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. 

Sink or Swim

Image from Trans Wellness Event. 
Jessie Hart Archives. 

Many times when I first entered the world as a new cross dresser or femininized male, I wondered if I was going to sink or swim.  

Leaving the mirror (who never lied to me) was difficult because the public didn't lie either and let me know if I blended in with other women or looked like a clown. Of course when I was stared at or laughed at I sank to depths of depression as I thought I was in too deep and would never make it to my transgender dreams. 

I discovered sometimes the hard way when I was out in the world, I could not turn back and needed to stick it out, even when the going got tough. It included the times that got so bad when I was laughed at. Then, something deep inside of me kept saying move on because times would get better. Similar to when I learned to swim at an early age, I gained confidence in the water and I began to swim onwards and learned women's fashion, hair and makeup which came closer to flattering me. 

Often my biggest problem was myself. My old male ego was telling me I needed to try to look a certain way when the opposite was true. I needed to blend in with other women in the venues I was going to which was especially important when I made it out of the gay venues I was going to and into the world I was used to as a man. Perhaps I was mistaken for a drag queen in the gay bars because I was dressing as one. Slowly but surely I started to be accepted as a transgender woman in the preferred venues I went out to and I began to swim with the big girls. By doing so I accepted the extra challenge of communicating with them. Far beyond just appearing as one of them.

As I always say, women lead a much more layered lives than men and here I was right in the middle of them trying to swim with the current. Which at times was difficult to do. I had so much to learn in a very short period of time. In order to not sink in the situation I was in  It took me tons of lonely soul searching to figure out if I was moving my life in the right direction and was losing all my white male privileges worth it. Of course you know I knew it was and I kept swimming towards my dream of living as a transgender woman. 

I was lucky when women along the way threw me life jackets to keep me afloat in my time of need. Their efforts just helped me to decide somehow I wanted to be more like them. If I survived my male to female gender transition, maybe then I could pay it forward and help other novice transgender women. Which is the primary reason I write. Most certainly I am biased but I think crossing the gender frontier is one of the most difficult tasks a human can undertake, so any assistance is good assistance Especially when we are swimming against the tide of society. 

Hopefully, if you are becoming tired or confused during your gender swim, I can throw you my version of a life jacket or boat. You can beat society's system and succeed if you are careful and keep trying. I sank so low once I tried severe self harm (suicide) to myself and was lucky I made it to the surface and survived. I bring it up simply as an example for those who think being transgender is some sort of a choice. It's what happens when trans women or men are round pegs being forced into square holes and never given the chance to sink or swim.

There are many ways to find your way to womanhood as a transgender woman, you just need to be patient until you find your path.

Dream on Or Transgender Dreams

Image from Randy Tarampi on
Unsplash

 I am fortunate, rarely do I suffer from not being able to sleep. Normally do I not benefit from my eight hours of slumber. Some nights it is even very entertaining. 

Early in life I remember vividly the mornings I would wake up from dreams in which I was a girl. I was immediately disappointed to learn  nothing had changed with my gender. I wasn't the girl of my dreams. Sadly for me my girl dreams were vastly outnumbered by my numerous boring male dreams. These days, following living forcibly as a male for sixty years, my nightly experiences are becoming more mixed according to gender. I guess the more I spend time as a transgender woman the more my subconscious mind is accepting it and is beginning to build a backlog of experiences of me in a feminine world. 

These days, I have made it to to a wonderful mix of gender dreams when I would have one dream as a man and the very next as a woman. Now interestingly I have reached the stage of being a cross dresser. Often I have to go through being exposed as a man in a dress and subjected to the normal rejection by the public. Perhaps I am just reliving the time in my life when I was coming out of my hidden feminine shell. Often to the stares and outright laughter at the hands of an ignorant public. 

Through it all, I am still dazzled by my subconscious which is able to switch my genders at will and put me in impossible situations in either. An example was the night, I started by dreaming of running a perfect shift during a very busy night at a restaurant I was running then going to a time when I was wearing a dress which was too short. To the point I was embarrassed and was trying to cover up my bare legs. 

I wonder if I live long enough, if my time as a transgender woman will overtake my time as a man. Which will be tough to do since to equal experiences out I would have to be one hundred twenty years old. Perhaps what will make up for the difference in years will be the intensity of the experiences I have been living through. Perhaps all the years of learning to find myself as a transgender woman will come back in my dreams. It will be interesting to find out. 

Using my very weak mathematical skills, I have calculated I spend approximately one third of my life sleeping. Since I do, I hope my dreams stay interesting. They remind of a rich life I have been able to live. One as part of the male gender I never wanted and the other as part of the female gender I always wanted to be included in. More examples of living as my authentic self will be welcome as reminders of my old unwanted male self fade away. Finally my transgender dreams will triumph as well as I have triumphed in my gender wars in real life.  

My First Black Friday

Prior to finally getting out of the closet and beginning to explore the world as my true feminine self, I always considered The Black Friday estrogen filled shopping experience as one I would never be able to explore.

Image Courtesy Marcus Spiske
on UnSplash

As luck would have it, my time to make it out with the largely feminine masses who frequent the Black Friday shopping experience was about  to happen. For those of you who may be across the pond and not know, Black Friday comes on the day after Thanksgiving and normally offers all sorts of sales to entice shoppers to spend their money. My second wife was a big fan (until she found herself in a retail job) and rarely missed a chance to shop very early. Often with a couple of her best women friends. Leaving me to be quite envious.

Finally since my wife was working the day shift at the bookstore she managed,  I saw my opening to be free to explore my first Black Friday shopping experience with many other women. Back in those days it took me longer to get ready and femininize myself so I sat my alarm to go off approximately the time I knew my wife would be leaving. Following making sure she had safely departed I climbed out of bed, knocked down a cup of coffee and proceeded to shave my legs and face. New pamty hose followed  by my bra, false breasts and padded hips. The excitement was building as I carefully applied my makeup and reached for my fuzzy oversized warm sweater which I wore with a knee length skirt, flats for comfortable mall walking and my blond shoulder length wig. Once I was satisfied with the way I looked, off I went to meet the great unknown, as a woman. 

Predictably, parking spaces were at a premium but I was able to park fairly close to the side entrance I always used. Once I was inside the mall, I was used to where I should try to go to pick up an extra gift or two and I was not surprised to see the crowd was at least two thirds women. All of which made it easier for me to blend in. As the morning progressed, I made my way through the mall with no problems what so ever since everyone else was in their own worlds and on a shopping mission. Giving them very little time to notice a stray transgender woman in their midst. 

Back in those days also I had sort of a cross dressing "bucket list" of new feminine experiences I just had to try to see if I could accomplish them. Braving the crowds of Black Friday shopping was on the list to conquer. Once I did make it through the experience I wondered what all the fuss was about. Similar to my women's restroom experiences. So called "sacred spaces" reserved for cis women just weren't that special to me. 

On the plus side, I was able to buy several gifts for my shopping list which were much more fun to shop for as a woman rather than my old male self. Once I accomplished going through a real live Black Friday experience successfully. I was finished with the thrill and actually have never done it again. I replaced it with trips to antique malls to search for vintage gifts for my wife who was really into gardening. 

All in all, discovering the vintage garden gifts made for better gifts anyhow and was more fun to do. So I was able to accomplish two priorities at once  The problem was when I had to return home with my treasures and have to return to my male cross dressed life. I couldn't wait until I could shed my old male clothes and sneak out the door as my feminized self again. When I was able to buy my wife a gift at the same time, it made it all so worthwhile.