Knowing the Rules before You Break Them

 

Image from Milan de Clercq 
on UnSplash

I had a very good idea of what it would take me to survive in a male world before I decided to see if the grass on the other side of the gender border would be any better or greener.

Growing up in a very male dominated family with the only girl being my mom, provided me with a so-called brightly lit path to my future. I was fortunate in some ways to have a larger male body to keep the bullies away as I played sports such as football and baseball regularly.  Of course, I came to dislike my body completely when I went through male puberty and had a difficult time finding any new fashionable girls' clothes to wear. 

When I went through the hated male puberty, the rules of the road so to speak, became clearer and clearer to me. Coming from a white middle-class family with two working parents in the 1950's to mid 1960's gave me a work ethic I used to scrape together the meager funds I needed to buy my own makeup and a few fashion accessories. I knew I could not ask my parents for the money because they would want to know what I needed it for. Any hint of femininity on my part would immediately break all the rules and would result in trips to a psychiatrist. Even then, I knew going to a therapist who knew nothing about gender issues would be a disaster. 

I knew the rules and played the game of male gender the best I could. I found good hiding places for my femininizing fashion and makeup while at the same time, dreamed of the day I could buy a nice wig. In those days, I was able to get by with a mirror who never lied to me by telling me I was a pretty girl. The feelings of joy or gender euphoria would continue several days before the pressure built up on me to cross dress again and again. When I began to realize I was just scratching the surface of my gender issues, I became quite good at knowing one of the primary male rules taught to me as a kid. If you did not like something, internalize it until it went away.

The problem I had was, my desire to be a woman never went away and it was so much more than just being a phase. From the darkness of my closet, I had what turned out to be a distorted idea of what womanhood meant to females everywhere. I only saw what I considered the good part was. Such as no military service and being able to enjoy the wonderful world of woman's fashion. I left out the challengingly part of women's lives such as child raising and toxic men, to name a few. As I was able to cross the gender border, I did realize the grass was not always greener and had I truly been a birth daughter to my mom, extra pressure to conform to her standards would have increased. I am certain she would have pushed me to go to the same university she did, all the way to pledging the same sorority.  I would have again been breaking rules. Just of a different sort.

When I arrived at a time when I was drafted into the military, I was forced into being a follower of rules more than I ever had in the past. Conforming to new Army standards to survive at least kept most of my mind off of my gender issues. I needed to put my desires aside and just dream of the day I could be free to be a transgender woman in my future. It was difficult, but I did it.

By the time I was honorably discharged three years later from the Army, I was able to settle back into the life I had before without one big exception. Without military service looming over my head, I could concentrate on my future. When I did, it became increasingly evident to me, there was a possibility I could break all the gender rules and achieve transgender womanhood. It was still going to be a decades long journey from there, but I was encouraged for once.

Of course, once I began to explore the world as a novice transgender woman, I found a whole new set of rules to deal with. To make matters worse, I had no knowledge of many of the rules I was about to break before I did them. The workbook I was using was blank and I needed to write the rules as I needed them. 

Again, I was fortunate, and I survived when I broke the rules, but I learned quickly since I was free.  Then as I safely continued along my gender path, I found I could make it safely to my dream. Mainly because I knew the rules from both sides of the binary gender and I was a better person for it. 

A Failure

 

JJ Hart at a Witches Ball.

There were many times in my life when I felt as if I was a failure.

I can blame a portion of my feelings on my parents who I feel placed unrealistic expectations on me in my male life. Of course, my up-and-coming female life was hidden from them, so I felt they had no control over me. Only the mirror seemed to. When I was able to transform myself into what I thought was a passable girl, no one could take the fact away from me I was a success in something. In fact, in those days, it was easy not to be a failure because I was so alone with my cross-dressing urges.

Even so, I still had problems thinking somehow, I was a failure. The major problem was I could never seem to get enough of viewing myself as a girl in the mirror. I began to think even though I had a temporary fix on my life, there was a deeper problem. Looking back now, I sense the problem was much deeper than just wanting to wear makeup and feminine wardrobe, I was going through the earliest stages of discovering I was transgender. The only problem was the transgender term and knowledge of had not been invented yet. Leading me to believe once again I was a failure.

