Friday, February 27, 2026

The Dream was Never Out of Sight

 

Image from Egor
Vikrev on UnSplash

On occasion, I write about my ultimate dream of someday living as a fulltime transgender woman. As is the case with any dream, making it a reality is often very difficult, and it forever remains a dream. The main problem I had was having the confidence to move ahead on my seemingly endless gender path. Somedays, it was like I was walking on air in my high heels and others, it was like I was walking through quicksand. I would be confidently clicking away in my heels until I hit an unseen crack in the sidewalk and almost broke my ankle, which was a prime example of my life at the time.

Even on the days when I was doing my best impression of a linebacker in heels, I tried to keep my head up and look to the future. Hoping for a better day when I could do a better job of presenting in the world as my dream woman. Growing up in my male life, I was accused continually by my parents of never finishing a task. It turned out, working towards my dream of crossing the gender border was the first real project I never quit on. Take my use of makeup for example, I would not rest and kept experimenting until I got it right. I became so good that my second wife would break down and ask me for advice on how to do her makeup. I don’t think she ever knew most of my makeup knowledge came from the night I gathered the courage to take off my wig and makeup and have a true professional redo my face and more importantly explain to me what he was doing as he did it.

Those were my shallow days of thinking being a transgender woman just meant looking like one. As I was told many times by my second wife, I made a terrible woman because I had not paid my dues to achieve my own womanhood. The whole process set my dreams way behind because there was little to no way of me sliding behind the gender curtain to gain the right to play in the girls’ sandbox. How could I ever achieve my dream, if no one would let me in was the frustrating question which I had over and over again. In the meantime, I was stuck cross-dressing in front of the mirror and keeping my dreams alive and knowing deep down someday I would achieve my own unique transfeminine womanhood.

The main problem I had was gaining the confidence I needed to keep my dream alive because deep down I had doubts about whether I could ever make it. Because at the time, all I had were the annual Halloween parties I went to. Even the parties were a struggle on occasion as I needed to figure out my “costume.” I went from thinking that sexy was the way to go, all the way to trying to fool the other attendees into thinking I was a ciswoman who just got off of work. By the time several Halloweens had rolled by, I had achieved my dream of being mistaken for a woman but then was faced with the dreaded what then? Looking ahead at waiting another year for a costume party was unbearable and damaged my dreams of trans womanhood. I knew from my party results I was becoming tantalizing closer to my dreams but getting there still seemed like they were miles away.

As I finally began to leave my mirror and gender closet and explore the world, I began to understand what my wife was trying to tell me. I was a terrible woman out of ignorance as I tried to mold an entirely new person. All I had to work with was my appearance which was just skin deep when I needed to communicate with mainly ciswomen in their world for the first time. For my “sandbox” I chose the bar scene which I was used to and provided me with many unique situations. Many of which I don’t recommend. Along the way, I found myself as a single woman in a bar attracting unwanted attention until I built a group of friends to mingle with. Fortunately, the vast majority of those people who wanted to interact with me were women, so I did not have to worry about a bunch of drunk toxic men.

As I survived this stage of my life successfully, it was time to seriously consider where I would go next. Would I stay where I was at, afraid to go any farther, or would I be brave and take the next step which would be HRT or gender affirming hormones. Following much thought, I decided to seek the HRT path by going to a doctor. By doing so, I discovered what a huge portion of my life I was missing. My body took to the hormones so naturally that I felt I should have been on them my whole life. Just another indication to me of how close my gender dream had always been. I just needed to reach out and grab it.

Perhaps, you may have a similar dream for your life. Mine turned out to be a single-minded pursuit of me wanting to cast aside being a man and start being a woman. Regardless, the way I did it could be different from yours. I chose a “stairstep” method of my male to female femininization process. What I mean is, every time I was successful at one level of my transition, I needed to choose another gender project. If I wasn’t shopping for that new favorite outfit, I needed to figure out where I was going to wear it, is an example.

When I finally made it to the point of being able to live my dream, I certainly had paid my dues and had a lot of help from friends to therapy. They all helped to lift me from being a so-called terrible woman into a well rounded trans woman living her dream which was never far out of sight.

