Showing posts with label cisgender woman. Show all posts
Showing posts with label cisgender woman. Show all posts

Tuesday, July 28, 2026

Who Got in Your Way

 

Image from UnSplash. 

Perhaps there was that special person or persons who stood in the way of you going along your formative gender path. In my case, I always tried to blame my second wife for being in my way of perfecting my male to female feminization project. My first wife was not a factor because I thought she was just along for the ride, no matter how bumpy it became and I always thought I could suddenly tell her I would be gone for several months because I was going to Thailand not to visit but for gender realignment surgery and she would say be safe.

That was all well and good until I met my second wife who I immediately fell in love with. I ended up divorcing my first wife and marrying my second in a fairly short time. Like my first wife, even though she knew I was a parttime cross-dresser when we married it was fine with her but unlike wife number one, she always resisted me going any further towards maturing into a transgender woman. Being as strong-willed as she was, I wonder how we made it through twenty-five years of marriage until she passed away.

Throughout the years, we somehow stayed committed to each other following many bitter battles over how I was wanting to live my life. She was much wiser than me over the years as she told me things such as I made a terrible woman (true at the time) and why didn’t I just go ahead and move away and live like a woman and save both of us the hassle. As I always point out, I did not know how to “make” a better woman because I had never been behind the feminine gender curtain to discover all the complexities of what I was taking on. As far as just going away and starting all over on my own, I was selfish or self-centered and wanted to maintain as much as I could of my male life which among other things paid most of the bills.

Through it all, faint glimpses of my transgender dream kept filtering into my life, and I did things like transvestite-transgender mixers and Halloween parties to experiment if I could make it at all. Once I received positive feedback from doing it, I was pushed forward to expand the boundaries of my marriage. Just to be met with an equal amount of pushback from my wife. The worst part about it was I understood where she was coming from as her marriage was unraveling right in front of her eyes at the hands of another woman. Who was me. I ended up resenting her in a couple of ways. First, because she was what I always wanted to be. Soft curvy body and all. And second because she stood directly in my path of achieving the same things that she took for granted, along with the rest of her ciswomen friends. Great makeup, hair and clothes could not hide the envy I felt for missing out on a feminine life I always wanted.

It took me awhile after she passed on at the age of fifty to realize who the real culprit was who was standing in my way of my male to female transition. All along it was all me who never responded the right way when my wife said be man enough to be a woman. As I said, I was too selfish to not want to give up all the male privileges I had earned over the years and wanted to live my life on dual gender impossible terms as long as I could.

I also tried therapy on the side to help the way I felt and even rejected their advice when essentially, they told me the same thing my wife told me. There was nothing they could do about me wanting to be a woman. She was a part of my inner self and only I could deal with her. When it came right down to it, I was scared of my inner woman and how she could ever carve out her own life in the world. It turned out, I just never gave her enough credit as over the years with help from strong feminine role models like my mom and wife, she was able to mold her own personality. Even though she had to keep it hidden for decades. Those same strong ciswomen showed her where there was a will, there was a way. Especially when you had to take the time and effort to get there.

Once I found myself firmly placed behind the gender curtain, the real work began to make sure I never “made” a terrible woman. I wanted to as much as possible, bring all the good feminine characteristics with me so I could do more than survive. I wanted to thrive as I made my way to my dream of living a transgender life. As I did, the major realization came to me that it was me and only me who was standing in my own way all those years when I was wondering what gender I was at all. Shame on me for not having the courage to face my true self in the mirror and not let my gender dysphoria get in the way. Worse yet, everything was screaming within me that I was doing the right thing when I approached my transgender womanhood. Freeing myself up to live was as if I was taking a ton of weight off of my shoulders.

Ironically, once I was approved to play in the girls’ club, the difference I had from the different upbringing I had made me a special sort of woman to the ciswomen who accepted me around me. Even though they knew I came with different baggage, the most radical advice I ever got was welcome to our world when I was complaining about hot flashes. As my body started to respond to the HRT or gender affirming hormones I was on that I had waited so long for. I don’t think the women ever realized how badly I wanted to be in their world.

If it was not for me being in my own way, I would have been in their world sooner. My proper place to be.

 

Thursday, July 9, 2026

On a Gender Vacation without a Passport

 

JJ Hart

I saw on the news this morning that shortly after the Fourth of July holiday is the busiest time to travel during the year. It got me to thinking about my own major vacations when I shed my male self and began my life as a transfeminine person.

Mainly, I remember the times when I just needed a passport to go past my natural fears, put my cross-dressing past behind me and step into the world of a transgender woman. That invisible passport was difficult for me to come by since I needed to overcome my fragile confidence to step out of my gender shadows to get it. It was difficult because my earliest days of going public as a trans woman were often brutal when the public got ahold of me and I was laughed at routinely. It literally took me years of work in my cross-dressing workbook to get to the point where I could go out into the world and make a good effort to blend in. When I did, I began to earn my vacation away from my male self.

The more vacations away from him that I had, the more I began to appreciate the new world of ciswomen I was allowed into. As rock and roll idol “Billy Idol” was singing, the more I did, I wanted “More, More, More.” (Rebel Yell, 1984) Early on, I was naive and did not realize what I was getting myself into and partially thought my need for a gender passport would eventually burn itself out and go away. But of course, the need to have a passport just burned brighter in my soul. It seemed because of the need for femininity increasingly felt so natural to me.

It turned out at that time, when I was out in the world as a trans woman, either I was getting it very right or very wrong. Mainly because I did not know what I was doing such as how to move the best I could as a woman or how I communicated with other women at the time. Because they were overwhelmingly the only people who were interested in talking to me at all as nearly all men shunned me. I was amazed at how many women in their own unique way wanted to see my gender passport and let me in behind the gender curtain.

