Gender Masks

 

Image from John Noonan
on UnSplash. 

In life, both genders learn early on what masks mean to their existence.

Think of it, at the earliest age, babies have only very limited ways to show their pleasure or anger by smiling or crying. Of course, as we advance through life all of it changes. I could be biased, but I think women in life have an advantage by using masks. 

While boys are squaring off on the playgrounds at school, girls are learning the basics of makeup, if their moms allow it. In many ways, makeup for women provides them with their ultimate masks. Anything from false eyelashes to skin foundations to wigs are permissible. It is not unheard of for a man to wake up to a totally different looking woman after a night out on the town. 

Makeup is not the only way women use masks effectively. I learned it the hard way several times when I was first out in the world as a transgender woman that a smiling face does not necessarily equal acceptance in the world. There were many times I relaxed too early in a situation with another smiling woman and ended up getting stabbed in the back. I fell for her friendly mask and paid the price. The whole process with women with me went back to feminine passive aggression versus the old direct aggression I was used to with men. Eventually, I came to consider the process as just another rite of passage into the world of women and I quickly became much better in being able to see what was going on behind another woman's mask. 

As my relationship with other women grew, the better I became at perfecting my own mask. I started at an early age attempting to perfect my art of makeup. It was all I could do to stop looking like a clown in drag. I stumbled along at my mask efforts before I made it into asking for and accepting professional makeup help. I happened into it during a cross dresser, transvestite mixer I was attending. Part of the mixer was given over to several professional makeup artists who offered free makeovers to anyone who wanted them. I gathered my courage, hitched up my big girl panties and stepped up for help. When the help I received was complete, I could not believe the change. The guy doing my mask had totally removed my old mask and designed a new one. The changes were so dramatic, I even received an invitation to go with the so called "A" list transgender women when they went out to bars after the mixer. To make matters even more dramatic, I was the only one approached by a man in a bar to stay for a drink. For many reasons, I did not stay and drink with him, (another story) but the point was made my mask could compete for a change with the "A" girls who the man ignored. 

The best part of finding my new mask was being able to keep it. The professional makeup guy managed to explain everything he was doing to my face and wig, so I understood it and could replicate it over and over. Once I had my mask, I was able to take advantage of it the same as any other woman would. In fact, more so, because I felt to succeed in the world as a transgender woman, I would need to be better than the average cisgender woman who had been born with a built-in mask advantage. 

Fortunately, I was able to step back and look at my new gender mask from a positive perspective and what it meant from view of a novice transgender woman. When I did, my life radically improved for the better and I understood how masks really worked in the world.

Preparing for the World

 

JJ Hart. Witches Ball Image.

Before we get started, I would like to take the time to respond to a comment from an anonymous reader to the blog.

For the sake of simplicity, I will condense the comment. The reader was responding to my post concerning my second wife never accepting my feminine self. The reader raised the question about if my wife was somehow jealous of the way I looked. Even though my ego often considered it, I never allowed myself the latitude to consider it. After all, I never considered both of us were in any sort of a competition when it came to appearance, we were simply different in our outlooks. As a cisgender woman, she believed in very minimal makeup and conservative clothes. I did not, and considered the makeup, hair and wardrobe process a woman goes through as part of the fun and challenge of being femininized. As it turned out, there was no way I could cross dress down to her level. If I did, I might as well not attempt it at all. As all of your regular readers know, I will never have a final answer to the appearance question because she passed away years ago. Thanks for the comment and now on to the rest of the post.

I found, as I evolved in life, it became more and more evident to me that cross dressing was more than the proverbial "sun" of my life. What I mean is, even though my entire life revolved in many ways around being a serious part-time cross dresser, deep down I knew I had so much more to accomplish in my gender journey. 

To arrive at where I wanted to be as a novice transgender woman, there was so much more I needed to do. When I put my so called "pretty, pretty princess" into motion into the world. No longer did I just have to worry about my appearance, I had to concentrate on how I was moving and communicating with the world. To say the least, it was a struggle to put all aspects of being a novice transgender woman together. My sun became my entire universe as I went out into the world as I attempted to completely feminize myself. I needed to stop with the ignorant way I was trying to present myself and learned the hard way, to survive in a world I found was run by women, I needed to be better. 

My brutal entrance into the world as a transgender woman, helped me to learn all I needed to know. Or so I thought. Every time I thought I knew where I was headed, only to find I had another wall to climb. Finally, I came to the conclusion in life, there would always be walls to climb and my life as a transgender woman prepared me to better attempt the climb. 

Since I was/am very afraid of heights, I could not spend much time enjoying the view when I had successfully climbed a wall. I needed to get busy and search for the next one. Plus, having a soft landing was never guaranteed. No one ever told me how many bruises I would suffer on my path to gender freedom. 

Finally, any purported competition between my second wife and my inner feminine being was put behind me and I could move on the best I could. 

