My Gender Timing was Everything

 

Image from Danny G
on UnSplash. 

For me, timing was everything when it came to completing my male to female gender transition. Plus, there was no way possible to think I would take nearly a half of century to do it.

The problem was, I never considered the extra layers of a ciswoman’s life rather than what a man had to go through to live. Just having to put up with a man in a relationship would have been enough for me to drive me into a lesbian relationship. Although I never really understood why more men don’t want to accept trans women because we understand so much about the way they think because after all, we had to live as a man for a while. But that is a long, drawn-out story to be saved for another time.

In many ways, timing comes down to everything when you decide to jump out of your closet and enter the world. Just a few things to consider are what would happen to you if you were out as your authentic feminine self and ran into someone you know. It happened to me one time long ago when I was married to my second wife. I was happily following my shopping routines in the small Ohio town we lived in when I parked in a parking lot, slid out of my car and right into the on-coming face of my wife’s boss. As I panicked and headed the other way as fast as I could, all I could hope for was he did not recognize me in my wig, makeup, mini skirt and matching leotard top. Fortunately, as I got a quick glimpse of his face, he showed no reaction to me at all.

I thought the experience was behind me until a week or so later, we were invited to a party at their house. At the party, her boss casually brought up how he had seen this big woman at a big box store he was shopping at the other day.  As I ignored the comment the best I could, I saw my wife suddenly glaring at me from across the room, and I knew what she was thinking. It was me; her boss saw that day. It took me a long time to live that one down because I was never supposed to leave the house as a trans woman unless I was somehow supervised.

Timing kept me living on the edge with my job too. What if my “hobby” of being a cross dresser was discovered? I knew I would not be able to function the way my male self-had all his life. I was stuck between the rock and the hard place on several personal fronts. I was becoming increasingly dependent on my lessons I was teaching myself as a woman and keeping my personal life together. All I could do was keep on working towards my dream of living as a transfeminine person. As I progressed along my often-rocky gender path, all I could do was look for a quick exit. But I found out, exits were as rare as on a long-deserted interstate highway.

It was not until I reached my mid-fifties, did I begin to see the faint out-lines of a possible gender exit ahead for me. All I needed to do was time my male exit correctly so I could cover the main living basics such as spousal support (or nonsupport), a job to support name changes, all the way to all the identification forms I would need such as a new driver’s license. For me, the name change was the most challenging because I needed to go before a very conservative judge I even knew before as a man. Surprisingly, he just smiled and approved my paperwork and name change and the rest was basically easy. So timing on that exit went smoothly with no roadblocks.

Other exits were not so forgiving for me. Such as what was I going to do about a job at that time. I had just closed my restaurant and was essentially broke, and I needed to find a job fairly quickly to support myself. I guess timing was everything and I took an easy exit into a job that I hated. I took the job anyway and managed to keep it for the couple of years I needed to work to claim my early retirement and keep myself afloat by selling vintage collections that my deceased wife and I had put together over the years. During this time of my life, there were other main detours which were difficult to navigate.

That was when my current wife Liz stepped in along with a huge push from destiny to erase any doubts in my mind that I was making the right decisions. I can not forget to mention this was also the time when I was able to begin HRT or gender affirming hormones and take another smooth exit away from my old male life. Putting him in my rearview mirror was the best move I had ever made in my life. I had a new me to go with my new name, and I was ready to go by the time I hit the age of sixty-two. I did not even have to revisit another job exit and just totally retired and moved in with Liz. Where I still am nearly a decade later.

Timing was everything for me, and even though it took me longer than I ever expected to reach my dream, the trip was worth it and I managed to even stay on a very rocky gender road full of roadblocks without wrecking.

 

 

 

Who Won the War

 

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

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

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

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

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

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

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

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

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

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

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

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

 

A Labor of Love

 

Image from Mor Shani

Lately, it has occurred to me that possibly my posts have been a little negative when describing my journey along my gender path. Sure, my trip had its ups and downs but overall, it was a labor of love. Gender euphoria always seemed to come along at just the right time to keep me centered on my dream of living a transfeminine life. Finally meaning to me that transitioning male to female was the only way to live for me.

From that point forward, I just had to figure out a way to do it. I knew I loved the lure of women’s fashion and makeup, and how it all changed around me on a seasonal basis. So far from the male fashion I was used to. Instead of just putting on a coat when the weather became cooler outside. Now I needed to choose between leggings, boots and fuzzy sweaters to keep me warm and stylish.  Furthermore, I loved the concept of seasonal change and the desirability of going through my wardrobe to see what could stay and what had to go to the thrift store.

