Was there Ever a Plan

Image from the JJ Hart
Archives

Looking back, I needed a very definite plan to follow as I transitioned into transgender womanhood. 

Similar to so many of you, I started by "borrowing" a few of my Mom's clothing when I could still fit into them. I would have added a sister in but I did not have one. When I became old enough to do it, I took on a newspaper delivery route in my neighborhood and combined my new meager funds with the allowance I received at home from my parents and with the money, I was able to buy a few clothes and my own makeup. Since we lived in a rural area outside of town, the plan was to stay a day or two with my Grandma who lived very close to stores *downtown where I could attempt to shop for what I wanted. The problem with the well thought out plan was my Dad worked downtown too and he was the last person I wanted to run into with my new "treasures." 

After I conquered my fear of shopping for cosmetics I did not really need, I was able to buy makeup which did not make me look like a clown. Another problem I had was, the only example I had of applying makeup came when I was able to watch my Mom do it. I wonder if she noticed me watching her. She was probably so entranced in her face, she did not notice I was entranced also. 

The older I became, the more entrenched the plan became. I was able to increase my small "collection" of feminine wardrobe and makeup as I went along and managed to hide it from my brother and the rest of my family. At the same time, I wanted to become better at the makeup arts and finding clothes which fit me. 

At the same time, I became comfortable with how I looked in the mirror and increasingly had thoughts of expanding into the world. I did try to come out fully dressed to one of the very few male friends who lived close by in the neighborhood but was quickly rejected and I scurried back into my dark, lonely gender closet. I stayed in the closet until several Halloween parties began to bring me out. From then on out, my plans really began to change.

During the parties, I learned how much I enjoyed my time out of the closet and I just knew I needed to figure out a way to live as a transgender woman without waiting for a whole year to go by. To do it, I knew I would need to start by telling my spouse what I was up to. So the plan was to find out what wife number one and two thought about me being a cross dresser before we were even married. It turned out wife one did not care and wife two was supportive to an extent which helped me along. 

The main rule I had with wife two was to never leave the house dressed as a woman. I started innocently enough before I veered off course and threatened our marriage of twenty-five years. I began going to women's clothing stores and malls where acceptance was easy to come by. Money was certainly more important than gender. I also would go to bookstores and even antique malls where I could browse with no problems to build my confidence. When my spirits went up, I planned ahead for my next big adventure which usually meant beginning to interact with more of the world as a transgender woman.

To do it, I began to stop and eat at restaurants along the way to make sure I had to communicate one on one with a server or bartender. Since I had an extensive background in the restaurant/bar business, I knew basically what I needed to do to survive. Just be nice, do not cause any trouble and tip well and I could be successful. 

From then on, I endlessly planned on what I was going to to next and how I could challenge myself in the feminine world. Sometimes I was successful, sometimes I was not but I always learned from the experience. In my life as a man, I had never really planned ahead on anything, so this was a big difference. Perhaps it was because I could not wait to try again to live out my dream of transgender womanhood.

*Those were the days of strong vibrant downtowns in many cities, including mine. Before malls took over and they tore the downtowns apart. 

All I Ever Knew

Circa 1940 image
of Virginia Prince

 Every once in a while I receive the question when did I know I was transgender.

The easy answer is I always knew but I needed to figure it all out. The more complex answer is I needed to figure it out after a series of transitions during my life. Two major ones occurred when I made the jump from from a very serious cross dresser all the way to a novice transgender woman. The second problem I had was back in those days, terminology to define a transgender woman or man had not yet been invented. Basically back in the pre-internet days when all we had was the preaching of Virginia Prince and her Transvestia publication which I could not wait to receive in the mail. Seeing all the pretty cross dressers just made me want to do more to improve my feminine appearance.   

I worked harder on my appearance than any thing I had ever done before and slowly began to see improvement over my testosterone damaged male body. It was all I ever knew. 

