Losing Through Winning

 

Image from Humphrey Muleba 
on UnSplash. 

Sometimes during our lives, we have to lose to send ourselves forward into a better place.

It seems, transgender women and transgender men have so much more to lose when they transition across the gender border. As I often mention, we have to consider spouses, extended family, friends and employment as we grow into our unique authentic selves. I spent years in anguish trying to determine what to do about the two women fighting about my life. I mean my strong inner woman and my equally as strong wife of twenty five years, both of whom, I loved dearly. 

It turned out, the only loser was my male self, and he was not going down without a fight. When I was stuck between genders, my mental health suffered greatly. Even leading me to a suicide attempt when I did not think I could make a decision and could not take it any longer. I was attempting to live my regular working life as a male and the rest of the time as a transgender woman, and it was tearing me apart. The gender nightmare I was going through, I would have not wished on my worst enemy.

Finally, I decided I needed to lose one of my genders attempting to run my life. Due to an ever increasingly deep down feeling I was doing the right thing; I chose to go deeper and deeper down the gender rabbit hole and pursue my transgender womanhood. When I did, an unbelievable exciting, fulfilling new life opened for me. All of a sudden, I was being invited behind the gender curtain to girl's night outs and even accepted a gift from my daughter to have my suddenly longer hair styled at her upscaled salon. Looking back, I think my hormonal estrogen level increased significantly that day due to osmosis. Suddenly I learned why all women value so much their time at the beauty spa's. I was learning again why I could never go back to the male world I was losing.

As I looked around, what else did I have to lose? My wife had passed away, I closed my restaurant, lost most of my close friends to cancer, so I had nothing but a temporary fast food managerial job I hated to get me by until I could take an early retirement. Plus, I was on gender affirming hormones (HRT) by then, and my body was femininizing fast. My wins were rapidly overtaking the losses in my life. 

During the space of approximately five years, I had walked through the gender door perceiving I was little more than a parttime cross dresser and came out the other side as a full-fledged happy transgender woman. My male self-had totally lost and it was time for me to enjoy the win with my new women friends around me who taught me more than they ever knew about valuing myself. 

As with the rest of you who have gender transitioned, or are seriously considering it, I am sure I don't have to tell you what a big decision it is. First you need to accept yourself, then see if others will accept you too. Once you do, you can begin to win and put your losses behind you.  

Creating Gender Tension

Image from Tim Mossholder 
on UnSplash.

 
I am aware of the natural tension which goes on between the binary genders of male and female. 

I am also aware of the added tension which goes on when a transgender woman or trans man tries to cross the gender frontier to live on the other side. For me, at least, the tension became ridiculous and ruined my mental health which was already fragile. Before I was diagnosed with gender dysphoria, I was diagnosed with being bi-polar also. At the time, the diagnosis seemed to be a double-edged sword because I was wondering why I suffered from deep mood swings and blamed the swings on my gender issues. When I found I had deeper mental health issues, in many ways, it was a relief they were not tied in with my cross dressing. On the other hand, ideally, I could treat being bi-polar with medications and move on with my life.

My worry was any future therapy I might seek out, would involve the therapist attempting to tie my mental health in with my need to be a woman. Even though it was true, my gender needs did conflict with my mental health and cause tension, they were both separate entities and needed to be dealt with separately. I was fortunate in that I had two long term therapists who agreed with me, and I was treated as such.

However, my gender tension never went away, and, in many ways, I just learned to live with it. What I did was, resort to what I did when I was younger and try to cross dress my way through my transgender life. Predictably, when I was cross dressing, life was good and when I was not cross dressing, it was not. I was mean and tried to take it out on the world around me. I became so mean on occasion; I lost a job because of it. What no one understood was, I was being tougher on myself than anyone else. In typical male fashion, I was internalizing my feelings until they exploded. I even used therapy as a crutch with my second wife who had to put up with me. The best way for me to explain it is, I would never quite tell my wife what my therapist said. The prime example I can give you is, very early in my sessions with a certified gender therapist, she told me there was nothing to do concerning me wanting to be a woman. Sooner or later, I was to just have to follow my instincts.

There was no way, I could tell my wife that when I was supposed to be undergoing therapy to save our marriage. So, I ignored what the therapist told me and predictably, the gender tension continued and even became worse. I did my best to tread water and try to live a life divided between being a man part of the week and a trans woman when I could the remainder of the week. It nearly killed me as I tried my best to maintain an impossible life. My best was not good enough and I attempted an ill-fated suicide. When I woke up the next morning after taking all the pills I had and chasing them with alcohol, self-preservation kicked in and once again I made the wrong decision and resolved to purge most of my feminine fashion and make up, then go back to my male life. 

We all know the majority of gender purges don't work. Certainly, it did not work for me, even when I grew a beard to satisfy my second wife that I was not doing anything related to cross dressing at all. Once again, my gender tension rose to a very ugly level, and I was very unhappy. Little did I know, my life was due to change in a very tragic and dramatic way when in approximately six months, my wife passed away from a sudden heart attack. 

The life changing experience led me back to my feminine self and I never looked back. When I did, the gender tension I was suffering from disappeared and I felt free.  

What is the End Game?

 

JJ Hart, Woman in Red.

Wow! My journey was a long one to transgender womanhood where I always thought I should be. Nearly fifty years from being a part-time cross dresser to fulltime transgender woman. 

