A Genderless Journey

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Jessie Hart
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Recently I needed to take our car to the oil change place to get the transmission fluid replaced. 

In the past I have written concerning my paranoia of going to male dominated places. Since normally I am the only feminine person at the oil change place, the usual paranoia set in. The last time I was there, I was called "Ma'am" several times and had no gender problems so I did not really expect anything else this time. 

To prepare, I shaved closely, put on my foundation and contour blush with lipstick and was ready to go after tying my long hair back. Off I went to get the car serviced hoping I would not be mis-gendered. 

It turned out all my paranoia was baseless. I was treated with respect and not referred to as sir. Plus it turned out the whole process needed much more work than a simple oil change. So the manager was very much involved in the process. At times, he was so involved I wondered if he was trying to impress me. He even went as far as helping me turn off the "perform maintenance soon warning" off. Maybe I was the recipient of female privilege. Or, I needed help and he volunteered. 

Very soon the process was over and I was free to go (after I paid) and it was time to go through the drive thru of our favorite coffee place for a treat. The pressure was off and once again I wondered why I got so worried about going at all. Looking back, I have never experienced any negative feedback when I have gone to male dominated spaces. I guess I am afraid of being taken advantage of. When most of the time the opposite has happened. For the most part, men have bent over backwards to help me.

Maybe I will never change but I doubt it because the transition scars  run too deep. My gender dysphoria ran too deep as a transgender woman. It could be time to change my own oil.   

Playing the Victim as a Trans Woman

Image from Jen Theodore on UnSplash

It has always been easy for me to play the victim at times during my life.

Primarily, when times started to get rough in my male life, I could day dream of escaping into my female world .Usually I try to point out after a particular difficult day on the football practice field, I could wistfully take a look at the cheerleaders not so far away and instantly feel better. Of course, I was quickly brought back to reality by my position coach. Or by the offensive lineman who was intent of driving me into the ground. 

Over time my escapism became a habit, especially when I discovered how intense my feelings became when I cross dressed and interacted with my mirror. Suddenly I was not the victim anymore when I looked at the girl in the mirror. Which was all good until I found I wanted so much more than an image of a girl, I wanted to test my new self in the world. 

At the same time, my work was training me not to be a victim. As I rose higher and higher in management structures, I learned the buck stopped with me and I was only as good as my employees who worked with me. My problem then became carrying the same ideas over to my life as a novice transgender woman. Even though, I was still married to my second wife and was interacting with many many strangers on a regular basis, I was still extremely isolated and alone with my gender issues. Just cross dressing in front of the mirror wasn't enough and still I felt as if I was a victim. Why did I have to suffer from extreme bouts of gender dysphoria. 

The answer was always the same, I was stuck with who I was and I needed to somehow make the best of the situation. I dedicated my life to finding out more and more of what my wife was telling me when she told me I knew nothing about being a woman. I learned I did not and instead of being a victim, I needed a way to be allowed behind the feminine gender curtain. It wasn't until I made the decision to put my cross dressing ways mentally behind me and pursued ways to enter the world as a transgender woman did I begin to make serious inroads towards my dream. I know I am just dealing with labels to some but to me the distinction between transgender and cross dresser was huge for one major reason. A cross dresser to me just wanted to look like a woman and a transgender person wanted to be a woman. My ideas led to several spirited discussions on message boards as you can imagine.

As life moved on, I hated to be called a victim and did all I could to avoid it. I went to any extent possible to not going back to my former self feeling sorry for himself. In my own way, I felt proud of the fact I had been able to put all the self destructive behavior behind me. I was especially happy my suicide attempt had failed because I found I still had so much to live for if only I was able to reach out and grasp it. It was amazing when I stopped being a victim and was trying to live two gender lives was behind me. The pressure was off and my mental health improved. 

Playing the victim as a trans woman just didn't work for me. I did not have to worry anymore about what gender I would have to live as on any given day. When my dominate feminine self was finally given her chance to live, she took over and made my life worth living again. The icing on the cake so to speak was when she was able to make and flourish with a whole new set of friends which included my wife Liz. All of them never knew my old male self and I was able to build a new person from the ground up. 

Life was exciting and fun again or maybe for the first time ever. My old male self predictably knew how to be successful but never knew how to make friends and be satisfied. I was so fortunate to have been able to slip behind the feminine gender curtain and discover how the other half lived. I was accepted and loved it and never had to turn back.  

Bonding with Yourself

 

Club Diversity Image. Columbus, Ohio

As strange as it may seem, it took me many years for me to fully bond with myself as a transgender woman.

For years I wondered if I was a woman or a man. Everyday was like groundhog day when I woke up in the morning. Some mornings I felt more like a girl and others as a boy before the reality of my existence set in. No matter how gender fluid I felt that day, I needed to be ready to compete in my unwanted male world. I wish I could say the competition just made me stronger as a male but it never did. Most of the time, the competition just made me want to head home and cross dress as a girl. Plus, I was put into an even deeper frustration place when my brother was home and I didn't have any privacy to try on my feminine wardrobe. 

Bonding was difficult when I was not allowed into the feminine world at all and was destined not to until much later in life. In the meantime, I struggled from one gender struggle to another, All the time, hiding my authentic self from everyone in the world. I suffered so much, I needed all the help I could get to maintain my life as a man and still have any sense of stable mental health. Especially when I was diagnosed with having Bi-polar depression. If you are not familiar, I suffered from terrible highs and lows. When I was up I could do anything. Including transform myself into an attractive woman and when I was down, all I wanted to do was lay in bed and sleep and try to drown out my gender issues with alcohol. Finally I was diagnosed by a therapist and was prescribed medications to help me out.

As we all know, the medication has not yet been invented to relieve the pain and tension of having gender dysphoria. Even now I suffer from dysphoria when I wake up in the morning and look at myself in the mirror. After all these years, I have learned to take the good along with the bad and take the middle road. It has been a good coping mechanism for me. Along with those mechanisms, I learned other ways to structure my life so I could finally bond with my myself. When I did, I found I was a stronger human because I had the chance to experience life from both sides of the binary gender spectrum. Since it is the rare individual who can claim to be all male or all female in the gender spectrum, I was able to find my special place where I could exist in society. The question always was, was society ready for me or any other transgender woman or trans man.

