Staring Down the Transgender Cliff

Image from Jimmy Conover
on UnSplash

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

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

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

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

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

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

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

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

Transgender Inspiration

The late Lynn Conway.

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

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

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

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

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

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

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

Just Weary

 

Image from Harry Quan
on UnSplash

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

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

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

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

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

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

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

Welcome to Reality

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

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

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

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

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

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

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

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

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

  

Opening New Doors

 

Ohio River image.

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

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

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

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

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

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

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

The Long Search

Early in my
search.

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

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

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

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

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

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

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

Broken

 

Ohio River image from the
Archives of Jessie Hart.

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

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

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

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

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

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

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

Doing it With Mirrors

Image from Paulious
Dragiunous on 
UnSplash.

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

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

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

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

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

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

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

Escalation or Escapism

Halloween image from the 
Archives. Min on right. 

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

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

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

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

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

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

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

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

Gender Prison

Image from Denis Oliveria
om UbSplsh

Many transgender women and trans men have spent numerous years in their own gender prisons. Sometimes referred to as closets. 

Unless you have had to spend time in your own prison with the walls closing in all the time, you have no idea of how bad it is. Just another proof being transgender is some sort if a choice. Why would we ever choose to possibly destroy ourselves with our gender issues. It all got to the point with me, I was doing all I could to manifest myself being as feminine as I could. When all along my male self was telling me I couldn't. 

I finally arrived at the point where I was given free time from my gender prison to explore the world as my new self. When I did, most certainly I discovered I wanted more and more free time. I discovered also, I needed a ton of work to prepare myself for freedom. I was not prepared for all the challenges I would have to face as a novice transgender woman. Since I had spent so much time cross dressing in my life, I thought how much harder could it be. I never factored in what my second wife was always trying to tell me, I did not really know much about being a woman and she was not going to do much to help me out of my gender prison. 

When she told me that, I reverted back to working ever harder to understand what she meant. Since I had studied women closely my entire life, I resolved myself to trying to get behind the feminine curtain to learn more. It would take me years to get there since it seemed I was living a life time sentence in my gender prison. Outside of a few varied chances to thrive, my prison seemed to be escape proof. How was I ever able to leave my prison without jeopardizing all the white male privileges I had worked so hard for such as family, friends and employment. It seemed the more I tried to escape, the more the walls closed in on me.

Once I staged my big gender prison break, there was no turning back. I discovered that even though my wife would not help me pull back the feminine gender curtain, other women would and I took advantage of their kindness. Even when I was able to, I found I was still looking over my shoulder for any male prison guards who were chasing me. It turned out, even in heels, I was faster than they were and I managed to outrun my naysayers which mainly was myself. 

With practice in the world, I finally put my prison time behind me and I set out to live my dream life as a fulltime transgender woman. One way or another, I had paid my gender dues for nearly half a century before I had the courage to fully transition. It felt so good to be let out of my gender prison and not have to go back. 

My parole officers turned out to be the women friends I found and cherished as I learned so much from them about living in a feminine world. When I used their input and included it with what my own inner woman was telling me, I was able to make a smooth transition even smoother. Plus, I was able to use my prison time as a powerful motivator of what not to do in the world. Even as a man, I tried to treat women differently than the other men around me. Mainly because I wanted so badly to be one of them. 

In the end, spending all the time in my gender prison did not do much for my life. I spent so much mental energy rebelling against my male world, I often wonder how much farther I could have gone if I had used all my resources. It wasn't to be because I was in my own gender prison and could not find the key.

Bridging the Gender Gap

 

Image from Samuel Reagan Asante
on UnSplash

It is a dirty job but someone has to do it, right? We transgender women and trans men are in a unique position to be the only go between both of the primary genders and make a difference. If society and politicians let us.

I did not set out to write another post criticizing a certain political party in my state of Ohio  which is trying to do away with all transgender rights. You all know where I stand. Instead what I am writing about is singing the praises of acquiring deeper gender knowledge. Very few humans ever get the chance to journey across the gender border and see how the other half lives. 

Interestingly, there were times I was asked for my feelings about how another woman's spouse or boyfriend was feeling towards her. Women are more intuitive than men and were seeking out my ideas because they knew I at one time, had occupied the male world. I was filling a void they could not find anywhere else. 

