A Destination or a Journey?

JJ Hart

 Early on when I was stuck in my dark gender closet, I viewed myself on a way to a destination, not much different than a vacation from my male self. 

Then, when I began to experience more "vacations" than I could handle, I began to notice I was on more of a journey than I thought. Looking back, I was missing all of the signs I was much more than a part time crossdresser, pursuing a harmless hobby. The difference always was I wanted to do more than look like a girl, I wanted to be a girl. Needless to say, I spent many hours of my spare time wondering what my true problem was. Time, I wished I could have back. 

Instead of getting any of the time back, I invested it in my femininized appearance in the mirror, and I still thought I was on some sort of a mysterious journey no one else knew anything about. It would be years before I was able to attend transvestite mixers to meet other likeminded people who I thought were on the same path as I. Imagine my shock when I found out I had waited so long to find out I did not fit in well with almost all of the others who were attending the mixer. Somehow, I just still felt different. Probably because most of the attendees viewed themselves as men in dresses and my views of my gender self were just beginning to form and they were so much deeper than thinking I was a man in a dress. 

It was about this time, I realized I was on more of a journey when I began to know transsexual women who were making the ultimate gender step in their life, gender realignment surgery to be exact. I was very intrigued by the idea and deep down I wondered if that was the journey I was headed on. The problem was I was stuck where I was in my male life and was not prepared like my friends were to make such a serious move. To be sure, gender surgery would certainly be a journey for me as I had quite the complex male life I was living and to be truthful, on occasion, I did enjoy the white male privilege I had earned. 

All I ended up doing on my journey was screwing up my mental health. Simply, the stress of juggling two of the binary genders became too much and I was very self-destructive. It was then I knew, my gender path was so much more than just a destination and I really needed to step up my game if I was going to survive. It was decision time. Either I went forward as a transgender woman or retreated back into my male world. 

The deciding factor was I felt so natural as a trans woman, so I did not stop my journey until I made it to a point where I could save my mental health and even my life. Certainly, even though I had reached many destinations along the way, my life turned out to be a gender journey which at times was touch and go. I ended up not going and stayed the course to my own form of transgender womanhood and was a better person for it. 

Gender Mandates

 When I was born, I did not have a choice of which gender I was supposed to be, my birth gender was male and there were to be no questions asked. 

In other words, I was mandated to enter a male world which I came to totally dislike and rebel against. Similar to many of you, I first had an idea something was wrong with my perceptions of my gender at a very early age when I went exploring in my mom's clothes. My first glimpses of myself in the full-length family mirror were memorable and electric. I knew right then, I needed to figure out a way to do more. 

The problem was, in my very male dominated family, I was mandated to go in only one gender direction and follow the male path. Afterall, if I made it, I was offered the promise of white male privileges. On the other hand, if I was caught cross dressing at all, I was surely on my way to see a therapist and perhaps be thrown into the dreaded conversion therapy. My answer was simple; I needed to continue in my underground cross-dressing ways and hope I did not get caught.  My major problem was my slightly younger brother who I was always stuck being with. Somehow, I did manage to do more and slightly lessen my mandate. When I did, I found I could enjoy my femininized self even more than I ever had before.

Of course, the most male mandate I faced was being drafted into the United States military during the Vietnam War. Since women were excluded from the draft, it was an exclusively male experience. I still resent having to face my time in the service when women did not, but I served my time for three years and was honorably discharged. I suppose too, my time in the Army disguised the true me to the outside world, since my friends and my dad already had served their country. It was mandated to be my turn if I wanted it or not. 

Slowly but surely, over the years, my mandate changed from male to female. I went very slowly to insure I would have less and less mishaps on my gender path. Each step I took gave me the confidence to take another. Of course, at some point, my mandates would collide. When they did, my mental health struggled, and I was fortunate (after several tries) to find a qualified therapist who helped me separate my bi-polar condition with my gender issues.

My largest feminine mandate came when I started gender affirming hormones. I knew almost immediately I had made the right decision. All the changes the hormones made to my body felt so natural. Inside and out, the changes were so dramatic, I think my body was always waiting for them. 

As mandates go, I would be remiss if I did not mention the gender privileges which go with the mandate.  Since I have spent quite a bit of time up close with male and female gender privileges, I know a little about both sides. As with most things, male privilege is more upfront and direct, while female privilege is more layered and indirect. 

One way, or another, mandates are a serious part of life and are difficult to control. Plus, they are so hard to deny.  

Transgender Dreams

 

Image from Alex Azabache 
on UnSplash.

My last question from my transgender grandchild for my yearlong book of questions I am putting together went something like this: If I had it all to do over again, what would I tell my twenty-year-old self about life.

First of all, before I answer, the questions come from a site called "Story Worth", and at the end of a year, they put all the weekly questions together to form a book on your life. It was a gift from my daughter. I am more than three-quarters through it already with a chance to add more questions for a small amount of extra money.

