Monday, May 11, 2026

The First Time

 

JJ Hart

There are plenty of first times in a person’s life that we can set up on a pedestal and remember. Such as, the first time you had sex or the first time you drove a car can create some memorable experiences.

I venture a guess that we transgender women and transgender men have more than our fair share of first times to look back on. I know I do. For example, I remember vividly the first time I went exploring in my mom’s garment drawers, and deep down something clicked inside me that I was on a new and exciting path I could never get off of. I also remember the first time I drove a car on a country road at the age of fourteen when no one else was around and I remember the first time I had sex with a woman, and she told me that I would never forget her and she was right.

For many reasons, these were the easy firsts to remember other than times such as when I was in the delivery room for the birth of my only child and negative ones such as when I needed to go to Ft. Hayes in Columbus, Ohio for my draft induction physical. Standing in a room full of naked men was not my idea of fun and a first time I did not want to revisit. There were also lesser first times such as graduating college and receiving my honorable discharge from military service that I was proud of but not as much as I was when I started to fill out my gender workbook and begin to advance towards a stable transfeminine future. It was only then that I began to grasp the importance of life’s first times that I was sometimes racing past before I even knew it. I was so bad about not living in the present and appreciating it for what it was. I was always thinking about the future before the present was over.

When I began to search for my feminine self in the world, I needed to stay in the present more than I had ever needed to in the past. If I did not, I would forget what I was trying to do that night as far as being a novice cross-dresser or transgender woman. I could be mirror-ready with my clothes, makeup and hair and still destroy that image with the wrong movements if I became too careless and forgot where and who I was. Who I was, was the most important time of my life as for the first time, I was attempting to see if I could (against all odds) survive a dream run towards my goal of living as a trans woman in a world of ciswomen everywhere.

As I did become successful, my mindset began to change, and I started to think of myself of a transgender woman more than some sort of a casual cross dresser. I knew it was completely a mental move but still a very important one as I scaled the steep walls of my gender path. At the time, the term transgender was just being used more and more, and for the first time in my life I found something that really described who I was. All those years I had gone to those “Tri-Ess” cross-dresser social mixers were wasted because I still came away with the idea that most of the others were not like me. It took me a while, but I finally began to appreciate the individual that I was for the first time. When I began to remove the cross-dresser word from my mental vocabulary, I was beginning to insert the use of woman and inwardly began to refer to myself as a she, became a milestone in my existence because I was coming to the point of understanding for the first time, I was a woman. Just one with a unique background which should be celebrated, not scorned.

My only problem I had with the whole direction I was heading in my life with my feminine self was that the potential I had to hurt others I loved in the process. And if I had followed my instincts and done the male to female transition, would I had been better off in the long run. For the first time in my life, I felt as if I was wasting my life as a man. What was left of it was only the physical image I presented to the world when I worked and when I was around friends. I was still under the impression I needed his male privileges to exist in the world which were nice to have in the short term but had to go for the first time when I decided to transition into a new, exciting transfeminine world.

Not to say the new world did not present constant challenges to not slip back into my old ingrained masculine ways from living nearly fifty years on and off in that world I was born into without a choice of getting out of. It seemed I was in a dark closet I could not get out of until I made more than a few serious efforts such as going out and carving out my own new life with people who knew nothing of my past. For the first time, I made it in a world full of ciswomen who saw nothing wrong with me being behind their gender curtain and it was as if I had always belonged to the new world I was in. Which was true, I had never been able to get there until I took chances and made the effort. Of course, back in those days, the world was in essence a kinder and gentler place with people less inclined to be in others business.

In my male life, I had always been quite guarded because I did not want anyone in my gender business. As I went female, everything changed and I did not mind anyone knowing my big secret. I was a woman of a transgender background, and I found people who respected me for my honesty on how I was living my life. For some reasons, especially lesbians who let me into their world, and socialized with me as we were regulars watching sports in a few big venues and regulars for the first time at lesbian mixers, I was invited too. In fact, often I was a better “mixer” at these socials than my friends were. I was having fun for the first time in a long time in my life.

I was moving so fast, I finally had to slow down and think of how far I was able to come with the help of my small circle of friends and my future wife Liz. I needed to work on staying in the present for the first time in my life I had a present worth living for, not just going through the motions.

Thank you all for staying with me through all my experiences, and responding with claps, comments and suggestions. As I always say, without you all, none of this is worth it to me.

 

 

 

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The First Time

  JJ Hart There are plenty of first times in a person’s life that we can set up on a pedestal and remember. Such as, the first time you had ...