Even still, bridging the gender gap was exceedingly difficult. There were so many things to learn about how the genders interacted with each other to survive in the world. In addition, I needed to adjust to being the pursued gender rather than the pursuer was all I thought it would be. I grew up with the idea girls or women had it easier because they did not have to go through the torment of finding dates, right into deciding what was the right date for me. That is if I was ever asked. Which was not often since I was mostly rejected by men. The feeling was mutual because I did not feel any particular attraction to them anyhow. Especially so when I was accepted into a group of lesbians who showed me my validation in the world did not involve men anyhow. 

My new friends taught me how to bridge the gap and learned so much from them while I did it. I was raising the bar in my life without, for the most part, realizing I was doing it. It was difficult learning to walk the walk and talk the talk as a transgender woman but slowly I managed to do it. I think now my major success came from the point I was finally putting my gender picture together. I was no longer a one man show, I was a one woman show. I could see my gender dream was possible following years of denial and struggle. 

Looking off the gender bridge proved not to be so intimidating any more. Even though I was still afraid of heights, I learned my gender issues did not involve heights at all. It was more a matter of me keeping my feet on the ground. 

Once I did, being able to help anyone else with understanding gender issues was a huge plus. Paying life forward for me has always been a powerful motivator. Plus, being able to shine a light on the gender differences between genders is not something to be feared. The differences should be embraced and celebrated. Including those of us who have been fortunate enough to have the chance to experience both sides of the binary genders. Even though, for me at least, all the down times and bumps in the road I experienced did not feel so good at the time. 

If I could tell my young self one important fact, it would be to relax, learn as much as I can and know I would be successful in the end and bridge the gender gap. Plus, if I stopped building unneeded bridges to climb and jump off of, I would be so much better off.

Trans Girl in a Beer Garden

Image from Igor Omilaev

Following moving in with my future wife Liz in a Cincinnati, Ohio suburb, I went through another unexpected transition. 

When I moved, I threw out all my male clothes and started living full time as a transgender woman and I still had my very small circle of friends who had ever known anything about my male self. What I ran into next was being accepted into Liz's circle of friends. Sure I was scared or terrified to meet them all, I had no choice to hitch up my big girl panties and go with it. Long story short, I survived and most of the group seemed to accept me with open arms. What it all did was add another layer of acquaintances to my transgender journey. 

Then the group began having Halloween Witches Balls in the metro Cincinnati area and Liz and I became organizers of the big party. By doing so, we needed to help select the annual venues. It just so happened, several of the potential venues were owned by brew-pubs in the area. In order to check out the venues, we (or I in particular) had to check out the craft beer. Through it all, I enjoyed myself immensely. One venue I remember in particular was in a retired huge old church and the second was a second floor area which featured an outdoor on street beer garden of sorts. After we looked at the party venue, we were able to find a table outside and enjoy a couple of their beers. Even though the brew was wonderful, the company was better. I was able to relax, not attract any undue attention and watch the world interact around me. As a relatively new transgender woman, it was the first time in my life I could live as a free person. 

From this point forward, I knew I was included in the group and had added another layer of gender transition to my life. I already know how much I enjoyed beer gardens from my days in Germany, so I was just combining the two for more success. Plus, for the first time, I was on the feminine side of life so I would not have to be envious of all the women around me. Now, since I drink so much less, experiencing an outdoor beer garden is a rarity. Fall, is not so far away and I hope I can experience several Cincinnati October fests to celebrate a big birthday I have coming up. Cincinnati is a heavily German heritage town and has some fantastic fests to experience along with the fall weather. 

Perhaps, it will be a great time for this transgender girl to experience more time in a beer garden. 

Procrastination

From the archives.
JJ Hart

I am well versed in most areas of procrastination. 

After all, I have spent most of my long life procrastinating as a transgender woman. Recently, I received the inevitable question of why I waited so long in my life to finally tackle my gender issues and transition. Even my daughter who has displayed the ultimate in acceptance in my transition over the years (and has a transgender child) shyly questioned me one day about if I had always known I was trans. With very little thought, I answered I had always known but I did not tell her how long I procrastinated doing anything about it.

One of my excuses has been times change over the years and the late fifties and early to mid sixties were dark times for anyone with gender issues. In fact, I remember the stories I saw about the police rounding up any transvestite or gay men in paddy wagons and taken to jail in the pre-Stonewall revolutions in New York City. So, when I included a very non accepting family life, the period of time was not a good time for me to outwardly explore any gender issues. 

Another excuse I had for procrastinating my coming out and living as my authentic self for so long was I lived in the pre-internet dark ages. In fact, my wife Liz and I went shopping for a new computer for her. Long story short, I was intimidated and totally lost in the whole process, I faded into the background. Liz needed a specific type of computer for her art business and had researched the whole computer situation. The only thing I could do was later on compare her research to mine when it came to me even considering I was transgender. Plus I was pleased when the clerk, checking Liz out referred to me as "she".