Now, back to my twenty-year-old self. First of all, at that time, I was consumed by two issues. Being drafted into the military along with a strong desire to be a woman. Conflicting problems to be certain which I was having a very difficult time dealing with. In the tried and true if I had known then what I know now, I would not have spent so much time worrying about basic training and beyond. I learned as I went through basic, that after I got into shape, it was just a team building experience with military realities built in. I made it through much easier than I thought I would and then prepared myself to serve out the remainder of my three-year enlistment. To be honest, I did not join the Army because I wanted to, or I thought it would make me anymore of a man. I was drafted into the service because of the Vietnam War. 

If anything, my gender issues became stronger when I was away in the military, as I constantly day-dreamed any spare moment I had about when I would become a civilian again and be able to pursue my dream of being a woman. It was all I had to get me by. 

Little did I know at the age of twenty, how complex and difficult my gender journey would take me throughout my life. To put it into perspective, the Army only took three years away from me, while deciding to finally come out as a transgender woman, took me forty more. I am sure my twenty years old would have asked why it took me so long to face the reality of who I really was and quit making excuses. I kidded myself for years thinking I was strong and would have to admit to my twenty-year-old, I simply wasn't. 

I would also have to tell my young self to not be afraid to dream because without dreams to achieve, often we arrive nowhere. I would have never made it to my goal of transgender womanhood unless I dreamed of it all those years and took steps to finally make it. Regardless of all the self-destructive behavior I put myself through. You only have one life to live and should try to do the best you can to preserve it. 

I was fortunate to have lived long enough to see my life come full circle from that confused twenty-year-old I was. When I did, I was able to achieve transgender dreams I never thought possible.  Of course, none of us know our ultimate destinies, the least we can do is accomplish goals which lead us in the right direction.

If you are in your closet, thinking you are trapped like I was, just do your best to look for the opportunities you may have to escape. Later on in life, it all may come back to help you with your transgender dreams.

Transgender Breakthroughs

 

Image from 
Shane Rounce  on 
UnSplash. 

Even though we are all at different points along the way in our gender journeys, we still have break throughs which keep us going. 

My earliest breakthrough was when I was still admiring my girlish reflection in the mirror, the first times I was able to try on my mom's clothes when I was all alone. I thought I looked great, and the feeling stayed with me for a couple days afterward until I could try to cross dress again. The problem was, I felt deep down there was still something missing, I wanted to do so much more than just look like a girl, I wanted to be a girl. The problem was, I did not have any gender information to go with my discovery of who I really was. I was still years away from even hearing for the first time about transgender women and what the term meant to me. I still have vivid recollections of the time I saw the transgender term used and just knew, for the first time in my life, being a trans woman fit me. Naturally it was a major breakthrough. 

Little did I know, just having a label to attach to myself, would prove to be a challenge for me as I went through life. No longer could I rely upon a mirror's image to get myself by. I needed to get out into the world and see if I could present well enough to mix in with the public. When I did, I found being a woman was no joke, and I needed to really work to achieve my goal of transgender womanhood. 

One of the big problems I had was, when I was coming out, I tried to keep one foot firmly in my closet. In case something went wrong, and I needed to go back. The only problem with keeping a foot in my closet was the time I spent in the world as a woman spoiled me, and I never wanted to go back. It was very difficult for me to tell my inner feminine self no. What I decided to do was, formulate a version of my own feminine bucket list. I would try increasingly more difficult things as a woman and see what would happen. For example, if I made it browsing in a bookstore, I would take it a step further by ordering a coffee and using the women's room the next time I was there. Or I would try to go to a different restaurant all together and order lunch. 

I try not to act as if I am recommending my path out of my gender closet to others because when it comes to leaving your closet, one size does certainly not fit all. Circmstances such as experiences in the public and where you live can vary so much. However, in my case, it did take a certain amount of courage to come out. There were many times when I waited in my car adjusting and readjusting my makeup before I gathered the courage to walk into a venue I wanted to try out as my new femininized self. Since a few of the venues I had been to several times as a man. 

Then, courage gave way to confidence and when it did, I could enjoy my new exciting life. Before that happened, it seemed to be a challenge every time I turned around. Perhaps I was expecting too much by thinking I could turn decades of living a reasonably successful male life around so quickly. Being a woman of any sorts presented a challenge because women lead a so much more layered and complex life than men. Once I accepted the challenge, I discovered I was in the right place as a trans woman and there would be no turning back. 

Even though the current barrage of anti-transgender legislation shows no sign of abating soon in many places, we have to remember transgender women and trans men will never be erased and have always existed and you can too. If you try, you can have your own breakthroughs and live a solid life out of your closet. You just have to be careful how you do it and keep an eye out for the bigots which are increasingly brave. In my case, I needed to realize the worst the bigots could do to me was not as bad as continuing to live in my gender closet. It was very dark and lonely, and I could not take it any longer and I set out to experience my own transgender breakthroughs.

Building Gender Bridges

 

Image from Alexander Rotker 
on UnSplash.

I have always been one to build too many bridges to jump off of in my life. 

In fact, if I don't have anything to worry about, I will create something. Looking back, I was especially bad at building huge, tall bridges when I was at the height of my trip to transgender womanhood. I felt I was partially justified in doing so because of all the problems I experienced when I was coming out of my gender closet. 

