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. 

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. 

     

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.

Tomorrow is Here

Labor Day 2024.

 Throughout my life, I was the best at putting everything off. From homework to attacking a gender issue, I kept putting it off, hoping it would go away. 

Of course it never did and I was stuck until the last moment trying to do something about it. My best laid plans for escape never did work. Especially when it came to my gender issues. When I was young, the whole plan seemed simple enough. Cross dress as a girl as much as I could get away with and then escape back into my male world. No matter how painful that was. 

It was a good plan until life became more and more complex and I wanted more and more from my cross dressing activities. In other words, I wanted out of the mirror and into the world. I started innocently enough with quick trips to the mail box during the day when I was the only one home. Of course I had to wear my shortest skirt and feel the cool air on my freshly shaven legs and I was hooked for life. 

The problem was, tomorrow was never quite here. Once I cross dressed for a quick day, I needed to go back and try to exist in a male world I never really wanted and I deeply resented it. Repeating the entire routine over and over again made me moody, grumpy and overall difficult to live with. Perhaps the worst part was, I had no one to talk to concerning my gender issues. So a full fledged gender tomorrow never came for me. I was just digging myself a deeper hole, thinking someday my life would change. Then, I didn't know it would but I didn't consider how much work it would take me to do it. 

Days, years and even decades went by and still I hid from myself all my gender truths. Most of the time I did not live in the present while I kept in the back of my mind the next time I could cross dress and enjoy my small but growing feminine wardrobe. All of the waiting created it's own set of issues. During that time, my male self was doing his best to survive and prosper in the world. Which at the same time, made the idea of transitioning into a transgender woman more complex and intimidating. It was easy to keep putting off what I knew deep down was true, I was always meant to be a girl. I just had to be in the position to reach out and grab her. 

During that portion of my life, it seemed my gender tomorrow would never be here and massive roadblocks stood up and blocked my way. Navigating them in my newly acquired heels would be a challenge I would have to accept as I crossed the gender border to play in the girl's sandbox. I found myself to be way past the tomorrow mode and started to believe my dream of living as a full time transgender woman was very achievable. 

Very quickly tomorrow became today and with the help of others, I seized the opportunity before I became too old to enjoy it. I am not shy of saying I waited until I was sixty to transition and begin HRT for what ever reason. I ended up feeling so natural, I wondered why I waited so long. 

Afraid to Try?

From the archives. Underground
Railroad House.
Ripley, Ohio.

During my male to female gender transition, there were so many times I was afraid, or should I say petrified to try new things.

Probably, first of all, I was afraid to cross dress in my home at all. Fearing my family would discover my deep dark secret and I would be punished. Even with all the threat hanging over my head, I decided somehow I needed to try to move forward in my femininization. When I did, I felt so natural and felt I was doing the right thing. Regardless of my deep seated fear. 

Anyway you cut it, my fears cost me time and effort in my life. Precisely, all the time I spent attempting to work around other members of my family so it could be my turn to cross dress in the mirror. The amount of time I spent thinking and dreaming of being a girl was ridiculous. Finally the pressure built so much, I had to put my fears aside and dress as a girl. Even to the point of shaving my legs. In the long term, I became better and better in hiding my wardrobe and makeup away from my Mom, Dad and brother. To this day, I do not know how I escaped detection. 

The older I became, the more proficient I became at the art of wardrobe and makeup with what I could accomplish on my very limited income. My presentation as a girl became a very real possibility but not a possibility which calmed any of my major fears. In fact, some of them were even worse. Such as how was I going to be able to live a successful life as a man when I wanted to be a woman. Plus, what was I going to do about the looming chance I would be drafted into the military and sent away to Vietnam and what would I do if I couldn't cut it in college and flunked out. I spent many sleepless nights worrying about those things and more.

More to me happened when I was in college and I started to work my way into being a novice transgender woman. In those days, presentation or appearance was always the main issue since the only time I was really out was Halloween parties. Only being out once a year put a tremendous strain on me until I couldn't take it any longer and began to sneak out of the house dressed as a woman. Initially at night in lonely places before I knew the threat of doing things like that and jeopardizing my personal security. In the meantime, I still remember vividly the first time at night when I caught my reflection in a nearby store window when I was seriously thinking about going into a nearby book/magazine store and shop for a book.  I did not because my fears got the best of me and I was overwhelmed. 