The problem was getting there, because the end game scared me so much. I was in my own gender quicksand and could not seem to get out. I had no dashing cowboy riding up to rescue the damsel in distress. I was on my own. So, I persisted through countless days in front of the mirror or combing through thrift stores searching for just the correct fashion statement.

The more I learned about my feminine self, the more I realized how strong she was and how I needed to protect our relationship. The more I did, the more I began to see the end game could be in sight, if I wanted it bad enough. I knew the possible pain of giving up family, friends, spouses and employment to see the end game in person. The problem was, I was gaining more and more experience in my feminine life and every time I did, I did not want to go back to my unwanted, boring male self but I did. Over and over again until it wrecked my mental health and almost cost me my life. 

Still, I kept my eye on the goals I had set which brought me ever closer to my end game of living life as a transgender woman. Along the path I had set for myself, I still had very real doubts if I could do it. I also found out quickly, just daydreaming my life away about being a woman or cross dressing in front of the mirror was not working anymore. I needed to get out in the public's eye and live to be certain I could do it all if I needed to. 

Spoiler alert, I needed to learn all I could to survive in the very competitive world of women. I thought men were bad, but women brought a whole new intensity of competitiveness to their world with other women. In order to survive in the girls' sandbox, I needed to bring a whole level of intensity myself to keep up because on occasion there was quite a bit of kicking and scratching going on behind my back. Once I adjusted to the new world I was in, I was OK after all the scratches on my back healed. Plus, I always kept in the back of my mind, I needed to be better than the average cisgender woman to survive. Mainly because I had so much more catching up to do and I never wanted to get discovered presenting the least bit as masculine. If I ever did and slipped back into old habits, I would have to work so much harder to regain my place in the world as a trans woman.

As I did, I found I naturally was fitting into my authentic life, I found myself at a crossroads of gender. Most importantly, at the crossroads I could see what my end game was. Since I was increasingly thriving in my transgender womanhood, I saw no reason to go back. When I did, a huge weight was lifted off my shoulders and life was livable again. 

I had found my end game was achievable and when I did, all things were possible.  

A Line in the Sand

Image from Lance Asper
on UnSplash

 It has been over a decade now when I decided to finally draw a line in the sand and give up on my well-worn, unwanted male self.

I say well worn, because I had spent nearly sixty years trying my best to live up to the supposed ideals of the male gender. It was exhausting keeping up with all the testosterone driven male "club." Still, I persisted and managed to build a fairly successful life. Once I was successful and had built up my share of male privilege, it was difficult to want to give it all up.

The pressure of having the possibility to live my dream of transgender womanhood finally got the best of me after a very serious suicide attempt. Finally, I needed to draw the line in the sand and do the right thing. The thing I had worked all those years of being a cross dresser to do. Even still, I knew deep down what I needed to face and do. It was just because at times, the line appeared to me as deep as a canyon. It was scary trying my best to jump it and exactly what was on the other side. I was fortunate in that I was able to research deeply what a life would be like as a transgender woman. 

I did my best to live out the life I would expect to live if I transitioned from a cross dresser to transgender woman. Against all personal odds, I was able to find a whole new set of friends and acquaintances who accepted my authentic self. They in turn, taught me so much about being myself. What worked and what did not. For example, I did not want to be too loud or impulsive but on the other hand I could not be very introverted because I would be mistaken for being bitchy. For a while, it was touch and go in my learning process, until I felt confident. 

I compare the process to a gentle pleasant wind coming up and blowing away my line in the sand. Very soon, I could not see where it even was. When it happened, it made up for every male privilege I lost. Quickly I forgot how I felt when I was "mansplained" by a guy or how I felt when I made to feel I had lost part of my intelligence just because I was a woman. I just knew how important I felt when I had finally arrived on the other side of my line in the sand.

Old friends, and part of my family were gone but quickly I was able to replace them with new friends and another accepting family unit. In many ways, life was still terrifying but so much more exciting and satisfying. I should have never waited as long as I did to erase my line in the sand. No more thoughts of suicide and for once being able to be myself were just a couple of the benefits. 

Never a Choice

 

Image from Mika
Baumeister on UnSplash

After all these years I still receive the comment of why I chose to leave my male gender behind and pursue transgender womanhood. 

Ironically, very few people removed from the transgender umbrella understand I never had a choice and spent nearly fifty years figuring it all out. Sure, there were brief moments of gender clarity which somehow, I refused to recognize. Then, as the years rolled by, I kept accumulating male baggage which became more and more difficult to consider leaving behind. Examples would be family, friends and jobs which being masculine depended on success. I was caught between having success as a male in a world I never really wanted. For the longest time, every time I was successful at something as a man, I fantasized if I could do it as a transgender woman. A stop gap measure which in the end just caused me more frustration. 

Plus, eventually, frustration turned into more gender pressure. The whole process turned me into a very self-destructive person. Along the way, I tried to tear down all the male successes I had built up. I drank too much, drove too recklessly and even tried suicide as a final solution to my gender pain. Finally, before it was too late, I realized my error. I never had a gender choice and attempting to live even a partial life as a male was a waste of time.

