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.  

A Toxic Male?

Image from Jurien Huggins
on UnSplash.

As I transitioned from a male to a feminine life, I often looked back at my life as a guy to determine if indeed I was a toxic male in any way. 

Of course I immediately mentally recoiled when I thought I could be toxic towards women in any way. After all I had spent a considerable amount of time worshipping the women around me, wondering how it would be to experience just for an instance being a girl. How come I couldn't wear the pretty clothes and be the gender who was so admired by the other. The problem with me was, I went way past just admiring a girl sexually, all the way to wanting to be a girl physically.  

Did any of it make me a toxic male? No, I don't think it did. In fact, I think the opposite happened as I put women up on some sort of an impossible pedestal. By doing so, and adding the fact I was extremely shy, I never had much of a chance to interact with girls or women growing up at all. From my perspective, the feminine grass always looked so much greener. 

Since I was forced into the male camp, I needed to learn to exist and had to put up with sexist comments directed towards women from many of the guys I grew up with all the way to adult hood. Mixed in too were the bullies I needed to somehow co-exist with. I learned to bluster my way around the bullies without jeopardizing my inner transgender self to ridicule or worse. In order to do so, I participated in as many of the male activities of the day as I could such as sports and cars. It worked and I was left alone for the most part and I even dated a few girls along the way. Since it is prom season around here, I am always reminded of the two proms I went to in high school. Even though I was the perfect gentleman at the proms, I wonder if my dates thought perhaps I was a little too timid and took it personally. I will never know because one of my dates and first serious girlfriend before college later in life committed suicide years later when her husband left her. What a shame. 

As I started college and started to date more regularly, I really began to see the results of toxic males around me. Especially in the fraternity setting I was briefly in. Certain fraternities were expected to co-mingle and party with certain women and sororities only where I went to college. I found out very quickly I did not fit in with the frats social system. Which was a forerunner to me not fitting in with the strict layers I encountered at the first cross dresser - transvestite mixers I went to. I felt so out of place and the only toxic people I saw were the "A" listers who were doing their best mean girls high school impressions. Maybe their male toxicity was bleeding through. 

I completely learned how not to be a toxic male when I settled into a career in the restaurant business. Along the way, as I progressed into higher management positions, I needed to coexist increasingly with women. Both crew members and managers. I learned quickly female crew members had the tendency to build cliques (not teams like the men) to be successful and the women managers I knew had to be tough but fair to survive. I on the other hand needed to be on their side when it came to battling any toxic males at all. Looking back, I think male toxicity was the prime reason for letting someone go. Which included sexual harassment which is a topic for another blog post.

My only regret was I wasn't a more vocal advocate for women my entire life as a man. I could have certainly spoken up when another guy joked about a woman. My only excuse is I was so intent on hiding my interior feminine self, I was afraid to do more. Transgender women and trans men speak of the importance of allies speaking up for us. I feel the same way about standing up for women before I transitioned. 

One Gender Size does Not fit All

Image from Grae Phillips 
on Geraldo television show.

 If the truth be known, all the way back when I was a kid struggling to understand what gender I was on any given day, I would have been known as gender fluid. 

Of course, gender fluid was a term which hadn't been invented yet. Anyone who was interested in cross dressing was branded as being a transvestite and even worse labeled as being mentally ill. In the middle of my gender vacuum, even I knew well enough I was not mentally ill just because I wanted to wear makeup and dresses. I hid my desires and hoped for the best, which mostly came when I was left alone to cross dress and admire myself in the full length hallway mirror at home. Most of all, I was trapped and could do nothing about it. Keep in mind, all of this was happening in the information "dark ages" before the internet and social media. The gender underground I was interested in came mainly from the pages of Transvestia Magazine and Virginia Prince. Even I knew the pages of the "National Enquirer" and other predecessors of Faux News who sensationalized cross dressers were not to be trusted.

Then came the barrage of so called reality television talk shows including, Donahue, Springer and Raphael. All of whom seemed to be pushing the theme of cross dressing husbands Except for the impossibly beautiful and talented "Grae Phillips" who put everyone else to shame. All of these shows probably did little or no good for my gender dysphoria except for publicizing the fact there were cross dressers of transvestites of all kinds at all. All I knew was I desperately tried to watch or tape every show I knew was coming up from my "TV Guide". My wife was trying to tape her soaps and I was trying to tape my talk shows and both kept us busy. Even though I still had to watch my shows in private attempting to learn anything I could about the outside world.

I did learn once again. my gender size was unique and did not fit all. In fact, I still felt out of place when I started to attend my first cross dresser - transvestite mixers here in my native Ohio. I discovered there were so many different levels of participation from transsexuals headed for gender surgeries down to the weekend cross dressing hobbyists.  For some reason, I was not part of either group and once again my gender size was not fitting in. The problem was, all of this happened before the transgender terminology was introduced. When it was and I started to have access to my first computer, I was able to research the term which was unknown to me. Suddenly I knew what had been missing my whole life, a gender size which fit me and I set out to discover more about being transgender. For me, it meant being part of a gender description which was somewhere in-between the spaces I had been in previously.

Even though my gender size did not fit all, finally I was able to locate my own niche to thrive in. Life became fulfilling, scary and exciting at the same time. I found out I was fine being who I was all along and it felt so natural. I was home. 

Transgender Lables

 

Hunter Schaefer at the Oscars.

Spoiler alert, this post contains unfortunate stereotypes. 

