Making Gender Decisions

 

JJ Hart

Living my truth as a novice transgender woman proved to be more than I bargained for.

Like many of you, I started innocently enough as I rummaged through my mom’s clothes for anything I thought would fit me. Too soon, I found I had fallen in love with the feel of feminine clothes such as undergarments and panty hose. The biggest problem I quickly encountered was the buzz I felt when I cross dressed in front of the mirror just did not last. In the space of a couple days, I yearned to repeat the process of doing my best to look like a girl, repeatedly. I did not know it then, but my mind was attempting to tell me I was transgender and not a cross dresser. In those days, the transgender word was years away from being used or understood.

When I finally reached the age to go out on my own, the mirror remained my best friend. All the way to the point of going places where I could enjoy seeing my transfeminine reflection. I would even go to the big home improvement stores to check out their mirror selection when in fact, I was checking me out and reinforcing my feminine image in my mind. Finally, even my simple search for gender acceptance proved to be too much to take on a regular basis. I needed the public to be my reflection which mattered the most. Or I began to interact with more clerks and servers on a one-on-one basis to see their reactions. The more I explored, the more confident I became, and life became so much easier. In fact, too easy.

The first main discovery I made was the fact that women were much more interested in me than men. It did not matter, if the woman was a clerk, a server or a stranger off the street, they all seemed to share a curiosity of why I was in their world. Many times, there was too much curiosity going around on both sides, I was as curious about them as they were about me. It was about this time when I began to really live my truth as a transgender woman. I always reasoned too, more than a few strangers were drawn to me for that precise reason. They knew I was living my truth. Certainly, there were haters and bigots along the way, but not enough to slow me down. I ended up learning to stay clear of them very effectively.

Confidence was always my key as I learned to live my truth. I knew I was transgender and anyone who paid close attention at all to me, knew I was also. With that out of the way, we could get down to real life and very soon the typical stranger realized I was not the normal cross-dresser they saw on television on one of the many talk shows. I was real and not evil in any way. It worked with other women I encountered and almost never did with any men. So, I was satisfied with my results. I was kicked out of the men’s club and that was the way I wanted it. I guess you could say I was in some sort of a new layered gender reality as I tried to live my new truth.

I would be remiss if I did not bring up how intensely difficult all of this was to the progress of my mental health therapy. Per norm, my therapist said it best when she told me there was nothing, she could do about my wanting to be transfeminine. If I wanted to enough, I would make the sacrifice to do it. All my visits were pointless until I faced my own gender reality. My excuse continued to be, leaving my male life with all the comforts of the privilege I had built up was very risky, so I continued to put it off until it was almost too late and I tried suicide as a solution.

Naturally, the attempt did not work, because I am here writing attempting to help others with similar gender issues as mine. I learned I wanted to live and needed to make the right choice with my life to do it. I was stubborn and waited until the age of sixty to make the change from living a partial male life to a full time female one. All the lessons I absorbed along my long gender journey came back to help me in my final decision. I still remember vividly, when I sat alone and decided to donate all my male clothes to thrift stores and give up my male life forever. A tremendous weight immediately came off my shoulders and I knew I had made the right decision.

 

 

 

 

A New Day

 

JJ Hart, Dining Out. 

This post is a little shorter than the recent ones I have posted but no less important and it involves last night's trip to a restaurant venue we always go to.

It seems, every day is always a new day for me. Last night, my wife Liz met her son for dinner at our favorite restaurant where we dine approximately every other week.

As luck would have it, since the venue is large, we have had the same server several times before. About three visits ago, I wore my new Margaritaville T-shirt I bought during our winter trip to the Florida Keys. Even though I thought it was appropriate to drink a Margarita when our regular server promptly called me the dreaded “sir” word. Sadly, my Jimmy Buffett Margaritaville shirt was not feminine enough for me to pass the gender test. So, I needed to relegate it to just wearing around the house. I was sad.

Last night was different. I wore one of my most feminine lace trimmed tops and our regular server seemed a little gender confused but did not call me “sir” and I was satisfied. Also, one of my favorite things about the venue is I never had any problems with being mis-gendered by anyone. I could just relax and be myself. It was one of the first venues where I could sit and ponder the old days when I struggled to exist as a transgender woman at all. I was revitalized every time I went. Which made it a new day.

In many ways the process taught me how far I have come in living my gender dream, but in so many ways can not give up or relax the process. Even though I don’t wear a lot of makeup, I need to make sure I wear the basics every time I face the public. No pun intended. The moment I let my guard down; I could be reverted to the “sir” word I worked so hard to put behind me.

In many ways, when I transitioned from a cross dresser to full time transgender woman, I knew every day would have to be the new normal for me. There would be no more planning ahead three days or so for the special days when I could face the public as a transfeminine woman. I would be doing it every day. I went into a major wardrobe expansion mode. Just to keep up being in a new gender world. As soon as I dropped my guard at all, I would risk slipping back into the world I waited so long and worked so hard to get out of. Fortunately, I was very paranoid about doing it and I was able to translate my fear into positive feelings about what I was trying to do.

There were many steps backwards on my journey to discover how uplifting and pleasurable my life could be at the age of sixty when I seriously began my transition. The longer I was able to live this new life, every day turned out to be exciting and I was less vulnerable to outside threats to going back to my ingrained old male life. Eventually, life took care of itself as I found new friends and part of my family accepted me. I was able to live long enough and escape the self-destructive behavior I exhibited. Life was just a huge circle, and I was on the slippery side of the circle. I could risk everything to selfishly live my life and make everyday a new one. Or stay the same and wither away.

Naturally, making every day a new day was a challenge. Waking up every day addressing a new life was all I asked for and all I ultimately received. It was who I really was and proved to be a wonderful overall experience of gender transition.

The Clash of Gender Ego's

 

Image from Sherest Gupta
on UnSplash. 

Through most of my long life, I needed to deal with the clash of egos, doing battle for my existence.

On one side, I had my well-worn and battle tested male ego who was doing his best to make it in a world where he did not want to be. On the other, I had my deeply hidden feminine side who only made her appearance in front of the mirror and then went back into hiding. In other words, my male ego attempted to dominate while at the same time, my female ego was hiding, just exactly where she did not want to be.

For the longest time, to make matters worse, I did not think women had much of an ego at all. Except maybe with their appearance. As I made my way through life, I discovered how wrong I was. On several levels, As I always warn about, my male ego dictated how I dressed early in my life when I was going out in public. I fell in love with several compliments I received about my legs when I went to Halloween parties and made sure I showed them off to the extreme when I was going out for the first time. The idea was all well and good except I was doing nothing to overcome my broad shoulders and torso. I had no fashion balance, and it showed with the number of times I was made fun of in public. My male ego had failed me. I was dressing to his tastes and was failing.

It took years to do, but my female ego finally took control and slowly but surely, I began to blend in with the other women around me. For a moment, I even thought my clash of egos was over, but I was completely wrong. My male ego was very stubborn and still thought he had some sort of control over my life. He refused to believe he had lost all his male privileges and nearly got us in trouble several times before he learned the hard way what problems could exist.

