Build the Plane before You Fly It.

 

Image from Miquel Angel
Hernadez on UnSplash. 

Early in my life I learned to build my gender plane before I tried to fly it.

When I was simply admiring myself in the mirror, life was easy, or so I thought. I could apply my makeup and put on my mini-skirt and journey to the mailbox, hoping the neighbors would not see me. Through it all, the mirror lied to me and said I looked wonderful even though I did not even have a wig. Even still, I kept going. Mainly because we lived in a very rural area and no one saw my mailbox adventures.

I suppose, during those days, I was merely experimenting with clothes and makeup, the same way any other young girl would do. The problem was, I had no one in my peer group to criticize me and help me to learn what was correct with make-up and fashion and it showed. I was attempting to fly my gender plane before it was fully built. The mirror never did any of it for me. It was simply there to tell me how good I looked.

It was not till much later in life, did I begin to replace the mirror with public feedback when it came to early adventures going out in the world as a transfeminine woman. I vividly remember all the nights I quickly returned home wiping the tears away after being followed by someone and laughed at. Mainly from teenaged girls. Somehow, I needed to keep taking my plane back to the drawing board to attempt to see what I was doing wrong. The good news is, I did begin to figure it out. I was dressing for the wrong gender. Trying to please men, when I should have been trying to please women. Out went the sleazy, ill-fitting clothes. Replaced by more sensible clothes as I did my best to cover my male poisoned body.

It worked as I began to blend into the world, as I gave myself the chance to experience my reality for a change. I was similar to the Wright Brothers during their first flights; I was not going far but I was doing it. During this time, my flights grew dramatically longer. I was finding my way out of the clothing stores where all they cared about was my money, all the way into restaurants where I had to interact with staff on a one-on-one basis. I was discovering how well my plane was built or not. Surely, I was still experiencing my ups and downs, but I was having more of the positive side of life.

The problem was, on my male side, he was still having success in his world with a very successful job. So, he wanted no part of helping to build a new gender plane. I was forced to build around him. Which made for a very shaky foundation. Especially for my already frail mental health. It hurt me deeply when I was flying high and he brought me back to earth with a crash. He even took me as far as an ill-fated suicide attempt.

In the short, and long term, I survived him and continued to build my plane, every time I thought I was done, there was more to do as I studied the nuances of living a transfeminine life. Adjusting to being passive aggressive alone to other women was a big adjustment, not to mention the communication issues I faced in the new world I was in. Other women were very curious about me and wanted to know what I was doing in their world. Very soon, my air space became very crowded with new people, mostly all women.

Many times, starting all over in life became a major challenge for me. I needed my plane to provide me with a better view of what was really happening in my life. I had too many fake, mean people to beware of. Even after all these years, my plane was still very fragile. Before I moved ahead any further, I just had to build in the inner strength I needed to pursue my dream of living fulltime as a transgender woman.

To accomplish my dream, I needed the friends I had found in my new life to do it. I always mention the Liz’s, Kim’s and Nicki’s of the world who helped more than they ever knew. It was all of them who finished building my plane more than I did and I will be forever grateful for them coming together to save me.

Growing up, I built plenty of model cars to look at and even race, but nothing helped me to prepare for the greatest building experience of my life. A gender transformation project which took me decades to complete. In fact, I am still working on it to this day even though I have been fully out for over a decade now. There was more building than I ever thought possible to start all over again with my life.

 

Building Bricks as a Trans Girl

 

Image from Marcus Spiske
on UnSplash. 

If nothing else, my long life has been a series of gender building blocks.

Ironically in my youth I spent hours building small houses with a set of plastic building blocks I was gifted. That was until I discovered the joys of mom’s clothes and began to admire myself in the family’s hallway mirror. Little did I know, from those humble beginnings, I was heading towards building a lifetime of building blocks. Transphobes as well as other assorted bigots were ruining my early days as a transfeminine woman. Which meant I needed to sort through my gender bricks until I could survive.

Very early on, I knew I needed to build a strong closet. To quote a famous “Doors” song, I was a “Rider on the Storm.”  Somedays my storm would be less as my gender dysphoria subsided on others it was unbearable and all I did was think about the next time I could cross dress in front of the mirror. It was on those occasions; the mirror would play tricks on me and tell me I was an attractive woman. I say tricks because on a good day, I had not mastered the art of makeup or fashion. I needed to be persistent in my building blocks because I would never have been successful if I did not. My dream of living a life in a transfeminine world was proving to be much more difficult than I ever imagined.

It turned out my wife was right, I did make a terrible woman until I paid my dues, but I couldn't pay my dues until I built enough gender bricks to be allowed behind the gender curtain to learn the nuances of doing it. One thing I did know was that I was my gender journey of a thousand miles did begin with that single step in front of the mirror. To keep up with my journey, more and more bricks would be needed for me to succeed. Once I was behind that imaginary but so real curtain, I became a complete sponge to be the best transfeminine person I could be. Some days I was thrilled to be where I was and on others, I was scared to death. Building a new life from scratch with very little help proved to be intimidating.

I learned and became better at dodging the barbs and smirks of the haters in the world. I had built enough bricks to replace my old gender closet with a new one which was built to last me. The new closet was good enough to take me to the point where I could authentically begin a new life as a transgender woman. Which meant I needed to be better than the average cisgender woman just to get by.

