Showing posts with label life lessons. Show all posts
Showing posts with label life lessons. Show all posts

Friday, October 3, 2025

No Way to Solve a Problem

 

Image from Babi on UnSplash.

When I discovered my true gender issues that were disrupting my life, I needed to try to solve the problems they created.

In order to do it, I set out on a lifetime journey of discovery. Like most of you, I began my explorations in my mom’s clothes and even tried my hand with her makeup samples. My mirror often lied to me and told me I presented as a pretty girl. Of course, in my pre-teen years before testosterone began to change me, I had an easier time of looking the best I could as a young girl.

When testosterone came along with puberty my problems became real. At the same time, I was becoming better at hiding my collection of feminine clothes I found and was able to buy from my meager allowance. I became very resourceful when it came to my cross-dressing desires, as I even resorted to a cheap Halloween costume wig to get me by for years until I could finally afford to buy one.

As I chased my feminine tail from one close call to another with my family, I wondered why I was cursed with the gender problems I had. In addition, I felt as if I was the only one who had them. I was trapped in a male dominated family who would never understand a boy who deeply wanted to be a girl. My only choice was to keep trying the best I could to solve my problem.

It took me years to realize my so-called problem was more of an opportunity than anything else. But first of all, I needed to face my problem woman to man. No more of my second wife telling me to be man enough to be a woman. It turned out, I was man enough to be a transgender woman, but it was going to be a real battle. By this time in my life, I had accumulated quite a bit of male privilege I knew I had to lose in order to be successful. Basically, for a while, my female self’s main strengths where she felt so alive and natural when given a chance to shine.

As she took advantage of her time in the public’s eye, almost all of my problems seemed to melt away, and I began to feel having the opportunity to experience both binary genders up close and personal in my life was not a problem at all. I just made it one due to my inability to deal with it. I just had too many gender obstacles to overcome. I had accumulated too much male baggage I doubted I would ever be able to live without. It turned out, I could live without most of them, and surprisingly, I could bring some of the baggage along. My prime example was my lifetime love of sports, which I found a group of cisgender women who were as serious about sports as I was, so I was able to fit right in and even have fun.

The new and improved me proved I had lived most of my life as a man as a lie. All the time I spent worrying about wearing dresses and makeup was a waste of time. I had my whole life backwards. My wife was right; I was not man enough to be a woman for the longest time. Once I was though, I never looked back. I can’t say I was prepared for all the changes I was about to make; I was excited about the opportunity I was given to make them. Which most people never get.

It was certainly never a way to solve a problem; I learned the hard way.

 

Sunday, September 7, 2025

Off or On the Transgender Highway

 

Image from David Valentine
on UnSplash. 


When I seriously pursued my male to female life as a transgender woman, along the way I was fooled into thinking I was on a smooth fast interstate highway.

What happened was I was stuck on slow-moving two-lane gender roads and going nowhere for years. Plus, I needed to keep an eye out for potholes bumps and sharp curves. Too many times, I led myself down dead-end streets when I transitioned. The entire process just slowed me down and I lost decades in the process. Then I discovered one of the main problems I had was my old male self was exercising too much influence on my life. My main example I always use were the ill-advised fashion choices I was making when I tried teen girl outfits in my thirty-year-old testosterone poisoned body. I was guilty of not looking around and noticing what other women my age were wearing or what I could wear to disguise the defects I inherited with my body. Even though I was always going to be a big woman, there were plenty of other women my size to blend in with in public. While I am not a huge proponent of age women’s fashion, I am a proponent of looking good and not shocking the world.

One way or another, as I was able to put most of the fashion mistakes behind me, I was able to speed up a little and enjoy the new small gender towns and cities I always wanted to visit as a woman when I was a man. There were to be no more miserable vacations when all I thought about was when I could cross-dress again in front of the mirror. I was far beyond that point. I had developed the confidence I needed as a transfeminine person to take the next two-lane highway ahead and see where the journey took me. More than anything else, the mini trips taught me I could not go to sleep on my gender journey as I was risking my life as I knew it at the time.

In many ways, I was used to the pressure of discovery all along since it had started when I was so young. I just ended up accepting the pressure as a way of life for me if I was ever going to achieve my dream of living as a transgender woman. It all started with the threat of a psychiatrist visit when I was quite young, all the way to losing my family and job if I was discovered later in life.

Perhaps the biggest mistake I made on my road was trying to internalize the entire process and going through the infamous ill-advised purges of everything feminine I owned. It turned out to be one of the dead-end roads I was facing when I found I could not purge my deepest feelings of wanting to be a woman. In no time at all, I was back on the road and ready to try to get on the gender interstate. Many times, I was guilty of taking the wrong exit and having to go back to start all over again when I made the wrong choice of a venue and tried out a red neck, rightwing venue when I should not have. One time, I even had the cops called on me when I visited one venue, I was not familiar with.

After being told to leave, I quietly did and regained my composure up the street at a place where I knew I would be accepted and got back on the road. Once my transgender life began to speed up, I was able to stay on the interstate gender highway thanks to a lot of help from my cisgender friends who taught me more than they ever knew about discovering myself as a trans woman. More than anything else, they propelled me forward towards my dreams. They validated me to a point where I did not have to hide myself anymore on a bunch of dark deserted two-lane roads and stay on the well-lit interstates. I mention them a lot because without them, I could still be hiding my true transgender self away in my dark closet.

It took me so long to transition, I wore out a couple of vehicles along the way, but I finally did it. Regardless of the naysayers who said I was not trans enough to make it, or I passed as a woman out of sheer willpower. I accepted my life for what is was finally at the age of sixty and did what I should have done years earlier. Stood up for myself and started gender affirming hormones (HRT) which was like getting a new sports car to drive on the gender interstate. Again, I was able to leave a lot of negative people behind and live the dream I always wanted to live, as a transgender woman.

 

 

 

Friday, September 5, 2025

Trans Girl Panic

Transfeminine person from 
the Baliente Agency
on UnSplash.
As I transitioned from male to female, I found myself in over my head more times than I can recall. But before I get started on them, I would like to wish my daughter a happy birthday. She has always been one of my biggest support mechanisms (ally), and I love her very much.

As I was initially venturing out of my gender closet for the first time, my daughter quite literally put me in over my head when she gifted me a visit to her up-scale hair salon she was a regular at. I will never forget the complete panic I went through as I had to walk a line of at least ten women in chairs getting their hair done as I made it to my stylist I was meeting for the first time. I needed to calm down and look around until I began to realize what women know about getting their hair styled. It is a gender affirming experience and there was enough estrogen in the room to help my minimal Estradiol dosage along. As my panic subsided, I began not to care what the other women thought of me, and I relaxed.