Real Life Impostors

JJ Hart at Key Largo.

 At various times in my life, I have suffered from impostor's syndrome when I was out with other women celebrating a girl's night out.

While I was overjoyed to be invited to the events and considered them to be a rite of passage to my transgender womanhood, I still could not shake my underlying feelings of doubt when I was allowed behind the gender curtain. 

As I went through the process, I began to wonder if all human beings go through a form of impostor syndrome in their lives. What I am trying to say is no woman is born a woman. They are socialized through life to achieve the status of women since they were born female. Men also go through the same process. It's the primary reason I had such a difficult time leaving my male past behind because in many ways I had made it to manhood which was miles away from just being another male. I needed to start all over again to travel to my gender goal of transgender womanhood. 

In the meantime, my confidence was building that I had as much right as the next woman to be at special functions. I had just arrived at the same point the other women did by using another path. I was aided also when I calmed down and began to contribute more to the group. I found I had more in common than I thought in this women's only space. Even though, I most certainly did not birth a child, I could bring up my own daughter and grandkids who I was so proud of. I just needed to flip the gender script to relieve myself of any possible impostor syndrome feelings. 

It wasn't just at the girl's nights out when being a gender impostor took a hold of me. Another prime example were the nights when I felt I was doing everything right. My fashion, hair and makeup all were on point and yet there I was wondering what I was doing there at all. I was devastated when I had come so far in my feminine presentation, just to have something else stand in my way. It took me awhile, but I worked my way through it all and put impostor syndrome in my rear-view mirror.

On the increasingly rare occasions when I encountered any resistance from the public, I finally came to the conclusion they were the true gender impostors. It was very clear to me why men left me alone as they were so insecure in their own sexuality. On the other hand, most cisgender women were more secure and not afraid to reach out to me. Especially interesting to me was the interaction I had with the lesbian community. Most of the lesbians I had a positive experience with had past encounters with men, so I was not so far from a person they would consider knowing. I learned quite early in my experiences in public, the various levels of the lesbian society. In fact, my first date with a man was with a very masculine lesbian on his way to becoming a full-fledged transgender man. Many times, the more masculine the lesbian, the more interest they showed in me. They were certainly not gender impostors.

Real life gender impostors are everywhere in this increasingly hostile world. We don't need insecure people in power using transgender women and trans men as crutches to increase their own power. 

From Obsession to Passion

 

Image from Kayshawn Herandez
on UnSplash. 

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

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

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

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

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

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

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

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

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

Why Not Me?

 

Image from Danielle
la Rosa Messina on
UnSplash

Going through life, I was very insecure concerning many things.

I always had a difficult time excelling at all in things such as sports because I was so insecure about winning. If I did not, which was common, I could run home and hide behind my makeup and pretty dresses and pretend I was a girl and all the pain of losing went away. Then, the more I cross dressed, the insecurities began to sneak in there also. Was I presenting well enough and how would I ever know if my only contact was between me and my mirror. I thought I looked presentable, but would the world agree and what if I looked like a clown in drag.

It took me years to even acquire the basic wardrobe and fashion I needed to even get myself a fair shake with my feminized presentation. All along, my lifetime dream was to be a woman, and I was so far away. I did try to make an excuse to cross dress and come out to a friend once, but it was a dismal failure when he was embarrassed and turned away. The whole experience sent me running back to my gender closet and slamming the door. I did not know what my next move would be.

Life went on for me and the desire to possibly living my feminine dream never went away. In fact, it became stronger and stronger. When I could, I made "investments" in better fashion, wigs and makeup which really helped me advance my overall presentation. As I did, I gave the public another try to see how I faired in the world out of my closet. I needed to put aside all my insecurities, gather up all my courage and give it a go. 

Initially, my path was a bumpy one, full of false stops and starts. I was flying blind with no handbook to help me, and it showed. During too many nights in failure, I had to run home in tears wondering if I was on the right path at all. Somehow, the faint voice of my inner feminine soul could be heard telling me not to give up as there were better times ahead. I listened, pulled up my big girl panties and managed to move forward as I discovered a better life as a novice transgender woman. 

I discovered the best way to combat my insecurities was with confidence. I resolved to never let the world see me sweat. First, it would ruin my makeup and second, if someone had a problem with me, it was their problem, not mine. I had put an incredible amount of time and effort into being the new transgender woman I was becoming, and I would be dammed if I was going to give it up easily to some bigoted transphobe. All the years of losing weight, learning makeup and skin care just could not go to waste as I chased my insecurities about living fulltime as a transgender woman. 

Still, I wondered, would I ever be good enough to join the world of women and would it be what I expected it to be. 

Unexpectedly, I received a giant push from women friends I found and cherished. With their help, I was able to put my insecurities behind me and become a part of a world I had only dreamed of. Why not me, became you can do it and I succeeded in my path into transgender womanhood. 

