Set Her Free

Image from JJ Hart

Throughout my long life, which included fifty years of being a cross dresser, I could feel the stress and tension of not freeing my inner girl.

It all started innocently enough with trips in front of our family mirror in clothes I had borrowed from my Mom. Of course that all ended when I outgrew her sizes and I needed to strike out on my own to find fashion which fit. With my meager allowance and money I made from delivering newspapers to the neighborhood, I managed to get by and buy a few items to add to my wardrobe which then I needed to carefully hide away from my family.  Somehow I survived and my life as a male set in, no matter how much I did not want it to. 

The gender stress and tension continued over the years and even became worse with every success I had when I tried to set my inner self free. It finally became evident my entire gender life was backwards, I was not a man cross dressing as a woman, I was a woman cross dressing as a man and it was no wonder I was feeling the confusion and pain. I would not have wished the mental anguish I felt on my worst enemy. I found being transgender was far from being a choice and somehow I needed to set her free.

The problem was, I needed to face the same set of hurdles transgender women and trans men face. Such as family or spouses, friends and occupations. The longer you go in life, the more gender baggage you acquire, the more you have to get rid of. Or figure out how much you can keep. My prime example always is how I was able to maintain my love of sports when I fully transitioned into transgender womanhood. I had help when I learned the women around me loved sports as much as I did and I felt right at home. It was easier to set my woman free. 

Finally, I arrived at the point where I could take it no longer. I ended up living more time as a trans woman than I did as my old male self. So much so, I was feeling totally out of place in a male world as a guy and would have rather attacked it as a woman. Plus I still had the age old problems of doing my best appearance wise as a feminine person. I began by losing nearly fifty pounds and taking better care of my skin on a daily basis and worked my way forward from there. Through days of trial and error, I was able to arrive at a point where I could provide a reasonable attempt at presenting as myself on a regular basis. The key was to settle in to what myself should look like which meant stopping doing things such as switching wigs on a regular basis. Finding who I was proved to be the key to setting myself free.

Once I did manage to set my dominant self free, she did all the rest. I learned to keep my old male self out of the way and let her go. Among other things, she picked my friends and lover and opened the door to a life I never thought possible.

It was like she was saying I told you so and should have done it sooner. 

Fall Leaves

Image from Alisa Anton
on UnSplash. 

I write substantially how fall is my favorite season of the year. I love the cooler temperatures, wardrobe changes and how the trees change into their brilliant colors. All before the colors go away and drab winter sets in.

Long ago, I felt all the seasonal changes deep down to my inner soul. Of course as a novice transgender woman the wardrobe fashion changes were challenging and fun. I learned I needed to look ahead for the best clothing bargains if I was to be successful in locating all the fashion firsts in sizes that fit me. After a few seasonal changes, I began to feel so natural, I automatically felt the changes coming on. Fall was especially fun when it was time to go through all of my leggings, boots and sweaters to see what I would have to add or subtract to make it through another season.

Even though fashion changes were exciting and fun, other aspects of the season just brought about melancholy depression. I vividly remember the nights when I went out and just drove around in my car watching all the leaves blow around in the headlights. Here I was still stuck in a gender I did not want to have anything to do with and not seeing a way out. Very soon, the fun of fall would turn into the depression of winter for me. My final fall before leaving for Army basic training was especially bad because I knew for a fact I would not be able to do anything about my transgender desires for a very long three years of my life. It seemed so unfair my new life into transgender womanhood would have to be put on hold through no fault of my own. I was bitter. 

Little did I know, after waiting over two years out of three in the Army, karma would come back to help me. During my last year I learned of a Halloween party which was being planned by a hospital group which my friends and I were invited to. Immediately my mind jumped to the possibility of me dressing up as a woman and going. Of course the problem arose how was I going to do it because I did not want to go halfway. I wanted to be the sexiest dressed woman at the party. Fortunately, I had access to an apartment where I could finally shave my legs and put on makeup with a wig I managed to buy at a downtown Stuttgart, Germany shop where I was stationed. Through it all, I knew I was risking harassment or worse by my superiors in the Army if the word got out about my so called "costume" which may have been a little too good. But nothing ever happened.