It turned out, my first trip to the hair salon was just the beginning of a lifetime full of panic filled experiences. Many of which were brought about by my own ignorance. Such as the night my daughter invited me along to join her women friends in Dayton, Ohio at a well-known drag show. The only problem was, I couldn’t let on I was her parent to several of the other women because my daughter did not know how they would react. No pressure, right? I did manage to talk only when I was talked to and enjoy the show from a well-known drag troupe which had raised well over a million dollars to AIDS research. By the end of the evening, I was confident I had done nothing to embarrass my daughter, which was my goal, and I calmed down.

Later on, as I branched out on my own, I found myself in plenty of embarrassing situations I brought about on my own. I went through ill-advised times when my water balloon breast forms exploded on their own and I needed to head quickly to the bathroom to try to repair the damage. Luckily, no one else seemed to notice the mess I made before I was able to pay my tab and leave. From then on, I made sure I purchased silicone breast forms and did away with the ill-fated balloons forever, so I did not have to worry at a time when I had so much else going on. I was busy trying to make the transition from male to transgender woman, so any unwanted disasters were not welcome.

Such as the time I pulled a very public slip and fall when I was wearing my new high heeled boots, I was so proud of. I learned fashion needed to take a back seat for me when the weather was bad. The only good thing I can say about the panic I was experiencing was it was teaching me valuable lessons. I learned when I entered a venue, all eyes were not on me, and I was OK to simply stand up straight and find my seat unless there was a hostess present.

The moral to my story is I had to be resilient and not collapse when feminine panic set in and I was completely out of my old environment as a man. All my previous escape mechanisms were stripped away, and I needed to form new ones. I even learned to use fear as a motivator when I began to change my mindset that I was a cross dresser to I was a transgender woman. I felt if I could make it through another major change in my life during my second transition, I could make it through anything, and my confidence began to soar. Also, I found I began to put my biggest fear behind me, and I could look another woman in the eye and communicate one on one. For once, I was free to completely explore the world as a new transfeminine person.

I used all my learning experiences as a trans woman wisely (including the mistakes) to calm my panic and move forward towards my impossible dream. As my mistakes began to fade into my past, so did my panic which helped me to be more efficient in the public’s eye. Having a clear head in a new world is so important to moving ahead. And maybe more importantly, deciding where I wanted to go as a transgender woman.

 

 



Monday, September 1, 2025

The Second Time Around

 

JJ Hart (middle) at my first
Girls' Night Out. 

If you are one of the rare human beings to experience a second time around in life, you owe it to yourself and others to live it the best you can.

Being transgender can give you that rare insight into two of the main binary genders which should give you an edge in dealing with the everyday world. Having an intimate knowledge of whatever the other gender maybe thinking of us as trans women or trans men brings out fear in the public's eye. Who are we to possess such a wonderful scope of knowledge anyhow? It is especially bad with the male gender who has such a poor grasp of their sexuality to begin with. I know when I transitioned from male to female, one of my main concerns was my own sexuality. Was I expected to suddenly change my sexual preferences which had always been with women and suddenly start liking men. I even went to the point when I first came out when a straight woman friend of mine told me to buy bananas and practice. I will let your imagination do the rest.

We all know though there is so much more to a gender transition than sex when you set yourself up for the second round in life. I found I was leaving a life as a man where I was mildly successful and entering a totally new world full of women who were able and willing to question my existence in their world at all. Away from men, the women were a complex tribe, and it was difficult for me to be given the access to play with them behind the obvious gender curtains. First and foremost, just looking like a woman just got me in the game and the difficult part was just beginning. I spent hours and hours in the world just learning how to be the new me.

Suddenly, before I knew it, the doors to a totally different world opened for me and I was invited to the girls’ night’s outs. The invites could never replace the learning experiences young girls have when they are in their formative years and they get to go to girls’ overnighters with friends, but they were all I had to attempt to catch up on my gender homework. No chance to experiment with makeup or gossip about boys or other girls.

The main problem was, I had another male life to deal with at the same time. Looking back, I don’t know how or why I put up with all the gender stress and tension I did to make it to my dream. I guess the reason was I did not have the confidence to know if I could make such a major life changing step at all. We all have a lot to lose when we undertake such a step, don’t we? Plus, as I slid towards the idea I could live fulltime as a transgender woman, I was being accused of being selfish. Which made me feel guilty until I finally came to the conclusion I was being selfish. Because I had to save my own life.

As I was accepted into the girls’ sandbox around me by the majority of the women around me, my confidence grew that I could indeed live a second time around life as a transfeminine person. My long hidden inner female took over and surprisingly became a rather social person as I formed bonds with my small group of lesbian friends which was the best of all worlds for me. As I always say, the first and main thing my friends taught me was I did not need a man for validation. Which included my sexuality. All I needed to do was still keep an eye out for the rare bigot who hated me for no real reason. It turned out the haters would have to go through my cisgender friends to get to me, if they wanted to.

At that point in time, I met my wife Liz, and my second time around became easier and easier for me to live up to. I say live up to because I found myself at a point where I always dreamed of being. But I never thought I could make it. Never say never became a reality for me when Liz told me she never saw anything male about me. I was in gender heaven and stayed there until I realized what a heavy burden I needed to face. Here I was with the rare chance for a do over in my life and to not repeat the same mistakes I made as a man.

So far so good I think as I head down the stretch run of my life and I can be thankful for the chance to live two lives regardless of what the gender haters say.

 

Friday, August 22, 2025

In Over my Head

Image from Alexander Mass
on UnSplash
In the beginning, it was all so simple. Pick something, I could squeeze into from my mom’s closet, try my best to wear her makeup and go from there. Very quickly though I found I was getting in over my head as I began to sink into my own personal gender quicksand.

My first problem was hiding my small but growing collection of feminine fashion. In addition to my parents, I had a slightly younger brother I needed to deal with. Somehow, I managed to keep the darkest and potentially most destructive secret I had away from him, I wanted to be a girl in the worst way. I had no way of knowing then how many times I would be in over my head as I chased my dream. Primarily because I had no way of knowing looking like a woman was just the first step of a lifetime of gender learning. As I like to say, my gender notebook was blank when I received my copy, and I needed to catch up the best I could.

I began by studying the women around me who were my age the best I could. It was all I could do at that time to keep myself from setting myself up for failure when I finally was able to escape my dark, lonely gender closet and explore the world for the first time. When I did, I was naïve and confident I would have no problems. After I was sent home crying after being laughed at, rudely I knew I was in over my head with a lot of work to do. For some reason, for the first time in my life I knew I could not give up and I refused to quit. I kept going back to the drawing board until my makeup art improved and I began to learn the benefits of dressing my self properly as a woman of my age and build. Suddenly, I began to pull myself out of my quicksand and began to move forward again towards my dream of living as a transgender woman.

