Preparing to Lose

 

JJ Hart speaking at a Cincinnati Trans Wellness 
Conference.

When I first began to explore my transgender womanhood in public, I was rejected so much, I was totally dejected by the whole outcome.

The only thing which kept me going was a deep feeling I was doing something right in my life for a change. Plus, I did experience very brief moments of gender euphoria when for once, I had my feet on the ground and was able to blend in with other women in the world. One night I remember in particular was when I dressed in my best oversized fluffy sweater and short black mini skirt and set out to do a portion of the family's grocery shopping. After shaving my legs and brushing out my favorite wig, I set out for the store which was not too far away. 

Once I arrived at the store, it was early, and I was relieved to see it was almost empty when I went about doing my shopping. Just to prove I could, I picked out a few items I thought we needed and headed for the checkout line where one woman and a young male bagger was working. As I was unloading my cart, I slyly caught the bagger looking me over and when I looked at him, he quickly blushed and looked away. Then I looked at the checkout lady who just gave me a knowing smile and asked if I needed any help taking my items to the car. It was the first time in my life I allowed myself a brief moment to think I looked good enough to fluster a young man. I carried the experience forward with me for weeks because it gave me such good confidence in my new feminine world. 

As we all know, confidence is so important to those of us working our way down our gender paths. It does not matter if we are experienced cross dressers or transgender women, having a healthy sense of confidence in ourselves helps our progress in the world immeasurably. People are like sharks and can spot a weakness in another person a mile away. Even though my newfound confidence was still very fragile, I could feel it growing. Which was all that mattered to me. 

From there, I tried to experience living more of my life as a novice transgender woman doing things a cisgender woman would do. Again, doing a portion of the grocery shopping was an example. Looking back on it now, I am surprised my second wife did not question what I was doing but she never did. Through it all, even though I was being successful for a change in my cross dressing or transgender experiences, somehow, someway I still prepared myself for failure. I suppose it was because I experienced so much failure earlier, I still expected it. 

Then, I began to think about what I was doing and came up with what I was really prepared to lose. Since I had advanced to the point of passing in my presentation, was I prepared to lose more and more of my male world. As much as I did not like it, through out and out effort, I was able to carve out a decent male life, and I needed to decide if I could make it without my spouse, extended family, friends and job. What was I prepared to lose?

Long story short, I decided I felt so good in my new transgender womanhood, I decided what I could lose, and it was everything. I should say, I risked it all for a better life and I had very few things to lose when I tried it. My wife and close friends all had passed away and it turned out my all-important daughter came all out to accept me. So, I was very fortunate. 

All along, I was still prepared to lose, it never really happened to me. I can't take much of the credit because I put myself out in the world and good women responded. They were all I needed to restore more of my inner confidence and start a new life.  

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.

Losing Through Winning

 

Image from Humphrey Muleba 
on UnSplash. 

Sometimes during our lives, we have to lose to send ourselves forward into a better place.

It seems, transgender women and transgender men have so much more to lose when they transition across the gender border. As I often mention, we have to consider spouses, extended family, friends and employment as we grow into our unique authentic selves. I spent years in anguish trying to determine what to do about the two women fighting about my life. I mean my strong inner woman and my equally as strong wife of twenty five years, both of whom, I loved dearly. 

It turned out, the only loser was my male self, and he was not going down without a fight. When I was stuck between genders, my mental health suffered greatly. Even leading me to a suicide attempt when I did not think I could make a decision and could not take it any longer. I was attempting to live my regular working life as a male and the rest of the time as a transgender woman, and it was tearing me apart. The gender nightmare I was going through, I would have not wished on my worst enemy.

Finally, I decided I needed to lose one of my genders attempting to run my life. Due to an ever increasingly deep down feeling I was doing the right thing; I chose to go deeper and deeper down the gender rabbit hole and pursue my transgender womanhood. When I did, an unbelievable exciting, fulfilling new life opened for me. All of a sudden, I was being invited behind the gender curtain to girl's night outs and even accepted a gift from my daughter to have my suddenly longer hair styled at her upscaled salon. Looking back, I think my hormonal estrogen level increased significantly that day due to osmosis. Suddenly I learned why all women value so much their time at the beauty spa's. I was learning again why I could never go back to the male world I was losing.

As I looked around, what else did I have to lose? My wife had passed away, I closed my restaurant, lost most of my close friends to cancer, so I had nothing but a temporary fast food managerial job I hated to get me by until I could take an early retirement. Plus, I was on gender affirming hormones (HRT) by then, and my body was femininizing fast. My wins were rapidly overtaking the losses in my life. 

