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!

Do We Have a New Neighbor?

 

Image of Porsche Boxster. 

Similar to so many of you, I struggled for years trying to figure out how to get out of my house without the neighbors noticing.

I was unfortunate in that I lived in a medium sized city on a very busy street. On the other hand, I was lucky my house was ancient and had many doors which I could escape out of if I was just trying to escape for a quick walk. Once I was able to cross the busy three lane street in front of the house, a quiet neighborhood awaited me with limited chances for even seeing anyone. 

From my walking adventures, I very soon wanted to get to my car and drive. At the same time, I needed to be ultra careful I didn't get caught by my second wife or any of her friends. The problem was, one of the only deals I made with my wife who knew I was a cross dresser was I could never leave the house and here I was doing just that. Plus, I had the additional problem of being seen at Halloween parties cross dressed by several friends who could connect the dots if they saw me again. Needless to say, the whole process was risky. 

For the longest time, I was able to park my car on a side street and hurry into it's temporary safety without being noticed. At least I hoped so. From there, I could leave the town in head out on the interstate where I could tease truck drivers in my mini-skirts which somehow validated me as a woman. Finally, I grew bored of truck drivers and concentrated on improving myself as a new novice transgender woman. I had issues such as moving and communicating in a new world, I needed to work on if I was ever going to be successful in achieving my gender dreams.

Still I was reckless in my quest to not be discovered by my neighbors. My prime example is the new car I was able to buy with my restaurant monthly bonus money which happened to be very successful. I had always wanted a new Porsche following my days in the Army when I was stationed near the company's headquarters in Stuttgart, Germany. I was able to afford a low end (for a Porsche) Boxster which I dearly loved. By buying the car, any ideas of driving a car the world would not recognize went out the window. Very early when I finally took ownership of the car, my thoughts turned to being the blond behind the wheel of a fancy sports car. 

I couldn't take it any longer and ended up compromising on the how's and why's I was going to drive my dream car as my dream woman. I started by cross dressing as far as I could except for my wig, Putting the top down and heading out of town. I needed to not wear the wig also because I was afraid of it blowing away in the air when I was driving. Very soon I found out how popular the car was when the first night I drove it to the lesbian bar I always went to. As soon as I arrived and ordered my first drink, another woman walked in and loudly said, who does the car belong to? I want a ride, so out the door I went wig and all to show off my dream. The woman was thrilled, as was I and my wig stayed put.

By this time, I didn't really care what anyone thought about me and I enjoyed being the blond in the Boxster for as long as I could before my restaurant went under during a huge economic downturn it could not survive. Sure I had the negative responses I had anticipated but it was increasingly not important as I was living my truth. As far as the neighbors went, they moved away and the new tenants basically either did not know me at all or did not seem to care what I was doing. Which was exactly the way I wanted. 

Trans Girls Dreams

Trans Ohio Archive Image from
the Jessie Hart Archives.

There were plenty of times when I thought living a transgender life was going to be impossible. 

All the days of staring into the mirror cross dressed in women's clothing come back to haunt me. As well as my poor attempts at the makeup arts when I turned out looking like a clown. Who knew being a woman was going to be as difficult as I was making it. But it was and took me years of work to come close to getting it right. 

Dreams of course can come during the night or day. As I was day dreaming my life away about being a girl/woman, I also tragically had the problem of dreaming of being a beautiful girl during my dreams. All my dreams, day or night, did was frustrate me even further. Most of the time, all my dreaming did was trigger my severe gender dysphoria. My cross dresser mirror visits were not doing any good and I couldn't see a way out of my gender issues. All the time shattering any hope I ever had of living life as a transgender woman. 

It turned out I was being a drama queen in many ways and was giving up a dream I really wanted way too early. What happened, all of a sudden I began to learn makeup and fashion skills so at the least I could survive in a world of women. It was a slow process to be sure but if I was ever going to achieve my trans girl dream, I just had to do it. Plus when I survived, I felt so natural and was elated at my progress. Perhaps my ultimate goal could be within reach after all. From then on, I still had a huge amount of work to do. As I delved deeper into the women's world I so admired, I then had to decide if I wanted to go all the way or not. Was the grass really greener on the feminine side? Again and again, I found it was as I tackled issues such as vocal training and just overall life surviving in the world as a trans woman. As I progressed, the light at the end of the tunnel turned out to be sunshine and not the train. 

