Showing posts with label makeup. Show all posts
Showing posts with label makeup. Show all posts

Friday, April 24, 2026

Nothing Lasts Forever...or Does It?

 

Image from Lucas Stankey
on UnSplash

Yesterday when I first went to the bathroom to begin my start to the day, I turned the light on and was greeted by a slight “pop” and the bulb going out. I was disappointed that it was one of those bulbs that is supposed to last forever. Then, I began to think that nothing lasts forever, especially light bulbs no matter what they say.

As I normally always do, I took the idea I was following to another level and compared it with my old broken-down self. No surprise, but I was not built to last forever either. Just like my transgender desires, or were they? I know when I was very young trying on my mom’s clothes and makeup, I thought perhaps I would outgrow my desire to be a girl as I became older. As it turned out, the opposite was true. I did not outgrow my desire to be feminine; I grew into it as I became more skilled in applying make-up and cross-dressing myself the more, I wanted to try my newfound skills in the public eye.

When I accomplished the seismic shift from mirror approval to public approval, I knew any approval would not last forever because of the mixed reactions I was having in public where I tried to go. Outside of the usual gaggle of teen girls who would laugh at me, I found that the largest part of society did not notice me when I took the effort to blend in with the other ciswomen around me. The mistake I was making was very simple when I finally took the time to figure it out. To dress for success did not mean to dress to attract unwanted extra attention. Success meant that I fit in with the public at large. Carefully, since I was a large woman, but a woman none the less when I presented myself correctly.

At that point, the responsibility of being a stable presentable transfeminine person began to set in. Just looking the part of a woman would not last forever as by then I certainly knew I would never just outgrow my feminine desires. By responsibility I mean it became time for me to fully accept what I was becoming in the world. To catch up, I took feminine vocal lessons to improve the nuances of my speech patterns and worked hard to listen to my progress. If nothing was going to last forever in my life as a trans woman, I was driven to do it right. Outside of the very good job I had and the relationship I was desperately clinging to with my wife, being a transgender woman who passed in the world was my ultimate goal.

That point in my life became a blur as I was learning almost daily what went on behind the gender curtain, I was given access to. It was not all good, but I knew the bad would not last forever if I continued past the stop signs, I encountered on my gender path to my ultimate goal of shedding my male past. The best part was no one knew him and I could build a new life from scratch with the good and bad of living as long as I did as a man. Everything was going so well for awhile that I was waiting for the next high heeled shoe to fall on me since nothing lasts forever. Sadly, I was right when my personal world around me began to rapidly crumble.

I call it my dark period when almost everyone I cared about passed away. I knew about the finality of death because of my parent’s death, but I wrongly assumed I would be the first to go in the small circle of friends and family I had built up because of my self-destructive lifestyle.

The person who helped me out of my dark age was my wife Liz who made me a believer in myself, and my forever could be with her. That was over twelve years ago now, and I hope it can go on forever too. I am just grateful I was able to find her when I needed her the most because I was drinking way too much and struggling.

The moral to the story is that life is but a circle and you can ride out the down parts if destiny shows you the way. It was true for me that the darkest hour was right before the dawn when I attempted the ultimate self-destructive act of all. Taking my own life. I failed and ended up being able to live the most exciting and self-fulfilling days of my life. I would have missed everything from the tour bus experiences Liz and I took all the way to being humbled in my two fairly recent hospital stays for Covid and pneumonia. Sometimes I think I was just given the chance to do as much living as I could in the time allotted to me. Being transgender just added to the mystique of my life.

Whatever the case, I was completely wrong when I was a kid thinking I would grow out of my dreams of being a woman, transgender or not. Growing into my dreams was certainly the most challenging thing I have ever attempted. Sometimes causing me joy and sometimes causing me extreme pain and suffering.

I know nothing lasts forever, but when mine ends, I will know I gave it my best shot.

Recently I learned that even backwards Ohio who only concentrates of passing anti-transgender bills, is considering a bill which would legalize euthanasia for terminally ill persons. Even though I seriously doubt the republican legislature will pass the bill, it would be nice to be able to end your own life when the time has come and gone to do it. I would love to have control of my own destiny. Nothing lasts forever, including humans.

Sorry to end this on such a negative tone but death is as sure as birth and we need to make the best of it.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Monday, April 20, 2026

I Always Was a Dreamer

 

JJ Hart

I always was a dreamer and a person who thought why not me if others could do it.

I guess it all started with the parents I had who were from the “greatest generation” or WWII and Great Depression survivors. Ironically, I was taught to think for myself as long as my thoughts did not conflict with theirs. That is why I could never tell anyone in my family of my dream to someday be a woman. I needed to fall back on my default answer that I wanted to be a doctor or lawyer which kept me out of the psychiatrist’s office.

My most difficult dreams were waking up when I was still male and my vision of being feminine was just that…a vision. I had only dreamed that I was the pretty girl I desperately wanted to be. It was then that I started to play the odds that I would not be caught wearing my mom’s makeup or dresses, or worse yet get caught shopping for my own makeup in a downtown store close to where my dad worked as a banker. As luck would have it, I managed to always be clean and dressed back into my unwanted male clothes by the time my parents or my only brother came home from wherever they had been. Even though I had been able to briefly help decrease the gender pressure I felt from cross-dressing, deep down I knew I had other urges and I began to dream of what I was ever going to do about them.

The first problem I had was I had little to no confidence in my ability to present as an attractive feminine being when I tried. I was fond of thinking I looked like a circus clown in drag. And I am sure I did before I was able to come to a basic understanding of how to use makeup. On most occasions, I could only dream of the time when I could look better as a girl in my mirror and I kept playing with the odds I would not be caught and ruin my whole future as I knew it.

