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.  

Empty Houses

Photo from the Jessie Hart
Archives

 As I grew up in a male world, I naturally adopted many male dominated activities and hobbies which I stored away in my house I had to build as a guy. 

Mainly because I was frantically chasing
my desire to be feminine, I sometimes jumped from activity to activity rapidly. Plus none of this was accounting for the traditional male things I was doing such as building a family and trying my best to provide as good of a house I could. As far as actual house goes, I was trying to follow in my Dad's shadow and come as close as I could to either remodel or build my own house. He built his own house while I worked hard to renovate an 1860's era brick tavern in the town I was from. I came close but I don't think he understood why I did it. 

Bu it wasn't easy. I needed to teach myself the basic's of plumbing and electricity among other important things associated with remodeling an old structure. The end result was my second wife and I were able to live comfortably there in the years before her death. Then, I was all alone with a couple dogs and a cat in this huge empty house. At that point, I needed to decide which direction my life would take physically and mentally. What I mean was, was I going to continue to try to live in the house I remodeled with all it's memories or try to move on. With all the animals of course. What I decided to do was make the house even emptier by selling all my wife and I's vintage collections on line and using the money to augment my Social Security money I was making. In doing so, I managed to keep the house going for awhile as I sought out the possibility of taking an early retirement. Eventually, years later, I was able to move us all in with my current wife Liz in nearby Cincinnati, Ohio. 

As it turned out, the physical aspect of having an empty house was much easier than the mental part. Since during my life, even though I started out shy, I became a rather social person with deep ties to my home town. Sadly, those ties had nothing to do with my increasingly dominant feminine self. With no one to stand in my way, I was actually able to pursue if I was indeed transgender or not. Or just a serious crossdresser who wanted to their best to look like a woman. Since I had the options and inspirations to discover my true self further, I finally gave in to my inner female and set out to attempt to build a new life.   

Surprisingly, leaving behind my old male life was easier than I anticipated. Destiny (and effort) led me to meeting a new group of cis-gendered women friends I could be social with and learn about a new house at the same time. Plus, all the years I dreamed about decorating a new empty gender house came to pass as I adopted relatively easy to my new gender affirming hormones and life as a fulltime transgender woman. Then my relationship with Liz, who I met on line flourished, and we were married years later after my daughter suggested we finally do it. She made sense, we married and moved on to a new chapter of building my feminine house and making it much less empty.

I am sure, when one discusses genders, not many humans get the chance to empty one house and start all over again in a new one. It is a scary yet exciting journey.