Since I started my journey with no obvious feminine characteristics, I had a long way to go. I started my path by trying out Halloween parties initially dressed as a trashy woman, all the way to presenting as a professional woman at others. So I could see if I could indeed present as a realistic woman. Finding out I could led me to believe my trans girl dream could indeed be realized. At that point, my life became a blur as I attempted to live as both a man and a woman. All my attempts did was create a tremendous amount of pressure on me and essentially wrecked my mental health. With the help of a good therapist as well as several good friends, I was able to survive and once again re-direct myself towards my dream. Once I felt I was back on the right track, I started gender affirming hormones following an approval from my doctor and there was no looking back for me. 

I never considered I could make it as far as I have when I was the kid staring longingly into our full length hallway mirror at home so many years ago. Even though there were many rough patches along the way as I battled my gender dysphoria, along with waiting until I was in my early sixties to out myself to the world as a transgender woman, I still somehow made it. 

I guess the old saying is true, if you don't dream it, it will never happen. My dream of living a feminine life was the only goal I could think of when I was young and someone asked me what I wanted to be when I grew up. Of course. I could not say a woman and ruin any life as I knew it, so I lied and said a lawyer or something more popular with my parents. I am sure many of you can relate to my story. 

Finally, after more failures than trials my trans girl dreams came through and somewhere within me there is an inner child who is rejoicing. 

Then I Went and Did It!

 

Trans Girl image from
Alexander Grey on 
UnSplash.

I played around for nearly a half a century being a very serious cross dresser. Sounds like a long time, doesn't it!

It was while I was doing it but now it seems like it was a blur. Most of it started with all the problems of sneaking around my home when I was growing up. I needed to use a ton of creativity to hide my cross dressing itself and not to mention the clothes I had accumulated. Somehow, I managed to do it all. Who knows, maybe it all made me a better person? I doubt it but at the least, the process helped me to be more creative with my life.

As I progressed slowly with my makeup art and improving my women's fashion choices by going to thrift stores, I found out I could do more. Then I went and did it by going out and testing the public's reaction to me as a novice transgender woman or at the least a skilled cross dresser. I found, the more I did it, the more successful I was and I felt so natural. To me, feeling natural was the best way I knew I was on the correct gender path and I wanted to keep going. Plus, feeling natural, gave me the confidence I needed to always push my gender envelope and try to do more and more. I even changed the way I viewed my Halloween costumes I was choosing. I started to go away from my trashy woman's look and then tried for a more realistic approach. I searched my brain for ideas which allowed me to try to present as a cis-woman at a Halloween party. Again, I went and did it when I succeeded at two parties where I was actually mistaken for a woman. Which in fact I was just learning I was.

By this time, it was too late to turn back and ignore my gender dreams. I was having so much success building a new life as a transgender woman, I just couldn't turn back. Even my sexuality was not a problem when I began to attract more attention from cis-women than I ever had as a man. I was validating myself as my own type of woman through my years of femininization and it felt so right. Then, I went and did it and jumped into the girl's sandbox and after a few bruises was successful. The claw marks I received on my back I felt were all learning experiences and I stayed and eventually held my own. 

All of this led me to my next transgender step of researching the possibility of beginning gender affirming hormones. Then I went and finally did by making my first appointment with a doctor who I heard would prescribe the hormones if a person was healthy. Thank the Goddess I was and the fun started. Like so many others, I needed to begin my hormonal journey on minimal dose of medication until my doctor and I could see how my body reacted. As it turned out, my body took to the new feminization hormones the way I hoped it would. It was like a big I told you so as my body changed. Inside and out. I needed all the help I could get in the appearance department and I was overjoyed when my facial angles softened and my hair quickly grew to a point where wigs became a part of my past. Luckily, my family history had no male pattern baldness for me to deal with. 

Since my overall appearance was becoming highly androgynous, I was loving it, I decided to give up on what was left of my old male life. I was to the point where none of my male shirts fit my breasts anymore, so rather than buy new bigger ones, I decided to go and do it. Give away what was left of my male clothes and live fulltime as a woman, transgender or not I was ready for the world. 

Since I had taken my time to make certain my gender decision was the correct one, I had no problems of never looking back. Many times now, I wish I had the courage to do it sooner and not have to worry about so many then I went and did its. 