The playing the odds attitude helped me considerably when it came time for me to serve in the military during the long drawn out and deadly Vietnam War. Rather than serve the basic two years if I was drafted, I could have a couple other choices such as enlisting for three years and attempting to get a job I wanted to do or even join the National Guard for six years and basically stay out of the war that way. As decision time approached, I made a split-second decision to turn down the guard offer and take the enlistment offer as I hoped I could get a job in the Army that I really wanted. Which was I really wanted to continue my radio DJ career in the military which was nearly impossible to do as the Army only had sixty broadcasters in their entire system. I played with the odds and won and the three years I spent serving my country turned out to be very beneficial to me as I got exactly what I wanted. A slot in the American Forces Radio and Television Service in Thailand, then Germany.

My success in my near to impossible military profession taught me that perhaps I could be successful in my transgender dreams also. Nothing might be impossible if I only kept trying and refused to stop during my gender journey. I was naïve, which was probably for the best because I had no idea of all the stop signs, I would continue to face before I was allowed to play in the girl’s sandbox. I always knew women led a more layered, nuanced existences than men, but I didn’t know how much more different I would have it as a transfeminine person until I tried.

I knew when I started to become successful in my dream to live in a world full of competitive ciswomen, my ultimate goal might have been within reach. My presentation in the world as a trans woman was benefitted from all those frustrating hours, I spent experimenting with makeup when I was younger. The next challenges turned out to be the most difficult ones when the world (primarily ciswomen) wanted to challenge me with their curiosity about what I was doing in their world. I discovered what I already knew from my past that whatever did not kill me just made me stronger from the rare negative interactions I had with other women. I was able to learn valuable lessons on how to look for passive aggressive disagreements and recover along with the claw marks up and down my back.

Another positive was that I rarely had a wishful dream that I was a woman anymore. My feminine dreams just went to the shallow extent of showing me how my life would be if I was more attractive or had the chance of not missing all the days of growing up in the world as the girl I always knew I was. Plus, I knew I must be doing something right because none of my feminine dreams turned out to be nightmares in the real world.

In addition to wondering what my second wife would think of me now as a trans woman who has had a decade or so to fill out her gender workbook, I wonder if my parents would have ever come to accept me either. Or at least recognize the mental seeds they planted in their oldest son who turned out to be their oldest daughter after all. Somehow, the irony is not lost on me how such rigid parents could raise such a child who turned out to be such a dreamer. Somehow, I believe my dad who was a self-made successful man would have come to accept me long before my mom who I tried to come out to and was rejected years before.

Even then, she could not break my spirit or my dreams.

 

Friday, April 10, 2026

I Had to do Something Right

 

Image from Mark Farias on Unsplash 

In my dark days of confusing cross-dressing, I vaguely knew I was doing something right. Or at least I thought so because I could not wait to try it again.

Looking back, it was the brief moments of gender euphoria which clouded all my doubts about my gender and kept me going. Even through the nights when I was the laughingstock of teen girls in malls, a little voice kept telling me to keep going and eventually I would improve my overall feminine presentation so that I would blend in and not get noticed. Along the way, I even needed to lower the expectations I was putting on myself to keep going. I was never going to be the most attractive woman in the room, but at least I could still be like most ciswomen I saw and live a decent life. Even though I started to feel this way, I never gave up the idea I could do better with my makeup, fashion and hair so I could survive. Simply because I was enjoying the experience so much.

Later on in my life, doing something right extended to my interaction with the world as a novice transgender woman. I was surprised when I attracted more attention from ciswomen than men and just thought they were curious about me and were welcoming me into their worlds, while men were just the opposite. Most resented the fact I was leaving all of the male privilege behind (along with the good old boys’ club) and moving to the other side of the gender border. I did not care because my need for companionship was being satisfied and I had always gotten along with women easier than men most of my life. Increasingly I found I never wanted to go back to the male life I was attached to by a spouse, family, friends and jobs. It seemed the longer I waited, the more male baggage I was building up when I really did not want to.

The next problem I ran into was the impostor syndrome I was feeling. Specifically on the girls’ nights outs I was invited to. It never failed that right in the middle of me enjoying the evening, I had suspicions sneaking up on me that I did not belong there at all. I was an impostor in a scene made up of women who had worked their entire life to get there. It took me awhile to come to the conclusion that I had worked my entire life also to make it to my own version of womanhood, and I deserved as much as the next woman to be attending. Fortunately, I received very little negative feedback from other women attending the get-together, so I did not have to face my impostor syndrome at all. I was doing something right for a change to even be invited to such special women only events.

I was able to take my experiences with girls’ nights out to my everyday life primarily because it built my confidence as a transfeminine person so much. With my newfound feelings, I worked even harder on my makeup, fashion and hair to appear more feminine than ever before. Primarily, I learned the power of contouring and colors on my face from professional makeup artists I met at the cross dresser-transgender social mixers I went to. One in particular, took the time to explain what he was doing in terms I could understand and repeat on my own. It was a powerful experience when I had to set my makeup ego aside and learn better results from a professional. From that point on I worked on taking weight off, so I had a better opportunity to find and buy more fashions that flattered my male figure at the many thrifts stores I frequented. When I arrived at that point, the problem then became getting out of the mirror and started putting my new improved feminine self into motion in the world. It proved to be the most difficult part of me doing something right.

Suddenly I had to consider how I was moving as I tried to mimic the unique way ciswomen move and put all my male linebacker moves behind me along with the scowl on my face I was used to wearing as my male defense mechanism. And the most difficult issue of all was learning to communicate one on one as a woman. I knew with certainty I would have issues with my communication, but not to the point that I did. I even went to the extent of taking vocal classes to improve my feminine basics and be able to talk easier in the world with women and men. It just made sense to do if I was continuing to do something right.

