Smiles Equal Confidence

 

Go Ahead and Smile from the
Jessie Hart Archives. 

Where ever I go in public, I try to lead with a smile to ultimately disarm any potential transphobic individuals. 

I have to remember also I look better when I soften my face which still has a tendency to go back to my old male scowl if I am not careful. A male scowl in my world always comes off as a bitchy look which I normally am never feeling. 

The whole process goes all the way back to the days when I was cross dressing my way to the front of the mirror. Since all the ups and downs which followed, I needed to learn to put my feminine image in motion if I was to succeed in following my transgender dreams. Since recently I have been getting out into the public's eye more and more again, I have needed to reinforce wearing a smile to boost my confidence as a senior trans woman. This morning was no different when I went with my wife Liz to her eye doctor visit. 

After I applied a light amount of makeup to go with my casual outfit, I thought for once I looked presentable for the world. I even tripped off my gender euphoria for a brief second. My euphoria lasted until I went through the door into the doctor's waiting room. For the briefest of time the two receptionists just stared at me and finally said how could they help me. Not the friendliest of greetings and I became worried about my presentation. Since I had quite a while to ponder the situation, I came up with the problem and it was all me.

I had forgotten the most important part of my presentation which is my smile. For the greatest majority of the public I face, a smile disarms them and allows me to communicate with them on a one on one basis. Plus when I am smiling, I am showing the confidence I need to enable the people in my world to be more friendly also. Most importantly, a smile is my best accessory when I use it properly. Not using it at all takes me back to the day when I was shopping for clothes and suddenly nearly ran into a girl child who was darting between the clothing racks. When she stopped and saw me, she exclaimed to her Mother "Look at the BIG woman." I had long enough to consider the kid at least called me a woman. Then she ruined the feeling by calling me a "BIG Mean woman." From then on I resolved to try to put a nicer look on my face and not scare the public with my bitchy look. 

After living a long unwanted life trying to exist in a male world, some habits are still hard to erase. Putting a smile on my face shouldn't be such a big deal but it is. So big, the whole process is as big as makeup, fashion and hair. Putting the whole image into motion is what counts for me to be truly successful as a full time transgender woman.  

Transgender Pressure Cooker

Image from Jeshoots.com. 

When someone writes or says something about me being a transgender woman being a choice, I have to laugh. 

I'm sure those of you who have gone through life the way I have with gender issues would agree. Primarily because we have given up so much to cross the gender frontier. Primarily, I am referring to losing family, spouses, employment and gender privileges to transition. Just losing male privileges alone is a major issue. Very quickly I discovered I lost a portion of my intelligence when by accident I became involved in a conversation with several men. I found I was not respected in their world until I finally got tired of being ignored and left the group. Then I began to not speak much until I was spoken to until I began to gain more confidence. 

When I began to be successful, the pressure to be even better as a transgender woman started to increase. For several reasons, my fragile mental health became worse as I started to try to live a life situated between the two main primary genders. In other words, I was stuck in a gender fluid universe I did not want to be in. Living one day as a man and the next as a transgender woman, nearly killed me.  It became so bad I needed to make a conscious effort daily determining what gender I was going to be that day. How was I walking and talking were just a few of the many gender considerations I was going through as the pressure kept increasing. 

All of a sudden, I was able to establish a whole new identity as a trans woman. I was talking to other women and building a small circle of friends which taught me so much about the world I so much wanted to be a part of. I kept going because the process became so natural to me and very soon the main source of pressure came from having to return to what was left of my male life. Even thinking about going back caused me stress and added pressure. 

Finally, I knew I had no way around it and never really had a choice with my life. As a gender therapist told me so many years ago, there ultimately would be no choice for me if I was a transgender woman. Sadly I did not believe her and stubbornly went on to fight a losing gender battle for years before I gave up and faced my gender reality. By doing so, I tried very self destructive measures including suicide and excessive alcohol abuse before I started to live my truth. 

I had no choice and needed to give up all the pressure I felt to transition into a feminine world before it all literally killed me. Thank goodness for all the friends and family I had who helped me through my difficult pressure packed days. The more good days I had with them led to my belief I could live my gender truth full time. Ultimately transitioning was similar to sliding down a hill towards a steep cliff for me. I had others around me who took the pressure off and made the landing a soft one.  

Growing into the Problem

Image from Karla Hernandez 
on UnSplash.

 Back in the day when I was growing up as a young gender dysphoric person, I felt I had been able to hide my femininization efforts from the rest of the family.

For years and years, I lived under the impression I was successful. After all, I was doing my best to compete in all the basics I needed to fit with a demanding, unwanted male world. I was born into an extended male dominated family, so there was considerable pressure to conform as one of the oldest sons of three competitive uncles. 

Along the way, my main goal was to properly hide my small but growing collection of feminine clothes and makeup. I used every cent of my allowance money plus money I earned from delivering the local newspaper to rural neighbors. I thought I was successful because I was never confronted by primarily my Mom about what was going on with me. Remember also, this all occurred during the late 1950's and early 60's. Information on gender issues was for the most part non existent and was considered to be a mental illness which was even worse. 

I think now, if indeed I was ever "discovered" as a truthful cross dresser, my Mom who essentially took on the major role of raising my brother and I, just decided I would just grow out of it. Plus, she may have thought I had some sort of fetish for woman's clothes rather than the deeper issue of wanting to be a girl. It could be described as kicking the rock or can down the road just hoping it would go away.

Instead of going away for me, I grew into the problem but it took me years of wasted time and effort to take advantage of my gender growth spurts. I say "spurts" because of the time I took fighting my transgender issues at all. Keep in mind too, I am referring to at over a half century of my life. Quite a bit of time to consider mistakes and successes when it came to accepting and then growing into my considerable gender dysphoria. For me, gender dysphoria could be described as looking in the mirror one day and seeing a feminine face then the next seeing a masculine one. The whole process just destroyed my fragile mental health. At the point, I sought out therapy to help me. Which provided me with various amounts of relief. 

I had one male therapist who told me to ignore the problem, all the way to a gender therapist who told me the truth. I needed to learn to live with being transgender because it wasn't going away. Easier said than done for me because I was too stubborn to listen to the advice I was paying for. 