During the space of approximately five years, I had walked through the gender door perceiving I was little more than a parttime cross dresser and came out the other side as a full-fledged happy transgender woman. My male self-had totally lost and it was time for me to enjoy the win with my new women friends around me who taught me more than they ever knew about valuing myself. 

As with the rest of you who have gender transitioned, or are seriously considering it, I am sure I don't have to tell you what a big decision it is. First you need to accept yourself, then see if others will accept you too. Once you do, you can begin to win and put your losses behind you.  

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!

Go Away!!!

 

Image from Military. Com

Well, the long arm of the felon running the country has reached all the way down into my life again, seemingly so soon after he got into office. 

Recently, the Veteran's Administration issued a new directive stating all healthcare for transgender veterans would be halted. For those of you who may not know, I am a transgender veteran who benefits from VA healthcare. Which means, I receive my gender affirming hormones from the VA. The meds are not free, and I pay a co-pay. In addition, for years, I took advantage of free mental health services which helped me immeasurably when I was beginning my transition. I was lost and needed the help. 

Of course, I was initially really upset that once again the felon attempting to run the country should be running my life for me again. At the age of seventy-five, I live a quiet life with my wife Liz and our two cats. I am not out to hurt anyone, so why should tRumpt be screwing around in my life. For sure, I knew it was coming when he was elected along with so many other politicians who used the transgender minority to raise false fears about us. After speaking to Liz, we immediately began thinking of ways to procure my hormones which made me feel better.

This morning as I began to research the directive, in typical government double speak, I read the VA would stop providing crucial care for new gender dysphoric patients. Which of course leaves me out but not all my transgender sisters and brothers who need help with their gender issues after being discharged from the military and I feel for all of them. Here is a statement concerning the problems which will be created by ceasing care:

"VA's rollback of crucial protections, specifically the elimination of Directive 1341, is a direct assault on the well-being of vulnerable LGBTQ+ veterans, jeopardizing their access to essential care," Rachel Branaman, executive director of Modern Military Association of America, said in a statement."

Every Friday, I attend a LGBTQ support group meeting virtually at the Dayton, Ohio VA, and this Friday I hope to find out more about this latest attempt to erase the transgender population. Already, the workers who are left in the offices have been told to remove all flags from their offices. Which as we all knew, meant all Pride flags. 

I hope to learn more then before I have a crucial May appointment with my Endocrinologist who dispenses my gender affirming hormones. 

In the meantime, you trans women who wrote in and said the felon would not be that bad are enjoying all the benefits of his lies. Even you cross dressers in your closet should beware. 

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. 

Back Up Plans

 

JJ Hart visiting Key Largo.

Following several near misses as a novice transgender woman out into the world, I began to smarten up and have back up plans when I was in perceived danger. 

After the near misses with security problems on dark streets where I should have never been alone, I hurriedly went home and looked to see if there was anything in my cross dressers handbook which would have alerted me to possible issues. Since I had a beginner's handbook, I found no such warning and because I had been raised male, I went on my way like nothing should ever happen. Well, it did, and I was fortunate to buy my way out of the problem with my last five-dollar bill. From then on, I learned my lesson and never went back there without an escort of some sort. Common sense had set in. 

Many other of my problems early in my public life as a cross dresser or transgender woman came from other less than intelligent decisions, I made on my own which set me up for failure. Such as the night when my second wife and I attended a diverse mixer in Columbus, Ohio. Against her wishes, I wore a very short mini dress with my long blond wig and ended up being trapped and nearly accosted by a much larger and aggressive "admirer" in a narrow hallway of the house we were in. My wife showed up and he backed off, giving her an ideal "I told you so" moment. From that experience I learned how helpless a woman could feel when trapped by an aggressive man. I went home and added it to my back up plans for the future and scribbled it into my mental gender notebook.

Other experiences were less stressful and even more humorous. One I will never forget was when I was tempting fate with wearing water balloons as breast forms. The double-edged sword of wearing the water filled forms was they were very fragile. Especially when I ignored the danger and made the balloons bigger. All went well, until the night one broke while I was out drinking in a venue, I was a regular in. I was lucky, when the mini flood cut loose, I was already heading for the women's room which happened to be deserted.  I was able to clean up, pay my tab and leave without further incident. I did not think telling the staff I was pregnant would have worked. When I arrived home, the water balloon breast forms became history for me, and I saved up for my first set of silicone forms. 

As the years flew by and I became more interactive with the public, I began to fill out more and more of my transgender workbook, complete with backup plans. I learned to be more cautious with my plans, allowing for more of the inevitable problems which would crop up. Even still, I was caught unaware on several occasions. One of which comes to mind when I was innocently chatting with another woman's husband when she went to the restroom. When she returned, in no uncertain terms, she made it clear I was not supposed to talk to him. My back up plan was to quickly leave, and I did.