Ironically, as I moved forward, I ran into many other obstacles in my way. Was I pushing myself into a world which was ready for me or not was one of the main questions I had. The more involved I became in the world as a trans woman, the more I needed to be accepted into women only spaces. The only way I would ever know was if I could conquer my fears and try. As I pressed on, somedays I was more successful than others, but overall, I found I was accepted by other women. The times I found myself in over my head as a novice transfeminine person were primarily when I was approached improperly by men. There were times I needed to run home and rework my gender notebook after close ugly calls with men. I learned quickly, those close calls did not validate my worth as a woman. They did provide me with an insight of what women go through in their lives and I learned fast.

As I was adjusting to the new life I was destined to live, It seemed as if the lessons I was receiving kept coming faster and faster. I learned from my lesbian friends how to validate myself as a woman and from men, what not to do. At no point in time was any of my life easy at this point, but it was scary and exciting at the same time. My dream became so close I could reach out and touch it. If I kept out of the quicksand and kept my head above water, I could make it. The hardest part was still yet to come as I was coming increasingly closer by the day to separating from the male life I resented for so long.

The final decision to change was brought on by my choice to seek out gender affirming hormones or HRT. As I urge everyone to do, I sought out medical approval before I went down the radical path I was on. I was approved, put on an initial minimal dosage and before I knew it, changes were happening which made me a highly androgynous person. One look in the mirror told me that I had made the right decision and I wanted to move past the minimal dosage of HRT I was on.

I can’t say I haven’t found my way in over my head in recent times because of the type of person I am. Did being transgender aid in it? Who knows. We all have our choices to make, and they are all tempered by the people around us. Some are fortunate and have discovered feminine gatekeepers such as spouses were there all along. While others are destined to go it alone. Whatever the case, try to not get in over your head and do the best you can.                                 

  


Tuesday, August 5, 2025

Is Purging Just a part of a Trans Journey we Need to Go Through?

 

Image from Shayan Rostami
on UnSplash. 

I received several wonderful comments to my “Purging” post yesterday including people such as Jeanie who has had gender issues for years such as me.

Here is the comment and we will go from there: “I just purged last Thursday. I wanted to see if there was a strong enough "desire to reacquire". I'd go months with the stash behind insulation in the basement under a bay window without dressing. It might be I was too chickenshit”.

Thanks for the comment! And it got me to thinking about all the ways we cross dressers or novice transgender women went to hide our small collection of feminine wardrobe and makeup from our family. As a kid, I even went as far as hiding my stash in plastic garbage bags in a hollowed-out tree in a neighboring woods. Where I hoped no one would ever discover it. In addition, I had two other small hiding places in the house I could go to if I was suddenly free to cross-dress in front of the mirror. The entire process added to hiding my gender issues in plain sight. Almost, as all along, I was desperately trying to escape being caught and being sent on an unpleasant trip to a psychiatrist who would have most assuredly pronounced me mentally ill. Which was the norm for mental health professionals back in those days.

Since I never completely purged my feminine stash ever, maybe I was too chickenshit to do it (as Jeanie said). Or, as I struggled throughout my life with gender issues, my own “desire to reacquire” would return to rule my life. As it turned out, I was never strong enough to purge totally. Which looking back should have given me a clue to who I really was, a woman cross dressing as a man. Deep down, I knew, every feminine item I had worked so hard to acquire could not so easily be thrown in the trash. It would ultimately come down to me wondering how much different I would look in the mirror if I had not thrown out my previous stash.

At first, it all got worse before it got better when I entered my strong going out in the world as a novice transgender woman with my second wife. Fortunately, when I was restoring the old house, we lived in, I was able to build in a closet we rarely used. So, I found a place to hide the many thrifts store finds I had made and purchased. Also, by this time I was in a place where I did not care what my gender foes thought. I was building my future public persona, so I needed to look my best. Essentially, I entered the “don’t ask, don’t tell” phase of our relationship when my wife never said a word about my increasingly large wardrobe. She knew, I knew I was never going to purge again. Which turned out to be not true.

Just before she passed away, I decided to throw away “most” of my wardrobe and makeup and even went to the extent of growing a beard. Which I considered the ultimate purge. Even as I did it, something told me to keep my favorite outfit, wig and shoes because I never could be sure when I would need my old friends again. Tragically, six months later I did when my wife passed away and I turned inwardly to my feminine soul for comfort. When I did, I was able to shave my beard and hit the ground running towards a new life. Or, should I say, heels on the ground.

One way or another, I was happy I was not strong enough to totally attempt to purge away my feminine life. It was time to open a new chapter, even if I was sixty, as a transfeminine person. It seems many of us, with gender issues are doomed to a life of denial. We try to sooth our transgender or cross dresser sides by trips to our mirrors until we are caught, or in a relationship which even makes it worse. We begin to feel guilty about many things such as forsaking our ingrained male habits, all the way to feeling selfish for wanting to do something as radical as changing our genders for ourselves.

A lifetime of purging falls right in line with all the other pitfalls we encounter on our gender journeys. We must be strong enough men to make it to transgender womanhood and purging is just another experience we have to go through.

As always, thanks for reading along with my writings and experiences! Your comments mean a lot to me also. They help me to know if I am headed in the right direction. Please keep them coming!

 

 

Monday, August 4, 2025

Kicking and Screaming.

 

My trans friend Racquel
with her fur-baby.

Sometimes I am asked why I waited so long to finally make the serious transition into a transfeminine world at the age of sixty.

The partial answer is I did not want to face up to my truth of who I really was. Instead, I internalized my gender desires as long as I could. Another reason was, I had a powerful male self who did not want to give up all the white male privileges he had fought to gain. Every bit of ground he lost to his transgender sister was hard earned. Plus, he had a powerful ally with him in my second wife who wanted no part of me to progress any further than the cross-dressing stage I was in when I met her.

My excuse is for not transitioning sooner goes past just ignoring the obvious. I just did not factor in the other major changes I would have to go through just to see if my dream of living as a trans woman was even feasible. Maybe I could never make it at all was a fatal flaw in my thinking because I needed the inner confidence to live. At that point, I opened my gender closet door and began to look around and my male self was dragged kicking and screaming into the world. Early on he was being laughed at in drag when he went out which hurt his male ego. Until he summoned up enough skill to stop the abuse.

All of this led up to finally realizing (for whatever reason) I was more than a cross-dresser. I was a transgender woman. It all led up to the scary, magical night when I decided to change my mind set when I went out for a drink in a venue, I had frequented many times as my male self and had always wondered what it would feel like to do it as a woman. As I said, I was scared to death, and sat in my car for what seemed like forever adjusting and readjusting my hair and makeup before I went in. I knew from previous visits, when the nearby mall closed, the bar would fill up with single professional women who just socialized with each other. As I steadied myself to go in, my male side was still screaming no as my feminine side was excited to finally get a chance to live. That night, for the first time, she had won the battle because I had a great time and even stayed for an extra drink just because I could.