Gender Puzzles

Image from Norbu Gyachaung 
on UnSplash

At what age can we act as if we understand our gender issues or dysphoria? Or will it forever be a big gender puzzle.

I suppose I can say, I never really understood exactly why something clicked with me the first time I tried on my Mom's clothes. The whole process caused me to finally understand I put so much into a process of dreaming of a feminine life which turned out to be so big, yet so small. The big view of course was having the success to go forth and conquer a sometimes negative world who was not used to gender explorers. The small view was thinking of all the pieces of the puzzle which allowed me to break out and break free in the world as a transgender woman. Just trying to remember all the facets of living as I do right now sometimes is very intimidating to me. 

Often, I just have to go back to pieces of the gender puzzle I was able to piece together so I could get a glimpse of how the final picture may look like.  I should have saved my energy since I am still putting together the puzzle. Since I don't have the patience for puzzles anyhow, it never mattered to me.  Through it all, the key word was outrageous since I never knew exactly what I was ever doing as I blindly followed my gender dreams. First I had to learn to not be outrageous in my dress and fashion and dress to blend with other women in the public's eye. Not what I thought I looked good as. I could also not be overstated or outrageous in how I acted. Again not to invite unwanted attention to myself. As a male I never liked crowds, so I had to learn all over how to conquer all my fears when I was out in the world with all my male/white privileges stripped away from me. So, outrageous to me at that time in my life was knowing I could indeed make it in the public's eye as a transgender woman.

Then I was back to the damn puzzle. It seemed when I was successful at piecing together one piece of the gender puzzle, I just could not figure out the next piece. Just when I thought I had made it, I was rudely awakened by a gender bigot telling me how much farther I had to go. My biggest example was the night when my wife Liz and I were at an lesbian Valentines Party. At one point, Liz left me alone for a couple of minutes to go get something to eat and in that brief time a lesbian TERF attacked me. She rudely asked me what my "real name" was and was extremely hard to dissuade from attacking me any further until Liz came back to save me. It taught me how far I still had to go in life since I essentially "raised" around accepting lesbians and was naïve when I was confronted.  I found in my new life I was young again and never too experienced to learn.

I was fortunate to finally having the basic resources to piece my life's puzzle together. I learned I could step into the feminine universe briefly then make my way into the larger universe of women eventually. All the nights with friends at the diverse mixer/parties I went to in Columbus, Ohio helped me to see and interact with all levels of the transgender and LGBTQ communities. By doing so, I learned where I belonged with my ongoing puzzle issues. I just knew I was excited often with how my journey was progressing. The problem I was soon experiencing was one which many other of you trans women have. What to do concerning  an unaccepting spouse. Sadly, too many marriages reach the end of the line when the gender rock meets the hard place with a trans spouse when the pressure becomes unbearable.

For the first time in my life, I had to have the patience and resilience to put my gender puzzle together. Now I am down to the final pieces as I reach the final stages of my life. All I can hope for is to pass on to the other side as painless as possible and I hope you are as successful with your gender puzzle as I managed to be. 

Teamwork makes the Dreamwork as a Trans Woman

Girls Night Out, I am on the bottom far left.

Similar to so many other cross dressers or novice transgender women I have heard from, they dream of enlisting a cis-woman to aid in their appearance.

I was included in having a similar fantasy. All the way to the point of begging my fiancé to completely dress me as a woman if I rented an out of the way motel room for privacy. Sadly, for me, she agreed and she did do her best to dress me as the woman of my dreams.  I say sadly for two reasons. The first being I did not see that much of an improvement over what I was able to do for myself since by that time I had practiced in the mirror myself for years. The second reason I say sadly came years later when I was facing being drafted into the military and being sent off to Vietnam. At the time she pressed me to tell the draft board I was gay to be deferred from going. Even though I didn't and don't have anything against the gay community, I knew I wasn't gay and wasn't going to lie to escape military service. The end result was she ended up breaking the engagement when I went off to the Army which I learned later was the best thing which could have happened in my life to that point.

As you can tell, I didn't have anyone to enable my teamwork work from any sort of a dream work. One of the problems I was having was working my way through exactly what my gender dream. I was still years away from facing my reality of being a transgender woman. So I suffered alone with my gender dysphoria before I was able to break out of my gender closet. It wasn't until much later when I discovered the beneficial beauty of having cis-woman friends who accepted the new transgender me for who I was. When I let it happen, my dreamwork began to flourish. 

