Not an Act, not a Phase

JJ Hart Speaking Up at a Trans Wellness
Conference.

Very early on in my crossdressing experiences with the mirror, the vast majority of feminine fashion and makeup I could find came from my mom. As I grew of course, I was guilty of stretching her clothes and ruining some of her makeup.

For some reason, she never brought up my passion for being feminine. Plus, she never found my secret hiding places for my clothes. I think now, rather than confront me about a problem so intense, she chose to ignore it, thinking it was a phase and would go away as I grew up. If the truth be known, there were times when I wished my gender issues were a phase too. Those were the times when I "purged" or threw away my feminine clothes and makeup, swearing never to cross dress again. Of course, every time I purged, the pressure would build again, and I would start all over again to femininize myself. Over the years, I came to learn my connection with the feminine gender was anything else but a phase. It ran much deeper in me. Ignorance was bliss until I began to face the reality of who I was. 

It certainly was not a phase in my life which made my cross dressing anything but an act also. My experiences helped to reinforce the fact I was not trying to fool anyone when I first entered the world as who I labeled as a novice transgender woman. 

So, if I was not in a phase, or just acting like a woman to fool the public, who was I? I was in a personal struggle to search for any idea I could latch on to until I finally had to face the reality of my transgender womanhood. Yes, I went through all the questions of just being in a gender phase, all the way to thinking I was just trying to fool the world when I attempted to present myself as an attractive woman. 

Once I did come to the point where I truly accepted myself as who I really was, the entire process helped me to establish myself in the world and make new friends. My worst fears of being viewed as just a man who put on a dress and makeup as a part time basis were never realized. On the other hand, I played upon the fact I was different from the rest of the public as a transgender woman. If I was to be unforgettable, I most certainly needed to make sure I was making a positive impression. I spent much of my time listening to other women. Trying to pick up the smallest nuances of a ciswoman's life and how I could apply it to myself. 

As I advanced along my long gender path, I needed every small boost I could get to get me by with several close calls in an unfavorable world. It took me years to understand my gender issues were anything, but a phase and I was not a glorified drag queen in the world. It just took me more time to prove it to others. Basically, because I was scared of the knowledge of who I really was and feel secure in my transgender womanhood.

The Forgotten Woman

Image from UnSplash.

 Over the years of gender infighting, I needed to carefully sustain my transgender womanhood because she often was the forgotten person.

To begin with, she began life as a second-class citizen in my world when I was born as a male in a male dominated family. Essentially, she had two walls to climb immediately to survive at all.   First of all, she did not have any on hands guidance from mom or girlfriends to show her the way through life and secondly, my male self was successful at all in the world, she was completely forgotten. The fragile complement between my genders had to be maintained at all times or she would disappear. Many times, I asked myself why I wanted her along to begin with, but the answer kept coming back, I needed her.

I discovered the hard way, the occasional trip to the hallway mirror dressed as a girl with full makeup, just was not going to cut it. I just needed more. If I could manage to look like a girl, why couldn't I be a girl, if only in my mind. The problem became, when I had to return to my male reality, I needed to forget my girl self altogether. Many days, it seemed like cruel and unusual punishment. when the only true punishment came at the expense of my already frail mental health. All too often, depression would set in when I forgot my feminine self and could not least appease her by cross dressing in the mirror. 

Another problem was, the more I appeased my forgotten woman, the more my male self-hated it. He fought hard when any portion of his life was threatened. He tried his best to make it easier in life by gaining white male privileges which were difficult to give up. I became successful as a male, but try as I might, I could not forget my inner woman. Who, at the time, was learning more and more how to establish herself in the world. Many times, my male self would win the battles in our life when along he was losing the war. A typical female move he was too blind to see as he blustered along in life. 

When my forgotten woman became less forgotten and more accomplished, my male self-started to panic as he could see the end in sight. Without being a winner. Basically, he teamed up with my second wife to attempt to save what they could of my life. At that point, decisions needed to be made in the worst way. My so-called forgotten woman had learned she could indeed live a life on her own terms. The ability to stand on her own two feet after all those years in a closet was so liberating, she knew she could never go back and, on the other hand, my guy knew deep down he was defeated. 

Living a transgender life she had always dreamed of was suddenly all that mattered. She dictated I start gender affirming hormones to feminize my body outside and inside and that was just the start to being accepted in the world. At that point my forgotten woman was not forgotten anymore, and she got her just due for all the years she waited for control. She loved every bit of it.

Just Being You

 

Paula from the UK.

In response to yesterday's post "In the Passing Lane". Paula wrote in and commented:

"I have often heard it said that the best accessory for passing is confidence. For me these days it is not so much a matter of confidence as familiarity, I rarely make an effort I am just being me.
I have a friend who uses the phrase "When the World experienced me as a man" while I like that it has emphasized to me that not only is the World now experiencing me as a woman, but that I am experiencing the World as a woman!"

First of all, thanks for the comment. It sounds as if you have reached the point in your transition where confidence is not such a huge factor but was early on in our lives.  I am similar to you in that I have reached the familiarity stage, and I am just being me. The point I always try to get across when I write is how long it took me to arrive at where I am at and how I got there. 

As I consistently write, gender dysphoria played a major part in my life, and I was very insecure on how I was appearing in the public as a novice cross dresser or transgender woman.  It took me years of effort to discover who the true me really was. So, I could go forward in the world and seek out a stable transgender womanhood. As Paula said, the world was experiencing me as a man, and it had to stop before it destroyed me.

I think one of the problems we have as transgender women and trans men in the world todays politically charged climate against us is, for the great majority of people, gender is a given and not something to be questioned. I cannot ever remember a time when I did not question my gender on a regular basis. What a strange and wonderful experience that would have been, and I can only imagine the strides I could have made in my life if gender dysphoria was not a part of it. Finally, I arrived at the point I could take my male life no longer and needed to do whatever I could to experience the world as a woman.

But what exactly does that mean? Do cisgender women consciously think of themselves as women or is it a series experiences a female naturally goes through which takes her to womanhood. Plus, let us be clear, not every female makes it to where they can experience life as a woman. Again, the overwhelming majority of the population never has to go through any sort of questions about their gender. Even to the point of not being able to separate gender from sex. With all those big questions, it's no wonder the average person has no understanding of the transgender community. 

