Living the Dream before it Consumed Me

 

JJ Hart

As I crossed the six-decades portion of my life and spent at least five decades of it trying to stay under control by cross-dressing, I was trapped and had nowhere else to go.

It happened because I had embarked on such a complete path of looking like and moving like a ciswoman and my gender bucket list was shrinking due to too much use. All the trips to malls, antique stores, and thrift stores just became boring when I was passing through them with no problems. Even though I was bored, the idea of being successful as a transfeminine person still consumed me. And, to make matters worse, I was finding less challenges to undertake as I increasingly painted myself into a gender corner I had always dreamed about but never thought I could reach.

I always made excuses such as I was never going to be good looking enough to present well in the new world I was seeking when truthfully my overall confidence as a trans woman had more to do with my approval than my appearance ever did once I had went beyond the basic point I needed to be to blend in with the ciswomen around me. Life changed when I realized there were plenty of women in the world who dealt with being bigger in stature and even had broad shoulders such as I had. My realizations helped to give me the boost I needed to continue to let my so called “hobby” consume me.

The reason was that I was ignoring the fact that cross-dressing was much more than a hobby, it was becoming a lifestyle. The biggest problem was that nothing I did as a novice trans woman was ever good enough. Even my second wife did not like the person I was becoming when I took the time and effort to show off to her as I thought were my best feminine efforts. Even though I desperately was seeking her approval, it was becoming obvious to me that my inner feminine self and my wife were lining up to fight it out. I was left behind to pick up the pieces as I was realizing how consumed I was when I had one of my rare, sanctioned (by my wife) outings at Halloween in NYC when my wife decided she did not want to go with me. The night turned out to be a dream evening as I ended up going out with four other women dressed to thrill as I was and they all happened to be as tall as I was in our heels. The night even ended on a high note when I was asked to dance by a guy in the venue we went to. I turned him down because he had no idea that I had one basic difference from the other woman I came with.

Anytime I experienced such a wonderful evening such as that Halloween party, I wondered if the gender euphoria I felt was worth it when I came crashing down. I was consumed with the moment and wanted to re-live it time and time again, but I was tucked away in my male work world and could not get out. Looking back, I don’t see now how I survived the balancing act I was putting myself through. I needed to physically show up as the man I never wanted to be. While at the same time spend all my mental energy remembering the transgender woman, I was. If I could have cried during that time in my life, I am sure I would have cried myself to sleep many nights worrying about my gender dysphoria and how it always threatened to wreck my life. Even to the point of almost destroying my marriage to the woman I loved deeply when my frustrations would boil over into yet another fight about me. Some of the fights were so severe that my second wife told me I was not man enough to be a woman, or why didn’t I just go away and fix the problem and make both of us happier.

Perhaps, by this time, you are wondering too why I did not take her advice and do it. The main reason was, at that time, I was not ready to give up totally on the life we had together when I was a man and even though I was increasingly being consumed by the idea I could be the trans woman I always dreamed of, I was not ready to pull the cord and jump out of the plane just yet. Because I was still afraid of the new gender heights I was reaching and selfish enough to think my wife may still come around to accept me. For those of you who don’t know, she never did and died tragically of a massive heart attack at the age of fifty.

The whole experience sent me into a major negative tailspin which I had a difficult time emerging from. I think the only reason that I did was because I had let my feminine self-consume me, and she could not wait for the opportunity to take over and live. My life had come full circle, and all the time and effort I put into my male to female femininization came back to help me. I had already put the work into how I wanted to look with my make-up and fashion basics and was already out into the world actually discovering how it would be to carve out a new transfeminine life for my very own. I had gotten what I needed as I moved ahead towards beginning HRT or gender affirming hormones. Which were something I always wanted to try as part of my overall commitment to being as close as possible to being who I always was destined to be.

When life consumed me, I was always somehow able to accept it and even thrive with it. Even though it took me decades to do it with all the ups and downs of what I had to go through. At the least, it made life interesting.