It all led me to finally legally change my name with the help of my daughter. We came up with a family name which honored one of my grandparents and my mom too. Who never supported her new daughter, but I forgave her and took her first name as my new middle name anyhow. As a plus, my new initials were easy for my three young grandkids to remember me by, so the name was well accepted by all.

Since I had my new permanent name in place, I could start building a new permanent feminine persona every time I went out to try to carve out a new life as a trans woman. As I was carving, sometimes I hit very hard granite and had to stop and start over until I could find the sandstone softer rock and keep moving towards my gender goal of living fulltime as a transfeminine person. As I carved, I needed to make certain I was always on the outlook for cave-ins which could cause havoc with my male life. Which was still very much in the picture. Because he still controlled most of my life the public saw as well as life with my second wife (who wanted no part of losing a transgender spouse) and a very good job I had at that time too.

As life moved on for me, I discovered brief moments of gender euphoria which kept me going through the dark days of my male to female femininization. Such as when I was able to leave the gay bar venues which I felt uncomfortable in and set out to be accepted in straight sports bars which I knew so well as a man. I was in my gender heaven when I worked my way into regular status in several of the venues I coveted. Once I was accepted by the staff, I could be accepted by their customers also and I thought I had it made. Sadly, by that time the one lesbian bar I used to go to and was accepted in closed its doors and that outlet for me was over.

These days, the closet thing that I have (so far) to an actual passport is my drivers license which has a “F” for female on it and my relocated copies of my name change documents I recently went with my wife Liz on the three-hour round-trip journey to my hometown to pick up. With all the turmoil caused by the idiots in Washington DC it seems in the future I may need a real passport to vote. So, I am getting ready for that if I need one.

Other than that, I am satisfied with the lifetime of progress I have made by having a suitable passport which allows me to live a public life mainly with the acceptance and help of the ciswomen around me. I was able to ignore the occasional hater like the pharmacist long ago when I started HRT who insisted in a crowded pharmacy in screaming loudly did, I know what the Estradiol medications would do to me. Not that she cared, but I promptly took my business elsewhere. It was no business of hers to judge me anyhow and try to out me to the world.

The passport I earned allowed me to open fantastic gender doors that I never thought I could do and the one I need to get will allow me to vote I am afraid here in backwards Ohio. I am not planning to ever travel outside of the country again in my life, so I won’t need a passport for that. Just the one I have already earned the hard way along my gender path.

I would like to take this opportunity to thank all of you who take the time to read along with my writing! It always means so much when you take the time to read and comment.

 

 

 

 

 

Friday, March 20, 2026

All Along, I was just Becoming Me

 

Image from Pea on UnSplash. 

As I always point out, becoming me was a very difficult concept to adjust to.

First of all, I needed to understand who the true me really was and work my way to the light out of my dark closet. Sadly, it took me decades to face the truth about who I really was. I was never the male I was seemingly born to be. I was born to be a feminine person, no matter what it took to get there. Which turned out to be the key term over the years, as I risked everything to discover who I truly was. As my male self was busy building a wall to his world by becoming successful in his job, my novice transgender self-needed to take a back seat and watch the clown show.

The problem was that often the clowns were not funny and just needed to stop before they caused complete damage to my life as I knew it. I was living the male dream in many ways with a good job, small family and a close knit group of friends and it was difficult to even thinking about giving it all up, but I did. Male privilege was very real to me and preparing to give it up was intimidating to say the least. Somehow, I needed to find the true me and quit being so self-destructive when my gender dysphoria hit me. In most cases, my morning mirror was to blame when I looked in it for the first time everyday and saw a woman lurking behind my male self-shaving.

I did not really begin to understand who I truly was, until I put my cross-dressing world behind me and started to explore the world as a transgender woman. Before I did though, I needed to draw an invisible line in the sand when I went out and see if I could cross it. When I did, I felt a deep sense of gender euphoria and wellness. When I did not I had to force myself to go back home, return to my cross-dresser drawing board and try again. Which I needed to do many times before I started to get it right. The important part is that no matter how down I felt on the days I was abused in public, there always seemed to be the slightest spark of hope which came from feeling good and natural as my feminine self. Suddenly, finding my true self did not seem to be so far away, if I could find the time out of my busy life to do it.

That is when I started to use every moment of my spare time in my transfeminine explorations of a terrifying yet exciting new world of cis women. Plus, if I was not exploring, I was busy thinking about it when I was working as a man. I wish I had back all the excess time I wasted in those days when I could have put the energy into my family, spouse or work. It would have made such a difference in my life. As it was, my life consisted of slowly sliding down a gender cliff. Not knowing what awaited me when I finally let go of my male self and headed towards a feminine world for once and for all. At that time, I did not realize I would have a team of gentle womanly hands to soften my fall. I still had a lot to learn about going behind the gender curtain.

Even though I was becoming accomplished as my authentic me, I found I still had many years ahead of me to continue my journey. I still had to round myself out as a new person very much from scratch. It was difficult to not automatically out my male self when I was talking to a new woman who turned out did not care about him anyhow. It was time to put him in the background and pick and choose the highlights of what benefitted me as a trans woman creating a new life. It was a different way to live and took a lot of getting adjusted to. Far beyond just worrying about my appearance and if I could use the right rest room. I needed to be on my toes all the time because just the wrong response about my past could give my whole male life away.

Once I separated the forest for the trees, I was allowed behind the gender curtain or rather followed my woman friends back there. For once, I was on the gender ride of my life. The same one I had paid so many dues over the years to be on, and once I got there, there was no way I wanted to give it up. So, as you can tell, I had a lot of help finding the real me. Women like Liz, Kim and Nikki showed me the way with their knowledge of playing in the girl’s sandbox. They all helped to bring out the true me in ways they never knew as my male past faded into my rearview mirror for good. It was the only time in my life that a mirror made the right call for me.