I am biased, but I think having the chance to experience life as a man, then a woman is difficult. But it makes for an enlightened life I never expected to have. Once I did arrive, I respected the process and never wanted to go back to my experiences as a man. Except to learn from the positives and the negatives which made me a better person. 

In the Passing Lane

JJ Hart.

Early on in my life as a very serious cross dresser before I came out as a transgender woman, I obsessed about my presentation as a woman. Or, in other words, was I "passing."

At first, I went overboard and tried to appease my male side and dress sexy. Naturally, I was a dismal failure with my choices and ended up attracting too much negative attention to myself. After too many disastrous evenings in the public's eye, I finally learned my lesson and began to blend in with the cisgender women around me.

The problem was, still trying my best to slip behind the gender curtain and survive as a transgender woman was very difficult. At the time, a transgender woman friend of mine said it best when she told me I passed out of sheer willpower. She was correct, and I knew I was never the most attractive woman in the room but none of that really mattered as I was beginning to live the life I always had dreamed of. If others somehow resented it, they would just have to get over it. 

Being the keen observer of women, I always was, I found out not all cisgender women passed in the classical sense either. The skillful ones worked around their physical appearance issues with fashion and makeup choices which flattered them. I figured if they could do it, so could I. Finally, my fashion and makeup became second nature to me. At that point, I was not passing out of willpower but more out of inner confidence in myself as a novice transgender woman exploring the world for the first time. Once I found myself in the passing lane, it became easier and easier to stay there.

Even though I had fewer and fewer accidents in my quest for transgender womanhood, I still suffered minor bruises along the way. Mainly from cisgender women who completely did not want me in their world and went out of their way to show me.  Many of the attacks I suffered from were passive aggressive in nature and they took me awhile to get used to, but I did. I developed the extra sense most women have for the world around them and went on with my life as a better person. Secure, I was doing the right thing in my life and did my best to stay in the passing lane. 

These days, I have the benefit of age on my side. The genders naturally blend with age, so with long hair and a little makeup, I can survive in the world. Also, I don't have the vanity about my feminine self I used to have. Plus, I am so fortunate to have my staunch ally and wife Liz by my side the overwhelming amount of the time. An example was the vacation we went to the Florida Keys on a tour bus. If you are not familiar, one way or another on a tour bus, you get to know others. On the trip, I knew I had it made in the passing lane when a couple of women asked if we were sisters. I immediately relaxed for the remainder of the trip.

Overall, since finding my way into the passing lane was a matter of sheer will power. I had always believed if you wanted something bad enough, you could achieve it. Deep down inside, I never had wanted anything more than to be a woman. To arrive at my dream, I needed to get into the passing lane and stay there. Using whatever feminine tricks, I could find and use.

As "Stana" from "Femulate" once said, make sure you properly signal before you get in the passing lane. Once you make it, you will love it.

Adjusting to Change

 

Image from
Rafella Mendes Diniz
on UnSplash.

I am biased, but I think adjusting to a lifestyle in a gender you were not born into is one of the biggest changes a human can make.

As many of you know, I took nearly a half a century to adjust to my gender changes. Looking back, some of the changes were a blur while others were so very slow. The reasons possibly were there were so many changes I made to arrive at the spot where I could take the big leap. For example, the night I went to an NFL Monday Night Football game with a lesbian friend of mine and her family. I was just coming out as a transgender woman and was scared to death but knew I needed to make the move and go with her. Needless to say, after the evening, my life changed forever.

The other night I mention often was when I went to see the Christmas lights at a local grist mill, by myself as a woman. I was not as nearly afraid as I was at the football game and ended up enjoying myself immensely. I felt secure in my fashion choices for the evening and was warm and cozy when I went up to one of the hot chocolate vendors for a warm drink with extra marsh mallows. Most importantly, I did not run into any major problems at either venue and my confidence skyrocketed. Maybe I could be secure in my transgender womanhood after all and live out my dream. 

By now, you may be thinking was that all it took to propel my confidence forward into a new life and leave the old male life behind. No, it was not. It is difficult to mention all the nights I spent out alone as a single lonely woman before I found friends to share my changed life with. Through it all, I needed to be so careful to separate my old male life with my new femininized one. Which meant to separate everything I was talking about to new people. Plus, I did not want to create a totally false past in my life and ignore everything I worked so hard to achieve. I found I could bring in the family I had and just change the perspective I was speaking from, and it worked. At the time, fortunately, I was busy closing out my old male life anyhow which had for the most part collapsed, so the time was right for a major change.

Surprisingly, change did come easier for me than I expected. My femininized life was a pleasure to adjust to. Since, I should have been living it all along. It was like my feminine inner soul was telling me she was right all along. If I just had the courage to make the gender change and stick with it. 

All the adjustments I needed to make in life to survive were worth it for me. Finally, at the age of sixty, I had seen enough of the small changes I was trying to make as a stopgap measure and I decided to rid myself of all my male clothes, start gender affirming hormones (HRT) and live the life I was always meant to live. 

How did I know I made the right change? Because, after I did it, I felt so relieved and natural. I let myself go to fall off my gender cliff and had a very soft landing. All those years which started out as just me in the mirror had come full circle and I was able to live my desired life. All because of the changes I went through.

Finding Your Comfort Zone

 

Image from UnSplash.

Being a transgender woman, trans man or cross dresser means you need to find your own level of comfort as you transition.

For all sorts of reasons, some of us decide to go all the way from gender realignment surgeries to deciding to stay in their gender closets. It is a difficult decision to face the possibility of losing everything in the life you have worked so hard so succeed at over the years. 

In my case, comfort levels came sparingly to begin with, then increased in frequency as time went along. For example, I had an exceedingly difficult time becoming situated as a novice transgender woman in the world. Possibly, most of my problem came from my own refusal to face up to who I truthfully was a person. My gender situation led me to a very bad situation where I was stuck between the two binary genders, male and female. Of course, I still needed to maintain my male world in the job I worked, but on the other hand, I was spending every spare moment I had trying to reach my comfort level as a trans woman. The end result was, because I was denying my true self (female), I was wrecking my already fragile mental health. 