The subject I am attempting to write about is about what actress Hunter Shafer said recently. I paraphrase but essentially she said she had turned down many transgender acting roles because she did not want to be stereotyped as a transgender actress in the future. She wants to be known as a woman only. 

In the first place, we all should be as fortunate as Shafer is to possess as much passing privilege as she has. I am sure in any situation, no one is saying "Hey! That's a guy," 

Now, that is the easy part of the post. Secondly, does she have any responsibility to the rest of the transgender world to keep the trans part of her name?  No she doesn't but the whole idea of exactly who is a woman was brought up again in the public's eye. In my case, I have always thought achieving the title of woman is a matter of socialization in life. Just being born female doesn't guarantee a person will ever make it into womanhood. The same goes for birthing children. My second wife never gave birth but in itself, that did not make her less of a woman. To be fair, many males never grow into being men either. Often becoming the toxic males we read so much about.

Then, there is the subject of gender surgeries. It used to be, some transsexual women looked down on all of us who did not have any surgeries at all. Viewing any and all transgender women as little more than glorified cross dressers or transvestites. At the time, as I was exploring what I wanted to do with my gender life, I saw no problem with fitting into their stereotype, even though I resented it and thought it was wrong. As the years went by, I resisted giving up all my male privilege I worked so hard to obtain and had no gender related surgeries at all. If it makes me less of a transgender woman in some people's eyes, so be it. I was still able to navigate the world as a feminine person, or, as my trans friend Racquel said I passed out of sheer willpower.

Of course I don't know Hunter Shafer but I respect her opinion to be referred to as only a woman, not as a transgender woman. After all, who would not want the same privilege after waking up in the morning and looking like her? On the other hand, there are zillions of women who don't have the same passing privilege's as she does and Hunter has been able to bring into some sort of focus what being a woman is all about. 

As we all walk our gender journeys, we have to come to our own conclusions concerning womanhood or manhood if you are a trans man. It is certainly more than how we look or what restroom we use. It involves life itself. For the sake of discussion, I hope Hunter Schafer's next acting role is of a so called cis-woman, she has paid her dues. 

Sadly being transgender will always be a weight we all will have to carry throughout our lives no matter how we look or how many surgeries we have undertaken. Personally, I don't need an actress to inspire me to be a woman instead of a transgender woman. I have made the decision for myself. I am just me. Looks don't make a transgender person. Your soul does. 

Climbing Transgender Walls

 

Image from Katherine Hanlon
on UnSplash

Just when I thought I had conquered one obstacle in my gender transition, another obstacle suddenly appeared for me to climb.

The problem I had was I am very afraid of heights and some of the walls were taller than others. For example, makeup was not a big wall since I had so many years at home alone in front of the mirror to practice. By the time I went public, I had perfected most all the makeup ideas I needed. Plus, benefiting completely from having a professional makeover at one of the transvestite/cross dresser mixers I went to. The makeup artist really showed me how to scale the wall which on occasion had made me look like a clown.

At approximately the same time, I was fighting climbing another obstacle called fashion. For years I dressed my feminine self for what my old male self thought was appropriate  The whole process was completely backwards as I should have been trying to present as close as I could to other women of my age so I blended in. Once I scaled the obstacle, my life as a novice transgender woman in public became so much easier. Once my life became easier, I thought I had it made but I was so wrong. What happened was gender doors began to open for me I wasn't really ready for. I found it was much easier for me to move around in society as my feminine self than it was to actually sit down and have a conversation with another woman or man. Communication for me was a huge wall to climb. So much so, I even ended up taking vocal lessons at one point in my life to sound like a woman. 

As I write this post on walls, it occurs to me, I should have added in all the stop signs I went through on my path to living as a fulltime transgender woman. Coming to mind were all the times my male self was screaming stop!!! when his domain was being challenged. All the times, I put my marriage at risk by sneaking out behind my wife's back when she was at work is an example of running a stop sign just to try to climb another gender wall. What I was doing was slowly but surely building a way around the old male obstacles I faced, to build a new life as a transgender woman. At that point, if I had been honest with myself, I would have known my new life felt so natural, it would win out in the end. But, I wasn't honest and boxed myself into what was left of my male life which I had hated so much.

Finally, the world around me changed because of dire situations where family and friends had died leaving me the freedom to climb the final walls out of my gender closet. I came to the point where I had the tools I needed to conquer my fear of existing in public as a trans woman thanks to gender affirming hormones and pure courage to live. 

The walls I kept facing kept declining to a point where I had no choice but to do the right thing for myself and go ahead to live my lifetime dream of living as a woman. Looking back, maybe I should have described all the obstacles or walls I went through were more of a maze. Maybe I should have paid more attention in the scouts or the military to find myself an easier way through. Although, after communicating with all the other transgender women and trans men I do, maybe an easier way just wasn't possible. 

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.

Carry on Baggage

My wife Liz (right) and I with
Brutus Buckeye in the
Ohio State student union...

Those of you who have transitioned genders or those who are seriously considering crossing the gender border need to figure out how much baggage they will take along. If you are into sports at all (which I am) this time of year is fun to me because of all the huge football games being played.

So for me, the amount of baggage to consider was considerable. I wondered if my love of sports would have to take a back burner in my life. Because, back in those days, the choices were basically black and white with very little gray. If you remember, there were really only two groups of individuals you could identify with. Those were transvestites (or cross dressers) and the transsexuals who were headed for genital surgical intervention. Plus, after the realignment surgery, you were expected to exclude your past, move from your home and family and start your life all over.  No room for any baggage from your previous existence. 

