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.

My Gender Workbook

 

Trial and error were my main learning directions when I was initially following my gender path in public. As my workbook on how to be a girl or woman was never filled out at all, I had no other recourse in which way to go. I just didn’t know, which meant I never would unless I had the courage to learn myself.

Missing the peer pressure other girls my age had when they grew up really hurt and I was jealous in so many ways. I missed sleep overs and other times girls came together and discussed so many secret issues I was not allowed to know. Which included when they compared makeup routines when I was left to experiment all alone.

Survival as a novice cross dresser became my inner motto as I struggled ahead in my male life which presented its other set of challenges. Such as dealing with sports, cars and bullies. Having interests such as sports helped to keep the bullies away, especially in my male dominated family. If I was careful in staying in my closet, no one had any idea of who I really was as I was filling in my workbook. Many times, I was in despair because it seemed I was not gaining any ground towards my dream of living as a fulltime transgender woman. First, I needed to discover if I had any possibility of success to succeed at all. Which started the so-called bucket list of things I needed to do as I pursued my workbook.

The biggest problem never changed. I never had much help when dealing with the basics of femininized fashion, hair and makeup. It seemed to me, every woman I met expected me to already know the basics and it was like a “C
atch 22” of being a woman. If I did not know the basics on my own, no one was stepping up to help me and If I did know, I did not need it. Sort of like when you cannot land a much-needed job because of no experience and you cannot find any experience because no one will give you a chance.

Perhaps, I am more fortunate than other cross dressers of transgender women because quite early in my life, I persuaded a cisgender woman to help me dress up head to toe as a woman. I thought if a woman with a lifetime worth of experience could help me, I could fill out my workbook, with help. Ironically, after the makeup was over, I was not impressed and felt all the time that I was on the right path and could do the same feminine work on myself. Of course, I need to point out I had already put years of time and effort into refining my fashion and makeup techniques.

Just when I thought I had reached a success point in my gender transition, my teen cross-dresser years set in. The problem was, I was already a testosterone poisoned thirty something man seeking change. My transition out of my teens was painful and not easy to do but I finally made it out after many tears from public abuse. On the other hand, my gender workbook gained another chapter I gladly filled out.

On another slightly different topic, I heard from “Michelle” who is working on her own gender workbook and was commenting on my “Seismic Gender” on the lesbian culture and transgender women: “I really love how you described finding your place along that femme spectrum. It makes me think about how much of this journey is trial and error—figuring out what to wear, where to go, how to be in these spaces without losing yourself. And yeah, sometimes it really does feel like the universe nudges the right people into our lives at the exact moment we need them.

Honestly? Reading this gives me hope that I’ll find my own version of that someday.”

Thanks for the comment! If it helps, at that point I had given up on ever finding another special person for the rest of my life, and the most amazing thing happened. I did find my wife Liz, or I should say she found me. It happened primarily because I gathered the courage to repeatedly put myself out in the public’s eye.

Just be careful when you do it and take your time to properly fill out your workbook and you can be successful on such a major undertaking as living as your authentic self.

 

 

 

Seismic Gender Shits...from Gay Bars to Sports Bars

 

My Trans Friend Racquel and Friend.

In many ways, this is only a continuation of yesterday’s post about seismic gender shifts. This time though, I am going to focus on my foray into leaving gay bars behind and beginning to go to several of the major sports bars in the area where I live.

As I see it now, going to lesbian bars was more of a learning experience but being accepted in sports bars was a dream come true. As far as the sports bars were concerned, I can break them down into two types. The smaller more diverse ones such as TGIF Fridays (which catered to single women) and the larger ones which catered to more of a beer drinking, wing consuming male crowd. I knew quite a bit about both from my male days being out and about with my drinking buddies. Not to mention, I had managed a major competitor to Fridays in the area. I only knew the number of times I was jealous of women who took advantage of going to both venues.

It was not until I seriously began to consider going to a sports venue where I enjoyed the cold beer and sports on the big screen televisions, did I begin to look around and see many other cisgender women mixed in with the rest of the patrons. I began to think, if they could do it, why could not I?

Before I even considered my adventure, I needed to insure my femininized presentation was up to the challenge of being in an atmosphere where I would be one of the very few transgender women (or cross dressers) in the venue. All in all, the process took every bit of courage I could summon and still was very scary. Even though I was scared, I pushed forward to see if I could achieve my dream. From my business experience, I knew if I could make it to the bar without being noticed, most of my risk would be averted. Bartenders are greedy creatures and are primarily focused on service and tips which would not be a problem for me.

