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. 

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.

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? 

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. 

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. 

From Obsession to Passion

 

Image from Kayshawn Herandez
on UnSplash. 

For years I considered my desire to cross dress was more an obsession than anything else.

Similar to many of you, I started my path to femininization innocently enough by rummaging through my mom's clothes. Whatever I could fit into was fair game for me. The pleasure of the overall experience soon turned into an obsession. When I returned home from school and was alone, I locked myself into the bathroom and got busy with mom's clothes and makeup. 

Even though I was wrapped up in my obsession at such a young age, doubts snuck through and slowly became evident. The biggest doubt was I was more than just a cross dresser. I wanted to be so much more. Such as the totality of being a girl. Looking back, it was sad I did not have more information on gender issues because I would have discovered and hopefully faced up to the fact, I was more transgender than cross dresser. 

As I trudged forward through life, I stubbornly held on to the best I could to my largely unwanted male ways as I idolized the girls around me. Thinking they had all the assets in life. Primarily the one in which they did not have to be forced to serve in the military during the Vietnam War as I did. Why did girls not have to serve, and I did, made me quite bitter. However, there was nothing I could do about it, so off to serving three years in the Army I went. 

As soon as I was honorably discharged from the military, I began to restart my cross-dressing obsession in earnest. Off came my Army mustache and on came the blond wig. Since my first wife knew I cross dressed and did not really care, I was able to do more exploration into the world of fashion, wigs and makeup. In essence, I was making up for all the lost time (three years) I had in the Army when I could not cross dress. The lone exception was a Halloween party when I dressed as a prostitute. The one night of bliss hardly made up for the three years of staying away from my obsession to at the least appear as a woman. 

When I finally had the courage to try out the world as my increasingly evident feminine self, my focus began to change from obsession to passion. I spent every spare moment daydreaming of how it would be to try out what I was doing as a man to a woman. During this time, gender reality shifts turned out to be a major point of my life. Especially when I actually began to live out my gender dreams.

What I did then was set up mini gender "bucket lists" to attempt to conquer. I say attempt because several were ill-advised and nearly impossible to accomplish. One in particular led me down a dangerous safety path when my male security privilege was lost. I almost learned the hard way not to be on dark city streets out of my car unescorted. Even though, I was still stubborn about my passion, I learned I needed to be careful. When I went back to the area where I was approached at night, I made sure I asked one of my transgender man friends to escort me. It was a new experience to ask for help. 

My passion to be a full-time transgender woman took me through gender affirming hormones and changes I never thought possible. I was grateful I was medically cleared to take the meds by a doctor at the advanced age of sixty.   

I am also grateful to be living my passion now with a wife who loves me very much. I took over a half a century to get there but I switched a basic obsession to a fulltime passion, and I never looked back. 

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. 

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. 

Once Your Eyes are Opened

 

JJ Hart, Club Diversity, Columbus, Ohio

In my case, once my eyes were opened as a transgender woman, I could never close them again.

Perhaps it is because I went through so many trials and tribulations to arrive where I wanted, or even desperately needed to be in my life. Since I had so few natural feminine traits to work with, I really needed to work hard to achieve a feminine presentation. I tried all sorts of ill-fated ideas before I ever got it right. Yes, it was me making the routine cross-dressing mistakes such as attempting to dress as a teen aged girl when I was thirty and had a testosterone poisoned body. All I accomplished was directing unwanted attention to myself. 

 It took me awhile to realize what I was doing, and my eyes were finally opened to what I was doing. The perception I had was I was dressing for men, when in fact, I should be doing the opposite and dressing for the women around me I needed to co-exist with. I learned the hard way, women ran the world I wanted to be part of, and I needed to do my best to get there. All of this meant I needed to keep my eyes open and do the best I could to study the women around me. Or how did the women react to the world around them, good or bad. 

Sadly, blocking my way were women such as my second wife who wanted no part of living with another woman, transgender or not. She was content with letting me learn on my own what women needed to survive in the world. Looking back on it, her process for me was the best way to go because once I learned something in my new transgender womanhood, I never forgot it. Also, magically, once I opened one door to my new life, my eyes were opened to another door. 