It turned out, the more I did right and received positive feedback, the more I wanted to do to refine my feminine approach as a transgender woman. Because I always had the belief, I needed to be better than the average ciswoman to just survive behind the gender curtain. When I was just trying to do something right, on occasion I paused to reflect on how far I had come along my gender path to arrive where I was. I did remember that scared little boy dressed in his mom’s clothes in front of the family’s hallway mirror, wondering what was next. For the most part, back in those days, there was very little to let the young boy know he was doing anything right.

Somehow, I survived all the negative feedback and impostor syndrome problems and continued forward to a better world. One I wanted to be in and dreamed of my entire life. As I love to say, as with any woman, I needed to socialize myself into the world. Being born female does not automatically make you a woman, you must learn to be one. The same was true for me. I just took a radically different path to earn my womanhood. I needed to do many things right to arrive at my dream.

 

 

 

 

Friday, April 3, 2026

A Labor of Love

 

Image from Mayur Gala

Once I stopped being a victim thinking I was the only male in the world who wanted to be feminine, I quit being so negative about my life as a whole. That is when I started to enjoy wearing my mom’s clothes and experimenting with her makeup. All I really knew was that the process of cross dressing took away the problems I was experiencing in everyday male life to the point of even relaxing me. The only real issue I had was when the next time was I could find the privacy to do it.

I even went to the point (in warm weather) of stashing a small collection of clothes and makeup in a hollowed-out tree in a woods next to our house. I was in my own world and enjoyed the privacy I had to feel the clothes and dreaming that I was one of the attractive girls I saw at school and envied very much. At that time, I did not understand how I would take on a lifetime of work to pursue my labor of love.

The first task I needed to accomplish was when I was financially able to do it, was shop for and acquire a whole new set of clothes so I could present better in a world of ciswomen I needed to compete with in many ways. The first task I needed to complete was to slim down my male body as much as I could so I could fit into more stylish clothes I was suddenly finding in all the thrift stores I was shopping at. I liked the stores for two main reasons, the first of which was price of the items displayed and secondly, I never had any problems using the changing rooms to see if the items I was looking at actually fit. Plus, the challenge of doing so much shopping was something I loved. The only problem was where I was going to store away all my fashion treasures from the prying eyes of my wife who would wonder where they came from. Fortunately, we had a huge old house with plenty of places I could store my clothes.

After I began to dramatically improve my worldly presentation and use the public as my mirror, I found myself in a position where I could blend in with the public. To test myself, I even did tricks such as wearing sunglasses where I could see the eyes of the public when they could not see mine. That way, I could tell if they were staring at me or not and I was overjoyed to learn I had passed the test, and the public was ignoring me. From there I could widen my horizons on where I was attempting to go as a novice transgender woman. I was in love!

My love ironically did not last long because very soon, I discovered the public actually wanted to interact with me. Suddenly, I needed to work on a presentable voice so I could attempt to basically communicate mainly with other women since men did not want to have anything to do with me since I left the men’s club, I used to be part of. The fact remained; I did not miss male interaction at all. It was something I never had in my male life either as I always preferred the company of women. Surprisingly to me, as I transitioned, I was having no problem gaining feminine company. Probably because ciswomen for the most part were curious about what I was doing in their world. Plus, the women did not carry the paranoia about their sexuality that men had, they were not scared of me. Finally, I was showing the ultimate honesty about who I was which many women appreciated. For any number of those reasons, I loved the interactions I was having and being able to learn more from them about being a woman than ever before.

The fact I was loving my life at this point as a transfeminine person led me to realize that for the first time, my life was headed in the right direction. I felt so natural and even happy when I followed my gender path to a point where I was allowed behind the gender curtain to see if I really wanted to give up all my male privileges and keep moving forward to my ultimate goal of starting gender affirming hormones or HRT. If I could be approved by a doctor to do it. As I always say, I was approved and the changes were magical and I was in love again.

Before you begin to think my love revolved just around me and not another human being, my future wife Liz came into my life over a decade ago and changed everything. I was in my sixties and was thinking about spending the rest of my life alone when Liz and I met on an online dating site. We got along and she turned out to be the final push I needed to leave the male world behind. She was the missing link I needed to turn my transgender life around, and I love her very much.

It feels good to say that I love someone else more than I love myself or my gender transition for the first time in my life. According to my second wife who died many years ago. It would be interesting to see now what she would have thought about the feminine person I have become.

My final point is it is said you must love yourself before you can truly love someone else. Maybe I needed to learn my true self as a transgender woman before I could love someone else. It certainly took me long enough to love myself, a lifetime for me which spanned over half a century. Once I realized my path was a long labor of love, I learned the hard way I needed to be patient. Which was difficult for me, but I made it through and learned from my labor of love.

 

 

 

 

Monday, March 30, 2026

Was I being Selfish?

 

Image from UnSplash and
Brooke Balentine.

When I was a maturing cross-dresser, one of my wives made it a prime point of her argument against my cross-dressing at the time saying that I was just being selfish. The problem I had with her saying that was deep down, I knew it was true. Mainly because I was spending all my spare time thinking about or doing my cross-dressing activities. I felt guilty, but there was little I could do about it as I wanted to be feminine so bad. So, I went on with my daily activities ignoring the best I could what she said.

Sadly, my selfish problem only became worse the farther along I traveled up my gender path. I simply wanted more from my life than what I was getting and I was pursuing it. I thought to hell with the risk I was doing to my male world and life as I knew it if my secret was discovered as it almost was several times. Like when I almost ran head on into my wife’s boss going to a big box store in a small Ohio town we lived in at the time. I did not think he recognized me, but he did bring up seeing a a particularly “big” woman the other day when he left work to pick up supplies at a party we were attending at his house one weekend. Of course, I could not let on it was me he was talking about, but my wife knew and questioned me about it later. I don’t think she ever believed my denials, but life went on until I made it to the next level of being selfish.

