Tuesday, October 20, 2026

Seeing It All Clearly Now

 

Image from Lola Rose
on UnSplash. 

As I journeyed for years along my decades old gender path, I discovered I could see life much more clearly.

Going back and forth across the gender border from male to female allowed me to see what goes on in the lives of both binary genders. Something that is very rarely accomplished by very many human beings who are stuck in their restrictive gender boxes from birth. But, what about the rest of us who for some reason, got put into the wrong box and were forced to live a life we never wanted until we went out on our own to change it. That is where we start to see the changes in our gender set in. Or maybe something was wrong when we were put into neat little boxes at birth.

In a classic what goes around, comes around, we go around searching for our authentic selves as transgender women or transgender men until if we are lucky, it comes around back to discovering our true selves later in life. How we can come to that conclusion is as different as human beings can possibly be. Some of us take shorter routes than others. If I use myself as an example, I took decades to come to my gender truth that I was hiding from me the whole time. If I had the courage to face my truth earlier, my life would have been so much different. I am sure it would not have been a completely positive experience, but at least, I would have been working towards living a transfeminine life much earlier than I did as a serious cross-dresser.

I was the classic person who does not see the forest for the trees. Since all my trees had a big transgender marked in every one of them and I thought it could not be for me. Even though I was going as far as cross-dressing three out of the seven days of the week if I could get away with it.

At the least, during those three days of the week, I was learning to present better in the world the way I always wanted to. As I did it, slowly I was seeing what I needed to know if I had what it takes to cross the gender border for good and would the grass be even greener when I did it. Plus, as I always mention, I had an increasingly successful male life and family to deal with. At the least, my second wife knew about and reluctantly approved of my cross-dressing but always drew the line if I was thinking about going ahead with the next step for me. Which would have been HRT-gender affirming hormones. She always said she did not sign up to live with another woman, and I never had the courage to tell her she already did. In the meantime, I clashed with my two main ciswoman role models, my mom and my second wife. I admired them for being strong women until it came to the times, they did not accept me.

The problem was I was seeing clearly the trans person I was becoming and every positive step I took led me to believe I never wanted to go back to the male life I never asked for. Most importantly, I was building the confidence to do it and ignore the gatekeepers like my wife and mom. I felt deep down, if I kept knocking on the gatekeeper’s door, someone would let me in, and I could experience for myself what went on behind the gender curtain.

When I finally made it behind the curtain, I found the feminine reality I was always looking for. Far past the shiny fashion, hair and makeup intangibles all the way into the complex lives that ciswomen lead. By that time, I had paid plenty of dues to get there and just figured my socialization as a woman was part of life I should cherish. If anyone wanted to get in my way, shame on them because by that time I could see clearly who I really was in my unique form of womanhood. Other women saw me too when I was asked to pose for a book about different women for a judging in Chicago years ago. It was to be my only experience as a photographer’s model, and I was nervous, but I enjoyed the attention immensely.

The rest of my life was not as exciting as posing for a photographer, but in other ways, as satisfying also. I was enjoying building new acquaintances with my wife Liz as we went to writers and crafters meetup groups to intermix with total strangers. The whole experience helped to get me out of my shell and lift the fog away from whom I was destined to be in life. Most importantly, I was happy doing it. Something I was never allowed to do when I was growing up when doing good was not good enough, there always had to be something better. I never imagined how much that carried over into my adult life until I began to come out of my gender shell. Even still, I had to work my way out of the idea that there always was a better dress or wig I could buy which would magically transform me into an attractive passable woman.  It was all good until I looked in the mirror or went out into the world attempting to be myself. Some nights being myself was within reach and some nights it just was not and I needed to go back home disappointed.

I went back to my gender drawing board continually until I slowly got it right and began to present myself in the way as the trans woman, I wanted to be.  I took advantage of all the time that I wanted to see the best woman I could become on my own terms. It was the best I could do. I was done with all the denial I had put myself through which should be the topic of another blog post.

Speaking of another post, I always invite you to join me again and read along. Thank you! 

Comments are always welcomed. 


 

 

 

 

 

 

 

 

 

 

Monday, October 19, 2026

On the Path to Being Me

 

JJ Hart. On the way to
being me.

On the road to being me sounds like one of the old “Bob Hope” and “Bing Crosby” classic movies if it was not so real.

It just so happens that the road I chose took me decades to travel and I finally arrived when I was in my mid-fifties and I tried to internalize my gender dysphoria by being an occasional but serious cross-dresser. Since I had very few natural feminine qualities, I had a lot of work to do.

Little did I know the lengthy journey in life that I was on would take me down so many side paths including three marriages. Including the one I am on now. All except one lasted over ten years, so I guess you can say I made up for in loyalty for what I lacked in other areas. Such as reoccurring gender problems I shared immediately with my wives before I married them. The major problem I had was I was never being honest with myself about who I really was which was a shame because deep down early on my path I knew I wanted so much more in life than just wearing the clothes and makeup of the women around me.