As the years crept by and the overall knowledge of gender issues increased, I began to realize I was less of a failure. However, at that point, I began to explore the world more and more as a novice transgender woman so again I was beginning to feel as a failure when life did not work out for me. I was struggling to maintain my demanding male life, my married life, and my new life as a transgender woman. In time, the strain became too much, and it wrecked my fragile mental health. Most of the time, I did not know which way I was going, especially in my gender life. I needed to be careful when I was at work in a macho atmosphere not to slip up and show my feminine side and vice versa when I was experimenting with my feminized self. I certainly did not want to show any of my well-worn masculine tendencies.

Another problem was I had the idea I knew everything I needed to know about being a woman. Afterall, I found myself in a place where I looked the part. When I found out I did not, the difficult portion of my gender journey began. Putting the femininized version of myself I had created into motion was very difficult. Specifically, when I needed to actually communicate for the first time with the world. I felt as if I was a failure all over again and needed to start all over on my extended path to transgender womanhood. It turned out I did not really have to but still needed to work hard to look the public in the eye and have confidence in myself and improve my overall communication with the world. Eventually, I needed to enroll in feminine vocal lessons to improve myself. 

By improving myself, I was able to re-enter the world as an improved transgender woman and survive. I needed to roll up my sleeves and got to work to be a non-failure in a very demanding world.

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.

Living the Reality of being Transgender

My wife Liz at "Harpoon Harry's"
Key West, Florida

Regardless of what the evil bigots think and say, the reality of being a transgender woman or transgender man, is starkly different to what they think.

Most transphobes say living a trans life is just a choice we can make at any time. Or there is some sort of magic gender switch we can throw to reverse the life we are living. If only it was the case, somehow, we all would be able to live simpler lives. We would not have to put our lives in such turmoil just to jump the gender border.

On the other hand, living the reality of being transgender can sometimes lead to a more interesting life. Especially around super fragile and toxic men who refuse to have anything to do with us. Think about it this way, transgender women have a basic understanding of men in ways cisgender women will never completely embrace. I was fortunate when I was able to form relationships with other women (lesbians) who taught me my reality was good enough to be proud of and I did not need a man to give me value. I was living the value of being trans in the best possible way. 

When I completed my second big transition from parttime cross dresser to transgender womanhood, it was a scary, surprising time for me. First of all, I did not know if I could do it at all and secondly, I did not know how to go about doing it. Finally, I decided I needed to hitch up my big girl panties and see if I could be accepted in a world where women dominated the action. That is when I ended up at the "TGI Fridays" restaurant and bar I talk about so much. I had been there as a man so many times when I saw all the women from the mall come in for a drink after their shifts and I was jealous. Badly I wanted to learn if I could somehow be a part of the feminine action.

Once I was successful, I knew there would be no going back to viewing myself as a harmless cross dresser. I was serious about being a better transgender woman and I needed to learn more on how to do it. It was about this time also when I began to consider what I thought was the next step in my femininizing progression and that was beginning gender affirming hormones or HRT. My problem was, standing directly in my way was my strongly disapproving second wife. So, I needed to put off my plans of jump starting a very serious process of battling my testosterone poisoned body. I reasoned, the better off I was when it came to my femininization, the easier time I would have in the public's eye. 

Even though I would have to wait until my second wife passed away from an unexpected massive heart attack, once my path was clear to HRT, I sought the opinion of a doctor and received my cherished meds. Once I did begin to go down the hormonal road, I thought I would be ready for the changes I went through during my second puberty. Hot flashes, along with rapid breast growth were just a few of the changes I went through quickly as my skin softened, hair grew, and I became much more emotional. 

Hormones really changed my reality of what it meant for me to be transgender and while I realize the meds aren't for everyone medically, they were for me.

If the world we live in would just slow down for a moment and understand the reality of being transgender is not so much different than the average human, we would be in a better place.

Building a Huge Bridge

 

Image from UnSplash.

When you cross the binary gender border from male to female, anyway you cut it, you need to be ready to build a huge bridge. 

In my case, I don't think I had any idea how far I would have to go until I seriously started my journey. When I was the "pretty, pretty princess" as my second wife called me, life seemed to be so simple. All I needed to do to live as a woman was to look like one. My wife also told me I made a terrible woman, and her view had nothing to with my appearance. I knew right then, I needed to find out what she meant and add it to the bridge I was starting to build. I discovered a lot. 