Little did my feminine side know, winning one big gender battle would only make the war seem further away. Following the evening out, she wanted more which caused severe problems with my marriage and life. Deep down, I wanted to experience the thrill of feeling natural in my skin for the first time, and when I could not do it, I became depressed and downright mean to the world around me. Internalizing my gender issues became less and less of a way to run my life. As a result, I started to sneak out from the house any spare moment I had to attempt to reinvent myself as a transgender woman.

I learned I could and began to slowly carve out a new life for myself with people who knew nothing of my past male self who was still strongly resisting every move I was trying to make out of my closet. Sure, I had my ups and downs with what I was doing but my overall trajectory was up, and I was proud of myself. I had come so far from the early days I had admiring myself in the mirror. Even the kicking and screaming from my male self was beginning to fade. But I found not to be too confident because I still had a long way to go on my gender journey to be a full-time transgender woman. Since my trans woman friend Racquel always told me, I passed out of sheer will power, I always had to work harder to make it in the world. I would forever have a testosterone poisoned body my male self-had left me to work around since I did not have the finances or will power for expensive facial femininization surgeries like Racquel did.

So, I did the best I could and managed to build a small tight knit group of women friends who accepted me while at the same time instructed me on the finesse points of being a woman. All of it brought the final curtain down on the kicking and screaming of my male self. I just wish he had not been such a formidable opponent. On the other hand, his interaction kept the bullies away from me for the most part and allowed me to get through the military in one piece, so all was not bad.

The end result was, he never felt as if he was the most natural person for me to be. That distinction always went to my feminine side who never gave up winning my own gender war. She ended up just ignoring all the kicking and screaming until it finally went away and the lack of extra noise in my life was a welcome change.

 

Friday, August 1, 2025

Life is too Short

 

Image from Brian Wangenheim 
on UnSplash.

Time is a precious commodity and life is too short.

Days, weeks, months and years are especially precious for many transgender women and transgender men. Mainly, if you waited until later in life to break out of your gender box and transition. Which is what I did.

I could and did look at my cross-dressing years as practicing for the big event of coming out as a transgender woman. While I improved my overall skills in wardrobe and makeup basics, there always seemed to be something I was missing. Actually, there were two main things I was missing, not just one. The first one was the realization I had my idea of cross-dressing backwards. I was never a man cross-dressing as a woman, I was a woman cross-dressing as a man. The second major realization was I would have to go through several transitions to meet my goal. An example was, I needed to transition from being a cross dresser to being a transgender woman if I was ever going to make it to where I wanted to go as a transfeminine person.

To accomplish my dream, I needed to take my second wife’s advice and set out to learn what a real woman went through in life. There was so much more than just being the “Pretty, pretty princess” as she called me. The problem was, she was always my feminine gatekeeper when I tried to explore the new and exciting world I was seeking. She did not want me to make it. She was a strong person and made it tough on me to progress in any way on my gender path but still I persisted.

Time went on and the years passed me by as I went to transgender-crossdresser parties and mixers to see what I could learn. Even then, when I hit my forties, I had a sense of desperation as time went on with me, and nothing major was happening on my gender front. It was during this time of my life when I started to escape my closet and explore the world. Mainly, I was carving out a totally new life where people knew nothing of my old male self. I was free to be the new me I wanted so bad.

After I went through the darkest period of my life when I lost nearly everything and everybody who was near and dear to me, did my life come full circle, and I began to notice the light at the end of the tunnel was not the train. My guess is I had paid my dues, and destiny was opening its doors to me. Among other things, it was about this time that the Veteran’s Administration health care system approved providing gender affirming hormones for veterans such as me. I jumped at the idea of taking advantage of less expensive HRT medicines and free mental health care. Even though I had already set up my hormonal medications through a civilian doctor.

By this time, it was becoming increasingly evident to me which direction my life would have to take before it was too late. I was in the middle to late fifties of my life and if I ever was going to ever have the courage to jump off the gender cliff, I would have to do it. One thing I did not want to do was continue to live the part-time gender existence I was already living. Plus, I was rapidly nearing the point in my life when I could take early retirement. Which would preclude me from having to go through any ugly transition on the job scenarios. I worked in a very male dominated profession, so switching genders on the go could have been quite challenging.

Finally, one night when I was out to be alone, I decided I was enjoying myself so much, I needed to end my gender turmoil forever. I decided to forsake all my male privileges I had fought to earn for decades and seek out my dream life as a transgender woman. It was not a decision I took lightly as I sent all my male clothes except my Army uniform to the thrift stores which were so beneficial to me when I was first acquiring my transfeminine wardrobe and fashion.

By this time, I was sixty and I figured I would never have a better chance to transition again. I took advantage of all the feminine “practice” I had done over the years. I was able to hit the gender ground running and never looked back.

 

Sunday, July 20, 2025

Can You Ever Enjoy the Ride?

 

Image from A. C. on UnSplash.

Lately, it has occurred to me how often I did not pause to enjoy my gender journey.

Perhaps it was because for the longest time I experienced very little gender euphoria for two reasons. The main reason was, I was never raised to feel any joy in my life. Nothing was ever good enough. So, when I entered the world as a novice cross dresser or transgender woman, life was very tough. The other main reason was, I was approaching my life from the exact wrong way. Deep down I knew when my “buzz” went away so soon from merely dressing up in feminine clothes in front of the mirror, I was doing something wrong. I did not know then my gender issues ran much deeper than just a love of fashion and makeup.

Before I knew it, I was in a vicious gender circle in my life when I needed to dress up rather than wanted to. There was a huge difference. When I needed to cross-dress, I had the tendency to take more chances and jeopardize my life as I knew it because I knew there was no way my parents would ever understand how their son was really their daughter. Plus, there were many other distractions too, such as not being able to afford my own wig until I was well into my college years. I hated running around with a towel on my head fantasizing that I had a full head of luxurious girls’ hair.

There was always something I was reaching for which ruined my present enjoyment. Such as a better dress, shoes or makeup which could help me look better as I had neared an impossible ideal of attractiveness. Facing my reality of appearance when the only feedback I had was in the mirror. As we all know, the mirror has a tendency to lie to you if you are not careful, and I needed a way to test my presentation as a transfeminine person in the public’s eye. Easier said than done, when I was busy living my own down low in a male life I was frustrated to be in anyhow.

Very quickly, I learned the mirror had been lying to me as I was rejected by the public. To succeed with my dream, I needed to pause my life and attempt to find out why I was having all the problems I was having. Almost immediately, I determined I needed to get my male self out of the way. He was dictating how my fashion presented itself and it was all wrong. For any number of reasons trying to dress sexy in the wrong places was getting me into trouble. My guy was dressing me for other guys when I should have been dressing for other women. Once I figured out, I was not a teen aged girl, my public life became decidedly better.