Even though, fashion and makeup remained a priority for me, a new love interest set in when I began to explore the world more as a transgender woman. Whole new gender vistas opened up for me relatively quickly as I needed to put my static mirror version of my trans woman self into motion. It became a labor of love to go out and start meeting new people. As I did, I came to the realization that most strangers I met did not mistake me for a cisgender woman, but on the other hand, I could be quite satisfied to be recognized as myself…a woman from a different background. I think in a couple of the venues I became a regular in; I became their token transgender woman to prove their overall diversity. Whatever the case, I loved the extra attention I was getting. Especially from the ciswomen I met who were basically curious what I was doing in their world.

All the on hands experience in the world I was getting helped me to want more and leave my male life behind. As I always say, the gender change concept seemed to be so natural for me as I went forward. The only problems came from wondering what I was going to do about all the male baggage I carried with me. I discovered I was much more than a man trying to put on a pretty face, I was a full-fledged person trying to build a life from scratch. All the nuances of doing so extended way psst making sure my shoes matched my purse, all the way to wondering how I was going to handle the woman sitting next to me when and if she tried to make conversation. In a very short period of time, I became used to the challenge, and it became part of my life and yes, I loved it.

As I increasingly loved this new life I was living, I was able to balance between the two main binary genders. Before it became too much to handle mentally for me. It became increasingly evident that if I was going to survive as a person, I was going to have to choose one of the genders pulling on me. At that point my lifetime of loving everything feminine kicked in for me. Long ago, I had realized I was much more than a casual crossdresser and made it a love affair to learn more about my dream of being a woman on my own terms. Which meant I did not necessarily need all the extensive facial or gender realignment surgeries. I just needed to present well enough in the world as a trans woman to be left alone. Mainly because of the circle of ciswomen friends who accepted me as an equal, I was able to achieve my goal. Even with the added surprise of finding a woman who loved me the way I was.

The tragedy probably was I did not realize the depth of the love affair I was having until much later in life. I would have preferred to have spent more time living as a transgender woman in a world I created. Rather than sharing it with a man I started a life with and had very little control over.

I will never know (of course) what life I missed and maybe the course of destiny I was on would have stayed the same anyhow. Just being able to acknowledge the lifelong love affair I was on is just enough to rationalize where I ended up. So if you are just starting or contemplating starting your journey, try to look down deep inside of yourself to see where your love affair has taken you. It may save you problems later on your journey.

 

 

 

 

Reflections on a Theme

 

Image from Alexsandra King
on UnSplash. 

Reflections on a theme could really go several ways.

The first one goes all the way back to my earliest days of gazing in the mirror at my new girl-like figure. Since I did not have much to work with as far as clothes and makeup went, I needed to use a lot of my imagination when I looked at myself. All I remember is, every article of clothing I could wear was cherished and I hoped I did not destroy it and clue my mom into someone had been into her clothes.

On the other hand, makeup was a little easier to hide, since mom had a whole drawer full of used makeup and samples for me to experiment with until I arrived at the point where I did not think I looked like a circus clown doing drag. As I said, imagination played heavily into my girlish pursuits back in those days until one fact came in loud and clear. Just dressing like a girl fell far short of meeting my expectations of how I wanted to feel. More than just looking like a girl, I wanted to know how it would be to feel like one. It turned out to be an idea I would carry with me throughout my life. Little did I know I would be writing about the same theme some fifty years later as I still struggle to understand all the aspects of the gender dysphoria I went through before I just gave up and went to my dominant side which was OK because in her own way my mom was a dominant woman and had to be to survive in the world of men she was in.

I guess you could say mom was the first feminine role model I had. As I reflected on her, I saw a person who worked hard to get a college degree during the depression years then ran off with a man her parents probably did not totally approve of. In other words, she was strong-willed and often got her way. Except for the daughter, she never knew she had who was watching more than just the way she applied her makeup. I was watching how she navigated the world. In my own way, I went through my own great depression as I learned how difficult it was going to be to be a transfeminine person. Long before the term was ever used.

During this time, I spent a lot of time reflecting on who I was and why I was this way. Surely, I was one of a very few boys around me who wanted to be a girl. One of the many ideas I reflected on was the fact that I was simply afraid to go out and compete with the other boys. Which even though was probably true to an extent, I knew I had to do it anyway, so I had no choice but to make a half-hearted attempt at doing boy things to throw gender doubters off my path when they realized what an effeminate boy I really was. Since I was not athletic enough to hang with the jocks or smart enough to hang with the brains, I ended up taking some sort of a middle path with a group of troublemakers which at least kept me away from the bullies. Sadly, there was no group for boys who wanted to be girls.

As I stayed in the mirror for years and years, I built up quite the love for my reflection as I went along. So much so that I caught my reflection lying to me. No matter how ridiculous I looked, the reflection I was seeing told me I looked great which hurt my overall feminine approach to life, out of the mirror. It was not until I gathered all my courage and began to explore the world as a novice crossdresser ot transgender woman, did my reflection begin to change. What happened was, for better or for worse, I traded out my home mirror for one in public. As strangers began to notice me, I very quickly received feedback on my reflection from them. Was I convincing the world that I was a serious transgender woman and not some sort of a joke or someone up to no good that was all the craze back in those days on television and in the movies.