Fortunately, I was able to work my way through my messy mental problems and come out rather unscathed with the help of a good therapist. Together, we were able to separate my bi-polar depression issues from my transgender issues which dominated my life. And I mean total domination. I was very into advancing my life in a feminine world and attempting to figure out how and when I should let go of my old male self. Finding my comfort zone finally began to come in stages.

What I did was set up what I thought was a mini bucket list of things I wanted to do as a woman. Or at least try to. As with anything else in life, I sailed through a few of the items on my list and hit a brick wall on others. Overall, I was able to use the confidence I gained from my successful feminine ventures and go back to the drawing board and figure out what I was doing wrong on the others. For example, one of the best things I did was stop going to the gay venues where I was only perceived as a drag queen and began going to the sports venues I was comfortable in. When I did, I was encouraged to begin to build a whole new person as I quickly began to establish myself as a regular. Since my business background was in similar venues, I knew the basics of establishing yourself as a regular. Show up often, try not to be a distraction, smile often and tip well were the basics. Since I already stood out from the crowd as a transgender woman, the rest was easy. 

Through it all, the comfort zone I needed the most was access to the woman's room, for obvious reasons since beer was my drink of choice. I was overjoyed when rest room access was granted to me when I became a regular. I even was invited to join other women when they made the short trip to the bathroom. I was very sure I had arrived. 

It is easy to equate being in a gender comfort zone with acquiring all important confidence to get by in a new world. Life was amazing when I was a woman and hell when I was not, so finally, even I could tell a change was needed. No matter how complete the separation would be.

My needs had changed from my old male days and to not face them head on would be a return to the same old gender problems I had faced my entire life. For once in my life, I decided to do the right thing, and I found my comfort zone. My male self-gave up and freed me up to build my transgender womanhood. 

A Destination or a Journey?

JJ Hart

 Early on when I was stuck in my dark gender closet, I viewed myself on a way to a destination, not much different than a vacation from my male self. 

Then, when I began to experience more "vacations" than I could handle, I began to notice I was on more of a journey than I thought. Looking back, I was missing all of the signs I was much more than a part time crossdresser, pursuing a harmless hobby. The difference always was I wanted to do more than look like a girl, I wanted to be a girl. Needless to say, I spent many hours of my spare time wondering what my true problem was. Time, I wished I could have back. 

Instead of getting any of the time back, I invested it in my femininized appearance in the mirror, and I still thought I was on some sort of a mysterious journey no one else knew anything about. It would be years before I was able to attend transvestite mixers to meet other likeminded people who I thought were on the same path as I. Imagine my shock when I found out I had waited so long to find out I did not fit in well with almost all of the others who were attending the mixer. Somehow, I just still felt different. Probably because most of the attendees viewed themselves as men in dresses and my views of my gender self were just beginning to form and they were so much deeper than thinking I was a man in a dress. 

It was about this time, I realized I was on more of a journey when I began to know transsexual women who were making the ultimate gender step in their life, gender realignment surgery to be exact. I was very intrigued by the idea and deep down I wondered if that was the journey I was headed on. The problem was I was stuck where I was in my male life and was not prepared like my friends were to make such a serious move. To be sure, gender surgery would certainly be a journey for me as I had quite the complex male life I was living and to be truthful, on occasion, I did enjoy the white male privilege I had earned. 

All I ended up doing on my journey was screwing up my mental health. Simply, the stress of juggling two of the binary genders became too much and I was very self-destructive. It was then I knew, my gender path was so much more than just a destination and I really needed to step up my game if I was going to survive. It was decision time. Either I went forward as a transgender woman or retreated back into my male world. 

The deciding factor was I felt so natural as a trans woman, so I did not stop my journey until I made it to a point where I could save my mental health and even my life. Certainly, even though I had reached many destinations along the way, my life turned out to be a gender journey which at times was touch and go. I ended up not going and stayed the course to my own form of transgender womanhood and was a better person for it. 

Gender Mandates

 When I was born, I did not have a choice of which gender I was supposed to be, my birth gender was male and there were to be no questions asked. 

In other words, I was mandated to enter a male world which I came to totally dislike and rebel against. Similar to many of you, I first had an idea something was wrong with my perceptions of my gender at a very early age when I went exploring in my mom's clothes. My first glimpses of myself in the full-length family mirror were memorable and electric. I knew right then, I needed to figure out a way to do more. 

The problem was, in my very male dominated family, I was mandated to go in only one gender direction and follow the male path. Afterall, if I made it, I was offered the promise of white male privileges. On the other hand, if I was caught cross dressing at all, I was surely on my way to see a therapist and perhaps be thrown into the dreaded conversion therapy. My answer was simple; I needed to continue in my underground cross-dressing ways and hope I did not get caught.  My major problem was my slightly younger brother who I was always stuck being with. Somehow, I did manage to do more and slightly lessen my mandate. When I did, I found I could enjoy my femininized self even more than I ever had before.

Of course, the most male mandate I faced was being drafted into the United States military during the Vietnam War. Since women were excluded from the draft, it was an exclusively male experience. I still resent having to face my time in the service when women did not, but I served my time for three years and was honorably discharged. I suppose too, my time in the Army disguised the true me to the outside world, since my friends and my dad already had served their country. It was mandated to be my turn if I wanted it or not. 

Slowly but surely, over the years, my mandate changed from male to female. I went very slowly to insure I would have less and less mishaps on my gender path. Each step I took gave me the confidence to take another. Of course, at some point, my mandates would collide. When they did, my mental health struggled, and I was fortunate (after several tries) to find a qualified therapist who helped me separate my bi-polar condition with my gender issues.

My largest feminine mandate came when I started gender affirming hormones. I knew almost immediately I had made the right decision. All the changes the hormones made to my body felt so natural. Inside and out, the changes were so dramatic, I think my body was always waiting for them. 

As mandates go, I would be remiss if I did not mention the gender privileges which go with the mandate.  Since I have spent quite a bit of time up close with male and female gender privileges, I know a little about both sides. As with most things, male privilege is more upfront and direct, while female privilege is more layered and indirect. 

One way, or another, mandates are a serious part of life and are difficult to control. Plus, they are so hard to deny.  