The women around me who helped me build my new gender fortress were the gate keepers who never knew how much they helped me live my dream. I was able to layer my feminine experience all the way to success.

Little did I know when I was a kid trying on my mom’s clothes for the first time, how far I would need to go to survive. My last adventure turned out to be my best.

 

The Big Risk

 

Image from Joshua Rawson Harris
on UnSplash.

When you jump from one of the main binary genders to the other. In my case of course it meant leaving all my hard-earned male privileges behind and move into a largely unknown world.

The risk was tremendous the farther I went along. Mainly because I was accumulating an increasingly amount of male baggage. Such as family, house and good job. At the same time, I was perfecting my transfeminine appearance, which encouraged me to move forward in the world. To be sure, I was involved in being tested with a double-edged sword. Or which way should I go? I spent many wasted hours trying to obsess over my future, which was still very vague. At that point I did not even know if I could even exist in a fully transfeminine world. On nights I was accepted by the public, gender euphoria told me I could. Then, on the nights I was rejected by the public, I thought there was no way I could ever live my dream, and it would remain just that…a dream. A dream which never would go away. 

Through it all, the idea of risking all my existence remained with me and naturally scared me to my bones. I was hiding away my biggest secret and even though I did internalize it well, it was a drain on my mental health. Which is a side story I tell often because it is something I think more transgender women and trans men can learn from. At least I hope so.

Something else, I don’t think the average person understands about us, is this is not a casual joke to us, and we just cannot stop putting on a dress on a whim. We are ready to risk it all to live an authentic life as our true selves. Free from our closets. The problem was at the end of a day out, most of us must go back to our old unwanted male selves (or female selves for trans men). For me, it was always a heart-breaking experience as I tried desperately to maintain my male façade for my wife and work.  The only alternative I had was to attempt to live part of my life as a trans woman and the other half as a macho man. It tore me up.

The entire process just became worse and worse when I began to carve out an all-new life in a feminine world. The more success I felt, the less I wanted to go back to my old life and began to research the prospect of living my lifetime dream. In fact, all I can remember all I really wanted to be when I was young was, I wanted to be a woman. Which of course, I needed to keep to myself. I was miserable as I felt as if I was the only boy in the world who felt that way. It took me years to learn I was not the only male in the world who wanted to be female and was prepared to take the risk to do it.

I was able to find a couple of real live acquaintances who took the risk, almost, so I could judge what it meant for me if I decided to follow in their footsteps. I say almost because one the transsexual women I knew was a very attractive retired firefighter in Columbus, Ohio and had a very good pension to live on. The other trans woman I knew was even more attractive in her own right and a very accomplished electrical engineer and would always find a job. I had a good job but not one which would carry over to a gender transition. So, I had much more to consider, not to mention neither of the women I mentioned were in a serious spousal relationship and I was. Right in the middle of a twenty-five-year marriage. I would later come to know how similar yet drastically different our transgender community is.

The pressure I was feeling to take the final risk continued to build. Aided by the success I was having in dealing with the public, I was encouraged to take the final risk in my life. At this point, destiny stepped in to show me the way. My two major stopping points were my second wife and what I would do for an income after I transitioned.

My wife tragically died, leaving me with one to speak of to object to me leaving my old life behind and beginning a new one. Then, by that time, I was in reach of being able to retire on early Social Security income plus what I could sell online. In many ways, the lightning did come right before the rain for me and then the sun came out. When it did, I could see my dream life had arrived and I could live how I wanted to.

 

 

 

Just Part of Being a Woman?

 

Image on Unsplash. 

Just part of being a woman meant several different things to me.

First, I needed to get there by being able to present well enough to being accepted by other women. Once I arrived, I was able to enjoy the benefits of living in my dream world as well as the drawbacks. The first night I had an idea I was arriving was when I began to be semi-friendly with a man I met at a venue, I was a regular in. He was part of a small, diverse group of people I mixed with often. Sadly, I followed the saga of his quickly failed marriage to another woman in the group. She was an exotic dancer with long black hair, and he was a big, bearded man who rode a Harley motorcycle. Not exactly a match made in heaven. But they went ahead with the ceremony anyway. It failed within a couple of weeks.

I really don’t know why, but from then on most of the group turned against him, except me. I felt sorry for him and could sense the hurt he felt, so we began to talk. Before long we became friendly enough to look for each other when we came in alone to socialize. I can’t speak for him, but I was in uncharted territory even talking to a man at all since I was basically scared to. Who was I to say no to this big good-looking guy who wanted to talk to me? You are right. I couldn’t. I was too shy to even ask him to see his Harley before he rode off to another job in another town and I never saw him again. How different my life could have been if I had pushed my luck as a transgender woman just a little farther.

That fleeting encounter left a deep impression on me, not because it blossomed into anything, but because it made me realize how much of life I had yet to explore. It was a bittersweet moment of clarity: I had spent so much time crafting a version of myself that fit into the world I longed to belong to, yet I was still afraid to fully embrace the opportunities before me.

In the days that followed, I thought a lot about courage to truly be brave, not just in appearance but in action. It wasn't about being bold for the sake of it, but about taking the step that felt impossible, the one that whispered promises of growth and self-discovery. And yet, even as I reflected, I knew that fear still gripped me, tethering me to the safety of the new family I was creating.