Today fortunately is different. Mainly because cis-women of all sorts these days have or are living more diverse lives. The lines between male and female genders have been blurred. 

In my case I found out the easy way how much baggage I could bring with me. When I basically gave up on going to gay venues for any number of reasons such as being overall rejected as a drag queen or hating the music. I found I much preferred going back to the big sports bar venues I used to enjoy as a guy. Ironically, I found I was discriminated to less in the sports bars where I could order a large beer and watch my favorite sports team dressed as a transgender woman. Outside of a few notable exceptions I was able to establish myself as a regular by minding my own business and tipping well. I also found I could use all the help I could get as I researched if I could indeed add sports to my baggage as a trans woman.

On a higher level, I even found I could meet other women who were into sports and become friends I could interact with on a regular basis. Over the years I had a great time with them meeting and arguing sports with our tight little group of women.  

When I learned I could take on the biggest baggage carry on I could imagine, the rest of my life became so much easier. I could concentrate on learning from my women friends who happened to be lesbians all I could concerning my new life as a transgender woman. Especially valuable to me was the fact I was finally able to validate my gender dream. In other words, I didn't did a man to be seen with to validate me anymore. 

As I said, the ability to establish my new life and bring quite a bit of carry on baggage with me made my transition so much easier. Hopefully, you will have the chance to validate your new self also and make friends in the process. I would also be remiss if I didn't mention my wife Liz who took a chance on me when she saw my on line profile. She is the cis woman who told me a decade ago she didn't see any maleness in me and why didn't I throw the rest of my male life away and live full time as a trans woman. Her validation naturally was tremendous.

As with any carry on baggage, you naturally will find items you didn't really need but having the time to live a new life to find out what you can't live without, is important as you move on. 

The Essence of Being Transgender

 

Go Buckeyes! Image from the
Ohio State Union...

It is very difficult to explain to another person why you are a transgender woman or trans man. 

I can only compare it to why a cis-woman just knows she is a feminine person. To just say I was born this way is a huge over simplification. To begin with just being assigned female or male at birth does not necessarily guarantee you will ever make it to being a woman or a man. Many people just don't for whatever reason. Perhaps you have encountered a person or two (or several) in your life who never seemed to grasp the ideals of their supposed gender. In most cases, they became unhappy and unfulfilled people. 

Transgender people have it harder since we were forced into boxes we did not want to be in. Or, the old square peg into the square hole status. First we trans individuals had to figure out what our problem was then try to have an idea what to do about it. In most cases we had to come out fighting to claim our limited space in society.

In many cases we faced other women who pushed back on our transgender essence...even trans women who wanted to say you were not trans enough to be included in their little clubs. These women were not unlike other cis-women (natural born females) who resisted our inclusion into their worlds. These transphobes or TERF's did and can attempt to make life miserable for unsuspecting transgender women. I have never figured out what their true problem was or is. I faced it head on one night at a lesbian Valentine's Day dance Liz and I went to. A lesbian came up to me and rudely asked what my "real" name was and was very nasty before she finally gave up and went her own way.

I have never figured out why other women would not want to be more inclusive of us and broaden their population base. Especially with all the attacks women are facing on all sides in politics and with personal safety. I write often how quickly I learned what could happen when my personal safety male privilege was taken away. I was cornered by a huge man at a party and had to be rescued by my second wife one night and then much later was stopped by two men when I was alone at night outside a gay bar in an a dark, lonely urban setting. I learned quickly never to be alone again in those situations. 

I guess the problem of explaining essence is because it is so vague. It has always been so difficult to tell others I have always known I am transgender simply because I was. I am as much as a woman as anyone else. I just had to take a different path to arrive at my goal of jumping from an unwanted male life to a fulltime feminine one. 

If they don't listen or can't understand, it is their problem. Not mine.

I'm More Trans than You???

 

Image from Alexander Grey
on UnSplash

How can that be? It shouldn't be but it's one of the many dividing points we face in the transgender community.

Plus, with all which has happened recently in our country with bigoted politicians we all need to stick together now as never before.

We also have to consider just how many factors go into considering why anyone would consider such a preposterous thought. It used to be surgeries were one of the dividing points over someone was more transgender than another. Years ago, Connie and I coined the term (probably not original) "Trans Nazi" for those who thought since we had not undergone extensive gender realignment surgeries, somehow we were not allowed to claim the term transgender. 

These days I feel as if the pressure to conform to being more transgender than anyone else is more involved with how you live. In other words, if you claim to be trans and don't live it on a daily basis in the public's eye, are you no more than a dedicated cross dresser. Repeating what I said in yesterday's post, gender doesn't come from what is between the legs, it comes from what is between the ears. Even though for whatever reason, the trans person just can't live everyday as their chosen authentic gender. Along the way, perhaps we have lost the perspective of the common point of what is was which brought us altogether. In the beginning perhaps we felt a need to feel somehow superior to other cross dressers because of appearance. I know I faced a superiority complex from a group of transvestites I referred to as the "A Listers". Sadly their beautiful appearances didn't carry over into their personalities. Most of the "A's" acted similar to the mean cheerleader types in high school. A few I knew did take the extra move to pursue surgeries to supposedly enhance their femininity and the rest I simply lost track of. 