When I was out in the world as a successful transfeminine person, just doing it a little bit was just not enough. Success bred success, and if I could not for some reason make it out into the world again, I grew angry and bitter with life and tried to take it out on the world around me. By doing so, I even almost lost jobs because of my attitude. Having a sullen selfish attitude got to be so bad, I even sought out gender therapy to help me from one of the few therapists in Ohio at the time who dealt with it. It turned out to be that she could not work miracles with my gender issues, but she did with my attitude which was influenced by being diagnosed with a Bi-Polar depression disorder. Following a few experiments with medication, I found one that worked and my life became better. Except for I did not magically quit my feminine ideas and remained on my selfish path to see if I could ever live my dream of going full-time in life.

What made matters even more frustrating was, even with all the mental energy which was going into my transgender issues my male self was still able to advance in his life too. Making it harder for me to think about moving along with my plans and even being selfish about them at all. Through it all, my guilt was building about why I was even cursed with being transgender at all. This was before I finally began to understand my gender problems were not a curse at all.

In the meantime, my wife and I were clashing every time she caught me being selfish and leaving the house as my feminine trans woman self. One time she was even mad enough to tell me why I wasn’t man enough to be a woman. If I was smart at the time, I would have listened to her advice. I should have faced my true self and started making plans for my ultimate male to female femininization project. I just was not ready for several reasons such I loved my wife very much and the life we had built together.

By now, you have probably noticed a theme here. I kept shooting myself in the foot by being supremely selfish when I set out to build a new life when I already had a perfectly good one with a loyal wife, good job and loving family. All of which helped to describe why I felt so much stress and tension during this portion of my life. All the therapy and medications in the world could not help me until I had the courage to face up to my true self as she looked at me in the mirror. She had been there all along, and I thought I needed to apply makeup to bring her out (which I did for the public) but one on one, she was very real to me. She appreciated all the outwardly things any ciswoman needs to survive but inwardly, she just needed to be recognized for the person she had the potential to become.

Ultimately, I outlived my second wife (and many family members and friends) which freed me up to not feel any selfishness at all about what I was doing with my femininization. I was just busy preparing my world for the truth I had so deeply known. I should have never been a male at all and was just a woman cross dressing as a man. Needless to say, it was an enlightening experience coming out of my gender shell and having the opportunity to live my feminine truth. Just having the chance to compete in a world of ciswomen on their level was an intimidating yet exciting experience which my true self was up to. After living life hidden away all so many years against her will. As with most all transgender women and transgender men, it is a major project to bring ourselves into the world and unfortunately, we must be selfish to do it. The good thing is, once we go through the selfish part of our lives, we have the potential to be good, loving partners. If we are destined to find that special someone to love.

Life dictates it is nothing but a circle, and we have to take the good with the bad. Selfish or not.

 

 

 

 

 

Saturday, March 28, 2026

Wishing and Hoping never Made it For Me.

 

Image from Abbot
on UnSplash.



Sadly, just wishing and hoping that we can make it to our feminine dreams just won’t get us there.

Since most of us started our gender journeys with very little natural external characteristics of the gender we want to become, it makes our struggle even more difficult. Even more so when you consider how far trans women like me had to go to hide my true self so I would not be bullied by the men around me. I played sports such as football and worked on cars to hide the fact I did not really want to follow a male path.

In the deep, dark recesses of my closet I spent my time wishing and hoping time would come along to magically change me. We all know how that worked. It did not and I grew more frustrated as I spent my meager leisure time wistfully cross-dressing in front of the mirror at home in the long hallway we had. After the initial success I felt from looking at my imagined self as a pretty girl, I knew it was just not enough. Looking back, I was going through the early stages of being transgender without having any of the terminology to go with it. In the meantime, I needed to keep my public charade alive of making the world think I was male.

Then, along came the shock of puberty with all its unwanted physical changes such as size of body and bone structure. I was helpless as all the changes took place and I was depressed that I was moving farther away from the feminine person I always wanted to be. All I could do was wish and dream for change which never worked. I finally had to do something about it, the pressure on me was intense. The little trips to the mailbox when I was dressed as a girl just were not enough anymore, I could no longer just exist on that little interaction with the world as I introduced my true self.

Early on, once I grew older and found a place of my own, I did venture out into shopping malls and often the experience was brutal. No matter how good the mirror at home was telling me I looked, the public quickly told me something else. Too many times I had to come home early crying because of being laughed at by groups of teenagers I attempted to dodge but couldn't. Fortunately, something deep down inside me kept telling me to keep trying to get better with my make-up and fashion and maybe then I could present well enough to get by in front of the mirror and the public both. The brief moments of gender euphoria I experienced were the indication I needed to know there was indeed more and I was on the right path after all.

Once I did discover I was on the right path, then I needed to stay on it and try to navigate all the blind curves, potholes, and stop signs I encountered. Initially, I was naïve and was not prepared for everything I was about to face. I thought I had a fairly good idea of what was behind the gender curtain with the ciswomen I would have to coexist with, but I did not. All of what I was seeing was the pretty clothes and passive aggressive nature without seeing all of what went into it later as I actually made my way into the world. I really misjudged how complex and layered a woman’s life could be if I decided to follow along.

At first, I thought I needed some woman to show me the way but again was so wrong when I tried. By the time I did, I actually had a better knowledge of makeup than she did, so basically, the whole experience was wasted, and I knew I would have to go up my path on my own if I was going to be successful as a transgender woman. Then, I had to figure out what being a trans woman meant to me. As in my earliest days in front of the cross-dressing mirror, I knew I wanted so much more, and I knew it would involve my evolution into a unique woman of my own. As with any other human born female, I knew they needed to be socialized into being a woman and so did I. It just was because my path to womanhood came from a different way than most women but that should not exclude me. Once I felt secure with feeling this way, I freed myself to more completely live my truth in the world with people who accepted me

Surprisingly, I had fewer problems than I anticipated when my trans friend Raquel told me I passed out of sheer will power, that became the story of my life. I was not trying to “fool” anyone into thinking I was the most attractive woman in the room. I was simply announcing my truth to the world, and they could take it or leave it. No more wishing and hoping for me, if someone did not like or approve of me, that was their problem not mine as I paid my dues to be where I was.

