Taking the Gamble

Photo Courtesy
Jessie Hart

 I have never been good at or desired to be good at any form of gambling. However taking a gamble was completely the case when I decided to play my gender cards and transition into a transgender woman. 

Since it took me nearly a half a century of being a very serious cross dresser, I had plenty of time to consider my next move before I made it. Over the past, I have given more than a few examples of my many failures attempting to break out of my gender closet, as well as successes also. One of my examples of success was the night I was by myself in Columbus, Ohio attending a party at a transgender friends house. For whatever unknown (now) reason, I decided to go all in black. I wore a pair of shorts which were not short with black tights, flats and a black sweater. A dark wig completed my outfit. I looked at myself in the mirror and decided my looks were attractive enough without going overboard and out the door I went.

Once I arrived at the party, I found everyone on the patio because it still was a warmish fall evening and found I had dressed appropriately for the evening. After awhile, a single woman approached me who I presumed to be a lesbian. Our conversation moved along smoothly until we decided to leave for awhile and go to a well known large lesbian venue in the nearby downtown area. I gambled and said yes since I knew my way around Columbus and could return if I needed to. Later on in the evening, we went on our separate ways and I never saw her at any other parties.

Another time I gambled in the opposite direction and didn't go/stay with a guy in a bar in Cleveland, It happened after I submitted myself to a professional makeover and couldn't believe the change, It was so dramatic I was invited to tag along with the transvestite groups "A-Listers" or the self perceived prettiest cross dressers. They were shocked when a man approached me to stay and play pin ball with him. I was flattered but told him no because I didn't know if he knew the gender truth about me and if something negative happened, I didn't know the way back to the hotel where we were staying. I left forever wondering what would have happened if I gambled and stayed. 

Overall, the biggest gamble I ever took was when I came out as a transvestite to a few close friends in the army. This was way back before the so called more liberal LGBTQ "Don't ask Don't tell" days in the military. I worked in a very public job as a radio disc jockey position in Stuttgart, Germany. I could have lost it as well as being dishonorably discharged if the wrong people found out. Which they never did. I went on to marry one of the friends I came out to and she is the mother of my beloved supportive daughter. My gamble really paid off.

These are just a few of the gambles I took in my life. I do believe if you don't take some gambles you won't get ahead in your life. Plus just living pushes you into taking gambles. Regardless, I always tried to play my cards the best way I could. 

Grounded

 Perhaps if you are similar to me you also have to "ground" your transgender feelings. 

Liz (left) and I during a night out.

Over the years it mainly meant I had to uncover my "collection" of feminine clothing and makeup then find the nearest mirror to examine my handiwork. The problem quickly became when I started to explore the world as my feminine self, I encountered many people who didn't share the mirror's idea of how I looked. It was after these occasions of being rejected I had to go back to the drawing board and attempt to ground myself again. 

As I progressed down my transgender journey, becoming grounded became more intricate. For example, when I advanced to the point of properly presenting myself as a feminine person, the time came to form a whole new personage. All too quickly it seemed people wanted to actually talk to me. Staying grounded while I learned to communicate as a woman was difficult. Especially when I began to understand the nuances of communication between the genders. After a day, or even part of a day, it was exceedingly difficult to adjust my grounding back to my non authentic male self. The stress of attempting to exist part time in both of the binary genders was intense and one I wouldn't wish on my worst enemy. 

All of the stress finally led me to another suicide attempt and I decided to take the path which was more natural to me and attempt to live fulltime as a transgender woman. Once I achieved my goal, unfortunately the stress of being grounded as my authentic self didn't cease. Even though I felt I might have it better than the average transgender woman I encountered in support groups, I still had my moments of not feeling grounded. Perhaps it is because I still took all of a half a century to fully transition. Perhaps it has just taken me a bit longer than I wished to lose all the figments of who I was,

Now I am fairly sedentary and still don't get out much even after Covid. During the time I have learned to finally accept myself for who I am. I am no longer fighting to be a false male self . Even still, when we can, I cherish the times Liz and I can go out to eat. It's a time I can reestablish my feminine self and get grounded again as my true authentic self.

Hopefully your path has been easier than mine and you have discovered and live as you please.