True gender growth for me didn't really begin until I started to escape my dark closet and began to explore the feminine world. Of major importance was the fact I finally outgrew what I call my cross dressing fashion adolescence. In other words, I stopped trying to dress as a teenager who was able to wear revealing or even sexy fashions. On the other hand, I just looked ridiculous or even trashy. Once I learned to dress for my age and body style, my presentation as a novice transgender woman improved and my new public life improved dramatically. I was growing into my so-called gender problem. I grew so fast, plus with the help of others, I discovered I didn't have a problem at all. 

Once I grew into my "problem" I discovered a wonderful world I had only dreamed of. I was even able to bring a substantial amount of my old male life with me and carefully weave it into a new existence previously dominated by my old male self but then taken over by my new feminine one. She quickly proved to me, she knew what she wanted in life and had learned from all those years of  rejection. She was like I told you so. 

Now I am not sure all the time and effort I took to grow into the problem was worth it. Many times I wish I wasn't so stubborn and had taken the time to listen to my feminine reality and just went ahead and transitioned into a transgender world.  

As always, thank you for following along with all my experiences here on the blog! I appreciate your time!  

Living in the Transgender Present

Image from Alexander Grey
on UnSplash.

As I lived and constantly thought about escaping my unwanted male world, I daydreamed major parts of my days away.

It became very difficult to stop looking ahead and live in the present when all I could think of was the next time I could cross dress as a girl or woman. Over the years, I wish I could reclaim just a bit of the time I lost due to my day dreams of being a woman. The problem I ran into was when I started to journey away from my dark gender enclosure and was successful, the more natural I felt and the more I wanted to challenge the world as my authentic self. My overall life became more and more complicated and further disrupted my already fragile mental health. At the time, I was seeing one of the few therapists in my native Ohio who dealt with transgender issues at all. Along the way, during one of my sessions, she (my therapist) told me the truth. There was nothing she could ever do about my gender issues and somehow, someday I would have to deal with them. On the positive side, she also diagnosed my bi-polar depression for the first time and was able to separate my two main issues, mental health and gender. 

Then I reached a  point  where I had to decide how to exist in the present dealing with two major issues. I was prescribed several different medications to deal with my mental health issues but as we all know, there is no magic medication to deal with being transgender. The only positives which ultimately came from seeing the specialized therapist came from my wife. She thought I was trying to help the problem she saw in our relationship which back in those days was considered cross dressing or being a transvestite. Which still was a long way from just being viewed as a guy who liked to dress as a woman for Halloween. Naturally, my wife was afraid of what our friends might say. During it all, we hoped seeing a therapist would help. I can only imagine, if I had listened to my therapist about the long term life expectations of being transgender would be, how much different my life would have been.

With each experience, as I started to explore the feminine world more and more, I began to begin living in my transgender present. Every time I was successful in the world, the more confidence I began to experience and maintain. My whole world essentially flipped. When before I day dreamed about being a woman, now I was dreaming in a negative way about going back to a male life I increasingly did not want. To help even more, I had a new therapist who helped me keep my two main life issues separate and even provided crucial assistance in aiding my search for gender affirming hormones. 

In my mind, the hormones, or HRT as they were called then, helped me to cement where my life had become. I loved the external and internal changes the hormones had aided me in achieving. In a short period of time, I had come so far I asked my therapist for her help in changing my legal name and other gender markers. She came through with flying colors and with the help of my daughter, I came up with a new family based name which reflected my heritage. I chose the name of one of my maternal grandparents as my first name and my Mom's first name as my new middle name so my initials would be easier for my three grandkids to remember and use. 

From there on to the present, I have gone all out to live in my transgender present and make up for all the lost time I had in my life daydreaming away for my next trip in the cross dressing mirror. 

Making it all Effortless

Image from the Jessie Hart Archives

When I decided to go all out and attempt to go public as a novice transgender woman, I found I had plenty to do before I go conquer the world as my authentic self. 

Reversing all I had learned to try to fit in to an unwanted male world proved very difficult to accomplish. Even more so when I learned I needed to make the gender transition seamless and effortless if I was to survive. The first problem I had to beat was getting myself out of my mirror. Just posing in my spare time cross dressed as a woman wasn't getting it anymore. Deep down, I knew I needed more if I was going to survive in my scary new world.

As I attempted to put my new feminine self into focus in the real world, I knew I needed to put away all my deeply ingrained male mechanisms. The prime example was doing away with my permanent leave me alone scowl on my face. I needed to replace it with a softer, kinder gentler look. I needed constant reassurance from myself to make it happen. Primarily because I didn't want anyone approaching me. I found out the hard way my methods were completely unfeminine and I was coming off as a bitch or worse yet, a miserable mean human being. I even was called a big mean woman in a clothing store one day by a little girl, so I knew I needed an immediate change.

The second most profound change I needed to make was how I moved as a transgender woman. Of course, it is no big secret women move differently than men and even though any added dimensions to my hips and butt were due to foam padding, I still had to practice overtime to accentuate my new figure. What I resorted to was trying to practice every second when I thought I was alone trying to walk like a woman. The problem I always encountered was everytime I thought I had put the total package together of makeup, hair and fashion and put the movement with them, I needed to go back to my male world and try to forget the whole thing. Through it all, I became very frustrated. I was having real problems making my whole feminine image effortless. 

Even still, I continued to make it a priority and finally began to see improvement in how I was perceived in the world as a transgender woman. I know, athletes call it "muscle memory" when they repeat a motion over and over again until they get it right and that is exactly what I needed to do. I started to look the public in the eye when I communicated with them and paid attention to what they were saying to me. By doing it, I was able to more precisely tell is someone was reacting negatively to me because I was trans and then what could I do next time to improve my presentation. 

Making it all effortless, did take a great amount of work but it was what I needed to do to accomplish my goal of leading a life as a transgender woman. Plus, I could not have done it without closely observing all of the women around me and the many ways they reacted to the world.    

Tearing Life Apart

 

Image from Darius Bashar 
on UnSplash

Sadly, before many things have a chance to change, you have to tear them apart and then reassemble the parts. 

In order for me to pursue a life as a transgender woman, it was necessary for me to essentially tear down my past male life and start all over again. This was painful for several reasons. The main one was I was giving up all the hard work I put into to surviving in a male world. Secondly, I needed to fight the male in me completely because he was totally fighting any gender change which was happening. 

