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 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.

Comments

 

Image from Bruno Acquire on UnSplash. 

In regard to yesterday's post concerning the Veterans Administration's announcement they were not going to cover gender affirming hormones, prothesis's, and even mental health treatment for new veterans suffering from gender dysphoria anymore. 

In my rant, I said, among other things, how much I disagreed with the move, even though it did not affect me. The VA said, those already receiving gender related care could keep getting it. Which, of course, means me. 

One huge problem I did not mention in my post was pointed out by Denise, who pointed out, the VA's decision to shut out trans women being discharged into the world to fend for themselves was just a smaller part of what the orange felon's presidential administration is trying to do to erase the rights of all women in our country today. Since transgender women are a unique form of women, our rights as women are being taken away too. Which gives me yet another chance to wonder why any clear-thinking woman, trans or not, would have ever voted for the felon at all. And I will leave it at that.

On another subject concerning a post called "Why Me?' a reader wrote in with this comment:

"Over many decades I often asked myself both “why me” and “why not me”. For decades I limited myself to underdressing…. something I told myself was just a (hopefully) harmless kink, out of the fear that if I explored further, I would irreversibly descend that slippery slope. I in my early 50s I finally allowed myself to experiment with makeup and women's clothing beyond underwear. I still vividly recall the moment when I looked in the mirror and saw myself for the first time. In that instant, I may have even said aloud, “I can do this!”

There have been subsequent periods of self-doubt, of course. Still, every day I find that I look forward to seeing myself and engaging with the world as a woman."

Thanks to both of you for the comments! I found many of your ideas to be very profound and meaningful. Plus, I had "aha" moments when I realized I had left all women out of the current political agenda and the moment when I too had realized when I was successful in public as a novice transgender woman that "I could do this", and it felt so natural. Deep down inside, something snapped, and I felt as if I was home.

The night I realized I could do it and felt at home in the company of women was and is so special to me. Just one of the reasons it disturbs me so much to see what is happening today with our rights continue. 

Speaking of continue, I love all your comments and wish I could answer them all, here on the blog in a public setting. Needless to say, I do the best I can!

Also (something I don't say enough) thanks to all of you who find the time and effort to read along on a regular basis. It makes it all worthwhile to me!

Why Not Me?

 

JJ Hart at Club Diversity
Columbus, Ohio

When I was very young, I had the tendency to hide behind my skirts when I needed to deny any masculine pursuits at all. 

Any time I failed, I ran home to see if I could lock myself in the bathroom and apply makeup and try on any of mom's clothes which still fit. I had a dream of finally making it to my own transgender womanhood when I grew older, but I had no idea of how. Back then, little did I know, the journey would take me over fifty years to complete and the path would be so curvy and full of hurdles. If I did, I wonder if I would have ever attempted to try it.

Of course, I started out innocently enough as a cross dresser in a mirror. My reaction was a double-edged sword. One side of the sword told me I was not doing anything really wrong, while the other side wondered if I was the only one in the world doing it. If that was the case, being a transvestite just could not be good. Right? All I had to rely on was my instincts which told me I was on the right path. So, I persisted and stayed on it. Since the only real feedback I had was from the mirror, I needed to rely on it when it was telling me I had advanced on from the clownish drag makeup stage I was into a more acceptable feminine form. At the time, I equated it with painting model cars which I was never good at and I was so proud when I thought I had conquered the basics of makeup. Even to the point of purchasing my own from the newspaper route I had when I was a kid. When my friends were buying model cars, I was buying makeup and loving it. It was not until many years later, would I receive the instruction I needed to really understand the art of makeup, but I was getting by at the time.

Clothes and hair were a whole other problem I needed to try to conquer at the time. With the very limited budget I was on, there was no way I could afford a nice wig all the way to my college years, when I was working a better paying job. In order to buy a wig, I needed the help of my fiancé who bought it under the idea she would possibly wear it. The wig was long and blond and was my cross-dresser's dream and luckily, she hated it, so I inherited it. Even with the abuse I put it through, the wig lasted for years before I needed to finally retire it. Clothes were another problem because again I did not have much money, and these were the days before larger sized women's fashions became available in a younger style. It was not until years later, when thrift stores became abundant, did I finally become fashion independent. 