To make matters worse, I was very stubborn, and I attempted to hang on as long as I could in my transgender world by trying to live partially in both worlds, male and female. Slowly but surely, I discovered I could not continue to live that way. The more I learned about living as a trans woman, the more feasible a complete transition became to me. The whole process took me back to my earliest days cross dressed in front of a mirror at home when I realized I wanted to do so much more than just look feminine. I wanted to be feminine but my upbringing in a male dominated family was throwing up all sorts of roadblocks for my future. So, I learned what most men learn. To internalize my feelings the best I could. Which would lead me too much more serious problems later on in life.

The biggest problem was I was fighting the gender battle of my life. Regardless of what my male self was telling me about maintaining the status quo, sooner more than later I would have to face reality and know my gender was never a choice. I could not rest and enjoy my life until I finally made the ultimate decision. 

One lonely night as I was again pondering my future at the age of sixty, I weighed the benefits of both of the genders I was trying to maintain. In a blinding moment of clarity, I gave up forever any rights I ever had to a male life. 

It was the best decision I had ever made in my life. All of a sudden, this huge weight was lifted off my shoulders. From that point forward I decided to pursue gender affirming hormones and give all my male clothes away. Most importantly, I faced up to the fact I had never been a male except biologically which had nothing to do with my brain. I followed my brain and never looked back. '

Without the gender monkey on my back, I had a chance to live my life my way. The way I never had a choice of and took too long to realize it. 

Gender Harmony

 

My friend Racquel and her dog.

When asked when I first realized I had issues with my gender I began to tell the truth and say I had known forever.

In fact, my statements were only partially true. I knew something was wrong with me, but I did not know exactly what. When I was young, I knew how much pleasure I received when I dressed as a girl. What I was lacking was the knowledge of how much harmony I was missing by learning the aspects of living in two genders.

Over a long space in time of nearly fifty years, my male and female selves battled it out, which naturally created huge disruptions in my life. My already frail mental health was in shambles most of the time. Since I had already been diagnosed as being bi-polar by a therapist before, my gender issues seemed to be a bigger problem. In reality, both issues were working together to make my life miserable before I took action and did something about it.

I started with the easier one, my bi-polar condition. After I tried several medications, I found the right ones which I am still taking to this day. The much more difficult of the two issues destroying my inner harmony was my issue with my gender. Had I listened to my first therapist years ago when she told me there was nothing, she could do with me wanting to be a woman, I would have been better off. Maybe I would have been able to relax more with my issues and realize my transition into transgender womanhood was going to be a scary yet exciting journey I should try to relax and enjoy. Rather than fight and destroy my mental health as I did it. Plus, what made matters worse was all the people around me I attempted to make miserable too. Leading my second wife to even consider telling me to be man enough to be a woman. The problem was, back in those days, I did not have the feminine experience yet to do it. So, my miserable life continued.  Any sort of gender harmony seemed to me an impossibility.

During that time, I really set out to seriously discover what measures I would have to take to restore any sort of harmony to my life. Which essentially saved my life after a failed suicide attempt. I found I had to discover harmony or face losing my life totally. 

Initially, I was obsessing on my feminine appearance over any other aspects of being a transgender woman until my trans friend Racquel told me I passed out of sheer will power. Deep down, I knew what she was talking about. I was not and never would be the most attractive woman in the room, unless I could afford the expensive facial femininization surgery. Which I couldn't. It did not matter anyhow, since I had already decided to move forward in the world with the best possible appearance I could put together. 

Long story short, I found my path to a new life and am very fortunate to live as a full-time transgender woman. Racquel went on to several appearance altering surgeries and moved away so I have not seen her for years. I owe her for the honesty she expressed to me concerning my coming out experience. As my wife said too, there was so much more to a woman than just looking like one. Finding harmony with myself, enabled me to find harmony with others. I made friends in my new life and moved on.

NOT for Entertainment Only

 

Image from Alice Alinari
on UnSplash

As I went along my path to transgender womanhood, I found the journey was never a choice and was not for entertainment only.

My journey did not begin that way. Similar to many of you, I started by exploring my mom's underwear drawer and wearing what would fit. All of that was seemingly innocent enough unless I was caught. Then there would undoubtedly be hell to pay, along with a trip to a psychiatrist. Later I would wonder if my mom ever knew because her underwear was stretched out, but she never approached me at all. 

It was all fun and games until it wasn't. Slowly, I learned wearing girls/women's clothes was not for entertainment only. I was becoming increasingly serious about it. For the first time in my life, I was obsessing over how I looked. How was my makeup and very limited access to a wardrobe appearing in the mirror. I even went as far as shaving my legs when I thought I could get away with it. In addition, I did my best to study the other girls around me. I did not know it then, but I probably was wearing makeup before a few of the girls I knew were allowed to do it. At the time when I could not seem to muster the same passion for building the model cars I had and painting them well, makeup was an entirely different challenge and one I could not resist doing my absolute best at doing well. With no help whatsoever. 

I found, for the first time in my life, I was completely serious about doing one thing and it was being a girl. Not just looking like one. It took me years to learn just gazing at my reflection cross dressed as a feminine person was just not enough. I needed more. My problem was early on was having the budget to do anything such as being able to afford having a nice wig. It was not until my college days until I could buy a long blond wig I cherished for years. Spending all the money on one specific fashion accessory proved my passion to look good was not for entertainment only. I was really serious.

