It is In Your Nature

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Following my fifty year battle with my gender issues, I just gave up and went with what felt so natural to me and completed my transition into transgender womanhood.

It was certainly a long drawn out journey of self discovery. It was full of ups and downs as I gained my footing along with confidence as I learned to just be myself. Looking back, I don't know what took me so long. Perhaps I can blame it on my male self wanting to hold on to the lifestyle he worked so hard to survive in. He put up quite the battle before giving in. But give in he finally did. 

When I finally began to explore the world, I learned how much of it was run by women and in order for me to survive, I needed to get along one on one with the other women around me since men rarely showed me any interest as a person. Women on the other hand were curious why I was in their world and I was somehow valued for being there. Perhaps it was my honesty showing through, which I gained from jumping the gender border into their world. I don't know for sure but I loved the attention I was getting. 

It was in my nature, because I had always valued the women friends I had over the very few men friends I ever was capable of having. I just did not fully ever recognize why until I was fully allowed to play in the girl's sandbox. Before I was allowed in though, I needed to earn my way in. I had to show my true nature was feminine and I needed to learn the rules of a brand new gender game. For example, I found myself in a world where passive aggressiveness ruled and a smiling face did not mean it was a friendly face. Much different in the world of men I was used to. It all was more of a mental game than I was used to also as I tried to anticipate where another woman was coming from. Especially when I came down to interacting with their men. On a few occasions, I came too close and felt the claw marks down my back for doing so.

The whole process just made me stronger and more confident in the woman I was becoming. Quickly I felt as comfortable in the new world I was in as I learned how the gender game was played. Women are more apt to form cliques than men who form teams and instead of finding the alpha male for acceptance, I needed to find the alpha female who was running the clique and I was in. 

Once I was in, my life became so much easier. Primarily because I did not have to fight being two genders anymore and the inner woman I was hiding for so long had her chance to run the show. She took to the process naturally. The only thing she did not do was harass me about why it took me so long for her to take over. Which she had every right to do. More importantly, I found she was a good person and got along with people including the all important world of other women. Essentially I found I good set and enjoy the show.

Of course before I could enjoy the show, I needed to understand the process of how to blend in with the world as a transgender woman. It was difficult putting my old male ego aside and realizing I was never going to be the most attractive woman in the room, I could present well enough to survive if I had the confidence to do so. 

What I really learned was, it was all in my nature to do so and if I relied upon it, I would be fine.

Finding your Happy Place

 

Image from Priscilla du Preeze
on UnSplash

These days you may think finding any sort of happiness as a transgender woman or trans man may be impossible but it is not.

Take this morning for me as an example. As I was getting dressed and viewed my bare thighs before I put on my pants, I had forgotten how nice it is to view their increasingly femininized form thanks to the use of gender affirming hormones. In other words, I have developed my own hips, finally following years of hormonal usage. In many ways I took the slow cautious route when I started down the medical transition path on the advice of my doctor. He advised me to take minimum dosages until we could judge the effects on my body.

At the age of sixty, my body took to the new feminine hormones wonderfully and naturally. Soon I was put on higher doses of HRT and bigger changes began to take place rather quickly. I had set up a semblance of a timetable of when I wanted to shed all my male clothes and live fulltime as a woman but it turned out the timetable was a waste of time. What happened was I became very androgynous looking in a very short period of time. While I was developing an increasingly noticeable set of breasts, my skin began to soften which in turn softened the lines of my face. So much so that anyone who knew me from before would notice the difference.

Even though I was shocked at the rapid exterior transformation of my body, the whole process felt so exciting and natural I could not wait to do more and more as I accessed my new transgender womanhood. It all meant setting up new plans and timetables on who I was going to tell and when. By this time in my life I had outlived most of my family and close friends, so telling many people was not going to become a problem. I had even retired so I did not have to worry about transitioning at a job. All of this left me with two main people to come out to. My only daughter and only slightly younger brother. 

I knew at the time, I had a better chance of succeeding at telling my daughter the truth about me than my brother. My daughter was much more liberal while my brother's in-laws were right wing Baptists and I figured he would sell me out to appease them. It turned out I was right on both accounts. I found my happy place when my daughter totally accepted me and was down when my brother did not. I took my fifty fifty win/loss record and moved on.

To this day my happy place continues with my daughter and her extended family. In fact, my wife Liz and I just accepted an invitation to Thanksgiving dinner at my daughter's Mother-in-Law's house which makes up for the decade long snub from my brother. 

As the holidays approach, I hope all of you can find a happy place to celebrate with family, blood relation or not. In the transgender community, often we find the best family in non traditional situations. It is a wonderful time of the year to discover or re-discover a new happy place for yourself.

Finding your Happy Place as a Trans Girl

Image from Trans Outreach, JJ Hart

As I negotiated my way through the gender wilderness I was in, I needed to reach out at times to find moments of gender euphoria or happiness. 

As I have written about in the past, happiness was a learned trait which was difficult to come by in my family. Being good was not good enough, there was always time to be better. Little did I know, I was seeking to enter a world where being better than the average cis-woman was not going to cut it. Being better meant survival. 

As similar to most of you transgender women and/or cross dressers, I started out innocently enough as I raided my Mom's clothes and tried to admire myself in the mirror before my family came home. The whole process worked well for awhile until I grew restless and wanted to increasingly explore the world as my femininized self. Sadly, most all of this occurred when I approached puberty and all the unwanted male changes to my body began to happen. Very soon, I found wearing any of Mom's clothes was impossible as I gained unwanted hair, bulk and angles I hated but were stuck with. It was the infamous testosterone poisoning setting in which I battle to this day.

Rather than be unhappy, the mirror and my mind helped me to battle my way through severe bouts of gender dysphoria. I worked hard on acquiring the proper clothes and makeup I would need on a very limited budget. Of course with no guidance, I experienced many disasters on my journey before I settled in on an appearance which could get me by in the public's eye. I needed to disguise all my testosterone poisoning. Still, I persisted without much help and slowly learned the art of makeup which finally I did get some assistance with. At one of the cross dresser - transgender mixers I went to, I put my ego away and sought help from one of the professional makeup artists they had giving free advice. In language even I could understand, the guy doing my makeup guided me through a truly amazing transformation. Even I thought I looked so good I was happy with the results. 