One of the biggest issues was the idea of my sexuality and how it would or would not change with my new transgender life. Of course, Mr. Macho recoiled at any thought of intimacy with a man, but Ms. Self wasn’t so sure. Like many women, she had a spectrum of ideas about sex which were not so rigid and paranoid. In fact, I made a concerted effort to date a few men to see what (if any) excitement would happen. It just so happened women turned out to be much more interested in me as a trans woman, my choice was easy to make. For once, my male ego won. For the wrong reason.

One of the earliest instances I can remember of a lesbian woman approaching me happened one night at a mixer/party I went to at a friend’s house in Columbus, Ohio. At the mixer, I ended up approaching another woman and having a brief conversation before we decided to leave for a while and go to a big lesbian club to mingle even farther. We ended up having a good time that night, but since I still had a wife to go home to, I could not stay long enough but visiting with another ciswoman who happened to be a lesbian was a wonderful experience and would set the path for my future. Although, I did not know it at the time, primarily because my male and female egos were still clashing.

By now, you may be asking the question, who was winning the struggle? My woman was, even though my male self would win every now and then, it was as if he would take one step forward and two steps back. On the occasions when my second wife would catch me coming back from a night on the town, he would jump forward into purge mode. Vowing to never wear any female clothes ever again. All the time knowing there was no way possible he could ever keep his promise. I had crossed too many lines in my gender sand to go back, and the fact was becoming increasingly evident to him and my wife, there was nothing they could do. They were waiting for me to face my own reality.

Solving my final gender issue was easier said than done. My male self was hanging on for dear life until the very end, and he nearly pulled all of us down in the process until therapy and suicide came into play. Finally, I needed to pick a winner in my gender ego clash, and I was wise and picked the only way I could go. I put my old male self completely aside and begin to live a transfeminine life I had only dreamed of. I wondered why I did not pick the winning side years ago and live my truth.

 

 

Just Part of Being a Woman?

 

Image on Unsplash. 

Just part of being a woman meant several different things to me.

First, I needed to get there by being able to present well enough to being accepted by other women. Once I arrived, I was able to enjoy the benefits of living in my dream world as well as the drawbacks. The first night I had an idea I was arriving was when I began to be semi-friendly with a man I met at a venue, I was a regular in. He was part of a small, diverse group of people I mixed with often. Sadly, I followed the saga of his quickly failed marriage to another woman in the group. She was an exotic dancer with long black hair, and he was a big, bearded man who rode a Harley motorcycle. Not exactly a match made in heaven. But they went ahead with the ceremony anyway. It failed within a couple of weeks.

I really don’t know why, but from then on most of the group turned against him, except me. I felt sorry for him and could sense the hurt he felt, so we began to talk. Before long we became friendly enough to look for each other when we came in alone to socialize. I can’t speak for him, but I was in uncharted territory even talking to a man at all since I was basically scared to. Who was I to say no to this big good-looking guy who wanted to talk to me? You are right. I couldn’t. I was too shy to even ask him to see his Harley before he rode off to another job in another town and I never saw him again. How different my life could have been if I had pushed my luck as a transgender woman just a little farther.

That fleeting encounter left a deep impression on me, not because it blossomed into anything, but because it made me realize how much of life I had yet to explore. It was a bittersweet moment of clarity: I had spent so much time crafting a version of myself that fit into the world I longed to belong to, yet I was still afraid to fully embrace the opportunities before me.

In the days that followed, I thought a lot about courage to truly be brave, not just in appearance but in action. It wasn't about being bold for the sake of it, but about taking the step that felt impossible, the one that whispered promises of growth and self-discovery. And yet, even as I reflected, I knew that fear still gripped me, tethering me to the safety of the new family I was creating.

It was around this time that I began writing the blog, capturing what I could of the small victories and the quiet heartbreaks that defined my journey. The act of writing became my sanctuary, a place where I could be unapologetically honest with myself, where I could acknowledge my fears without judgment. The words became a mirror, reflecting not just who I was but who I could be if only I dared to push beyond the limits I had unconsciously set for myself. By doing so, I hoped I could help others.

Life has a way of surprising you, though. Just when you think you've missed your chance, it presents you with another, often in the most unexpected of forms. Sort of like the first night I found myself in the middle of four men discussing guy things which of course I knew quite a bit about. Not realizing exactly where or who I was, I attempted to add my comments to the group. The men paused for a moment, then went on with their conversation as if I was invisible. I learned my lesson, entering a male only domain was a big no-no and exposed my new feminine life of having a lesser IQ. 

On my very few encounters with men, I learned to let them lead the way in conversations. No matter how inane the subject matter was. A prime example was the night I always mention when my car broke down and I needed to call a tow truck. Also, to my chagrin, a well-meaning policeman showed up out of nowhere to help. Between the cop and the tow driver, they refused to even listen to the directions I tried to give to my house. Then everything became worse when I had to ride home with the driver. By the time I arrived home, I had nearly reduced myself to playing the dumb blond just to survive the trip.

Just part of being a woman just meant leaving my male self behind, which is what I was trying to do anyway. What I did not count on was how fast I would lose most all of my male privileges I took for granted when I transitioned. All cisgender women go through the same process when they grow up around boys. It just took me a little longer to get there. Or, as my lesbian friends said, welcome to their world.

Plus, there was the new magical world of gender affirming hormones to consider. The HRT certainly contributed to my internal part of life as a woman.

Riding the Gender Merry go Round

 

Image from Stanley Kustamen 
on UnSplash. 

Catching the gender merry go round when it was in mid-spin was never easy. As I always point out, I had no workbook on how to achieve my feminine desires that were available to me.

I often wondered what magical experiences were available to the girls around me but were off limits to me. What did the girls really learn about being feminine from each other? Was makeup one of them? I was jealous because I had none of the early basics of applying makeup. The closest I came when I was painting the model cars I had. I never was very good at skillfully painting cars, so I wondered how I would ever be good at painting myself. Enamored, I remember watching my mom apply her makeup as I looked for any small hints I could follow but I never seemed to learn.

Of course, there was much more to jumping on a spinning merry go round than just skillfully applying makeup. There were clothes to worry about too, and how could I afford them on the very limited budget I was on. I resorted to taking any small jobs I could as a kid to augment the meager allowance I received at home. In fact, my major source of income was a neighborhood newspaper route I took on. When I added all my funds up, I usually had enough money to buy my own makeup, panty hose and other rare items such as a pair of shoes I was lucky to find.

Once I was able to be confident in my ability to jump on the merry go round, then I needed to worry about hanging on. In the early days of my public explorations, I was having a very difficult time presenting well at all and I often was laughed at by others on the merry go round until I began to learn what I was doing wrong, and I could fill out my feminizing presentation workbook. It was a win for me when I could quit using crayons on my face and use them to color my workbook, I was less and less a clown in drag, and more and more an androgynous person for the public to judge my gender. For once, I could rightfully claim my seat along others on the merry go round because I had earned my spot as much as they did.