It was around this time that I began writing the blog, capturing what I could of the small victories and the quiet heartbreaks that defined my journey. The act of writing became my sanctuary, a place where I could be unapologetically honest with myself, where I could acknowledge my fears without judgment. The words became a mirror, reflecting not just who I was but who I could be if only I dared to push beyond the limits I had unconsciously set for myself. By doing so, I hoped I could help others.

Life has a way of surprising you, though. Just when you think you've missed your chance, it presents you with another, often in the most unexpected of forms. Sort of like the first night I found myself in the middle of four men discussing guy things which of course I knew quite a bit about. Not realizing exactly where or who I was, I attempted to add my comments to the group. The men paused for a moment, then went on with their conversation as if I was invisible. I learned my lesson, entering a male only domain was a big no-no and exposed my new feminine life of having a lesser IQ. 

On my very few encounters with men, I learned to let them lead the way in conversations. No matter how inane the subject matter was. A prime example was the night I always mention when my car broke down and I needed to call a tow truck. Also, to my chagrin, a well-meaning policeman showed up out of nowhere to help. Between the cop and the tow driver, they refused to even listen to the directions I tried to give to my house. Then everything became worse when I had to ride home with the driver. By the time I arrived home, I had nearly reduced myself to playing the dumb blond just to survive the trip.

Just part of being a woman just meant leaving my male self behind, which is what I was trying to do anyway. What I did not count on was how fast I would lose most all of my male privileges I took for granted when I transitioned. All cisgender women go through the same process when they grow up around boys. It just took me a little longer to get there. Or, as my lesbian friends said, welcome to their world.

Plus, there was the new magical world of gender affirming hormones to consider. The HRT certainly contributed to my internal part of life as a woman.

Survive or Thrive as a Transgender Person

 

Image from The Blow Up on UnSplash.

It is easy to say, there is a major difference between just surviving and thriving as a transgender woman or transgender man. 

During my very long gender journey, I spent most of the time just surviving. Mainly when I existed by admiring my femininized version in the mirror. I did not understand at the time the difference in wanting to look like a girl, I wanted to be a girl. The entire process caused me huge amounts of duress and ruined my fragile mental health. Primarily because I had no one to explain to me how there were many others who were suffering in their own closets. In those days, there was no internet to provide any information whatsoever. No one to connect with at all. On some days, the loneliness was unbearable.

Still, I survived and continued to follow my own path. I was able to do what worked for me and gradually was able to join the public flow as my own extreme novice version of being a woman. As with any other newcomer, I paid my dues as ugly as they were. Along the way I kept thinking about what I was doing. Why would I ever consider trying anything as crazy as actually following through on my feminine desires to live a transgender dream.

Following a certain tipping point I went through, my desire to do more than just survive as a transgender woman became too much to handle. I was becoming increasingly more mentally unstable and self-destructive to the point of attempting suicide when I could take my life any longer. Fortunately, I was not successful and then set out to do more than survive.

I knew enough to know what I needed to do. Make a deeper dive into myself and explore my own femininity. I also knew I had to leave the mirror behind and substitute it for the world. To do it, I had to set my fears aside and look the other women I inevitably faced as the primary gate keepers in their world. A primarily had to learn the basics of passive aggressive behavior. Was another woman really letting me into her world or just acting as if she was. I learned the hard way to have eyes on the world from behind my back.

By succeeding in the world in my transgender womanhood, I was essentially carving out my own niche. Primarily because most of the world had never seen a transgender woman at all. When I immediately established, I was not a scary person at all up to no good, normally I received a good reception from other women, not men. With women at least, the gate was open for me to walk through. With men, my interactions were few and far between as their frail sexuality was threatened. I adjusted to my new world very easily and thrived more than I ever thought I would.

Suddenly, nearly all my spare time was living as my feminine self and when I was not, I was thinking about her. Or why was I wasting my precious time as a man when I was thriving in my new world as a woman. Each evening, I was out I had the opportunity to discover more and more the nuances I would need to thrive in the world as a transgender woman. Still, some nights I was still struggling to take everything in as my senses were barraged from many different angles. Specifically, when I started gender affirming hormones. From that point forward, I was able to attempt to sync up my internal with my external self. As I thrived, my mental health improved as I was finally able to live as my true gender self.

With age, I learned life is, but a big circle and I was able to find my way into thriving more than surviving. Many days, it was a struggle but finally finding my way was certainly worth it in the long term. Since I spent such a long time just surviving, I felt so much better in my new life.

 As the image says, success only comes from failure.

Adjusting to Change

 

Image from
Rafella Mendes Diniz
on UnSplash.

I am biased, but I think adjusting to a lifestyle in a gender you were not born into is one of the biggest changes a human can make.

As many of you know, I took nearly a half a century to adjust to my gender changes. Looking back, some of the changes were a blur while others were so very slow. The reasons possibly were there were so many changes I made to arrive at the spot where I could take the big leap. For example, the night I went to an NFL Monday Night Football game with a lesbian friend of mine and her family. I was just coming out as a transgender woman and was scared to death but knew I needed to make the move and go with her. Needless to say, after the evening, my life changed forever.