 

Thursday, February 26, 2026

Honesty was Always the Best Policy

 

Image from Jon Tyson on 
UnSplash. 

Very early on in my life, I thought my default mechanism to anyone challenging my masculinity would be to lie about it. Fortunately, I did not have to take that route often because of all the elaborate ways I utilized to hide my feminine desires. Examples were the times I was competing in sports or working on cars. People close to me just assumed I was a “normal” male.

It wasn’t until much later in life when I began to get serious about dating women, did honesty become a real priority when it came to explaining my life. My first experience with telling a woman I was serious about, has been relayed several times here as recently as in the last several days. She is the one I coerced into dressing me head to toe as a woman which was the first time a ciswoman had attempted to do it for me. The whole plan turned out to be a disaster because of so many things. As I have mentioned before, I just wasn’t that impressed with the outcome she presented to me as she applied my makeup and the long blond wig I so desperately wanted. By then, I had spent years doing my own makeup and I thought I did a better job.

Little did I know that disappointment would only be the beginning of many with her. Being honest in our relationship early on led to an engagement but then a total break up because of a date I had with Uncle Sam and the Vietnam War. Rather than support me as I served, my then fiancé insisted I tell the draft board and the world I was gay to try to not get drafted which would have been a total lie. I knew I was a cross dresser but also had a pretty good idea I was not gay. Instead of wrecking my personal life as I knew it, we broke the engagement and went on our not so merry ways. I knew where I was headed, the US Army for three years. It was not the most pleasant time I ever spent in my life, but at least I was honest with myself.

Time went by in the Army until I found myself in a place to exercise some of my cross-dressing desires by going to a hospital Halloween party I was invited to by friends. By doing so, I through caution to the wind and decided to go all out dressed as a woman. I only had about eight months or so to go in the Army, so I was willing to risk getting in trouble to satisfy my need to cross-dress after such a long time of being denied.

All three of my closest friends that I socialized with all the time were at the party too, and as luck would have it, several weeks later, the subject of our “costumes” came up after a long night of enjoying very good German beer. When my turn came to talk about how I had went to all the effort to femininize myself for one night (including shaving my legs), I finally just was honest with my friends and told them I was a transvestite and the Halloween party was far from being just a one night deal of seeing what it would be like to dress as a woman. It was the first time I had ever admitted to anyone that I had a fondness for being a woman, so it was quite the liberating experience.

It was also a far-reaching experience because included in my group of friends was a woman who I got to know quite well. So, well in fact that later on we went on to be married and she became the mother of my only daughter who I cherish to this day and is one of my biggest supporters. Obviously, from day one in our relationship, she was aware of my feminine desires and accepted them.

Much of the same happened with my second wife, who was much more strong willed than wife number one. Even so, I felt honesty was the best policy and I nervously told her again I was a transvestite or cross-dresser before we were married. Ironically, the problem came with me not cheating on her with myself. What I was increasingly doing was doing exactly what I had sworn not to do. Leave the house dressed as a woman. By doing so, I broke one of the main bonds of our marriage which was not lying to her about what I was doing all the time.

Needless to say, like any other ciswoman, my second wife had keen instincts of what I was doing and was constantly on the outlook for things like extra forgotten makeup on my face when I was out and about as a novice trans woman. Since I prided myself in the rest of my life on my honesty, the constant lying I was doing to the woman I loved broke my heart. Especially when I could not stop doing it.

My heart was further shattered when she passed away quite unexpectedly from a massive heart attack and I was on my own after twenty-five years of marriage. The only redeeming thing I did was completely purge my feminine side for six months before she died. Even to the point of growing a beard. It was the only thing I could do to try to redeem myself.

Ironically, her death forced open the biggest door to my honesty there was, being honest with myself. When I looked deep, I found that all along I had been just wasting my time trying to be a man with all the privilege that came with it. I had learned to play the male game effectively but did not want any thing to do with my gender prizes after I won them. Being honest with myself for a change was the best feeling of all except I did feel guilty about all the stress and tension I had put others through because of my inner weakness. Total honesty certainly would have been the best policy in my life.