As times changed and more and more information concerning gender issues became available, I changed too. But not to the point I was ready to accept the fact I wanted to do more than just look like a woman, a part of me was screaming I was a woman. Now I know some would argue there is no way I will ever be a woman and I argue back my mind tells me I am even though in between my legs tells me I am not. Even though I could not experience periods or being pregnant, I went through so many things cis woman could never conceive of doing. Even so, I still went against my inner feelings and procrastinated again and again that I was indeed transgender. 

Deep down, I knew the truth but kept putting off the fact I was trans and letting the pressure build on myself. Finally when I went out into the world, I knew I wasn't trying to fool anyone. I was just being myself. When I couldn't lie to myself any longer, on a magical evening I will never forget I faced an internal mirror and decided who was looking back at me. No longer was I am a victim of the world and I was done procrastinating. From that point forward, I decided to go all the way and move forward to explore my full potential as a transgender woman. Major moves were ahead and exciting yet terrifying such as the major impact of adding gender affirming hormones to my system. 

It wasn't until I was truthful to myself and decided to follow a feminine path which I should have followed years ago did I become happier than I ever thought possible. My mental health improved and I got off almost all of the alcohol I was so fond of. Procrastination was behind me and just do it became my theme. 

The Ultimate Gender Grab

Image from the author, 
JJ Hart.

In many ways, this is an extension of yesterday's post which partially examined my transition from my male self into a feminine world. 

Along the way, there needed to be an ultimate gender grab to be successful. Very early on, the desire to view my image in the mirror was the fun part. I struggled to dream high and stay grounded with my gender desires which always threatened to change my life for the worse if anyone discovered my secret life in dresses and hose. I found I needed to reach out quickly and grab on any small amount of unattended time to cross dress away from my male self into my authentic transgender self. 

Sadly, my male self and society kept trying to grab my gender reality away from me. Some of it was my fault early on with how I presented myself in public. I found any edge I gave the public to "discover" me often led to a bad reaction. Serious side effects included my fragile novice transgender confidence being shattered. When it all happened, it took me weeks or even months to try again to grab my true gender back from the world. 

At that point, all the pushing and grabbing became almost too much to bear and I resorted to therapy to shore up my frail mental health. Plus, I fell back on a high level of alcohol abuse. When I went out to venues to see if I could make it as a woman, invariably I appreciated the false sense of bravery the alcohol gave me. The only positive came when I discovered other women friends in the venues I went to and they helped me to make a giant feminine gender grab which helped me towards my dream. All of a sudden, actually living as a transgender woman became a reality. The need for alcohol faded away.

The grab became so close, my male self panicked and did his best to hang on to all the work he had put into my old life. My feminine self came to the rescue and grabbed back her share of my life and ultimately won the war, even though she had lost all those battles over the years. Amazingly, all the battle scars she had sustained were easy to heal. She was saying, she had been there and done it as a subservient second fiddle to my male self and had enough of the lies. She thrived under the new life she had inherited and grabbed back all of the gender privileges she had only dreamed of. Better yet, she didn't care what the public thought of her and her confidence soared. 

It's no secret to anyone how the final gender grab would end up with me. My trans woman over achieved to an extent I never thought possible. When I was able to set back and trust her to run the show, the future was secure.   

 

Gender Anxieties or Paradise

Image from Cacique 
Nacimento on'
UnSplash

During my gender transition, all the way to today, I have experienced my share of anxieties.

Early examples revolved basically around the way I looked when I was cross dressed in my very limited feminine wardrobe. I kept telling myself I was OK when I with my cross dressing and I was for a couple of days before my gender anxiety returned. Making me difficult to live with. Paradise was fleeting and hard to find. 

Much later on in life, when I began to try out the public's perception of me, the whole process was anxiety ridden. When I used to shop till I dropped in clothing stores, my feminine life was easy because everyone was just interested in selling me something. Or I was in thrift stores where the clerks barely looked at me at all. Maybe because they were used to waiting on cross dressers? Very soon I came away with feeling no anxiety at all when I shopped so I felt I needed to challenge myself further. I needed to see if it would ever be possible to live my dream of being a full-time transgender woman. It was close to this time also when I began to seriously challenge the world as a woman at various Halloween parties I went to. Most of them happened when I was married to my first wife who knew I was a crossdresser  when I married her, so there were no surprises when she saw the "costume" I settled on. 

