Tuesday, November 25, 2025

Stopping was Never an Option

 

Image from Josiah Niklas
on UnSplash.

Very early on, during my very confusing crossdressing years, I wondered if I could just stop the madness of wanting to change my gender as I grew older. I did not know at the time that stopping would not be an option.

As I grew older, my desire to be a pretty girl (then a woman) grew with me. The more I cross-dressed in front of the mirror, the better I became at the basics of makeup and whatever fashion I could get my hands on. Plus, the better I became, the more I wanted to do more to improve myself. Increasingly I knew stopping and purging all my feminine clothes was never going to be an option even though I tried and tried. At that point, I tried a clumsy attempt to come out to a couple friends I had but was rudely rejected. I needed to return to internalizing all my feelings of wanting to be a girl if I was to survive in my world. Which was cruel and unusual punishment for me and more importantly, my fragile mental health. I was already stuck in long periods of depression before I was diagnosed as being bi-polar by a therapist I went to as I grew up and away from my parents.

When I did move away to college, I actually lost my desire to cross dress and act like a girl for almost a year. I did not know how to act when stopping all of a sudden became an option.

Of course, before I knew it, my gender dysphoria came creeping back into my life. I then needed to build my wardrobe fashion, undergarments and makeup all from scratch. I vividly remember the trigger object which started it all. My future fiancĂ© for some reason, found a short wig to cover her long straight hair, and tried to surprise me with it. I was not pleased and let her know it. I then set out to get her a wig I liked. Funds were tight as I worked at a small radio station where I went to college, but I managed to scrape together the money to buy a beautiful long blond wig I had seen in the window of a beauty shop in my hometown. Under the guise of buying, it for her, I had really wanted it for myself. As luck would have it, she did not like it, and I was able to “inherit” the wig when we separated years later.

I kept the wig until I joined the Army for my Vietnam War tour of duty and beyond, as I was able to hide it away on the rare occasions, I could use it to “top” off my outfit when I cross-dressed. Even with all the traveling I was doing with “Uncle Sam” I still was able to anchor myself with the belief that stopping my idea of being a woman was not a fairy tale and could still be possible someday.

It wasn’t until I seriously began to explore the public’s perspective of me as a newly minted transgender woman, did the world start to change and I knew nothing that I was trying in my new world was going to change…ever. Even still, ever became a big word for me as I hit a series of roadblocks to become a full-fledged transfeminine person. Just when it seemed I was moving in the right direction, something would come along and temporarily stop me. At that time, through all the roadblocks, I finally realized I could see my dream of living like a woman was certainly not an option and it would be a shame to waste all the time and effort I put into my path.

I also needed to make the final decisions I would need to successfully put my male life behind me. What I would do about supporting myself and coming out to my remaining family became very important decisions. My only child (daughter) made it easy on me because she accepted me totally. While on the other hand I was rejected by my only sibling (brother) and we became estranged. My parents, second wife and most of my friends that mattered had passed away which made my coming out process easier. One way or another, I had decided to go my own way no matter what anyone thought.

If I had realized earlier that stopping my male to female gender transition was never an option, life would have been so much easier for me. I would have been allowed to live the best I could, make all my mistakes earlier and achieve my ultimate dream sooner. Rather than stubbornly hanging on to a male life I was born into but never wanted.

 

 

 

Monday, November 24, 2025

Transgender Dreams

 

Image from Felipe Delgado
on UnSplash

Obviously, we transgender women and transgender men do a lot of dreaming when it comes to the ultimate results of our lives. For example, when I was very young, I could never speak truthfully when an adult asked me what I wanted to be when I grew up. Saying I wanted to be a woman would have never been acceptable and would have rewarded me with a visit to a psychiatrist. So, I said something more acceptable such as a lawyer or a veterinarian.

I had to save my ultimate desires to be feminine for my dream world and often went to sleep thinking of how it would be if I could wake up as a pretty girl. Of course, I was never able to take advantage of such a thing happening to me and I needed to make the best of what I had to work with. Which was about ready to radically change for the worse when I went through male puberty. As I started my growth spurt, I rapidly outgrew all my mom’s clothes I had tried to squeeze into and had to rely on my meager allowance added to my newspaper route delivery money to try to sneak out to stores and buy my own clothes and makeup.

Through this portion of my life, my mirror was my friend and helped me to bring dreams of being a pretty girl to life, no matter how I really looked. It wasn’t until I began to experience the public’s reaction to me did, I finally get a fair and accurate reaction to how I really looked. I desperately dreamed of being more than a clown in drag. After tons of work and trial and error experiences, I finally made it to where the public at least knew I was being serious about achieving my dream of being a woman. Little did I know, the real work I would need to do to achieve my dream was about to begin.

The more I explored the world as a novice transgender woman, the more I found I had to do to survive in the new exciting feminine world I had dreamed of being a part of. When I was in the public’s eye, I found I attracted the attention of ciswomen as never before and as I did, I needed to get radical and do things such as talk to them. Initially, I was very shy and completely unprepared to take such a big step, but I was way past the point of ever turning back. For the first time in my life, my dream appeared to be within reach, if I kept learning what my new world meant.

I found I was stuck in some sort of a gender never-never land. Ciswomen instinctively knew I was not Cis but on the other hand, wanted to be in their world. Fortunately, I found most of them let me into their worlds and showed me a path to being successful, if they knew it or not. I did not care how I received the help and guidance; I was just trying to achieve my dream of living as a successful transgender woman. As I tried to point out in yesterday’s post, I went past the point of trying to be trans all the way to just being me. Which I think the women around me accepted because of my honesty. By now, you may be thinking what about the men around me? For the most part, they left me alone. Which was fine by me. I wanted out of their club and wanted nothing to do with going back if I had anything to do with it. I was successful and never did. My dream increasingly appeared to be reachable, and destiny opened her doors for more success for me. Primarily when it came for time to consider going down the path of gender affirming hormones or HRT.