It wasn't until much later when I was able to conquer those fears and come out into the world as a transgender woman but it wasn't without complete panic attacks on occasion. The one I remember the most was when I was thinking of making the jump from serious cross dresser to transgender woman in the parking lot of an upscale sports bar/restaurant I had been to many times as a man. I must have sat in my car for a half hour looking at myself in the mirror trying to gather the courage to go in. I don't know now how I did but I somehow put my fears behind me and went in. By doing so, my life changed forever for the best. I thought.

What really happened was, I set off a new round of fears because my male self (as well as my second wife) were digging in against me becoming anymore of a trans woman than I already was. While I was sure HRT or gender affirming hormones was my next step, my naysayers were against me. All of the process added to my fears of ever transitioning full time which increasingly my mental health was telling me was the only way to proceed. 

All of my new fears even took a back seat to my new everyday life as a transgender woman. At this time, the world was so new and different as I was learning so much as I built a new life. I hated for the old embedded fears to hold me back but they did. No matter how far I had come, the farther I had to go. Major issues such as finances, family, relationships and even sexuality had to be decided before I could move one.

 Fortunately, I put my fears behind me and conquered each of  my major conflicts as they arose. Victories equaled more confidence to achieve the transgender life I had always dreamed of. When I looked back, most of my fears seemed to be so petty. They certainly weren't at the time and became major mileposts on my gender journey.

Dsyphoria is Never Pretty

Image from Jen Theodore on UnSplash.

It was years before I knew what gender dysphoria was all about and what it meant to me.

Essentially what it meant was understanding the depth of how far I wanted to go towards my feminization. I started out innocently I thought, similar to most of you, with explorations into Mom's wardrobe. and makeup. I wonder if she even noticed the fascination I had watching her put on her makeup. 

All along, I wondered what was going on with me and was I the only one who felt the same as I did. On those days, my gender dysphoria ran deep even though I still had no idea of what my future held. I looked in the mirror and saw a male even though on some days I felt decidedly I wanted to be a girl. In fact, if you had asked me then what I wanted to be when I grew up, I would have said a successful woman. Sadly, there were almost no successful transgender women to model myself after, so I internalized my feelings and carved out a very tentative life as a male. In fact painful internalizing became a theme in my life and led to further gender dysphoria.

All of a sudden, as my life progressed and more gender information became available, my dysphoria became more in focus. I could see what the problem still was but I still wasn't in any position to do anything about it except cross dress my life away. I knew deep down, I did not want to harm anyone, especially myself. However, when I still saw my male self in the mirror in the morning, harm still came. The more I attempted to cross dress my dysphoria away, the quicker and stronger it seemed to return just wrecking my mental health.

The only thing which kept me on any sort of a feminine path was when I expressed my female side to myself, I felt so natural. I felt from that reason alone, I was doing the right thing which in turn positioned me in direct opposition with my male self and increased my dysphoria to the max. Because my male self was fighting back with all the tools he had. In those days, he held all the cards, making life miserable for me which sadly I passed along to those people closest to me. I did everything I could to relieve the stress and live a pleasurable life. 

As fashion and makeup became easier for me as far as going out and entering the world as a novice transgender woman but more difficult when I needed to re-enter the world as a guy. My job did not make it any easier because I was in a very male dominated profession. I would do quite a bit of day dreaming of my other life while I was working in my reality. I even was quietly embarrassed when someone would mistakenly refer to me as a woman when I was working as a man. I figured my "aura" was overpowering female on those days and tried to project female more when I was out in the world as a transgender woman. I believe projecting my gender became an important accessory to be added to present successfully. Which I still do.

Still my dysphoria persisted and does to this day. Some days I wake up and sneak a peek in the mirror and see a feminine person which makes me happy. Other days, I see the same old male person I had ever been and become depressed. From there I have learned to take the middle road, or nothing is as good or bad as it seems including my dysphoria. 

At my advanced age, I seriously doubt I will ever be finished with my transgender dysphoria. Since I have an aversion to any extreme facial femininization surgeries, there will be no radical moves to change what I have to face the world. Dysphoria be damned, I will do the best I can.

A Night at a Concert

Image from the Jessie Hart Archives

Following the time when my wife passed away, I actually tried to date another cis woman, once.

During this brief period of my life, my old male self was still desperately hanging on to the idea he could still exist at all. At that time, one of my servers came into my restaurant with her very attractive Mother. After several inquiries I found her Mother was single and she would ask if she would go out with me. She did and we started our very short history of dating. 

