Out of My Mind, Into the World

Image from
the JJ Hart
Archives.

There were many times during my transgender transition I was thinking I was somehow out of my mind. 

I even went as far as telling others there was something wrong with me. Of course there was something wrong and it was because I was trying to live as a man, not my natural woman. It just took me too many years to realize I was doing everything so backwards when it came to dealing with my gender issues. I was not a man cross dressing as a woman, I was the opposite, a woman cross dressing as a man trying desperately to get by. It seemed so unfair because of all the time and effort I put into having my man card. 

Then, I began to put as much effort as I could into my girl self. I tried my best to observe the girls around me in school and model myself after them. Of course in those days, I was severely limited  by my family and financial situation. Even still, I persisted through the idea I had something wrong with me just because I wanted to be a girl. Plus, I knew if I was ever caught cross dressing into my more normal self, I would be sent off to the first non-understanding therapist my parents could find and he would label me mentally ill when I knew deep down I wasn't.

Adding to my gender difficulties was the fact I was so alone. In the pre-internet days, any information about men wanting to be women was very hard to come by and I was convinced I was the only person in the world who felt the same way I did. It wasn't until somehow I discovered Virginia Prince and Transvestia magazine did I understand there was quite the community of men who called themselves transvestites. Once I did make the discovery, I knew somehow I needed to interact with the nearest group to me in a suburb of Cleveland, Ohio which was still quite the distance away. Regardless, I knew I needed to make the connection. I still vividly remember the diversity of the mixers I went to. I thought by reading the so-called hetero restrictions on the members would limit the diversity of attendees but it did not. There were everyone from cigar smoking cross dressers in cowboy hats seemingly afraid of losing too much of their masculinity all the way to the impossibly feminine transsexuals who had  worked hard to lose all of their maleness.

In the middle of it all, was me wondering where I fit in. I was too much woman for the cross dressers and not enough for the transsexuals. Once again I was frustrated with my results as I worked my way out of my mind and into the world. 

It took me quite a bit of work to fully make it into the world. The steps I took led me away from the old restrictive transvestite mixers, all the way to being invited to smaller diverse parties in Columbus, Ohio which I enjoyed immensely. Primarily because I was accepted for the person I was becoming. I was heading into the world for once because no one knew or cared about knowing my old male self. I even took the process another step farther when I began to go out by myself and become a regular in my favorite venues I was used to going to as a guy.

I found I was never out of my mind as the world accepted me. I just had to wait for them to catch up. If I had realized it years ago, how much easier my life would have been.

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.  

Transgender Inspiration

The late Lynn Conway.

 In my formative years growing from a beginning cross dresser into a novice transgender woman, there were very few inspirations for me to follow. One of the few I knew about was the very accomplished and talented Lynn Conway, a computer scientist and electrical engineer.  

Deep down I knew I was not on the same level as Conway and the very few I did know about followed the same path as most transsexuals face when they transition into a feminine life. We were expected to leave our past behind, have all the needed operations and relocate ourselves to start over. Since I was my usual stubborn self, I could not see me going down all of the same roads as well known transsexuals. In fact, I knew a couple trans women nearby who were ready to go down the surgical road and change their lives forever. 

As in most cases each of their lives were totally different than mine. So they were more of an interest to me than an inspiration. By getting to know them closer, I had hoped to gain more knowledge of what I would face if I decided to go further with my own gender transition. I did learn, as I went on, everything was different when I was living as a transgender woman. I had my own preconceived ideas of how it would be to live as a woman from all the years I had spent closely observing the women around me. However I found most of my conceptions were wrong as I slipped behind the gender curtain. The prime example was how I was presenting myself as a woman. I wasn't dressing to blend in and was drawing unneeded attention to myself. My efforts came from my old male ego dictating my fashion and wardrobe. I had no inspiration to guide me the correct way.

I think I tried to use my second wife as inspiration but I was just not in the proper mental space to accept her criticism. In other words, my feminine self had not had the chance to grow up past my adolescent years as a trans woman. During those years, happiness was looking very lonely as my wife and I constantly fought over my appearance among other things. I think she knew she was fighting a losing battle as my internal feminine self fought with her all the time. Every now and then, I did talk her in to going out to eat as two girls and I really tried to dress down for the date. As a matter of fact, if I dressed down any more, I might as well just have gone as my male self. 

I was getting nowhere fast in my quest to learn more about being a quality transgender woman, so I was forced out on my own. Which added in it's own set of problems. Primarily, here I was sneaking around behind my wife's back to see if I could live as a woman. In doing so, I found I could create another life. Furthering the divide between my wife and I.

The divide widened until her death and inspiration or not, I continued on with my search for my feminine self. What I discovered was, she was with me all along. Just waiting for a chance to live. When she did, she became my own inspiration and I never looked back. In many ways I found she adopted many of the mannerisms and personality of my Mom, who was very outspoken and not shy. I admired her so much, I took her first name as my middle name when I legally changed my gender markers. 

These days, with all the internet and social media access transgender inspiration is much easier to come by and we need the inspiration with all the negative coming our way from politicians. We have to do all we can to keep the positives coming.

Options or Paradise

 

Liz on Left, out to eat! 

During our gender transitions, many times we have the choice of options or paradise. 

Often, options come about as not being a choice. Examples include all the days we had to rush around and hide our feminizations from our family and friends. We had no option but to hide our truths. For some if us also, our cross dressing options never became any better when we had to pursue stints in the military. Certainly, the military provided every roadblock in the world for pursuing any route to paradise for gender conflicted individuals. 

As a whole, back then, paradise was very difficult to achieve. In fact I can now refer rare paradise as gender euphoria. For many years and even decades my gender balance never changed. I was still sneaking around risking life as I knew it to momentarily express my true inner gender. Fortunately, I had the time to work on perfecting my femininized presentation. When I finally was able to pursue paradise by going out in public, I was closer than before to achieving success. In fact, once I learned to blend in with  other women in the world, I was more likely to find a fleeting sense of paradise. 

