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

Wednesday, August 5, 2026

The Vampires Approved Me

 

Image from Mike Lloyd 
on Unsplash. 

Yesterday I needed to visit the Veterans Administration vampires to have my blood labs done. Fortunately, I could just go to my local branch office to get them done and not have to go to the congested mess which is the downtown Cincinnati VA Hospital.

I chose yesterday to go because it was a beautiful early August day here in Ohio with coolish temperatures and bright sunshine for the relatively short drive I needed to make to get there. For the occasion, I decided to wear my new Libra themed tank top with leggings and my new tennis shoes. After a close shave, a lite coating of makeup, and lipstick, I brushed out my long hair and was ready to go. Actually, compared to the few other ciswomen I encounter at the VA, I was nicely dressed and ready to face the world as a transgender woman.

When I arrived at the VA, it was a very uneventful visit as no one seemed to notice me for anything other than who I was, an elderly woman who did not have to wait long to be seen and have my blood drawn. Since I was emboldened by the experience, I decided to stop by my wife’s Liz and I’s favorite coffee shop to pick up some breakfast sandwiches and coffee. My morning continued to go good as their drive-through was nearly empty and I was greeted cheerfully. Before I knew it, I had my order and was headed home. It is the coffee shop we go to which has the big LGBTQ flag on the wall, so we always try to support it.

The best part was that only a couple of hours later, the doctor who wanted the bloodwork done received the results and everything came back OK. Which means I am clear with the vampires until I have my Hematologist visit downtown this fall. It is important mainly because it is when I have my Estradiol levels checked. It is certainly no fun going downtown and having to find a parking place and walking but there is nothing I can do about it.

In the meantime, I took my brief moment of gender euphoria and enjoyed it for what it was…a brief moment to be the person I always wanted to be. I was just being me basically for the first time in my life. Now all I need to do is string together more of these moments to make them my reality.

Just a short post today to let you know where I have been and I will be back with you with a longer post tomorrow.

Monday, August 3, 2026

Letting Tomorrow take care Of Itself as a Transgender Woman

 

Image from Valentina Conde
on UnSplash.

Since I was always a person who had a difficult time living in the present, tomorrow always loomed large in my mind.

I think it all started when I began to rebel against the masculine world I was being forced to live in and always thought tomorrow could be better. It turned out that all the wishing and hoping I did for a better tomorrow turned out to be wasted time and energy, I finally needed to take matters into my own hands, stay in the present and do something about me being stuck in my dark, restrictive, gender closet with only a mirror to help me.

It took a quantum shift of thinking on my part to even thinking about how I could change my life. First of all, it was nearly impossible for me to quit daydreaming about the next time I could cross-dress in my mom’s clothes and try on her makeup. Any time I was not actively being engaged in male activities, I was hoping that soon I would be glimpsing a view of me in a favorite miniskirt I had found by accident at school outside of the girl’s locker room. If the girl who left it behind did not want it, I certainly did before a janitor found it and threw it in the trash. I was overjoyed to add it to my small but growing feminine wardrobe at home. Hopefully away from any prying eyes who may find it.

Somehow, I managed to hide my “treasures” away and add to them with my own meager funds I had earned from my rural newspaper route and from chores I was doing around the house. I will never forget the excitement I felt when I found a pair of women’s shoes that fit me in the department store where I was sneaking in to buy my makeup and panty hose. The whole process made me feel good because for once I was not relying on anyone else to help my cross-dressing along. It all was just me, and I was in the present doing it.

As I moved along in years and experience, I increasingly wanted to break out of my dark closet to see if I could exist in the world, in the present for once as the person I was coming to believe could be my true self. I learned the hard way that the public would not be as forgiving as much as my mirror was as I was treated quite rudely the first several times I went out. Even in places I should have had no problems in such as the big shopping malls back when they were popular. I couldn’t seem to dodge the giggles and stares I got from the teen girls before I learned to stay in the present, be who I was and begin to blend in with the group of other ciswomen in the mall. I learned the hard way to dress for them and not rely on some sort of trashy look that appealed to men. Which was getting me clocked as a man in drag every time.

All this new reality was teaching me I could indeed enjoy the present when I was out in the world. But not enough to keep me there when I was back in my unwanted male world. I have always wished I could get back just a portion of the time I wasted daydreaming of how it would be if I was the only ciswoman in a business meeting I was in. I know I could have been more effective…if I could have been accepted. Which I would not discover how difficult that would be until I got out further in the world as a transgender woman. I will always remember how I was shunned by a small group of men I somehow became involved in a discussion with when I first came out of my shell. Quickly I discovered, as a woman among cismen, I would have to fight for my right to be heard on an equal basis.

The more I was out in the world, the more I was forced to stay in the present. If I did not, I could find myself slipping back into old male habits which would give my past away much sooner. Such as not employing my old “stay away” male scowl and replacing it with a much more pleasant feminine look which said I was happy to be here. Which got me by. Other areas of just being a woman I needed to concentrate on was how I moved around in the world when I was still trying to juggle being in both worlds of male and female. One day I needed to be feminine, and the next masculine ended up taking a real toll on my mental health as I did not know somedays what present I was supposed to be in.

Plus, the one aspect of being in the now as a transgender woman was the one I always mention, communication. As I was blissfully (sometimes) going along my gender path, suddenly more and more ciswomen wanted to know about me and were curious why I would be in their world. I was totally blindsided when I needed to start and participate in entire conversations with other women who appeared in my world. I discovered communication went way past just how my voice sounded into exactly what I was saying and how fast I could pick up two uniquely feminine communication aspects. Non-verbal communication and passive aggressive behavior. The normal ciswomen who interacted with me ended up using all their skills to size me up and often it turned into quite the contest that I needed to stay on my toes to get through.