Right from the start I found she was a bit of a prima donna when we met on a date in downtown Cincinnati. I suggested stopping at a micro brewery for a quick appetizer when she wanted to go to an upscale steak house on my dime. I should have known then she was out of my league but I kept on trying anyhow. In a very short period of time, I told my daughter I was dating again. In response, she came up with two tickets to a local park pavilion near her house. The concert performer was Joe Cocker, so I could not wait to go. I even asked the new woman I was dating if she wanted to go and she initially said yes and the date was on, or so I thought. A couple days later and a week before the concert in the park, she called me and broke up our brief affair. I was slightly shocked but then again not so much as I began to consider what I would go with an extra ticket to see Joe. 

At the time, I was increasingly exploring the world as a transgender woman, so I thought why not take myself on a date in the park. I knew exactly what I would wear .My long silky black slacks with my black matching sleeveless top and black flats for comfortable walking. I then applied my makeup and topped my outfit off with my long black straight wig and I was ready for the half hour drive to the venue. By this time all of this happened, I was becoming very comfortable with my feminine self so I was really looking forward to the evening as it approached. I had spent many a evening being alone with myself. I wasn't very nervous as much as excited by the expectation of having a good time. 

The evening of the concert turned out to be ideal weather wise, a beautiful warm but not too humid Ohio summer evening. I showed my ticket and was admitted to the venue without a problem. Before I went to my seat, I decided to buy a drink and then headed to sit down. Again I experienced no problems with anyone in the venue in my section. I was able to enjoy my drink and relax even further before the music started. I especially enjoyed the silky sensation of my clothes in the summer evening air.

I was glad I went because I had been a Joe Cocker fan since the Woodstock concert days and it wasn't too long following the concert, he passed away and I was still able to be completely enjoy his performance before it was too late.

As far as I was concerned and as selfish as it may sound, the whole exciting evening was more fun for me than taking a woman I barely knew. Plus my experience even further increased my confidence as a novice transgender woman. Even to the point of coming out to my daughter who I told that I enjoyed the concert very much but never added who my "date" was. 

The night at the concert was one of those lifetime experiences I will never forget. It was the last time I ever tried to date as a man and the first time I was ever to seriously explore my life as a transgender woman. Once I did, the more I understood it was the life for me. 

Refining the Gender Lines

 

Photo from the
Jessie Hart
Archive

As I began to face the world as a novice transvestite, cross dresser or transgender woman, I discovered I had many blurred lines I needed to address. 

In other words, I needed much more work before I ever could understand completely the odds I was facing. The biggest problem I had was I was never naturally feminine, or so I thought. So I needed to begin from scratch to build my feminine self. I write long and often concerning all the public humiliation I suffered when I initially began to leave my gender closet and go out in public. At the beginning, I was ultra careful to go to dark places which were not well populated by the public. Something I learned the hard way later on not to do in my transition. 

One of the few good things I can say about that time in my life was, I had the time I needed to experiment with my presentation. I could secretly go to thrift stores and purchase clothes (at a bargain price) which I thought would look good on me and even fit properly. During my quest to improve my look, I was able to spend very little money and at the same time hide what I was doing from my wife. I remember saving every little bit of extra change I could manage and spend it during the thrift stores bargain or dollar days. Because of the experience, destiny was on my side and I was slowly able to improve my presentation. Especially when I really saved up and was able to purchase a fairly nice wig. 

Ironically, the more lines of my looks I was able to refine, the more I discovered I needed to work on. Back in those days I obsessed on having no hair on my legs, putting together a perfectly matched outfit and finishing it off with just the right accessories. I would spend hours shopping for just the right addition to my presentation. It was around that time when I finally was able to recognize and try my best to blend in with the women around me. I had acquired a business professional wardrobe to wear when I went to upscale malls as well as the new club venues I was trying out. On the other hand, I had other clothes which scaled my look back a bit for when I was first trying out going to large sports bar venues. My goal was to refine my myself so I would do my best to fit in.

The more I worked at it, the better I became and I learned if I didn't listen to my male self and try to dress too sexy and/or trashy, I actually could make a small place in the world for myself as a transgender woman. 

Even at that point, I discovered I still had a ton of refinement to go through as I progressed towards my goal. Primarily, I needed to learn to communicate with the new world I discovered as a feminine person. Quickly I was presented with public levels which went from those people who didn't bother to notice me at all, all the way to those curious types who wanted to know more about transgender women. I can only say making the transition was not easy. It seemed to me for awhile every stranger had their own potential questions to pursue. Finally, I learned they didn't and again life became easier when I discovered the whole world wasn't looking at me. Or, as my second wife told me, it wasn't all about me. 

Refinement in the gender world comes difficultly to everyone. Born female does not make you a woman, you need to grow into it. It just seems, refining our gender lines as a transgender woman or trans man comes as a much more difficult process. Because for the most part we didn't have any help.