Transgender Dreams

 

Image from Alex Azabache 
on UnSplash.

My last question from my transgender grandchild for my yearlong book of questions I am putting together went something like this: If I had it all to do over again, what would I tell my twenty-year-old self about life.

First of all, before I answer, the questions come from a site called "Story Worth", and at the end of a year, they put all the weekly questions together to form a book on your life. It was a gift from my daughter. I am more than three-quarters through it already with a chance to add more questions for a small amount of extra money.

Now, back to my twenty-year-old self. First of all, at that time, I was consumed by two issues. Being drafted into the military along with a strong desire to be a woman. Conflicting problems to be certain which I was having a very difficult time dealing with. In the tried and true if I had known then what I know now, I would not have spent so much time worrying about basic training and beyond. I learned as I went through basic, that after I got into shape, it was just a team building experience with military realities built in. I made it through much easier than I thought I would and then prepared myself to serve out the remainder of my three-year enlistment. To be honest, I did not join the Army because I wanted to, or I thought it would make me anymore of a man. I was drafted into the service because of the Vietnam War. 

If anything, my gender issues became stronger when I was away in the military, as I constantly day-dreamed any spare moment I had about when I would become a civilian again and be able to pursue my dream of being a woman. It was all I had to get me by. 

Little did I know at the age of twenty, how complex and difficult my gender journey would take me throughout my life. To put it into perspective, the Army only took three years away from me, while deciding to finally come out as a transgender woman, took me forty more. I am sure my twenty years old would have asked why it took me so long to face the reality of who I really was and quit making excuses. I kidded myself for years thinking I was strong and would have to admit to my twenty-year-old, I simply wasn't. 

I would also have to tell my young self to not be afraid to dream because without dreams to achieve, often we arrive nowhere. I would have never made it to my goal of transgender womanhood unless I dreamed of it all those years and took steps to finally make it. Regardless of all the self-destructive behavior I put myself through. You only have one life to live and should try to do the best you can to preserve it. 

I was fortunate to have lived long enough to see my life come full circle from that confused twenty-year-old I was. When I did, I was able to achieve transgender dreams I never thought possible.  Of course, none of us know our ultimate destinies, the least we can do is accomplish goals which lead us in the right direction.

If you are in your closet, thinking you are trapped like I was, just do your best to look for the opportunities you may have to escape. Later on in life, it all may come back to help you with your transgender dreams.

Transgender Breakthroughs

 

Image from 
Shane Rounce  on 
UnSplash. 

Even though we are all at different points along the way in our gender journeys, we still have break throughs which keep us going. 

My earliest breakthrough was when I was still admiring my girlish reflection in the mirror, the first times I was able to try on my mom's clothes when I was all alone. I thought I looked great, and the feeling stayed with me for a couple days afterward until I could try to cross dress again. The problem was, I felt deep down there was still something missing, I wanted to do so much more than just look like a girl, I wanted to be a girl. The problem was, I did not have any gender information to go with my discovery of who I really was. I was still years away from even hearing for the first time about transgender women and what the term meant to me. I still have vivid recollections of the time I saw the transgender term used and just knew, for the first time in my life, being a trans woman fit me. Naturally it was a major breakthrough. 

Little did I know, just having a label to attach to myself, would prove to be a challenge for me as I went through life. No longer could I rely upon a mirror's image to get myself by. I needed to get out into the world and see if I could present well enough to mix in with the public. When I did, I found being a woman was no joke, and I needed to really work to achieve my goal of transgender womanhood. 

One of the big problems I had was, when I was coming out, I tried to keep one foot firmly in my closet. In case something went wrong, and I needed to go back. The only problem with keeping a foot in my closet was the time I spent in the world as a woman spoiled me, and I never wanted to go back. It was very difficult for me to tell my inner feminine self no. What I decided to do was, formulate a version of my own feminine bucket list. I would try increasingly more difficult things as a woman and see what would happen. For example, if I made it browsing in a bookstore, I would take it a step further by ordering a coffee and using the women's room the next time I was there. Or I would try to go to a different restaurant all together and order lunch. 

I try not to act as if I am recommending my path out of my gender closet to others because when it comes to leaving your closet, one size does certainly not fit all. Circmstances such as experiences in the public and where you live can vary so much. However, in my case, it did take a certain amount of courage to come out. There were many times when I waited in my car adjusting and readjusting my makeup before I gathered the courage to walk into a venue I wanted to try out as my new femininized self. Since a few of the venues I had been to several times as a man. 

Then, courage gave way to confidence and when it did, I could enjoy my new exciting life. Before that happened, it seemed to be a challenge every time I turned around. Perhaps I was expecting too much by thinking I could turn decades of living a reasonably successful male life around so quickly. Being a woman of any sorts presented a challenge because women lead a so much more layered and complex life than men. Once I accepted the challenge, I discovered I was in the right place as a trans woman and there would be no turning back. 

Even though the current barrage of anti-transgender legislation shows no sign of abating soon in many places, we have to remember transgender women and trans men will never be erased and have always existed and you can too. If you try, you can have your own breakthroughs and live a solid life out of your closet. You just have to be careful how you do it and keep an eye out for the bigots which are increasingly brave. In my case, I needed to realize the worst the bigots could do to me was not as bad as continuing to live in my gender closet. It was very dark and lonely, and I could not take it any longer and I set out to experience my own transgender breakthroughs.

Building Gender Bridges

 

Image from Alexander Rotker 
on UnSplash.

I have always been one to build too many bridges to jump off of in my life. 

In fact, if I don't have anything to worry about, I will create something. Looking back, I was especially bad at building huge, tall bridges when I was at the height of my trip to transgender womanhood. I felt I was partially justified in doing so because of all the problems I experienced when I was coming out of my gender closet. 

Before I began my trip, I was a fairly freewheeling person. If something happened for me to take care of, I would and at the same time, not spend much time worrying about my future. Even though I still faced major problems in my life, I could still conquer them, or escape back behind my skirts, heels and hose to hide. As I progressed in my life, I found my time was running out as a parttime cross dresser. Either I needed to do more or purge myself altogether of a pastime which had kept me from jumping off so many bridges I had built. 