 

 

 

 

Wednesday, February 25, 2026

Everything was OK Until it Wasn't

 

JJ Hart. Frozen in Florida

So many times, when I was caught between my genders, I learned everything was Ok, until it wasn’t.

A prime example would be when I was coming home from a night in the gay venues I was frequenting and my car decided not to start when I was twenty miles away from home. Then I needed to figure out how to get the car home before my wife came home and took off all my make-up acting like nothing had happened. What I did was call a towing company and get the car towed back home as I sat in the cab with the driver, trying my best to present as a blond woman just trying to get her car home. Somehow, I did make it that night and learned to never take that car again when I went out on such a pressure packed adventure.

Sadly, I needed to learn the hard way as I followed my gender path through many blind curves and major potholes. I would usually start out with a final look in the mirror thinking I made an attractive woman from the testosterone poisoned male I had to work from. Confidently, I moved ahead to whichever venues I decided to go to that night. And the stakes were raised significantly when I decided to leave the relative safety of the gay venues behind and attempt to see how I could do in the straight world of big sports bars. It turned out, if everything was going to be OK, I would find out quickly.

Normally I found everything was going to be OK, except on the nights I encountered problems using the women’s restroom and I ended up having the police called on me. That turned out to be more embarrassing than anything else because the cops had better things to do as I was just sent on my way. A more embarrassing night came along much later when a group of drunk guys decided it would be fun to play “Dude Looks Like a Lady” about five times in a row on the juke box. Which ended me getting asked to leave by the manager, even though I was a regular. Well, liked by the staff, who actually tracked me down at a close venue not long after and asked to come back. Telling me, the manager who told me to leave got fired. I was flattered and accepted my welcome back because everything I thought was OK, actually was.

Other times, I was not as fortunate as I began to learn the basics of being allowed to play in the girls’ sandbox. Learning the time-honored tradition of passive aggressive behavior which ciswomen practice so well, proved to be a challenge. I was used to taking another man at face value most of the time until he proved himself unworthy which did work with women. I learned a smile could be hiding something much more sinister. Resulting in claw marks down my back. Once I did, again everything really did turn out to be OK and stayed that way for the most part.

In no way, do I want anyone to think this gender male to female feminization project was a quick one. There were so many nights when I hurried home to return to my old unwanted male self that I wondered what I was doing. I was risking so much on what often seemed to be an empty dream of someday being able to live as a fulltime transgender woman. What kept me going was the deep feeling I had that when I was my feminine self, I felt so natural and I felt as if I somehow was home. And someday, all the setbacks I had would just disappear and everything would truly be OK.

Through the magic of gender affirming hormones (HRT), and strong ciswomen role models, I was able to weather the transition storm I was going through. I knew everything was going to really be OK when I found I could validate myself in the world as a trans woman without the validation of a man, or anyone else. The whole process was so much more complex rather than just looking like a woman. I needed to be my own woman, on my own terms so I could exist on the path I had always been on. Even though sometimes I did not realize it myself. Those were the days of feeling like a failure when a group of teenagers laughed at me for how I looked. Rather than staying and trying to do better, I had to run home crying and go back to my cross-dressing drawing board. Seeking the idea that everything was going to be OK, even though it was not at the time.

As I said, what kept me going was a small spark of feminine energy deep down inside me. Knowing for sure, being the woman I dreamed of being was going to be an incredibly complex gender journey to make. Just lacking the communication skills, I needed to survive in the world as I went one on one with other women made my life a scary one. Since I was shy to begin with, I needed to start from scratch in a new world and work hard to gain an equal footing as a novice trans woman trying to make it alone in the world until I was able to make new friends.

The new friends I made helped me to cushion when I got into situations when everything was OK until it wasn’t. During those times, I could fall back into the group and learn from what was going on. Every learning experience became so important because I could make sure to never try that again. Even what was left of my stubborn male self-learned the misconceptions he had about how women truly lived and did he really want to let go of his life for good.

When he did, I found that everything was going to be OK and it always was.

Monday, February 23, 2026

I Needed Help

 

Image from Kelly Sikkema on UnSplash.

Starting at the very beginning of my long gender journey, it seemed I needed help at every turn.