I was far from being any sort of a gender architect and had a long way to go. Mainly because I started with so little cross dresser privilege. I had few feminine traits to work with when I started and needed to learn the basics in fashion to disguise my testosterone poisoned male body to do my best to present as feminine in the world. When I did, I began to build a stable base for my gender bridge to stand on. To do so, I needed to cast my mirror aside and begin to explore more and more of the world as a novice transgender woman.

About that time, my bridgework became very complex. I began to be accepted in small, diverse circles of acquaintances which included everyone from lesbians to a big burly motorcycle rider who I had a small crush on. I learned to build a support structure from all of them and my bridge began to come together. Even still. with all of my newfound success in the world, I found I needed to keep building to be successful. Along the way, I needed to adjust to losing part of my intelligence to toxic men, all the way to be mansplained about the simplest of things by other men I considered to be beneath my level. I adjusted to all of it and considered it to be a rite of passage into a woman's world and went on. Plus, at the time, I was making the transition from basic cross dresser to novice transgender woman. I needed to strengthen my new bridge to make it.  

Bridge building never became much easier for me until I gained the expert guidance of other strong women. Their acceptance was invaluable in making my way in the world as a transgender woman. Basically, they showed me how to value myself as I was. At that point I found it much easier to walk from my old male side of my bridge all the way to the new, scary side of the bridge and live fulltime as a transgender woman.  

I learned when I tried to cross my bridge, and it held, I knew I had built it correctly. Much of the time, my life was not easy, but I again considered it all a rite of passage to gain what I always considered to be my ultimate dream of transgender womanhood. 

The bridge was huge and intimidating but I stayed the course and learned the basics of gender bridge building. The effort was worth it. 

Preparing for the World

 

JJ Hart. Witches Ball Image.

Before we get started, I would like to take the time to respond to a comment from an anonymous reader to the blog.

For the sake of simplicity, I will condense the comment. The reader was responding to my post concerning my second wife never accepting my feminine self. The reader raised the question about if my wife was somehow jealous of the way I looked. Even though my ego often considered it, I never allowed myself the latitude to consider it. After all, I never considered both of us were in any sort of a competition when it came to appearance, we were simply different in our outlooks. As a cisgender woman, she believed in very minimal makeup and conservative clothes. I did not, and considered the makeup, hair and wardrobe process a woman goes through as part of the fun and challenge of being femininized. As it turned out, there was no way I could cross dress down to her level. If I did, I might as well not attempt it at all. As all of your regular readers know, I will never have a final answer to the appearance question because she passed away years ago. Thanks for the comment and now on to the rest of the post.

I found, as I evolved in life, it became more and more evident to me that cross dressing was more than the proverbial "sun" of my life. What I mean is, even though my entire life revolved in many ways around being a serious part-time cross dresser, deep down I knew I had so much more to accomplish in my gender journey. 

To arrive at where I wanted to be as a novice transgender woman, there was so much more I needed to do. When I put my so called "pretty, pretty princess" into motion into the world. No longer did I just have to worry about my appearance, I had to concentrate on how I was moving and communicating with the world. To say the least, it was a struggle to put all aspects of being a novice transgender woman together. My sun became my entire universe as I went out into the world as I attempted to completely feminize myself. I needed to stop with the ignorant way I was trying to present myself and learned the hard way, to survive in a world I found was run by women, I needed to be better. 

My brutal entrance into the world as a transgender woman, helped me to learn all I needed to know. Or so I thought. Every time I thought I knew where I was headed, only to find I had another wall to climb. Finally, I came to the conclusion in life, there would always be walls to climb and my life as a transgender woman prepared me to better attempt the climb. 

Since I was/am very afraid of heights, I could not spend much time enjoying the view when I had successfully climbed a wall. I needed to get busy and search for the next one. Plus, having a soft landing was never guaranteed. No one ever told me how many bruises I would suffer on my path to gender freedom. 

Finally, any purported competition between my second wife and my inner feminine being was put behind me and I could move on the best I could. 

I Was Ready but Was the World?

 

Image from the Trolley Stop, Dayton, Ohio

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

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

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

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

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

  

Gender Lighthouse

 

Image from Juan Gomez
on UnSplash.