Needless to say, finding my true self after all those decades really opened the world up for me and made life so much more pleasant. Since I was not suffering from all the gender in-fighting I was going through, my mental health improved along with everything else. It did not hurt that the HRT gender affirming hormones I was on were making serious in-roads on how I felt internally as a trans woman and how I was viewed by the public. I felt better all around.

The only problem that I see now is how long it took me to come up with my own gender truth. If I had faced the facts long ago, I could have saved myself and the people I loved around me all the emotional stress I caused. Finding the true me cost me the most precious commodity I had. My time.

 

Wednesday, March 18, 2026

Time is All I Had

 

JJ Hart, Trans Wellness Outreach. 

Time is a fickle beast which sometimes comes back to help us, and other times it comes back to haunt us.

Depending on how far you are in your gender journey, perhaps you can remember your first experiences with the clothing of the gender you desired so much. Then again, I have heard from several readers who started their explorations at a much later age. Either way, time became a concrete reckoning to be dealt with. Mainly because time is a finite way of restricting all of us during our lives.

Since I have been fortunate to have been given a long/full life to live (I am seventy-six), I have seen my life come full circle in several areas. I have seen the joys of gender euphoria which kept me going when I hit the deep depression of stop signs and blind curves on my gender pathway. Through it all, I tried my best to learn from all my mistakes and successes. Little did I know I would live long enough to take advantage of everything I had learned. Or much of it as for much of my life I was always second guessing the decisions I was making. Did I make the right decision on taking a new job, or more importantly when I started to go out in public as a transgender woman and risking it all, was I doing the right thing.

What I did not take into consideration I had no real choice in what I was doing. From birth I was destined not to be the male person I was supposed to be. I had bigger and better things ahead of me if I broke the mold and was able to do it. I had the time to finally decide which path was right for me as I diligently explored the world of all the cisgender women around me. Then, a major roadblock arose when I was not allowed behind the gender curtain. The only time I was really getting out in public as a trans woman in hiding was at Halloween when nearly everyone knew me as a man. I badly needed other escape routes into the public eye if I was ever going to have the time to achieve my dream.

It turned out time was cheap in the middle years of my life as they turned out to be a blur. More and more, I began to sneak out of the house and explore the world around me as my transfeminine self. It was only then that I began to be allowed to be behind the gender curtain to see if life there what was really what I wanted. Spoiler alert, it was very much what I wanted as I even though many times I was terrified (yet excited) when I explored. I thought I had forever to do it and took my time trying to find new things to do as a transgender woman in a woman’s world. Which at times, still had me baffled about how it worked because I was still carrying around too much of my old male baggage. His expectations for the most part of how a woman acted in the world were formed from stereotypes he learned growing up as he watched women from afar and for the most part putting them up on a pedestal.

What I did not realize was my indecision to go all the way into the women’s world I was immersed in, was costing me years later on in life that I wanted back. Like everyone else I had assumptions, and mine were that I had plenty of time to research the difficult layered life of  and being a woman, when I simply did not which led me all the way to the age of sixty before I made the fateful decision to throw gender paranoia to the wind, pursue HRT, and change my life forever. While I still had the time because all the people I loved and respected in my life were rapidly passing away around me. The finality of death became a very real reality to me and if I was ever able to live my gender dream of living life as a woman, I had better do it while I still had the chance to enjoy it.

All I had was time was quickly fading away with all the people around me and I had very few people to make my own gender reveal to. For the most part, except for my brother and sister-in-law, my gender reveals were successful with most people telling me they were happy to see me happy. I guess one way to look at it is, if you wait long enough for your reveal you can be the last man standing becoming the last woman standing.

Going back to a theme which has popped up around here recently, if you are transgender you have given up all your rights to be a second-class citizen. And at least all you have going for you is that your journey has been an interesting one. From the earliest days of admiring yourself in the mirror all the way to earning your way behind the gender curtain, you have done it all.

Even though it maybe took a few years to do it, you know how difficult it has been to do it and every step needed to be carefully planned. One false move could send you back down your path and sometimes even worse than that. Ridicule by spouse, family and friends can happen at the same time your gender privileges were revoked. You feel helpless until you get your feet back on the ground to where you can continue and begin moving to a place where you always have known you should be.

For me, the time was now or never when I decided to live full-time, I had taken working on my feminine presentation, as well as being out in as many situations (good and bad) as I could. Anymore and I was just wasting my time and kidding myself if I did not pull the plug on my male life and get on with my future which I felt could be bright.

I saw the light at the end of the tunnel and for once it was not the train. I had paid my dues and was ready to live my life the way I wanted. Even though I ended up taking so long to do it, I was happy when I did. Age turned out to be more than a number for me, it turned out to be the magic time of my life.

Thanks to all of you for taking your precious time reading along!

 

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.

 

Tuesday, January 20, 2026

Her Way or the Highway

 

Image from Joshua Rondeau
on UnSplash. 

Very early on, it became evident to me that my feminine self was very demanding. Who knows, maybe she took after my mom who had to be strong in a very male dominated family.

Wherever it came from, I always felt a strong push from her to be let out into the world to live. Even so she would have to wait years and go through constant trials and tribulations to do it. The gender journey I was on proved to be much longer and challenging than either of her competing souls thought possible. Nearly a half a century of trying before I got it right.

To make matters worse, my male self never was one to give up easily and he fought every move intensely along the way. Making everything even worse was that he was fairly successful in carving out a life he never really wanted as a man. The more baggage he accumulated, the more difficult it became leaving it all behind in a male to female transition situation.

Even more stressful was the fear of the unknown which followed me everywhere. It started with the feelings of not knowing if I was a boy or a girl when I was growing up and continued onward from there. Seeking gender answers always took a lot of energy out of my life that I wished I could get back. Of course, that was impossible and I needed to learn to live with the way I was with my gender dysphoria until I hoped I could do something about it. What I did do was get out of my closet/mirror and began to see what the world would be like for a transgender woman like me. Would it be her way or the highway after all. Following a rough start with my public presentation, I lost nearly fifty pounds of weight and began to perfect my art of makeup. I put a tremendous amount of work into my feminine presentation, more than anything else I had ever done in my life.