Even still, the transformation was fleeting and all too soon, I needed to go back to my boring unwanted male life and the happiness I felt went with it. Leaving me in a state of depression. I did not realize having a feminine appearance was only the beginning and achieving any standard of looks went only to the upper levels of feminine achievement for me. Beauty was fleeting and very skin deep for me as I continued on my gender journey. I was told several times by my second wife I made a terrible woman and in no way was she talking about my appearance. She was right and it took me years to put my male ego behind me and learn what she truly meant. 

I also had a close transgender friend who told me one time I passed out of sheer willpower. Which I took as a backward compliment. Meaning I was going to engage the public and do my best to be happy even though I was not the most attractive woman in the room. When I did, I made a huge step forward towards becoming my authentic self. It was not until then did I begin to gain new friends and become happier. 

Sadly, my second wife passed away before she ever had the opportunity to meet the new improved me but I did have several friends who did. Their main comment was how much more happier I had become. I guess I never realized how much my gender issues had shown through to others in my male life. 

When I reached this point, I knew my family and upbringing was wrong. I could be happy in life and appreciate it. Along the way, I learned the truth that all the money and beauty in the world could not buy me happiness. I spent way too long living in the mirror to keep doing it. The friends and wife I made when I put my male self behind me proved happiness was not impossible for me. 

Hitting the Transgender Wall

 

Image from Selin 
on UnSplash

There were so many times during my journey to finding my authentic self that I hit a wall or two or more. 

The easy walls came when I was younger and was trying to find makeup and wardrobe items to admire myself in the mirror. During that time and into the future, finances were a major set back. As much as I admired the pretty clothes the girls around me were wearing, I just did not have the money to afford any of them. There was no way I could go to my parents and ask for a pretty dress for my birthday or Christmas. Plus, I was stuck at a major point of my overall femininized image when it came to my hair. In those days, I was stuck with very short hair cuts such as burr or crew cuts and there was no way I could afford a wig. A major wall, to be sure as I think having the first wig I cherished did not come around until my college years in the late 1960's till the early 1970's when my military days took over. Of course I was against the wall again when my hair needed to be kept very short.

After I had served my time in the Army, I was able to secure the finances to afford a more update feminine wardrobe and my walls began to take on a more mental aspect with me. The more I was able to sneak out of the house and into the public, the more I knew I had little or no knowledge of where I wanted to go as a novice transgender woman. It seemed everything was being thrown at me at once and my mental health crumbled after I was hitting many walls at once. My male life was becoming more and more demanding as I became successful at my job and I discovered the more I explored the female world, the more I liked it. 

Even so, climbing the feminine walls were difficult. It seemed everytime I mastered one aspect of being a transgender woman such as walking, I would catch my heel in the crack of a sidewalk and ruin my whole day. As I continued along my bumpy gender path, I found mishaps with walking in heels were indeed minor in the scope of my transgender life. On the horizon loomed much more serious walls such as communication with the public and with women in particular. Overwhelmingly, men ignored me and women were curious about what I was doing in their world, I discovered quite quickly I was interacting with more women than I had ever done as a guy which was scary in many ways, including what would I say and how would I say it. 

I wondered what had I done when I was forced to actually talk the talk of the person I had become. I resorted to what had worked for me in the past as I had encountered tough trans walls to climb. I basically tried to shut my mouth and observe what was going around me. It worked to an extent until people (women) began to warm up to the new person I had become. I even was giving other women advice on how to understand their boyfriends or spouses. 

Anyway you cut it, I guess for me, gender affirming hormones created the last major wall for me to climb. At the time, I was doing my best to appear as a woman and communicate as one to the world. Beginning the hormones in many ways was a selfish move because I did it for myself. When I did, instead of more walls crashing down, they melted. HRT, when I was approved for it was a magic potent stimulant my body had been craving for years. Very quickly, I knew I had made the right move as I was able to tear the final walls down and make my way into fulltime transgender womanhood. 

Surely, I was bruised and battered by hitting all the transgender walls I needed to scale to live the life I wanted but I made it. When I look back on all the terrifying yet exciting steps I took to get to where I am mow, I wonder how I made it. First there was my appearance and battling testosterone poisoning then overcoming the problems of male behavior which also effected my life that all made for a rough journey. Surely there were too many walls to count.   

Happlily Ever After?

 

Image from Dave 
Goudreau on
UnSplash. 

When it comes to transgender women and trans men, is there ever a happy ending?

As we examine our lives , again and again, we inevitably encounter many pains as we make the transition from one gender to another. Most of us (including me) go through a period of time when we consider ourselves to be cross dressers or transvestites. We were in our own state of limbo, not knowing where we were going. I am amazed when anyone in the outside world thinks our life was so much easier and we were wearing the clothes of the opposite sex as some sort of a lark.

The fact remains, amidst the brief moments of gender euphoria in front of the mirror, we never actually had a choice when it came to our gender issues. In the case of many people such as me, my journey was very lonely and singular and I wondered if I could ever live happily ever after as a transgender woman. It seemed like the impossible dream and if I could ever arrive there, perhaps I could finally become happy. But happiness for me had always been fleeting. Probably because I had never seen much of happy in my family growing up. We were taught anything we did was never good enough. It carried over into my life as a novice transgender woman. 

No matter how attractive I thought I was, there always had to be more. I needed to be better as a trans woman. It turned out I did need to be better to survive in a new feminine world but getting there was a challenge when I went too far, too fast in the wrong direction. Primarily when I went over board in how I was dressing myself way too slutty and attracting the wrong attention to myself. It wasn't the type of validation I was seeking. It took me awhile to realize I could not make it to any semblance of happiness on the path I was on. 

I learned I never would have a chance to be happy in transgender womanhood, unless I began to change my ways and began to dress to blend in with the world. Once I did, I learned I had a whole new set of challenges I needed to face to be happy. Similar to many of you, I faced spousal issues as well as job, family and friends. I always considered changing my gender was a difficult task to take but I never knew all the nuances of making the change I would have to take. Being a woman, trans or not, was a very layered process and I would ever be happy if and when I ever arrived at my goal of living fulltime as my authentic self. 

Then there were the gender affirming hormones I decided to pursue. Before I could begin the meds, I needed permission from a doctor and a therapist to begin. Adding to the importance of the move but once I started the hormones, I knew I was in the right place and I would not turn back to my old unwanted male life.