I knew first, I needed to find a doctor to approve taking the hormones and I found one in one of the Dayton, Ohio LGBTQ publications. He had openings and I was able to get in for a checkup and then receive my precious prescriptions for initial minimum dosages for estradiol and spiro to get started on a new path towards achieving my dream as never before. After I began the minimum dosages, I had no adverse reactions and in fact the opposite was true. I felt as if I should have been on the meds for my entire life. They made me feel so good.

By this time, I felt as if I was living proof that transgender dreams come true if you pay your dues such as I did. The dues I paid were certainly the best investment I ever made.   

 

Sunday, November 23, 2025

Is There a way to Be Transgender

 

JJ Hart in Mystic, Connecticut.

To be fair, I saw this question posed on a couple different sites on the internet and thought I would comment on it. The question is, is there a way to be transgender.

As I thought about it, I initially thought for years that there was a way to be a transgender woman and that would be to copy all the other cisgender women around me. Even though I thought this was the best way to go, in the long run doing it hurt me. Why? Because doing it stopped me from becoming my true authentic feminine self.

Surely, cis women are guilty of forming cliques while men form teams and to be included in a feminine clique, you have to look and act the part…at first. I discovered that once I was accepted by an alpha female, my entrance requirements became easier to come by. But what I did not realize was how perceptive the other ciswomen in the group would be to me and how women can spot a fake a mile away. I would have to proceed with caution if I was going to succeed at the invisible goal of being transgender. To succeed, I did all the usual things such as obsess on my appearance so I could blend in with the other women when I received a cherished invitation to a girl’s night out.

Then, when I arrived at the function and my fear began to subside, I needed to look around and judge all my reactions to the conversations going on around me. Which marked my first real idea that there was not a real way to be transgender. Afterall, when the conversation turned to kids, I still could participate because I had one that of course I did not birth but still participated in the trials and tribulations of raising her. Similar to the other women in the group. It was just a small example of how I survived the evening as I added in my input when I could. It seemed to work because all the other women except for one accepted me and I ended up enjoying myself.

As the years went by, and I began to experience many nights as my transfeminine self, I found there was no way to be transgender but there was a way to be myself. When I did was when I became more and more successful in the world as a trans woman and my ultimate dream of living a full life as such could be realized. Also, during that time, I spent quite a few evenings socializing with a transgender woman friend of mine before she moved away to Dallas. The two of us were prime examples of differing ideas on how we wanted to pursue our lives as trans women. My friend Racquel wanted surgery to look the best she could and attract men, while I found myself comfortably in the company of lesbians who I found for the most part accepted me for who I was.  I did not and have not to this day desired any major gender surgeries. Mainly because I did not need them to help me to realize my way to be transgender.

Of course, as human beings, we are all different and one of the problems we have now is being forced into one small box by a society which does not understand us and for the most part has never met a transgender woman or man, that they know of. Some, like me, are forced into forms of living stealth just to survive. When just using the bathroom becomes a threat to your existence in some parts of the country, something needs to be done, yet we continue to be forced backwards in most parts of my native state of Ohio. It all makes just being transgender so difficult to do.

Enough of the negative, and now on to the positive. Even here in Ohio, the LGBTQ winds of change are blowing with several more communities proclaiming they are safe zones for us. And, with the strong showing so far for the Democrats in the country, real change could be on the horizon for change as we need it.

If and when change does happen, it will make it easier to live your gender dreams and realize one thing. In the end you are much more than just another transgender woman or trans man. You are you, and that is the most important fact to realize if you are to be successful in your world.

There is no way to be transgender but there is a way to be you. 

Saturday, November 22, 2025

Down but not Out

 

Hair by JJ Hart, Beret hand beaded
by Liz T Designs on Etsy.

One point I always worry about making is how many times I was not successful when I was trying to survive in the world as a novice cross dresser or transgender woman. Or how many times, I walked completely out of my way to escape groups of teenaged girls coming towards me. Perhaps, similar to many of you, I was out and out laughed at by girls seeking their own sense of femininity.

Too many times, that I would like to remember, I needed to rush home with tears in my eyes to go back to the drawing board and reassess what I was doing because obviously, something was wrong. After years of failure, I finally found the person I needed to blame, my old male self and his ego. He was the one who kept urging me on to dress trashy in a failed attempt to show off my own femininity primarily to other men. It turned out I learned I was trying to impress the wrong gender; I should have been trying to impress the ciswomen I encountered. Blending in with them became my primary goal so I could be successful.

Many times, blending myself into a completely new and terrifying world became very difficult due to the layered life women live in. Every time I thought I had turned the corner in my gender life, something would come up and slow my progress down. Again, I was frustrated many times and ended up with me being down and out again in my transgender thinking. Through it all, I needed to keep my head up and be aware of any possibilities I may run into. Or, I should say opportunities to improve.

Out of all the opportunities I faced, I like to point out that communication was the hardest problem I faced once I finally got my appearance situation taken care of. To do it, I needed to solidify who my feminine person was. No more changing wigs and names every other time I went out. I had to settle on what wig and name I would use every time I went out because I was so recognizable. The pressure was on to make sure I was doing all I could to make a good first impression as a transgender woman. I needed to make sure I was properly social without coming off as being bitchy. When in fact, I was just shy with all strangers.