Before I began my trip, I was a fairly freewheeling person. If something happened for me to take care of, I would and at the same time, not spend much time worrying about my future. Even though I still faced major problems in my life, I could still conquer them, or escape back behind my skirts, heels and hose to hide. As I progressed in my life, I found my time was running out as a parttime cross dresser. Either I needed to do more or purge myself altogether of a pastime which had kept me from jumping off so many bridges I had built. 

Another problem I discovered was when I began to be more skilled at building my gender bridges was becoming, I was increasingly under more pressure to be successful. The more success I felt as a transgender woman, the easier my life became except for the very serious bridges I faced such as communication with the world. 

The best time I have for building my bridges is late at night when I am trying to sleep. These days, I have plenty of things to worry about. In fact, next week, my wife Liz and I will be heading north to my daughters, mother in laws lunch. During that time, I hope to find out what has happened to my transgender grandchild job offer as a civilian nuclear engineer with the Navy in Maine. Hopefully they have been able to stay under the radar so far and has maintained the job which they wanted to start this fall. (They is their preferred pronoun.)

Going to see the family is always very affirming as I have been accepted for years as my authentic feminine self. Early on it was very difficult for me to adjust to because nearly everyone in the room had known me for years as my old male self. Others including my first wife, who is the mother of my only child usually always attends, and she has a difficult time sometimes not referring to me with the proper pronouns when recounting a few of the long-ago days when I was trying to live as a macho man. Plus, we also met each other while we both served in the Army in Germany. With all the extra baggage I carry when it comes to her, I think she has done a good job of building a new bridge to me over the years.

Now, at my advanced age of seventy-five, I find myself looking ahead at the biggest bridge of all. When it is time to enter a new reality when I pass on. I have decided to do the best I can with all the aches and pains I have and keep a positive attitude. Of course, there are other major bridges to think about also when and if I need to enter assisted living, which I am not looking forward to. Liz and I were supposed to attend a special seminar put on by an attorney specializing in "elder law", but Liz got sick, and we did not go. So sometime in my future, I need to insist we find an attorney to give us a consultation. 

In life, it seems, there are always bridges to build. It is just a special problem unique to gender conflicted transgender women and trans men. Overtime, we can become very good builders and even better at hiding our results. Fortunately, there are more and more trained therapists to help us these days. Ironically, some of us have to go through several therapists until we can find the proper fit. So, we can find someone who can build a solid bridge, rather than tear it all down. Which, if you are like me, you tried to do many times during various purges. 

I Made Nothing

 

Image from Camillo 
Contreras on UnSplash.

Several of my earliest memories of success as a cross dresser came during the Halloween parties I went to. 

When I wore my very short mini dresses, showing off my freshly shaven legs, I found I had several women come up to me and say, I "made" a good-looking woman. Years later, when I began to understand "woman speak" better, what they probably meant was I "made" a good-looking woman, for a man dressed as one. 

Furthermore, I soon came to realize, I was not making anything. I was simply being who I was. In order to learn that simple fact, I needed to live decades of life as a parttime cross dresser or novice transgender woman. Or I needed to live my gender truth before I could claim it. I needed to get out of the mirror and into the world to learn if I really belonged there. Those were the days when no one in the world around me would give me a break. The public was laughing at me (rightfully so) because for the most part, I was dressed like a clown in drag. Plus, my old male self, my second wife and my mirror did not want to let go of me. Making my life miserable and destroying what I had left of my mental health.

Juggling two genders at once was a tremendous challenge when I caught myself practicing living one gender when I should not have been. Being called "Ma'am" at my macho management job was certainly not cool or good but somehow, I survived to live on to the next day when I was determined to do better.  What happened was, I did keep getting better at my feminine side and increasingly began to leave my male side behind, which scared him.

Fear, as they say, is a powerful motivator and instead of giving up, my male side and my second wife grew increasingly close and forced a battle of the wills. In other words, neither one of them wanted to lose their place in the world. Which included my universe. It turns out, I did make something...a huge mental mess for myself. It is one of the excuses I make for taking nearly fifty years to break out of my gender bonds and flourish out of my closet and mirror. I just had to make sure I was making the right choice and there was so much pressure on me. 

As I grew out of the mental gender mess, I had made for myself, I gained the critical confidence I needed to establish myself as a secure transgender woman. Not just a femininized man. Since I had spent a lifetime getting there, the personal coming out was extra special to me. It was as if my feminine self was telling me what took so long. As it turned out, I shared her belief in wondering why I took so much time and wasted so much nervous energy I wish I had back. As we all know, worrying over what we did in the past is a waste of time, unless we are learning from our mistakes.

I felt better when I realized I did not make anything, when it came to my gender issues. Rather, I inherited them from some unknown source which made life a challenge. A challenge I needed to finally accept before the pressure I put on myself had grown too heavy to carry and I had to put it down and go with the life which made me feel natural and alive. When my transgender womanhood became secure thanks to friends I had, I felt so much better as I built a new life.

Do the Right Thing

 

Image from UnSplash.