Even with the HRT, happiness was still fleeting as I faced a wonderful new world. Most likely because there were still instances of public setbacks I still had to negotiate, which included times when my mind was playing gender tricks on me. I was still influenced by sixty years of living a male life and being conditioned to never be happy.

Now, at the age o seventy five, I know I certainly have fewer years ahead than behind me. Now I have to make a concerted effort to be happy. If I don't, it will be too late.

Intimidating Women

Library of Congress 
image from 
UnSplash.

During my life, surprisingly so, I have encountered many intimating cis-women. 

Probably the most intimidating of all was my Mom, a dynamo at a mere five foot two inches tall.  From early as I can remember, we clashed on many different issues probably because we were so much alike. On the girl side, I was fascinated from a young age when I watched her skill with makeup and hair. I could only dream of ever duplicating her prowess. Of course I would never get the chance for her to ever see the fashion skills I finally developed as the daughter she thought she never had. 

As I grew up, my intimidation of girls of all kinds increased. I was so jealous of their ability to dress in pretty clothes and wear makeup continued. In addition, I was so shy, I was afraid to communicate with girls at all. So my problems continued to get worse. I never had the chance to circle back to where I began. All the time I was cross dressing in front of the mirror, it was a very solitary, lonely experience as I craved the peer feedback other girls my age had to work with. 

The older I became, the more I admired women who were stronger and spoke their minds. You might say I was intimidated in the most positive ways by strong women. I was even attracted to them to the point I chose one for my second wife who I was married to for twenty five years. Even though she knew I was a cross dresser from the very beginning, somehow I secretly thought she would help me with my on-going quest to be a feminine person. She never really did help me much and very much resisted any ideas I had I was a transgender woman. 

Perhaps I am attracted to strong successful women because I wish I was one. I so admired the women managers I worked with because of all the extra skills they had to use to be successful. Most if not all of them had families to support at the same time they worked a full-time job. I was in the restaurant business and some of my best kitchen managers were women who dealt with macho kitchen crews. 

Being a transgender woman, I think sometimes I intimidate other women. Sometimes they seem to melt with kindness such as the hostess last week when my wife Liz and I went out for my birthday dinner. She was beside herself to make sure we were satisfied with our experience. As I can remember, intimidation on my part of a guy was when I was shopping at a grocery store years ago for the families groceries. In those days, a fashionable woman who had the legs wore an oversize sweater with flats and a mini -skirt, so I did on that day. As I chose our food, I tried to contain my fear in checking out, I found I was wrong.  As it turned out, the store was nearly empty and only had one check-out lane open with a woman cashier and a male bagger. 

It turned out, I really intimidated the bagger, he blushed and stuttered when he asked me if I needed help taking my bags to my car. I looked at the cashier and him when I said I didn't and she gave me a slight knowing smile. I wondered then, if she knew I was transgender at the time or not. Regardless, it was quite the experience. 

It wasn't until I transitioned into a feminine world as a trans woman did I fully understand all the nuances of what it takes to be an intimidating woman. For example, some women use their heels to begin the process. Heels give a shorter woman a height advantage to be able to compete with the men in their world. Plus, these days, more and more young women are becoming educated to give themselves an extra advantage in the world. 

It turns out, in my life, intimidating women are becoming the norm as the future is female. 

 

Building a Dream

Image from Moreno Matkovic
on UnSplash

 Similar to many of you ,my journey to building a dream took me many years.

As I am fond of saying, over a half a century of construction. A long time when you think about it. At first the steps were obscure and very shadowy as I snuck behind my family's attention to cross dress in front of the mirror. I did not know much about what I was doing, or the tools to do it so I looked as if I was clownish, most of the time. As luck would have it, the mirror often lied to me and gender euphoria set in, before I even knew what it was and what it meant. All I really knew was how at night when I slept, I dreamed of being a girl and was sad when I woke up and needed to face the same old male world.   When I was able to escape into my feminine world, I felt so natural and exhilarated, I just couldn't stand to go back.

The years flew by and I was able to learn more and more about the femininization process I was facing. At the same time, small glimpses of what if slipped into my mind. Or, what if, someday I could make living as a woman trans or not part of my reality. As I did, the reality of building a transgender dream became increasingly difficult. Partially because, at the same time, my male life was becoming increasingly successful and it became  harder and harder to give up what I had built. Still I moved ahead as the feminine forces within me were so powerful.

Since it is coming close to the Halloween season around here, I would be remiss if I did not mention how going to Halloween parties dressed as a woman did not help me build my dream of perhaps being a full time woman some day. Back in those days, the term transgender was still in it's infancy and I did not know how it fit me. All I knew was, I worried and stressed for months ahead of Halloween about what my "costume" would be. Predictably my outfits started out slutty and evolved into going to parties dressed as business professional to see how many people would notice I was a guy at all. Overall, I had several meaningful experiences at Halloween which provided quality building blocks I could use when I seriously began to enter the world as my authentic self. As promised, I will write more about them as Halloween comes closer.

In the meantime, I was having more and more opportunities to learn I was so much more than a man who wanted to look like a woman. I even received a  comment from "Paula" across the pond in the UK concerning a blog post I wrote on the subject:

"I often think that the moment of realization that you are a trans woman rather than a cross dressing man is the Biggy! After I accepted who I am everything else that followed was just a natural consequence of that initial revelation. After I had accepted that I was in fact a woman it was perfectly logical that I would want the world to experience me as such, so I went full time. As I wanted to experience the fullness (as much as possible) of life as a woman it was perfectly natural to get medical help, leading first to hormones and then surgery. All of those decisions were the natural consequences of that first understanding that this is who I am not something I do."

Thanks to Paula and all of who comment! I could not have put it better. 

As it was, I kept on building until I formed a solid foundation to finally achieve my dream. It was never easy but on the other hand, building something worthwhile never is.  All the lonely nights I spent going out just to be alone come to mind as well as the occasions I was shunned or even laughed at. At that point my dream seemed to be so far away. Deep down I knew I was doing the right thing and kept on building. It turned out happiness was just a build away. 

Man, I Feel Like a Woman

Shania Twain

 Maybe you saw country star "Shania Twain" as she hosted the 2024 People's Choice Country Awards. 

If you did, you probably remember when she sang the iconic song "Man I feel Like a Woman.". The song meant quite a bit to me for a number of reasons. The main one of course was I did feel like a woman, not to mention I would have given anything to have her appearance. 