All of this reflection on a theme quickly became very important to me since I had finally made the move to get out of my closet and see the world through the eyes of a very serious trans woman. Soon I reached the point of no return and just had to rely on my home mirror to apply my makeup and fix my hair. The rest was up to me to do in the public’s eye, where my true reflection always was. My theme always should have been I was a feminine based individual all of my life with strong ties to woman role models. My goal never was to be the, “Pretty, pretty princess” as my wife called me. I was just going through a phase so get to a point where I could become a strong independent trans woman. I did not know at the time how much the world would change and I would need every bit of my new self to survive under a corrupt president who wants to erase the LGBTQ community.

Now, when I see myself in the mirror, the only reflection on a theme that I see is me. I am a survivor of my internal gender dysphoria wars and external problems along the way too. Some were interesting, some I learned from and most were quickly forgotten as life intervened. All I know is, I would never have found out if I had been stuck in my reflection on a theme. Which was being a woman. Being stubborn enough to keep pushing ahead was what kept me going. Deep down, I knew I was right.

 

 

 

 

Practice, Practice, Practice

 

Image from Mor Shani
on UnSplash. 

Sometimes I wonder if some people don’t take the time to understand how much practice I needed to do as I became my authentic self. I guess I could say I went through nearly a half century of work to become who I dreamed of being. It was far from easy.

Starting at the beginning, I never had much to work with as far as being an effeminate boy. Not to mention, I was born into a very male dominated family. Very early I learned I was going to have to work hard to not look like a clown in drag when I tried my best to look like a pretty girl in front of the family mirror. I always equated putting on makeup with painting the plastic model cars I had. Which I was always very bad at doing.  

It did not help when I earned my own meager amount of money working around the house or delivering newspapers in the neighborhood. Then I used the money to try to shop for makeup. I still remember to this day, the first time I was confronted by the sheer number of various makeup brands and variations to try. I finally selected several products out of desperation and hoped for the best as I was trying not to use my mom’s makeup anymore. Now, I don’t remember how successful I was, but I kept on trying to practice on my face until I got it right. Or so I thought. It wasn’t until years later that I visited a true professional makeup artist that I discovered I was not working on the true potential of my makeup to its maximum effectiveness. I was merely making the same basic mistakes over and over again.

I was fortunate to have the makeup artist who was able to explain to me in terms of understanding what he was doing, so I could repeat the process later. Practice for once made perfect. I was able to paint my model cars in a way that my friends admired them. But this time, I was actively admired at the crossdresser-transgender social mixer I was at, and this time when I tried to hang out with the “A” listers (as I called the beautiful, more advanced crowd of attendees) I was accepted. The best part of the whole evening was I then had a basis of where I needed to be as far as being an accomplished cross dresser but on the other hand, I was presented with a deeper set of questions about what I was going to do about my male life as I knew it.

What I decided I had to do was take my transfeminine show on the road so to speak and see if it would play at all in the public’s eye. Away from all the safety of mixers and gay or lesbian mixers. That is when the real practice set in. I needed to stop all of the hard-earned male muscle memory I had learned and start to learn the best that I could the graceful, fluid moves of a cisgender woman. Naturally, the whole process was difficult to do. Especially when I was switching back and forth between the two main binary genders almost daily. Constantly, I needed to remind myself of who and where I was so I would not end up at the wrong place at the wrong time.

Through it all, when I thought I was being successful in going down my transgender path, roadblocks always emerged which sent me back to my drawing board and started setting up more practice. Those were the days of taking every spare moment I had to sneak out of the house and begin to carve out a new life for myself as a trans woman. Once I made it successfully out of the gay venues I was going to and into a few of the big sports bars I was used to going to as a guy, I started to relax and enjoy my new exciting life even more.

No matter how much I try to gloss over this part of my life, the fact still remained I was essentially cheating on my wife when I went out as myself. Deception was never my strong suit, and I was never proud when I needed to lie about what I was doing. By this time, I had reached the point of no return but still was afraid to face it. I hid it by staying in the so-called practice mode I was in. If I could have just one more experience being a transfeminine person, it would make it so much easier when I decided to permanently put my old unwanted male self behind me for good.

Finally, I quit kidding myself, and I was doing so much than practicing over and over again to live a transgender life. I had always dreamed of doing it, so it was time to do something about it and live it. Who knows, maybe all that practice at living a feminine life saved me in the end as I finally learned to move and communicate my way around in a ciswoman’s world.

 

You're so Vain

 

Image from Ava Sol
on UnSplash

Expressing yourself to the world as a transgender woman carries with it a certain amount of vanity.

