Tired of Looking Over my Shoulder

 

Christopher Morley
1974 movie
Freebie and the Bean.

In a continuation of yesterday’s post in many ways, today’s post is about how I grew weary of looking over my shoulder as a transgender woman.

Looking back, all I can remember from the earliest days I had cross-dressing in front of the mirror were the all too brief moments of gender euphoria I experienced and the all too numerous times I spent looking over my shoulder to see if anyone was going to catch me. Then life as I knew it would be ruined. To stop this from happening, I became very good at hiding my clothes and makeup away from the prying eyes of my slightly younger brother and the rest of my family. I even resorted to hiding a small amount of clothes, makeup and a mirror in a trash bag in a hollowed-out tree in the woods next to our house in the country. Even with all of this hiding, I still found myself spending a lot of time looking over my shoulder.

Somehow, I thought when I grew older, I would conquer all my gender issues, and they would magically disappear, but they just grew with me. The better I became applying makeup and selecting feminine clothes, the more I wanted to do. Like a dog chasing its tail, the more success I had led me to want to do more in the public’s eye. Sadly, as I grew into my high school and precollege years, I was still stuck in the same old routine of dressing at home, hiding from my family and looking over my shoulder. The only relief I remember was the night friends and I went to a high school carnival and one of the male students was parading around dressed as a pretty girl. I was fascinated but again was looking over my shoulder to make sure none of my friends noticed how interested I was.

Which was exactly how I felt when I saw the movie “Freebie and the Bean” in 1974. I did not know it or had never heard of actor “Christopher Morley” who was an accomplished female impersonator. He had a part in the movie which I found amazing because he was so believable as a woman. As with the student cross dressed as a pretty girl, when I saw Morley, I needed to look over my shoulder at my friends to see if they noticed my newfound interest in the film we were watching. I guess I was pretty good at hiding my interest because nobody ever said anything about it.

Moving forward, there were the early cross-dressing days when I was still trying to perfect my everyday presentation as a transgender woman. I constantly worried about someone sneaking up behind me and pulling off my ill-fitting wig. What would I do then? Put it back on or just pick the wig up and run out the door. Fortunately, I never had to find out when I figured it was my inner female paranoia talking to me that I was not looking good enough to pass her standards yet.

By this time, looking over my shoulder became a habit. There was a time when my second wife and I moved to a small town in southern Ohio to run a new restaurant there. In order to suppress all my cross-dressing desires, I started to do the grocery shopping as a woman then go ahead and do a little lite shopping for myself. One day when I was blissfully doing my thing as a transfeminine person, I unexpectedly ran straight into my wife’s boss doing his errands. As bad luck would have it, my wife and I were invited that weekend to a small party at her boss’s house and I needed to really look over my shoulder when I heard him mention to my wife about the “big woman” he had seen in a store. Rightfully so, I was always guilty until proven innocent with my wife and she turned directly to stare the look of death at me. It took me weeks of denial to finally live it down.

Denial, lying and other mistruths became a way of life for me with my wife before she passed away after twenty-five years of marriage. The only thing I am proud of is that I did manage a full out purge six months before she died. To prevent any backsliding, I even grew a beard. Needless to say, I was miserable during this time but nothing like I was going to live through later.

After all the tragedy I went through during this time, I finally had enough of looking over my shoulder for decades and decided to follow my instincts and come out to the world as a transgender woman. Not spending all that time and effort was completely refreshing and allowed me to totally concentrate on my new life as a trans woman.

 

It is Right When you Know it Is

 

Image from Caroline Herman
on UnSplash.

Some have asked me over the years, when did I know it was the right time for me to leave my closet and emerge into the world as a transgender woman. It is a complex question with a very easy answer. I always knew I was having problems with my gender but did not have a clue for years what to do about it.

The only relief I had was the brief time I had to rapidly cross dress in front of the mirror, away from my family and friends. Even when I was able to accomplish my goal of looking like a pretty girl, I still was aware deep down that something was not right with my life. In my own way, I set out to find any gender solutions I could, on my own, with no available sources to aid me. Plus, at the time, my male self was rapidly settling into a relatively successful life, and he wanted nothing to do giving up any of it to my inner feminine self. It turned out, this would be a battle I would have had to face for decades of my life to come. I would spend any available free time I had as a cross dresser, only to have what I learned rejected when I went back to my male life.

The only thing which kept me going was the deep idea I had that what I was doing was actually the natural part of my existence. And the parttime male life was an act. The act which became so good over the years that I shocked a number of people I knew when I finally came out as a transgender woman. I always had assumed they had thought something was up with me when they saw me at Halloween parties dressed as a woman but never did. It was like my male self-tried to dig a deep hole to bury my female self was never quite successful as she kept digging herself out.

The years at that point seem to fly by with the continuing fights with my second wife over considering if I was transgender at all and at the same time, me improving my transfeminine presentation during the times I was out in the public’s eye. I started to do more than just walk around in malls to see if I could present well and started to accomplish small tasks such as doing part of the family grocery shopping as a woman. I found I could do the tasks, and my life began to feel so natural again. The opposite of when I needed to go back to living as a man. It seemed unfair to me when my wife and my male self-ganged up on me to protect their interests in the relationship and I did not know what to do because I was just doing what was becoming more natural to me.

All the infighting only did one thing and that was prolonging the truth from coming out. I had always been destined to be feminine and when the time was right, I would be able to claim my birthright. The longer I lived as a transgender woman among ciswomen I knew I was in the right spot and had to face the facts about myself. My wife unexpectedly passed away from a massive heart attack leaving only my male self to protest any idea of me being trans and starting the HRT medical treatment. Under a doctor’s care of course.

