Welcome to Hell

Inside "Casa Susanna" A dream trip I never made. 

My early days of dealing with a severe case of gender dysphoria can only be described as being in hell.

For those of you who can remember the dark days of information before the internet and social media, you also recall the days of being completely alone in your dark gender closet. Since I was raised in a very male dominated family, I knew escaping my own closet was going to be difficult at it's best. I was forced to sneak around behind my family's back to steal away the time to cross dress in my small stash of girls clothes and makeup. I even resorted to storing away my clothes and a spare mirror in plastic bags in a hollowed out tree in the woods next to our house.

Through it all, I knew the whole process of dressing as a girl made me feel better but somehow would have to be enough to get me by. I followed the vicious cycles of feeling the gender euphoria of being feminine in my mirror with deep depression when I was denied access to my clothes. I learned very early I wanted to do more than look feminine, I wanted to be feminine. Way before the term transgender was ever invented. to put the date in perspective, I would have been in the 1960's before I hit my teenaged years and still years away from my military duty and discovering Virginia Prince and her "Transvestia" publication which only dealt with so called heterosexual cross dressers or transvestites. I mention "Tranvestia" again because it was my first link to other like minded people. 

From then on, I knew I wasn't alone and could even go to transvestite mixers which were within driving distance of me. Even though I had discovered others, it turned out I was still dealing with my own personal hell. I still needed to be able to deal with the gender euphoric times followed by longer periods of gender dysphoric down times. Ironically I brought much of my hell on myself by not knowing the best ways to dress and apply makeup to best present my inner female to the public world. I had a difficult time dealing with all the stares, all the way to laughter when I tried to take on the world. Once I began to learn how to best handle the public, along came the Army to disrupt my life. As much as I didn't really want to experience military life at all, specifically I didn't know how I could exist three long years without having a chance to express my feminine self. For years, as I waited for the Vietnam War to draft me, I went through hell considering it's ramifications to me.

One way or another, I made it through the three years and couldn't wait for the relative freedom I had to escape my own personal gender hell, no matter how briefly. 

My big escape came when I made the highly personal decision to stop considering myself a cross dresser when I went out and I transitioned into thinking of myself as a transgender woman. Semantics to be sure but a huge move for me mentally. By mentally transitioning I was able to take a huge step out of my own personal gender hell. In many ways, I entered my golden years of MtF gender transition by leaving much of my hell behind and be able to increasingly explore the world. 

From then on I was able to free myself from my gender dysphoric hell and start to live my dream life as a transgender woman. Although I want to say the process was worth it, I wouldn't wish my journey on my worst enemy.

Coming Out to Employees?

 

Halloween Witches Ball Image
Liz on Right 

As we rapidly approach Halloween and my wife Liz's operation coming up, I thought it was time  for another Halloween experience while I still had time. 

This one happened when I was managing a fast food restaurant just outside of the New York City  metro area. More precisely, very close to the Bronx. As Halloween rolled around, once again  I was stressing out about what I was going to wear. The pressure was on since it was nearly impossible for me to leave the house we lived in dressed as my feminine self. I was back in the mode of waiting another year to escape from my mirror until the next Halloween rolled around.

As I faced the pressure head on, I decided to go all out as I decided what my "costume" was going to be. I put together what I thought would be a potentially a sexy look without crossing the line into being trashy. I pulled out my shortest dress, along with my highest heels. Most certainly, my wife's most hated outfit on me. In this case, I used her motivation of me to spur me on. For once, since she wasn't going anyhow, I decided she would have to get over it. I would have to put up with her displeasure with me for the next several weeks but it was worth it for me to pursue my dreams.

As I said, my outfit was going to be short and sexy as I to the best of my ability fool the world to what my true gender was all about. Little did I know, I would be able to find a situation where I was able to blend right in. 

As it turned out, one of my assistant (woman) managers was going out to one of her local taverns to celebrate Halloween with her friends and she invited me along. After I dressed, did my makeup and hair and was ready to go. When I arrived at my manager's house, it turned out the friends she was going with turned out to all be tall and beautiful . As it turned out, by pure accident, At least in the height department., I fit right in. When I first saw all of them, as the room grew silent, you could have heard a pin drop. Time seemed to stop for me as they examined me from head to toe. Of course I could only guess what they were thinking as we left for the short walk to the venue where we were going. Thank goodness for me (in my heels) it was not a long walk.

