Halloween and Gender Breakthroughs

Halloween
Image from
the JJ Hart
Archives. 

Back again we go to Halloween and the effects it had on me as I developed into a novice transgender woman.

Very early on I learned when I cross dressed head to toe as a woman for a Halloween party, I would be cut out of the male club and my male friends would ignore me. Very early signs of losing any male privilege I had built up over the years. On the other hand, I was not ignored by many of the other women I knew from before who took the time to comment on my shaved legs and "costume." Both were small but definite signs of what I would face in the future if and when I decided to enter the public as a transgender woman. 

Over the years, my tastes in Halloween "costumes" changed from just wanting to be slutty, all the way to trying to present myself as a cis-woman would at a party. Plus I needed to overcome any fears I had of going to the party as a woman and mostly giving up on having a traditional good time partying with friends I had known for years. Again, just a small dose of what it would be like to cut all ties with my old male life and start all over. 

Everything began to change when my "costumes" began to evolve. One party in particular stands out in my mind. It happened when my second wife and I were living in the metro New York City area and I was managing a food location. It just so happened I was invited by one of my assistant female managers to go with her and several of her friends to a Halloween party they were going to. Without hesitation I said yes and wondered how I was going to explain it away to my wife. She never was into Halloween much and turned out she did not much care so I set out to put together an outfit for the evening. I decided to go semi-sexy (or try to) and chose my short mini dress, heels and dark wig for the evening. Off I went into the great unknown of not knowing where I was going and with whom.

It turned out, where I ended up first of all was at the house of my manager and to my pleasant surprise I learned all of her friends who were going were all tall attractive women dressed approximately the same as I was. As I walked into the room where they all were waiting, you could have heard a pin drop as they all looked me over from head to toe. Once they realized who I was, off we went to the real party which was being held at a small bar near to her house. The first thing I thought of was how far was I going to have to walk in my heels but the distance was not too bad and I was on my own cloud nine. I mean, here I was with three other women my height dressed the same way headed for a party. I was scared but excited by the time we arrived at the venue. Once I got to the bar and had a drink or two I started to calm down and learned another couple of gender break throughs. 

The evening turned out to be my first ever girl's night out because I was able to blend in so well with the other women I was with and I learned the power of being able to blend in with the feminine world. The second big breakthrough I learned was how to handle being approached by a man who perhaps did not know he was talking to a transgender woman. I was even asked to dance by one man. Finally, I learned single women of a certain age have a tendency to mark out their own territory when it comes to attracting male companionship. Once we all arrived in the venue, I was left very much on my own. 

I did not know it then, but all of the gender lessons I learned would come back to help me later in life. So much more than an empty comment about how good my shaved legs looked. As my second wife kept trying to tell me, I hadn't paid my dues yet to be considered a good feminine person. Trans or not.   

A Spectator in my Own Life

 

Image from Author JJ Hart

There were many times in my life when I felt as if I was a spectator in my own life.

From the first glimpse in a mirror when I cross dressed as a girl, all the way to when I first went out determined to be a woman rather than just look like one, often I was on the outside looking in. Being on the outside was certainly not a great place to be. I literally spent decades of my life worrying about where I actually stood with my gender issues.

Along the way, I grew tired of being the spectator and wanted more inside information on how the feminine system I so admired worked. I discovered the hard way, I was not going to be allowed to learn more until I made the drastic step of increasing my transitioning efforts. Naturally, it was very difficult to do when I was totally immersed in leading a male life which I had become quite successful at doing. Overall, I was becoming the victim when it came to my life as a whole. I kept wondering why me when it came to my desire to live as a transgender woman. I finally had to shake it off and move forward with my gender transition before I lost everything I knew in life. 

It turns out the real culprit was myself.  I was afraid to face my truth and it cost me. I even tried to out run my desire to live as a woman by moving and switching jobs. Once I talked my wife into moving from our native Ohio to the New York City metro area. Then back again a couple years later. Living in different parts of the country was certainly an eye opening experience but did very little to help my gender issues. On the rare occasions it did like the night on Long Island when I went to a transvestite mixer and the hosts thought I was a cis-woman was flattering but did me no good the next morning when I crashed back into my male life. Then my poor wife had to put up with my mood swings.

