened when we were able to donate a fairly large sum to one of the local homeless shelters. Karma is real and it is always nice to pay forward when you can. 

Since I live fulltime as a transgender woman for so long now, I don't need the feminine experience of a Halloween costume to shore me up. But on occasion I still miss what Halloween did for me in my life. Along the way, it became my most important, influential holiday. It opened my eyes to what could be possible and I could actually live out my gender dreams.   

Halloween

 Well, it's here. The day I have been seemingly writing about forever and a day which paved the way for my current out transgender lifestyle. It's Halloween of course.

Throughout the years often I wished I could have followed the path of nearly everyone I knew. Costumes were for fun or creativity. Not as serious as mine were. Then there were all the years due to work situations I couldn't wear a "costume" at all. 

All of that is in the past now. Looking back at it all, I was fortunate enough to be able to live most all of my Halloween fantasies. 

On this Halloween, I hope you have too!

My Political Connections

 As Halloween rapidly approaches, as promised, I thought I would share several closet opening experiences I went through. These experiences were instrumental n helping me to gain courage to pursue a life in the feminine world. 

The experiences are not in chronological order and this one actually occurred a couple years after my earliest attempts at going out as a woman on Halloween. 

As it turned out, a friend of mine owned a huge spooky Victorian mansion and was going to have a fairly exclusive Halloween party. I was a fairly well known radio DJ and somehow made the cut for an invitation, along with one of the news girls. 

Since this wasn't my first Halloween rodeo dressing as my true self, I deiced to steer clear of my previous "slutty" costumes and try to dress as a cis woman to see what would happen. 

To make a long story short, I had a great time. I ended up going with the news person somehow instead of my wife. One of the few times she left me unattended. It was first page news when the news girl saw my "costume" all the way down to my freshly shaven legs. It turned out the evening was only going to get better. 

The party was well attended and everyone I encountered remarked how "real" I looked, especially one of the area's up and coming politicians and his wife. They wouldn't leave me alone, all the way to inviting me to come along with them to another party they were attending. Since I didn't drive myself that night, I said no and decided to go back with the news person who drove to the party. 

Needless to say, the whole experience was a prime case of gender euphoria for me. At the least, I found I could present in the world as a feminine person. The down side came the next day when I had to return to my boring male world. Except for questions at work about my so called "costume", which I quickly laughed off.

I will always wonder though what would have happened if I had left with the political couple and went to another party.  Also, unfortunately I have no pictures. It was a long time ago in the late 1970's.  

I did pass along a close replica of how the house looked.

Was it Halloween or...

Or a fun night with friends in a neighborhood tavern in Cincinnati?
Actually both as I ended up with four genetic beer drinking jello shot slugging women. Times were rough? Not so much! As you can see in the pictures, I wasn't drinking. Haha.
I would estimate only about a third of the customers were in costume. I told the girls before we got there I was a little apprehensive of walking into a red neck bar, being the only ones in costume and being "underdressed" in huge red hair and boots.

Well, I was right about the no other costumes to begin with. Just one other person- but it was early and the tavern was neighborhood not redneck and none of us got much attention.
Most of the patrons were engrossed in a high school playoff football game on the televisions between two Cincinnati teams-forget Alabama/LSU.

As the night wore on, the bottom picture shows what happened when all of the sudden I experienced wig slippage.  (Haven't worn it much!) .Interestingly enough though,  a newcomer to the table at the same time asked me if the hair was mine. A couple of the other women assured her it was- until I had to adjust it!

Overall, it was one of those evenings that makes you wish Halloween lasted just a little bit longer!