Usually, my paradise did not last long because I needed to quickly return to my male world which I was increasingly feeling uncomfortable in. I was desperately seeking other options to find more gender euphoria other than the annual Halloween parties I was going to as a woman. The parties and the transvestite/ transsexual mixers I started to go to helped me to understand the gap I was facing when I considered the ultimate outcome of where I wanted to go with my life. Instead of just embracing the usual male attributes in life, I needed to include the very real possibility I would have the option to live life out as a transgender woman. The reason I thought this way was I encountered paradise when I was experiencing the world as my true authentic self. I felt so natural and wondered why I had waited so long to do it.

What if I had experienced paradise a decade earlier than I did when I went to a TGIF restaurant and bar determined to mix with other single women. Maybe I was just waiting for the world to catch up to me but more than likely the opposite was happening. I had the options to catch up to the world and I took the chance. By the time I ventured out into the world, I had certainly paid my dues and was  ready to reap the benefits. 

Still I was frustrated when the benefits of my new life were just out of reach. Such as the times when I was so comfortable in my new feminine world I actually forgot where I was and caught myself slipping back into a male mode. I still did not have the full closure from my old male self I so desperately needed. I kept running into unexpected roadblocks and stop signs on my gender path such as a spouse's death which changed my ideas of where I was headed but not for long. Soon with fewer and fewer options to consider as well as a solid new life I was building, paradise was closer than ever before. 

As transgender women or trans men, we often experience periods of options or paradise as we follow our difficult, unique gender paths which separate us from other humans. The whole journey hopefully makes paradise worth it.  

Building from the Inside Out

 

Image from Brooke Cagle
on UnSplash

Years ago I began to understand I was building a new human being from the inside out.

I began to realize it when a person very close to me told me how fortunate I was to be able to start over in the world as a transgender woman. At first I was scared, could I really re-create myself as a woman and at the same time achieve my ultimate feminine dream. Following years of living and training, I found I could indeed live a life as a trans woman.

Before I did, I needed to decide what old male baggage I would have to discard or adjust to the fact I would have to bring it with me. It was difficult since I decided to seriously began my gender transition at the age of sixty, I had years to consider what to do with my baggage. Initially, I was part of the old transsexual school which believed you had to totally uproot your life and move when you transitioned and start all over. The problem I had was, there was some baggage from my old life I wanted to bring with me. For example, I wanted to try to preserve contact with my family and wondered if my wife (who I loved completely) would ever accept me. Not to mention other key points of my life including my passion for watching sports. 

Fairly quickly, as I transitioned, I was able to indirectly control all I was building from the inside out. By this time, I had worked out most of the appearance or fashion challenges I faced, allowing me to work on expressing my internal self. First of all, I learned my only child accepted me totally and my only sibling (a brother) did not. Sadly, we have not communicated in over a decade now. I know I have survived and I have assumed he has also and we moved on. Since I was now a different person now and he is entrenched in his ways, I am sure it has all been for the best although it hurt me how he handled it by rejecting my invitation to the family's annual Thanksgiving feast.

In many ways, having the opportunity to rebuild myself was terrifying yet exciting. Along the way, I found I needed to transition again. Mainly when I finally decided to make the mental move from cross dresser to transgender woman. I say mental move because I wasn't doing anything outwardly any different as I was doing my best to put my best appearance foot forward as a woman. I knew if I was successful, there would be no turning back on my gender path. It was a huge continuing beginning in the process of leaving my male world behind.

By this time, I was well on my way of deciding what baggage I could bring with me and what I could leave behind. I was preparing to give what was left of my male clothes to a charity and I had fairly quickly established myself as a regular in a couple of the big sports bars I had frequented as a guy. By doing so, I could meet my small group of new women friends I had met and watch the games we all enjoyed. My new life was coming together from the inside out and I was loving it. 

Even still, it sometimes took all the concentration I had to remember I was living a new life and I needed to rely on my inner female to carry it out. By doing so, I was able to say what I was thinking and not screw it up by injecting any of my old toxic male self. The only thing I could rely on was my new friends and their reaction to me since they had no clue of the old me. It was very liberating to say the least. 

Overall, I have to say, building the interior person was more intense when compared to the exterior woman the world saw. Especially when I needed to communicate more and more with the public as my new self. When I did build from the inside out, I learned to live my truth and empower my life as a transgender woman.

  

A Want or a Need?

 

Summer image from
the Archives. 

Are gender issues a want or a need. 

Initially I know I thought being a girl was a want, rather than a dream. During one of my classic if I had known then what I know now phases, all I knew was I loved my cross dressed image in the mirror and could not wait to see her again and again. The worst part is I could find no outside information on my gender issues. Mainly because deep down I knew I wanted to do more than look like a girl, I wanted to be a girl. Those were the pre-internet dark ages, well before the transgender label was even used. Perhaps, had I had access to gender information I would have known the way I felt went way past being a cross dresser or a transvestite, as we were known in those days.

In my mind, the separation between a gender want or need was I could enjoy cross dressing for awhile when I wanted to but wanted to be feminine because I needed to. Sadly, it took me years to figure out what was going on. I went ahead playing the same old male role I disliked so much as I tried to be accepted into a macho male world without becoming a toxic man. Naturally, it was a difficult game to play and wrecked havoc with how I treated the world. My gender issues and how I dealt with them made me so frustrated and mean, I even lost jobs because of them. 

As the information age caught up to me, I began to understand I was not alone in the world any longer and there was even a label for my gender questioning. It was called transgender and it explained why I had never quite felt at home when I started to explore the cross dresser mixers I went to. Most certainly I knew I met a diverse mix of people. Including some of whom were headed for gender realignment surgery. To go that extent went way past being a want and into being a need. Especially if you were going to all the pain and expense to solve the gender problem they may have had. Even though I was intrigued by the transsexuals as they were called then, I knew somehow I quite did not fit it into their world. The same as I felt for the majority of the cross dressers attempting to express their femininity the best they could. I was stuck in the middle again.

