Gender Boxes

Image from the Jessie
Hart Archives.

When I was very young, my parents did what so many others do. They constructed a gender box and forced me into it.

As I grew up, I had no choice. I was a boy and was expected to do boy things. Even to the point of receiving gifts on Christmas I did not really want. My primary example came one year when I secretly wanted a doll or kitchen set and I received a BB Gun instead. I was the opposite from the "Ralphie" character in the "Christmas Story" movie. For you that don't know, Ralphie wanted a BB Gun in the movie in the worst way.

 As I grew and began to gain confidence in cross dressing as a girl, my gender box became smaller and smaller.  On most days, it was a struggle to just exist in the world as I knew it. The worst part about it was I never had a choice. It was like I was a round peg being driven into a square hole and being told to like it. I didn't like it and my struggles led to a worsening of my gender dysphoria and mental health. Perhaps the worst part about my situation in those days was I had no one to talk to about it and knew no one with similar gender issues. I was so alone in my little gender box.

As I struggled forward in life, I discovered there were others who were in their own gender boxes and struggling with similar problems also. I like to refer to those days as my "Virginia Prince" and "Transvestia Magazine" days. First I could not believe there were so many other cross dressers in the world and they even had a regular publication I could subscribe to. Looking back, I think "Transvestia" came every two months and I could not wait until I received my new issue. Just reading and gazing at all the other pretty transvestites in the issue made living in my box a bit more bearable. Especially when I learned there were regular "socials or mixers" being held in a location I could actually drive to. I was dazzled when I went to my first mixer and saw all the different people who attended. All the way from weekend cross dressers to transsexuals' heading for gender surgeries. 

Even seeing all those different people in their own little boxes did not help me with mine. Deep down I knew I still didn't fit in with most of the cross dressers I met because I was way more serious and certainly not with the transsexuals because I wasn't serious enough. So I remained in my little box, mainly trapped until the transgender term made it's way into the mainstream consciousness in Ohio. Once I heard or saw transgender, I knew it described me better than anything I had ever seen. Finally, I could take a big marker and write proudly transgender on my box.

From there, it was a matter of connecting the dots and removing the box altogether from my existence. Of course, learning to live a new life as a new gender was a major process and not one which was to be taken lightly. To make matters worse, sometimes I tried to jump into new gender boxes and missed my step and had to retreat to try again. Even still, life had taught me by this time, nothing was going to be easy when it came to escaping being pounded into the square hole I was in but when I did, I could be happy. 

I was fortunate in that I lived long enough to escape my gender box and enjoy a new world as a transgender woman free from many worries I used to have. The process was difficult but worth it.  

Afraid to Try?

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

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

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

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

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

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

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

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

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

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

Transgender. Complex or Simple

Is the art of being transgender very complex or simple? It depends on where you are in your gender transition cycle.

Anyway you cut it, femininization is a difficult process and I assume the same is true for transgender men seeking to enter a male world. In my past, I have had conversations with a trans man friend of mine about the trials and tribulations of using the men's room. The process seemed different to me because I had always taken for granted using the men's room and ignoring everyone else in it. I experienced a much different world full of complexity when I started to use women's room. Just making sure I looked another woman in the eye was a challenge, not to mention everything else I needed to remember to survive. 

Of course the biggest complexity was fashion, hair and makeup. Since we transgender women don't have the luxury of growing up feminine, we have a ton of catching up to do. It is often more painful than fun but is something we just have to if we want to ever make it to the simplicity side of our lives. In addition, the complexity of living trans comes full circle when it comes to our emotions. Then emotions lead to our overall mental health, so it has a very deep relationship with our everyday lives. If we are fortunate, we settle into and come to an uneasy acceptance of being our authentic gender selves is the goal. 

