A Point of No Return

 

Image from the Jessie Hart
Archives.

For nearly a half a century I considered myself a more or less serious cross dresser or transvestite. In addition, I considered the transvestite label little more than just that, a label which was appropriate just to  use around others. Even though I rarely told anyone else about my gender issues.

The only people I can remember telling would number under ten before I finally came out into the world as a novice transgender woman. The first people I ever trusted enough to share my biggest secret oddly enough were friends I had in the Army. My disclosure came after I risked what was left of my time in the Army by dressing totally as a woman for a Halloween party.  Following the party, several weeks later under the influence of great German beer, the subject of the party came up. Of course then, the conversation went to what our costumes were. 

When the subject turned to me and how good I looked, I gathered the courage and told the three others the night was not the first time I had cross dressed as a woman and in fact I was a transvestite. I ended up taking a major leap of faith telling them because I still had approximately six or seven months to go on my enlistment and conceivably I could have encountered problems if the gender information I disclosed got into the wrong hands. After making it so far towards an honorable discharge, I certainly did not want to destroy the time I had put in. Plus, what would I tell my friends and family at home when I arrived back there early. 

To make a long story short, nothing negative happened with telling my friends I was in reality a transvestite and the experience was very liberating. On the other hand, I was not going to tell the rest of the world my secret. Of importance is the fact one of the people I told that night turned out to be the mother of my child and future wife. So I did not have to worry about telling her once we became married. I see her to this day and we still get along. Sadly, the other two friends I told are now deceased and I lost track of them almost completely before they passed. 

All of this brings me to the next person I told which was my Mom. It happened one night shortly after I was discharged and I was living at home for a very short while. One night when I came home from partying with my friends she was waiting up for me just like back in my college days. Somehow the conversation turned to my life and what I was up to. Out of the clear blue sky I decided to tell her my deepest secret about being a transvestite. I was still feeling liberated from telling my friends in the Army and felt secure in telling her, betting she would never tell my Dad. Just about the time I was feeling good about including Mom in my world, she turned around and roundly rejected me. All she really did was offer to pay for psychiatric care to solve the problem. Very quickly I rejected her offer and said no one was going to, in essence, plug me into a socket for electro-shock therapy.  From then on until she died, the subject of my growing gender dysphoria was never brought up again. 

The last person I came out to when I was still in my gender closet was my second wife. I write extensively concerning our gender battles but the fact remains she supported me as a cross dresser until I began my transition into a transgender woman. In essence, over the span of our twenty five year marriage, we just grew apart until her untimely death. 

Once I reached the point of no return in my male to female gender transition. there was no point in worrying about telling anyone I was transgender. It was obvious to the public who interacted with me what I was and they were left to draw their own conclusion. All of a sudden, all the pressure was off of me. All I needed to do was to do my best to present to the public who I really was. Plus, I would be remiss if I did not mention the roles gender affirming hormones played in my experiences. I was so happy with the results I was experiencing, I never wanted to go back to a testosterone filled life. For once, a plan came together for me and the point of no return never had to be challenged. 

Close Encounters of the Transgender Kind

 

Image from the 
Jessie Hart Archives.

Very early in my life, similar to so many of you, I suffered many close calls when it came to being caught in my feminine clothes by my younger brother or worse yet my parents. 

As with most inquisitive younger brothers, if I was out of his sight for any length of time, he wondered what exactly was going on. To make matters worse, we were just a couple of grades apart at the same school, so we rode the same bus home and arrived at the same time. Leaving me very little time to cross dress and admire myself. I even had to hide out in the woods when the weather was good to dress up.

My parents were partially a different story. My Dad was a banker and Mom was a high school teacher, so they arrived home usually in time to sit down to dinner. If you remember those days. My point being, seemingly for weeks at a time I couldn't find a way to explore my gender closet at all and the pressure to do it just increased to the point of no return. Which meant I needed to take risks. We had two bathrooms in our house and sometimes I could barricade myself into the one which contained most of my Mom's makeup. When I combined her makeup with mine, I had plenty to experiment with. 

On the exceedingly rare days I was left all alone, I went all out. Even to the point of being able somehow to get away with shaving my legs. I was completely in love with how wonderful the air felt on my freshly shaven legs when I took the chance to walk to the mailbox which was some distance away. No matter how good I thought I looked, the biggest problem I had was with my hair. In those days, I was stuck with either the ultra short burr haircut my Dad had or the equally as bad crew cut. A wig of any kind to me in those days just seemed like the impossible dream and it wasn't until my college years when I could afford to buy a nice wig I cherished for years. I even hid it, as well as other cross dressing necessities away when I went away to the Army. Hoping they would not be discovered. They weren't. 

