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.