Not Scared? In the Wrong Room

 

Image from Alexandra Gorn
on UnSplash.

I cannot begin to tell you how terrified I was to interact with the public when I first began to attempt to live in the public's eye.

One night in particular always stands out in my mind. It was the evening when I had pre-determined my cross-dressing days were behind me and I was going out as a transgender woman. Furthermore, I knew if I was successful, it would change my life forever. As I prepared for my big night out, I took extra care with my outfit, makeup and hair. I wanted to make sure I blended properly with all the other women I would be interacting with at an upscale bar I was going to which was heavily frequented by professional women who worked at a nearby mall.

Once I made the short trip to the venue and found a parking spot relatively close to the front door. As I sat in the parking lot, the pressure to go in increased dramatically. As I nervously checked and adjusted my makeup in the car's rearview mirror, again and again the fact was not lost on me I could be changing my life forever. By the time I gathered my courage to actually enter the venue, I could barely breathe and was gasping for air. 

It took me awhile to gather my courage and enter the front doors of the place and interact with the hostess stand. Deep down, I was hoping the hostess would be busy seating other patrons so I could sneak on through and find a seat at the bar. The short distance from the hostess stand to the bar seemed to be miles to me but I made it and luckily found a corner seat at the bar by myself. Plus, the bar itself was supported by two large thick pillars. I figured if I found a seat next to one, I could blend in and hide if I needed to. I did not need to hide as I was approached for my order by a friendly bartender. 

Immediately, my fears began to melt as I ordered my first drink and even started to relax a bit and watch all the other women who had begun to arrive at the bar to enjoy each other's company. As I observed the group, I saw no one was noticing me. So far, so good. No one noticed a very scared novice transgender woman in their group. 

Of course, this evening was only the beginning of my new transgender journey. I knew my life had changed forever. I could never go back to the old unwanted, boring male life I was living. To move forward, there would be many nights when I would be very scared. Somehow, I learned to feed off my fear to propel me forward. No longer was I a weekend cross dresser, I was reborn as a very serious transgender woman.

My end game was using fear to refine my push forward by putting extra time and effort into my fashion and makeup. That way, when I needed to walk past a crowd of strangers in a new venue I was in, I could do it without any issues. 

I finally decided, if I did not feel any fear at all, I was in the wrong room. Especially, in today's climate, it pays to always be aware of your surroundings. Maybe fear is a strong word, but awareness is not. 

The Gender Envelope

 

Image from Alexandru
Zdobau on Unsplash.

Sure, I spent or waisted far too many years before I fully transitioned into transgender womanhood.

I was too slow for such a long time actually pushing my personal gender envelope when I was busy telling myself I was no more than part-time cross dresser. I saw no harm in just doing my best to look like a woman until it just wasn't the answer I was looking for. The more I cross dressed and improved my feminine presentation, the more I pushed the envelope and looked for more. Very quickly, my yearly Halloween adventures just were not enough.

I began to wonder if I made a good impression at Halloween, could I make the same impression if and when I tried to go out in public as a novice transgender woman. Following many trials and error experiences, I found I could survive a public which largely did not care about me. The big error I always point out is when I was not receiving any attention to speak of as a woman, I began to dress trashy to attract the wrong sort of attention. I was mistakenly pushing my gender envelope the wrong way. When I finally began to understand the best ways to dress my male body and apply the proper makeup, did I begin to be successful and blend in with other women in the world. 

Once I had accomplished all of the fashion, hair and makeup necessities, I allowed myself to further push my gender envelope. When I did, I found myself needing to understand how women exist in the world. Or how do they communicate with other women and men. I had a quite a bit of catching up to do since I was attempting to catch a moving train heading down the tracks. I did not have the benefit of growing up female with a mother or peer group to guide me. I always point out; the passive aggressive system of interaction most women operate under was the most difficult for me to learn. Since childhood, I was always used to the full-frontal confrontational world men operate in so I was attempting to survive in a whole new world.

Once I did survive, I began to push even harder, ignoring warnings from my wife on what would happen if I was ever caught. I put the male gay bars behind me and moved on to big sports bars and lesbian bars where I could actually be myself. I thought I had reached my peak when a dear friend of mine invited me to a trip to a NFL Monday Night Football game in Cincinnati. Even though I was very scared at the thought of going, I could not turn down a chance to empty my envelope and lay my gender cards on the table. Since I am not really a gambler, I hoped the lifetime of preparation I put into this moment would serve me well. 

The moment did serve me well. As always, I survived and became a better woman for it. Plus, I learned the game was only the beginning. The life in my transgender womanhood I was going to experience, would be extremely fulfilling and everything I thought it could be when I started pushing my gender envelope.

Transgender Destiny?

 

Image from Marvin 
Kuhn on UnSplash.

When some unknowing person says something like I had a choice to be transgender, I just laugh and say being trans was simply my destiny.

I believe my journey began before birth when my mom was prescribed the D.E.S. medication which was popular at the time for women who had a history of experiencing problem pregnancies. Since my mom had undergone three still births before me, it seems to me, she would have been a prime candidate for the drug when I was born in 1949. 

From the very brief studies I have seen on D.E.S., it was supposed to flood the mother's womb with estrogen. Which of course affected the fetus also. 

How ironic would it be that the initial dose of estrogen I received in the womb would later on come back to help me. It took me fifty years, but eventually I discovered when I went on HRT or gender affirming hormones, how natural I would feel. No adverse effects at all, just a warm feeling I was finally doing what was right. In other words, I was coming home. The only problem was my life was filled with the gender torment of fighting my basic will to be feminine. What if I had just given in to my instincts so much earlier. Would life had been more pleasant?

The problem was though, gender was never cut and dry with me. I was cursed with a male body which on one hand kept the bullies away but on the other, made it very difficult to obtain a feminine look when I found the secret time to cross dress as a girl. I had to take one or another which caused me considerable stress to my mental health. Waking up every day wondering if I was a boy or a girl, was certainly no fun. 