These days I am stuck in some sort of a middle point in the argument of being more transgender than the next person. On one hand, I could put myself up on some sort of a fragile pedestal. On the other, I could feel the rejection from others because even though I live full time as a woman, surrounded by those who only see me as such, on the other hand, for whatever reason I have never undergone any gender surgeries. I am sure more than a few could consider me as no more than a glorified cross dresser. Or, as one reader pointed out so rudely years ago...just another old man on hormones. I found the comment to be humorous and if the truth be known there are very few people who I care what they say anyhow.

As precarious a position most transgender women or men find themselves these days with anti LGBT legislation, there is no time for petty bickering concerning who or who is not better situated to represent our community and should not be so segmented. We need everyone from those deep in the closet to those who have undergone genital realignment surgeries to understand their paths contribute to an important path to guide others. 

Being more transgender than someone else, simply should not exist for the welfare and advancement of us all. 

Re-Connections

 

Image from Priscilla Du Preez on
UnSplash 

Often in life we are capable of living out full circles during our time on earth, if we live that long. 

My lifelong journey to find and live with my authentic feminine gender gave me the opportunity to go full circle several times and then reconnect with myself. My biggest issue was to finally establish myself as a transgender woman. To do accomplish my reconnection,  it seemed I had to live my way through being a cross dresser (on two stages) or a transvestite if you prefer that term. I say cross dressing on two stages because for the longest time I considered myself cross dressing as a woman while I was primarily living as a man. When in truth, I was just doing the opposite, cross dressing as a man when I was primarily a woman inside. 

Along the way, I experienced several confidence building experiences to help me along. Sadly, most all of the character building changes occurred to my male self and it took many years for my inner female to catch up. Examples included my successes in career fields as well as being able to influence how my daughter was being raised. Both came back to aid me later in my gender reconnection but at the time didn't seem so positive. The salary I earned at my jobs helped me to earn enough and accept an early retirement which helped me clear a path to transition. And, as far as my daughter went, later on in life she has gone on to be one of my staunchest gender allies. I don't know how my life would have been without her. 

The problems with re-connections if you have ever done any plumbing work, you have to make sure the connection is secure before you move on. I experienced many problems with my gender transition as I tried to move on. I stubbornly refused to dress my age and to blend in with other women around me when I first tried to leave my closet. The entire process caused me deep grief until I began to learn the basics of getting by when it came to my presentation.  When I finally developed the confidence to try harder to secure my initial connection, it seemed something else would appear and get in the way. It turned out, moving and communicating as a woman presented a much more difficult problem for me than the appearance part.

After a while, when I was extremely self destructive to the point of suicide,  it turned out I was going to live long enough to go full circle with my gender in my life. I was fortunate to find and keep a small group of women friends who helped me secure and adjust to the societal demands I  was going to have to face in my new life as a transgender woman. 

By this time I had gone full circle and put my male past behind me. My re-connections were secure and I had a lot of life to look forward to. 

   

The Gender Buck Stops Here

 

Image from the Jessie
Hart Collection

It took me over fifty years of cross dressing as a woman to decide I had enough and I finally decided to come out full time as a transgender woman.

At that point, I either threw out my old male clothes or donated most of them to a local thrift store which was the demarcation point of when I flipped the script and stopped cross dressing as a man. For awhile it was difficult deciding what I would wear everyday as a trans woman. I knew I desperately wanted to blend in with the other women around me but knew I had to put in considerably more effort than they did to do it. Plus the effects of the hormone replacement therapy I was on was beginning to drastically change my old male appearance. So a change was needed. My skin was softening, along with the lines of my face, so I was beginning to appear quite androgynous. 

With all these changes taking place, I finally had a one on one talking with myself and decided enough was enough. The gender buck stopped there and then. It was time to take advantage of a lifetime of preparation and cross the gender border and live as a transgender woman. All those years of admiring my self in the mirror and attending transvestite mixers in Columbus, Ohio would be put to the test. During the mixers I was able to see and meet many different types of cross dressers all the way to transsexuals to determine just where I fit in. It was about that time when the term "transgender" was being publicized and I immediately thought the term fit me. It turned out it actually did and my life would never be the same again.

When the buck stopped with me and I began to take complete responsibility for my gender questions, my life suddenly became easier. Even though I was still facing questions in the harsh light of the public's eye. I needed to learn being a successful transgender woman took so much more than just taking care of my appearance. Surely appearances were the path to opening doors but what happened after the door was opened became very stressful. How could I handle actually communicating with a man or another woman when I was so new at doing it. Possibly the most frustrating part of the whole communication process was how much it changed with each person I encountered. The process was not unlike playing tennis and waiting for the other person to serve. Finally I began to relax and make the best of a situation I never knew where it was going.

It turned out relaxation was another key to my new ability to exist in the world as a trans woman. I learned for the most part men left me alone and women were just curious as to why I wanted into their world at all. I valued my communication with other women because I was learning so much about playing in the girl's sandbox.  My confidence was high and I thought I had as much business as other women did in the sandbox. From there, I made the most of it. 

It is also important to note, when I determined the gender buck did end with me, there would be no turning back. I became so involved in learning my new feminine life and it felt so natural, I would actually take the gender buck and spend it. 

Deep Gender Frustration

My attempt at formality.
From the Jessie Hart Archives.

One of the first deep seated internal  frustrations I felt with my gender dysphoria was when I first encountered the challenge of attending my junior-senior prom in high school. 

