Trip Number One

 

Hair after salon image 
Jessie Hart
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Way back when, one of the first priorities I had was coming out to my only child, a daughter. Of course I was properly scared to death the morning I told her at breakfast. 

It turned out all the paranoia I felt was unfounded when she wholeheartedly supported me. Which she does to this day. Outside of my wife Liz, she is one of my biggest transgender allies. Especially since her oldest child came out to her as trans, so she had some experience with the entire situation. 

When I came out to my daughter, I had a chance to let my hair grow out to the point where it could be styled professionally at a beauty salon. Which at the time seemed to be the impossible dream. It also was close to my birthday so as it turned out my birthday gift was a trip to her (daughter's) very upscale salon for a color and trim. 

Even though the entire idea of going to a women's beauty salon  really scared me, how could I refuse such a wonderful gift. Before I knew it, the time to meet her and go through with the visit was upon me. For my first visit my daughter came with me to essentially hold my hand, because I was almost ready to panic and run out the front door. But I didn't. As I nervously sat and waited with a cup of coffee, I wondered what was going to lie ahead and what color was I going to choose for my new hair. Since I had retired, I didn't have to worry about any negative responses from employers or fellow employees. Freed up from all that worry, I was able to worry about my choices.

Finally, it was my turn to be called back to my new stylist. Predictably, the salon itself was long and narrow with a single line of women in chairs being styled. Walking in front of all of them and feeling their eyes on me did not do me any favors when it came to my nervousness. After greetings were exchanged, the first priority was picking a color to change what was left of my dark hair which was my natural color. By mutual agreement between the stylist, my daughter and myself, we decided to go with a streaked light red and blond look. Plus, since my hair is naturally wavy, the stylist straightened it out. Which later on I found I didn't like.  

By the time all of this was happening, I thought I was getting a contact buzz from all the estrogen in the room. Through it all, I quickly discovered what I was missing by never being able to go to a woman's only space such as an upscale beauty salon. Before I moved, I ended up going back several times before I moved away to Cincinnati. Plus, the more I went, the more I relaxed and enjoyed the experience. 

It took awhile but I found and set up many appointments with a new stylist here in Cincinnati who happened to have a transgender son. Again she was very good at her craft and I enjoyed going to her for hair advice and stylings before she retired due to problems with her hands. With her though, the experience was singular because there were no gauntlet of women to walk past everytime I went. She had her own little cubical. 

I will forever be in debt to my daughter for her birthday gift so many years ago which brought me into the  world of beauty salons. From that point forward, I began to understand why women spend so much time and money on their hair.

Making Lists

Image from UnSplash

 Every once in a while I receive a question about how I transitioned into a different transgender world. 

For a time I made mental lists, outlining where I would go and what would I do. Before I became involved with lists, I needed to decide once and for all I was indeed a transgender woman and had transitioned from being a very serious cross dresser or not. Once I did, my existence became so much more complex. In essence I had to decide a new path for the rest of my life. What would I do about my family, friends and finances. It was all so easy and fun and games when my only worry was how I looked in the mirror. After I decided to do so much more, I really needed to make my mental lists for the gender challenges I was suddenly facing.

The first lists I made involved where I was going in the world. I needed to challenge myself and do extra trips away from the usual women's clothing stores and seemingly safe gay venues I was going to. My expanding life was all too predictable and provided me no chances to expand my new feminine perspectives. Clerks in stores were just interested for the most part in my money and the gay venues just mistakenly thought I was a drag queen. One big exception were the lesbian bars I discovered. I went primarily to two of them. I was hated in one and accepted in another. The lesbians in the second bar were intrigued by me and I was even asked one night to sing karaoke by a large butch who wouldn't take no for an answer. Since I am a terrible singer, I sang in a low background voice and somehow made it through my musical challenge. I crossed the evening off of my lists and made a mental note to attempt to never see her again. Which I did not. 

On occasion, my activities collided head on with me hiding all of this from my wife. When my wife needed to work her retail job at night, many times I would use the time to head out the door and explore knowing I would need the time to be home, take my makeup off and appear as if nothing happened when she returned. Many times I was not successful and a huge fight would ensue when she saw vestiges of eye makeup left behind. Somehow we were able to make it through the skirmishes and most of the time I made it home before her.

Many nights it was difficult to pull myself away from my list to keep from getting in trouble. I remember vividly the night another butch said to me she should take me home. I had no idea if she knew the truth about me and what she was bringing home but I was out of time and couldn't wait around to find out. I couldn't imagine what excuse I would have had to come with for my wife if I had explored the evening farther. I had to rip up my list and forget it, for a time. 

From the confidence I had built up in the lesbian venues I went to, I then listed sports bars as my next challenge. I had always enjoyed going to sports bars to drink beer and watch the big screens when I was a guy and wanted to see if I could do the same as a transgender woman. Fairly quickly I found I could and I needed a new list of goals to conquer. 

By this time, I was ready to try gender affirming hormones and plan ahead to the strong possibility of being able to discover a fulltime life as a trans woman. During this time, I was checking skills such as public communication off of my check lists and set out to try to conquer a brave new feminine world. Finally, my new life became second nature and I didn't need any more lists at all. 

Supporting Casts

 

Girls Night Out. I am on the Left.
From the Jessie Hart Archives

One aspect of my gender journey, I don't mention enough is the importance of the supporting cast I had around me to help me along.

They clearly helped me during the times of my life when I was down and almost out when it came to me going any farther as a transgender woman. A prime example was when I started gender affirming hormones and was wondering if it was the right move to make. By just being a part of my life and understanding what I was going through brought about a significant need for moral support. Another example was when I began having hot flashes and my women friends (cis-gender) just smiled and said welcome to their world. Which is exactly where I wanted to be. 

Over the years, there was only one woman who held my gender issues against me. She was my first fiancé who in the past, one time cross dressed me head to toe as a woman. The whole process turned out to be a bittersweet experience. For the first time in my life I had tried to share my deepest secret with another person and turned out to be less than impressed with the entire outcome. When she had finished with my makeup, I saw no real improvement over my efforts which ended any ideas I had that women had an edge over cross dressers when it came to makeup applications. So, the sweet part was limited and doomed to fail to begin with. The bitter part came later on when my fiancé broke up with me after I refused to say I was gay in order to not be drafted into the military during the Vietnam War. Lesson learned and I went back into my deep dark gender closet for years until I met my first wife. Even though she always knew I was a cross dresser or transvestite, she never made a big deal about it. 

Around that time of my life the biggest support I received ironically came from a man. A stranger who was doing makeovers at a cross dresser mixer I attended. I put on my big girl panties, removed all my makeup and let this stranger work his makeup magic on my face. When he was finished, I couldn't believe the transformation. Plus, I was actually able to understand and redo the makeup steps and repeat them. The entire process takes me to my experiences with my second wife. Similar to my first wife, she knew I was a transvestite from day one in our marriage and even supported me...to an extent. Keep in mind, we were married for twenty five years and during this time, I was slowly transitioning more and more into the transgender woman I am today. Before my wife's untimely death, we had numerous fights over my desire to be a woman and begin gender affirming hormones. Her stance until the end was she didn't sign up to be with another woman. To make matters worse, I don't think she ever liked my inner feminine self and the two women battled continually.

After she passed on, it took me a few years for me to recover from the shock and get on with my life. One positive I carried with me was how affirming the presence of my feminine side turned out to be. As it turned out, destiny led me to other groups of women who essentially adopted me into their tribes and helped me to flourish. 

I can never say enough how much I learned from all our girls nights out together. Without all of them I can never imagine how much longer and which direction my transgender transition would have taken.