The song was popular during the time I started to find and patronize two small lesbian bars near where I lived. One was a very rigid lesbian biker bar and the other was a much more mellow atmosphere where I happened to know one of the bartenders as my male self. Even though I was begrudgingly served in the biker bar, I always sought to poke the bear. I discovered the easiest way to do it was to play Twain's song on the juke box. For some reason, the owner and other patrons resented me even playing it. I found it to be great fun until I came in one night and the music machine was completely turned off. From that point forward, I took the pressure off  and just started to go to the other small lesbian bar where I was welcome.

In the other bar, I was able to learn many of the nuances of the lesbian community and figure out where I fit in, if at all. In my jeans, boots and makeup I discovered I was closer to being a femme or lipstick lesbian and found I drew the attention of the very serious bull or butch lesbians. I even was heavily induced into singing karaoke by a huge woman in a cowboy hat. Since I am a terrible singer, I tried to let her take the lead and I quickly left the bar shortly after singing. The only thing I heard her say was my voice was lower than hers. I never saw her again.

On the other hand, a super butch who was on his way to becoming a full fledged transgender man just happened to be my first dinner date with a guy. He later told me how scared I was,  he was right. 

Through it all, I still did feel like a woman and did appreciate the acceptance I gained from the lesbian community. I never had to try to adjust my sexuality and was validated as my new emerging self without needing a man and all the potential problems which came with it. On the other hand, there were a few men I did feel a connection with just enough to wonder how the other half lived. At the least I knew I would not have to operate on the gender fringes forever if I had to. 

Needless to say, I will never achieve the appearance standards of a Shania Twain but most other women (trans or not) will not either. Plus my womanhood was achieved in a different way than most cis-women. None of it was my fault and I did the best I could with what I had to work with. And, in the end result, I do feel like a woman.  

  

Complacency

 

Summer Image with padding.
JJ Hart

As I did my best to transition from male to female there were many times I experienced moments of complacency.

It happened slowly enough as I kept throwing lifelines to myself so I could survive a life burdened with gender dysphoria. To add insult to injury, I was not gifted with feminine external attributes to help me along as I initially tried to make it in the world as my authentic inner self. Disguising my testosterone poisoned body was a total learning experience. Angles needed to be changed into curves using everything from pads to balloons to foam. Anything it took to perfect my image and avoid complacency. 

The main problem I had was I could not avoid all the years I had lived as a man. The male trip was never easy for me to learn and even a more difficult time to forget. I had survived and even flourished and now I was trying to give it all up and for what. To live as a woman which became an all encompassing goal. I would practice the best I could walking and moving as a feminine person. Even to the point of being called "Ma'am" when I was at work as a man. I figured it was because I projecting a feminine "aura" to the world and resolved to add the idea to my accessories when I was out in the world as a novice cross dresser or transgender woman. 

I started to project very strongly that I was a woman to any stranger I was interacting with. Along with looking them in the eye, I was able to be accepted for the first time as the person I wanted to be but I still had to guard in not letting up my guard and not slipping back into any of my old male ways. Just one time walking like a linebacker or not paying any attention to my new feminine communication skills could essentially ruin my whole day. It did not matter how much time, effort or money I put into my appearance, if I forgot who I was, nothing mattered. For years, my entire existence was still so fragile until I put in the years and work to tip my gender balance.

I can't say, even today I don't experience moments of complacency. It is easy when the cis-women my age and younger are for the most part very casual in their appearance. Ironically, when I see a woman in heels and hose in the grocery store dressed to the nines, my "trans-dar" goes up and I want to take a closer look. Perhaps the person could be part of the transgender or cross dresser sisterhood. 

Through it all, complacency or not I have never forgotten how the differences in female fashion is and was one of the fun parts of transitioning. No longer was I confined by the drab and boring male fashions. I had forever admired how the woman around me had the freedom to express themselves through fashion and now I could also.

On another topic, I attended two other LBGTQ support group virtual meetings recently. The groups moderator is a trans man and does a good job of keeping everyone involved. The group is very diverse and I was surprised to see a couple of the transgender participants seemingly have partially de-transitioned over the years. Plus I learned the Veterans Administration has finally approved electrologist visits under their care and my mammogram was approved after four tries. The main problem was the hospital I wanted it done at still had an old chart on me with my dead name so getting a new one was the problem. The VA needed to approve the process and did so my dead name information has been changed on yet another document. Progress is progress I guess.

At least I was not being complacent and stayed the course until I saw results.

Feeling the Pain

 

Image from Eugenia 
Maximova 
on UnSplash.

Learning on the fly all I needed to know concerning my authentic life as a transgender woman often resulted in pain.

The pain, early on mainly materialized when I rushed the process of going out in public as a novice transgender woman or cross dresser. Many times I was reduced to tears following being stared at or even laughed at when I was simply out walking around. I felt the pain for years until I finally realized I was the problem and sought out the reasons why. The main reason was (as I always mention) my male ego was dictating my femininized fashion sense. He was thinking attempting to dress sexy would somehow validate myself as a woman. Of course, it didn't and just made me look ridiculous. On the other hand, when I dressed to blend in with other women, they validated me as a woman.

My frustration and pain increased until I became fed up with the entire process and changed it. My thrift shopping adventures began to change to reflect my new fashion sense. I was held back in many ways by my budget and knowledge of what fashion I was trying to buy. Sizing was an example, as I struggled to find what looked best on my testosterone poisoned body. I did not have the benefit of having any feminine characteristics to begin my journey so trial and lots of error is what I went through. Every time I learned a fashion choice I made  just would not work, I felt the pain return again.

My situation improved when my overall confidence improved to a point where I was able to use the women's changing rooms. When I could afford to go to a mall clothing store, I always checked with a clerk first to see if I was to be accepted so as not to feel the sting and embarrassment later. In the thrift stores I went to, the changing  rooms were not monitored anyhow, so I never had to ask. As I said, when I had the opportunity to try on clothes ahead of time, my improvement rate went way up and my fashion pain way down.