Eventually, surviving all the gender wars I went through, made me a better, more well-rounded trans woman who could hold her own in the world. Primarily because I had built up the confidence to do it, and it became my number one accessory. So, what if my makeup or walk wasn’t exactly correct, I knew who I was and it showed. There was no blood in my water for the human sharks around me to come after.

All those years of trying to get into my present and stay there finally paid off for me, but only after I had paid all my dues.

 

 

 

 

 

Sunday, August 2, 2026

Violating Gender Boundaries

 

JJ Hart. Pushing my gender\
boundaries. 

Very early in life I learned that violating gender boundaries could result in severe trouble.

It was obvious to me that the male dominated family I was born into would ever accept a son who wanted to be a daughter. So, I had no choice but to turn inward with my developing feminine senses in the male world I was trying to be a part of. I was born way too early to take advantage of the forthcoming online information world with the advent of computers and social media. Again, I was trapped into trying to cross-dress my feelings away anytime I had the chance.

The other main problem I had was that the gender boundaries were so rigid and demanding I could not see any way out of my dark, lonely gender closet. I lived in a rural area with mostly boys and no girls to have a point of reference from. I only remember one occasion when the only girl in the neighborhood was persuaded by a couple of the boys to show her naked genitals to the group, and I was not excited but embarrassed for her at the time. Just another example of how my sexuality was developing away from the “normal” male’s. I had no need to see her private parts and wondered why I was so different. Little did I know, it was just the beginning of challenging my gender boundaries during my life.

As far as the rest of my life went, I wasn’t much of a challenger of anything. It wasn’t until I reached my college years and was drafted into the military during the Vietnam War, did I begin to challenge the system. At the same time, I was starting to challenge the war and the politics around it, I was pushing my cross-dressing boundaries by starting to leave my house more dressed as the person I wanted to see if I could become. I even made what turned out to be a huge mistake by coming out to my fiancĂ© as a transvestite or cross-dresser back in those days. I say huge mistake because she wanted me to tell the draft board I was gay to stay out of the military service. Even then, I knew a lot about myself and did not have to push my gender boundaries so far to lie and tell someone I was gay. As a side note, then and now I did not have anything against the gay community, but I just knew there was a real difference between them and me.

Of course, the military stopped any gender challenging I was thinking of doing dead in its tracks for nearly three years of my young life. The only challenge I could do was mental in nature as I imagined how life could be better for me as a transfeminine person when I was discharged from the Army. Even then, I was restricted in my gender thinking to the reality in life. What I almost did was send a letter (remember them?) to my future first wife explaining it maybe a transwoman picking her up at the airport when she arrived for the first time. She was in the Army too and was discharged about nine months after I was.

Little did I know, if I had decided to test my gender boundaries then it may have been one of the better times to do it because I did not have the chance to build up all the troublesome male baggage I would acquire later in life. On the plus side, I had a very new car that I had shipped home from Germany, my stereo equipment and a sizeable bank account to start a new life with. On the negative side, I thought I had a good chance of losing my family, friends and job if I started all over as a woman.

Long story short, I did not have the courage to push my gender boundaries any further than they were at the time. Except for a few Halloween adventures, and the occasional night out, my life as a trans woman was mundane. It was not until I could not take it any longer the annual yearly adventures at Halloween, did I start to really push my luck by going out more often. My early explorations were rough to say the least until I settled down and learn how to blend in with the ciswomen who I found really ran the world I wanted to be a part of.

As the world let me in as a transgender woman and/or I finally learned the truth of who I was, I kicked and pushed until my gender boundaries came down. It was like the steep slope I write about as I slid down trying my best to hold on to what was left of my old male life but failing miserably. As I continued to gain my new feminine ground behind the gender curtain, which was hidden from me for so long, I had pushed by gender boundary so far, I was too far gone. I was no longer afraid of the fall and knew I was too far gone to ever go back to being my old male self.

From then on, gender boundaries did not mean much to me except from my former history as a man, I could see both sides of the border from where I lived as a trans woman. Leaving the man’s club scared almost all of the cismen away but attracted as many of the ciswomen that I needed to set up a new boundary. The new boundary was one which validated myself as a woman for the first time in my life and it seemed I was learning daily how to adjust to my new situation.

From that point forward, I changed my legal name and became extra serious about my physical and mental well being by being approved for HRT or gender affirming hormones. It just seemed by that time, I was just doing what came natural in solidifying my new gender boundaries. Sure, they were all big moves in my life, but good ones that I had always dreamed of making.

As always. Thanks to all of you who read along with my lifetime worth of experiences. Your responses and comments make it so worthwhile for me!

 

 

 

 

Thursday, July 30, 2026

How Much Courage did it Take You?

 

Image from Jon Tyson
on UnSplash.

Often, I hear the words courage or bravery kicked around when it came to mentioning someone coming out of their closet into the real world.

In my case, I would have to replace either of the words with just being afraid of what would happen if I did not pursue my gender dreams of living as a transgender woman. Mainly because I was so self-destructive when it came to causing self-harm to my unwanted male self. I drove too fast and recklessly, drank way too much and even tried to actively kill myself once because of my gender dysphoria.

Especially after I had the rare chance to talk to my friends who survived brutal combat in the Vietnam War, I reserved the terms brave and courage for them. Because in many ways, I was just doing what came naturally when I cross-dressed in front of the mirror at home. It turned out staying in my own little feminine world was very easy until I began to want to see if I could stretch my luck and actually leave the house looking as close as I thought I could to a pretty girl. The only reality I did know was I was scared to death.

Little by little, my fear began to subside, and I wanted to expand my explorations to bigger and better venues such as the malls which were just beginning to come into their own back in those days. Still. I didn’t think I was brave enough to do it. Or was I just being stupid by risking losing everything that I worked so hard to build up in my male life. My ego dictated that I did not dwell on the stupid aspect of trying to femininize my testosterone poisoned body. I just wanted to blend in with the rest of the ciswomen I envied so much. As much as I was being abused by certain segments of the public, I began to use another term to describe myself and that was stubborn. In fact, I think that would be a great title to a new PBS show (Public Broadcasting System) called the “Stubborn Cross-dresser.”