Of course, then I really started to step up my gender game. When I was released from my military service, I began to seriously explore the world as the feminine trans woman I was destined to become. As I write about often, my journey was filled with ups and downs and my mental health suffered. Definitely not the way I thought it would be when I looked at myself dressed as a girl in the mirror early in my life. What I never had a chance to consider was I was not a transvestite or cross dresser at all. In fact, I was a transgender woman and needed to accept it. I was never in it for the entertainment and my life depended on a successful outcome. 

What I mean is, I needed to stop all the self-destructive behavior I was exhibiting as I sought to destroy everything successful, I had ever done. Along the way, I had tried to lose jobs, drink too much all the way to trying to kill myself with pills. Never realizing how much I had to live for if only I followed my transgender path far enough. 

I wonder now, if I had realized how difficult my journey would be and not be entertaining would I have ever undertaken it at all. I also realize now, I never had a choice, and my life would have been better had I realized it sooner. I would love to get back just a tiny portion of the stress and tension I lost during my life as I worried about my gender. Outside of a few therapists who tried to help me by telling me the truth about myself, I was on my own. My life was never for entertainment only as I followed a gender path full of turns and dead ends before I discovered my truth in my transgender womanhood. 

Now What?

 

Image from JJ Hart

As I cautiously discovered I could make it in the world as a transgender woman, rapidly I kept coming to the conclusion of now what.

How would I face a whole new life without the old male standbys to fall back on. I had taken the time and effort to build a family, friends and a fairly successful job which I had to possibly give up. Naturally, I spent hours, days and weeks trying to figure out what I would do once I entered fulltime transgender womanhood. I had long since passed the point of just being satisfied with existing as a part-time cross dresser. 

Ironically, every time I was successful in public as a novice trans woman, I wondered now what I  have I done and what was next in my life. The problem was, I had several major roadblocks which were looming in my life, such as helping to care for aging parents and a spouse who was totally against me transitioning any further than I was. To diminish the impact of all the gender stress I was dealing with, I did what many males try to do and internalize all of my problems. Even though I was going out as much as I could as my authentic feminine self, the fact remained I would have to go back to my old unwanted male life sooner more than later. As Paula from the UK put it in response to a previous post:

"For me it was the depression that followed "putting Paula back in her box", each time I went back to being "him" it was like a bereavement, in the end it was bowing to the inevitable. Arguably transition was the most selfish thing I have done, but like so many others I was insufferable trying to maintain my male persona, in the end it wasn't so much choosing my feminine side as choosing life."

Similar to Paula, the entire transition process for me came down to life and death for me. Like so many other transgender women or trans men, I attempted suicide to relieve myself of the brutal gender related stress I was feeling. Fortunately now, I was unsuccessful and lived to write about the experience. In fact, it was one of the reasons I began to author a blog.  In order to help others. 

Perhaps you are wondering how now what worked following my attempt at self harm. I still was not smart enough to listen to my inner female and tried to purge my fairly extensive feminine wardrobe and makeup. It was during this time too, I began to notice my second wife's health was slipping badly and she would end up passing away at the age of fifty.

Then I really entered the now what part of my life. The door had suddenly opened for me to live my dream of living fulltime as a transgender woman. I followed my soul and began gender affirming hormones at the age of sixty and never looked back.

All the days of wondering now what were behind me. All the risks I took were with it as I began to happily live an authentic life. And, by the way, Paula thank you for the comment and thanks to all of you reading along. 

De-Transition?

 

Woman's get together. I am on the 
bottom row, far left.

Several posts ago I may have written something which made some readers think I was considering ever de-transitioning back to my old male life.

To begin with, there is no way I would go back to a life I never appreciated. Even though I was mildly successful at living a male life, something was always missing. It turned out what was missing was my feminine soul. The problem was I needed to develop my feminine soul to the point where she could flourish. It took me years to discover the truth with many starts and stops along the way. For years it seemed everytime I took a step forward as a transgender woman then I took a step or two back. The entire process was very frustrating. I was finding out leaving the men's club and entering the woman's club was going to be much more complex than I ever thought. 

Even with all the threats to the transgender community today, the easy way out would be for me to go back to the life I used to have. Also during my life, I have learned taking the easy way out is not often the best way to exist and be true to yourself. Trans womanhood was my true self and when I recognized it, my fragile mental health as well as my life in general improved. So, I knew completely I had done the right thing by stopping the cruel joke I was leading trying to live as a man. The major reason I would never go back to an unhappy existence which led me to alcohol abuse and even a suicide attempt.   

When I transitioned into a feminine world, I finally also learned how to be happy. Something I had never learned how to be. All the time, effort and work I put into relearning how to live made the whole process so worthwhile. So why would I give it all up?

Then there were all the magical hormonal changes I went through when I started gender affirming hominess nearly a decade ago. When I did, it seemed my body took to the changes so naturally and was so ready for change. Even though I experienced many external changes to my body, I also went through major internal changes such as emotional growth. I constantly worry about giving all of the hormonal gains up from HRT if I had a medical emergency or if the government tries to take them away. 

I also had a question from Georgette about the picture I used for the post. She asked if I ever had seen any of the women again and were any LGBTQ orientated. I do keep in occasional contact with two of the women in the group and no I don't think any of them have or had any other contacts in the LGBTQ community. In essence, I was really just one of the girls except for one woman who seemed to really resent me.

