Tuesday, December 9, 2025

Transgender Game Changers

 

Image from Andre Fonseca
on UnSplash.


One of the positives to being able to live a long life is to be able to look back on all the key moments in my life when a decision one way or another could have made a huge difference in my life.

Perhaps the biggest moment was when I discovered the enchantment of looking at the pretty girl in the mirror where my boy self was just standing. Sadly, the moments were fleeting as my life was calling me.

As I grew up and my life became more complex, so did my dealings with my transgender issues. One of the most important lessons I learned came early when my second wife and I encountered a handsome Harley motorcycle rider at a tavern we were at one day in Cleveland, Ohio waiting for a transvestite mixer we were going to, to start. I was very new  to being out in the world as a cross dresser and was completely surprised at my reactions when this guy came into the bar and started flirting with my wife. Then, I was even more concerned about my wife when she started to flirt back, completely ignoring me. What was I going to do since I was stripped of all my male reflexes of what to do when another man was flirting with my wife. I had to just sit there and be quiet and hope she did not go for a ride on the Harley with the man. Of course, my wife sensed my concern but let the situation play itself out to teach me a lesson in feminine competition. One I never forgot.

Another evening, I never forgot and could have been a bigger game changer than it was, was the night I had my makeup done by a professional makeup artist in Columbus, Ohio at another transvestite-transgender mixer I was attending. After the makeover, I was stunned at all the positive changes the artist made for me. I was flattered with all the compliments I was receiving and decided I did not want the evening to end early. I wanted to join the so called “A” listers who always went out on the town and show off my new look. Plus, for some reason, my wife decided not to go to this mixer, so I was free and on my own. We ended the evening at another tavern which I could not tell was LGBTQ friendly or not but one way or another I bought a beer and headed for one of the unoccupied pinball machines. When I did, amazingly I was approached by a younger good-looking man who wanted me to stay and play pinball with him. By this time, the rest of the “A” girls were ready to leave, and I needed to make a split-second decision on if to stay or go. Since I had no idea if the man knew my true gender or not, and I was in a strange city, I decided to go with the “A”’s who were jealous of me because I was approached by a man and they were not.

I never knew what would have happened if I had stayed and would the evening change my life forever, which also happened the night I went on a date with Bob. By this time, my wife had passed away, and I had not met Liz yet (my future wife) so I was free to explore my own boundaries. Bob was not from my area of the country and on occasion passed through the Dayton, Ohio area on business where I lived. On one of those nights, I knew he wanted to meet me in person at one of the venues I was a regular at. I had never partied with a man at a sports bar before, so I did not know what to expect. What I did not expect was the great time I had. It was the first time in my life that I had been treated completely as a woman, and I loved it. It was even a karaoke night, and he sang for me. And yes, Bob did know I was transgender. We shared a rather passionate kiss together and the night was over. Never to be repeated again.

There were other trans game changers such as girl’s nights outs and the conversations I shared with a man who I thought I could have gone farther with if he had stayed around. The “what if’s” remain big questions for me as I grow older, and I know you can’t have it all. In many ways I crammed a lot of life into my years which I am grateful for.

I should not be selfish though because I have been blessed during my life with people who have loved me, and I did my best to love back in return. Sadly, my gender issues were in my way through most of them and if I had faced reality, I could have been a better transfeminine person. Which is a topic for another blog post altogether.

 

 

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Transgender Game Changers

  Image from Andre Fonseca on UnSplash. One of the positives to being able to live a long life is to be able to look back on all the key mom...