Down the Rabbit Hole

 

Summer Image, JJ Hart.

Over the years, I began to sink rapidly or was stuck in an increasingly large and deep transgender rabbit hole.

Sadly, I did not have the information I needed at a young age to help me to understand I was much more than a boy who preferred to dress in girls' clothing. I just knew I was not satisfied with cross dressing in front of the mirror on the rare moments I was alone. I always had problems with what I called the gender roller coaster, or I was up when I cross dressed for a couple days before I crashed to the depths of depression and daydreamed my life away thinking of the next visit, I would have in front of the hallway mirror. 

Only one of my thoughts was for certain, I was falling down a gender rabbit hole which I could never return from. For many years, I thought I would possibly grow out of my gender issues, and they could possibly be a phase. Of course, wanting to be feminine in all aspects of my life, was never just a phase and just grew stronger as I aged. 

It turned out, the older I became, the fonder I became of my rabbit hole and wanted to stay there. When I did go out, I was like a real rabbit, cautiously surveying the world for predators. It was not until I began to arrive at a financial point when I started to build confidence in my cross-dressed presentation, did I begin to enjoy my trips out of the hole and into the world. 

It was about this time too, when I began to expand my rabbit hole. I needed more space for my wardrobe and wigs of course. Not to mention the mental room I needed to grow into the person I was becoming. Once I saw the light of my new gender day, there could be no turning back. The light felt so good and so warm; I was loving my new life. 

I ended up forsaking my gender rabbit hole for a new universe of women. To be truthful, it was the most difficult experience of my life. Since I had left my old comfort zone of white male privilege, establishing a new base was difficult in my new transgender womanhood. I had dug my gender rabbit hole so deep; it was difficult to find my way out. 

Sadly, I see too many transgender women and trans men who are stuck in their gender holes. Especially, in the current negative situations we are living in right now, I understand why so many LGBTQ people want to stay out of the public eye. It is just a shame we need to do it.

Transgender Destiny?

 

Image from Marvin 
Kuhn on UnSplash.

When some unknowing person says something like I had a choice to be transgender, I just laugh and say being trans was simply my destiny.

I believe my journey began before birth when my mom was prescribed the D.E.S. medication which was popular at the time for women who had a history of experiencing problem pregnancies. Since my mom had undergone three still births before me, it seems to me, she would have been a prime candidate for the drug when I was born in 1949. 

From the very brief studies I have seen on D.E.S., it was supposed to flood the mother's womb with estrogen. Which of course affected the fetus also. 

How ironic would it be that the initial dose of estrogen I received in the womb would later on come back to help me. It took me fifty years, but eventually I discovered when I went on HRT or gender affirming hormones, how natural I would feel. No adverse effects at all, just a warm feeling I was finally doing what was right. In other words, I was coming home. The only problem was my life was filled with the gender torment of fighting my basic will to be feminine. What if I had just given in to my instincts so much earlier. Would life had been more pleasant?

The problem was though, gender was never cut and dry with me. I was cursed with a male body which on one hand kept the bullies away but on the other, made it very difficult to obtain a feminine look when I found the secret time to cross dress as a girl. I had to take one or another which caused me considerable stress to my mental health. Waking up every day wondering if I was a boy or a girl, was certainly no fun. 

Plus, there was absolutely no one I could explain my gender issues to. I grew up in a male dominated family and knew there would be no way I could be accepted. I knew, even being caught in girls' clothes would earn me a trip to a psychiatrist. Deep down, I knew there was nothing mentally wrong with me, so I did want not any part of a visit. Remember, this was back in the 1950's when there was little to no knowledge of gender issues. In fact, gender issues were labeled as mental disorders. All that happened was, I was driven deeper into my feminine gender shell.  

As time went on, I developed a very thick shell which when I finally ready to do so, was difficult to escape from. In other words, I needed to establish too many levels of feminine escape before I made the final jump to the other gender frontier. I needed to slowly discover if the other gender as a transgender woman would provide me what I had been missing all of my life. I felt as if I was sliding down a slippery slope into a valley, I knew very little about. 

As I slid down the slope, I saw bit and pieces of my old life go by as I mourned some of the pieces and I rejoiced at others. As I felt more and more comfortable in my new transgender womanhood, I knew the landing would be as soft as possible. I found my gender needs had changed, for the best. I finally took my chance at the age of sixty to forever change my life and live fulltime as a transgender woman.

I finally had my chance to fulfill my D.E.S. destiny. I could not reclaim the time I had lost but I could lead a better life going forward.

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.  