For the longest time, I thought any ciswoman could help me improve my major concern of just looking as feminine as I could. When it finally happened to me in my college days, I was so practiced in the art of makeup, I thought I could still do a better job than the woman who was working on me. I was truly disappointed and all I ended up doing was out myself as a transvestite (or cross-dresser) to someone who would hold it against me later in life. Lesson learned and it took me years to trust anyone at all with my secret. Ironically, my secret carried over all the way to the transgender-crossdresser mixer where I had the courage to take off my wig and makeup and experience the makeup magic of a professional artist. “He” was able to work wonders with my appearance and even explain what he was doing. More than any ciswoman had ever been able to do for me. So it wasn’t a woman at all who helped me initially, it was a man.

As the years flew by though, the next help I tried was therapy. I needed it to help save my long-term marriage to my second wife who was always against me leaving the house as a transfeminine person. Several times, when she caught me, I volunteered to go therapy to hopefully solve my “problem”. It turns out, therapy ran the gamut for me from very good to very bad. But overall, the good was very good and outdid the very bad, where the therapist did not know anything about gender issues or even care to learn by listening to me. I even went to the extent of driving a long distance to one of the only practicing gender therapists in Ohio at that time. She was good and even was the first therapist to diagnose my Bi-polar depression at a time when I had to fight a major battle just to get out of bed and go to work.

On top of that, she gave me the best advice that I have never listened to. That she could do nothing about me wanting to be a girl. Only I could fight that battle, if I chose to. As I said, I chose not to listen and went on to fight a losing gender battle for years which turned out to be a waste of time and energy.

The next therapist of note that I had turned out to be a match made in heaven by such a place as the Veterans’ Administration. When I applied for gender affirming hormones under VA’s new program way back then, I had to go through therapy to be approved. It ended up working so well that not only did my new therapist pave the way for HRT, but she also ended up producing the paperwork I needed to change my legal gender markers within the VA and in the outside world too. I was with her for years before she moved on to another hospital and now the only therapy, I need is the LGBTQ support group meeting I attend most every Friday.

As you can tell, therapy has been a mixed blessing for me. At times, it is a total waste of time and energy but at other times a real-life saver. Perhaps it was my own fault because I did not understand you can only get out of therapy what you put into it. Being the self-contained, stubborn person that I am, it took me a while to understand what I was trying to accomplish.

As I backed off therapy as my major impact in my male to female femininization process, I began to rely on my dealings with the public to get me by in life. I still needed major help, but I needed to find different places to find it. That is where my socialization process as a transgender woman became so valuable. Since I had become a social person as a male before my wife and close friends had all passed away, I was intensely lonely with no where to turn except to my inner feminine self.

She guided me slowly to a spot where I still needed help but could hide it. What I mean is I could learn from every social interaction I encountered. The small group of ciswomen I socialized with became my teachers and even my protectors without them even realizing it. I was going through a master’s class in gender at such a rapid pace I could not believe my good fortune. For the first time in my life, other women were coming to me for help as a transgender woman. They sensed my background in both the major binary genders could prove to be valuable lessons for them as women with men.

It felt good to me to be able to pay forward in any small way I could any of the lessons I had learned the hard way. Being with therapy or any other help I could give. It is another reason I decided to start blogging about my gender dysphoria so many years before. It is interesting to read any of those ancient posts and see how many of them just revolved my appearance as a cross dresser before I transitioned into a full-time trans woman.

Sometimes too, help can come in ways when you least expect it. From a supporting spouse, all the way to finding your whole new LGBTQ community, there are many ways to find help. Hopefully, you can find your own help. No matter how large or small it could be. Just be ready to accept it when it is offered.

 

Sunday, February 22, 2026

Did I Believe in Magic?

 

Image from Delphian Lacub
on UnSplash.


It is rare, but on occasion, I still hear the question of when I knew I had gender issues.

The truth of the matter is, I always knew I was transgender. I just did not know how to express it until I was older. It was after my early explorations into my mom’s clothes did, I realize the potential magic I was holding when I carefully tried on her clothes knowing fully it would not be long until I would outgrow all her wardrobe and I would be in never-never land when it came to finding feminine clothes to wear.