Plus, there was absolutely no one I could explain my gender issues to. I grew up in a male dominated family and knew there would be no way I could be accepted. I knew, even being caught in girls' clothes would earn me a trip to a psychiatrist. Deep down, I knew there was nothing mentally wrong with me, so I did want not any part of a visit. Remember, this was back in the 1950's when there was little to no knowledge of gender issues. In fact, gender issues were labeled as mental disorders. All that happened was, I was driven deeper into my feminine gender shell.  

As time went on, I developed a very thick shell which when I finally ready to do so, was difficult to escape from. In other words, I needed to establish too many levels of feminine escape before I made the final jump to the other gender frontier. I needed to slowly discover if the other gender as a transgender woman would provide me what I had been missing all of my life. I felt as if I was sliding down a slippery slope into a valley, I knew very little about. 

As I slid down the slope, I saw bit and pieces of my old life go by as I mourned some of the pieces and I rejoiced at others. As I felt more and more comfortable in my new transgender womanhood, I knew the landing would be as soft as possible. I found my gender needs had changed, for the best. I finally took my chance at the age of sixty to forever change my life and live fulltime as a transgender woman.

I finally had my chance to fulfill my D.E.S. destiny. I could not reclaim the time I had lost but I could lead a better life going forward.

A Spectator in my Own Life

 

Image from Ryan 
Mangino on UnSplash.

There were many times during my life as a transgender woman, I felt as if I was a spectator looking in on the action.

The whole process was very strange to say the least as I was thinking, just who was that person. Plus, having the chance to think what I was doing was a totally different sensation. The entire problem stemmed I think, from the earlier years of my life when I was positive, I was two different people all together. One male and one female. It was not until much later on when I began to realize I was always feminine and fought all things male when I could.

Slowly but surely, I began to realize the truth and began to notice my cross-dressing nights out involved much more than just attempting to look the best I could. My spectator began slowly to change away from watching a male life unfold to watching a female one do the same. Helping me were the girls-night-out invitations I received. Following a bout of impostor's syndrome, I suffered through, I settled down and enjoyed myself. When I came to the conclusion I had just as much right there as the next woman. We had all came to our right of womanhood through different paths and mine was just different.

Finally, I grew tired of just being a spectator in my feminine life and wanted more. More meant being a spectator in my male life. Since I was still working and living part-time as a man, it meant I really needed to concentrate on my speech and movements when I was still a guy. In fact, there were a couple of embarrassing times when I was called Ma'am at work when I was in male mode. 

Early on, being a spectator in my own life was certainly a curiosity. Especially, when I thought I was just a cross dresser and putting on a dress was just a hobby. The closer I moved to true transgender womanhood, the more I learned that was not true. As I always say, the key moment in my life came when I realized I was not a man cross dressing as a woman, I was a woman cross dressing as a man. The tragic part was I went through male puberty and was testosterone poisoned as I grew up. I did not appreciate when my soft body turned to hardened angles as well as the other male changes but there was nothing I could do.

When I found my gender destination, I stopped being a spectator and began to be a more involved participant. For me, flipping my gender became an intensely frightening but natural part of my life. Living my dream was so dominant in my thought pattern, I had no problem with girls-nights-out and even could not wait for them. My newfound confidence as a woman completely pushed any idea of me being a spectator aside and opened the door for me to be a more well-rounded participant. Of course, confidence always grows more confidence, and I grew to the point where I had nothing else to prove to the other women I was around.

As I look back, being a spectator in my own life as sometimes a necessary but very different part of my existence. The entire process sometimes helped me to understand where I was going towards my dream of transgender womanhood.  

And Then he Was Gone

 

JJ Hart at Club Diversity
Columbus, Ohio

It took me nearly a half a century to rid myself of my male self and begin living as my authentic feminine self.

Even though much of my progress towards my gender goal was physical, much was mental also. The physical part I am referring to was the portion of my transition which revolved an intense period of time I went through attempting to judge my appearance in my own personal mirror. I was so into myself, my wife began to call me the pretty, pretty princess and told me I was ignoring what a woman really was. She was right and it took me years of research and struggle to learn what she really meant. 

As I learned, the more my male self-fought me as he did not want to give up any of his life and male privileges he had fought so long to earn. It seemed every small gender victory was hard earned until he was gone.

Perhaps the biggest factor against him was I felt so excited and natural in the new world of transgender womanhood I was creating. Surely, I was still having my ups and downs when I tried out the public when I went out, but the downs were becoming fewer and farther between. Plus, my amount of terror I was still experiencing as a transgender woman was decreasing by the day. I think now, the major reason was I finally made the mental decision to go forth in the world as a woman on my own terms rather than the part time cross dresser I had somehow portrayed myself to be. Some may say I was dealing in semantics, but the thought pattern was a revelation for me. 

As he disappeared, my female self-had no problems filling the void in my life. My long-buried woman self-had no problem putting her past behind her as she stepped out into the bright lights of a new world. I think having no resentment made her a better person people could relate to and like. In fact, I found many new people related to me as a woman than ever before as a man. 

Ironically, after a very slow start to the fifty years of gender discovery I endured, once I seriously started my transition. time went very fast. Perhaps, it was because every night I went out, I was learning so much new on not being just the pretty, pretty princess and finally experiencing what my wife told me about being a woman was all about. Or I was finally given the chance to go behind the feminine gender curtain into a world dominated by women. When I did, I found women ran their own world their own way without the help of men. During the girls' nights out, I was invited to I learned what was important to women and not men. Even along the way, I learned the power of non-verbal communication between women when one night I was warned away from an intoxicated man in a venue I was a regular in by a bartender I knew. With one look, I immediately went the other way away from him and was safe.

Finally, after so much learning and experiencing a new life as a transgender woman, I think my male self-saw the writing on the wall and decided he was done. When he did, a huge weight was lifted from my shoulders. It seemed carrying two people all those years took a toll on me, and I wanted out. 

Burning Gender Bridges

 

Image from Adam Wilson
on UnSplash

During my life, I have always excelled in self-destruction. It seemed, whenever I had succeeded in anything positive, I always tried to tear it down. 

