Finding your Happy Place as a Trans Girl

Image from Trans Outreach, JJ Hart

As I negotiated my way through the gender wilderness I was in, I needed to reach out at times to find moments of gender euphoria or happiness. 

As I have written about in the past, happiness was a learned trait which was difficult to come by in my family. Being good was not good enough, there was always time to be better. Little did I know, I was seeking to enter a world where being better than the average cis-woman was not going to cut it. Being better meant survival. 

As similar to most of you transgender women and/or cross dressers, I started out innocently enough as I raided my Mom's clothes and tried to admire myself in the mirror before my family came home. The whole process worked well for awhile until I grew restless and wanted to increasingly explore the world as my femininized self. Sadly, most all of this occurred when I approached puberty and all the unwanted male changes to my body began to happen. Very soon, I found wearing any of Mom's clothes was impossible as I gained unwanted hair, bulk and angles I hated but were stuck with. It was the infamous testosterone poisoning setting in which I battle to this day.

Rather than be unhappy, the mirror and my mind helped me to battle my way through severe bouts of gender dysphoria. I worked hard on acquiring the proper clothes and makeup I would need on a very limited budget. Of course with no guidance, I experienced many disasters on my journey before I settled in on an appearance which could get me by in the public's eye. I needed to disguise all my testosterone poisoning. Still, I persisted without much help and slowly learned the art of makeup which finally I did get some assistance with. At one of the cross dresser - transgender mixers I went to, I put my ego away and sought help from one of the professional makeup artists they had giving free advice. In language even I could understand, the guy doing my makeup guided me through a truly amazing transformation. Even I thought I looked so good I was happy with the results. 

Even still, the transformation was fleeting and all too soon, I needed to go back to my boring unwanted male life and the happiness I felt went with it. Leaving me in a state of depression. I did not realize having a feminine appearance was only the beginning and achieving any standard of looks went only to the upper levels of feminine achievement for me. Beauty was fleeting and very skin deep for me as I continued on my gender journey. I was told several times by my second wife I made a terrible woman and in no way was she talking about my appearance. She was right and it took me years to put my male ego behind me and learn what she truly meant. 

I also had a close transgender friend who told me one time I passed out of sheer willpower. Which I took as a backward compliment. Meaning I was going to engage the public and do my best to be happy even though I was not the most attractive woman in the room. When I did, I made a huge step forward towards becoming my authentic self. It was not until then did I begin to gain new friends and become happier. 

Sadly, my second wife passed away before she ever had the opportunity to meet the new improved me but I did have several friends who did. Their main comment was how much more happier I had become. I guess I never realized how much my gender issues had shown through to others in my male life. 

When I reached this point, I knew my family and upbringing was wrong. I could be happy in life and appreciate it. Along the way, I learned the truth that all the money and beauty in the world could not buy me happiness. I spent way too long living in the mirror to keep doing it. The friends and wife I made when I put my male self behind me proved happiness was not impossible for me. 

It is Fall and Time for Halloween

 

I have heard Halloween is the national holiday for cross dressers everywhere.

I know it was for me as I could not wait for the trees to change colors and the temperatures to dip so I could plan my "costume" for the season. I was fortunate when I began to learn so many feminine basics thanks to my Halloween experiences. Such as, the first night I went out with friends to a late night showing of a silent movie in a beautiful restored theater in Columbus, Ohio. The primary lesson I learned was to either get a close parking spot or wear comfortable footwear as my heels began to bother me very shortly into the evening. Regardless, I had a great time in my short mini dress and I was disappointed when I did not see anyone else cross dressed (that I know of) and the night went by so quickly. My friends we went with did not even mention my shaved legs. I remember thinking it was going to be a very long year before I again could challenge the world as my feminine self.