My biggest problem was acting as if I was not a single woman in the bar area. One of my tricks was to always use my cell phone as a prop to act like I was expecting company. For the most part I think it worked until I began to meet another transgender woman for drinks and there was strength in numbers. I was fortunate too; in that I was slightly ahead of the curve of cisgender women enjoying sports as much as men. When my lesbian friends and I were together enjoying the games, no one cared, and we fit in.

Through it all, there were only a few occasions when I was called out and embarrassed. One of which occurred when I was in a red neck leaning sports bar and had the local police called on me for using the women’s room. After a brief discussion with a female cop, I was sent on my way to a venue up the road where I knew I had rest room privileges.

Probably the most glaring and potentially problematic time I had was one night at a smaller sports bar I had gone to often with no problems. That night, my transgender friend Racquel and I were sitting at the bar minding our own business when suddenly, “Dude Looks Like a Lady” by Arrowsmith comes on the juke box. Not once, not twice but four times in a row, and to make matters worse, the new manager came up to us and said it was time to go. So, we did and went up the street to a bigger venue where we knew we would be welcome. Never to come back, or so we thought.

Several weeks later, one of the bartenders from the venue we were kicked out of found me and apologized. She went on to say, the manager who had banned me had been fired for drug abuse and I was invited back. I happily went back and never had another problem except a bathroom experience which I will save for another blog post.

More than likely, all the success I had in establishing myself in sports bar venues had to do with knowing the people on the other side of the bar were there for the money as much as the store clothing clerks I used to see in my old shopping days in malls when all they cared about was my attitude and the color of my money. On the other hand, the people in the gay bars treated me much worse and often I had to wait for service altogether.

At the end of the day (or several) my transition into the big sports bars was much easier than I ever thought it would be.

What an Adventure!

Image from Phillip Rawstron
on UnSplash

 Admittedly, at the age of seventy-five, I spend a lot of time looking back at my life, attempting to look at all the successes and failures that I went through.

The end result is normally wow! Did I do all of that? I remember the adventures I went through when I first left the house in my short skirt with freshly shaven legs and felt the cool night air on my body. At the time, I felt as if there was no other feeling like it and I could not wait until I could do it again. Then, there were all of the Halloween parties I went to cross dressed as a woman from head to toe. The parties were exciting to say the least but also showed me I could possibly make it in the public's eye as a transgender woman in the near future. It is important to note, I went through the stages of trying to dress sexy as a woman to trying to encourage the others at the party I really was feminine. 

When I started to try to enter the world regularly, I found I had many adventures ahead as I went from being laughed at to my face to at least presenting well enough to blend in with the world at large. Out went the short miniskirts and in came the jeans and tops which other women were wearing on a regular basis to the venues I was going to. At the time, it was less fun for me but at the least, my new fashion choices were saving me the torment of coming home in tears. For the first time in my life, the public was not laughing at me for simply trying to be who I felt I should be. 

From there, the adventure really started for me as I made the second big transition in my life. From part time cross dresser to fulltime transgender woman, if only in my mind. The entire idea was huge in that it took me back to the earliest days of admiring my girl-self in the mirror, and thinking that was good, but there was still something missing. The missing part became evident over the years; I wanted to be the girl I saw in the mirror. Little did I know at that time; my gender path would be a long and intense process. Nearly fifty years to be exact before I was able to come to terms to who I really was as a person. 

Before I was able to build a small number of friends I saw on a regular basis, I was intensely lonely, and on many nights was just going out to be alone. Hoping no one would bother me. Fortunately, they did, and my life took an adventurous turn for the better.  I ended up being invited to lesbian mixers, the women's roller derby and even an NFL Monday Night football game. To say I was scared would be too easy a term. Excited would be another appropriate way to think about what I was going through. Where had all of this been all the time I was stuck in my closet? 

Another big adventure was evident when I discovered I had more than one gender closet to escape. There was the physical closet of fashion, makeup and presentation to overcome, and then the major hurdle of the intense mental closet I lived in. I experienced major problems with overcoming the life my male self-had built for me. He was intense and did not want to let go. By then, it was too late, and I was never going back. 

All my adventures proved to be worthwhile, and I succeeded in living my dream of transgender womanhood. Plus, for those of you who think you have waited too long to live your dream, I waited until I was sixty before I started. 