Quickly I began to learn the world from the aspect of being an invited participant in girls' nights out. I was invited along to several different groups of women. All the way from married women to younger girls still in the dating pool. Neither mattered to me because I was learning so much about living a women's life with no men around. Even though when I went out with the younger group, I found how it was to be the decidedly older and less attractive woman in the group. Again, it didn't matter as I flattered and happy to be invited to begin with. 

This was an exciting time of my life when all of a sudden my dream of living a life of a fulltime transgender woman seemed to be so reachable. Being included and  embraced by the women I met was the difference. We went to birthday dinners together, went to parties with each other and of course used the rest room together, All of which turned into the ultimate bonding experience as a new trans woman.

Was I scared? Sure I was but the embraces I received within the group quickly put me at ease so I could enjoy myself and gain confidence in the new feminine person I was creating. It turned out I did not have much creating to do because once my feminine soul hit the world, she flourished. 

Even still, being in a women's world and experiencing their teamwork, did make the dream work happen for me. I was a better person for it once I left my gender dysphoria behind. My mental health improved as well as everything else in my life once I left my male self behind.

Leaving me For Years

Image from Brock Wegner
on UnSplash

I become a little amused when someone thinks I overnight completed my gender transition from a fairly successful male to a struggling novice transgender woman. 

To put everything in perspective, it took me nearly half a century to figure out my gender issues and how I needed to deal with them. Perhaps you noticed I used the word needed and not wanted because deep down I knew I never had a choice in my life. My gender journey was pre-written for me and I just had to follow the script.

For me it meant dealing with years of extreme gender dysphoria which wrecked my life and several relationships along the way. It was an extreme struggle for dominance from the two binary genders which lived within me. Naturally, even though he wasn't happy or satisfied, my pre-destined male life just didn't want to give up all the male privileges' he had worked so hard to gain. While, on the other hand, my feminine side had to put up with the fact she felt so free and natural when she was let out of my gender closet. 

The struggle left me in a situation for years where I couldn't win. I was in some sort of a gender trench warfare when one side had a little success, the other side would come back to reclaim victory. Battles were won, purges were made but the war went on and on. First I tried to hide in the mirror but that didn't work when I began to escape into the world as a cross dresser. All of a sudden, I discovered I might be actually able to live a dream life as a transgender woman if I worked hard enough to do it. At that point, I sat out to take better care of myself and lost nearly fifty pounds so I could fit into the woman's fashions I so admired. Plus I started to take better care of my skin so my makeup was easier to apply and I looked more natural doing it. 

At that point, I tried to outrun my gender dysphoria the best I could by changing jobs and locations where I lived way too quickly. In a space of three or four years my second wife moved from our home in Ohio to the metro NYC area, back to a very rural area where we heated with wood and finally back home again. All I finally learned was I couldn't out run my problems. They all began and ended with my gender issues. 

Even with all the problems I mentioned, I still did not want to give up totally on my male self. In many ways, the life he had carved out from such a bleak beginning was just too comfortable. What happened then were the years I spent as a novice transgender woman. All of them were scary yet exciting times to live through. 

So no, my decision to leave the male world behind was not an overnight decision. It just turned out he was leaving me for years. 

A Transgender Inch Equals a Mile

Image from Jessie Hart Archives
Civil War Cemetery Cincinnati

Distances are often very blurry when it comes to beginning and pursuing a gender transition. 

The meaning wasn't lost on me when I began to remember what many of my more experienced dating male friends said when it came to discussing their girlfriends. The biggest complaint was when the guys gave in an inch with their women, the women took a mile. 

As I transitioned into the feminine world, often I thought the same thing about my inner girl self. Or, as soon as I cross dressed in front of the mirror, the more she wanted. Specifically, she wanted out of the mirror and into the world. Quite early, it meant making the trip to the mailbox to check to see if there was anything in the box. I so enjoyed the feel of the outside air on my freshly shaved, panty hose covered legs. 

What I discovered was as soon as I made the very short trip out of the door, my girl dreamed of doing more and more in the world. So much so, my entire life was effected to the point I would become very grumpy almost to the point of disorientation when I couldn't cross dress again. The whole process just didn't seem fair because I was doing the best I could with the very limited resources I was able to put together. Fashion was difficult to find for my rapidly growing body but I could manage to buy my own makeup with my very small allowance I earned plus the money I put together from having my own newspaper delivery route.