After conquering most of my fashion pain, next up came my paranoia over communicating as a transgender woman in the world. Of course I quickly discovered I had no idea of how women communicate between themselves. I found myself on several different levels when I dealt with the world. Once I figured out I was not "fooling" anyone else and just resorted to being myself, my life improved. One level of woman just did not care and basically ignored me while another level was curious and wondered what I was doing in their world. Overall, I was learning on the fly and had my share of pain such as the one transphobic woman I encountered at a party Liz and I attended many years ago. She was actively harassing me about what my dead name was. She was so evil, the experience still causes me pain to this day.

Overall though, when I compare my transgender journey to others I read about, I suppose I have had it lucky. Even though I had suffered a lifetime's worth of pain when I lost my wife, several close friends and my business in a span of five years, I was able to find new friends and rebound. Mainly because the friends and Liz accepted me as my authentic feminine self. I guess karma was paying me back for a lifetime of wondering what I was doing about my transgender self. All the years of doubting my gender existence came back to be a strength when I quit being a victim in my own life. 

Sure I was transgender but suddenly it became a strength not a weakness and the pain was behind me. 

     

A Spectator in my Own Life

 

Image from Author JJ Hart

There were many times in my life when I felt as if I was a spectator in my own life.

From the first glimpse in a mirror when I cross dressed as a girl, all the way to when I first went out determined to be a woman rather than just look like one, often I was on the outside looking in. Being on the outside was certainly not a great place to be. I literally spent decades of my life worrying about where I actually stood with my gender issues.

Along the way, I grew tired of being the spectator and wanted more inside information on how the feminine system I so admired worked. I discovered the hard way, I was not going to be allowed to learn more until I made the drastic step of increasing my transitioning efforts. Naturally, it was very difficult to do when I was totally immersed in leading a male life which I had become quite successful at doing. Overall, I was becoming the victim when it came to my life as a whole. I kept wondering why me when it came to my desire to live as a transgender woman. I finally had to shake it off and move forward with my gender transition before I lost everything I knew in life. 

It turns out the real culprit was myself.  I was afraid to face my truth and it cost me. I even tried to out run my desire to live as a woman by moving and switching jobs. Once I talked my wife into moving from our native Ohio to the New York City metro area. Then back again a couple years later. Living in different parts of the country was certainly an eye opening experience but did very little to help my gender issues. On the rare occasions it did like the night on Long Island when I went to a transvestite mixer and the hosts thought I was a cis-woman was flattering but did me no good the next morning when I crashed back into my male life. Then my poor wife had to put up with my mood swings.

Still I was a spectator in my own life when I walked down the long hallway in heels to get carded for my true gender to the times I did the family grocery shopping in sweaters, mini skirts and flats, I wondered who was that? It took me years to come to the conclusion the other feminine person was me and she had a right to be here in my life. Slowly but surely, I was building the life experiences needed to cross the gender border but it kept taking me so much time. I kept running into so many road blocks, I thought I was some sort of a gender construction engineer. 

Regardless as time flew by, it was time to put my gender cards on the table to finally determine which gender was going to be the primary provider in my life. What I attempted to do was live as much as I could as a novice transgender woman to see if the lifestyle was for me. Even though initially I did not attempt to do it, the trans life rapidly snuck up on me. Before I knew it and maybe before I was ready, I began to carve out a brand new life as a woman. Quickly I needed to develop feminine communication skills which was difficult for me to do since I was overwhelmingly dealing with other women in my life.

Through it all, slowly I grabbed total control of my life and became a spectator any time I was forced back into my old unwanted male life. In other words, I finally faced my own truth and flipped the ultimate gender script in my life.    

Staring Down the Transgender Cliff

Image from Jimmy Conover
on UnSplash

 As I transitioned from my very active male self into an accomplished transgender woman, there were many times I found myself staring down a cliff on my gender path.

The more I walked on and was successful, the more scared I became. The cliff I was looking at, increasingly appeared to be steeper and riskier than I ever imagined when I first put on a dress and makeup so many years before. After all, I was risking so much such as a spouse, family and a job to name just a few. To add more pressure, I was becoming increasingly more and more successful in my choice of occupations. I had worked years to arrive at where I was and now I was risking it all to try to be a successful out transgender woman. By successful, I mean I was able to increasingly move about in society as I carved out a new life.

Mixed in with all the life changing experiences I was going through were many failures as I would sneak up to the cliff and look over. The entire process was scaring me more and more and threatened pushing me back into the gender closet I had worked so hard to leave for all of those years. 

Finally, I could take it no longer and began to gather the courage to take a leap of faith as I approached jumping off my personal cliff into a risky world I thought I knew something about. Before I did, I tried to come up with a survival plan when I jumped into the sometime snake pit which was the feminine world. I needed to learn the basics of the indirect passive aggression. Slowly but surely I learned to fasten my seatbelt and learned to ready myself to jump. I had conquered so much on my journey and it was time to quit staring down the gender cliff. 

Ironically, the women friends I had made like Liz and Kim helped me to a soft landing. They taught me what it would take to for me to become a transgender woman on my own terms. More importantly, all the fears I felt concerning my fear of gender heights proved they were like new gender guardian angels to me. Certainly, I found there were transphobes who would never like me but on the other hand, I found most people just didn't care. I was left alone to make a soft landing around my friends and enjoy my new life. 

I have always tried to be a proponent of the idea that something you are proposing to do will not be as bad as you think it will be or as good as you think it will. The same happened to me with I took the chance and gave up my male life and undertook the biggest adventure of my life. 

The soft landing off of the cliff coincided with my softer life as a transgender woman. When I did land, I wondered what took me so long. My excuse was I was afraid of heights, when in reality, I was just afraid of losing what was left of the white male privilege's I enjoyed. But it turned out, I could not have my gender cake and eat it too. It became too much pressure to attempt to live part time as a trans woman and a man. 

I closed my eyes, hoped for the best and jumped. It did not matter how intimidating the cliff seemed to be, the steep gender cliff proved to be the least of my problems. 

Transgender Inspiration

The late Lynn Conway.

 In my formative years growing from a beginning cross dresser into a novice transgender woman, there were very few inspirations for me to follow. One of the few I knew about was the very accomplished and talented Lynn Conway, a computer scientist and electrical engineer.  

Deep down I knew I was not on the same level as Conway and the very few I did know about followed the same path as most transsexuals face when they transition into a feminine life. We were expected to leave our past behind, have all the needed operations and relocate ourselves to start over. Since I was my usual stubborn self, I could not see me going down all of the same roads as well known transsexuals. In fact, I knew a couple trans women nearby who were ready to go down the surgical road and change their lives forever. 