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

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

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

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

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

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

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

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

Trans Girl at the Roller Derby

 

Transgender Roller Derby Woman

Way back when, as I was building my transgender confidence, a group of lesbian friends invited me to tag along to their roller derby experience. 

Even though, I was slightly petrified to say yes, I enthusiastically went along with the idea. What could possibly go wrong with a small group of lesbians drinking one dollar beer watching women's roller derby in Cincinnati? Actually, nothing did go wrong, and I ended up having a great time. 

Also, I was amazed at the number of women in the crowd and on the rink who were more masculine than I still was.  All of them helped me to calm down and have a better time at the event. The only problem I almost encountered was when I used the women's room. It involved an evil stare from a woman coming out as I was going in. It also turned out to be one of those days when I was wearing more makeup than the majority of the women in the venue. Of course, I tried my best to apply the bare minimum of makeup so I could blend in, but it turned out to be impossible. There seemed to be no one wearing any makeup at all. I guess I identified as a "lipstick lesbian" for the afternoon. 

After I settled in, I found I could even enjoy the action on the rink, even though I did not understand all the scoring moves I saw. Plus, I had read the story of a transgender woman who had skated for a Long Island, New York, team who had fought and won her right to to participate. This was way before todays bigoted transgender backlash around the country. 

Sadly, I never went back to the Cincinnati Roller Girls matches again. My excuse is I was never invited back until my mobility issues made it difficult for me to do. Plus, my small group of lesbian friends drifted apart. In the meantime, I was able to check off another item I did not really know I had off my bucket list of things to try as a transgender woman. My friends were doing a wonderful job of pushing me out of my gender shell and if they wanted to do something as a group, I was included.

Everything I was able to check off enabled me to grow my all-important confidence in the world. From there I was able to begin going with my future wife Liz to "Meet Up" groups in the Cincinnati area. "Meet Up's" are groups of strangers who get together to discuss all sorts of topics from writing to knitting and beyond. Meeting strangers again did wonders for my confidence in the world as a transgender woman. I equate the whole process as building a new foundation in life away from anyone ever knowing my old male self. 

Finally. the wall became thick enough and high enough my old male self was completely shut out and he became the one stuck in a dark gender closet. My trip that afternoon just became one more success story on my journey to transgender womanhood.

Trans Girl at the Symphony

 

Cincinnati Music Hall

I really don't know why but this experience usually slips my mind. Even though, it is one of the most dramatic experiences I have ever had. 

All of this happened several years ago when I was still attempting to navigate the world as my authentic self for first time. Also, my future wife Liz felt the time was right for me to accompany her to the Cincinnati Symphony Orchestra Christmas concert. The whole idea petrified me, but I could not say no and I set about preparing for what I could wear to a semi formal event. My first.

Fortunately, thrift shopping came to my rescue as I found a very sparkling gown to wear in black. As I prepared by shaving, applying makeup and doing my hair, my nervousness subsided a little as we waited for the Uber, we called to take us downtown to the concert hall. 

When we arrived, my nerves returned as we were stuck in a crowd of people waiting to go to their seats. The only thing which saved me was, no one seemed to be paying me much attention. When I sensed no one cared about me, I began to calm down. As far as the musical performance went, I admit I had never been much a fan of classical music, but I did the best I could to enjoy it, and I did. Once I calmed down. Ironically, I was very calm until the lights came up and intermission began. People were moving around which put me in danger of being discovered as a transgender woman. I was not, and the concert resumed. 

Before I knew it, the experience was over, and I could breathe again until we stopped at a venue along the Ohio River for a drink or two to celebrate the holidays and our relationship together. Once again, my nervousness increased until we settled in at the new venue. Again, we were treated very well. I even used the women's room with no repercussions which was becoming a necessity.

What I learned from the entire experience, I found if I did not try harder to expand my horizons as a transgender woman, I never would. Plus, there was never a better time in my life to do it. Because I was spending my time with Liz, it made the whole time so much more pleasurable.

The concert was only the beginning of me building my confidence in my transgender womanhood. Liz wanted to travel, so I learned to travel and again learn new horizons of fitting in with strangers as a woman. I viewed it as a layered trip to learn more and more about my new world. Most importantly, I learned to interact one on one with other women and basically ignore the men who were ignoring me. 