At this time, at least, I was not getting laughed at. I was learning what I needed to do not to be down and out as a transgender woman. Plus, I was still amazed how many other women wanted to communicate with me and understand what I was doing in their world. At that time, it was so important to me not to make a fool of myself and go back to my gender drawing board again. In my case, practice did make perfect, and I was finding myself less and less in potentially embarrassing situations. The problem was (if I had one) was keeping myself engaged at all times in my old male life. In fact, I was always flipping the script when I featured my female life over my old dominating male life. I needed to really concentrate what was left of my male life to make sure I preserved what I worked so hard to build up.

Looking back, I don’t suppose I was ever completely down and out as a transgender or transfeminine person. Even though everything I faced was not a positive situation, deep down I realized I was in a total learning situation, and I could (or should) work my way through it. Sure, I was blindsided in numerous situations, and I needed to rise above my limitations but somehow, I made it.

Every now and then I find myself in a position to give out advice. This time, I am challenging you to challenge yourself if you are actively seeking to change your gender life from male to female, or female to male. It will never be easy as you are attempting one of the most challenging experiences a human can undertake. But your positives will outnumber your negatives if you learn from your opportunities to improve.

Finally, you can get to the point where your old unwanted gender will not pull you down and you will not be down and out as a trans person. When you begin to trust yourself and build your confidence, you will be able to enjoy your new life for a change. You will be an up-and-coming person in a brave new world. Then maybe you to can be down but not out.

 

 

Friday, November 21, 2025

Gender Professionals

 

Image from Alysha Rosly
on UnSplash.

On occasion, I can just sit back and observe other women. Through my observations, it has occurred to me that some ciswomen are better at being women than others. For example, they walk straighter with their shoulders back and are proud of their femininity.

It has also been my theory that all females do not have the right to claim their femininity or the right to be called women just because they were born that way. Transgender women in particular know that becoming a woman can take many paths and we have can claim our own womanhood when our gender workbook is filled out.

Does it make us gender professionals? No, not in its own right but it does give us a leg to stand on when we are out in the public eye just trying to live our lives. It could be argued that transgender women and trans men must be better than our gender counterparts to get by and stand a chance of becoming gender professionals.

The question could be also, what does being gender professional really mean. I am only one gender conflicted person of course but for me to understand what a gender pro really meant, I needed to go into the world and live it. First, I tried to go to gay venues to see if possibly I was attracted to other men, or would they be attracted to me as a transgender woman. They were not attracted to me in any way and considered me no more than another drag queen on their turf. Which I wanted nothing to do with. Next, I tried the few lesbian venues I could find in the Dayton, Ohio area. There were three, and I found I was hated in one, had a neutral reception in another and was warmly accepted in a third. From the experience I mainly learned the different levels within the lesbian community and was it possible to work my way in at all.

The third and final venues I ended up at were the big sports bars I frequented as a man. In them, I was surprised to learn how quickly I could establish myself as a regular if I did not cause any trouble, learned to smile and then tip well. I learned too, to try to carry myself as a gender professional. Leaving no question of who I really was. I had to learn also carrying myself as a gender professional was completely different from being a gender professional. It meant I could carry myself well if I was wearing a fancy sweater and slacks, or my favorite team’s football jersey with a pair of jeans and boots. I discovered, more than anything else, I needed the confidence to do it and the rest of the world be damned if they did not like me. I was just having fun in the world as my self and taking advantage of all the fashion perks of being a woman.

Even with all the learning I was doing at the time, I still made learning from the ciswomen around me a priority. I figured they held the secrets that I needed to complete myself as a professional woman. The times to talk and communicate and the times to keep quiet and shut up and learn come to mind. You might say, I was exploring all the nuances of being a woman and trying to improve myself at the same time. I was fortunate in that almost all of my friends came from the lesbian community, so I came up with a unique view of the world. Especially around men which I learned did not validate my womanhood.

As you can tell, pursuing my quest to be a gender professional overtook much of my thinking. There was so much happening when I met my wife Liz, and I started to accompany her to her meetings she went to for various reasons. What happened was I had no choice but to expand my horizons again and meet a whole new set of people. When I did, I fell back to all the lessons I had learned about communicating with strangers. Not as a transgender woman but as just me.

Most Importantly, I had built back a portion of the self esteem I had lost as a gender professional growing up. I lost the inferiority complex I had put myself through during the rocky days of coming out earlier in life. Believing in myself for the first time as a transgender woman was all it took to get me by and enable me to become a true gender professional.

 

 

Thursday, November 20, 2025

Five Million

 

Original image. 
JJ Hart writing.

Recently, I reached a milestone as far as my blogging “career” goes.

This week, I reached and went over my five millionth hit to the blog which was amazing to me when I considered the humble way this all got started. I actually started blogging a long time ago when I barely even knew what the term meant. And I did it mainly because of the discussions I had with “Connie” an online transgender woman friend I had met from Seattle. Along the way, on another site we were on, we discovered a mutual dislike for what we called “trans-nazi’s” or transsexuals who based their worth on the number of gender operations they had undergone. Somehow, they felt better than the rest of us and were not shy about letting us know it.

From there, I had started to relay the experiences I was having as I initially began the trip out of my closet and into the world. “Connie” thought my experiences would be worth sharing and here we are so many years later. In many ways, both of us share the same sarcastic sense of humor, so we matched up well.

On a much deeper level than just harassing the “trans-nazi’s”, I hoped sharing what I went through in my lifelong gender journey would be a great way to pay forward my experiences and help others. Every time I receive a comment or two from a person in need of guidance as a beginning cross dresser or transgender person, I feel honored that they reached out to me. While all our trips are different, at the same time we are similar and have all have the same opportunities to learn from each other.