Opening Transgender Doors

 

Image from Sara Darcaj on Unplash.

To me, life is a process when we are born and doors open and when you die, and doors close.

For transgender women and trans men, sometimes the process is more intense. Depending upon where you view yourself in the gender process, we go through a series of doors until we reach our dreams. On a personal note, I think I went through at least three or four transitions before I arrived where I am today. The first realization I had was when I was quite young and understood when I looked in the mirror cross dressed, it was only the beginning. I wanted to do so much more than just look like a girl; I wanted to live her life also. I equated it to the problems I had with my gender roller coaster. When I was able to dress as my feminine self, I was satisfied and happy, for a couple days until I became depressed and moody again. Looking back, I equate the process with knowing I was transgender but back then, the information on being trans just wasn't available.

My second big transition came when I learned I did not have to wait another whole year between Halloweens to test the world as me. I was desperate not to have to wait a whole year before I could learn again the feminine lessons I needed to move on to my next major transition. I refer to it quite a bit as the time I suddenly realized I wasn't a part-time cross dresser at all, I was a much scarier prospect, I was a transgender woman. A term which was just being known and popularized. I say scarier because accepting the fact I was transgender meant I needed to apply a deeper understanding to who I was on another level. Not just reapplying myself to more effective feminine presentations. Along the way, I had reached the point when I could blend in with society as myself, so I had the time and inner energy to move my life forward towards my dream which involved my next transition. 

The important aspect of my next major door to go through was the simple knowledge I could indeed establish a new life on the other side of the gender frontier. Confidence was everything as I decided to knock on the door of gender affirming hormones. I bravely sought out a doctor who would prescribe my minimal dosages of the meds until he could see I had no adverse problems. At that point, it was obvious to me my body had taken to the new hormones in a very unprecedented way. It was as if I should have been on the new treatment all my life. 

In turn, the changes the hormones made were nothing short of amazing. I could and have written entire blog posts on the hormonal subject and what it meant to me. At the least, all the doors I was able to go through in my life, made life much less boring and interesting. Just wondering what would be behind the next door was scary but exciting since changing genders into what you always should have been, made life worthwhile for me. 

Without doors to encounter, my life began to slow, and I had a chance to enjoy my true self thanks to new friends I had made. Along with my desire to see what is behind the next door.

No Struggle no Progress

 

Image from UnSplash.

Basically, when it comes to doing anything really important in life, to progress you need to struggle.

As far as being transgender, often it seems our struggles are impacted. First of all, most of us are not blessed with any natural feminine characteristics to work with. At least, I did not think I had any except perhaps my legs which often ruined my fashion sense when I tried to focus on my legs and not try to cover up my wide torso and broad shoulders. I struggled with my overall image until I got it right and I began to blend in with the public at large. 

Far more important to me was the mental struggle which went along with my journey to transgender womanhood. For the longest time, it seemed as if every step forward I achieved in the world as a novice transgender woman was met by taking three steps back. Or when I thought I had conquered the world of high heels, I would catch my heel in a sidewalk crack and break it. Who knew you had to put so much work into being a girl and it was only the beginning. 

Along the way, my life became a battle between two genders and for the most part, the battle destroyed me. Especially, my already frail mental health since I was already diagnosed as being Bi-Polar, I did not need any other problems I never asked for. Regardless, life moved on as I tried to roll with the punches. I was cross dressing as much as I could while at the same time, I was trying to live a life as a successful man. I managed to stay married to the same woman for twenty -five years while at the same time making good progression in my employment career. Sadly, I was stubborn, and struggle was all I knew as I lived my life. If I would have ever relaxed and looked around, I would have seen much of my progress came from just running from my problems and not facing them. My wife said it best one day when we were locked in yet another brutal argument. She said, why did not I be man enough to be a woman. The logical answer to the question was, I simply was not ready and still had a lot to learn before I jumped the male gender ship and began to live as a transgender woman. 

Very soon, my struggles reached a critical tipping point where progress was becoming the norm. I was reaching the point where I could be man enough to be a woman out of sheer determination. Sadly, by this point, my wife had passed away, so she never had a chance to meet the woman I had become. Again, I needed to struggle through a new reality of being alone after all of those years. It did not take me long to turn to my feminine self for help. In fact, the last date I had set up with another woman as a man was to an outdoor concert. At the last minute, the woman backed out, so I did the next best thing and took myself. My feminine self-had a great time and I never tried to go out with a woman as a man again.

As I began to see and reach my potential as a transgender woman, my mental health improved as well as my life as a whole. When it did, my struggles went with it.