Back then, my self was very under developed. The mirror still had a hold of me and I really had very little knowledge of where I truly wanted to go as I researched the gender world. Would the mirror be my home or could I succeed as a novice transgender woman. In it's own very important way, Halloween helped to point me in the right direction. The first parties I went to, I simply tried to dress sexy as my "costume" and took the easy way out. I was seeking validation as a woman  essentially by doing a form of drag, which never worked for me. For the most part, I was left alone by other men and women. It took me several parties to understand what I was doing wrong. 

From there on out, I started to attempt to tone down my "costume." For example, one year early on in my transition I wore all black. Starting with black flats, black tights and sweater. I paired it all with my short black skirt, long blond wig and topped it off with a black beret hat. I tried it all out at one of the big dance clubs Halloween party in town and was enjoying myself immensely until a person in a mask came up to me and said I know who you are. Initially I was a mixture of being scared and devastated some one could see through my "costume" so easily I did manage to laugh and say who was I and the person said I looked just like my Mom. Then I realized who he was and he went on his way. It turned out I grew up near him in the rural neighborhood where I lived. Even with all of that I had a great time and was saddened that Halloween only came around once a year.

It turned out there were many other lessons to learn from the cross dressers national holiday as I was going to find out. One of the biggest ones was when I realized how rare it was to find another possible "non civilian cross dresser" in their own "costume." Again, I was feeling alone in the world. Another one was there was no way I could wait another year to venture out into the world as my authentic femininized self. At the same time of my Halloween adventures, the internet became a part of my life and I was able to research terms such as transgender to see if they fit me. I found there was so much more to learn. 

There were more Halloween parties where I continued to learn from too. I haven't forgotten my pledge to share them also since for the most part, they had such a profound effect on my life as a novice transgender woman. 

Hitting the Transgender Wall

 

Image from Selin 
on UnSplash

There were so many times during my journey to finding my authentic self that I hit a wall or two or more. 

The easy walls came when I was younger and was trying to find makeup and wardrobe items to admire myself in the mirror. During that time and into the future, finances were a major set back. As much as I admired the pretty clothes the girls around me were wearing, I just did not have the money to afford any of them. There was no way I could go to my parents and ask for a pretty dress for my birthday or Christmas. Plus, I was stuck at a major point of my overall femininized image when it came to my hair. In those days, I was stuck with very short hair cuts such as burr or crew cuts and there was no way I could afford a wig. A major wall, to be sure as I think having the first wig I cherished did not come around until my college years in the late 1960's till the early 1970's when my military days took over. Of course I was against the wall again when my hair needed to be kept very short.

After I had served my time in the Army, I was able to secure the finances to afford a more update feminine wardrobe and my walls began to take on a more mental aspect with me. The more I was able to sneak out of the house and into the public, the more I knew I had little or no knowledge of where I wanted to go as a novice transgender woman. It seemed everything was being thrown at me at once and my mental health crumbled after I was hitting many walls at once. My male life was becoming more and more demanding as I became successful at my job and I discovered the more I explored the female world, the more I liked it. 

Even so, climbing the feminine walls were difficult. It seemed everytime I mastered one aspect of being a transgender woman such as walking, I would catch my heel in the crack of a sidewalk and ruin my whole day. As I continued along my bumpy gender path, I found mishaps with walking in heels were indeed minor in the scope of my transgender life. On the horizon loomed much more serious walls such as communication with the public and with women in particular. Overwhelmingly, men ignored me and women were curious about what I was doing in their world, I discovered quite quickly I was interacting with more women than I had ever done as a guy which was scary in many ways, including what would I say and how would I say it. 

I wondered what had I done when I was forced to actually talk the talk of the person I had become. I resorted to what had worked for me in the past as I had encountered tough trans walls to climb. I basically tried to shut my mouth and observe what was going around me. It worked to an extent until people (women) began to warm up to the new person I had become. I even was giving other women advice on how to understand their boyfriends or spouses. 