Five million hits later, I now realize the strain of finding subjects to write about on a daily basis really takes it out on me until I run across a comment or two which keeps me going. It fulfils the original idea I had when I started writing something I did not know I could keep on doing for any length of time. When the comments kept rolling in, I knew I was on the right track because I thought the audience I was writing to represent is a very narrow part of a potential audience. Then I thought, if I was reaching just one person out of the vast majority of readers on the internet, I would be doing my job. I learned to be more satisfied with being more of a niche blog, designed for the transgender audience or those that were questioning being trans and would their life look similar to mine. Because switching your main binary gender is so difficult and intimidating to do.

The bottom line is, I would not have all those hits if it was not for you and I cannot comprehend how many of you come from around the world to visit the blog. My deepest thanks go out to all of you no matter where you are.

Even though now I write on two separate platforms, I still write for free because I feel it is the right thing to do. It just makes me feel better.

Once again, I cannot thank you enough for joining me in my gender journey and I should do it more. Just be assured, it means a lot to me when you read along and even take the time to comment!

May we continue on to many subjects together in the future. 

 

Wednesday, November 19, 2025

Transgender Week of Awareness and Remembrance

 


As we finish up the Transgender Week of Awareness then honor all trans women and trans men, we have tragically lost over the years during TDOR, or Transgender Day of Remembrance, it is time for me to add in what I have done recently to be out in public to advance the awareness of who I am in the world.

As I mentioned a couple of days ago, yesterday was the day I needed to go to the main Cincinnati Veterans Medical Center to visit my hematology doc, who in turn ordered all of my blood work I needed from all sorts of providers including my primary doctor all the way to the nurse practitioner who monitors my depression and anxiety medications. So, the bottom line was I ended up seeing several people in a short span of time.

Of course, as luck would have it, the weather was beyond terrible for a mid-November day in Southwestern Ohio. During our trip to a very congested VA medical center my wife Liz had to battle torrential downpours, strong winds and even thunder and lightning. Through it all Liz got us there safely and it was time for me to meet the public as a transfeminine person. Fortunately, there is a drop off point at the front entrance, so I did not have to walk far in the rain with my walking stick. As I waited for Liz by the door, I sat near a group of four women who ignored me completely, so I thought I was off to a good start. In the distant past, I have caught people staring at me and worse at that VA, but not yesterday.

In some ways I am stealth these days as I transitioned into a senior citizen transgender woman. So, I can’t say I add much to the celebration of transgender people everywhere. Instead of all the people I did see yesterday, most of them paid me no extra attention except for the intake nurse who called me Miss Jessie and another volunteer who called me Mam when she was asking if I needed any help.

As far as the hematology doctor went, he was very nice and accommodating. He agreed to and set my estradiol blood test and even volunteered to give me more refills on my prescription. I left with a good feeling about him and if he ever knew I was transgender, he never said anything about it.

All that remained then was to make my appointment for next year and wait for the results of all the blood tests I did. It used to be I would have most of them within twenty-four hours before the ridiculous cuts to the VA that the Epstein crook made. So now I wait longer.

Now it is time to stand with all of you transgender women and trans men everywhere to make sure the public knows we have not gone anywhere. Even if you are still in your closet waiting to come out, be aware there are others to help you currently out in the world. You can join in the celebration also.

Just remember, the week ends with TDOR, the Transgender Day of Remembrance. It’s the time we pause to remember those trans people who tragically died just for who they were. Now, more than ever before, we have to stick together for change and in many areas such as Ohio, get our rights back.

As far as my wife Liz and I went, we stopped at our favorite coffee shop for a holiday joe and light breakfast sandwich which was a welcome sight for me after I needed to miss my breakfast and fast due to the blood tests. We went through the drive thru and headed home with our treats.  

Hopefully, all will turn out okay with my blood tests which I will be able to share with my daughter’s mother-in-law who always wants to know how my health is getting along. We shall see. In the meantime, take the opportunity if you can be a visible transgender woman or man. Except for those of you who have gone through the time and effort to go stealth in the world. Congratulations to you too.

I will keep you informed of my trifecta of medical reports which seem to pile up on me at certain times of the year. Anymore, it is my primetime to be out and about as a transfeminine person and do my bit for transgender week of awareness.

 

 

   

Monday, November 17, 2025

Completing Myself

JJ Hart doing Transgender Outreach Speech



I knew very early on in life that just cross-dressing as a girl in front of the mirror was not going to complete me in many ways. There just had to be more if I was risking my life as I knew it as a boy to dress as close as I could as a pretty girl.

Sadly, I had to ignore my gender truths, went on living life as a boy successfully and learned how to internalize my gender dysphoria. It all came back to haunt me later in life when the effects set in to my already frail mental health. Especially when I had started to go out more and more in public as a self-proclaimed transgender woman and I really put off hiding who I was to the most important person to me who was myself. I refused to make the changes needed to make myself whole for the first time in my life.

In the kindest words available, gender dysphoria was hell for me in my life. What made it so bad was when I applied my makeup correctly, I could actually see what could have been possible in life if I had not had to struggle with my gender identity. What made matters worse was when those brief moments of gender clarity were ripped away when I needed to go back to my male world. In other words, I never allowed myself to be made whole in my life until much later.

What had to happen first was the all-out decision made to do it. I was very cautious in the moves I made because I had so much at risk in my life. Losing my wife, family and job all weighed heavily into my decision. All the time and effort my male self-put into building a successful life would be wasted.  In so many ways  I was in a bad space which I think is humorous for anyone to think I ever had a choice in my battle with gender dysphoria. It was stopping me from being whole and living my life to the fullest.