The other night I mention often was when I went to see the Christmas lights at a local grist mill, by myself as a woman. I was not as nearly afraid as I was at the football game and ended up enjoying myself immensely. I felt secure in my fashion choices for the evening and was warm and cozy when I went up to one of the hot chocolate vendors for a warm drink with extra marsh mallows. Most importantly, I did not run into any major problems at either venue and my confidence skyrocketed. Maybe I could be secure in my transgender womanhood after all and live out my dream. 

By now, you may be thinking was that all it took to propel my confidence forward into a new life and leave the old male life behind. No, it was not. It is difficult to mention all the nights I spent out alone as a single lonely woman before I found friends to share my changed life with. Through it all, I needed to be so careful to separate my old male life with my new femininized one. Which meant to separate everything I was talking about to new people. Plus, I did not want to create a totally false past in my life and ignore everything I worked so hard to achieve. I found I could bring in the family I had and just change the perspective I was speaking from, and it worked. At the time, fortunately, I was busy closing out my old male life anyhow which had for the most part collapsed, so the time was right for a major change.

Surprisingly, change did come easier for me than I expected. My femininized life was a pleasure to adjust to. Since, I should have been living it all along. It was like my feminine inner soul was telling me she was right all along. If I just had the courage to make the gender change and stick with it. 

All the adjustments I needed to make in life to survive were worth it for me. Finally, at the age of sixty, I had seen enough of the small changes I was trying to make as a stopgap measure and I decided to rid myself of all my male clothes, start gender affirming hormones (HRT) and live the life I was always meant to live. 

How did I know I made the right change? Because, after I did it, I felt so relieved and natural. I let myself go to fall off my gender cliff and had a very soft landing. All those years which started out as just me in the mirror had come full circle and I was able to live my desired life. All because of the changes I went through.

All I Saw were Walls

Image from Cristina Hernandez 
on UnSplash.

 I saw walls everywhere as I needed to build my own gender closet to protect me.

When I discovered I needed walls to protect my gender secret from the world when I was quite young, I managed to build strong ones. Difficult for anyone to penetrate because I felt something was basically wrong with me and if I was discovered, I knew a psychiatric visit was in my future. Back in the late 1950's and early to mid 1960's, any form of cross dressing was still considered a mental illness, and I knew well enough I was not mentally ill from wanting to try on dresses and makeup. None of that served any positive purpose, and I was driven deeper into my closet of walls. 

Soon enough, I began to escape my walls and began to explore the world as a cross dresser, long before I made my second major transition into a transgender woman. In the beginning, and for years afterwards, I grew frustrated on my progress and began to take more and more chances when I left the house as a woman. It was almost as if I was trying my best to get caught. So, everyone could see in my closet of walls and discover what was really going on with me. One way or another, discovery could lead me to a release of the gender torment I suffered from, and I could go on to live the life I had always dreamed of.

What I discovered was, dreams and reality were two different things. Or could I ever hope to go out and mix in well enough with the world of everyday cisgender women and survive. I was quite naive for years and thought I could be accepted as my form of an everyday woman by simply looking the part. Which led me to many memorable experiences in the girl's sandbox. Many of which I barely survived because I had allowed the wrong woman access to my closet. I had wrongly thought some women would allow me behind the gender curtain without a struggle and I needed to escape the sandbox with new claw marks up and down my back. Over time, my wounds healed, and I became a seasoned veteran of survival in a world ruled by women. 

As I did, my walls became the path of transition to transgender womanhood I was taking. I needed to plan far past just a day at a time presenting as a woman the best I could. How was I going to approach the time which was rapidly approaching when all of my life would be consumed by living my dream, and how did I stop it from becoming a nightmare? To make matters worse, I kept running headfirst into walls set up by my old male self. He never wanted to let go of his world and I needed to be careful I did not slip back into it when I was not paying attention to the way I walked or communicated in the world as a transgender woman. I was capable of ruining my whole day by forgetting to smile at the world, doing my best to talk like a woman, or move like a linebacker in drag. It took me years for muscle memory took over from my feminine side and I began to climb the walls I needed to be successful in the new gender world I was in. 

The best part was, I was seeing fewer and fewer walls. I had passed most of the challenges I had set up for myself. When I did, I became much happier and knew if I tried to stop the train I was on, I would go back to the miserable life I was trying to live between two genders. There was no way I was going to do that because of all the time and effort I put into releasing myself from all the walls I had built.

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.

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. 

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.

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.

A Push versus a Dream

 

JJ Hart

I often describe my journey to transgender womanhood as the impossible dream. 

On the other hand, I cannot ignore all the pushing I needed to do to arrive at my goal. My pushing started at a very young age when I was first cross dressing in front of the mirror. To begin with, I needed to push hard to find hiding places for my exceedingly small, treasured collection of feminine wardrobe selections. I resorted to old boxes in the garage attic, all the way to a hollowed-out tree in the woods next door to our house. In trash bags. Anything to stay safe with my secret. I knew if I was exposed, life as I knew it would be over.

I did push on and survive so my dream was still intact when I went to college and then served out my time in the military. My military time was especially stressful as I needed again to carefully conceal any idea, I was feminine at all. Through it all, I needed to keep my thoughts centered on a far-away dream I had of being able to live as a transgender woman. Sadly, there were too many times when I did not see how I could make it at all. Especially when the Army was strongly reinforcing my manhood. 