Anyway you cut it, I guess for me, gender affirming hormones created the last major wall for me to climb. At the time, I was doing my best to appear as a woman and communicate as one to the world. Beginning the hormones in many ways was a selfish move because I did it for myself. When I did, instead of more walls crashing down, they melted. HRT, when I was approved for it was a magic potent stimulant my body had been craving for years. Very quickly, I knew I had made the right move as I was able to tear the final walls down and make my way into fulltime transgender womanhood. 

Surely, I was bruised and battered by hitting all the transgender walls I needed to scale to live the life I wanted but I made it. When I look back on all the terrifying yet exciting steps I took to get to where I am mow, I wonder how I made it. First there was my appearance and battling testosterone poisoning then overcoming the problems of male behavior which also effected my life that all made for a rough journey. Surely there were too many walls to count.   

Happlily Ever After?

 

Image from Dave 
Goudreau on
UnSplash. 

When it comes to transgender women and trans men, is there ever a happy ending?

As we examine our lives , again and again, we inevitably encounter many pains as we make the transition from one gender to another. Most of us (including me) go through a period of time when we consider ourselves to be cross dressers or transvestites. We were in our own state of limbo, not knowing where we were going. I am amazed when anyone in the outside world thinks our life was so much easier and we were wearing the clothes of the opposite sex as some sort of a lark.

The fact remains, amidst the brief moments of gender euphoria in front of the mirror, we never actually had a choice when it came to our gender issues. In the case of many people such as me, my journey was very lonely and singular and I wondered if I could ever live happily ever after as a transgender woman. It seemed like the impossible dream and if I could ever arrive there, perhaps I could finally become happy. But happiness for me had always been fleeting. Probably because I had never seen much of happy in my family growing up. We were taught anything we did was never good enough. It carried over into my life as a novice transgender woman. 

No matter how attractive I thought I was, there always had to be more. I needed to be better as a trans woman. It turned out I did need to be better to survive in a new feminine world but getting there was a challenge when I went too far, too fast in the wrong direction. Primarily when I went over board in how I was dressing myself way too slutty and attracting the wrong attention to myself. It wasn't the type of validation I was seeking. It took me awhile to realize I could not make it to any semblance of happiness on the path I was on. 

I learned I never would have a chance to be happy in transgender womanhood, unless I began to change my ways and began to dress to blend in with the world. Once I did, I learned I had a whole new set of challenges I needed to face to be happy. Similar to many of you, I faced spousal issues as well as job, family and friends. I always considered changing my gender was a difficult task to take but I never knew all the nuances of making the change I would have to take. Being a woman, trans or not, was a very layered process and I would ever be happy if and when I ever arrived at my goal of living fulltime as my authentic self. 

Then there were the gender affirming hormones I decided to pursue. Before I could begin the meds, I needed permission from a doctor and a therapist to begin. Adding to the importance of the move but once I started the hormones, I knew I was in the right place and I would not turn back to my old unwanted male life.

Even with the HRT, happiness was still fleeting as I faced a wonderful new world. Most likely because there were still instances of public setbacks I still had to negotiate, which included times when my mind was playing gender tricks on me. I was still influenced by sixty years of living a male life and being conditioned to never be happy.

Now, at the age o seventy five, I know I certainly have fewer years ahead than behind me. Now I have to make a concerted effort to be happy. If I don't, it will be too late.

Intimidating Women

Library of Congress 
image from 
UnSplash.

During my life, surprisingly so, I have encountered many intimating cis-women. 

Probably the most intimidating of all was my Mom, a dynamo at a mere five foot two inches tall.  From early as I can remember, we clashed on many different issues probably because we were so much alike. On the girl side, I was fascinated from a young age when I watched her skill with makeup and hair. I could only dream of ever duplicating her prowess. Of course I would never get the chance for her to ever see the fashion skills I finally developed as the daughter she thought she never had. 

As I grew up, my intimidation of girls of all kinds increased. I was so jealous of their ability to dress in pretty clothes and wear makeup continued. In addition, I was so shy, I was afraid to communicate with girls at all. So my problems continued to get worse. I never had the chance to circle back to where I began. All the time I was cross dressing in front of the mirror, it was a very solitary, lonely experience as I craved the peer feedback other girls my age had to work with. 