After a while, the spinning became too much for me and challenged my fragile mental health. The biggest problem I had was my refusal to face myself and my innermost truth. I was never a man cross dressing as a woman; I was a woman cross dressing as a man my entire life. The basic thought of who I really was consumed all my spare thinking. I am amazed now how much I still accomplished in my life as I suffered my mental duress. At times, it seemed my merry go round was spinning completely out of control. Plus, at the same time, I kept accumulating extra male lifetime baggage I did not really want. Sadly, the life I was living kept me from making very many close friends because I just thought I was knowing them under some sort of false pretense. I wasn’t the man they saw before them; I was a fake. Which I hated and added to my problems.

I finally came to the point where I needed to either slow down my merry go round or get off altogether. I just couldn't take it any longer. I certainly was not getting any prizes for putting myself through the anguish of staying on. I had given my ride the best shot I could, and I needed to grow in my transgender womanhood. I had tried my best to outrun and out drink my gender issues, and it was time to face the reality of who I was.

When my merry go round glided to a stop and I was able to look ahead to the new life I was about to enter. I was excited to see and live my feminine reality. I had filled out my workbook and paid my dues and was ready to go. The next time I was at an amusement park I could really enjoy the experience as a transgender woman. If anyone in the world did not like it or approve of me, I didn’t care. I had spent a major portion of my life thinking I was in the wrong. When in fact, the bigots were the ones in the wrong and they were the riders who needed to get off the merry go round first.

Tomorrow Sometimes Comes

 

Image from Mark Attree on UnSplash.

I finally knew tomorrow was here when I started gender affirming hormones or HRT as it also is known as.

It was always my dream to try hormones as a natural progression towards my ultimate transition. By the time I sought out medical care to help my hormonal goals, I had pretty much exhausted my old cross dressing bucket list of situations I could put my femininized self into. I even went as far as pushing myself into situations I should not have been in. But I learned how far I could go.

Through it all, I still did not know how far I could go or have to. Would something come along to change my course or ultimately change my mind. It turned out, hormone therapy turned out to be the salvation to my problems I thought it would be. Quickly, I moved from a minimum dosage to an amount of the meds which would really produce changes. It was as if my body was taken to the HRT as naturally as it could and provided me with yet another what took you so long as I suffered through changes such as my first hot flashes as I was going through puberty again. What took you so long, echoed through the recesses of my mind.

The biggest problem was I was going through all these dramatic changes alone. All my Ciswoman friends would just smile knowingly and say welcome to their world if I brought anything up. So, I did not. I brought back my old unwanted male art form of internalizing my feelings once again. In my mind, it was a shame I could not share the beautiful changes I was going through with no one else. This all happened before my current wife Liz, and I became serious a decade ago.

I continued to realize my tomorrow was here when I was forced to stop wearing male clothes all together and donate mine to the area thrift stores. My protruding breasts were the first thing which gave me away, along the fact my rapidly growing hair was already long enough to wear in a ponytail. My body was telling me it was time to put all my male privilege aside and face the world as a transgender woman. Which meant several things. The main one was I could no longer pick and choose where I wanted to do and how I wanted to dress as a casual cross dresser. Everyday was important and I needed to plan ahead if I was ever going to be successful in finding and living my dream of living as a woman. After going through the motions for nearly fifty years, tomorrow was here.

Fortunately, by this time in my life, I had developed a strong set of allies who had only ever known the new me, so I did not have to worry about my old male self-coming into play. My friends, along with my daughter and Liz formed a strong bond for me and I was able to experience uniquely feminine experiences such as beauty salons with them. In many ways, they made up for the female peer group I never had growing up. My daughter even asked me to speak in front of her temple for my oldest grandsons Bar-Mitzvah not long after tomorrow came and Liz took me on traveling tour excursions as a transgender woman I would have never done without her. You could say, once I got started, tomorrow came crashing down on me. I was receiving what I had asked for all those years. Destiny was telling me, you wanted it, now you got it.

Of course, then I found how the life of women everywhere is more layered and difficult than a male existence. My daughter and I are prime examples when we needed to work together to explain my gender transition to three young grandchildren. We came up with a new name for me which reflected a family background, and the remainder of the process was amazingly easy.

Ironically, my brother came along to ruin my good karma by refusing to back my transition with his wife’s family who are a bunch of right-wing haters. I guess I need to see how the other half lived when it came to the transgender community personally.

As I said, my tomorrow waited long enough to arrive, which was my fault and could only be described as an exciting process when it got here. At least though, I did not crash and burn following a bumpy landing on the runway. I was able to still have enough time to live the life I had always dreamed of in my transgender womanhood. My tomorrows proved to be worthwhile as I lived them out.

 

 

 

 

 

Climbing Walls

JJ Hart

 When I transitioned from male to the feminine person I was all along, I hit many walls.

As it turned out, some were short walls and easy to climb, and some were almost insurmountable. The problem quickly became which were which. Very early on, when life was simpler, the act of applying eye makeup initially presented itself as a major hurdle, or wall. Once I conquered that challenge, I was able to move on to bigger and better things. Little did I know, I would be facing bigger walls to climb. A few were so tall I could barely see my dream of living fulltime as a transgender woman at all.

Leaving my safe yet dark gender closet and trying my hand at living as a novice cross dresser or transgender woman in public suddenly presented me with many new walls to climb. Iniitally, there was the omnipresent pressure of presenting properly in public as a woman. To do it, I needed to overcome how my old male self-thought I should look and change it to how my femininized self knew how I had to look to blend in with her cisgender counter parts. Plus, I needed to do it on a regular basis as people were starting to remember me. There were no more changing names to fit a new wig I was wearing. At least I needed to understand that even though strangers knew I was not a cisgender woman, I needed to prove I was a person who was nice to know and got along in the world. Most of all, I was not some sort of a freak, and I needed to remember in the overwhelming number of cases, I was the first and only transgender woman the public had ever met.

The frustrating part of this time of my life came when I was taking a step forward towards climbing another wall, then slid back down when I hit it. I was rapidly losing all the press on nails I bought as I was trying to climb. I seemingly always had problems with moving like a woman. No matter how much I tried, I still ended up moving like a stiff football player in public when I walked into a venue. I worked long and hard to correct the problem and finally succeeded to an extent. Putting femininized self into motion was a problem so large, it was only topped by the communication problems I was having dealing with the public. Basically, I was scared to death of talking to anyone. It was particularly frustrating when I began to talk to other women, who I very much wanted to be friendly with.

On the other hand, men were not a problem at all, since for the most part, they left me alone. The problem was partially solved when I took feminine vocal lessons and the rest with pure practice. Finally, before I came off being unfriendly with other women, I just gave up, relaxed and did the best I could to enjoy and learn from the conversations I was having.

Before I knew it, the walls were coming down and I was gaining the all-important confidence I needed to reach my lifetime dreams of being a woman on my own terms. My terms became rather obvious over time. No major gender surgeries which I thought were too expensive and risky for a person my age of sixty. I would just have to take all my learned experiences out of the closet, put them together and do the best I could.

