The Ultimate Confirmation

 

Image from George Pagan III 
on UnSplash.

My ultimate confirmation in life came when I arrived at a point when I knew without a doubt, I needed to live out the remainder of my life as a transgender woman.

My journey took me to the age of sixty when I finally put my male clothes away and live my dream. Along the way of writing the blog, I have received many interesting comments. Many concerning why I took so long and equating my time as a very serious cross dresser as somehow meaning I was never actually transgender at all. The best all time comment I received was, I was just another old guy on hormones. The comment came so long ago, I do not even remember how I responded.

I can make many excuses as to why it took me so long to transition completely such as I had a wife, I dearly loved who was against it, and a job I worked years to get which paid me well. While those are the given reasons, my ultimate confirmation came from the fact, I just did not have the confidence in myself to do it. For years, I was still being laughed at any time I went out in the world as my femininized self. Before I became very serious about my presentation and lost nearly fifty pounds off my masculine frame and began to take better care of my skin so I could wear less makeup. At that point, the laughter stopped, and I began to acquire the all-important confidence I needed to live my new transgender womanhood. 

Without confidence, I had nothing and little by little, I began to acquire it by doing trips into the world which took me away from the easy malls and clothing stores I was accepted in for my money, to the restaurants which presented me with whole new challenges to overcome such as having to communicate with servers and bartenders one on one. I even went as far as to stop going to the gay bars I thought were safe and going back to the big sports bars I was used to going to as a man. At that point, my ultimate confirmation was establishing myself as a regular at a couple of key venues where I was even given restroom privileges. Obviously, my confidence skyrocketed to a point where it never had been before. I could not wait to do more and more. 

Even with my newfound confidence, a fulltime life as a transgender woman eluded me. There still were huge life questions such as what would I do to support myself, all the way to how I would tell my friends and family. It was about this time in my life when destiny stepped in and answered nearly all my problems. In the space of a couple tragic years, my wife passed away, along with nearly all of my close friends. Leaving me all alone to guide my life in any direction I wanted to. The direction it took me was straight to gender affirming hormones which the Veterans Administration health care system was just starting to prescribe. Since I already was a VA health member, I went through the approval steps and was approved for the HRT program. 

My male self was stubborn about letting to but even he could not fight the ultimate confirmation he was facing. He should have never been in my life to start with and once he got there and established himself, he was difficult to remove. 

If you Know, you Know

 

JJ Hart from Key Largo, Florida

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

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

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

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

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

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

The Biggest Risk

 

Image from Engin Ackurt
on UnSplash. 

Recently, I had a comment from "Indigo" on a post I had just completed.

"Indigo" mentioned she was just beginning her transition and wanted to know what I thought was the most important male privilege I had lost when I crossed the gender border. My answer was, by far, the biggest privilege I lost was my personal security. In the space of one year, I needed to fend off potentially harmful attacks from men which I write about often in the hopes of protecting others searching for their transgender womanhood, or even novice cross dressers. 

The first negative learning experience I had was from a person, I will refer to as a transgender admirer at a small party I was attending with my second wife. The admirer was a much larger person than I and had literally trapped me in a narrow hallway in the house we were in. It was the first time in my life I had felt powerless to fend off another person who I thought meant me harm. Ironically, it was my wife who had to rescue me when she showed up in the nick of time. Since she did not approve of the provocative short mini-dress I was wearing that night, I had to hear way too many I told you so's on the way home. It turned out the lesson I learned was to do my best to judge the surroundings I was in before I could place myself in trouble. Not in any way shape or form what I was wearing. My wife was telling me about the right things for the wrong reasons.

The second main situation I found myself in was one night when I was walking alone between two gay bars in downtown Dayton, Ohio. Out of nowhere, I was approached by two men asking for money. I was lucky when they were satisfied with taking the last five dollars I had and let me go. From the experience, I asked for friends to accompany me when and if I ever went back there. By that time in my life, I was nearly done with gay venues anyhow, so it did not matter. 