When I thought I was taking the easy way out about hiding my deepest desires, I was only masking my problems which made me a very bitter and nasty person to live with. Not a good recipe for a stable marriage, but somehow, I managed to maintain them anyhow. At the same time, I was trying to internalize my gender dysphoria, I would put extra pressure on myself to do more in my search for my own brand of womanhood. What I did not realize was all that I was doing when I began to explore the world outside of my closet was just socializing myself to the male to female femininization path I was going down. And every high heeled step was getting me closer to my goal. Even though, it was taking its own sweet slow time to do it. I found that every time I took a step forward, I would catch myself taking two steps back.

What would Bing and Bob do should have became my motto as I moved on in my mainly male world I was stuck in and could not get out. The only thing I did know was that I was stuck in a cruel gender comedy show I needed to get out of. I wanted so bad not to be perceived as a clown in drag coming from a local circus. The only thing I could do was stay on the dual path I was on to maintain the only life I knew. We were living paycheck to paycheck at the time so there was no way I could quit my job and try to start a new life over. I did the best I could to keep a balance between my two genders until the cavalry came to rescue me. The only problem was that the cavalry never came and I was on my own and was forced to learn to stand on my new high heels.

For years, I went into a self-imposed transgender exile as I needed to do a deep dive into who I really was and what I really wanted in my life. Sadly, I kept on betraying my true feminine side for my macho male side who was only good for paying the bills. The only relief I got came as I learned of the term transgender and immediately appreciated how it affected me. No pun intended, but it fit me to a “T” since I knew I was much more than a casual cross-dresser at the time. But at the same time, I did not have the desire for any extensive/expensive gender alignment or facial femininization surgeries, Somehow, I was going to have to find a way to pursue my trans womanhood on my own terms. All that was remaining was to figure out what those terms would be.

The only thing I knew for sure was I was becoming certain about who I wanted to be. I was tired of lying to myself and decided to start to carve out my own authentic transfeminine life. As I did it, I was beginning to get my glow back and love the skin I was in. The problem I had was loving the skin I was in, but I had not considered all the aspects of what I was seriously considering. For example, how was I going to tell the remaining close family and friends around me and how was I going to support myself when I started to live my dream life I always dreamed of doing. It turned out my procrastination came back to help me when nearly all my immediate blood family had passed away. Along with the only long-time male friends who I still had. Since I had always had such a difficult time making friends with me, I was not worried about making anymore anytime soon. It all left me too how I would support myself financially.

Once again, procrastination worked when I waited long enough to transition that I was old enough to collect my social security and sell collectables on the side so I could get by. I made enough money to keep going out in the world as a trans woman and keep carving out my new and exciting life. I went up, down and sideways to do everything right in my power to finish my dream of being able to live fulltime as a transgender woman on my own terms. My own terms were very simple; I just had the basics of living how I wanted. But again, I was frustrated when I went to do it. I wanted the path to finding my future to finally end and I could get on with my new life.

Most importantly, my new life was all I expected it would be and I could not wait to experience more of it.

Experience in life is all we have and I hope you get a chance to experience yours!

Thanks for reading along and any comments are always appreciated.

 

 

Sunday, October 18, 2026

Putting Yourself Out There as a Trans Girl

 

Image from Sasun Bughdarian
on UnSplash.

Putting myself out there in public was probably the hardest thing I ever have done in my life.

Most of the time I was in a high-risk-high reward situation as I tried and failed miserably at presenting myself in public as a novice transgender woman. I kept on working until I put myself into the low risk-high reward category when I finally was able to pass reasonably in the world I discovered was run by ciswomen if I ever wanted to succeed. I was so far away from the world of cross-dressing/transgender parties and socials I kept going to, I was learning so much more every time I did it. I was on thin ice on my gender path and I knew it. I just hoped the ice would hold my weight. Even though I was on a crash diet to be able to purchase more fashionable clothes and look better. It was questionable. 

All along, I knew there was no way I could go halfway and make it to my dream of living fulltime as a transfeminine person. Trying to live a life stuck between two genders was no way for a person to live and when I did, the gap between the two genders was too much to overcome. My mental health suffered and I was very self-destructive and had to do something about it. The last thing I wanted to happen was that my gender dysphoria would doom my life as I knew it.

In the meantime, I did the only thing I knew how to do which was continuing to hide my cross-dressing from the world behind a wall of male macho intentions. Again, it was so hard to hide my truth that much later in life I was surprised that no one had guessed my dirty little secret when I finally cracked my gender egg and made it out of my closet for good. Another problem happened as I had to keep building a successful male life, I never wanted, I knew some day soon I would have to tear it all down and start all over again. Internalizing and putting that day off, just hurt me more as I continued to put myself out in the public’s eye.