As I continued on my gender path towards finally being allowed to join the girls’ club, my stubbornness in trying new things was both a blessing and a curse. A prime example was when I was trying to hang on to my teen fashion sense way too long. It was a curse, and my blessing came along when I became stubborn enough to keep going back to my cross-dressing drawing board until I fixed the problem and became able to blend in better with the women, I wanted to notice me. After the death of my second wife of twenty-five years, I was desperately lonely and did not want to attempt to build another life as a man when the possibility of building one as a trans woman was right in front of me. If I was brave enough to take advantage of a life I had only dreamed of. Was I going to take the easy way out and try to be a man again or build upon what I had learned as a novice transgender woman became my major question to answer.

Finally, I needed to “man-up” and be a woman as my second wife used to tell me and when I had the courage to do it, I felt a deep happiness in life I never had before. In fact the feminine privilege I found to be the most pleasant was the fact that I was allowed the opportunity to be happy. For the first time in my life, I was able to align my sun, moon, and stars so I did not have to fight a gender battle on two fronts which kept me unhappy and on edge. I positively loved my new life along with my first chance ever to just be happy with what I had.

If you are one of the many gender conflicted individuals trying to decide if and when you will make the ultimate choice to go for the gender border as a trans woman or trans man, my only advice must be, look deeply inside yourself for your answer. Your answer is there If you are stubborn enough to find it. Life is like an old merry-go-round and often it is difficult to slow it down to see the real world spinning in front of you. And if destiny puts you on the right path to do it, you can discover a group of well-meaning friends (ciswomen or men for you trans men) who can help you along. Making you a better person than you ever thought you could be. I would never have thought that the gender dysphoria that I felt would end up causing me so many problems in my life.

Before your life ends and you move on to whatever other place of existence you believe in, you have the basic right to be happy. You can deal in semantics and call your gender journey as being brave or having courage all you want but the end result is you being the natural person who you always should have been.

Somehow, we have been chosen to lead a different life’s journey than most of the others in the human race. Call us brave or courageous if you want but as a tribe, we are doing what we were always been destined to do. It is just too bad we are met with such resistance by haters in the world. As well as the gatekeepers who want to keep us away from our chosen genders. When I speak about gatekeepers, immediately radical feminist TERFs come to mind who have no business in ours.

Best wishes on your successful gender journey and summoning enough courage (if you want to call it that) to get out into the world and live your best life.

Thanks again to all of you who join me in my experiences, and I hope we can all learn from them. I apologize to all of you who have commented. I am a little behind getting back to you because of technical problems.

 

 

 

 

 

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.

 

Monday, July 27, 2026

Staying in the Present as a Trans Woman

JJ Hart at Trans Ohio.
Staying in the present has always been a difficult task for me. Perhaps it all started when I was a very young gender distracted person and could not seem to stop daydreaming about being a pretty girl. The daydreams were nearly always a great escape from my everyday boring male world where I was always competing for the same rights to be recognized at all.

Overtime, I was rarely successful as a boy and just put in the amount of effort to get by. The only thing I was moderately successful on was hustling on my newspaper route and doing extra chores around the house to make extra money. Which in turn, I used to buy my own feminine articles such as makeup, and pantyhose for when I was able to shave my legs. Overall, my plan worked and eventually I was able to build up my own collection of cross-dressing essentials. As I discovered I could get away with shopping at a couple of small local department stores for everything I needed to shatter my dream of doing it and stepping into my own form of reality.

The older I got, the more I did not grow out of my cross-dressing gender desires. In fact, I grew into them when the world became more and more accessible to me. I was building an increasing sense of confidence in my new self and going out briefly into the world as a novice when the Vietnam War and the persistent military draft caught up with me. For the first time in my life, I could not daydream of something as major as a war going away. It was as real as my draft card. Which I resented having because none of the ciswomen around me needed one. Why should I be forced into an unfair war when they were not was what fueled my resentment. A resentment which just made me feel worse as I wasted my time worrying about the war which was staring at me in the face.

To make matters even worse was the fact my fiancé who knew I was a cross-dresser told me we would break up unless I told the draft board I was gay. Which, there was no way that was going to happen, so we did end our relationship just before I headed out to Ft. Knox, Kentucky for Army basic infantry training. Even though I fought military service as long as I could, in many ways it did me good because I needed to stay in the present most of the time when I was going through basic. If I was not, I would feel the wrath of the drill sergeants which was not a place I wanted to be. I guess you could say, I was going through a whole different basic training by teaching me to stay in the present.

After I had served my time, I tried my best to pick up where I left off by trying to join the world as a transgender woman. A new life was just starting to come to me with the realization I was much more than a part-time cross-dresser and needed to experience more of a woman’s life to satisfy me. Change was upon me with the birth of my daughter and a new wonderful world of mall shopping experiences to explore. After a rough start, I was able to present well enough to enjoy being out in the world. In other words, the teenaged girls who made me a target suddenly left me alone. The rest of the mall time was easy because I discovered that my money was green and that was more important to the store clerks who waited on me than my potential gender.

Eventually, more reality than daydreaming set in with my life. I was becoming so successful in carving out a new transfeminine life I knew that I had gone too far to ever turn around on my gender path to ever go back. Sure, I was scared but a voice in the back of my head kept telling me this was so natural that my new world deserved to be the reality I always sought and I needed to stay in the present to do it.