While all of this was going on, I was attempting to learn as much as I could about living as a transfeminine person. I was going out every spare moment I could in the world to see if I could make it at all. And when I did, I knew I felt increasingly natural, and something was going to have to change in my life if I was to go on living. What happened was I loved the feminine world I was in and even though I experienced several rough spots, I knew I wanted (and needed) to learn more about my own form of womanhood. As I like to say, I was essentially starting from point zero and had everything to learn about feminine existence. Especially an existence where not everyone accepted me. Amazingly most everyone did and I was able to ignore the rest.

As the challenge of turning my life over to my feminine side and living a fulltime transgender existence, again the stress on me increased. Should I go through the process of being approved for gender affirming hormones of HRT was a major hurdle to cross. It would represent to me a final step in making me whole. If the hormones did what I thought they would, and everything I read about also. Even though I knew I could still go off the HRT is something went wrong, nothing ever did, and my body took to them like I should have been born this way.

It did turn out to be the final big step I took to combine my inner Yin and Yang gender selves and make myself a whole productive person. When I found out what I was missing, I had wished I had tried to make myself whole years before I faced the reality of my life and moved forward. Now I know what I did but it is way too late to make up for lost time for me at my advanced age of seventy-six.

Now seems to be the time to (no pun intended) transition into some busy work I have to bring up. The first is, there will be no blog post tomorrow because I am going to my trifecta of medical appointments. Tomorrow is my hematology appointment at the big Cincinnati Veterans Medical Center. It is my yearly visit when they check all sorts of blood related issues such as my all-important estradiol. I just hope it comes out as good as the last major trip to the vampires and my recent eye appointment last week. My eyes were the same as they were several years ago and I did not even need new eyeglasses. The third part of the trifecta won’t be until February when I go for my annual mammogram. So there is a lot going on. When I made my life whole. 

Sunday, November 16, 2025

What Makes You...You

 

JJ Hart

Recently, I have taken an informal poll with my wife Liz. We walk a lot and stop to talk to our neighbors quite a bit. Just once I would like to ask the neighbors, we see what makes them, them. Just kidding of course, I can’t imagine doing such a thing in our neighborhood. If I did, I would guess that they would all take for granted their gender and they would look at me as if I was crazy.

Predictably, the women who live on both sides of us are very friendly and the men are rather standoffish to me which brings me to my point of what is up with the men in the world today. First of all, as difficult as it is to being a woman today, in many ways, being a man carries its own set of potential problems. Primarily, having a very fragile idea of their own sexuality. Plus, men are still expected to be primary providers in many families which is added pressure not to lose your job.

For me, growing up, my gender became an early issue, but my sexuality never did as I was attracted to all things woman. At least, in my mind, I had one constant to hang on to about what made me, me.

As I started to grow into myself, I began to understand the differences in what I was facing which were different than the mass majority of the other men around me. When I inwardly did not embrace the male culture, I was born into of competition and posturing, all it caused was extreme mental conflict. Which I am or was sure the other men around me did not have to deal with. Most of my stress was caused by the pressure I put on myself in the highly competitive restaurant business I was in. Even though I was outwardly very successful, inside I wanted to run and hide as my increasingly transfeminine self. At the same time, I wished I could just be like the other men around me and not have to carry around the gender issues I carried. I was resentful either way I turned by not being the ciswoman I wanted to be or the man I always was.

At the same time as all of this was happening, I went exploring in the world as my exciting yet terrified new feminine self. The first move I made was to transition for the second time in my life from being what I perceived as an innocent guy who just liked to look like a woman, all the way to a guy who wanted to be a woman and see if she could interact one on one with other cis women when I was out. Which took me to the fateful evening at TGIF Fridays when I finally decided I had enough of what used to make me, me and wanted a change. As frightened as I was of losing my male privileges, I went ahead with the move, was successful and knew my life would never be the same again.

As I continued my explorations into the new me, I had glimpses of how my life as a transgender woman could be and could not get enough of the learning process, I was a part of. I made it a point to try new situations as a trans woman that I always wanted to be a part of when I was on the outside looking in as a man. I tried gay bars, lesbian bars and even the big sports bars I was familiar with as a guy before I settled into a venue where I was accepted and felt comfortable. In other words, I was involved with learning what made me, me. Something I had been missing my entire life.

I do believe if you are starting your gender journey from scratch these days, you may feel the same sort of resentment I felt when I started, which was something like why me? It was not until I embraced who I really was and learned the benefits of being able to see and live out both sides of the binary gender spectrum. In my case, I needed to put the feminine image I saw in the mirror to the test in the public’s eye to see if I could really pass the public’s scrutiny. Until you get out of your mirror and prepare for the bumps and bruises of your gender path, you will know the truth about yourself. There is absolutely nothing wrong with going back to being a cross dresser in your closet or a transfeminine person in the world.

As gender challenged transgender women or trans men, we face many uphill battles that other women and men don’t have to face. Such as the basis of our gender at all. It is one of the basics of human nature that we take our gender for granted, but what if we don’t? Then the search starts for who you really are and what makes you, you.

 

 

 

 

Saturday, November 15, 2025

Stranger Things have Happened

 

Image from Alexander
Krivisly on
UnSplash.

My gender journey has proven to me that stranger things have happened, just not to me.

What I mean is, on a scale of one to ten at succeeding in ever living a life as a transgender woman, I would have ranked myself some where around an eight. Meaning I was giving myself very little chance of ever making it to my dream life. Along the way now, I wish I had kept more track of every time I succeeded at and then passed a goal I had set for my feminine self.

In many ways, the early days of shopping in mall women’s clothing stores was easy and gave me a false sense of hope. I was naĂŻve and did not realize for the longest time, I just represented as a dollar sign in front of the store clerks, I was facing. Most certainly, I was not the first man in a dress and makeup they had ever seen in their store and would not be the last. Regardless, the false sense of confidence I was giving myself raised my faint hope of ever succeeding at my dream.