I learned also, as I transitioned away from the male gender, very quickly I lost all my male privilege too. The old bluster my way through potentially dangerous situations went away. All of a sudden, I needed to look ahead and not put myself into those situations to start with became important. Many times, I needed to think if things could go wrong, they would. Before it was the same for my spousal relationship, I needed to begin coming home earlier so I could take off my makeup and clothes before my wife returned home from her night shift. Most of the time, I did make it, but when I did not, there was hell to pay. 

Finally, when I became freed up to live my transgender womanhood, I could store away most of my back up plans and move on. However, many of the plans I discovered were just part of being a woman anyhow, so I considered them a rite of passage. Other women grew up learning about the gender rules (right or wrong) and I needed to do the same. 

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. 

The Grand Search for Discovery

 

Image from Gints Gallis
on UnSplash.

Along the path to transgender womanhood, I made many discoveries. 

It wasn't until I finally made it into the world did, I begin to pick up the pace in being allowed behind the feminine gender curtain, so I could learn for myself what was going on. In other words, I needed to earn my stripes as a trans woman to be allowed in to play in the girl's sandbox. Now, I can't quite remember what my expectations were of being allowed in, I only remember I basically forced my way in. Many times, causing the sand to really fly. 

I discovered most other women accepted me for myself and let it go at that, and I learned quickly to let the others go on their own way. After all, you cannot please everyone at the same time. Plus, the acceptance I gained far outweighed any negatives I experienced. I discovered once I made it past the idea I was attempting to "fool" anyone into thinking I was a cis-gendered woman, the better off I was. When I was satisfied to just be myself, more women reacted to me positively. Probably because they appreciated, I was being truthful with them. I was just busy learning how to live my dream and meant nobody harm.

Even still, my gender path was very winding, and steep with many roadblocks. Similar to many of you, I experienced the pain of separation from family, friends and life in general as I transitioned and femininized myself. Many times, I needed to stop and rest on my path because the effort exhausted me.

Out of all the discoveries I made, one of the biggest ones was when I made the transition from weekend or parttime cross dresser to novice transgender woman. Even though I was just dealing in basic gender semantics, the shift in thought was a major one for me. All of a sudden, I began to feel I was achieving my childhood dream of being a woman. Not just looking like one. When I did make the discovery, to change my life, my path ahead became fairly well illuminated. Now, I had the usual hurdles to jump through such as how to make my way out of the mirror and into the sandbox but overall, I had the confidence to move forward.  

The other main discovery I made as I entered transgender womanhood, was how important the gender affirming hormones would be to me. Of course, I knew the physical changes I would go through such as changes to my body such as breast growth. However, nothing prepared me for the internal changes which would go on. All of a sudden, for the first time in my life, I could cry tears of joy as well as sorrow. In essence, estradiol softened my entire life and quickly took the testosterone related universe I lived in away from me. A huge discovery. 

Of course, every discovery does not have to be a good one. When my second wife discovered I was sneaking out of the house to live as a transgender woman was certainly not a good discovery for me. It took me weeks of apologizing and even therapy to save what was left of our twenty-five-year marriage. Which I managed to do until she unexpectedly passed away. When she did, I discovered what loneliness was all about. 

Every human life is filled with discovery if you are living it right. It seems transgender women and transgender men live have an extra amount of discovery. It is very rare a person who has the chance to explore the two binary genders to determine which one they want to live as. I feel it is one of the reasons so many people these days misunderstand our trans community and treat us poorly or even with hate. We have found how deep trans bigotry suddenly runs in our country, led on by a certain felon as president. Which is all I am going to say about it. 

In the meantime, I hope all your discoveries are positive and exciting.

Should You Be a Jumper?

 

Image from Jeremy Bishop
on UnSplash. 

As we go through life, many of us have chances to jump and try to improve our status. 

As I lived, I certainly registered in the jumper category. I have no idea if many of the decisions I made concerning employment changes and resultant family moves had anything to do with my gender issues, but I always assumed they did. What if I was trying to just jump and hide from wanting to live a feminine life and escape the old male one, I was forced to live. 

The one thing I did learn relatively early in life was I did not have to put up with seemingly huge obstacles put in front of me. The biggest example was when it became obvious, I was going away to serve my country during a very unpopular and deadly war in Vietnam. Immediately, since I worked for a congressman's radio station, I sought out help to work in a very small section of the military...American Forces Radio and Television. I thought, why not try and see if I could pull off a miracle of sorts, so I went ahead and jumped by sending off letters to Washington, DC. Amazingly, I received a fairly positive letter back and went on to eventually landing a spot on the network. So, jumping really helped me, and actually spoiled me for the near future.