Still I was a spectator in my own life when I walked down the long hallway in heels to get carded for my true gender to the times I did the family grocery shopping in sweaters, mini skirts and flats, I wondered who was that? It took me years to come to the conclusion the other feminine person was me and she had a right to be here in my life. Slowly but surely, I was building the life experiences needed to cross the gender border but it kept taking me so much time. I kept running into so many road blocks, I thought I was some sort of a gender construction engineer. 

Regardless as time flew by, it was time to put my gender cards on the table to finally determine which gender was going to be the primary provider in my life. What I attempted to do was live as much as I could as a novice transgender woman to see if the lifestyle was for me. Even though initially I did not attempt to do it, the trans life rapidly snuck up on me. Before I knew it and maybe before I was ready, I began to carve out a brand new life as a woman. Quickly I needed to develop feminine communication skills which was difficult for me to do since I was overwhelmingly dealing with other women in my life.

Through it all, slowly I grabbed total control of my life and became a spectator any time I was forced back into my old unwanted male life. In other words, I finally faced my own truth and flipped the ultimate gender script in my life.    

Running as Hard as I Can

Image from UnSplash

Throughout my life, I frenetically ran from one thing to another.

In theory I was never much of a runner and only ran  when I was forced to during times I was in the Army and/or played football. So running never came naturally to me. for some reason though, when I was discharged from the military was when I free to face the world again would I settle down or run again. My answer started to emerge. It didn't take long as  I remembered when I was discharged and was heading home to Ohio from Ft. Dix in New Jersey. Before I arrived home, I had the entire Pennsylvania Turnpike to drive. Before I did so,  I paused for a second to ponder what I was going to do with my life. Surprisingly, at that time gender played just a small part of my future. Perhaps I was saving my gender issues for the future. 

Possibly also, at the time, I was still basking in the glow of coming out as a transvestite or cross dresser to three of my closest friends in the Army. Included in the group was a woman who was also in the Army. We had worked out she would meet me following her discharge and we would decide what would come next in our relationship. After we decided to visit her parents in California from Ohio, we decided to get married and as I said, she was fully versed in my gender issues. At least to the point which I considered them to be. At the time, I considered myself a serious cross dresser and I had a long way to go to being transgender.

As time went by, I switched professions from being a commercial radio disc jockey to the restaurant industry which at the time was expanding rapidly. To support my new family (daughter), I needed to be able to make more money. During the same time, I wedged in buying a small bar with a friend which eventually became a fairly successful pizza and beer restaurant. To make matters worse, I was beginning to feel the gender pressures I would need somehow to learn to live with. Even though I managed to dress in drag on various Halloween parties I went to, the rest of the time, I lived in my dark lonely gender closet knowing the next day I would be back in my male drag. 

To make up for my issues, I tried to offset my thoughts by moving our home as well as switching jobs. In addition, when I could, I tried to participate in civic groups which gave back to the community. Anything it seemed to take my mind off my desire to be feminine. Along the way my second wife and I moved from our native Ohio to the New York City metro area and then back to a new very rural area of Ohio which bordered on West Virginia. In the space of a couple years we went from living in very upscale Westchester County, New York to living in a farmhouse near the Muskingum River in Ohio where we heated with wood and needed water trucked in during times of the year which were drier than others. I was running from my problems as fast as I could.

The end result was I finally had enough and I needed to face my problems head on. One lonely night, I realized I had experienced enough of living a transgender life, I wanted to live it full time. My old male self had lost the battle and my new life felt so natural. 

It turned out I was never very good at running to start with. 

   

Destruction

Image from Mika Baumeister
on UnSplash

At various stages of my life I survived being so very self destructive to everything around me. 