I was very shy and nervous when it came to being around girls of any type. I didn't have any sisters or any girls in the neighborhood I grew up in, so I had no experience. When I made it to the time when my first prom came up in my junior year, I was stuck in a new high school with very few friends period. Especially no female ones. So I had no one to even summon up the courage to invite to the prom. It turned out, the problem was going to take care of itself without much effort on my part. 

What happened was a group or clique of popular girls noticed one of their group did not have a date to the prom. At that point, they reached out to me to find out if I was interested in attending the event. I nervously said yes and the planning began. Little did I know what I was getting into. As the male part of the date (back in those days) I was expected to provide everything from transportation, to dinner to flowers for my date.  My deep problem was I was the one who wanted to wear the fancy gown and be given a corsage then dined and danced with. I was deeply frustrated. The only good parts of the entire night were my parents were proud and probably a little relieved I was finally going out with a girl. On my part I was interested to see how I would finally find out how I would react to a real live date.

As predicted, my first prom did absolutely nothing to relieve any of my deep seated gender frustrations. In many ways, the whole process just made it worse. At  the least at that point I had began the process of learning what dating a girl was all about. In my senior year I actually met and stayed with another girl until I went away to college. The time included another prom in my senior year which I needed to suffer through since once again I wanted to be the girl, not the guy. I hated the tuxedo I had to wear all the way (again) to not being the one in the glitzy dress. The only revenge I ever received came years later, the supper club we went to eat at prom became a large gay venue and I was able to use the same women's room my date used. A small amount of retribution but meaningful none the less.  

When I went way to college, the initial months on campus provided one of the few gender respites I ever experienced from my transgender life. But to make a long story short (as you know) my desires to love everything feminine never went away. In fact, years later my jealousy re-surfaced in a major way. During my years working for a major restaurant chain franchisee, the company threw lavish Christmas parties for the store managers and upper level assistants.  The parties were semi formal  so once again I was thrown in to being downright jealous of the women who would be attending. Several were very attractive and needed to try to negotiate getting in and out of the limousine the company provided  for transportation in the fancy gowns. As the other men admired the women and their attempts to stay modest when they entered and exited the limo, I on the other hand, wanted to be one of the women in the beautiful dresses. 

It wasn't until fairly recently when I came even remotely close to achieving close to the same feeling cis-women feel when they are able to dress up. During recent Christmas's and other banquets I have managed to come up with a semi formal dress up look. It provided me a respite from a little of the gender frustration  I experienced over the years.  I also discovered women all along were aware of their own insecurities of semi formal events. Often the grass is not always greener on the other side of the gender fence. 

Endless Possibilities

 

Image from the 
Jessie Hart
Collection

When I was young, the only vocation I could think I wanted to follow was I wanted to be a woman. 

Somehow along the way, I hoped I would grow out of it. As the years went by, not only did the thoughts of being a woman not go away, they just became stronger.  Initially all of this made me even more frustrated with my life. Possibilities seemed far from endless. I was stuck living an unwanted male life. The only possibility I faced was making my male existence as successful as I could. So I followed traditional male activities and pursuits such as sports and having a successful profession. For years, it seemed I was going backwards towards my dream and/or goal of living as a transgender woman.

Before I did begin to look for my gender possibilities, I needed to learn more completely what the process meant to me. About that time was when the transgender term became known at all. Just having an idea of who I might be gave me a starting point on my gender development. The more I explored getting out of my closet and into the world, happily the possibility of opening more doors began to evolve. I started with the basics such as doing a portion of the grocery shopping all the way to going shopping for Christmas gifts. All as my feminine self. The more I explored, the more possibilities opened up to me. For once in my life, I was finding a way to feel more natural and complete. Deep down I knew I was right when I lived as my authentic feminine self.

All of sudden, I was starting to think I actually could follow the biggest dream of mine to someday live fulltime as a transgender woman. In other words, my sun, moon and gender stars were beginning to come together. Before I knew it, I was going to previously off-limits venues and thriving.  Issues such as one on one communications with strangers began to fade away when I learned living as a transgender woman meant so much more than just looking like one in the mirror. I can't stress enough (for me) learning the many and various layers cis-women live through. I called the process being allowed to play in the girl's sandbox. I was helped along when I was invited to "girls night out" parties as well as other gender specific activities When I pulled the feminine curtain back. I really progressed with the new knowledge I learned. 

If you have ever experienced being tantalizingly close to a lifetime goal and not achieving it, that is where I was. I could see what my life as a woman would be like but taking the final step would not be easy and was all so terrifying. My male self just didn't want to give up all the white male privileges  he had worked all those years to earn. At the time I viewed the process as similar to sliding down a slippery slope towards a steep cliff. When and if I fell off the cliff, I didn't know if I could ever return. Well, I never was able to return to my old male self and I have a series of friends to thank for making my landing as soft as possible.

Included in my circle of friends was my own inner feminine soul. I had no idea once I turned my life over to her, she knew exactly what to do. She had been waiting all those years for her endless possibilities to materialize.  

Finding New Friends

 

Image from Dave Goudreau
on UnSplash

In an extension of yesterday's post, I promised to write another post explaining how I found a complete new circle of close friends as a transgender woman.