None of the conquering of the transgender complexities came easy for me. I needed to work my way through dressing as a teenaged girl in my mind all the way to being able to present to blend in the world successfully. I needed a whole new attention to detail if I was ever going to achieve my lifetime dream of being a fulltime woman, trans or not. It took awhile but I slowly adjusted my life to a much simpler mode which included being feminine. Fashion and makeup became second nature to me as well as the difficult attempts of dealing with the public which meant mainly with other women. 

There were so many serious facets of my everyday such as being to deal with such as what my sexuality was going to be. After all, since I was living as a woman, would I be expected to have sex with men. Since I had never had sex with men, I had no idea of what to expect. Would I have any pleasure, or would I have been doing it just for my own validation. Thankfully, I did not ever have to explore the new frontiers of sex as I found I was still attracted to women and my lesbian women friends taught me it was fine to be so. So the sexuality of my life didn't change and stayed very simple.

Life is complex enough on it's own without adding in the complexities of being transgender, so we face the ups and downs of following our paths. We somehow find we are carrying pocket knives to solve a problem when all I needed was a set of pliers. It was all part of the simplification process. All along I knew women live a more complex lives than men but adjusting our existences to fit was the challenge. Ultimately, I needed to accept the challenge to save my own life. On occasion, the complexities of learning a new gender world in my femininization process became too much and I needed to try to fall back and take a break. However, breaks were short because the more I learned about being a woman, the more I wanted to learn which was aided to a large degree from finally beginning gender affirming hormones. The new hormones simplified my life even further by aligning my inner and outer selves. 

Suffering through all the complexities of transitioning genders turned out to be so worth it for me. The long journey I took led me to a much simpler world I wish I had be able to know years ago.

Dsyphoria is Never Pretty

Image from Jen Theodore on UnSplash.

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

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

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

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

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

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

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

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

Flashing a Trans Girl

From the Archives. Club Diversity
Columbus, Ohio.

Before you think I am preparing to write a post about me "flashing" another person. No my skirt was not too short or anything else on that occasion. I was wearing my typical fall fashion, boots, jeans and sweater. 

In truth and as boring as it may seem, the only person  who was flashed was me and I don't think anyone else noticed. At least, I hoped not. As it was, my flash occurred just after I increased my dosage of gender affirming hormones. On the evening in question, I was out doing what I normally did, trying to enjoy myself with a drink at one of the venues I regularly went to. 

Suddenly out of the clear blue sky, I felt my face flush and I felt as if I was internally combusting. As I attempted to slyly look at the patrons around me, I was surprised and please to note, no one was rushing towards me with a coat or blanket wanting to put out the flames. Then, as quickly as it came on, my first hot flash as a transgender woman was over and I went back to my drink. I can not say the whole experience was as unpleasant as much as it was unexpected. Up to that point, my gender affirming hormones had ushered me into the second puberty of my life...a feminine one. 

While I could not go back and totally erase all the unwanted benefits of my first puberty which I called testosterone poisoning, my new HRT could help me into a new world. As my breasts and hair grew, my skin softened, along with my facial contours. Not having to wear wigs anymore as well as using less makeup helped my feminization in the public's eye as well as giving me a new found confidence. What I missed the most was having anyone to talk to about my second puberty. When I did bring up the facets of changes I was going through, my female friends just said welcome to their world. Little did they know how long and how much I wanted to be in their world. 

Up to the point of my flash, I had never cried in my life, even during the passing of both of my parents. The best way to describe the new me who could cry was when my testosterone was driven down, the hard edges were taken off my life. All of a sudden, my first good cry occurred one evening when a thunderstorm rolled through my Ohio town and I quietly mourned the loss of my male self. I took no real pity and for the first time, I was able to understand the difference between a good cry and a bad one.

As you can imagine, I was elated with the results of my second puberty in life which did not occur until I was in my sixties. Even though, if I had it all to do over again and transition earlier, I would not have wanted to miss out on the times of accomplishment and fun I had carved out as my old male self. He had taken me a long way in life on a basically successful journey which gave me highlights of having a daughter who supports me to this day, all the way to living with wives/women who helped me unknowingly be a better transgender woman. 