So much better, I was even able to enjoy several of the solo nights out I went on to be by myself. Even though I knew I was a transgender woman, I was just being me, and the public (amazingly enough) was accepting it also. My mirror even came back into play, and I used it more often in places such as women’s rooms to adjust my hair and makeup.

Life then began to roll on very fast. All the way to the point I was having a difficult time keeping up. I was learning so much about the feminine side of life, it was too late to turn back then and more and more, I was discovering how much I loved this new side of life I had always dreamed of.

Also, my life was reaching a new level of complexity as I was shutting down the male side and giving full access to my female side who had waited so long to be free. My problem was I was still trying to live part time in both genders as I transitioned, and I was afraid of what would happen when I lost all my male privileges. Finally, my mental health could take it no longer and I had to jump off the gender cliff I have written about.

As I jumped, the ride down was scary but fun in its own way, not unlike a big rollercoaster at an amusement park, the ride up in many ways was worth the ride down. All the fear and terror I had experienced when I had come out to a close family disappeared when I was accepted by my daughter and my wife Liz and a warm set of relief sat in. I could not wait until I could get back in public and live my true existence out of the closet. I was creating my own universe for a change and not relying on someone else to do it.

I began to build my own female privilege and thrive in it. It continues till this day and is the topic for another day. In the meantime, I often try to pause my life and enjoy where I am in my life.

 

 

Monday, July 14, 2025

Unlearning LIfe

 

JJ Hart

Over time, I spent so much time and effort unleashing my male past, I cannot remember it all.

As soon as I could think about myself, I knew something was wrong. I just did not know what. Primarily, I did not know I was trying my best to survive in a male world I wanted very little to do with. Perhaps the biggest problem came when it was time to unlearn all the male life I was forced into. I was the proverbial round peg in the square hole, and I did not like it, even though I was rewarded with white male privilege when I was successful.

By choice or not, it seemed I was always fighting myself or the world for my gender dreams or goals. Very early I knew somehow, I wanted to be a woman someday, a deep dark secret I needed to keep to myself. Overall, I was deeply conflicted about where my life would end up because it seemed as if I was on a runaway gender train I could not get off.

A prime example was when I entered male puberty. I watched in shock as my body grew angles, and I needed to walk like a man. I am sure I was a comical sight, but I tried. I did not want to be referred to as a sissy and bullied in school and I was successful. Until it was time to reverse it all. When I left the cross-dressing mirror and entered the world as a novice transgender woman, there was so much to do as I was busy unlearning my male life. First of all, there was that male walk I needed to get rid of. There was no way I could overcome the positive feminine presentation I had succeeded at doing, if I was going to continue to walk like a man. Plus, I had the challenge of doing it in heels.

When I learned to walk in heels, I learned the inherent power of female privilege. Suddenly, my legs looked better, and men paid closer attention to the clicking of my heels. I just needed to match the rest of my fashion to blend in with my shoes. Since I loved my boots, the first thing that I did was try to save up for a pair of nice, heeled boots and find them in my size. Thank goodness for Payless Shoes. For the most part, I did good in my heels except for the time I got a heel stuck in a sidewalk crack in a mall I was walking in and the time I fell on a wet spot in one of my regular venues I was in. I survived and learned I needed to be more comfortable.

Another major gender response I needed to unlearn was to always look another woman in the eye when I talked to her, especially in bathroom situations. Eye to eye contact was normal in women’s rooms and totally not in men’s rooms. The new rules of the “room” I needed to unlearn and relearn if I was to survive as a transfeminine person.

Another major point of contention I write about often, is the difference between male and female aggression. I needed to unlearn the old male aggressive ways of coming right at you. On the other hand, I was clawed many times when I failed to recognize the passive aggressive intentions of a woman I was dealing with. Often behind that smile was a sharp pair of claws waiting to take a shot at my back. I needed to keep my head on a swivel and always be careful when I was dealing with other women in the girl’s sandbox. Lesson learned and I moved on as a better transgender woman.

Finally, all these lessons began to come together in my life, and I started to become a whole human being again. But this time, a human I wanted to be. No more unwanted male who I still needed to fall back on in times of duress. Afterall, I had to live with him for nearly fifty years, so there was some good to remember. I found I could relate to both binary genders better and understand where they were coming from. Of course, men were the simpler of the two genders as I suspected and women were more complex, and they led more layered lives.

None of it mattered to me as my world opened in ways I never imagined. Going to the extreme of unlearning my old life was radical but then again, I was able to make it work in my own way. If you are searching, just be aware everyone’s journey is different but maybe you can make it too if you are careful. There are huge inherent problems when you decide to forsake your male privileges and enter a new gender world.

 

 

Saturday, July 12, 2025

Did I think Life Would Turn Out this Way

 

JJ Hart.

Did I think life would turn out to be this way, I would have said NO!

In the earliest days of just exploring my mom’s clothes and admiring myself in the mirror, I never thought life would have become as complex as it did. For years, I thought my cross-dressing urges were an innocent hobby which hurts no one. I was entertained and it was all that mattered in my selfish world.

Little did I know, all I was going through was just the beginning of my life I would have to adjust to if I was going to survive. I was embarking on what turned out to be a very unique life as I had the opportunity to live life in two of the main binary genders.

To put it all together on a timeline, I was in my thirties when I first read the term transgender for the first time, and I thought I had finally found a term which described me. Or, at least put words to my gender dream of possibly living a transfeminine life. Up to that point, I had only experienced the other gender variant people I met at various mixers I went to. When I attended the mixers, I met everyone from cross dressers in cowboy hats barely covering their masculinity all the way to impossibly feminine transgender women who were on their way to surgery. I certainly did not think the mixer I went to would turn out that way. I was expecting to attend, meet people like me and come away with new answers about myself. Of course, it did not turn out that way, and I came away with more questions than answers afterwards.

Primarily, I found myself on a sort of a gender balance beam. I was very clumsy and became well versed in playing both sides of the gender spectrum. At times I was good at my games and at times I was very bad, and I suffered. Through the bad times I needed to keep my eye on my gender dreams, be selfish and do the best I could. Perhaps the worst part was, I still did not know how any of it would turn out.

It was only when I managed to escape my dark, lonely gender closet and explore to learn if my future transgender dreams were possible at all. I was in a long-term marriage with a woman I loved, in a successful job and outwardly living a good male life. Why would I want to sacrifice any of the white male privileges I had earned. I did not think on occasion that I ever could.

