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. 

Pushing too Hard

Jean Skirt Look
Back in the day

Over the many years I spent trying to find my way into a feminine world, often I was guilty of pushing too hard. A primary example was when for once I was able to put my cross dressing act all together. In other words I was able to walk without falling in sidewalk cracks plus I felt my makeup, outfit and hair all looked as good as possible. I felt good and the whole experience was a positive one. 

The next time I went out I thought I would build on the last experience but didn't quite do it. In those days I was still validating my life as a cross dresser or transvestite by what men thought of me. It wasn't until much later when I learned it was so much more important to me to be judged and validated by other women around me. So, to make a long story short, I went overboard in my dress, makeup and especially hair. The end result was similar to a matador waving a red cape at a bull. I stood out like a sore thumb wherever I went. In addition, many times I was thrown back to square one and had to start all over with how I dressed myself. 

It took awhile of tough loving my feminine self but I finally learned all my trashy outfits and crazy wigs weren't working, I finally settled into a more or less everyday persona of who I would eventually become on an everyday basis. I substituted too short and tight mini skirts for more proper yet flattering jean skirts and I used flowing fun blouses/tops to help disguise my all too hated male figure. In essence I ended up killing two birds with one stone. My appearance was still on the cutting edge of having fun without going so far I was attracting unwanted attention.

Also around that time was when I quit pushing so hard and began to relax on most fronts. Now I could pay more attention in rounding out more of my total self. The way I moved, the way I talked began to come together, From then on pushing harder was out and a new confidence was in. I even settled on the same wig which I nearly wore out. 

Through it all though I don't want to give the idea that anything was a pushover when it came to my gender transition. It was just like I could start on starting on settling more of the more mundane problems I was experiencing. One of which was not so mundane was using the women's restroom which is a topic I revisit fairly often in my posts. It is no secret I like to drink beer and beer doesn't stay with you long so I had to use the women's room frequently. Often it was the ultimate answer to how I was presenting as a transgender woman. I found in many venues other patrons would draw the line and complain if I needed to pee. Having the cops called on me was a decidedly unpleasant experience

Another small thing I did to try to normalize being a single woman in a hetero bar was to use my cell phone as a prop. I would sit down, order and act like I was texting someone else to join me. As you can tell I was trying every little thing I could to make it in feminine world and earn my right to play in the girl's sandbox.

When I quit pushing so hard, the easier it became. 
      

Girls Night Out

Girls Night Out #1 
I am on the left.

As I was first attempting to survive in the feminine world without the "Ha-Ha" moments Connie mentioned in a recent comment on my :Ah-Ha" post, I craved any opportunity I had to join a women's night out. In a relatively short period of time I was fortunate and was invited to four, One of which was even a bachelorette party which sadly was cancelled. Two of the remaining invites were with a group of cis women friends I became close to until similar to many women they got married and moved away from the group. Children were involved also.

Perhaps the most exciting was my first invite because I had no idea of what to expect seeing as how there were going to be a couple other women attending who I didn't know. How would they accept a transgender woman? The answer was one didn't seem to care and the other rejected me quickly.  

My first issue was what to wear of course. I wanted to appear as attractive as I could without over-dressing the other women. As you can see in the picture, I think I achieved the desired effect. My second issue was what would the conversation be when no men were present and again how would I fit in. The whole process (per norm) turned out to be just a whole lot of worry about nothing. Most of the conversation dealt with family and children so I just inserted my daughter's examples when I could. During the space of the evening I even forgot to worry about my voice. Everything must have worked out fine because shortly after the first night out, I was invited to another before I moved away with Liz to Cincinnati.

Perhaps the most surprising girl's night out occurred when I was invited by a group of servers from one of the venues I was going to on a regular basis to join them for a get together at another trendy venue. I was terrified when I said yes. How would I react to going with a group of younger, more attractive women to a venue I had only been to a couple of times. This time there wasn't much conversation because of the amount of guys the rest of the group attracted. It turned out to be like I was almost invisible as the night went on. Lesson learned.

As far as other lessons learned, I discovered no new earth shattering gender secrets when women gather.  Naturally, it was no big surprise when the younger women I was with got their flirt on with men and forgot about the group all together. Even though all of that happened I was pleased I survived the evening without doing anything gender ignorant.

Overall, all of the girls nights out I was invited to were fun and learning experiences. I was happy to accept the invitation.