It all started when I left the mirror as a novice cross dresser and went into the world. I learned the mirror was an easy challenge until I faced the public. Primarily because the mirror didn't move and neither did I so when I may have stumbled on the perfect look with my makeup and fashion, it all had to change when I needed to put it all into motion. Was I walking and talking like a woman? The whole process caused me extreme gender confusion when I was trying to separate the days when I was a trans woman with the days I was in my everyday working life as a guy. Perhaps the biggest problem I faced was dismantling one life and beginning another in the middle of the entire transitioning process. I felt everytime I was successful in public as my novice transgender self, I had to stop and return to a male world I increasingly didn't want anything to do with. 

Even though, I was risking all I had worked for in life including a loving wife and family and a good job, the fact still remained I thought I was living a lie. I just couldn't keep living a lie and continued to tear down my old life and prepare myself for a possible dream scenario where I could possibly live as a fulltime transgender woman. The entire process was cruel and unusual punishment to me and destroyed my mental health until I could get it restored much later in my life. In the meantime, I needed to find ways such as diverse gender mixers I was going to, to try to feel better. It seemed everytime I attended a party made up of everything from cross dressers to transsexuals, I learned more about myself and where I fit in to a new expanding LGBTQ community. Primarily the new term (transgender) which seemed to fit me the best. 

As I was busily considering tearing down one life, I had other serious others issues to contend with. Such as my sexuality and how was I going to be able to communicate in a new world as a trans woman. It turned out, I was overthinking the whole process and destiny would come along to answer my most pressing questions. You regulars know the story of how I found and was adopted by a small group of cis-gender women who taught me the basics of communication and how to conduct myself in my new world. And then there was my wife Liz who rescued me from very dark times, took me in as my authentic feminine self and eventually married me.

It has been such a long trip from standing cross dressed in front of the hallway mirror growing up and the ups and downs of tearing one life apart to start another has been scary. But eventually I made it.  

Gender Euphoria

My wife Liz on the left
From the Jessie Hart archives.

Sadly, gender euphoria is too rare for most transgender women and trans men.

For too many of us (including me) gender dysphoria rules the life.  Throughout my life when I get up in the morning to begin my day, a quick look in the mirror tells me I am living my external gender as yet another day as a guy and my gender dysphoria sets in. I describe my gender dysphoria as being a deep seated issue caused by my desire to live as my authentic feminine self. From then on my day is set on how it will go.

However, every now and then something comes along to reassure me I am doing the right thing with my life. It could be as little as my wife Liz referring to me as "she" all the way to a server calling Liz and I "ladies" at dinner when we eat out. Whatever the case, gender euphoria is brief and dysphoria is always lurking in the background. 

I think part of the problem is all the difficulty I experienced as I followed the path to living my transgender dream. In the days when I just considered appearance as my number one feminine dream, of course there were always plenty of other women (trans or cis) to compete with because they were far more attractive than me. My impossible dream was to do the best I could to survive in a sometimes brutal world as a novice cross dresser or transgender woman. Initially, I made the mistake of attempting to dress sexily to validate myself in the world. All too often, my attempts came off as trashy or even clownish. Plus, one night my wife had to rescue me from a huge man at a party who had pinned me against a wall in a narrow hallway. In no way was there any gender euphoria or feminine validation involved that night. Just my wife reprimanding me for not taking better care of myself ahead of time. Not to mention, she hated what I wore. In my mind, I was trying to keep up with the beautiful transsexual women who were there also.

Through it all, I managed to have enough moments of pure gender euphoria to keep my gender dreams alive. Very early on all the visits to mall and women's clothing stores provided me with positive one and one feedbacks with the clerks to think I was doing everything right as a novice feminine cross dresser. It took me many years to realize, the clerks were mostly nice to me because of my money. Years later, after I came out to my daughter, she told me of her days working at Victoria's Secret when the occasional man would come in shopping for lingerie in his size. Other clerks would refuse to wait on him but my daughter did and pocketed the commission. I could have been green and most of the clerks would have still liked me.

My mall days continued my gender euphoria to an extent I never thought possible. I used to go to the up-scale malls in the area in my very best business professional fashions. Including a very stylish black jumpsuit I loved with my black heels and blond wig. It seemed I never had any problems and my euphoria soared along with my confidence. Sadly, I normally found a way to push the so called envelope too far and get rejected in the world and my gender dysphoria would set in again.

It wasn't until I began gender affirming hormones did I reach the point of no return in my male to female gender transition. Regardless of what happened to me, negative or positive, I needed to attempt to move forward towards my dream. Happily, the feminine hormones improved my exterior image. My skin softened, my hair grew and my facial angles softened which made my whole presentation easier to do, since I needed to do it every day. 

Even with all the help. I still have the dysphoria/euphoria battle with the mirror every morning. Sometimes I win the battle, sometimes I lose but most importantly, I have learned neither aspect of my appearance should rule my day. Nothing is as good or bad as it seems.

Thanks to all of you who join me for my experiences! I appreciate you taking the time to stop by and even comment. It all means the world to me.

It Was Never Easy

Image from Alexander Grey
on UnSplash

 Two things amaze me when people bring up to me when they learn I am transgender. The first is when someone thinks I had a choice and the second is the entire process was at all easy. 

Since I was never a so-called natural feminine person to begin with, I needed to struggle completely to reach my goals of surviving in the public's eye at all as a woman...trans or not. The best description of my passing struggles came when my transgender friend Racquel told me I passed out of sheer will power. I knew what she was trying to say. I wasn't the best looking woman in the room but I was going to force the issue anyhow. 

Early on, I had only the mirror to do my gender battles with. I finally learned too late the mirror often lied to me. Night after night, I would think I looked great only to be immediately stared at or even laughed at in public. It was difficult learning how to try to dress myself so my feminine fashion helped me to live a life I had only dreamed of, not hurt it. At the same time, I tried to lose as much weight as I could and take care of my skin so I could wear less foundation. None of it was easy. But it was worth it.