I learned early on from my parents when in doubt, you should always do the right thing. At the same time, I learned from them, dressing to look like a girl was not doing the right thing. So, I needed to completely hide it.

Later, when I attempted to navigate my gender path, I found many obstacles I did not foresee hurting me. But they did and brought about many doubts. Of course, the main doubt was, should I be doing all the cross dressing I was doing in public at all. Still, I persisted and improved my craft at presenting well as a femininized person. Finally, I arrived at a point where I could leave my dark gender closet and attempt to live a new scary yet exciting life. The more I explored as a novice transgender woman, the more I wanted to do. Which brought me back to the question, was I doing the right thing. 

Similar to so many of you, I suffered from extreme guilt as my second wife kept telling me my gender desires were selfish pursuits. The sad part of it was, for the most part, she was right. She wanted very little to do with me wanting to be a woman, so I kept it away from her. Not the right thing to do in a marriage but was my only recourse. At that time, I only had a distant dream of perhaps living someday as a transgender woman. All I needed was the courage to face my reality. 

Because of a number of reasons, I needed to do much more exploring the world as a transgender woman to see if I could survive. First, I had to look the part, then I needed to live the part. Standing in my way, were the usual questions of transitioning to another gender such as what would become of my family, friends and job. As well as did I really hate my male life that much. I wasted hour upon hour antagonizing over what I should do and would it be the right thing. 

I was stubborn of course and refused to do any more than observe several transsexual women I knew from a distance. From their stories I did know they had really good safe jobs or were close to retirement so they could support themselves whereas I did not and had no idea of what I would do for an income. Plus, I also needed to consider, both of them were flat out gorgeous and had no problems presenting in the world as women. I did not labor under any idea I even came close to being as attractive as them and did not have that going for me either. After taking all of this and much more into consideration, I did not know what I could do about my gender dilemma which was not doing my mental health any favors.

What I did do was try to continue on the path I was on. To increase my awareness of the world as a transgender woman as much as I could at a time, I went as far as I could. Even absorbing major clashes with my wife over what I was doing. I can't always say I did the right thing as I learned more and more about living in the new world I was seeking. There were too many times when I had to out and out lie to get out of situations, I found myself in. In all fairness to my wife, she told me to stop it and just become a woman to bring peace to both of us. Still, I did not have the courage to change my life and leave her behind. I did not do the right thing. 

You regulars know what happened next. My wife passed away quite tragically from a heart attack leaving me all alone with my dogs to put my life back together. I rapidly turned to my inner feminine self as the strongest person around and did the right thing and finally turned to a life I always just dreamed of. 

On a side note, I may be missing a day of blogging tomorrow as my wife Liz and I have a daylong seminar to attend. Sorry for the inconvenience!

When too Much Wasn't

 

JJ Hart (Middle) with two friends.

As I continued along my long and winding gender path, I (on occasion) ran into situations when the public seemed to be too much. 

Examples were the times I was approached in public by strangers when I did not want to be. Very quickly I needed to judge their motives. Did they see me as a man in a dress on one hand, or as a woman on the other. Naturally, it made a big difference when I returned home and rated my experiences as a novice transgender woman out in the world for the first time. How did I do? Was I too much for my own good and did I need to tone it down, or attempt to do more?

There were the times when I managed to thrive in situations where women dominated and times I could not and ran home. Back to my gender drawing board. There seemed to be so much to learn, I was overwhelmed by the task ahead of me if I was ever to achieve my dream of living a femininized life as a transgender woman. 

In the end result, normally I found too much just was not when I was trying to get ahead in a new world I was just getting used to. The problems occurred mainly in the areas of fashion and makeup, as well as where I was trying to go when I went out. Once I got them under control, I was able to build a stable new life in the girls' sandbox. Once I earned my way in. Often earning my way in, had its own set of challenges. Mainly I had to find out how to play correctly to be accepted. On the other hand, even though it was difficult to do, I had to play to learn a life's full of lessons in a hurry. As I always say, my women's workbook was blank to this point, and I needed to write it. 

I found as I struggled to fill out my workbook, I needed to be extra vigilant in how I viewed other women, since I was totally on their turf. For the most part, I did my best to hold back on my opinions and speak mainly when I was spoken too. It worked well enough until I could get my feet on the ground, and I could move forward as a transgender woman. My goal was to build my new life as a confident, intelligent woman in society, but I needed to prove to myself my goal was not too much and would destroy my dream of transgender womanhood. Fortunately, throughout my life, I had several strong positive feminine role models to work from and add to my workbook. When I was able to add their influences to the inner female, I already knew was there, the women formed a strong bond to guide me through my struggles.

Overall, I discovered rarely too much just was not. What was happening was, I was just paralyzed by fear to move on with my new life. Once I got over most of my fears, I was able to move on and be free to live a better life. A better mental health life waited for me when I quit fighting two genders to survive. 

Wait? There is More?

 

Hand Beaded Hair Beret
by Liz T Designs
Haur by JJ Hart. 

When I reached every dead end on my gender path, I thought I was finished with my dream of ever being a transgender woman.