I quickly discovered most of the world did not care if I was trans or not. They had lives to live and were busy doing it. On the rare occasions I did encounter a negative transphobe, my strong personal bonds gave me the confidence to survive. 

Again, bonding my unwanted male self with my stronger, more natural female self took me years to complete. Mainly because I did not have the courage to admit who I was to my true self. Once I did close the gap, my long awaited bond was complete and I could move on in life as a total person as a transgender woman but never forgetting the man who helped get me here. A topic for another blog post. 

Cha-ch Changes

 

Vote BLUE!

After many years of keeping the blog title the same, I have decided to modernize it to reflect the name I adopted as my legal moniker approximately seven years ago. 

How I came by my final name change requires a little explanation. As many of you know, my daughter was and has been one of my biggest supporters. In a very short period of time she brought up the idea of where did I come up with my name of Cyrsti. Even though it is spelled different than the usual Kristi because of the way a light reflects when it goes through a prism. My daughter did not like it. Regardless of any of that, my daughter and I had a quick meeting of the minds and decided I needed to come up with a different name. Mainly a name which would be easy for my three grandkids to deal with and remember.

For a name, I decided to go back into my family history and select from the people I respected. For a first name I decided to go with a femininized version of my paternal grandfather's name. Then for my middle name, I decided to go a little rogue and honor my Mom by selecting her first name as my middle name. I say rogue because my Mom roundly rejected me when I came out to her years ago when I was home from the Army. As the years passed by and I became mellower with age, I began to have a better understanding of where she was coming from. 

She was firmly planted in the WWII/Great Depression mentality. Which left little room for understanding so called radical ideas such as gender issues. After her rejection, I was left to deal with my gender dysphoria on my own and we never discussed it again before she passed. I came to look at it this way, she put in the effort to birth me and raise me, so I could honor her as the daughter she never had. 

Happily, the name change has worked well. The kids seem to like it and outside of a very few instances. I have had no problems remembering  not to sign my old dead name. 

To preclude any added confusion, Cyrsti and JJ are the same person in the blogging world although Cyrsti does not exist anymore in the real world.

On another topic, even though I was saddened to see Joe Biden step down for reelection, I am extremely excited to see the quick progress Kamala Harris will have to get up to to speed and beat the former president who I have ranted against so often. If any knowledge you may have gained about Project 2025 has not swayed you against him by now, I can't say anymore except you are done living in a country we all used to know. 

Running from the Pain

 

Image from jc 
gellidon on UnSplash

Most certainly, I know I am not alone running from the pain of my gender dysphoria.

Most of you have been through it also. You know it takes a great amount of effort to out-run your issues. For me, it has been a survival of the fitness scenario. I was stuck between the proverbial gender rock and the hard place. Exactly between the two primary binary genders, or male and female. Of course I was raised male and often resented it. When I did resent where I was in life, I just became more and more frustrated and the pain set in. 

As the pain set in I had two alternatives as I saw it. Internalize the fact I was transgender or run from it. At the time, I hit a personal wall I didn't even know was there. When I became tired of totally internalizing my gender issues, I set out to outrun them. I ran from my native Ohio to the suburbs of New York City then back again to rural Southern Ohio along the Ohio River. At the same time, I was switching jobs almost as fast as I was changing my shoes. I was fortunate in that I was in an industry which was expanding rapidly and there were quite a few new job opportunities to be had. At least when I landed a new job, I had the opportunity to take my mind off of my true problems. 

None of the running worked and the pain increased. The only things I learned were there were pockets of acceptance wherever I went, including unlikely ones such as Parkersburg, West Virginia which had a small but active LGBTQ community. The problem became I could not become too involved with any transgender related activities without resistance from my second wife. So again my frustration and pain increased because I was so close yet so far away. 

Finally, I could stand it no longer and needed to face up to my gender problems. At the time, I was increasingly exploring the world as a transgender woman. At one point, I was even living half and half male and female. I was learning I had much more energy when I was in the feminine world than when I was living as a man. Even when I faced giving up all my hard earned male privileges. Increasingly, I shed a majority of my gender pressure and decided for sure I was transgender and then go for a life which reflected my new decision.  Since I had cross dressed so long I figured I was doing something  right especially when I felt so energized and natural in my life. I will forever remember the exciting yet scary night when I decided to do away with my male life and transition into a feminine world.

By doing so, I put my pain behind me and could stop all the running I was doing. It felt so good to relax and take a breath after all those years of running. Initially, I did not know how to act with all the gender freedom I was experiencing. Of course I learned to live a new life I had only ever dreamed of and was able to actually bring a portion of my old male baggage with me and discard the rest.

Baggage is actually a topic for another post but simply put, trying to carry all the extra baggage of two genders was exhausting. I don't see now how I did it but I survived, barely at times. Running from my pain nearly got to me and led me to suicide. Life then went full circle and I was paid back with the help of friends together we pushed back what was left of my male self and my female self prospered.

Much More than a Phase

 

Civil War Cemetery image
from the Jessie Hart Archives. 

When I was first experimenting with wearing woman's clothing, I worked long and hard to hide all my feminine wardrobe and makeup. 

Due to transportation and financial constraints I always had a difficult time adding to my very limited collection. Plus, I always wondered if my Mom ever really discovered her clothes and others I managed to "borrow" for my cross dressing trips to my mirror. If she did, she never confronted me about it. Perhaps she thought it all was a phase and I would grow out of it. Similar to the fallacy, being transgender is ever a choice, I learned my gender issues were much more than a phase.

Very early on, I discovered a lesson I should have relied on but kept on ignoring. The lesson was, I wanted to be a girl, not just look like one. The very beginning of the realization I was transgender as I envied everything girls around me did.  Which went far past their pretty clothes while I was stuck in my drab male clothes. All along I was stuck in a family which valued male superiority and I wanted to rebel but couldn't. I often wonder if I had been born into a more diverse family (if that was possible back in those days) I could have made my feelings known and thrived. Instead, I did the only male thing I knew how to do and internalized all my inner feelings. I even thought, if I ignored my gender issues long enough, they would turn out to be a phase and go away.