By doing so, my risk situations leveled out to a point where they almost balanced each other. I was in the ultimate high-risk situation of losing essentially my whole life but at the same time conquering the higher risk of being able to carve out a new and exciting feminine life from scratch. It seemed to me that every corner I went around on my new path had different obstacles to take on as I was intimidated by the complexities of the ciswoman’s world I so badly wanted to live in. As I left the male world I wanted nothing to do with, it seemed nothing was easy to do as I had to learn everything I could quickly if I ever wanted to survive. The worst part of it was, I wanted just to keep running back to the privilege of the male life I had given up but just could not.

So, I kept putting myself out there to make a lot of bad mistakes on the way to my own form of womanhood. Like ruining hours of prep time getting ready to go out, only to discover I was moving like a linebacker in drag when I did it. Or the time when I had everything down when I went out and promptly got my heel stuck in a sidewalk crack and almost fell down. I made it to the point of being so paranoid about going out, I kept on wondering if I would ever be able to put my feminine self in motion for the world. Even though it was difficult to do, I kept forcing myself back out and getting better in my overall presentation. Making it less of a high risk that I could do it. Since I had already been laughed out of venues in the past, what was the worst that could happen to me.

Ironically, my path took me another direction right into the worse than could happen experience when I was almost molested by two men when I was alone on a dark city street and I was lucky to get out of it by giving them my last five dollar bill. It was too close for comfort for me, and I almost learned the hard way what ciswomen are raised to know about the dangers of toxic men. I started to always plan to ask for a transgender man friend to walk me to my car after that. I know I mention that experience a lot but it is my way of always warning you that when you go behind the gender curtain and transition, you lose your male privilege of personal security so be careful when you go out because it is certainly a different world for a trans woman.

For years, I kind of just drifted along in the female world learning what I could to increase my knowledge until I learned too much and found I could never go back to the male life I had before. Almost all the risk on not doing it suddenly became extremely shallow to me as the why’s I should not transition started to fade. I had put so much time and effort into my womanhood, what I was waiting for.

I had even survived the worst moments of my male life when almost everyone around me passed away, leaving me tragically lonely and sad. The only bright light I had to fall back on was the knowledge that my strong feminine self was always there for me and it would be extremely low risk to reach out and ask for her help. Even to the point of helping me find a new social circle to hang out with.

I stepped out of my dark closet again and was fortunate to find a small circle of diverse friends I could socialize with and even grow into my new HRT hormonal changes with. I stepped out of my social box and utilized the so-called straight venues I was already a regular in, along with a transgender woman friend of mine and against all odds found new friends who all happened to be lesbians. From there, I even took the risk of going online to the trashy dating sites and tried my hand at attracting someone else. At that point, what did I have to lose. After a very low-risk, high gain deal, my future wife of over fourteen years contacted me. We clicked and have been together ever since, so I am still enjoying the results of my low risk move. But I must stress, none of that success would have been possible without my determination to put myself out there and try.

Certainly, I failed quite a bit, but from failure came learning and I made it thank goodness.

As always! Thanks for reading along and all of your comments are welcome.

 

 

Saturday, October 17, 2026

Was It Ever Too Easy or Difficult

 

Image from Brian Lawson
on UnSplash.

Looking back at your gender transition, was it ever too easy or too difficult? From many of the comments I receive, I would say the answer is difficult. Even if you are an everyday cross-dresser all the way to a post opt transgender woman.  

For me, it went both ways like my gender as it depended on the experience or even the day. For example, when I was getting laughed out of venues I should have been passing in, my whole life was too difficult as the opposite of gender euphoria set in. My inner stubbornness set in, and I just had to do something to make my life better.

By this time, I was in survival mode. Clinging to every shred of gender euphoria I could find. By taking the time and effort to make my dysfunctional life better, I was making it worse. Just in time, when I was in total despair, I learned what I was doing wrong in the world to blend in and begin to prosper as a novice trans woman. Mainly I was dressing way too inappropriately for a woman my age, and when I started to look around at the ciswomen around me, life began to change. As I began to build a new professional women’s wardrobe, suddenly I found myself presenting and blending into feminine situations I never could before. It was not easy, but I was getting closer.

By closer, I meant my all-important confidence that I was doing the right thing was growing too. It helped when I was able to look another woman in the eye and have a face-to-face conversation too. It was very difficult for me to get there because of my inherent shyness and other factors but with a lot of work I did it. I was far from perfect, but I was learning.

Before I knew it, I became an accepted regular at the ciswomen’s get togethers after work at a local TGIF Fridays and I was in heaven every time I did it and wanted to branch out into other similar venues which accepted single women at their bars. Even though I was having no problems at those venues, it was never easy for me as I was always waiting for the other foot to fall when someone would ask me why a man in a dress and makeup was doing there. Needless to say, it never happened and I was able to enjoy my drinks in peace. I did not think of it then, but I was suffering from an age-old condition which was instilled in me as a kid that nothing was ever good enough. If I was succeeding in the venues I was going to, why shouldn’t I try new ones.

