A Push versus a Dream

 

JJ Hart

I often describe my journey to transgender womanhood as the impossible dream. 

On the other hand, I cannot ignore all the pushing I needed to do to arrive at my goal. My pushing started at a very young age when I was first cross dressing in front of the mirror. To begin with, I needed to push hard to find hiding places for my exceedingly small, treasured collection of feminine wardrobe selections. I resorted to old boxes in the garage attic, all the way to a hollowed-out tree in the woods next door to our house. In trash bags. Anything to stay safe with my secret. I knew if I was exposed, life as I knew it would be over.

I did push on and survive so my dream was still intact when I went to college and then served out my time in the military. My military time was especially stressful as I needed again to carefully conceal any idea, I was feminine at all. Through it all, I needed to keep my thoughts centered on a far-away dream I had of being able to live as a transgender woman. Sadly, there were too many times when I did not see how I could make it at all. Especially when the Army was strongly reinforcing my manhood. 

As in many other facets of life, the Army came and went leaving me a sense of freedom of what I could do concerning my gender issues. My first marriage came shortly following my discharge from the military and left me still wondering about what was going on. My first wife knew I was a cross dresser and did not really care, so I was left on my own to make any gender decisions I might decide on. This was back in the late 1970's and there was very little information on even being a cross dresser available. Again, I was on my own until the computer became a reality, and I was able to reach out to others. I learned quickly I was not alone and began to push for more clarity in my life. I even was able to dream more frequently of being able to live as my authentic self.

Before I did, I needed to determine what my authentic self really was and push to get there. This meant going down a largely selfish road as I carefully checked my gender boxes. It took me years to figure it out until I was able to merge how hard I was pushing with my ultimate gender dream of a being a transgender woman. My authentic self which was revealing her-self When she did, she left no doubt on why I felt the way I had my entire life. Something was not quite right, and I pushed on to figure out what the problem was. In the meantime, I treaded water cross dressing in front of the mirror until I found the courage and confidence to try going public.

Each and every time I was successful at all in dealing with the world, my dream was re-ignited, and I started to push through or totally ignore any gender warning signs I encountered. Everything I was doing put me completely at odds with my second wife, who again knew I was a cross dresser but never wanted me to leave the house dressed. Not only did I break my promise to her, but I also went as far as beginning a whole new life. My new life rapidly became very important to me mainly because I was happier and the whole life felt so much more natural.

My lifetime full of pushing finally aligned with my ultimate dream of transgender womanhood. Destiny opened my gender doors at the age of sixty and I took complete advantage. 

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.   

Why Me???

 

Image from Paige Cody
on UnSplash

Earlier in life, when my journey into transgender womanhood was weighing heavily on me, in despair I would look in the mirror and whisper why me.

During that portion of my life as I was still learning the benefits of being a trans woman, I had not had the opportunity to witness the positives I could achieve. Perhaps, the positives are one reason a certain political group is dead set on erasing us. As always, the group has ignored the times in history when entire societies worshiped dual spirted or transgender members of their civilizations. Since I do have a degree in history, I often took the chance to do extra research on the subject in my spare time.

I also think outside TERF's or transphobic women do not trust us because we have spent time in a male dominated society enjoying male privilege. When in fact, we were not enjoying our experience at all and desperately wanted out.  As far as men go, so many are desperately hanging on to their frail sexuality, they become scared and bitter as they secretly watch their trans porn. Sadly, the men's frustration turns into violence towards the transgender woman the man wanted so badly. 

Perhaps the biggest thing I did not realize until I spent time in the public's eye as a transgender woman was how much both binary genders secretly value our knowledge of the world. I remember vividly the numerous times I was approached by other women dealing with man problems of their own. I found the other women really valued my insight into the male world. Through it all, I began to lighten up on my poor, poor pitiful me idea of life and began to see the benefits of living partially between the two main genders. Once I put being a gender victim behind me, my life brightened considerably.

The entire process went far beyond other women asking me about their men, all the way to me being able to increase my overall confidence in the new life I was living. Rapidly, my life was approaching a point of no return. The pressure was on to make the right decision on how I was going to live the rest of my life. I did not think the rest of the world could understand how badly I was torn by my gender decisions, so I did the male thing and internalized them. My mental health struggled badly until two things happened.

One of which was when my wife Liz came along and told me in no uncertain terms, she had only seen a female in me, and I should stop the remainder of life I was living as a man. The other was when I began HRT or gender affirming hormones. When I finally did begin the new hormones, my body took to the new regiment of meds as if I should have always been on them. 

Between the two, even the very stubborn part of me which was desperately hanging on to what was left of his old male life could not resist any longer. Overall, when I looked for my gender truth I found it. Why me? became my truth and when I accepted it, I knew I had done the right thing. My life became softer, richer and more colorful than ever before.   

To arrive there however I needed to pay my dues and learn many important lessons before I could move forward. 