And Then he Was Gone

 

JJ Hart at Club Diversity
Columbus, Ohio

It took me nearly a half a century to rid myself of my male self and begin living as my authentic feminine self.

Even though much of my progress towards my gender goal was physical, much was mental also. The physical part I am referring to was the portion of my transition which revolved an intense period of time I went through attempting to judge my appearance in my own personal mirror. I was so into myself, my wife began to call me the pretty, pretty princess and told me I was ignoring what a woman really was. She was right and it took me years of research and struggle to learn what she really meant. 

As I learned, the more my male self-fought me as he did not want to give up any of his life and male privileges he had fought so long to earn. It seemed every small gender victory was hard earned until he was gone.

Perhaps the biggest factor against him was I felt so excited and natural in the new world of transgender womanhood I was creating. Surely, I was still having my ups and downs when I tried out the public when I went out, but the downs were becoming fewer and farther between. Plus, my amount of terror I was still experiencing as a transgender woman was decreasing by the day. I think now, the major reason was I finally made the mental decision to go forth in the world as a woman on my own terms rather than the part time cross dresser I had somehow portrayed myself to be. Some may say I was dealing in semantics, but the thought pattern was a revelation for me. 

As he disappeared, my female self-had no problems filling the void in my life. My long-buried woman self-had no problem putting her past behind her as she stepped out into the bright lights of a new world. I think having no resentment made her a better person people could relate to and like. In fact, I found many new people related to me as a woman than ever before as a man. 

Ironically, after a very slow start to the fifty years of gender discovery I endured, once I seriously started my transition. time went very fast. Perhaps, it was because every night I went out, I was learning so much new on not being just the pretty, pretty princess and finally experiencing what my wife told me about being a woman was all about. Or I was finally given the chance to go behind the feminine gender curtain into a world dominated by women. When I did, I found women ran their own world their own way without the help of men. During the girls' nights out, I was invited to I learned what was important to women and not men. Even along the way, I learned the power of non-verbal communication between women when one night I was warned away from an intoxicated man in a venue I was a regular in by a bartender I knew. With one look, I immediately went the other way away from him and was safe.

Finally, after so much learning and experiencing a new life as a transgender woman, I think my male self-saw the writing on the wall and decided he was done. When he did, a huge weight was lifted from my shoulders. It seemed carrying two people all those years took a toll on me, and I wanted out. 

Burning Gender Bridges

 

Image from Adam Wilson
on UnSplash

During my life, I have always excelled in self-destruction. It seemed, whenever I had succeeded in anything positive, I always tried to tear it down. 

I blame the entire process on two basics, one of which on how I was raised. My parents never accentuated the positive at any time. If I received a "B" in any class, invariably I heard, why didn't I earn an "A" and I was not applying myself properly. The other basic was anything I accomplished as my male self; I did my best to reject. I did not in any way want to accept any success I earned as a male. So, I did my best to burn the gender bridge I created. 

Of course, the more I went down my gender path towards transgender womanhood, the more bridges I needed to burn. Everywhere I looked, the stakes were higher in life. All along I was accumulating more and more success as my unwanted male self which made my decision so much more difficult. Still, I forged on with my torch burning brightly. To hell with the results, I was going to attempt to follow my gender dreams anyway. Finally, I arrived at the point where seemingly I was subconsciously trying to sabotage myself. In many ways, I was desperately attempting to hide my deep dark cross-dressing secret while, on the other hand, I secretly wanted everyone to know I had always wanted to live as my authentic feminine self and did not care what they thought. Still, I needed to be careful as I had deep roots to my male past. Spouses, family and jobs were at stake. So, I tried to be sure of what I was doing before I cut the gender tree down.

Perhaps the most substantial bridge I needed to burn was to my job. I was a very successful restaurant manager in a regional/national casual restaurant chain. The management was very male dominated, and I knew there was no way I could ever transition in the same job. 

I decided to try going to other similar food/bar competitors thinking no one would recognize me. Long story short, I found out the hard way I was recognized as a version of my male self. To make matters worse, I tried to frequent my own operation and was close to being immediately recognized. In doing so, I burnt a major bridge which I don't think my wife ever found out about. It was bad enough when she knew I was breaking the agreement we had for me to never leave the house as a transgender woman.

The new bridge I built when I burnt the old one was when I decided to buy my own restaurant. I figured if I was the owner, no one could tell me what to do. That was true to an extent until one night a very evil former acquaintance met me in the parking lot to tell me my lifestyle was keeping the public away where we operated. I don't know how true what he said was but one way or another, I had burnt all my gender bridges and there was no way I could ever go back. 