It turned out, when I researched every dead end, most were just blind curves I needed to negotiate, so I pushed on. It turned out, one of my biggest problems I had was dealing with my own fears. Would I be discovered and laughed at or worse. When neither started to happen, I gathered my courage to do more and more in the world.

Mentally, I was able to make another major transition from cross dresser (which never worked for me), all the way to transgender, which did. The process turned out to be one of the biggest mental moves of my life and in many ways saved me from harming myself. All the years of not making a connection and connecting my gender dots were over, and finally, I was able to understand why my life had been so difficult. Mainly, it was because I was so busy fighting myself, I did not have the room to search for anything else. Keep in mind too, while this was going on, I was also trying to juggle a male life which I was succeeding at. Making it more and more difficult to give up.

Through it all, I did find out there was so much more to my femininized life than my old male one. To get there, I needed to keep pushing. I set up mini bucket lists where I wanted to try out as a trans woman to see if I would be accepted. At first, I went to the easy venues such as malls, clothing stores and bookstores to see if I could make it in my new world. Once I did, I attempted to step up my layers of difficulty to challenge myself to be better, and at the same time build my confidence to seek out more in my new life. My end goal with all of this was to discover if I indeed did have any chance to live my lifelong dream of being a woman. Even though I went too far on my bucket list ideas, I still had to push forward because so much was at stake in my life. Afterall, I had family, friends and jobs to consider among other things I did not consider yet because they were beyond the next blind corner. 

Sometimes, what was behind the next blind corner was easy to deal with and other times presented me with situations which were very difficult to deal with. Such as the time I had the police called on me due to an ill-advised rest room visit, all the way to being run out of my regular venues by a group of men who were harassing me. Predictably, it took me quite a bit of time to regain my confidence, but I did and moved on to greener gender pastures. 

One of my biggest obstacles to finding the greener pastures was my lack of knowledge in communicating as a woman. I never thought the public would want to interact with me as quickly as they did, and I was not in the least prepared for it. For the first time in my life, I needed to really listen to other people and prepare early for a proper response which was good enough to get me by. I even resorted to taking feminine vocalization courses at the Veterans Administration to help get me to the next corner to see if there was more to do. 

It always seemed there was more to do as I attempted to immerse myself into my transgender womanhood. Especially when I started gender affirming hormones. When I did, welcome changes began to happen quicker than I expected and once again, I was not prepared for what I was facing. For example, I had a timetable in my head for when I could finally put all the male life behind me and start a new life from all the gender work, I had done. Primarily, because of early surprising breast development, I needed to scrap my mental timetable and get started on my new life. From there, there would be no looking back.

From HRT forward, I thought there would be fewer mores in my life, but I was wrong. My wife Liz came along and with her, she expected me to accompany her in the world doing things I had never tried before. We went on vacations, went to the symphony as well as junk yards for car parts and made a life together. 

Now as I look to the final chapters coming up in my life, I know there are many more significant mores in my life coming up. It is just a part of life. Maybe transgender women and trans men just have more to navigate than the average person as we seek a new gender life. 

It's Complicated

Image from John Barkiple
on UnSplash.

 
In many ways, this post is an extension of yesterday's post.

In it, I attempted to write about the connection (or lack of it) between members of the transgender or cross-dressing communities. What continues to amaze me on many levels is how complicated the outside world does not see in our world. So many in the world still think all we have to do to "solve" our gender problems is as simple as not putting on a dress for transgender women, or a pair of pants for a transgender man. Granted, it is very difficult to explain what is going on in our own gender challenged minds. How could I explain my desires to others, when I could not explain it to myself. Back in those days, there were not even therapists available who had any knowledge in the gender field to provide any help.

In the meantime, I internalized all my feelings and dreams of being a transgender woman someday, much to the detriment of my own already fragile mental health. My problem was (among many) I was naive and did not realize how complicated my genders were. I had no workbook to study from. Being completely on my own, forced me into making many mistakes I did not foresee coming as I followed a curvy gender path. The only woman I sought guidance from, withheld any significant advice, basically because she just clashed with and did not like my inner feminine self which was trying to emerge. 

What I did then was move past my wife and discover what my new world as a transgender woman had in store for me. All of it was difficult in the worst way when my old male self-ganged up on me. Both of them were losing traction on claiming my world and resented it on so many levels. It stayed so complicated because I loved my wife deeply and we had built a twenty-five-year marriage often on the ashes of my gender conflicts. When I was down and out emotionally, my wife was the first to bear the brunt of my frustrations. I knew I was wrong, but there was nothing I could do to battle my overwhelmingly frequent desires to being a woman. In fact, when my second wife was still alive, I was very actively exploring the world as a transgender woman. Primarily to discover, if I could survive at all.

My explorations proved what I suspected all along. Women lived a very layered and complicated existence and being able to join in at mid-stride would not be easy. Similar to attempting to jump on a very fast moving merry go round without it slowing down. Once I found myself on the feminine ride, I was given a chance to really learn and absorb what a woman's life was all about as my brain was rewired to survive. What amazed me was how quickly I was welcomed into a woman's world as one of their own. The worst which happened to me was when I was gently laughed at by my new cisgendered women friends when they said, welcome to our world. Which I was overwhelmingly happy to be a part of.