I need to mention also, both of these learning lessons occurred years ago, and times have changed for the worse. However, the fact remains, women still have to protect themselves in the world from far too many toxic men. As another reader, told me, women are raised to be aware of situations which could be dangerous, and men are not. These days, a lot matters on where you live and how far along you are in your presentation. I am fortunate to live in a city (Cincinnati) which flies the transgender flag on the Transgender Day of Visibility and in an upscale suburb of the city which I have found to be very accepting to me. On the other hand, if I would drive ten or twenty miles to the next suburb, it is very conservative and non-accepting of transgender people. Plus, under current Ohio law, which is being challenged in the courts, I am not allowed in the women's restroom, which is a problem of course regardless of where I am. 

The best I can say is to anyone who is starting your transition, is to just be careful. You have to remember you do not carry your man cards anymore. Always, park at night in lighted lots and keep your head on a swivel. I know too, many transgender women who carry small firearms to protect themselves, but as far as I have ever gone is having Mace with me at all times. On top of all of this, under the current administration, if the wrong person senses something is wrong with your presentation, they could be emboldened enough to actually say something negative. Much worse than the old days when the worse which could probably happen was when you could get laughed at by a group of teenaged girls. 

It has always been very difficult to succeed as a transgender woman or man because to make it, often we have to be better than the next person. But once again please be aware of your own personal safety when you lose all your man cards. It is the biggest risk. For every negative, there is a positive and it is there are many supporting LGBTQ or transgender groups who will support you when you need it. There is a light at the end of the tunnel which is not the train. 

I Was Ready but Was the World?

 

Image from the Trolley Stop, Dayton, Ohio

It took me years to understand and accept my transgender womanhood, but once I did, what was the world going to think.

Once I had worked very hard to cross the threshold into being able to put a reasonable effort into presenting as a woman, the difficult work started. Even back in those days, I was able to learn basic tricks to take a good-looking picture but then I found putting the picture into motion was the problem. The whole scenario presented me with big new challenges, The largest mistake I made was underestimating how quickly the world would want to communicate with me. All of a sudden, when I was going out to be by myself, someone (usually another woman) would invade my little world. Which was suddenly growing rapidly. Initially, until I grew used to it, just trying to look another woman in the eye and talk to her was a real challenge.

I started by merely trying to mimic the tone and sound of the person I was talking to, then took femininizing vocal lessons to aid my efforts. I discovered quite quickly, I was more ready for the world than I thought. I found putting too much effort into communicating with a stranger could be a turn off and too little interaction could come off as being bitchy. So, I needed to be careful and usually let the other person lead the conversation. 

For the most part, I found the world was ready for a stray transgender woman just learning her way. I even was able to converse with several other women I met regularly in venues where I was a regular and so were they. I was amazed I had such an easier time talking to them woman to woman than I ever did as a man. One venue in particular in my world was a tavern called the "Trolley Stop" in Dayton, Ohio. It was/is the oldest continuing tavern in Dayton and I quickly became a regular of Gabby the daytime bartender. I knew from previous experiences, having support from the bar staff was key to my overall acceptance. So, I did my best to be friendly, spoke only if I was spoken to, and tip well. Being accepted in the Trolley Stop helped to really expand my world as a transgender woman and prove I was ready to do it. To make matters even better, the Trolley Stop even hosted a lesbian mixer every month or so and I enjoyed good times there as well. 

All of a sudden, the more I was out in the world as a trans woman, I proved I was ready to make it completely in the new universe I was in. It turned out to be one of the most exciting and satisfying times of my life. I was interacting and communicating with others. When I did, I made a whole new circle of friends (mostly women) I write about frequently. They provided me with the building blocks I needed to find my gender dreams. Once I had the solid foundation I needed, the rest was easy and fulfilling. Especially to my long hidden inner feminine self who had been punished for my entire life.  

  

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.

Nobody Understood

 

Virginia Prince

What really hurt me when I first realized I had gender issues was when I had no one to share them with. I was all alone with my problems, or so I thought.

I lived in fear of discovery all the time from my parents or my slightly younger brother. Even then, I knew discovery meant an unpleasant trip to a psychiatrist. The closest friend to me who may have shared a few of the same feelings, ended up moving away. With him, both of us were allowed to experiment wearing his mom's old clothes and putting on her makeup. It was the closest I would ever come to having anyone to share my true life with. Ironically, we never talked about the cross dressing we were doing. We just did it. 