In other words, I was not stopping my trip up my male to female femininization journey to enjoy my progress. I was still looking over my back for trouble. Another problem I always mention it was how ill-prepared I was for the internal lives' women lead. I had never been allowed to see behind the feminine gender curtain and was left to my own to imagine how it was. Naturally, I played up the good such as the pretty clothes, hair and makeup and downplayed aspects such as passive aggressive behavior all the way to having to learn all the basics of womanhood from peer group approval. I had no sleepovers with other young girls to work with or mascara lessons from mom. As it turned out, I was probably wearing more makeup at a younger age as the daughter she never faced the fact she had.

Which always made another part of my life difficult because deep down I wanted for her to accept me for who I was. Even though I tried to explain to her one night that I always wanted to be a woman, the best she could do was reject me and offer therapy. We never mentioned it again as I struggled for acceptance in my new feminine existence. I could never understand how she could reject me so quickly with no discussion whatsoever. She was part of the “greatest generation” which I guess did not include emotional support for gender issues. Since I was used to my parents not making my life easier emotionally, it was easier for me to move on.

As I did move on in my own new and exciting transfeminine world, I was able to discover social sources of emotional backup they never knew they provided. What they provided was a learning experience for me to do away with any vestiges of my male past. After the years of fighting the gender changes, he was facing, my male self finally gave up his throne fairly easily and let my long hidden feminine self-take over and erase the scars from all the fighting she went through. Most importantly, my new circle of ciswomen friends never questioned my femininity and I flourished with them. Making up for all the lost time I had as a man trying in vain to hang on to what he had in male privilege he had earned but had never had the chance to appreciate because he never really wanted them after all.

It all brings me to the now of life. I still bear the recent scars of the two new Veterans Administration nurses who kept referring to me as “he” behind my back because my doctor never does. The difference is now the gender slings don’t hurt for long because I have long since concluded, I am only me and that must be good enough. Plus, I just learned that the VA is facing a shortage of the Estradiol patches I use and I only have a couple weeks of patches on hand to use. So, once again, hormonal injections may become a reality for me. It’s another bridge I am building that hopefully I will not have to jump off.

Perhaps I will always carry with me some of the difficulties which come with a transgender life that I never started with any natural feminine qualities. Testosterone poisoning tore me up and I have paid the price ever since. But, like before, I will get over the bad and embrace the good from the family and friends who are around me.

Thanks for reading along and I hope you gained serious insight from my writings. Any comments or claps are always appreciated by you!

 

 

Friday, October 16, 2026

What Could Possibly Go Wrong

 

JJ Hart

What could possibly go wrong when you transition genders from one side of the gender border to another? We all know the answer to that question. A lot can go wrong when you start the process of traveling your long gender path out of your closet into the world.

It seems the path never gets any easier the longer you go. If you start early in life, and happens to be in an understanding family, you may be able to begin hormone blockers before you enter the hated results of the gender you want nothing to do with. And that door is rapidly closing in backwards states like my native Ohio which are doing their best to ban any gender care at all for anybody. Especially minors.

On the other hand, if you are forced to wait in life for the hormonal poisoning which goes on in puberty, you end up playing catch up your entire life as you either have to go through extensive, expensive operations to present more authentically as the person you want to be or stay the course and try to present effectively with makeup and clothing skills. Which was the path I needed to take. Plus, let’s not forget the obstacles we face when we are first considering the HRT gender affirming hormonal route. To do it right (which you should) you should seek the help of a doctor to help you along which is an unwanted expense that many transgender women and transgender men may not have the finances to cover. Then there is the extra route I had to take with the Veterans Administration of having to go through mental health screenings before they would approve my HRT at all. I was fortunate to be matched up with a VA therapist who had knowledge of the LGBTQ world so all that could have gone wrong never did.

When you male to female transition later in life like I did, many risks come along with doing it. All of us must give up almost all we have worked so hard to achieve, such as having spouses, friends and jobs reject us as we must start all over in life. What could possibly go wrong with wrecking your own life often becomes a reality.  I know firsthand of several trans people who had their lives wrecked, simply by wanting to live as themselves. It seems no one under the transgender umbrella gets a free ride out of the rain. Let’s say you are very passable but still must worry about a stray toxic man threatening you physically when he discovers your truth. It all takes what a ciswoman fears most in the world as far as sexual violence goes and takes it to a whole different level.

It is difficult to live a life when you forever are looking over your shoulder if you are transgender, but it happens. For example, when you leave what was left of your old male privileges behind, you leave much of your personal safety privilege with it. You better begin to learn what ciswomen are taught from a young age to know. Think ahead and do not put yourself in potentially dangerous situations such as dark city streets when you are alone. It happened to me before I almost learned the hard way not to be in the wrong place at the wrong time.