I made the best of it by trying my best to research both sides of the spectrum I was observing. At the same time, I was doing my best to improve my femininization presentation so I could observe closer the transsexuals to see if their path could be mine. My biggest deterrents to following the TS route was my second wife who I loved very much and not having the insurance coverage to complete all the expensive surgeries. What I did have was the need to make a gender change. It had long since gone way past being a simple want. By doing so, I put myself into a gender pressure cooker which took me many years to release the pressure and escape.

Even still, the pressure release was not immediate and took me many years of exploration to accomplish. So many days and nights of being lonely and searching for my identity as a transgender woman finally came around to help me. 

I was able to learn my gender issues were so much more than a want because I never had a choice. They were a need I had to survive.      

Opening New Doors

 

Ohio River image.

It took me over a half a century to open all the possible doors I could before I decided to begin gender affirming hormones and transition into a full-time feminine life.

For any number of reasons. I over-reacted and resorted to excessive experimentation  before I quit knocking on so many doors. Such as, behind door number one was a wife who did not approve.  Other doors had the usual questions such as what would I do with my friends. extended family and employment. 

Before I could make it to the other main doors, I needed to prove to myself beyond any shadow of a doubt, I belonged in the world as a transgender woman. What took me so long was I needed to live my male life at the same time as my new femininized life. Switching back and forth between the male and female genders took a toll on me but I kept slowly finding new doors to knock on and walk through. What I did was single out a door to go through and then judge the reaction. If I was successful, I would look for another door and if I was not, I would go back to the drawing board and attempt to figure out what went wrong. Often I found out the hard way that even though I was accepted in many venues, in others I was not. Mainly when I pushed the envelope too far and journeyed into the wrong redneck venue just to see if I could. 

Other doors I attempted to open and was successful is when I went to very small diverse mixers at an acquaintance's house in Columbus, Ohio. During the parties, I was able to meet all levels of the transgender community and see how I measured up. Especially with one of the transsexual women who I admired so much. Even though I did admire her, I learned her life was not applicable to mine and I had to keep looking for my own door. Since her path would not work for me. She was a soon to be retired Columbus fire person and was looking forward to a good pension to support her as a single woman. Plus she had good insurance, and I had none of them, I wondered how I was ever able to make it to my dream. 

On occasion, I grew frustrated with the number of doors I needed to go through. It seemed just when I thought I was successful, I was met with a dead end and needed to turn back. I did purge a few times and tried to put my male self in total control but deep down inside I knew the purge was only temporary and my girl self would re-emerge. She always did, stronger than ever searching for the mysterious, magical next door to go through. Sometimes it seemed as if I was stuck in a huge gender maze trapped and looking for a way out. 

Finally, I knew it was time to put my maze, doors and gender past behind me and do the right thing. I found the way out I was always looking for and she was with me all along. All I needed to do was admit the truth. All those years of looking behind all those doors made me aware of one main thing, don't wish for what you want because you just may get it. 

I wished for a full time transgender existence and kept opening doors until I got it. 

Gender Black-Mail

Image from JJ Hart, Ohio River
in background.

 Even though I have been living as a transgender woman for over a decade of my life now, my male past still comes back to haunt me. 

I suppose I am expecting too much from my gender transition since I spent such a long period of my life trying desperately to fit in with a male world I did not really want any part of. Recently, sadly an acquaintance of mine who was a fellow DJ on a local radio station passed from cancer. When I learned, memories flowed in including good ones and those not so good. One of the more interesting memories I have was of the time his wife (also deceased) told me about a new DJ at the station I used to work at who actually was starting her gender transition. I was surprised she had a fairly positive reaction to the gender issues so long ago. Way before the term transgender was popularized. Why I am mentioning it at all is it always amazes me what I remember or don't remember from my male past.

As I moved closer and closer to crossing the gender border, it seemed my old male self had an unfair advantage over me because he always mentally pointed out the good times there were when I was a guy. It was similar to gender black-mail. He would always say what about all the good times I had with guy friends when we were out partying. Essentially, overuse of alcohol allowed me to forget about my gender dysphoria for awhile and I could have a good time for the wrong reasons.

In addition, it was so so easy to fall back into my old male patterns and enjoy all the privileges I had earned from surviving as a man. When I transitioned into a feminine world, losing those privileges made a significant impact in my life. It seemed at the time, when I encountered most men, single or in a group, they held it against me that I had left the male club for greener gender pastures. Their way of black-mailing me was to shun me from any or all contact. At that point, their resistance just showed me I was on the correct gender path and I was more and more encouraged to try to advance to my dream.

Another facet I mention often is how my second wife and my male self enjoyed ganging up on my novice transgender self. My wife in very begrudgingly situations would let me go out with her as my authentic self. Predictably, she didn't like me no matter what I did and when she was mad at me would say I didn't know anything about being a woman. I equate it to applying for a job you have no experience in and the company won't hire you because you have no experience but won't allow you to gain any. I was learning the hard way, she would not help me to go behind the gender curtain to women only spaces. It would take me years to earn the respect or right of other women to play in their sandbox. Even if I was getting sand thrown in my face. 

It was obvious at the time, I was experiencing gender black- mail from many women also. I was too much of a woman to be accepted by men anymore and still too much of a man to be accepted by many women. Eventually, I solved the problem by keeping pushing forward towards my feminine dreams. It was very difficult to stay laser focused on my goal when I was still trying to maintain a life in both of the binary genders. So before I totally destroyed myself, one had to go. At the time, I compared where I was at to standing at the precipice of a very steep cliff and fearfully looking over the side. When I could not take it any longer, I took a long time to consider my gender options and came to one conclusion. I had always been living a lie as a man and no matter how much black-mail I had to put up with, I knew which path to take and I jumped. 

The path took me to gender affirming hormones and I never looked back. I knew I had made the right choice when I felt so natural and satisfied with my life. It turned out the only real black-mailer in my life was myself.

 

Damn it is Complicated

 

Image from Amanda Dalbjorn
on UnSplash

Crossing the gender border is never easy for the average human being. 