Somehow in the near future, I made do with stretching elastic girl’s clothes I found in the lost and found box at the school I went to. I had a short skirt I managed to squeeze into that I cherished forever it seemed. Around that skirt I managed to build the basics of my style with the money I earned from allowances and stray jobs I found. I delivered newspapers and even mowed a cemetery for a dollar a hour in the hot summer sun, just so I could sneak out to a store and buy more feminizing items. Through it all, I believed in the magic which made me who I truly was.

It was always difficult for me to hang on to my trans truth because at the same time I was experimenting with being a girl, my male self was actually able to establish himself successfully in the world. Which just served to tear up my fragile mental health enough. Until you must wake up in the morning wondering if you are a boy or a girl, you don’t know what I am talking about. I would not have wished it on my worst enemy.

On certain occasions, my magic was strong and I felt like a girl when I looked at myself in the mirror. On other occasions, life was hell when I could not find the time to sneak around and cross dress as the girl I was. It was during those times; I had to rely on just that small amount of magic to get me by. One of the problems was I was so envious of the other girls around me at school in their pretty clothes and admiring looks from all the boys. I dreamed of being just like them.

It wasn’t until I began to explore the world as a novice transfeminine person, did I finally realize what my magic was all about. All of the doubts I had on where I was headed in my life began to dissolve when I began to feel so natural in my progression. Life was a blur as I was going out to be by myself in the world as a transgender woman. By doing so, I was able to meet strangers who accepted me for who I was. For the first time in my life, I was able to shed the long shadow of the remnants of my male past.  Every night, I was able to find my way out to one of my regular venues, be it lesbian or straight, I never wanted to return to my male self at all and lose my magic.

It turned out, my magic never went away, it just became stronger. So much so that I made the move to forever give up my male ways and start gender affirming hormones or HRT. The hormones just reaffirmed and strengthened my belief that magic could happen and I could indeed be the transgender woman who could forever lose her male past and survive. I could change my life from being married, with friends, family and a great job into a much more mellow existence.

It just took me too long to realize how deep my magic went in my life, and how backwards I had my whole existence and how much pain it caused me. It was my fault because I did not believe in my own magic enough to do something about it rather than be a part-time cross-dresser. I always point out I have nothing against cross-dressers at all because I depended upon it to live my life for so long.

Did I believe in magic? No. Should I have, absolutely.

 

 

Saturday, February 21, 2026

A Little Success Goes a long Way

 

Hair by JJ Hart. Bead Work
by Liz T Designs

In the life of a novice transgender woman or man, a little success can go a long way. Mainly because very few of us are blessed with the natural gender characteristics of the gender we feel is truly us to get us started.

At that point, we must feel our way along. Sometimes submitting ourselves to abuse from the public as we go forth in the world for the first time. In my case, I make no secret of the many times I headed back home in tears after being laughed at to my face in public. Somehow, through it all, I was able to catch and enjoy brief moments of gender euphoria to keep me going to a distant dream of possibly living a life as a full-time transgender woman. Of course, I did not have any idea that I actually could do it.

I was fortunate that practice made perfect (or close to it) as I was able to improve my makeup and clothing skills to where I could survive in public when I left my mirror. Which I discovered was one of my biggest problems because it had the tendency to lie to me when it came to my overall appearance as a woman. Too many times, I went out thinking I looked great and then had the world slap me down in laughter because of the mirror. Plus, my male ego was giving me the wrong impression of how to look as I attempted the sexy look when I was in my thirties not in my teens. There could be no shortcuts in being able to present myself well as a trans woman, I would have to concentrate harder on my makeup and wardrobe than anything I ever tried before. Just because I was trying to dress sexy and show too much skin would not work in the real world if I was to blend in with the other ciswomen around me.

Finally, success did come to me as I haunted the thrift stores in my area for just the right fashion to attempt to flatter my testosterone poisoned body. It turned out I could not attempt to test my success until I left the gay venues I was going to and tried to go straight with my public excursions. The gays did not care how I looked and just viewed me as a drag queen any how so I was wasting my time until I discovered how I could make it or not in the big sports bars I was used to going to as a man. When I followed my three-step method of acceptance, I had no problems being accepted. My three steps were to put my fear behind me and smile, never cause any trouble and tip well earned me the right that every regular had. Especially the one I cherished more than anything else, the right to use the women’s restroom.