Ironically, if I was prepared or not, I entered a world much more complicated than the gender conflicted world I left. Plus, what happened was, the more I grew into my new world of transgender womanhood, I grew away from my wife. Before she unexpectedly passed away, it became obvious our marriage was doomed to at the worst being a total split, to at the best living as two women on their own. One-way or another, fate decided the question for me.

In many ways, I wonder if I had ever imagined such a complicated journey through life was going to be in store for me. I guess at the least, I could say, life was never boring as I suffered from being the round peg being forced into the wrong square hole. My reward was being able to say I learned how both sides of the binary genders lived, and I could choose which one I wanted to live as.

I Just Couldn't Live Without Her

 

Image from Brian Kyed
on UnSplash.

At a certain moment in my life, I had reached the point of no return where I was living with two women, the one inside of me and my wife of twenty five years.

The question remains, how did I find myself in such an untenable, precarious situation. The answer was, it was not easy, and I really had to work hard to get there. Decades, to be exact. Once I pulled myself out of the mirror, and put her into the world, I knew I could never go back to being a parttime cross dresser. I could never live without her.

Many times, I have gone through the many steps I took on my path to transgender womanhood. To provide you all with a more precise look at my actions, we need to go back to the years when my second wife was still alive. What I began to do was sneak out of the house when she was working cross dressed in the world just to see if I could. After a very rough beginning, when I was laughed at, I began to get my high-heeled feet on the ground and do better. So much better, I began to think my ultimate goal of living as a transgender woman on my own terms may actually be possible. 

From there, I began to spend every spare moment I had alone as who was to become my authentic self. I became so immersed in becoming a woman, I needed to concentrate on the times when I still had to be a man at work, or with my wife. The biggest problem I had was, deep down inside I knew which gender route I had to take to survive in the world, but I was afraid to face it. The fights between my wife and I became so bad, a couple times she just told me to be man enough to be a woman. I was not man enough to do it, but I was stubborn enough to keep trying to live a middle of the road gender life, which became impossible to maintain. My mental health suffered, and I began to be more self-destructive than I already was. All the way to attempting suicide one night.

Fortunately, I was not successful in my suicide attempt, and I proceeded down the same path I had been on before. This time taking my cross-dressing activities into my own restaurant and threatening my substantially good job. Again, deep down I felt if everyone knew of my deep, dark secret, I would be relieved of the hell I was living because I had to make a change away from the male life I was living. 

Just before my wife suddenly died, I made one last ditch effort to partially purge myself of my femininizing supplies. I went all the way to growing a beard, so at least I was telling myself I was making an effort to return to the male world. However, there was one big problem, I was miserable and about the time I needed to go back into my feminine world, my wife suddenly and tragically passed away from a massive heart attack at work. Through all of our problems, I loved her deeply and we were married twenty-five years.

I often wonder what would have happened had she lived. I think now, my internal female would have won out and I would have completed my gender transition. She would have won because I felt so natural in the world as a transgender woman. When it came down to which woman I could not live with, I would have had to have chosen the woman I should have been all along and hopefully patched up my life with my second wife. So, at the least, we could have stayed friends.

Living the Dream

Image of dreaming woman from 
James Forbus on UnSplash.

 For the greater part of a half a century, the thought of transgender womanhood remained a distant dream for me.

The main reason was, I spent decades denying who I really was, as my male self-sought to rule me. Sadly, he either won many gender battles or made life overall miserable for me. When he was doing it, my dream remained in place as I wondered how big my rainbow was and would I ever live my dream. In the meantime, I kept experimenting in the world as an out transgender woman. 

When I had the chance, I would do things such as attend downtown festivals all the way to watching an outdoor concert as my new exciting authentic self. I had a black leotard top I often wore with a favorite pair of flair legged silky pants and a glittering pair of black and gold sandals. I even went as far at the daylight festival I went to; I added a pair of sunglasses so I could see anyone checking me out in a negative way without them being able to see my eyes. My biggest discovery was no one paid me any real attention. In other words, I was beginning to think I could actually live out my dream of transgender womanhood. 

From there I attempted to expand my new exciting life. I completely enjoyed the time I spent living my dream and soon, never wanted to go back to my male life. When I was forced back, I hated it. Often, I took it out on my second wife and other close people around me. By internalizing my dream, I grew angrier and angrier and almost lost good jobs because of it. 

It was not until I began to spend almost all of my spare time living my dream, did I realize I could really succeed at it. Finally, I had made the transition from the mirror to the world and was ready to attempt to learn to do more. Overall, I began to have more success than failures when I learned not to push my gender envelope too far. I was accepted at several venues where I wanted to go to watch sports and drink beer plus, I gained a couple unexpected female friends when I did it. I was discovering I was closer and closer to my dream of transgender womanhood was almost here and I wanted more and more of it.

