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. 

It is Fall and Time for Halloween

 

I have heard Halloween is the national holiday for cross dressers everywhere.

I know it was for me as I could not wait for the trees to change colors and the temperatures to dip so I could plan my "costume" for the season. I was fortunate when I began to learn so many feminine basics thanks to my Halloween experiences. Such as, the first night I went out with friends to a late night showing of a silent movie in a beautiful restored theater in Columbus, Ohio. The primary lesson I learned was to either get a close parking spot or wear comfortable footwear as my heels began to bother me very shortly into the evening. Regardless, I had a great time in my short mini dress and I was disappointed when I did not see anyone else cross dressed (that I know of) and the night went by so quickly. My friends we went with did not even mention my shaved legs. I remember thinking it was going to be a very long year before I again could challenge the world as my feminine self.

Back then, my self was very under developed. The mirror still had a hold of me and I really had very little knowledge of where I truly wanted to go as I researched the gender world. Would the mirror be my home or could I succeed as a novice transgender woman. In it's own very important way, Halloween helped to point me in the right direction. The first parties I went to, I simply tried to dress sexy as my "costume" and took the easy way out. I was seeking validation as a woman  essentially by doing a form of drag, which never worked for me. For the most part, I was left alone by other men and women. It took me several parties to understand what I was doing wrong. 

From there on out, I started to attempt to tone down my "costume." For example, one year early on in my transition I wore all black. Starting with black flats, black tights and sweater. I paired it all with my short black skirt, long blond wig and topped it off with a black beret hat. I tried it all out at one of the big dance clubs Halloween party in town and was enjoying myself immensely until a person in a mask came up to me and said I know who you are. Initially I was a mixture of being scared and devastated some one could see through my "costume" so easily I did manage to laugh and say who was I and the person said I looked just like my Mom. Then I realized who he was and he went on his way. It turned out I grew up near him in the rural neighborhood where I lived. Even with all of that I had a great time and was saddened that Halloween only came around once a year.

It turned out there were many other lessons to learn from the cross dressers national holiday as I was going to find out. One of the biggest ones was when I realized how rare it was to find another possible "non civilian cross dresser" in their own "costume." Again, I was feeling alone in the world. Another one was there was no way I could wait another year to venture out into the world as my authentic femininized self. At the same time of my Halloween adventures, the internet became a part of my life and I was able to research terms such as transgender to see if they fit me. I found there was so much more to learn. 

There were more Halloween parties where I continued to learn from too. I haven't forgotten my pledge to share them also since for the most part, they had such a profound effect on my life as a novice transgender woman. 

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. 

 

When Every Night is Girls Night

Grae Phillips is still active
on Facebook if you want to 
see more. Or just keep up. 

I know I make a big deal out of my second huge transition, when I mentally moved from being a serious part-time cross dresser into being a novice transgender woman.

Sometimes I feel as if I am putting myself on some sort of a gender pedestal when I write about not considering myself a cross dresser anymore. If it comes off that way, I don't mean it to. On occasion, the written word gets in my way. Getting back to the cross dresser versus transgender statement I made, I think in my case, it was a matter of me judging my own life. Originally, as I was working my way through my early years of admiring my girl self in the mirror, I knew it could never be enough. There had to be more. I was so tired of cross dressing for one day and then two or three days later wanting to do it again. 

As I always mention, all of this occurred back in the pre-internet information era when any news and contact with like minded gender individuals, be they transvestites or transsexuals, was very difficult and rare to come by. This was even before the barrage of talk shows led by the late Phil Donohue who interviewed female impersonators such as "Grae Phillips", all the way to transvestites seeking approval from a doubting world. It was quite a bit for me to sort out. But I did. I knew I could never be as beautiful and talented as Grae but I could reach the standards of most of the transvestites I saw on my television. There was hope for my future after all.

As I progressed into meeting more and more diverse cross dressers or the women known as the new transgender group I began to think what it would mean if I went all the way and every night became girls night. In other words, a time when I would never have to go back to my old male self and live. Deep down I knew there would have to be some sort of line drawn in the sand if I did. As much as I loved all the fun of the newness of applying makeup and picking out clothes, I wondered what would happen when the newness wore off and I needed to settle into the daily routine of the transgender womanhood.

