Connections through Isolation?

 

My wife Liz on left
from the JJ Hart Archives

When I finally began to be successful in my femininized public pursuits away from the mirror, I was content to be alone in the world.

By being alone, I didn't have to face any communication problems with anyone else I faced. Essentially, I just passed through their world quickly and was gone. I did not want to know them better and have to challenge myself into interactions with strangers. Ironically, my idea did not last long as I was increasingly thrust into public interactions as a transgender woman I did not want. In the beginning, I just was not ready to look another person in the eye and risk ridicule.

I learned quickly, my public interactions would be overwhelmingly with other women. Initially, I interacted with clerks in clothing stores who were mainly interested in helping me with my money, except for the few who wanted to help me with my fashion. It did not take me long to realize what was going on and then move on. 

I began to stop and eat lunch to extend my shopping trips which meant ordering from a menu with a server and/or bartender. I found sitting at the bar made for a more personal experience unless the staff was very busy with other patrons and I could try out speaking with others as a trans woman. Very soon out of forced habit, I found myself relaxing more and even enjoying the experience. It was like I was completing a long lost part of my new personality as I left the mirror and entered the world. It was a challenge and I grew to love it. I discovered also many more women than men wanted to know more about me. Women were curious while men were scared of me it seemed and I loved it. 

Along the way, when I first began to communicate I tried to mimic the voices I was hearing from other women and try to repeat doing it until I thought I was doing it right. I even took voice lessons for awhile to improve my vocal presentation for my transgender womanhood.

Still, after my second wife passed away, I was extremely lonely. Not only was I facing finding another person I loved at the age of sixty, I also had the added pressure of doing it as my new version of my authentic feminine self. I was prepared to spend the rest of my life by myself. Little did I know I would not have to. Initially, when I went out to supposedly socialize and find new friends, I was going out to be by myself. If my gender was never challenged I would have taken the easy way out and would simply go back home to my two dogs. 

If it wasn't for a bartender at one of the venues I had become a regular in, I would have remained in the social rut I was in. One night not long after I arrived, she served me my first drink and quickly asked me if I would be interested in meeting her single lesbian mother. Of course I said yes, and a friendship  started that has continued over ten years till today. She is the woman who took me to the NFL Monday Night Football game. A very scary experience which cemented my arrival as a full-fledged transgender woman in the world. But that wasn't all that happened at my favorite venue. Another night, as I sat alone to be by myself, another woman came in to pick up her to-go order. While she was waiting, she slipped a note down the bar to me asking if I was interested in having a drink sometime. I said yes and the three of us ended up having a great time the next couple of years as we watched sports, drank too much and had fun at lesbian mixers. My two new friends ushered me into a world I never thought I could go.

Against all predictions, my connections through isolation worked very well for me. My new friends which included my wife Liz who also identifies as a lesbian, all helped me into my own important version of transgender womanhood. Destiny was certainly helping me during this period of my life.  

How Far will You Go?

Image from UnSplash.

I have always viewed my transgender journey as a series of upward steps. A few of the steps were short and easy to take, while others were the opposite. The steps seemed to be impossibly steep and dangerous to proceed. 

Early steps were thrilling and even exciting as I snuck behind my family's back to cross dress in front of the mirror. Even so, the risk of discovery was anything but easy because I was risking so much. In those days, discovery meant a trip to a therapist who knew nothing about gender issues and even worse being treated as if I was mentally ill. 

At that point, looking ahead, I probably knew deep down, things would not get any easier with my gender issues. But, time would tell. As I progressed during my life, it suddenly became obvious  my gender issues were not going to go away. In fact, they were only to become much more serious. Mainly because my male life was becoming so much more serious too. Once I made it through my military service, I settled in to raising my new, small family which I hoped somehow would make me more of a man, while deep down I knew it would never be the case. I wondered how far I would have to go to carve out a good life. 

Fortunately, I was able to even though the trip was difficult, I made it by deciding I would go as far as I needed to go to satisfy living as my feminine authentic self. Initially, I had several major hurdles to conquer. Such as, did I want major surgeries which were much rarer and expensive back in those days as well as how my sexuality would play out as my new self. 

Since I did not have any insurance to cover the surgeries, paying for them was out of the question so I moved on. Next was my sexuality. Since I had absolutely no experience in sexual time with men, I did not know how it would go. It turned out, I did not need to experience much time with me, I never had to move on from my sexuality with women. I was becoming a transgender lesbian. 