As my feminine life was coming together, slowly I began to realize transgender womanhood may not be such a reach for me after all. I was beginning to explore all facets of the world as a trans woman and it all felt so natural. The more I attempted and succeeded at in my new life, the less I wanted to go back to my old, boring male world. So, I did not.

I was on a slippery gender slope my path had led me to, and all of a sudden, I did not fear it anymore. Somehow, I knew there was a soft landing out there for me. The stop signs were gone, and I knew at the age of sixty, if I did not try to live my transgender dreams, I would never have the chance and would forever regret my decision. From there, I decided to follow my heart and seek medical help to begin gender affirming hormones or HRT. The hormones forever sealed my trans life, and I never looked back. I always felt my body was looking for the hormones the whole time. Again, a scary gender transitional moment felt so natural. 

Why not me, turned out to be why should not it be me? 

Gender House of Cards

 

Image from 
Nathan Dumlao
on UnSplash.

As I progressed along my gender path, I regularly built houses of cards.

I became used to showing my cards regularly when I was a novice cross dresser. Sadly, I was coming off too often as the joker. I can't mention enough how I was the victim of the beginning cross dressers' curse. I was trying to dress as a teen aged girl when I was a wide-bodied male just trying to survive in a new exciting yet scary new world. My life existed by taking a step forward and another two steps back. Gender euphoria was very rare in my life, so I needed to cherish it when it came about. 

In order to make up (no pun intended) from the long lapses of gender euphoria, I needed to step back and try to build my house of cards with a better, more solid foundation. Every time I was rejected, I had to resolve myself to go back to my cross-dressing board and work harder on something like I had never worked so hard on before. Finally, my efforts paid off and I began to blend in with the public with less effort. I was ecstatic and I readied myself to move forward play more cards. Did someone say success breeds success? If not, I will, and it happened to me. I gained the all-important confidence I needed and headed on up my gender path.  

I proceeded to keep building my house of cards against all odds, I realized who I truly was. Much more than a relatively innocent parttime cross dresser and much more of a transgender woman. It seems like such a small difference in thought pattern could make such a huge difference in my life. Suddenly, it seemed the world opened up for me and I thought I had found the missing card I had always been looking for.  

Having said all of that, I knew I would have to set out to build a whole different house of cards. No longer did I want to just look like the women around me, I wanted to be treated as an equal. Which seemed to be an impossible dream. When I was successful in hanging out with other women, I developed a whole new set of confidence and began to relax and enjoy the experience. I was at home with myself for the first time ever. Perhaps the best result was, my house of cards was being built so much stronger and more resilient to the outside world. 

From then on, the race was on to enable my inner feminine self to play her own cards. When she finally did, she was extremely successful and made the best of her situation. Plus, she was able to build upon the mistakes of her male counterpart and never having to play the joker. Then my wife Liz came along and re-enforced my new transgender womanhood, while at the same time rapidly building my house of cards. When I experienced a collapse, Liz was there to catch me. 

I am sure you agree, building your own gender house of cards is not an easy task to complete. You need to show an uncommon level of patience when your cards collapsed, and you needed to start all over. It shows how difficult a transgender life can be. Especially in these difficult times.  

Gender Masks

 

Image from John Noonan
on UnSplash. 

In life, both genders learn early on what masks mean to their existence.

Think of it, at the earliest age, babies have only very limited ways to show their pleasure or anger by smiling or crying. Of course, as we advance through life all of it changes. I could be biased, but I think women in life have an advantage by using masks. 

While boys are squaring off on the playgrounds at school, girls are learning the basics of makeup, if their moms allow it. In many ways, makeup for women provides them with their ultimate masks. Anything from false eyelashes to skin foundations to wigs are permissible. It is not unheard of for a man to wake up to a totally different looking woman after a night out on the town. 

Makeup is not the only way women use masks effectively. I learned it the hard way several times when I was first out in the world as a transgender woman that a smiling face does not necessarily equal acceptance in the world. There were many times I relaxed too early in a situation with another smiling woman and ended up getting stabbed in the back. I fell for her friendly mask and paid the price. The whole process with women with me went back to feminine passive aggression versus the old direct aggression I was used to with men. Eventually, I came to consider the process as just another rite of passage into the world of women and I quickly became much better in being able to see what was going on behind another woman's mask. 