In fact, because of the Halloween party, my life changed nearly full circle that fall. A couple of days after the party, when my closest friends gathered once again over potent, tasty German beer I blurted out the costume I wore was more than a casual fun idea I came up with on the spur of the moment. I was a transvestite as we were known back in those days and I enjoyed wearing women's clothes, makeup and wigs. I knew at the time, again I would be risking what was left of the time I had left in the Army if what I said found it's way into the wrong hands. It did not matter at the time as the first time I left my gender closet felt so good. So good, I tried to come out to my Mom who promptly slammed me back into my closet. 

All of this happened during the fall which still remains my favorite season of the year. As a  transgender woman, I appreciate the re-birth of spring but summer is too hot and winter is too long and drab. It's why fall leaves are so important to me.  

Connections through Isolation?

 

My wife Liz on left
from the JJ Hart Archives

When I finally began to be successful in my femininized public pursuits away from the mirror, I was content to be alone in the world.

By being alone, I didn't have to face any communication problems with anyone else I faced. Essentially, I just passed through their world quickly and was gone. I did not want to know them better and have to challenge myself into interactions with strangers. Ironically, my idea did not last long as I was increasingly thrust into public interactions as a transgender woman I did not want. In the beginning, I just was not ready to look another person in the eye and risk ridicule.

I learned quickly, my public interactions would be overwhelmingly with other women. Initially, I interacted with clerks in clothing stores who were mainly interested in helping me with my money, except for the few who wanted to help me with my fashion. It did not take me long to realize what was going on and then move on. 

I began to stop and eat lunch to extend my shopping trips which meant ordering from a menu with a server and/or bartender. I found sitting at the bar made for a more personal experience unless the staff was very busy with other patrons and I could try out speaking with others as a trans woman. Very soon out of forced habit, I found myself relaxing more and even enjoying the experience. It was like I was completing a long lost part of my new personality as I left the mirror and entered the world. It was a challenge and I grew to love it. I discovered also many more women than men wanted to know more about me. Women were curious while men were scared of me it seemed and I loved it. 

Along the way, when I first began to communicate I tried to mimic the voices I was hearing from other women and try to repeat doing it until I thought I was doing it right. I even took voice lessons for awhile to improve my vocal presentation for my transgender womanhood.

Still, after my second wife passed away, I was extremely lonely. Not only was I facing finding another person I loved at the age of sixty, I also had the added pressure of doing it as my new version of my authentic feminine self. I was prepared to spend the rest of my life by myself. Little did I know I would not have to. Initially, when I went out to supposedly socialize and find new friends, I was going out to be by myself. If my gender was never challenged I would have taken the easy way out and would simply go back home to my two dogs. 

If it wasn't for a bartender at one of the venues I had become a regular in, I would have remained in the social rut I was in. One night not long after I arrived, she served me my first drink and quickly asked me if I would be interested in meeting her single lesbian mother. Of course I said yes, and a friendship  started that has continued over ten years till today. She is the woman who took me to the NFL Monday Night Football game. A very scary experience which cemented my arrival as a full-fledged transgender woman in the world. But that wasn't all that happened at my favorite venue. Another night, as I sat alone to be by myself, another woman came in to pick up her to-go order. While she was waiting, she slipped a note down the bar to me asking if I was interested in having a drink sometime. I said yes and the three of us ended up having a great time the next couple of years as we watched sports, drank too much and had fun at lesbian mixers. My two new friends ushered me into a world I never thought I could go.

Against all predictions, my connections through isolation worked very well for me. My new friends which included my wife Liz who also identifies as a lesbian, all helped me into my own important version of transgender womanhood. Destiny was certainly helping me during this period of my life.