What I Intended to Be

Image from Jen Theodore
on UnSplash

Early on in my life, I was all in on pretending to be someone I thought I was not. (a girl) I was reinforced by all the lonely times I spent in front of an admiring mirror which was telling me I looked wonderful as a girl. All along, the mirror was just reinforcing what I was pretending to be. Feminine (or what I perceived it to be) dominated my free time thinking.  I wrote "what I perceived femininity to be" because as life went by and I acquired more experience cross dressing and/or being a transvestite. I was so protected back in those days, I didn't even have the time or access to really consider what either term meant. In either case, I discovered both were just labels anyhow.

The whole gender process I went through ended up taking me nearly a half a century to go through which sounds intimidating. The trip also was very laden with various ups and downs which I revisit frequently. I do it in the hope others who are considering such a venture can learn from my successes or failures. Similar to everything else in life, we have to learn from our failures and move on until we can finally experience the successes. I experienced more failures than successes before I finally  learned to present as well as I could as a woman in public. When I did, I needed to settle on one look and build my new self from it. 

From there I was able to move away from any thinking I was moving away from pretending and moving increasingly towards a life to be lived as it was intended to be. The main reason was the process felt so natural. Even though for the most part I was terrified to give up my old male life. Each step I took as a novice transgender woman proved I was on the right gender path. On the path I was able to carve out my own safe places to go to. I started out in gay venues. In which I quickly rejected for several reasons. The main one was I did not want to be mistaken for or treated as a drag queen. From that point I started to go to a few upscale bar/tavern venues similar to what I was used to managing in my restaurant days. I had one main positive going for me in that I knew the venues were primary revenue driven. And, if I did not cause any trouble and tipped well, I could survive if I did the best I could to dress to blend. I became a regular bar fly and was able to build from there. 

Again, the more I quit pretending to be a woman and started to believe I was one...transgender or not, the better I did. The new world I was in provided me many challenges to move forward into a feminine world I had only dreamed of. The whole process led me to quit pretending all together I was ever a male in the world and onward into a dream world of being a woman on my own terms. Sure I faced the haters who said I could never be a woman because I could never bear children to which I replied what about the cis women who for whatever reason can't have children either. For the most part, I never heard from them again.

As it turned out, life started all over for me once I made it to my early sixties and I was able to start all over and live my life as it was always intended to do.  

It's Complicated

 

Photo from the 
Jessie Hart Collection

Often I wonder why I chose such a difficult path in life. It all would have been so much easier if I had only followed the male journey which was set out for me. In other words, if I had been content to be the square peg fitting into the square hole would I have been happier.  Here I was stuck in a white world in a middle class family with all the expectations laid on me of a first born son. 

The problem was, for some unknown reason to me, I never had a choice. From the earliest age forward I always suffered from gender dysphoria. I just couldn't shake the fact I wanted so badly to be feminine. How much easier life would have been if I had accepted the male role I was thrown into without the uncertainty I faced if I had the courage to accept my true gender and build a new life. Compounding the problem was nothing changed when I became older, in fact things just became worse. The more I explored when I snuck out of my dark gender closet, the more I wanted to explore. The world just felt so much more natural when I was living as my feminine or transgender self. The more I explored and had to return to my increasingly unwanted male world, the more frustrated with life I became. Why was this happening to me.

What did happen was, when the pressure built to the point I couldn't handle it, I escaped to my secret feminine world which embraced me. The more I was embraced, of course the more I did not want to go back. The whole process caused me to dwell on the next time I could run to and escape the male world as a woman. When I was in what I call the "hell" times, I became mean and nasty and very difficult to live with. It became so bad, I even lost a job one time when I was being nasty to my crew. I often wish I had the time back when I was obsessing about being a woman as I was trying desperately to go forth and be a man.  How much farther could I have gone?

Again and again I am humored when I read someone who says all along I had a choice to be transgender and live with all the hell I lived with as I followed my path. I was driven hard to be a successful man as a father and a provider and gave it all up when I transitioned. The whole process was unbelievably complicated and stressful. Perhaps the worst part was I didn't completely understand what I was going through. The only thing which was obvious, come hell or high water, I needed to go through it. All I know is when I gave up all my hard earned male privileges to live a full time life as a transgender woman, I did the right thing. The ripping and tearing of my two genders fighting for supremacy just destroyed whatever life I was still trying to live. 

What I didn't understand was how complicated life would be as a transgender woman. I needed to look the part first, then learn all the nuances of a gender which is certainly the most complex of the two binary genders. Male and female. Just communicating with other women as an equal took me a long time to learn. Plus playing in a world built around passive aggression left me scarred on many occasions before I began to understand exactly where the claws were coming from. It was complicated but I was able to learn as it didn't take long for my long hidden female self to gain total control. 

It was my favorite time of my life. As I love to put it, I gained my right to play in the girls' sandbox. 

Transgender Bruising

Photo from
the Jessie Hart
Collection

As we all have experienced, the path we have chosen for ourselves to find and live as our authentic selves is often filled with walls, curves and potholes. Once we think we have conquered one obstacle, another pops up to bruise us. 

Even after all these decades, I still carry the mental bruises when I didn't pass and was stared at or even laughed at in public. Worse yet were the times I was told to leave a venue after a group of guys insisted on playing "Dude Looks Like a Lady" time after time on the juke box. Following my refusal to leave after all of that, I was asked to by a manager. Ironically, I had my revenge not long after that when a group of employees found me in a nearby venue and asked me to return. Telling me the manager who asked me to leave was fired for drug use. Even still, it took awhile for my gender bruising to go away. 

Little did I know I was at a new point in my life as a novice transgender woman when I was just getting started. Only one aspect of my life remained the same and that was change. I had always been a person by nature to push the boundaries and I still did as I climbed my gender path out of my closet. Even though I was excited and at the same time terrified when I was exploring the feminine world, I took my bruises and moved on. Not knowing what the next experience would be. Amazingly, I was able to forget the nights I came home in tears and made myself ready to try again. The learning curve would vary from deep bruises all the way to small hits to the ego. 

Through it all, I was for the most part, learning on my own with no one to guide me. It seemed the path I was on had very few street lights or signs to help. During this period of my life, the internet was just getting established and I was in the middle of a twenty five year relationship with my second wife  who disapproved completely when I suggested in any way I was transgender. Two major obstacles I needed to work around if I was ever able to advance up my gender path without sustaining any other major bruising. Somehow I managed to keep moving forward until sadly my wife suddenly passed away and I had choices to make on my future.

On my path ahead I had already seen plenty of signs promoting HRT or hormone replacement therapy. As I considered the huge consequences of such a move, I thought maybe a increased dosage of estradiol in my system would make up for some of the bruising I had experienced in my past. I figured at the least, the hormone therapy would help to feminize my exterior self which was exposed to the public. Plus the process would help me sync up my inner woman with my exterior man. As I went up the gender path this time, at least I had HRT to help me. Plus, while I am on the subject of help, I always need to pause and thank all the women I met on the path after I started hormones. Without all the women I met, the bruising would have continued longer. My path was telling me I still had a long way to go to truly learn and embrace the layered feminine lifestyle I so desperately wanted. 

To make a long story short, my friends embraced me, healed my  gender bruises and helped shorten my pathway to living my dream life...a full time transgender woman. 

Maybe I was fortunate in that all of my bruises were mental. Not psychical like so many women trans or not have to go through. However mental bruises are hard enough to heal.