Not Ready for Public Consumption

Porsche Boxster.

 As I made my way into a feminine world for the first times, I was amazed how different it was.

My male self-had grown used to pretty much getting his own way. He was successful in the business world even to the point of buying a new Porsche sports car of his dreams, primarily through the substantial restaurant bonus checks I was earning. Little did anyone know, my female side wanted the new car as much as my male side. She wanted to be the blond in the fancy new car.

New car or not, I was not sure I was ready for public consumption as a transgender woman. After all, I was still new to the world and was afraid to being discovered and ridiculed. So, I continued on through the recesses of my mind, until I presented well enough to get by in the world. 

One of the first major moves I made was to leave the confines of gay bars behind except for the lesbian ones I enjoyed so much. As with anything else, there was a learning curve to be dealt with. I learned there was nothing much I liked about the gay bars who for the most part either shunned me or treated me as some sort of drag queen. Oddly enough, the venues I did learn I was ready for public consumption were the big sports bars I was used to going to as my old male self. It was as if I flipped the switch and was able to go and enjoy a beer and watch my favorite sports as a trans woman and not a man and I loved it. 

Very quickly, I began to also love the attention I was getting in the new venues. I fit in quickly because I was friendly, made no trouble and tipped well. Once the staff at the venue's I went to understood I was only there for a good time and not any nefarious reasons, I was embraced as who I was and all of a sudden, I was ready for public consumption. One thing I need to point out was, none of this came easy to me. I started out with very little in the way of feminine features and I was used to surviving in a male world the hard way. I needed to work hard to feminize myself. Before I began to have an idea of how to feminize myself, I needed to understand how to do it. I spent many long hours in front of my mirror trying my best to perfect my makeup and fashion before I even had the courage to leave the safety of my own house. 

Once I did summon the courage to go out in the world, I also needed to figure out exactly what I needed to accomplish.  Early on, I was just trying to see if I can make it in the world, then it became more refined. Fairly quickly, I went from a man just trying to look like a woman, to actually exist with cisgender women in the world as an equal. Needless to say, the entire idea frightened me completely. I was totally out of the only comfort zone I had ever known as I explored a new feminine world. The good news was freeing myself the toxic relationship I had maintained all those years as I gave my best effort to live as a man. 

The best part was my dream did not turn into a nightmare when I transitioned into the authentic life I always should have been living. When I was finally ready for public consumption, I was ready. 

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 End Result?

 

Picnic time with my wife Liz on the right with
JJ Hart. 

Even though I write often about reaching my dreams of living as a transgender woman, sometimes I wonder if I had made it at all.

One of the problems I faced was thinking once I made it to my goal, there was always something else which was challenging me on my gender journey. When I was younger and so naive, I labored under the impression, looking like a woman should be my main goal. After I made it to the point where I could successfully blend in with the other women around me, I found there was so much more to do. I grew impatient with mediocrity and continually looked for more. There had to be so much more for me to discover around the next corner of my life. My prime example always was when going to the malls and clothing stores became too easy for me to do, I sought out other more difficult releases for my transgender challenges. I began to stop at restaurants to order lunch which forced me to interact one on one with employees. It all taught me the basics of communication with the public. 

I say the basics, because communication became the longest and most important part of transition which led to the end result of living my dream. How could I ever hope to live a fulfilling life as a transgender woman if I could not even talk to anyone else. I was also paranoid about anyone wanting to talk to me at all when I was out and about. First of all, I needed to relax and quit putting words in the mouth of the people I met and sit back and listen carefully what they were trying to say. For the first time in my life. The end result was I began to be able to interact with the over-whelming majority of the cisgender women who were curious about me. On the other hand, the majority of men I met wanted little to nothing to do with me, and vice versa. 

Once I arrived at a point when this transgender woman thought she had it all, something else would come along and proved me wrong. I learned the hard way; I needed to be careful where I went on my own as a woman in the world when my male security privilege was taken away. Navigation in a new world proved to be difficult for me. My theory of going out to be alone was at times dangerous as I actively sought out someone to be with. Overall, I was intensely lonely as a man and as a transgender woman. A complex difficulty to be sure in my life dealing with two genders. Primarily, I needed to choose what stayed and what went in my life. All I knew was, I was receiving more positive attention when I was out as a single transgender woman than when I was out as a single man. So, my choice became increasingly easier. 