To begin with, you need to be very serious concerning your gender passion. You need to trust your instincts, close your eyes and leap. I took over fifty years before I could come to the point of being able to trust myself. After all, I had spent all of the time as a very serious cross dresser exploring the world to see if I could survive as a transgender woman. Some times I was good about making plans, sometimes I was not. As I took the good with the bad. Ultimately, taking the good with the bad, just walking a path I knew very little about. 

As I walked my new path, there were several points of reference along the way. Such as the mixers I was attending in nearby Columbus, Ohio. Many were big and more than a couple were very small and intimate. Regardless I learned from both and how internally complicated they were. All layers under the so called transgender umbrella attended one or the other. Everyone from seasoned transsexuals to very novice cross dressers often out for the first time in their lives away from the mirror. Through it all, I was trying just to find my way to discovering who I really was. All I did finally learn was I did not fit the mold of a stereotypical transsexual or a weekend cross dresser. I was somewhere in between. I found I was not everyone's cup of tea, I enjoyed being my own. 

Examples were everywhere, including the guys who cross dressed for certain mixers but not for others all the way to the impossibly feminine transgender women who made their appearance. I was drawn to the feminized crowd but often I was left out because of my looks. I had a long way to go with my appearance but I was trying hard. With the help of a professional makeup artist provided by the group one night, I learned the intricacies of applying makeup and could really help me because he explained everything to me. Thanks to his magic, I was able to move up in the eyes of the transgender or transsexual crowd. Even still, mainly because they shunned most of the rest of the average cross dressers, I stayed to myself. Except when the trans women went out to other gay venues after the regular mixers were over. When I did so, I was exposed to a whole new world of exposure in the world in my own transgender universe. 

As I did, my life became increasingly complicated. I needed to overcome inner clashes with my genders as well as trying to deal with the problems of dealing with my second wife who was against any idea I was transgender. The major problem, every bit of my self was telling me being feminine was the only way I could survive. All of my turmoil just led to more stress to my already fragile mental health. I ended up in therapy again, which did some good but were for the most part wasted because I refused to face the truth about myself. My authentic self was feminine and I needed to express it. The only thing therapy did was make my wife think somehow it was going to magically "cure" me or at the least, I was trying to help the situation. Which at the time was growing into a major problem between us.

When I first looked into the mirror as a kid so many years ago, little did I know how complicated my life would become as I grew into my gender issues. My gender path was so convoluted as I followed it, I often became lost. The only aspect which kept me going was the deep down knowledge I had been born to be a girl. Dealing with it was always the issue.

It's All in the Eyes

Sad Eyes
Image from
the Archives.

Over the years, my eyes have helped me out in many ways.

Of course there is the obvious reason such as the blessing of eyesight but then, life steps in- very importantly for a cross dresser or transgender woman trying her best to improve her makeup art. For me at least, the hardest part of conquering the mystery of makeup  involved making up my eyes. At the time, I equated it with applying paint to the plastic model  cars I was fond of building because I struggled with both. Ironically, at the age I was at, I am fairly sure my Mom would have did her best to forbid any use of makeup at all by the daughter she never knew she had. 

Still I persisted and grew more proficient with buying then applying my eye makeup, The availability of all the colors fascinated me. Along with the chance to match colors up with my limited fashion choices I was capable of finding. It was close as I could come to all the girls around me who I admired so much. 

Fast forwarding many years, my eyes continued to be a focal point in my makeup art. I had learned along the way women communicate through the eyes in many ways. Much more than men who rely on vocal cues. I knew as I transitioned into transgender woman, I was on the right path with my makeup techniques. All the years I put into my art was worth it.

Perhaps the most rewarding feedback I received from my eyes came from my wife Liz. For all the wrong reasons. We met on line when she responded to a post I listed as woman seeking woman. Keep in mind I immediately pointed out I was a transgender woman. Thankfully, none of my gender issue mattered to Liz and she said she was attracted to me because I had sad eyes. If the truth be known, during that part of my life, I did have sad eyes. Over the past two or three years before the picture, I had just gone through very dark portions of my life. Primarily due to death of my second wife and four of my closest friends, mainly to cancer. Along with the loss of my business, I had lost nearly all the self confidence I had ever had in myself. In fact, the only concrete thing I had to grasp onto was my identity as a trans woman. 

Regardless of my sad eyes, my girl self became my deepest passion. In many ways, just to get by, I needed to become a deeper researcher of women. Instead of becoming my father's son which I had chased for many years, I became my mother's daughter she never wanted, to my knowledge. The gender guilt I felt was only grief with no where to go. 

Led by my eyes when I communicated with other women, I found my way out of the darkness of life I was in and regained my confidence. Even though it was a different confidence than I had ever felt before. My confidence as a transgender woman was a hard earned quality which went all the way back to the days when I was struggling with makeup and shaving my legs when I was a kid. Living and learning was always an exciting experience. Even in the days when I was a dismal failure in the world. Somehow, deep down, I knew I was doing the right thing by pursuing a life as a trans woman. 

It was always in the eyes, I just had to learn how to use mine. They were such an important part of my life when it came to communicating with other women. Perhaps it is true when it is said your eyes are the window to the soul.

Transsexual Harassment

 

Pow Wow Image from the
Jessie Hart Archives. 

In a previous post I promised to write about the times I was sexually harassed as a transgender woman. 

The first time I experienced harassment came when I attended a nearby mixer/party with my second wife in Columbus, Ohio. The parties were relatively small but very diverse group. Anyone from cross dressers to transsexuals headed for gender surgery to male admirers attended. 

To begin with, my wife did not approve of the outfit I was wearing, saying it was way too short to start with. Of course I did not listen to her and went with the dress I wanted to wear anyway and yes it was very short on me. Even to the point of making it very uncomfortable to sit down even though I had freshly shaven legs and new panty hose.