I hope this answers some of the comments I receive here. For obvious reasons, I can't answer all of them in a post but I thought the de-transitioning comment was important enough to share. As always I really appreciate all the input I receive. Thank You. 

 

Down but Not Out

 

First Girl's Night Out.
I am on the bottom row, left.

There have been many times during my transgender journey which I have felt down.

However, a little voice in my head kept telling me to keep going and if I did, I could achieve my dream of living a feminine life.  I write many times (mainly for those of you who are still new to the transgender or cross dressing world) how I was ridiculed intensely when I first tried to explore the public as a woman. After being laughed at, I always headed home in a hurry and tried to go back to the drawing board to try to determine what I was doing wrong. It took me awhile to figure out I needed to get past my male ego of what a woman should look like and into blending in with the rest of the female world. The mirror and my head turned out to be powerful opponents. 

I need to stress, it took me years of being down to turn my learning curve the opposite way and turn my frown into a smile when I was out in the world. Along the way, I needed to adjust my thinking on how I was accepted. I needed to realize I would never be the most attractive woman in the room and begin to fall back on my personality to get along. I was transgender and different but so what I was a good person. When I accomplished being at the least friendly to others, I began to be accepted into small groups of acquaintances who accepted me for my true self. In one of the venues I became a regular in, I have vibrant memories of a group of five diverse women and even a few men who I could set in with and have a beverage. 

It all proved to me I was resilient and could survive most things, including my growth as a transgender woman. Even though life was about ready to deal me several severe setbacks I was not expecting, I could make it. 

When life did hit me with setbacks, they were sledgehammer type blows. It seemed life was fond of giving me setbacks such as my wife passing away along with most of my best friends. It nearly finished me off when I had to close my restaurant I worked so hard to buy. More or less, I was left with my house, two dogs and an old car to re-erect my life. 

The old saying the darkest hour was right before the dawn was true for me  I was down but I had one huge card up my favorite blouse's sleeve. Since I was so far down why not start all over again as my dream self. My inner female had always been strong enough  to fight for her existence, so why no let her have it. Karma was on my side also, as it was about this time the Veterans Administration  health care system which I was already a part of suddenly approved the use of gender affirming hormones for transgender veterans. I only needed approval from a VA therapist to start the program. It turned out I was with Dr. C. my therapist for over ten years and she worked miracles for me.

Maybe it was because I was able to outlive a suicide attempt and years of self destructive behavior that I was able to come full circle in my life and end up on my heels. I was down but not out and discovered people in the world who could and would step up to accept me as my authentic self. Even though I needed to make the effort first. Which for me was very difficult. In the end, the whole process made me a better person.

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.

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.

It was All so Natural

Image from the Jessie Hart Archives. 

Even though I was facing tremendous hurdles as a cross dresser and/or novice transgender woman, everytime when gender times became tough, I kept on trying. Mainly because deep down  I felt so natural when I was cross dressed head to toe as a girl my age.

Although the time I was cross dressed felt so good, the length of time I was able to do it was never enough. Had I had more knowledge back then, I would have realized I was a transgender person. A big difference to me from only being a part-time male who enjoyed cross dressing in women's clothes. As I discovered more and more about myself, I discovered I was a woman cross dressing as a man during the majority of my life. I only knew I was not enjoying or was being fulfilled as a guy. The whole lifestyle never felt natural to me. 

As time went by, I increasingly followed the natural path no matter how difficult it proved to be. More often or not, I encountered very many severe twists and turns. Again, I was encouraged by the natural moments I experienced when I finally encountered the public as a trans woman. It was like the path had big sign boards along the way with directions on how to proceed. Or once I made it to a certain spot in my new gender life, I could set new goals. The example I always use was when I started to progress past just going shopping in clothing stores where they didn't care if I was a man dressed as a woman or not (because my money was green) and began to challenge myself in restaurants where I needed to interact one on one with the serving staff.  

From there, my goals became to refine and test my restroom skills if nature called during one of my longer outings. It was during some of my restroom visits when I  really needed to feel natural and spread my gender wings. I found out quickly I needed to be able to look other women in the eye and smile even though I was very scared. 

Through it all, I lived and was able to move forward towards new enticing goals of living life as a transgender woman. It was during this period of my life when I began to seriously consider moving forward with gender affirming hormones. Sadly, my second wife was very much against any idea of me being on hormones saying if she had wanted to marry a woman, she would have looked for one. In other words, she didn't sign up to live with another woman, trans or not. I loved her deeply and no matter how difficult it was, I tried to honor her wishes until her untimely death after we had been married twenty five years. 

Her rejection of any idea of me moving forward with HRT just put an extra strain on my mental health which in turn, led to a suicide attempt. Following the attempt, I tried yet another "purge" of my feminine wardrobe which of course didn't work. It wasn't too long after my final purge, she passed away very suddenly from a massive heart attack. As I write about often, her death was the ultimate shock to my system because I was always so self destructive there was no way I thought I would out-live her but I did.

When I did, I decided it was time to live my dream of being a full-time transgender woman. I took the natural path and never looked back.  

Living in Your Own Prison

 

Image from Engin Akyurt
on UnSplash

When someone says living a life as a transgender woman or trans man is a choice I get a huge chuckle. 