I discovered as a transgender woman, the present was a very great place to be. For once, I had access to the gender I wanted to be with which were all the ciswomen who showed interest in what I was trying to do in their world. I had always had a difficult time making friends with other men when I was acting like one and I finally figured out why…I should not have been in the boys’ club to begin with. Living a lie was a total mistake which should never have happened. I was not interested in a club where I never belonged, and that was OK.

Old habits are hard to break, and maybe even more so for transgender women and transgender men. Primarily because we have to decide what baggage we are taking with us or leaving behind as we journey along our gender journey paths. Bring too much, and you can’t carry it all or don’t bring enough and end up losing all of your building blocks you need for a new life are all things to consider. And most of all, it is important you stay in the present, so you don’t forget where and who you are and slide back into your old self. It is frustrating when something as small as the look on your face can destroy all that you have worked so hard to perfect. That old male “stay away” scowl may have worked in your old world but in your present one, it certainly doesn’t.

It was difficult for me to find my present. Determine if it was the right choice and then stick with it. As I went through my male to female feminization efforts, I needed to finally decide on a wig to wear on a regular basis and quit looking for the miracle wig which would instantly make me attractive. Why? Because people were starting to recognize me as a person, and I needed to build on that. Instead of just carving a new person, I was blasting one and having the time of my life doing it.

I just wish I could have stayed in the present earlier in my life, which I know would have given a better understanding of who I was at the time. I almost did more after I served my time in the Army, but it was in the mid 1970’s and the world was different, and I did not have the courage to do it. Instead, I played my status-quo cards and thought I could help my life along by just cross-dressing. By doing so, I just ended up losing so much of my life when I ignored living in the present. One way or another, it is much too late to cry over time that was wasted and remember the good time when I discovered my present and lived it.

Thanks for reading along with me. Hopefully my insights can help you with yours and comments are appreciated.

 

 

 

 

  


Wednesday, July 22, 2026

Imagine your Dream

 

JJ Hart on left, Pic Nicking with Liz on right.

Yesterday, I went with my wife Liz to her appointment with her “vampires” to have her blood labs done.

When I did, I had a chance to sit around and watch the other ciswomen in the waiting room and see if they were watching me at all. They were not and went on as they all were too busy on their cell phones to even come close to noticing the trans woman in the room. Instead of me joining them on my phone, I thought back to a time when just going to a doctor’s appointment was not such an easy task because of all the gender paranoia I was feeling. A gigantic case of impostor syndrome to be sure.

Early in life, as I imagined my dream of living a transfeminine life, I never factored in all the mundane things a woman does during her life. I was too busy being the “Pretty, pretty princess” as my second wife always called me. And to her I would have been about the furthest thing away from being any sort of a princess in the waiting room that there was. I would have never dreamed I would have been seen in public without being dressed from head to toe as close to an attractive woman than I could.

Nobody but me cared that my dream had changed and I was alright in jeans, t-shirt and light makeup to be seen anywhere in public. I was just another person with very long hair and breasts in a doctor's office. Had I become lazy in my old age or just dressing to blend in with a public who increasingly does not seem to care about feminine appearance.

Maybe I was just being selfish in that I was OK with just dressing to blend in with the rest of the world around me who were too busy on their cell phones to notice me at all. Is that what my dream had become? Perhaps I am being too demanding in my dream that I wanted it to turn out a certain way. And, I certainly did not set out to be some sort of a leader in the ciswomen’s fashion world, I had had enough pressure on me to lead for a lifetime when I was living in a cisman’s world. I just wanted to fade into a new world and learn it totally. As I come closer to the age of seventy-seven, I think I can safely say I have reached that goal I set so long ago.

Coming up Saturday, my daughter and son-in-law are making the trip down to Cincinnati from Dayton, Ohio to bring me a scrap book of family pictures and have breakfast with Liz and I. For that visit, I will certainly attempt to dress up more for the occasion, which will include a new top I bought, along with new flats and even tying my long, long hair back also. She is the only accepting blood relation I have left, so it will be good to get out of the house and see them.

In many ways, the visit will prove my dream is not dead as I get to relive the fun of dressing up different as a transgender woman. Which was one of the fantasies I had when I started so long ago up my gender path. I should have known that my path would have been different as I veered away for just wearing skirts and dresses and sticking with slacks and women’s pants. Much to the chagrin of the cross-dressers around me who kept asking me why I would want to wear pants when I had to wear them all the time as a guy. My only answer was that I liked the way I looked in them, so now you can go away and mind your own business.

I guess you can say that even in my formative years as a novice transgender woman, I have always been a “tom-boy” of sorts. Which is probably another reason I fit in so well with the lesbian culture that I did in my jeans and boots. One way or another, the pieces of my lifetime dreams puzzle were coming together and even though I was too stubborn to initially accept it, the finished puzzle was all me. “Tom-boy” and all.

I was fortunate too when I discovered that and became a firm believer in my gender was completely between my ears and not between my legs. Which made feel less bad about not having any access to the early sex-change or gender realigning surgeries which were available at the time. My complex life was slowly coming into focus, and the best part was that I increasingly felt comfortable and confident with it.

Coming full circle back to Liz’s blood work appointment, I had the chance to remember the bad old days when even such a mundane trip such as that could cause me strain and paranoia. It felt so good to feel good about myself and confidently walk in proudly holding Liz’s hand. I never wanted to go back to the early days of gender dysphoria and impostor syndrome that I suffered through.

The moral to the story is that if you are on your path to a gender dream goal, there is no real unique way to get there. Ciswomen lead such complex lives that they leave you many ways to carve out your own. Way past the shallow aspects of appearance and sexuality. Which gives you more interesting sidelights of your life to explore and live. Just remember to stay safe as your personal safety privileges you had as a man go away forever. You are just learning what ciswomen have always known…stay clear of toxic men.

In the end, it is your dream to claim if you can get there, and to do it you may face challenges until the final pieces of your puzzle come together. Just remember, you are attempting one of the complex and difficult efforts a human can try and even if it so difficult to do, it can be worth it in the end.