When I transitioned and began my life as a transgender woman, I was able to build new strong bridges for the first time in my life. It was like my feminine soul was excellent in her building skills and could not wait for a chance to thrive.

The sad part was/is how much destruction I had to go through just to arrive at where my dream could be born. It turned out the birth was the easiest part of it all, as I set out to live a fulltime new life in my transgender womanhood. I finally had the chance to put my fire out. At least the destructive one.   

Why Me???

 

Image from Paige Cody
on UnSplash

Earlier in life, when my journey into transgender womanhood was weighing heavily on me, in despair I would look in the mirror and whisper why me.

During that portion of my life as I was still learning the benefits of being a trans woman, I had not had the opportunity to witness the positives I could achieve. Perhaps, the positives are one reason a certain political group is dead set on erasing us. As always, the group has ignored the times in history when entire societies worshiped dual spirted or transgender members of their civilizations. Since I do have a degree in history, I often took the chance to do extra research on the subject in my spare time.

I also think outside TERF's or transphobic women do not trust us because we have spent time in a male dominated society enjoying male privilege. When in fact, we were not enjoying our experience at all and desperately wanted out.  As far as men go, so many are desperately hanging on to their frail sexuality, they become scared and bitter as they secretly watch their trans porn. Sadly, the men's frustration turns into violence towards the transgender woman the man wanted so badly. 

Perhaps the biggest thing I did not realize until I spent time in the public's eye as a transgender woman was how much both binary genders secretly value our knowledge of the world. I remember vividly the numerous times I was approached by other women dealing with man problems of their own. I found the other women really valued my insight into the male world. Through it all, I began to lighten up on my poor, poor pitiful me idea of life and began to see the benefits of living partially between the two main genders. Once I put being a gender victim behind me, my life brightened considerably.

The entire process went far beyond other women asking me about their men, all the way to me being able to increase my overall confidence in the new life I was living. Rapidly, my life was approaching a point of no return. The pressure was on to make the right decision on how I was going to live the rest of my life. I did not think the rest of the world could understand how badly I was torn by my gender decisions, so I did the male thing and internalized them. My mental health struggled badly until two things happened.

One of which was when my wife Liz came along and told me in no uncertain terms, she had only seen a female in me, and I should stop the remainder of life I was living as a man. The other was when I began HRT or gender affirming hormones. When I finally did begin the new hormones, my body took to the new regiment of meds as if I should have always been on them. 

Between the two, even the very stubborn part of me which was desperately hanging on to what was left of his old male life could not resist any longer. Overall, when I looked for my gender truth I found it. Why me? became my truth and when I accepted it, I knew I had done the right thing. My life became softer, richer and more colorful than ever before.   

To arrive there however I needed to pay my dues and learn many important lessons before I could move forward. 

A Trans Girl's Baggage

 

Image from UnSplash

Like many women, we trans girls carry a lot of baggage when we travel.

If you remember the old Paris Hilton commercials of her mass amount of luggage she brought along when she traveled, it reminded me of the size and number of bags we trans women have to have to transition from a male life to a feminine one. To the typical outsider, they think all we have to worry about bringing along is fashion and/or wardrobe necessities. When in truth, we know which wardrobe to bring is just the beginning. Examples are many and varied, often determined by when we decide to transition in our life cycle. Needless to say, an older transgender woman may have more aspects in her life to consider with family, friends, spouses and employment to think about.

In my case, I waited so long to enter trans womanhood, nearly everyone I cared about as far as family and friends went, passed away. I would not recommend it, but my method really simplified the process of telling my deepest darkest secret to others was made so much easier. In fact, I only had two family members to tell of my authentic life. My daughter and my brother which went half and half for me. My daughter remains a steadfast ally to this day while my brother and I have not talked in over a decade.

Thus far, we have only discussed the larger baggage items and not any of the smaller yet still important things we have to bring along with us as we enter a scary yet exciting new world. Such as, what would we do about the interests and hobbies we have built our male lives around. As far as I am concerned, what I always bring up is my lifetime love of sports. For years, I considered I would have to give up my interest in sports in order to transition. Because I knew so few women who were into sports.

Fortunately, the world around me began to change or I began to see more clearly what was really going in the world I was in. In other words, I began to see other women in the sports bars I was in as interested in the games as I was. It was around this time also when the National Football League began to market their product to women. It became stylish for me to wear my team's jersey into the sports bars I became a regular in. In addition, the other women I began to be friends with were sports fanatics.