As it turned out, all my effort was rewarded and my transfeminine self-began to emerge and live her life. The days of just going out to be alone in the world subsided as I was able to make new social contacts for the first time as a trans woman. For the first time in my life, the gender teeter-totter I was on began to favor my feminine side which proved to be a real problem for my male side who still was working fulltime in the world and bringing home a good income. I was actually ahead of my timetable in how I wanted to work out the gender issues in my life and increasingly it was becoming her way or the highway when it came to my life.

The pressure to change became enormous and wrecked my mental health leading me to alcohol abuse along with self-harm (suicide) attempts. I drove too fast and took too many chances hoping something would come along and put me out of my misery. Nothing ever did until I realized the answer was screaming at me all along. I should have never been born into the male world that I was and now would have to overcome the testosterone poisoned past I had lived to do something about it.

Her way became a real reality to me when my second wife passed away unexpectedly from a massive heart attack at the age of fifty. I was so disappointed that she never did anything about her health until it was too late that I never properly grieved the loss of someone I had been married to for twenty-five years. Instead, I turned to the waiting arms of my feminine self for comfort in my times of severe despair and loneliness. She was all I had as I sleepwalked through my life, and her highway began to look better and better. My new timetable of a possible jump across the gender border dramatically increased when suddenly the greatest barrier to stopping my leap had been taken away.

Before I knew it, the new highway I had dreamed about living on was upon me and it was fast and smooth since I had worked through most all of the bumps and potholes earlier than I had experimented. For once, I was not frustrated with all the time it took me to make my final gender transition decision. I always compared the road I was on to the Autobahns I drove when I was in Germany which were always well maintained and built for high speed. I even had to be careful that I was not going too fast as I had to figure out who was left to talk about my authentic self. My daughter came first, which went exceedingly well and then my brother which went exceedingly bad. Then I moved on to what was left of the very few friends I had left or just began to not see them anymore as I built my new life.

I am very glad now that it was her way or the highway in my life. She kept telling me it was the way life should have always been and the brief moments of life I saw which were so fluid and natural were only the beginning. Maybe I had been too cautious for my own good when I tried to take the back roads towards becoming a full-fledged transgender woman, but it was the only way I knew. Hiding who I was started so early in life, I never saw my way out of it for so many years until it was too late. I was stuck in a habit I could not get out of. Until I woke up to the fact that her way or the highway was a realistic path my life should take. I have enjoyed the highway ever since.

I was more like my mom than she ever knew.

 

Saturday, January 17, 2026

No One Way is Correct

 

Image from Gabor Kaputi
on UnSplash. 

Even though we transgender women and trans men often follow similar gender paths to get to our goals or dreams, it is still true that one path (the one you are on) is the only correct one. Plus, don’t forget there are so many side trips to take such as surgeries and hormones to help us along.

For example, I read about and hear from other transgender women who have elected to undergo major and costly gender surgeries (like Amber) which they deeply feel they need to feel whole, while me, on the other hand have decided to steer clear of any surgeries. Mainly because they don’t define me as a trans woman. I know what my brain is telling me gender-wise and just don’t need the corresponding equipment between my legs to improve my overall being. Although let me say I understand why somebody else would and if I was younger, I might have considered the surgical route. It just took me too long to figure out who the true me was.

Other than surgeries, I took the same path as many of you. I experimented with my mom’s clothes and makeup since I did not have any sisters, all the way to service in the military from those of you who are approximately the same age as I am such as Bobbie W. who even served on her version of the American Forces Radio and Television service as I did, although she was in the Navy. It amazes me how small the world has become because of the internet that many of us did not have in our formative cross-dressing years. Besides Bobbie, over the years, it has amazed me how similar some of our paths have been and it would not have surprised me if we had not met along the way. Except if you were like me, you were desperately attempting to hide your true self from everyone else in the world.

Then there were the evenings when I did see another transgender woman in one of the venues, I was a regular in, other than Racquel who was a trans friend of mine. One in particular was at a TGIF Fridays I went to quite a bit. I watched this well-dressed large woman step up to the bar and order a red wine, then before I could even attempt to introduce myself, she was gone and I never saw her again. So, on that occasion, I did have my path crossed by another transfeminine person since I could not attach a label to her such as a very accomplished cross dresser. Outside of a few “women” I saw shopping in the grocery store over the years, I learned how rare our tribe really is.

One of the reasons we are so rare is that all of those still in the closet due to their gender issues have not had the chance to be out and be counted. Mainly because of all the male baggage they have fears of losing. It is terrifying to think of losing baggage such as spouses, family, friends and jobs to name a few of the bigger ones. At least it was for me as I went through life frustrated with the amount of male baggage I was accumulating.

Even though, when I started blogging years ago to pay forward and help others similar to me in the closet, it occurred to me my plan had backfired to an extent, and I became a role model to some of my readers. Some even wrote in and called me some sort of a hero to them which humbled me because I never set out to do anything like that as I was just trying to live my life the best I could. Writing about my life was Now adays I keep trying to say I am no hero but merely someone who was terrified to leave her closet and live in the world as I knew it. Certainly not a hero by any sense of the word.

Recently, another point that I have been trying to make is there is no right way to achieve leaving your closet and living an authentic feminine life. Sure, it takes a lot of work and effort to achieve doing something the greatest majority of humans have never considered trying. Especially when we live in a negative atmosphere where a certain melon felon and his political party are trying to demonize us. Hopefully, that all will stop happening when the population finally tires of us and seizes the opportunity to vote on the real issues. Which makes it so important that even if you are in your closet, you vote your true conscience this coming midterm. So much for my political rant which is urging you all to get on the right gender path and stay there through the elections and beyond.