In a nutshell, very few humans have the opportunity to go back and try again. By going through a second puberty and flashing myself, I had the rare chance to not screw it up and be a better person. While I consider my hot flash learning experience as one of the top moments in my life, I also consider the process part of my passage into my unique womanhood. Not unlike having a mammogram. I am just glad, no one else noticed I was on fire one minute and reaching for my coat the second because my thermostat was broken and I was freezing. All part of my second puberty.

See, I told you this post wasn't going to be part of a sensual flash in anyway. Sorry! 

Mansplaining a Trans Girl

Woman being 
mansplained by Al Eimes
on Unsplash .

First, mansplaining to me is a highly insulting way to communicate with women and one I tried my best not to do before I transitioned into the world of a transgender woman. 

In fact I think I went out of the way to not mansplain anything to the women I worked and lived around. I hope now it wasn't noticeable and I was coming off as dismissal. Regardless, I did my best until I was admitted behind the gender curtain and was able to see how the female half lived. 

The problem was, I took so many years to get to the point of being allowed to look behind the curtain and play in the girl's sandbox. So I never quite understood what the mansplaining fuss was all about, until it slapped me one night in a regular venue I was accepted in. What happened was somehow I became part of a small group of men discussing a topic I knew a lot about, like sports. I was still new to the system and tried to interject my thoughts into the conversation. Just as I would have as my male self. To my surprise, I was rudely ignored by the men and I quickly left and went on my way. The whole process was another of my life changing moments when I was transitioning. 

I didn't know what I was expecting since I had seen mansplaining all my life from other men around me when they interacted with women. Why would I be any different? Well, I wasn't and the better my presentation as a transgender woman became, the more I was talked down to. It was like I had lost most of my intelligence and all my life time experiences in addition to other male privileges. 

Quickly I learned to play the game of being a dumb blond, which I was most of the time back in those days. A prime example came one night when my car broke down and I had to call a tow truck. As luck would have it, a well meaning policeman showed up to help and between the driver and the cop figured out the best route to get my car home without even asking me. I was infuriated until the whole evening declined even farther when the tow driver started to explain to me how his wrecker worked. on the ride back Finally, I relaxed and started to ask him questions about what his wife packed him for dinner and why were wheels round. (Just kidding.) But I tried to make the questions of my status as a woman for him which was obviously very low. 

Maybe I should have been happy I presented so well that I lost a main part of myself forever. I learned how women are really treated and prepared myself for other gender lessons. The main one I write about often is the loss of personal security I witnessed up close and personal when I transitioned. I learned to park in the most well lit and safest places I could with the shortest walk to wherever I was going, to name one important point. For the first time in my life, I was the prey when I was out in the public's eye and it was quite the change.

Slowly but surely on the rare occasions I needed to communicate with a man, I learned to draw from my personal experiences and understand where he was coming from. I waited for him to come to me and interject my ideas when I could as a transgender woman. By doing so, I was able to build my confidence back up in public. 

Today when I am mansplained, I take it with a grain of salt because I know there are plenty of women who reverse the process with their communication with men. I remember several nights when I was fine with talking to the woman in a couple I didn't know and having it all change in a flash when he started to show any interest at all in me. There was no womansplaining going on as I instantly knew where I stood. It also never took me long to understand all the non-verbal cues women use to signal each other. 

 It is one of the reasons both binary genders have such a difficult time of communicating. Upper level understanding of the genders is one of the rare benefits of being transgender and should be embraced. When you can do it, you truly have the chance to advance as a human. 

On the Transgender Precipice

 

Image from Wira Dyatmika on
UnSplash.

As I followed a winding, difficult path to my dream of living as a fulltime transgender woman, I took years to climb the gender mountain.