As it turned out, going out to be alone resulted in me being embraced by several other cis women I met in person in the venues I became a regular in. The first came when I was approached by a bar tender who was always very kind to me and treated me with respect. One night she asked me if I would consider meeting her lesbian mother for a drink. Without hesitation I said yes  and a friendship was formed which continues to this day. Her name is Kim and she is the person who included me in a small group of family and friends who went one night to a NFL Monday Night Football game. Of course during that time, I was still fairly new to going out in the world as a transgender woman and this would be a major undertaking.  Attempting to blend in and enjoy an entire pro-football game with my ill fitting wig was going to be a challenge and I was terrified I would be spotted and harassed by another drunk fan. But I wasn't and the game went off without any big problems. In fact, the only big one was my team was defeated and I had to accept it as the new woman I was. The whole experience will go down as one of the major coming out points of my gender journey. Proving once again to me I was much more than a casual cross dresser or transvestite and quite possibly learn to live full time as a transgender woman. Kim's kindness will forever be appreciated.

The second of three lesbian cis women I met was Nikki. In the years that have gone by, she has been off social media and I have lost contact with her. We met (similar to Kim) in a venue I was a regular in. One night when I was doing my usual being alone, Nikki came in to pick up a to-go food order. While she was there she glanced down the bar at me and sent a message down to me. Sadly, I don't remember now what the message said but we ended up meeting and drinking together for several years afterward. Usually, Kim, Nikki and I would meet somewhere and watch sports or just talk. Plus, Nikki is the person who got me involved in going to Lesbian mixers with her and Kim. Since I had support, usually the mixers were a good time and as always I learned a lot.  One night I was even asked to be a "wing person" and was asked to summon my courage and ask another woman to respond to Nikki's desire to know her. I thought, I only live once, so why not.

The third woman I met came from an on-line dating site. Of course I needed to work my way through tons of rejections and trashy people before I stumbled upon a big winner. To expand my experience and the possibility of finding someone I always told the truth about being transgender, To change it all up, I would sometimes go on the women seeking women page and on occasion reverse it to men. One day I received a response from a nearby person who lived in Cincinnati, Ohio. This all happened nearly twelve years ago and the woman who contacted me was my current wife Liz. To this day, she is very open to anyone who is interested that she picked me up because I had "sad eyes." From there we started to write each other after work daily until I had enough courage for her to hear my voice over the phone. Finally we decided to meet in person when I asked her out to a drag show which was happening at a venue nearly halfway between where we both lived. To make a long story short, we enjoyed ourselves and have been together ever since. Plus we were just married last October. 

Along the way, I felt my success in being able to locate and keep the relationships I did came from me going full circle in life. My good times made up for the extreme low points I felt when I was so lonely and confused due to my gender dysphoria. To this day, I am never shy of giving the new friends I found the credit they deserve for helping me with my intense MtF gender transition.

 

I Failed my Gender Assignment

Vintage Edition of
Transvestia Magazine

 My initial gender assignment was very simple. I was born a boy, now be one. The problem quickly became I was failing the assignment and I just didn't want to be the gender which was assigned to me. 

Instead of following all of the basic rules I was given about being male, sooner more than later I began to realize something was wrong and essentially I had no choice but to follow the rules. As they were presented to me. My parents were members of the "greatest generation" who survived a great economic depression and a world war.  They were well versed in taking what was presented to them and making the best of it. The same was expected from me. I had no way out when it came to my gender issues. I was alone with my problems. 

In response I did the best I could. I participated in sports and did my best to present myself as a so called "normal" boy. While I was doing it, I also was doing my best to use my limited funds to accumulate a small collection of makeup and feminine clothes which freed me up from helping myself to my Mom's belongings. Of course at the time I was outgrowing my Mom in all the size categories, so it was good to finally go out on my own when I could. I guess you could say, this was the first time I actually passed my gender assignment, in my chosen dream world of being feminine. 

At the same time, I learned the male so called attributes of being emotionally distant and keeping my feelings bottled up. I would carry those with me until I was able to more completely transition my gender.  I was able to not fail this part of my gender exam. In many ways, in order to receive a pass or fail grade in either gender, I needed to wait for the world to catch up to me. Since I was a part of the pre-internet generation, information of any kind was very limited. In fact, I was completely isolated in my closet until I learned of "Virginia Prince" and her "Transvestia" publication. I was so relieved when I found I wasn't alone in the world and there were other so called transvestites in the world and some even met for mixers in cities close enough for me to attend. 

Once I did attend, my path to a different gender assignment became clearer. I was able to interact with others dealing with the same gender issues I was dealing with  and come up with a new plan for my life. It was about this time the transgender word became popular and I strongly believed it fit me. It was becoming increasingly evident I needed to take another gender exam. I was failing my initial male assignment and wanted so badly to attempt taking the new exciting feminine assignment or exam. Before I was able to, it turned out I had a lot more studying to do. Being a woman was a lot more than just looking like one. I can compare the process to higher education. Just being able to blend and mix in with the public as a transgender woman was similar to having an undergraduate degree. Then being able to communicate with other women one on one was the equivalent to obtaining a masters degree and so on.

Finally I accepted the fact I had failed my male assignment completely. No matter how hard I tried to succeed as a man, the whole process seemed to be an empty pursuit. Even though I was relatively successful in obtaining male privilege, I found I didn't want it. On the other hand, attempting to go as far as I could with a feminine gender assignment proved to be the answer to all my gender issues. Why? Primarily because the whole process felt so natural to me.