As we arrived, I learned a valuable lesson about being with other single women who were attractive. The first thing the women did was essentially split and worked the room. They left me on my own which was an experience in itself. After I bought a drink and found a seat at a small table, I settled in to try to enjoy my evening in the world as a novice transgender woman or even a transvestite. And it turned out, the night was far from over. As I tried to sit by myself, I attracted attention from an older guy who kept bugging me to dance. Which I refused although deep down I was flattered. Finally, the night was over, the group of women broke up and headed their own ways. 

I ended up back at my restaurant which I knew was closed by then. What I didn't count on was, the closing crew would just be getting done and they would see me in my "costume." Surprisingly to me, the response was positive even to the point of one of the guys saying I had good legs. 

More importantly, the backlash from me dressing as a woman for Halloween was a non starter for most of my crew and life went on. The only variable was my assistant manager who I think couldn't wait to tell my boss who smiled at me differently for awhile. However it was New York and there were bigger issues to deal with than me dressing as a woman for Halloween. Which was one of the reasons I wanted to move there from our native Ohio to begin with. 

As far as my second wife went, she finally made me pay my dues as only a woman knows how to do. I learned from it and moved on. Knowing I had been able to experience a truly wonderful evening to think about and remember forever. 

Pre-Political Meetup

Image from the 
Jessie Hart Archives...

 Long ago, following a few of my Halloween adventures when I did my best to stay away from looking trashy on Halloween. I was determined to do my best this night to be mistaken for a cis-woman. 

I decided to attend a party I was invited to as a professional business woman. The get-together was being held at a restored Victorian mansion which was owned by a casual friend I knew. A wide range of people were invited. I worked at a radio station in town at the time and since my first wife never really was into Halloween, I was left on my own to find someone else to accompany me. It turned out one of the news reporter women at the radio station had an invitation also, so we agreed to go together.

In no time at all, it was time to put together my "costume." I started with shaving my legs and putting on a brand new pair of panty hose. From there, it was very easy to choose an outfit from my growing feminine wardrobe. The years have clouded my memory so I do not exactly remember what I wore except it included heels and my red wig which I loved so much. Of course when my "date" saw me she was amazed and amused I would go to such lengths to be noticed on Halloween. Plus she was more than impressed when I was able to do such a good job walking in heels "for the first time." 

When we arrived, the hosts had done a wonderful job of decorating their old mansion. Even including a vintage glass topped coffin with a real skeleton. Most importantly, I was able to relax and enjoy being out of my gender closet for the first time in a year in public. I was truly a novice transgender woman just exploring the possibility for the first time if I could be accepted in the feminine world. 

As the night progressed, guests came and went and the alcohol flowed. Also I was receiving plenty of positive feedback on my "costume." I had made the correct choice to dress as a professional woman for the party. Most of the other guests assumed I was just arriving late from work and didn.t have a chance to dress up. Which was exactly my goal. 

The most flattering happening came when this couple approached me and said how impressed they were with my "look." They were totally fooled into thinking I was a woman. Through it all, I recognized the man and his wife as a newly elected politician on his way to Washington, DC. Plus they wanted me to tag along with them to another party they were going to,. Since I didn't know where they were going and was with someone else, I had to politely decline the invitation. Leaving me to forever wonder what would have happened if I had decided to go along with them. 

Who knows? Perhaps my political career was ended before it even had a chance to begin. At any rate, the evening turned out to be a blast and my "date" never mentioned how I looked again. It wasn't too long when she landed another news job and moved away anyhow. 

As far as the politician goes, he turned out to be re-elected several times to congress. I lost track of him also when his political career was over. I stayed friends with the owners of the mansion over the years until I moved away and they divorced. Maybe deep down inside I was disappointed no one brought up how I looked on Halloween that night so long ago. I was probably desperately trying to out myself and no one cared. Or I was so good at hiding my feminine side with my intense male self, no one could see my true self. 

It wasn't to be until years later, my feminine self finally took control and Halloween "costumes" became a thing of the past for me.

Secure Beginnings

 

1966 Transvestia Cartoon

This morning I read a post by a transgender man I follow on another writing format. 

The number one fact I took away from his post was how accepting his grandparent was when he was growing up. In fact, the grandparent took him to get his hair cut and purchased him clothes to match his authentic gender. After I read the post I responded by saying how good it must have been to have a supporting person in their life. 

Sadly, I was never able to take advantage of having anyone even knowing about or having any inkling about my gender issues. I knew without any shadow of a doubt, I was expected to be a boy in all aspects of my life. My parents were of the "Greatest Generation" which was the WWII and Great Depression generation. As a child growing up in the 50's, I was expected to fit neatly into a square male hole and survive the best I could. in a world I did not embrace.