As in most cases each of their lives were totally different than mine. So they were more of an interest to me than an inspiration. By getting to know them closer, I had hoped to gain more knowledge of what I would face if I decided to go further with my own gender transition. I did learn, as I went on, everything was different when I was living as a transgender woman. I had my own preconceived ideas of how it would be to live as a woman from all the years I had spent closely observing the women around me. However I found most of my conceptions were wrong as I slipped behind the gender curtain. The prime example was how I was presenting myself as a woman. I wasn't dressing to blend in and was drawing unneeded attention to myself. My efforts came from my old male ego dictating my fashion and wardrobe. I had no inspiration to guide me the correct way.

I think I tried to use my second wife as inspiration but I was just not in the proper mental space to accept her criticism. In other words, my feminine self had not had the chance to grow up past my adolescent years as a trans woman. During those years, happiness was looking very lonely as my wife and I constantly fought over my appearance among other things. I think she knew she was fighting a losing battle as my internal feminine self fought with her all the time. Every now and then, I did talk her in to going out to eat as two girls and I really tried to dress down for the date. As a matter of fact, if I dressed down any more, I might as well just have gone as my male self. 

I was getting nowhere fast in my quest to learn more about being a quality transgender woman, so I was forced out on my own. Which added in it's own set of problems. Primarily, here I was sneaking around behind my wife's back to see if I could live as a woman. In doing so, I found I could create another life. Furthering the divide between my wife and I.

The divide widened until her death and inspiration or not, I continued on with my search for my feminine self. What I discovered was, she was with me all along. Just waiting for a chance to live. When she did, she became my own inspiration and I never looked back. In many ways I found she adopted many of the mannerisms and personality of my Mom, who was very outspoken and not shy. I admired her so much, I took her first name as my middle name when I legally changed my gender markers. 

These days, with all the internet and social media access transgender inspiration is much easier to come by and we need the inspiration with all the negative coming our way from politicians. We have to do all we can to keep the positives coming.

Just Weary

 

Image from Harry Quan
on UnSplash

Following a lifetime of doing my best to maintain a male lifestyle, I grew weary of living a lie.

Similar to many transgender folks and/or cross dressers I grew impatient with the progress I was making with my gender transition. I had two main problems, the first of which I did not know where I was going and the second was I had no basic idea if I was ever going to learn the basics of what I was doing. Very quickly, I tired of just looking at myself in the mirror and wanted more. I wish now I would have seen my feelings as being transgender but all of this occurred well before the term transgender was invented and became popular.

At the time, my frustration level was rising to an all time high. I was doing my best to learn the basics of feminine presentation but rarely had the chance to try my efforts in a public setting. Those occasions just happened to be Halloween parties which I learned many new basics from. Such as what happened when I dressed slutty compared to when I dressed in feminine professional attire. As Halloween rapidly approaches, I will try to be more in-depth on what I learned which helped me along on my journey to be a transgender woman.

As I went along, my femininization lessons just increased my weariness of being male. I grew extra tired of all the games guys play when they size each other up in the world and I wanted out. I could not wait until I could head home and escape into the safety of my woman's world, The whole problem was, my world was still so isolated and I needed to get out. To enter the world, I dreamed up ways to do it and began by going shopping where clerks had to accept me for my money, not my gender. I also started out by going to gay bars thinking I was safe there. In the long run, I discovered neither did me much good as I was not challenged to build a better feminine self. As I said, acceptance was a given in the clothing stores I went to and not a given in the gay or lesbian venues I went to. Through it all, with the ups and the downs, I learned I was on the right track to my gender discovery. Even though I needed to make sure the light up ahead was not another on-coming train.

My salvation turned out to be being myself, as I ended up going full circle and enjoying the sports venues I enjoyed going to as a guy. Sure I was scared at first, but I followed my instincts of being friendly to the staff, dressing to blend in with the other women and tipping well. Before I knew it, I became a regular at several venues as I enjoyed myself. During this point of my life, even though I was still intensely lonely, I still was increasingly weary of any idea I was still a man. 

To do away with any of my masculine traits became a primary goal of mine. I worked hard to lose weight and take care of my skin to do my best to improve my femininized appearance Plus the addition of the gender affirming hormones I began very much improved my confidence and outlook on life, I finally had arrived at my gender tipping point when all the male clothes had to go and it was time to consider coming out to the closest friends and family I had left. 

It was time to leave my weary life behind and open the doors to an exciting new life as a full-time transgender woman.  .  

Welcome to Reality

Out with my girls. Liz on left, Andrea on
right.

I worked very hard to get to the point where I could live as a transgender woman. 

Once I began to arrive, I understood the real work was still ahead. When I finally began to establish myself as a new person, I needed to start all over again. It primarily affected me when I was in a conversation with other women, since men barely talked to me at all. Main examples came when I was invited to several girl's nights out. I learned to interject my family experiences in the older group of women. Instead of saying I was specifically a mother or a father in my life, I said I was a parent to a daughter I was very proud of. By doing so I was able to become an active participant in the give and take women use to communicate when there are no men around. 

It was all a great learning experience for me as I was building my confidence to stay out in public and slip behind the feminine gender curtain. For the most part, I found acceptance except from a few women in the older group who did not accept me. All the younger women did accept me for who I was and I enjoyed going out with them immensely. Since they were all younger and more attractive than I was, they attracted all of the attention, leaving me basically to fend for myself which was fine. It was only the reality of being in the feminine world setting in. 

I also had to deal with a big dose of impostor syndrome when I went behind the gender curtain. I needed to keep telling myself I belonged with a group of women while I was doing it. Following many battles with myself, I finally came to the conclusion even though my path to womanhood was different than most of the world, I still followed a difficult path to arrive where I wanted to. Plus, I needed to remember, being born female did not necessarily entitle a person to being a woman. It was a social title not a biological one. When I arrived at that point, the reality of my situation was easier to understand.

The more I worked on the new me, the better life became. I felt natural when I slipped behind the gender curtain and for the first time in my life, I could say I was happy. Mainly because all of the gender tension I felt attempting to fill an unwanted male role was over. Understanding all the differences between the two main binary genders was never easy but for the first time in my life, I attacked a problem head on and did not try to run behind makeup and a dress to escape. I was the one in makeup and a dress and I had to make it work.