As my relationship with other women grew, the better I became at perfecting my own mask. I started at an early age attempting to perfect my art of makeup. It was all I could do to stop looking like a clown in drag. I stumbled along at my mask efforts before I made it into asking for and accepting professional makeup help. I happened into it during a cross dresser, transvestite mixer I was attending. Part of the mixer was given over to several professional makeup artists who offered free makeovers to anyone who wanted them. I gathered my courage, hitched up my big girl panties and stepped up for help. When the help I received was complete, I could not believe the change. The guy doing my mask had totally removed my old mask and designed a new one. The changes were so dramatic, I even received an invitation to go with the so called "A" list transgender women when they went out to bars after the mixer. To make matters even more dramatic, I was the only one approached by a man in a bar to stay for a drink. For many reasons, I did not stay and drink with him, (another story) but the point was made my mask could compete for a change with the "A" girls who the man ignored. 

The best part of finding my new mask was being able to keep it. The professional makeup guy managed to explain everything he was doing to my face and wig, so I understood it and could replicate it over and over. Once I had my mask, I was able to take advantage of it the same as any other woman would. In fact, more so, because I felt to succeed in the world as a transgender woman, I would need to be better than the average cisgender woman who had been born with a built-in mask advantage. 

Fortunately, I was able to step back and look at my new gender mask from a positive perspective and what it meant from view of a novice transgender woman. When I did, my life radically improved for the better and I understood how masks really worked in the world.

Let the World be your Classroom

 

Image from Aleksandar Andreev on
UnSplash.

It certainly is difficult to reach a space in gender time when you can relax and let the world be your classroom.

First of all, you need to acquire the confidence in yourself to view what other women around you are doing. Personally, I took the stairstep method on my gender path to finally acquire the stability I needed to grow into a stable transgender womanhood. Literally, for years, nothing seemed to come easy for me. I was very good at taking one step forward in my new world and then taking two steps back when I was rejected by the public. It was similar to the day when I thought I was on point with my fashion, makeup and wig. I was confidently walking down a mall sidewalk when one of my heels became stuck in a small crack in the walk and I almost fell. What were the odds? 

It was like the transgender gods were telling me I needed to keep learning and maybe what I just went through had happened to many other women in the past. I rapidly learned from then on to keep an eye out for any potential sidewalk issues. I was stubborn and slowly I kept acquiring the basics to stop looking at myself so much and begin to look around at what the other women around me were doing. They became my classroom at work where I worked with many women and out in the world with a group of strangers. Once I was allowed behind the gender curtain, I began to learn a lot. 

My first big lesson was women ran their world separate from men quite well. Women had their own forms of communication and style. The more accomplished women were the ones who were good at letting men think they were getting their way. I never really had to learn about dealing with men because the great majority of them left me alone. So, it was women I needed to worry about communicating with. Initially, I had few problems with other women because I was dealing with store clerks who did not care or were just interested in my money. It was not until I began to explore other facets of the world as a transgender woman did, I begin to learn the actual basics of looking another woman in the eye and talking to her. I even made it to the point where I initiated the conversation with such basics as a compliment on a dress or a piece of jewelry. When I did, I "broke" the ice so to speak and made it OK for the other woman to talk to me.

My second big lesson was there were actual alpha females who I knew from work. They were the ones who did an amazing job of balancing supervising others at work and still running a family at home. I realized, once I received a vote of support from an alpha female, I was in good shape. The whole process brought into focus how much I was able to learn from the women I worked with and secretly looked up to. I say secretly because I worked for a very male dominated company, and I did not have the support to provide the women what they needed to totally thrive. I simply was not that far up that ladder. 

As my classroom expanded, I began to write this blog, over a decade ago. Every once in a while, I go back and look over a few of my original posts. I noticed a big shift in the blog over the years. Initially, my posts revolved around how I looked and how I arrived where I was in life. On the other hand, currently my writings involve what is happening in the world now and how I arrived where I am now. Or, how I got to the point to stand in my gender space and be proud of it. What does remain constant here is all I set out to do was help others with the same gender issues I had. It just took a classroom to do it. Something I never considered when I was trapped in the dark confines of my own gender life. 