With my success came responsibility. I needed to be on the alert for other strangers who wanted to talk to me. Especially ciswomen who were curious about why I wanted in their world. Success in my communication skills led me to learn more about living behind the scenes as a ciswoman than I ever though I could. My primary example I always use is how women use the power of nonverbal and passive aggressive communication to get by in the world. Especially when it comes with dealing with men. It was very difficult for me to learn the basics women use to live but as I did, a whole exciting new world opened to me. Perhaps the best part of it all was that it felt so natural, so I knew I was on the right gender path in my life for the first time.

My success then began to go a long way when I discovered a small circle of women friends I could socialize with on a regular basis. I was always a social person anyway, so the fit seemed fun and natural to me as I gained the confidence I never had before when I was a solitary, lonely cross-dresser. And the best part was, I was having the opportunity to learn from the other women around me about knowing how it really was to interact with the world as a transgender woman rather than how I always dreamed it would be. Needless to say, I learned a lot.

I looked at my whole experience as paying dues as I went from being laughed at in public all the way to having my own set of ciswomen friends to socialize with and even marrying one later in life. Ironically, it was my wife Liz who convinced me once and for all to put my male self behind me, give away all my male clothes and start gender affirming hormones. Which I had always considered the next logical step in my male to female gender transition. It turned out, hormones would be the great “aha” moment in my life as the femininization process took hold. It was as if I should have always been on the hormones because the process felt so natural. The changes went way past the external softening of the skin, breast and hair changes all the way to all the internal changes such as emotions and more.

For me, success took a long time coming, and early failures at passing in public made me very timid. Once I made it through all of that, success came more naturally to me. All the way from just leaving the house cross dressed to HRT, my life became a blur of changes. Sure, the battles I needed to fight came at me fast and furious because I was so embedded in the male culture but I was able to fight my way through them and be successful as I discovered a little success went a long way and kept me going along my gender path towards a life I had only dreamed of.

Friday, February 20, 2026

Time Flies When you are a Crossdresser

Image from UnSplash. 
Since now I have been blessed with making it to the age of seventy-six, I spend a lot of time wondering what I did with my life.

As I mentioned in yesterday's post, I spent much of my time running from myself by changing jobs and moving my family. At the same time, I was doing all of that, I was busy cross-dressing to keep my fragile mental health together. I started the same way most of you with gender issues did by trying on my mom’s clothes and moving on from there. The urge was so strong that I even went out and got a newspaper delivery route (back when newspapers were relevant) so I could make extra money to buy my own makeup, panty hose as well as other feminine items I could afford. Before I knew it, I was becoming fairly proficient at applying my own makeup. So good that the first time I talked a ciswoman into making me over into a woman, I thought I had done a better job with my makeup.

Those were during my college days which were split in two by my military duty during the Vietnam War and all cross-dressing activities were brought to a complete halt. When you are younger, years are more precious and the time away from my makeup, dresses, and wigs seemed impossible to face. Somehow, I made it through and even discovered the magic of attending a Halloween party dressed as a woman while I was in the Army. The good news is I did it but the bad news was the time was very limited, and I had a lot to go over in my mind including Halloween was then another year away. What would I do in the meantime to help solve my cross-dressing dilemma.

What I tried to do first was to drink my gender problems away, which only partially worked because when I sobered up, my issues were still with me and sometimes potentially worse when one night in the Army I told three close friends I was actually a transvestite and like to wear women’s clothes. Not just at Halloween. I was lucky, the word about my gender issues never got out to my higher ups and I went on to serve out my time with a honorable discharge.

When I rejoined civilian life, I had the chance to seriously consider making the gender jump from a male life to a female one. Following serious consideration, I felt the leap would just be too far to make, so I reluctantly chose to stay on the cross-dressing path I was on. To do just enough in front of the mirror to maintain my sanity.