Of course, the further I progressed in my new world, the more I had to lose as far as family, friends and employment. I needed to prepare to lose it all if I needed to. I needed to determine if it all would be worth it. In my case, all the years of fear and struggle proved to be worth it. Thanks to my lesbian wife Liz, I was accepted for who I was. 

To arrive here, I did not have to go through extensive operations and change my sexuality. I have always thought gender was between the ears and not the legs so it did not matter to me. I guess it proves how diverse the transgender community is, if we allow it to be. None of the "I'm more trans than you" syndrome which is hurtful to us all. Especially now, in a political environment which is setting out to erase the trans population, we ALL need to be united and not divided behind a bunch of archaic labels, such as cross dresser and transsexual individuals. 

Regardless of the label, we all had to decide how far we want to go to satisfy our gender urges. Or sadly, how many risks did we want to take to change our life forever. It all proves how we never had a choice in who we are as transphobes seem to think we do. How far you go is entirely a personal decision which takes a lot of work and trial and error to accomplish. It' all depends how in depth you want to go. For example, the night I went out to see if I could meet and blend in with other single women on their own turf and survive. I did make it and knew I could never go back to the life I had before in the mirror. I wanted to go more in-depth. 

From then on, I needed the confidence to do it.

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. 

What Would Mom Say

Image from Jenna Norman
on UnSplash

This week my question to answer on the year long bio I am writing for my daughter and family as well as my wife Liz involved what parent I learned the most from.  

As I compared my Mom and Dad, easily I learned the most from Mom. Outside of the usual circumstances, I found I could find many more opportunities to spotlight Mom's influence on me. For example, I remember at a very early age watching Mom put on her makeup. Being a product of the "greatest generation" she was not shy about dressing up. However, I don't think watching makeup being applied led me to being a transvestite or even a transgender woman really mattered. Somehow the gender issues I faced went much deeper. Perhaps as deep as the medication Mom took during her pregnancy (DES) which was offered to women at the time to prevent problem births.

It turned out, I was successfully delivered just before my parents had decided to give up after three still births and adopt a child. I think because of all of that, my Mom put an extra emphasis on raising me and my brother who came along two years later. So much so, I wonder now what would have happened if Mom would have realized she had a daughter rather than a son. In all fairness to her, the fifties during my youth had very little information on gender issues. When it was available, gender issues were known as mental illness. 

Throughout the years, I always mistakenly thought girls had all the benefits in life I always wanted. Girls were able to wear the pretty clothes I wanted, be gifted the dolls I wanted and even never had to worry about being drafted and serving in the military. Male privileges were not known to me in those days because I had not yet earned any. As a side note, once I did earn the benefits of being male, I learned some of them were automatic and I did not want them anyhow.

I have forever wondered what my life would have been with Mom had I been born a biological female. Being as similar personality wise as we were, we fought quite a bit as mother/pseudo son and I have to think it would have been worse as a daughter. Mom was very headstrong and I am sure we would have had battles over fashion styles in the 1960's as well as when I could begin using makeup. In fact, when I was sneaking around using her makeup, I was probably younger than I would have been had I been her actual daughter.  I am sure too, Mom would have tried to influence me into going to her college and joining her sorority. She would have done her best to push me down a certain path which was certainly going against my generation's rules at that time in history during the upheaval in the later 1960's.

By this time, you may be asking where was Dad during all of this. It was not like he was not an influence in my life but he was not as hands on as Mom was. He was long on providing and short on emotions which I struggled with for most of my life. One thing I remember most about him was how desperate I was to never disappoint him and since I rarely if ever heard a positive from him, I never knew what he really thought of my life. He was blessed with excellent health and outlived my Mom by ten years and I never came out to him before his death from Dementia.

I did try to come out to Mom but it was a dismal failure for both of us. Predictably, when I told her I wanted to be a woman, she offered up mental health counseling. The conversation took place just after I was finished with my military duty and was never mentioned again until her death fifty years later. I used to hold her thoughts against her and was quite bitter but I gradually mellowed with age and came to realize she was just a product of her generation. 

To honor all her sacrifices, I used her first name as my middle name when I legally changed my gender markers nearly ten years ago. Had I had the opportunity to be accepted as her daughter from the beginning, it would have been interesting how our lives would have intersected. Way past the pushback I would have received for wearing my skirts too short and wearing too much makeup when I was a teenager. I know what Mom would have said. You aren't leaving the house looking like that. Maybe I should have thought of that when I tried and failed to dress that way later in life.  