Once we arrived at the party, I grew restless and needed to move around. Space was limited in the small house of the host so everyone was basically confined to the living room. There was also a hallway which led to a bedroom and bathroom. When I did get up, I didn't notice one of the male cross dresser admirers got up to follow me also. I was/am a big person and had never experienced any problems with my size before and was shocked when I saw how big the person who was suddenly stalking me was. Before I knew it, he had me cornered in the hallway and for the first time in my life I felt helpless. I didn't know what I was going to do until I looked up and saw my wife glaring at both of us. He saw her too and immediately backed off and the threat was over but not before my wife gave me the I told you so lecture concerning what I wore. Even though deep down I knew my wife was right, the deeper meaning of what happened to me never went away.

From that point onward, I knew how a woman could be overpowered and sexually assaulted by a man. I found out the difficult way, once I put on heels and hose and cross dressed as a woman, my male privileges changed forever. Gone was the idea I would not be stalked and attacked on a dark lonely city street or parking lot. Of course I needed to learn the safety lesson the hard way too. 

When I first came out of my gender closet, I frequented my share of three male gay venues clustered together on a city block in downtown Dayton, Ohio. Once I made into the venues themselves, I normally did not have any problems. It was when I was going back to my car one night, I ran into problems.  As I was walking down the sidewalk, I was approached by two men who ended up stopping me. I was lucky that night and was able to "buy" them off with the last five dollars I had. 

From that point forward, I told myself I would be safer where I went. I made sure I parked in lots which were safely lit and park as I could to where I was going. I even would ask friends to follow me to my car when I was out. I was lucky to escape any actual harm when I first ventured out of the closet as a transgender woman. I discovered negative harassment in no way validated me as a woman. All it did was put me in danger. In fact, it wasn't until I began to hang out and visit my lesbian friends did I learn I didn't need a man at all to validate my existence, transgender or not. 

Once I learned losing my personal safety as a former man was behind me, I could move forward and recognize what being an out and proud trans woman was all about. Transsexual harassment became an unwanted and unneeded determent to my life.   

Saving my Own Life

Image from Alysha Rosly 
on UnSplash
 

 
I make no secret of my Bi-Polar mental condition which went undiagnosed for a good part of my younger life. 

Ironically, it was my first gender therapist who connected the dots and determined my condition when I told her I often spent days struggling to even get myself out of bed. I just thought I was riding the waves of gender dysphoria  which kept me so depressed or elevated when I was experiencing brief moments of gender euphoria. During this time of my life, I was far from being the easiest person in the world to live with. At the least, I was prescribed medications which evened out my moods. The meds also helped me sort out my gender issues and finally figure out one mental issue had nothing to do with the other. In fact my gender dysphoria was not a mental issue at all but instead an organic one. Had I listened to my therapist, she was trying to tell me all of that but I was unwilling to listen. Primarily because at the point of my life I was in, I was still a novice transgender woman and didn't know if I could live my dream life.  There were still too many gender bridges to cross such as telling family, friends and bosses I was transgender. 

The furthest I had come at that point was telling approximately five close friends and spouses I was a transvestite. A long way from living as a transsexual with all the resultant rules I would seemingly have to follow Such as major gender operations, moving away and then starting all over again. To make matters worse, I hadn't even thought much about my sexuality. Would I suddenly desire men sexually? I was overwhelmed with all the big questions and just continued my life as a very serious cross dresser. At the least, I was able to work on my presentation as a woman and go from there.

Even though, my solution was far from perfect, I was saving my life the only way I knew how. The problem kept reappearing when I started to go out more and more behind my second wife's back. When I did, I fairly quickly began to build up a robust life as a transgender woman. Every step I took, the more natural I felt when I could never see how I could go back to living a male life. The whole process created tremendous pressure on my already fragile mental  health. I became increasingly self destructive, all the way to an unsuccessful, ill advised suicide attempt. Essentially, from the point of suicide, I purged most of my feminine belongings and even grew a beard to prove to my second wife I could do it. By doing so, I was intensely unhappy for the short time she lived until passing away from a massive heart attack. I often wonder what would have happened with us had she lived.

Following the tragedy in my life, over a short period of time, I regathered myself and refocused  on a new feminine life. I quit dwelling on death and began living a preferred life as a transgender woman. By doing so, I was all of a sudden needing to quickly learn more than I ever imagined about my new life. Throwing out or giving away all my male clothes was at once liberating and  on the other hand, very scary. I had never purged my male self my entire life and he resisted. 

Regardless, scary or not, the process of a gender transition saved my life. Over a space in time, my mental health has stabilized and with the help of gender affirming hormones, for the first time in my life, my body and mind are beginning to mesh. The entire process took me a lifetime to figure out but as I always say, it all was so worth it. 

Trans Lost and Found

 

Lost woman from UnSplash

During a transgender persons' life, we experience many enormous periods of  lost and founds. 

Perhaps the biggest loss most of us face is with our families. In the transgender transition process, often many in families choose not to understand our journeys to living as our authentic selves. I am very familiar with the process when my brother decided to end all dealings with me when his family decided they did not want me at a family Thanksgiving dinner. We have not spoken since and that was over ten years ago. Needless to say, I am not happy about all I lost with my brother. As I always write is how fortunate I was when I found other family to fill the void. Between my wife's Liz's family and the acceptance I found from my daughter's in laws, I found more than I lost. 

Another major portion of our old male lives we have a tendency to lose is much of the old baggage we have to try to bring along. Interests such as mechanics and sports are stereotyped as male and are frowned upon back in the day when transsexuals were expected to go through gender realignment surgery and then move away and start a brand new life. I saw the whole process as one of the biggest obstacles of me potentially giving up everything which I earned to start all over again. I wanted in a large part to have my cake and eat it too. Could I really, transition into a feminine based life and keep most of my interests? 

I was stubborn and found out I could when destiny led me to a whole new group of friends who helped me into a new world. In essence, I found more than I ever lost, even though going through the separation from my old male life was very traumatic and stressful. More than anything, the finality of the loss off of many of my old male friends to death was tough to take, including losing my wife of course. Before the found began to flourish in my life, it seemed the losses would take over and they almost did. 