The older I became, the more I admired women who were stronger and spoke their minds. You might say I was intimidated in the most positive ways by strong women. I was even attracted to them to the point I chose one for my second wife who I was married to for twenty five years. Even though she knew I was a cross dresser from the very beginning, somehow I secretly thought she would help me with my on-going quest to be a feminine person. She never really did help me much and very much resisted any ideas I had I was a transgender woman. 

Perhaps I am attracted to strong successful women because I wish I was one. I so admired the women managers I worked with because of all the extra skills they had to use to be successful. Most if not all of them had families to support at the same time they worked a full-time job. I was in the restaurant business and some of my best kitchen managers were women who dealt with macho kitchen crews. 

Being a transgender woman, I think sometimes I intimidate other women. Sometimes they seem to melt with kindness such as the hostess last week when my wife Liz and I went out for my birthday dinner. She was beside herself to make sure we were satisfied with our experience. As I can remember, intimidation on my part of a guy was when I was shopping at a grocery store years ago for the families groceries. In those days, a fashionable woman who had the legs wore an oversize sweater with flats and a mini -skirt, so I did on that day. As I chose our food, I tried to contain my fear in checking out, I found I was wrong.  As it turned out, the store was nearly empty and only had one check-out lane open with a woman cashier and a male bagger. 

It turned out, I really intimidated the bagger, he blushed and stuttered when he asked me if I needed help taking my bags to my car. I looked at the cashier and him when I said I didn't and she gave me a slight knowing smile. I wondered then, if she knew I was transgender at the time or not. Regardless, it was quite the experience. 

It wasn't until I transitioned into a feminine world as a trans woman did I fully understand all the nuances of what it takes to be an intimidating woman. For example, some women use their heels to begin the process. Heels give a shorter woman a height advantage to be able to compete with the men in their world. Plus, these days, more and more young women are becoming educated to give themselves an extra advantage in the world. 

It turns out, in my life, intimidating women are becoming the norm as the future is female. 

 

Becoming Me

Image from the 
JJ Hart
Archives. 

As I bridged the gender gaps in my life to survive, I did what I perceived to be cross dressing as a woman in my family's mirror. 

Slowly I began to learn the makeup and fashion tricks the girls around me used to look their best. At times it seemed I was attempting the impossible as puberty set in and my body began to go through many unwanted male changes. Like it or not, I was stuck with testosterone poisoning and I would somehow have to get use to living with it. I was becoming a me which was very much unwanted. 

As I got by in life, I learned to camouflage my broad shoulders, and torso (among other negatives) and try to emphasize my positives, even if I needed to do it with feminine style padding in all the right areas. Since I was told I had good legs at the Halloween parties I went to, naturally I tried to emphasize my legs when I dressed. 

Sadly it took me many years to learn the truth about myself. Yes, it was true I was a cross dresser but not the way I always thought I was. In no way was I a male cross dressing as a female, all along I was a woman cross dressing as a man. Once I arrived at that point in my life, suddenly everything began to be so much clearer. I just wish I could have come to the realization so much earlier than I did. I always use the excuse to myself the world itself held me back in the pre-internet years before very little was being published or researched about gender issues. In fact, I still remember in my youth the news stories about the police rounding up and arresting men dressed as women. How could that be? 

Still I persisted and remember vividly the night I dressed up in a mini skirt, panty hose, heels wig and makeup and headed to a nearby gay bar when my wife was away. I was so scared and once I got there and was admitted through a locked door, I only had one drink and left before I even relaxed and I never had the opportunity to go back before the owner died and it closed. Even still, my adventure that night helped me to become the transgender person I wanted to be. At that point, the problem still was, I did not totally know who I was, or face up to her yet. But I was diligently working on the problem by researching my feminine life. 