Of course my gender dysphoria never did go away and just grew worse as I began to understand the full depth of what I was facing. As I look back, Halloween parties were my first indication I could do more than living a shallow life in front of the mirror as a cross dresser. I learned the hard way, heels weren't so much fun when I first wore them on long walks all the way to how much fun I had experimenting with the clothes and learning from the parties as a whole. Another step towards showing me my phase was not going away, I was just growing into it.

Halloween parties proved to be false feedback in many ways. Most people who saw me were friends who thought Haha I was the clown dressing as a woman for a laugh. Even though I was going as far as shaving my legs. In my mind, my legs alone would do the trick and everyone would know I was much more than a once a year man putting on a dress. At least I wanted it to as I grew confident I could present more and more as a real woman at the party. When I had achieved my goal, I felt I was ready to pursue a future as a successful transgender woman. 

When I did, the work really started. Life was so much more challenging as I left my male phase in my past. I wonder now if my Mom ever thought my simple love of girls clothes was a phase, what would she think now. Outside of the one time I tried to come out to her as a transvestite and she rejected me, we never discussed it again before her death. I can't help but look back and regret how much life I may have lost if she would have ever accepted me. I on the other hand took the high road and honored her by using her first name as my new legal middle name.  

Normally, phases come and go but certainly none of it applies to being a cross dresser or transgender person. Once the public at large learns to accept we are not a phase, trans kids especially could benefit from more understanding when they are young. Parents and siblings could have a more serious outlook of what being trans is all about, helping the whole situation. Or, leave the phase out and help the person. 

Finding your Happy Place

From the Jessie Hart Archives 

 As a transgender woman or trans man, it is often very difficult to find your happy place.

A happy place can often be called gender euphoria for all of us who suffer from gender dysphoria. If you don't know, dysphoria is the often evil process of hating the gender you were born in. After all these  years, I still dread the first look in the mirror every morning. Who will I see looking back? My same old masculine self, or a femininized version of him. Some mornings I land in my happy place and others I don't. I usually settle on a middle point until I am done with the mirror.  On occasion too, I suffer from having an impostor syndrome. When I think do I even belong here at all. Happily, the syndrome goes now away quickly because I know I have earned my place as a transgender woman.

Earning my place was never easy as I never inherited any feminine characteristics to start with. What I did have was a testosterone damaged body to work with. The only positives I had to work with were the compliments I received  on my freshly shaven legs at Halloween parties.  Then I had the tendency to overdue it when I explored feminine fashion. I thought I should emphasize my positives such as my legs and at the same time play down my body negatives such as a thick torso. All of it led to massive fashion mistakes before I learned to dress to blend in with the other women I encountered in public. I lived through all of those and found a happy place I could live with.

Around this time was when my happy place location started to change and move around. It shifted from appearance only into a personality based place. Mainly because, suddenly I was closely interacting with the public as a trans woman. It all meant so much more to me than my days as a casual cross dresser. All I know was I was up to the challenge and enjoyed my new happy place everytime it presented itself to me. Outside of a few instances of impostor syndrome, I was learning more and more I could indeed live my dream of being a transgender woman in the world. It turned out my happy place did exist in the feminine world and more and more I wanted out of my old boring male existence. 

Still I had a lot of climbing to do to rid myself of the old baggage I needed to lose to transition. I wondered at the time what I would do about everything I loved in life such as my daughter, (hobbies such as sports) and what was left of my business. It turned out destiny took it's own course with my baggage. My daughter supported me completely while my brother rejected me, so I was the recipient of the best part of the deal. As far as my business went, it mercifully closed due to a weakened economy and other factors, leaving me close to having an early retirement. As far as hobbies went, ironically I found a group of women who were as passionate as I was about sports, so I had friends to watch our favorite games with. So as you can tell, outside of the obvious gender issues, I was able to restart my happy place without a whole lot of extra effort. 

When I found my new happy place, it felt so natural I wondered why I did not pursue it earlier. I know early on I was into my appearance as a woman completely and often missed the basics of movement and communication to further my femininity. It turned out I did not have to worry because the deeper I delved into my new life, the more fluid and natural I became. Practice made perfect in so many ways along with the fact I became secure into who I was. When I did, I didn't care what others thought of me and my confidence as a trans woman increased.

It turned out, destiny took it's time but ultimately led me the right direction.    

A Transgender Marathon

Archive Image

 I'm sure you have heard the saying it's a marathon, not a sprint. This is especially true for transgender women and trans men.

Yesterday, I read a social media post from a first time transgender woman going out in public for the first time. In the post, she was bemoaning the fact after applying her makeup and seeing pictures, she did not look as good as she thought she did. My heart went out to her and I mentioned I went down the same path. Learning the art of makeup is just the first part of a transgender marathon into understanding yourself. 

Others who read the post chimed in with similar thoughts and even expanded it into impostor syndrome as a future possible reaction the person might have to face. 

Looking back, I could remember vividly how badly I felt when I first started my visits out of the house and into the public's eye. Back then, pictures were difficult to come by and were mainly only accessible by the old "photo kiosks" and drug stores. Only one time get I get brave enough to take a roll of film to one of the kiosks to see how I looked on film. I was shocked, and not in a good way, I obviously looked like a cross dresser and a bad one at that. The worst part was, the person who developed and gave me my pictures knew me and even worse yet, his Dad worked with my Dad. My marathon was almost over before it started. If I liked it or not. 

As it turned out, I moved back into the mirror and did my best to remove the negative self image I still had from the ill advised pictures. It actually took me years to try to attempt more pictures as my marathon moved on. As with anything else, the more you work on something, the better you become. Also technology was on my side with better cameras, which offered more than the very expensive Polaroids giving instant pictorial feedback. I was fascinated with my first cell phone which took pictures and better yet I had my first computer that I used to upload cross dressed pictures of myself. By doing so, I attracted attention, flattering to begin with in chatrooms until my wife caught on. She learned the computer skills faster than I did, so I needed to try to catch up as fast as possible. 