 

Just Weary

 

Image from Harry Quan
on UnSplash

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

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

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

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

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

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

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

Damn it is Complicated

 

Image from Amanda Dalbjorn
on UnSplash

Crossing the gender border is never easy for the average human being. 

To begin with, you need to be very serious concerning your gender passion. You need to trust your instincts, close your eyes and leap. I took over fifty years before I could come to the point of being able to trust myself. After all, I had spent all of the time as a very serious cross dresser exploring the world to see if I could survive as a transgender woman. Some times I was good about making plans, sometimes I was not. As I took the good with the bad. Ultimately, taking the good with the bad, just walking a path I knew very little about. 

As I walked my new path, there were several points of reference along the way. Such as the mixers I was attending in nearby Columbus, Ohio. Many were big and more than a couple were very small and intimate. Regardless I learned from both and how internally complicated they were. All layers under the so called transgender umbrella attended one or the other. Everyone from seasoned transsexuals to very novice cross dressers often out for the first time in their lives away from the mirror. Through it all, I was trying just to find my way to discovering who I really was. All I did finally learn was I did not fit the mold of a stereotypical transsexual or a weekend cross dresser. I was somewhere in between. I found I was not everyone's cup of tea, I enjoyed being my own. 

Examples were everywhere, including the guys who cross dressed for certain mixers but not for others all the way to the impossibly feminine transgender women who made their appearance. I was drawn to the feminized crowd but often I was left out because of my looks. I had a long way to go with my appearance but I was trying hard. With the help of a professional makeup artist provided by the group one night, I learned the intricacies of applying makeup and could really help me because he explained everything to me. Thanks to his magic, I was able to move up in the eyes of the transgender or transsexual crowd. Even still, mainly because they shunned most of the rest of the average cross dressers, I stayed to myself. Except when the trans women went out to other gay venues after the regular mixers were over. When I did so, I was exposed to a whole new world of exposure in the world in my own transgender universe. 

As I did, my life became increasingly complicated. I needed to overcome inner clashes with my genders as well as trying to deal with the problems of dealing with my second wife who was against any idea I was transgender. The major problem, every bit of my self was telling me being feminine was the only way I could survive. All of my turmoil just led to more stress to my already fragile mental health. I ended up in therapy again, which did some good but were for the most part wasted because I refused to face the truth about myself. My authentic self was feminine and I needed to express it. The only thing therapy did was make my wife think somehow it was going to magically "cure" me or at the least, I was trying to help the situation. Which at the time was growing into a major problem between us.

When I first looked into the mirror as a kid so many years ago, little did I know how complicated my life would become as I grew into my gender issues. My gender path was so convoluted as I followed it, I often became lost. The only aspect which kept me going was the deep down knowledge I had been born to be a girl. Dealing with it was always the issue.

Independence Day?

 

On this Fourth of July weekend, many think there is a possibility this will be the last we will ever be able to celebrate as transgender women, trans men or otherwise. Since the Supreme Court recently installed the president as a king, the coming election looms as a scary proposition. As the former president has already indicated he will never be unseated if he wins again. Plus, if you doubt me, google Project 2025 and read it. The entire LGBTQ community is in danger.

Regardless, this post is not going to be political in nature as most of you know who I support for the presidency and I will never change anyone else's mind. Plus, I don't see it as a done deal President Biden will run again.

This post is about my own independence day from the bonds I suffered when I was living as a man. 

I have plenty to celebrate since I took over a half a century to shake free of all the unwanted male life style I inherited, if I wanted to or not. Over my half century, I played all the male games presented to me such as sports and service in the military. Secretly hoping one or both would help me to just settle into a male life. Even becoming a father didn't help. I was stuck as the round peg being hammered into a square hole.

The longer I lived as a man, the stronger my ties became to the gender I never really wanted to have anything to do with. Especially difficult to break were all the male privileges I accumulated when I became a fairly successful middle aged white man. If I liked it or not, I became an automatic "sir" to the public I encountered. 

All the years it took me to sever the male bonds I had were worth it as I began to live as a transgender woman. Sure, it was different to live under a different set of gender rules but each one made sense when I did it. Major changes included being excluded from male conversations since seemingly I had lost a large portion of my intelligence, all the way to learning the all important rules of being a woman in public and how the security would change me forever. There were more changes to be sure but those were the big ones.