It all was an important springboard into my future desired life which I had to do in a hurry, since I had such a late start at the age of sixty. I can't stress enough, when I did start, despite my fear or nervousness, I enjoyed it immensely. The entire process, proved once again, I had made the right decision when I chose to live as my authentic self. Plus, I needed to discover for once and for all, who was my true self before I could move on with all the major decisions I needed to make.

As I said before, I had never been a real fan of classical music, but it started me down the path to a beautiful future. 

Someone is Paying Attention

Image from Alena Garrett
on UnSplash. 

One thing I immediately noticed when I left my mirror and went into the world as a novice transgender woman was when I was suddenly noticed more by both primary genders, male and female.

Of course, being raised in an unwanted male world, I knew how many guys made a big deal about the appearances of the women around them. What I was not prepared for was the amount of attention I received from other women. Especially, younger ones as teen girls were especially observant. I cannot or prefer not to recount the times I was stared down by a group of teenaged girls or younger. 

My primary example was the day I was out shopping in the racks of a women's clothing store when around the corner came a small child who startled me. Obviously, I startled him also because he ran back to his mother (who was close by) and said, "Look at the BIG woman!" Initially, I was relieved because he had called me a woman. Then he continued and said, "The big MEAN woman." Naturally, I learned a big lesson. The BIG mean woman should always be prepared to be friendly, which means I needed to immediately learn to wipe that old male scowl off of my face. If that was all I needed to do to not scare little kids, it was an easy lesson to learn. 

For a while, I was intimidated by all the attention I was receiving until I began to understand where it was coming from. The more I dressed to blend in with other women, the less attention I received from men. Primarily, because I just wasn't that attractive. On the other hand, the increased attention from women came from the fact most of them were just curious what I was doing in their world or were appreciative of my efforts to look the best I could. If I had a dollar for every time I was complimented on my jewelry or earrings, I would be a rich person now. 

It took me time but eventually I learned my lessons well and adjusted to the fact, my appearance as a transgender woman was a fact of life and in many ways a form of female privilege I needed to live up to. My observations made me work even harder on my feminine presentation. In other words, it was all part of my rite of passage into transgender womanhood. Plus, in many ways, I needed to work even harder to present well than the average cis-gender woman who was just getting by because she happened to be born female. Which, by the way, did not automatically allow her to be a woman. Neither gender birthrights allow them the permission to claim an automatic right to claim a title of man or woman. Which comes from socialization. 

I learned if someone was paying attention, I should make the most of it and adjust to my new surroundings. Once my confidence built to a point I could do it, I was able to project a strong feminine aura. When I did, questioning my gender became someone else's problem. Not mine.

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.

Your Personal Best

 

Image from Markus Winkler
on UnSplash.

If you have ever worked in any sort of a competitive industry, perhaps you have heard a phrase similar to keep your eye on the ball.

Many times, in my long journey to being a full-fledged out and about transgender woman, I have wished I paused to remember such a goal. One image comes to mind when years ago I was trying to pump gas into my car at a gas station along the interstate when I was traveling back to Cincinnati to meet Liz before we were actually married. 

To begin with, I was a little flustered, even to the point of panicked when I discovered I did not have much money at all on my debit card and had no cash at all. As I said, I was nearly panicked and ended up pulling up to the wrong pump to try to fuel my car. For some reason, I had chosen a diesel pump and fortunately was having no success in putting the nozzle into my gasoline powered car. As I struggled, a man pulled up nearby and came to my aid by telling me I was at the wrong pump. I profusely thanked him and moved to the correct pump but not before I needed to go in the station and pay. Exactly what I did not want to do. I had no choice due to my mistake and needed to finally go inside and confess my mistake to a clerk inside who had no sympathy for the dumb person making the mistake. 

It was just one of many times, I took my eye off the ball and barely snuck by with a little help from above. Another time I remember was one night when it was snowing quite a bit, but I decided I needed to go out anyhow. With out giving anything much thought, I figured the night would be ideal to wear my new medium heel boots to give my fashion image a personal boost. All was going well until I went into one of favorite regular venues and found a seat at the bar. All along, I was confident I could slide down off the bar stool without falling. It turns out, I was overconfident as I tumbled very a womanly fall to the hard floor. I was lucky and all I hurt was my pride. From then on, the boots remained in my closet when it was snowy or even wet outside. 