My marathon marched on, I gained more and more confidence until I reached increasing problems with my gender dysphoria. It seemed, no matter how much effort I put into my feminine appearance and deportment, the more I felt like a guy in a dress. To survive, I finally had to come to a basic conclusion. I was not as good looking as a woman I thought I was, or as bad. There was always the middle point I needed to shoot for. Finally, I knew who I was and I had the confidence to move on from new problems such as impostor syndrome. 

Again, I needed to come to a middle point where I could survive as a person. While I could never reclaim a girl's childhood experiences, or the problems associated with having periods or pregnancies, I had to go through my own set of experiences which presented their own problems. For example, I needed to try to escape my own gender demons which everyone in life seems to have, male or female, trans or not. I finally had to end the part of my marathon I agonized over for so long and claim my own brand of womanhood. Somehow I always found a way to survive and found a path. I was able to chase it and find success...in my own way. Which turned out was all I could do.

Going all the way back to the person who was just starting their public journey as a transgender person, try to make your marathon as easy as you can, Roll with the punches and move along as quickly as you can but always remembering the entire process is a marathon, not a sprint and sometimes, you are your own worst enemy. 

Good Together

 

Image from Columbus, Ohio
from the Archives.

As I grew into expressing my authentic self, I felt the pressure of attempting to placate what was left of my male self while I was increasingly living as a transgender woman. 

Increasingly, I felt as if I was living with a stranger when I tried to express my male self. He was fading quickly into my past, much quicker than I thought possible. Who was this man who controlled my life for so long? It took me so long to have the courage to figure it out. As I always point out, the answer was an easy one. I never was a man cross dressing as a woman, I was a woman cross dressing as a man. Once I figured it out, my life became so much easier. 

Sadly, my male and female sides never were good together. My second wife was fond of teaming up with my male self against my femininized insecure self. When she needed help the most, it was extremely difficult to find. Fortunately, I was stubborn enough to mentally tell them to go to hell. Mainly, because I felt so natural when I was following my transgender instincts. 

Instincts led me to improving my natural presentation as a woman including fashion and make-up arts. Maybe as I improved, my wife and male self became more and more scared. Somehow they saw me glimpse my reality and they did not like the future they saw. Specifically, the very few nights, my wife actually went out to eat with my femininized self, she made it painfully obvious she did not like me. More than anything else, her attitude hurt my feelings since I had attempted to dress down to meet her standards of wearing jeans, boots and sweaters. My next step down for me was to wear no makeup at all which would have defeated the purpose of going at all. Essentially, I gave up on any idea of us co-existing as women of any type. We were never good together. 

All I really wanted was an even break, or so I thought. The more I ended up exploring the world as a novice transgender woman, the more I wanted to do. Eventually, I could take it no longer and took the only way out I had. I went the gender affirming hormone route and decided to pursue a life as a trans woman and the rest of the story is relatively easy. The more life I lived, the more I felt more relaxed and good together with myself. 

Life was good again as I had come full circle from the dark days of death and gender dysphoria. 

A Zig-Zag Trans Life

Party night at Club Diversity
Columbus, Ohio.

 Maybe I should have called this post I should have zigged when I should have zagged. Or vice-versa.

In many ways, I see all sorts of transgender women or trans men in the same situation. I started at a very young age when I would zig away from my younger brother when we were home alone and I was able to get away from him when I cross dressed by locking myself in the bathroom. Fortunately, I never needed to zag because somehow, he never caught me and told my unapproving parents.

Somehow I thought when I got older, my life would improve. The first thing I learned was my urge to be or at least cross dress as a girl my age would not magically disappear. In fact, it became stronger when I learned it was not just a phase and I began to understand my gender dysphoria better. At that point, I really had to start zigging and zagging just to maintain my fragile mental health. When I was old enough, I even began taking myself to therapists to seek out help. My only main success which came out of it was when I was diagnosed with a bi-polar depressive disorder. It had nothing to do with my gender issues at all. As far as zigging or zagging, I was able temporarily save my marriage and received my money's worth when my gender therapist told me the truth. She could do nothing about me wanting to be a woman. Overall, my desires should not be a problem and I should face my truth. Of course, I wasn't smart enough to follow her advice and resumed all the zigging and zagging. 

It took me years and years to grow up and away from my male self and settle into a life as my authentic feminine or transgender self. By this time, I was growing so tired of all the zigging and zagging I was going through. Even though the whole process was an exciting time of my gender life, I was still becoming fatigued by my life the way it was. Ironically, when I was, I settled into a long term set of appointments with a very understanding therapist. She talked me off the ledge several times and along the way helped me secure gender affirming hormones and the paper work I needed to change all the legal gender markers I could. All of a sudden, I was able to visualize myself living my dream as a full fledged transgender woman. With my daughter's help, we were even able to come up with a new legal name which would reflect my family history and would be easy for my grandkids to use.

Finally all my exhaustion came to an end and I was able to live how I pleased. All the zigging and zagging had worked. All the times I hurried to hide myself away from friends and family, were put behind me. Through it all I learned one difficult lesson. If you can somehow believe in yourself, you can live your best life. Even though you may (like me) take years and years to evolve into your authentic self, the trip is usually never boring as you lead a zig-zag trans life. Overall, it takes a ton of effort to weave your gender issues into a life of family, spouses, jobs and friends. You learn to be forever vigilant in protecting yourself and end up internalizing way too much of your life. It seems the entire process is just ingrained as part of a transgender life as breath itself. We just have to finally zig to get around it. Then zag to adopt your new life as a trans woman.

On the Transgender Precipice

 

Image from Wira Dyatmika on
UnSplash.

As I followed a winding, difficult path to my dream of living as a fulltime transgender woman, I took years to climb the gender mountain.

Just one of the problems was  I was afraid of heights. The higher I climbed the rarer the air became because I had never been in all the situations I encountered. As I entered the world as a trans woman, there were so many situations I never expected to happen. I knew women led multi layered lives but not to the extent I encountered. Initially I thought if I had conquered all the fashion, hair and makeup basics, I had it made in the world. Needless to say, I was wrong. 