As I opened a new door, I knew I could never go back to my old male life which was bringing me down. I felt so good and natural in my new life, there was really no choice to be made. The only problem was what was I going to do with all the male baggage I had acquired over the years. Similar to most of you, I had the usual assortment of spouses, family, friends and employment to deal with. Fortunately, I started my transition process with the person who turned out to be the most accepting of all my family and friends. I am speaking of my daughter and her immediate encouragement helped pave my way to more attempts at telling the world about my authentic self. I ended up going one for two in the family process when I was roundly rejected by my brother and his family. He opened my eyes to what transgender rejection could really be like.

Still, I persisted, knowing I was on the right path and my eyes were not deceiving me. It took me awhile, but I finally gained the confidence to look another woman in the eye and communicate one on one with her. To do so, I needed to not concentrate on how I sounded and instead put an emphasis on what I said. In order to survive, I needed to keep my eyes open at all times because certainly every other woman was not going to be my friend. 

I did keep my eyes open and learned the hard way to keep my head on a swivel. There were many claws I needed to be aware of. Quickly, I was hardened to what the new world was like around me. More and more, I could never go back to the male privileges I had before. Even though, I lost much of my intelligence according to most men and especially lost my personal security, I still wanted more and more of my transgender womanhood. 

You might say, I acquired new 20-20 vision and it was perfect in many ways. It was a long and difficult learning process, but it was the best life I could have ever imagined, and I just felt I had done it sooner. 

The Comfort Zone

 

My trans friend Racquel

As a transgender woman or a trans man, you often encounter major barriers when it comes to reaching our gender comfort zones.

We have all sorts of setbacks such as family and spouses, employment and potential loss of friends. Giving up the life we had been leading is never an easy decision to make. It's definitely more than just an easy choice which a percentage of people (or transphobes) think it is. For some reason, they think it is just a matter of transgender people putting away their clothes and returning to their birth genders. They don't understand how deep our experiences run. Along the way, we become very resilient in our journeys and for the most part, our tribe is strong.

We are strong, in part, because of the time and experiences we went through to reach our comfort zones. I know I had to endure stares all the way to out and out laughter in the early days when I went out and challenged the world. Catching up with all the years I lost not growing up as a girl really came back to haunt me when I had to struggle to catch up. No one taught me the basics of fashion and makeup. More importantly, I did not have the confidence I needed to move forward to even learn if my gender dreams could ever become a reality. Which was the most important thing to me.

Slowly but surely, with success, my time in the comfort zone came around and I survived. It was never easy. To this day, when we traveled to the Florida Keys recently, after all I had been through in my life chasing my gender, I still was very nervous about several things I would face along the way on the bus tour.  I did not know how I would fare as a transgender woman on a bus full of strangers. Especially when it came to having restroom privileges as we traveled through the deep south. However, I can't spotlight the deep south for its anti-transgender laws when my native Ohio recently has passed some of the most restrictive trans laws in the country. I guess you could say, I could run but I could not hide.

Quickly, my fears dissolved as the other women on the bus began to not so slyly question my wife Liz and I's relationship. The reason was one woman said to Liz, she thought we were sisters. Which really increased my confidence and put me in a comfort zone which would last for the rest of the trip.

My comfort zone expanded, and I was able to enjoy my new reality of acceptance in my transgender womanhood. Of course, it was all challenged when I caught Covid on the way back to Ohio and ended up in a suburban Atlanta hospital. I was fortunate in that I had my Covid vaccine three months before and my case was lessened in its severity. My three days stay in the hospital really challenged my comfort zone because I have never had any gender altering surgeries. So, even though the staff initially thought I was a woman, it quickly became evident I was still a biological male. Hopefully, I won't have to go through an experience such as that for a while again.

As we all know, comfort zones are fleeting and have to be earned. You need to be patient and do the best you can until your confidence as a transgender woman or trans man comes along, and you are finally comfortable in your own skin. 

Trans Girl at the Symphony

 

Cincinnati Music Hall

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

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

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

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

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

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

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

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

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

Always Running

 

Image from JJ Hart

Much of my life was immersed in running from my gender problems. 

As fast as I could, I changed jobs and even places my wife and I lived so I thought would make a difference in my life. The prime example was when I picked up and moved my small family from our native southwestern Ohio to the huge bustling New York City metro area to operate a fast-food restaurant. By doing so, I thought deep down I would be closer to a population which would be more friendly to my cross-dressing desires.  I only made it a year before the culture shock pushed me back to our native Ohio.