I blame the entire process on two basics, one of which on how I was raised. My parents never accentuated the positive at any time. If I received a "B" in any class, invariably I heard, why didn't I earn an "A" and I was not applying myself properly. The other basic was anything I accomplished as my male self; I did my best to reject. I did not in any way want to accept any success I earned as a male. So, I did my best to burn the gender bridge I created. 

Of course, the more I went down my gender path towards transgender womanhood, the more bridges I needed to burn. Everywhere I looked, the stakes were higher in life. All along I was accumulating more and more success as my unwanted male self which made my decision so much more difficult. Still, I forged on with my torch burning brightly. To hell with the results, I was going to attempt to follow my gender dreams anyway. Finally, I arrived at the point where seemingly I was subconsciously trying to sabotage myself. In many ways, I was desperately attempting to hide my deep dark cross-dressing secret while, on the other hand, I secretly wanted everyone to know I had always wanted to live as my authentic feminine self and did not care what they thought. Still, I needed to be careful as I had deep roots to my male past. Spouses, family and jobs were at stake. So, I tried to be sure of what I was doing before I cut the gender tree down.

Perhaps the most substantial bridge I needed to burn was to my job. I was a very successful restaurant manager in a regional/national casual restaurant chain. The management was very male dominated, and I knew there was no way I could ever transition in the same job. 

I decided to try going to other similar food/bar competitors thinking no one would recognize me. Long story short, I found out the hard way I was recognized as a version of my male self. To make matters worse, I tried to frequent my own operation and was close to being immediately recognized. In doing so, I burnt a major bridge which I don't think my wife ever found out about. It was bad enough when she knew I was breaking the agreement we had for me to never leave the house as a transgender woman.

The new bridge I built when I burnt the old one was when I decided to buy my own restaurant. I figured if I was the owner, no one could tell me what to do. That was true to an extent until one night a very evil former acquaintance met me in the parking lot to tell me my lifestyle was keeping the public away where we operated. I don't know how true what he said was but one way or another, I had burnt all my gender bridges and there was no way I could ever go back. 

When I transitioned and began my life as a transgender woman, I was able to build new strong bridges for the first time in my life. It was like my feminine soul was excellent in her building skills and could not wait for a chance to thrive.

The sad part was/is how much destruction I had to go through just to arrive at where my dream could be born. It turned out the birth was the easiest part of it all, as I set out to live a fulltime new life in my transgender womanhood. I finally had the chance to put my fire out. At least the destructive one.   

Take Nothing for Granted

 

A night out with JJ Hart.

Last night, my wife Liz, her adult son and I went out to dinner at our favorite Mexican restaurant. When we did, several questions came to mind.

I wondered of course if I would encounter any unapproving vocal fellow patrons who were protesting the mere presence of a transgender woman in the venue. Since we had been there many times in the past, I did not have much fear of that happening. Again, last night, nothing happened as I was treated the same as any other guest in the very busy venue. 

Then, I began to worry further about the influence of our current felon in chief and his attacks on illegals. I wondered what the Hispanic staff thought or worried about future ICE raids in Cincinnati which is considered a sanctuary city which should make it a target from the tRumpt goons. 

I had plenty to think about as we waited our fifteen minutes to be seated. As I people watched, I naturally wondered how many had voted for the felon. How could they? But, on the plus side, I was back out after myself imposed Covid quarantine. It felt great to be out and about and finally free from all the disease's evil effects. 

Everyone around us was minding their own business and we were minding ours. All the way to being addressed to as "ladies." Which is always very affirming. Through the entire evening, I was able somehow to put my election bitterness behind me and have a good time.

Hopefully, I did not overdo it and will have the opportunity to do it again soon. Also, I hope the masses who voted for the administration who is trying to erase all transgender people everywhere in the country will somehow feel the error of their ways. My personal paranoia date is coming up in May with my endo doc. Then, I will need a refill to my Estradiol hormones. Since I am under the Veterans Administration health care system, at any time I fear, the orange felon could reach out and try to cancel my care. We shall see and I will be forced to take it one day at a time.

In the meantime, I can take nothing for granted. It seems as if someone could always be coming for my back simply because I am transgender and I refuse to be erased. 

Set Up for Success

 

My wife Liz who set me up 
for success. 

As we follow the complex gender path, we are on, there are many ways to set ourselves up for success or failure in the world.

Being the stubborn person I am, I kept making the same mistakes over and over again until I finally righted myself and was able to blend in with the public. Looking back, too many times, I returned home with tears in my eyes after the mirror lied to me about how I looked. I was somehow not setting myself up for success and had to keep going back to my feminine drawing board until I finally began to improve.  

One of the earliest forms of success I discovered was the power of the thrift store. The stores provided me several avenues to improve my novice transgender self. First of all, the stores fit my very limited budget, and I was able to try on or purchase clothes I would normally not. Secondly, I was allowed to shop to my heart's content without any interference from commissioned clerks who were more interested in my money than me. Finally, my third form of success was the entire experience helped me to discover a newfound sense of confidence in myself as a transgender woman. 

Slowly but surely, I was learning how to dress myself properly as a transgender woman without being trashy. When I did so, I stopped all the unwanted attention I was receiving Or, all attention as a woman, was not good attention.

Setting myself up for success in my transgender womanhood meant going to the right venues. I found out the hard way not to go where cis women already knew not to go. I started to stay out of dimly lit streets and parking lots. Even more so, I began to stay out of red-neck venues where I tried to go to for a beer and to watch sports. Sadly, the police were called on me in one of the places and in another, two guys thought it would be cute and necessary to play "Dude Looks Like a Lady" repeatedly on the juke box. I solved the problem by establishing myself in venues which accepted me.  Which did not include the gay bars I did not feel a part of either.

Through it all, as I learned to accept myself as a trans woman, being set up for success was a long process discovered mainly by trial and error. Since I had no real role models to show me the way. Fashion and makeup were only the beginning before I needed to explore communicating with the world as a woman. I discovered very quickly how many women wanted to know what I was doing in their universe. 