As in many other facets of life, the Army came and went leaving me a sense of freedom of what I could do concerning my gender issues. My first marriage came shortly following my discharge from the military and left me still wondering about what was going on. My first wife knew I was a cross dresser and did not really care, so I was left on my own to make any gender decisions I might decide on. This was back in the late 1970's and there was very little information on even being a cross dresser available. Again, I was on my own until the computer became a reality, and I was able to reach out to others. I learned quickly I was not alone and began to push for more clarity in my life. I even was able to dream more frequently of being able to live as my authentic self.

Before I did, I needed to determine what my authentic self really was and push to get there. This meant going down a largely selfish road as I carefully checked my gender boxes. It took me years to figure it out until I was able to merge how hard I was pushing with my ultimate gender dream of a being a transgender woman. My authentic self which was revealing her-self When she did, she left no doubt on why I felt the way I had my entire life. Something was not quite right, and I pushed on to figure out what the problem was. In the meantime, I treaded water cross dressing in front of the mirror until I found the courage and confidence to try going public.

Each and every time I was successful at all in dealing with the world, my dream was re-ignited, and I started to push through or totally ignore any gender warning signs I encountered. Everything I was doing put me completely at odds with my second wife, who again knew I was a cross dresser but never wanted me to leave the house dressed. Not only did I break my promise to her, but I also went as far as beginning a whole new life. My new life rapidly became very important to me mainly because I was happier and the whole life felt so much more natural.

My lifetime full of pushing finally aligned with my ultimate dream of transgender womanhood. Destiny opened my gender doors at the age of sixty and I took complete advantage. 

Dream On

 

Image from Darius Bashar
on UnSplash.

Last night I had a dream which may have signaled my subconscious mind has finally caught up with my reality. 

For the longest time, since I transitioned into transgender womanhood over a decade ago, I wondered why my dreams still had me as a man. All the way to people using my dead name with me. I woke up frustrated it was even happening at all. When I was very young, all the way to my teen years, I cherished the nights I could fall asleep and dream of being an attractive girl. Of course, when I woke up, I was very disappointed to learn I was still stuck in my same old male world. 

Years passed by and I proceeded to work very hard to resolve my gender issues but still had the same old male dreams. Who would have thought it would be this difficult to change me completely, including my subconscious dream world. For some reason, last night, the dream switch was flipped. As I said, even to the point of the world using my legal feminine name I changed years ago when I journeyed out of the closet.

Maybe the dream was reflecting all the tension I am feeling on my wife Liz and I's upcoming trip to the Florida Keys. Since it is a bus trip from Ohio, we will be traveling through several states not known for easily providing rest room privileges to transgender women. Not to mention, the possibility of encountering a stray transphobic gender bigot on the bus itself. Liz keeps telling me I am overreacting and just being paranoic. I hope she is right. Maybe last night's dream was a higher power telling me to relax and enjoy the vacation. 

Regardless, I am going to take a ten-day break from writing during our trip. It will be coming up this weekend and will give me a chance to refresh and start all over again when we return back to Ohio. 

During my vacation and beyond, it will be interesting to find out if my dream world has reached the tipping point to my authentic feminine self. Perhaps it is unrealistic of me to think ten plus years of trans womanhood could overcome nearly sixty years of living as a man in my subconscious mind. The whole process isn't the most trying problem I have to conquer. But it would be good if I could. Even in a dream world, I still do not like to be referred to as my old male name or be back living in a male world at all. 

Total erasure of my past is my goal. Although I cannot ignore all work my guy self-put into our life to set me up for success as a transgender woman, it is still a process I feel I need to complete. In the meantime, I know dreaming is a natural part of life. Now I can hopefully relax and look forward to a good night of sleep in my authentic world.  

All I Ever Knew

Circa 1940 image
of Virginia Prince

 Every once in a while I receive the question when did I know I was transgender.

The easy answer is I always knew but I needed to figure it all out. The more complex answer is I needed to figure it out after a series of transitions during my life. Two major ones occurred when I made the jump from from a very serious cross dresser all the way to a novice transgender woman. The second problem I had was back in those days, terminology to define a transgender woman or man had not yet been invented. Basically back in the pre-internet days when all we had was the preaching of Virginia Prince and her Transvestia publication which I could not wait to receive in the mail. Seeing all the pretty cross dressers just made me want to do more to improve my feminine appearance.   

I worked harder on my appearance than any thing I had ever done before and slowly began to see improvement over my testosterone damaged male body. It was all I ever knew. 

As I entered my transgender womanhood, I felt deep down inside I was doing all the right things, even though I was jeopardizing all the facets of my male life I had worked so hard to put together. What would I do when my family, friends and bosses discovered my deep secret. It ran so much deeper than just wanting to wear women's clothing. I wanted to be a woman and live a feminine life. 

During that portion of my life, I basically went into attack mode, doing every thing I could to learn how being a transgender woman would affect me. Every free moment I had, either I was out in the world as a woman or day dreaming of the times when I could. Naturally, I learned a lot, good and bad about what life had in store for me if I kept on going towards my gender dreams. I found the grass wasn't always going to be greener on the other side of the gender border as I lost all of my male privileges but hadn't gained any of the female ones. 