Finally, when faced with the reality of my future life, my male self-gave in to my inner feminine self who had waited so long to live and prosper. More importantly, I was tired of all the internal fighting and knew I had readied myself to make a choice. All the frustrating years of playing with makeup and clothes came back to help me. I did not have to worry so much about my presentation when I made the decision to permanently be in the public’s eye as a transgender woman. I found a great majority of the world either didn’t pay any attention or were just curious of me which was a great surprise. I could relax and enjoy the wonderful new world I had always dreamed of.

When I finally stopped the gender in-fighting I suffered through all those years, I felt like a huge weight had been lifted from my shoulders at the age of sixty. Why I waited so long to face my true self in the mirror and decide to do the right thing will forever be a mystery to me. My only excuse is, I just knew the time was right.

 

A Thing of Beauty?

 

My Trans Friend Racquel.

During my male to female gender transition years, I always stressed to the max about my appearance as a transgender woman or cross dresser.

Every now and then, I go back into my very early blog posts to see what I was fixated on and quickly noticed I was all about how I looked. In those days, I thought being a woman was all about looks and beauty and I wanted to overcome my testosterone poisoned body to achieve what I could.

The big test of my so-called beauty pageant was when I began to free myself from the mirror and break out of my closet into the world. By doing so, I found I had a lot of work to do if I was able to make it in the world as a transfeminine person at all. My first big test was too present well enough that the teen girls would not notice me and send me home in tears. During that time, my makeup had to be just perfect, and I did not want to ruin my mascara and carefully applied eyeliner by crying. Even when my makeup and hair was done just right, I struggled to think I was anything close to being beautiful. I just wanted to be presentable and live my new experience as a transgender woman.

It wasn’t until my second wife began to call me the “Pretty, pretty princess” when we fought about my cross-dressing desires, did I begin to think about what she was really saying. Since she was an attractive but a no-nonsense makeup woman, and she was my idol in so many ways, I tried to tone down my makeup the best I could to please her. On occasion, she would even go out with me as my feminine self, so I wanted to do the best I could to not embarrass her or myself with how I looked. Of course, the problem continued to be I could not get away with wearing no makeup like she did which led to more fighting.

Many years later, after she passed away, I began to build my own feminine self from what I had learned about beauty and how it related to other ciswomen around me. The first thing I did was becoming a better student of women than I had ever been before. I needed to remove the male blinders I still had to get a realistic view of the world I so desperately wanted to enter and be a part of. I discovered I paid an inordinate amount of time admiring the beautiful ciswomen I saw and not notice the vast majority of women who were doing the best they could with the physical attributes they had to work with. An example was, I was always worried about my height as a trans woman until I began to notice plenty of other tall successful women in the world I was in.

I became less of the “princess” and more of the trans feminine person who was just trying to blend in an survive. It was about this time when Racquel, a trans woman friend of mine told me I passed out of sheer will-power. My willpower took me into a world of lesbian women when hers took a different path into facial operations and men. I guess, in our own ways we were successful transitioning into the world at large with her as a tall, slim beauty and me on a completely different level socializing at lesbian mixers with my friends. By doing so, I learned valuable lifetime lessons on how to live my life without the validation of men at all. If they liked me fine, and if they didn’t (which most did not) that was fine too. Afterall, I was not the ideal girl to being brought home to see the family for the holidays.

Years later, after I met my wife Liz and we became serious, it was difficult enough for me to meet her family for the holidays. Her dad was an extremely right-wing gun rights supporter, and her brother never talked so I did not know what they thought about me. I will never know, since dad passed away years ago and her brother lives south of Cincinnati in Louisville, Kentucky. All I know is, I was extremely ill at ease during holidays with the family.

Now, all I know is that I present well as being old with non-age-appropriate long hair. I can’t do anything about my age and love my hair, so it is not going anywhere. Perhaps I am making up for all the years I had to have my hair cut short in my youth and military days.

As with all other ciswomen, over the years, I have learned to work with what I have been given physically. I was extremely fortunate to have found people who accepted me for who I am as I presented as myself out of sheer willpower.

 

What Was I Walking Into

 

Image from the 
Paris Photographer
on UnSplash. 

Many times, in my life, I have wondered what I was walking into. Sometimes, it did not have anything to do with being transgender but many times it did. And sometimes I was wearing high heels which I was not used to which increased the risk of what I was doing.

The main time it did not was when I went into the Army during the Vietnam War. I had no idea what basic training would have in store for me except I would need to get in better physical condition. I did make a half-hearted effort at trying but failed miserably and gave up. On another negative side, I knew I would have to give up all my cherished cross-dressing activities for the next three years of my life.

It turned out, in the scheme of life, three years did not turn out to be that long as traveling the world to three continents kept me plenty busy and I grew used to the idea of not knowing what I was walking into. So much so that I adopted “Call me the Breeze” by “Lynard Skynyrd “as my official song when I was on the radio. Because I was always rolling down the road. Through it all, I learned that my affinity for women never changed. I wanted deeply to live in their world and all the running I was doing would never change that. It was a lesson in life I wished I would have listened to later.

When I served my three years in the military, my restless spirit continued to dominate me and caused me to try to outrun my gender issues. I constantly was trying different jobs in different places unsuccessfully trying to run away from being transgender. Sometimes I had secret agendas, sometimes I did not. Like the time we moved from Ohio to New York City. Somehow, I thought being closer to a more liberal populace would help me to be able to come out of my gender shell. It did not work out that way because of several different reasons which would take another blog post to explain.