All of this combined to make my path to my transgender womanhood so much easier. I can compare it to just having to bring a carry-on bag with me on a plane instead of a large piece of luggage. I was more secure and did not have to give up any of my interests I so enjoyed. 

Perhaps the only problem I had was when I talked to men. With them, I often had to dumb myself down when I talked about topics, I knew a lot about. One time, with a tow truck driver, I needed to finally act as if I knew nothing about the mechanics of the truck, we were in to satisfy his ego. It was my first interaction one on one with a man, so I was surprised how it went. Basically, I was forced to give in to him to just maintain civility on the short trip. The lesson I learned was one I kept with me every time I was with a man.

It turned out I had unpacked a whole new set of transgender baggage.

Master of Myself

Transgender Flag from Lena Balk
on UnSplash. 

Or would have it been proper to say, Mistress of myself?

Probably so, as one way or another, I really struggled to arrive at where I needed to be to achieve my goal of transgender womanhood. Often, I write about how many nights when I came home in tears following being laughed at by an unfeeling public. Looking back now, I have a difficult time wondering what kept me going along my gender path. 

I suppose the little flashes of gender euphoria I experienced kept me going. Such as when I was accepted in malls and clothing stores before I realized all the clerks were seeing was my money, not my gender. Before long, the more experience I put behind me as a cross dresser or novice transgender woman, slowly the path was smoother and the happier I was becoming.

Then there were the small mixers I went to in nearby Columbus, Ohio. When I attended, I was able to see and meet all levels of the LGBTQ community. From admirers to transsexuals to lesbians, they all were there. It was one of the mixers where I was cornered by a much larger crossdresser admirer who was trying to take advantage of me and could have until I was rescued by my second wife. It was also there when I had my first encounter with a curious lesbian, and we left the mixer to visit a bigger lesbian bar. At that point, I was still heavily questioning which way my life would go. What kind of a path was I on and did I control it at all. 

In order to gain control, the only thing I could do was try to gain more and more experience as a transgender woman to learn if I was headed in the right direction with my life. So much was at stake and the pressure was on to make the right decision. In the meantime, I continued to follow my path and learn if I could indeed flip my gender script and attempt to be truly happy for the first time in my life. Perhaps, discovering the truth about myself, would finally provide me the missing link I was seeking. Of course, just dressing to appear as a woman did not solve the problem. As I gained confidence in the world, the world wanted to know more about me. The whole process opened up a whole new range of life opportunities. Such as how was I going to learn to communicate as a woman, all the way to adjusting to a whole new world of passive aggressive women. 

Again, it took a while for me to regain control of my life. Of course, attempting to change genders into my authentic self was a seismic shift in my life. On one hand, my authentic self-felt so natural but on the other, the entire process was so scary. So, I took my time before I started taking gender affirming hormones, so I burned all my gender bridges behind me. Looking back now, I wish I had done it all sooner and taken better control of my life.

I did not however and ended up not transitioning until I was in my sixties. Once I did, there was no looking back and I became the mistress of myself. Finally.  

 

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.

I Never Felt at Home

 

Image from JJ Hart

Rarely, every now and then someone asks me when I knew I had gender issues. 

The answer I give everyone is I knew forever there was something wrong with me. I just did not know what. Plus, by the time I realized what was wrong, I felt as if I was alone in the world with my gender issues. I was very confused. As I grew through my teen years, I knew I wanted to be a girl but just did not see a path forward. 

Through it all, I kept searching for answers. I knew for certain I felt elated and natural when I cross dressed as a girl and never quite felt at home when I was with a group of males. I felt as if I was an outsider looking in. 

The older I became, the better I was at hiding my feelings. I tried my best to do all the usual male activities such as playing sports and working on cars. I played the male game well to hide my inner most feminine feelings but all along still felt like an intruder. It wasn't until I began to seriously explore my transgender womanhood did, I finally learned the truth, I was not meant to live a male life at all. As I recently wrote, I was stuck in some sort of a gender never-never land I was destined to never escape. I spent too much time pitying myself and playing the gender victim before I stepped up to face my problems.

In the meantime, the biggest problem I faced was deciding what to do with the increasingly immense amount of male baggage I was accumulating. After being discharged from the Army and finishing my second college degree, we added my daughter to the family, and I suddenly needed to become serious about beginning a career which I could support a family on. Then came the route I followed to a successful job I would probably have to give up if I transitioned to a transgender woman. As I advanced up the corporate ladder, at all the macho leaning meetings I needed to attend, I still felt completely out of place. No matter how successful I was.