As I look back at all the wishes and dreams I had when I hoped to somehow live my dream as a transfeminine person, I know I wasted a lot of my time which I could never get back. Once I did get my late start and began to make up for lost time, I did begin to learn what I needed to survive in the girls’ sandbox once I was allowed in it to play. Once I did, I resolved to never look back and enjoy what I helped to create. A woman with an unique background allowing her to arrive at where she wanted to be.

Before I wrap this post up, I would like to thank Sara E for writing in and commenting. She is in a similar position as most of us went through. A married man, working through her feminine side.

Thanks to all of you who take the time to read my writings and comment!

 

 

Wednesday, March 25, 2026

It was Always in my Way

JJ Hart on Left, wife Liz on Right.
Every time I turned around, my gender issues were always in my way. When I was younger and my life was simpler, the issues manifested themselves mainly around the sports I was trying to play. Since I was never good enough to win consistently, I usually had to head home to my makeup, mirror and skirts to feel better. One way or another, I always was soothed by looking at my feminine self in the mirror.

Of course, with age came complexity in life which included a military disruption of three years during the Vietnam War. My Army training very much was in the way of expressing any of my feminine qualities. Drill sergeants frowned upon any miniskirts or lipstick during basic training. So, I needed to resort to deeply hiding my secrets away, not unlike what I had done my entire life. I kept thinking against hope that someday I would be the pretty girl in the new car I was saving up for. I did get the new car, but being the pretty girl was very much up for debate and something I was always trying to achieve.

To remove the obstacles, I faced to living the transgender dreams I had, I needed to do a lot of living I discovered. Life was never going to be as easy as just looking the part of a ciswoman. If I truly wanted to go through all the living to earn the title, I needed to get out of my shell and into the world as a novice trans woman. Sadly, as I followed my gender path, there was always something emerging to get in my way. Such as a wife, family, friends and job which I did not want to risk losing. It seemed the better I did as a man, the more I had to lose.

All along, I thought the gender curtain would be more of a gentle barrier to cross to see how the feminine half of the population lived without men. I was not prepared for all I needed to go through to earn my way to having female privileges to replace the male ones I was losing. To begin with, I was painfully shy and insecure about talking to any other woman at all. Plus, as I learned all the different forms of communication women use, adding them into my world was a challenge. Such as having to stay in the present when someone talked to me and not try to anticipate what they were going to say. I discovered it was much easier to anticipate what a man was going to say from all my years as living as one, than a woman with non-verbal (eye to eye) communication skills. Not to mention, a ciswoman’s passive aggressive behavior which I misjudged several times before I adjusted to the new world I was in.

When I was able to get communication out of my way, I could move on to other obstacles in my way. I was still having problems with putting together a complete convincing picture as a transfeminine person. I had not practiced enough to feel natural in my world of makeup and high heels to feel natural and relax. Every time I was able to relax and enjoy myself as a transgender woman, I would do something to give myself away. It was not until I quit thinking I was fooling anyone into thinking I was a ciswoman did I do better. Mainly because I was just being me. At this point, I needed to overcome another major hurdle I had when I was a man. I never thought, or was raised to think, I was ever good enough to excel in the world and if I could never make it as a man how could I ever make it as a trans woman. It was a major boulder to move from my path.

It took a while, but I did build the self-esteem as a woman that I never had as a man. I did it slowly with the explorations I took into the world. I was able to build the all-important confidence I needed slowly but surely with the help of a totally new set of friends and acquaintances I built up who had no knowledge at all of my former life as a man. As my wife Liz told me, very few people ever have the chance to start over again, so make the best of it and I was able to. Soon enough, I was as comfortable in my tennis shoes as I was in my high heeled boots, and I was able to build upon nothing being in my way as I built my female privilege.

I knew then, I had made the right choice to follow my dreams into a trans woman world because I felt so natural. The light at the end of the tunnel was not the train as it beckoned me into a new world. It turned out, the main thing that was in my way all along was myself. Once I got me out of the way and for once was truthful with myself, I was able to move forward with a mental clarity I had never known before.

It was certainly worth the struggle to make sure my second chance in life was worth it. Sure, my gender issues were a major hurdle to move but it was no big surprise when I considered how deep gender runs in all humans. In many senses, discovering the true nature of me made life that much more interesting.

 

 

 

 



Thursday, March 19, 2026

How Much Discipline do you Need

 

Image from Brett Jordan
on UnSplash.



One thing I learned the hard way in my transgender travels from male to female was that it took an intense level of discipline to do it. In fact, cross-dressing as a girl was the first thing I ever did in my life which took a large amount of discipline. School was easy enough and sports were something I always tried at but never excelled at.

Growing up, I was always under pressure from my parents to finish any projects that I started and do them right. That is when the struggle began. I have written fairly extensively about how I struggled with the makeup arts when I first discovered all the makeup samples my mom had stashed in a drawer beside her sink in the bathroom. Using the samples meant I would have less chance of discovery when and if she discovered someone was in her makeup.

The only parallel I always use was how I tried miserably to paint all the plastic model cars I put together. My cars never seemed to come out as well as my friends and I really did not want my makeup to be the same failure as my attempt at modeling cars was. For the first time in my life, I developed the discipline to do something about wearing makeup and I set out to become better at it. Which included being able to purchase the right supplies with the meager amount of money I had to work with. I was under a lot of pressure when I did my own shopping for feminine accessories, so I needed to make sure I did not make a mistake and buy something which made me look like a clown in drag going to the circus.