Another problem I discovered was when I began to be more skilled at building my gender bridges was becoming, I was increasingly under more pressure to be successful. The more success I felt as a transgender woman, the easier my life became except for the very serious bridges I faced such as communication with the world. 

The best time I have for building my bridges is late at night when I am trying to sleep. These days, I have plenty of things to worry about. In fact, next week, my wife Liz and I will be heading north to my daughters, mother in laws lunch. During that time, I hope to find out what has happened to my transgender grandchild job offer as a civilian nuclear engineer with the Navy in Maine. Hopefully they have been able to stay under the radar so far and has maintained the job which they wanted to start this fall. (They is their preferred pronoun.)

Going to see the family is always very affirming as I have been accepted for years as my authentic feminine self. Early on it was very difficult for me to adjust to because nearly everyone in the room had known me for years as my old male self. Others including my first wife, who is the mother of my only child usually always attends, and she has a difficult time sometimes not referring to me with the proper pronouns when recounting a few of the long-ago days when I was trying to live as a macho man. Plus, we also met each other while we both served in the Army in Germany. With all the extra baggage I carry when it comes to her, I think she has done a good job of building a new bridge to me over the years.

Now, at my advanced age of seventy-five, I find myself looking ahead at the biggest bridge of all. When it is time to enter a new reality when I pass on. I have decided to do the best I can with all the aches and pains I have and keep a positive attitude. Of course, there are other major bridges to think about also when and if I need to enter assisted living, which I am not looking forward to. Liz and I were supposed to attend a special seminar put on by an attorney specializing in "elder law", but Liz got sick, and we did not go. So sometime in my future, I need to insist we find an attorney to give us a consultation. 

In life, it seems, there are always bridges to build. It is just a special problem unique to gender conflicted transgender women and trans men. Overtime, we can become very good builders and even better at hiding our results. Fortunately, there are more and more trained therapists to help us these days. Ironically, some of us have to go through several therapists until we can find the proper fit. So, we can find someone who can build a solid bridge, rather than tear it all down. Which, if you are like me, you tried to do many times during various purges. 

I Made Nothing

 

Image from Camillo 
Contreras on UnSplash.

Several of my earliest memories of success as a cross dresser came during the Halloween parties I went to. 

When I wore my very short mini dresses, showing off my freshly shaven legs, I found I had several women come up to me and say, I "made" a good-looking woman. Years later, when I began to understand "woman speak" better, what they probably meant was I "made" a good-looking woman, for a man dressed as one. 

Furthermore, I soon came to realize, I was not making anything. I was simply being who I was. In order to learn that simple fact, I needed to live decades of life as a parttime cross dresser or novice transgender woman. Or I needed to live my gender truth before I could claim it. I needed to get out of the mirror and into the world to learn if I really belonged there. Those were the days when no one in the world around me would give me a break. The public was laughing at me (rightfully so) because for the most part, I was dressed like a clown in drag. Plus, my old male self, my second wife and my mirror did not want to let go of me. Making my life miserable and destroying what I had left of my mental health.

Juggling two genders at once was a tremendous challenge when I caught myself practicing living one gender when I should not have been. Being called "Ma'am" at my macho management job was certainly not cool or good but somehow, I survived to live on to the next day when I was determined to do better.  What happened was, I did keep getting better at my feminine side and increasingly began to leave my male side behind, which scared him.

Fear, as they say, is a powerful motivator and instead of giving up, my male side and my second wife grew increasingly close and forced a battle of the wills. In other words, neither one of them wanted to lose their place in the world. Which included my universe. It turns out, I did make something...a huge mental mess for myself. It is one of the excuses I make for taking nearly fifty years to break out of my gender bonds and flourish out of my closet and mirror. I just had to make sure I was making the right choice and there was so much pressure on me. 

As I grew out of the mental gender mess, I had made for myself, I gained the critical confidence I needed to establish myself as a secure transgender woman. Not just a femininized man. Since I had spent a lifetime getting there, the personal coming out was extra special to me. It was as if my feminine self was telling me what took so long. As it turned out, I shared her belief in wondering why I took so much time and wasted so much nervous energy I wish I had back. As we all know, worrying over what we did in the past is a waste of time, unless we are learning from our mistakes.

I felt better when I realized I did not make anything, when it came to my gender issues. Rather, I inherited them from some unknown source which made life a challenge. A challenge I needed to finally accept before the pressure I put on myself had grown too heavy to carry and I had to put it down and go with the life which made me feel natural and alive. When my transgender womanhood became secure thanks to friends I had, I felt so much better as I built a new life.

Do the Right Thing

 

Image from UnSplash.

I learned early on from my parents when in doubt, you should always do the right thing. At the same time, I learned from them, dressing to look like a girl was not doing the right thing. So, I needed to completely hide it.

Later, when I attempted to navigate my gender path, I found many obstacles I did not foresee hurting me. But they did and brought about many doubts. Of course, the main doubt was, should I be doing all the cross dressing I was doing in public at all. Still, I persisted and improved my craft at presenting well as a femininized person. Finally, I arrived at a point where I could leave my dark gender closet and attempt to live a new scary yet exciting life. The more I explored as a novice transgender woman, the more I wanted to do. Which brought me back to the question, was I doing the right thing. 

Similar to so many of you, I suffered from extreme guilt as my second wife kept telling me my gender desires were selfish pursuits. The sad part of it was, for the most part, she was right. She wanted very little to do with me wanting to be a woman, so I kept it away from her. Not the right thing to do in a marriage but was my only recourse. At that time, I only had a distant dream of perhaps living someday as a transgender woman. All I needed was the courage to face my reality. 

Because of a number of reasons, I needed to do much more exploring the world as a transgender woman to see if I could survive. First, I had to look the part, then I needed to live the part. Standing in my way, were the usual questions of transitioning to another gender such as what would become of my family, friends and job. As well as did I really hate my male life that much. I wasted hour upon hour antagonizing over what I should do and would it be the right thing. 

I was stubborn of course and refused to do any more than observe several transsexual women I knew from a distance. From their stories I did know they had really good safe jobs or were close to retirement so they could support themselves whereas I did not and had no idea of what I would do for an income. Plus, I also needed to consider, both of them were flat out gorgeous and had no problems presenting in the world as women. I did not labor under any idea I even came close to being as attractive as them and did not have that going for me either. After taking all of this and much more into consideration, I did not know what I could do about my gender dilemma which was not doing my mental health any favors.