Then there was the biggest piece of baggage of all which was my second wife. Although, she knew from day one I was a cross dresser, she drew a line in the sand when it came to any idea at all I was transgender and wanted to begin gender affirming hormones. She and my male self-formed a formidable pair when it came to any idea of me going any further towards transgender womanhood. When she unexpectedly passed away at the age of fifty from a massive heart attack, my male self-lost his strongest supporter and he just faded quickly away.

At the same time, I was building a new set of friends who happened to be women and lesbian and I had never felt so at home in my life. They embraced me for my authentic self while at the same time I relaxed and learned so much about womanhood from them. I never thought possible, life would ever be so fulfilling again since I was already sixty. It was well over a decade now and during the same period I met my current wife, Liz. 

Feeling at home for the first time in my life was the best possible feeling I could ever have. 

Expedition Transgender

 

Image courtesy JJ Hart

The half century journey I embarked on to finally come up as my true authentic self was certainly an expedition. 

As I always mention, my discovery began with going through my mom's underwear drawer and trying on nylons, bras and girdles I could still fit into before testosterone poisoning really set in. From there, I progressed into makeup and very slowly began to increase my craft. I did not really want to look like a clown in drag so I did the best I could. 

Life went by and so did my expedition. Sadly, for several reasons, I developed several coping mechanisms to mask my gender truth. I tried and tried to convince myself my desire to wear women's clothes and look feminine was just a harmless hobby and perhaps was just a phase in life I was going through. It took me years to realize the true phase I was going through was that I was a male at all. With sheer willpower, I managed to learn to play the male game fairly successfully and lived a life which shielded my feminine self from most all intrusions. I went into my dark lonely gender closet and slammed the door.

It took me years to have the courage to open my closet door and tentatively look around. When I did, my expedition took sudden and encouraging turns. The more I tested the public as a transgender woman, the more successful I was. I set out to sample as much as I could of a woman's lifestyle and discover my feelings on what would happen next. I tried going to gay and lesbian bars as well as big sports bars and found I could carve out a spot as a regular in a so-called straight venue. I also tried to go to various other places such as bookstores and other retail venues single women would go. In other words, I was obsessed with coming as close as I could on my expedition to seeing what a cis woman went through in her life. By doing so, I could make the final decision on where I wanted to go with my life, as a man or as a woman. 

As my expedition transgender progressed, I found myself in a face-to-face decision on beginning to take gender affirming hormones or not. Since my only real opposition to beginning the hormones had passed away, my ultimate path was clear, and I sought out a doctor for approval. He checked me out and determined I was healthy enough to begin HRT with minimum dosages of Estradiol and a testosterone blocker and my life changed forever. All the changes which occurred would fill another blog post themselves. Perhaps the biggest overall surprise was how quickly my body took to the new hormones. So fast, I needed to rethink how quickly I was going to have to change the timetable of when I ultimately wanted to finish my expedition and enter my own transgender womanhood.

I learned the fact of the matter was, I was always living a gender lie. I had refused to accept the fact I was always deeply feminine and was forced into a male lifestyle from some cruel twist of fate. All the time I thought I was a man attempting to be a woman was wrong. I was a woman attempting to be a man.

I wish I could have a portion of my life back to re-center my expedition and start all over again.  

 

Creative Gender Tensions?

 

Image from Levi Stute
on UnSplash

As I moved along my long and bumpy gender path, seemingly I created many gender tensions which were overblown or not needed at all.

It all started innocently enough when I first caught a glimpse of myself for the first time wearing makeup and a dress in the family's full length hallway mirror. Immediately, I knew I was hooked and could not wait to cross dress again for my own personal pleasure and delight. Sadly, the gender tension began when I could not dress again for a while. All of it sometimes became unbearable when I woke up in the morning not knowing if I wanted to be the boy I had always been, or the girl I was increasingly wanting to be. To say the least, life was very confusing, and I felt I had to be the only person in the world dealing with the same gender issues.

In the pre-internet years (along with social media), I was in the so-called dark ages of information. I had very little in the way of outside information to guide me along or challenge the many new ideas I was considering when it came to my gender life. Everything was out of focus including my sexuality. Did I like girls at all or did I just want to be one. The tension was real but still I kept struggling along trying to be the best male bodied person I could be. 