Trans Girl at the Roller Derby

 

Transgender Roller Derby Woman

Way back when, as I was building my transgender confidence, a group of lesbian friends invited me to tag along to their roller derby experience. 

Even though, I was slightly petrified to say yes, I enthusiastically went along with the idea. What could possibly go wrong with a small group of lesbians drinking one dollar beer watching women's roller derby in Cincinnati? Actually, nothing did go wrong, and I ended up having a great time. 

Also, I was amazed at the number of women in the crowd and on the rink who were more masculine than I still was.  All of them helped me to calm down and have a better time at the event. The only problem I almost encountered was when I used the women's room. It involved an evil stare from a woman coming out as I was going in. It also turned out to be one of those days when I was wearing more makeup than the majority of the women in the venue. Of course, I tried my best to apply the bare minimum of makeup so I could blend in, but it turned out to be impossible. There seemed to be no one wearing any makeup at all. I guess I identified as a "lipstick lesbian" for the afternoon. 

After I settled in, I found I could even enjoy the action on the rink, even though I did not understand all the scoring moves I saw. Plus, I had read the story of a transgender woman who had skated for a Long Island, New York, team who had fought and won her right to to participate. This was way before todays bigoted transgender backlash around the country. 

Sadly, I never went back to the Cincinnati Roller Girls matches again. My excuse is I was never invited back until my mobility issues made it difficult for me to do. Plus, my small group of lesbian friends drifted apart. In the meantime, I was able to check off another item I did not really know I had off my bucket list of things to try as a transgender woman. My friends were doing a wonderful job of pushing me out of my gender shell and if they wanted to do something as a group, I was included.

Everything I was able to check off enabled me to grow my all-important confidence in the world. From there I was able to begin going with my future wife Liz to "Meet Up" groups in the Cincinnati area. "Meet Up's" are groups of strangers who get together to discuss all sorts of topics from writing to knitting and beyond. Meeting strangers again did wonders for my confidence in the world as a transgender woman. I equate the whole process as building a new foundation in life away from anyone ever knowing my old male self. 

Finally. the wall became thick enough and high enough my old male self was completely shut out and he became the one stuck in a dark gender closet. My trip that afternoon just became one more success story on my journey to transgender womanhood.

Trans Girl at the Symphony

 

Cincinnati Music Hall

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

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

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

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

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

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

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

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

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

Always Running

 

Image from JJ Hart

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

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

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

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

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

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

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

Not Scared? In the Wrong Room

 

Image from Alexandra Gorn
on UnSplash.

I cannot begin to tell you how terrified I was to interact with the public when I first began to attempt to live in the public's eye.

One night in particular always stands out in my mind. It was the evening when I had pre-determined my cross-dressing days were behind me and I was going out as a transgender woman. Furthermore, I knew if I was successful, it would change my life forever. As I prepared for my big night out, I took extra care with my outfit, makeup and hair. I wanted to make sure I blended properly with all the other women I would be interacting with at an upscale bar I was going to which was heavily frequented by professional women who worked at a nearby mall.

Once I made the short trip to the venue and found a parking spot relatively close to the front door. As I sat in the parking lot, the pressure to go in increased dramatically. As I nervously checked and adjusted my makeup in the car's rearview mirror, again and again the fact was not lost on me I could be changing my life forever. By the time I gathered my courage to actually enter the venue, I could barely breathe and was gasping for air. 

It took me awhile to gather my courage and enter the front doors of the place and interact with the hostess stand. Deep down, I was hoping the hostess would be busy seating other patrons so I could sneak on through and find a seat at the bar. The short distance from the hostess stand to the bar seemed to be miles to me but I made it and luckily found a corner seat at the bar by myself. Plus, the bar itself was supported by two large thick pillars. I figured if I found a seat next to one, I could blend in and hide if I needed to. I did not need to hide as I was approached for my order by a friendly bartender. 

Immediately, my fears began to melt as I ordered my first drink and even started to relax a bit and watch all the other women who had begun to arrive at the bar to enjoy each other's company. As I observed the group, I saw no one was noticing me. So far, so good. No one noticed a very scared novice transgender woman in their group. 

Of course, this evening was only the beginning of my new transgender journey. I knew my life had changed forever. I could never go back to the old unwanted, boring male life I was living. To move forward, there would be many nights when I would be very scared. Somehow, I learned to feed off my fear to propel me forward. No longer was I a weekend cross dresser, I was reborn as a very serious transgender woman.

My end game was using fear to refine my push forward by putting extra time and effort into my fashion and makeup. That way, when I needed to walk past a crowd of strangers in a new venue I was in, I could do it without any issues. 

I finally decided, if I did not feel any fear at all, I was in the wrong room. Especially, in today's climate, it pays to always be aware of your surroundings. Maybe fear is a strong word, but awareness is not. 