The entire experience of being totally alone in the world as a boy who wanted to be a girl led me quickly to extreme cases of gender dysphoria. It wasn't until many years later when I learned of Virginia Prince and her "Transvestia" publication did I discover there actually other transvestites as they called themselves back then. Thinking back, I am fairly sure the publication was mailed out every two months and I couldn't wait until the next one arrived. Thanks to "Transvestia", I was able to learn about actual mixers which were close enough for me to go meet  other cross dressers or transvestites. As I began to see others in those mixers up close and personal, I learned how many levels of difference there were in a community which I imagined to be so similar. For example, the idea of the mixer being for only heterosexual transvestites only was quickly dispelled when too many of the participants disappeared behind  their hotel room doors too quickly.

Ironically, through it all, I still didn't feel as if I had found any sort of a home with others who supposedly were supposed to feel similar to me. Looking back, I think it was because the concept of being transgender had not been widely publicized at the time. I knew I did not belong with the cross dressers trying to deny their male selves or the transsexuals in the group considering radical gender realignment surgery. In those days, anyone who went down the surgical path was recommended to move away and begin a totally new life. As severe as my gender dysphoria was at the time. I couldn't imagine myself doing all of that.

It took awhile but I eventually stopped blaming my parents for ignoring my gender issues. Part of it was my fault for never attempting to tell them what was really bothering me, so I took the traditional male approach and just bottled it all up. I hid it all so well until the night after I returned home from the Army. I came home late from drinking my share of beer and found my Mom waiting up for me. We started to talk and along the way, I tried to come out to her. She followed her instincts and offered to pay for mental health counselling and I followed mine and never brought it up to her again. She has long since passed away so the best I could do to honor her anyhow was to change my new legal middle name to hers nearly five years ago. 

I needed to realize the "Greatest Generation" was good at providing and not so good at emotional support,  at least in my family. Once I accepted the facts of my upbringing, I really needed to work hard to not repeat the cycle of my upbringing. Once I began to feel secure in my transgender life, I was able to  do it.    

First Impressions

 

Picnic Photo, Liz on Right

Following up on my Halloween post from yesterday, I began to think of all the first impressions I noticed when I first went out in public as my cross dressed feminine self.

My biggest takeaway from the experiences came when I was interacting with men I knew. Nearly immediately I felt a rejection as if I had been excluded from the male club. Later in life, I would figure out I was just experiencing a loss of my male privileges. The better I presented as a trans woman, the quicker my male life went away. When I did, I learned I needed to live my public life with a perceived loss of intelligence and personal security among other things. I just didn't realize in those early days of public interaction exactly what I was experiencing. 

Along the way I also learned how the power of first impressions changes between the binary genders. Men seemed to concentrate on sizing other men up as more or less another threat while women were more accepting. To this day, I need to adjust to smiling first when I meet another woman and not to walk around with what is left of my old male scowl on my face. The problem I have is pre-judging the reaction someone else is going to have to me. You would think by now I would not be so affected by my thoughts anymore but I am. Most likely my thoughts still come from when I first started meeting up with the public. Halloween or not.

First impressions also involve how much confidence you have in yourself. When you can summon the courage to know without a doubt you are in the right place at the right time leads others to believe you are too. In her own way, my wife Liz encourages me to step forward as a confident transgender woman when we are interacting with the public in places such as restaurants. Even so, confidence in public can be a very fragile thing as I found out very early. Even when I was going out under the cover of having a Halloween "costume." 

The more parties I went to, the better I became at refining my outfits. I wanted to try my best to be mistaken for a genetic or cis-woman and not myself. The good news was it actually worked on occasion and the bad news was I needed to wait another year before I could build on my experiences and discover if I could really be able to ever live out in the world as a trans woman. Spoiler alert, I could but the process was to be a very difficult one for me. 

The first problem I had was figuring out which wardrobe I could choose to hide my testosterone poisoned male body. I started the process by losing nearly fifty pounds and finished by undertaking HRT or hormone replacement therapy. When I did, more and more I was pushed out of my old male comfort zone and into a new and sometimes terrifying feminine world. I had to learn all over again the power of first impressions and how to deal with people. 

For the most part, my life experiences now have been positive ones. The problem people I run into often have a negative world of their own which has nothing at all to do with me. I am merely invading their space. 

It is the best I can do!  

The Power of Halloween

 

Image from Danie Franco
on UnSplash

During my life of realizing how deeply my gender issues went, the more important Halloween parties became to me. 