As I entered my transgender womanhood, I felt deep down inside I was doing all the right things, even though I was jeopardizing all the facets of my male life I had worked so hard to put together. What would I do when my family, friends and bosses discovered my deep secret. It ran so much deeper than just wanting to wear women's clothing. I wanted to be a woman and live a feminine life. 

During that portion of my life, I basically went into attack mode, doing every thing I could to learn how being a transgender woman would affect me. Every free moment I had, either I was out in the world as a woman or day dreaming of the times when I could. Naturally, I learned a lot, good and bad about what life had in store for me if I kept on going towards my gender dreams. I found the grass wasn't always going to be greener on the other side of the gender border as I lost all of my male privileges but hadn't gained any of the female ones. 

Soon I learned, it was truly all I ever knew. Somehow I was born to be feminine and not masculine. Which meant years of struggle to right the gender wrongs I was living. The struggles on occasion were crushing and keeping going was very difficult but I did. Probably because I was behind before I even started. I was born into a very male dominated family which had very few girls to play with. Plus, I never had any feminine characteristics myself to begin with. Add it all up, then include me never having any girl time with anyone all teamed up for a rough start for me on my gender journey.

Even still, my gender path was all I ever knew and staying on it finally made me successful. 

Trans Woman in the Sisterhood

 

JJ Hart on left out with Friends.

I write often concerning my gender transition into transgender womanhood. 

Sometimes I wonder if I emphasize the complexity of doing it. Securing a place for me in an unwanted male world seemed to be so simple. Men have just a few power bases to interact with as they proceed through life. Such as money, or athletic prowess. Plus many males never have the chance to grow into manhood at all and never mature into quality human beings. 

Women face the same hurdles. Many females never make it  to womanhood. Which is a socialization process. Transgender women face additional obstacles during their journeys to be accepted into the sisterhood. As my second wife always told me, I did not really know the gender processes cis-women go through and she was right. I had not earned my right to be there...yet. It was not until I made it out of the mirror and into the world did I begin to learn what she meant. In many ways, she forced me to learn it on my own without her help. She was much wiser than I was but I was stubborn and determined to learn on my own about what being truly accepted into the world of women meant.

First of all, I needed to discover women operate in a parallel universe than men and somehow I needed to slide behind the feminine curtain and learn from other women how their world was run. I discovered that just like men, there were the alpha women who once they accepted you, you were in. With women, the difference was they were much more layered than men. Take appearance as an example. While I started out obsessing on how I looked, other women around me were noticing how I acted. I needed to walk a thin line with my communication efforts with women. On one hand, I was the quiet observer of what was going on but on the other hand, if I was too quiet I was coming off as too aloof or worse yet, bitchy. In the end, I was able to walk the communication tightrope and survive in a new exciting world as a transgender woman.

The biggest surprise I continued to have was how layered the whole experience was and is. Take conversations about children as an example. Women who have birthed kids share a special bond with other women who have done the same. I needed to interject my daughter and grandchildren experience on occasion without going too far. I felt the entire process femininized me and kept me behind the gender curtain. Being apart of the group was good. 

After awhile, being in the sisterhood had it's rewards. I mostly socialized with two or three cis women all the time which kept any potential problems from materializing. I was able to be protected from being a single woman out by herself and learn about the life I wanted to live in the meantime. One evening at a time, I was earning my way into my own level of transgender womanhood. Many times the process was scary. Such as the evening I went to a pro-football game with friends but the offer was too good to turn down no matter how frightening the situation was. Since it happened when I was first climbing away from my dark closet into the world. 

In so many ways, I owe several women friends whom I always say helped me more than they will ever know. They ushered me into being a trans woman in the sisterhood. 

Ironically, it was only the beginning as I needed to keep building on the feminine experiences I was having. A prime example was when I moved in with my wife Liz in Cincinnati. When I did, we started to attend small meetup groups with total strangers which added to the layer of meeting and being accepted by other people. The entire process for the most part was very positive and a great way to immerse myself even farther into the sisterhood.