The Gender Envelope

 

Image from Alexandru
Zdobau on Unsplash.

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

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

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

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

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

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

Amazing

 

Image from JJ Hart

As I sat and watched a singer do a wonderful rendition of John Lennon's "Imagine" and watched the ball in New York drop to ring in 2025, I had the chance to look back and think about how amazing my life has been.

As in everybody's life, destiny stepped in and took me in directions I never thought possible. The entire process was how I perceive the supposed death experience people have when they die. In other words, they get to see their life pass in front of their eyes. If indeed that does happen, I may have to ask for a little extra time to view all of mine.

Over a long life, I have been so fortunate to experience so many things. Outside the all-encompassing world of gender for me, was when I managed to land a job in the Army with the American Forces Radio and Television Service in Thailand and Germany as a radio disc jockey. To put it into perspective, there were only sixty other troops in the entire Army who did what I did. Since back in those days, we were basically the only connection our listeners had with home, it was a very serious job. 

Once I had served my time of three years and was released from active duty, I needed to take on again my larger issues of gender identity. To do so, I undertook serious research and development. Any time I could such as Halloween parties, I began to explore public reactions to my femininized self. For the most part, people I knew were astounded and I moved on. Perhaps it was my shaved legs which gave me away. Whatever the case, time flew by, and I started to cross dress more and more in the public's eye. Plus, at the same time, I slowly began to perfect my knowledge of fashion, makeup, and hair. I discovered the more I did, the more natural I felt and the more I wanted to do. In no time at all it seemed I was accomplishing tasks such as doing the family grocery shopping as a woman and it felt amazing.

Imagine my surprise when I then discovered I was going through another major gender transition. All of a sudden, I was losing my desire to just look like a woman and I more and more wanted to explore a path to transgender womanhood. Mainly because I was feeling alive and amazing when I did it. Now we all know how difficult a gender transition is for the average human being, and I was no different. I had very few natural feminine characteristics to work with and I had to struggle completely to survive in the life I wanted to live. Especially when I hit what I call the dark period of my life when I lost nearly everyone close to me to death. 

In order to bounce back, amazingly, I was able to rely on my strong inner feminine soul to survive at all. She helped me find my way. During the bounce back period of my life was the time I found a whole new set of women friends to instruct me on how to live my new life. Included in the trio of new friends, was my new wife Liz who I never expected to meet. At my advanced age of sixty plus, I would never find another person to be close to the rest of my life. Especially since I carried so much gender baggage with me. At the time, I still maintained one tentative foot in the male world, until Liz told me she did not see any male in me at all and what was I waiting for. Go ahead and fully transition. I was amazed and still am since it was over thirteen years ago when our relationship happened and is still going on strong today. 

The end result of watching the ball drop to welcome the scary year of 2025 was I have been so fortunate to have led an amazing life so far. Mainly because destiny has been on my side, and I have lived long enough to accept it.  

All Hands on Deck

 

Image from UnSplash

As I progressed farther along my long and difficult gender journey, there were many times where I wished I had company to aid my path.

Even though I often whine and cry concerning the lack of assistance novice cross dressers or transgender women have early on in their progression, the fact remains we need to work our way through it and do the best we can with our fashion and makeup. Until I began to see positive results, I am sure I looked like a clown in drag. Still, I was alone with my thoughts. I am old enough to remember with "Virginia Prince" and her Transvestia publication first came to my attention. It provided me with the first real look at others who shared the same interest in being femininized and looking like a girl. I was mesmerized with more than a few of the cross dressers I saw in the publication. I so badly wanted to be like them.

For years as I worked alone to look more realistic as a cross dresser, I still yearned for feminine help. I thought any cis woman could help me because of their years of practice and interaction with their peers. When I was engaged in college, the opportunity to be dressed from head to toe as a woman by another woman finally came my way. Somehow, I begged my fiancé to do it even though I don't remember now how I did it or was so persuasive. I went all the way by even renting a motel room for all the pre-prep work such as shaving my body I would have to do. 

Once I shaved and dressed, I was excited to undergo the long-awaited makeup process. Since she wore quite a lot of makeup, I was confident she could do a great job. It was finally time for all hands-on deck in my young cross-dressing life. Back in those days, mini skirts and dresses were in vogue so I brought one I found and purchased along with panty hose, heels, and a long blond wig and started the transformation process. To say I was excited would be an understatement. Time flew by as she finished my makeup, and I headed for the mirror. Instead of the beautiful blond I thought I was going to see, I was actually disappointed. I could not see much difference in her efforts from my own. Even still, I acted as if I was really impressed with her expertise when in fact, I was impressed with how much I had learned on my own over the years. 