Most of the time, when I was pushing the envelope and taking my eye off the ball, it was not because I was trying to do my personal best as a novice transgender woman. Even though I had established "safe" places I could go, I kept trying to go other places where I was not welcome such as the one lesbian bar I kept trying to go to. Unlike the other lesbian venue, I was accepted in (which accepted me), the first place tried to make my visit as uncomfortable as possible. Until I finally just stayed away and gave all my money to the place where I was liked. Once I did that, I could relax and enjoy myself.

I learned also, my personal best was not exploring the limits of where I should go as a transgender woman. It meant staying off dark urban streets by myself, or even unlit mall parking lots. I had not realized yet I had lost my male security privilege and needed to add a whole new level of security to my life.

Through it all, as I made my gender journey, I slowly learned how to keep my eye on the ball and do my personal best. Anything less, and I would revert back to my old unwanted male life and find myself back to where I started. Equally frustrating, was the fact I would have wasted all the time I put into pursuing my goals. I found my path and decided to stick with it.  

Meeting in Person

JJ Hart in a warmer time.

Do you remember the moment you met your authentic self in person?

Looking back, I can recall several profound moments when I saw the feminine person I was always meant to be. My earliest memories came when I was quite young in the days when I was first experimenting with my mom's makeup and clothing. Even though I probably looked like a clown, the mirror told me I was beautiful. No matter what I looked like, I refused to face the truth. 

It was not until much later in life, when I began to realize how much work it was going to take to really see my true self, did I get serious. If I was going to make it to my dream of transgender womanhood, I would have to profoundly change my way of thinking. The first change I made was how my male ego interacted with my appearance the public saw when I went out for the first times. 

The truth of the matter was, if I dressed "down" to blend in with public, I received very little attention, so I started to dress too trashy to please my old male self. What quickly happened was I attracted the wrong type of attention and did not pass well. Or, at all. Back to the cross-dressing drawing board I went time after time until I drove my male ego out to the point where I was successful in blending in with other women in the world. What were the women wearing and when were they wearing it became my motto. The time I spent was worth it when success as a novice transgender woman was becoming mine. 

Suddenly, my visits to the mirror became more and more friendly. I adjusted to the fact I would never be the prettiest woman in the room, but I could rely on other feminine attributes to get by. I began to closely study other women who may not be the most attractive, yet still be popular, fulfilled women. What I did was, I began to concentrate on what my new personality would be as a transgender woman. After all, I had an unique opportunity to start all over again as a human being. My new time was a scarce commodity, and I could not miss my opportunity to do it right. 

I was fortunate in that I already had a women friend who was ready to help me. She had been there all along, just waiting for her turn to lead my life. She was the feminine inner me. It turns out she was a nice person who saw the best in others. When I met her in person, I was excited and knew I was in good hands.

I was in good hands and began to expand my small circle of friends in the world. My wife Liz and I started to go to small and medium sized "Meet Up" groups in Cincinnati where I learned the benefit of a different group of strangers accepting me. None of us knew each other previously, so I was on an even level with them. The great equalizer. 

All of the process was extremely beneficial when it came to meeting myself in person until I became used to it. Perhaps the best part of the entire process was the time I realized I had really expanded myself as a woman, transgender or not.

Not Scared? In the Wrong Room

 

Image from Alexandra Gorn
on UnSplash.

I cannot begin to tell you how terrified I was to interact with the public when I first began to attempt to live in the public's eye.

One night in particular always stands out in my mind. It was the evening when I had pre-determined my cross-dressing days were behind me and I was going out as a transgender woman. Furthermore, I knew if I was successful, it would change my life forever. As I prepared for my big night out, I took extra care with my outfit, makeup and hair. I wanted to make sure I blended properly with all the other women I would be interacting with at an upscale bar I was going to which was heavily frequented by professional women who worked at a nearby mall.

Once I made the short trip to the venue and found a parking spot relatively close to the front door. As I sat in the parking lot, the pressure to go in increased dramatically. As I nervously checked and adjusted my makeup in the car's rearview mirror, again and again the fact was not lost on me I could be changing my life forever. By the time I gathered my courage to actually enter the venue, I could barely breathe and was gasping for air. 