It turned out, I had nothing to worry about. I settled into my new feminine routine as if I had always should have been living this way. I found I didn't have to do much special on many days such as most cis-women do and then again still have the fun of dressing up for special occasions. It was true, once I jumped the gender border from cross dresser to transgender, I could experience what life could be like if every night was girls night.  

The Prom Gown

Image from Joeyy Lee
on UnSplash

Years ago, I received a prophetic statement from an unknowing doctor when our family was on vacation in Canada. 

When we were not out fishing with Dad, we played football on a hard-packed lot behind the fishing camp with a bunch of local kids. Being the budding football star I never was, I decided to try to play running back and was actually successful bulling my way through the opposing boys on the other team, for awhile. On a play I would learn to regret, I was picked up and thrown down on my shoulder and suffered a broken collar bone.

I say regret primarily because my Dad was not amused about having to interrupt his vacation to take me to a hospital for treatment. At the hospital, I had X-rays taken and was diagnosed with a broken collar bone. I was seen by a doctor and had my shoulder bandaged up in a sling and was told it would heal on it's own. Leaving only a tell tale bump which showed it had ever happened. Then the doctor said, since I would not be wearing any prom gowns in my future, it would not matter anyway.

I thought at the time, wait a minute! What if I wanted to wear one of the beautiful gowns I had seen on women in my future. What then. I think that comment hurt worse than the actual breaking of the bone. Plus, when I did go to proms and was stuck in an ugly tuxedo, I always looked at the girls around me for any tell-tale bumps to show a collar bone break. I never did see any. 

Along the way, I had several other instances of my feminine aura shining through. I have/had a nephew who from an early age developed a very unsavory attitude towards life which sometimes carried over to me. It started with my politics clashing with his right wing bigotry and going from there. On several occasions, he secretly complimented me by saying I threw a football like a girl. He even said one time when I bought my new Porsche Boxster, I had bought a girls car. Like I said, he was trying to hurt me but was secretly making me feel good. I could not wait to be the attractive blond woman in a sharp sports car.

There were other times when I was called feminine when I was doing my best to be a macho man. Several times at work, I was called "Ma'am" out of the clear blue sky in the middle of a normal conversation with a customer. Looking back, I think it was my feminine aura slipping through my male fence. 

Even though it took me years to realize my dream of living as a transgender woman was much more than living as a part-time cross dresser, I realized there were several tell-tale signs along the way. Maybe the doctor was trying to tell me someday I would want to actually wear a beautiful prom dress which showed off my collar bone break bump. Or my evil nephew would go on to having his own insecurities to deal with. I have not seen him for over a decade, so I don't know or care. He would probably just say he was right about calling me a girl. 

It turned out there were many people who saw through my disguise and at the least knew I wasn't who I was desperately trying to be. A stable, non toxic, productive man. I failed miserably and all I ever wanted was to be the one wearing the beautiful prom gown.   

Calling me a woman was the ultimate compliment. 

A Cajun Night Out

Ohio River Pride Image
of Author JJ Hart

Recently I passed my seventy fifth birthday. To have a mini celebration, my wife Liz took me to one of our favorite restaurants which happens to be a Cajun food place called the "Swamp Water Grille." 

Even though we live miles and miles away from Cajun country, the chef/owner of the venue studied down in New Orleans and his food is incredible. Before I could get to the food, I had to go through the usual steps most women go through to get themselves ready. Since we just finished watching the Ohio State - Iowa college football game and the venue is quite casual, Liz and I decided to wear our Ohio State University sweatshirts. In addition, I added a close shave, foundation, contouring and lipstick and was ready to go after I brushed and tied back my hair. 

As I prepared, I realized I was putting the effort in to be invisible in the venue but I wasn't. For some unknown reason, I went first to the hostess stand to put our name in on the wait sheet. The first thing which happened was the hostess gave me a big smile and complimented me on my glasses so I was not so invisible after all. She was obviously of the younger generation which does not have a problem with transgender women or men so I felt warmly welcomed to the venue. Not to mention feeling a little relieved of my anxiety I was experiencing. I was further confused because I had been at the venue before with no problems what so ever. It is just a sample of the anxiety I live with. 

From there, it was clear sailing and no one seemed to notice me at all. They were all so busy with enjoying their food, friends and surroundings they did not have time for me. The only person who we were dealing with was our server who addressed us as "ladies." Which is wonderful of course. I went through so many years of disavowing my true authentic self, I don't think I will ever tire of being referred to in the feminine tense. 