The end result was, I made it to my goal of living as a fulltime transgender woman, I thought. Even though I was living my dream I never thought was possible, I found I had several other issues to conquer. All of a sudden, with all my male clothes gone and, in my past, I had to plan on what I was going to wear daily in the world. A big difference from the old days when I could look ahead a couple of days to my fashion choices. After several false starts, I made it to the world I always dreamed of, and none of it let me down.  Happiness was always fleeting in my life, but I finally found a slice of it. At times it was quite the adventure as I made my way from cross dresser to transgender woman. 

Even though my adventure had its ups and down to be sure but looking back there were more ups than downs as I made my way (or I should say, learned my way) to my ultimate end result.

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.

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.

Adjusting to Change

 

Image from
Rafella Mendes Diniz
on UnSplash.

I am biased, but I think adjusting to a lifestyle in a gender you were not born into is one of the biggest changes a human can make.

As many of you know, I took nearly a half a century to adjust to my gender changes. Looking back, some of the changes were a blur while others were so very slow. The reasons possibly were there were so many changes I made to arrive at the spot where I could take the big leap. For example, the night I went to an NFL Monday Night Football game with a lesbian friend of mine and her family. I was just coming out as a transgender woman and was scared to death but knew I needed to make the move and go with her. Needless to say, after the evening, my life changed forever.

The other night I mention often was when I went to see the Christmas lights at a local grist mill, by myself as a woman. I was not as nearly afraid as I was at the football game and ended up enjoying myself immensely. I felt secure in my fashion choices for the evening and was warm and cozy when I went up to one of the hot chocolate vendors for a warm drink with extra marsh mallows. Most importantly, I did not run into any major problems at either venue and my confidence skyrocketed. Maybe I could be secure in my transgender womanhood after all and live out my dream. 

By now, you may be thinking was that all it took to propel my confidence forward into a new life and leave the old male life behind. No, it was not. It is difficult to mention all the nights I spent out alone as a single lonely woman before I found friends to share my changed life with. Through it all, I needed to be so careful to separate my old male life with my new femininized one. Which meant to separate everything I was talking about to new people. Plus, I did not want to create a totally false past in my life and ignore everything I worked so hard to achieve. I found I could bring in the family I had and just change the perspective I was speaking from, and it worked. At the time, fortunately, I was busy closing out my old male life anyhow which had for the most part collapsed, so the time was right for a major change.

Surprisingly, change did come easier for me than I expected. My femininized life was a pleasure to adjust to. Since, I should have been living it all along. It was like my feminine inner soul was telling me she was right all along. If I just had the courage to make the gender change and stick with it. 

All the adjustments I needed to make in life to survive were worth it for me. Finally, at the age of sixty, I had seen enough of the small changes I was trying to make as a stopgap measure and I decided to rid myself of all my male clothes, start gender affirming hormones (HRT) and live the life I was always meant to live. 

How did I know I made the right change? Because, after I did it, I felt so relieved and natural. I let myself go to fall off my gender cliff and had a very soft landing. All those years which started out as just me in the mirror had come full circle and I was able to live my desired life. All because of the changes I went through.

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.

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. 

All I Saw were Walls

Image from Cristina Hernandez 
on UnSplash.

 I saw walls everywhere as I needed to build my own gender closet to protect me.

When I discovered I needed walls to protect my gender secret from the world when I was quite young, I managed to build strong ones. Difficult for anyone to penetrate because I felt something was basically wrong with me and if I was discovered, I knew a psychiatric visit was in my future. Back in the late 1950's and early to mid 1960's, any form of cross dressing was still considered a mental illness, and I knew well enough I was not mentally ill from wanting to try on dresses and makeup. None of that served any positive purpose, and I was driven deeper into my closet of walls. 

Soon enough, I began to escape my walls and began to explore the world as a cross dresser, long before I made my second major transition into a transgender woman. In the beginning, and for years afterwards, I grew frustrated on my progress and began to take more and more chances when I left the house as a woman. It was almost as if I was trying my best to get caught. So, everyone could see in my closet of walls and discover what was really going on with me. One way or another, discovery could lead me to a release of the gender torment I suffered from, and I could go on to live the life I had always dreamed of.