Through it all, I managed to get by when my inner trans self wanted to take an extra mile when I was giving her an inch. I thought it was some sort of a gender poetic justice when my male friends complained about their girlfriends and I knew exactly what they were talking about when I wasn't outwardly involved with a girl at all. 

It wasn't until much later in life when I could begin to give up more than just an occasional inch to my transgender self and discover all I was missing. More and more I was able to take the extra mile. Even though I was scared (or even terrified) to do it. Such as the first night I went to a "Fridays" bar/restaurant for a cocktail. I ended up sitting in the parking lot for a good thirty minutes checking my makeup before I gathered the courage to go in. Once I did, and began to breathe again, I was able to relax and enjoy myself.

At that point, I was very proud of myself and considered I wouldn't challenge my novice transgender woman for more. After all, I had just given her the mile she wanted and I thought she should be satisfied for awhile. Needless to say, none of that worked. Instead of going to the so-called gay venues she had been going to, she wanted more of the "Fridays" vibe she succeeded in. I found she could become a regular fairly easily by being friendly, minding her own business and above all, tipping well. All of a sudden, a new life was beginning. No matter how scared of it I was at the time. 

Perhaps the biggest transgender inch becoming a mile was when I started gender affirming hormonal treatment. In what seemed a very short period of time, my body femininized as well as my inner self. I was feeling more emotional than ever before in my life as the new hormones took effect. The whole process was close to running a record setting mile. 

All along, my old male self was fighting giving up every inch he could. Not wanting to lose his life and all he had worked for. It turned out, once I went all the way into an new exciting transgender world, he lost the battle and the victory belonged to my stronger half. My feminine self as she took the final mile.

Joining an Inclusive New Club

Girls Night Out Image, I am on the
first row far left.
From the Jessie Hart Archives

 In many ways, this is just an extension of yesterday's post concerning transgender love affairs. 

In the post I mentioned indirectly when I was finally able to play in the girl's sandbox without having to deal with un-due harassment or even scorn. In my post yesterday (and often) I mention how difficult I had it dealing with my second wife dealing at all with me as a novice transgender woman. She was having nothing to do with the process, even though she knew from the beginning of our marriage I was a cross dresser. In no uncertain terms did my wife show my emerging feminine self any encouragement what so ever. She wasn't going to help me join an inclusive new club.

I accepted her ideas on my gender because we both agreed being married to another woman wasn't anything my wife ever signed up for. At that point was when I decided to go it on my own and find out if indeed I could carve out a life in a new gender world. Slowly and very unsurely, I found out I could make it as a member of a new club. Game changers as well as the occasional bouts of gender euphoria helped me along. Examples included the successful Halloween parties I went to. Compliments were easy to come by when people told me how good I looked as a woman. For the longest time, I didn't realize the true extended compliment was how good I looked as a woman, who was really a man. None of it mattered as I made my way along a path to becoming a fulltime transgender woman.

Overall, I am proud of all the work I put into joining a new very exclusive club. To begin with I faced the necessity of learning all the basics of makeup and fashion. Starting from point zero, compared to other girls, catching up was difficult. Especially when I really didn't have much of a feminine body to begin with as well as having a very non-approving male dominated family. More than anything else gender confusion reigned supreme in my life.

What I don't mention enough is the feedback I received later in life from other women when I transitioned. I get the idea from other trans readers I hear from, sometimes acceptance is not so hard to come by but is such a powerful tool when it comes to a transgender transition. We all know, women live a different more layered existence than men and a life which takes no small amount of work to learn. If you do learn the intricacies of what if being offered to you when you are invited to women's only spaces, you will know you have made it into an inclusive new club. Once you are there, chances are, you will never have to go back to an old unwanted male life.   

I will forever remember the  women who helped me along in my journey and opened their worlds to me. Being able to exist on my own in the girls' sandbox or club was something I never thought I could do on my own.

They will never know all they did for me. Even to the point of saving my life. It was the major spark I needed to discover my true sexuality and live as I always dreamed of.

Dreams versus Priorities

Image from Marcos Paulo Prado 
on UnSplash

 Seemingly forever, I had the dream of leading a feminine life. 

As I progressed along my bumpy gender journey, slowly but surely I learned perhaps I could achieve my number one dream.  Other guys I knew dreamed of having a great job or a beautiful wife while, all along, all I wanted was to change my gender. It all seemed simple enough except it wasn't. In fact, it proved to be extremely difficult. 