What changed everything for me was the further I went on my journey, the more natural I felt. I began to think more about my life was meant to be this way. When I was selfish in my gender choices and I did my best to be a chameleon with my life. These days, I would be known as being gender fluid. Another term not known in those days, instead I thought of myself as an androgynous person. Especially when I started gender affirming hormones or HRT. What happened was, I really started to play with fire then. I had given myself a loose timetable until I made the final transition from male to female but could not keep it when the changes to my body became much more noticeable than I had ever imagined.

I never had thought in a million years, my life would turn out this way and I needed to arrive at a point where I needed to be selfish again and give up on my male self. My longer hair, softer skin and budding breasts were giving me away. It was time for a change. In fact, way past time for me to face the inevitable, I should have been living a transfeminine life all along.

All the torment and balancing acts I put myself through were no more than tormenting myself needlessly. Perhaps the final clue was how quickly my body took to the new feminine hormones. There was no negative to the process at all and the calm I suddenly felt led me to feel I was in the right place.

So, no, I never thought I would be in the spot I am in today. I am living as a transgender woman with a wife who supports me totally. The only slice of life I lost was my brother’s acceptance which was overcome by my daughter’s. It has been over a decade since I have spoken to him and truthfully, I haven’t missed our interaction. I am sure I had a few lucky breaks along the way, but for the most part, I think destiny was leading the way. Along with my stubbornness to continue my journey. It does not matter as it all worked out.

 

 

Friday, July 11, 2025

It's Just Life...Not a Joke

 

Image from Engin Akyurt on UnSplash.

It took me awhile before I finally came to the point in my gender transition when I gave up and thought the whole process was just life and not some sort of an evil joke.

I had struggled enough through the years when my male self-put up quite the struggle to exist at all. It was as if he was on a slippery slope towards losing his life altogether. To make matters worse as I always point out, my male side’s life was not always that bad. I had a long-term marriage, close friends and a good job to fall back on when I needed it.

Through it all, I thought it was only the draw of the feminine clothes which kept me longing for another trip to the mirror. I did not realize my feelings went much deeper than that. I was feeling life itself. It took me many years and even decades traveling a very curvy and bumpy gender path to realize where I was. Plus, many times, when I realized where I was, I became scared of losing everything. Falling off a gender cliff became a real possibility.

No matter how frightened I became, somehow, I kept on moving forward thanks mostly to the brief moments of gender euphoria I was feeling. The interludes helped me to determine if my dream goal of living a transfeminine life was possible at all. Back in those days, I was immersed in the struggle to present well as a woman and not much else. In fact, when I go back and read my earliest blog posts, I cannot believe how much they emphasize fashion and makeup. It all happened long before I needed to learn the layers of life a woman goes through to live her life. It was like my wife told me be man enough to be a woman. In those days I was not as I made weak attempts to live in both main binary genders.

In the short term, I did not understand what my wife meant as I became semi successful in presenting well in the world as a woman, but I had not paid my dues. I found I would have to wait until my wife had passed away before I could earn my way behind the feminine gender curtain to be allowed in by the ciswoman gatekeepers. It was about that time too when I began to understand my dream of ever becoming a fulltime transgender woman could be possible. It was much more than a hobby or part-time profession; it was my life. Then my realization led me to understand what my wife was talking about. I needed to set off on an all-out journey to live my best life as a transfeminine person. I even needed to understand questions about my own long held sexuality. If I lived as a woman, would I suddenly have to like men sexually? I just didn’t know until I set off to experiment.

Along the way, I did manage a couple dates with men which led to kissing but not much else and I did not feel much of a spark of any kind. On the other hand, I was surrounded by curious ciswomen (including lesbians) who wanted to socialize with me, so I was happy, I had always been a contradiction in terms socially, meaning I always enjoyed company even though I was shy and I could continue to feel that way. My life was beginning to come together in ways that I never imagined possible.

For example, I never imagined I would have been able to enjoy a small closely knit group of women friends who taught me more about life than they ever knew. Without any pressure, I was able to sit back and live vicariously through them and primarily how they lived their lives without the validation of men. It was not too long until they began to invite me along to their lesbian mixers, which I loved. I was even approached by other women and kissed. Which provided me with a huge amount of validation.

With my sexuality and life coming together, I could concentrate on enjoying my life on my new gender affirming hormones or HRT. The hormones went a long way in syncing up my internal and external self. Along with softening my skin and facial lines, my whole world was changing too. My emotions heightened as well as my senses as the world around me was softening. A perfect match to my rapidly expanding social life.

I will never know if waiting so long to transition into a feminine world was worth it or not because I had so many excuses why I never had done it. All I really know is, I did it before it was too late and have never looked back. That’s life.

 

 

Thursday, July 10, 2025

At the Gender Crossroads

 

Image from Timelord on UnSplash

Many times, in my life, I have found myself at a gender crossroads.

Of course, like most of you, I learned from the situations I put myself into. As I always mention, the first one was when I needed to leave the comfort zone I had created with the mirror and attempt to live in the world as a transfeminine person. Initially, I was slapped down as people laughed and smirked at me. Until I learned to own who I was, which was a huge crossroad to negotiate.

Over the years, I began to think I had seen everything, but I had not. My main problem was I needed to make the final decision on which way I would go if I was faced with a making a final decision on which gender I would ever live as. Plus, I did not know if I even could live as a transgender woman. I kept searching and learning until I found I was not a man cross dressing as a woman; I was a woman cross dressing as a man.

I discovered also, I would need to transition more than once if I would ever try to make it to my dream life. Primarily when I learned it on the night I finally decided I would quit going out as a cross dresser and change my inner thought pattern. I was fed up with just trying to look like a woman and wanted to feel like one and see as if I could mingle with a group of ciswomen with no issues. I did make it with the other women and crossed another road I knew I could never go back. I mingled and socialized with other women and even used the women’s room with no pushback at all. It was amazing.

The next transition I need to make was when I needed to begin communicating with other women. It was never easy and a complete learning process. It does not take a genius to know women and men communicate on a different level. I knew well how to do it as a man, but I was a total novice as a woman. The first lesson I learned was I had to pause and listen to the other woman I was talking to. As a man, I could often make the first move and hope for the best. With women, I never did and often waited for a passive aggressive response. The real intent behind the smile often startled me until I caught on to the game.

All of it led me to the success I needed to this day to be successful with other women who indirectly try to bully me in their own way. An example was the ciswoman I wrote about in a recent post when she could not adjust to me being a parent not a dad to my daughter. In fact, I had a reader (Michelle) who responded to the woman and my return comment: “You handled it with so much more grace than I probably would’ve. And Liz’s quick response? Perfection. I’m so glad you still got to connect with your daughter and your grandchild, that’s what really matters. The rest is just noise.” Thanks for the comment! The woman was very noisy and was trying to bully me in her own way.