When I got up this morning, my wife Liz said "Happy Independence Day" and I don't mean the national one. I didn't have to think long and feel very positive about what she said about me coming a long way in my life. After all, she was one of the main influences when I finally put what was left of my male existence behind me. She told me she had never seen any male in me at all which was all I needed to hear to transition totally.

I had a question from a reader the other day which asked me did I think women were the most accepting of a transgender person. I said, in my opinion yes, by far I had been supported so much more by the women in my life and would have had a much more difficult time playing in the girl's sandbox without their help. I learned among other things, there was so much more to a woman's life than makeup and fashion. Which I had to learn to move forward to live my gender dream. Thanks for asking!

My independence day turned out to be one worth celebrating more than I ever considered.

 

Back from the Brink

Picnic with my wife Liz on right. 
 

As I changed out my estrogen patches this morning, I thought about how far back from the brink I have come over the years towards my dream of becoming a full time transgender woman. 

Along the way, it became evident to me I needed to streamline my life If I was ever going to succeed in my goals. I carried way too much old male baggage with me and if I ever expected to actually to succeed, I needed to determine what I needed to leave behind. Since I was attempting a later aged MtF transition, I had a truck load of baggage to consider such as family, friends, employment etc. As it turned out, I received an even break with my family as I retained my daughter in my life but lost my brother along with his extended red-neck family. So, I considered I did well, all things considered. As far as close friends went, I never made many which probably due to the fact I always thought someday I would have to disclose my gender issues to them. But first, I needed to be truthful to myself and realize my dreams went far beyond just looking and cross dressing as a woman. I wanted to be one, a huge difference when it came to telling another person. 

My issue with telling other friends became a non issue when sadly, most of my other close friends passed away. Leaving me on the brink by myself and looking down a very steep gender cliff. During this time, the pressure was continually building to make a decision on how my life was to be lived. Would the status-quo be good enough to get by, or did I need to make a radical change and hope for the better. By this time also, my second wife had passed away, leaving me with no real relationship obstacle to hurdle. Essentially, I had free reign to do as I pleased. If I wanted to take my feminine self to a downtown festival or an outdoor concert I did it.  The whole process helped my to decide my gender future as I continued to feel so natural. Even though I was on the brink.

In the meantime, I was slowly shedding as much of my old male baggage as I could. If I could help it, I never bought any male clothes as I expanded my feminine wardrobe. If and when I stood on the brink of my cliff, I wanted to look as feminized as possible. It worked as I was able to interact in a whole new world to me. 

Eventually, what happened , my new friends shoved me off of my brink and at the same time provided me a safe, soft landing. They took me at face value as a transgender woman and did not want to know anything about my male past, so I was happy beyond belief, I couldn't figure out why I had such good fortune but could only surmise it was because of all of the years of gender struggle I spent getting to the brink. My world was finally coming full circle.

I also need to mention women such as Kim, my wife Liz and my therapist Dr. "C" who helped me negotiate me coming back from my brink. Plus, as I write this, I realize I never came back from the brink, I made my way through it. 

Even still, being at the brink for all those years was  the mental challenge of a lifetime and without all the help I received from the women around me, I am not so sure I would have made it. Or, at the least I would have been a different person today.  

Blog Comment

I follow a non transgender based blog on Word Press called Lifes Fine Whine. Today she posted she wanted comments about childhood dreams and how they came out. I decided to provide a comment about mine. The comment was designed to explain some of the angst of being transgender without getting too in depth. Here it is:

All through my childhood, I wanted desperately to be just like the girl next door. Unfortunately I was a boy born into a male dominated family.
So, I played football when I wanted to be a cheerleader. Went to the prom in a tux instead of the beautiful dress my date wore.

After college, I was drafted into the military during the Vietnam War. I served my time but never lost the idea I was somehow living a lie. I cross-dressed every time I had the chance to relieve the pressure and explored the idea of living a feminine life.

Along the way, I went through two marriages to women who knew of my "secret." The second passed away quite unexpectedly leaving me free to make a decision in my life.

Finally, at the age of 60, I came out as transgender and started hormone replacement therapy to feminize my body as much as possible.
I began to live my life as a transgender woman. Found an incredibly accepting partner and settled into living my dream.

It took me awhile but now I feel blessed to have lived on both sides of the gender fence.
I have also benefited from my daughter and three grand kids who also are extremely accepting.
In many ways I feel I should come out sooner.
However the wait was worth it.