Along the way, one thing I needed to learn was to be patient and judge each step carefully since I had so much to lose. Setting myself up for success was so difficult on so many levels. I needed to make sound decisions to make sure I was making the very complex move I was contemplating. I have always viewed a gender transition as one of the most difficult moves a human can undertake.

Sometimes I feel, I took too long to set myself up for success, but I had to be sure I was doing it right.   

Now What?

 

Image from Kolos Kevie 
on UnSplash

During my long journey to transgender womanhood, I have encountered several "now what" moments. 

The first I can remember came during a Halloween party I was attending. For the party, I was dressed in a very short mini dress which showed off my freshly shaven legs completely. Even though the men mainly stayed away from me, several women took it upon themselves to compliment me on how good my legs looked. Now, I remember vividly telling one of the women thanks but a lot of good my legs will do me. I did not finish the thought by telling her having good legs will not do me much good if I need to wait another year to show them off again at Halloween.

As life flew by, I finally was able to show the public my authentic self, to very mixed reviews. Predictably, I went too far overboard building my wardrobe around my legs which was correct to do during the eighties when short skirts and oversized sweaters and tops were all the fashion vogue along with big hair. It was like the fashion gods were playing right into my hands as a novice transgender woman. 

As we all know, fashion trends change, and I was forced to also if I was to do my best to blend in with the other women around me. Finally, I needed to lengthen my skirts and adopt shorter wigs. I was not happy but had to adopt a new "now what" fashion mode. 

What came along to save me was a new realization about what presenting as my autentic self-meant to me. I began to survive on my new personality as the public began to want to know more about me. When I did, I began to encounter many new "now what" moments on a regular basis. In other words, I was in very deep trying my best to discover if I could or should attempt a gender transition into a new scary, exciting world. 

I discovered I very much did want to be in the new feminine world I was discovering, and I could not under any circumstances turn back to the old male life I was in. "Now what" had passed me by and it was too late. I had passed all my personal tests seeing if I could do it.

It was a long road, but I managed to do it. I just wish I had listened to my inner gender questions years or even decades ago.

Trans Tipping Points

 

Image from Darius Bashar
on UnSplash

Many times, in the quiet of the night, I have the opportunity to look back at my long life.

When I do, I always ultimately come to the conclusion that I was always feminine and just refused to accept it. Even more, there were several times when I realized the many tipping points, I crossed along the way which heavily influenced my life. 

The first I always mention is very early when I cross dressed in front of the mirror at home, deep down I knew just looking like an attractive girl was never going to be enough. Instead, I wanted to be one. Which would become my lifetime goal. In order to arrive at my goal of course, there would be many obstacles to overcome. What would I do about my increasingly complex male life was one good example. Each good thing which happened to me as a man would have to be let go if and when I was able to transition into my preferred transgender womanhood. 

It was then I learned there would be many small tipping points to make it through to achieve my goal. I was finding I had a unique life which just had to be lived if I was to survive at all. The whole experience was at once terrifying and exciting. Here I was on the edge of doing something I had only ever dreamed of. I had arrived at the point where every night I went out as my authentic self, the feedback I received told me I was on the right path. Primarily, for the first time in my life I was feeling natural about what I was exploring with my gender. The main tipping point came when one night I put cross dressing behind me mentally and decided I would join the world of women as an equal, or another woman.

All of a sudden, the slick slope I was on became very slippery and I began to plan ahead for the time when I could begin to live my dream life as a transgender woman. I began to cherish as much as I could, each interaction which was happening in my new exciting world. I was successful in my new life, and I was loving it. Even the mistakes I still was making became fewer and easier to overlook. Through it all, I had no idea I could make it this far.

Perhaps my final and most potent tipping point came when I started gender affirming hormones. I knew when I started them, there would be no turning back. Even though I felt that way, I was not prepared for all the changes I was going to go through. Of course, I knew and hoped for a rapid increase in my breast size and increased growth of my hair. All of that happened as well as a complete softening of my skin. But most unexpected was the quick change I experienced with my emotions. I went through puberty again, even experiencing my first hot flashes. The bottom line was my life just softened, and I could cry tears of joy and anguish over the life I had left behind. Mainly tears of joy over what I had gained.

Tipping points for me became a way of life. Each one I went through brought me closer to my ultimate goal which I never knew was achievable. It was not until then did I understand how deep my gender issues ran. I needed to go through all the transgender tipping points to learn my lesson. 

  

Never a Choice

 

Image from Mika
Baumeister on UnSplash

After all these years I still receive the comment of why I chose to leave my male gender behind and pursue transgender womanhood. 

Ironically, very few people removed from the transgender umbrella understand I never had a choice and spent nearly fifty years figuring it all out. Sure, there were brief moments of gender clarity which somehow, I refused to recognize. Then, as the years rolled by, I kept accumulating male baggage which became more and more difficult to consider leaving behind. Examples would be family, friends and jobs which being masculine depended on success. I was caught between having success as a male in a world I never really wanted. For the longest time, every time I was successful at something as a man, I fantasized if I could do it as a transgender woman. A stop gap measure which in the end just caused me more frustration. 

Plus, eventually, frustration turned into more gender pressure. The whole process turned me into a very self-destructive person. Along the way, I tried to tear down all the male successes I had built up. I drank too much, drove too recklessly and even tried suicide as a final solution to my gender pain. Finally, before it was too late, I realized my error. I never had a gender choice and attempting to live even a partial life as a male was a waste of time.

To make matters worse, I was very stubborn, and I attempted to hang on as long as I could in my transgender world by trying to live partially in both worlds, male and female. Slowly but surely, I discovered I could not continue to live that way. The more I learned about living as a trans woman, the more feasible a complete transition became to me. The whole process took me back to my earliest days cross dressed in front of a mirror at home when I realized I wanted to do so much more than just look feminine. I wanted to be feminine but my upbringing in a male dominated family was throwing up all sorts of roadblocks for my future. So, I learned what most men learn. To internalize my feelings the best I could. Which would lead me too much more serious problems later on in life.