I did not think I would ever make it to my dream, but destiny was on my side and all of a sudden, at the age of sixty, I realized I was at a huge make it or break it time of my life. Either I completed my gender transition then, or I never would have the chance again. I seized the opportunity and even had the chance of meeting the cisgender woman of my dreams who accepted and even encouraged me to be a better version of myself. She told me very few humans ever have the chance to reinvent themselves, so I should strive to do it right. As I did.

At my age of seventy-five now, I still have the everyday pain which comes with age, but I try to write and walk every day to stay active. Perhaps by doing so, I can expand my dream to the fullest. 

Thanks for reading along! I hope you can live out your dream also.

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.  

I Was Ready but Was the World?

 

Image from the Trolley Stop, Dayton, Ohio

It took me years to understand and accept my transgender womanhood, but once I did, what was the world going to think.

Once I had worked very hard to cross the threshold into being able to put a reasonable effort into presenting as a woman, the difficult work started. Even back in those days, I was able to learn basic tricks to take a good-looking picture but then I found putting the picture into motion was the problem. The whole scenario presented me with big new challenges, The largest mistake I made was underestimating how quickly the world would want to communicate with me. All of a sudden, when I was going out to be by myself, someone (usually another woman) would invade my little world. Which was suddenly growing rapidly. Initially, until I grew used to it, just trying to look another woman in the eye and talk to her was a real challenge.

I started by merely trying to mimic the tone and sound of the person I was talking to, then took femininizing vocal lessons to aid my efforts. I discovered quite quickly, I was more ready for the world than I thought. I found putting too much effort into communicating with a stranger could be a turn off and too little interaction could come off as being bitchy. So, I needed to be careful and usually let the other person lead the conversation. 

For the most part, I found the world was ready for a stray transgender woman just learning her way. I even was able to converse with several other women I met regularly in venues where I was a regular and so were they. I was amazed I had such an easier time talking to them woman to woman than I ever did as a man. One venue in particular in my world was a tavern called the "Trolley Stop" in Dayton, Ohio. It was/is the oldest continuing tavern in Dayton and I quickly became a regular of Gabby the daytime bartender. I knew from previous experiences, having support from the bar staff was key to my overall acceptance. So, I did my best to be friendly, spoke only if I was spoken to, and tip well. Being accepted in the Trolley Stop helped to really expand my world as a transgender woman and prove I was ready to do it. To make matters even better, the Trolley Stop even hosted a lesbian mixer every month or so and I enjoyed good times there as well. 

All of a sudden, the more I was out in the world as a trans woman, I proved I was ready to make it completely in the new universe I was in. It turned out to be one of the most exciting and satisfying times of my life. I was interacting and communicating with others. When I did, I made a whole new circle of friends (mostly women) I write about frequently. They provided me with the building blocks I needed to find my gender dreams. Once I had the solid foundation I needed, the rest was easy and fulfilling. Especially to my long hidden inner feminine self who had been punished for my entire life.  

  

Gender Lighthouse

 

Image from Juan Gomez
on UnSplash.

As I grew older and more in touch with my possible transgender womanhood, it often seemed to me to be a distant light at sea in my life. 

In fact, I equated my brief encounters with gender euphoria as moments in time when I was hopelessly adrift in a huge sea of life around me. I was rowing my little boat as fast as I could against a strong current, I mostly did not understand. Long ago, my gender notebook had been washed overboard, leaving me on my own to understand a new and exciting feminine world. 

As I was stuck rowing in circles in my shrinking male world, faintly in the distance, I could see a lighthouse which would ultimately show me the way to gender freedom. As I kept on against all odds, the light grew brighter. The entire ordeal was difficult, and I needed to battle tons of self-destructive behavior on my part to just survive at all.

Plus, through it all, my mental health suffered terribly. Since I was already diagnosed as being bi-polar, the last thing I needed was gender dysphoria to worsen my condition. Worse yet, I tried to self-medicate my problems with too much alcohol. Which ultimately caused me to lose my way more dramatically and take more self-destructive chances. I was taking my eyes off the lighthouse, and it was fading away in the distance. Just in time, I was able to regain my equilibrium and was able to set my eyes firmly on the light again.

I was able to get out of my boat and try the world at its best and worst. As I said, my feminine workbook long ago disappeared and I had to go it alone. As I mentioned in my last post, out of sheer good fortune, I was able to work my way out of potentially dangerous situations when I could have hit the rocks in my little fragile boat. I reacted to the experiences as surviving points on my gender learning curve. I resolved to learn from each one and keep my eyes on the light which was slowly becoming brighter. Maybe, I could achieve my dream of transgender womanhood after all. 

For a long time, the person who kept the key to my dream was my second wife who told me on occasion to me to be man enough to be a woman and being the pretty, pretty princess just was not going to be enough to make it. The problem was, she made me figure out what she meant, and it took me years to do it. I needed to wait until I had rowed to shore on the feminine side of the beach and found my way behind the gender curtain by learning lessons cisgender women grow up understanding from lifelong lessons. Or the pretty, pretty princess better learn how real women live in a world they control. I started to dress to blend in with other women on one hand and how I lost intelligence in my conversations with men on the other. Very quickly, I grew tired of being "mansplained" on the very simplest of topics. 