I could say going to Halloween parties dressed as a woman began innocently enough. All I really wanted to do was go out and feel the thrill of wearing a short dress with freshly shaven legs and new silky panty hose. Little did I know, I would experience so much more as the years went by.

My first "costumes" were simply trying to dress as trashy as I could, trying my best to "thrill" my friends into thinking I could be an attractive woman. It turned out to be a process I would go through for Halloweens to come. Dressing to thrill just wasn't enough, dressing to be mistaken for a woman became my goal. 

Even still, my first Halloween party when I seriously dressed as a woman was a memorable one from several different reasons. Ironically, the party happened when I was in the Army stationed in Germany. I was fortunate when I was assigned to work at the AFN (American Forces Radio and TV Europe). Naturally, compared to others with more strictly military duties. I also managed to live in a separate barracks with others assigned to a medical commissary. We had it easy. 

When Halloween rolled around, the people in the medical group decided to have a big party and it was my big chance to put two years of being cross dressing frustrated behind me. Finally I had the opportunity to cross dress again if only I could find the clothes and makeup I needed to look the part, Since it has been so many years ago, 1975, I don't really remember how I came up with all the necessities I  needed to dress as a prostitute but I did. Short mini dress, high heels and long blond wig completed my outfit and to the party I went. I ended up having a great time, which included too much German beer and Jägermeister. Through it all, I remember all the prying hands I needed to fend off from places they should not have been.

The big question I had was, did I do too good of an effort to be attractive? I always considered shaved legs was the deciding point between someone who casually dressed as a woman for Halloween and someone else who was way too serious. Plus, I still had to keep in mind, I still had a year to go in the Army and I did not want to lose my chance for a honorable discharge if someone looked at my "costume" and decided it was too gay. 

It turned out not to matter anyhow. A couple weeks later when my group of three close friends and I got together for dinner (and beer) I ended up being indirectly asked how serious I was about looking like a woman. I blurted out very serious and that I was a transvestite. The first time I had admitted it to anyone. As free as I felt at the moment, putting myself out there could have been potentially very harmful to me as I tried to finish my military service. Fortunately nothing ever came of my letting others in to my "secret" and I served out my time with an honorable discharge. 

From then on, I couldn't wait for my next chance to leave the mirror behind and express my feminine self in the world. Sadly, the only time I could do it was Halloween which I will have plenty of interesting posts about coming up.   

Opportunity or Challenge

Image from UnSplash

During our often long and torturous gender journeys, we often face many difficulties.

The first obstacle we face happens simply because we faced the problem of having no chance to really experience the world as a youth as the gender we really wanted to be. Transgender woman or trans man, both have to catch up with what we missed as a youth. Not being able to socialize with others as our authentic selves really would come back to haunt many of us when we first ventured out from our dark and lonely gender closets. Of course, in the case of trans women, we needed to learn the basics of makeup and wardrobe before we could seriously move forward in the world. 

In my case, moving forward meant saving my meager allowance and adding it to my paper route money (I had a rural newspaper delivery route) so I could purchase my own make up and even was able to buy my first pair of women's shoes. I learned quickly, just having the money was one thing but having the courage to spend it was another. I needed to gather my funds and courage then try to sneak out from where my Grandma lived to visit a nearby Woolworth store which featured (among other things) an intimidating section of makeup supplies. I do not  remember now how I was able to maintain any sort of composure to buy anything but I did and was able to slowly build my own small collection of makeup which I was able to hideaway from prying eyes at home.

It turned out I had faced the challenge of purchasing my own makeup and then had to face the opportunity of how to apply it. I was on my own and had no peer group to question me if I was doing it right. I only had the mirror to rely on. During this time, I only tried once to come out to a male friend of mine who was my age and was completely rejected. So back into the closet I went. The only relief I had that there was anyone remotely similar to me was another young male friend of mine who sued to dress in his mother's clothes. However, before our explorations moved ahead too far, he ended up moving a couple states away and I was alone again.

Much later in life did the challenges begin to disappear and the opportunities began to become very relevant in my life. The days were upon me when the term "transgender" was becoming widely used and more importantly I could apply the word to myself. In addition, my trips into the world became less and less anticipation and more and more realization. Step by step I was learning who the real me was and she felt so natural. 

I was able to keep my thirst for change up and kept finding ways to meet new people (primarily women) who accepted me for the trans woman I was and with them at least, they had never met and had no knowledge of my old male person at all. Challenges became fewer and fewer until it was time for me to consider taking the step and starting hormone replacement therapy or HRT. The changes in my gender hormones provided me with opportunities I had only previously dreamed of. As my skin softened and my hair grew, I was able to present a more natural version of myself to the public. 