Until you begin to relax in your new feminine world, I think you need to obsess over every detail of your exterior appearance. Since we all have such a vast amount of catching up to do to compete with other ciswomen in the world, details matter. Perhaps one of the first lessons you learn is how competitive the world is when you are a trans woman. Ciswomen are every bit as competitive as men but in certain areas not readily visible to the male gender.

For example, the major question comes to mind that do women dress for men or for each other. Sadly, we never had the input of mothers, sisters or girlfriends saying, “are you wearing that?” I know if I had that sort of input, it would have saved me a lot of embarrassment when I first began to go out into the public’s eye. It was a resounding yes for me when I learned who women really dress for…themselves. My problem was, my male self-kept getting in the way and had me dressing like a trashy teen girl. All poorly concealed in a testosterone poisoned male body. It was no wonder I was creating negative attention and getting laughed at. When all I was doing was trying to present myself well the best way I knew how.

After I began to learn and change my thought patterns concerning fashion and makeup, I began to have success in the world. So much so, that on occasion (when I was so vain and did everything right) I received a compliment or two from a cisgender woman. One thing was for sure; it takes a woman to know the work it takes to perfect a public image with makeup and fashion. Plus, I needed to be better than the average woman because I was working at the whole image after I started as a man.

It turned out, having to be better in the world worked well with my increasing source of transfeminine vanity. All I thought of was how much better I could look if I tried just the right foundation and mascara, as I haunted the many thrift stores, I went to looking for just the right piece of clothing to add to my wardrobe of feminine clothes. My personal newfound male to female femininization vanity was in full force as I was having fun. In reality, I saw nothing wrong with being vain in how I appeared as my authentic self, until I clashed with my second wife.

She rarely wore makeup or dresses at all and did not like the way I presented myself at all. On the rare occasions we went out together as women, I tried to tone down the amount of makeup I was wearing along with putting on my most conservative clothes. All because I wanted her approval, which I never got. If I wore any less makeup, I might as well say to hell with it and go out with her as my old male self. I was stuck between the rock and the hard place as far as my feminine vanity was concerned.

As I progressed with my makeup and fashion experience, I understood how much work I would have to put out to achieve the transgender goals I wanted. I knew I would never be able to transform my old male self into the prettiest girl in the room but on the other hand I could present well enough to get by. Everything that I was doing at that point just became a blur of change. Especially when I was approved for gender affirming hormones or HRT. As my skin softened, hair and breasts grew, it all was a welcome addition to all the work I had done all those years to just survive in the world. As I wrote yesterday, just not having to wear a wig anymore was a huge deal for me since I had no male pattern baldness to contend with. All of a sudden, I needed to contend with a new form of vanity when I went to beauty parlors to have my hair done just a certain way.

During all the years it took me to fully come out into the world as a trans woman. I learned the true meaning of competing with ciswomen in the appearance arena. Once I did. I needed to move ahead to the larger context of being allowed to exist in women only spaces by the alpha-female gatekeepers. In many ways, my second wife was an alpha female who never let me in, so I wonder what would have happened if she had lived long enough to see/know the person I am today. One thing is for sure; I am no longer the “pretty, pretty princess” she used to call me because I have paid my dues as a transgender woman.

All I know is I did go through my periods of extreme selfishness and vanity to arrive where I am today and I don’t know if there is any other way to go down the path, I ended up taking. Changing a gender is such an intense way to live, especially when you started with so much success as a male that it took me a massive effort to change. Not to say, all of the effort was not enjoyable but at least, it was interesting and challenging to see behind the gender curtain.

For many of us stuck in our own form of gender dysphoria, vanity is just one aspect of our larger need to survive.

 

 

 

Dark Side of the Gender Moon

 

Image from Maria Kovalets
on UnSplash.

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

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

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

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

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

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

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

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

 

 

 

 

 

 

 

Fearing Change as a Gender Challenged Woman

Image from Joshua Gaunt 
on UnSplash. 

Gender change came so very slowly for me during my life.

First, I needed to free myself from the male bonds I was born into which I had no control over. Looking back, I think one of the main problems I had was fearing the changes I was looking to go through if I faced up to reality. From that point forward, life became a struggle as I feared changing it.

What I became was the best transgender procrastinator I knew. Any excuse I could come up with not to go through with living my dream, I clung to like a survivor on the Titanic. What I would do about spouses, family and employment were a few of the major questions I was asking. So, what did I do? I ran as hard and as fast as I could from the problem. I was running so hard, I even changed jobs very quickly so I would not be bored with my life as a transfeminine fugitive. Eventually, even though I grew tired of the pace, I found a stable good job and settled part of my life down. I say part of my life because during that time my gender issues were raging out of control.