I was fortunate in the fact my inner feminine soul had been watching and learning all along. She was just counting the days until she could take control and quit fighting my male self for domination. Once she was free, activities such as girl's nights out were just icing on the cake. 

Once I discovered my feminine reality and was able to live my truth as a transgender woman, life was so much easier.

Quickly, on another topic, I have decided to go to another LGBTQ Veterans support group meeting coming up soon. I have been to two now and they have been tolerable. The only real problem I have had is explaining what I did in the Army because I was in the American Forces Radio and Television Service. A very small segment of the Army. So, you needed to be deployed overseas to be exposed to AFRTS at all anyhow. During the last group meeting, I think I at least was able to explain what I did in the service and I was in way before "Don't Ask, Don't Tell" military LGBT policy was in effect. It is all so difficult to explain but the moderator seems to want me there, so I am on the week to week participation plan. Past that, we shall see how it goes.    

  

Opening New Doors

 

Ohio River image.

It took me over a half a century to open all the possible doors I could before I decided to begin gender affirming hormones and transition into a full-time feminine life.

For any number of reasons. I over-reacted and resorted to excessive experimentation  before I quit knocking on so many doors. Such as, behind door number one was a wife who did not approve.  Other doors had the usual questions such as what would I do with my friends. extended family and employment. 

Before I could make it to the other main doors, I needed to prove to myself beyond any shadow of a doubt, I belonged in the world as a transgender woman. What took me so long was I needed to live my male life at the same time as my new femininized life. Switching back and forth between the male and female genders took a toll on me but I kept slowly finding new doors to knock on and walk through. What I did was single out a door to go through and then judge the reaction. If I was successful, I would look for another door and if I was not, I would go back to the drawing board and attempt to figure out what went wrong. Often I found out the hard way that even though I was accepted in many venues, in others I was not. Mainly when I pushed the envelope too far and journeyed into the wrong redneck venue just to see if I could. 

Other doors I attempted to open and was successful is when I went to very small diverse mixers at an acquaintance's house in Columbus, Ohio. During the parties, I was able to meet all levels of the transgender community and see how I measured up. Especially with one of the transsexual women who I admired so much. Even though I did admire her, I learned her life was not applicable to mine and I had to keep looking for my own door. Since her path would not work for me. She was a soon to be retired Columbus fire person and was looking forward to a good pension to support her as a single woman. Plus she had good insurance, and I had none of them, I wondered how I was ever able to make it to my dream. 

On occasion, I grew frustrated with the number of doors I needed to go through. It seemed just when I thought I was successful, I was met with a dead end and needed to turn back. I did purge a few times and tried to put my male self in total control but deep down inside I knew the purge was only temporary and my girl self would re-emerge. She always did, stronger than ever searching for the mysterious, magical next door to go through. Sometimes it seemed as if I was stuck in a huge gender maze trapped and looking for a way out. 

Finally, I knew it was time to put my maze, doors and gender past behind me and do the right thing. I found the way out I was always looking for and she was with me all along. All I needed to do was admit the truth. All those years of looking behind all those doors made me aware of one main thing, don't wish for what you want because you just may get it. 

I wished for a full time transgender existence and kept opening doors until I got it. 

The Long Search

Early in my
search.

The problem I often ran into during my life was taking my eyes off the goal and becoming lost.  

Perhaps my biggest problem was I did not have a clear cut gender goal. Essentially, I was wondering around just trying to get by as I cross dressed my male self in the mirror.  The work I put it sadly only lasted me a few days before the thrill of being femininized wore off and I was firmly back in my male world. The long search for better results resumed.

It took me years to realize the ultimate end to my search was me facing my own truth. Until I did, all the mirrors and Halloween parties in the world would not help me. Still, I was very stubborn and did not want to give up on all of the privileges of my white male life. I wanted my gender cake and a chance to eat it too. I suffered totally because of my idea I could live a life somewhere between both of the main binary genders. The long search went on as I struggled. 

Keep in mind also for over a half a century I searched for my gender identity and the entire journey had it's ups and downs. The ups happened when I was able to present realistically as a woman and the downs when I could not and engaged in self destructive behavior with myself and worse yet those around me who I loved. I did many things I am not proud of today but can not get back.

The search also led me to abusing alcohol and my mental health. Through therapy, I was able to salvage my mental health and fortunately, I was able to curtail my drinking before it caused permanent damage. So my search continued in better shape than it was in before. Plus, I was really able to step up my feminine presentation game to help my confidence when I went out. Through much more work than I can ever admit to, I arrived at the point where I could ghost my male self altogether and leave him behind. 

It was only then when I gathered the courage to end my long search and face my reality My search led me to the spot where I needed to finally accept the fact I needed to fill in the gender blanks in my life. I learned I was born to be feminine and was forced into a male life I really never wanted. Even still, I lived on in a mostly male life I felt guilty being in. It was time to put all my gender lies behind me and end the long search for good. 

I will forever resent I took so long to face my truth but it is something I will have to live with. My goal now is to live a positive transgender existence in my life. Now that the search is over.  

Broken

 

Ohio River image from the
Archives of Jessie Hart.

I am selfish, I want all the time back when I felt I was broken somehow because of my gender issues or dysphoria. 

The way I look at it, I lost years when I stressed over what gender I wanted to be in my day to day life. If I just had a portion of it back how much more I could have accomplished. 

I guess the problem would have been, if I had followed my truth, how many barriers outside of my control would have been placed in my way to stop my progress. For example, I can not imagine any scenario where my parents would have accepted me switching over from my boy self to live as a girl. The best case would have been endless, fruitless trips to a therapist who knew little to nothing about gender issues and back in those days, I would have been labeled with some sort of a mental illness.

If I had gone the route of trying to live as my authentic feminine self at an early age, I would have been broken to start with and have had no chance to change it. So, I needed to develop ways to cope with my broken situation. Early on, I resorted to wearing what I could of my Mom's clothes and buying my own makeup to experiment with. It was a fairly easy fix to get me by until I could risk my life by trying to cross dress again. If I was caught, I knew all hell would break loose in my family. Somehow, I hid my emotions and desires and got by.

As the years flew by, I became used to feeling broken and so alone in my gender issues. I had only one friend who seemed to feel the same way and he ended up moving several states away before I could find out if he shared my desire to be feminine. I ended up with another dead end and feeling broken again.