As I went not so blissfully on my high-heeled way, I did pick up bits and pieces of information I would need to survive. For once, I thought far enough ahead to set up time away from my wife so I could slip away and shop with the rest of the women in the malls on Black Friday after Thanksgiving. Which had been on my trans bucket list for years. By this time, I had experienced enough time in public as a woman, I knew things such as wearing comfortable footwear was a must for the long trips from the parking lot to the stores, all the way to being stylish but not overdone in my fashion choices for the day so I could blend in well with the other ciswomen I met. Stranger things happened and I had a great time which I will write about in a later blog post.

All of my continued success combined to make me think maybe, just maybe I could achieve my dream life, and I could increase my scale to a four out of ten. What helped me were the short trips I made to Columbus, Ohio to the small diverse parties I went to where I could meet and interact with anyone such as transsexuals on their way to surgery to cross dresser admirers who were there just to watch. I even met a stray lesbian there one night who I left with briefly to go to a big gay club together. Through it all, I was just trying to see where I fit in at all. I figured if I had any success at all at understanding where I was, I hoped I could see the light at the end of my gender tunnel was not the train and just maybe I could live my dream.

As much as I liked the interaction in Columbus, I knew I had to leave the relative safety of the group and try to carve out my own life as a transgender woman in the world. Sure, I was terrified to do it but I knew I had to overcome my fears if I was ever going to be able to move up my scale from a five to a seven. When I made it to a lucky seven, the pressure to live the way I wanted to really be increased. The reason for the increase came because of the new interactive experiences I was now having with other ciswomen around me. What I did was watch the women around me and try to learn how they were living their life and learn my own way.

From then on, when I could see the dream life I had hoped for was in sight, I could really concentrate on my future as a transfeminine person. At that point, I needed to begin my preparations for what do about telling the family close to me about my male to female gender transition, all the way to what I was going to do about surviving financially. I was to the point where I did not have to make it as a transgender woman, I just needed to let it happen. I had to stay in the new moment I was in and live it for all it was worth. It turned out my scale was worth it, all the way.

Stranger things happened to me. I may not have looked like a ten, but I felt like one.

Friday, November 14, 2025

A Marathon not a Sprint

 

Image from Peter Boccia
on UnSplash.

In my life, I have rarely ever had to run any distance at all. The only times when I did was when I played football and was in the Army. So, I was never a sprinter until I discovered my love of cross dressing as close as I could to a pretty girl. I could not wait until I came home from football practice, and no one was home so I could put on a short skirt like the cheerleaders I admired so much, were wearing.

I wonder now, if I knew how long it would take me and all the trials and tribulations I went through to arrive where I am today, would I have given up on my journey. I doubt it because along the way, my gender feelings ran so deep and I felt so natural as my feminine self, I could have ever turned back. I needed to settle in for the gender marathon I was facing because sprints (which I compare with brief moments of gender euphoria) were hard to come by. It is a good thing, because I was always better at marathons anyway.

I can blame my marital situation on the fact that I was still trying to run gender sprints. Rather than face up to the truth of who I was, for years I tried to maintain the delicate balance of a stable marriage and a rapidly growing love of public living as a transgender woman. All my sprints did were cause problems at home when I was caught and put a tremendous strain on my twenty-year -plus marriage. On occasion, life between us became so bad my wife on several occasions simply told me to be man enough to be a woman. I hadn’t been yet, but I was working on it. She did not know it, but her challenges kept me going during my gender marathon. I just needed time to get it through my old unwanted male head that being a woman (transgender or not) meant more than looking like one.

I receive many comments from those individuals who are just wondering where their gender path will take them. When I do, I try my best to point out I did not magically appear where I am now. It took me a lot of work and disappointment to realize I needed to be better than the average ciswoman to survive in their world. They had a head start on me in the race to womanhood and I needed to work hard to catch up. Along the way too, I found some ciswomen were eager to help me into their world, and some were not. Maybe they had their own marathons they were running in life.

Another thing I learned from running a gender marathon was I had the time to relax and enjoy the journey on occasion. I felt much different than the fast pace of fleeting gender euphoria when I was involved in a gender sprint. Then, it was back again to living in the present as a transfeminine person, rather than living in the future and missing most of the enjoyment. Slowing down also gave me time to research who I really was and who I was, was on the right path in my life. Because I had huge decisions to make. Family, marriage, jobs and friends could have been all on the line. At times I was crushed under the pressure of it all and had to put it down for a different day. Something I could have never done as a gender sprinter.

The moral to the story was that slowing down helped me to determine my own pace. The problem was that I wasted valuable time coming out of my male closet longer than I should of. I finally came to the conclusion that I could not have it both ways. I ended up doing what was right for me keeping in mind that your story you are writing in life could be totally different.

Either way, what you consider is a gender sprint or a marathon is a personal matter and has a lot to do with how old you are. Even though I have read about male to female transitions well after the age of sixty (when I did it) I think it is rarer because those who think they can put it off longer because they have put it off as long as they could. But then, on the other hand, there are people like me who realized their gender truth and could not put off making a move any longer. Before I had to sprint for the finish line of life itself.

 

 

 

 

 

Thursday, November 13, 2025

Staying in the Present

 

ss
Image from Ekka Wessman
on UnSplash. 


As I progressed in my cross-dressing life to a novice transgender woman, it proved to be difficult for me in several different areas.