Even though I was slowly becoming successful at blending my feminine self in with the world of cisgender women, I still had many fears to conquer. Just when I thought life was improving for me, I would hit another roadblock and send me running back to my cross-dressing drawing board. Which was crazily marked with clownish makeup until I got it right. The fear of applying skilled makeup kept me occupied for years it seemed. On the other hand, when I got my male ego out of the way and realized I needed to dress for other women and not men, did I begin to improve my overall look and the laughter I used to receive in public began to die away. When it did, I learned the most powerful force I had to combat gender change was having confidence in myself. Surely, I would never be the prettiest most beautiful woman in the room, but a lot of other cisgender women were not either and they were surviving and even thriving just fine. There were many layers to building womanhood and I just needed to find mine.

For some reason, the more success I felt as a transgender woman, the more fear I had. I guess it was because of my old male self-starting to panic because he was losing his dominance over my life. For years, what had seemed like the impossible gender dream was now looking as if it could become a reality. As he fought his new reality, the stakes towards living a successful life as a trans woman, increased dramatically. Every step I was taking towards my dream seemed to feel as if I was walking in quicksand since at any time, life as I knew it could be disrupted beyond repair in the little backwards town I lived in. I still lived in mortal fear that any day I could be discovered and the acquaintances I had built up over the years would realize I was living a gender lie. Which I was.

I finally made it to a point where I could not procrastinate my life any longer and I began to use every spare moment to explore the world as a transfeminine person. It all meant I accepted the challenge to finally go all in with making the final preparations for my new life. The bittersweet part of it all was part of my male to female final transition was built on tragedy. In the space of a couple short years, I lost my second wife as well as all of the friends I had built up over the years to death, and I had to start all over again. Sure, I was still afraid to do it but deep down I knew transition was the only way I could go. Suddenly it was up to only me to decide if I wanted to take the ultimate step and try to get a doctor’s permission to begin HRT or gender affirming hormones. I was approved and then the changes I was hoping for began to really happen for me. The changes were so dramatic, I sometimes take an entire blog post to relate them to you.

What frustrates me now are the haters who say that because I took so long to transition, I am not trans enough for them. Normally, they are younger LGBTQ individuals who have no idea of what the world was like way back when I was growing up. We all have our own gender crosses to bear, and we need to understand each other’s journey.

Sadly, there are all those transgender women and trans men who can’t take the burden of gender change fear any longer and tragically try to take the self-harm way out. The suicide rate in our community is completely too high and could come down with proper help and understanding.

In my case, my excuse is I had a heavy dose of ignorance combined with fear and procrastination as reasons it took me nearly a half a century to come out of my gender shell and live freely in the world as a transgender woman. These days, if you can steer clear of all the online trolls and haters, you can still get valuable information on the internet concerning ideas on how to build a new life as a woman from scratch. Plus, fear for me was a powerful motivator and when I was forced into a corner because of my gender, I came out fighting because I believed I was right.

It turned out I was.

 

 

 

  

More Gender Dreams

 

Image from Robin Edqvist
on UnSplash.

Last night I had one of those dreams I always had hoped I would have when I was young. I dreamed I was dressing myself into a pretty woman and actually going out into the world. The experience was different because of some reason I still dream that I am male in the vast majority of dreams that I have.

Even better, the usual suspects in my world at the time were all present and encountered for in my dream. To the point I was even sneaking around my second wife’s back to cross dress. Another interesting point was my hair. As many of you know, through the power of genetics and HRT, I have been able to grow an amazing head of thick long hair at the age of seventy-six. Going without wigs and having my own hair styled was always an impossible dream for me, until it magically happened. Which is an experience for another blog post.

In the dream, I remember trying to choose between wearing a wig and brushing out my own hair, which I chose. For some reason, I was trying to throw caution to the wind and go out for something to eat with just women’s clothes, my hair and no makeup. Also, I was calling my wife at work to make sure she was still there, which was something I always did back then to not get caught. My second wife was the one I lost to a heart attack at the age of fifty and when and if I dream of her, she always is a blur. So, I was surprised when she appeared in this dream. My guess is it is because my habit of sneaking around her back and cross dressing was so prevalent in my life at that time that it stuck in my subconscious. And it just decided to make an unscheduled surprise appearance.

In the past, I have corresponded with other transgender women on how many of their dreams were with which gender. Interestingly, many of them responded that they dream mostly as women. I do too, sometimes, but mainly I am stuck with being a man in my dreamworld. Perhaps it is because I needed to battle so hard to maintain and even advance in a male world, I wanted no part of. I just needed to survive. That portion of my life still equals roughly two thirds of my time on this planet. So, the more time I spend as a transfeminine person should equal out to the more dream time I have as a woman.

Exactly like when I was young and could not wait to go to sleep and dream of waking up as a pretty girl, this morning I did not want to wake up and rejoin reality. It made no sense to me why I felt that way because I have been so fortunate to have been living a transgender dream in a real world for over a decade now. I guess change comes slow in my subconscious, and I should take advantage of still living part time on the other side of the gender border (male).