Another idea I had which actually worked out better for me was the time we moved from a very rural area of Southern Ohio along the Ohio River to Columbus, Ohio which was a couple of hours away. This time, I knew for sure that I could get back in contact with the friends I had made in years previous at the gender diverse parties and mixers I was going to. I was successful and reestablished myself with the group and tried to make up for lost time and at the same time, settle down.

When I did settle down, I was able to start exploring the feminine world as a transgender woman which meant almost nightly, I was walking into new situations I had never seen before. From gay and lesbian venues to big sports bars, the world was new and sometimes scary. Again, “Call me the Breeze” should have been my theme song due to all the new situations I was facing. Anything I enjoyed doing as a man, I tried to do as a woman to see if I still enjoyed it. Spoiler alert…I did and kept on trying more and more new situations to see if I could handle what I was walking into.

On the flip side, I am hesitant to recommend this type of transgender lifestyle to anyone. Too many times, I boosted my confidence through alcohol abuse and was fortunate to have never caused any major problems all the time I drove when I shouldn’t have. These days I barely drink at all and never drive when I do. The other problem comes from the increasingly nasty anti-transgender reaction which will undoubtedly be stirred up again in the upcoming elections by the orange Russian asset’s minions across the country. We have a close senate race coming up here in Ohio and I am sure I will see the transgender lies about the Democratic candidate before too long. He has run before, and the television ads were nasty.

Regardless, I am fortunate that these days, I present mainly as old and don’t have many problems walking into new situations. I will have several coming up in the next six months or so to keep me on my transfeminine game. I have an eye appointment at the VA as well as a hematology visit coming up soon as well as another bus tour vacation south in January. Not to mention my mammogram which will be in February this coming year.

It has become part of life for me to wonder what I am walking to at my stage of life. Especially hematology where they are going to do a total blood work check up on how my body is working but I will jump off of that bridge when I come to it. Which is what I have done through most of my life. This time I had to do it without all the male privilege I had built up which as scary.

 

 

Up the Down Gender Slide

 

Image from Abbs Johnson
on UnSplash.

Maybe you remember Ralphie (In a Christmas Story movie) who desperately wanted a BB Gun for Christmas and froze up when he was in a department store telling Santa what he wanted for the big day. What happened was Ralphie got kicked down the slide when Santa told him he was getting a football. Finally, Ralphie struggled his way back up the downslide and told Santa he really wanted a BB Gun and was then told he would shoot his eye out.

This scene paralleled my life in several ways. The main one was, I never asked for a BB Gun but got one anyway and secondly, I never asked Santa for the baby doll I really wanted. In many ways, the whole idea of struggling up the down slide when I considered my gender became routine. Instead of shooting my eye with a BB Gun, I became more concerned with hurting my eyes with my mascara stick. Plus, when I tried to hide my cross-dressing activities from my second wife, I tried to be more effective in removing all of my eye makeup so my wife couldn’t tell. It was a challenge to say the least. But not the biggest challenge of all.

First, I needed to break all the male tendencies I had built up over the years. How did I present as a trans woman, all the way to how did I move and communicate. I knew ciswomen operated on a different wavelength than men but how different I never planned on. For example, the amount of nonverbal communication between women surprised me. I quickly learned to watch for the visual cues I picked up when I was in a potentially dangerous situation, I was not aware of.

Ironically, the more I struggled to go up the down slide, the more slippery it became. I had to become more mentally tough as a transfeminine person to even survive in a potentially hostile world. It meant going back to the drawing board when I was pushed down the up-gender slide even more. By mentally tough I mean with my resources, facial feminization would not be possible and there was nothing I could ever do about the testosterone poisoned thick male body, I would have to work with what I had. That damn slide was not going to get to me. What I did do though, was put myself on a highly effective diet which ended up in me losing approximately fifty pounds as well as beginning to take better care of my skin after I shaved every day. By doing better skin care, I was able to use less makeup and look more natural.

With these changes, I was able to actually start climbing up my gender slide, so that someday maybe I could get the baby doll I wanted to have instead of a BB Gun. Mentally, at least.

Other changes I had to make as I climbed to the top of my gender slide was conquering my fear of heights. There came times when I thought I was moving too fast, and I was in danger of losing all my hard-earned male privileges such as family, marriage, jobs and friends. I did not want to beat myself and my male self-had me looking over my shoulder. Then I resolved to never stop working towards my goal of transgender womanhood and moving on to a totally different goal of being able to interact more effectively with the ciswomen I met. I always called it playing in the girls’ sandbox.

Maybe it was my gender paranoia weighing in on me, but I kept seeing potential problems coming at me when I was out of the mirror and into the world. Some turned out to be real, but most were not. I found I did not meet as many gender bigots or anti-transgender ciswomen TERFs as I thought I would. Men were for the most part always standoffish and ciswomen just were not for whatever reason. Maybe, in their own ways, they had climbed their own gender slides and understood what I was going through and did not mind sharing with me.

If you are starting your own gender slide, or even reaching the top, just remember the trip will never be easy. But to coin a saying, if it was easy, would have it been worth it. I know for me; it was the toughest trip of my life. Plus, you are human and will make a mistake on occasion. Especially, when you are not allowed behind the gender curtain to learn the basics cisgender women were raised with. At that point in time, it is up to you to climb your slide and thrive. Not just survive.

