Poor Executuion equals a Hot Mess

Image from Author, Columbus, Ohio.

More times than I would care to remember, evenings when I went out to explore the world as a cross dresser or novice transgender woman turned out to be a hot mess. 

Particularly frustrating were the evenings or days when I thought I had planned everything out so well. I picked out the perfect outfit and applied my makeup just right and was ready to go. Perhaps my biggest issues had to do with figuring out where I was going to go and when I needed to be back before my wife returned home. Did I have a relatively long time to explore the world, or a short time to visit a few of my favorite venues and be back in time to remove all vestiges of my makeup and attempt to return to my male life. 

In the beginning, big mistakes would appear to ruin my time and turn it into a hot mess. I did not understand because I thought I was doing my best to put my new feminine cross dressed image to the public test. Some of my problems came from taking too many chances and others came from just purely being new to the world. Examples of taking a chance came when I used water balloons as breast forms, knowing full well how fragile they were. Predictably, one broke when I was out in public, making a huge mess in a rest room I was in. The only good thing which happened was, the room was empty except for me and I was able to clean up my mess and exit before anyone else came in.  From there, I learned the hard way to invest in silicone breast forms which I was able to use until I was able to grow my own breasts with gender affirming hormones. 

Other mistakes I would put under the title of ill-advised were the times I was simply having too good of a time and lost track of what time it was. Those were the evenings, I came home and ran directly into my second wife who was not amused. A huge fight always ensued until she settled down days or even weeks later. The whole process was not pleasant and just kept repeating itself essentially until just before she passed away. Finally I decided to purge my trans-feminization self and grew a beard for the last six months of her life. During this time, I didn't know she was as sick as she was and she passed totally unexpectedly and I often wondered if we could have stayed together for any length of time had she lived. All I do know was, I was making a hot mess out of our life because of my transgender issues. 

During this time also, I was desperately trying to catch up with all the small issues a woman has done to live her life. I did so many things such as wedging my heels in sidewalk cracks, which of course destroyed any image I was doing my best to project as a confident well dressed professional woman. 

Through it all, my wife still prodded me on by telling me I still didn't know anything about really being a woman. I wasn't able to learn until later how correct she was. My excuse is I wasn't allowed to play in the girl's sandbox until I earned it. I compare the process to being able to land a job by finally having all the qualifications needed. Until someone gives you the chance to move up, you have to earn your way or you never get the chance. I was always under qualified to play with the rest of the girls until I forced my way in.

Getting there wasn't easy. I needed to find a group of women I could learn from and not be judged at every turn. I also need to locate women who had no knowledge of my previous male self. He was never mentioned and most certainly, I never brought him up. When I did my life became so much easier. I did not have to worry about my transgender execution and hot messes became increasingly a part of my past.

Trans Girl Secrets

Image from Ben White 
on Unsplash.

Secrets became a very important part of my life at a very young age.

It all started when I viewed myself in women's clothes  in front of the mirror for the first time. I realized my life would never be the same again. Plus I also knew my desire to be a girl would not be well received by my family at all. It was in the late 1950's and early 1960's when cross dressing was still considered to be a crime where I lived near Dayton, Ohio. In those days any sort of gender dysphoria was thought to be a mental illness. Even then, I couldn't see the act of cross dressing in women's clothes to be an act of mental illness. 

What happened then was I needed to go into a dark secretive closet, I would not come out of completely for a half a century. Along the way, I included very few outsiders in my secret. Four or five to be exact. I did not even include myself in my secret. What I am referring to is the fact I wanted to do much more in my life than just cross dress as a girl, when in reality, the reverse was true. I was a woman cross dressing as a man the entire time and I was indeed transgender after all.

Predictably, one secret leads to another and another and in my case led to lies being told later on. My dishonesty came when I refused to admit to myself who I really was and took out my frustration on those closest to me. I became a very unpleasant person to be around when my gender dysphoria was at its worst. Even to the point of me losing a job because of what I was going through. It was like I was setting myself up for failure at every turn in my life as I waited for more and more people to discover my secret. 

The longer my secret was hidden away and on the other hand, I was desperately trying to discover a new feminine world as a transgender woman, the heavier my secret became. I attempted to hide all my transgender activities from my second wife and was reasonably successful. I say reasonably because I would do more and more as a trans woman until she caught me and the gender battle between us would continue. She was wiser than I was when at one point she told me to just leave her and live a life as a woman. That made her the second woman in my life who I should have listened to when they told me the same thing. The first was my gender therapist years before. 

Sadly, my male self was not ready to give up the strangle hold he had on my life and encouraged me to do the male thing and try to ignore and internalize all my struggles. Of course in the end run, the only thing which happened was the pressure just kept on building as I managed to keep my secret. However, no matter how hard my male self tried to protect his domain, he was slowly sliding down a cliff of no return. Finally, with the help of several close friends I made the gender leap of faith. I gave away all of my male clothes, started gender affirming hormones (HRT) and never looked back. 

Perhaps the best part of not having to protect my secret and not live a lie was my new friends never knew my old male self at all. My inner feminine soul was finally free to live her life. When she did, she became the third woman in my life to tell me the same thing.

The only secret I really ever had was I was never really a man at all. 

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.