It takes a strong individual to seek admission into the transgender tribe. We must go through a lot of trial and error to learn what is right and wrong on the path we are taking. In my case, often more error than trial as I had to keep going back to my cross-dressing drawing board over and over again before I was able to overcome all the testosterone poisoning I was subjected to and I learned to blend in and exist in the feminine world I had always dreamed of but then again, I kept finding out what could I be doing wrong and kept on going. Sometimes I pushed my trans envelope too far and had to lick my wounds and get back in the game.  It took me awhile to regain my confidence and get back out in the world. So far away from my privileged male life as I could get. Again, I asked myself what could possibly go wrong with what I was doing with my life.

The answer kept coming back that everything could go wrong and I could be forced into before I was ready into the feminine world I wondered so long if I could live in. I was at the crossroads and needed to get off the middle gender ground and do something about it. I ended up again following my instincts and making the only decision I could. It was not everyday that I had the chance to reassess where I was in life. I needed a real conversation with myself possibly for the first time ever. I was surprised at how fast the conversation went as I thought why was I continuing to put myself through all the gender problems I put myself through. I was paying for all the stress without any benefits. Somewhere along the way I veered from my male path and never wanted to go back which was the most important decision of my life. It was time to attempt to find some joy because who I had become and time to build a new life from my old male self.

It turned out I was engaged for years in a long-term relationship with my feminine self. Not being closer hurt, me sometimes drastically and I had to repair them. No more internalizing my feelings for a change. I was finding out what could possibly go wrong if I did not face my truth. Shame on me for not doing it.

I faced my truth again yesterday when I went for my annual physical exam at the VA. I have been lucky to have the same doctor look at me for years now, so she has never questioned my transgender status at all. I had a lot to do yesterday, including blood work. flu shot and overall exam when things became a little sketchy. When she was listening to my heart, my doctor heard something she did not like and immediately ordered an EKG. She did not think it was anything to worry about but just wanted to send it to a cardiologist to look at. It means a lot to me because my mom passed away from heart problems at approximately the same age that I am. Now I am awaiting the results. On the bright side, all my blood work came back fine. Even my estradiol, which surprisingly, agreed to check it for once at the new clinic I was going to for the first time. It should mean I won’t have to have my blood work done when I go to Hematology next month.

What is the worst that could happen? Hopefully I can stay active and continue to lead a productive life.

Thanks for reading! Any comments are always welcome!

 

 

 

Wednesday, October 14, 2026

She Was Always There

 

Trans Ohio Symposium
JJ Hart

No matter where I went in my life, she was always there.

It did not matter if I was in the middle of playing a football game as a defensive end, she was always with me wanting instead to be a cheerleader. She carried over into my everyday life also as I daydreamed all the time what if would be like to cross the gender border and live a feminine life. As I dreamed my life away, my feminine side may have had an unfair advantage because I was only seeing the positives of being a girl or a woman. It seemed so unfair to me that they could wear all the pretty clothes, have long hair and not have to worry about being forced into military duty during the Vietnam War. Plus, why did I have to be the chaser whenever I wanted to ask someone out. I never saw the competition between the girls for attention, being able to wear makeup and more. They were far from the simple life I was seeing but had no one to tell me so.

Even so, she was always lurking in the background as I fought off the shyness, I felt when I had to be around people I did not know in public. Especially other girls. I did not know then why I was attracted to them in a non-sexual manner because it would be the way I would live my life as I grew older. I learned my natural comfort zone in public always came with other women and I never felt comfortable making friends with men at all. Maybe it was because she was always there in the background. Telling me what to do.

When she did, often major conflicts in my life would occur because in my male life I was always trying to put up a macho front to keep the bullies away. It was difficult to do when she was always whispering in my ear, I was doing the wrong thing when all I was doing was to survive my gender dysphoria and live. It was the beginning of a lifetime of warring genders that would consume me to the point of self-destructive behavior.

When I progressed in my career into management, she was always with me when I needed to handle the women in my crews different than the men. She was studying the way I handled myself and how the ciswomen I was dealing with handled me. Primarily, I learned a lot about how women exist with each other and how alpha females can control a clique of other women. It would be valuable experience later in life for me when I was trying to gain acceptance to the girls’ club. If I had an alpha or two helping me along, they could make my life so much easier.

It began to matter more to me when I began to listen more and more to the feminine voice who was talking to me. She was a powerful influence when other women approached me to investigate what I was all about. Somehow, I was like them but yet so different as a transgender woman. I would have to learn how to build trust with other women as a like minded person and only use the long unwanted male basics of my life when I was asked to. Such as when women asked me questions about understanding their boyfriends or husbands. The last thing I wanted to say was I never understood them either, so I helped the best I could and I was flattered by the questions.