In order to accomplish all I wanted to do on my difficult gender journey, I needed to learn something new and different. I had to learn to be my own best friend. I never liked my old male self and was just learning all the new possibilities of my feminine inner soul. She had many problems to face as she fought for acceptance from my male self who fought completely for all of his rights. At times, it was an ugly, bloody battle I never want to go through again. It was anything but easy and never a choice to go through as I was to find out later. 

I ended up suffering so much, I almost ended my life several times from various reckless self harm attempts all the way to an attempted death by pills which failed before I decided enough was enough. In order to survive I had to make a choice, so yes I guess I did have a choice and it was a very desperate one. Self survival meant I needed to pursue what measures I could and change my life forever. The final determination was deep down I felt more natural as a transgender woman and needed to find out where I would need to end up in the new pack of women in society. It was then I learned how deeply layered a woman's life could be and perhaps even more so as a trans woman. I had all the extra baggage of my previous life as a man which I carried with me to the other gender side. I knew the male gender expectations men had of women which made me extra shy of the entire gender dance between men and women. Primarily I learned why both genders often have a difficult time communicating in their relationships and wished often I could go back and do my life different. Maybe then, my second wife would have never said I made a terrible woman. Which I did and thought it only had to do with how I looked.

The final example for this post I will use was the amount of time it took me to finally face reality and come out fully as a transgender woman. Adding up the years, I struggled with my ultimate gender issues for nearly a half century. It was certainly difficult to break out of my old male chains and live the life of my dreams. I realized I never had a choice.

You Can't Buy Love

Image from the 
Jessie Hart Archives

 One of the first lessons I learned when I was first brave enough to date girls was spending more money equaled to more dates with certain girls. Sadly, the plainer the girl, the less potential spending was going to happen. When I flipped my gender, I found out how evil it was.

As a transgender woman, I was or am not the prettiest woman in the room. As such, I never managed to have many dating interactions with men who most of which just saw me as some fetish object. They wanted the first date to be a motel room. I drew the line at any sketchy first dates and demanded a meeting in a public place of my choice. What happened then was a predictable amount of being stood up on possible dates. While I did have a couple meaningful dates with men, often they were unscripted moments in the regular venues I went to often. One night in particular happened with a man called Bob who treated me completely as a woman and I loved it. He lived far away and was married so there was no chance at any further involvement. 

Through that period of my life I was questioning my sexuality also so any dates with men added to my possible knowledge. The farthest I ever went was very brief episodes of heavy petting or making out. From it all, I learned I still preferred the attention and company of women. With the help of a few female friends I learned the meaning of what it meant to be to be a transgender lesbian. In order to do it, I found I didn't have to have a lot of money spent on me to be happy. I was more into spending more money on my feminine self to attempt to improve my public's appearance. I ended up saving every extra penny I had to buy that next extra wig I didn't really need to be more attractive than ever before. At least in my mind. As I acquired more fashion and makeup, slowly but surely was acquiring more acquaintances to try my new fashion out on.   

Which leads me to another woman I don't mention much anymore who is Amy. Amy is the woman who recommended me practice with a banana to get ready for my intimate moments with men. So as you can tell she wasn't shy. One day in particular  with her comes to mind when she invited me over to her house for a spaghetti dinner with friends. I didn't really ask who else was coming, I jumped at the chance to enjoy a home made dinner. Fashion wise, Amy had only seen me in my short denim skirt days, so I decided to wear one over to her house again not thinking who else would be there. It turned out she also invited two men so the group included a cis woman, a transgender woman and two men who were seemingly ill at ease with me. I made the decision to join Amy in the kitchen and serve the men their delicious Italian dinner. I decided if the men were going to be ill at ease with me, I wasn't . I enjoyed the meal, helped clean up the mess, stopped to socialize with Amy and left the men behind. Just another learning experience.

I finally was able to slow down on expenditures on fashion and makeup and spend more on my personal interactions. My experience with dealing with both sides of the binary gender spectrum helped me to truly understand what buying love really meant. I understood both genders often expect intimacy in return for how much money you spend. The last woman I ever dated me as a man suggested to me we go to an expensive steakhouse for food before our first date. I politely saw through what she was up to and declined and we went to a more reasonably priced venue of my choice. Probably dooming our relationship from the beginning. She was quite attractive and a diva to begin with so I figured she thought she could do better than me and our brief fling ended after three or four dates.

Since we live in a money driven society, buying love is hard to do and even more difficult to resist as a transgender woman.  

Following the Path

 

Image from the 
Jessie Hart
Archives

The path I followed as I chased my gender truth at times turned out to be very difficult. 

It all started with having a very unaccepting family environment and continued from there. Similar to so many of you, I needed to wait for just the right time to pull out my small stash of girls clothes and cross dress. Because of that my available times to dress up and do my best to follow my new path were few and far between. Plus, the signs I desperately were looking for were distant and difficult to read. When I came to gender cross roads, I was having a hard time figuring out which one to follow. 

This was all happening during my pre teen years so I was confused enough about my life to start with. On top of the usual questions kids had growing up, I had added problems wondering what gender I was, all the way to my sexuality. I felt as if I was attracted to girls during puberty but the how I was attracted became the problem. I was facing the sexuality issue of desiring women because I wanted to have sex with them when all I really wanted was to be them. To make matters worse, I was extremely shy around people I didn't know. Especially girls. None of it was making my path any easer to follow.

To make matters worse, when I was in high school, the political powers to be decided to dramatically expand the United States presence in Southeast Asia or the Vietnam War in particular. On top of all my other worries I needed to add possibly being drafted to serve in the military. Not a good feeling to carry with me all those years. How could I possibly serve if I didn't want to be a man at all. It turned out, I didn't have the choice after I stayed in college for four years, I was drafted anyhow and my path became very clouded. 

The best I could, I went down my path adding three years in the Army to my life experiences. At the least, I had more knowledge of the world to base my gender decisions off of. Or, at least I thought so. Not long after I was discharged from the military, I went through the life altering experience of having witnessed the birth of my first and only child, a daughter who turned out to be my biggest supporter to this day.

As I was building a rather successful life as a man, I also began to explore other cross roads on my gender path. Possibly the biggest one was when I started to think of myself as more than just a casual cross dresser and more of the newly minted transgender individual. Most certainly just thinking I was trans rather than a guy in a dress petrified me. To make up for all my gender fears, I did my best to hide my true authentic self from the world. When I did, I kept hitting more and more dead ends on my path. 