Nothing changed until I began to leave my mirror behind and experience life in the public eye as a novice cross-dresser. Or so I thought. All was good, until the night something clicked in my mind when I was getting ready to go out to the straight venues I was visiting when I left the gay spots behind. As I examined myself in the mirror, I stopped and said what I was doing.  I suddenly felt empty and needed more and then concluded I had taken just dressing as a woman as far as I could. I needed to experience the next step which was actually interacting one on one with other women as an equal. Even though the idea scared me to death, I needed to hitch up my big girl panties and transition again into a full-fledged transgender woman. The venue I chose was TGIF Fridays I was familiar with as a man and I knew if I could make it past the hostess stand with no extra attention, I had a good chance of finding a seat at the bar with the other women who were just getting off work at the nearby mall. Amazingly, my plan worked to perfection, and I made it to the bar and claimed my seat. The bartender waited on me without showing any signs of gender disgust and I even ordered a second drink to celebrate my successful major transition in life. From serious cross-dresser to novice transgender woman. Even saying the word felt good to me.

By the time, time was flying by as I was trying desperately to build a new transfeminine life while at the same time maintaining a long-term marriage and successful job. I found I was not too successful as a juggler because the same time I was feeling good and natural as a trans woman my male life would sneak back it and ruin it for me. Eventually, it all became too much for me to handle mentally, and a suicide attempt followed.

Maybe I spent too much time in my life obsessing over my feminine appearance which I attribute into being a very serious cross-dresser. Certainly, all the successful public appearances I made as a woman were not helping me with my ultimate goal of living my dream. In the long-term, I never bargained on going through two major male to female femininizations to even come close to discovering if I could find my true life and live it as a successful trans woman. Maybe I was too shy or scared to go too fast. One way or another, it is too late now to cry over torn panty hose. Life gives us only one chance to get it right.

Wherever you maybe in your gender transitory journey, I hope you can steer clear of the major roadblocks’ politicians are attempting to out in our way as transgender people. May your path be as smooth as possible as your own time flies by as a cross-dresser or transgender woman.

  


Thursday, February 19, 2026

What is Chasing You?

 

Image from Filip Mroz
on UnSplash. 

As human beings, we all have something that is chasing us. As transgender women or trans men, that something which is chasing us may be more serious.

As we all know, gender is one of the most basic wants and needs for a person. At birth, we are put into a male or female box which is often very difficult to change. In my case, I was born into a very male dominated family as their first-born son, so changing anything with my gender was totally out of the question. In addition, information on gender dysphoria was difficult to find in the pre-internet days.

All of this set me up for a chase which would dominate my life for nearly five decades. Mainly because my male self-had a huge head start on the race to claim myself. He was born into male privilege that he just had to compete in the world to claim. Along the way, he managed to do quite well in the privilege race, which made it more difficult to give up his male life when the time came to do it.

As I became older and more settled into a routine, what was chasing me became more evident. I wanted to be a transgender woman more than anything else in my life. It all set me off in a collision course with changing jobs and moving from my native Ohio as I desperately tried to outrun what was chasing me. I thought each move I made would bring me closer to living the dream life I always hoped was possible. Examples included moving from a small conservative town in Ohio to the huge metro New York City area so I could be closer to a more liberal cross-dressing area. Even though that proved true to an extent, I found I still had the same restrictions on expressing my feminine self as I had in Ohio. So, I moved back to a very rural area where I thought I could hide my cross-dressing ways. Ironically, the best move I made was the next one when I moved back near to Columbus, Ohio where I could reconnect with the small group of diverse friends I had made before at crossdresser-transgender mixers I had went to.

Through it all, all my running was becoming increasingly exhaustive on my mental health. I was taking one step forward towards my goal of living a transfeminine life, while at the same time taking a step or two back when my public persona as a woman was discovered and I was crushed mentally. I kept going back to my gender drawing board until I got it right, or to the point where I could go out in public without the fear of abuse.

When I did reach that point, the feminine person chasing me upped her game and I needed to get better when I interacted with the world. What happened was people started to recognize me, so I needed to start building a whole new person. I needed to choose a new name to fit my personality and stick with it. Which also meant I needed to attempt the most difficult task of all for me, the time I spent communicating one on one with other women. I needed to throw my innate shyness out of the window and learn the basics of eye-to-eye communication which I learned was so big with cis women. Plus, I really wanted to learn to interact with women because I could learn so much from them while at the same time not coming off like a mean bitch.