What I did do was try to continue on the path I was on. To increase my awareness of the world as a transgender woman as much as I could at a time, I went as far as I could. Even absorbing major clashes with my wife over what I was doing. I can't always say I did the right thing as I learned more and more about living in the new world I was seeking. There were too many times when I had to out and out lie to get out of situations, I found myself in. In all fairness to my wife, she told me to stop it and just become a woman to bring peace to both of us. Still, I did not have the courage to change my life and leave her behind. I did not do the right thing. 

You regulars know what happened next. My wife passed away quite tragically from a heart attack leaving me all alone with my dogs to put my life back together. I rapidly turned to my inner feminine self as the strongest person around and did the right thing and finally turned to a life I always just dreamed of. 

On a side note, I may be missing a day of blogging tomorrow as my wife Liz and I have a daylong seminar to attend. Sorry for the inconvenience!

When too Much Wasn't

 

JJ Hart (Middle) with two friends.

As I continued along my long and winding gender path, I (on occasion) ran into situations when the public seemed to be too much. 

Examples were the times I was approached in public by strangers when I did not want to be. Very quickly I needed to judge their motives. Did they see me as a man in a dress on one hand, or as a woman on the other. Naturally, it made a big difference when I returned home and rated my experiences as a novice transgender woman out in the world for the first time. How did I do? Was I too much for my own good and did I need to tone it down, or attempt to do more?

There were the times when I managed to thrive in situations where women dominated and times I could not and ran home. Back to my gender drawing board. There seemed to be so much to learn, I was overwhelmed by the task ahead of me if I was ever to achieve my dream of living a femininized life as a transgender woman. 

In the end result, normally I found too much just was not when I was trying to get ahead in a new world I was just getting used to. The problems occurred mainly in the areas of fashion and makeup, as well as where I was trying to go when I went out. Once I got them under control, I was able to build a stable new life in the girls' sandbox. Once I earned my way in. Often earning my way in, had its own set of challenges. Mainly I had to find out how to play correctly to be accepted. On the other hand, even though it was difficult to do, I had to play to learn a life's full of lessons in a hurry. As I always say, my women's workbook was blank to this point, and I needed to write it. 

I found as I struggled to fill out my workbook, I needed to be extra vigilant in how I viewed other women, since I was totally on their turf. For the most part, I did my best to hold back on my opinions and speak mainly when I was spoken too. It worked well enough until I could get my feet on the ground, and I could move forward as a transgender woman. My goal was to build my new life as a confident, intelligent woman in society, but I needed to prove to myself my goal was not too much and would destroy my dream of transgender womanhood. Fortunately, throughout my life, I had several strong positive feminine role models to work from and add to my workbook. When I was able to add their influences to the inner female, I already knew was there, the women formed a strong bond to guide me through my struggles.

Overall, I discovered rarely too much just was not. What was happening was, I was just paralyzed by fear to move on with my new life. Once I got over most of my fears, I was able to move on and be free to live a better life. A better mental health life waited for me when I quit fighting two genders to survive. 

Wait? There is More?

 

Hand Beaded Hair Beret
by Liz T Designs
Haur by JJ Hart. 

When I reached every dead end on my gender path, I thought I was finished with my dream of ever being a transgender woman.

It turned out, when I researched every dead end, most were just blind curves I needed to negotiate, so I pushed on. It turned out, one of my biggest problems I had was dealing with my own fears. Would I be discovered and laughed at or worse. When neither started to happen, I gathered my courage to do more and more in the world.

Mentally, I was able to make another major transition from cross dresser (which never worked for me), all the way to transgender, which did. The process turned out to be one of the biggest mental moves of my life and in many ways saved me from harming myself. All the years of not making a connection and connecting my gender dots were over, and finally, I was able to understand why my life had been so difficult. Mainly, it was because I was so busy fighting myself, I did not have the room to search for anything else. Keep in mind too, while this was going on, I was also trying to juggle a male life which I was succeeding at. Making it more and more difficult to give up.

Through it all, I did find out there was so much more to my femininized life than my old male one. To get there, I needed to keep pushing. I set up mini bucket lists where I wanted to try out as a trans woman to see if I would be accepted. At first, I went to the easy venues such as malls, clothing stores and bookstores to see if I could make it in my new world. Once I did, I attempted to step up my layers of difficulty to challenge myself to be better, and at the same time build my confidence to seek out more in my new life. My end goal with all of this was to discover if I indeed did have any chance to live my lifelong dream of being a woman. Even though I went too far on my bucket list ideas, I still had to push forward because so much was at stake in my life. Afterall, I had family, friends and jobs to consider among other things I did not consider yet because they were beyond the next blind corner. 

Sometimes, what was behind the next blind corner was easy to deal with and other times presented me with situations which were very difficult to deal with. Such as the time I had the police called on me due to an ill-advised rest room visit, all the way to being run out of my regular venues by a group of men who were harassing me. Predictably, it took me quite a bit of time to regain my confidence, but I did and moved on to greener gender pastures. 

One of my biggest obstacles to finding the greener pastures was my lack of knowledge in communicating as a woman. I never thought the public would want to interact with me as quickly as they did, and I was not in the least prepared for it. For the first time in my life, I needed to really listen to other people and prepare early for a proper response which was good enough to get me by. I even resorted to taking feminine vocalization courses at the Veterans Administration to help get me to the next corner to see if there was more to do. 

It always seemed there was more to do as I attempted to immerse myself into my transgender womanhood. Especially when I started gender affirming hormones. When I did, welcome changes began to happen quicker than I expected and once again, I was not prepared for what I was facing. For example, I had a timetable in my head for when I could finally put all the male life behind me and start a new life from all the gender work, I had done. Primarily, because of early surprising breast development, I needed to scrap my mental timetable and get started on my new life. From there, there would be no looking back.

From HRT forward, I thought there would be fewer mores in my life, but I was wrong. My wife Liz came along and with her, she expected me to accompany her in the world doing things I had never tried before. We went on vacations, went to the symphony as well as junk yards for car parts and made a life together. 