Years later, as I was stumbling along attempting to find my way, I sustained so many bumps and bruises I could take it no longer. I made the effort to see a doctor and be approved for HRT and all of a sudden my path became more of a highway to my future. I guess it was more like an interstate as I was able to easily pass more and more milestones on my journey. 

It certainly took me long enough to get to my destination but once I did, it was all worth it.

The Home I Don't Live In

Image from Daiga Ellaby
on UnSplash

It certainly took me awhile but I finally learned my male self was simply an empty shell I existed in to get me by in the world.

Over the years, even though it was difficult, he managed to secure a spot in the world and earn his white male privileges. Participation in such male dominated activities such as sports and muscle cars led the public at large off the beaten track of who I really was. I was a cross dresser or a woman pretending to be a man. Along the way, I was still able to build a fairly strong home I didn't live in.

Around that time, my life in an an empty house became predictably lonely, even though I was doing all the traditional male activities. I was married, had a child and served my time in the Army to add to two college degrees. It seemed the more I tried to do, the less fulfilled I felt with my life. It wasn't until years later when I understood much of my frenetic pace in life had to do with my gender desires being off center. In essence, I was building a home I couldn't live in. 

In it's place, I was increasingly becoming more and more serious about discovering if I could actually pursue a dream of living as a transgender woman. What I was doing was observing others in the trans community who were moving towards living fulltime feminine lives. I wondered if they could do it, why couldn't I? I was learning consistently by going to small mixer/parties in nearby Columbus, Ohio. The get together was hosted by a soon to be retired firefighter who restored an old house in a well known restoration district. I was extremely interested in her path because she was going against all the so called "rules" back in those days. Back then it was expected when one fully transitioned into being a trans woman, she was expected to leave her old life behind and start all over again. The woman I knew was going to not do any of that and I dreamed of doing it also. The same as her. Plus her parties included a diverse group, including the occasional lesbian and I learned early of the attraction I felt for lesbians' and vice versa.

Even though I did manage to slightly follow in her footsteps, leaving the male house I built proved to be anything but easy for me. To arrive at my destination, I would have endure intense moments of pain and suffering. As my old male self finally crumbled, I would be remiss, if I didn't mention the group of friends I found to help me build a new house. This time the correct one, complete with a life in my chosen gender. 

Even though the challenge was there to build my new house the correct way, I still needed to make sure all the improvements were built in to further make my new life more pleasurable. Out went the old male clothes and in came women's clothes including shoes, wigs, and makeup. 

The end result was, I discovered I could indeed build a brand new gender house and redirect the rest of my life living in it. The home I didn't live in was long gone and I felt a freedom I never thought I would ever have again in my life. 

Procrastination

Image from Brett Jordan
on UnSplash

For as long as I can remember I have been a procrastinator. Unless I was really pressed, it was always easier for me to put off until tomorrow what I should have done today. 

Later in life, being a procrastinator in my gender life came back to haunt me. As I continually gained ground in learning if I could exist in a feminine world, the more the pressure on me increased to decide what I was going to do with my life. Primarily effecting my already fragile mental condition. I had previously been diagnosed as Bi-Polar along with having elevated anxiety so I already had plenty to deal with mentally. So, I was not in any position to improve my mental condition by procrastinating over my transgender issues. Still I persisted and my problems only escalated. 

I was frustrated when every success I found as a transgender woman, seemingly just led me to the ultimate decision I was having a problem facing. Was I ever going to be follow my dream and live as a woman. Plus, all my procrastination led me to was an increasing reliance on alcohol to limit the mental pain I was suffering. What happened was, the effects of alcohol gave me courage to explore further if I could make it in a feminine world as a full time trans woman. Was I gay, was I trans? I needed to know.

Finally,  rational thinking took place and I could take it no longer. My gender truth was slowly but surely killing me. One night I sat down by myself and made the biggest decision of my life. As soon as possible, I decided I would seek a doctor's approval to begin gender affirming hormones and never look back on an old male life which was always a struggle to maintain. What a relief it was to finally face my truth and move on as my authentic self. It was time to put all my procrastination behind me and my life immediately began to improve. 

Still I was not up on any pedestal. As I always mention, I could have never have accomplished what I did without the help from several key cis-women friends and family. In essence my friends pushed me over the cliff into a world I had only ever dreamed of. Perhaps, not so surprising, my reliance on alcohol started to decline as at the same time my overall mental health began to improve. 

Ironically, my only problem became that I procrastinated coming out as a transgender woman as long as I did. I would have loved to have the years back when I anguished over which of the binary genders I would live as. In other words. sometimes I think I wasted too many years to claim a life as my feminine self I just kept putting off. The only excuse I had was, during my procrastination years, the world around me was changing. In the pre-internet years, there was a definite lack of information and contact. Our dark lonely LGBTQ+ closets were difficult to escape. 

The fact remained I still grew up putting off the most important aspects of my life and it continued until I finally decided enough was enough and it was way past time for me to live as a transgender woman fulltime.   

An Opportunity or Challenge

Image from Dylan McLeod 
on UnSplash

If you are similar to me and if you had a quarter for every time you heard a so called problem was no more than an opportunity to improve, you would be wealthy.

As I moved forward down my gender path, I found an increasing number of opportunities. As I mention often (or all the time), I had a difficult time adjusting to how I should try to present myself as a novice cross dresser. All outfits which included too short mini skirts or shorts were out. In place came a more conservative wardrobe which I found I could blend in with the other women I encountered. The challenge or opportunities I encountered were exciting yet terrifying. 

I had many firsts to deal with in my wide wonderful new feminine world. Many of the firsts I encountered, did not go smoothly and I went home sobbing. When I did, in the safety of my own home, I took ownership of the damages and attempted to build a plan to do better in the future. I went through every opportunity to improve such as better makeup, wigs and wardrobe as examples. I was very focused on the entire process. To the point, I had a difficult time when I still had to function as my old male self. I experienced a new challenge to stay in cross dressed mode when I flipped my gender script. Slowly but surely I was spending more physical time as my feminine self. It took me years to realize I was a woman cross dressing as a man. Not the opposite. 