As I said, my friend and his family ended up moving far away and years later, I often wondered if he had any gender issues too which stayed with him. Plus, as I always point out, I spent my youth and the years leading up to college in the information "dark ages", or the time before the internet became so popular along with social media. All I had was my cherished copies of Virginia Prince's "Transvestia" publication to get me by. At the least, "Transvestia" showed me there was a community of others with the same gender leanings I had. Also, in my well-worn issues I saw meetings or mixers within driving distance of me which I could go to. I was excited when I learned I could actually meet other self-proclaimed transvestites in person. The problem was, once I learned I could meet them, was I brave enough to do it. 

You all know, I was brave enough to meet them but then I encountered another problem. No one at the mixers still seemed to understand me. I was too much of a woman for the cross dressers and not enough of one for the transexuals. This was back before the transgender term and meaning was even used and popularized, so once again, I was stuck with no one to understand me.

Finally, the world began to catch up with me and I understood where I was when it came to the cross dresser - transgender community. Even better, with the help of the internet and social media, I began to stay in touch with others with similar views. Suddenly, in many ways, everybody had some sort of an understanding about how I felt. It may have taken me a lifetime to do it, but I made it into the only community who knew what I went through.  

Maybe the problem with the world as we know it these days has been influenced by people who have never met a transgender woman or trans man at all. To understand a trans person, it certainly helps to have followed a similar path. Even briefly. 

In recent years, I went from no one to understand me to having a whole group of people who have not taken the time to even accept me on a basic human level. It seems, I have gone full circle to arrive nowhere. 

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. 

Someone is Paying Attention

Image from Alena Garrett
on UnSplash. 

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

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

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

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

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

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

Down the Rabbit Hole

 

Summer Image, JJ Hart.

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

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

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

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

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

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

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

Your Personal Best

 

Image from Markus Winkler
on UnSplash.

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

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

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

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

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

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

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

Meeting in Person

JJ Hart in a warmer time.

Do you remember the moment you met your authentic self in person?

Looking back, I can recall several profound moments when I saw the feminine person I was always meant to be. My earliest memories came when I was quite young in the days when I was first experimenting with my mom's makeup and clothing. Even though I probably looked like a clown, the mirror told me I was beautiful. No matter what I looked like, I refused to face the truth. 

It was not until much later in life, when I began to realize how much work it was going to take to really see my true self, did I get serious. If I was going to make it to my dream of transgender womanhood, I would have to profoundly change my way of thinking. The first change I made was how my male ego interacted with my appearance the public saw when I went out for the first times. 

The truth of the matter was, if I dressed "down" to blend in with public, I received very little attention, so I started to dress too trashy to please my old male self. What quickly happened was I attracted the wrong type of attention and did not pass well. Or, at all. Back to the cross-dressing drawing board I went time after time until I drove my male ego out to the point where I was successful in blending in with other women in the world. What were the women wearing and when were they wearing it became my motto. The time I spent was worth it when success as a novice transgender woman was becoming mine. 

Suddenly, my visits to the mirror became more and more friendly. I adjusted to the fact I would never be the prettiest woman in the room, but I could rely on other feminine attributes to get by. I began to closely study other women who may not be the most attractive, yet still be popular, fulfilled women. What I did was, I began to concentrate on what my new personality would be as a transgender woman. After all, I had an unique opportunity to start all over again as a human being. My new time was a scarce commodity, and I could not miss my opportunity to do it right. 

I was fortunate in that I already had a women friend who was ready to help me. She had been there all along, just waiting for her turn to lead my life. She was the feminine inner me. It turns out she was a nice person who saw the best in others. When I met her in person, I was excited and knew I was in good hands.

I was in good hands and began to expand my small circle of friends in the world. My wife Liz and I started to go to small and medium sized "Meet Up" groups in Cincinnati where I learned the benefit of a different group of strangers accepting me. None of us knew each other previously, so I was on an even level with them. The great equalizer. 

All of the process was extremely beneficial when it came to meeting myself in person until I became used to it. Perhaps the best part of the entire process was the time I realized I had really expanded myself as a woman, transgender or not.

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. 

Happy Valentines Day

 

Happy Valentines Day Liz!!!

Admittedly, I have never been much of a romantic, as a former man or a woman. Over the years, I have started to change as I entered transgender womanhood. 

