Staring Down the Transgender Cliff

Image from Jimmy Conover
on UnSplash

 As I transitioned from my very active male self into an accomplished transgender woman, there were many times I found myself staring down a cliff on my gender path.

The more I walked on and was successful, the more scared I became. The cliff I was looking at, increasingly appeared to be steeper and riskier than I ever imagined when I first put on a dress and makeup so many years before. After all, I was risking so much such as a spouse, family and a job to name just a few. To add more pressure, I was becoming increasingly more and more successful in my choice of occupations. I had worked years to arrive at where I was and now I was risking it all to try to be a successful out transgender woman. By successful, I mean I was able to increasingly move about in society as I carved out a new life.

Mixed in with all the life changing experiences I was going through were many failures as I would sneak up to the cliff and look over. The entire process was scaring me more and more and threatened pushing me back into the gender closet I had worked so hard to leave for all of those years. 

Finally, I could take it no longer and began to gather the courage to take a leap of faith as I approached jumping off my personal cliff into a risky world I thought I knew something about. Before I did, I tried to come up with a survival plan when I jumped into the sometime snake pit which was the feminine world. I needed to learn the basics of the indirect passive aggression. Slowly but surely I learned to fasten my seatbelt and learned to ready myself to jump. I had conquered so much on my journey and it was time to quit staring down the gender cliff. 

Ironically, the women friends I had made like Liz and Kim helped me to a soft landing. They taught me what it would take to for me to become a transgender woman on my own terms. More importantly, all the fears I felt concerning my fear of gender heights proved they were like new gender guardian angels to me. Certainly, I found there were transphobes who would never like me but on the other hand, I found most people just didn't care. I was left alone to make a soft landing around my friends and enjoy my new life. 

I have always tried to be a proponent of the idea that something you are proposing to do will not be as bad as you think it will be or as good as you think it will. The same happened to me with I took the chance and gave up my male life and undertook the biggest adventure of my life. 

The soft landing off of the cliff coincided with my softer life as a transgender woman. When I did land, I wondered what took me so long. My excuse was I was afraid of heights, when in reality, I was just afraid of losing what was left of the white male privilege's I enjoyed. But it turned out, I could not have my gender cake and eat it too. It became too much pressure to attempt to live part time as a trans woman and a man. 

I closed my eyes, hoped for the best and jumped. It did not matter how intimidating the cliff seemed to be, the steep gender cliff proved to be the least of my problems. 

Transgender Inspiration

The late Lynn Conway.

 In my formative years growing from a beginning cross dresser into a novice transgender woman, there were very few inspirations for me to follow. One of the few I knew about was the very accomplished and talented Lynn Conway, a computer scientist and electrical engineer.  

Deep down I knew I was not on the same level as Conway and the very few I did know about followed the same path as most transsexuals face when they transition into a feminine life. We were expected to leave our past behind, have all the needed operations and relocate ourselves to start over. Since I was my usual stubborn self, I could not see me going down all of the same roads as well known transsexuals. In fact, I knew a couple trans women nearby who were ready to go down the surgical road and change their lives forever. 

As in most cases each of their lives were totally different than mine. So they were more of an interest to me than an inspiration. By getting to know them closer, I had hoped to gain more knowledge of what I would face if I decided to go further with my own gender transition. I did learn, as I went on, everything was different when I was living as a transgender woman. I had my own preconceived ideas of how it would be to live as a woman from all the years I had spent closely observing the women around me. However I found most of my conceptions were wrong as I slipped behind the gender curtain. The prime example was how I was presenting myself as a woman. I wasn't dressing to blend in and was drawing unneeded attention to myself. My efforts came from my old male ego dictating my fashion and wardrobe. I had no inspiration to guide me the correct way.

I think I tried to use my second wife as inspiration but I was just not in the proper mental space to accept her criticism. In other words, my feminine self had not had the chance to grow up past my adolescent years as a trans woman. During those years, happiness was looking very lonely as my wife and I constantly fought over my appearance among other things. I think she knew she was fighting a losing battle as my internal feminine self fought with her all the time. Every now and then, I did talk her in to going out to eat as two girls and I really tried to dress down for the date. As a matter of fact, if I dressed down any more, I might as well just have gone as my male self. 

I was getting nowhere fast in my quest to learn more about being a quality transgender woman, so I was forced out on my own. Which added in it's own set of problems. Primarily, here I was sneaking around behind my wife's back to see if I could live as a woman. In doing so, I found I could create another life. Furthering the divide between my wife and I.

The divide widened until her death and inspiration or not, I continued on with my search for my feminine self. What I discovered was, she was with me all along. Just waiting for a chance to live. When she did, she became my own inspiration and I never looked back. In many ways I found she adopted many of the mannerisms and personality of my Mom, who was very outspoken and not shy. I admired her so much, I took her first name as my middle name when I legally changed my gender markers. 

These days, with all the internet and social media access transgender inspiration is much easier to come by and we need the inspiration with all the negative coming our way from politicians. We have to do all we can to keep the positives coming.

I Am I Said

 

Archive Image, JJ Hart

One of my favorite Neil Diamond's songs is "I Am I Said". I particularly was drawn to the line saying I was lost between two shores. Neil was referring to New York and Los Angeles and I adapted it for me to signify being lost somewhere between being male and female.

The song's lyrics go on to say "I am, I said to no one there " I again felt the same way because I had no one to discuss my gender issues with other than the occasional therapist who went quickly through my life with little or no benefits until I reached a point much later in my life. In addition, the pressure to conform to the successful male life I was leading was intense. One of the few positives of my job was I was named a managerial training manager so I was able to take medium ranged business trips from my home in Ohio (yes I am from the much maligned Springfield) and travel by car to Lexington, Kentucky. Usually, I was asked once every six months to make the trip which I quickly saw as an opportunity to pack a few of my feminine items and cross dress. 

I usually worked it out with my second wife I was taking a second night at the company headquarters so I would not have to drive back at night. When I did, I was able to either cross dress and head out to one of the Lexington gay bars. It turned out, there were several back in those days, since the University of Kentucky is there. When I went out, at the least I didn't have to tell the chair or mirror I was actually someone feminine. On one occasion, I hit the jackpot and my training seminar just happened to coincide with Halloween. I thought ahead and when I packed away from my wife's prying eyes, I added a few slutty outfits to put together a Halloween "costume." The difference this Halloween was I was going to try my luck at going to a big straight club and not a gay venue. After a few wrong turns, I found the place and gathered my courage to go inside. Here I was dressed in an all black mini-dress with black heels, hose and blond wig doing my best to ignore all the guys pinching my behind as I walked across the dance floor, Since I needed to be up and fresh early the following morning, I needed to be back early to go to bed.

All along, I was learning what I was and was finding out the hard way what could happen if I dressed the wrong way. One night, I decided to stop at the halfway point on the way home which was Cincinnati. I got a hotel room and proceeded to seek out one of the more infamous gay bars in town for hookups, I thought since my black outfit worked so well before, I would try it again. This time, a very drunk guy at the bar tried to pick me up...until his wife showed up. I was embarrassed and was trying my best to back pedal from the whole situation when he made things worse by telling her why did she not have legs like mine. By this time, I headed for the restroom to hide and when I came out they were gone. As was the black outfit.

Through it all, all the lying I was doing to my wife was wrecking my moral code and when I asked who I was, I did not know. Which made the Diamond song so important to me. 

Finally, I did climb out of the pit I was in and was able to learn who I was but sadly was never able to reconcile my transgender life with my wife before she passed away. All along she was urging me to find myself and by the time I did, it was too late. I was no longer stuck between two gender shores. I had found myself and she was feminine.