Little did I know, developing discipline in my feminine pursuits was just the beginning of a lifetime search for a transgender future. Every time I turned around, I faced a new challenge, it seemed like I first went out in the world of ciswomen. Where I needed to be better to just survive. A prime example was early in my life as a novice transgender woman, I had a difficult time of getting out of the mirror and putting a complete feminine image together for the world to see. It seemed as if every time I thought my makeup and fashion looked good, my movements and voice were totally off, and I would ruin the whole image. I just had to develop the discipline to do it all and complete myself as a transfeminine person.

Experience was the only way it happened. The more I went out into the world, the more I learned about if I could ever achieve my trans woman dreams. It was very important to me to explore all my options before I made such a huge and important decision in my life. Before long, I was sneaking out of the house every spare moment I had to live the new life I was carving out as a transgender woman. The problem was, the whole experience was terrifying while at the same time, it felt so natural. Further confusing me on which way I should go with my gender issues.

One way or another, I was developing the discipline to conduct myself in the world of women with my own set of standards. I learned to dress and makeup myself to blend in where I was going and more importantly how to communicate with others around me when I got there. It took tons of discipline to do it. Especially when I was making the mistake of trying to live in both binary genders at once. I needed to force myself to make sure I was projecting the right gender at the right time mainly when I was at my job as a successful man. I can’t tell you how many times customers tripped up and called me “mam” when I was going about my male business. Secretly I was pleased but could not show it. The bigger problem I always mentioned was that the gender ping-pong I was playing took a tremendous toll on my mental health. Switching back and forth was terrible.

The only positive was that I developed more discipline than I had ever had before. When I was a man, I knew I was temporarily holding on to a lifestyle I no longer cared about and when I was a woman, I totally had bought into where I wanted to go with the rest of my life. The only thing left to do was to seal the deal and do it. And learn the fine little nuances ciswomen know how to exist in their world. Like figuring out who the alpha female is and going after her approval. Through it all, I was building layer upon layer of confidence in myself. Which I would need later when the dark period of being extremely lonely set in. The intimidating thought of finding anyone remotely able to partner with again looked very dim until all of a sudden it was not. That is when I found my current wife Liz over a decade ago and she made a believer out of my self again and I could drop all my personal defenses to ever loving someone again.

It turned out that all the work I put into disciplining myself into being a totally different person worked out for the best. I emerged from my work with a newfound lease on life as the transgender woman I had always dreamed of becoming. I proved my parents wrong. I could take on a project and see it through successfully. Just not the one they had chosen for me. I tried once to come out to my mom and was rejected and never to my dad, so I doubt they would have ever approved of what I did. Even though what I did was save my own life by shattering my gender shell.

It took a lifetime worth of work to improve my feminine discipline. Mainly because I was blindly entering a world of ciswomen I knew nothing about as my gender workbook was blank when I started. After making up for lost time, I fairly quickly caught up and entered the world as myself.

 

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!

 

Saturday, March 14, 2026

I Could Never Say No

 

JJ Hart with two Special People who 
made it Impossible for me to say No.
Liz on left, daughter on right. 




I discovered early in life that saying no to cross-dressing as a girl was something I could never do.

I tried many times, but I was a miserable failure as the pressure would build to run to my makeup and wardrobe to look at myself in the mirror. I even went as far as trying to shave the ugly unwanted hair off my legs with my mom’s electric razor. When I did, the world seemed to come together for me…for a while. Like clockwork, I could almost predict when the pressure would start to build again to cross-dress. Like most of you, I even purged or threw out most all of my feminine belongings in a wild rush which felt so good at the moment, until my old urges came rushing down on me. Saying no was just not an option.

For a while, I thought being feminine to the point of living as a transgender woman fulltime was always going to be just a dream. At other times, I thought that some point in my life I would just outgrow my gender urges and revert to a fulltime male life, no matter what my brain was telling me. I guess you could say, sometimes I thought a permanent purge would be in my future. I was kidding myself. That permanent purge never came as I tried many times to no avail. It seemed each time I tried to say no, my urges to follow my transgender needs came back even stronger. This time fueled by the positive feedback I was receiving when I was able to present better going out in public as a novice trans woman in a world of ciswomen. Just entering their world was much more difficult for me than I ever thought possible.

One of the problems was my old male self and my second wife did not participate in my dreams. It was far from my wife’s fault because none of what I was doing was anything she signed up for when we got married. She tried to help as much as she could, but my dream was growing so fast I could not control it. I started out the marriage as a cross-dresser and now I was into a transgender woman, and I did not have the courage, or knowledge to explain it. I just knew, I could not say no to pursuing my dreams. I am sure all she saw was her man slipping away. Sometimes slowly and sometimes quickly and I understood why she did not like it.

As I said, I really always knew saying no was not an option in my pursuit of a transfeminine life when I really went out into the world and found myself in the middle of new friendships who knew nothing of my past. growing Just trying to look the part of a woman faded away as I always thought it would when I found myself at the point of wanting to be that woman. Doing my best to communicate with the world on their terms. As I continually searched my soul for guidance on the path I should take, the answer always came back the same. Follow your instincts and do what you need to do to feel natural. With input such as that, why should I ever say no to myself again.

Finally, I reached the point of no return in my life when I needed to look at myself in the mirror to see who I really was. With no makeup at all one morning, I had a chance to see the real me and the words my wife Liz said to me came through loud and clear. There was no male in me and for once everything with a “no” word in it made sense. Plus, I was mentally exhausted from fighting myself all my life. I had enough, and it was time to make my final decision.

When I replaced no with yes, my life opened up to new horizons I never thought possible. Yes, meant I could be the long-hidden self I could never find. If you are on a gender path of your own, I hope you can do a better job of facing your truth than I did. I kept saying no too long and missed a significant amount of my life trying to outrun myself. On the other hand, changing a gender is a huge move, and one that cannot be taken lightly. You have to get to the point where saying no is not an option to you anymore.