Most certainly, she was more than in the background when I started to explore the world as a trans woman. To do it, interaction and communication was the key as I had to come way out of my closet to do it. I even went as far as taking feminine vocalization lessons to learn more about how to communicate more effectively one on one in the world. The lessons were wonderful and taught me more than I ever thought they would. I knew of course that ciswomen had their own way of communication, but not as much as I learned about the nuances of feminine speech patterns. It was a huge change for me as I had developed many bad listening habits as a man that I needed to change…quickly, if I wanted to survive and thrive as a transfeminine person. Such as beginning to closely listen to what another person was telling me rather than skipping over it to how I was planning on answering it.

As I added layer upon layer in the world to the feminine self I was building, I did not have to pay attention to the woman within me that had always been there in the background. She was having a chance to see the fruits of always being with me come to bear as she was able to take over my world. Since I had already put in years of effort into my presentation as a trans woman and had taken it about as far as I could, my background woman was overjoyed to see me take the extra step and listen to her where to go next. That step was to put the communication mode fully into my life and complete my feminine image in the world. I finally made it out of my closet’s mirror and had a chance to be happy. Something that was never emphasized in my family when I grew up. I did not know how to act with such a new emotion.

Then it became time to flip my gender equation. My male self still vaguely exists as my female self runs my life. I discovered it was nearly impossible for me to erase the decades I had in life doing my best to make it in an unwanted male world. So, I tried to take the best and leave the rest behind. It is working for me so far.

Speaking of working for me, I will not be writing tomorrow as I must go to my new Veterans Administration clinic for my annual checkup, Flu and Covid immunizations and even blood labs. I have not had any problems for years at the VA because of my gender, so I do not expect any tomorrow. But if past Flu and Covid shots are any indication, I will not feel like writing. If any thing crazy happens with the clinic’s personnel disrespecting me, I will report it.

Thanks as always to reading along with my gender journey exploits. Hopefully my thoughts can be of value to you.

 

 

 

 

Tuesday, October 13, 2026

Spending Your Whole Life Changing a Person

 

Image from Hoite Prins
on UnSplash. 

Sometimes, change comes slow in the life of a transgender woman or transgender man. I can speak from experience since my change came roughly over a fifty-year span.

During the old if I had known then what I know now experience, if I had known my male to female femininization project would have taken that long, would I have tried it at all. Then again, I would have had too because becoming a woman with my own standards was always the main dream I always had. I never knew how I was going to make it, or if I even could but I was determined to try.

And try, I did. Repeatedly until I came closer to getting it right. I spent countless hours in front of the mirror as a youth trying to get my makeup and clothes just right and dreaming of the day when I could afford a nice wig. I had had enough of my short male haircuts, and as far as change of hair styles went, I would be forced to wait until after I got out of the Army before I could begin to grow my hair out to where I wanted it. In the meantime, I was able to buy a beautiful long blond wig to help my change along.

About that time, I realized I could help my way along with a major change by going on a crash diet. By doing so, I was able to lose enough weight so I could finally fit into the more fashionable women’s clothes I was finding at all the thrift stores I was shopping at. Even the weight loss, along with my new skin care program, did not help me enough in the change department. I wanted more in my desire to be the most attractive woman I could possibly be and worked constantly at it. Much to the chagrin of my second wife who wore nearly no makeup at all. We clashed about it all the time, but I stayed on my path to always do better.

Sadly, before my second wife’s death, my formative years of change as a novice transgender woman set in. I wonder now, how I made any strides with all the restrictions which were put on me. I did know one thing that I could not see any real changes in my feminine life until I could make it out of my restrictive lifetime closet and be allowed to explore the world. Something my wife was dead set against, adding an extra barrier on my gender path. In place of being able to explore more in the world, I daydreamed my life away. Thinking what it would be like to live the experiences I had as a cisman as a woman. I would like to get back just a portion of the time I wasted daydreaming and have often wondered what I could made of my male self if I had been constantly focused on him. Of course, I could not get the time back and had to make the best out of what I had been given.

When I was able to finally break out of my closet and begin to explore the world as a transgender woman, change began to come quicker for me. I got to the point where I could not wait for the next time I had the chance to go out so I could have the opportunity to learn more about the life I should have always been able to live. In an extraordinarily short period of time, I was able to establish myself and begin to carve out a new and separate life away from my old male one. For once, I did not have to wonder what the life of a ciswoman was like as I was experiencing it for myself. The time was especially valuable to me when I began to lose most all my friends to death and I was desperately lonely. I needed a new place to turn and all the changes I had worked so hard on over the years really came back to help me.

Perhaps the biggest change which helped was that I came back as a wiser/nicer self than I ever was before. All the years of watching and learning from the ciswomen around me did come back to help me after all because I learned that all women did not fit the kind and giving stereotype of the feminine world everywhere. I gained some basic knowledge of which women to look out for in the world and how to change around their often-passive aggressive spirit. Lessons I learned the hard way on many occasions when I learned a smiling face did not mean a smiling spirit.