When I was discharged from the military, I played around for a while and ended up on a cross-country car trip with my future first wife and mother of my only child. Since we were driving from my home in Ohio to her home in California, we covered many miles with side trips to visit friends in Texas and Seattle. It was fun as my fairly new Chevrolet Vega held together well enough to make the trip. And all the jumping helped me to briefly forget all my gender issues. 

When we returned, I pooled together my savings with a friend and bought a small neighborhood tavern in my hometown. It was quite the jump as my dad described it best as a place which had two doors, so the Flys did not have to stop when they went through. Even though dad's opinion spoke for itself, we worked on the tavern and finally made it a success when we added homemade pizza and deli sandwiches. Sadly, I destroyed all of my hard-earned success because of excessive alcohol abuse, and I lost the whole operation. 

Ironically, I did not learn my lesson with restaurants because later on in life, I quit a very good commercial chain restaurant job to risk a fairly sizeable inheritance I inherited when my dad died. This time, due to a severe economic downturn in the town I lived, I lost the whole gamble after about five years. Proving once and for all, my jumps did not all turn out well. 

Later on in life, I blamed much of my dependence on alcohol as just a way to jump life and not have to deal with being a transgender woman. Even still, I was far from finished from jumping. As I began to go public as a novice trans woman, I learned I could actually live the dream life I wanted. To do it though, I would have to jump through a set of very serious hoops to succeed. What would I do with the fairly successful male life I had worked so hard to succeed with. When each of us considers a total gender jump to the other side, we have to wonder what will become of our family, friends and employment. Rather than considering the process as a jump for me, I always thought of it as sliding down a steep gender slope towards a cliff of unknown depth. 

Regardless, I gathered all of my courage and put my male life behind me. I gathered up all my male clothes and gave them to the thrift store and set out with my gender affirming hormones into an exciting new world. 

In the world of transgender women and transgender men, it is extremely difficult to advise or give much guidance to each other. Frustratingly, many trans people share the same path but on the other hand don't. It shows up in the maddening ways we can't seem to truly unite as a strong "T" under the LGBTQ umbrella. It is difficult for all of us to jump together. I can't say you should be a gender jumper or not. It has to come from deep inside you.

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. 

Born This Way

Image from Vonecia Carswell
on UnSplash. 

 I had no choice; I was born with gender issues which I would have to deal with my entire life.

It is also International Women's Day, so in many ways, the gender issues I did deal with intersect with each other. Along the way, I have received pushback about saying I was a woman at all which I understand. At first, the transphobes attacked me with the old broken argument that I could not be a woman because I could not birth a child. I simply pointed out, many females for whatever reason cannot or choose not to have children. Their choice certainly does not make them any less of a woman.

So, how can I claim Women's Day as my own? Mainly because I worked so hard to gain my transgender womanhood and it should be included with every woman everywhere. At the least, I can provide unique perspectives on my life. Trans women everywhere are fighting now for their very right to exist as women and should accepted as such. In fact, I had some good news-bad news from the VA where I obtain my gender affirming hormones about my future availability of the meds. In my Veterans Administration LGBTQ support group meeting yesterday, the moderator passed along the good news about the long reach of the current felon's administration. The good news was there would be no changes to transgender care, but the bad news was, it said for now. We all know that is not good news. In the meantime, I received my new shipment of estradiol patches this week along with three refills which are plenty to hold me over to my next endocrinologist visit in the early part of May. 

Back I go to the subject at hand. As I always mention, transgender women never had the girl's workbook to benefit from. We never had on hands advice or guidance from our mothers or from the other girls around us. We were left on the outside looking in. What it meant was, we really had to hit the ground running when we came out into the world, we had a lot to learn. Lessons in femininity were often swift and brutal. As I survived mine, I earned my way into celebrating International Women's Day and you should too. 

I sense from the comments I receive here on the blog; I have a wide range of readers from weekend cross dressers, all the way to post operative transgender women. The only point I am attempting to point out is, no matter where you might be on the gender spectrum, you still matter. None of us have a crystal ball telling us the future. For you cross dressers, sooner or later, you may have the chance to open your closet door and live a life you possibly just dreamed of. As I found out, never say never is a good quote when it comes to a possible later in life gender transition. Along the way also, I learned I had tons of knowledge of the world I could offer to other women. Because of my life masquerading as a man, I have a leg up on demystifying the male world for other women.

Even though transgender women may be the underdogs in the overall women of women, we belong in celebrations such as International Women's Day because we were born this way.

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.  

  

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.