 

 

 

 

Monday, July 20, 2026

Exceeding my Expectations

 

JJ Hart

I once worked at a great job where the company’s motto was, we exceed expectations.

As luck would have it, about the time I worked there was the same time that I really kicked my gender explorations into hyper-speed. It was the time when if I was not spending time with my second wife or working, I was out the door as a novice transgender woman learning the world. Looking back, that period of my life seems like a blur as both sides of my gender personality competed for attention.

In many ways the competition was not fair because I was beginning to feel so natural in the feminine world as my fear of doing it subsided. I was discovering that my testosterone poisoned body could indeed be shaped into something that could blend in with the ciswomen who ran the world I wanted to be part of. My confidence rose every time I succeeded in presenting successfully in the world as a transfeminine person. I was exceeding my expectations and many times I could not believe it was me.

To do so, when I could, I picked out many feminine things I could do to prove to myself that I could. Such as the time I was able to do the “Black Friday” Christmas shopping with the overwhelming majority of the women in a mall I always wanted to go to back when malls were still the place to be to shop after Thanksgiving for deals. I had tried for years to schedule such an adventure but finally, the sun, moon and stars came together for me, and I was able to do it.

When I pulled into the mall, it was already packed and I was lucky I found a close parking place to a side entrance and wore my most comfortable boots with my big soft sweater and leggings to brave the Ohio cold and headed inside the warm mall. As I said, the place was packed with women on a shopping mission, and I soon learned they could not be bothered with worrying about a single trans woman going about her business. Sadly, I did not have a long time to spend there because I needed to go to work later in the afternoon, so I had to leave my adventure behind and drive home. But, on the plus side, I could mark another experience off my feminine bucket list as I finally was able to take on the world as a woman during one of their favorite activities…getting the best shopping bargains at the post-Thanksgiving Black Friday deals.

As I took that off my transgender bucket list, I needed to rack my brain to think of other primarily ciswomen dominated things to do. Next, I decided to try my hand on seeing if I could be accepted in a couple of the small lesbian bars I had heard of in the Dayton, Ohio area. I turned out to be extremely successful in one of them and extremely hated in another. Which at the time, I did not think was too bad. The venue I was intensely disliked in was essentially a lesbian biker bar which did not accept trans women such as me at all. But the other bar did and I ended up having several great experiences there.

Such as the night when I was forced to sing karaoke by a super-butch lesbian in a cowboy hat who I did not think she ever realized I was trans. At any rate, I made sure I had paid for drinks and left before she realized why my voice was deeper than hers when we both tried to sing a classic country song by “David Allan Coe.” Then there was the night I was approached by another butch who bought me a beer and told me she ought to pick me up and take me home with her. The only problem was that I was still married at the time, and my wife would have never believed me if I told her I was abducted by an alien lesbian. Probably the best part was, out of all the people I knew in the bar was the main bartender who by accident I learned knew my male self. I never knew if she had given my secret away that the “lipstick femme lesbian” everyone was approaching was transgender. Before I found out, sadly the venue had closed, but my expectations were exceeded when I knew I could be accepted by the lesbian culture.

Perhaps my biggest win came when I was able to get away from the gay venues, I was seeking refuge in from the world and try to become more of a regular in all the straight I sports bars I used to be a regular in when I was a man. I say the biggest win because for the first time in my life I was coming out of my gender shell with the chance to learn who I really was in my new trans womanhood. All of my expectations were quickly exceeded the night I finally gathered my courage to go back to the nights I thought I was only a part-time cross dresser and prove myself wrong. I was so much more as I struggled to learn about and live my reality. The night I did it for the first time at a TGIF Fridays, set a standard for me and taught me a lesson I could never unlearn, I could never go back to being a man again.

Setting up a whole new set of expectations for me was never easy. Especially when it comes to something as complex as living as a whole new gender. I was naive about how complex a ciswoman’s life could be, as I primarily learned I had so much more to work through than just worrying about my appearance. Which was just the first high heeled step into the real world of women. Many times, I needed to kick my heels off and dive barefoot into the girls’ sandbox to survive and exceed all the expectations I had ever had.

Hey You!!!! Thanks for reading along with all my writings and as always thanks for any comments you may have.

 

 

 

 

 

Friday, July 17, 2026

Trusting the Process

 

JJ Hart Very Early On, 
Trusting the process in a 
rest room. 

One of the hardest things to do as a transgender woman or transgender man, is to trust the process as you continue along your gender path.

Especially when your path is lasting longer and taking you places you never thought of going to. Then you have the probability of picking up more of the gender baggage than you never thought you would. Trusting what you will take with you and what you will leave behind becomes a huge problem.

As you build your new personality, you can use your old gender baggage as positive building blocks if you can take the leap of faith to learn from your past. Perhaps, more than anything else, you must trust in yourself to believe in what others may think of you. This was very important to me as I began to build from my small core of ciswomen friends and have the courage to spread out into society.  I started following my new wife’s Liz lead and joining her spiritual group to start and then spreading out further into other “Meet-Up” groups in Cincinnati which matched our potential interests such joining writers’ groups for me, along with craft groups for Liz. It worked well for me as I was able to work my way out from being so shy around strangers and build more trust in myself.

Trust comes with a couple of drawbacks such as what if your trust is betrayed and how you will ever build trust again. Going way back to my second marriage, I destroyed most of the trust my wife and I developed over the years by breaking the deal I made to never go out of the house alone cross-dressed. I certainly was not proud of what I did but just could not stop myself from doing it. Essentially, I felt as if I was cheating on her with another woman who just turned out to be me and whatever she did was just not good enough for me. As I was busy destroying her trust, she was correct in telling me I made a terrible woman, and it had nothing to do with my appearance. Which at that time meant the world to me.