What I discovered was, dreams and reality were two different things. Or could I ever hope to go out and mix in well enough with the world of everyday cisgender women and survive. I was quite naive for years and thought I could be accepted as my form of an everyday woman by simply looking the part. Which led me to many memorable experiences in the girl's sandbox. Many of which I barely survived because I had allowed the wrong woman access to my closet. I had wrongly thought some women would allow me behind the gender curtain without a struggle and I needed to escape the sandbox with new claw marks up and down my back. Over time, my wounds healed, and I became a seasoned veteran of survival in a world ruled by women. 

As I did, my walls became the path of transition to transgender womanhood I was taking. I needed to plan far past just a day at a time presenting as a woman the best I could. How was I going to approach the time which was rapidly approaching when all of my life would be consumed by living my dream, and how did I stop it from becoming a nightmare? To make matters worse, I kept running headfirst into walls set up by my old male self. He never wanted to let go of his world and I needed to be careful I did not slip back into it when I was not paying attention to the way I walked or communicated in the world as a transgender woman. I was capable of ruining my whole day by forgetting to smile at the world, doing my best to talk like a woman, or move like a linebacker in drag. It took me years for muscle memory took over from my feminine side and I began to climb the walls I needed to be successful in the new gender world I was in. 

The best part was, I was seeing fewer and fewer walls. I had passed most of the challenges I had set up for myself. When I did, I became much happier and knew if I tried to stop the train I was on, I would go back to the miserable life I was trying to live between two genders. There was no way I was going to do that because of all the time and effort I put into releasing myself from all the walls I had built.

Reality

JJ Hart, middle, with Min and Kathy

 It took me years of denying my true gender identity to finally face the reality of who I was really was.

To do so, I needed to transition more than once to my surprise. I was naive and thought when I just put on a dress and makeup I was done transitioning. When in truth, I was only beginning my gender path. Deep down I knew there was something deeply wrong with how I viewed the world in all ways. Did I view it as male or a female. The only fact I did know was I was completely alone with my gender issues. There was no one else to talk to. 

Reality was a dark closet with no doors I could escape from. My only outlet was admiring my image in the family mirror growing up. I even went to the extent of taking on a rural newspaper route to add to my meager allowance to buy my own makeup and panty hose. By doing so, I could stay out of my mom's makeup and stop risking the possibility of snagging or running her hose. If you remember the panty hose which came in an plastic egg, I was a huge fan. The difference between just dressing in the clothes I found or bought was growing huge. No matter how much I cross dressed and admired myself in the mirror, the reality was, it was just never enough. Whatever I was doing, I could do it better. 

One of my biggest problems or dreams was to have my own glamorous wig. I grew up in the era of crew cuts or shorter hair for boys so there was nothing I could do to style what hair I had into anything resembling a feminine style. I was caught for many years, college in fact, before I could manage to sneak around and buy myself a wig I loved. It was long and blond, and I cherished it. I viewed the wig as one of the final pieces of my cross dressing puzzle. Maybe then, I could actually try to enter the world as who I was actually beginning to perceive as my authentic or true self. Little did I know, I was just spreading the seeds of my gender future.

The reality was, suddenly I was realizing I was following a life's path I wanted to be on. Each time I attempted to jump off of it, by purging all my feminine possessions. When I did, I could barely live with myself and could not wait to return to the protective confines of my transgender womanhood. Even though the path was bumpy and often threatening, the alternative of going back was even worse. The path allowed me to enter an oasis from life for me to judge where I was and where I wanted to go. As I always say, I was careful and took my time because I had so much to lose in my male life. I needed to make sure I was doing the right thing before I entered the world of women fulltime. 

Reality showed me the way; I finally put aside everything I had which screamed male and never looked back. As I said, the path I took was long and dark and I made my share of mistakes when I ran into the walls. The powder keg which was me needed to be de-fused so I could live a free life in a very pleasurable environment. I can't say the wait was worth it since I had no choice. I was stuck in a male world of my own making and did not have the courage to realize I had the power to break out and live my truth...or reality. 

Was I Outdated?

 

My wife Liz. Key West Florida.

Along the way in my increasingly long life, I have considered myself to be outdated. 

As I grew up through the late fifties and the early to mid 60's, I went through my mom's fashions, all the way to the short mini skirted times when I was in middle school. By the time I had cross dressed my way in the mirror to a place where I could control it at all, the world of fashion had changed, and I was outdated for the first time. My miniskirts gave way to hippie boho fashion. I loved the long-haired hippie women around me.