The biggest problem was I was fighting the gender battle of my life. Regardless of what my male self was telling me about maintaining the status quo, sooner more than later I would have to face reality and know my gender was never a choice. I could not rest and enjoy my life until I finally made the ultimate decision. 

One lonely night as I was again pondering my future at the age of sixty, I weighed the benefits of both of the genders I was trying to maintain. In a blinding moment of clarity, I gave up forever any rights I ever had to a male life. 

It was the best decision I had ever made in my life. All of a sudden, this huge weight was lifted off my shoulders. From that point forward I decided to pursue gender affirming hormones and give all my male clothes away. Most importantly, I faced up to the fact I had never been a male except biologically which had nothing to do with my brain. I followed my brain and never looked back. '

Without the gender monkey on my back, I had a chance to live my life my way. The way I never had a choice of and took too long to realize it. 

Survival versus Impostor Syndrome

Conch Shells

 Many times, during my journey into transgender womanhood, I have experienced my fair share of impostor syndrome when I was able to slip in behind the gender curtain.

Most of the time, my fight with impostor syndrome happened early in life when I was first coming out. It was so unfair when I had spent so much time and effort to perfect my feminine presentation, only to be rejected by my own thoughts. The syndrome was especially strong when I was invited to girl's night's outs or used the women's room. 

On our recent vacation trip, I am happy to say, I think the old curse of impostor syndrome went totally away. Since the trip in reality had very few men in relation to women, many times when we ate meals, we ate with other women. I knew I had it made when others asked if we were sisters. Sadly, the overall physical stress of the trip began to take its toll on me. The sicker and weaker I became, the only thing I was trying to do was make it home in one piece. No matter how hard I tried, Covid was stronger and ended up putting me in a hospital in suburban Atlanta for several days, until I could regain my strength and travel again. I have written before how my daughter had to drive down from Ohio to rescue us when there were no rental cars available. 

Again, survival became the priority over worrying about petty issues about what rest room I was going to use. The only time I wavered in deciding what rest room I was going to use was when we stopped at a little seafood place in Florida around the Everglades. There were only two restrooms to use, clearly marked male and female, so the line to the women's room was very long. After a short time, a few brave women began to go ahead and use the men's room, not unlike you are able to see if you go to any major sporting events. I thought long and hard about going ahead and using the male side but ultimately decided it would be a bad idea. Since I did not have to go that bad and did not want to destroy my perfect restroom record which has gone back over a decade, I decided to wait and use the women's room. 

As we waited for our boat tour of the Everglades, we had lunch, and I was able to order a first for me, Conch Fritters. So, I was able to cross another item off my personal bucket list. During lunch, we found a seat at a table with a couple and a very gruff man wearing an Army hat. He did not seem to want to talk much to me and even though I very badly wanted to ask him where he served, I did not. In some ways, impostor syndrome had set in. 

Of course, in the hospital, as I have written about before, pure survival on my part had set in.  All I wanted was to feel better and be discharged. There was no time to be worried about any sort of impostor syndrome at all. In fact, the whole deal I went through made my ancient worries about fitting in seem very petty in comparison. 

So petty, I wonder if I was ever the same person who was so completely into obsessing on my feminine appearance. Perhaps I needed that time in my life to grow into the transgender woman I am today. I was not aware there were going to be multiple transitions as I grew into my authentic self. Being a functional woman meant so much more than just looking like one. There were factors such as developing communication and personality skills also.

Gender Harmony

 

My friend Racquel and her dog.

When asked when I first realized I had issues with my gender I began to tell the truth and say I had known forever.

In fact, my statements were only partially true. I knew something was wrong with me, but I did not know exactly what. When I was young, I knew how much pleasure I received when I dressed as a girl. What I was lacking was the knowledge of how much harmony I was missing by learning the aspects of living in two genders.

Over a long space in time of nearly fifty years, my male and female selves battled it out, which naturally created huge disruptions in my life. My already frail mental health was in shambles most of the time. Since I had already been diagnosed as being bi-polar by a therapist before, my gender issues seemed to be a bigger problem. In reality, both issues were working together to make my life miserable before I took action and did something about it.

I started with the easier one, my bi-polar condition. After I tried several medications, I found the right ones which I am still taking to this day. The much more difficult of the two issues destroying my inner harmony was my issue with my gender. Had I listened to my first therapist years ago when she told me there was nothing, she could do with me wanting to be a woman, I would have been better off. Maybe I would have been able to relax more with my issues and realize my transition into transgender womanhood was going to be a scary yet exciting journey I should try to relax and enjoy. Rather than fight and destroy my mental health as I did it. Plus, what made matters worse was all the people around me I attempted to make miserable too. Leading my second wife to even consider telling me to be man enough to be a woman. The problem was, back in those days, I did not have the feminine experience yet to do it. So, my miserable life continued.  Any sort of gender harmony seemed to me an impossibility.

During that time, I really set out to seriously discover what measures I would have to take to restore any sort of harmony to my life. Which essentially saved my life after a failed suicide attempt. I found I had to discover harmony or face losing my life totally. 

Initially, I was obsessing on my feminine appearance over any other aspects of being a transgender woman until my trans friend Racquel told me I passed out of sheer will power. Deep down, I knew what she was talking about. I was not and never would be the most attractive woman in the room, unless I could afford the expensive facial femininization surgery. Which I couldn't. It did not matter anyhow, since I had already decided to move forward in the world with the best possible appearance I could put together. 

Long story short, I found my path to a new life and am very fortunate to live as a full-time transgender woman. Racquel went on to several appearance altering surgeries and moved away so I have not seen her for years. I owe her for the honesty she expressed to me concerning my coming out experience. As my wife said too, there was so much more to a woman than just looking like one. Finding harmony with myself, enabled me to find harmony with others. I made friends in my new life and moved on.

Amazing

 

Image from JJ Hart

As I sat and watched a singer do a wonderful rendition of John Lennon's "Imagine" and watched the ball in New York drop to ring in 2025, I had the chance to look back and think about how amazing my life has been.