Even though my male self contributed to me feeling petrified as I climbed, I kept going. As I decided to leave the male gay venues I was going to and try lesbian and straight bars, I really needed to climb to a new level to survive. When I reached a new level, I paused to look around and see what I had accomplished if anything. What I did accomplish was a degree of acceptance from the venues I went to. Except for one evening when three guys kept playing "Dude Looks Like a Lady" on the jukebox over and over again, I begrudgingly held my spot and became an accepted regular in several places. As I did, my view of the world as a transgender woman became clearer and clearer. My gender dysphoric fog was clearing and increasingly all I could see was a future life living as a woman. 

At the same time, I was still a regular at the diverse mixers in Columbus, Ohio where I met a total range of people from cross dressers to transsexual women who were headed for gender realignment surgery or a sex change as it was known back then. By meeting and learning from all these people, I was able to chart my own path to my transgender precipice. 

The two main things I remember are how desperate I was for information on my gender issues and how scared I was of receiving an answer. Was my therapist right and I could do nothing about my feminine desires? If so, I had reached a precipice in my life and I needed to make a decision which would change my life forever. Of course my spoiler alert is, from my gender view, I could see a wonderful if not difficult future ahead as a trans woman. What happened was, as I built a new circle of women friends who never knew me as my past male self, I kept pushing and pushing myself to the edge of my transgender precipice until I fell down the cliff. 

Unknowingly, for the most part, I had set myself up for a soft gender landing. I gave away the remainder of my male clothes and set out to quit climbing and live a new life. What a relief it was to stop expending all the energy I was using to live two gender lives. The process exhausted me and ruined my fragile mental health. My friends helped me through this difficult time of my life more than I can ever say.

With my fears of gender heights behind me, I met my wife Liz and she helped me seal the deal and live my life as a transgender woman. That was fourteen years ago and we have been happy ever since. I don't think I could have ever envisioned I would meet up and marry another woman in my long life but I did. I guess the fog on my mountain was hiding my future.  

Trans Girl Secrets

Image from Ben White 
on Unsplash.

Secrets became a very important part of my life at a very young age.

It all started when I viewed myself in women's clothes  in front of the mirror for the first time. I realized my life would never be the same again. Plus I also knew my desire to be a girl would not be well received by my family at all. It was in the late 1950's and early 1960's when cross dressing was still considered to be a crime where I lived near Dayton, Ohio. In those days any sort of gender dysphoria was thought to be a mental illness. Even then, I couldn't see the act of cross dressing in women's clothes to be an act of mental illness. 

What happened then was I needed to go into a dark secretive closet, I would not come out of completely for a half a century. Along the way, I included very few outsiders in my secret. Four or five to be exact. I did not even include myself in my secret. What I am referring to is the fact I wanted to do much more in my life than just cross dress as a girl, when in reality, the reverse was true. I was a woman cross dressing as a man the entire time and I was indeed transgender after all.

Predictably, one secret leads to another and another and in my case led to lies being told later on. My dishonesty came when I refused to admit to myself who I really was and took out my frustration on those closest to me. I became a very unpleasant person to be around when my gender dysphoria was at its worst. Even to the point of me losing a job because of what I was going through. It was like I was setting myself up for failure at every turn in my life as I waited for more and more people to discover my secret. 

The longer my secret was hidden away and on the other hand, I was desperately trying to discover a new feminine world as a transgender woman, the heavier my secret became. I attempted to hide all my transgender activities from my second wife and was reasonably successful. I say reasonably because I would do more and more as a trans woman until she caught me and the gender battle between us would continue. She was wiser than I was when at one point she told me to just leave her and live a life as a woman. That made her the second woman in my life who I should have listened to when they told me the same thing. The first was my gender therapist years before. 

Sadly, my male self was not ready to give up the strangle hold he had on my life and encouraged me to do the male thing and try to ignore and internalize all my struggles. Of course in the end run, the only thing which happened was the pressure just kept on building as I managed to keep my secret. However, no matter how hard my male self tried to protect his domain, he was slowly sliding down a cliff of no return. Finally, with the help of several close friends I made the gender leap of faith. I gave away all of my male clothes, started gender affirming hormones (HRT) and never looked back. 

Perhaps the best part of not having to protect my secret and not live a lie was my new friends never knew my old male self at all. My inner feminine soul was finally free to live her life. When she did, she became the third woman in my life to tell me the same thing.

The only secret I really ever had was I was never really a man at all. 

Prom Time

 

Image from Amy Kate
on UnSplash

I graduated from high school way back in 1967 and where I went to school in Ohio, going to prom was a big deal.

I was very shy and as it turned out my junior year in high school prom was my first date with a girl ever. I didn't even really ask my date out, it was pre-arranged by her friends who knew she did not have a date nor did I. So I was set up for success. 

Of course success for me was scary. I had no idea how I could ever spend an entire evening with a girl. What would I say? How would I even communicate? The only real interactions with girls were with my Mom. All others just seemed to be up on a far away pedestal I had invented. Then my gender issues came crashing in to make my problems even larger. All I really knew was deep down inside, I wanted to be the one wearing the pretty fancy gown rather than the restrictive monkey suit called a tuxedo. Worse yet, I had to spend my own hard earned money to rent a tux. 

It turned out renting the tuxedo was only the beginning of my expenditures. I was fortunate at the time to have had a very well high school paying job so my parents did not have to contribute much to my initial adventure with a girl. In order to go all out for the evening, tradition was the guy paid for nearly everything from flowers, to dinner at a supper club, to tickets to the after prom which was a way to spend the entire night out. What I didn't factor in was how much my date had to spend on finding a dress, having her makeup and hair done and of course locating matching shoes. All of the processes the girl went through for prom to me felt like a labor of love to me I couldn't have waited to try. 

My date's parents were doctors so Dad even went the extra mile and let me borrow his car for the evening. Needless to say, I was scared to death in my tux when prom time approached. Somehow I managed not to blurt out anything stupid when I was introduced to my date and let her Mom put the corsage on for me on my date's spaghetti strapped gown which I loved and told her so. Just didn't happen to mention just why I loved her dress so much as I wondered how it would look on me. Fortunately, we were meeting another couple for dinner, so I didn't have to feel so stressed about carrying any sort of a conversation myself. So far so good, my first date was coming off without a hitch and ironically I was able to experience some sort of transgender revenge when I went to the old supper club when it became a gay venue. I was there one night and was able to use the women's room completing some sort of gender circle in my mind.