I suppose I should be lucky I don’t have gender dreams which turn into nightmares. I do hope I have the chance to meet my second wife in another world after I die and finally learn that she accepts me and not just in a dream. Afterall, she was right when she told me to man up and be a woman. I finally did and became happy.

 

 

 

When a Trans Girl is Serious

 

Image from Bruce Mars
on UnSplash. 

When I first came out of the closet, I wondered how I was ever going to convince the world I was serious about jumping the gender border into my transfeminine world.

Probably, before I started to convince any strangers of who I was, I needed to totally convince myself. Was I a cross dresser, accomplished drag queen or what. The last thing I wanted to come off as was some sort of a clown putting on a dress and makeup for laughs. I think, all the time I spent practicing in front of the mirror attempting to learn the art of appearing as a woman paid off. Because in a fairly short time, I was presenting as a convincing transfeminine person in the public’s eyes. I was far from being the most attractive woman in the room but at least I was making do with what I had to work with and getting by and the public perceived me as being serious also.

At that point, I was not getting the negative feedback I used to get when I left my male self and traveled to the feminine side of life. The worst that was happening to me was when other ciswomen gave me a knowing smile. Showing that they knew I was attempting to play in their sandbox or world. Even better was when I began to see the same people over and over again and they knew I was serious about where I wanted to be in their world.

As I gained more experience and began to understand all the layers which existed in a ciswoman’s life, I knew I had a long way to go if I was ever to be successful in pursuing my gender dreams. Then I purposely set out to try to experience new situations as a transgender woman because my feminine workbook was given to me blank. I did not have the same benefit other women had by growing up out of a female birth into a woman. I was doing it exactly opposite as I was trying to leave my male birth rite behind. Something that I had never asked for. Each time I successfully conquered something new in life I tried to experience, I looked for other things to do that I had never done. An example would be, once I conquered just going to bookstores and searching for books on gender, then I gathered the courage to stop at their coffee shop for a cup o joe. After that, I took it a step further and used the women’s room to wash up and check my makeup.

By now, you probably are getting the point of how I was branching out and expanding my life as a new trans woman. The world was becoming so new, exciting and scary that I was like a kid in a candy store and could not stay away. Even if I wanted to, which on certain days I did when I felt all my gender issues were out of control and my male self along with my second wife were aligned against me pursuing a transgender life any farther. The problem was that my inner woman was telling me the path I was on felt so natural and deep down I knew it was the right way to go.

Still, I tried to stick it out and try to maintain a presence in both my old male world and my new transfeminine one. By doing so, I certainly did myself and those around me more harm than good. Very simply, the stress was too much for my already frail mental health, and I took it out on myself and those around me. I needed to figure it all out and get very serious about how I was going to run my life before it was too late. Internally, I was out of control while externally I was just trying to hold on to my wife, job and family as I knew it. I would have not wished what I was going through on my worst enemy.

Thankfully, destiny stepped in and showed me the way.  My wife of twenty-five years tragically passed away leaving no major hurdles for me to move ahead with my plan to start gender affirming hormones or HRT. Amazingly, at the same time the Veterans Health Care System which I was/am part of approved a program of affirming hormone therapy along with a therapist to go along with it. Which I took advantage of immediately. Under her care, I became ultimately serious about the direction my gender transition should take, and I even went to my therapy visits as my authentic self. Even better, my therapist helped me change my legal gender markers within the VA and provided me with the documents I would need to change my other legal markers such as my driver’s license.

Changing my legal name and gender markers finally proved to myself as well ss my inner female how serious I could be about my future. Even still, with all I was doing with my life, a little voice kept telling me I should not have taken the easy way out and tried to get serious earlier in life about who my true self really was. Of all people, my second wife told me to do it on several occasions during the fights we had about what I was doing along the way on my gender path. It turns out I was going to travel it with or without her and it was my duty to make the call that I had to do it alone.

Sadly, I think most transgender women and trans men have a lonely path to follow before they are fortunate enough to find someone to share their path with. It is surely difficult to negotiate alone, and you certainly have to be serious enough to do it.

 

                                                                                                                                                       

Tiny Ripples of Gender Hope

Image from Rosie Kerr on UnSplash.

During the overwhelming sense of darkness I felt when I began to come out of my gender shell, were moments of gender hope and euphoria. More than anything else, they kept me moving slowly towards living my ultimate dream. All I could think of was the possibility of living as a woman later in life.

Having to run and hide my small “collection” of feminine clothes and makeup every time I tried to get in front of the mirror and cross dress did not help. I resented the fact I could not be free to do what I wanted, no matter how radical it was…like being a girl. I could not imagine the pain and suffering I would have if I was caught. What saved me was the vision of a pretty young girl which came peeking on through when I was able to be alone and try on my precious clothes. Even though I was depressed I had to go back to being a boy, the brief moment of femininity carried me through the dark days and gave me a ripple of hope.