It took me awhile to gather my courage and enter the front doors of the place and interact with the hostess stand. Deep down, I was hoping the hostess would be busy seating other patrons so I could sneak on through and find a seat at the bar. The short distance from the hostess stand to the bar seemed to be miles to me but I made it and luckily found a corner seat at the bar by myself. Plus, the bar itself was supported by two large thick pillars. I figured if I found a seat next to one, I could blend in and hide if I needed to. I did not need to hide as I was approached for my order by a friendly bartender. 

Immediately, my fears began to melt as I ordered my first drink and even started to relax a bit and watch all the other women who had begun to arrive at the bar to enjoy each other's company. As I observed the group, I saw no one was noticing me. So far, so good. No one noticed a very scared novice transgender woman in their group. 

Of course, this evening was only the beginning of my new transgender journey. I knew my life had changed forever. I could never go back to the old unwanted, boring male life I was living. To move forward, there would be many nights when I would be very scared. Somehow, I learned to feed off my fear to propel me forward. No longer was I a weekend cross dresser, I was reborn as a very serious transgender woman.

My end game was using fear to refine my push forward by putting extra time and effort into my fashion and makeup. That way, when I needed to walk past a crowd of strangers in a new venue I was in, I could do it without any issues. 

I finally decided, if I did not feel any fear at all, I was in the wrong room. Especially, in today's climate, it pays to always be aware of your surroundings. Maybe fear is a strong word, but awareness is not. 

Happy Valentines Day

 

Happy Valentines Day Liz!!!

Admittedly, I have never been much of a romantic, as a former man or a woman. Over the years, I have started to change as I entered transgender womanhood. 

After my wife passed away, I was intensely lonely and began to look around for company. At first, I started by going on-line under various platforms. For example, one week I would list under woman seeking woman, then the next week, I would list under woman seeking man. In total, predictably, I received very few responses. None, I considered quality except one and her name was Liz who contacted me under woman seeking woman. She was from nearby Cincinnati.

In the meantime, I did make a couple other lesbian friends out of sheer will power by forcing myself into going out and being social. The first friend was introduced to me by her daughter at one of the sports bars I was a regular in. The daughter noticed I was always alone and thought it would be fun to do a little matchmaking.  The great part is, we still are friends to this day. 

Then one night when I was out to be alone, another woman came in to pick up a to go order and ended up sliding a note down the bar to me. We ended up meeting and she became part of a small group of women I partied with almost nightly. Plus, as I always say, these two women taught me so very much on what it would be like to live life as a woman, more than they will ever know. 

By now, you may be thinking, were there any men in my life? Yes, there were a few including all the ones who would stand me up on dating sites. I did have a couple memorable dates with guys which never went beyond the kissing stage. Even though I enjoyed being on the other side of the dating spectrum, I still much preferred the company of women. Especially when I was accepted for me. I was satisfied on where I was in my dating preferences and saw no need to change. Plus, when I went to lesbian mixers, I found I could further my preferences as a transgender lesbian.

Perhaps my biggest discovery was how many lesbians were not of the "gold star" variety which meant in their past they had some dealings with men. With me, they found a curious gender middle ground which the majority of insecure men were afraid to pursue. During this learning portion of my life, I ended up enjoying myself immensely.

What I have left out of all of this on purpose was my interaction with Liz. Through it all, we had continued to talk back and forth. Once I was brave enough for her to hear myself on the phone. We finally arrived at the point where her and a group of women friends from work were going to a drag show near Cincinnati. The drag show ended up being our first date nearly fourteen years ago. Obviously, everything went well and ten years later, we were married. 

On this Valentines Day, I credit Liz with being the only woman who ever told me she never saw any male in me at all. In many ways, she helped me back on my feet after some rough years of my life. Happy V-Day, Liz!

The Gender Envelope

 

Image from Alexandru
Zdobau on Unsplash.

Sure, I spent or waisted far too many years before I fully transitioned into transgender womanhood.

I was too slow for such a long time actually pushing my personal gender envelope when I was busy telling myself I was no more than part-time cross dresser. I saw no harm in just doing my best to look like a woman until it just wasn't the answer I was looking for. The more I cross dressed and improved my feminine presentation, the more I pushed the envelope and looked for more. Very quickly, my yearly Halloween adventures just were not enough.