Then, when I really started to seriously cross the gender frontier and deal one on one with the public, other opportunities or challenges became important. By this time, I was becoming very courageous in how I lived my life. I sought new venues to see if I would be challenged as a transgender woman. Some worked out and some didn't, so I crossed many off of the list. Many of the opportunities became challenges back in those days when I first began to seek access to women's restrooms. The whole process was an overall success with some notable failures when I had the police called on me. Still I persisted and earned my rest room privileges the hard way by learning the etiquette involved with using the women's room. Such as always looking other women in the eye, not putting my purse on the floor and pausing to wash my hands (no matter how much attention I was creating) among so many other nuances I was learning. To go into it all would entail a whole different blog post.

Another huge challenge or opportunity I faced was when I decided to begin gender affirming hormones, formerly HRT. There was no way I could anticipate the changes by body would go through. Both externally and internally as I was suddenly seeing the world in a softer version of it's former self. My sense of smell heightened and my thermostat changed as I became colder easier are just two examples. All in all, my body took to the changes easily and I felt as if I should made the change years before I did.

If I had utilized all the time and energy I needed to overcome the challenges of changing my gender and put the energy into my male self, how much farther could he have gone. The end result was so powerful, there was no way I could ever look back and change my reaction to anything.  

The Elephant in the Room

Halloween Girls Night Out
Kathy on left. 

Many times in my life I have felt as if I was the elephant in the room and it had nothing to do with my physical size. I was a pretty good sized man at around six foot tall and two hundred fifty pounds which kept the bullies away when I was younger so I wasn't a huge man.

All my problems began to surface in my unwanted male life when I went to family events and felt strangely out of place. As my male self I was the elephant in the room, or you could refer to it as the impostor syndrome. All along I was a woman pretending to be a man. 

As life went by and I had more experience presenting in the world as my authentic feminine self, I felt even more out of place at family events such as my brother's house. It was the place we always gathered for big sporting events with him (my only sibling) and his two sons. All was good until I started my hormone replacement therapy and started to appear decidedly more androgynous. Even then, before my breast growth started to happen along with me being able to grow my hair long, I was able to wear a loose fitting shirt and tie my hair back to still remain vaguely male. My last attempt "purging" my feminine self came approximately six months before my second wife unexpectedly passed away from a massive heart attack. 

As I "purged" I vowed to grow a beard which would make it technically impossible to go out dressed as a transgender woman and/or cross dresser. It worked and I was extremely unhappy but my macho cooks at least responded in a positive way, saying I looked more "masculine." Not a compliment I wanted to hear, 

One of the first things I did after my wife's death was shave off my beard and resume attempting to learn more and more how to live a feminine life. When I did, I learned my size could be dealt with and it had nothing to do with being the elephant in the room. In fact, during a couple of my initial girls nights out, one woman acquaintance in the group was even bigger in size than I was. I finally figured out it wasn't so much how much bigger than most women I knew, it was so much more important how I carried myself, as well how well my fashion sense blended with the other cis-women around me.  

However, there were many times when I still did feel like the elephant in the room, when it came to be invited to other girls nights outs. One night in particular comes to mind when I accepted an invite to go with a group of servers and bartenders to party one night at another close by venue. Even though I was warmly accepted in the group, I couldn't shake the idea I just did not come up to their level of attractiveness, which included size. I finally concluded there was nothing I could do about it, relaxed and had a good time. For the most part, they were surrounded by guys trying to pick them up so I very much just faded into the background anyway. 

As with anything else in life, a person has to take the good with the bad. In the long run, my body has provided me with a successful base to operate from. I was big enough and barely athletic enough to keep the bullies away and not too big and masculine I could not squeeze myself into women's fashions. I guess you can say, my elephant ran enough interference for me to get by until I could establish myself as a transgender woman. 

I was the elephant in the room and felt it on many occasions as a impostor man and a trans woman. I lived to tell the tale...so far. 

Under Twinkling Holiday Lights

Image courtesy Clifton Mill 

In my past, when I was progressing down my very difficult gender path and leaving my old male self behind, I began to try to experience new and exciting things. 

Part of my plan was to experience activities I enjoyed as a man and experience them as my new feminine self who was enjoying the time in the public's eye. Keep in mind she did not  know how being in public would work at all. She had so little time having done it. 

One of the activities my second wife and I enjoyed doing on a regular basis was taking the short trip to a vintage working grist mill It has become famous in the area for it's Christmas decorations To put it all into perspective, the venue says there are four million lights although I don't know who is patient enough to count them all. None of that mattered to me as I planned for my chance to experience life as my authentic self which was becoming much more than an impossible dream. At the time, my second wife had not passed away as yet and I was very much sneaking around behind her back when I cross dressed as a woman and left the house. I arranged my work schedule to have a rare Friday night off, knowing she would have to work because she was in retail as a manager of a major book store. My plan worked to perfection and in the holiday season hustle and bustle she indeed had to work. She knew all along of my cross -dressing desires but drew the line at me going public as my feminine self. 

As the time went by, I needed to plan what I was going to wear for this all-important evening. I needed to plan for the weather and for my comfort at the same time. I knew the parking situation at the Mill was not the best and I would need to walk a distance to see the lights and holiday displays. For the evening, which turned to be an ideal mid-December, chilly winter evening. The moon and stars were out and I was ready for the magic which was coming my way. But first things first, I had to choose my warmest, fuzziest sweater, leggings and comfortable boots which were suitable for walking. After putting on my clothes and makeup I thought I looked the part of an upscale woman out for a night at the Mill. Little did I know how wonderful the evening would turn out to be. Under the sparling stars and twinkling Christmas lights I finally would have the chance to live as the feminine transgender person I always felt I could be. 

Of course, the first obstacle I needed to conquer was the fairly simple task of stopping and waiting in line for a much-needed hot cocoa with marshmallows. Once I reached the front of the line, I was so nervous, I could barely order. I summoned every ounce of my courage to tell the woman behind the counter and in a low voice ordered my beverage. I was happy and my confidence grew when she smiled at me, took my money, and gave me my drink, and she even wished me a Happy Holidays.  From then on, I had to make a conscious effort to slow the evening down because I was moving so fast and not enjoying the moment as much as I should. From then on I slowed down and enjoyed being in the public's eye as the feminine person I always wanted to be. To celebrate, I even splurged and stopped at another concession for hot cocoa. 