For the most part, I can now relax in the world and look around for any possible other reactions which are happily becoming increasingly rare. The classroom has gone full circle into a space I enjoy. I like going out to eat and even the LGBTQ peer support group meetings I attend virtually. They give me a chance to put on a little makeup and nicely brushout my hair. Every little bit helps in the world of a transgender woman or cross dresser. 

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. 

Real Life Impostors

JJ Hart at Key Largo.

 At various times in my life, I have suffered from impostor's syndrome when I was out with other women celebrating a girl's night out.

While I was overjoyed to be invited to the events and considered them to be a rite of passage to my transgender womanhood, I still could not shake my underlying feelings of doubt when I was allowed behind the gender curtain. 

As I went through the process, I began to wonder if all human beings go through a form of impostor syndrome in their lives. What I am trying to say is no woman is born a woman. They are socialized through life to achieve the status of women since they were born female. Men also go through the same process. It's the primary reason I had such a difficult time leaving my male past behind because in many ways I had made it to manhood which was miles away from just being another male. I needed to start all over again to travel to my gender goal of transgender womanhood. 

In the meantime, my confidence was building that I had as much right as the next woman to be at special functions. I had just arrived at the same point the other women did by using another path. I was aided also when I calmed down and began to contribute more to the group. I found I had more in common than I thought in this women's only space. Even though, I most certainly did not birth a child, I could bring up my own daughter and grandkids who I was so proud of. I just needed to flip the gender script to relieve myself of any possible impostor syndrome feelings. 

It wasn't just at the girl's nights out when being a gender impostor took a hold of me. Another prime example were the nights when I felt I was doing everything right. My fashion, hair and makeup all were on point and yet there I was wondering what I was doing there at all. I was devastated when I had come so far in my feminine presentation, just to have something else stand in my way. It took me awhile, but I worked my way through it all and put impostor syndrome in my rear-view mirror.

On the increasingly rare occasions when I encountered any resistance from the public, I finally came to the conclusion they were the true gender impostors. It was very clear to me why men left me alone as they were so insecure in their own sexuality. On the other hand, most cisgender women were more secure and not afraid to reach out to me. Especially interesting to me was the interaction I had with the lesbian community. Most of the lesbians I had a positive experience with had past encounters with men, so I was not so far from a person they would consider knowing. I learned quite early in my experiences in public, the various levels of the lesbian society. In fact, my first date with a man was with a very masculine lesbian on his way to becoming a full-fledged transgender man. Many times, the more masculine the lesbian, the more interest they showed in me. They were certainly not gender impostors.

Real life gender impostors are everywhere in this increasingly hostile world. We don't need insecure people in power using transgender women and trans men as crutches to increase their own power. 

Why Not Me?

 

Image from Danielle
la Rosa Messina on
UnSplash

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

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

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

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

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

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

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

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

Torn Between Two Lovers

 

JJ Hart in Key Largo

For too many years I care to remember, I was torn between two lovers.

The lovers I am referring to, were my second wife and my inner feminine self. The battle was often intense as both of them decided to take no survivors or prisoners.  Plus, the problem intensified when I became immersed in the feminine world and my second wife grew increasingly resentful about it. Which meant when and if I went to her for any assistance, I was rejected. In fact, on the rare nights when she had to come to me for makeup advice, I could tell it really hurt her to do it. 

I distinctly remember one night she agreed to go out to dinner with me cross dressed as my increasingly important self. I knew at the time, if I was to have any hope of acceptance from her, I would have to make my attempt to dress like her. Which meant I needed to pick out my best jeans and blouse for the date. I even went as far to be careful to tone down my makeup. Predictably, all of my efforts were not enough. She made it clear she did not like or wanted to do anything with me. It was the last "date" I can remember. 

The gender conflict caused many rifts and giant fights between us. When the fights happened, somehow, we were able to patch up our relationship. Often with the promise I would never go out of the house into the world again. Which led to a huge problem. Deep down, I knew there was no way I could keep my promise. Because, at the time, I was so into the scary, exciting new world I was exploring, there was no way I could go back. The problem was, I felt so natural as a transgender woman. 

It turned out, the emergence of my novice transgender self-began to make my wife and male self very uneasy. After all, their very existence was being threatened. 

The whole process tried to destroy me. It was often too much to take when the battle for myself reached an all-time high intensity. Certainly, being torn between two strong women was no fun and I would not wish it on my worst enemy. 