Another of one of my remaining tallest walls was doing more for my inner self. I solved it by becoming eligible for gender affirming hormones. My initial thought was the changes I would experience would be external, not internal. It turned out, the internal changes were more immediate and far reaching than the external changes. In fact, I can and should write an entire blog post about my changes on HRT. Briefly, I entered an entirely, the new, softer world. Suddenly, I could cry, and my senses improved. Perhaps the biggest one was I was more susceptible to changes in temperature. I learned all those years of thinking women were faking it when they were cold was true. When I was reaching for my coat on a chilly evening.

Certainly, HRT helped to tear down most of the final walls in my gender journey. I say most because I do not think all my walls will ever be totally gone. After all, I have lived most of my life as a man with all the resultant experiences and privilege. No matter what I do what is left of him will still be with me. His former life will always be with me. I just need to learn from him and conquer all the walls he put up in protest.

Coming Home

 

JJ Hart (Center) Wife Liz on Left, 
Daughter on Right. 

The process of crossing the gender border from male to female, always felt as if I was coming home.

From the beginning, my dual genders clashed, causing me to often sacrifice my already fragile mental illness when I was diagnosed as being bi-polar. Naturally, it was difficult to separate one issue from another when I became depressed and just wanted to curl up in a ball and left alone. On most occasions, I could just cross dress in front of the mirror and take my mind temporarily off my trip to find my true home.

The trip proved to be much longer than I ever thought it would. I never considered it would take me on a fifty-year odyssey. Complete with too many blind curves and dead ends to mention. If I was to attempt to mention any of the major problems I had with my transition was there would be so many more transitions than one. The gender border crossing was so complex, it would take me several different ways at once. I finally came to the point where I was simply trying to raise the bar of living as a transgender woman every time I went out in public. In my earliest days, it meant concentrating on more than just my feminized appearance. I needed to put my appearance, no matter how good or bad, into motion. What good would it be to look like an attractive woman if I was moving like a linebacker.

Every time I made a move forward in my transition, I could imagine myself living my gender dream. Which in most cases scared me more than anything else. What would my life be like without all the male privilege I worked so hard to earn. Perhaps the only stable idea I learned was I was much more than the casual cross dresser who just wanted to put on a dress for certain occasions. As suspected from my earliest days of admiring myself in the mirror as a girl. I wanted to do much more such as be a girl or at the least find out if the public would accept me as one.

I put many hours of work into my femininized presentation. I tried and tried to get my makeup right, even to the point of losing nearly fifty pounds on a diet I undertook. When I lost weight, I was able to fit into my stylish clothes, so it was a huge win for me. Along with the intense skin care routine I followed. Suddenly, I discovered I could use less make up and prove less was more. All these moves proved coming home indeed may be reality if I kept working hard enough. For the first time in my life, I made a concerted effort to achieve a very real goal. My transgender womanhood.

As I said, coming home involved several other minor and major transitions. I began to do so called womanly duties such as grocery shopping into my days when I could. I also added gift shopping at Christmas (and other times) to my time as a woman. Through it all, I was learning how the world would possibly accept me when I was able to make it home. All these actions showed me the feasibility of proceeding with my gender plans, though many questions remained unanswered.  Such as, what would I do about the basics of my life such as what to do about my wife, extended family, friends and having a basic income to live on.

It was around this time when destiny set in to provide me with major answers in my life. Tragically my second wife passed away, at the age of fifty, along with most all of my very few male friends. As far as family was concerned, my daughter stepped up to be my most steadfast ally, until my third wife Liz stepped into my life. Finally, I learned if I waited a relatively short period of time, I could take an early retirement on Social Security and solve my financial issues. The only loss I sustained was with my brother and his extended family who roundly rejected me. So much for close family ties.

When I made it to my true home, it was like day and night. It was as if a huge weight was lifted off my shoulders. My mental health improved with the help of therapy, and I was better able to face my life on a more equal basis than I ever had before. Surprisingly, I had very little re-arranging to do to live in my new house. It seemed my inner female self-had been not so patiently waiting for her chance to take over my life. Once she earned her spot in the public eye, she knew exactly what to do to survive.

 

 

The Gender Comfort Zone

Image from Thomas
Vitali on UnSplash.

 It took decades to reach a point where I could say I was comfortable with my gender issues. The point where I could look at myself in the mirror and say I was satisfied with the image I saw.

Before that time, I always just saw my old male face staring back at me. Finally, I glimpsed the beginning of seeing a femininized version of myself. I had hope for the future. The frustrating part was trying to figure out what to do with my new gender life. Up to that point, I felt my gender desires for the most part was unreachable.

Even still. I worked very hard to take myself out of the world of being male and did see glimpses of seeing my authentic feminine self-hiding behind my everyday boring life. Before long, I was spending every spare moment thinking of the next time I could work on my femininized life. Little did I know at that time how long and difficult my gender journey would be. Up to that point, I considered a woman’s life to be mostly tied in with their ability to wear pretty clothes. Along with the seasonal changes to their wardrobes. At the time, my second wife was telling me the truth about pursuing my dream. In other words, a woman’s life was so much more than how you looked.

I found out the hard way, she was correct when I started to enter the world as a transgender woman. I needed to really begin to study the cisgender women around me if I was ever to be successful. I did not know it at the time; she meant learning all the layers of existence women go through in their lives. Such as having the man she was married to (me) go away because he wanted to be a woman. I have the utmost respect for her because she put up with me when she did during our twenty-five-year marriage before she passed away. From a totally unexpected massive heart attack. Tragically, the only unwilling gender mentor I had in my life was suddenly gone.

I ended up making the best of my new life without her and ultimately did find my comfort zone as a transgender woman. The most difficult time in reaching my new zone (as I always point out) was when I was forced to communicate one on one or face to face with another woman. I was so scared to speak I tried not to talk at all. Quickly I learned that idea only portrayed me as being either unfriendly or worse yet, bitchy. No way to make new friends as I found my new comfort zone.

Once I began to arrive totally at my transgender womanhood, I was unbelievably relieved. Even to the point of wondering if I could finally be happy for the first time in my life. Happiness was never a priority in my family, and it took me shedding my old male life to find how it was to be happy.

On occasion, I think I oversimplify the transition process I (or other transgender women or men) go through just to live their lives. Especially, these days when so many roadblocks are thrown up in our lives by the orange hater in the White House. But that is another topic all together, since my views are known.

Wherever you may be in your life of gender transition, don’t despair too far if your closet is dark and locked to the world. You never know when your life can change, and you can achieve your own level of gender comfort. Plus, your level of comfort could be vastly different to mine or anyone else’s. There is no right or wrong when it comes to any of these.

It has also seemed to me; I leased my old male life and was simply looking for my deposit back when I was allowed to finally go behind the gender curtain and cross the border. What the ciswomen gatekeepers did not tell me was I not going to get much of my deposit back I had built up as my old male self. Male privilege was gone, along with any security I had built up. In the end, I was able to give up and sacrifice all I had lost in order to enter the comfort zone I had gained.

 

 

The Inner Girl I Never Knew

 

JJ Hart, Club Diversity, Columbus, Ohio. 