As I learned to relax and interact with my new world, the inner female which was chasing me could relax a little too. At the same time, my male self-began to finally realize he was losing the race for dominance in my world. More and more, I felt the fear of giving up my male privileges fade away as the introduction of female privileges set in. For the first time in my life, I felt free of the gender struggles which had defined me. I remember vividly the night I sat by myself and added up all the pluses and minuses to the moves I was considering making. The end result was in my life as a novice transgender woman, I had never felt so natural and free. The decision was an easy one for me as I decided to take the next step and seek a doctor’s approval for gender affirming hormones or HRT. A move I considered for once and for all, end any questions about what was chasing me.

That decision brought all the exhaustive chases to an end in my life. The only problem was it took me until the age of sixty to face my inner truths and find peace in my life.

 

Wednesday, February 18, 2026

Innocence Lost

 

JJ Hart

Looking back at my long life, I reflected on the more innocent times, or were they?

One of the many things that amuse me about a certain political movement that pretends to want to make America great again, was when was it great? Was it the pre-civil rights era struggles of the 1950’s? Or the seismic changes of the 1960’s when the Vietnam War raged on. Plus, it is easy to forget how much of this country was built on the back of slavery.

During the 50’s as I was watching the plethora of westerns on our new television, I was also running to cross-dress in front of my mirror and pretended I was the pretty girl I saw on television being saved by the handsome cowboy. Totally ignoring the fact that the native Americans fighting the cowboys and Army were fighting for their land which was being stolen from them. But I stayed innocent behind my skirts and makeup until the Vietnam War caught up with me. Which made it impossible for me to remain neutral anymore. What the hell were we doing as a country fighting a losing war in a southeast Asian country anyhow?

It was about that time that I had to draw a line in the sand and reject the beliefs of my “greatest generation parents” who had survived a great depression as well as WWII. I just could not accept their thoughts about life any longer which included my ideas about my gender. Which were developing quickly. I knew for the longest time that something was wrong in my life, I just couldn't tell completely what it was.

Again, it was the military which covered up my desire to be feminine. Going away to Army basic training proved to the most dedicated people watching me that I was nothing more than a so-called normal male. All my time in the military did was strengthen my idea of who I was as a human and give me the extra ability to take advantage of who I truly was as a transfeminine person. Around this time also, was when I discovered the power of the internet which led me to a whole wide world of information and people to know. The people were the first I ever met who shared the same transgender desires than I did. My innocence was forever lost.

As I became more active in the world as a transgender woman and transitioned from being a serious cross dresser, I found I did not have the same rights as the typical American was supposed to have. For awhile under a previous President, our trans situation was better such as transgender military members being allowed to serve their country. Today, all that has changed of course under the current regime in Washington. I can’t say any of my innocence was lost because I could see all of this happening years ago when he was elected for the first time.

Even though, we transgender women and trans men make up a very small portion of the population we have to bear the unrestricted hate and bigotry of one of the political parties which is heart breaking to me. Especially when I need to take into consideration the transgender youth in the country who will have to fight these unfair laws forever it seems. Their innocence never had a chance to start before it was disrupted.

How do we truly make America great again? Try to restore the basic goodness of people everywhere. While I was in the hospital, I had several nurses tell me how mean the public has become. So, it is just not towards transgender people at all. It all starts at the top in Washington and works its way downward into society.  At my age of seventy six, my age of innocence was lost years ago when I first glimpsed myself as a girl in the mirror. Even then I knew I needed more than clothes to succeed in life as a feminine person. I just wish I had acted on my desires earlier. Other than that, I fear we have lost years of developing a creative nurturing society that we need to help all of us. Including the small but vibrant transgender community. Who can’t afford to take many more shots.

I wish I could be more positive about our lives, but I am just looking at my life as I see it and comparing it to my past. I just hope together we can all make it. Innocence or not.

 

 

The Dream was Never Out of Sight

  Image from Egor Vikrev on UnSplash On occasion, I write about my ultimate dream of someday living as a fulltime transgender woman . As is ...