My Last Date as a Man

 

JJ Hart in the long black wig
I wore to the concert. 

My last date as a man was very eventful as destiny was sending me a powerful message.

It all began a couple of years after my second wife passed away and I decided to again seek out feminine companionship from a ciswoman. Then I made a mistake and became enamored with the mom of one of my servers at the restaurant I owned. Mom was about my age and extremely attractive and I gathered up the courage to ask her out when I learned she was single. From there we went on several dates including one in her native Cincinnati. I was quite naïve and thought things were going fairly well until my daughter got me two tickets to a “Joe Cocker” concert at an outside summer festival near to where she lived in Dayton, Ohio.

I guess the idea of perhaps meeting my daughter scared her off, because after initially saying yes, a week before the concert she abruptly said no and I wasn’t to call her anymore. By this time in my life, I don’t think anything could surprise or hurt me more than what I was already going through, so I picked up the pieces of this brief ill-fated relationship and prepared myself to move on. But I had one problem, what was I going to do with the other ticket I had for the concert. Then my mind came up with a plan, why not invite my feminine self? It would be yet another test to see how successful my transition was coming along as well as soothing the ego wounds from being turned down by what turned out to be the last date I would ever have as a man with a ciswoman in my life.

At that point, I was very much still in the closet to my daughter, so I planned to pick up the tickets as my male self then go home later and get ready. Getting ready proved to be an adventure as I knew I could put together an upscale/casual outfit for the evening. I ended up choosing a black outfit with a three-quarter sleeve mesh top and wide legged silky black pants with black sandals. Topping it all off, I chose my long black straight-haired wig and sunglasses on my head as an accessory. After carefully applying my makeup, I was ready to take on the world as a transgender woman out to her first concert. I felt good and confident for a change as I left the house for the half hour drive to the concert venue.

Once I arrived, I gathered myself, checked my makeup and took off walking to the concert which was filling up with people fast. Since it was still light outside, I could wear my sunglasses to check out anyone who was staring at me without them knowing. I was relieved when no one noticed the tall, long-haired woman in black making her way through the crowded sidewalk to her seat. I even had enough time to walk up to the concession stand and order me a refreshing drink before the late “Joe Cocker” started his show. By this time in his career, he played his hits and I was happy.

I ended up immensely enjoying the concert. Even more so since I was spending unique public time with my transfeminine self. I walked away from the experience with a new-found confidence in myself to live my life the way I had always dreamed of. In a world where ciswomen ruled. And maybe most importantly, I don’t think I embarrassed myself by the way I looked.

Maybe I was a little too over dramatic when I mentioned destiny setting in that night, but it did because never again did I set out to date a ciswoman as my male self and go through all the dating contortions I hated so much. I don’t know why but I always had felt so much more at ease when I was dealing with women as a trans woman and I never looked back.

My last date as a man was uneventful because it never happened it seemed for a reason. In the future I was able to have much better times going to places such as roller derbies with my lesbian friends where I could relax and have fun. Something I rarely did when I was trying to date as a man.

 

 

A Night at a Concert

Image from the Jessie Hart Archives

Following the time when my wife passed away, I actually tried to date another cis woman, once.

During this brief period of my life, my old male self was still desperately hanging on to the idea he could still exist at all. At that time, one of my servers came into my restaurant with her very attractive Mother. After several inquiries I found her Mother was single and she would ask if she would go out with me. She did and we started our very short history of dating. 

Right from the start I found she was a bit of a prima donna when we met on a date in downtown Cincinnati. I suggested stopping at a micro brewery for a quick appetizer when she wanted to go to an upscale steak house on my dime. I should have known then she was out of my league but I kept on trying anyhow. In a very short period of time, I told my daughter I was dating again. In response, she came up with two tickets to a local park pavilion near her house. The concert performer was Joe Cocker, so I could not wait to go. I even asked the new woman I was dating if she wanted to go and she initially said yes and the date was on, or so I thought. A couple days later and a week before the concert in the park, she called me and broke up our brief affair. I was slightly shocked but then again not so much as I began to consider what I would go with an extra ticket to see Joe. 

At the time, I was increasingly exploring the world as a transgender woman, so I thought why not take myself on a date in the park. I knew exactly what I would wear .My long silky black slacks with my black matching sleeveless top and black flats for comfortable walking. I then applied my makeup and topped my outfit off with my long black straight wig and I was ready for the half hour drive to the venue. By this time all of this happened, I was becoming very comfortable with my feminine self so I was really looking forward to the evening as it approached. I had spent many a evening being alone with myself. I wasn't very nervous as much as excited by the expectation of having a good time. 

The evening of the concert turned out to be ideal weather wise, a beautiful warm but not too humid Ohio summer evening. I showed my ticket and was admitted to the venue without a problem. Before I went to my seat, I decided to buy a drink and then headed to sit down. Again I experienced no problems with anyone in the venue in my section. I was able to enjoy my drink and relax even further before the music started. I especially enjoyed the silky sensation of my clothes in the summer evening air.

I was glad I went because I had been a Joe Cocker fan since the Woodstock concert days and it wasn't too long following the concert, he passed away and I was still able to be completely enjoy his performance before it was too late.

As far as I was concerned and as selfish as it may sound, the whole exciting evening was more fun for me than taking a woman I barely knew. Plus my experience even further increased my confidence as a novice transgender woman. Even to the point of coming out to my daughter who I told that I enjoyed the concert very much but never added who my "date" was. 

The night at the concert was one of those lifetime experiences I will never forget. It was the last time I ever tried to date as a man and the first time I was ever to seriously explore my life as a transgender woman. Once I did, the more I understood it was the life for me.