 

 

 

 

 

 

 

 

 

Gender "Muscle" Memory

 

Image from Jeremy Bishop
on UnSplash

Perhaps you have heard an elite athlete talk about having muscle memory when they play their sport. Especially professional baseball players who make a living off of hitting curve balls. Which has nothing to do with presenting as a transgender woman, or does it?

I remember the days when I was going through an unwanted male puberty, and I was so self-conscious of how I was walking as a man. I did not want to attract any bullies by thinking I was too effeminate. I must have been fairly successful because I rarely had any problems. I was just a boy who liked sports and cars and stayed under society’s bigotry radar.

Then, when I started to explore the feminine world, I needed to throw out all of my walk like a man training and start to mimic the distinctive walk of a woman the best I could. I took me a while to do it, but I finally came up with a transfeminine walk that did not look like a linebacker in drag. The problem became doing it enough to have it become muscle memory. Mainly because I was not doing it all the time. Spending a day as a transgender woman learning the world, then reverting back to being a man on a job which demanded control was literally mentally killing me. On the days I had to be a man, I felt as if I was in some sort of a gender fog as I could see and feel my dream of womanhood but could not quite achieve it.

What I did was try to practice my feminine muscle memory anytime I did not think anyone was watching. Big box stores later in the evening were my favorites because they were largely empty of other shoppers. Later I wonder if I made the store’s security cameras and they were amused by a man trying to walk like a woman. But, of course, I never found out because I was not doing anything wrong. At least I found out I was being a success as a novice woman when on a few occasions on my male days at work, I was referred to as a woman.

Finally, practice started to make a successful feminine presentation possible for me, and I started to relax when I was out of my closet and the mirror exploring the world. The only problem I ran into was when I became too comfortable and forgot what I was doing. Like the time I was walking through a mall not paying attention when one of my heels became stuck in a sidewalk crack and I twisted my ankle. Lesson learned as from then on, when I was wearing heels, to watch out for cracks in the sidewalks. Muscle memory the hard way.

Until I began to live my life increasingly more as a transgender woman was I able to put the image I always saw in the mirror into motion. The pretty pictures I was able to take of myself were one thing but surviving in the world of cisgender women was another. Every time I thought I had learned all I needed to know, something else came along to shock me into going farther. I was growing increasingly frustrated and again my fragile mental health was suffering. Until I found a good therapist to help me face my truth. I should never had attempted to assume the male role I was in and all of the muscle memory which came with it. All it solved was making my life more complex when I tried to change it and enter the feminine world for good.

Especially with the help of the gender affirming hormones I was approved to take, my confidence as a trans woman grew and any resistance to losing my old male muscle memory went away. I carved out a new life and even found away to be happy in it. I was similar to the very successful baseball player who is winning the world series as my outward motion fit my inward feminine feelings. Even the HRT hormones enabled me to develop my own hips I was so envious of on other women. Anything I could do to come closer to my dream was welcomed.

Having the gender muscle memory from so long ago is something I still think about to this day. Even though I am highly immobile. It was the way I could get started towards another huge step in my male to female gender transition.

 

It's Halloween Season

 

Image from Andrea Li
on UnSplash.

It is finally here, the season that all cross dressers and novice transgender women dream about, Halloween. It is the magical day when we can be ourselves without all the paranoia of being caught and exposed as a man wanting to be feminine. The time when everyone has a chance to cross the gender line and be themselves.

These days, since I sadly don’t participate in Halloween much anymore, I don’t write much about it. But back in the day, I was fanatical in my Halloween preparations. Without fail, I would begin thinking of my “costume” the first of October and change my mind several times before Halloween itself. I always felt a transgender woman had the right to change her mind. Would I try to be sexy this year or try for a more authentic “costume” such as a professional woman look. Major decisions I needed to make with the added pressure of knowing it would be another year before I could take advantage of the parties again.

Ironically, the “costumes” I chose followed in many ways my progression as an early transgender woman. In the early days, I would try to dress sexy and get away with the shortest mini dresses and highest heels I could find. Of course, then, I would give myself away as more than just a casual “jokester” at Halloween by shaving my legs, wearing a long sexy wig, and having great looking makeup. Which my wife took credit for when she wasn’t and didn’t wear any makeup at all. Even the most casual ciswoman observers at the parties I went to could tell how serious I was about looking my best as a woman.

As I said, I quickly grew out of my sexy/trashy Halloween costumes and began to dream of being accepted my mistake as a “real woman” at the parties I went to. That began my era of actually being mistaken for a woman just getting off work and coming to one of the parties I went to. I was professionally dressed in a dress and heels and ended up surprising other guests I had known for years. For the evening, I went with another woman other than my wife and had to sadly turn down a request to go with another couple to a different party. Later on, I learned that the man was a politician who was elected to Washington, so my political career was quickly ended by saying no.

Outside of that party, there was only one other party I went to when I was dressed in a moderately sexy “costume”. It was during my stay in New York and another night I got out of the house without my second wife going with me, for some reason. This time, my invitation came from one of my female managers where I worked, so I looked forward to what the evening had in store for me. It turned out my sexy “costume” hair and makeup fit it perfectly with the other women I ended up meeting for the first time.

I ended up meeting everyone in my manager’s house and they were all there when I arrived. I will never forget the delight I felt when I saw they were all dressed like me, so unknowingly I had dressed to blend with them. Also, I will never forget the hush that fell over the room as the other women looked me over from head to toe. I ended up tagging along in my heels, hose and mini skirt with all the other women who were almost as tall as I when we made our way to a close by neighborhood bar where the party was taking place. I had my misgivings about how I would be treated there, but after I was in the bar for a while, there was no indication from anyone that I was not anyone different than I appeared. I was even asked if I wanted to dance by a man. All I know was the night flew by in a hurry and my wife did not speak to me for days because she saw my “costume” before I left.