Fast forward through the difficult days of puberty and adolescence everyone goes through, I needed to deal with my gender dysphoria also. There were so many dark days when I just went through the motions of life that I did not know what was going to become of me. When I did, I desperately needed to find refuge behind my dresses and makeup to give me hope. Perhaps the only good thing which was happening was that I was slowly perfecting my use of makeup. When all my friends were showing off their painted model cars, I was stuck not being able to show off my new eye makeup. I had to internalize my feelings of hope and euphoria when I saw my new pretty eyes. Sadly, I needed to become good at removing all traces of the makeup so my brother and parents would not notice.

I guess you could say I was in the dark through my college years and beyond until I began to be able to enter the world for the first time as a novice cross dresser or transgender woman. These were the days of attending transvestite mixers and small parties in nearby Columbus, Ohio. Being around like minded people who were searching for their gender answers almost made my search seem normal for the first time in my life. I was so protected from the world in the pre-internet days that I thought I was the only one like me stuck in their own personal hell. I was experiencing ripples of hope for the first time in my life on a scale I could appreciate. I even upped my appearance game when I went to Columbus from trashy woman to hopefully a passable ciswoman. One of my favorite outfits to wear was what I called my knit black out. I paired a loose fitting black wide knit top with a black leotard, shorts, tights with a pair of black flats and my red wig and was ready to go. After makeup of course.

For me, the whole outfit helped me to tone down and refine my look and it worked so well that I had my first ever encounter with a lesbian from the party when we left and went to a big lesbian venue for a break. I learned many valuable lessons that night which provided me with ripples of hope for the future. Mainly, if I could not be as feminine or beautiful as the transsexuals who were there, I still could be attractive myself to have a good time and most importantly, learn to be just me. Developing the future, me gave me real hope for the future as I learned it would be possible to achieve my transgender dreams if I worked hard enough. I had to learn the new transfeminine me meant so much more than the ripples of hope I had gained in the past went way past how I looked and into how I acted.

Suddenly, acceptance became my main goal, as my interior feminine self-stepped forward in my life. I knew who I wanted to be but still was not quite sure how to get there. For example, I knew for sure I did not want to be like the “Trans Nazi’s” as we called them or the bitchy trans women who thought they were better than anyone else simply because of their appearance or the number of gender surgeries they had undertaken. I suppose I should owe them a debt of gratitude for showing me what not to do to be a gracious, friendly transgender woman.

All of this came together for me when I began HRT or gender affirming hormones when I was sixty. I had spent enough life in the dark to appreciate the light and grasp a ripple of hope when I saw it. The hormonal medications proved to be a natural success when I began taking them. My body seemed to be saying again what took you so long. But on many levels I don’t think even I understood the basic limits I went through back in those days to salvage my life through the brief ripple of hope I received way back in the days when I lived for the mirror.

More importantly, I found myself in a situation where I could pay forward my experiences to helpfully help others. Especially those of you who are struggling to find answers on how to escape your dark gender closets and find your own ripple of hope. 

The Rise of Transfeminine Privilege

 

JJ Hart (Middle) wife Liz (Left)
daughter (Right)

When I began to seriously leave my closet and mirror and attempt to join the world as my true self, I quickly lost all my male privileges and gained very few feminine ones. In fact, early on, the only privilege I felt was having doors opened for me by the men around me.

On the other hand, the most extensive male privileges I lost were my intelligence and my personal security. When I was around men, I learned to keep my mouth shut until I was spoken to, which was not very often because I think most all men knew I was transgender and wanted no part of me. And as far as personal security went, I needed to learn what ciswomen know from an early age to keep themselves out of possible bodily danger by being in the wrong place at the wrong time.

All along, during this time, I was wondering when and if the gender teeter-totter I was on would balance itself out and I would see the positives of what I was doing. It took a combination of things happening before I ever did. One was seasonal around Christmas, and the other one was when I decided to give up on men all-together and concentrate on knowing other women. A preferred topic in my mind, since I did not have to consider changing the focus of my sexuality, which had always leaned exclusively towards women. But I digress, the meaning of Christmas and what it meant to me as a transgender woman, is the real reason for this post.

To begin with, Christmas was always a major holiday for me and my second wife especially. Finding an exceptional, unexpected, rare gift was always the priority for me and even my brother’s family. The difference became to me was when I decided the Christmas shopping, I had been doing as a man would be much better accomplished as a woman. If I was able to pull it off, I could accomplish so much more during the Christmas rush I was in the middle of.

