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.

 

 

 

 

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.

 

 

 

 

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.

 

 

 

 

 

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!

 

 

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.

 

 

 

 

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.

 

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!

 

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.

 

 

 

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.

 

 

 

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.

 

 

 

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 Dream was Never Out of Sight

 

Image from Egor
Vikrev on UnSplash

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

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

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

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

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

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

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

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

 

Everything was OK Until it Wasn't

 

JJ Hart. Frozen in Florida

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

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

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

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

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

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

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

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

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

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