After my wife passed away, I was intensely lonely and began to look around for company. At first, I started by going on-line under various platforms. For example, one week I would list under woman seeking woman, then the next week, I would list under woman seeking man. In total, predictably, I received very few responses. None, I considered quality except one and her name was Liz who contacted me under woman seeking woman. She was from nearby Cincinnati.

In the meantime, I did make a couple other lesbian friends out of sheer will power by forcing myself into going out and being social. The first friend was introduced to me by her daughter at one of the sports bars I was a regular in. The daughter noticed I was always alone and thought it would be fun to do a little matchmaking.  The great part is, we still are friends to this day. 

Then one night when I was out to be alone, another woman came in to pick up a to go order and ended up sliding a note down the bar to me. We ended up meeting and she became part of a small group of women I partied with almost nightly. Plus, as I always say, these two women taught me so very much on what it would be like to live life as a woman, more than they will ever know. 

By now, you may be thinking, were there any men in my life? Yes, there were a few including all the ones who would stand me up on dating sites. I did have a couple memorable dates with guys which never went beyond the kissing stage. Even though I enjoyed being on the other side of the dating spectrum, I still much preferred the company of women. Especially when I was accepted for me. I was satisfied on where I was in my dating preferences and saw no need to change. Plus, when I went to lesbian mixers, I found I could further my preferences as a transgender lesbian.

Perhaps my biggest discovery was how many lesbians were not of the "gold star" variety which meant in their past they had some dealings with men. With me, they found a curious gender middle ground which the majority of insecure men were afraid to pursue. During this learning portion of my life, I ended up enjoying myself immensely.

What I have left out of all of this on purpose was my interaction with Liz. Through it all, we had continued to talk back and forth. Once I was brave enough for her to hear myself on the phone. We finally arrived at the point where her and a group of women friends from work were going to a drag show near Cincinnati. The drag show ended up being our first date nearly fourteen years ago. Obviously, everything went well and ten years later, we were married. 

On this Valentines Day, I credit Liz with being the only woman who ever told me she never saw any male in me at all. In many ways, she helped me back on my feet after some rough years of my life. Happy V-Day, Liz!

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.

A Spectator in my Own Life

 

Image from Ryan 
Mangino on UnSplash.

There were many times during my life as a transgender woman, I felt as if I was a spectator looking in on the action.

The whole process was very strange to say the least as I was thinking, just who was that person. Plus, having the chance to think what I was doing was a totally different sensation. The entire problem stemmed I think, from the earlier years of my life when I was positive, I was two different people all together. One male and one female. It was not until much later on when I began to realize I was always feminine and fought all things male when I could.

Slowly but surely, I began to realize the truth and began to notice my cross-dressing nights out involved much more than just attempting to look the best I could. My spectator began slowly to change away from watching a male life unfold to watching a female one do the same. Helping me were the girls-night-out invitations I received. Following a bout of impostor's syndrome, I suffered through, I settled down and enjoyed myself. When I came to the conclusion I had just as much right there as the next woman. We had all came to our right of womanhood through different paths and mine was just different.

Finally, I grew tired of just being a spectator in my feminine life and wanted more. More meant being a spectator in my male life. Since I was still working and living part-time as a man, it meant I really needed to concentrate on my speech and movements when I was still a guy. In fact, there were a couple of embarrassing times when I was called Ma'am at work when I was in male mode. 

Early on, being a spectator in my own life was certainly a curiosity. Especially, when I thought I was just a cross dresser and putting on a dress was just a hobby. The closer I moved to true transgender womanhood, the more I learned that was not true. As I always say, the key moment in my life came when I realized I was not a man cross dressing as a woman, I was a woman cross dressing as a man. The tragic part was I went through male puberty and was testosterone poisoned as I grew up. I did not appreciate when my soft body turned to hardened angles as well as the other male changes but there was nothing I could do.

When I found my gender destination, I stopped being a spectator and began to be a more involved participant. For me, flipping my gender became an intensely frightening but natural part of my life. Living my dream was so dominant in my thought pattern, I had no problem with girls-nights-out and even could not wait for them. My newfound confidence as a woman completely pushed any idea of me being a spectator aside and opened the door for me to be a more well-rounded participant. Of course, confidence always grows more confidence, and I grew to the point where I had nothing else to prove to the other women I was around.