Once I found the lighthouse and made it to shore, the hard work started, and I needed to learn how to communicate with the world, one on one. Nothing told me, my communication efforts would be mainly with the women I met in the world as most men mainly left me alone. I knew most of the women started the conversation because they were curious what I was doing in their world. I did not really care because I was learning what I needed to know to keep my boat on the gender beach. 

Thanks to the world of women I encountered, I found the lighthouse at the end of my search and was able to find my way in a new world as a transgender woman.

Why Not Me?

 

Image from Danielle
la Rosa Messina on
UnSplash

Going through life, I was very insecure concerning many things.

I always had a difficult time excelling at all in things such as sports because I was so insecure about winning. If I did not, which was common, I could run home and hide behind my makeup and pretty dresses and pretend I was a girl and all the pain of losing went away. Then, the more I cross dressed, the insecurities began to sneak in there also. Was I presenting well enough and how would I ever know if my only contact was between me and my mirror. I thought I looked presentable, but would the world agree and what if I looked like a clown in drag.

It took me years to even acquire the basic wardrobe and fashion I needed to even get myself a fair shake with my feminized presentation. All along, my lifetime dream was to be a woman, and I was so far away. I did try to make an excuse to cross dress and come out to a friend once, but it was a dismal failure when he was embarrassed and turned away. The whole experience sent me running back to my gender closet and slamming the door. I did not know what my next move would be.

Life went on for me and the desire to possibly living my feminine dream never went away. In fact, it became stronger and stronger. When I could, I made "investments" in better fashion, wigs and makeup which really helped me advance my overall presentation. As I did, I gave the public another try to see how I faired in the world out of my closet. I needed to put aside all my insecurities, gather up all my courage and give it a go. 

Initially, my path was a bumpy one, full of false stops and starts. I was flying blind with no handbook to help me, and it showed. During too many nights in failure, I had to run home in tears wondering if I was on the right path at all. Somehow, the faint voice of my inner feminine soul could be heard telling me not to give up as there were better times ahead. I listened, pulled up my big girl panties and managed to move forward as I discovered a better life as a novice transgender woman. 

I discovered the best way to combat my insecurities was with confidence. I resolved to never let the world see me sweat. First, it would ruin my makeup and second, if someone had a problem with me, it was their problem, not mine. I had put an incredible amount of time and effort into being the new transgender woman I was becoming, and I would be dammed if I was going to give it up easily to some bigoted transphobe. All the years of losing weight, learning makeup and skin care just could not go to waste as I chased my insecurities about living fulltime as a transgender woman. 

Still, I wondered, would I ever be good enough to join the world of women and would it be what I expected it to be. 

Unexpectedly, I received a giant push from women friends I found and cherished. With their help, I was able to put my insecurities behind me and become a part of a world I had only dreamed of. Why not me, became you can do it and I succeeded in my path into transgender womanhood. 

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.  

Nobody Understood

 

Virginia Prince

What really hurt me when I first realized I had gender issues was when I had no one to share them with. I was all alone with my problems, or so I thought.

I lived in fear of discovery all the time from my parents or my slightly younger brother. Even then, I knew discovery meant an unpleasant trip to a psychiatrist. The closest friend to me who may have shared a few of the same feelings, ended up moving away. With him, both of us were allowed to experiment wearing his mom's old clothes and putting on her makeup. It was the closest I would ever come to having anyone to share my true life with. Ironically, we never talked about the cross dressing we were doing. We just did it. 

As I said, my friend and his family ended up moving far away and years later, I often wondered if he had any gender issues too which stayed with him. Plus, as I always point out, I spent my youth and the years leading up to college in the information "dark ages", or the time before the internet became so popular along with social media. All I had was my cherished copies of Virginia Prince's "Transvestia" publication to get me by. At the least, "Transvestia" showed me there was a community of others with the same gender leanings I had. Also, in my well-worn issues I saw meetings or mixers within driving distance of me which I could go to. I was excited when I learned I could actually meet other self-proclaimed transvestites in person. The problem was, once I learned I could meet them, was I brave enough to do it. 

You all know, I was brave enough to meet them but then I encountered another problem. No one at the mixers still seemed to understand me. I was too much of a woman for the cross dressers and not enough of one for the transexuals. This was back before the transgender term and meaning was even used and popularized, so once again, I was stuck with no one to understand me.

Finally, the world began to catch up with me and I understood where I was when it came to the cross dresser - transgender community. Even better, with the help of the internet and social media, I began to stay in touch with others with similar views. Suddenly, in many ways, everybody had some sort of an understanding about how I felt. It may have taken me a lifetime to do it, but I made it into the only community who knew what I went through.  

Maybe the problem with the world as we know it these days has been influenced by people who have never met a transgender woman or trans man at all. To understand a trans person, it certainly helps to have followed a similar path. Even briefly. 

In recent years, I went from no one to understand me to having a whole group of people who have not taken the time to even accept me on a basic human level. It seems, I have gone full circle to arrive nowhere. 

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.