As in everybody's life, destiny stepped in and took me in directions I never thought possible. The entire process was how I perceive the supposed death experience people have when they die. In other words, they get to see their life pass in front of their eyes. If indeed that does happen, I may have to ask for a little extra time to view all of mine.

Over a long life, I have been so fortunate to experience so many things. Outside the all-encompassing world of gender for me, was when I managed to land a job in the Army with the American Forces Radio and Television Service in Thailand and Germany as a radio disc jockey. To put it into perspective, there were only sixty other troops in the entire Army who did what I did. Since back in those days, we were basically the only connection our listeners had with home, it was a very serious job. 

Once I had served my time of three years and was released from active duty, I needed to take on again my larger issues of gender identity. To do so, I undertook serious research and development. Any time I could such as Halloween parties, I began to explore public reactions to my femininized self. For the most part, people I knew were astounded and I moved on. Perhaps it was my shaved legs which gave me away. Whatever the case, time flew by, and I started to cross dress more and more in the public's eye. Plus, at the same time, I slowly began to perfect my knowledge of fashion, makeup, and hair. I discovered the more I did, the more natural I felt and the more I wanted to do. In no time at all it seemed I was accomplishing tasks such as doing the family grocery shopping as a woman and it felt amazing.

Imagine my surprise when I then discovered I was going through another major gender transition. All of a sudden, I was losing my desire to just look like a woman and I more and more wanted to explore a path to transgender womanhood. Mainly because I was feeling alive and amazing when I did it. Now we all know how difficult a gender transition is for the average human being, and I was no different. I had very few natural feminine characteristics to work with and I had to struggle completely to survive in the life I wanted to live. Especially when I hit what I call the dark period of my life when I lost nearly everyone close to me to death. 

In order to bounce back, amazingly, I was able to rely on my strong inner feminine soul to survive at all. She helped me find my way. During the bounce back period of my life was the time I found a whole new set of women friends to instruct me on how to live my new life. Included in the trio of new friends, was my new wife Liz who I never expected to meet. At my advanced age of sixty plus, I would never find another person to be close to the rest of my life. Especially since I carried so much gender baggage with me. At the time, I still maintained one tentative foot in the male world, until Liz told me she did not see any male in me at all and what was I waiting for. Go ahead and fully transition. I was amazed and still am since it was over thirteen years ago when our relationship happened and is still going on strong today. 

The end result of watching the ball drop to welcome the scary year of 2025 was I have been so fortunate to have led an amazing life so far. Mainly because destiny has been on my side, and I have lived long enough to accept it.  

I Never Felt at Home

 

Image from JJ Hart

Rarely, every now and then someone asks me when I knew I had gender issues. 

The answer I give everyone is I knew forever there was something wrong with me. I just did not know what. Plus, by the time I realized what was wrong, I felt as if I was alone in the world with my gender issues. I was very confused. As I grew through my teen years, I knew I wanted to be a girl but just did not see a path forward. 

Through it all, I kept searching for answers. I knew for certain I felt elated and natural when I cross dressed as a girl and never quite felt at home when I was with a group of males. I felt as if I was an outsider looking in. 

The older I became, the better I was at hiding my feelings. I tried my best to do all the usual male activities such as playing sports and working on cars. I played the male game well to hide my inner most feminine feelings but all along still felt like an intruder. It wasn't until I began to seriously explore my transgender womanhood did, I finally learned the truth, I was not meant to live a male life at all. As I recently wrote, I was stuck in some sort of a gender never-never land I was destined to never escape. I spent too much time pitying myself and playing the gender victim before I stepped up to face my problems.

In the meantime, the biggest problem I faced was deciding what to do with the increasingly immense amount of male baggage I was accumulating. After being discharged from the Army and finishing my second college degree, we added my daughter to the family, and I suddenly needed to become serious about beginning a career which I could support a family on. Then came the route I followed to a successful job I would probably have to give up if I transitioned to a transgender woman. As I advanced up the corporate ladder, at all the macho leaning meetings I needed to attend, I still felt completely out of place. No matter how successful I was.

Then there was the biggest piece of baggage of all which was my second wife. Although, she knew from day one I was a cross dresser, she drew a line in the sand when it came to any idea at all I was transgender and wanted to begin gender affirming hormones. She and my male self-formed a formidable pair when it came to any idea of me going any further towards transgender womanhood. When she unexpectedly passed away at the age of fifty from a massive heart attack, my male self-lost his strongest supporter and he just faded quickly away.

At the same time, I was building a new set of friends who happened to be women and lesbian and I had never felt so at home in my life. They embraced me for my authentic self while at the same time I relaxed and learned so much about womanhood from them. I never thought possible, life would ever be so fulfilling again since I was already sixty. It was well over a decade now and during the same period I met my current wife, Liz. 

Feeling at home for the first time in my life was the best possible feeling I could ever have. 

Expedition Transgender

 

Image courtesy JJ Hart

The half century journey I embarked on to finally come up as my true authentic self was certainly an expedition. 

As I always mention, my discovery began with going through my mom's underwear drawer and trying on nylons, bras and girdles I could still fit into before testosterone poisoning really set in. From there, I progressed into makeup and very slowly began to increase my craft. I did not really want to look like a clown in drag so I did the best I could. 

Life went by and so did my expedition. Sadly, for several reasons, I developed several coping mechanisms to mask my gender truth. I tried and tried to convince myself my desire to wear women's clothes and look feminine was just a harmless hobby and perhaps was just a phase in life I was going through. It took me years to realize the true phase I was going through was that I was a male at all. With sheer willpower, I managed to learn to play the male game fairly successfully and lived a life which shielded my feminine self from most all intrusions. I went into my dark lonely gender closet and slammed the door.

It took me years to have the courage to open my closet door and tentatively look around. When I did, my expedition took sudden and encouraging turns. The more I tested the public as a transgender woman, the more successful I was. I set out to sample as much as I could of a woman's lifestyle and discover my feelings on what would happen next. I tried going to gay and lesbian bars as well as big sports bars and found I could carve out a spot as a regular in a so-called straight venue. I also tried to go to various other places such as bookstores and other retail venues single women would go. In other words, I was obsessed with coming as close as I could on my expedition to seeing what a cis woman went through in her life. By doing so, I could make the final decision on where I wanted to go with my life, as a man or as a woman. 