In the meantime, I did have several moments when I was in New York which I will always fondly remember. One of which was the night I actually got out of the house by myself without my wife and drove myself out to Long Island for a transvestite mixer I had read about. Once I was out, I had two major surprises waiting for me. The first of which was I was happy I found the venue at all. The second one happened when I tried to get in. There were two women at the door monitoring who got in or not. I was flattered when they refused to believe I was a man at all and asked for an I.D. to prove who I was under all the hair, makeup, and fashion. 

The second most memorable night was again when I managed to be out alone in the world as my authentic self. Quite unexpectedly, I was invited to a Halloween party by one of my female assistant managers. Of course, I did not to think twice before I accepted her invitation and began to plan ahead on what I could wear that my wife would approve of. Finally, I learned she would never approve anything I wanted to wear, so I set out on my own to come up with a costume I would have fun with. It turned out my short tight dress and heels matched perfectly with what the other women in our little group were wearing. Plus, the women were all tall and I really blended in well in our heels.  

As I said, the culture shock of NYC over Ohio wore me down and we ended up moving back. When I did, I immediately fell back into the whole cross-dressing culture I was in before. I was unhappy and hidden away from the world, so I found another place to move to and uproot our lives. The job I was working offered me an opportunity opening restaurants along the Ohio River in southern Ohio. A very conservative area to be sure so I needed to up my cross-dressing outings. Somehow, throughout the whole adventure I grew tired of having limited places to go and wanted another move to improve myself. 

This time, I tried to move back to the Columbus, Ohio area where I knew several very diverse friends in the LGBTQ community, specifically the transgender crowd. Following a lot of work, I finally landed the job I wanted, and we moved again.

Finally, I grew tired of all the running I was doing, and I needed to settle down and face my gender issues head on. It took me until I was sixty to realize I needed to make a change to a full-time transgender lifestyle. When I did, a giant weight was lifted off my shoulders and I went on to start gender affirming hormones or HRT. It was a wonderful way to live. 

Someone is Paying Attention

Image from Alena Garrett
on UnSplash. 

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

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

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

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

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

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

Down the Rabbit Hole

 

Summer Image, JJ Hart.

Over the years, I began to sink rapidly or was stuck in an increasingly large and deep transgender rabbit hole.

Sadly, I did not have the information I needed at a young age to help me to understand I was much more than a boy who preferred to dress in girls' clothing. I just knew I was not satisfied with cross dressing in front of the mirror on the rare moments I was alone. I always had problems with what I called the gender roller coaster, or I was up when I cross dressed for a couple days before I crashed to the depths of depression and daydreamed my life away thinking of the next visit, I would have in front of the hallway mirror. 

Only one of my thoughts was for certain, I was falling down a gender rabbit hole which I could never return from. For many years, I thought I would possibly grow out of my gender issues, and they could possibly be a phase. Of course, wanting to be feminine in all aspects of my life, was never just a phase and just grew stronger as I aged. 

It turned out, the older I became, the fonder I became of my rabbit hole and wanted to stay there. When I did go out, I was like a real rabbit, cautiously surveying the world for predators. It was not until I began to arrive at a financial point when I started to build confidence in my cross-dressed presentation, did I begin to enjoy my trips out of the hole and into the world. 

It was about this time too, when I began to expand my rabbit hole. I needed more space for my wardrobe and wigs of course. Not to mention the mental room I needed to grow into the person I was becoming. Once I saw the light of my new gender day, there could be no turning back. The light felt so good and so warm; I was loving my new life. 

I ended up forsaking my gender rabbit hole for a new universe of women. To be truthful, it was the most difficult experience of my life. Since I had left my old comfort zone of white male privilege, establishing a new base was difficult in my new transgender womanhood. I had dug my gender rabbit hole so deep; it was difficult to find my way out. 

Sadly, I see too many transgender women and trans men who are stuck in their gender holes. Especially, in the current negative situations we are living in right now, I understand why so many LGBTQ people want to stay out of the public eye. It is just a shame we need to do it.

Your Personal Best

 

Image from Markus Winkler
on UnSplash.

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

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

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

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

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

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

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

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. 

The Gender Envelope

 

Image from Alexandru
Zdobau on Unsplash.

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

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

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

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

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

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

What is the End Game?

 

JJ Hart, Woman in Red.

Wow! My journey was a long one to transgender womanhood where I always thought I should be. Nearly fifty years from being a part-time cross dresser to fulltime transgender woman. 