Of course being gender dysphoric as well as bi-polar didn't help. Before I was diagnosed and received medications it seemed all I did was go from being very depressed to being very mean and nasty. I am surprised my wife was able to stay around as I tried to tear down everything I attempted to build. Often I would change jobs at a frenetic pace just to see if I could. During the process I uprooted and moved my wife and I from our native Ohio, to New York City, then back again to West Virginia. She didn't like the moves but came along anyway.

It took me awhile but finally I came to the conclusion I was trying to out run my gender issues by all the moving we were doing. Since my inner feminine self didn't respect all of the work was male self was doing to be a success, she did her part to resist and tear all the work down. Very self destructive to say the least. 

One of the biggest pillars of my life which was left was my marriage to my second wife which I write about often since it lasted twenty five years. She knew I was a cross dresser or transvestite from the very beginning so in many ways dressing like a woman for me was a non starter with her. She didn't really care and/or put up with it. The deciding factor came when I began to feel the urge to see if I could actually live as a transgender woman. I can still hear her words echoing in my head, I never signed up to live with another woman. After tremendous gender focused battles and me essentially cheating on her by leaving the house behind her back, I finally gave in and tried to purge most all of my feminine belongings before she passed away. I view the whole experience now as a fight between two strong willed women, my wife and my female self.

After I began the MtF gender transition to living life as a transgender woman, I needed to go through a relearning process of sorts to not be so self destructive. Among other things, I needed to dress more conservatively to blend in to where I wanted to go and I needed to be much more wiser when I did it. I almost learned the hard way about being in the wrong place at the wrong time as a trans woman. My male safety privileges were stripped from me when I crossed the gender border and I needed to learn the new rules of being a woman...fast. 

As it turned out, my new feminine self was much less self destructive than my old male self. Once she had finally got her way, she wanted to keep it and build a much more pleasant life.

Welcome to Hell

As I continue my Cyrsti's Condo post from yesterday, the best place to pick up the story is when I was honorably discharged from the Army. All of the sudden I had this incredible sense of freedom.

As in all freedom's though, this one carried a price. It all started with the naive notion I could continue to come out to others as a transvestite (the common term for a cross dresser) in the mid 1970's. As I have written about several times, I was soundly rejected by my Mom and from there mostly headed back into my closet.

By "mostly" I meant, only my wife really knew anything about my cross dressing desires except for a few Halloween adventures when perhaps I looked a little too accomplished as a woman in front of a few of my friends. Amazingly though my normal macho exterior I worked so hard for carried the day.

As you can probably guess, the yearly Halloween adventure and dressing up at home behind closed doors wasn't nearly enough. The formula was fairly simple. The more I cross dressed the better I became at it and then I felt more and more natural which led to more gender confusion.

Virginia Prince 1940

About that time I learned of Virginia Prince and her Transvestia Magazine. I quickly learned I was not alone and I felt it was time to meet others like me. I also found there were mixers going on within driving distance of me.

As I attended the mixers, I learned quickly there were layers of different people. All the way from the cross dressers who were desperately trying to hold on to their masculinity by smoking big cigars in drag all the way to impossibly feminine figures.  This created yet another quandary for me. Where did I fit in?

I was far removed from most of the macho cross dressers but was curiously attracted to the fabulous feminine creatures. Of course at that time (and in many instances still do) I ended up in a middle niche I carved out for myself.

The problem this all created for me was it caused me more extreme gender dysphoria pressure. My answer was increasing my alcohol consumption, getting a divorce, losing a business and moving from Ohio to the New York City area. In other words, I was out of control...sort of. Out of the chaos came another marriage to a woman who knew of my cross dressing desires and who I was destined to be married to for twenty five years. She passed away quite unexpectedly from a heart attack at the age of 50.

The problem with all of this was, slowly I was coming to grips with the fact I was probably more of a new term I was learning more about. Could it be I was transgender? 

Being transgender meant all kinds of potential problems and changes.

The pressure became so intense it led me to try to commit suicide.

More on that in my next post.