I began to wonder if I made a good impression at Halloween, could I make the same impression if and when I tried to go out in public as a novice transgender woman. Following many trials and error experiences, I found I could survive a public which largely did not care about me. The big error I always point out is when I was not receiving any attention to speak of as a woman, I began to dress trashy to attract the wrong sort of attention. I was mistakenly pushing my gender envelope the wrong way. When I finally began to understand the best ways to dress my male body and apply the proper makeup, did I begin to be successful and blend in with other women in the world. 

Once I had accomplished all of the fashion, hair and makeup necessities, I allowed myself to further push my gender envelope. When I did, I found myself needing to understand how women exist in the world. Or how do they communicate with other women and men. I had a quite a bit of catching up to do since I was attempting to catch a moving train heading down the tracks. I did not have the benefit of growing up female with a mother or peer group to guide me. I always point out; the passive aggressive system of interaction most women operate under was the most difficult for me to learn. Since childhood, I was always used to the full-frontal confrontational world men operate in so I was attempting to survive in a whole new world.

Once I did survive, I began to push even harder, ignoring warnings from my wife on what would happen if I was ever caught. I put the male gay bars behind me and moved on to big sports bars and lesbian bars where I could actually be myself. I thought I had reached my peak when a dear friend of mine invited me to a trip to a NFL Monday Night Football game in Cincinnati. Even though I was very scared at the thought of going, I could not turn down a chance to empty my envelope and lay my gender cards on the table. Since I am not really a gambler, I hoped the lifetime of preparation I put into this moment would serve me well. 

The moment did serve me well. As always, I survived and became a better woman for it. Plus, I learned the game was only the beginning. The life in my transgender womanhood I was going to experience, would be extremely fulfilling and everything I thought it could be when I started pushing my gender envelope.

Transgender Destiny?

 

Image from Marvin 
Kuhn on UnSplash.

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

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

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

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

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

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

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

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

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

Transgender Lines

 

My friend Racquel.

During my journey to transgender womanhood, I often went past gender goals without even realizing it. Or, I was too busy living my life, I could not slow down enough to enjoy where I was.

Along the way, I was careful to set goals for myself such as not being satisfied to present successfully in mall and clothing store situations where people were more into my money than gender. What I started to do was go to lunch or an early dinner when I was cross dressed to judge the reactions I was getting. Even though I was not totally successful in my feminine presentation, I was learning. I found employees at restaurants were more apt to accept me when I was pleasant, minded my own business and of course, tipped well. Plus, I was easy to remember and became a protected regular quite easily when I made wise decisions on where I decided to go.

In other words, stay out of the redneck venues so prevalent where I lived in southern Ohio. I learned the hard way in one place I went when I had the police called on me as I tried to use the bathroom. After it happened, I gathered myself and went a short distance up the street to another venue I knew I would be accepted in. I certainly should have seen that line coming up before I tried to step over it. The stubbornness which I carried over into my transgender struggles, served me well as I kept trying to succeed.

At the same time, I had a new set of confidences set in. I encountered a diverse set of acquaintances which I write about often. The give and take I went through as a brand-new trans woman helped me to stabilize who I was searching to be. Before I knew it, there were many new lines I was crossing. Since the groups I was socializing with were very diverse, I needed to confront lingering questions about my sexuality. One group had a man I was getting along with wonderfully and on the other side, I had several lesbians I was getting along with too. Mixed in also, was Racquel, a transwoman who often joined our group, and who to say, any of them really liked me.

It was about this time all the lines I was attempting to cross started to blur. Was I into the man, I liked, the lesbians I liked or even the transgender woman I knew? I knew I had quite a bit to consider so I kept going out and researching to hopefully come to a better understanding of who I was in my new life. 

Finally, I was able to sort it out, or it sorted itself out for me. The man I knew, and Racquel moved away and I was able to maintain my relationship with several lesbians. In essence, my decision was made for me. Choices have consequences and with a little help I made mine. 

All the lines I did not see did not trip me up. I was more flexible than I ever imagined possible, and I made my way into my transgender womanhood. 

Opening Transgender Doors

 

Image from Sara Darcaj on Unplash.

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

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

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

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

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

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