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.

A Trans Girl's Baggage

 

Image from UnSplash

Like many women, we trans girls carry a lot of baggage when we travel.

If you remember the old Paris Hilton commercials of her mass amount of luggage she brought along when she traveled, it reminded me of the size and number of bags we trans women have to have to transition from a male life to a feminine one. To the typical outsider, they think all we have to worry about bringing along is fashion and/or wardrobe necessities. When in truth, we know which wardrobe to bring is just the beginning. Examples are many and varied, often determined by when we decide to transition in our life cycle. Needless to say, an older transgender woman may have more aspects in her life to consider with family, friends, spouses and employment to think about.

In my case, I waited so long to enter trans womanhood, nearly everyone I cared about as far as family and friends went, passed away. I would not recommend it, but my method really simplified the process of telling my deepest darkest secret to others was made so much easier. In fact, I only had two family members to tell of my authentic life. My daughter and my brother which went half and half for me. My daughter remains a steadfast ally to this day while my brother and I have not talked in over a decade.

Thus far, we have only discussed the larger baggage items and not any of the smaller yet still important things we have to bring along with us as we enter a scary yet exciting new world. Such as, what would we do about the interests and hobbies we have built our male lives around. As far as I am concerned, what I always bring up is my lifetime love of sports. For years, I considered I would have to give up my interest in sports in order to transition. Because I knew so few women who were into sports.

Fortunately, the world around me began to change or I began to see more clearly what was really going in the world I was in. In other words, I began to see other women in the sports bars I was in as interested in the games as I was. It was around this time also when the National Football League began to market their product to women. It became stylish for me to wear my team's jersey into the sports bars I became a regular in. In addition, the other women I began to be friends with were sports fanatics.

All of this combined to make my path to my transgender womanhood so much easier. I can compare it to just having to bring a carry-on bag with me on a plane instead of a large piece of luggage. I was more secure and did not have to give up any of my interests I so enjoyed. 

Perhaps the only problem I had was when I talked to men. With them, I often had to dumb myself down when I talked about topics, I knew a lot about. One time, with a tow truck driver, I needed to finally act as if I knew nothing about the mechanics of the truck, we were in to satisfy his ego. It was my first interaction one on one with a man, so I was surprised how it went. Basically, I was forced to give in to him to just maintain civility on the short trip. The lesson I learned was one I kept with me every time I was with a man.

It turned out I had unpacked a whole new set of transgender baggage.

I Was Led Kicking and Screaming

 

Summer Image. JJ Hart

One good question I receive a lot is why it took me so long to finally accept I was a transgender woman and move on. 

The answer is I was literally led kicking and screaming towards my gender dreams of accepting my feminine self. I know it seems like a contradiction in terms, but it is true. Looking back, there were two things I can attribute my problems to. The first one was my male self-put up a real fight every time his territory was encroached on. He always seemed to come up with good reasons why I should not consider going any farther into my increasingly natural feeling feminine world. When I was feeling more and more secure with my decision to live as a transgender woman, a good time as a male would come along and challenge my thought pattern. It was like he was saying, I told you so and I could continue living as a weekend or part-time crossdresser, more or less as a hobby. While other men my age golfed, I wore women's clothes in the secrecy of my house.

Deep down, I knew that would never be the final solution. I knew it from the first days I looked at myself in the mirror cross dressed knowing in a couple of days I would have to do it again because merely dressing in women's clothes just wasn't enough.

The second major problem I had was my twenty-five-year marriage to my second wife. Through all the ups and downs of living together that long, I dearly loved her. Plus, I am always careful to say she knew of my cross dressing before we became married and accepted it. It wasn't until I began to embrace the idea, I was transgender did she begin to put up serious resistance to her ever living with another woman which she equated me with if I started gender affirming hormones. The whole process led to the most shameful period of my life when I began to cheat on my wife, with myself. What I mean was, I would lie to my wife about where I would be and what I would be doing as a man when in truth, I was out testing the public as my new authentic self. I was led kicking and screaming into a new exciting world mainly because it felt so natural to me. 

For once in my life, I began to feel the possibility I could find happiness and just maybe my gender issues were the problem all along. When I reached that point, I ultimately knew deep down what decision I would have to make. It would be selfish of me to give up on our marriage just because I wanted to live as a woman. Ultimately, my decision was made for me when my wife unexpectedly died from a massive heart attack at the age of fifty. Following my tragedy, I decided my resistance to entering transgender womanhood was behind me and the time was now or never to accept my ultimate gender destiny. Start HRT and begin the process to give away all my male clothes, along with all vestiges of his old life.

From then on, my male self was finished.  I went on to find a whole new circle of friends who in turn taught me a deeper meaning of what it meant to be me. There was certainly no more kicking and screaming from my old male self as he had given up to the feminine master of my soul and universe. She had won the battle and never looked back. 

 

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.