During this time and beyond, it was difficult for me to try to trust the process I was on during my gender journey. It seemed nothing was going fast enough for me to ever see if I could make it to my ultimate goal of living full-time as a transfeminine person. I guess if you take into account all the years, I spent cross-dressing my life away from the male world I disliked so much, it is no wonder I felt that way.  From start to finish, it took nearly a half a century for my male to female femininization project, which should have been more than enough time to trust the process and have faith where I was going.

My excuse that I always hang onto is that my male life was not that bad and my male self was a powerful ally with my second wife on me ever transitioning into transgender womanhood. And did I trust what all of that meant to me anyhow. I did realize any sort of a gender transition would mean I stood a very real chance of losing all the materialistic male privileges I had built up over the years. In an instance, my spouse, family, friends and job could be wiped out and I would have to start all over again. At that time, I did not think I trusted myself to do it, so my made the worst choice I have made in my life and tried to juggle a life somewhere on the gender border between male and female.

As I am always hesitant to write about, my choice to walk the narrow gender line wrecked my mental health and led me to a self-harm event. I was already diagnosed with being a Bi-Polar depressive person, so it did not take much to send me over the edge. Fortunately, I had a good therapist to help me realize my truth and help me through it. I was slowly coming to a point where I could trust the process and understand where I truly fit into the grand plan of my life the way it always was meant to be. I should have never embarked on any path to being male at all. A place which was foreign to me and I just did not belong. I was no wonder I felt the way I did around other men I was with. Full of mistrust in them for the most part.

Once I was over that hurdle in my life, I needed to begin to trust the world through the eyes of a trans woman which was hard to do. Mainly since I knew the way toxic men treated women from my past. Once again, cis women with their open minds to me joining their club were my secret to building trust again. Even though I still carried the scars from attacks by passive aggressive ciswomen, I was able to build my own new life with a feminine confidence I had never had before. I felt so good, I went ahead with my long-awaited legal name change and even longer awaited plan to be approved for HRT or gender affirming hormones. By doing so, I effectively painted myself into a gender corner I could not escape from. I had to trust the process and not try to turn around no matter how attractive the idea sounded at times when I learned what I was losing with my male privilege being taken away.

Primarily, I lost much of the knowledge of life I had learned as a man as well as needing to keep a closer eye on my personal security. Which was quickly at risk as a transgender woman joining the world for the first time and learning first hand what ciswomen already knew about being around toxic men.

As I said, trusting the gender process path I was on was never easy, but it turned out it was the only path I had.

 

Thursday, July 16, 2026

Finding Comfort in your Own Skin

 

Image from Ayesha Rosley
on UnSplash.

I believe the way to finding comfort in your own skin as a transgender person is having the confidence to do it.

Just think of all the time you may have spent in front of your mirror as you gathered the courage to take on the public and work from there. Like many of you, I experienced severe gender dysphoria every time I looked in the mirror and saw a man dressed as a woman and was afraid to go out into the world and face the public. To this day, on occasion, I still suffer from my lack of confidence in who I really am when I look in the mirror in the morning. I do my best to just ignore it and move on and take on my day knowing I am doing my best with what I have to work with. Or as a transgender woman friend once told me, I pass out of sheer willpower.

My willpower was tested during the many times that I failed in public and needed to start all over again. At that time, I had very little confidence that I was doing the right thing with my life. I had to go through years of trial and even more error before I began to build the confidence I needed to succeed in the world as a transfeminine person. When it came right down to it, many times I was excited about the prospect of going through another trial to learn if I could be successful. When I was a success as a trans woman, I wanted to do more on my transgender bucket list of things to try in the new exciting world I was in.

Most the major changes for me came when I began to really look around at what all the ciswomen in the world were wearing and I needed to put away the stubborn attitude of what I thought I should look like. As I began to successfully blend in with the world at large, my confidence began to rise, and I could relax and feel more comfortable in my own skin. It was the beginning of a life-changing gender experience which I discovered I was along for during a very bumpy ride.

In many ways, the ride to being comfortable was like my favorite roller coaster ride at a big nearby amusement park. Often the ride up was slow and uncertain to the top but was made up by the rush of going down the gender hill. It did not take me long to appreciate the rush of coming down my own personal coaster. Even though I feared climbing the heights I was climbing (as well as the threat of falling) the risk was worth it as I began to carve out a small life as a trans woman. Which I always wondered if I could do at all.

I found I could do it thanks to the welcoming embrace of several ciswomen I was introduced to. It was scary yet powerful when I began to receive invitations to special girls ‘nights out. Once I figured out what I was going to wear, then I needed to figure out what I was going to add into the conversation with the other women who I had never met. I desperately did not want to act standoffish and worse yet bitchy by not joining in with the other women who I had a chance to make friends with. Looking back, I think I was successful because outside of one woman who kept glaring at me, I was treated well by everyone else. All this sudden attention led me to a newfound confidence in being in my own natural skin that I never had before in my old male life where I always needed to be on the outlook for someone trying to take away the life I had. I was always competing for what I had earned in a what you had done for me recently world.

The reverse was true in the transgender woman’s world I had found my way into. As I became more confident and successful in just being the me, I always wanted to be, the only competition I ever felt was when I needed to use the women’s room in a venue, I was not a regular in. And even that began to fade when I learned the proper etiquette to use in the typical women’s rest room. There was no thrill in doing just what came naturally, just the relief of being allowed in women only spaces to do it. Taking away any sort of a transphobe’s argument against me using the restroom of my choice.

In my case, becoming comfortable in my own skin was a constant problem which started with the way I was raised. My parents were long on material support and short on any emotional needs I may have had. Which led me to be alone with my gender dysphoria. It was a very lonely, confusing place to be and left deep scars on my internal confidence as I had no deep connection to what my true gender skin really was. The male world I was forced to live in, and the female world I wanted to be in. So, for me, the process of gaining any sense of who I really was a difficult and time-consuming process. Plus. My confidence was so fragile that the slightest problem could send me back to my cross-dressing drawing board to look for solutions.