Even at Halloween, I experienced growth with my gender issues. When I dressed trashy, early on, I was treated the same way but when I decided to see if I could present as a business woman at the party, I was treated with more respect and even surprise at my true gender. Little did I know at the time when I dressed as a woman, I was presenting as my true gender. Very quickly I learned, Halloween was never enough and I needed to express my authentic self as a woman more than once a year. When I did, I began to do more of the household grocery shopping as a novice transgender woman as well as haunting the antique malls and bookstores for the perfect gift for my wife. Anything to take me out of my male comfort zone. When I was successful I was in paradise and when I failed, of course the opposite occurred and  I was sent back to my gender drawing board to re-think my plans. Could I ever make it to my dream the way I was heading. 

Spoiler alert, I could and did make it. Somehow and through the help of therapy I was able to work my way through a large amount of my gender anxiety. My therapist helped me to realize there was absolutely nothing wrong with my transgender desires. Which was as close as she could come to telling me I should proceed with my dreams. Paradise was reachable if I wanted to pursue it farther and I had already accomplished most of the hard work. I had established myself a foothold in the world as a transgender woman and it felt so good and natural, so what was I waiting for.

The answer to what was I waiting for was the outside chance my male self would finally get on board with my decision. He didn't and hung on to the bitter end. In fact he tried to ruin my transition all the way to when I was medically approved to begin gender affirming hormones or HRT. What happened was, the HRT changes were so dramatic, even my male self needed to finally give up and go away. He finally did, leaving most all of my gender anxiety behind and replacing it with a lifetime of feeling freedom such as I had never felt before. 

I had paid my dues and it was time to move on.

Trans Girl Destiny

 

Image from
the JJ Hart
Archives.

When I was given the keys to a transgender existence, on occasion I have to pause and consider how I have arrived here.

Unlocking all the mysteries of crossing the gender border proved to be more than I could deal with on occasion but I kept on moving forward. Trying to find out what it meant to achieve my dream of living as a transgender woman. Finally I learned to relax and let destiny take it's course. Before I could even begin to relax, I needed to learn the new rules of the road.

The rules of being a woman were not easy to learn before I was accepted for admittance into the club. I discovered along the way there were more female privilege's other than having doors opened for me by men. One of the biggest ones was being allowed to communicate with other women on a mostly non confrontational-passive aggressive platform. Along the way, the lessons learned were brutal and I ended up walking away with many scratches or claw marks on my back. Primarily I found not to even try to look at or get close to a woman's man. It frustrated me because the man always made the first move and I had no real interest at all but none of it mattered to the other woman. Another mystery solved as I worked my way towards my transgender destiny. 

During the years in between my final solution to my gender issues, I was held back by many circumstances beyond my immediate control. I felt pressure to maintain my marriage of twenty five years and a job I was rapidly progressing in. To maintain my life, I tried to balance my existence between the two primary binary genders which only provided temporary relief and in some cases, even made it worse. When I became more successful in living as a trans woman, I felt so good and natural, I just wanted more and more. Which included no going back to my old male life which ironically I worked so hard to maintain. Destiny was trying to tell me eventually I would have to give it all up and start over but I could not find the courage to do it.

As I waited and waited for my chance to transition, I came to the point of no return. Magically, at the age of sixty destiny really came into play. First of all, I was to the point when I considered gender affirming hormones as the next huge move I could make concerning my chance to live as a full-time transgender woman. As I was considering the move, the Veteran's Administration suddenly announced they would now cover HRT as part of their health care for veterans. Which I happened to be a part of. The only hold up was I needed to see a therapist at the VA for an approval. I still remember how nervous I was the first time I went to see my therapist and after a second visit, I had my approval for my life changing hormones. 

It was around this time too, my second wife had passed away. Leaving me very much on my own to consider any gender decisions. My choice as clear and impactful as destiny was showing me the way forward and leave my ill-fated dual gender life behind and live as a transgender woman. When I did, I found I had other major decisions to make such as the possibility of undergoing major gender realignment surgeries. I decided against it for several reasons such as I did not have any insurance to cover it and the VA in those days was not covering SRS at all. Similar to Medicare covering breast augmentation or facial femininization surgeries. I am not sure how much any of those entities support those surgeries to this day, so don't quote me on it. The only aspect I decided on was my gender was between my ears and not my legs and those closest to me viewed me as a woman. So I had achieved my goal.