As we finished our wonderful dinner and drinks, it was time to bring the evening to an end and we headed to the car. Ironically, I felt the benefits of being largely invisible to the world as an older transgender woman while at the same time being very visible to myself. It seemed everyone of my senses were heightened as I waited for someone to stare at me and say something negative. I guess no matter how successful I am in my relatively new life, I will always experience the stress and tension of be confronted in my life.

In the meantime, a little (or lot) of great Cajun cooking helped me to experience a huge dose of gender euphoria. The best gift I could have ever experienced.
    

What If?

 

Marci Bowers

As I spent all the years as a very serious cross dresser, I dreamed of perhaps becoming a transgender woman and what it would be like to live a feminine life.

For many, many years I was my own worst enemy as I learned the parameters of what I needed to work with. First of all, I needed to play catch up with all the girls around me who were already experimenting with makeup and fashion. I remember vividly back in the mini-skirt days how the girls in my class would not so shyly sit and cross their legs to tease all the boys. Little did they know, the affect they had on several boys such as me. I wanted to be them and wear the skirt and panty hose and tease the boys.  I was so envious of the stories my wife told me of how she would roll up her skirt when she went to school and was out of sight of her Mom. 

I always wondered what if I could ever escape the mirror and experience life the same way she did. Of course I did not and had to set my own course. A course with no guidance or peer pressure on how I looked. What if I could live as a woman remained an illusive dream. To keep my frail mental health balanced, I tried to improve my presentation on my own  As I am fond of saying, I experienced quite a bit more error than trial as I slowly learned to express and embrace myself as a novice transgender woman. To add to my excitement, my wife and I purchased our first computer and I was able to learn about other transgender women in the world. 

One of trans women I learned about and was suggested to me by a reader (thank you) was renowned sex change surgeon Marci Bowers. Even though I knew I would never consider gender surgery for myself. Just reading Bowers journey gave me hope for my future.  My fondest desire her story would pave the way for an easier gender transition for the rest of us. 

I followed my new found confidence by exploring more and more as I tried  to carve out a niche to build my dream life. Even though I was rejected on many occasions, I still managed to climb the steep slope towards my transgender dream which was coming into focus. The main discovery I made was if I was myself, I could actually have the opportunity to live on into trans womanhood. If I did, I knew the risks were great and I was jeopardizing years of male life I had sacrificed to build up. 

Still I learned I had to follow my inner soul and see what if meant to me. Since I had worked so hard to climb dual gender mountains in my life, it was time to jump and head for a hopeful safe landing.  Even though I could never hope to be as accomplished and attractive as an Marci Bowers, I discovered just enough people valued me as my authentic self, I could survive. These were the people who never knew my before person and I was starting all over with. 

Even though I was still doing the pushing, they were the ones doing the pulling me into my new world. Proving what if was possible. 

The Sixty Four Crayon Box

Image from Leisy Vidal on UnSplash

I view gender in light of all the recent attacks  on the transgender community from a certain political party here in Ohio not called the Democrats, as a big box of crayons. The whole shameful process just shows how little the Republicans care to know about the trans community,

Rather, if they like it or not, almost all humans fall on some sort of a gender spectrum. It seems, men have fewer crayons to pick from because of their innate insecurities concerning their own gender and or sexuality. Which is a whole separate subject.

I know when I began to color in my own life, I needed the big box of crayons because I did not fit the male mold I was in. Whatever the world thought of me, I needed more out of my life than a restricted male existence. Instead of viewing myself as the round peg being forced into the square hole, I started to see myself as a multi-colored individual with many new gender frontiers to explore. My journey was destined to take me far past the rather quick romance with all the pretty fashion, all the way into a in-depth dive into what a life as a transgender woman would be all about. As I was busy coloring my future, I found I needed different colors to enable me to express myself more completely.

Examples were plentiful. Such as when I looked the part of a woman, how was I ever going to communicate as one. I was so busy coloring, I needed a whole new box of crayons to keep up with my life I was attempting to balance between two genders. To further stereotype the whole process, I quit using all the drab and darker colors and began to use the lighter more vibrant ones as I lived more and more in a femininized world.

The more I went to diverse transgender mixers in nearby Columbus, Ohio, the more I learned about others who were coloring in their gender lives too. I was able observe everyone from those who had almost completed their new lives, all the way to those who were working with broken crayons and severely struggling. All of it was an extreme eye opener for me because I was so naïve when it came to the transgender or LGBTQ world as a whole. Normally what happened was, I took everything in and ended up going back home and thinking about it. A solitary pursuit since I did not have anyone to talk to about it except for the occasional therapist. 