If I had not let a lifetime of change help me, then shame on me. So, I needed to make the best of a life which on occasion seemed to be totally out of reach. It was not until I realized it was that I resolved myself to do the little things to make me a better transfeminine person. That is where the little circle of women friends who I built up around me came in to help me. All the girls’ nights out and lesbian mixers helped me to round off the remaining rough male edges that I had and send my life in the right direction where I did not need a man’s support to validate me as a person. Another woman’s validation was just as valuable to me without all the resultant drama and sexuality questions I would have had to have gone through.

I suppose all the changes I went through in the military when I was stationed on three continents in three years got me used to change and in fact, I often craved it. It worked to my advantage later in life when I had all the gender changes I could handle. Even though my immensely influential male self as well as me trying to appease my second wife went, they never won and I changed anyhow. A drastic change from societies’ standards as I was able to cross the gender border and femininize myself from male to female.

I certainly was fortunate to be able to do it all and see the world the way I could behind the feminine gender curtain. Even though I ignored the obvious about myself and it took so long to do it.

Thanks so very much for joining me on my gender journey!

Any comments or thoughts are always welcome.

 

 

 

 

 

Monday, October 12, 2026

More Than Just a Passing Fantasy

 

Image from Alexsy Turenkov
on UnSplash.

As I made my way into the public’s eye as a novice transgender woman, I needed to prove to the average person I was much more than a man in a dress with a wig and makeup.

It meant I needed to change my entire thought pattern too about who I thought I was because for the longest time, I considered myself more or less a feminine “hobbyist” who dabbled in wearing feminine clothes and makeup. I considered myself as serious about my hobby as much as I did my brother being serious about his golf game.

Ironically, I can not put my finger on the exact moment I started to change my overall thoughts on myself, but it was a gradual process. Triggered by me being exposed to the transgender term for the first time in my life. It all came from the fact that I knew there just had to be more to what I was doing with my feminine self than just a casual process and the transgender terminology appealed to me. Being trans took me another step towards living my ultimate dream of living as a transfeminine person more than anything I had ever read before.

All my research into gender dysphoria and its effects on me led me to slide myself increasingly on the gender scale to the feminine side of the spectrum internally. Which was the easier part initially. Then, all I needed to do was internalize my feelings and keep on living my male life so no one would notice that I was different at all. The problem was, I did not know how much internalizing my gender dysphoria would hurt me in the short and long term.

As I always knew, but tried to hide, just cross-dressing was never going to be enough for me, as I wanted to do more with my life as a woman. Of course, once I realized it, I needed to plan a course to do something about it. Being stuck in a restrictive single occupant closet was not going to be enough. Somehow, I needed to gather the two C’s, courage and confidence to take on the world as my authentic feminine self if I was ever going to do more than jut survive in the male world I wanted nothing to do with. I needed to get out of it and convince others I was so much more than some sort of a drag queen playing a part of a woman.

Little did I know, the drag queen problem would take care of itself everywhere but in the gay venues I was going to often. After I was done hitting my head against the wall in the gay venues, I decided to go back into the world once again to see if I could be viewed than more than someone’s fantasy object. Accomplishing it became easier to me than I ever thought possible when all I had to do was to keep going back to the venues I had frequented as a man but this time as a trans woman. If I managed to wear the same wig and look the same, I was hard to miss and easy to remember if I followed my basics of always being pleasant, never causing problems and tipping well. By doing so, I became a regular before I knew it and I started to carve out a whole new feminine life away from my male past. Most importantly, there were no passing fantasies involved for me, no smoke and mirrors as I was actually doing it.

I continued to take my trans show on the road, so to speak, as I tried to live every spare moment as a woman to see if my dreams were more than just dreams and not turn out to be nightmares. I was trying to make sure I had all my life’s basics covered if I was ever going to give up everything I had earned as a man. Use what I could as a transgender woman and start all over again. That way, I would not totally be starting over, I could take what I learned as a so-called cisman and apply it all towards the scary but exciting new world I was living in.

Doing the same things over and over as a woman helped me to carve out the new life I had always wanted to live. Other ciswomen knew my name and wanted to know more about my life because they were curious why I wanted into their world. I was in heaven and continued to want more as my life changed for the better. It all did because I had the courage to put myself out in the public’s eye. While I never managed to be the most attractive woman in the room, I was the most consistent with my look. Which was all I could do with what I had to work with in my testosterone poisoned body. It took me a lot of time and effort, but I put away all my old misgivings about my life’s journey and kept my momentum up towards my extreme male to female femininization project.