Soon I learned, it was truly all I ever knew. Somehow I was born to be feminine and not masculine. Which meant years of struggle to right the gender wrongs I was living. The struggles on occasion were crushing and keeping going was very difficult but I did. Probably because I was behind before I even started. I was born into a very male dominated family which had very few girls to play with. Plus, I never had any feminine characteristics myself to begin with. Add it all up, then include me never having any girl time with anyone all teamed up for a rough start for me on my gender journey.

Even still, my gender path was all I ever knew and staying on it finally made me successful. 

Building a Dream

Image from Moreno Matkovic
on UnSplash

 Similar to many of you ,my journey to building a dream took me many years.

As I am fond of saying, over a half a century of construction. A long time when you think about it. At first the steps were obscure and very shadowy as I snuck behind my family's attention to cross dress in front of the mirror. I did not know much about what I was doing, or the tools to do it so I looked as if I was clownish, most of the time. As luck would have it, the mirror often lied to me and gender euphoria set in, before I even knew what it was and what it meant. All I really knew was how at night when I slept, I dreamed of being a girl and was sad when I woke up and needed to face the same old male world.   When I was able to escape into my feminine world, I felt so natural and exhilarated, I just couldn't stand to go back.

The years flew by and I was able to learn more and more about the femininization process I was facing. At the same time, small glimpses of what if slipped into my mind. Or, what if, someday I could make living as a woman trans or not part of my reality. As I did, the reality of building a transgender dream became increasingly difficult. Partially because, at the same time, my male life was becoming increasingly successful and it became  harder and harder to give up what I had built. Still I moved ahead as the feminine forces within me were so powerful.

Since it is coming close to the Halloween season around here, I would be remiss if I did not mention how going to Halloween parties dressed as a woman did not help me build my dream of perhaps being a full time woman some day. Back in those days, the term transgender was still in it's infancy and I did not know how it fit me. All I knew was, I worried and stressed for months ahead of Halloween about what my "costume" would be. Predictably my outfits started out slutty and evolved into going to parties dressed as business professional to see how many people would notice I was a guy at all. Overall, I had several meaningful experiences at Halloween which provided quality building blocks I could use when I seriously began to enter the world as my authentic self. As promised, I will write more about them as Halloween comes closer.

In the meantime, I was having more and more opportunities to learn I was so much more than a man who wanted to look like a woman. I even received a  comment from "Paula" across the pond in the UK concerning a blog post I wrote on the subject:

"I often think that the moment of realization that you are a trans woman rather than a cross dressing man is the Biggy! After I accepted who I am everything else that followed was just a natural consequence of that initial revelation. After I had accepted that I was in fact a woman it was perfectly logical that I would want the world to experience me as such, so I went full time. As I wanted to experience the fullness (as much as possible) of life as a woman it was perfectly natural to get medical help, leading first to hormones and then surgery. All of those decisions were the natural consequences of that first understanding that this is who I am not something I do."

Thanks to Paula and all of who comment! I could not have put it better. 

As it was, I kept on building until I formed a solid foundation to finally achieve my dream. It was never easy but on the other hand, building something worthwhile never is.  All the lonely nights I spent going out just to be alone come to mind as well as the occasions I was shunned or even laughed at. At that point my dream seemed to be so far away. Deep down I knew I was doing the right thing and kept on building. It turned out happiness was just a build away. 

What If?

 

Marci Bowers

As I spent all the years as a very serious cross dresser, I dreamed of perhaps becoming a transgender woman and what it would be like to live a feminine life.

For many, many years I was my own worst enemy as I learned the parameters of what I needed to work with. First of all, I needed to play catch up with all the girls around me who were already experimenting with makeup and fashion. I remember vividly back in the mini-skirt days how the girls in my class would not so shyly sit and cross their legs to tease all the boys. Little did they know, the affect they had on several boys such as me. I wanted to be them and wear the skirt and panty hose and tease the boys.  I was so envious of the stories my wife told me of how she would roll up her skirt when she went to school and was out of sight of her Mom. 

I always wondered what if I could ever escape the mirror and experience life the same way she did. Of course I did not and had to set my own course. A course with no guidance or peer pressure on how I looked. What if I could live as a woman remained an illusive dream. To keep my frail mental health balanced, I tried to improve my presentation on my own  As I am fond of saying, I experienced quite a bit more error than trial as I slowly learned to express and embrace myself as a novice transgender woman. To add to my excitement, my wife and I purchased our first computer and I was able to learn about other transgender women in the world. 

One of trans women I learned about and was suggested to me by a reader (thank you) was renowned sex change surgeon Marci Bowers. Even though I knew I would never consider gender surgery for myself. Just reading Bowers journey gave me hope for my future.  My fondest desire her story would pave the way for an easier gender transition for the rest of us. 

I followed my new found confidence by exploring more and more as I tried  to carve out a niche to build my dream life. Even though I was rejected on many occasions, I still managed to climb the steep slope towards my transgender dream which was coming into focus. The main discovery I made was if I was myself, I could actually have the opportunity to live on into trans womanhood. If I did, I knew the risks were great and I was jeopardizing years of male life I had sacrificed to build up. 