It took me a long time working with makeup to learn each of us has a blank face to work with and we need to learn the best way to work with it. My fiancé was doing the best she could with the knowledge she learned from her own face, not mine. She was far from being a professional such as the help I finally received from a true makeup pro at a transvestite, transgender mixer I attended years later after I was discharged from the Army. He taught me lessons about my face I had never even considered such as which features to play down and which ones to build up. To this day, I owe him a huge vote of confidence and thanks.

It turned out the opposite happened with my fiancé. Due to knowing my deepest, darkest secret about being a cross dresser, she said I should use it to dodge the draft and stay out of the Vietnam war. There was no way I was going to do that, so we split up shortly before I was to leave for basic training. Actually, it was the best thing which has ever happened to me in my life. The pain it caused immediately would have been nothing like the suffering we would have gone through if we had stayed together.  

Looking back, at my life's work as a transgender woman, for the most part, it has been a solitary experience. Not having a female peer group to interact with and learn from was a problem to be sure but one I learned to work around. The end result was, I needed to be better than the next woman to make it. 

Expedition Transgender

 

Image courtesy JJ Hart

The half century journey I embarked on to finally come up as my true authentic self was certainly an expedition. 

As I always mention, my discovery began with going through my mom's underwear drawer and trying on nylons, bras and girdles I could still fit into before testosterone poisoning really set in. From there, I progressed into makeup and very slowly began to increase my craft. I did not really want to look like a clown in drag so I did the best I could. 

Life went by and so did my expedition. Sadly, for several reasons, I developed several coping mechanisms to mask my gender truth. I tried and tried to convince myself my desire to wear women's clothes and look feminine was just a harmless hobby and perhaps was just a phase in life I was going through. It took me years to realize the true phase I was going through was that I was a male at all. With sheer willpower, I managed to learn to play the male game fairly successfully and lived a life which shielded my feminine self from most all intrusions. I went into my dark lonely gender closet and slammed the door.

It took me years to have the courage to open my closet door and tentatively look around. When I did, my expedition took sudden and encouraging turns. The more I tested the public as a transgender woman, the more successful I was. I set out to sample as much as I could of a woman's lifestyle and discover my feelings on what would happen next. I tried going to gay and lesbian bars as well as big sports bars and found I could carve out a spot as a regular in a so-called straight venue. I also tried to go to various other places such as bookstores and other retail venues single women would go. In other words, I was obsessed with coming as close as I could on my expedition to seeing what a cis woman went through in her life. By doing so, I could make the final decision on where I wanted to go with my life, as a man or as a woman. 

As my expedition transgender progressed, I found myself in a face-to-face decision on beginning to take gender affirming hormones or not. Since my only real opposition to beginning the hormones had passed away, my ultimate path was clear, and I sought out a doctor for approval. He checked me out and determined I was healthy enough to begin HRT with minimum dosages of Estradiol and a testosterone blocker and my life changed forever. All the changes which occurred would fill another blog post themselves. Perhaps the biggest overall surprise was how quickly my body took to the new hormones. So fast, I needed to rethink how quickly I was going to have to change the timetable of when I ultimately wanted to finish my expedition and enter my own transgender womanhood.

I learned the fact of the matter was, I was always living a gender lie. I had refused to accept the fact I was always deeply feminine and was forced into a male lifestyle from some cruel twist of fate. All the time I thought I was a man attempting to be a woman was wrong. I was a woman attempting to be a man.

I wish I could have a portion of my life back to re-center my expedition and start all over again.  

 

Getting What you Want

 

Image from Aiden Craver
on UnSplash.

This is not really a Christmas post, even though in many ways, it fits in well with the season. 

As I was growing up, I vividly remember being asked what I wanted to be when I grew up into an adult. I also remember lying and saying something like a lawyer or doctor. Anything to make my parents happy without telling whoever asked, I really just wanted to be a girl when I grew up. An answer such as that would have landed me in all sorts of trouble.  

I progressed through life doing my best to navigate a very dark and bumpy gender road without much help from anyone except the occasional therapist. Through it all, for the longest time, getting what I wanted was a faraway dream. During my gender journey, I faced all sorts of problems such as my reoccurring issues dealing with my feminine appearance. Like so many of you, I needed to learn the fashion and makeup arts all by myself with no one to help. Back in those days, there were not the plethora of on-line makeup videos and special makeup stores to help a novice cross dresser along.

Then there were the up close and personal meetings I had with the impossibly feminine transsexual women I met. Interacting with them made me feel again how impossible my dream of becoming a full-time woman of any sort would be. However, it was about this time I began to take better care of myself, so I had a chance of becoming a better feminine version of myself. 