I was just fortunate that both Liz and I had been through similar situations, so we were ready. Somehow, the woman thought she had me over a gender barrel with the dad comment and that was when Liz took over. The woman asked Liz who I was to her and Liz said wife and the woman shut up.

My point it, both Liz and I had been through situations with other women such as her before, so we were able to handle the noise and go across yet another crossroad. By this time, I think there always will be another road to cross as I see my gender dream come together.

As Michelle said, the world is full of noise, and we must separate it into genders to make sense of it. Which would be another blog post altogether. In the meantime, for all of you approaching your own crossroads, try to feel secure on your journey and be careful. Especially these days when depending upon where you live transgender rights of any kind are in danger.

 

 

Wednesday, July 2, 2025

The Second Act

 

JJ Hart doing Trans Wellness Outreach. 

Will the second act of life be better and more successful than the first? How many people even get a second chance?

That is the question I needed to answer when I finally shed my male life and entered a transfeminine existence. Since I did it at the age of sixty, I have had plenty of ground to catch up with. Many times, it seemed I never would. My internal gender clock was moving one step forward and two steps back as I attempted to transition. I had times when the picture was clear in my mind, and I was able to put it into motion. Such as the night I took myself out to see a major Christmas light display in a nearby village and was warmly accepted in my soft bulky sweater, leggings and boots. Then, as I rode the wave of gender dysphoria, I would do something wrong such as how I was moving. I am fond of saying, I looked like a linebacker in drag.

The problem was, if I relaxed at all going into the second act of my life, I had the tendency to fall back into old habits. I was learning the hard way over and over, to take nothing for granted in my new life. Many times, I tried and failed not to be too hard on myself since I was making up for a first act in my life which lasted so long, and I had to concentrate so much on it just to survive. It was around this time when my male self really began to set up roadblocks on my gender path. Suddenly, he began to see that this road I was on was not a phase or joke and I was deadly serious.  He started to ask questions such as how I was going to live in my second act with no job and how I was prepared to do it without the wife I dearly loved and had been married to for nearly twenty-five years. To be sure, all very real and very scary questions.

I put off deciding my life as long as I could as I attempted to learn if I could really live a transfeminine life at all. Were the obstacles insurmountable or not. Through it all, the one overriding feeling which kept me searching was the deep down feeling I was doing the right thing. I was headed in the direction I should have been going in my life all along and I kept going through the ups and downs of transitioning into my second act.

Once it was clear I was successfully transitioning into my second act, I needed to make sure I was doing it correctly. It turned out I had all the help I needed. In addition to the cisgender women I always mention, there was one important person I don’t mention enough. That person turned out to be very real and important to me. She was my inner feminine person who had been waiting for all those years and decades for her chance to fully come out into the world. Once she finally did, she knew completely what to do and what was ahead for my second act of my life. Mainly, all the nuances of life as a woman if I really wanted to go there. She knew the best part of my life was yet to come.

More importantly, I had finally made it through the bleak years when often I thought there would be no tomorrow. Or at least my dream of living a feminine life would never be realized. Often it set off a series of insecurities in myself which set back my life. Act one was bleeding because I could not get to act two.

When I finally made it to my second act, it was as if I had lifted a heavy weight off my shoulders, and I came to a point where I needed to be more understanding and approachable in the world. I could not get away with the old male ways of internalizing my feelings and start living again. If I did try to hide as a transgender woman, I would never have a chance to provide myself with a positive outlook to other women and not come off as an unfriendly transfeminine woman which was the last thing I wanted or was.

Since I was one of the few humans who ever had the chance to stop their life and begin again so there was no way I could mess it up. I needed to enjoy life and live it the best I could.  

Monday, June 23, 2025

The Biggest Lie

 

Image from Dave Goudreau 
on UnSplash.

Sadly, the biggest lie I’ve ever told in my life regarded my biggest truth.

The lie of course, regarded my gender identity. For simplistic reasons I could say the problem I faced early in life was having a complete lack of information to lean on. It was back before the internet information years, and I thought I was the only boy in the world who wanted to be a girl part of the time.

To compensate for my cross-dressing activities, I was prepared to lie my way through it. If I was ever caught red handed because of leaving lipstick on my fingers. Due to whatever circumstances which were beyond my control and very lucky, I was never caught by my family. Although I always have wondered if my mom somehow knew but hoped my fascination with her clothes was just a phase I would grow out of. The best part was, I never was caught or questioned so I did not have to lie my way out of an ill-advised trip to a psychiatrist. Back in those days, being a transvestite (the term which was used) was a mental illness problem. Not something I wanted to face. So, I hid in fear.

As I weighed the two alternatives, fear or lying, I chose to internalize the fear I was feeling every time I put on feminine clothes. Once again, I was able to put off lying to the one biggest person in my life…myself.

All was well until I was discharged from the Army and returned to civilian life. Once I did, I began to pick up where I had left off with my gender issues. I even went as far as almost telling my first wife who was also in the Army and was being discharged several months after I was, to expect a totally different me when we met again. I was totally thinking of meeting her as my transfeminine self. As much as I secretly wanted to, deep down I knew I was not ready for such a big move, so I hid my feelings again and lied my life away, for a while.

You know what they say about lies, the more you lie, the more you have to. Just to stay above water. Before long, I was drowning in my own personal lie, until I met my second wife. She was much stronger than my first wife who never said anything negative to me at all considering my gender issues. I often thought wife number one would not protest at all if I told her I was leaving for a period of time for sex realignment surgery. She was just too easy, and I divorced her to be with my second wife who also knew of my cross dressing. Which started out good but deteriorated

I say deteriorated because my second wife did all she could to support my growing gender issues until I had outgrown both of us. All of the times she encouraged me to go ahead and rent a motel room and spend the day out as a woman taught me valuable lessons. First and foremost, I could make it in the world as my feminine self after all. Then, the big lies started as I began to go out on my own when my wife was at work, from the house. Which was something I told her I would never do. By doing so, I began to live the biggest lie of all, as I was increasingly aggressive in my attempts to do more and more in the world away from my masculine self.

Naturally, the tailspin I put our marriage into put a strain on both of us. Especially when she caught me going out. When she did, a massive fight would break out for days until somehow an uneasy truce would be called. At times, things would be so bad, my wife told me just be man enough to be a woman. The problem was, I was still lying to myself thinking I could keep my married life balanced with my transfeminine one. I just was not that good a juggler to do it. Again, mainly because I could not face my truth.

Sadly, my second wife passed away before I faced my truth. Being the wise one in the relationship, she knew me better than I knew myself. Pushing me to pay attention to what it really meant to be a woman.

Now I just wish I did listen to her and went ahead and transitioned. Sure, it would have been difficult but living the life we lived was difficult too and I could have started living with a clear conscience. Being the stubborn person that I was, I kept on living a lie until I could take it no longer and finally made the move into a life I could enjoy as a fulltime transgender woman.