Over the years, I flat out wore that old cross-dressing drawing board out until I began to figure out my problems were right in front of me. All I had to do was have the courage to do something about them. One of the problems was  they were so much deeper than just trying to look like a ciswoman. I was tired of thinking I was fooling anyone into thinking I was a ciswoman and settled into trying to build myself into the quality new feminine me I wanted to be as I had earned my womanhood from a difficult, unique path.

I seized the opportunity to finally be comfortable in my own skin.

 

 

 

 

 

 

Wednesday, July 15, 2026

Existing in a Male World from the Perspective of a Trans Man

Image from Nicola Dowie
on UnSplash. 
 


In response to yesterday's post praising transgender men, I received a comment from “Gio”, a trans man who follows my writings and thoughts.

Here is his comment word for word on what he has gone through during his transition from female to male:

Thank you JJ for this nod. You know, they are a tough bunch, on the exterior. They are also exhausting. Try to teach them how to be a real gentleman and right out of the gate they label you a sissy. I always counter with being raised to respect and honor women. In the Italian Culture in which I was raised the women were savvy. The women in my family ran the show and they somehow left the men feeling like they were in charge. I witnessed this with my parents (first generation born in America) and my grandparents (immigrants - who escaped Mussolini; everything old becomes new again but that's another story). The Cis men I encounter, many of whom are wealthy Trump supporters, posit they own their women. She is to do what they say. A woman, if raped, deserved it because of how they acted or what they wore. It boggles my mind. So, I remind them that women are to be revered, they remain underpaid yet they have more talent than their male counterparts. I remind them that if married they took a vow to cherish and protect their wives. I could go on and on here. Suffice to say, it’s usually a bipartisan type of conversation and they often end pleasantly. Luckily, I've not been fired yet because mostly these are the people who keep me employed. I'm also amused by how they request me as their chauffeur to drive their wives and daughters. It's these little things that cause a ripple effect”. First of all, “Gio” thanks for the comment!

I really liked your insight into how exhausting men are because on the few times I went out with a man, I could not relax and be myself when I was catering to his ego. In my family growing up, we were a heavily male influenced crew but like you, mom ran the show from behind the scenes, so I learned a lot from her on how to be a woman, She is rolling over in her grave as we speak to hear of such a thing but it is true.

Fortunately, since I am retired, I don’t have to worry about working with any tRumpters and their backward gender ideas. But when I was employed, I always did my best to protect and advance the careers of the ciswomen around me. To the point of even hiring a transgender server at one of the restaurants I worked at. Sadly, I was transferred and she was fired by the next manager, but I tried to do my part.

Looking back, it was my love of sports and military service which kept me from wearing the “Sissy” tag early in my life and when I advanced as far as I did up the business ladder I was in, I understood that males form teams and I was able to benefit from that even though I detested everything I was doing most of the time when I needed to play the gender game I was in. Maybe the whole time, I was exhausted too about playing the male game and just wanted out to go to my transfeminine world. I took what my mom taught (more than dad) and was able to beat the system which was stacked against me.

When we are transgender, it is certainly a complicated world we live in when we need to go outside the confines of a so-called normal world. The old world is on its way out and hopefully a younger more progressive gender-neutral generation will power a better world. Especially for transgender men such as “Gio” who was kind enough to share his thoughts with us on his world.

 

Sunday, July 12, 2026

A Want...or a Need

JJ Hart Discovering her Needs
I am in the first row on the left.

When a want turns into a need, sometimes you can feel it. Other times, not so much as if it sneaks up on you from behind.

As I began to wear dresses and makeup as a young boy, for the most part, it was because I wanted to do it. Cross-dressing just relieved the pressure of my unwanted everyday male world. It did not take me long to figure out my want was much more than just a casual appreciation of women’s fashion and makeup.  I did not know it then (and the term had not yet been widely used) that I was transgender more than a cross-dresser. I could not feel the change because I did not have the gender knowledge to do it.

Life began to change for me when I started to cross-dress for the thrill of it and attend Halloween parties. The parties ended up teaching me the basics of being a woman in public around people I knew, and I wanted to take it a step further by not having to wait another year to try again to get out of my dark closet and into the world. That is when my story turned out to be dark as I was not met with many positives by the public as a novice trans woman, cross-dresser or whatever you would like to label me as. To too many people, I was simply a man in a dress and clown makeup. I learned the hard way to get back to my drawing board and work harder on my feminine craft to find out if I was ever going to be able to succeed at all at my dream.

I also learned that if I was ever going to find success on my gender path, I was never just going to make it by just thinking it was just a want. It had to become a deep-seated need. I went back and dieted, worked on my skin and did everything I could to improve my testosterone poisoned body. All it really taught me was how much deeper I needed to travel along my gender path to make it at all and I needed to do it very badly. As the pounds melted off, I was able to find more stylish feminine wardrobe items to fill out my fashion needs and dress for success to blend in with the rest of the ciswoman crowd. Who I learned the hard way, were the people who ran the world I was attempting to be a part of. Or I could go casual if I needed to and a more polished business look when I needed to upscale my appearance. Fashion-wise I was learning that looking the best I could and blending in with the public at the same time was a definite need not some sort of a frivolous want just to justify something I wanted.