Now as I look to the final chapters coming up in my life, I know there are many more significant mores in my life coming up. It is just a part of life. Maybe transgender women and trans men just have more to navigate than the average person as we seek a new gender life. 

It's Complicated

Image from John Barkiple
on UnSplash.

 
In many ways, this post is an extension of yesterday's post.

In it, I attempted to write about the connection (or lack of it) between members of the transgender or cross-dressing communities. What continues to amaze me on many levels is how complicated the outside world does not see in our world. So many in the world still think all we have to do to "solve" our gender problems is as simple as not putting on a dress for transgender women, or a pair of pants for a transgender man. Granted, it is very difficult to explain what is going on in our own gender challenged minds. How could I explain my desires to others, when I could not explain it to myself. Back in those days, there were not even therapists available who had any knowledge in the gender field to provide any help.

In the meantime, I internalized all my feelings and dreams of being a transgender woman someday, much to the detriment of my own already fragile mental health. My problem was (among many) I was naive and did not realize how complicated my genders were. I had no workbook to study from. Being completely on my own, forced me into making many mistakes I did not foresee coming as I followed a curvy gender path. The only woman I sought guidance from, withheld any significant advice, basically because she just clashed with and did not like my inner feminine self which was trying to emerge. 

What I did then was move past my wife and discover what my new world as a transgender woman had in store for me. All of it was difficult in the worst way when my old male self-ganged up on me. Both of them were losing traction on claiming my world and resented it on so many levels. It stayed so complicated because I loved my wife deeply and we had built a twenty-five-year marriage often on the ashes of my gender conflicts. When I was down and out emotionally, my wife was the first to bear the brunt of my frustrations. I knew I was wrong, but there was nothing I could do to battle my overwhelmingly frequent desires to being a woman. In fact, when my second wife was still alive, I was very actively exploring the world as a transgender woman. Primarily to discover, if I could survive at all.

My explorations proved what I suspected all along. Women lived a very layered and complicated existence and being able to join in at mid-stride would not be easy. Similar to attempting to jump on a very fast moving merry go round without it slowing down. Once I found myself on the feminine ride, I was given a chance to really learn and absorb what a woman's life was all about as my brain was rewired to survive. What amazed me was how quickly I was welcomed into a woman's world as one of their own. The worst which happened to me was when I was gently laughed at by my new cisgendered women friends when they said, welcome to our world. Which I was overwhelmingly happy to be a part of.

Ironically, if I was prepared or not, I entered a world much more complicated than the gender conflicted world I left. Plus, what happened was, the more I grew into my new world of transgender womanhood, I grew away from my wife. Before she unexpectedly passed away, it became obvious our marriage was doomed to at the worst being a total split, to at the best living as two women on their own. One-way or another, fate decided the question for me.

In many ways, I wonder if I had ever imagined such a complicated journey through life was going to be in store for me. I guess at the least, I could say, life was never boring as I suffered from being the round peg being forced into the wrong square hole. My reward was being able to say I learned how both sides of the binary genders lived, and I could choose which one I wanted to live as.

I Just Couldn't Live Without Her

 

Image from Brian Kyed
on UnSplash.

At a certain moment in my life, I had reached the point of no return where I was living with two women, the one inside of me and my wife of twenty five years.

The question remains, how did I find myself in such an untenable, precarious situation. The answer was, it was not easy, and I really had to work hard to get there. Decades, to be exact. Once I pulled myself out of the mirror, and put her into the world, I knew I could never go back to being a parttime cross dresser. I could never live without her.

Many times, I have gone through the many steps I took on my path to transgender womanhood. To provide you all with a more precise look at my actions, we need to go back to the years when my second wife was still alive. What I began to do was sneak out of the house when she was working cross dressed in the world just to see if I could. After a very rough beginning, when I was laughed at, I began to get my high-heeled feet on the ground and do better. So much better, I began to think my ultimate goal of living as a transgender woman on my own terms may actually be possible. 

From there, I began to spend every spare moment I had alone as who was to become my authentic self. I became so immersed in becoming a woman, I needed to concentrate on the times when I still had to be a man at work, or with my wife. The biggest problem I had was, deep down inside I knew which gender route I had to take to survive in the world, but I was afraid to face it. The fights between my wife and I became so bad, a couple times she just told me to be man enough to be a woman. I was not man enough to do it, but I was stubborn enough to keep trying to live a middle of the road gender life, which became impossible to maintain. My mental health suffered, and I began to be more self-destructive than I already was. All the way to attempting suicide one night.

Fortunately, I was not successful in my suicide attempt, and I proceeded down the same path I had been on before. This time taking my cross-dressing activities into my own restaurant and threatening my substantially good job. Again, deep down I felt if everyone knew of my deep, dark secret, I would be relieved of the hell I was living because I had to make a change away from the male life I was living. 

Just before my wife suddenly died, I made one last ditch effort to partially purge myself of my femininizing supplies. I went all the way to growing a beard, so at least I was telling myself I was making an effort to return to the male world. However, there was one big problem, I was miserable and about the time I needed to go back into my feminine world, my wife suddenly and tragically passed away from a massive heart attack at work. Through all of our problems, I loved her deeply and we were married twenty-five years.

I often wonder what would have happened had she lived. I think now, my internal female would have won out and I would have completed my gender transition. She would have won because I felt so natural in the world as a transgender woman. When it came down to which woman I could not live with, I would have had to have chosen the woman I should have been all along and hopefully patched up my life with my second wife. So, at the least, we could have stayed friends.

Living the Dream

Image of dreaming woman from 
James Forbus on UnSplash.

 For the greater part of a half a century, the thought of transgender womanhood remained a distant dream for me.

The main reason was, I spent decades denying who I really was, as my male self-sought to rule me. Sadly, he either won many gender battles or made life overall miserable for me. When he was doing it, my dream remained in place as I wondered how big my rainbow was and would I ever live my dream. In the meantime, I kept experimenting in the world as an out transgender woman. 

When I had the chance, I would do things such as attend downtown festivals all the way to watching an outdoor concert as my new exciting authentic self. I had a black leotard top I often wore with a favorite pair of flair legged silky pants and a glittering pair of black and gold sandals. I even went as far at the daylight festival I went to; I added a pair of sunglasses so I could see anyone checking me out in a negative way without them being able to see my eyes. My biggest discovery was no one paid me any real attention. In other words, I was beginning to think I could actually live out my dream of transgender womanhood. 

