I “Doesn’t” Know It

From my Dating Days. Photo Credit Cyrsti Hart

The title above is a phrase from a former Hall of Fame Cincinnati Reds baseball announcer, used when he didn’t know something. I borrowed it from him as I thought about today’s Cyrsti’s’ Condo post. My idea was to write about dating while transgender. 

Way back in the day in my earliest days of coming out of my closet into a feminine world, I had to decide who I was going to date since I had abruptly became single at the time and a widow. Very quickly I faced the differences between gender preference and sexual preference. At that time I had never even kissed another man. 

As it turned out, it would be a while longer before I did. I craved being with a man because it would validate my femininity in public but it seemed destiny  had another path charted for me as far as my sexuality was concerned. I did have a very few dates with men and a couple I enjoyed immensely when I sensed they were treating me as a woman. However those dates were few and far between.  

In the meantime, my contact with women continued. My first dinner out was with a friend who eventually came out as a trans man but was still undecided (?) when we went out. I hung out in lesbian bars and even left a mixed party I went to one night with a lesbian and went to an upscale club. Destiny has a funny way of hiding around corners when lifestyle changes are considered.

Through this all, I really had very little knowledge of how to date while transgender. In fact, I was still on the gender fence as far as which way I would go. I just knew my attraction to women had not changed during my transition. 

All of this leads me to my final attraction to and acceptance by a group of lesbians I met in a sports bar. Including my current partner of ten years Liz.

I have led a sheltered dating life. 

These days I see on social media many more alternatives to dating between various groups such as transgender women. Even now though I still see very few trans women with men. It seems to be the last frontier of dating. At times it puzzles me because transgender women are uniquely qualified to be with men. After all, we understand what men go through in life. 

As with so many other things in life, I know most men have a very fragile sexual ego. So I do know this one.

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