As my expedition transgender progressed, I found myself in a face-to-face decision on beginning to take gender affirming hormones or not. Since my only real opposition to beginning the hormones had passed away, my ultimate path was clear, and I sought out a doctor for approval. He checked me out and determined I was healthy enough to begin HRT with minimum dosages of Estradiol and a testosterone blocker and my life changed forever. All the changes which occurred would fill another blog post themselves. Perhaps the biggest overall surprise was how quickly my body took to the new hormones. So fast, I needed to rethink how quickly I was going to have to change the timetable of when I ultimately wanted to finish my expedition and enter my own transgender womanhood.

I learned the fact of the matter was, I was always living a gender lie. I had refused to accept the fact I was always deeply feminine and was forced into a male lifestyle from some cruel twist of fate. All the time I thought I was a man attempting to be a woman was wrong. I was a woman attempting to be a man.

I wish I could have a portion of my life back to re-center my expedition and start all over again.  

 

Creative Gender Tensions?

 

Image from Levi Stute
on UnSplash

As I moved along my long and bumpy gender path, seemingly I created many gender tensions which were overblown or not needed at all.

It all started innocently enough when I first caught a glimpse of myself for the first time wearing makeup and a dress in the family's full length hallway mirror. Immediately, I knew I was hooked and could not wait to cross dress again for my own personal pleasure and delight. Sadly, the gender tension began when I could not dress again for a while. All of it sometimes became unbearable when I woke up in the morning not knowing if I wanted to be the boy I had always been, or the girl I was increasingly wanting to be. To say the least, life was very confusing, and I felt I had to be the only person in the world dealing with the same gender issues.

In the pre-internet years (along with social media), I was in the so-called dark ages of information. I had very little in the way of outside information to guide me along or challenge the many new ideas I was considering when it came to my gender life. Everything was out of focus including my sexuality. Did I like girls at all or did I just want to be one. The tension was real but still I kept struggling along trying to be the best male bodied person I could be. 

Then the internet came along and with it, my life was changed forever. Once we could afford a computer, suddenly I found how un-alone I was and how many others there were in the world with similar gender issues to mine. Of course, I was just not content to read about others, I needed to try to interact. I became involved with several early chat rooms which eventually were discovered by my second wife when she learned how to search my browsing history. Even though the great majority of the people I chatted with were not geographically close to me, I found one who was. In fact, he was within fifty miles, so a meeting was certainly possible. That was until my wife found out and an all-new battle broke out over the control of the computer. Until I learned more about erasing my history on the computer, I needed to stay off of it. Which created a new set of gender tensions. 

Living with my tensions became second nature over the years. I followed the same old up and down patterns of being up when I cross dressed, to being down when I was forced back into my male life. I rode the edge of a double-edged sword for years until I finally decided to face the truth about myself and be me. Still, it took me years of careful exploration of my transgender womanhood before I cautiously decided I was on the right path. Once I did, much of my gender tension disappeared and I knew I was making the right move for a change. All that was left was to make the crucial decisions about who I was coming out to and when.  When I did come out, I was met with approval from my daughter and rejection from my brother, so I suppose it could have been better or worse. I still had immediate family when I did it which decreased my tension along with providing me extra confidence in myself, I never had known before. 

By now, perhaps you are wondering where the creative portion of all of this comes in. All the time when I was traveling my gender path to transgender womanhood, there were many chances to zig when I should have zagged, and I ran into problems I needed to get out of. Mostly trying to navigate the problem of expressing my new transgender self while still being involved in a committed relationship. All I can say is somehow I survived and made it to my new life as a trans woman. 

When I did, my tension went away, and I was able to live a life free of gender problems which had plagued me my entire life. The relief was real. 

NOT for Entertainment Only

 

Image from Alice Alinari
on UnSplash

As I went along my path to transgender womanhood, I found the journey was never a choice and was not for entertainment only.

My journey did not begin that way. Similar to many of you, I started by exploring my mom's underwear drawer and wearing what would fit. All of that was seemingly innocent enough unless I was caught. Then there would undoubtedly be hell to pay, along with a trip to a psychiatrist. Later I would wonder if my mom ever knew because her underwear was stretched out, but she never approached me at all. 

It was all fun and games until it wasn't. Slowly, I learned wearing girls/women's clothes was not for entertainment only. I was becoming increasingly serious about it. For the first time in my life, I was obsessing over how I looked. How was my makeup and very limited access to a wardrobe appearing in the mirror. I even went as far as shaving my legs when I thought I could get away with it. In addition, I did my best to study the other girls around me. I did not know it then, but I probably was wearing makeup before a few of the girls I knew were allowed to do it. At the time when I could not seem to muster the same passion for building the model cars I had and painting them well, makeup was an entirely different challenge and one I could not resist doing my absolute best at doing well. With no help whatsoever. 

I found, for the first time in my life, I was completely serious about doing one thing and it was being a girl. Not just looking like one. It took me years to learn just gazing at my reflection cross dressed as a feminine person was just not enough. I needed more. My problem was early on was having the budget to do anything such as being able to afford having a nice wig. It was not until my college days until I could buy a long blond wig I cherished for years. Spending all the money on one specific fashion accessory proved my passion to look good was not for entertainment only. I was really serious.

Of course, then I really started to step up my gender game. When I was released from my military service, I began to seriously explore the world as the feminine trans woman I was destined to become. As I write about often, my journey was filled with ups and downs and my mental health suffered. Definitely not the way I thought it would be when I looked at myself dressed as a girl in the mirror early in my life. What I never had a chance to consider was I was not a transvestite or cross dresser at all. In fact, I was a transgender woman and needed to accept it. I was never in it for the entertainment and my life depended on a successful outcome. 