By now you are probably thinking I was resistant to change or was simply ignoring the overall basics of women's fashion. The biggest basic is that fashion always changes. A woman is encouraged to go with the flow of fashion for a number of reasons, good or bad. As I see it, the good or fun aspect of fashion are the seasonal changes. I write occasionally about when the seasons do change here in Ohio, how satisfying it is for me to go through my wardrobe and judge what stays and what goes. It is at these times; I have to figure out if I am outdated or not and most importantly, does it still matter to me at my age. 

As I am sure you all know, as cisgender women age, they go through progressions especially involving their hair. Many start wearing the longer hair of their youth and as they age, the hair becomes shorter and shorter. It was the one age trend I resisted until I had quite a bit of my hair trimmed off at the end of last year before my wife Liz and I went on vacation. It turns out, I fit right in with the other women on the vacation tour we went on to the Florida Keys. 

Just fitting in, was something I never wanted to do. Preferably, as much as possible, I wanted to be on the cutting edge of fashion, if, it involved having a Boho lean. I never got over the admiration I had for the women during my college and military days when I was required to wear my hair short. I made up for the short buzz cuts I had to wear by wearing my hair longer than almost all other women during my senior years. 

If you are familiar with "Stana Short" on the famous Femulate blog, the short she is referring too is in regard to her length of hemlines on her famously long and shapely legs. I never had to face the skirt length dilemma following my love affair with miniskirts in my youth until the eighties I believe it was when they briefly returned. One of my favorite outfits I had was a black mini I wore with one of my fluffy long sweaters and a pair of flats when I went out shopping. It was one of the few times in my life as a transgender woman that my fashion matched the majority of what cisgender women were wearing.

These days, at the age of seventy-five, I am happy to be able to stay active and mobile at all. Sometimes I think my favorite colorful leggings make me outdated in my fashion, but I love them and that is all that matters. I suppose too, I am allowed to be outdated. 

Every Eye was on Me

JJ Hart

 When I was first entering the world as a novice cross dresser or transgender woman, I felt as if every eye was on me.

For the most part, most eyes were on me. Especially from other women. I vividly remember the times I was looked from head to toe by another woman. Slowly but surely, she was undressing every aspect of my fashion and making no secret of it. I thought at the time, I was just being introduced to the aspect of womanhood and to just get used to it.

At the same time, I was working on my overall femininized presentation, I was trying my best to mimic the way women move so I would not appear as a linebacker in drag. My adventures took me as far as trying to walk like a girl in large box stores late at night. I wonder now how many security cameras I made it on trying to perfect my walk. Through it all, I needed to be careful I was not walking the wrong way at the wrong time. Or for example, remember to not try to walk like a woman when I was working as a man. The entire process became more difficult the more I began to split down my time increasingly in favor of being a woman. I started with just cross dressing when I could a few days a week and ended with splitting my time four days a week in a feminine world versus three as a man. The whole process became even more complicated because I was still working my full-time job as a man. Especially when it came time to getting a new pair of glasses and I wanted to change over to feminine frames. 

The most difficult aspect of what I was attempting to do was the mental aspect of trying to juggle both main binary genders. I needed every moment to work on my transition and get used to all the nuances of it. A big portion of the process involved being looked at. At the least, no matter how well I applied my makeup, styled my hair and picked the right clothes for the occasion, I was still a big woman and would naturally attract attention. I attempted to conquer the size issue by losing weight. I responded by losing a significant amount of weight which helped in two ways. I could fit into better fitting women's clothes and at the same time look better when I went through another woman's inspection.

Of course, I was inspected by men too, but the inspection was much simpler, and I knew what it would involve. Women on the other hand, had more to look for since they had experience in the fine points of putting outfits together. At some point in their life, they had to put together everything from shoes to wardrobe to hair to put an outfit together. Since I needed to do it too, I knew what they were looking for and tried to plan for it. My accessories needed to match the rest of my hand-picked outfit to succeed. Even still, the times I went through helped me to prepare my future life as a transgender woman. 

If every eye was going to be on me, I was just going to have to adjust and do the best I could. If it was possible, I would try to thank all those women who looked me up and down. They taught me what I needed to do to succeed in my future. 

Opening Your Eyes

 

Image from Jesper Brouwers
on UnSplash.

I found I needed to be careful as I tried to negotiate a difficult gender path to transgender womanhood. 