   

Living the Trans Dream

Summer in Ohio
from the Jessie Hart
Collection

Every so often I have the chance to sit back and wonder how I ever made it to the place in life I have arrived at now. I spent so many years living a mostly frustrated male life, wondering how it would be to permanently cross over the gender frontier and live life full time as a transgender woman. For the longest time, I thought I would never make it to the point where I could ever live my dream. 

In the beginning and during several years following, I went down the same rabbit holes as other cross dressers or transvestites I knew. The same old male egos showed through our fancy feminine clothes to reveal we didn't know much about being women at all. Just doing our best to look like one.  Finally I came to the point of knowing I wanted to discover more in depth just what I would be facing if indeed I decided to try to complete a MtF gender transition. Before I knew it, years and life had slipped away and destiny opened a few doors for me which enabled me to transition fully. Recently I received a comment from fellow blogger Paula Godwin who described her journey a little different:

" For those of us who transition later in life it is "interesting" when we get the revelation that after spending the first 50 (or so) years of our life trying to work out if we are a woman at all, that then we suddenly have to work out what sort of a woman. Although having said that I'm not at all sure how much choice we actually get in the matter, much like being Trans at all, I suspect that much of what sort of a woman I would turn out to be was not a choice but an inevitable!" 

You can read more from Paula by following her "Paula's Place" blog here or by checking out my "Do You Wanna Hook Up" section of the blog which contains her latest post.

Thanks for the comment and I too spent fifty years or so exploring being a woman at all. Then when I decided I couldn't deny my feminine nature any longer, jumping into the world and out of my closet was quite the experience. The first lesson I learned was all the years I thought my appearance as a woman was the most important facet of my life just wasn't true. I had no knowledge of all the other facets of a woman's life she had to live through on her path from being just a female to being a woman. My second wife so profoundly put it during a huge fight we were having about me being a crossdresser, that I made a terrible woman and she was not talking about just how I looked. At that point I was forced to put my male ego aside and seriously consider what my wife was talking about. The entire process of learning more concerning women's lives was difficult because I was shielded from what really went on with women because I was still presenting nearly fulltime as a man. In other words, I could not be trusted with secrets until I made the huge step of coming out as my authentic feminine self, which was sensed and embraced on many levels by several of the cis-women who befriended  me. 

During this period of gender discovery, much of my life was a blur as I increasingly set my male self aside and allowed my woman self to flourish. As Paula put it so well, it wasn't a choice, it was an inevitable. 

All I Ever Wanted

 If you would have asked me when I was young what I really wanted to be when I grew up, the honest answer would have been to be a woman. That's right. When all the other boys my age wanted to be sports stars, corporate presidents or whatever, my goal was so simple yet so difficult. Somehow I needed to lead a feminine lifestyle. 

Photo Courtesy
Jessie Hart

How to arrive there was the problem. The first hassle I ran into was my impending date with the Vietnam war military draft. I tried to outrun the draft as long as I could by attending and graduating college but was finally caught when my draft lottery number came up to 23. Which meant my fate was sealed. I immediately began looking for the military branch which offered a job classification as close as possible to the job I was doing when I went to college. I worked at a local small radio station which was owned by a fairly powerful congressman. Through his influence, I was able to secure a spot in the Army's Defense Information School which in turn enabled me to be eligible to work in the American Forces Radio and Television system. This was very fortunate of course but none of it served to help me to achieve my goal of being a transgender woman. 

After the Army I was able to resume my journey in earnest. This was my time to explore living a feminine lifestyle out of the mirror by sneaking out of the house when I could all the way to the exciting Halloween parties I went to. Over this period of time I learned many lessons the hard way but on the other hand I was learning leading a feminine life in a women's world was indeed possible. 

Ironically,  the more I learned, the more I needed to learn. The life I so desperately wanted to pursue still was far away. An example is when I learned how walking in heels was fine, looking other women in the eye when I communicated with them wasn't as easy. Plus, surely wearing a frilly nightgown or lingerie was wonderful but it ultimately didn't help me in the regular world where other woman were wearing jeans and sweaters. Somehow I needed to temper what I thought would happen when I jumped out of my gender closet to what was really happening. 

Another problem is I have a mind which I really have to push to stay on a topic or goal. It's the primary reason most of my posts don't go over three minutes in length. I have this problem which ended up serving me well when I was making all my early cross dressing mistakes. After the countless times I was laughed at and came home crying, I was able to fairly quickly go back to my feminine drawing board and try again. The major problem I discovered was when I learned to stop my expectations of how men viewed me and begin to focus how the women viewed me. Once I began to focus on women, I began to present easier and I could concentrate on letting my long suffering feminine inner person out and into the world. 

From that point forward when my wife Liz said it best to me, when she asked what type of woman would I want to become. Would I bounce out of bed every morning and do my makeup and hair with heels and hose or would I rely on casual jeans, T-shirts and tennis shoes for everyday non public wear. Since I always have a difficult time waking up in the morning, I chose to settle in to the casual feminine lifestyle. Hormone replacement therapy has helped me also with adopting a casual lifestyle since I have my own long hair, soft skin, breasts and developing hips to reassure my femininity. I know who I am now the world needs to accept me also. 

All I ever wanted was to lead a feminine life and I finally made it but it was a long struggle. My life was certainly a marathon not a race. 

Busting Out in "C-Bus"

I had a former boss who called Columbus, Ohio  "C-Bus". I used to attend regional management meetings at his office in Columbus. Ironically, I had a difficult time keeping my mind on the business subjects because I was so happy to be back to where I had so many experiences coming out as a novice transgender woman. 