As I was growing up, the girl I saw in the mirror did not seem to be quite real. Mainly because I was still caught in the male world I was born into. It seemed the more I struggled with my reflection, the more depressed I became. It did not seem fair I could not enjoy all the perceived benefits I observed from the girls around me. I say perceived, because it was not until I was able to go behind the gender curtain to see life was not always easier for the women around me.

Life moved on and I discovered always being the pursued by the opposite gender (males) was not often good. The problem was being pursued by the correct male. Not a scary, creepy or toxic one. Another problem I had learning from the females around me was I was so very shy and afraid to talk to any girls at all. So, I watched the dating scene from afar and wondered why I couldn’t be a part of it.

The main problem I had other than being shy was the gender dysphoria I was always suffering from. I was riding a dual edged sword. On one edge, I was struggling to meet the demands of my parents as their oldest son, and on the other hand, was the fact that some days when I woke up, I did not know what gender I wanted to be that day.  Problems I would not have wished upon my worst enemy. Finally, I did the only thing I knew how to do to survive, I went exploring. Or I should say, as I was growing up, I saw the girl looking back and then my transgender side went exploring.

My male self-stayed home as my feminine side attended transvestite – cross dresser mixers searching for answers to my true self. Ironically, the mixers just added more questions than answers. I discovered more layers in the cross-dresser community than I imagined existed. There was everything from male admirers at the party, all the way to impossibly feminine transsexuals I never knew existed. The biggest surprise was that my inner girl was again having a hard time fitting in.

One of the problems was, the transgender term or the knowledge around it had not been widely known at the time. When I finally heard of it, I thought it really described me, and I began to research it more. The tipping point came as I began to explore the public more and more. As I began to experience a new life I only dreamed of, the more natural I felt, and my missing girl was finally freeing herself from the confining world of my closet’s mirror. At that point, my pressure of transgender womanhood began to increase. It was less and less a fun game and became a very serious journey. The real reason why was the trip to my dream was becoming possible and was I going to risk everything my male self-had worked so hard to achieve.  

Nothing turned out to be easy as it seemed as I entered the world as a transgender woman. My focus needed to be dealing with other women on a one-on-one everyday basis. Over a relatively short space of time, I grew into the woman I needed to become to survive. Or my inner girl was growing up into a woman and I needed the gatekeepers to allow me to play in the alpha girls’ sandbox. Very soon, I reached the point of no return, and I had lost most of my past anyhow, so I had nothing to lose. My second wife had passed away along with many of my close male friends, so there was no better time to put my old male self completely in my past.

For the longest time, I never understood what my inner girl was observing and learning from. I found out when she finally had the chance to emerge into the world, she knew what to do. I thought in a small amount of time, she made a major gender adjustment and began to enjoy the dream I had attained. By I, I mean my male self was needed to propel the changes I went through. He provided many of the materialistic necessities I needed such as fashion, hair and makeup to get by. At the least, the entire process was very complex when I put my life into a gender mixer and hoped for the best.

There were plenty of times when I had the opportunity to purge my feminine belongings and return to a male life I never really wanted. When I kept coming back, I finally learned my inner girl was screaming at me to do the right thing. The right thing was to live out the remainder of my life as a transgender woman. Destiny led me to success.

Survive or Thrive as a Transgender Person

 

Image from The Blow Up on UnSplash.

It is easy to say, there is a major difference between just surviving and thriving as a transgender woman or transgender man. 

During my very long gender journey, I spent most of the time just surviving. Mainly when I existed by admiring my femininized version in the mirror. I did not understand at the time the difference in wanting to look like a girl, I wanted to be a girl. The entire process caused me huge amounts of duress and ruined my fragile mental health. Primarily because I had no one to explain to me how there were many others who were suffering in their own closets. In those days, there was no internet to provide any information whatsoever. No one to connect with at all. On some days, the loneliness was unbearable.

Still, I survived and continued to follow my own path. I was able to do what worked for me and gradually was able to join the public flow as my own extreme novice version of being a woman. As with any other newcomer, I paid my dues as ugly as they were. Along the way I kept thinking about what I was doing. Why would I ever consider trying anything as crazy as actually following through on my feminine desires to live a transgender dream.

Following a certain tipping point I went through, my desire to do more than just survive as a transgender woman became too much to handle. I was becoming increasingly more mentally unstable and self-destructive to the point of attempting suicide when I could take my life any longer. Fortunately, I was not successful and then set out to do more than survive.

I knew enough to know what I needed to do. Make a deeper dive into myself and explore my own femininity. I also knew I had to leave the mirror behind and substitute it for the world. To do it, I had to set my fears aside and look the other women I inevitably faced as the primary gate keepers in their world. A primarily had to learn the basics of passive aggressive behavior. Was another woman really letting me into her world or just acting as if she was. I learned the hard way to have eyes on the world from behind my back.

By succeeding in the world in my transgender womanhood, I was essentially carving out my own niche. Primarily because most of the world had never seen a transgender woman at all. When I immediately established, I was not a scary person at all up to no good, normally I received a good reception from other women, not men. With women at least, the gate was open for me to walk through. With men, my interactions were few and far between as their frail sexuality was threatened. I adjusted to my new world very easily and thrived more than I ever thought I would.

Suddenly, nearly all my spare time was living as my feminine self and when I was not, I was thinking about her. Or why was I wasting my precious time as a man when I was thriving in my new world as a woman. Each evening, I was out I had the opportunity to discover more and more the nuances I would need to thrive in the world as a transgender woman. Still, some nights I was still struggling to take everything in as my senses were barraged from many different angles. Specifically, when I started gender affirming hormones. From that point forward, I was able to attempt to sync up my internal with my external self. As I thrived, my mental health improved as I was finally able to live as my true gender self.

With age, I learned life is, but a big circle and I was able to find my way into thriving more than surviving. Many days, it was a struggle but finally finding my way was certainly worth it in the long term. Since I spent such a long time just surviving, I felt so much better in my new life.

 As the image says, success only comes from failure.

Seismic Gender Shifts

Image from AC on UnSplash.

I received a response from a reader seeking more input on how I was able to integrate myself into the lesbian and sports bar cultures.

First, thanks for the question as it is a complex one to try to answer. It turned out, the lesbian culture was the most difficult to be accepted into.  I began my journey in Dayton, Ohio around the year 2005 while my second wife was still alive. Back in those days, there were still lesbian bars in business for me to go to. It is important to note, one of them was essentially a lesbian biker bar and they hated me. Especially when I played “Shania Twain’s” I Feel Like a Woman in the bar. Even still, they barely put up with me until I found a better venue to go to.

It turned out, relatively close along the road was another small lesbian bar which had just opened, so I tried it out. Imagine my surprise when the first bartender I saw, knew me as my male self also. She saw through my femininized appearance, and I was treated very warmly, which helped me gain acceptance from the other patrons. I was able to relax and look around at the dynamics around me.

What I immediately noticed was where I fit in the layered levels of women in the bar. There was everything from very masculine butch lesbians, all the way to their femme girlfriends who came with them. I learned very quickly, with my jeans, boots and makeup, I fit right in with the femme lesbians, even to the point of attracting attention of a few of the butches. Who, on occasion, bought me beers and flirted with me. In fact, my first dinner date was with a super butch who went on to become a full-fledged transgender man. Keep in mind also, back in those days, I was much younger and could present much easier in public once I learned the basics. Such as, what I was going to wear when I went to a lesbian bar. There would be no dresses or skirts for the evening.