Just one of the problems was  I was afraid of heights. The higher I climbed the rarer the air became because I had never been in all the situations I encountered. As I entered the world as a trans woman, there were so many situations I never expected to happen. I knew women led multi layered lives but not to the extent I encountered. Initially I thought if I had conquered all the fashion, hair and makeup basics, I had it made in the world. Needless to say, I was wrong. 

Even though my male self contributed to me feeling petrified as I climbed, I kept going. As I decided to leave the male gay venues I was going to and try lesbian and straight bars, I really needed to climb to a new level to survive. When I reached a new level, I paused to look around and see what I had accomplished if anything. What I did accomplish was a degree of acceptance from the venues I went to. Except for one evening when three guys kept playing "Dude Looks Like a Lady" on the jukebox over and over again, I begrudgingly held my spot and became an accepted regular in several places. As I did, my view of the world as a transgender woman became clearer and clearer. My gender dysphoric fog was clearing and increasingly all I could see was a future life living as a woman. 

At the same time, I was still a regular at the diverse mixers in Columbus, Ohio where I met a total range of people from cross dressers to transsexual women who were headed for gender realignment surgery or a sex change as it was known back then. By meeting and learning from all these people, I was able to chart my own path to my transgender precipice. 

The two main things I remember are how desperate I was for information on my gender issues and how scared I was of receiving an answer. Was my therapist right and I could do nothing about my feminine desires? If so, I had reached a precipice in my life and I needed to make a decision which would change my life forever. Of course my spoiler alert is, from my gender view, I could see a wonderful if not difficult future ahead as a trans woman. What happened was, as I built a new circle of women friends who never knew me as my past male self, I kept pushing and pushing myself to the edge of my transgender precipice until I fell down the cliff. 

Unknowingly, for the most part, I had set myself up for a soft gender landing. I gave away the remainder of my male clothes and set out to quit climbing and live a new life. What a relief it was to stop expending all the energy I was using to live two gender lives. The process exhausted me and ruined my fragile mental health. My friends helped me through this difficult time of my life more than I can ever say.

With my fears of gender heights behind me, I met my wife Liz and she helped me seal the deal and live my life as a transgender woman. That was fourteen years ago and we have been happy ever since. I don't think I could have ever envisioned I would meet up and marry another woman in my long life but I did. I guess the fog on my mountain was hiding my future.  

Transgender Reconnections

 

Image from the
Jessie Hart
Archives

As I followed the path to a transgender transition, I made several important reconnections. 

Little did I know or realize how many twists and turns I would take before I found my truth. Most importantly I needed to realize I was not a man cross dressing as a woman, I was the reverse. A woman trying to make it as a cross dressed man in life. Because of that, nothing seemed to quite fit in my life as I struggled to survive in an unwanted male world. As I attempted to outrun all my problems,  I drank alcohol to excess as well as moved around and changed jobs way too much. I was always running, searching for my transgender reconnections. Sadly, I searched for nearly a half a century before I was able to have any success and connect with my authentic gender self.

During all those years, I was teased with success as I left my cross dressing mirror and slowly entered the world as a novice transgender woman. Along the way, I made all the mistakes I could think of plus some I could not have imagined happening. In my haste to reach the conclusion to my reconnection, I needed to first discover what it was. Through it all, my inner female was screaming at me for more and more attention but my male self did his best to play all his cards and hang on. The game they were playing wrecked havoc with my mental health and I sought out therapy for help. As with anything else, therapy is what you put into it and I went through several very good therapists as well as a couple not so good ones. Then there was the problem of me listening to what they had to say to start with because my male self was telling me therapy was just a waste of time and money. On the other hand, my female self saw the benefits, especially if the therapy process was slowly opening her world at all. 

Sometimes too, reconnections were tantalizingly close. There were so many days or nights when I could relax and enjoy a glimpse of what a life as a transgender woman could be like. The more reconnections with a feminine world I could make, the more natural and better I felt. Probably, most importantly, all of the gender progress I was making was because I believed in myself and my confidence was building. I had escaped the basic confines of the wardrobe and makeup challenges and made it to the one on one communications I was suddenly faced with as a trans woman. It was during this point of my transgender reconnection process I learned the most. Mainly because, I was relaxing and letting my long hidden female self take over. It turns out all those years of having to quietly sit back and watch my male self struggle enabled her to be a better person when she got the chance. 