What I remember the most about the whole experience was how heightened my senses were. The lights were brighter and twinkled even better than before. The only thing missing was a visit from Santa Claus himself. He was scheduled to appear later, much to the joy of all the kids in the crowd. In the meantime, I was able to shop the Mill's gift shop but could not buy anything for several reasons. The main one being having my wife questioning what I was doing there in the first place without her.

Before I knew it, I had seen all the animated attractions, plus the Santa doll display. All in full view of an accepting world which was a first for me. From that point forward I had the confidence to do more and more towards exploring the world as the person I always wanted to be. When I had the chance, I started to do the rest of my Christmas shopping as a transgender woman. I look back on my trip to the Mill as the beginning of a wonderful lifetime transformation. I discovered I could be me no matter how difficult the path may prove to be. Discovering the basic differences, the binary genders deal with was a major path to follow.

In many ways, the excitement of the first evening under the holiday lights would be a wonderful beginning to the life I was always destined to live. It was never as easy as walking among the crowds of people un-noticed sipping a hot drink, it was enjoying the totality of being myself. Which would become so increasingly complex as the years progressed in my life. All in all, the holidays lights were a wonderful, even magical beginning to a better life. Without knowing it, I was giving myself a wonderful holiday gift my inner self was wishing for. 

Sadly, time was up too soon and I had to head home to beat my wife there as well as take all vestiges of my makeup off my face. I knew one thing; I couldn't wait to experience such a fun night out again.  

Fear as a Motivator

 

Image from Amanda Jones
on UnSplash

Most of the time I can't remember the number of times I was paralyzed with fear as I pursued my gender path from a serious cross dresser to novice transgender woman. 

Examples include nights I sat in my car sitting in fear trying to figure out if I would go into the venue at all. Some decisions were easy such as entering gay venues but others were much more difficult.  Along the way also I made poor choices on which venues I was trying to go into which caused me to have more fear in the future. Mainly when I tried to visit redneck-ish places to see if I could present well enough to be accepted. The end result a couple of times were not good when I had the police called on me. I learned my lesson and was much more selective on where I went. It worked and the power of my fear was ultimately rewarded when I discovered venues where I could relax, have rest room privileges and become a regular patron.

There was a time when I considered the rush I received when I conquered my fear was a primary reason I cross dressed at all. Of course I finally realized fear was not why I wanted so badly to be a woman. The entire process went much deeper than all of that. What it did do was encourage me to go farther down my gender path. I set up goals I wanted to achieve. When I considered fear as a factor in future cross dressing decisions, it soon was reduced to just being nervous. Ironically, being nervous still sticks with me to this day. I need to push myself to certain restroom decisions because years ago, choosing the women's room was the primary reason I became a target of the public. By years ago, I mean the last time I experienced any restroom problems was nearly three decades ago but then again I am still nervous even though I know my way around the etiquette of using the women's room.  

Eventually I began to understand fear and used it as a powerful motivator. When I was considering not going to a party or a new venue I use fear as a reason to move forward. Of course now since it is rare I go anywhere without my wife Liz, we make a couple which keeps most transphobes at bay. 

Since I am mentally predisposed to having anxiety, I still have a tendency to worry about things such as me being mis-gendered again at my upcoming colonoscopy. Even though I keep thinking if that is all I have to worry about, I really don't have any issues at all...relatively speaking. I better begin to worry about the results of the exam as well as the unpleasant prep process I will have to go through before hand. 

It has occurred to me also, maybe I should have done a better job separating fear with excitement. My earliest days of exploring the world as a transgender woman were very exciting and the fear on occasion was a powerful motivator to conquer the gender anxiety in my life and move on. Plus, overcoming my fears gave me the all important confidence to move into a transgender life.  

Owning It.

 

Image from the Jessie Hart
Archives

Long ago I learned the hard way the power of owning my public appearance as a novice transgender woman or very serious cross dresser. 

I was tied too closely to my mirror and didn't realize until it was too late how it could lie to me. Examples included how the mirror told me I was an attractive woman who could go anywhere just to be bounced almost immediately by the public. Many times I would come home in tears wondering where I went wrong. Finally I came to the conclusion I was putting my feminine priorities in the wrong place. In reality my mirror was not in my house but was in the public's eyes. When I learned to dress to blend in with the other women around me, I began to own my existence as a transgender woman. No longer did I have to worry as much about being laughed at in public. 

Also, when I owned my life as a trans woman, I gained the all-important confidence I needed to follow and improve my right to exist in the world. If someone had a problem with me, it became their problem, not mine. The biggest pressure I faced was needing to communicate with the world as my transgender self. Suddenly the process went way past how I sounded into what I was saying. Owning the new gender world I was in meant learning to operate on an entire new spectrum involving an internal look at how the two main binary genders (male and female) communicated. Quickly I learned why men and women couldn't connect on the basics of communication. I learned also both genders put up a sort of invisible barriers when it came to talking to each other. Ironically, I began to be asked by each gender why their spouses or partners didn't understand them. 

I truly didn't find out why I had a key insight into both genders until I was allowed by other women into their world of life and communication. I learned the power of non-verbal communication as well as the seismic power shift between the genders. Basically the process is very simple. Men deal with power systems such as money and athletics when women deal with a more passive aggressive world. I was fortunate in that I was aware of how women formed smaller cliques (not teams like men did) and reacted passively aggressively to those with power. Such as management. When I was in my male management days, I learned the hard way if I wanted something done with my female staff, first I had to sell it with just a few key women on the staff.  Dealing with an alpha female was much different than an alpha male in more than the obvious ways. The ways I needed to learn if I was ever allowed to completely be welcome in the women's sandbox. I needed to win over the alpha females first.

I made it when I paid my gender dues and was able to own my life. The confidence I live with now is but a side benefit.

Shopping 201

Image from Brett Jordan
on UnSplash

Over the years I did quite a bit of shopping in clothing stores and malls, mostly successfully.

It took a while but I finally learned much of my success had to do with the fact my money was more important than my gender to the average store clerk. Many I think worked on commission and anything they sold was added to their paycheck. Even still, the experience was valuable in building my confidence as a novice cross dresser in the days I was running from the idea I could be transgender. I was paying my way to people so they would be nice to me. Only one time did I run into any problems when an older clerk told me my skirt was too short. In response, I left and never returned since there were plenty of clothing stores to go to.