It took awhile but slowly and surely. I began to climb out of my valley and begin to climb again at the age of sixty. I shed (or lost) almost all the parts of my male life and even though I was scared of the future, I could at the least look ahead to better times ahead. Finding more than I lost became a fun goal for me as my life changed. 

I hear from so many other transgender women whose lives parallel mine. Either they continued with a skill they earned earlier in life or were able to meet others who made their gender transitions so much easier. One way or another,  the losses didn't feel as bad. Sadly, there are the other trans women and transgender men who never seem to not struggle with their loss of family or employment. It is just another example of how being transgender is everything but a choice. 

Perhaps, as being transgender continues to be better known thanks to the internet, everyone will have the chance to pick and choose with more confidence what is lost and what is found with their life. Then have a chance to cherish what is found.

Sizing Up the Crowd

 

Image from Roberto 
Nickson on 
UnSplash

Recently, when I met friends at a local brew pub for brunch, I needed to walk the distance of what was called the "great hall" to meet the group.

Once again I needed to make sure I was standing up as straight as I could, while throwing my shoulders back and faced the reality all transgender women face, was I going to be spotted as some sort of a gender impostor and even laughed at. I didn't and even though the brief walk felt as if it went on forever, I made it to our table without incident. At that point I thought I had it made, until the young server called me "sir". Which is another sad experience I have previously written about. 

For some reason, when I transitioned into a feminine transgender world, I didn't think the public would share the same fascination with studying other women as I did. I can't tell you how many times my old guy self aggravated my second wife (and others) by trying to sneak a peek at an attractive woman. For whatever reason, I couldn't explain to them I wasn't looking because I desired the woman, it was because I wanted to be the woman. At the time, I was having a difficult time wondering if I could ever achieve my dream of cross dressing out of my old unwanted male self. There were so many working parts of a woman to duplicate, the whole process seemed impossible. I needed to fashion my own hips, breasts and hair just to arrive at a point where I could put the entire feminine package into motion. 

It wasn't until I began to leave my dark and lonely gender closet behind and attend transvestite mixers did I begin to think I could succeed. Through the help of the mixers, I was able to judge how other cross dressers were successful with their presentations...or won't. I saw everything from men in beards and dresses, all the way to beautiful transgender women who were completely undetectable as former boys or men. As I sized up the crowd, I knew which direction I was headed. Most certainly I did not want to be with the bearded crowd and wondered to myself if the transsexual group was where I needed to be. Keep in mind, this was back before the transgender label was widely understood or used. What amazed me too was how intense the pressure was to size up the crowd and fit in to where you belonged. 

Little did I know, I was just beginning my trip out of the closet and into the world and I would need to obsess on my appearance until I gained the confidence to go forward as the person I was. Deep down I knew I would never be the prettiest woman in the room, I just wanted to be the trans woman at peace with herself. So when the crowd sized me up, they recognized who I truly was and it was good enough. I learned also, the greatest majority of the world didn't care about me anyhow and they were involved in their own little worlds. My second wife was always fond of telling me it always wasn't all about me when it came to my cross dressing and she was right. It was just the ones who did care who became the problem. As I made my way along my gender path, I was fortunate to dodge most of the haters and live my life without severe incidents.

I am a firm believer in the younger generation doesn't see gender as a threat and in the future sizing up a younger crowd will be less of a threat to transgender women and men everywhere. I, on the other hand, when I chose to live a life as the high maintenance gender chose to always be on the stage of life. 

It's Your Journey

 

Image from the Jessie Hart
Archives...

There are many different paths on our transgender journeys. Some are eerily similar some are very different.

On occasion, our paths align due to age considerations. We were the ones who grew up in the pre-internet days before it was invented as well as the social media which has become all so powerful. We are the ones who grew up in very lonely and dark gender closets which made it feel as if we were the only ones in the world who wanted to be another gender. At that point many of us chose to subscribe to Virginia Prince and then received our cherished and closely guarded issues of Transvestia. The magazine Prince published. 

Perhaps you are younger and experienced another journey through the internet. I remember vividly the days when my wife and I could afford our first computer along with the ultra slow dial-up internet. Almost immediately I found myself in trouble when my wife caught me corresponding with a like minded individual on a message board in a nearby town. She turned to be more computer savvy than me and learned to track my movements on our system. What I learned was, I needed to better hide what I was doing or stay off the message boards all together.   

At that point, I was using my issues of Transvestia to locate transvestite mixers close enough to me in Ohio so I could travel to them. When I did, I was able to see and meet other cross dressers who were following similar journeys as well as many who weren't. There were the ones who seemingly trying to out run their feminine desires by still acting super masculine in a dress and heels. I certainly didn't feel a part of that cigar smoking crowd. (Before cigars became cool for women). Then there were the future transsexuals on the other end of the spectrum. They were impossibly feminine and I felt were far out of my league as I was very insecure about my appearance as a cross dresser. Even though I wanted to be a part of their world, it was difficult to be admitted. I partially solved my problem with blatantly tagging along with the so called upper class when they normally would go out to gay venues and continue to party after the majority of the group had retired to their rooms in the hotel where we were meeting. 

It wasn't until many years later, after many errors and successes in the world as I tried the basics of living as a transgender woman did destiny set in and I was accepted by small groups of cis-gender women who allowed me to really learn the basics of existing in the feminine world. 

Over the years of writing a blog, I have been able to correspond with other trans women who were able to benefit from similar situations. Mainly when they were invited into "women only" spaces. It was during these times I learned the true essence of communication women use when no men are present. My obsession changed from appearing feminine to actually acting feminine. I learned how much I have changed when I go back to the earlies days of blogging to see what I was up to. 