I can't forget the final part of my transition life which destiny played an important role was the financial part. Since age wise I was so close to being able to retire early on social security, I could sell my vintage items on the side and make enough to go ahead and retire. Which meant I would not have to worry about doing a gender transition when I was working. 

So, I had secured my big three aspects of my transition so I had no real reason not to pursue my transgender dreams. Destiny worked for me.

Major Gender Differences

 

Image from Jamie'
on UnSplash

From the outside looking in, many see transgender women and trans men merely as people who have decided to dress different.

As I was applying my estradiol patches this morning, I thought how different the entire process is when you decide to come out into the world as your authentic self, be it as a woman or a man. It is the same process as when you transition from being a cross dresser to being a full fledged transgender person. For me, finding my gender destination was a long term process. I write often concerning the years of transforming myself into the feminine person I always knew I should have been my entire life. 

What I did not understand for the longest time, I was joining a whole new culture when I transitioned. No longer could I bluster my way through a world filled with white male privilege. I needed to strike out on my own to find out what living in a woman's world was all about. I learned quickly, I knew very little about it and what I did know was usually wrong. I kept feeling stuck until I could work it all out. Was I even doing the right thing trying to cross the gender border. Plus, what was I going to do about those who did not want me crossing the border at all. Fortunately, I learned fairly quickly most of the world did not care what I wanted to do one way or another and most of the public I was interacting with were in a financial situation when I essentially was paying their salary. Either from a commission at a clothing store or from a tip in a food or bar venue. Either way, being friendly worked wonders in my transition. 

Very quickly, people began to see me as a new person. A person I wanted them to see which caused me to add major differences of changes to my life. A prime example was how was I going to suddenly attempt to talk to the world as a transgender woman. The whole communication process was similar to starting all over again when I first explored the world. At first I was petrified to talk at all until I tried to mimic the women around me. The problem was if I didn't talk, I was coming off as mean or stand-offish.  I needed to solve the problem and solve it fast if I was going to survive in the world as a transgender woman. I needed the voice to match my appearance the best I could. It was a major gender difference I always put off pursuing because I was so obsessed with my appearance. One of my favorite accessories was my sunglasses which helped me watch the public's perception of me without them seeing mine. I could better judge if my appearance was making the grade. Which I hoped was a passing score. 

Naturally, the more progress I was able to attain in the world as a trans woman, the more confidence I had to try more living. Again and again, outside of a few ill advised trips to red-neck venues, I was able to stay out of the gay bars and make my way through the world. I had fun in the lesbian and sports bars I was accepted in and was learning more and more about myself. To be sure, seeking a place in the world of women was never easy and I needed to earn it. I worked long and hard to learn from my mistakes in public and go back to the drawing board when I needed to. Finally, I reached a point where I could put the drawing board away and make it on my own.

Validation as my new feminine self then became a priority if I was going to keep living as a transgender woman. I attribute my lesbian friends with giving me the guidance I needed to succeed, They showed I did not need a man to validate me and my sexuality did not have to change to live as I was. All important lessons I needed to learn if I valued my independence in a new world. 

Learning gender differences meant so much more than looks was very inciteful to me.  All the catch phrases such as walking the walk and muscle memory come to mind when it came to my transition. I had such a long way to go to separate myself from a very convincing male life, there were many times I did not see how I could make it,

To do it, I needed to attempt to study all things feminine until I got it right and when I did keep doing it until practice made perfect. Then and only then was I able to move forward on my very long gender path.

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.

It's All in the Eyes

Sad Eyes
Image from
the Archives.

Over the years, my eyes have helped me out in many ways.

Of course there is the obvious reason such as the blessing of eyesight but then, life steps in- very importantly for a cross dresser or transgender woman trying her best to improve her makeup art. For me at least, the hardest part of conquering the mystery of makeup  involved making up my eyes. At the time, I equated it with applying paint to the plastic model  cars I was fond of building because I struggled with both. Ironically, at the age I was at, I am fairly sure my Mom would have did her best to forbid any use of makeup at all by the daughter she never knew she had. 

Still I persisted and grew more proficient with buying then applying my eye makeup, The availability of all the colors fascinated me. Along with the chance to match colors up with my limited fashion choices I was capable of finding. It was close as I could come to all the girls around me who I admired so much. 

Fast forwarding many years, my eyes continued to be a focal point in my makeup art. I had learned along the way women communicate through the eyes in many ways. Much more than men who rely on vocal cues. I knew as I transitioned into transgender woman, I was on the right path with my makeup techniques. All the years I put into my art was worth it.