Even though my Halloween highs were very high, sadly they were accompanied by very lows I needed to suffer through. I became very depressed and mean and tried to make everyone around me feel the same way. My problem was only ultimately solved by getting out of my dark gender closet more than just once a year.

In order for me to exist in a life I was discovering I needed, I had to set Halloween aside as just another day. Which ultimately took all the fun and drama away from it. But sacrifices had to be made for me to live as a transgender woman and Halloween was just one of them.

 

Taking a Break from the Elephant?

 

No more Elephants! JJ Hart,

Taking a break from the elephant? I guess finally I am.

This morning, with groceries running low in the house, my wife Liz and I decided to run out in the rain to our nearby coffee shop to grab coffee and a breakfast snack. Since I was not anticipating meeting anyone else in the world, I just grabbed my purse and headed out the door with Liz. No makeup or anything since we were just going through the drive through. When we returned home and in a dry space, it occurred to me that I had retired the elephant in the closet of my life.

Excuse my language, but that damn elephant has always been a part of me for as long as I can remember. It was somehow a part of every decision I made. I could not take a break if I wanted to. If I was on a vacation with my second wife, I could not relax because I was thinking so much how I would feel if I could do it as a woman. Usually, after the vacation was over, I just wanted to get back to work to take my mind off the elephant in the room…my transgender issues.

I finally came to a point when I quit worrying about who I was gender-wise. I was just me and that had to be good enough. Surely though, I needed a lot of help to make it to that point in my life. I was deeply insecure about my transfeminine self and needed whatever public reassurance I could get. More than not, the reassurance came from having no feedback at all when I was out in the world. No laughing or staring to ruin my entire experience. I just could not take any sort of break until I became better at my public presentation all the time. I was still two people trying to come together.

All of this extended over to my writing which at this count is over seven thousand posts over ten years on one platform I write on. On occasion, I go back through my earlier posts to see what if there were any changes there were.  When I did, I was amazed at how centered in I was on my feminine appearance and not much else. I still had not learned what the elephant in the room was trying to tell me, there was so much more to being a woman than my appearance. I could not take a break until I learned that ciswomen lead a more difficult, layered life than men, and I needed to adjust and do better if I was ever going to really succeed.

I don’t think I truly conquered all of my fears of merging my worlds together until Liz and I began to take bus tour vacations to various parts of the country. Primarily, when I needed to stand in line for the first time in many years with other women waiting to use the restroom. The entire process tested my new outlook on the world in a space which was considered a women’s only environment. I remembered what I learned from all my past experiences, did what I had to do, washed up and left. With no adverse feedback from any potential haters or bigots. I was just me using the restroom.

With all of that behind me, I began to relax even farther and enjoy all the new scenery the trip had to offer, for the first time as me. I was on my own and to hell with the elephant which had taken up so much room in my closet. Another chapter in my life had been closed. The only break I took was from my daily writing routine, to allow myself a chance to recharge my batteries and hopefully do a better job which I had never been professionally trained at. I just started writing to hopefully help others with similar issues.

These days, since I have retired from my elephant and am still taking a break from all the problems and commotion he caused, sometimes I don’t know how to act. After all, I needed years to rebuild the damage he caused. Taking a break, now, means a lot more to me than just taking a vacation. I am sure before the next adventure we take; I will still feel the same residue from past gender world mishaps I needed to overcome and move forward, but at least I don’t have to ruin my days worrying about it.

It is much easier to pack for a trip for just one person. The only person which really mattered all along which makes taking a break much easier to do.

 

 

If I was a Betting Person

 

Image from Jeshoots.Com on 
UnSplash.

In my life, I have never been much of a betting person at all.

In addition, there were many times I would have bet against myself when I thought of ever making it to my dream of being a fulltime transgender woman. I had a real problem remembering all the negatives I encountered when I first left my closet and went out into the world. As I always mention, my gender woman’s workbook was totally blank when I started my life. The only fact which was rapidly becoming sure to me was that was I positive something was wrong with me.

Probably the only thing I would have been certain of was the gender issue I dealt with was deep and very complicated. Had I known how to bet on it, I would have. The only thing I would never bet on was I had my life completely backwards. Since I was born into a male world, I stayed there way too long. Staying on course to be the best man I could.

For awhile I thought I was successful in my male life as I held the bullies at bay by playing sports and working on cars. The proof was when I finally did work through my issues and transitioned, the very few people who knew the old male me were totally surprised when I told them. Proof I hid my true self very well, often sadly. I was hiding myself too well and, in the meantime, hurting my already frail mental health.

By this time, my male self was betting against any idea I could ever come out into the world as a transfeminine person. In fact, he did not know what the term meant. Following the adversity I went through coming out, he found out what perfecting our new life was all about. It was about going out as much as I could and exploring an exciting, yet scary, new world. It was about buckling up and staying the gender course I was on, when the times got rough. Which was often. I never had any of the feminine attributes a few cross dresser or transgender women had, so my path was often difficult.

As I became better at my feminine presentation, I began to think my dream was possible after all. I could even bet on it. For once, the optics of gender were working for me. Controlling the optics took a lot of work when I was rejected as a woman for so long. I would have pulled my chips back off the table and headed home. The big difference now was, I was able to outbluff others around me and stay in the game. I am sure no one mistook me as a cisgender woman, but on the other hand, no one was mistaking me as some sort of a bogus person trying to fool the public as a beginning drag queen. Betting on myself as an authentic person turned out to be the best move, I ever made in my life.