The more I tested the world as a transfeminine person, the more I needed to do to help myself along in the learning process of just belonging in the world I always should have been a part of to begin with. It was a real chore just to put the mirror image I thought I had perfected into the public and into motion to see how it worked. For the most part, I was improving to the point where I needed to start trying to communicate with the world as a more complete trans woman. As I always point out, the communication challenge to me was immense because I had always been a lazy communicator in my life. By that I mean, I had never really had to listen closely to what another man was telling me. I knew instinctively how to respond to another man but was clueless when it came to woman to woman talk. Which I always had known was different but how different I did not know until I was made aware of it. For example, for the first time ever in my life I needed to really stop and listen to whomever was talking to me. Were they trying to point out danger to me or just being friendly as a ciswoman who was curious of me or a toxic man who just viewed me as some sort of a fetish object.

Quite possibly, the communication aspect of my male to female femininization need passed my desire to be as attractive as I could as a transgender woman in the world. Instead of just wishing and wanting to be accepted as an equal by the other ciswomen I met, I needed to make it a priority. I even swallowed my pride and took female vocal lessons to make the process easier. It was difficult, but I think I gained enough confidence to help with my overall presentation and life.

I was helped too when the pressure to succeed was relieved here and there by the new success I was having in the world carving out a new life which on one hand to be terrifying and on the other feeling so natural like I was coming home to the self I always should have been.

I found I did not discover all my true self until I could step away from me for a minute to look at how far my gender path had taken me. After years of experimenting and trying different things, I finally achieved my need to be allowed to play in the girls’ sandbox and I was not disappointed with what I found there. Even though I had to put up with the occasional hater or TERF who wanted me out, but the majority of women made me feel welcome in their world and that was all that mattered to me.

The sandbox provided me with firm lessons and reassurance in what I was trying to accomplish in life. The want I always felt was always a hidden need which took me years to realize was my true problem in life to solve.

I hope you can realize your true wants and needs on your gender path also and life becomes easier for you if you are searching like I always was.

 

 

 

  

Friday, July 10, 2026

It's Your World to Live In

 

Image from Gabriel Silverio
on UnSplash. 

When it comes down to it, it is your life to live and no one else’s. But life comes in the way.

The problem is often for transgender women and transgender men, it is easier said than done to live our own lives. Especially for those of us who had to wait until later in life to go after our dreams of transitioning into a feminine world. Perhaps, you were like I was and called selfish for my one-sided obsession about even seeing if my male to female dreams could ever become a reality. My second wife was fond of telling me my cross dressing should not be all about me.

The longer I pursued life on my new transfeminine gender path, I realized she was right. In order for me to move ahead in a world which felt so natural to me, I had to be selfish. It was the only way I could make the difficult decision to take a leap of faith and try to jump the gender border.

Back in those days, the only thing I could hang my pantyhose on were the annual Halloween parties I was going to dressed in my feminine finest. During these early parties, I learned a few of the basics I would need to survive as a trans woman later in life. Such as how visibly trained the human animal is to the genders, and if I was to go to the feminine side, everyone (male and female) would be noticing me. My new visible role in the world took some time and effort to get used to, but I did finally do it when I learned to dress to blend with the other ciswomen around me. It was my life to live, and I was coming closer and closer to deciding how I wanted to live it.

Before I did, I discovered I still had a whole lot of living to do before I made my decision. The problem was my male life on occasion was not that bad. Which gave me false hope that I could save it. All it did, as I juggled two genders at once, was to make my life a mental health hell as I struggled to maintain any sort of life I wanted. On one side, I had the increasingly financially successful male self-making it harder to give up all that he had earned and the male privileges which came with it. Struggling with my feminine side which felt she was in a more natural position to thrive. The end result was whatever decision I made just had to be the right one. With so much at stake in my life, I needed to go back to being very selfish with myself to make it.

In the meantime, I went into a heavy experimentation period of my life as a novice transgender woman. My goal was to try to live every moment that I could discover what a ciswoman has to go through in her life. So, I could tell if I wanted to do the same thing. I wanted to be more than the “pretty, pretty princess” that my second wife always called me when she was trying to make fun of my femininity to learn what she was really talking about. It was a struggle, but eventually I did by setting up my own version of a transgender bucket list of things to do. What did a ciswoman know that I did not became my main goal in life when I shed my male clothes and went out in the world as a trans woman. Overall, my plan worked well for me except the times I tried too hard and ended up in redneck bars where a single woman should have not been to begin with.

I did so much, I wore out my bucket list of obvious things to do and began to examine the difference between male and female privilege in society. Losing my male privilege brought about no real surprises such as having my intelligence challenged and learning to be more careful with my personal safety. While the main feminine privilege I felt was the freedom to be myself in the world and went way past just having doors opened for me by men. Needless to say, I was in love with the whole path I was on as a transfeminine person and could not wait to get back to it anytime I had to leave and go back to my increasingly unwanted male life.  I was stubborn but then again, I slowly realized I could never go back to the life I had lived before. No matter how successful it was.

As I reached the age of sixty, I could put it off no longer no matter how stubborn my male self-had become. When my second wife passed away from a massive heart attack, he was left with no allies in my life to fight with and was done. I had paid my cross-dressing dues by doing the best I could with what I had to work with appearance wise and had gone out of my way to experiment with how ciswomen live by putting myself in actual situations in life which I could expect to happen. After all of that, I just needed the final push off my gender cliff, and land in a world of my own choosing. Without a perpetual balancing act.

In other words, I guess you could say I went too far in paying my own dues during the approximately fifty years it took me to lead a life to discover who I always was. I decided long ago tt was too late to cry over what I did or did not do and to look forward to the time I have left in the world. At the least, I found living a life on both sides of the binary gender border was as scary as it was interesting. How many other humans get to experience what a transgender women or transgender man gets to see in one lifetime.

Sure, we experience our ups and downs but so does everyone else and we can have such an interesting path to claim a life which was always meant to be ours.

HEY YOU! Thanks for joining me in my journey and commenting or clapping for my posts. You make it all so worthwhile.

 

What Female Privilege Means to Me

  Image from Barbra Burgess on UnSplash. This post came about from a comment I received from an Australian woman called “Rachel” who asked w...