 

 

 

Friday, March 13, 2026

The Power of Fear

 

Image from UnSplash.


The power of fear has always been a major factor to be dealt with as I made it through life.

At the beginning, I always used to run from fear by heading home to my makeup and skirts. Then, when that did not work as well, I needed to find another way to deal with the stress my fear brought on. All of a sudden, the extra feelings I brought to the whole cross-dressing experience began to be intertwined with the fear I felt about having my deep dark secret discovered. Every time I was not discovered, the relief I felt was intense.

As I grew older, the stakes I felt grew bolder when I took my image in the mirror public and into the world. The more I attempted to do it in public, the more my fear of discovery grew right with it. I guess it was because at the same time, my male life was flourishing and it was becoming riskier to give it all up, no matter how self-destructive I continued to be. I operated with the idea that if I had nothing to lose in life, it would be easier if I was discovered and life as I knew it came to crushing down on me.

My prime example of turning abject fear into success came from the night I decided to try going into one of the big venues I had visited as a man but this time as a woman. Something clicked in my mind, saying I was no longer a cross-dresser, I wanted more, like a ciswoman in the world doing the same things I had done as a man. Before I did though, I needed to see if I could even cross the threshold in the TGIF Fridays I was going to, to try to find a seat at the bar. Sure, I could have chosen a table instead, but I wanted to go all out and try to look for more interaction at the bar instead.

As I sat in the car, before I went in, I was literally so scared I could hardly breathe. I don’t remember how many times I checked my hair and makeup in my car mirror. Finally, I had enough, hitched up my big girl panties, took a deep breath and headed for the venue’s entrance. Deep down I knew if I was successful, I was facing yet another major transition point in my life and I knew I could never go back. Spoiler alert, I worked my way through all the fear I was feeling and managed to have an enjoyable time with the rest of the women just getting off work at a nearby mall. Even to the point of ordering another drink. Plus, I was right, I found my life could never go back to the male existence I was forcing myself to live. I had discovered new transitions as a transgender woman in the world.

More importantly, I discovered fear of what I was about to do in my new exciting world just came with the territory. It became as much a part of me as a well-worn set of panty hose when I went out into the world. Eventually, I just learned to live with my misgivings about giving up all my male privileges I had earned in life. Another example came much later after I had completed my male to female femininization, even to the point of starting HRT, or gender affirming hormones.

It happened one hot summer day when my future wife Liz suggested we go to one of those auto junk yards where you pick your own parts. We needed a side mirror for one of our cars and it would be much cheaper if we could find one there. All of a sudden, my old fears materialized about going back into a male-dominated environment. Again, I remembered the old days when I battled fear all the time and I had to keep reassuring myself I was not back in the not so good old days, and I would be fine. It turned out, all the fear and trepidation I felt about going was wasted because the men at the junk yard barely noticed me as they went about their business and we found a mirror for our car.

These days, since I have been out in the world for over a decade now, almost all my lifetime fears and anxieties about being a woman have passed like I do most of the time now. Mainly, I pass now as old which there is nothing I can do about. There are times when I do miss the adrenaline flow of being afraid propelled me into the world as a novice transgender woman. I do think, however, that conquering my gender fears came from my days in Army basic training when everyday we needed to fight to make it through. Then somehow, I used it all to help me be a better woman. Before I became a better man at the very end before I transitioned because I was allowed behind the gender curtain to get a look at how ciswomen live.

The end result was that fear helped me battle through the conflicts I felt because of gender dysphoria. It sounds different I know, but that is the way it worked for me.

 

 

 

Monday, March 9, 2026

Set in Stone?

 

JJ Hart

When we are born, we are assigned a gender which is arbitrarily based on our genitals the doctor sees. Often, at that point, gender reveal parties are set up by new proud parents. Of course, the problem is what if the child does not agree with how the reveal was going but had no say in the process. That was exactly where I found myself.

I was born as a first son into a male dominated family, so as I grew, I learned what was expected of me. Be a success, compete for it and earn my male privilege was my only path. I was caught with no way out, seemingly, I was stuck in stone. My only path to sanity was the very limited time I had to cross-dress in front of the mirror and try to transform myself into the pretty girl I always wanted to be.

The first time I saw a glimmer of hope in my future as a transgender woman was when I started to go to Halloween parties dressed as a woman, just to see how I was perceived. Overall, I felt as if I got a fair reception and could not wait for Halloween to roll around again. I found I could not wait and began to come up with other ways to test my feminine presentation in the public’s eye by simply going out to malls and women’s clothing stores. Looking back, some of my adventures were just OK and others were brutally bad as I learned what I was doing. One of the main things I learned was presenting as a woman was not set in stone. Often, I could take advantage of the seasonal variations in women’s fashion to change up my own look, which made the fashion process so much more challenging and fun. I needed to up my diet game to fit into more stylish clothes I hunted down at the thrift stores I shopped at. I liked many of them because I could try on my potential treasures in the women’s dressing rooms with no problems.

All of this led me to believe that maybe my gender situation was not set in stone, perhaps I could find my way out of the life I was given. I just needed to be sure that escaping the stone I was in did not put me in quicksand. Or was the transgender frying pan worse than the fire. With my newfound confidence, I set out to discover the answer to as many of my gender questions as I could. I knew I felt an energy in life I had never felt before and it felt so natural that I wanted to experience more. But even with all of that, it wasn’t enough to keep me satisfied with my slow transition. The basic question remained that could I ever gain the courage and where with all to live my dream of existing as a full-time transgender woman on my own terms. Sadly. I was not going to learn that answer for years because my male life kept getting in the way.

By in the way, I mean he kept setting up major roadblocks of my proposed path such as what to do about my wife of twenty-five years and the very successful job I had worked so hard to get. I cherished both of them and did not want to let them go. I am sure, this sounds familiar to many of you in the same situation. Especially when you think your male situation is set in stone and you can’t get out.