First of all, I needed to up my crossdressing game to give me the best possible chance to succeed in my shopping conquests. I went through my closet and pulled out my fancy, sleek, black pants’ suit for trips to upscale malls and my leggings, boots and sweaters when I combed through the huge local antique malls for just the right gift for my wife. I knew if I was to succeed, I had to be better than the average Ciswoman so I would not be potentially embarrassed. Also, the right makeup and hair was a priority because of all the up close and personal time I would be spending in the public’s eye. Through it all, I wondered where the magical feminine privilege would kick in for me.

The first major time it did was when I was shopping for a matching oak bookcase for my wife’s roll-top desk. One night, I found one which worked beautifully in an oak furniture store in nearby Columbus, Ohio. It just so happened I was returning from a shopping trip to a local Columbus upscale mall when I stopped into the store on the way home. After I found the bookcase I wanted, my old male self-wondered how in the world would I get it in my truck/SUV. Would anyone come to the aid of a tall blond in a black pants suit and heels? After I paid, I found out they would because for the first time in my life I was able to sit back and watch two young men load the bookcase carefully into my vehicle and finished their job off with a nice thank you mam. Because I had finally discovered a dose of feminine privilege, the half hour trip home went quickly, and I wanted to do more shopping, but I was out of time and money.

Sadly, once I returned home and had safely unloaded my prize gift, it was time to return to the place I did not want to be…my old male self. On the plus side though, the whole experience taught me (and provided the confidence) to move forward to my dream life of being a fulltime transgender woman and would not have to return home every night in a hurry to switch back into a gender I wanted nothing to do with. My feminine privilege was being established in the newfound senses I was feeling. Especially when I was doing something for others, such as buying gifts.

The experience made all the learning and trial and error experiences I went through during my male to female femininization process deeply worthwhile. There were other Christmas stories to share as I will do later. Such as when my wife decided we would have a special gift giving time for my feminine self.

 

 

 

 

A Trans Girl's First Christmas

 

Clifton Mills, Clifton, Ohio. 

The newly fallen snow around here in southern Ohio has brought back my Christmas spirit and memories of my earliest days of coming out of my gender shell and exploring the world.

Years ago, my second wife and I used to make a regular trip to a wonderful Christmas light display at a place called Clifton Mills, which was/is a restored grist mill approximately twenty miles from where we lived. Even though I did enjoy going with my wife, in the back of my head, I always wondered what it would be like to experience the evening as a woman. Finally, when my wife began to work retail in the book business and had to work many nights, I got the chance to live my dream.

Before I did, I needed to figure out what I was going to wear for my special evening. I knew the weather would be rather crisp and cool, and I even had the chance of snow flurries if I was able to pick the right night when I was off work and she was working. I started my wardrobe with a warm fuzzy oversized sweater I loved and paired it with a pair of fleece leggings which would be warm enough to keep me warm as I wandered around enjoying all the lights and displays. Back in those days I had access to my own finances and was able to come up with enough money to buy me a pair of low-heeled snow boots which would help me navigate the long distances I would have to walk safely and comfortably as I walked through the village to get to the mill itself.

Once I figured out what I was going to wear, I had to make time to apply just the right amount of makeup to blend in with the other women in the crowd. I applied my makeup, got dressed and finished off my outfit with my shoulder length wavy blond wig. As I left the garage and slipped past my neighbors, it was dark, which helped me and my anticipation of what was coming up heightened. Would my expectations of spending my first evening out as a transgender woman at Christmas fulfil my dreams?

The twenty-mile drive seemed to take forever but I finally arrived, found a parking spot in the village, adjusted my makeup and hair and left the relative safety of the car. As I walked, I passed several people who did not give me a second look, so I started to calm down and enjoy myself and breathe in the night air as a free person. I even became so comfortable I stopped in one place for a hot chocolate and another for a hot spiced cider in the mill itself. The reaction to me at the hot chocolate stand was as warm and friendly as the drink itself which helped me to build confidence but the reaction from the younger girl where I bought the cider was as cold as the evening, so I did not wait around to buy anything else.

I found the only real problem I had was the lack of time I had to enjoy myself because I needed to be home and return into a boring man before my wife made it back. The end result was I completely enjoyed the experience of being a trans girl at Christmas and wanted more. The evening proved to me I could present well enough to enjoy myself and the only disappointment came when it was all over. My solution was, I needed to come up with other Christmas related transgender woman activities to test my abilities to present well in the midst of ciswomen doing the same thing. As Christmas approaches, I will share other experiences I had with you which turned out to be fun and eventful

The bottom line was, I found my confidence in my womanhood I never knew I had and at the same time bought gifts for others that meant something. A win-win situation for me and the evening I enjoyed the Christmas lights at the mill somehow were brighter and more festive than ever before as I was able to see them through my feminine eyes. Maybe a precursor to when I started HRT or gender affirming hormones which really opened my world to a whole new set of sensory perceptions.

If I had realized what my body was telling me earlier and reacted, maybe I could have saved myself and others around me a lot of turmoil and problems.