I did not know for years how strong my inner woman was. The years she had spent being hidden away had taken their toll. She became strong on her own by default. Sadly, the battle ended without a true winner when my second wife unexpectedly passed away due to a massive heart attack. By default, my stronger feminine self, pushed my weaker male self aside and took over. 

I had lived through an unique transgender situation. I was torn between two lovers, my wife of twenty five years and my developing inner feminine self who was busy telling me she had been along for the ride for my entire life. I suffered through it all and came out on the winning end. As I said, being torn between two lovers was no fun. 

Nobody Understood

 

Virginia Prince

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

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

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

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

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

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

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

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!

A Spectator in my Own Life

 

Image from Ryan 
Mangino on UnSplash.

There were many times during my life as a transgender woman, I felt as if I was a spectator looking in on the action.

The whole process was very strange to say the least as I was thinking, just who was that person. Plus, having the chance to think what I was doing was a totally different sensation. The entire problem stemmed I think, from the earlier years of my life when I was positive, I was two different people all together. One male and one female. It was not until much later on when I began to realize I was always feminine and fought all things male when I could.

Slowly but surely, I began to realize the truth and began to notice my cross-dressing nights out involved much more than just attempting to look the best I could. My spectator began slowly to change away from watching a male life unfold to watching a female one do the same. Helping me were the girls-night-out invitations I received. Following a bout of impostor's syndrome, I suffered through, I settled down and enjoyed myself. When I came to the conclusion I had just as much right there as the next woman. We had all came to our right of womanhood through different paths and mine was just different.

Finally, I grew tired of just being a spectator in my feminine life and wanted more. More meant being a spectator in my male life. Since I was still working and living part-time as a man, it meant I really needed to concentrate on my speech and movements when I was still a guy. In fact, there were a couple of embarrassing times when I was called Ma'am at work when I was in male mode. 

Early on, being a spectator in my own life was certainly a curiosity. Especially, when I thought I was just a cross dresser and putting on a dress was just a hobby. The closer I moved to true transgender womanhood, the more I learned that was not true. As I always say, the key moment in my life came when I realized I was not a man cross dressing as a woman, I was a woman cross dressing as a man. The tragic part was I went through male puberty and was testosterone poisoned as I grew up. I did not appreciate when my soft body turned to hardened angles as well as the other male changes but there was nothing I could do.

When I found my gender destination, I stopped being a spectator and began to be a more involved participant. For me, flipping my gender became an intensely frightening but natural part of my life. Living my dream was so dominant in my thought pattern, I had no problem with girls-nights-out and even could not wait for them. My newfound confidence as a woman completely pushed any idea of me being a spectator aside and opened the door for me to be a more well-rounded participant. Of course, confidence always grows more confidence, and I grew to the point where I had nothing else to prove to the other women I was around.

As I look back, being a spectator in my own life as sometimes a necessary but very different part of my existence. The entire process sometimes helped me to understand where I was going towards my dream of transgender womanhood.  

Amazing

 

Image from JJ Hart

As I sat and watched a singer do a wonderful rendition of John Lennon's "Imagine" and watched the ball in New York drop to ring in 2025, I had the chance to look back and think about how amazing my life has been.

As in everybody's life, destiny stepped in and took me in directions I never thought possible. The entire process was how I perceive the supposed death experience people have when they die. In other words, they get to see their life pass in front of their eyes. If indeed that does happen, I may have to ask for a little extra time to view all of mine.

Over a long life, I have been so fortunate to experience so many things. Outside the all-encompassing world of gender for me, was when I managed to land a job in the Army with the American Forces Radio and Television Service in Thailand and Germany as a radio disc jockey. To put it into perspective, there were only sixty other troops in the entire Army who did what I did. Since back in those days, we were basically the only connection our listeners had with home, it was a very serious job. 

Once I had served my time of three years and was released from active duty, I needed to take on again my larger issues of gender identity. To do so, I undertook serious research and development. Any time I could such as Halloween parties, I began to explore public reactions to my femininized self. For the most part, people I knew were astounded and I moved on. Perhaps it was my shaved legs which gave me away. Whatever the case, time flew by, and I started to cross dress more and more in the public's eye. Plus, at the same time, I slowly began to perfect my knowledge of fashion, makeup, and hair. I discovered the more I did, the more natural I felt and the more I wanted to do. In no time at all it seemed I was accomplishing tasks such as doing the family grocery shopping as a woman and it felt amazing.