Whatever your journey, I hope it has been a successful one for you. There are so many facets to consider such as family and spouses which lead to staying in some sort of a closet by choice. Which there is certainly nothing wrong with that. I will forever wonder what would have happened with me if my wife would have lived on. Would we have ultimately split up when she said she would never live with another woman or could have a compromise been reached for both of us. Pursuing gender affirming hormones for me was the breaking point which I was free to do after she passed. So as you can understand I am not putting myself up on any sort of a pedestal because destiny led my journey to living as a fulltime trans woman. Pedestals are very fragile and easy to break. 

Hopefully it has been your journey and you have been able to live it with a positive outcome.  

Labels

 

Coccinelle, early transsexual woman

As a long time transgender woman, I have seen my share of different labels coming and going over the years.

The first one was the declining use of the word transvestite. I remember the days when there were very much only two labels you could use to describe yourself,  If you cross dressed in the clothes of the opposite gender, you were a transvestite and if you desired a sex change (as it was known then) you were a transsexual. Over the years, the sex change terminology went through it's own changes, As I remember, the sex change became known as gender reassignment surgery. Then gender realignment surgery. All these labels lead to the same result. As most labels seem to do in the LGBTQA+ community.

While we are on the subject of the LGBTQA+ letters, the expansion of the letters themselves needs mentioning. As our community expanded and the knowledge of the overall gender spectrum expanded, more letters needed to be added to the initial LGBT letters. To include more people the abbreviation was expanded to include more than the initial, gay, lesbian, bisexual and transgender community. At that time the queer or questioning was included plus the "A" which stands for Asexual and/or Ally. I guess the plus just stands for any more possible additions in the future.

Way back when, transgender wasn't even a term at all and even though it is rumored Virginia Prince (transvestite pioneer) was the first to use the term, it's true history is murky.  The best history I could find is transgender (or it's shortened trans term) first appeared in the 1950's and 1960's. I only know I started to be aware of the term in the 1970's. The whole process meant so much to me because all of a sudden I had a term or label which applied to me since I knew I was much more than a cross dresser and not as much as a transsexual. The perfect fit for my gender questioning mind. So I adopted it as my own.

These days, labels seem to change as fast as the world around us. The word transgender sadly has been made infamous by all the political attacks' against it. In the same way, LGBTQ+ has been popularized also when associated with the unfortunate uproar over the trans situations. Yet another change has recently been updated also. Hormone replacement therapy or HRT is now known as gender affirming  hormones.   

Of course the bottom line is all these terms are nothing more than labels which often lead to confusion all the way to altercations. Especially in the transgender community when people start to think they are more trans than someone else. It all comes at a crucial time when we all have to stay together to present an unified front to the world.

Through it all, if you are into the increasingly complex world of labels, I hope you have found one which fits you. 

Creating a Tangled Gender Web

Image from Robert 
Anasch on UnSplash

When I look back at my life, I wonder if I knew all it would entail would I do it all again.

The only change I would make would be to have have the courage sooner to go ahead and transition from male to female. Even though it sounds like a good idea to have jumped off my gender cliff earlier, the problem became the world around me. I am seventy four and the world at large has gone through several different realities when it comes to the transgender world. Back in the day, there was very little feedback when it came to being transgender at all. Basically, there were only two categories, transvestite (or cross dresser) and/or transsexual. Neither of which felt very natural to me, Plus if you went the transsexual route, you were expected to move and leave your old life completely behind. I never thought I could do it either. I still had a daughter I loved plus enjoyed small parts of my male life.

In other words, I was stubborn to the point I thought I could still transition my own way. If indeed I ever came to the conclusion I was trans. As I procrastinated through life, I created an increasingly tangled gender web. I was trying to balance what was left of my male life along with a long term marriage with a woman I loved very much. At that point, I was trying my best to try to discover my true gender self. My web grew ever tangled the more I tried to either escape or relax and enjoy the ride. The ride included taking my transition one step at a time. I found as I struggled in my tangled web I needed more than one transition to move forward. It took the evening when I finally decided to go out to be a transgender woman rather than as a very serious cross dresser just out to escape my male world. to change my mind The difference was major in that I was striving to discover who I really was rather than just playing some sort of game I had indulged in for most of my life. Much of it was in front of a mirror. Naturally the world was much more brutal and I needed to be better.

As it turned out, I was increasingly successful in both of my lives in the main two binary genders which caused my web to be even bigger and more tangled. I ended up sneaking out behind my wife's back, which caused severe problems with my marriage. It was increasingly evident I was stuck in a battle between two women. My wife and my inner woman were both strong feminine people and the war weighed heavily on my overall mental health. Before it killed me, I needed to finally escape the tangled web I was in and begin to live as a woman. Or, as my wife told me, be man enough to be a woman. 

Once I escaped, and with the help of several key friends, I was able to start all over in a new feminine  life. Although, once I began the life, I understood the fact my new life wasn't so new after all. My inner self had been waiting and observing my life just waiting to take over. Of course after I escaped the web, she had her chance and I was living my dream life.  At the least I never led a boring life. 

   

The Ultimate Obsession

 

Image from Brett Jordan
on UnSplash

As I recall, the ultimate obsession I had with being feminine began with explorations into my Mom's clothing and makeup. Once I started I couldn't let it go.

Little did I know, I would need to follow quite the winding and rough path as I crossed the gender border from male to female. As soon as I conquered one of my goals and escaped my very dark and lonely closet another wall or barrier would crop up to challenge my obsession. An example would be how I imagined just improving my outward feminine appearance would be enough to help me live in the world as a transgender woman. All the process really did was set me up for other huge challenges.

Challenges such as how I would or ever could learn to communicate with other women in their world. Nothing in the process was easy and often terrifying. The old "no pain-no gain" saying proved to be all too true. Just attempting to modulate a feminine sounding voice to match my appearance was the ultimate challenge. Plus I needed to learn to always make eye contact with other women as we engaged in conversation. A simple statement saying I loved another woman's ear-rings often proved to be the ice breaker I needed to survive in my new gender world. 

Through it all, my male self was fighting me all the way. Every move I made to try to enable me to be more feminine was a problem to him. Deep down he knew he was fighting a losing battle because when I was pursuing my authentic self I felt so natural. So everytime I was questioning the path I was taking, the bottom line was if it all felt so natural, it was the right thing to do. Somehow I needed to conquer my fears and temporary setbacks and follow my own personal ultimate obsession. Follow it I did.