I dieted and lost nearly fifty pounds and began a regular skin routine which really helped with using less makeup and achieving better results. Suddenly, there was a light at the end of my presentation tunnel which was not the train. Maybe I could get what I wanted after all. At that point, I really became serious about exploring the world as a transgender woman. The rest as they say is history. When I did gather the courage to enter the world, I found I could survive. I discovered a great majority of the world did not care and a smaller percentage was just curious and amazingly enough, a smaller percentage yet respected me for living my truth. The bottom line was I survived and became better at life as a transgender woman.

When I did survive and relaxed, I saw my reality shining through. Maybe, just maybe, I could shed the shackles of my old male existence and live my gender dream. I could answer finally my own question of what I wanted to be when I grew up. A woman. To further the process along, I was able to begin gender affirming hormones which femininized me even further. My facial lines softened, my hair and breasts began to grow, and my emotions softened to the point where I could cry freely for the first time in my life. Through it all, my body was asking me what took so long to start HRT.

Looking back, getting what I wanted was the most difficult trip I had ever taken in my entire life. Pure perseverance and destiny helped me along to a full-time life away from my old unwanted male self, into a life I always wanted.   

Trans Girl Shopping

 

Image from Sam Headland on UnSplash.

Many Christmases ago, in the early two thousand's I began to do most of my special gift shopping for my second wife as a transgender woman. Needless to say, I learned a lot. 

My wife was a huge gardener, so greenhouses and specialty garden stores were my first places to go to if I was to ever find the special gift, I was looking for. To find the best selections, I normally made the hour trip to Columbus, Ohio which had bigger greenhouses and even a specialty garden store in one of their upscale malls. Since at that time, I had a reasonable amount of spendable income, almost nothing was out of reach for me as a gift for her. 

Normally, I made the trip during the day and wore professional women's business attire. My hope was I could present well as a woman just on her lunch break shopping for last minute gifts. Even though, I was beginning to feel more and more at home as a woman in the world. Still, I felt I needed to work hard to be able to present the best I could as a transgender woman to avoid detection. Seeing as how I was knocking out two birds with one stone, I needed to do it well. 

I should not have worried because one way or another I was treated warmly by more than a few of the clerks I faced and at the worse with indifference by others. I found the older clerks were more apt to help me and the younger ones left me on my own to shop. Even being left alone was alright with me because I was so intensely trying to find just the right gift for my wife who did not know it was my feminine self-doing almost all her shopping. Along the way, I found all sorts of unique gifts from new garden tools all the way to vintage seed boxes in antique malls. Which is a different story for another blog post which I will write before Christmas. 

Perhaps you are wondering what I wore for these new yet scary shopping adventures I was on. Depending upon which mall I was going to, I attempted to scale up or back on my outfit so I would not appear out of place. At that time, Columbus featured two very upscale malls, and I could not miss out blending in by dressing in my finest silky black pant suit, blond wig, and heels along with my very best application of makeup. All my efforts worked well as nearly everyone ignored me, except a few men. 

Since I was being successful in my transgender womanhood, and I was able to be out in the public's eye for an extended period of time, I decided to push my boundaries and stop to eat and use the lady's room. Both were a challenge for me since I had rarely done it before. I gathered my courage and stepped into one of the sit-down restaurants in the mall and just took a seat at the bar to eat. Sure, I was scared of having any one-on-one communication with the public but on the other hand, I was so successful so far in the day, why not push my luck. 

It turned out all my fears were unfounded as I was treated well in the venue I chose and the only problem I had in the restroom was navigating my way around using the toilet in my pantsuit. I did not think far enough ahead when I chose my outfit for the day and put fashion ahead of rest room utility. Fortunately, I was able to complete my struggles successfully, take care of business and leave the lady's room before anyone else came in. 

I finished the day of trans girl shopping as a very successful experience with the added positives of finding great gifts for my wife. I could not wait to do it again.

Outreach Lunch

 

Today is the Alzheimer's Association diversity council holiday luncheon.  

It will be interesting on several levels. The first level will be the near hour drive to get to the venue in a rainstorm. Of course, I put off getting gas in the car so I will have to stop in the rain to fill the car up with gas. Which will undoubtedly ruin all the time and effort I put into doing my makeup and hair this morning. One of the problems of being a woman.

The second level I will face is all the people I will be meeting for the first time in person. Since I joined the diversity council, all the meetings have been virtual, so I did not have to worry as much about my overall appearance. Resorting to a close shave and light makeup to get me by. This morning, I needed to be on point with my makeup and hair regardless of the weather, so I put more time and effort into my appearance. 

Plus, there will be more people at the luncheon since the Dayton, Ohio chapter is joining us for the holiday luncheon.  Since I have been received well by all the people in the Cincinnati chapter, I have no reason to believe the other new people will be any different. 

When we go around the table for any new news, I can even come up with my own. I can tell the experience of mine with the television reporter who supposedly wanted to interview me concerning LGBTQ elder care when in fact he kept steering the interview towards my feelings about the election. I will try to explain to the group why I turned him down and with it, a chance to publicize the work of the Alzheimer's diversity council. 