Still I learned I had to follow my inner soul and see what if meant to me. Since I had worked so hard to climb dual gender mountains in my life, it was time to jump and head for a hopeful safe landing.  Even though I could never hope to be as accomplished and attractive as an Marci Bowers, I discovered just enough people valued me as my authentic self, I could survive. These were the people who never knew my before person and I was starting all over with. 

Even though I was still doing the pushing, they were the ones doing the pulling me into my new world. Proving what if was possible. 

The Rock and the Hard Place

 

Image from
the JJ Hart
Archives

Recently, I received a comment from a reader who said in essence, I was too hard on my second wife when I mentioned her.

After thinking the comment over, I can see why it was made. First, some quick history. My second wife and I were married for nearly twenty five years until her sudden and untimely death at the age of fifty. She knew I was a transvestite or cross dresser when we were married and accepted it up to a point. The demarcation line was always HRT or me pursuing  a life as a transgender woman. For years it was fine with me as she approved me going to a motel to cross dress and go out into the world. We had an uneasy gender truce and I ended up abusing it.

The problem was, I always blamed myself for our gender problems because naturally, they all originated with me. Primarily when I began to break the promise I made to never leave the house dressed as my feminine self. Of course, I eventually was caught and all hell broke lose. She was a strong woman and knew how to emotionally battle me. She was the rock keeping me from my increasingly obtainable goal of trans-womanhood and I was in the hard place of knowing deep down it was where my life was headed.

Along the way, my second wife imparted good information about being a woman but withheld other very important facts. She would just tell me I made a terrible woman and then adding in she was not implying anything about my appearance. Leaving me to wonder for years what she meant. Mainly I found my old male ego was still in the way of my gender progress to the future. It wasn't until she had passed on and I took the opportunity to really explore the world as a transgender woman, did I understand what she meant. I finally had to walk the walk and talk the talk to move my hard place along. Femininization was difficult yet exciting for me on many occasions.

My second wife also tried to tell me to follow my dreams and give up our relationship but I still tried to have it both ways which just made things worse. She knew me better than I knew myself. 

So, as you can tell, I owe her quite a bit and wonder if we could have at least arrive to a point where we could have been woman friends. I obviously don't say it enough if I am receiving comments to the contrary. I also don't praise the cis-women who stay in marriages with their transgender spouses. I know if the shoe was on the other foot, I would have an incredibly difficult time accepting a trans spouse. As my wife said, living with another woman  was something she never signed up for. 

The rock and the hard place cost me dearly over the years. The pressure of attempting to maintain a relationship and a male life with the increasing knowledge it was all a lie built up an enormous amount of pressure and all but ruined my fragile mental health. I resorted to trying to drink away my problems to no avail and just became more depressed. I was not freed until I basically had nothing else to lose after her death. Once I was freed, I could look back on our relationship for what it was and all the good times we had and how I basically hurt it all.

Bridging the Gender Gap

 

Image from Samuel Reagan Asante
on UnSplash

It is a dirty job but someone has to do it, right? We transgender women and trans men are in a unique position to be the only go between both of the primary genders and make a difference. If society and politicians let us.

I did not set out to write another post criticizing a certain political party in my state of Ohio  which is trying to do away with all transgender rights. You all know where I stand. Instead what I am writing about is singing the praises of acquiring deeper gender knowledge. Very few humans ever get the chance to journey across the gender border and see how the other half lives. 

Interestingly, there were times I was asked for my feelings about how another woman's spouse or boyfriend was feeling towards her. Women are more intuitive than men and were seeking out my ideas because they knew I at one time, had occupied the male world. I was filling a void they could not find anywhere else. 

Even still, bridging the gender gap was exceedingly difficult. There were so many things to learn about how the genders interacted with each other to survive in the world. In addition, I needed to adjust to being the pursued gender rather than the pursuer was all I thought it would be. I grew up with the idea girls or women had it easier because they did not have to go through the torment of finding dates, right into deciding what was the right date for me. That is if I was ever asked. Which was not often since I was mostly rejected by men. The feeling was mutual because I did not feel any particular attraction to them anyhow. Especially so when I was accepted into a group of lesbians who showed me my validation in the world did not involve men anyhow. 

My new friends taught me how to bridge the gap and learned so much from them while I did it. I was raising the bar in my life without, for the most part, realizing I was doing it. It was difficult learning to walk the walk and talk the talk as a transgender woman but slowly I managed to do it. I think now my major success came from the point I was finally putting my gender picture together. I was no longer a one man show, I was a one woman show. I could see my gender dream was possible following years of denial and struggle. 

Looking off the gender bridge proved not to be so intimidating any more. Even though I was still afraid of heights, I learned my gender issues did not involve heights at all. It was more a matter of me keeping my feet on the ground. 

Once I did, being able to help anyone else with understanding gender issues was a huge plus. Paying life forward for me has always been a powerful motivator. Plus, being able to shine a light on the gender differences between genders is not something to be feared. The differences should be embraced and celebrated. Including those of us who have been fortunate enough to have the chance to experience both sides of the binary genders. Even though, for me at least, all the down times and bumps in the road I experienced did not feel so good at the time. 