By the time my senior year rolled around, I was a seasoned prom pro and ended up going to two proms in one night. Since I was dating a girl who went to a competing high school, we decided to go to both proms. I even drove my own car since she was familiar with it and I didn't have worry about asking my Dad for his car. Overall, I managed to have a good time since I wasn't so frightened of the whole experience. For the rest of my life, my prom experience was over. For better or for worse. 

Probably, my parents were relieved I was finally dating girls. I on the other hand wasn't doing anything to relieve my gender dysphoria. I still wanted to be my girlfriends and live their lives. My cross dressing tendencies continued all the way until I was drafted into the military and had to stop for obvious reasons. By this time, I had more to worry about than how I looked as a girl. I was looking at surviving college so I could stay out of Vietnam as long as I could.     

Today I see the young high schoolers seem to view proms as less structured affairs than we did so long ago. It's all for the best.

One Gender Size does Not fit All

Image from Grae Phillips 
on Geraldo television show.

 If the truth be known, all the way back when I was a kid struggling to understand what gender I was on any given day, I would have been known as gender fluid. 

Of course, gender fluid was a term which hadn't been invented yet. Anyone who was interested in cross dressing was branded as being a transvestite and even worse labeled as being mentally ill. In the middle of my gender vacuum, even I knew well enough I was not mentally ill just because I wanted to wear makeup and dresses. I hid my desires and hoped for the best, which mostly came when I was left alone to cross dress and admire myself in the full length hallway mirror at home. Most of all, I was trapped and could do nothing about it. Keep in mind, all of this was happening in the information "dark ages" before the internet and social media. The gender underground I was interested in came mainly from the pages of Transvestia Magazine and Virginia Prince. Even I knew the pages of the "National Enquirer" and other predecessors of Faux News who sensationalized cross dressers were not to be trusted.

Then came the barrage of so called reality television talk shows including, Donahue, Springer and Raphael. All of whom seemed to be pushing the theme of cross dressing husbands Except for the impossibly beautiful and talented "Grae Phillips" who put everyone else to shame. All of these shows probably did little or no good for my gender dysphoria except for publicizing the fact there were cross dressers of transvestites of all kinds at all. All I knew was I desperately tried to watch or tape every show I knew was coming up from my "TV Guide". My wife was trying to tape her soaps and I was trying to tape my talk shows and both kept us busy. Even though I still had to watch my shows in private attempting to learn anything I could about the outside world.

I did learn once again. my gender size was unique and did not fit all. In fact, I still felt out of place when I started to attend my first cross dresser - transvestite mixers here in my native Ohio. I discovered there were so many different levels of participation from transsexuals headed for gender surgeries down to the weekend cross dressing hobbyists.  For some reason, I was not part of either group and once again my gender size was not fitting in. The problem was, all of this happened before the transgender terminology was introduced. When it was and I started to have access to my first computer, I was able to research the term which was unknown to me. Suddenly I knew what had been missing my whole life, a gender size which fit me and I set out to discover more about being transgender. For me, it meant being part of a gender description which was somewhere in-between the spaces I had been in previously.

Even though my gender size did not fit all, finally I was able to locate my own niche to thrive in. Life became fulfilling, scary and exciting at the same time. I found out I was fine being who I was all along and it felt so natural. I was home. 

You got it...Now Live with It!

 

From the Archives, Club Diversity. Columbus 
Ohio.

For some unknown reason, I have been remembering more and more what my gender therapist told me so long ago, she couldn't do anything concerning me wanting to be a woman. Now I don't remember if she told me I could not do anything about it either. 

If she did and had I listened, I would have saved myself so much inner torment over the years from my gender dysphoria. At the time my male self was not even close to being ready to give up any claims to his life which at the time was becoming relatively successful. After all, he had worked long and hard to arrive at the point where he was. 

If I wanted to blame anyone but myself for not accepting my true authentic self, I would blame my home environment. I grew up in a very male dominated family. My Dad had two competitive brothers and his competitive personality filtered through to my brother and I. It seemed no one had girls in the family and if they did, they were second class citizens. How I existed was by keeping my true feminine desires a deep dark secret. I learned early the very male trait of internalizing any negative thoughts or ideas. The whole concept turned out to be very self destructive over the span of my life which included the years of being a very serious cross dresser or transvestite. The whole process nearly took my life before I finally figured out I had it, now I needed to live with it. 

All I wanted was the impossible. Give me back just a fraction of the time and effort I had wasted by trying against all odds to maintain any sort of a male life. The cruel and unusual punishment came in when the more I achieved as a guy, made it more difficult to give it all up. I had a spouse, family, friends and good job to suddenly consider. What would my daughter think? Not to mention my wife and brother. All of a sudden I needed to draw a line in my gender sand and decide which route in life I was going to take. 

Everything changed for me the night I finally decided I had put enough exploration as my feminine self to make the ultimate leap over the gender border. Needless to say, it was a huge weight off my shoulders. I had a chance to go back in life to a point where I was not so jaded by either gender and experience for myself what the future held for me. It was at this point friends jumped in and showed me the way I never thought possible. I found I had it all along. I was a transgender woman and now I had the rare opportunity to live with it. I discovered there was so much more I needed to learn when I entered the world as a trans woman. 

Plus it took a while for the overall excitement of transitioning into my dream life to wear off. Everything I did was new and different and even when I was not accepted, I learned from my mistakes and for a change, my inner stubborn streak served me well. I had it and now I was living with it. I guess if you are able to live long enough as I have, you have the opportunity to see life go full circle. I paid my dues as a guy and what he learned turned out to be beneficial in my new life as a woman.

Quoting the singer/songwriter Joni Mitchell song "Both Sides Now",  only when I was able to see the world from both sides of the binary genders, was I able to relax and enjoy my life. All along I had it and just missed out on the real possibilities of what I was missing. Living with being transgender was all that mattered.

Transgender Plan B?

A Bright Idea from Diego PH
on UnSplash

In life, did you ever have to come up with a new plan if the one you were working on didn't work?