Overall, I hope I can catch a break with the heavy rain which is forecast and enjoy my lunch. Sometimes I struggle being social around strangers, so we will see.

In the meantime, you do not need to be in Cincinnati to volunteer your time to a local or regional Alzheimer's chapter.  If I am any kind of an example, you will be welcomed with open arms. Also, in my case, I am trying to pay forward the assistance my family received when my dad passed years ago from the very ugly disease.

If anything happens good or bad at the luncheon, I will write about it later. 

Tennis Anyone?

Image from Tony Luginsland
on UnSplash.

 Back when I managed a prominent casual dining/bar venue, we had two women who would frequently come to our bar after finishing their round of tennis. 

Of course, I always noticed and was jealous of their short tennis outfits. I immediately put acquiring some sort of a tennis outfit on my cross dressing to do list. Since I had always admired short mini skirts and dresses on women, finding a short mini white dress to wear as the primary part of a tennis outfit was a priority.

As luck would have it, I found the ideal dress at a women's clothing shop in a mall I always went to. Once I had the white dress, I discovered the rest of the outfit would be fairly easy to put together. I ended up finding an inexpensive pair of white tennis shoes and socks to go with the shoes. The only problem I had then was what I was going to do about the hair on my legs. 

Even though my wife knew I shaved my legs on occasion, she was not overjoyed when I shaved. Primarily because she worried, I was up to no good when I shaved my legs, and she was right. On this occasion, I could not wait to show off my legs and new tennis outfit in one of the malls I always went to. Before I went to the mall, as always, I needed to create the time to do it away from my wife's disapproving eyes. I waited until she was working a day shift, and I began the fairly intense process of shaving my face and legs. 

Once I completed the shave and applied my makeup and hair, I was ready to test out my new tennis look outfit on the world. Immediately, I felt the thrill of my shaved legs in the short white dress I was wearing. So out the door I went into the world. As I arrived in the mall, I noticed my supposedly admiring public was primarily made up of retired men in the mall just to walk and admire the view. Since I was the view, I wore a pair of sunglasses so I could watch their reaction to me without being obvious. It worked and I could see them staring at the tall blond in a tennis outfit.

As I saw it, I received all the pleasure from tennis without putting in all the work. Now all I needed to figure out was how to hide my extra women's clothing. On this occasion, I used a little used closet and hid my new treasured outfit among a set of my old male clothes I never wore. 

For a change, my ideas of how to come as close as I could to learning for myself how a woman would feel in a tennis outfit came together. I could show off my legs and have fun doing it. Plus, I could cross another item off my transgender bucket list. Quickly, I was off to another quest. 

The Double Edged Gender Sword

Image from JJ Hart. Wife Liz on left.

The longer we live as transgender women and trans men, often we find many aspects which represent a double edged sword. 

One of the edges of the sword has to be the duress we feel when at first we arrive in public for the first time. To make matters worse, we have no peer group to help us out of the mirror to be judged by the harsh eyes of the world. No one to tell us we looked clownish as we tried the makeup arts for the first time. I can't tell you how many times I hurried home in tears following being stared at at the least, or laughed out of a venue at the worst.

From it all, I learned to develop a thick skin and always go back to the drawing board as quickly as I could to help solve any presentation problems I might have had. Even when I was doing it, the cross dresser drawing board was certainly difficult to figure out. What happened was, I used the very brief moments of gender euphoria I earned and moved forward attempting to tightrope my way along the sharp edge of my sword. I was risking ridicule at the least and the loss of family, friends and employment at the worst. Failure as a transgender woman was a very real pressure.

Once I began to learn how to present in public more effectively as a transgender woman, I began to use my sword more effectively.  Then the world became much more comfortable for me in my quest to live my femininized dreams. In addition, my makeup arts became better as well as my use of hair to enhance my appearance. 

It bares mentioning also, going through the overall transgender experience, made me a more resilient person and set up to battle the more challenging times we face. I learned in my research transgender folk have always been around and always will be, no matter who tries to erase us. Battling the sword all these years helped me be more secure in my transgender identity. 

In all fairness to my sword, it started out very dull. I worked long and hard to sharpen it by going out in public which was the best indicator of my progress.  So I took all the good and bad and did the best I could with it. All my interaction with the public included the dark evenings when red-necks repeatedly kept playing "Dude Looks Like a Lady" on the juke box in a venue where I was a regular. Since management at the time would not support me, I left to find another venue and took my money elsewhere. I was rewarded months later when an employee from the venue I was discouraged from coming to, found me in another venue and invited me back. To make matters even better, the manager who would not back me up was fired for drug use. Excluding a stray bigoted woman in the woman's room, I never had any further problems there again.