As I look back, being a spectator in my own life as sometimes a necessary but very different part of my existence. The entire process sometimes helped me to understand where I was going towards my dream of transgender womanhood.  

No Struggle no Progress

 

Image from UnSplash.

Basically, when it comes to doing anything really important in life, to progress you need to struggle.

As far as being transgender, often it seems our struggles are impacted. First of all, most of us are not blessed with any natural feminine characteristics to work with. At least, I did not think I had any except perhaps my legs which often ruined my fashion sense when I tried to focus on my legs and not try to cover up my wide torso and broad shoulders. I struggled with my overall image until I got it right and I began to blend in with the public at large. 

Far more important to me was the mental struggle which went along with my journey to transgender womanhood. For the longest time, it seemed as if every step forward I achieved in the world as a novice transgender woman was met by taking three steps back. Or when I thought I had conquered the world of high heels, I would catch my heel in a sidewalk crack and break it. Who knew you had to put so much work into being a girl and it was only the beginning. 

Along the way, my life became a battle between two genders and for the most part, the battle destroyed me. Especially, my already frail mental health since I was already diagnosed as being Bi-Polar, I did not need any other problems I never asked for. Regardless, life moved on as I tried to roll with the punches. I was cross dressing as much as I could while at the same time, I was trying to live a life as a successful man. I managed to stay married to the same woman for twenty -five years while at the same time making good progression in my employment career. Sadly, I was stubborn, and struggle was all I knew as I lived my life. If I would have ever relaxed and looked around, I would have seen much of my progress came from just running from my problems and not facing them. My wife said it best one day when we were locked in yet another brutal argument. She said, why did not I be man enough to be a woman. The logical answer to the question was, I simply was not ready and still had a lot to learn before I jumped the male gender ship and began to live as a transgender woman. 

Very soon, my struggles reached a critical tipping point where progress was becoming the norm. I was reaching the point where I could be man enough to be a woman out of sheer determination. Sadly, by this point, my wife had passed away, so she never had a chance to meet the woman I had become. Again, I needed to struggle through a new reality of being alone after all of those years. It did not take me long to turn to my feminine self for help. In fact, the last date I had set up with another woman as a man was to an outdoor concert. At the last minute, the woman backed out, so I did the next best thing and took myself. My feminine self-had a great time and I never tried to go out with a woman as a man again.

As I began to see and reach my potential as a transgender woman, my mental health improved as well as my life as a whole. When it did, my struggles went with it.

And Then he Was Gone

 

JJ Hart at Club Diversity
Columbus, Ohio

It took me nearly a half a century to rid myself of my male self and begin living as my authentic feminine self.

Even though much of my progress towards my gender goal was physical, much was mental also. The physical part I am referring to was the portion of my transition which revolved an intense period of time I went through attempting to judge my appearance in my own personal mirror. I was so into myself, my wife began to call me the pretty, pretty princess and told me I was ignoring what a woman really was. She was right and it took me years of research and struggle to learn what she really meant. 

As I learned, the more my male self-fought me as he did not want to give up any of his life and male privileges he had fought so long to earn. It seemed every small gender victory was hard earned until he was gone.

Perhaps the biggest factor against him was I felt so excited and natural in the new world of transgender womanhood I was creating. Surely, I was still having my ups and downs when I tried out the public when I went out, but the downs were becoming fewer and farther between. Plus, my amount of terror I was still experiencing as a transgender woman was decreasing by the day. I think now, the major reason was I finally made the mental decision to go forth in the world as a woman on my own terms rather than the part time cross dresser I had somehow portrayed myself to be. Some may say I was dealing in semantics, but the thought pattern was a revelation for me. 

As he disappeared, my female self-had no problems filling the void in my life. My long-buried woman self-had no problem putting her past behind her as she stepped out into the bright lights of a new world. I think having no resentment made her a better person people could relate to and like. In fact, I found many new people related to me as a woman than ever before as a man. 