By this time, most all the family and friends who meant anything to me had passed away leaving me all alone in the world to do what I wanted. After all those years of playing around with thinking I was a casual cross-dresser had completely left my mind and looking like a woman was much more than a mere fantasy, I was ready to move forward into the world I had always should have been a part of. It turned out to be a for better or for worse deal for me by this time. I had put so much effort into the struggle to femininize myself and get out of the male world that it all turned out for the better as I entered a win-win situation in the world.

In fact, during my life, there was no way I ever could have fantasized arriving in the place where I had arrived. I love it when a plan comes together. Even though it took me so long.

Thanks for reading along with all my hopes and desires during my life.

Thought are always appreciated!

 

 

Sunday, October 11, 2026

A Destination or a Retreat into Trans Womanhood


Image from Brian Wangenheim
on UnSplash. 

As a youth, all I did when I failed at a male task was to seek the reassuring feelings of my feminine clothes and makeup. I knew then I would not have the male world I hated for a while.

The pattern continued with me into adulthood and was even expanded to include a better sense of wardrobe and makeup as I ventured into the world. But then it started to slowly reverse as I started to blend in with the ciswomen around me. Increasingly, I was feeling better about the progress I was making as a serious cross-dresser and wanted to do more as I moved towards being a transgender woman in my mind. Even though I was still extremely lonely as my feminine self, I was starting to embrace the unique person that I was. Afterall, how many people get to experience both sides of the primary genders in their lives.

On occasion, I even reverted to appreciating all the male privileges I had learned after a particularly brutal day of exploring the world of cross-dressing. Early on there were many I needed to go through as I continued to pay my dues to get to my dream of possibly living my life as a transfeminine person. Not a man.

Even though mixing genders was beginning to have a bit of normalcy for me, I came to the point where I would not recommend the journey to just anyone who was not totally committed to it. My mental health, which was already frail at the time, did not take easily to the journey ahead and it suffered. Again, sending me back to the comparative safety of the only other life I had learned to live successfully when I was competing as a man in the world.  At that point, it was difficult to tell if I was on a trans destination or a male retreat. The only thing that kept me going down my path was the deep sense of satisfaction or gender euphoria I felt when everything was going better when I interacted with the world as my true authentic self. Free and out of the closet for a change.

It took me years of experimentation in public, as I set up my own personal bucket list of what I perceived to be the real-world ciswomen had to face in their lives. I figured out why I would want to go there if I could not make it. In other words, I kept challenging my feminine self to do more and more such as do more than just spend very little time in public just walking around or shopping in easy venues such as women’s clothing stores where your money overcomes any reaction to your possible gender when it came to testing myself. I certainly then was setting myself up for a possible transgender destination in my life as I worked my way through my bucket list.

As with anything else in life, all I had learned about being in the world was not all positive and I found myself deeper into my quest to cross the gender border and complete my male to female femininization project. I learned the hard way to try to not get myself into questionable safety situations that women know not to get into that do not bother men. It seemed the gender universe was testing me on certain nights such as the one I needed to fend off negative advances from a much bigger cross-dresser admirer at a party I was at with the help of my second wife. Something I never bargained for as I went around a blind corner on my gender path. It was easier to think about erasing all my male privileges such as safety but harder to learn what to replace them with.

I do not think I ever did replace my new lack of intelligence with the cismen I interacted with as I was mansplained more times than I cared to remember by men of questionable intellect. Such as the tow truck driver I was forced into a conversation with one night when he was towing my car home. I had to sit there, and act interested when he had to tell me all the workings of his truck. Like I cared when all I wanted was to get home safe and sound. Which I did. All the bucket lists in the world did not prepare me for the reality of living a feminine life, but even still, I was loving everything I learned behind the gender curtain. If I was ever a girl scout, I would earn merit badges like what to do if your car breaks down when you are by yourself and the first person who stops to help is a sheriff. Who would not listen to me when I was trying to explain to him and the tow driver the easiest way to my house. I finally just gave up.

It soon was becoming obvious to me that I was no longer retreating behind my dresses and makeup to cover any vestiges of a male life I wanted to cover up. Instead, my full-fledged female life was a complete destination. A destination I wanted to do more than anything I ever had done in my life. There would be no more retreating back to my male world. No matter how easy it would have been to do it because he had always kept a comfortable home for me if I ever wanted to return. Much to his disappointment, I continued my feminine destination into the world of HRT gender affirming hormones which separated me farther from ever hiding again in my old unwanted male world.

HRT was certainly the end for any thoughts of ever returning to my old male self because I felt to increasingly natural when I took them. It was as if my body was telling me what took so long as my external self-synced up with the woman, I always saw myself to be. It just took me years to get there. Which was the tragic result of me not listening to myself.

Thanks for reading along on a few of my trials and tribulations of my gender journey. I hope yours is much smoother. Any comments are always appreciated.

 

 

Seeing It All Clearly Now

  Image from Lola Rose on UnSplash.  As I journeyed for years along my decades old gender path, I discovered I could see life much more clea...