In a short period of time, I grew tired of the same old shopping I was doing and started to expand into stopping for lunch where I needed to interact one on one as a woman with servers. The entire process opened a whole new gender world to me and for the most part I was treated politely with respect. Overall the process took me to a whole different level of Shopping 101. I grew bored and was ready for a new course I called Shopping 201. 

The new course ended up providing me with endless possibilities to expand my horizons as a very serious cross dresser. At the time, I was searching for ways to do different things in the feminine world. One way to sneak around behind my wife's back was to start doing part of the grocery shopping. I would pick times I knew the grocery store we went to would not be busy and out I went. The women's fashion trends back in those days fit me well. I could wear one of my oversized soft sweaters along with a mini-skirt and flats and look like any other fashionable woman without going overboard. One morning in particular was memorable. 

On the day, I carefully shaved my legs and prepared my wig. After dressing and putting on a light amount of makeup I took off to the grocery when my wife was at work. I arrived at the store, grabbed a cart and proceeded to pick up a few needed items. Then I headed up to the register line to be checked out. This was back in the days before self checkout so there was only one way to go. At the register there was one older cashier and one kid bagging groceries. When he saw me, his eyes immediately went to my legs and when he noticed me watching him, he blushed and stammered something about helping with my groceries to the car. Never before and rarely since have I affected a male such as that. The cashier just gave me a knowing smile. 

From there, I couldn't resist reverting back to Shopping 101 and made a quick stop at a nearby big box store to pick up another pair of panty hose and shop for new makeup. By doing so, I was able to hide my expenditures along with what I spent at the grocery store. 

I was able to negotiate the morning as my feminine self and learn so many new things so I could graduate Shopping 201 and move on towards life in a transgender world.   

Going Back

Image of Liz on left and Daughter on right
from the Jessie Hart Archives.

 Recently I read a rather sad post from a person who was giving up her gender transition and going back to her original life. 

Even though I consider myself very fortunate in how my gender path turned out, I could understand the facts the person mentioned when it came to her new life. Among other things, the person related experiences which have haunted many of us following a transition. Such as having problems with loneliness, finances etc. So many transgender women are stuck in their houses, often with just having a computer to provide any contact with the outside world. This de-transitioner was older and provided a picture which showed a very presentable senior woman. My heart broke when I saw her image, I just can't imagine going back after putting so much work towards accomplishing a goal. Perhaps it is because I tried so hard and risked so much when I crossed the gender frontier. Plus, possibly for one of the few times in my life when I ever set specific goals, I was able to achieve what I set out to do. 

One of the major differences I saw when I read the post was how I approached the gender goals I was attempting to accomplish than most others. One of the examples was how I approached on-line dating services. I went all in with three or four services with the usual results of receiving tons of trash back in the process. I tried everything such as woman seeking woman to man seeking man. Amazingly, when I was giving up, some how I ended up meeting my current wife Liz who lived within driving distance in Cincinnati, a city I had always loved. That happened over ten years ago and it all started with a date to a drag show. As an aside, Liz identified as a lesbian witch so I was intrigued. 

In addition, the lucky move I made to create a new social life came when I decided to not go to anymore male gay venues and decided to go to the sports orientated big venues I was used to. I figured if I was going to risk being discriminated against, I might as well go to a place where I could enjoy myself. The gay bars aggravated me because I was always treated as a drag queen. What I don't recommend is the amount of alcohol I consumed along the way. On the other hand, I ended up meeting several other women in the venues who became friends. 

Very quickly, going back in my transition never had to be an option. By the time I decided to go all the way as a transgender woman, I knew my daughter would support me as well as Liz and my small circle of friends. As I made the final slide down the gender slope my landing turned out to be very soft. Even still, my heart goes out to those who are considering going back. Perhaps the whole experience could be thought of an ultimate experience which failed. Or maybe, they just wanted their old male privilege's back. 

Then again reversing my life again would be unthinkable because I would be so unhappy. I am afraid the person who did decide to go back would never be happy on either side of the binary gender border. 

Changing the Gender Locks

Image from Adam J
on UnSplash

It took awhile for me to change the locks on my old male self. He kept hanging on and on to the smallest reason not to go all the way with my gender border crossing.

Through it all, he was quite comfortable on occasion taking advantage of all the male privileges he had come to take for granted. He was used to taking personal security and even intelligence for granted. Age seemingly was the only prerequisite in gaining respect. When the locks were changed years ago, life changed with it. 

Changing ones' gender is nothing to be played with. I'm biased but I think transitioning as a transgender person (woman or man)is one of the hardest things a human can experience. All the cards are stacked against you as early in life you are forced into a square hole when you are certainly a round peg. Perhaps the interesting fact of the whole gender experience is when one door opened and you went through it, often it was slammed shut and locked behind you. You then had to be quick on your feet and learn what to do next. Surely mistakes were made but it was the only way to learn. Some would call it tough gender love. 

The farther I went in life as a novice transgender woman, the more locks I needed to change. The more I entered the world and was successful as a feminine person, I felt natural and couldn't wait to lock the old male door behind me. Even when it led me to potentially dangerous situations. I write often of the times I was on the verge of being seriously molested or worse in my early days of exploring the world. One night I was dressed way to skimpily and attracted the wrong set of man. My second wife needed to bail me out of the situation so I never heard the end of it. Even still I locked that door behind me and moved on with an important lesson learned. 

I was doing what I believed in so I was stubborn and any progress gave me hope. To follow in someone else's path would just have not worked. So I said to hell with the possible consequences such as losing my three "F's" family, friends and finances, I kept changing the locks behind me. I needed a huge lock as well as amazing amount of duress and thought before I decided to go through with donating all of my male clothes and deciding to live a fulltime life as a transgender woman. Also, hormone replacement therapy was in my future should I decide to explore the possibilities of furthering my femininity through HRT.

Along the way, I became very proficient at changing my gender locks and hiding them from the everyday world. Depending on the door, often I had to stop and look around at a totally new and exciting world. Once I did, I always decided to move on seeking a new door to go through.