Jessie Hart Columbus Photo

Very early I was able to attend what were referred to as transvestite mixers in "C-Bus". I learned the true value of the mixer label when I met a number of new acquaintances throughout the gender spectrum. Anywhere from crossdressers who were fighting the urge to dress as women to impossibly beautiful and feminine transgender women carefully considering their next step. In other words to explore surgery and live full time lives as an out transgender woman. Most importantly I needed to discover more and more about where I wanted or needed to go with my gender dysphoria. I was stuck in the middle of the two gender binaries.

As I have mentioned, about half of the time, I was able to attend these mixers alone. Either my wife had to work or just didn't want to go. Plus the mixers had decreased in size to exclusive parties at one of the transgender woman's houses. She owned and lived in a restored brick house in the "German Village" restoration district just south of the downtown business district. The nights I was alone allowed me to explore several of the "what if's" of my transition. 

Perhaps one of the biggest back then was the need to be validated as a woman through a feminine appearance. It was all well and good until one night I was cornered by a much bigger "admirer" who used to attend the parties to admire the other guests. By my own admission I was dressed more trashy than classy and he cornered me in a hallway. I found out very quickly how a woman can get into trouble. 

Other times I did tone down my appearance and was able to flirt my way into perhaps interesting situations. I say interesting because I knew deep down I would never cheat on my wife. (I never did). Another night with an interesting outcome came when I casually met up with one of the lesbians who were checking out the mixer with a friend. I flirted my way into taking off and going to a nearby predominately lesbian club with her. Predictably that was about as far as it went.

As I look back on all my experiences at the mixers, I see them all as a giant learning experience. Through it all I was desperately searching for my true gender identity. The early mixers in C-Bus were both frustrating and inspirational. Frustrating in that I knew I was light years away from coming to a gender decision but at the same time, my successes were propelling me forward into always seeking more

To this day when we can afford it, my partner Liz and I always still love to "Bust it Out in C-Bus." 

 

Achieving a Transgender Goal

 Similar to other human beings, we transgender folk follow a long path to hopefully discovering our  true selves. 

Even though we face a difficult and often cruel journey to arrive where we are heading, others are not immune from going through similar yet different struggles. It is my belief that even though cis women and men are just born female or male they have the chance to hopefully grow in life to be quality women and men. I see the same struggle with transgender women and men as they grow into their authentic selves. 

Connie and I used to refer to them as "trans nazi's" back in the day. They were the ones who seemingly held the number of gender surgeries you had or didn't have against you. More than likely another version of "I am more Transgender than you" movement. How sad is it any of us have had to go through anything like it. 

Early Cross Dressing Picture
Jessie Hart Collection

My earliest remembrances go back to my first visits to "transvestites' mixers" in Cleveland and Columbus, Ohio. Out of all the different types of cross dressers in the room, the ones who perhaps influenced me the most were the ones I called the "A" Listers. The attendees who were impossibly feminine and attractive. Unfortunately, they were the biggest bitches in the crowd. I didn't want to act like them, I just wanted to look like them. With the help of practice and a timely makeover, I finally earned my right to go out with them and party after the mixer was over. 

Slowly but surely, I was achieving a transgender goal I didn't really know I had. Ironically, I never did fit into a niche group there either. I wasn't one of the "A" listers, nor was I a so called run of the mill  cross dresser. Finally, the term transgender came along to save me. I found my niche. 

Overall though, goals are difficult to achieve for many transgender women and men. We have huge hurdles to overcome when we come out to friends and family. Many times, those same friends and families don't understand they have to transition also. Rarely do we stay the same as we make the journey across the gender frontier. Hormone replacement therapy alone takes awhile to fully set in so transitions are far from complete when a trans person comes out. 

Then there are the gender surgeries. All the way from breast enlargement, to facial feminization, to gender realignment it's often a difficult and painful path to take. It takes a special friend or family member to understand and follow one through such a drastic journey.

Perhaps the most cruel goal of all is the conscious desire to forsake any gender privilege you may have built up over the years living as your non authentic self. Depending upon your age, you had potentially accrued the so called right and knowledge to live a certain way. I was to the point in my life when I had earned the hated "Sir" word. If I was deserving or not. 

I'm fortunate in that I have been able to achieve my transgender goals but I have had plenty of help along the way. I can't forget any of them.   

A Step Forward?

 Recently, I have been reading about and even know a couple people who describe themselves as non binary humans. It's my guess most of them would also be known as gender fluid or even androgynous back in the day. 

Then again, I don't like to become mired in labels. Plus, as Connie has brought up in a few of her comments about how years ago, there were only two recognized genders. Then as the years progressed the transgender term became a reality. I remember the first times I became aware of the idea of a transgender person, the more it made sense to me.

All of the sudden, the impossibly feminine cross dressers I encountered at the very early transvestite mixers I attended made sense. They weren't cross dressers at all but rather, they were transgender. While we are on the topic of labels, a few of them even made the jump to transsexual and went all the way to sex change surgery. As it was known as then. 

Now, I personally have gone way past the idea of operating outside of the gender binary. I am firmly in the transgender camp and have no desire to vary my existence at all back to any aspect of my previous male life. 

On the other hand, I am fascinated by those who aren't and are able to be gender fluid or non binary. Hopefully, all of it represents a step forward for humans everywhere.  

In the meantime, here is the transgender flag. (I think) Because these days, everything changes so quickly in the world of gender.