In my life, I had many "Plan B's" because I didn't think things out before I did them. A prime example was when I was engaging in all the cross dressing I was doing in front of the mirror when I was very young. If the truth be known, I didn't know what I would do if I was caught. Except to lie and promise to never do it again. Plus, what if I was caught shopping for makeup in a downtown department store close to where my Dad worked. In the vacuum I lived in, I just plowed blindly ahead, hoping for the best and expecting the worst never happened. Which it never did.

I suppose I always thought there was a "Plan B" somewhere if I was discovered. Somehow I would magically give up on my dream and keep marching ahead in a male world. In reality or not, I always thought there had to be some sort of back up if I failed at anything. There was always going to be another chance to put on a dress and apply makeup if I was careful. 

The first time I encountered a situation where the only back up plan was applying myself in the system was when I enlisted in the Army during the Vietnam War to evade the draft. When I went through the human machine called basic training, the threat of failure was real. The drill sergeants made it clear if you failed at something you could be recycled back to the beginning and have to start all over again. No one wanted to face that "Plan B." The result of going through basic built my confidence in that if I was forced into a situation I certainly did not want to be, I could still survive. The main problem I had was I couldn't (of course) cross dress at all and had to put my gender issues aside. During the several years which occurred before I could indulge in cross dressing again, my back up plan was to do quite a lot of daydreaming about when I finished my military service and could resume my life as I had lived it before. 

When I did finish, I found myself needing a whole new set of "Plan B''s." What happened was, I started to go all out at Halloween parties dressed as a woman. Where I learned the basics of surviving in a new exciting world as I was slowly growing up as a novice transgender woman, which was my dream. Of course the problem was Halloween only came around once a year and what was I going to do the rest of the time about my gender dysphoria. What I decided to do was sneak out of the house and into the world as my new transgender self. When I did it, I needed plenty of "Plan B's" if I was caught. My rule of thumb was to be as careful as I could and deny anything which happened if I was caught by my second wife. Not the best plan. 

As my femininization presentation improved, I found I needed a whole new plan to survive in the world as my authentic self. Primarily I needed a way to communicate with women I was meeting who were curious why I was in their world. Initially, I tried to mimic who I was talking to as far as using their vocal pitch and then even moved on to taking voice lessons to sound more like a woman. Finally, I moved to a point where I was half way comfortable with the way I sounded and I did the best I could.

I am biased of course but I feel the back up plans we transgender women or trans men face are far more impactful than those of the average person. We trans folk often face the possibility of losing almost everything as the "Plan B" we have when we enter the world. All too often, I read the sad, tragic stories of trans women losing their entire families, jobs and even friends when they made their way out of the closet. 

Hopefully, in the future, society will come around and we won't have to rely on severe "Plan B's" to survive.

Walking the Transgender Tightrope

 

Image from Johannes Plenio on 
UnSplash

I have never been accused of being coordinated at all which completely held me back when it came to me being able to participate in any sort of athletics except for football which often meant dealing with brute strength. 

Little did I know, I would have to develop my own sense of gender coordination to deal with my gender dysphoria. It turns out the better I became navigating the world as a novice transgender woman, the more balance I would need to survive in life. What happened was, the better I became with makeup and fashion, the more confidence I felt and in addition I was gaining the all important confidence to try more and more exciting yet terrifying experiences as my feminine self. 

Doing the more I could possibly hope for led me to trying to walk part of my life in my old male gender and part in my newer female one. My second wife even approved of a plan where I could have three days a week to leave the house dressed as a guy, go to a motel, cross dress as a woman and basically do whatever I wanted. Then dress back into my boring drab male clothes and come home. It didn't take long for me to become bored with this arrangement and I began slipping out of the house behind her back when she was working. Out of sheer willpower I needed to begin being more coordinated in how I was trying to run my gender conflicted life. There was really only one thing I knew for sure, I loved my feminine side and wanted to do more and more to let her out. 

Sadly, the whole process of trying to balance the two genders fighting for dominance within me was destroying my already bi-polar fragile mental health. I tried therapy and for years had only one therapist tell me the truth...there was essentially nothing I could do about wanting to transition into a transgender woman. I was what I was and I should accept it. Of course I wasn't smart enough to take her advice. I still wanted to save what was left of my long term marriage to my second wife while at the same time exploring what could be possible if I actually had the courage to transition into a fulltime world as a transgender woman. 

Finally, after falling off the tightrope more times than I can say, I could take the mounting gender pressure no longer and tried suicide as a solution. Just before my wife passed away from a massive heart attack, I thought I "purged" for the final time and got down from my tightrope. I grew a beard, gained a bunch of weight and overall was miserable but I gave it my best effort. 

I proved to myself I wasn't coordinated enough to navigate something complex enough as a gender tightrope and moved on to living a life as my authentic self. I am not one for regrets but if I allowed myself one, it would be I would have had the courage to transition earlier in life (before the age of sixty.) I would have saved myself so much time, effort and frustration as I attempted to balance my gender tightrope.      

A HUGE Relief

 

Image from the Jessie Hart
Archives 

What a huge relief it was when I finally decided I was living a lie barely surviving  as a male person. I remember the evening vividly when I made the decision years ago.

Even still, It took awhile for my male self to gave up and concede all along my feminine self was cross dressing as a man and not the opposite. His ploy was he was cross dressing as a woman to relieve stress or whatever the current excuse was,  because there were many. Such as was I just pursuing a fetish or some sort of a hobby such as golfing. Needless to say, in a short amount of time I discovered I had mush deeper issues when it came to dealing with my gender dysphoria. My desire to seek out the truth kept me searching for nearly fifty years.

The search also wrecked my fragile mental health along the path I was pursuing and I regularly sought out therapy for answers. On occasion, I felt better after visits with my therapist but overall my feelings never really improved. Mostly because I was not facing the truth I had always known but was afraid to face. I never was the man I pretended to be. 