As I lived a reasonably successful male life, it became more and more difficult to just give it up and just walk away. To do it, my dream needed to become a priority. Around this time, was when I entered what I refer to as my second major transition. It was when I went from being a very serious cross dresser to being a transgender woman or going from just wanting to look like a woman, I wanted to be a woman. The entire process seems like semantics it probably is but I was serious and I was led into gender areas I never dreamed of. Primarily when I needed to step up my game from just concentrating on my appearance to needing to learn a whole new form of communication in the world.

I was in shock when I learned how quickly my white male privileges could be swept away leaving me with very little to fall back on. My previous "hit and run" approach to facing the public needed to change if I was going to survive and keep my dream alive. 

For the longest time, I was by myself in the world as a man and a woman. My male self had lost almost all of his friends and family to death leaving him mostly all alone. Plus my trans woman self had not had the chance to establish herself as a person in the world. I was stuck in a gender limbo, until my life started to change for the better as I began to set priorities for myself. Since I really had nothing to lose, I went all out on on-line dating sites which predictably I had very little success with. Partially I think because in those days there were no sites which catered to transgender women who were not fetish items. It was complicated but I went on regular sites under different listings such as everything from woman seeking woman to woman seeking man. After sorting through tons of being being rejected, my wife Liz responded to an ad I ran asking for a woman seeking woman and we have been together ever since.

Destiny at that point intervened more completely in my dreams when my regular trips to straight venues ended up with me meeting two different lesbian women on separate occasions and quickly we became a tight knit small group. My dreams quickly became my priorities at this time of my life because I needed to step my gender game up to learn and understand what the other cis-women in my life were showing me. If they knew it or not. 

When I started gender affirming hormones (HRT) around this time, there was no turning back. I faced an all out priority to live a life I had only dreamed of. For the first time, it was so close I could reach out and touch it. Even though my life turned out to be different than I ever imagined it would be, I still couldn't conceive of living it any other way. My dreams had turned into the priority of allowing my inner feminine soul a chance to live. 

Thanksgiving and Beyond

Image from Kevin Dowling
on UnSplash

 As much as Thanksgiving was always a given as a time to meet up with family and eat a delicious feast.  Early on, the day was more enjoyable because one of my right wing nephews at that time did not want to start a political argument with me. 

Through it all, in the back of my mind, I knew something was wrong. In my own way, I was engaging in impostor syndrome. I wasn't the man I was portraying to be. Each year I used alcohol to dim the pain and move on the best I could. Even though I had very little control over Thanksgiving itself, there was a day I still thought eventually I may have some control over. The day in question was the Black Friday shopping event my second wife always insisted on going to. This all happened in the latter part of 2005.

Finally, I waited long enough or persisted long enough I was able to try out a Black Friday shopping experience on my own at a well known mall close to where I lived. My opportunity to cross another feminine experience off of my novice transgender woman check list came when I learned my wife (who worked in retail) had to work on Black Friday morning. Suddenly, since I didn't go in to my job until late in the afternoon, I had my chance to experience the shopping madness which was Black Friday as a woman.

When the day finally arrived and my wife left for work, my time to get dressed in my best sweater, skirt and comfortable shoes, added my blond wig, sensible make up and was ready to go. I was excited about finally having the chance to again live my dream. 

Once I arrived at the mall, predictably parking spots were at a premium but I finally found one. From there I had to gather my courage and enter the mall. Once I was in the shopping area, all my nerves faded away and I was able to concentrate on the relatively short time I had to fulfill a long term dream of mine. I wanted to experience the estrogen laden atmosphere of Black Friday.

All too soon, as I browsed a few of the stores for a gift or two, I found in particular no one paid me any attention at all. It was so crowded with mainly women, I was able to blend in with no problem. It was time for me to return to my boring unwanted male life and move on back to my impostor syndrome. I was learning I was never a guy cross dressing as a woman. I was a woman cross dressing as a guy.  

After I went into my work and became immersed in my job, at the least I was still mentally able to bask in the glow of being able to live out one of my big feminine dreams... to experience a Black Friday shopping experience as a transgender woman. As it turned out, my start to the holiday season was destined to grow and grow into one of the major holidays for me. Replacing even Halloween. Throughout the month of December, I will be writing more in depth about my times as I grew into a fulltime trans woman.