A good plan went a long way as I was able to carve out a new life in a relatively short time. I was not as shy as I was as a man and the world opened for me. After many false starts, success began to happen. I was staying out of my own way as a trans woman and letting my inner woman run my life.

I also learned where I was welcome to be a betting person in the world. For the most part, cisgender women accepted me in their world and let me play. Men, on the other hand, never wanted to bet me on anything. Which I quickly learned was not important to me after all. As long as other women validated me, that was all that mattered and again, my life improved.

Pushing my chips to the middle of my life’s gender table and betting I could make it to my dream I always wanted to live was all that mattered. Doing away with my conservative past helped me immeasurably during this portion of my life. I did not view myself as being any sort of courageous person. Just a person who had to do what she had to do to survive in a challenging world. The question became how fast I could learn the new rules of being a woman on my own terms. Decoding the difference between male and female privileges was the biggest challenge.

At that point, the betting game I was playing became closer to a game of mental gender chess. As an excuse, I kept telling myself I was not betting at all. Just playing the odds, I was right when it came to gender. When I expected I would make it as a transgender woman I did. I finally was right when I bet on myself.

 

 

 

 

 

Here Comes Tomorrow

 

My wife Liz, anniversary image.

Liz and I’s wedding anniversary was yesterday, and of course we had to go out and celebrate the event. It is actually our third anniversary after being together well over a decade.

Over the time I have written this blog, I hope I have not been short on trying to relay what my wife Liz has done for me. So much, as a matter of fact, she kicked me totally out of my closet, and showed me tomorrow was here. I could live a life as a transgender woman, finally free from my old male self. She was the direct opposite from my second wife who kept telling me there was no way she wanted to live with another woman. Liz told me she saw no male in me at all, and the rush was on to complete my male to female transition.

By the time all of this happened, and my second wife passed away, I was well into my sixties and had given up any hope of ever finding another serious relationship. Preferably with another woman who would accept me. As I always point out, to combat my severe loneliness, I was working the bar scene and even tried online dating which turned out to be a joke…until I met Liz. Or she met me. She responded to a “woman seeking woman” ad I put on a dating site and as luck would have it, she lived relatively close to me in Cincinnati. At the time she commented on the picture I used, saying I had sad eyes. Which I did, seeing as how I was going through the toughest time of my life. I had just lost my wife of twenty-five years as well as nearly all of the close friends I had to death as well as losing my business. I was grasping at any straw I could to stay afloat, sad eyes or not.

The only main straw I had was my sudden dependence on my strong inner feminine self. In a time of darkness, when my male self-had deserted me, she stepped up to provide the comfort and strength to move on. It was up to her to carve out a new life with new friends who had no previous contact at all with my old male self. Against all odds, in a sometimes-hostile world, she managed to do it, and my life slowly began to improve. With all the help and attention, I was receiving from my new ciswomen friends, I did not have to even give much of a second thought to the men who were afraid to approach me or just wanted to treat me as some sort of a fetish object. With my base sexuality settled again, it made it easier to feel secure in myself and move on with my male to female transition. Often it seemed my life was coming full circle and Liz was a major part of it.

During our anniversary dinner last night, we were fortunate that the venue was very empty without even the usual screaming kids so we could reminisce about our past and dream about the future. And of course, Liz took all the credit (as she always does) for reaching out to me first as a “woman seeking woman” post was an exceedingly rare response coming from any other women in those days. Plus, I was not shy in pointing out I was a transgender woman made my odds even more remote. If I received any responses at all, I felt like I had won the lottery of dating as a trans woman.

Because of Liz, I won the lottery for all the reasons I went into and more importantly, my gender transition which was always tomorrow became today. It was time to give away my remaining male clothes and follow Liz’s instructions on following my heart. A heart, it turned out, was feminine to start with and needed little to no encouragement to live. Regardless, when tomorrow finally came, it hit me hard and I needed time to adjust I really did not have. I needed to fall back on the decades of cross-dressing practice I had to feel more comfortable in the world. When I did, the joy of life I experienced was wonderful and even more so because I had someone special to share it with.

To be able to live the way I do still feels like a dream to me and Liz has helped me to realize my transfeminine dream more than anybody else ever did in my previous life.

Happy anniversary Liz and may we be able to celebrate many more together. And, thanks to all of you who have joined me in my journey. If you have not reached your tomorrow yet, keep trying. I am living proof it can still happen.

 

Home at Last

 

JJ Hart on left with wife Liz on right.

I know I start out too many posts with reference to exploring my mom’s clothes and makeup when I was very young, but I did. Even though I was caught in the thrill of the moment, I knew quickly that a couple things would be happening. The first of which was, I knew deep down I would not be escaping the urge I had to dress in girl’s clothes anytime soon. And the second of which was, I knew somehow, I wanted to do more than look like a girl and parade in front of a mirror, I wanted to experience the world girls around me lived in

All of this created severe stress and tension as I tried to internalize my thoughts. I daydreamed during any spare moment I had trying to figure out how I could live out my feminine dreams. I will forever wonder about how much quality life I lost when I was in another gender dimension. In fact, my daydreaming took me way into the years of my military service when I was able to take a spare moment and dream about living as I pleased as a transgender woman after I was discharged from military service. My biggest dream was to show off my new beautiful appearance in a new car in front of my former fiancé who rejected me when I came out to her. Just when I needed her the most. I can’t say any of that ever happened except in the dreams I kept alive in my mind.