Just one of those areas was the amount of time I needed to stay in the present for the first time in my life. My problem was compounded by the fact I had trained myself to daydream my life away as I wanted nothing more than to be a girl. Then, when I took my feminine image out of the mirror and put it into motion, I needed to constantly stay in the present to remind myself where I was and what I was doing. If I did not, I would be in danger of slipping back to my old ingrained male self. The problem was particularly intense when I was trying my best to mimic the magical way ciswomen moved.

Sadly, I found if I relaxed at all, no matter how attractive I thought I looked as a trans woman, all would be lost if I looked like a linebacker in drag as I walked. And to make matters worse, I needed to quickly learn to change the old stay away masculine scowl I had perfected and replace it with a more welcoming feminine look. As I shopped and interacted with ciswomen in public, they wanted to smile at me, so I needed to be pleasant and smile back. Especially if they suspected all was not as it seemed gender wise with me. I did not want to appear as any sort of a threat.

Staying in the present brought about other pleasant rewards also, such as when I communicated with other women, I needed to look them in the eye and listen to what they were saying, not jumping ahead and anticipating what I thought they were going to say. My communication game with women had really changed.

After a lifetime of hiding in the future, the present started to be a very pleasant place for me to be. I could take the time to feel the different clothes and talk to different people from a whole new viewpoint. I could take and give compliments from others regardless of their hidden motives. I found just the most innocent mention of my earrings from another woman was not about my choice of jewelry at all, she was gently starting a conversation to find out more about me. It all carried into the learning curve I experienced when I began to take lessons in passive aggressive aggression, from other women. I never had needed much knowledge of passive anything with the alpha macho men I hung out with. They were upfront with me for the most part. Ciswomen, on the other hand, could smile at you while they clawed your back for whatever reason they had. For a while, I thought I was going to have to carry band aids in my purse for any surprise attacks such as one night when a woman was coming back from the restroom and caught me talking to her man and took a dim view of the situation.

The more time I spent in the present, the better my life had become, and I got to the point where I missed out on all the time, I spent daydreaming of my life away. As I wondered how it would be if I could shed all my male existence and redo it as a transfeminine person which made me unapproachable to family and friends as well as making me totally miserable. Also, all the jealousy I felt towards ciswomen would have been swept away if I had had the chance to live and compete with them in their own world. To be sure, it was a different world but a life I discovered I enjoyed immensely as I found my new life to be all I thought it would be and more.

To arrive at the point I wanted to be, I first had to be confident in how I arrived at my own womanhood and if someone did not like me, it was their problem not mine. Then and only then could I fully live in the present and most importantly, try to forget most of my past. The future is still a problem for me as I wonder what will become of me if I have to encounter an assisted living situation where my gender issues are not addressed. The difference now is that I don’t spend the time dwelling on it as I used to. The present is just more important for me, which was a hard lesson to learn.

 

 

Wednesday, November 12, 2025

Playing the Short Gender Game

 

Image from Jayson Hindrichsen
on UnSplash.

During my life, I always have taken the easy way out and thought about important things such as my gender as a short-term issue.

I write often of my love for the mirror when I was young. I hated seeing my male self-reflected back at me but completely enjoyed it when the mirror came to life and I was cross dressed as a pretty girl. Perhaps it was then that I started to think of my life as a short-term basis. Would I eventually outgrow my desire to be a girl when I became older, or if I did not, what would happen to me then. To make matters worse, the Vietnam War was ramping up and I had the constant threat of military duty to think of. Normally when I did, and the coast was clear, I ran back to the mirror and escaped behind a dress and makeup.

As I wrote about yesterday on Veterans’ Day, military duty finally caught up to me when my draft lottery number was fifty-two, so all the short-term thinking and worrying I did was a waste of time. I was going to have to put all my love of being feminine behind me and survive the best I could. It turned out that all the worrying I did about my gender issues and sexuality was wasted too. As I stayed very short-term in my cross-dress thinking, destiny took over in my life, and I started to do more and more in the world to express my new feminine self. Even though I found myself living on the edge more than once, I learned to live there until the next challenge came along. These were the years of changing jobs and moving my family way too much.

As I frenetically moved through life, I was moving too fast to slow down and see what the real issue was. It was gender, and sooner or later I would have to deal with it one on one. Until I did, I would be living a lie and a very messy one at that. Out of the one transgender woman I personally know who told me she was never gender dysphoric, I would guess she would tell me also that she never encountered any messy moments in her life when she transitioned. If she did not, she is one of the few that I know who didn’t.

Many of my messy moments stemmed from me being selfish and wanting to maintain my twenty-five years of marriage to a woman I really loved when she was against me going any further as a transgender woman and starting gender affirming hormones or HRT. By attempting to have it all in my life, my mental health suffered, and I made many mistakes as I tried indirectly to out myself to the world. The biggest one was when I insisted on going into my own restaurant dressed as a woman and being immediately recognized which I could have been fired for.

By this time, I was in a downward spiral which I could see no way out of. It all led me to a suicide attempt and more dissatisfaction with life. Through it all, I had a little voice within me saying everything would be OK someday if I just followed my transfeminine instincts. But before I did, I was stubborn and had a lot of life yet to live. Just when I thought I could not go any lower, I did. I lost my wife and three out of the only four male friends I had to death. Which sent me even lower into depression. I was at a point the experts say with drug addicts who must hit bottom before they can start the path upward. Just change the wording to my male self was at the bottom of his journey and it was time to give my inner female a chance to live. Because, at this time, there was no longer time for short term solutions, my male self just had to be done.

Fortunately, I was able to salvage all the years of practice and learning I put into my femininizing projects and did not have to start from scratch when it came to working on my presentation as a transgender woman. I could look at the long-term benefits of my male to female gender transition. It was such a relief to be able to finally change my thought processes around and not play the short-term gender game at all.