I thought the same thing for years as my mental health deteriorated as I drank way to much trying to self-medicate my problems. The part I never understood was how I could think what was true today would be true tomorrow. Destiny for me completely turned me around during the dark days when my wife and almost all of my close friends passed away, leaving me almost completely by myself. Except for my daughter and my brother. On top of all of that, the Veterans’ Administration healthcare system, which I was a part of suddenly approved the use of HRT or gender affirming hormones for qualified veterans who were approved through a therapist to receive them. I was approved and prepared myself for my second puberty and the greatest most profound changes of my life.

Suddenly, everything I thought was set in stone, was not. I was free to live the way I had prepared for all my life had come true. I could even dare to be happy for the first time in my life. It was always set in stone that happiness could not be part of my life. Thankfully I was wrong about that. It was just a matter of learning where I truly belonged and then getting rid of that giant roadblock I was born with. My so-called gender because it turned out to be true, I was never supposed to live a male life after all. All the years of struggle and emotional pain were wasted on a fight that I was never destined to win.

As I always say, I was not a man cross dressing as a woman, I was a woman cross dressing as a man to just get by in life. I was fortunate in that my gender destiny was not set in stone no matter how determined my family around me was to keep me male, I always found a way to sneak around their backs and keep that feminine flicker of hope alive. Now it is able to burn brightly due to no small help from mainly new friends and family. Roadblocks were moved and now the path is straight and smooth as I am able to live the dream I always wanted.

As I said, remember that today does not dictate what tomorrow may bring. I always say, life can change on a dime. If you can find the dime.

 

 

 

Thursday, March 5, 2026

More Euphoria

 

Image from Marcus Winkler 
on UnSplash.

Yesterday, I wrote a post describing the joys of gender euphoria and promptly received this comment from “Joey”:

Hello JJ! I am Joey. I discovered your blog today from a link on Stana's blog, femulate.org I am a crossdresser who presents male while wearing tasteful, feminine outfits. I do feel some euphoria, primarily when I have been out in normal life while dressed pretty for a couple of hours, and all of the stress hormones go away. Only my wife and a few other people know about this side of my life, so it is stressful when I go out in public every week or two. But after the stress, it is very freeing and happy!

First of all, Joey, welcome to the blog! Hope you enjoy it. The feelings you described were similar to mine too. I know I could not wait until I could shed my male clothes, wear something pretty and sample what the world had to offer for me that day before I had to go back to my old boring stressful male existence. Sure, I felt stress going out as a transgender woman when I first started to do it, but it was nothing compared to my male life. When I was mistaken for a ciswoman, my heart literally sang with joy, and the best part about it was, it all felt so natural. What a homecoming!

My only caution about seeking out more of the male to female femininization process is, it led me to take premature chances with my life. I did not understand all the layers that went into a woman’s life and the only way to gain understanding was by doing it. It was only then that I was given the opportunity to look behind the gender curtain to see what really went on. As I did, I was surprised to learn that many things were the same and women learn in their lives to keep certain things secret from men. Which is why both genders have such a difficult time understanding each other. For example, ciswomen have developed two basic ways of negotiating their lives which have to be understood by any novice transgender woman.

The first is the use of non-verbal communication. Women often give information to other women through their eyes and bypass men all together. I can’t tell you how many silent warnings I got from other women when I was in potential danger from a toxic male.  The second major lesson I learned was how to operate in the new world of passive aggressive women. I needed to have my head on a swivel to look for some other woman coming after me after she initially was smiling and was nice to me. I looked at both of these major changes in my life as just another way of playing the game, and the only problem I had was switching gears when I had to go back to my male life. I had built a career of being aggressive in my business and the change was often difficult for my mental health.

Even though the path went quite slowly for me several times in my life, on occasion, it sped up. Almost to the point of being out of control. My male self-had a unique way of saving his existence when it was on the brink of being taken away. Which made matters worse in my convoluted gender world. How could he continue to be so strong in his resistance when my gender euphoria was so strong when I was successful as a trans woman? I am sure you can understand my dilemma and perhaps have even been there yourself. Somehow, someway, I needed to arrive at a point where I did not define myself as a transgender woman. I defined myself as just me.

Sadly, that point did not come for many years in my life. As my male self-fought long and hard for his right to live on in the world he was successful in. Many times, I good old shot of gender euphoria was all I had to keep going if I was ever going to have a chance of reaching my feminine dream of attempting to live full time. Fortunately, for my life-long dreams, my gender euphoria turned out to be strong too, in its own way. Far past the feel of hose on shaved legs and the sound of my high heels when I walked, all the way to having the confidence knowing who I was. Acquiring the ability to look and another woman eye to eye and communicate on her level was so important to me as I needed to break the communication gap I had with the world when I started to live as a transgender woman.

I am aware that gender euphoria can be different for all of us as we follow our gender paths. Referring back to “Joey’s” comment that she enjoyed being tastefully dressed when she went out. That became so important to me too when I was able to begin to blend into the everyday world as I knew it. Out went the too short miniskirts, replaced my more tasteful denim skirts was a prime example. I was told my legs were always a fashion positive for me so I wanted to show them, but I learned moderation was the best way to go when it came to my male to female femininization process. When I did, my moderation led to a different kind of gender euphoria when I searched for the best way to find my dream.

Euphoria, I found, is also joy of living in a feminine world. Where I always dreamed, I could be. More importantly, once I got there and was living my dream, it was everything I thought it could be and I started to wish I had not waited so long to do it. Of course, thinking that way was just wishful thinking because we are given only one life to live.

I learned I had made the best choice I could and living as a woman was the way to do it.

 

 

The Last Line of Defense

  Image from Gayatri Malthroa   on UnSplash . Throughout nearly half of a century, my male self -fought the complete transition I made into ...