If I could tell my young self one important fact, it would be to relax, learn as much as I can and know I would be successful in the end and bridge the gender gap. Plus, if I stopped building unneeded bridges to climb and jump off of, I would be so much better off.

Never Going Back

Archive image. Liz on left.

Once I started down the road to living my dream as a transgender woman, I found I could never go back.

I am sure it all started the first time I viewed myself in my Mom's clothes and makeup in the mirror so many years ago. All I knew was something clicked inside me and I enjoyed the process immensely and couldn't wait to do it again. Going back to my male self became increasingly difficult. 

It stayed a problem the older I became as I began to be better with the makeup and fashion choices I could find. I even went as far as shaving my legs when I was young to get rid of the hated hair which came along with my unwanted puberty into a testosterone poisoned body. Still I persisted living a secret yet powerful life in the mirror as a girl. Through my often clownish makeup, I could still see my authentic feminine self peeking at me and I loved her. 

Over the years, practice made perfect and in many ways I was able to cover up my male body and present well enough as a woman to try out the world. Even though I took many bumps and bruises along the way, I persisted and small victories helped me to want to never return to the male life I never really wanted. Every now and then I was able to be successful in the world as a novice cross dresser. Still not understanding I was so much more than wanting to just look like a woman. I wanted to be a woman. Cross dressing was a welcome bridge to getting me to the big picture of my life, my desire to be a trans woman. Once I came to the point of wondering just where I fit in with my big picture in life, then I needed to see if I could make all the needed sacrifices to get there. All of my "secret" adventures as a transgender woman could cost me all I had worked so hard on in my male life. If discovered, I could lose my marriage, family, friends and jobs. As you can tell, a lot to be considered.  

During that time, destiny kept setting in and deep down kept telling me I could achieve my ultimate gender dream. Every blind corner I turned and every step I climbed on my path was showing me the way as I carved out a new life as a transgender woman. All of a sudden, my doubts started to disappear I was succeeding more and more when I sought to flip my male life to female. I even began to go to the same venues I went to as a guy with little to no problems. When I did, deep down I was terrified of losing my life as I knew it but on the other hand, I knew I was never going back. There was no way.

By the time I decided I was never going back, my decision was made so much easier by several things. Including unconditional acceptance by my daughter, the very few friends I had passing away and not having a job to worry about (since I was able to retire) made my decision so much easier. Even my very stubborn old male self could see no future and he faded away as I took the final steps to completing my gender transition. I even was able to solve my marital situation the hard way when my un-approving second wife passed away and I unexpectedly became involved with a very supportive third wife who loves me for who I am. 

I believe pushing forward and never quitting was something I learned from my parents. I am sure they would have never envisioned their teachings turning out this way with me.

Stuck on Me

 

Image from Monika Kozub'
on UnSplash

My second wife used to be fond of telling me, my gender issues were all about me.

Looking back, I think she was right. In so many ways I was single handily attempting to cross the gender frontier with no help from anyone else, including hers. Among many other things, she just did not care for my inner feminine self. She always called me the "pretty, pretty princess." Even though the comment always hurt my feelings, I knew I was too immersed in my appearance and then lacked the actual experiences in the life of a woman to prove her wrong. Plus, I was selfish in my pursuit of a better feminine cross dressed experience. Not to say very frustrated when I was only getting out into the world very infrequently to explore and learn to explore what she was talking about. Just going out on Halloween and very infrequent transvestite mixers was not enough to relieve my gender tension or dysphoria. 

Since she passed several years ago, I will never know for sure but I think she never did want me to survive as a transgender woman and return to my full-time male self. I know I came off as being selfish and I was. I couldn't wait for the next time I could cross dress as my authentic self who at the time was really learning how an intense a time it was going to be. It was an incredible time in my life of learning and I was extremely disappointed my wife could not or would not come along. On the other hand I understood when she told me she never signed up to live with another woman, which I could not disagree with. I was stuck between my transgender rock and the hard place many trans people find themselves in. Either discontinue my gender journey I was on to become a transgender woman or at the same time I give up on my twenty five year marriage.  To a woman I loved very much. 

Along the way, I learned I was so much more than the "pretty, pretty princess." I am sure if my wife had lived, sooner or later I would have had to follow my true gender path and we would have needed to separate. My fondest desire is we still could have remained friends and she would have liked the new feminine person I became. After I paid my dues.  As it was, when she passed so unexpectedly, she left me on my own. Which meant relying on the gender basics I had come to trust over the years. It was then, there was nothing holding me back to going forward towards a gender transition. Even as stubborn as my male self was, he finally gave up the effort to maintain his place in the world.

So once again I was stuck on me and this time, it was the true me. The me I always dreamed of becoming with the help of my wife Liz and other lesbian women friends I had made. When I gave of myself, they gave it back to me. So, in many ways, I was stuck on them. There was no more princess in my future. I had paid my dues and applied to play in the girls' sandbox. Even though there were plenty of times I had sand thrown at me or suffered claw marks, I survived and earned my right to be there. At my age (sixty-ish), I thought I was too old to start over again but found out I was not. 

Through the miracle of gender affirming hormones and life experiences, I was able to reboot my life and live a dream I never thought possible. I guess you could say I became stuck on life. The princess was gone and she was replaced by a secure public transgender woman. Buh-bye!