In the meantime, always hope for the best when you are out as your authentic transgender self. Your confidence will keep many of the middle of the road haters and bigots away because humans are like sharks, they sense blood in the water. How you get there is determined by many factors, but the main one is you can only gain confidence by going out into the world in your heels and doing it. Other than that, a disarming smile will take you a long way too. Keep in mind that most people don’t care about you, they are only concerned about themselves, and you will be ok.

As you do it, don’t worry about making the big mistake and you will be much freer to be you. You are on the right gender path because you are on it. Sure, it will have many curves and roadblocks but sometimes all of them make the journey much more worth it.

 

 

Friday, January 16, 2026

You being You or Playing up Being Different as a Transgender Woman

JJ Hart
At first glance, the statement of what makes you, you, seems like an easy one to answer. Especially if you are not transgender. Because you are in the majority and not perceived as being different.

For cisgender women or men, lives are set up to be lived in a certain pattern from birth till death. Using a baseball reference, life throws you a real curve ball when you are trans. Because you are different and often pay the price. The sad part is, for the longest time, we have such a hard time explaining to others our gender issues when we don’t understand them ourselves. In my case, it took me years to come to the conclusion I was not a man cross dressing as a woman, I was a woman cross dressing as a man, and I was not stuck with some sort of a weak excuse such as I was a woman stuck in a man’s body.

I grew up in a semi-dysfunctional family which valued being different. Until it infringed on what mom and dad thought was right. So having their oldest son want to be their daughter would never have been accepted. Or that was way too different for them to understand. I basically went on with my life knowing I was different and not knowing the information I needed to know if anyone else felt the same way.

Before I knew it, I was on the path to male privilege if I just did my best to earn it. The only problem was, I did not want to be on it. It was as if some invisible force was keeping me there against my will. Sometimes, it was easier not to expend my energy fighting my gender issues than to actually begin to leave my mirror and seek out attention in the world. It was only then did I begin to learn if my transgender dreams could ever become a reality or would forever remain a dream until I die. I just knew, both of my parents had lived relatively long lives so I should have time enough to do what I wanted.

In the meantime, I did what was expected of me. Such as reproducing an offspring daughter, earning two college degrees and serving my country in the military. I was not different than many of the other men around me, and life was a blur during this time. The worst part was, I was still not coming any closer to learning if I had any possibility of living my transgender dreams other than the occasional Halloween party. I was still paranoid that others around me would learn of my gender difference and often I would wake up in the morning wondering if I was a man or a woman. Which certainly set my day off on the wrong foot and I am not even adding in the vivid dreams I was having when I was a pretty woman. It would often take me hours to fully return to the disappointing relationship I had with my life as a man.

All the relationship did was continue to cement my unwanted claim of being a semi-successful man. I often wonder what I could have accomplished if I could have given my male self the full attention he sometimes deserved. Not the partial attention he received when I was inwardly thinking of what my life would be like if I could live it as a transfeminine person. It was as if something was telling me to put the brakes on acquiring any extra baggage as a man that I would have to get rid of when and if I was able to transition from male to female. It turned out, the learning curve I went through as a male helped me anyhow as a transwoman, because I was a stronger person. Which really came in handy on those lonely nights when I was out trying to be myself and not the self that made me different.

It was not until I made my gender differences an accepted part of me did I begin to experience success with finding new friends in the world. Since I could not deny what I was, why not utilize me to make me more attractive and I don’t mean in the physical sense. I was like other cisgender women who may not be the most attractive woman in the room but there was something about them which set them apart with their inner glow. I knew if I could harness my inner glow, I could go much farther in life and dispel for good that there was any dreaming left for me to do.

Literally without thinking about it I had crossed the line and transitioned again. I had went from being a serious cross dresser all the way to being a transgender woman and then to being just me. I had spent all the time around the cisgender women that I knew for them to accept me as an equal behind the gender curtain and I did not have to feel any different any longer. I did not have to seek out a mirror to reinforce in my mind who I was. I had sorted my male baggage and kept what I wanted and discarded the rest, so I was ready for my next big challenge which was being approved for gender affirming hormones or HRT. When my body took to them so naturally, I was able to take another big step towards doing away with what made me different from other ciswomen around me. In fact, I wondered what hormones some of the mean women I knew were on. They must have had an overdose of testosterone somehow in their diet.

While it is often difficult to emphasize the differences which make you different as a transgender woman or trans man in today's world, your differences can still be a positive influence when someone gets to know the real you.

 

  


Tuesday, January 13, 2026

Following your North Star

 

Image from Heidi Fin 
on UnSplash. 

I define my own personal “North Star” as the basic direction I had to go to be truthful to myself. Many times, I found how valuable my star was when I was lost in my own transgender woods and couldn’t see the forest for the trees.

Along my path, there were many times I lost sight of my North Star and needed to regain it before I could continue. As I did, I spent many a very dark night searching for my life’s truth of wanting to shed my male existence for a feminine one. I would not recommend what I went through to anyone because it was a long, lonely journey. Even still, I was fortunate in that I seemed to always have just the right amount of gender euphoria to propel me forward. It did not matter if I was just gazing at my image in the mirror and thinking I was a pretty girl, or shopping for groceries in our local market, something possibly positive came along for me to see my star and wondered if it was still within reach.

Sometimes, life was cruel and dealt me roadblocks which kept me from following my dreams such as the unplanned birth of my daughter. Which turned out to be the best thing that ever happened to me in my life. At the time of her birth in 1976 I was very much out of control and needed something to ground me. Much more than the excessive amount of alcohol I was drinking at the time. All the beer did was help me to lose sight of my North Star until I could regroup and find it. I did not learn until much later how alcohol was a depressant and did not mix well with my already depressed personality. Even though I was dazzled by the miracle of birth and the rapid growth into a little person by my daughter, life was still not good as I was sliding by in a haze most of the time and losing track once again of my North Star.