I wish the people who think my life was a choice, needed to live a small time in my shoes and  then they could truly decide my life was never a choice. I was living in my gender prison. In many ways, I could describe my confines to a bigger version of what was called my personal closet. Either way, I was stuck in a very dark and isolated space where I was all alone. Especially in the pre-internet days when I was living.

When the internet came along with social media, I was able to locate a few others who were cross dressers or transgender women , which made life a little easier in my prison. My biggest problem then became hiding my new on-line contacts from my wife who was more tech savvy than I was. Let's just say I needed to learn the hard way when my wife found a discussion I was having with a person in nearby Indiana and I had to become much too comfortable with.

Looking back, I could call the few, brief times when I tried to purge my feminine wardrobe and be a full time man as being out of my prison on parole. The problem was deep down I knew what I was doing was wrong and the pressure would build to build a new feminine wardrobe and try again in front of the mirror. I could almost predict when I would go back to my gender prison. 

Yet another casualty of me serving time in my closet was one I always mention, my mental health. Since it was already fragile and I was going to therapy for help, I didn't need any extra problems to push me closer to the edge.  I was becoming a hot mess as I took more and more chances when I left the house as my novice transgender self and explored the world. The problem became, I was feeling more and more natural when I escaped my prison. Even still, the process was not easy and involved too much scary trial experiences when I first went out. 

The entire process became all I thought about and when I was in my my male mode I caught myself thinking too much of the next time I was going to be able to experience life as a transgender woman. Plus, at the least I was busy studying the mannerisms of all the cis-women around me. I was locked in to one thing only and it was being a woman myself. It was a good thing I had my therapist to talk out my exploding feelings about my gender. 

I guess the only frustrating part of trying to explain to the outside world what it means to be transgender is there was no choice. If I would have continued in my self destructive male ways, I would have killed myself and become yet another statistic. Fortunately, destiny had other ideas for me when I escaped my gender prison and started to live an authentic life as a trans woman. Similar to so many others in the transgender community I was a survivor and thrived when I was free to do so. 

Un-Common Risks as a Trans Girl

Liz on left. Date Night. 

Most people undertake a risk or two as they make their way to the undertaker in the end. 

When you come right down to it, which person you chose to marry is a risk as well as which profession you choose. Transgender women and trans men seem to have an added layer of risk in their lives. Along the way as we pursue a gender transition, we have to make many difficult choices which aren't really choices at all. They are paths we have to follow or face devastating self harm to ourselves. Which results in extremely high suicide rates in the transgender community. 

When we are growing up in a world where our families often don't accept us, the entire process makes the risk factor even more important. I am so blessed to have a daughter who completely accepts and supports her transgender child and I am proud to have been a role model for my grandchild to follow but it wasn't easy. 

When it came to my marriages, seemingly destiny has led the way into several different areas of acceptance. Acceptance of course led to risks being taken. My first wife was very easy going and knew of my cross dressing desires before we were married and had our daughter who turned out to be my only child. My first wife accepted without question my desire to cross dress as a woman and venture out on Halloween adventures. I often thought if I came home from work one day and told her I was checking into a hospital for gender alignment surgery, she would have said that's fine, just be careful. As it turned out, I was not ready for that sort of surgical risk and would never be.

Then destiny threw me a curve ball with my second wife. The moment I saw her for the first time, I knew I wanted to be with her in the worst way. Even though she too knew I was a cross dresser, she still restored feelings I long ago had forgotten when I was ready to compete with another man for a woman. In order to win the competition I needed to divorce my first wife and move on to a totally different strong woman who knew somewhat of my gender issues. I say somewhat because back in those days I was just learning myself how deep my transgender feelings ran which were to cause strong problems in our twenty five year marriage later on after the newness wore off. From the start, I always thought she would be the one who would help me to break through in my cross dressing world and help me to be successful in my dreams. As it turned out, she wasn't that person and always drew the line if I suggested at all I wanted to go further into the transgender world. By the time she had passed away, our relationship had deteriorated into an ugly cat and mouse game of me taking risks and seeing what I could get away with.

Another main risk I took was with my job. Slowly but surely I had been promoted through the managerial ranks to a successful position as an executive general manager of a big popular casual restaurant chain. A position with a company I knew would not accept me transitioning into a transgender woman. In my haste to destroy myself anyhow, I began to go to my competition as a woman thinking no one would recognize me. Well, I was wrong and the roof began to fall in on me. It was tough but I denied all the rumors and kept on going.

By this time, my second wife's life was coming to an end and she suddenly without warning passed away from a massive heart attack. By this time I had purchased my own restaurant and was somewhat in control of my own financial destiny until a recession in the Rust Belt where I lived wiped out the population. I ended up losing my restaurant as well as my inheritance by taking a major risk and losing nearly everything I had. I finally was able to find me a fast food job to hold me over till I could take an early retirement from Social Security and sell vintage items my wife and I had collected over the years. Between the two I survived.

I then found myself in a period of wonderful gender discovery, when with the help of new women friends everyday seemed as if I was reborn. Specifically Kim and Liz helped me the most. Liz lived in nearby Cincinnati and we met on line. After corresponding by email  for months, I finally became brave enough to talk to her in person and our first date was at a drag show. That date was nearly twelve years ago and we are coming up on our second anniversary of marriage. Liz cemented her place with me when she told me she had never seen a man in me and why didn't I finish my transition into a feminine world with her.