Therapy produced mixed results when several I went to did not want to discuss or see my colored design of who I truly was. It wasn't until I sought out one of the rare gender therapists back then who told me the truth. Basically, she said my picture was beautiful and there was nothing I could do about wanting to proceed on my path to transgender womanhood. I wish I would have listened and started to change my life back then but I was stubborn and hung on to my part-time male existence which at the least, paid the bills. 

As transgender women and men, we really need the extra courage to keep coloring our pictures. For example, in my case, if my health holds up, I will be on gender affirming hormones the rest of my life. Hopefully, I will need another sixty four box of crayons as my life expands as a transgender woman.

 

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.  

  

The Ultimate Challenge

Vacation image from Kansas
by JJ Hart

I am biased but I think changing how you live to reflect your authentic gender self is one of the toughest things a human can do. 

Perhaps you noticed I said reflect your gender tastes not change them. I believe our transgender selves are already determined and we are attempting to sync them up to our extremal selves the world can see. The path varies for most of us but the final goal is always the same. Sadly we have many obstacles in our way. 

One of the main ones is trying to overcome the effects of testosterone poisoning which gives us the hated male characteristics we did not ask for. I remember hating all the changes which were happening to my body and how the changes would effect me when I attempted to cross dress in front of the mirror. All I knew was my life was changing for the worst and I did not want it. Much later on when I became much more serious about my femininized presentation in public, my goal was to hide my broad shoulders and the angles of my body with new fashion. 

It turned out, testosterone poisoning and new fashion were the least of my problems as I continued along my path to the ultimate challenge of living as a full time transgender woman. There were so many times I never thought I was going to make it. I had so much baggage to sort through as a man as I had acquired over the years. Since I had spent so long doing my best to build my life, then I needed to decide what to do about my family, job and friends. Leaving me between the gender rock and a hard place. Often I did not know how I was going to find my way out of my predicament. Was I still a man, or a woman and what about my long standing sexuality.

Obviously, the ultimate challenge was to sort through all my issues while I was still attempting to live my so called normal life as a man. I ended up trying to live a little at a time as a trans woman until it began to feel so natural I never wanted to go back. Slowly but surely I was proving to myself I had been born feminine and just forced into the wrong gender by some sort of a cruel twist of fate.

It was around that time, I found I was not alone and began to discover other challenges on my path to transgender success. I learned from others around me about their own successes and failures or triumphs and purges. Often my own feminine wardrobe would be gifted by an acquaintance's giant purge. In fact, my first set of expensive silicon breast forms were gifted to me. The breast forms were a real step forward from what I had ever had before and would help me to present better so I would not be discovered as a man.

As Paula wrote in and commented: "I don't know if we ever get over that fear of being found out, of being exposed and ridiculed. I think this is much more about how we see ourselves than how others see us, I look in the mirror and see all my history, the Dan Dare chin and the prop forward shoulders, others just see a late middle aged woman who happens to be on the tall side."

Thanks for the comment and as I am fond of saying, these days I present as old. Since the genders have a tendency to merge together later in life. I am also happy to have made it to the place I have in my life but as I near my seventy fifth birthday, I know the ultimate challenge is yet to come.  

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.    

I Am I Said

 

Archive Image, JJ Hart

One of my favorite Neil Diamond's songs is "I Am I Said". I particularly was drawn to the line saying I was lost between two shores. Neil was referring to New York and Los Angeles and I adapted it for me to signify being lost somewhere between being male and female.

The song's lyrics go on to say "I am, I said to no one there " I again felt the same way because I had no one to discuss my gender issues with other than the occasional therapist who went quickly through my life with little or no benefits until I reached a point much later in my life. In addition, the pressure to conform to the successful male life I was leading was intense. One of the few positives of my job was I was named a managerial training manager so I was able to take medium ranged business trips from my home in Ohio (yes I am from the much maligned Springfield) and travel by car to Lexington, Kentucky. Usually, I was asked once every six months to make the trip which I quickly saw as an opportunity to pack a few of my feminine items and cross dress. 