Somehow, I was able to emerge from this part of my life on my feet and ready to search for my truth again. But not enough to accept what I was finding. Even though that bright light of a transfeminine existence seemed close enough for me to reach out and grab it, I just kept denying its existence and taking the route of least resistance and was existing the best I could as a part-time cross-dresser.

When I changed professions and entered the professional restaurant business, I developed a love/hate relationship with what I was doing. I loved the extra money and advancement it brought me but hated the hours and extra pressure the job brought with it. I guess the good part also was that the new profession cleared the way for me to reset my existence and locate my North Star again.

Once I located my star, I had to finally face the reality of where it was leading me. Gone were the evenings or days of going out into the world thinking I was nothing more than an innocent man trying to look like a cisgender woman. In, was a new reality that I wanted much more than to look like a woman. I was a woman and needed to see if I could live my truth, I knew all along but refused to face. Even though I was terrified of doing it, I was advancing down my gender path, and the skies were clear so I could see my star and have an idea of where I wanted to go. Better yet, once I was passing my gender mileposts of very much socializing with cisgender women as an equal in my mind, there was no going back.

As I did it, I made certain I was trying to cover all my basics such as what I would do to live in a new transgender world I dreamed of and in reality, had never seen. Such as how I would support myself because I knew my current male job would never support a mid-gender stream male to female transition. At that time, I was still several years away from an early Social Security retirement, so I needed to be careful of what I decided to do. What I decided on was a low impact non pressure job I could work just to get by for the time I needed until I retired. I found that was impossible and I had to backtrack into fast food again and work a job I hated until I could quit and pursue my star.

By this time, I had paid a lot of dues playing in the girls’ sandbox and I had a very good idea of what I was facing if I went full time into a transgender world. I don’t think it is possible to ever capture your North Star, but I do think you can come close to living it. There are many paths to get there, and no one is right. Some transition on their own while others have help like I did. I was always a social critter, and my process happened to work for me but yours could be different. Plus, destiny can often alter your path to following your personal star. Do not panic until you find it again and revive your journey.

Remember, you are in uncharted gender territory, often without a compass. When it happens to you, you need to just hitch up your big girl panties and do it.

 

 

 

Monday, January 12, 2026

Who Won the War

 

I call this a fake image of me.
Pre Hormonal padding and hair.

Relax, this post is not another of my political rants!

As my life enters its senior stages, I have the luxury of looking back and wondering what the hell happened. Or, who won the gender battles and who ultimately won the war.

Even though the cards were stacked against her to start (and continued for years), my feminine side managed to hold her own enough to survive. Which was amazing when I looked at the beginnings of our life and what she had to put up with. To start with, I was born into a very male dominated family with a highly competitive nature to contend with, so I always had to be ready for a battle of some sort. For the longest time, I would have to accept defeat at the hands of my brother who was always the better athlete and I would quickly run and hide behind my dresses and makeup. When I did, my feelings were soothed and I was ready to try to compete and win.

One way or another, I found the only winning I was doing was when I was a girl in front of the mirror. The mirror kept telling me I was pretty, and that kept me going. I was far from winning any gender war within myself, but I was managing to tread water and stay afloat…barely because I had no where else to turn. My desire to be a girl was shutting me off from the world. What happened then was, I grew tired of just presenting in front of the mirror and wanted to test how well I did in front of the world. The whole scenario forced me into major battles once again.

This time, I found amazingly I could compete in the world as a transgender woman and I did not have to accept defeat every time I went out in public. Maybe I was finding my home gender after all. I think at this time too, I was battle hardened from all the defeats I had sustained in my male life, and it was easier for me to continue to move forward.

As life started to change, I wanted to explore the consequences of what I was doing more and more. Then my battles became more serious and far reaching which led my male self and my second wife to panic. They suddenly realized I was becoming a more accomplished trans woman and could possibly make it after all to my dream of living a full-time life as a transfeminine person. For her part, my wife kept telling me I made a terrible woman, which I learned later was true. Simply because I had not spent enough time behind the gender curtain to claim my womanhood, yet, but I was coming alarmingly close enough to find out what she was talking about to set her alarms off. And my male self, not to be outdone was doing his part too by relaying all the new jobs and moves he was making into a personal success story.

Between the two of them, they made formidable gender foes, and I needed to become better at exploring who I really was. Whenever I could get off work, I attended cross dresser-transgender mixers, both large and small to determine if I could do what I saw other successful people living on the gender frontier. By doing so I could see my major battle lines being drawn up ahead, and I was like a runaway train headed for them. Major decisions were coming up in my life if I like them or not because I had spent too much time and effort in my explorations to turn tail and run again. I had nowhere to go this time because I had blocked all my exits. All my skirts, dresses, heels and makeup were ready for action.

By this time, my male self was in pure panic mode knowing that his ace card of military service had backfired on him. He thought somehow an ultra-macho experience that Army infantry basic training would make me more of a man when in fact, the whole experience made me a stronger person and believer in myself. When push came to shove and the times were darkest, I could make a decision and live with it. Even if was the decision that would effectively be his final battle and win the war for his feminine counterpart.

Also, I was coming up with a clearer idea of why I had struggled with who I truly was for all those years. I had blindly followed the idea that I was a man cross dressing as a parttime woman when, in fact, I was a woman cross dressing as a parttime man who happened to be married to a strong ciswoman. Plus, he was the primary wage earner in the family. Covering all those gender tracks was exceedingly difficult and put a tremendous strain on his mental health but he kept on fighting the gender battles against all odds. Out of some misguided idea that he had to. It was such a relief when he surrendered and gave up the remainder of his clothes to a local thrift store. The only thing he saved was his Army uniform which had taught me so much about life and winning,

When he realized he had lost, there was no time for wild celebrations. Only time for serious contemplation of what was next and how my victorious trans woman would react. It turned out, she took her win quietly and set out to build a life she always knew was possible. A life which was enhanced even further when she was approved for therapy and HRT through the Veterans Administration. Finally, she had the help she needed to match her internal needs with her external appearance. Which is the subject for another blog post altogether.