Little did I know I was stuck on an extended trip as I was making my way back home. At that point, I had made it from my mom’s clothes, all the way to having a collection of feminine belongings I could take with me when I traveled, just in case I had the opportunity to make one of my rare public outings as a novice transgender woman. Home seemed as if it was a long way away.

I struggled to with the idea of giving up all together with being a male as I was building successes in a male world, regardless of myself. Every time I would have success in the world as a transfeminine person, my male self would come along and try to destroy her. It was frustrating and hard on my mental health to say the least and home at times looked so far away in the distance.

Another problem I had was I did not know where my true home was, and I went on several frantic searches to locate it. As I started to change jobs and move my family to different locations, I still could not find myself. I moved my wife all the way to the metro New York City area from Ohio, all the way back to very rural Ohio along the Ohio River to chase my tail. To no avail, I was attempting to chase a dream which in reality was so close to me. I could not see the forest for the trees. She was standing tall and proud in front of me the whole time.

Plus, I did not realize I never had the choice to live in the gender I preferred at all. Had I taken the time to really think about who I was and face the fact that I should have been a woman all along, it would have saved me so much turmoil in my life. It took me finally finding my gender home to do it. It all seems so simple to me now that I sometimes am ashamed to admit it. I was simply the same as so many other ciswomen in the world, I would have to face the same obstacles as they did, plus then some since I was transgender, I needed to be better. I would have to face tougher obstacles in being accepted for employment, education and other issues. But I knew all of that coming home, so I was ready.

Arriving home was such a relief when I finally arrived. The gender battle I always faced was done and my mental health improved. All the nights out when I was alone as a trans woman came back to help me because of all the lessons I needed to learn as I pursued my own womanhood.

Giving up on any idea of ever living as a man again freed up my inner woman to proudly show off the home she had built over the years. It was a long wait for her, around fifty to be exact, but she made it home.

 

 

 

Pause and Reflect

 

Image from UnSplash.

Yesterday, as I waited for the doctor to see me, I had a chance to pause and reflect on my long gender journey so far.

In doing so, I had the opportunity to think about how scared I was in the early days of going to the doctor as well as other things. Naturally, I discovered some other things I was trying in the new world I was in, totally over my head at times. On occasion, I don’t think I point out enough how little I had to work with when I started my male to female gender journey. I was from a very male dominated family so there were no understanding moms or sisters to help me. In addition, my body was very testosterone poisoned which meant I had no effeminate body parts to work with, except my legs which I received several compliments on at various Halloween parties I went to as a woman. While I was flattered by the attention, I rapidly became more paranoid. I began to take compliments on my legs by thinking the people left out the part that I had on my legs as I had good legs as a man dressed as a woman.

As I reflect on those confusing days, I wondered how I had continued to persist as well as I did. I guess the reason was because what I was considering doing felt so natural even though it was so scary to me. I spent hours and hours pausing my life and reflecting on where I wanted to go. Too many hours, to be exact as I needed to be careful, I was missing out on my regular life as a man. Even though I did not worry about losing my male life the way it was. I wanted him to go away, but I needed to make sure I did it right. In doing so, I was selfish. I wanted to keep some of my male privilege and transition at the same time. All I did was hurt myself and those around me in the short and long term.

In the short term, I knew had problems dressing my body as a woman. I had the overweight thick torso and broad shoulders to worry about which would not go away no matter how much I attempted to display my legs. I was doomed to failure by wearing too many short miniskirts. My male ego was working overtime, and it cost me many embarrassing moments in the public’s eye before I finally learned my lesson and learned to blend with the percentage of the world I really needed to deal with, which were the other women. It is like the other women I dealt with at the VA yesterday, I made sure I thanked all of them for being there, and they really appreciated it and treated me better. In the past, I would have been too shy to do such a thing.

As I continued to reflect on my past evolution of my transfeminine person, I remembered again how self-conscious I was on my early visits to the VA clinics I went to for care. I was so afraid of being stared at, all the way to being laughed at. Which I never actually was. It took me several years of progress to overcome where I was in life. It took me the visits I made to the venues I went to when I left the gay bar scene I was involved with and moved on after I was tired of being mistaken for a drag queen. Which I had nothing against, but it just wasn’t me.

At this point, I was wondering exactly what to do. Some I have talked to mentioned the “courage” word with me when I thought of going out in the world. On the other hand, I thought pursuing a transgender life was in many ways, my destiny I had been working on for decades. As I reflected, I thought how right I was. From the mirror to the world, I had carefully followed my path and just had to keep doing it. Or, instead of courage, I would never forgive myself if I had never tried to try out living my dream. Especially when I had proved to myself that I could do it. I had a giant inferiority complex concerning my entire life as a trans woman which I had to conquer.

By this time, my doctor was ready to see me, and I needed to return to the reality of today’s world. At the advanced age of seventy-six, I view each annual exam as very important of course. Even though it was invading my time to pause and reflect.

 

If I Had Known Then

Image from Hc Digital 
on UnSplash. 

The age-old question is, if I had known then what I know now, what would I have done differently.

Realistically, since I don’t have some sort of a magical time travel machine, I could not do anything differently. But if I had it all to do over again, I would have tried to come out of my male gender closet much earlier in life. I would have taken advantage of the youth I had and invested it in progressing to being a transgender woman. Even though I was well into my thirties before the term “transgender” was even invented or discussed. The truth of the matter is, I wasted too much time between Halloween parties when I could safely cross dress as a woman. Finally, once a year just wasn’t enough and I needed to open my closet door a little more and explore the world as a transgender woman.