Imagine my surprise when I then discovered I was going through another major gender transition. All of a sudden, I was losing my desire to just look like a woman and I more and more wanted to explore a path to transgender womanhood. Mainly because I was feeling alive and amazing when I did it. Now we all know how difficult a gender transition is for the average human being, and I was no different. I had very few natural feminine characteristics to work with and I had to struggle completely to survive in the life I wanted to live. Especially when I hit what I call the dark period of my life when I lost nearly everyone close to me to death. 

In order to bounce back, amazingly, I was able to rely on my strong inner feminine soul to survive at all. She helped me find my way. During the bounce back period of my life was the time I found a whole new set of women friends to instruct me on how to live my new life. Included in the trio of new friends, was my new wife Liz who I never expected to meet. At my advanced age of sixty plus, I would never find another person to be close to the rest of my life. Especially since I carried so much gender baggage with me. At the time, I still maintained one tentative foot in the male world, until Liz told me she did not see any male in me at all and what was I waiting for. Go ahead and fully transition. I was amazed and still am since it was over thirteen years ago when our relationship happened and is still going on strong today. 

The end result of watching the ball drop to welcome the scary year of 2025 was I have been so fortunate to have led an amazing life so far. Mainly because destiny has been on my side, and I have lived long enough to accept it.  

All Hands on Deck

 

Image from UnSplash

As I progressed farther along my long and difficult gender journey, there were many times where I wished I had company to aid my path.

Even though I often whine and cry concerning the lack of assistance novice cross dressers or transgender women have early on in their progression, the fact remains we need to work our way through it and do the best we can with our fashion and makeup. Until I began to see positive results, I am sure I looked like a clown in drag. Still, I was alone with my thoughts. I am old enough to remember with "Virginia Prince" and her Transvestia publication first came to my attention. It provided me with the first real look at others who shared the same interest in being femininized and looking like a girl. I was mesmerized with more than a few of the cross dressers I saw in the publication. I so badly wanted to be like them.

For years as I worked alone to look more realistic as a cross dresser, I still yearned for feminine help. I thought any cis woman could help me because of their years of practice and interaction with their peers. When I was engaged in college, the opportunity to be dressed from head to toe as a woman by another woman finally came my way. Somehow, I begged my fiancé to do it even though I don't remember now how I did it or was so persuasive. I went all the way by even renting a motel room for all the pre-prep work such as shaving my body I would have to do. 

Once I shaved and dressed, I was excited to undergo the long-awaited makeup process. Since she wore quite a lot of makeup, I was confident she could do a great job. It was finally time for all hands-on deck in my young cross-dressing life. Back in those days, mini skirts and dresses were in vogue so I brought one I found and purchased along with panty hose, heels, and a long blond wig and started the transformation process. To say I was excited would be an understatement. Time flew by as she finished my makeup, and I headed for the mirror. Instead of the beautiful blond I thought I was going to see, I was actually disappointed. I could not see much difference in her efforts from my own. Even still, I acted as if I was really impressed with her expertise when in fact, I was impressed with how much I had learned on my own over the years. 

It took me a long time working with makeup to learn each of us has a blank face to work with and we need to learn the best way to work with it. My fiancé was doing the best she could with the knowledge she learned from her own face, not mine. She was far from being a professional such as the help I finally received from a true makeup pro at a transvestite, transgender mixer I attended years later after I was discharged from the Army. He taught me lessons about my face I had never even considered such as which features to play down and which ones to build up. To this day, I owe him a huge vote of confidence and thanks.

It turned out the opposite happened with my fiancé. Due to knowing my deepest, darkest secret about being a cross dresser, she said I should use it to dodge the draft and stay out of the Vietnam war. There was no way I was going to do that, so we split up shortly before I was to leave for basic training. Actually, it was the best thing which has ever happened to me in my life. The pain it caused immediately would have been nothing like the suffering we would have gone through if we had stayed together.  

Looking back, at my life's work as a transgender woman, for the most part, it has been a solitary experience. Not having a female peer group to interact with and learn from was a problem to be sure but one I learned to work around. The end result was, I needed to be better than the next woman to make it. 