Regardless, victory was sweet as my old male self-faded into the past. She lost many battles, but ultimately won the war.

 


Monday, January 5, 2026

What was Meant to be, Will Be

 

JJ Hart doing Trans Outreach program.

The longer I lived and experienced a feminine based experience, the more I realized my life was turning into what I always expected it to be.

Yesterday, I spoke about the “aha” moment I had when I transitioned from being a serious cross dresser to living as a novice transgender woman. Even though I was scared to death to do it, after the experience was over, I felt so extremely natural I knew my life would never be the same again. In other words, my new life as a trans woman was always meant to be and felt like it. Over the years of thinking about my new life and seeking answers, the only excuse I could find was that my mom had several still births before me and resorted to the new (at the time) DES drug which was prescribed to help problem pregnancies. DES was known to flood the uterus with estrogen to help the birth mother and was “rumored” to be a cause of gender dysphoria in children later in life. But all of that was just a theory.

I was left to be on my own forever wondering why I felt so natural when I tried to cross that gender border into womanhood. As my mind wandered into all the different scenarios I could have been confronted with, nothing was ever placed in concrete. As much as I disliked competing in the male culture, still I was relatively successful in doing it and had managed to carve out a life in a gender I wanted nothing to do with. So, it was not that.

The older I became, and the more experience I forced my way into, the more I felt living in a cisgender women’s world was the place for me. If I could make it happen. First, I needed to get past my appearance paranoia/obsession and open my eyes to what was really going on around me in the world when I was exploring it as a transfeminine person. I was naïve in my gender thinking about women as a whole and tended to put them all up on a pedestal. Which I found out was completely wrong.  Quickly I learned that although women operate on different wave lengths as men, almost all the basics were still there for me to learn. At that point, I had plenty of other “aha” moments when I realized the intricacies of how the two main binary genders operated on a daily basis.

I learned too that there were simply some things I could not do by simply observing the ciswomen around me, I needed to interact with them before they would let their guard down and let me see their true selves. The more immersed I became in their culture, the more I wanted to be and again for the first time in my life I began to feel natural in my own skin and felt like my life was meant to be.

I found I was a quick learner when it came to being a quality trans woman and not a standoffish bitchy one. I learned I could make friends easily with most all other women and the rest did not matter anyhow.  Most of them were evil in their own ways, and I did not need their problems if I was ever going to get where I was trying to be. I had bigger issues to face such as how I could learn to communicate effectively as my new, out, authentic self who I learned could not wait for her chance in the real world. She knew exactly who she wanted to be if she ever got the chance. All of a sudden, I was having fun in my life again and the male to female transition problems I was experiencing began to fade into my past. Even though I carried an immense amount of baggage with me from my male life, I was still able to pick and choose what I always wanted to remember from the male world I came from.

If I paid attention to the knowledge, I had gained from having experience on both sides of the gender border, it gave me a real head start on how to conduct myself around men and women. I even was asked questions from women about how to deal with their man and how he may be feeling and I was very flattered to have tried to help.

As I always bring up, my biggest problem with all of my gender transition was how long it took me to do it. Waiting until the coast was clear and when I was nearly sixty years old took away valuable years of my feminine life which I could have experienced more of the world. If I had it all to do over again, I would have been braver and known the huge gender move I was about to make was always meant to be, so just do it. Pull the bandage off my old male life and get on to the future.

Maybe, if I ever have a tombstone, I can have it engraved with the simple words, “She was always meant to be.”

Monday, December 29, 2025

Dark Side of the Gender Moon

 

Image from Maria Kovalets
on UnSplash.

Exploring the dark side of the gender moon for me meant a lot of work.

I equate it to the first times I could experience wearing my own hair in public without the help of a wig of any sort. The satisfying part was that I did not have to worry about the style and color of the wig I selected and how hot it was going to be on my head during the warm summer months when my makeup threatened to melt off of me as soon as I put it on. On the other hand, I needed to master the art of looking at the back of my head in a mirror to see how my new hair looked. I began to think of it as the dark side of the moon. No longer would I have the ease of styling a wig on a wig stand in the back so I knew it would look good on my head.  

Also, not wearing wigs anymore opened up a new wonderful world for me of visiting women’s beauty salons. I will forever remember the first time my daughter gifted me a visit to her upscale salon/spa. I was just coming out of my gender shell and the whole prospect of having my hair done terrified me, but I hitched up my big girl panties and said yes. Little did I know what was instore for me. Thanks to my daughter, first of all I needed to walk through seemingly an endless gauntlet of women in chairs in various stages of having their hair done. I gathered up all of my courage and tried to walk as femininely as I could until I met my new stylist.

The first of many decisions I needed to make was what color I wanted my new hair to be. As my daughter and stylist hovered over me with what seemed like an endless set of examples to choose from, I chose a red/blond streaked shade and then had to pick how long or short I wanted my new hairstyle to be. I had no idea choosing the dark side of my gender moon would be this difficult. Quickly though, I chose an off the shoulder look which maintained most of the hair I had grown. All too soon, my appointment was over and I was spun around in the chair to see the new me and I loved her! All the years of frustration of not being able to afford quality wigs or take care of them faded away and the best part was I had been blessed with visits to women’s spaces such as beauty salons and I walked away from the experience knowing why so many ciswomen value their beauty visits to the hair salon the way they do. The day following my first visit to a serious upscale salon, I thought I had been exposed to so much estrogen, I could skip my daily dosage.