Ironically, after a very slow start to the fifty years of gender discovery I endured, once I seriously started my transition. time went very fast. Perhaps, it was because every night I went out, I was learning so much new on not being just the pretty, pretty princess and finally experiencing what my wife told me about being a woman was all about. Or I was finally given the chance to go behind the feminine gender curtain into a world dominated by women. When I did, I found women ran their own world their own way without the help of men. During the girls' nights out, I was invited to I learned what was important to women and not men. Even along the way, I learned the power of non-verbal communication between women when one night I was warned away from an intoxicated man in a venue I was a regular in by a bartender I knew. With one look, I immediately went the other way away from him and was safe.

Finally, after so much learning and experiencing a new life as a transgender woman, I think my male self-saw the writing on the wall and decided he was done. When he did, a huge weight was lifted from my shoulders. It seemed carrying two people all those years took a toll on me, and I wanted out. 

Staying in your Own Lane

 

Image from Gabriel
Silverio on UnSplash.

As I transitioned into my own version of transgender womanhood, there were plenty of opportunities to not stay in my own lane.

First of all, I needed to get my presentation house in order so I could even receive a fair chance at starting. Paraphrasing "Stana" of "Femulate Blog" fame, in order to pass properly, I needed to first signal before I accelerated and moved to the outside lane. For me, acceleration was not an immediate or easy thing to do. Before I began to see any progress, I needed to put the mirror behind me and seek approval from the public at large. Once I was able to do that, then I needed to push away any of my ingrained male thoughts I was having on how I should look. He was leading me towards a totally trashy look which was attracting too much negative attention. If I wanted to stay in the feminine lane and be successful at all, I would have to change...quickly.

Once I began to be more comfortable and accepted in the feminine lane I was in, I needed to then learn all the nuances of the new life I had chosen. Immediately, the concept of passive aggression got to me. Too many times, I was fooled by another woman's smiling face or indirect suggestions. Examples included the times when I was complimented on how I looked. I was told how good I looked without the extra statement, for a man dressed as a woman. Regardless, I had too many claw marks down my back from encounters with women who I perceived as harmless. It took me awhile to learn the new lane I was in with other women. Once the scars healed on my back, I developed the knowledge and thick skin I would need to get in the passing lane and survive.

As I cautiously began to live more and more in my new gender lane, the more natural life became. I developed a whole new group of women friends and learned tons of ideas from them on how to stay where I was. The group of us partied into many nights and I discovered I was still messing up by trying to live in both gender worlds. I guess you could say, when the going became rough in the feminine lane I was in, I could always escape back into my male privileged world I knew so well. Finally, with the help of my friends who were primarily lesbians, they taught me my validation did not have to come from men, it could come from within. It was the only signal I needed to switch gender lanes and stay there.

These days, with the current political climate, we transgender women and trans men are trying to be forced back into our original lanes. It is in times such as these when we still have to be as visible as possible and live our lives as authentically as possible. As I have written several times, my own demarcation point of support is coming up in May with the Veterans Administration health care system. In May I have an appointment with my Endocrinologist and the opportunity to get my Estradiol prescription renewed. I naturally don't have total confidence the government won't step in and block my gender affirming hormones. I am sure, I will be writing about my fears as the date gets closer.

I am desperately trying to stay in my own lane which meant years ago I was able to live as the person I was always meant to be. At my current age of seventy-five, there is no way I am going back to my old lane I was unhappily living.     

A Push versus a Dream

 

JJ Hart

I often describe my journey to transgender womanhood as the impossible dream. 

On the other hand, I cannot ignore all the pushing I needed to do to arrive at my goal. My pushing started at a very young age when I was first cross dressing in front of the mirror. To begin with, I needed to push hard to find hiding places for my exceedingly small, treasured collection of feminine wardrobe selections. I resorted to old boxes in the garage attic, all the way to a hollowed-out tree in the woods next door to our house. In trash bags. Anything to stay safe with my secret. I knew if I was exposed, life as I knew it would be over.

I did push on and survive so my dream was still intact when I went to college and then served out my time in the military. My military time was especially stressful as I needed again to carefully conceal any idea, I was feminine at all. Through it all, I needed to keep my thoughts centered on a far-away dream I had of being able to live as a transgender woman. Sadly, there were too many times when I did not see how I could make it at all. Especially when the Army was strongly reinforcing my manhood. 