Life became especially difficult for me when I grew older and friends, family and spouses began to pass away. When each death happened, it was like my feminine self was asking when was it going to be her turn to live before it was too late. Still I kept on searching, unwilling to totally give up on the male life I had built. Finally, when I was living my life torn between the two prime binary genders, it all became too much for me to bear. Either I needed to end it all and indulge in self harm or in a sense give up and do the right thing. Which was begin to live a full-time life as a transgender woman. What a HUGE relief it was. As I gave complete control to my inner woman, it was as if she had been watching and learning from the world the entire time I tried to hide her.

It turned out, all the days and nights I was so paranoid about facing the world turned out to be unfounded because I relaxed and let her take charge. The more my old male self stayed out of her way, the better she did. The prime example was appearance. She followed the basics of establishing a fashion sense which blended with other women around her and made life so much easier. The more she did, the more I wondered why I waited so long to give her control. 

Perhaps the biggest change was in my mental health. It improved so much, for the first time in years, I was able to leave my therapy behind. 

All in all I was fortunate in how I was able to transition into a new gender life as a trans woman. I already had a circle of supporting cis-woman friends who never knew much of the old male me, plus an accepting daughter and future wife who were pushing me forward into an authentic life.   I read of so many other transgender individuals who were not so lucky. I can never not give all my friends and family I often mention, enough credit for helping me to restart my life. The entire process of sliding down the male hill into a soft female landing was such a huge relief. 

Gender Chaos

 

Image from the 
Jessie Hart Archives 

Over time, I began to consider the chaos being transgender caused in my life. 

Looking back, I wish I had just a portion of the time back I wasted as I worried about how I was going to deal with all my gender issues. Every time I was able to set aside precious time to cross dress as my feminine self, I was only able to feel better for a short time before reality set back in and I started to resist my same old unwanted male self again. When it happened, I would become a terrible person to be around. Even to the point of losing jobs because of my actions.  Needless to say, this portion of my life was very self destructive. 

What I ended up doing was trying to outrun my gender issues which in my case I describe as gender dysphoria. I tried by changing jobs (which often involved moving) often and drank entirely too much alcohol as I attempted to out macho all my male friends while at the same time dulling my pain. Fortunately, I was able to stop my alcohol abuse in time to lessen any further chance of lasting damage to my body.

Backtracking a bit to all the moves I subjected my second wife to, we picked up and moved from our native Southwestern Ohio to the metro New York City area to run a fast food franchise. Perhaps an ulterior motive was to move to a much more liberal community which would provide more potential possibilities for my cross dressing gender expressions. After surviving almost two years, it was time to move again, as we returned to our native Ohio. As it turned out, yet another move awaited both my wife and I as I accepted a job to open fast food venues in Southern Ohio which turned out to be the exact opposite living situation than we faced in New York. We ended up renting a very rustic house in a rural area where we heated with a wood stove and utilized a cistern for our drinking water. Even still, I found ways to learn more about my gender challenges as I traveled into the nearest town.

Ironically, during this point of my life, I fueled my gender chaos by being successful with my feminine presentation. It was around this time when I started to begin doing the grocery shopping for the family as well as sneaking in quite a bit of shopping for myself. In essence, I leaned I could be on the right track thinking I could follow my secret dream of living as a fulltime transgender woman.  Little did I know how much chaos would lie ahead as my future played out. 

Recently I heard a comment which describes a large portion of the chaos I was to face. As I write about often, my deceased second wife knew and didn't object to my transvestite or cross dressing desires but never approved of me beginning hormones and starting to live more and more as a woman. As I headed down a path to no return with my gender desires. The comment involved the concept of emotional cheating and I immediately applied it to me. During my twenty five year marriage to my wife, I never physically cheated on her with anyone. However, as I became increasing involved with learning to exist in a feminine world, I started to sneak around behind my wife's back to live my new life. I wasn't proud of what I did but my only excuse was my chaos was so severe I could only do what I needed to do to survive. As I emotional cheated. 

All I know for sure, living through gender chaos is no joke and proves once again being a transgender woman or trans man is not a choice. Any transphobe who says it is needs to walk in our shoes for just a short time to see our truth.   

Transgender Vacation Blues

 

Image 
from UnSplash 

Back when my second wife was still alive, in the early fall or late summer we used to vacation close to the same area every year. 

We used to just take off and travel from our home in Southern Ohio and make the trip up through Toledo and Detroit up into northern Michigan. Often trying to escape the late summer heat, we went as far North as the Upper Peninsula of Michigan. It was a great time to go because many upscale venues in places such as Traverse City discounted their prices for off season tourists and we didn't have crowds to deal with. 

During that portion of my life, things should have been going good. My restoration efforts on our 1860's brick home, were coming together and both my wife and I enjoyed jobs which provided us with a little spendable income. What could possibly go wrong? In reality, just one major one. My battle with gender dysphoria. I was just beginning to experience more success as a novice public cross dresser and or transvestite and I wanted to do more. I was also riding the waves of gender euphoria when I went out and gender repression when I couldn't. Part time exploration of my transgender needs just wasn't working. 

It figured then, if I wasn't able to try to experience my gender euphoria just before we went on vacation, most certainly I would mentally crash and burn during our vacation. Of course when I did I would grow grumpy to the point where my wife would ask me what was wrong. She would ask what else I needed in life to be happy. At that point I just couldn't tell her the truth. The only thing which would have made me happier at that moment was if I was making the vacation trip as a transgender woman. From then on I did the usual male response and internalized my feelings and acted as if I was feeling better.

Sadly my gender dysphoria managed to ruin several vacations for me as time after time I fell into bouts of gender depression. I was even affected when we made our annual stop in the village of Frankenmuth, Michigan to look for rare Christmas tree ornaments my wife didn't already have since she was a Christmas fanatic. I over compensated by encouraging her to over buy every year. As we walked through the stores, no matter what I was outwardly feeling, inwardly I wanted to be doing it with her as two girlfriends. Naturally, the entire process ruined the vacation time I should have been enjoying.  I had the vacation blues which at times frustrated me even more because I should have been enjoying my hard earned time away from my pressure packed job.

Since I never had the courage to face my transgender truths until much later in life, my vacation blues never changed until I retired and met Liz, my current wife. The vacations we have taken changed the vacation narrative for me. The blues have disappeared and for once I have been able to enjoy myself. .