When I reconnected with my female self, I was able to be a full person again and I knew one of my therapists said it right when she told me there was nothing either of us could go about me wanting to be a woman. If I had followed her advice and set out to discover what my second wife had told me all along, I would have taken the time and really looked into what a women's world was all about. Other than the outward appearances of fashion and makeup. It was the biggest reconnection I couldn't make until I had earned it by actually adopting and living a life as a trans woman. Even to the point of beginning HRT or gender affirming hormones. 

In many ways, the new hormones were the final piece of the puzzle in reconnecting my transgender self to the world. Physically and emotionally I was ready to face the world as a united human being.  

Down the Transgender Rabbit Hole

 

Image from Benoit Baumatin on UnSplash.

Long ago, I sought out a rabbit hole I found I did not want to escape.

In the beginning, I did not go deep into the hole so I could supposedly easily escape if I wanted to. The farther I went, the harder it was to escape even I wanted to. What happened was gender euphoria set in and the entire cross dressing experience became increasingly pleasurable as well as feeling incredibly natural. The problem I faced was how to cover the entrance to my rabbit hole so no one else in my family could discover it. Very early it was easy when I could attempt to borrow select clothes from my Mom's closet which ended when I became too big to wear them. Then I had to rely on my own limited financial resources to buy fashion and makeup accessories. 

For awhile, the pressure to go away and cross dress became so intense I needed to find a spot away from the house to establish another private rabbit hole. I found the best spot in a quiet wooded area next to our rural home. I was able to protect my secret collection of feminine clothes in plastic bags and hope they would be protected enough as well as not be discovered. I did well, because they never were and I was provided another place to go to cross dress. If even for a short period of time. 

The better I became at perfecting the "art" of fashion and makeup, the more I wanted to leave my novice transgender rabbit hole and look around at the world. At first, the world proved to be a very difficult place to be. After too many public failures I was sent scurrying back to my rabbit hole to seek comfort and try to figure out what all I was doing wrong with my feminine presentation. The entire feminization process for me proved to be a difficult one as my entrenched male self fought for his dominance and kept on trying to cover up my rabbit hole with ill advised purges. Very quickly he found out the gender purges I was going through were a complete waste of time and money. 

Once I reached the middle portion of my life, my rabbit hole needed to be expanded from a crossdresser rabbit hole into one large enough to contain a full fledged transgender woman. I needed room for more wigs, shoes and women's essentials to survive in the world. As I was entering a new exciting yet scary world without my white male privilege, the sunlight outside my rabbit hole was at times blinding. Even more so when the world all of a sudden expected me to communicate with them when at the least, I had to order face to face with servers or bar staff trying to take my order. What was a novice trans woman to do? What I attempted to do was make the best of a potential destructive situation. Very early in the game, I came to the conclusion the world knew I was transgender for the most part and those who cared, could just get over it because I was just living my truth.

Of course, once I was able to leave my rabbit hole in my past and live, I had no desire to go back to it's dark confines. Each time I was successful in the feminine world, my male self lost more and more of any control he had left. 

The writing was on the rabbit hole wall when I started gender affirming hormones. I knew I had made the correct decision when my body and mind took to the new hormones so naturally. In addition to all the bodily changes which took place, I cherished the new emotions I felt. Being able to cry for the first time in my life was quite the experience. 

Perhaps, most importantly, was when I discovered the lack of predators I really had when I left my rabbit hole. Of course dealing with the occasional man was a problem but with my circle of lesbian women friends, not so much as they taught me true validation as a person. Once I learned to validate myself, I was freed from my old male rabbit hole for good and jumped into the sunlight.