It is also important to note, my next foray into the lesbian culture was pure luck or destiny if you don’t believe in luck. This is where my sports bar experience comes in. Keep in mind, I had managed sports bars for a living in my past and had a basic knowledge of how I would go about becoming a regular. Again, I needed to dress to blend, stay friendly, smile and tip well. My plan worked well and soon I did become a regular at several venues where I had gone to as a man and always wondered if I could repeat my visit as a transgender woman.

On one night, one of the bartenders asked me if I would be interested in meeting her single lesbian mother and I said yes. We ended up getting along well and even ended up adding another lesbian woman by complete chance who I ended up partying with for years until I met Liz and moved to Cincinnati. As destiny would have it, Liz identified as a lesbian also, so my circle was complete. I was basically protected from the world until I could learn many of the nuances of being a transgender woman. Such as, I did not need a man to justify my existence.

I guess you could say, my seismic gender shifts just came along when I needed it, or when I was questioning my sexuality. I had always gotten along with women easier than men and their interest in me sealed my future in the world. I enjoyed immensely going to lesbian mixers and being flirted with on occasion. I always thought it was because I was hitting some level of middle gender with some women who were not intimidated by a woman who used to be a man. They were intrigued and even impressed by my honesty in how I approached my life.

Sadly today, around here at least, there are very few pure lesbian bars left to learn in, and the younger generation seems to be more accepting of the transgender world. Which is what is scaring all the politicians, shoving unjust laws down our throat. However, I don’t want to get too far off the subject and just say my acceptance into a totally new culture as a transgender lesbian came at a cost. But a good one and I had friends.  

Not an Act, not a Phase

JJ Hart Speaking Up at a Trans Wellness
Conference.

Very early on in my crossdressing experiences with the mirror, the vast majority of feminine fashion and makeup I could find came from my mom. As I grew of course, I was guilty of stretching her clothes and ruining some of her makeup.

For some reason, she never brought up my passion for being feminine. Plus, she never found my secret hiding places for my clothes. I think now, rather than confront me about a problem so intense, she chose to ignore it, thinking it was a phase and would go away as I grew up. If the truth be known, there were times when I wished my gender issues were a phase too. Those were the times when I "purged" or threw away my feminine clothes and makeup, swearing never to cross dress again. Of course, every time I purged, the pressure would build again, and I would start all over again to femininize myself. Over the years, I came to learn my connection with the feminine gender was anything else but a phase. It ran much deeper in me. Ignorance was bliss until I began to face the reality of who I was. 

It certainly was not a phase in my life which made my cross dressing anything but an act also. My experiences helped to reinforce the fact I was not trying to fool anyone when I first entered the world as who I labeled as a novice transgender woman. 

So, if I was not in a phase, or just acting like a woman to fool the public, who was I? I was in a personal struggle to search for any idea I could latch on to until I finally had to face the reality of my transgender womanhood. Yes, I went through all the questions of just being in a gender phase, all the way to thinking I was just trying to fool the world when I attempted to present myself as an attractive woman. 

Once I did come to the point where I truly accepted myself as who I really was, the entire process helped me to establish myself in the world and make new friends. My worst fears of being viewed as just a man who put on a dress and makeup as a part time basis were never realized. On the other hand, I played upon the fact I was different from the rest of the public as a transgender woman. If I was to be unforgettable, I most certainly needed to make sure I was making a positive impression. I spent much of my time listening to other women. Trying to pick up the smallest nuances of a ciswoman's life and how I could apply it to myself. 

As I advanced along my long gender path, I needed every small boost I could get to get me by with several close calls in an unfavorable world. It took me years to understand my gender issues were anything, but a phase and I was not a glorified drag queen in the world. It just took me more time to prove it to others. Basically, because I was scared of the knowledge of who I really was and feel secure in my transgender womanhood.

The Forgotten Woman

Image from UnSplash.

 Over the years of gender infighting, I needed to carefully sustain my transgender womanhood because she often was the forgotten person.

To begin with, she began life as a second-class citizen in my world when I was born as a male in a male dominated family. Essentially, she had two walls to climb immediately to survive at all.   First of all, she did not have any on hands guidance from mom or girlfriends to show her the way through life and secondly, my male self was successful at all in the world, she was completely forgotten. The fragile complement between my genders had to be maintained at all times or she would disappear. Many times, I asked myself why I wanted her along to begin with, but the answer kept coming back, I needed her.

I discovered the hard way, the occasional trip to the hallway mirror dressed as a girl with full makeup, just was not going to cut it. I just needed more. If I could manage to look like a girl, why couldn't I be a girl, if only in my mind. The problem became, when I had to return to my male reality, I needed to forget my girl self altogether. Many days, it seemed like cruel and unusual punishment. when the only true punishment came at the expense of my already frail mental health. All too often, depression would set in when I forgot my feminine self and could not least appease her by cross dressing in the mirror. 

Another problem was, the more I appeased my forgotten woman, the more my male self-hated it. He fought hard when any portion of his life was threatened. He tried his best to make it easier in life by gaining white male privileges which were difficult to give up. I became successful as a male, but try as I might, I could not forget my inner woman. Who, at the time, was learning more and more how to establish herself in the world. Many times, my male self would win the battles in our life when along he was losing the war. A typical female move he was too blind to see as he blustered along in life. 

When my forgotten woman became less forgotten and more accomplished, my male self-started to panic as he could see the end in sight. Without being a winner. Basically, he teamed up with my second wife to attempt to save what they could of my life. At that point, decisions needed to be made in the worst way. My so-called forgotten woman had learned she could indeed live a life on her own terms. The ability to stand on her own two feet after all those years in a closet was so liberating, she knew she could never go back and, on the other hand, my guy knew deep down he was defeated. 

Living a transgender life she had always dreamed of was suddenly all that mattered. She dictated I start gender affirming hormones to feminize my body outside and inside and that was just the start to being accepted in the world. At that point my forgotten woman was not forgotten anymore, and she got her just due for all the years she waited for control. She loved every bit of it.

Transgender Adjustments

 

Image from Markus Winkler
on UnSplash.

No matter how you cut it, life is nothing if not a series of adjustments.

As we enter school and learn to adjust to the other kids around us, we discover the basic differences which go far past the genders. As far as boys go, we learn some are toxic, some are athletic, and others perceive themselves as leaders at an early age. I went to a very small rural school and basically went to class with the same students from kindergarten through the ninth grade. Plenty of time to form cliques such as who were the brains, the hell raisers, the athletes and yes, even the losers. 

The one clique which I never had the chance to join was the one with gender issues, or the boys who wanted to be with the girls. I was very sure I was the only one with such issues, so I needed to make whatever adjustments I needed to make on the down low. No other person could ever learn of the adjustments I truly wanted to make but could not. 