Then the internet came along and with it, my life was changed forever. Once we could afford a computer, suddenly I found how un-alone I was and how many others there were in the world with similar gender issues to mine. Of course, I was just not content to read about others, I needed to try to interact. I became involved with several early chat rooms which eventually were discovered by my second wife when she learned how to search my browsing history. Even though the great majority of the people I chatted with were not geographically close to me, I found one who was. In fact, he was within fifty miles, so a meeting was certainly possible. That was until my wife found out and an all-new battle broke out over the control of the computer. Until I learned more about erasing my history on the computer, I needed to stay off of it. Which created a new set of gender tensions. 

Living with my tensions became second nature over the years. I followed the same old up and down patterns of being up when I cross dressed, to being down when I was forced back into my male life. I rode the edge of a double-edged sword for years until I finally decided to face the truth about myself and be me. Still, it took me years of careful exploration of my transgender womanhood before I cautiously decided I was on the right path. Once I did, much of my gender tension disappeared and I knew I was making the right move for a change. All that was left was to make the crucial decisions about who I was coming out to and when.  When I did come out, I was met with approval from my daughter and rejection from my brother, so I suppose it could have been better or worse. I still had immediate family when I did it which decreased my tension along with providing me extra confidence in myself, I never had known before. 

By now, perhaps you are wondering where the creative portion of all of this comes in. All the time when I was traveling my gender path to transgender womanhood, there were many chances to zig when I should have zagged, and I ran into problems I needed to get out of. Mostly trying to navigate the problem of expressing my new transgender self while still being involved in a committed relationship. All I can say is somehow I survived and made it to my new life as a trans woman. 

When I did, my tension went away, and I was able to live a life free of gender problems which had plagued me my entire life. The relief was real. 

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. 

Joy to the World

Image from JJ Hart Liz on right.

Gender euphoria is so wonderful to a transgender woman or trans man striving to present themselves in the world as their authentic selves. On the other hand, it is often very rare to obtain. 

The brief moments I experienced euphoria in the world when I first went out as a novice trans woman or cross dresser, kept me going but barely. The reason was, I suffered from huge bouts of  gender dysphoria which wrecked my life. It seemed every morning when I woke up and looked in the mirror, would I see the same old male I never wanted to be or somehow see behind him and view the girl I always dreamed of being. My dreams even reflected my gender issues when I would awake following a very vivid dream where I was the pretty girl. When reality set in, I was very sad.

It took me years to realize I could fight back against my gender dysphoria and do more to live out my dream of living as a woman. Years of sorrow when I failed became years of joy when I succeeded. Progress was very slow at first as I went out shopping in the world and sought out every mirror I could find to restore my faith I was indeed a presentable woman just minding her business in the world. When I discovered most people did not really care about me, my life became much easier and took quite a bit of the pressure off I was feeling. 

Still, I needed more. On every occasion I could, I was out the door seeking new places to visit as my new exciting self. I was walking the gender border and feeling the joy on some of the days I was successful and torment on the days I was not. My main problem was trying to find feedback with what I was attempting to do. The only time I did receive any response was when I went to the small, diverse parties I went to at an acquaintance's house in nearby Columbus, Ohio. From transgender admirers to inquisitive lesbians, I had a chance to meet new people in my world and see how I measured up to them. I knew I could never be a beautiful as a few of the impossibly feminine transgender women who attended but just maybe I could elevate my appearance to a feminine level where I could get by. The parties also proved to be the initial starting point of developing my own new personality as a trans woman, so they were very beneficial.

As I experienced the joy of being my true self, something had to give. Sadly, the something turned out to be my male self and my marriage of twenty five years to my second wife. Both of them suffered terribly. Naturally, neither of them wanted to lose any power. My male self was quite comfortable in the life he had built and my wife did not want to lose the man she married, so I was in for very difficult times. What happened next was my mental health went into a very steep decline. I did not know where to turn and at that time did not have a good therapist to fall back on. Then I resorted to the worst possible choice when I tried to internalize everything. By doing so, I made everything worse. 

I continued to go out as much as i could but ended up just forcing the gender issue and losing any of the joy I had previously felt. It wasn't until I decided to begin gender affirming hormones and transition fully, did I begin to reclaim the happiness I felt. 

Was it worth it? Sure as I finally achieved my dreams of living fulltime as a transgender woman. I just wish I had the courage to do it sooner. Or as my second wife told me a number of times when we bitterly fought...be man enough to be a woman. 

Trans Bucket List

 

Image from Pepe Nero on UnSplash.

On my way to achieving my version of transgender womanhood, I started my trans woman bucket list.

It all started on the fateful night when I decided to go out and mingle with a group of professional women as an equal. Not as a man cross dressed in their company to see if I could make it in their world. There was so much else at stake that evening because I knew if I was successful, I could never go back to just living my life as a man. 

