I Made Nothing

 

Image from Camillo 
Contreras on UnSplash.

Several of my earliest memories of success as a cross dresser came during the Halloween parties I went to. 

When I wore my very short mini dresses, showing off my freshly shaven legs, I found I had several women come up to me and say, I "made" a good-looking woman. Years later, when I began to understand "woman speak" better, what they probably meant was I "made" a good-looking woman, for a man dressed as one. 

Furthermore, I soon came to realize, I was not making anything. I was simply being who I was. In order to learn that simple fact, I needed to live decades of life as a parttime cross dresser or novice transgender woman. Or I needed to live my gender truth before I could claim it. I needed to get out of the mirror and into the world to learn if I really belonged there. Those were the days when no one in the world around me would give me a break. The public was laughing at me (rightfully so) because for the most part, I was dressed like a clown in drag. Plus, my old male self, my second wife and my mirror did not want to let go of me. Making my life miserable and destroying what I had left of my mental health.

Juggling two genders at once was a tremendous challenge when I caught myself practicing living one gender when I should not have been. Being called "Ma'am" at my macho management job was certainly not cool or good but somehow, I survived to live on to the next day when I was determined to do better.  What happened was, I did keep getting better at my feminine side and increasingly began to leave my male side behind, which scared him.

Fear, as they say, is a powerful motivator and instead of giving up, my male side and my second wife grew increasingly close and forced a battle of the wills. In other words, neither one of them wanted to lose their place in the world. Which included my universe. It turns out, I did make something...a huge mental mess for myself. It is one of the excuses I make for taking nearly fifty years to break out of my gender bonds and flourish out of my closet and mirror. I just had to make sure I was making the right choice and there was so much pressure on me. 

As I grew out of the mental gender mess, I had made for myself, I gained the critical confidence I needed to establish myself as a secure transgender woman. Not just a femininized man. Since I had spent a lifetime getting there, the personal coming out was extra special to me. It was as if my feminine self was telling me what took so long. As it turned out, I shared her belief in wondering why I took so much time and wasted so much nervous energy I wish I had back. As we all know, worrying over what we did in the past is a waste of time, unless we are learning from our mistakes.

I felt better when I realized I did not make anything, when it came to my gender issues. Rather, I inherited them from some unknown source which made life a challenge. A challenge I needed to finally accept before the pressure I put on myself had grown too heavy to carry and I had to put it down and go with the life which made me feel natural and alive. When my transgender womanhood became secure thanks to friends I had, I felt so much better as I built a new life.

Do the Right Thing

 

Image from UnSplash.

I learned early on from my parents when in doubt, you should always do the right thing. At the same time, I learned from them, dressing to look like a girl was not doing the right thing. So, I needed to completely hide it.

Later, when I attempted to navigate my gender path, I found many obstacles I did not foresee hurting me. But they did and brought about many doubts. Of course, the main doubt was, should I be doing all the cross dressing I was doing in public at all. Still, I persisted and improved my craft at presenting well as a femininized person. Finally, I arrived at a point where I could leave my dark gender closet and attempt to live a new scary yet exciting life. The more I explored as a novice transgender woman, the more I wanted to do. Which brought me back to the question, was I doing the right thing. 

Similar to so many of you, I suffered from extreme guilt as my second wife kept telling me my gender desires were selfish pursuits. The sad part of it was, for the most part, she was right. She wanted very little to do with me wanting to be a woman, so I kept it away from her. Not the right thing to do in a marriage but was my only recourse. At that time, I only had a distant dream of perhaps living someday as a transgender woman. All I needed was the courage to face my reality. 

Because of a number of reasons, I needed to do much more exploring the world as a transgender woman to see if I could survive. First, I had to look the part, then I needed to live the part. Standing in my way, were the usual questions of transitioning to another gender such as what would become of my family, friends and job. As well as did I really hate my male life that much. I wasted hour upon hour antagonizing over what I should do and would it be the right thing. 

I was stubborn of course and refused to do any more than observe several transsexual women I knew from a distance. From their stories I did know they had really good safe jobs or were close to retirement so they could support themselves whereas I did not and had no idea of what I would do for an income. Plus, I also needed to consider, both of them were flat out gorgeous and had no problems presenting in the world as women. I did not labor under any idea I even came close to being as attractive as them and did not have that going for me either. After taking all of this and much more into consideration, I did not know what I could do about my gender dilemma which was not doing my mental health any favors.

What I did do was try to continue on the path I was on. To increase my awareness of the world as a transgender woman as much as I could at a time, I went as far as I could. Even absorbing major clashes with my wife over what I was doing. I can't always say I did the right thing as I learned more and more about living in the new world I was seeking. There were too many times when I had to out and out lie to get out of situations, I found myself in. In all fairness to my wife, she told me to stop it and just become a woman to bring peace to both of us. Still, I did not have the courage to change my life and leave her behind. I did not do the right thing. 