Fortunately, all this negativity has a good ending. I finally learned I was not broken at all. Society was and all I had to do was learn to exist in my own little transgender world. Not to say, the whole process did not take a tremendous amount of work but it all turned out to be a singular gender effort which was so worth it. Plus, I needed to remove the chip from my shoulder I felt from worrying about all the time I had wasted in my life before I made the all out effort to femininize myself and live my truth. Time is nothing you can ever get back, so I hoped I could learn from my losses. 

I had so much help along the way when I became older and more secure in my gender. Hopefully they all realized I was not trying to live a lie and just was trying to get by and it was the reason we all could become friends. During our lives, we meet so many people who are just passing through and a few leave lasting impressions, I was just lucky I met positive ones. People who showed me I was not broken and never had been.

Doing it With Mirrors

Image from Paulious
Dragiunous on 
UnSplash.

For a time, I thought my entire female life revolved around my interaction with mirrors. 

In many ways, it did as I could not wait until I could slip away from my family and spend time cross dressed as a girl in front of the mirror. I even had a special mirror I was very fond of. It seemed my Dad was thinking of me when he designed the house he built for us to live in. He laid out the house with a long hallway connecting the bedrooms and a bath and finished it off with a full length mirror. The mirror and the distance it provided gave me precious space to admire myself in the mirror as my femininized self.

The only problems I experienced were I had no feedback from the mirror and would not until I experienced the world as my novice feminine self. So, good or bad, I could convince myself I looked great when in fact I had so much work to do to achieve my goal of passing well in public. Even though I was still barely getting by in the public, I still relied on mirrors to get me by and reassure my mind I belonged. What I did was look for the nearest mirror in clothing stores to see how I looked. It turned to be a singular approach to presenting well with the world. 

There were times when I took my mirror worship to the extreme in stores, one in particular comes to mind. There was a coat discount store I was fond of going to since they had coats which came in my larger size. During my shopping trips I fell in love with a pale blue, wool mix, long coat which I thought looked great with my long blond hair. I so loved admiring myself in the store mirror so much, I thought someone would come up and tell me to buy it or leave. While it never happened, sadly, there was no way I could afford it and end up smuggling it into the house away from my wife. So I needed to leave my dream coat behind. 

It took me years to quit doing it with mirrors and begin to live my truth. It was still a struggle to leave my best friend behind. I had subconsciously trained myself to look for the nearest mirror to fall back on to to reassure myself I was an attractive transgender woman. It was a real struggle to rely on myself for a change without the mirror. All of a sudden, the public became my mirror and it was very difficult to adjust to because not all interactions were positive. I needed the confidence to look a transphobic individual in the eye and win the moment. At the least, the transphobe would have to walk away from the interaction thinking they had actually met a transgender woman and we were not so bad. 

The process of interacting with the public over time became automatic and my only interaction with the mirror became my morning check in or when I am applying makeup for a trip out. Ironically, now the mirror is not always my friend anymore. Now I still have to battle what is left of my gender dysphoria when I look in the mirror. Sometimes I see my old male self peeking through which I hate but others times I see a much more pleasant femininized version of my old self. When my old male self weighs in too heavily on me, now I have developed the coping skills to get by and put him back into his place.

Never, in my wildest dreams, did I think mirrors would play such an important part of my life. From the earliest days of cross dressing to my current days of dealing with gender dysphoria, mirrors have allowed me to survive.      

Escalation or Escapism

Halloween image from the 
Archives. Min on right. 

During my life, I spent many uneasy moments in my transgender transition when I was caught between escalating my feminine gender craft or escaping back into my well worn, boring male world. 

The problem quickly became the more I escalated my attempts at being a girl, the more I wanted to do. More and more drama set in as I viewed myself in the mirror. Through it all, I wondered if I could ever put it all together and go out into the public as a novice transgender woman. Following years of escaping back, I finally did take a few tentative steps into the public eye. The first night I tried, I had decided to go to a small book and carry out convenience store just to see what would happen. I arrived and walked down the sidewalk near the store in a shopping center. As I tried to gather my courage to go into the store, I attempted to sneak a look at myself in the clothing store nearby. I could not really see my reflection and began to re-think my idea of going into the store I planned on. Then I decided my idea was not a good one and I headed home to escape back into my male self. 

For awhile, I felt relieved at my decision but then began to think I had taken the easy way out and if I continued on this path I would never discover if I could make it in the world as a transgender woman. Once I was able to locate and buy better fashion choices, including shoes and wigs, my mind started to change as far as escalating myself in the world. After going down a very bumpy road, my confidence increased to the point where I could try out the public again without escaping back to my safe male self. Even still, each time I did escape back, I grew increasingly disappointed in myself and very frustrated in the fact I was wasting all the time and effort I was putting into my femininization. 

Through all the ups and downs, I was slowly but surely gaining small amounts of confidence in what I was attempting to accomplish. In fact, I was scared of how intimidating the entire gender transition process was to me. Many times, I thought I was in too far over my head and was going to drown my entire existence in my quest to be a woman. Something always told me to keep going and the dream I was following would be worth it, so I continued to escalate my transition. 

At that point, one of the biggest surprises which happened to me occurred when I found out how welcoming other women could be. Very quickly I found women were way more apt to approach my feminine side and in return, I could learn how to interact with them also. There was nowhere to go and nowhere to hide. so escaping was out of the question. Mainly because I was living through one of the most exciting times of my life. Why would I ever want to escape. 

Still I found I needed to escalate my gender transition. My primary example was when I suddenly had a major mental shift one night when I was going out into the world. As I was going through what I was going to wear and how I was going to do my hair and makeup, it came to me I was no longer going out to trick the world into thinking I was a female, I was going out as a full-fledged transgender woman. I had taken my escalation to a whole other level and one I never wanted to go back to.  When I turned out to be successful. 

When my male life was crashing around me, the easy answer was to keep escalating into my feminine world. Which I did with gender affirming hormones. The magic little pills I started with almost immediately began to femininize my body and my inner emotions. To this day, when I change and apply my Estradiol hormone patches, I thank the powers to be I was healthy enough to undertake the program. 

I believe now, escalating into my feminine world saved my mental health and my life. The more confidence I gained as a transgender woman, the quicker my male self evaporated away. There would be no more escaping.