By the time I transitioned most of the important friends I had known (including my wife) had passed away. Leaving me alone in the world to carve out a new life in my sixties. It would have been very difficult, but I wish I had listened to my wife and been man enough to be a woman sooner.

 

 

Wednesday, June 11, 2025

Riding the Gender Merry go Round

 

Image from Stanley Kustamen 
on UnSplash. 

Catching the gender merry go round when it was in mid-spin was never easy. As I always point out, I had no workbook on how to achieve my feminine desires that were available to me.

I often wondered what magical experiences were available to the girls around me but were off limits to me. What did the girls really learn about being feminine from each other? Was makeup one of them? I was jealous because I had none of the early basics of applying makeup. The closest I came when I was painting the model cars I had. I never was very good at skillfully painting cars, so I wondered how I would ever be good at painting myself. Enamored, I remember watching my mom apply her makeup as I looked for any small hints I could follow but I never seemed to learn.

Of course, there was much more to jumping on a spinning merry go round than just skillfully applying makeup. There were clothes to worry about too, and how could I afford them on the very limited budget I was on. I resorted to taking any small jobs I could as a kid to augment the meager allowance I received at home. In fact, my major source of income was a neighborhood newspaper route I took on. When I added all my funds up, I usually had enough money to buy my own makeup, panty hose and other rare items such as a pair of shoes I was lucky to find.

Once I was able to be confident in my ability to jump on the merry go round, then I needed to worry about hanging on. In the early days of my public explorations, I was having a very difficult time presenting well at all and I often was laughed at by others on the merry go round until I began to learn what I was doing wrong, and I could fill out my feminizing presentation workbook. It was a win for me when I could quit using crayons on my face and use them to color my workbook, I was less and less a clown in drag, and more and more an androgynous person for the public to judge my gender. For once, I could rightfully claim my seat along others on the merry go round because I had earned my spot as much as they did.

After a while, the spinning became too much for me and challenged my fragile mental health. The biggest problem I had was my refusal to face myself and my innermost truth. I was never a man cross dressing as a woman; I was a woman cross dressing as a man my entire life. The basic thought of who I really was consumed all my spare thinking. I am amazed now how much I still accomplished in my life as I suffered my mental duress. At times, it seemed my merry go round was spinning completely out of control. Plus, at the same time, I kept accumulating extra male lifetime baggage I did not really want. Sadly, the life I was living kept me from making very many close friends because I just thought I was knowing them under some sort of false pretense. I wasn’t the man they saw before them; I was a fake. Which I hated and added to my problems.

I finally came to the point where I needed to either slow down my merry go round or get off altogether. I just couldn't take it any longer. I certainly was not getting any prizes for putting myself through the anguish of staying on. I had given my ride the best shot I could, and I needed to grow in my transgender womanhood. I had tried my best to outrun and out drink my gender issues, and it was time to face the reality of who I was.

When my merry go round glided to a stop and I was able to look ahead to the new life I was about to enter. I was excited to see and live my feminine reality. I had filled out my workbook and paid my dues and was ready to go. The next time I was at an amusement park I could really enjoy the experience as a transgender woman. If anyone in the world did not like it or approve of me, I didn’t care. I had spent a major portion of my life thinking I was in the wrong. When in fact, the bigots were the ones in the wrong and they were the riders who needed to get off the merry go round first.

Tuesday, June 3, 2025

Climbing Walls

JJ Hart

 When I transitioned from male to the feminine person I was all along, I hit many walls.

As it turned out, some were short walls and easy to climb, and some were almost insurmountable. The problem quickly became which were which. Very early on, when life was simpler, the act of applying eye makeup initially presented itself as a major hurdle, or wall. Once I conquered that challenge, I was able to move on to bigger and better things. Little did I know, I would be facing bigger walls to climb. A few were so tall I could barely see my dream of living fulltime as a transgender woman at all.

Leaving my safe yet dark gender closet and trying my hand at living as a novice cross dresser or transgender woman in public suddenly presented me with many new walls to climb. Iniitally, there was the omnipresent pressure of presenting properly in public as a woman. To do it, I needed to overcome how my old male self-thought I should look and change it to how my femininized self knew how I had to look to blend in with her cisgender counter parts. Plus, I needed to do it on a regular basis as people were starting to remember me. There were no more changing names to fit a new wig I was wearing. At least I needed to understand that even though strangers knew I was not a cisgender woman, I needed to prove I was a person who was nice to know and got along in the world. Most of all, I was not some sort of a freak, and I needed to remember in the overwhelming number of cases, I was the first and only transgender woman the public had ever met.

The frustrating part of this time of my life came when I was taking a step forward towards climbing another wall, then slid back down when I hit it. I was rapidly losing all the press on nails I bought as I was trying to climb. I seemingly always had problems with moving like a woman. No matter how much I tried, I still ended up moving like a stiff football player in public when I walked into a venue. I worked long and hard to correct the problem and finally succeeded to an extent. Putting femininized self into motion was a problem so large, it was only topped by the communication problems I was having dealing with the public. Basically, I was scared to death of talking to anyone. It was particularly frustrating when I began to talk to other women, who I very much wanted to be friendly with.

On the other hand, men were not a problem at all, since for the most part, they left me alone. The problem was partially solved when I took feminine vocal lessons and the rest with pure practice. Finally, before I came off being unfriendly with other women, I just gave up, relaxed and did the best I could to enjoy and learn from the conversations I was having.

Before I knew it, the walls were coming down and I was gaining the all-important confidence I needed to reach my lifetime dreams of being a woman on my own terms. My terms became rather obvious over time. No major gender surgeries which I thought were too expensive and risky for a person my age of sixty. I would just have to take all my learned experiences out of the closet, put them together and do the best I could.

Another of one of my remaining tallest walls was doing more for my inner self. I solved it by becoming eligible for gender affirming hormones. My initial thought was the changes I would experience would be external, not internal. It turned out, the internal changes were more immediate and far reaching than the external changes. In fact, I can and should write an entire blog post about my changes on HRT. Briefly, I entered an entirely, the new, softer world. Suddenly, I could cry, and my senses improved. Perhaps the biggest one was I was more susceptible to changes in temperature. I learned all those years of thinking women were faking it when they were cold was true. When I was reaching for my coat on a chilly evening.

Certainly, HRT helped to tear down most of the final walls in my gender journey. I say most because I do not think all my walls will ever be totally gone. After all, I have lived most of my life as a man with all the resultant experiences and privilege. No matter what I do what is left of him will still be with me. His former life will always be with me. I just need to learn from him and conquer all the walls he put up in protest.

I Never Missed a Beat

  JJ Hart Once I started down or up my long gender path , I never missed a beat, even though on occasion, the beats were far apart. The be...