I guess you could say, having my hair done was just the first of dark side of the moon gender moments in my transfeminine life. When you add in all my other journeys into women only spaces, there were plenty of other experiences to mention. Like the one I rarely recall when I was invited to go out and party with a few of the servers, I met at one of the regular sports bars I hung out at. Like the experiences of having my hair done, I had been out several times on girls’ nights out invitations in my past, but never like this one. These women were all much younger and prettier than I was so I wondered how I would fit in. The answer was that even though they were all nice to me, I did not really fit in at all. The other women were too busy getting hit on by guys so there was little time for other socializing. I quietly sipped my drinks and pleasantly left with the group when most of them did. More lessons learned.

As far as any major male to female feminization process goes, there are inherent risks to be taken when you go through the process of losing your male privileges and discovering your new feminine ones. I know in my case, I was starting to know I was successful as a transgender woman when I began to be treated in certain ways. Such as when men in particular began to question my intelligence as I talked to them. I thought to myself, did I treat women this way?  I was definitely on the dark side of my gender moon as I explored a new world.

As you begin to explore your new world, there is plenty to do such as gathering the courage to use the women’s rest room. Which is a natural need when you are out and about for any length of time as your new trans woman self. Not any of the rightwing paranoia being spewed by the bigots saying we are men using the women’s room.

Actually, exploring the dark side of your gender moon can be an exciting experience and one you have waited your whole life to take. Take it far past just styling your own hair and/or wig and expand it all the way to discovering a new world you wanted to live in so badly. Just try to enjoy the discoveries you make and any aha moments you live through. There is so much to be learned when you jump the binary gender border to live on the other side. All the work I put in was certainly worth it.

 

 

 

 

 

 

 

Monday, December 15, 2025

More Downs than Ups on the Gender Roller Coaster

 

Image from Pietra K. 
from UnSplash.

The gender rollercoaster of life was very real to me.

That is the reason I attempt to mention all of the ups and downs I have experienced over the years as I battled gender dysphoria. For me, the trip up the coaster was not often worth the trip down as my depression set in. Until I received the proper care for my depression, I would often not want to even get out of bed for days at a time. Of course, I could not do that, and life would have to go on. That life included an increasing interest in cross-dressing. When I was on an upswing, life was better and I thought I was even making strides towards possibly living my future dream of living in and competing with a world of cisgender women. All of which had a very large headstart on me towards possibly achieving their womanhood before I could.

All this turmoil sent me down the rollercoaster of life and right back to where I started from…deeply frustrated. It was not until I began to leave my closet or shell and explore the world, did I begin to experience any relief. In the world, I discovered that not everyone noticed me and it was true what my second wife told me that it was not all about me. I was relieved when I learned that most of the world was just living life on their own terms and outside of few haters, I could live my life too. It was when I discovered that I was able to ride the level part of my dysphoric roller coaster, for a while.  

It never failed that when I started to come off the flat spot of my coaster, I needed to fight my depression again. Nothing I was doing was good enough as a man or a woman. I was so involved in wanting a transfeminine future, I could not maintain a good solid relationship with my long term (25 years) wife. The only things I was doing was keeping my head above water at work as I carved out the beginnings of a new transgender life. While I did all of this, I managed to make myself miserable as well as those around me. If I could not live with myself, how could anyone else, was my main thought pattern as I rode the roller coaster of life. All I knew was, I needed to hang on tightly for the ride ahead.

Of course, you all know I did manage to hang on, or I would not be here writing this today. Many times, it was because deep down inside I had this unmistakable idea of what I was doing was right. I had waited a long time in line to ride this gender rollercoaster, and I was not ever going to give up my spot. Once I came to this conclusion, I was able to stand in line with other ciswomen and not be so intimidated. And they were less intimidated by me and the rollercoaster hit another exhilarating turn as it headed into a tunnel. This time though, coming out of the dark did not mean I was heading into so much depression. Still, I knew I had a lot of work to do before I could reach my goal or dreams of living a fulltime transgender life.

Every time I thought I had finished a ride on the roller coaster, I found I needed to turn right around and get right on. A ciswoman’s life was so much more complicated than I had ever planned for, there were more challenges ahead. I still had key decisions to make concerning how I was going to live my new life. Such as how I was going to support myself and what was I going to do about telling my remaining family and friends that all along I had been living a lie. Last but not least, I would take the major step of seeking out approval to begin HRT or gender affirming hormones.

Amazingly, each time I jumped on the roller coaster, my rides became shorter and less eventful. I had taken the time and effort to set myself up as a regular in certain venues I went to all the time, so I did not have to go out just to be alone. I was always a social animal as a man and now I was too in my new exciting feminine world. Most importantly, I was able to develop a small circle of ciswomen friends who unknowingly boarded the coaster with me. They showed me the final steps I would have to take to get off my lifetime ride permanently. Maybe the best part was they never knew what they did for me. Eventually, what came out of it all was my marriage to my third wife Liz. A lesbian ciswoman who was instrumental in kicking me off my roller coaster permanently.

Even though I was ultimately successful in reaching my transgender dreams, I am not so sure I would recommend how I did it to anyone. I took too many chances and consumed too much alcohol along the way. Often, I used alcohol to give me a false sense of security when I was riding a scary coaster. Those were the days when I had to internalize my emotions and fear and “be a man.”

Finally, and thankfully, the world around me changed and I stepped down off my roller coasters all the way to less intimidating merry go rounds. Even they didn’t last as I decided to leave the gender amusement park altogether. Truthfully, I never got much of anything which was amusing anyway, and on some occasions, bigots and haters even put me into the freak category. Sadly, I never won any prizes for the most rides on a roller coaster or had a chance to reach for the ring on the merry go round. I was at least a survivor. I did not have to be a man at all.

Who Got in Your Way

  Image from UnSplash.  Perhaps there was that special person or persons who stood in the way of you going along your formative gender path....