To do the research, I needed to risk everything and leave the safe surroundings of the mirror and enter the world. I started with going to more gay venues and becoming quickly disillusioned when they all thought of me as a drag queen. Lesbian bars were better but I did not find true acceptance until I became brave enough to go to straight places. There I could watch my sports, drink my beer and become accepted as a regular fairly quickly by the staff. I minded my own business, tried to be friendly and tipped well and was in. Even though I knew they knew I was transgender. it did not matter and along the way I think it even helped me. One way or another, I was taking giant steps towards being me and I knew there was no way I could ever go back.

Perhaps the biggest step I ever took on the gender path to being me was when I started on gender affirming hormones. After being approved by a doctor, the changes occurred quickly.. In addition to the external changes such as breasts, hair and skin, I experienced internal changes also. My emotions changed as well as my whole life just softened. The entire time of gender adjustment was one of the most magical times of my life. 

Overall, the discovery of who I really was as a transgender woman was a terrifying yet exciting journey. One I don't regret taking, once I faced up to her, I was so much happier.   

Connecting the Gender Dots

 

JJ Hart, from
the archives.

Many outside of the LGBTQ community, or more precisely the transgender community, think connecting the dots between male and female is as simple as putting on a dress and makeup.

One of the problems is, in order to  walk a mile in our transgender shoes, you have to learn to tie the laces first. Very few people have the patience or understanding to do it. The complexity of gender scares most people off. They think gender is cut and dried but is the opposite. 

Even those in the community have a difficult time connecting the dots and don't realize that even if we have similarities as trans women or trans men, we have just as many differences. Obstacles such as male lives, spouses and sexuality face us as the next dot to connect becomes bigger and bigger or worse yet out of reach.

During my male to female transition, many times, connecting the dots seemed downright impossible and I would never be able to move ahead in my life. My primary problem was my spouse and my male  self were standing directly in my path to gender realization and they would not move or give up their spot in my life. What I did in the meantime, was fall back into a more realistic journey to the next gender dot. An example would be when I began to get out of the non challenging mall shopping experiences and into actual interaction with the public as a transgender woman. 

Many times, the dots would totally fool me when I totally had a mis-conception of what a woman's life would be like. For some reason, I did not think I would be the one whose personal security would be challenged or my intelligence would be diminished when I jumped the gender border into trans womanhood. I was wrong in my judgement and needed to rapidly rethink my path to another dot. Of course I always knew women's lives were much more complex than men's but I did not really know until I succeeded in connecting my dots. 

The frustrating part of my whole experience was two-fold. The first part was I needed to accomplish it on my own with no help and the second part was everytime I thought I had accomplished something, immediately it seemed I needed to accomplish another milestone or dot on my gender journey. It was not until I was accepted in a small tight knit group of women friends did I really begin to make progress in the world. I learned through them, I could validate myself in the world as a trans woman without the help of much of the public, including men. Connecting these dots made my life fun again and so liberating. 

I can not begin to completely describe my experience connecting my own dots because they could be so much different than yours. The one thing we may have in common is, in order to have success in the world, you have to summon the courage to put yourself out there. Of course the problem these days is the concern for your personal safety. You have to be very careful, be aware of your surroundings as any other woman would and connect your dots the right way.       

 

Building a Dream

Image from Moreno Matkovic
on UnSplash

 Similar to many of you ,my journey to building a dream took me many years.

As I am fond of saying, over a half a century of construction. A long time when you think about it. At first the steps were obscure and very shadowy as I snuck behind my family's attention to cross dress in front of the mirror. I did not know much about what I was doing, or the tools to do it so I looked as if I was clownish, most of the time. As luck would have it, the mirror often lied to me and gender euphoria set in, before I even knew what it was and what it meant. All I really knew was how at night when I slept, I dreamed of being a girl and was sad when I woke up and needed to face the same old male world.   When I was able to escape into my feminine world, I felt so natural and exhilarated, I just couldn't stand to go back.