Perhaps the most rewarding feedback I received from my eyes came from my wife Liz. For all the wrong reasons. We met on line when she responded to a post I listed as woman seeking woman. Keep in mind I immediately pointed out I was a transgender woman. Thankfully, none of my gender issue mattered to Liz and she said she was attracted to me because I had sad eyes. If the truth be known, during that part of my life, I did have sad eyes. Over the past two or three years before the picture, I had just gone through very dark portions of my life. Primarily due to death of my second wife and four of my closest friends, mainly to cancer. Along with the loss of my business, I had lost nearly all the self confidence I had ever had in myself. In fact, the only concrete thing I had to grasp onto was my identity as a trans woman. 

Regardless of my sad eyes, my girl self became my deepest passion. In many ways, just to get by, I needed to become a deeper researcher of women. Instead of becoming my father's son which I had chased for many years, I became my mother's daughter she never wanted, to my knowledge. The gender guilt I felt was only grief with no where to go. 

Led by my eyes when I communicated with other women, I found my way out of the darkness of life I was in and regained my confidence. Even though it was a different confidence than I had ever felt before. My confidence as a transgender woman was a hard earned quality which went all the way back to the days when I was struggling with makeup and shaving my legs when I was a kid. Living and learning was always an exciting experience. Even in the days when I was a dismal failure in the world. Somehow, deep down, I knew I was doing the right thing by pursuing a life as a trans woman. 

It was always in the eyes, I just had to learn how to use mine. They were such an important part of my life when it came to communicating with other women. Perhaps it is true when it is said your eyes are the window to the soul.

Gender Expectations

Image from the JJ Hart
Archives

As I progressed through my gender transformation, I had so many expectations.

All I really wanted to be when I grew up was a woman but I had no idea of how I was going to achieve my dream. Unlike most of the major professions available to me, there were no schools I could apply to to be femininized. I just wanted to find my passion and follow it. 

To do it, I finally had to be free of the mirror and join the world. Even when I discovered that, I had to often snatch defeat away from the jaws of victory. Or I was defeating myself by going exactly the wrong way with my women's fashion, hair and makeup. At the rate I was going back then, there was no way I was ever going to exceed, or even make it, to my gender expectations.

Another problem I encountered was the complexity of the new life I was trying my hardest to live. Every time I turned one corner it seemed I had another blocking my way. I began to see life as a series of walls I needed to climb. For example, if I couldn't learn to communicate with the world, how could I ever hope to bring my dreams to life. Many times as I journeyed out into the world, I was flying blind not knowing what to expect. The whole process was at once scary yet exciting. It took me many evenings out on my own to establish myself in venues I wanted to be secure in. At the time, I was doing my best to separate myself from the gay bars I was going to where I did not enjoy being treated as a drag queen. 

It was very difficult at first to be accepted as a single transgender woman in the sports bars I was going to. Often I resorted to using my cell-phone as a prop to fend off anyone who thought I was going to be alone for any length of time. It was during this time when I started to meet a trans woman friend of mine and socialize in many venues I was fearful of going into by myself.  There seemed to be an extra amount of security when I was with a friend. When we were together my gender expectations were satisfied because I was allowed to relax and be more social in the world.

From there I transitioned into having my lesbian friends and had a chance to really blossom. All of a sudden, I did not need a man to validate my existence as a woman and they helped me climb another big wall towards achieving my dream. My experiences at lesbian mixers, roller derby matches and even professional football games helped me to come out of my gender shell fast. By doing so, I needed to free my long dormant feminine inner being so she could help me to become a new person. She gladly did so and took off tons of pressure from my gender expectations. If I did not know what to expect, she did and took charge and maybe most importantly gave me the chance to build a quality trans person. I had the rare second chance in life to learn from my mistakes as a cross dresser and a man.

I finally ran the string out and had seen all I needed to see as a transgender woman and couldn't wait for the gender affirming hormones or HRT I was approved to take to take further charge of my body. All my expectations had been exceeded and there was no way I could have dreamed of coming this far in life the first time I slid into hose and a bra when I was a kid. 

I don't completely know why I made it but I sure am happy I did. Along the way, my gender expectations were often confusing to me and impossible to explain to others. Even though internalizing my feelings was brutal, good therapy helped my mental health. Even more so if I had listened to my gender therapist years ago who told me there was nothing either of us could do about my desire to be a woman. Of course I was stubborn and did not listen. If I had, my gender expectations may have really changed for the better much earlier in life.