Finally, after a half century of wondering and suffering over my gender dysphoria, someone else recognized my truth and wanted to accept it with me. My un-common risks were over. I accepted her advice, gave away my male clothes and never looked back.

A Toxic Male?

Image from Jurien Huggins
on UnSplash.

As I transitioned from a male to a feminine life, I often looked back at my life as a guy to determine if indeed I was a toxic male in any way. 

Of course I immediately mentally recoiled when I thought I could be toxic towards women in any way. After all I had spent a considerable amount of time worshipping the women around me, wondering how it would be to experience just for an instance being a girl. How come I couldn't wear the pretty clothes and be the gender who was so admired by the other. The problem with me was, I went way past just admiring a girl sexually, all the way to wanting to be a girl physically.  

Did any of it make me a toxic male? No, I don't think it did. In fact, I think the opposite happened as I put women up on some sort of an impossible pedestal. By doing so, and adding the fact I was extremely shy, I never had much of a chance to interact with girls or women growing up at all. From my perspective, the feminine grass always looked so much greener. 

Since I was forced into the male camp, I needed to learn to exist and had to put up with sexist comments directed towards women from many of the guys I grew up with all the way to adult hood. Mixed in too were the bullies I needed to somehow co-exist with. I learned to bluster my way around the bullies without jeopardizing my inner transgender self to ridicule or worse. In order to do so, I participated in as many of the male activities of the day as I could such as sports and cars. It worked and I was left alone for the most part and I even dated a few girls along the way. Since it is prom season around here, I am always reminded of the two proms I went to in high school. Even though I was the perfect gentleman at the proms, I wonder if my dates thought perhaps I was a little too timid and took it personally. I will never know because one of my dates and first serious girlfriend before college later in life committed suicide years later when her husband left her. What a shame. 

As I started college and started to date more regularly, I really began to see the results of toxic males around me. Especially in the fraternity setting I was briefly in. Certain fraternities were expected to co-mingle and party with certain women and sororities only where I went to college. I found out very quickly I did not fit in with the frats social system. Which was a forerunner to me not fitting in with the strict layers I encountered at the first cross dresser - transvestite mixers I went to. I felt so out of place and the only toxic people I saw were the "A" listers who were doing their best mean girls high school impressions. Maybe their male toxicity was bleeding through. 

I completely learned how not to be a toxic male when I settled into a career in the restaurant business. Along the way, as I progressed into higher management positions, I needed to coexist increasingly with women. Both crew members and managers. I learned quickly female crew members had the tendency to build cliques (not teams like the men) to be successful and the women managers I knew had to be tough but fair to survive. I on the other hand needed to be on their side when it came to battling any toxic males at all. Looking back, I think male toxicity was the prime reason for letting someone go. Which included sexual harassment which is a topic for another blog post.

My only regret was I wasn't a more vocal advocate for women my entire life as a man. I could have certainly spoken up when another guy joked about a woman. My only excuse is I was so intent on hiding my interior feminine self, I was afraid to do more. Transgender women and trans men speak of the importance of allies speaking up for us. I feel the same way about standing up for women before I transitioned. 

Saving my Own Life

Image from Alysha Rosly 
on UnSplash
 

 
I make no secret of my Bi-Polar mental condition which went undiagnosed for a good part of my younger life. 

Ironically, it was my first gender therapist who connected the dots and determined my condition when I told her I often spent days struggling to even get myself out of bed. I just thought I was riding the waves of gender dysphoria  which kept me so depressed or elevated when I was experiencing brief moments of gender euphoria. During this time of my life, I was far from being the easiest person in the world to live with. At the least, I was prescribed medications which evened out my moods. The meds also helped me sort out my gender issues and finally figure out one mental issue had nothing to do with the other. In fact my gender dysphoria was not a mental issue at all but instead an organic one. Had I listened to my therapist, she was trying to tell me all of that but I was unwilling to listen. Primarily because at the point of my life I was in, I was still a novice transgender woman and didn't know if I could live my dream life.  There were still too many gender bridges to cross such as telling family, friends and bosses I was transgender. 

The furthest I had come at that point was telling approximately five close friends and spouses I was a transvestite. A long way from living as a transsexual with all the resultant rules I would seemingly have to follow Such as major gender operations, moving away and then starting all over again. To make matters worse, I hadn't even thought much about my sexuality. Would I suddenly desire men sexually? I was overwhelmed with all the big questions and just continued my life as a very serious cross dresser. At the least, I was able to work on my presentation as a woman and go from there.

Even though, my solution was far from perfect, I was saving my life the only way I knew how. The problem kept reappearing when I started to go out more and more behind my second wife's back. When I did, I fairly quickly began to build up a robust life as a transgender woman. Every step I took, the more natural I felt when I could never see how I could go back to living a male life. The whole process created tremendous pressure on my already fragile mental  health. I became increasingly self destructive, all the way to an unsuccessful, ill advised suicide attempt. Essentially, from the point of suicide, I purged most of my feminine belongings and even grew a beard to prove to my second wife I could do it. By doing so, I was intensely unhappy for the short time she lived until passing away from a massive heart attack. I often wonder what would have happened with us had she lived.

Following the tragedy in my life, over a short period of time, I regathered myself and refocused  on a new feminine life. I quit dwelling on death and began living a preferred life as a transgender woman. By doing so, I was all of a sudden needing to quickly learn more than I ever imagined about my new life. Throwing out or giving away all my male clothes was at once liberating and  on the other hand, very scary. I had never purged my male self my entire life and he resisted. 