As I made it through my early school years, the complexity of my adjustments to gender increased. I remember going to a high school festival where I saw a male student in drag for the first time in my life and was fascinated. If he could do it, why couldn't I? It was around this time of my life also when I heard the rumors of one of my fellow students who had attended a Halloween party dressed as a girl and was prettier than his sister. All of it gave me a brief glimmer of hope for my future. Perhaps there were other males who wanted to be girls also. Sadly, it was just two instances of learning of an outside world of gender adjustments before "Virginia Prince" and her "Transvestia" Magazine came into my world.

"Transvestia" rocked my world with its articles and pictures of cross dressers or transvestites everywhere. Seemingly, the only acceptance requirement you needed to have been, was to be heterosexual which was no problem for me. Of more importance was the fact the side organization call "Tri-Ess" I believe, held monthly mixers in Ohio within driving distance of where I lived. All I needed to do was fill out an application and be approved to meet others with similar gender adjustments for the first time in my life. 

As I discovered, when I first began to attend the transvestite-cross dresser mixers, how much more adjusting I would need to do. I met so many others of differing backgrounds from basic admirers to ultra feminine transsexuals, my life was changed forever. Sadly, I had plenty of time between mixers to figure out how I was going to adjust to the new world I found myself in. The only realization I came up with was, there were very few at the mixer who were close to me in my desires and adjustments I wanted to make. Plus, I had a spouse to attempt to explain it all to. 

Sometimes, I am not as naive as I let on, and I knew all the action behind closed hotel room doors was not heterosexual in nature but beyond that, nothing I saw really surprised me. Like I said, I came away from the mixers knowing I had many more adjustments in my gender journey which in reality was only beginning. Little did I know, life would take me in so many different directions before I could settle into my transgender womanhood. I would have a daughter to raise, marriages to negotiate and jobs to take on in my life. 

In many ways, I am no different than the rest of the world except I have gender issues to contend with. I don't expect any special treatment but then again, I don't need to be discriminated against either. I was only doing what came natural to me by trying to survive in the only world I knew. 

In the Passing Lane

JJ Hart.

Early on in my life as a very serious cross dresser before I came out as a transgender woman, I obsessed about my presentation as a woman. Or, in other words, was I "passing."

At first, I went overboard and tried to appease my male side and dress sexy. Naturally, I was a dismal failure with my choices and ended up attracting too much negative attention to myself. After too many disastrous evenings in the public's eye, I finally learned my lesson and began to blend in with the cisgender women around me.

The problem was, still trying my best to slip behind the gender curtain and survive as a transgender woman was very difficult. At the time, a transgender woman friend of mine said it best when she told me I passed out of sheer willpower. She was correct, and I knew I was never the most attractive woman in the room but none of that really mattered as I was beginning to live the life I always had dreamed of. If others somehow resented it, they would just have to get over it. 

Being the keen observer of women, I always was, I found out not all cisgender women passed in the classical sense either. The skillful ones worked around their physical appearance issues with fashion and makeup choices which flattered them. I figured if they could do it, so could I. Finally, my fashion and makeup became second nature to me. At that point, I was not passing out of willpower but more out of inner confidence in myself as a novice transgender woman exploring the world for the first time. Once I found myself in the passing lane, it became easier and easier to stay there.

Even though I had fewer and fewer accidents in my quest for transgender womanhood, I still suffered minor bruises along the way. Mainly from cisgender women who completely did not want me in their world and went out of their way to show me.  Many of the attacks I suffered from were passive aggressive in nature and they took me awhile to get used to, but I did. I developed the extra sense most women have for the world around them and went on with my life as a better person. Secure, I was doing the right thing in my life and did my best to stay in the passing lane. 

These days, I have the benefit of age on my side. The genders naturally blend with age, so with long hair and a little makeup, I can survive in the world. Also, I don't have the vanity about my feminine self I used to have. Plus, I am so fortunate to have my staunch ally and wife Liz by my side the overwhelming amount of the time. An example was the vacation we went to the Florida Keys on a tour bus. If you are not familiar, one way or another on a tour bus, you get to know others. On the trip, I knew I had it made in the passing lane when a couple of women asked if we were sisters. I immediately relaxed for the remainder of the trip.

Overall, since finding my way into the passing lane was a matter of sheer will power. I had always believed if you wanted something bad enough, you could achieve it. Deep down inside, I never had wanted anything more than to be a woman. To arrive at my dream, I needed to get into the passing lane and stay there. Using whatever feminine tricks, I could find and use.

As "Stana" from "Femulate" once said, make sure you properly signal before you get in the passing lane. Once you make it, you will love it.

A Complex Day

 

JJ Hart. (right) Mother's Day 
last night. Liz on left.

Another Mother's Day is here and as always, it presents me with many complex emotions.

First of all, as I was growing up, my mom was many times the dominant parent in the family, I remember vividly watching her apply her makeup, heels and hose. She was from the WWII generation where a woman's appearance was very important. I think she did a wonderful job maintaining a family of males immersed in boyish struggles. Dad was always present, and was often the deciding factor in our family disputes but mom ruled in all the other areas such as day-to-day discipline between my younger brother and I.  

My mom and I were much alike in many ways. I resembled her except I was close to six foot tall, and she was only five foot two, which made it quickly impossible for me to squeeze into her clothes. Over the years, she never let me know that she knew anything about my cross-dressing habits. Looking back now, I do not think I could have hidden all my feminine collection of clothes and makeup so well from her. She was somehow just ignoring me and my gender issues as just a phase. 

My life as a "transvestite" (as it was known back then) stayed hidden as a topic between mom and I until I was back home after being discharged from the Army. The sit-down did not go well and ended with her offering psychiatric care. From there, the subject of me wanting to be a woman was never brought up again during her life. For years, I held her feelings against her but then started to slowly change after I started to mellow within my own transition. I began to realize, mom was just dealing with life under the only circumstances she had ever known, and change was not in the cards.

What I ended up doing, was honoring her when I legally changed my name. I femininized my maternal grandfather's name as my first name and used my mom's first name as my legal middle name. It was my way of honoring her for all of the sacrifices she made for me.

Then, there was the complex problem on what the kids in my life were going to call me on Mother's Day. Initially, my daughter referred to me as her "parental unit", then began to slowly change over the years. Several years ago, I wrote a blog post which mentioned the first Mother's Day when my daughter referred to me as Mom. Even I was embarrassed to refer to myself as a mom, but I was surprised and flattered my daughter did. 

Now, both my daughter and my wife Liz's son both refer to me as mom on Mother's Day. One way or another, the day will forever bring complex emotions to me. I did receive many negative reactions to my Mother's Day posts, so I will temper this one by saying whatever you believe and however you are referred to, have a wonderful day. 

Doing the Work

 

Image from UnSplash.

In my case, I spent decades doing the work to be able to express my true self as a transgender woman. 

Perhaps you noticed I did not say the work I put into changing my gender, because my gender was always set and it was never the birth gender (male) I was stuck with. The first reality I needed to deal with was I had no feminine characteristics to speak of, so I needed to work harder. When I became serious about women's fashion I could find to fit me, I better shed as much weight as I could. In a fairly short period of time, I managed to lose nearly fifty pounds which made it much easier to find fashion which fit me. 