You regulars know what happened next. My wife passed away quite tragically from a heart attack leaving me all alone with my dogs to put my life back together. I rapidly turned to my inner feminine self as the strongest person around and did the right thing and finally turned to a life I always just dreamed of. 

On a side note, I may be missing a day of blogging tomorrow as my wife Liz and I have a daylong seminar to attend. Sorry for the inconvenience!

When too Much Wasn't

 

JJ Hart (Middle) with two friends.

As I continued along my long and winding gender path, I (on occasion) ran into situations when the public seemed to be too much. 

Examples were the times I was approached in public by strangers when I did not want to be. Very quickly I needed to judge their motives. Did they see me as a man in a dress on one hand, or as a woman on the other. Naturally, it made a big difference when I returned home and rated my experiences as a novice transgender woman out in the world for the first time. How did I do? Was I too much for my own good and did I need to tone it down, or attempt to do more?

There were the times when I managed to thrive in situations where women dominated and times I could not and ran home. Back to my gender drawing board. There seemed to be so much to learn, I was overwhelmed by the task ahead of me if I was ever to achieve my dream of living a femininized life as a transgender woman. 

In the end result, normally I found too much just was not when I was trying to get ahead in a new world I was just getting used to. The problems occurred mainly in the areas of fashion and makeup, as well as where I was trying to go when I went out. Once I got them under control, I was able to build a stable new life in the girls' sandbox. Once I earned my way in. Often earning my way in, had its own set of challenges. Mainly I had to find out how to play correctly to be accepted. On the other hand, even though it was difficult to do, I had to play to learn a life's full of lessons in a hurry. As I always say, my women's workbook was blank to this point, and I needed to write it. 

I found as I struggled to fill out my workbook, I needed to be extra vigilant in how I viewed other women, since I was totally on their turf. For the most part, I did my best to hold back on my opinions and speak mainly when I was spoken too. It worked well enough until I could get my feet on the ground, and I could move forward as a transgender woman. My goal was to build my new life as a confident, intelligent woman in society, but I needed to prove to myself my goal was not too much and would destroy my dream of transgender womanhood. Fortunately, throughout my life, I had several strong positive feminine role models to work from and add to my workbook. When I was able to add their influences to the inner female, I already knew was there, the women formed a strong bond to guide me through my struggles.

Overall, I discovered rarely too much just was not. What was happening was, I was just paralyzed by fear to move on with my new life. Once I got over most of my fears, I was able to move on and be free to live a better life. A better mental health life waited for me when I quit fighting two genders to survive. 

If you Know, you Know

 

JJ Hart from Key Largo, Florida

One of the reasons, we transgender women and trans men have to put up with so much evil misinformation about us in the public's eye is so many people don't even know a transgender person. 

The main reason is, we are so few when you consider the population as a whole. However, within the trans community, we share many similarities. For example, many of first trips into a feminine lifestyle came when we went through our mom's dresser drawers (or sister's) and came away with a wonderful experience. Sadly, then we could not understand why all the people and family around us could not be trusted with our secret. To make matters worse, our secret was so rare, the chances of finding anyone around us who understood was nearly impossible. I only tried to relay my secret to someone who understood twice. Once I was quickly rejected and once I was not. Of course, with the first person, I went back into my closet and was never seen again. But with the other, I found a friend I could share my desires with. Until he moved away with his mother who did not care if we experimented with her clothes and makeup. I don't know for sure, all these years later but perhaps I had found the proverbial needle in the haystack. Another person who knew what I did, we loved all things feminine.

As life continued on, I began to attend various transvestite - cross dresser mixers where I received mixed feedback on how I felt about knowing others. I discovered I did not form as many gender bonds I thought I would. I figured simply we were both into cross dressing and beyond, we would get along better. Quickly I learned, I did not know most of the attendees better than the rest of the world simply because we shared the same need to be femininized. I was exposed suddenly to different layers of the world who had the same gender issues than I. Or so I thought. I found I did not know anymore how the cowboy cross dressers who I called that because they wore cowboy hats and smoked big cigars while they wore a dress, could do that. I had my upbringing when I wore slacks to a mixer and was attacked for doing it. 

Then there were the "A" listers who were very attractive an acted just like the stuck-up girls I went to high school with. I did not get along with them either and did not understand why they could not have been nicer to everyone. I guess, if you know, you know wasn't working for me just because I put on a dress. I was learning the hard way, the differences between cross dressers and transgender women. 

These days, I am involved in just one support group through the VA, which used to be known as a LGBTQ peer support group before the changes forced upon us by the orange felon. Now we are just a support group made up primarily by the gay and lesbian attendees. In fact, out of twelve or fourteen participants, I am one of only two transgender women in the group. What I have learned is, out of all the LGBTQ people in the group share many of the same problems, especially with the upcoming problems in the Veterans Administration. Once again you could say I was so involved in my little world, I did not consider others. For example, I assumed gay and lesbian people understood or supported transgender people because we are cousins so to speak. Whereas they don't understand us any better than the rest of the world. That is why I love to share my experiences with the gays and lesbians in the group. 