Most likely, my eyes were open for the first time when I explored my mom's wardrobe for clothes and makeup I could try and see myself in the family's full length hallway mirror. When I saw myself, my eyes somehow were opened, and I knew I could never go back. Being a so-called normal boy was not going to cut it. 

From my humble beginnings, a small fire within me grew to a point where I knew I could never turn back from at least trying to set feminine goals and living up to them. The problem was, I had no workbook to rely on when the going got rough. I had no girls sleep overs to go to, or a mom to council me on my appearance. It came down to my relying on the mirror to tell me everything I needed to know about my femininized life, and it turned out the mirror could easily lie to me. It would tell me I was pretty, when in fact, I looked like a clown.

Following being rudely rejected by the public, my eyes were finally opened to the fact I needed to make changes in what I was doing if I was ever to survive. Soon I was haunting every nearby thrift store I could find for just the right feminine wardrobe items to add to my closet. It took a while, but I began to turn the corner and began to work my public presentation to a point where I could blend in with the cisgender women around me. My only real problem came when I did not have the finances to purchase the rare item, I thought I needed in the worst way. An example I still remember was a full-length wool powder blue coat I found at a discount coat store. It was in my size, went with my blond wig and I desperately wanted it. Long story short, no matter how many times I went back to the store and admired myself in the mirror, there was simply no way I could buy it. The main problem outside of affording it, was where would I hide it from my wife when I got it home. I needed to give up and move on to a cheaper alternative to keep out the Ohio cold. 

My eyes were really opened when I was allowed behind a rather formidable feminine curtain which women use to protect themselves from men. First of all, I needed to earn my way into their inclusive club by proving I was much more than a casual observer of women and most of all, not another drag queen. Step by step as I earned my way into a new and exciting gender world, I knew I was making the right move away from a male life. Mainly because I felt so natural in my experiences I was having. I cannot say my life was easy back in those days because I was stuck between two genders but on the other hand, each time I reached a new point of success, then I could not ever turn back. Again, because I was feeling I was headed in the right direction. 

Another problem I had during my journey was making sure my vision was correct. It was easy to have 20/20 vision when I was looking at myself in the mirror, but much harder when I was having a conversation with a strange woman. I was burnt many times when my vision of what was going to happen was blurred. 

Each time my eyes were opened, deep down I knew I could never go back. 

Wishes were not Enough

 

Image from Delphina Iacub on UnSplash.

In yesterday's post, I wrote about the amount of time I spent wishing I was a girl as I went about attempting to live a male life.

As I pointed out yesterday, I finally arrived at a point where every spare second, I was becoming dedicated to my pursuit of becoming a girl. Which included watching the girls around me closely at school. I was desperately jealous of their fashion and lifestyle. 

As I became older, in order to survive in the world, I put less time wishing I was feminine and adding more time into actually doing it. Which meant of course I needed to unlock the door to my gender closet and try to enter the world as a novice cross dresser or transgender woman. Back in those days, I took a lot of rejection, as I thought I looked like a clown in drag. Stubbornly, I persisted until I could find the right mixture of makeup skill, fashion and wigs. Once I did, my life across a new and exciting gender border became much more satisfying and fun. So much so, I was fooled into thinking my feminized wishes were coming true. 

It was about that time when I hit a gender wall as I found out what my wife was telling me all along, I had a long way to go on my path to transgender womanhood past just looking like a woman. I needed to quit wishing and find out what she was talking about. 

The more I explored the world as a trans woman, the more the world opened to me as gender curtains were pulled back. Of course, I knew cisgender women had their own world to exist in but I did not know how strong and in-depth that world was. For the longest time, my head was spinning as I tried my best to absorb the daily lessons I was learning. Primarily about communication and co-existence with other women on their playing field. Certainly, wishes were not enough when it came to surviving in a woman's world. I found I drew the curiosity of other women who wondered what I was doing in their world, and I had to be better than the average ciswoman just to get by. 

It was about this time; I decided to take a shortcut in my external femininized appearance and research doctors to see if I was healthy enough to begin gender affirming hormones (or HRT). I was, and the hormones almost immediately went about making changes such as softening my skin and producing breasts. All of which helped me to help my presentation skills. Especially, since I did not have any male pattern baldness and quickly was able to grow my own hair out and go wigless. 

I found by this time, wishes did not have to be enough, and I could move up my final transition timeline. Finally, my long-awaited dream could become a reality, and I could put my hated male clothes away forever. Perhaps the best part was, I never wished for him to return.