As in many other facets of life, the Army came and went leaving me a sense of freedom of what I could do concerning my gender issues. My first marriage came shortly following my discharge from the military and left me still wondering about what was going on. My first wife knew I was a cross dresser and did not really care, so I was left on my own to make any gender decisions I might decide on. This was back in the late 1970's and there was very little information on even being a cross dresser available. Again, I was on my own until the computer became a reality, and I was able to reach out to others. I learned quickly I was not alone and began to push for more clarity in my life. I even was able to dream more frequently of being able to live as my authentic self.

Before I did, I needed to determine what my authentic self really was and push to get there. This meant going down a largely selfish road as I carefully checked my gender boxes. It took me years to figure it out until I was able to merge how hard I was pushing with my ultimate gender dream of a being a transgender woman. My authentic self which was revealing her-self When she did, she left no doubt on why I felt the way I had my entire life. Something was not quite right, and I pushed on to figure out what the problem was. In the meantime, I treaded water cross dressing in front of the mirror until I found the courage and confidence to try going public.

Each and every time I was successful at all in dealing with the world, my dream was re-ignited, and I started to push through or totally ignore any gender warning signs I encountered. Everything I was doing put me completely at odds with my second wife, who again knew I was a cross dresser but never wanted me to leave the house dressed. Not only did I break my promise to her, but I also went as far as beginning a whole new life. My new life rapidly became very important to me mainly because I was happier and the whole life felt so much more natural.

My lifetime full of pushing finally aligned with my ultimate dream of transgender womanhood. Destiny opened my gender doors at the age of sixty and I took complete advantage. 

Burning Gender Bridges

 

Image from Adam Wilson
on UnSplash

During my life, I have always excelled in self-destruction. It seemed, whenever I had succeeded in anything positive, I always tried to tear it down. 

I blame the entire process on two basics, one of which on how I was raised. My parents never accentuated the positive at any time. If I received a "B" in any class, invariably I heard, why didn't I earn an "A" and I was not applying myself properly. The other basic was anything I accomplished as my male self; I did my best to reject. I did not in any way want to accept any success I earned as a male. So, I did my best to burn the gender bridge I created. 

Of course, the more I went down my gender path towards transgender womanhood, the more bridges I needed to burn. Everywhere I looked, the stakes were higher in life. All along I was accumulating more and more success as my unwanted male self which made my decision so much more difficult. Still, I forged on with my torch burning brightly. To hell with the results, I was going to attempt to follow my gender dreams anyway. Finally, I arrived at the point where seemingly I was subconsciously trying to sabotage myself. In many ways, I was desperately attempting to hide my deep dark cross-dressing secret while, on the other hand, I secretly wanted everyone to know I had always wanted to live as my authentic feminine self and did not care what they thought. Still, I needed to be careful as I had deep roots to my male past. Spouses, family and jobs were at stake. So, I tried to be sure of what I was doing before I cut the gender tree down.

Perhaps the most substantial bridge I needed to burn was to my job. I was a very successful restaurant manager in a regional/national casual restaurant chain. The management was very male dominated, and I knew there was no way I could ever transition in the same job. 

I decided to try going to other similar food/bar competitors thinking no one would recognize me. Long story short, I found out the hard way I was recognized as a version of my male self. To make matters worse, I tried to frequent my own operation and was close to being immediately recognized. In doing so, I burnt a major bridge which I don't think my wife ever found out about. It was bad enough when she knew I was breaking the agreement we had for me to never leave the house as a transgender woman.

The new bridge I built when I burnt the old one was when I decided to buy my own restaurant. I figured if I was the owner, no one could tell me what to do. That was true to an extent until one night a very evil former acquaintance met me in the parking lot to tell me my lifestyle was keeping the public away where we operated. I don't know how true what he said was but one way or another, I had burnt all my gender bridges and there was no way I could ever go back. 

When I transitioned and began my life as a transgender woman, I was able to build new strong bridges for the first time in my life. It was like my feminine soul was excellent in her building skills and could not wait for a chance to thrive.

The sad part was/is how much destruction I had to go through just to arrive at where my dream could be born. It turned out the birth was the easiest part of it all, as I set out to live a fulltime new life in my transgender womanhood. I finally had the chance to put my fire out. At least the destructive one.