The years flew by and I was able to learn more and more about the femininization process I was facing. At the same time, small glimpses of what if slipped into my mind. Or, what if, someday I could make living as a woman trans or not part of my reality. As I did, the reality of building a transgender dream became increasingly difficult. Partially because, at the same time, my male life was becoming increasingly successful and it became  harder and harder to give up what I had built. Still I moved ahead as the feminine forces within me were so powerful.

Since it is coming close to the Halloween season around here, I would be remiss if I did not mention how going to Halloween parties dressed as a woman did not help me build my dream of perhaps being a full time woman some day. Back in those days, the term transgender was still in it's infancy and I did not know how it fit me. All I knew was, I worried and stressed for months ahead of Halloween about what my "costume" would be. Predictably my outfits started out slutty and evolved into going to parties dressed as business professional to see how many people would notice I was a guy at all. Overall, I had several meaningful experiences at Halloween which provided quality building blocks I could use when I seriously began to enter the world as my authentic self. As promised, I will write more about them as Halloween comes closer.

In the meantime, I was having more and more opportunities to learn I was so much more than a man who wanted to look like a woman. I even received a  comment from "Paula" across the pond in the UK concerning a blog post I wrote on the subject:

"I often think that the moment of realization that you are a trans woman rather than a cross dressing man is the Biggy! After I accepted who I am everything else that followed was just a natural consequence of that initial revelation. After I had accepted that I was in fact a woman it was perfectly logical that I would want the world to experience me as such, so I went full time. As I wanted to experience the fullness (as much as possible) of life as a woman it was perfectly natural to get medical help, leading first to hormones and then surgery. All of those decisions were the natural consequences of that first understanding that this is who I am not something I do."

Thanks to Paula and all of who comment! I could not have put it better. 

As it was, I kept on building until I formed a solid foundation to finally achieve my dream. It was never easy but on the other hand, building something worthwhile never is.  All the lonely nights I spent going out just to be alone come to mind as well as the occasions I was shunned or even laughed at. At that point my dream seemed to be so far away. Deep down I knew I was doing the right thing and kept on building. It turned out happiness was just a build away. 

When Every Night is Girls Night

Grae Phillips is still active
on Facebook if you want to 
see more. Or just keep up. 

I know I make a big deal out of my second huge transition, when I mentally moved from being a serious part-time cross dresser into being a novice transgender woman.

Sometimes I feel as if I am putting myself on some sort of a gender pedestal when I write about not considering myself a cross dresser anymore. If it comes off that way, I don't mean it to. On occasion, the written word gets in my way. Getting back to the cross dresser versus transgender statement I made, I think in my case, it was a matter of me judging my own life. Originally, as I was working my way through my early years of admiring my girl self in the mirror, I knew it could never be enough. There had to be more. I was so tired of cross dressing for one day and then two or three days later wanting to do it again. 

As I always mention, all of this occurred back in the pre-internet information era when any news and contact with like minded gender individuals, be they transvestites or transsexuals, was very difficult and rare to come by. This was even before the barrage of talk shows led by the late Phil Donohue who interviewed female impersonators such as "Grae Phillips", all the way to transvestites seeking approval from a doubting world. It was quite a bit for me to sort out. But I did. I knew I could never be as beautiful and talented as Grae but I could reach the standards of most of the transvestites I saw on my television. There was hope for my future after all.

As I progressed into meeting more and more diverse cross dressers or the women known as the new transgender group I began to think what it would mean if I went all the way and every night became girls night. In other words, a time when I would never have to go back to my old male self and live. Deep down I knew there would have to be some sort of line drawn in the sand if I did. As much as I loved all the fun of the newness of applying makeup and picking out clothes, I wondered what would happen when the newness wore off and I needed to settle into the daily routine of the transgender womanhood.

It turned out, I had nothing to worry about. I settled into my new feminine routine as if I had always should have been living this way. I found I didn't have to do much special on many days such as most cis-women do and then again still have the fun of dressing up for special occasions. It was true, once I jumped the gender border from cross dresser to transgender, I could experience what life could be like if every night was girls night.