From there I attempted to expand my new exciting life. I completely enjoyed the time I spent living my dream and soon, never wanted to go back to my male life. When I was forced back, I hated it. Often, I took it out on my second wife and other close people around me. By internalizing my dream, I grew angrier and angrier and almost lost good jobs because of it. 

It was not until I began to spend almost all of my spare time living my dream, did I realize I could really succeed at it. Finally, I had made the transition from the mirror to the world and was ready to attempt to learn to do more. Overall, I began to have more success than failures when I learned not to push my gender envelope too far. I was accepted at several venues where I wanted to go to watch sports and drink beer plus, I gained a couple unexpected female friends when I did it. I was discovering I was closer and closer to my dream of transgender womanhood was almost here and I wanted more and more of it.

I did not think I would ever make it to my dream, but destiny was on my side and all of a sudden, at the age of sixty, I realized I was at a huge make it or break it time of my life. Either I completed my gender transition then, or I never would have the chance again. I seized the opportunity and even had the chance of meeting the cisgender woman of my dreams who accepted and even encouraged me to be a better version of myself. She told me very few humans ever have the chance to reinvent themselves, so I should strive to do it right. As I did.

At my age of seventy-five now, I still have the everyday pain which comes with age, but I try to write and walk every day to stay active. Perhaps by doing so, I can expand my dream to the fullest. 

Thanks for reading along! I hope you can live out your dream also.

Losing Through Winning

 

Image from Humphrey Muleba 
on UnSplash. 

Sometimes during our lives, we have to lose to send ourselves forward into a better place.

It seems, transgender women and transgender men have so much more to lose when they transition across the gender border. As I often mention, we have to consider spouses, extended family, friends and employment as we grow into our unique authentic selves. I spent years in anguish trying to determine what to do about the two women fighting about my life. I mean my strong inner woman and my equally as strong wife of twenty five years, both of whom, I loved dearly. 

It turned out, the only loser was my male self, and he was not going down without a fight. When I was stuck between genders, my mental health suffered greatly. Even leading me to a suicide attempt when I did not think I could make a decision and could not take it any longer. I was attempting to live my regular working life as a male and the rest of the time as a transgender woman, and it was tearing me apart. The gender nightmare I was going through, I would have not wished on my worst enemy.

Finally, I decided I needed to lose one of my genders attempting to run my life. Due to an ever increasingly deep down feeling I was doing the right thing; I chose to go deeper and deeper down the gender rabbit hole and pursue my transgender womanhood. When I did, an unbelievable exciting, fulfilling new life opened for me. All of a sudden, I was being invited behind the gender curtain to girl's night outs and even accepted a gift from my daughter to have my suddenly longer hair styled at her upscaled salon. Looking back, I think my hormonal estrogen level increased significantly that day due to osmosis. Suddenly I learned why all women value so much their time at the beauty spa's. I was learning again why I could never go back to the male world I was losing.

As I looked around, what else did I have to lose? My wife had passed away, I closed my restaurant, lost most of my close friends to cancer, so I had nothing but a temporary fast food managerial job I hated to get me by until I could take an early retirement. Plus, I was on gender affirming hormones (HRT) by then, and my body was femininizing fast. My wins were rapidly overtaking the losses in my life. 

During the space of approximately five years, I had walked through the gender door perceiving I was little more than a parttime cross dresser and came out the other side as a full-fledged happy transgender woman. My male self-had totally lost and it was time for me to enjoy the win with my new women friends around me who taught me more than they ever knew about valuing myself. 

As with the rest of you who have gender transitioned, or are seriously considering it, I am sure I don't have to tell you what a big decision it is. First you need to accept yourself, then see if others will accept you too. Once you do, you can begin to win and put your losses behind you.  

I Was Ready but Was the World?

 

Image from the Trolley Stop, Dayton, Ohio

It took me years to understand and accept my transgender womanhood, but once I did, what was the world going to think.

Once I had worked very hard to cross the threshold into being able to put a reasonable effort into presenting as a woman, the difficult work started. Even back in those days, I was able to learn basic tricks to take a good-looking picture but then I found putting the picture into motion was the problem. The whole scenario presented me with big new challenges, The largest mistake I made was underestimating how quickly the world would want to communicate with me. All of a sudden, when I was going out to be by myself, someone (usually another woman) would invade my little world. Which was suddenly growing rapidly. Initially, until I grew used to it, just trying to look another woman in the eye and talk to her was a real challenge.

I started by merely trying to mimic the tone and sound of the person I was talking to, then took femininizing vocal lessons to aid my efforts. I discovered quite quickly, I was more ready for the world than I thought. I found putting too much effort into communicating with a stranger could be a turn off and too little interaction could come off as being bitchy. So, I needed to be careful and usually let the other person lead the conversation. 

For the most part, I found the world was ready for a stray transgender woman just learning her way. I even was able to converse with several other women I met regularly in venues where I was a regular and so were they. I was amazed I had such an easier time talking to them woman to woman than I ever did as a man. One venue in particular in my world was a tavern called the "Trolley Stop" in Dayton, Ohio. It was/is the oldest continuing tavern in Dayton and I quickly became a regular of Gabby the daytime bartender. I knew from previous experiences, having support from the bar staff was key to my overall acceptance. So, I did my best to be friendly, spoke only if I was spoken to, and tip well. Being accepted in the Trolley Stop helped to really expand my world as a transgender woman and prove I was ready to do it. To make matters even better, the Trolley Stop even hosted a lesbian mixer every month or so and I enjoyed good times there as well. 

All of a sudden, the more I was out in the world as a trans woman, I proved I was ready to make it completely in the new universe I was in. It turned out to be one of the most exciting and satisfying times of my life. I was interacting and communicating with others. When I did, I made a whole new circle of friends (mostly women) I write about frequently. They provided me with the building blocks I needed to find my gender dreams. Once I had the solid foundation I needed, the rest was easy and fulfilling. Especially to my long hidden inner feminine self who had been punished for my entire life.