Regardless, scary or not, the process of a gender transition saved my life. Over a space in time, my mental health has stabilized and with the help of gender affirming hormones, for the first time in my life, my body and mind are beginning to mesh. The entire process took me a lifetime to figure out but as I always say, it all was so worth it. 

Transgender Pressure Cooker

Image from Jeshoots.com. 

When someone writes or says something about me being a transgender woman being a choice, I have to laugh. 

I'm sure those of you who have gone through life the way I have with gender issues would agree. Primarily because we have given up so much to cross the gender frontier. Primarily, I am referring to losing family, spouses, employment and gender privileges to transition. Just losing male privileges alone is a major issue. Very quickly I discovered I lost a portion of my intelligence when by accident I became involved in a conversation with several men. I found I was not respected in their world until I finally got tired of being ignored and left the group. Then I began to not speak much until I was spoken to until I began to gain more confidence. 

When I began to be successful, the pressure to be even better as a transgender woman started to increase. For several reasons, my fragile mental health became worse as I started to try to live a life situated between the two main primary genders. In other words, I was stuck in a gender fluid universe I did not want to be in. Living one day as a man and the next as a transgender woman, nearly killed me.  It became so bad I needed to make a conscious effort daily determining what gender I was going to be that day. How was I walking and talking were just a few of the many gender considerations I was going through as the pressure kept increasing. 

All of a sudden, I was able to establish a whole new identity as a trans woman. I was talking to other women and building a small circle of friends which taught me so much about the world I so much wanted to be a part of. I kept going because the process became so natural to me and very soon the main source of pressure came from having to return to what was left of my male life. Even thinking about going back caused me stress and added pressure. 

Finally, I knew I had no way around it and never really had a choice with my life. As a gender therapist told me so many years ago, there ultimately would be no choice for me if I was a transgender woman. Sadly I did not believe her and stubbornly went on to fight a losing gender battle for years before I gave up and faced my gender reality. By doing so, I tried very self destructive measures including suicide and excessive alcohol abuse before I started to live my truth. 

I had no choice and needed to give up all the pressure I felt to transition into a feminine world before it all literally killed me. Thank goodness for all the friends and family I had who helped me through my difficult pressure packed days. The more good days I had with them led to my belief I could live my gender truth full time. Ultimately transitioning was similar to sliding down a hill towards a steep cliff for me. I had others around me who took the pressure off and made the landing a soft one.  

Trans Crisis Management

 

Image from the Jessie
Hart archives. From the Ohio 
State Student Union. 

Over the years as I went through the process of living my life as a transgender woman, I encountered many instances of crisis management. 

Some of the encounters were funny, some were anything but funny. Several come to mind as I write this post. Probably the most humorous account came at the ill fated expense of a water balloon I used as a breast form one night when I was going out to my regular venues I loved the feel of the balloons. They provided a realistic bounce and even matched my body temperature if I filled them with water of a certain temperature. Of course, as I was doing all of this, I knew how fragile my fake breasts would be. And, a night I remember well, it happened, one of my beloved water balloons broke sending water down my clothes. I was lucky in that I was headed from my seat at the bar to the rest room and had just made it to the safety of the women's room, if it was empty at the time. It was empty and it saved me from any rushed explanations of the water which I caused. The only crisis management statement I could come up with was I was pregnant and my water broke. What really happened was, I gathered my one breast self together and left the venue like nothing happened, then headed home determined to find another form of realistic breasts. 

The next  profound crisis management encounter I remember was one of the worst I ever have had. It happened in another venue I went to regularly. After consuming my usual amount of beer, I naturally needed to innocently use the women's room. When I did, I didn't notice the woman who came in after me and I should have. I saw her and an older woman  I perceived to be her Mom come in the door and pass nearby me at the bar. The older woman wasn't shy about glaring at me but kept on going, minding her own business. I should have known my relaxation would come back to haunt me because when I came out of one of the stalls in the restroom, I was confronted by the daughter. Out of the clear blue sky, she started screaming at me and began her tirade by calling me a pervert. 

At first, my fight or flight mechanisms kicked in and my first inclination was to vacate the rest room. Instead, my inner female kicked in and faced the red faced screaming woman. Somehow during her rant, I was able to learn she ran her own hair dresser salon. When she slowed down, I asked her for a business card so I could pass it along to a very influential local LGBTQ organization and naturally tell them about my negative experience with her. It worked because she abruptly stopped and left the rest room while I not so calmly washed my hands, checked my makeup and returned to my seat. The whole experience taught me to always be aware of my surroundings and other potential problem people in it. 

Of course, these two examples are just the tip of the iceberg when it comes to dealing with our own brand of trans crisis management. From makeup and fashion  struggles when we first come out of the closet, all the way to unwanted government discrimination, we face it all. I am sure all of you have faced your own crises over the years. Maybe going back all the way to being caught cross dressing in your Mom's or sister's clothes when you were growing up. Surviving it all was the challenge while preserving our mental health. Sadly, with the extremely high rates of suicide in the transgender community, too many don't make it. In fact, we just had a local trans musician commit self harm and die last week. 

Crisis management with all of us just needs to be a priority. 

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.