At that point, I needed to go on a thrift shop shopping binge to show off my new femininized body. If I was careful and shopped well, I learned I could really find a few fashion gems at a price I could afford. After I was able to lower my body weight, I began to work on my skin. Since I was already exfoliating on a daily basis by shaving, I began to apply regular moisturizer to help maintain a soft appearance and use less makeup. Soon, it became apparent to me, my work was paying off to being able to jump the external gender border I was facing.

Little did I know, the real work was yet to come. I was sadly mistaken when I learned just appearing as a woman was not going to be enough. The deeper I went into my new feminine rabbit hole, the darker my journey became as I kept discovering new ways to move forward or back. As I let my gender lantern burn the surroundings finally began to look familiar. But it was only after I put in the work to know the people who were trying to interact with me. Mostly women approached me because I think they were just curious what I was doing in their world and were not afraid of me. Doing the work, I was doing, almost meant women in particular reacted to the honesty of living out the life I desired. Men for the most part just steered clear of me because I threatened their sexuality.

Little did the women know, I was learning as much from them, as they were from me. I was fairly sure I was the first transgender person they had ever met and when I repeatedly appeared in front of them was proof, I was more than just a guy putting on a dress for the fun of it. I was enjoying the entire process more than anything I had ever done in my life, and the time I spent learning was very much not like work. 

What I did learn was doing my gender work and had the opportunity to graduate from all the work and live my reward as a full-time transgender woman. The work was difficult but enjoyable because of all the layers of experiences I needed to master before I could move on. If I was to recommend any basics to a gender compromised person, it would be not to get disappointed with your progress. You can progress on your own timeline. Mistakes will be made, but you can learn from them. 

Perhaps, most importantly, keep in mind the gender work you put in represents your journey is not a sprint but a marathon. How you finish is the most important facet to consider.  Some will run faster and some slower but just finishing is the main goal if you want it to be.

Finding Your Comfort Zone

 

Image from UnSplash.

Being a transgender woman, trans man or cross dresser means you need to find your own level of comfort as you transition.

For all sorts of reasons, some of us decide to go all the way from gender realignment surgeries to deciding to stay in their gender closets. It is a difficult decision to face the possibility of losing everything in the life you have worked so hard so succeed at over the years. 

In my case, comfort levels came sparingly to begin with, then increased in frequency as time went along. For example, I had an exceedingly difficult time becoming situated as a novice transgender woman in the world. Possibly, most of my problem came from my own refusal to face up to who I truthfully was a person. My gender situation led me to a very bad situation where I was stuck between the two binary genders, male and female. Of course, I still needed to maintain my male world in the job I worked, but on the other hand, I was spending every spare moment I had trying to reach my comfort level as a trans woman. The end result was, because I was denying my true self (female), I was wrecking my already fragile mental health. 

Fortunately, I was able to work my way through my messy mental problems and come out rather unscathed with the help of a good therapist. Together, we were able to separate my bi-polar depression issues from my transgender issues which dominated my life. And I mean total domination. I was very into advancing my life in a feminine world and attempting to figure out how and when I should let go of my old male self. Finding my comfort zone finally began to come in stages.

What I did was set up what I thought was a mini bucket list of things I wanted to do as a woman. Or at least try to. As with anything else in life, I sailed through a few of the items on my list and hit a brick wall on others. Overall, I was able to use the confidence I gained from my successful feminine ventures and go back to the drawing board and figure out what I was doing wrong on the others. For example, one of the best things I did was stop going to the gay venues where I was only perceived as a drag queen and began going to the sports venues I was comfortable in. When I did, I was encouraged to begin to build a whole new person as I quickly began to establish myself as a regular. Since my business background was in similar venues, I knew the basics of establishing yourself as a regular. Show up often, try not to be a distraction, smile often and tip well were the basics. Since I already stood out from the crowd as a transgender woman, the rest was easy. 

Through it all, the comfort zone I needed the most was access to the woman's room, for obvious reasons since beer was my drink of choice. I was overjoyed when rest room access was granted to me when I became a regular. I even was invited to join other women when they made the short trip to the bathroom. I was very sure I had arrived. 

It is easy to equate being in a gender comfort zone with acquiring all important confidence to get by in a new world. Life was amazing when I was a woman and hell when I was not, so finally, even I could tell a change was needed. No matter how complete the separation would be.

My needs had changed from my old male days and to not face them head on would be a return to the same old gender problems I had faced my entire life. For once in my life, I decided to do the right thing, and I found my comfort zone. My male self-gave up and freed me up to build my transgender womanhood. 

Gender Bystander

JJ Hart (left) and wife Liz (right).

It took me many years to learn I was nothing more than a gender bystander in my life.

As a young male type, I was always painfully shy of strangers first and women in particular. Girls seemed to live a magical life I could only dream of. In particular, the girls were the ones who were allowed to wear the colorful, pretty clothes while I was stuck in the same old drab male fashions. The closer I watched though, the more benefit the girls around me had. While I was too shy to even ask any girls out on dates, the attractive girls always seemed to have no problem with attracting attention. 

The problem with being a bystander was I saw only one side of the spectrum I was looking at. For example, I learned much later in life being the pursued gender (women) did not always mean good results. As if, what if no one pursues you? And what if the male pursuing you happens to be a toxic guy and you are stuck trying to get rid of him. So much to consider when you are a gender bystander on the outside looking in. 

I needed to pay my dues before I could ever begin to consider I was anything more than a bystander in my own life. Specifically, I needed to get past the impostor syndrome I was feeling on the nights I was feeling comfortable in my transgender womanhood. I needed to stop feeling I was looking down somehow on another completely different person, when in essence, it was the dominant feminine me all along. It was not until I completely accepted my true self, did others accept me also. Magically it seemed, my gender doors swung open, and I was given access behind the gender curtain of cisgender women everywhere. It was then I began to explore what I would do about my sexuality.

When all of this was happening, most everyone around me I knew from the transgender mixers I went to were seeking their feminine validation from seeking a man. Which meant also pleasing a man sexually. My problem was, being a bystander or not, I had never desired a man in anyway shape or form, so what was I to do? What I attempted to do was explore the world of men from a transgender woman's perspective. I went online, and I tried to find men to date to no avail as I was stood up more times than I care to remember. I only was able to go out with men a few times and one of those was with a transgender man. 

Finally, destiny stepped in, and I found a group of lesbians who would accept me which I always mention. Primarily, the lesbians showed me I could stand on my own two feet as a femininized person, and I did not need at all a man to validate my existence. When I did, I stopped being a gender bystander. I knew where I was coming from, and my goals were clear. I needed to begin HRT or gender affirming hormones as soon as I was approved for them. By doing so, I was giving my feminine self an extra tool to assist in her development. 

For the first time in my life, I was no longer a gender bystander in my own life. I discovered women did not receive all the breaks and, on the other hand led a very complex and layered life. Sometimes carefully crafted with or without men. It was quite the journey, and I was so pleased I could do it and survive. It was so enlightening not to be a bystander in my own life anymore. On hands help was the only way to live.