I am doing my best to change and understand just because I am transgender, I understand what other trans people are going through. Or they understand me. It is difficult because today more than ever, we need each other in the world to survive. 

I Just Couldn't Live Without Her

 

Image from Brian Kyed
on UnSplash.

At a certain moment in my life, I had reached the point of no return where I was living with two women, the one inside of me and my wife of twenty five years.

The question remains, how did I find myself in such an untenable, precarious situation. The answer was, it was not easy, and I really had to work hard to get there. Decades, to be exact. Once I pulled myself out of the mirror, and put her into the world, I knew I could never go back to being a parttime cross dresser. I could never live without her.

Many times, I have gone through the many steps I took on my path to transgender womanhood. To provide you all with a more precise look at my actions, we need to go back to the years when my second wife was still alive. What I began to do was sneak out of the house when she was working cross dressed in the world just to see if I could. After a very rough beginning, when I was laughed at, I began to get my high-heeled feet on the ground and do better. So much better, I began to think my ultimate goal of living as a transgender woman on my own terms may actually be possible. 

From there, I began to spend every spare moment I had alone as who was to become my authentic self. I became so immersed in becoming a woman, I needed to concentrate on the times when I still had to be a man at work, or with my wife. The biggest problem I had was, deep down inside I knew which gender route I had to take to survive in the world, but I was afraid to face it. The fights between my wife and I became so bad, a couple times she just told me to be man enough to be a woman. I was not man enough to do it, but I was stubborn enough to keep trying to live a middle of the road gender life, which became impossible to maintain. My mental health suffered, and I began to be more self-destructive than I already was. All the way to attempting suicide one night.

Fortunately, I was not successful in my suicide attempt, and I proceeded down the same path I had been on before. This time taking my cross-dressing activities into my own restaurant and threatening my substantially good job. Again, deep down I felt if everyone knew of my deep, dark secret, I would be relieved of the hell I was living because I had to make a change away from the male life I was living. 

Just before my wife suddenly died, I made one last ditch effort to partially purge myself of my femininizing supplies. I went all the way to growing a beard, so at least I was telling myself I was making an effort to return to the male world. However, there was one big problem, I was miserable and about the time I needed to go back into my feminine world, my wife suddenly and tragically passed away from a massive heart attack at work. Through all of our problems, I loved her deeply and we were married twenty-five years.

I often wonder what would have happened had she lived. I think now, my internal female would have won out and I would have completed my gender transition. She would have won because I felt so natural in the world as a transgender woman. When it came down to which woman I could not live with, I would have had to have chosen the woman I should have been all along and hopefully patched up my life with my second wife. So, at the least, we could have stayed friends.

The Light in the Mirror

 

Image from Alessandro 
Bianchi 
on UnSplash.

I spend quite a bit of time here attacking my mirror when I was growing up.

Recently, I have come to the conclusion some of my negativity could have been wrong. First of all, I was fortunate to have a beautiful full length mirror dad installed at one of the ends of the hallway in our house when I was growing up. When no one else was home, I would spend as much time as I had admiring myself in the hallway mirror. As I did, I could always see a brief dim light in the mirror when I viewed my feminine self for the first time. Even when I knew, the light would have to be extinguished soon, and I would have to go back to my unwanted male world. 

As I grew up and began to explore the world for the first time as a beginning cross dresser, I made plenty of mistakes the mirror did not tell me about. In fact, the mirror light shone brightly and told me I looked great when in fact, I looked just the opposite. I was presenting as a clown in drag with no one to warn me. For a long time, the light in the mirror nearly went completely out as I was rejected in public time and time again resulting in a deep depression for me.

I kept trying though, and the light began to come back on. I lost weight and began to find styles of women's fashion which flattered my body shape and finally began to present better. Especially when I was making the mental transition to novice transgender womanhood from cross dresser. To do it, I needed every break I could muster. Plus, I needed to turn up my light in the mirror, and let my femininized light shine through, so I could see her better. 

The extra light turned out to be all I needed to become more skilled at my makeup art and do the best I could with my testosterone damaged male face. With a little help from a professional makeup person, my light in the mirror grew even brighter, and more importantly, I could trust it. With trust came confidence which equated to more acceptance as a transgender woman in the public's eye. All of a sudden, my lifelong dream to lead a feminine life was within reach. If my light in the mirror stayed on. 

It did and I was even able to turn up my light to a brighter level with the addition of HRT or gender affirming hormones. Among the many other positive changes I went through was when the overall texture of my skin softened. Which meant the male lines in my face softened and I could use less makeup. Specifically, foundation. I quickly learned with more femininized skin and being able to wear my own hair, I was suddenly more presentable to the world. 

Looking back, I may have been too quick to judge my light in the mirror. It just took a little longer (along with the rest of me) to become more situated with living a new life away from my old male self, and perhaps it was my fault for not switching to a brighter bulb sooner. Plus, I was fortunate in that my light in the mirror did not burn out altogether. 

 

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.