What I mean is, I needed to stop all the self-destructive behavior I was exhibiting as I sought to destroy everything successful, I had ever done. Along the way, I had tried to lose jobs, drink too much all the way to trying to kill myself with pills. Never realizing how much I had to live for if only I followed my transgender path far enough. 

I wonder now, if I had realized how difficult my journey would be and not be entertaining would I have ever undertaken it at all. I also realize now, I never had a choice, and my life would have been better had I realized it sooner. I would love to get back just a tiny portion of the stress and tension I lost during my life as I worried about my gender. Outside of a few therapists who tried to help me by telling me the truth about myself, I was on my own. My life was never for entertainment only as I followed a gender path full of turns and dead ends before I discovered my truth in my transgender womanhood. 

Gender House of Cards

 

Image from Erick Langfield on Unsplash.

Just when I thought I had my life altogether, the world collapsed on me.

For example, when I thought my makeup and hair was the best, I could do, I would walk or scowl like a linebacker and ruin my entire feminine image. Of course, then, I would have to recount my steps and see what I was doing wrong. It took me years to build a solid foundation to build my gender future on because my base was so weak.

What made matters worse was the fact at the same time, I was beginning to do so much better as a man with my career. It was like I was succeeding despite of myself. Down deep, I attempted to destroy everything I worked so hard to achieve. All the self-destruction really took a toll on me and my mental health. To make matters worse, on my worst days I would attempt to take my gender frustrations out on the people closest to me. I became so bad; I even lost a job over my actions. Perhaps the worst part was, I did not grasp what was happening to me. I kept repeating the same old stop-gap routine of cross dressing once or twice a week, feeling better for a day or two before I would revert back to my old gender frustrations again. Predictably, my frustrations would repeat, and my gender house of cards would come crashing down again. 

Finally, as I began to acquire more confidence in my transgender womanhood, I started to increasingly build a better base and feel better about the major struggles I knew were coming up ahead. Primarily, what was I going to do about my twenty-five-year marriage to a woman I loved and a successful job I would have to leave behind. And all of that just scratched the surface of all the obstacles I would need to face such as what would my sexuality be if I decided to live full-time as a transgender woman. The path ahead, at the least was very murky. 

Since I was a very social person, I needed to figure out how not to be so lonely anymore. I just could not keep going out to be alone. My dilemma was men did not approach me seriously and I did not know how to react if they did. My first date with a man was with a transgender man who afterwards said I was very scared. Which was true. The problem became when the only other path to being social for me came by approaching other cis women. Fortunately, I did not have a problem because more and more of them approached me. For whatever reason. Regardless, when I went out socially, I ended up at the least talking with other women. Just having the chance to practice my feminine communication helped me to build a better gender base to build from. 

From that point, life became easier, and my path became clearer. Increasingly I understood I needed to leave the male life I never really wanted behind and jump the gender border at whatever the cost. I was near the age of sixty and was so tired of living a lie and was to the point if I did not complete my transition, I would never have the chance to live my dream.

By this time, I was able to build a solid gender house of cards, so everything turned out successfully when I made the final move. Perhaps here would be a good time to quote Paula from the UK: "For some of us there is a real need not just dress as a woman, for the world to experience us, and accept us as a woman ~ it is not enough that in our mind we are women, we need to go all the way; and that is why we need to transition. I too remember my wife saying (with no intended irony at all) "It takes balls to be a woman"

Most certainly Paula our wives were right. That is the primary reason it takes a solid foundation to approach transgender womanhood. Thanks for the comment!

Joy to the World

Image from JJ Hart Liz on right.

Gender euphoria is so wonderful to a transgender woman or trans man striving to present themselves in the world as their authentic selves. On the other hand, it is often very rare to obtain. 

The brief moments I experienced euphoria in the world when I first went out as a novice trans woman or cross dresser, kept me going but barely. The reason was, I suffered from huge bouts of  gender dysphoria which wrecked my life. It seemed every morning when I woke up and looked in the mirror, would I see the same old male I never wanted to be or somehow see behind him and view the girl I always dreamed of being. My dreams even reflected my gender issues when I would awake following a very vivid dream where I was the pretty girl. When reality set in, I was very sad.

It took me years to realize I could fight back against my gender dysphoria and do more to live out my dream of living as a woman. Years of sorrow when I failed became years of joy when I succeeded. Progress was very slow at first as I went out shopping in the world and sought out every mirror I could find to restore my faith I was indeed a presentable woman just minding her business in the world. When I discovered most people did not really care about me, my life became much easier and took quite a bit of the pressure off I was feeling. 

Still, I needed more. On every occasion I could, I was out the door seeking new places to visit as my new exciting self. I was walking the gender border and feeling the joy on some of the days I was successful and torment on the days I was not. My main problem was trying to find feedback with what I was attempting to do. The only time I did receive any response was when I went to the small, diverse parties I went to at an acquaintance's house in nearby Columbus, Ohio. From transgender admirers to inquisitive lesbians, I had a chance to meet new people in my world and see how I measured up to them. I knew I could never be a beautiful as a few of the impossibly feminine transgender women who attended but just maybe I could elevate my appearance to a feminine level where I could get by. The parties also proved to be the initial starting point of developing my own new personality as a trans woman, so they were very beneficial.

As I experienced the joy of being my true self, something had to give. Sadly, the something turned out to be my male self and my marriage of twenty five years to my second wife. Both of them suffered terribly. Naturally, neither of them wanted to lose any power. My male self was quite comfortable in the life he had built and my wife did not want to lose the man she married, so I was in for very difficult times. What happened next was my mental health went into a very steep decline. I did not know where to turn and at that time did not have a good therapist to fall back on. Then I resorted to the worst possible choice when I tried to internalize everything. By doing so, I made everything worse. 

I continued to go out as much as i could but ended up just forcing the gender issue and losing any of the joy I had previously felt. It wasn't until I decided to begin gender affirming hormones and transition fully, did I begin to reclaim the happiness I felt. 

Was it worth it? Sure as I finally achieved my dreams of living fulltime as a transgender woman. I just wish I had the courage to do it sooner. Or as my second wife told me a number of times when we bitterly fought...be man enough to be a woman.