Tuesday, November 11, 2025

United States Veteran's Day 2025

 

Female Service Person
from UnSplash.

Today is Veteran’s Day in the United States. The day we salute our numerous numbers of military veterans who served and serve our country. Especially those who made the ultimate sacrifice with their life.

As most of you know, I am a veteran myself and survivor of the Vietnam War conflict. Plus, I know I have plenty of other veterans who read and respond to the blog. To all of you, I would like to thank you for your service to our country.

In all my Veteran’s Day posts, I always make it a special point to mention all of those who were serving as they were in the closet or questioning their own gender issues when they lost their lives. It is suspected that there is a higher percentage of transgender people who try to serve but can’t or just hide it and go deep into their closets. I can’t imagine what that would feel like.

In my case, I have a couple of different positives which came from my time in the Army. First, infantry basic training taught me how to have a deeper respect for myself and the pressure I could endure. Secondly, I was able to travel the world on the military dime and learn how other cultures lived. Thirdly, I was able to come out of my gender closet for the first time and admit to close friends I was a transvestite after a Halloween party I went to as a woman. And perhaps the most important positive I gained from my time in the military was the chance I had to meet my first wife who was in the “Woman’s Army Corps” in Germany. She went on to be the mother of my only child (my daughter) who turned out to be one of my huge support systems in the future, and now. The gift that has kept on giving from the Army.

While I am on the topic of gifts, my continuing use of the Veteran’s Administration health care system has been a tremendous help in my life. It initially came at a time when I was financially broke and could not afford to buy my depression medications and gave me life giving hope especially when I sought out hormone replacement therapy and mental health help. So, as you can tell, I have been repaid many times for the service I gave to the country.

I am but one example of what is possible for veterans, but the fact remains that too many veterans young and old are suffering from PTSD or are homeless on the streets. If our country can afford to fight wars, it can afford to take care of those who fight them.

On this Veterans Day, please pause for a second and remember (or more importantly thank) those around you who have served our country or who are serving.

Monday, November 10, 2025

Tired of Looking Over my Shoulder

 

Christopher Morley
1974 movie
Freebie and the Bean.

In a continuation of yesterday’s post in many ways, today’s post is about how I grew weary of looking over my shoulder as a transgender woman.

Looking back, all I can remember from the earliest days I had cross-dressing in front of the mirror were the all too brief moments of gender euphoria I experienced and the all too numerous times I spent looking over my shoulder to see if anyone was going to catch me. Then life as I knew it would be ruined. To stop this from happening, I became very good at hiding my clothes and makeup away from the prying eyes of my slightly younger brother and the rest of my family. I even resorted to hiding a small amount of clothes, makeup and a mirror in a trash bag in a hollowed-out tree in the woods next to our house in the country. Even with all of this hiding, I still found myself spending a lot of time looking over my shoulder.

Somehow, I thought when I grew older, I would conquer all my gender issues, and they would magically disappear, but they just grew with me. The better I became applying makeup and selecting feminine clothes, the more I wanted to do. Like a dog chasing its tail, the more success I had led me to want to do more in the public’s eye. Sadly, as I grew into my high school and precollege years, I was still stuck in the same old routine of dressing at home, hiding from my family and looking over my shoulder. The only relief I remember was the night friends and I went to a high school carnival and one of the male students was parading around dressed as a pretty girl. I was fascinated but again was looking over my shoulder to make sure none of my friends noticed how interested I was.

Which was exactly how I felt when I saw the movie “Freebie and the Bean” in 1974. I did not know it or had never heard of actor “Christopher Morley” who was an accomplished female impersonator. He had a part in the movie which I found amazing because he was so believable as a woman. As with the student cross dressed as a pretty girl, when I saw Morley, I needed to look over my shoulder at my friends to see if they noticed my newfound interest in the film we were watching. I guess I was pretty good at hiding my interest because nobody ever said anything about it.

Moving forward, there were the early cross-dressing days when I was still trying to perfect my everyday presentation as a transgender woman. I constantly worried about someone sneaking up behind me and pulling off my ill-fitting wig. What would I do then? Put it back on or just pick the wig up and run out the door. Fortunately, I never had to find out when I figured it was my inner female paranoia talking to me that I was not looking good enough to pass her standards yet.

By this time, looking over my shoulder became a habit. There was a time when my second wife and I moved to a small town in southern Ohio to run a new restaurant there. In order to suppress all my cross-dressing desires, I started to do the grocery shopping as a woman then go ahead and do a little lite shopping for myself. One day when I was blissfully doing my thing as a transfeminine person, I unexpectedly ran straight into my wife’s boss doing his errands. As bad luck would have it, my wife and I were invited that weekend to a small party at her boss’s house and I needed to really look over my shoulder when I heard him mention to my wife about the “big woman” he had seen in a store. Rightfully so, I was always guilty until proven innocent with my wife and she turned directly to stare the look of death at me. It took me weeks of denial to finally live it down.

Denial, lying and other mistruths became a way of life for me with my wife before she passed away after twenty-five years of marriage. The only thing I am proud of is that I did manage a full out purge six months before she died. To prevent any backsliding, I even grew a beard. Needless to say, I was miserable during this time but nothing like I was going to live through later.

After all the tragedy I went through during this time, I finally had enough of looking over my shoulder for decades and decided to follow my instincts and come out to the world as a transgender woman. Not spending all that time and effort was completely refreshing and allowed me to totally concentrate on my new life as a trans woman.

 

Stopping was Never an Option

  Image from Josiah Niklas on UnSplash. Very early on, during my very confusing crossdressing years, I wondered if I could just stop the mad...