The problem was getting there, because the end game scared me so much. I was in my own gender quicksand and could not seem to get out. I had no dashing cowboy riding up to rescue the damsel in distress. I was on my own. So, I persisted through countless days in front of the mirror or combing through thrift stores searching for just the correct fashion statement.

The more I learned about my feminine self, the more I realized how strong she was and how I needed to protect our relationship. The more I did, the more I began to see the end game could be in sight, if I wanted it bad enough. I knew the possible pain of giving up family, friends, spouses and employment to see the end game in person. The problem was, I was gaining more and more experience in my feminine life and every time I did, I did not want to go back to my unwanted, boring male self but I did. Over and over again until it wrecked my mental health and almost cost me my life. 

Still, I kept my eye on the goals I had set which brought me ever closer to my end game of living life as a transgender woman. Along the path I had set for myself, I still had very real doubts if I could do it. I also found out quickly, just daydreaming my life away about being a woman or cross dressing in front of the mirror was not working anymore. I needed to get out in the public's eye and live to be certain I could do it all if I needed to. 

Spoiler alert, I needed to learn all I could to survive in the very competitive world of women. I thought men were bad, but women brought a whole new intensity of competitiveness to their world with other women. In order to survive in the girls' sandbox, I needed to bring a whole level of intensity myself to keep up because on occasion there was quite a bit of kicking and scratching going on behind my back. Once I adjusted to the new world I was in, I was OK after all the scratches on my back healed. Plus, I always kept in the back of my mind, I needed to be better than the average cisgender woman to survive. Mainly because I had so much more catching up to do and I never wanted to get discovered presenting the least bit as masculine. If I ever did and slipped back into old habits, I would have to work so much harder to regain my place in the world as a trans woman.

As I did, I found I naturally was fitting into my authentic life, I found myself at a crossroads of gender. Most importantly, at the crossroads I could see what my end game was. Since I was increasingly thriving in my transgender womanhood, I saw no reason to go back. When I did, a huge weight was lifted off my shoulders and life was livable again. 

I had found my end game was achievable and when I did, all things were possible.  

A Trans Girl's Baggage

 

Image from UnSplash

Like many women, we trans girls carry a lot of baggage when we travel.

If you remember the old Paris Hilton commercials of her mass amount of luggage she brought along when she traveled, it reminded me of the size and number of bags we trans women have to have to transition from a male life to a feminine one. To the typical outsider, they think all we have to worry about bringing along is fashion and/or wardrobe necessities. When in truth, we know which wardrobe to bring is just the beginning. Examples are many and varied, often determined by when we decide to transition in our life cycle. Needless to say, an older transgender woman may have more aspects in her life to consider with family, friends, spouses and employment to think about.

In my case, I waited so long to enter trans womanhood, nearly everyone I cared about as far as family and friends went, passed away. I would not recommend it, but my method really simplified the process of telling my deepest darkest secret to others was made so much easier. In fact, I only had two family members to tell of my authentic life. My daughter and my brother which went half and half for me. My daughter remains a steadfast ally to this day while my brother and I have not talked in over a decade.

Thus far, we have only discussed the larger baggage items and not any of the smaller yet still important things we have to bring along with us as we enter a scary yet exciting new world. Such as, what would we do about the interests and hobbies we have built our male lives around. As far as I am concerned, what I always bring up is my lifetime love of sports. For years, I considered I would have to give up my interest in sports in order to transition. Because I knew so few women who were into sports.

Fortunately, the world around me began to change or I began to see more clearly what was really going in the world I was in. In other words, I began to see other women in the sports bars I was in as interested in the games as I was. It was around this time also when the National Football League began to market their product to women. It became stylish for me to wear my team's jersey into the sports bars I became a regular in. In addition, the other women I began to be friends with were sports fanatics.

All of this combined to make my path to my transgender womanhood so much easier. I can compare it to just having to bring a carry-on bag with me on a plane instead of a large piece of luggage. I was more secure and did not have to give up any of my interests I so enjoyed. 

Perhaps the only problem I had was when I talked to men. With them, I often had to dumb myself down when I talked about topics, I knew a lot about. One time, with a tow truck driver, I needed to finally act as if I knew nothing about the mechanics of the truck, we were in to satisfy his ego. It was my first interaction one on one with a man, so I was surprised how it went. Basically, I was forced to give in to him to just maintain civility on the short trip. The lesson I learned was one I kept with me every time I was with a man.

It turned out I had unpacked a whole new set of transgender baggage.