No matter how complex my life became as I ended up attempting to share a life between the two primary genders, until the pressure became too intense to survive, I did my best to live my life. My male self kept resorting back to what he had always done...internalize his feelings and hope for the best. His best never came as I continued my path towards my ultimate obsession. Even then, I had no idea if I could make it to my ultimate goal of living a life as a transgender woman. Fulltime with no interference from my old male self. 

As I always point out the struggle nearly killed me and I would not wish it on my worst enemy. I was one of the lucky trans women or trans men who all of a sudden found the doors opening which would allow me to finally follow my obsession which had followed me my entire life.  Destiny showed me the way around life's setbacks such as close friends and family dying. It all allowed me to have very little resistance to living my own life as I saw fit. Also near the same time, the Veterans health care system I was part of started to provide help with hormone replacement therapy, which I was fortunate enough to be healthy enough to be a part of.

In short, my life which was very much in shambles faded away and I was finally able to achieve my ultimate obsession. To lead a feminine life and even to become remarried again to my wife Liz who accepted me all the way. 

The path I took was never easy but on the other hand, my trip was never boring and provided me with a unique look at life others never have.  

The Light

Image from Junior
Ferriero on UnSplash

 
Sadly, most transgender women or trans men experience complete darkness in their gender closet before they are able to come out and explore the world.

Of course in the pre-internet period, gender information was very difficult to come by and it wasn't until pioneers such as Virginia Prince came around did printed material begin to surface on a regular basis. As well as the so called transvestite mixers which began to crop up in other areas except the East coast. For those of us in the Midwest and other places, finding and meeting other like minded cross dressers seemed to be the impossible dream. The light in the gender closet was dim to say the least. 

Perhaps the worst part of seeing the light was determining exactly what it was. Could it be a beneficial beginning to escaping the severe gender dysphoria I was facing, or was it merely the light of a train rolling uncontrollably towards me. At any point of time, discovery of my feminine desires could lead to severe consequences to the male life I had worked so hard to survive in. It took me years and even decades to figure out the light wasn't the train. Partly because of all the time I wasn't sure it wasn't the train.

Those were the dark days of my gender despair. The days of venturing out in the public's eye only to be laughed at and rejected which led to ill-advised "purges" of my feminine wardrobe. Somehow, deep down, I knew the "purge" would only last a few days and the fleeting freedom I felt wouldn't last. I was right and before long, my desire to rebuild a feminine wardrobe and wear it became strong again. This time I wanted to climb on board the train and ride it to a new found transgender freedom, away from my old male self.  Rather than the light at the end of the tunnel being a negative, I deeply wanted to turn it into a positive.

It was approximately this time of my life, in my thirties and early forties, when I met others whom I could identify with as far as my gender struggles went. I found I didn't have to drive far to Columbus, Ohio for small mixers with a diverse group of people ranging from cross dresser admirers all the way to transsexuals. All of the sudden, the light became a beacon on what my life could become if I worked on it hard enough. I found achieving my possible goal of living a feminine life meant so much more than just appearances. My second wife kept pounding on me to be more and I took a long time to realize what she was saying. Surviving as a trans woman would mean learning to live a new multi-layered life.

Even though I had made it a huge priority to study women all my life, I needed to use the light to take my studies to another level. Think of it this way, I was pursuing a new masters program in gender before I could put the male past behind me and move forward.

Finally I arrived at a point where my closet door had opened widely and my long hidden feminine self was able to take over. She was able to take over the light and enable it to be so much brighter.

The Ship has Sailed

Image from Sebastian Bjune
on UnSplash

Very early in life, I learned being a male in any way was going to be a struggle.

In response I went through all the necessary contortions I could find to seek approval in a gender world I wanted no part of. Ironically I found I needed to be proficient as possible at being a male or be bullied. Even though, deep down, I knew I had missed my male ship all together, I kept on trying. I did my best to succeed in all the male-centric activities I tried. Even though I was a dismal failure at playing sports, I tried my best to play football and baseball through high school. It was my attempt at jumping aboard what was left of my male ship before it sailed totally out of sight over some sort of a distant horizon. Through it all, women still remained a mystery to me. As I wrote yesterday, I didn't have my first date with a girl until halfway through my junior year of high school. Deep down I felt girls had all the benefits of life because they could sit back in their pretty clothes and wait to be asked out.

I on the other hand, had to summon all of my courage to ask a girl out, which again, I was a dismal failure at. My first dates with girls were always set up by friends who I thought felt sorry for me. I never understood until much later in life the grass was not always greener on the feminine side of the gender border when my spouses explained to me the torment they felt as they waited to be asked out. 

As it turned out, my gender ship had already sailed no matter what I did. Even though I tried my best to lead a successful male life, I was always haunted and  pushed along by the fact I was always supposed to be feminine or any label you wanted to place on me. There were many such as cross dresser or  transvestite all the way to transsexual and finally transgender. None of them really mattered as I desperately searched for my gender truth. Finally, all the stress and tension my gender dysphoria caused me led me to a very serious suicide attempt. 

After taking all the pills and not dying, I returned to my old male life with a new purpose. I knew my masculine existence I worked so hard to maintain couldn't continue. The ship had sailed and if I was ever going to have a chance at living a meaningful life, it had to be as a transgender woman.

When I did come to my gender conclusion, I never looked back. I started my life all over again in a woman's world by beginning hormone replacement therapy or HRT. At that point I never did miss my old male ship at all. It was as if a huge weight had been lifted from my shoulders and I was allowed to live again. As I was given a second chance at life, I most certainly did not want to destroy it and I set out to become the best person I knew how to be. 

It turned out I wasn't alone in starting over. My inner feminine self was waiting for my male ship to sail also and lend a hand. She did a great job because she waited so long.to have her way. It was good because I needed all the help I could get.