Once my gender sword swung back into doses of gender euphoria, I began to appreciate all it had done for me. Transgender womanhood was finally mine to enjoy when I learned I was not a quitter and was in my transition for the long haul. 

Trans Girl at Black Friday

Woman Shopping on UnSplash.

As I advanced on my feminine path to transgender womanhood, at certain points I needed to do more and more traditional feminine activities which cemented my claim to be a trans woman.

One of those was joining all the women in the world who were out and about shopping for the bargains bright and early on "Black Friday" or the day after Thanksgiving. My second wife for years was part of the crowd and made sure she was one of the early shoppers. 

Of course, I always wondered what the attraction was to go out and battle all the crowds, except for saving a little bit of money. Finally,  many years of wanting to shop with my wife as another woman came to an end but suddenly, on the other hand, I had the chance to shop on "Black Friday" as a woman by myself. Along the way, my second wife became the assistant manager of a large bookstore and of course "Black Friday" was one of their biggest days. So, I knew in advance she would have to work and I arranged my schedule so I did not. 

On the morning of shopping, I was excited as I prepared myself for a morning I had only ever dreamed of. First I did all the shaving preparation, including face and legs. I needed to calm down before I dressed in my favorite bulky sweater along with my best denim skirt and comfortable flat walking shoes. Then I began the more crucial part of applying my makeup and wig after I had calmed down...somewhat. After I reached what I considered to be a good presentation which would blend in with all the other women shoppers I would encounter, I gathered my courage to leave the house and head to a nearby upscale mall which I was very familiar with.

Unbelievably, in a very crowded parking lot, I found a space close to one of the entrances. As I checked my makeup and hair for the final time, I thought back to all the times I wondered what it would be like to shop with the other women on "Black Friday" and here I was and into the mall I went. My initial reaction was one of calm because no one was watching me, they were on a mission to find the best bargains and complete their shopping lists to bother about a transgender woman in the crowd. 

Since I wasn't really there to shop anyhow, I just browsed a few stores and bought a few small gifts for my wife before my shopping came to an end. After all, I had accomplished my goal of experiencing "Black Friday" shopping up close and personal as my authentic self. It was another item I could check off of my transgender woman bucket list.

Time flew by and  I needed to be back home to change back into my old boring male clothes to go to work, I needed to bring my dream day to an end earlier than I liked. 

Possibly the biggest lesson I re-learned that exciting day was the power of blending in with the rest of the women around me. As long as I could accomplish looking similar to everyone else, I could present well enough to get by. My first Trans Girl at the "Black Friday" shopping experience was certainly worth it.

Ditching Good for Better

 

JJ Hart with Ohio River.

As I made my way along my gender path, I was always looking to go from just good to better. 

I always wanted to present better as a girl my age all the way to moving like one and even doing my best to act like one. I did my best to be a keen observer of what the feminine gender around me was doing at all times.. If they were wearing mini-skirts, so should I was a prime example.

Sadly, I was hindered by my meager financial situation until I grew older and could afford more fancier accessories such as clothes and wigs. Even still, nothing was stopping me from pursuing my gender dreams of living as a woman. If only I could. That is where my path became more and more important. For example when I finally broke out of my closet and did all my own shopping, I learned the hard way what looked good on me and what did not. From there I could build on to my success and go from good to better.

I became especially good with my feminine business attire wardrobe. At thrift stores I managed to find a black pant's suit which paired nicely with heels or flats and my should length blond wig. I even had a wool full length coat to go with it for the winter time when I went shopping. For the warmer times of the year, I found a lime green business suit with a shorter skirt which I paired with pastel green opaque panty hose and matching kitten heels. I found I went from good to better either time of the year and presented relatively easier for the first time in my life. Gender euphoria at it's finest.

All of my fashion advances did not prepare me for face to face encounters with other women in the world. Chance encounters with store clerks were easy until I began to stop at restaurants to eat. I needed to order from a menu while at the same time doing my best to sound like another woman just having lunch away from her job. Until I gathered the confidence to practice it, the entire idea of talking like a woman was once of the most difficult things I had ever attempted.  I even went as far as going from good to better by taking vocal lessons to usher me into my transgender womanhood. 

I often think I inherited my drive to always do better from my parents. Nothing was ever good enough for them. If I had received a B in a class, why did not I get an A was the routine I grew up with. Imagine the irony my parents would have felt when they found I applied the same thought pattern to a gender issue they were very against. All I ever wanted was to be a woman, transgender or not and needed to work very hard to overcome my male bonds to do it. Plus I always felt if I was going to be successful as a transgender woman, I would have to try harder than the average woman to succeed. 

So along the way, I needed to not accept good and kept trying to achieve being better and better as a transgender woman. I wonder what my parents and my second wife would have thought of me now. Hopefully they would be happy for me, since I have arrived at the place I have always wanted to be in life. If I had done it sooner, I would have undoubtedly been an easier person to live with.