I Never Felt so Alive

Image from JJ Hart

 
One of the main reasons I found my way into transgender womanhood was when I was exploring the lifestyle of a trans woman, I never felt so alive.

It all started when I resolved one night to change my basic mind set from just thinking I was a part time cross dresser all the way to considering changing my mind all-together to I was a woman pretending to be a man, and I was so tired of feeling that way. All of my new thoughts centering on my gender led me to what I came to consider as my second grand gender transition on the night I went out to a venue to blend in with all the other professional women who were getting off of work. The difference was I did not just want to blend in, I wanted to be them. Even though I was petrified of what I was attempting, I made it through and even was accepted by all I encountered. 

The bottom line was I never felt so alive in my life and knew my life had changed forever. The problem was, in those days, I had serious male baggage to deal with. Similar to many of you, I had a spouse, family and good job to think about even though dealing with them as a male was pulling me down. Regardless, I kept on fighting and learning more and more about the femininized life I was considering undertaking. I was naive and thought I had achieved my goal of learning everything I could about living as a woman when I was just starting my path. I put all those years of just thinking my life would be just one of appearance. As my wife kept trying to tell me, I had a long way to go to learn what the life of a woman was all about. She was right, and I resolved myself to find out what she meant. 

Primarily, what I learned was a woman's life was very layered and difficult to experience because finding women who were willing to allow me behind the gender curtain were difficult to find. I was left to learn it all by myself until I reached a certain level of transition. In other words, I needed to pay my gender dues until I earned my path to the girl's sandbox. Often the route was bumpy, rough, and unforgiving but I lived and learned. Even though (as I always mention) I found friends to help me, I needed to basically keep my mouth shut and observe how the world around me was going about their everyday lives behind the gender curtain as women. 

Through it all, I continued to feel more alive than I had ever felt before as a male. I can compare the process to being guided by a searchlight in a gender fog which was my gender dysphoria. Call it gender euphoria or whatever, I could not wait until I could take the next step towards a complete life as a transgender woman. 

Pain

Image from Tony Frost
on UnSplash

Looking back, I don't think I write enough about the pain I felt during my life which was closely related to my gender issues. 

First of all, I was living in a world where nothing was ever as it seemed. Life had wedged me into living a male pattern I never felt a part of, and I could not escape. One of the problems was I was privileged in so many ways and was told constantly about it. After all, I was white, middle classed male child and all I needed to do was find a way to fit in. The pain was considerable when I learned I just couldn't. I did not have a choice, all I really wanted to do was be a girl.

Much later in life, when information began to become more available, my problem began to be known as gender dysphoria. Having a term was good enough but did nothing to relieve my pain. The only cure was to cross dress in front of the mirror and try to imagine how it would be to be a girl. I was successful in blissfully thinking I was headed in the right direction, until I started to head out of my closet and explore the world. When I did, the public took the mirror's place, and I was judged (sometimes very harshly) by an unforgiving world. Unless you happen to be a natural as a transitioning male to female person, perhaps you have been in the same circumstance of having to learn to present well as a woman. At times, the entire journey I was on seemed to be a steep insurmountable path. 

Still, I learned from the days and nights of pain I endured and kept on trying to improve my feminine presentation. My tears finally subsided, and gender euphoria set in. Maybe I could achieve my dreams of transgender womanhood. What I did not realize was how far I still needed to go. No matter how far along I thought I was with my makeup, hair and fashion, there were still hurdles to jump with communication and interaction in the real world as a trans woman. Plus, there was the very painful life I was leading as two genders when I needed to hide what I was doing from my unaccepting second wife. I always considered myself a very honest person, so being dishonest with her about my truth caused me great sorrow and pain but at that point I could not turn back.

Before I knew it, she passed away and a new pain such I had never known set into my life. It seemed I learned again how death was forever, and loneliness would follow. What I did not realize was how life could go full circle if you are fortunate enough to live long enough as I was. Slowly but surely, the fleeting wisdom of age taught me life offered both joy and pain along the way. It just so happened in my life; gender played a very important part. 

Also, life taught me feeling gender dysphoria or pain helped me to appreciate gender euphoria or joy even more. Regardless, I need to point out my gender journey was never easy and required my utmost attention. So, I could survive all of my pain.