Now I look at all my gender challenges as opportunities to grow and do better in life. I ended up living my dream and succeeding in experiencing both sides of the binary gender border. Not always fun but always satisfying. A place I never thought I never could achieve.  

Staying in Your Own Lane

 

Image from UnSplash

Staying in each others own lane has been increasingly difficult for the transgender community. 

Much of our existence changed under the four year rule of a certain former president who brought out hate in our country. All of a sudden, more and more people became less reserved about changing lanes and invading the LGBT world. Recently I have a close friend whose world was invaded by gender bigots crashing her world. It happened at a relatively upscale casual dining restaurant very close to where my wife Liz and I live and I felt so bad for my friend. 

To make a long and personal experience short, her and her wife's dinners were ruined by other patrons who referred to her as a "Fa--ot" and worse, such as religious slurs. In our experience in the venue, I was laughed at once by a server but that was about it. Even then, we felt bad enough about it to never go back. Plus, that was years ago and people and times have changed. So many think it is acceptable to hurt others with their feelings. So now, it could have been so much worse for me. 

I have said or written it many times how fortunate I am to have Liz with me most of the time when I interact with the public. She is approximately the same height as I am and opens many gender doors for me and others have a tendency to stay in their own lanes. An example happened a couple days ago when Liz went to one of her pre surgical appointments. As always, I didn't have any issues in the doctors offices and especially when we went to a nearby coffee shop to order a cup of caffeine and a breakfast sandwich. The coffee shop was very near one of the  local major university campuses, so the extreme majority of the patrons were college students who certainly had no gender issues other than their own.

In other words, all the people I encountered had no reason to leave their own lane and enter mine and I was free to enjoy my own transgender life. 

For all of you who are attempting to live as your authentic gender selves, I hope people stay out of your lane and you can enjoy your life. I know I am preaching to the choir but you deserve a stable and pleasant gender existence. My blog gently weeps for all of you locked in your dark closets or are just out in the world trying to stay in your own lane. I know my basics of being out in the world is easy, be nice to everyone I can and tip well when I need to. I also benefit on occasion from being easily remembered because of how well I present as a transwoman or don't. 

Either way, I am sadly waiting for the day when a gender bigot decides to veer out of their lane and into my own. 

Always on Stage

Image from
the Jessie
Hart Archives

Very early on I learned when I entered the world as a novice cross dresser, I was always on stage. 

More precisely, not only were men judging me, I also needed to worry about other women. Even more so than men as it turned out. As women in particular had the tendency to be more picky than anyone else because they had been through the process of appearing in public. Women know all of the intricacies of fashion and makeup. Even if they decide to follow the rules or not. At the least, genetic or cis-women don't have to follow the rules when they go out in public. 

How this all translates to transgender women is, we all have to try harder than the average woman just to get by in the world. Not only do we have to blend in with the women of the world in general, we have to do it better. My biggest mistake was when I began to transition, I was still mainly interested to pleasing men which eventually led me to try to dress sexy. Which eventually turned out to be trashy for me. The entire process for me led to me creating too much negative attention that resulted in embarrassing situations. I was trying to fit my testosterone poisoned male body into teen girl fashions, which in no way worked. 

Finally I learned the hard way to blend in but with an edge. By an edge I mean I still had to work hard on my feminine image. I needed to out do other women but not look like I was trying. To work towards accomplishing my task, I had to perfect an understated fashion look. What were other women wearing and how could I come close. Not to mention the makeup I chose for where I was going. 

Since I was always on stage, I became used to it. I became secure enough not to retreat when I was approached mainly by other cis-women. I kept my cool and was able to learn from them. How did they handle the world around them. Specifically their interaction with other men. It turned out, for whatever reason, I never was able to have much interaction with men to worry about. As I said, women were a different matter. Other women often were able to start a conversation with me by complementing me on an accessory such as my ear-rings. probably because most were just curious why I wanted to be in their feminine world. Through it all, I found overall acceptance and was able to slowly perfect my on stage presence. So much so, I began to feel natural doing it.

Feeling natural soon became a primary goal for me. As my old unwanted male self began to slip away, I felt better and better about myself. 

Even though being on stage was very un-nerving for me in the beginning, I became used to it as a normal way of life for all women in the world. Both men and other women were always looking at me. Once I got used to it, life became so much easier to survive as a transgender woman in the world.