I usually worked it out with my second wife I was taking a second night at the company headquarters so I would not have to drive back at night. When I did, I was able to either cross dress and head out to one of the Lexington gay bars. It turned out, there were several back in those days, since the University of Kentucky is there. When I went out, at the least I didn't have to tell the chair or mirror I was actually someone feminine. On one occasion, I hit the jackpot and my training seminar just happened to coincide with Halloween. I thought ahead and when I packed away from my wife's prying eyes, I added a few slutty outfits to put together a Halloween "costume." The difference this Halloween was I was going to try my luck at going to a big straight club and not a gay venue. After a few wrong turns, I found the place and gathered my courage to go inside. Here I was dressed in an all black mini-dress with black heels, hose and blond wig doing my best to ignore all the guys pinching my behind as I walked across the dance floor, Since I needed to be up and fresh early the following morning, I needed to be back early to go to bed.

All along, I was learning what I was and was finding out the hard way what could happen if I dressed the wrong way. One night, I decided to stop at the halfway point on the way home which was Cincinnati. I got a hotel room and proceeded to seek out one of the more infamous gay bars in town for hookups, I thought since my black outfit worked so well before, I would try it again. This time, a very drunk guy at the bar tried to pick me up...until his wife showed up. I was embarrassed and was trying my best to back pedal from the whole situation when he made things worse by telling her why did she not have legs like mine. By this time, I headed for the restroom to hide and when I came out they were gone. As was the black outfit.

Through it all, all the lying I was doing to my wife was wrecking my moral code and when I asked who I was, I did not know. Which made the Diamond song so important to me. 

Finally, I did climb out of the pit I was in and was able to learn who I was but sadly was never able to reconcile my transgender life with my wife before she passed away. All along she was urging me to find myself and by the time I did, it was too late. I was no longer stuck between two gender shores. I had found myself and she was feminine. 

It Was Never Easy

I am amused when anyone thinks my gender journey has ever been an easy one. 

To begin with, I was born into a very male dominated family. Being the oldest son of two, I had heavy male expectations forced on me. Very early on, I learned I was in the wrong place at the wrong time. I did not belong in the male world at all. The problem was coming to the knowledge I did not belong as I was sneaking around my family's back to cross dress as a girl. As I remember, I had two hiding places for my small collection of feminine wardrobe and makeup. 

The first place was up in the attic of our family garage and the second was more creative when I discovered a hallowed out tree trunk in a woods next door to my house. What I did was use plastic trash bags to protect my precious belongings from the elements and it provided an extra way I could be alone and dress which relieved (for a day or two) my gender tension. So none of my drastic measures were easy but I survived without anyone detecting my secret, to my knowledge. 

As years went by and my life as a girl began to be more complex, I was pressured to do more and more to protect my life. Sneaking around became more intense as my wardrobe increased, along with my knowledge of the makeup arts. In all fairness to me, I attempted to ease my gender pain, I told my first and second wives ahead of our marriage I was a transvestite or cross dresser which I thought would help my world. My idea worked for awhile, until I essentially out grew the idea I simply wanted to wear women's clothes and makeup. More and more I wanted to be a woman.

Making the jump from cross dresser to transgender woman often was brutal. Partially because I still had my male life to contend with. It probably would have been easier on me if I was not involved in such a male intensive job which automatically would completely throw me totally and publicly back into a world I never wanted. Ironically, my life as a man I worked so hard to build was now in direct competition with a feminized life I was growing into. 

At the same time, my biggest challenge became was deciding if I was transgender at all, Could I continue a life where I lived in both binary genders temporarily or would I need to choose between being a man or a woman. I ran from the decision for years before I grew so tired of running I could go no farther. Making a decision was never an easy one but one I needed to make. Finally, one night I had yet another soul searching discussion with myself and decided to live a life as a transgender woman. The world as I knew it was showing me the way. For the first time in my life I was single and did not have to worry about a spouse to deal with when I changed.

I went even further and decided to go to a doctor to see if I was healthy enough to begin gender affirming hormones. I was and my body took to them very rapidly, making my decision to give away what was left of my male wardrobe to charity and add to my feminine wardrobe. It was not easy to make the decision but it was easy to live with the results. I only knew my new feminine life would never be easy but still would so much better than the life I had lived,

It was never an easy life and my gender dysphoria certainly did not make it any easier. Waking up in the morning after dreaming if I was a boy or a girl never got my day started on a good foot. All of it became some sort of a daily routine I never wanted. With all the highs and lows, somehow I learned to live with it all. 