Even with all my precautions, I still ran into the times when I had to hurriedly wipe the makeup off my face and change my clothes when my parents came home early. I don't know how but I somehow survived without a gender confrontation which would have been a disaster. At the time, I thought when I became older I would have more control over my cross dressing desires and life would be better. In no way did I feel as if all of the sudden I would wake up with no gender dysphoria and life would be much better. On the other hand I still felt I would not have to hide my true self to others. To compensate, I developed a very macho exterior self and avoided making very many friends who I may have to come out to later. A process I would come to regret later in life.

It turned out, mainly because of my wanting to not come fully out as a transgender woman, hiding away my true self from a loved one would reach new heights of desperation. The loved one I am referring to is my second wife who knew from the beginning of our relationship I was a cross dresser and accepted it. Everything in our relationship was good until I finally faced the truth of me being transgender, which my wife soundly rejected. Increasingly, when she was working nights, I was out exploring the world as a trans woman to primarily see if I could make it or not. When I found I could, I began to go out more and more which led me to having more chances of being caught. All of which led to huge fights when I came home as my feminine self and she was waiting for me. It was like I was a kid again and resented the process completely but it was like a train wreck waiting to happen.

Our relationship became so strained, my wife told me things like why didn't I just man up and live as a woman. A great point which I never did while she was alive. Somehow, it was similar to me trying a last gasp attempt at saving what was left of my manhood at her expense.

When she did unexpectedly pass from a massive heart attack, at the age of sixty, I finally was able not to worry about any close gender encounters. I had paid my dues and was so happy to fully come through an often very uncertain life and live in the world as a fulltime transgender woman with no negative people in tow. A dream I thought I could never achieve.   

Gender Euphoria

Image from Mohammed Nohassi 
on UnSplash.

During my circle of life which I am fortunate to still be living, there have been tines of intense gender euphoria. Those times seemed on occasion to correspond with  my severe bouts of gender dysphoria. 

Examples of euphoria came when I gathered the courage during a cross dresser-transvestite mixer I attended to have my makeup applied by a professional makeup person. He ended up working miracles on my face and I looked great (in my humble opinion) which was to be proven later that evening. What happened was I ended up tagging along with the "A" list cross dressers or transgender women in the group who always continued the party at an outside venue after the main mixer closed down. The first venue we went to was a large gay and lesbian dance club which I never really liked but I went anyhow. 

During the evening, the group broke up even further and we went to a much smaller venue which I couldn't tell was gay or not. All I knew was I enjoyed the music better and the place had pinball games I could entertain myself with. In a case of timing wasn't everything, about the time the remaining "A" listers wanted to call a cab and leave, I was approached by a handsome man who wanted to buy me a drink and play pinball. It turned out to be one of the pivotal moments of my cross dressing life when I politely declined his invitation and left. I was then forever caught wondering what would have happened if I would have stayed. Primarily I didn't because I would have been stuck in a strange city which I had very little knowledge of with a man I didn't know. On the positive side, I was the only one in the group who was approached by any other patron at all. In that moment my gender euphoria reached one of it's peaks. Perhaps the best part of the experience were the advanced makeup tricks I was able to understand and remember later. 

Of course there were other moments of intense euphoria such as the night I needed to show my male drivers license to be admitted to another transvestite mixer I went to. The greeters at the door thought I just had to be a cis-gender woman. Sadly, with every success I had with these cross dressing experiments, there were the downsides also. Mainly because of my ego which still in many ways was dictated by my old male self. For lack of a better example, every up comes with a down and when I crashed over a gender euphoric high, I was not an easy person to live with. To make matters worse, my crash was so bad, I couldn't keep my mind on anything other than the next time I could cross dress and go out as my feminine self. None of which my second wife approved of. Looking back, I don't see now how our twenty five year relationship survived. 

Regardless of these few and far between gender euphoric moments, I can safely say gender dysphoria ruled my life. Starting with the days when I was a kid wondering if I was a boy or a girl and continuing into and with daily combat with my mirror. Again and again I suffered the gender torment of seeing feminine in the mirror one moment and masculine the next. It was during my darkest moments when I found I could indeed lead a life as a transgender woman that got me by in life, barely. 

By the time I had reached my sixties and had started HRT, I knew I would never have wished my life's journey on anyone else. Going behind the gender curtain and learning life from both sides of the binary gender spectrum had certainly taken a toll on me. On the other hand, the experiences I went through taught me to be a better human being. 

Balancing gender euphoria with massive gender dysphoria in life can be a daunting task and one which should not be taken lightly as it can effect a person's overall mental health. Gender is one of the deepest emotional issues a human can have. It can never be taken for granted it seems with a transgender woman or trans man, unlike a large portion of the rest of the population. Which could be a topic for a future blog post.