Once I was successful, I began to think of  things I could accomplish as a trans woman to add to my bucket list. Once I was accepted as a regular in one venue, could I possibly add another to increase where I could go to add variety to my evenings. For the most part I was successful in being accepted. Even to the point of being thrust into a diverse small group of acquaintances I could regularly socialize with. The group included the sister of one of the bartenders, a lesbian, a couple men and an exotic dancer to name a few. All of this occurred before I met the transgender woman and two lesbians I socialized with on a regular basis.

Also on my bucket list at the time was how was I going to handle my sexuality with men. I almost found out when I became attracted to one of the men in the group. Or should I say he was becoming intrigued with me. All the way to him seeking me out on the nights when I was there all alone. I felt comfortable talking to him and even enjoyed his company before he switched jobs and abruptly moved away. It turned out there were very few men on my bucket list but even so, there were a couple which left a deep impression on me. 

Both of the men were met through social media dating sites and happened after I sorted through an amazing amount of trash responses. Because I was careful to meet any responders in a setting I approved of, we met in my regular venues I felt safe in. Both treated me with respect and I leaned a little of how it would be to interact with an interested man as a woman as I was wined and dined. It was terrifying and exciting at the same time. I still remember both dates and how special I felt but on the other hand, I never really lost my attraction to women. As impossible at it seemed to me at the time, I was headed towards being a transgender lesbian...if I could be accepted. 

I continued my quest for a new bucket list as I learned how to be a woman from other women. It seemed nightly I was learning new ideas such as I did not need a man to be validated in my new life. The lesbians I were around were both very strong and confident in their own right, so I could be also. 

Then, there was my relationship with my wife Liz which has been going on for over thirteen years now. I never though I would find another person who would be serious enough about me to want to build a relationship at my age. But I did and amazingly, Liz found me on a dating site defying all odds. 

Just when I thought I was done with my bucket, it became filled with happiness and I hope to keep it that way. 

Running and Hiding

Image from JJ Hart archives,

I spent over a half of a century in my life running and hiding from the gender issues I faced all of the time. 

First, most of the time I hid my desire to dress like all of the girls around me. Of course, in order to accomplish anything, I needed to suppress any urges I had to be at one as a girl in the mirror. My Mom never knew how much she helped me in my early days of cross dressing. Before I outgrew her, I took advantage of wearing her fashion wardrobe, not to mention her makeup too. Much pressure to hide to be sure because if I was discovered, intensive therapy or worse would be in my future.

Also very early on, I ran to places I thought I would be safe. I hid a collection of clothes and makeup in the woods beside our house in the country. In my own world, I could escape my brother and family and briefly enjoy my small attempt at gender freedom. On other very rare occasions, when my family was not home, I escaped to the bathroom and applied my clothes and makeup which was an ideal time to see myself in the full-length mirror in the hallway.   

As I grew older and my male life became more complex, running and hiding became much more difficult. Plus, I had so much more to lose in my life if I was discovered. The more I ran from my issues, the more pressure I faced. What happened was, after I was freed from the restrictions of my military service, I was able to run harder hoping to free my gender issues even better. I changed jobs and locations frequently trying to outrun my life and for the most part was more miserable than ever before. I moved my small family to the suburbs of New York City, then back again to my native Ohio. Along the way, we lived in an old farmhouse in rural Southern Ohio and back again to urban areas such as Columbus, Ohio.

Sadly, it took me many years to understand all the running and hiding was doing me no good. The problem was inside me and could not be out-ran and was mentally exhausting.  Once I learned the solution to my problems were closer than I thought, my journey to transgender womanhood became clearer but in many ways no easier. I still needed to strip back all the layers of femininity and do my best to cross the gender border. I think now, the communications I had with the world as a novice transgender woman were the most difficult part of the journey. I needed time and effort to overcome the fear I had with looking another women in the eye when we spoke. For the most part, I just wanted to run and hide. 

Every time I did not run, I developed more confidence in myself. In other words, with the help of other cis-women friends I had, I found and embraced my own transgender womanhood. No longer was I stuck in an old male life I never really wanted regardless of all the privileges I had accumulated from just being older and white. 

Running and hiding just became too exhausting and demanding to continue with it. I finally gave into the pressure and began to live in my truth. What took me so long. I still wonder. My male life just wasn't so much fun and successful to continue. I consider myself one of the fortunate humans to escape the bonds my gender roots had confined me with.    

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.