Building from the Inside Out

 

Image from Brooke Cagle
on UnSplash

Years ago I began to understand I was building a new human being from the inside out.

I began to realize it when a person very close to me told me how fortunate I was to be able to start over in the world as a transgender woman. At first I was scared, could I really re-create myself as a woman and at the same time achieve my ultimate feminine dream. Following years of living and training, I found I could indeed live a life as a trans woman.

Before I did, I needed to decide what old male baggage I would have to discard or adjust to the fact I would have to bring it with me. It was difficult since I decided to seriously began my gender transition at the age of sixty, I had years to consider what to do with my baggage. Initially, I was part of the old transsexual school which believed you had to totally uproot your life and move when you transitioned and start all over. The problem I had was, there was some baggage from my old life I wanted to bring with me. For example, I wanted to try to preserve contact with my family and wondered if my wife (who I loved completely) would ever accept me. Not to mention other key points of my life including my passion for watching sports. 

Fairly quickly, as I transitioned, I was able to indirectly control all I was building from the inside out. By this time, I had worked out most of the appearance or fashion challenges I faced, allowing me to work on expressing my internal self. First of all, I learned my only child accepted me totally and my only sibling (a brother) did not. Sadly, we have not communicated in over a decade now. I know I have survived and I have assumed he has also and we moved on. Since I was now a different person now and he is entrenched in his ways, I am sure it has all been for the best although it hurt me how he handled it by rejecting my invitation to the family's annual Thanksgiving feast.

In many ways, having the opportunity to rebuild myself was terrifying yet exciting. Along the way, I found I needed to transition again. Mainly when I finally decided to make the mental move from cross dresser to transgender woman. I say mental move because I wasn't doing anything outwardly any different as I was doing my best to put my best appearance foot forward as a woman. I knew if I was successful, there would be no turning back on my gender path. It was a huge continuing beginning in the process of leaving my male world behind.

By this time, I was well on my way of deciding what baggage I could bring with me and what I could leave behind. I was preparing to give what was left of my male clothes to a charity and I had fairly quickly established myself as a regular in a couple of the big sports bars I had frequented as a guy. By doing so, I could meet my small group of new women friends I had met and watch the games we all enjoyed. My new life was coming together from the inside out and I was loving it. 

Even still, it sometimes took all the concentration I had to remember I was living a new life and I needed to rely on my inner female to carry it out. By doing so, I was able to say what I was thinking and not screw it up by injecting any of my old toxic male self. The only thing I could rely on was my new friends and their reaction to me since they had no clue of the old me. It was very liberating to say the least. 

Overall, I have to say, building the interior person was more intense when compared to the exterior woman the world saw. Especially when I needed to communicate more and more with the public as my new self. When I did build from the inside out, I learned to live my truth and empower my life as a transgender woman.

  

Follow your Passion

It does not seem possible but Labor Day is here and for the most part, summer is another memory.

Of course, the fall season brings more with it other than temperature changes (in my part of the world) which leads to necessary wardrobe changes. Even though here in Ohio we normally have a late summer come back, it is time to think about bringing out the leggings and long fuzzy sweaters for the fall.

Perhaps, as important to me and my wife Liz, it is time for football season to kick off again. There was a time when I wondered if my favorite time of year would have to be diminished somehow  when I transitioned into the feminine world. My love of sports was the only big piece of male baggage I did not want to give up. 

It turned out I did not have to worry when I began to notice and meet other women who were as passionate about sports as I was. Especially my wife Liz who shared my passions for The Ohio State Buckeyes and the NFL's Cincinnati Bengals as well as my friends Kim and Nikki. 

I guess I was lucky when I was able to bring my passion for sports with me into my new world.  

This weekend, for a new kick off season, I invested in a new The Ohio State Buckeye sweatshirt. I am very superstitious when it comes to my sports teams and my new soft and snuggly sweatshirt needs to be broken in with a few wins. 

I guess my main message here is almost nothing is off limits to you if you want to transition into a new feminine life as a transgender woman. If you look around, there are women who have the same passions you do. Loving sports takes nothing away from your innate femininity. It's all part of being part of a gender which is allowed to be more layered and enjoy more things. 

If you look around, you can find many feminine fashion sports items to wear. Who knows, if you are still in the closet, you can still wear panty hose under your jeans until you can do more. In this case women are rapidly catching up with men in their love of sports. So you are free to be you.

And one more thing, GO BUCKEYES!!!!

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.