If I had known then, I would have realized there would be no shortcut towards my ultimate goal of living as a trans woman. I would have to find my own unique path to being a woman that any other female has to do. For years, my second wife tried to tell me the truth, but my male ego stood in the way, and I refused to listen. I thought just looking the part of a woman was enough until getting out into the world proved me wrong. I needed to pay my dues just like any other cis woman before I was allowed to play in the girls only sandbox. It was a difficult struggle to get there, full of many setbacks, but somehow, I persevered and kept moving forward, often at the expense of my marriage and my male life. Primarily, my marriage since I was very close to my wife and she was my best friend. If I could go back, I would have tried even harder to be closer to her before she suddenly passed away at the age of fifty.

I would tell her she was my role model and all I really wanted to do was to have her like my feminine self, which she obviously did not. Instead, we fought like cats and dogs until she would tell me to go away and be a woman and spare her the pain. As much as I secretly knew she was right, I was still determined to hold the marriage together and pursue my transfeminine dreams the best I could. It all turned out to be the wrong plan and I suffered. There was not enough therapy in the world to help me through such a cut and dried situation. Sooner or later, I would have to make a decision in my life and choose between my two strong women…my wife and my inner feminine self who was becoming stronger and stronger by the day.

If I had it all to do over again, I would have set my male self aside and det out to build a new life as the transgender woman I was always meant to be. In the short term, it would have been difficult, but in the long term I would have been happier, and my mental health would have been better with the gender pressure off. Also, I need to bring up my excessive use of alcohol to mask my pain. Somehow when I drank, I felt more like a man and less like the woman I wanted to be. It was not until I was well into my male to female transition that I could decrease my addiction to alcohol and now I am lucky if I have two drinks a month.

Even If it is impossible to go back, I wonder how my life would have been if I had pulled the plug on my male life earlier. I certainly would not have missed all the time I was daydreaming my life away about how it would be to live a feminine life. How much better and productive could I have been. On the other side of the coin, I know I would have lost valuable time learning all I needed to learn to survive in such a new radical feminine world. Time seems to always erase the negatives and accentuates the positives.

Even still, knowing how successful I was able to be in my gender transition, it is impossible for me to not think what could have been possible if I had made the move earlier.  Even though my path was difficult enough, I may have had a smoother path if I had done then what I know now.

 

  

Dressing for Success

 

Image from Mohammad Nadir
on Unsplash. 

During my earliest days when I was forced into being a boy, anytime something negative or even challenging happened to me, I would run home and seek solace in my soft and colorful feminine clothes.

Soon I called the cross dressing I was doing, dressing for success. Mainly because I felt better as I did it. The sad part was, very soon the feelings of gender euphoria went away, and I was back in my unwanted male world where I was expected to succeed. During that time in my life, I was able to barely keep my head above water and still slowly improve my feminine basics in such things as the makeup arts. I guess all those hours of watching my mom apply her “face” as she called it, came back to help me. This was the 1950’s when women took their appearance much more seriously than today. All women were expected to dress for success.

As I barely stayed afloat with my cross-dressing challenges, it soon became more evident to me that there was much more going on with me than met the eye in the mirror as I tried to appreciate myself. It was about that time, when the internet showed up, and I was able to research terms such as gender dysphoria and transgender. Suddenly, I discovered who I might be and certainly found I was not all alone. It all started to make sense why my urge to cross dress never really seemed to go away. It was always with me in the back of my mind.

Soon, as I joined the world as a novice transgender woman, dressing for success largely depended on if I could go out into the world and blend in. I began the easy way by trying my hand with shopping mall clerks who for the most part were only nice to me for the money I needed to spend so I could be more fashionable and feminine. From there, I branched out to challenge myself by stopping to eat lunch and face servers one on one to see how I did. I did well, and very rarely did I have to run home and wonder what I did wrong and go back to my gender drawing board. I did not realize it but what I was doing was replacing my mirror time with time in front of the public. A very valuable learning experience as I discovered venues such as coffee shops, bookstores and even antique malls where I could shop and relax.

Each experience helped me to learn more about myself as a transfeminine person and then dress for success from it. To quit being so flamboyant with my wardrobe and wigs became my new goal as I was settling into my new life. People began to know me quicker, so I needed to be better in my approach to dressing for success. I learned I did not have to lose any of the enjoyment I experienced as a trans woman; I just needed to follow the lead of the cisgender women around me. I did not necessarily have to dress down for the grocery store and up when I mixed with the professional women out for a drink, but it helped me to feel better and relax. Plus, heels and hose would have certainly not worked when my lesbian friends, and I got together.

At times I even took my dressing for success to the extremes to be able to judge what the public was thinking of me. I used to wear my best sunglasses so that strangers could not see my eyes and tell I was looking at them, but were they looking at me? And one of my favorite “props” to use when I went out to be alone was my cell phone which I always had handy when I turned out to be the only woman at the bar. That way, I was trying to show anyone else I had someone else on the way, and I was saving their seat.

To be sure, dressing for success as a transgender woman was always a more complex process than doing it as a man. From undergarments to accessories such as jewelry, wigs and purses, women naturally lead a more layered life which can be reflected in the way they dress. I certainly had many more compliments on my outfits as a woman than I ever did as a man. Primarily, it was because it was something men never do and often, many cisgender women used compliments as simple conversation starters when they were curious about me.

As with all cisgender women, dressing for success is something transgender women must learn. The problem being we come from such a vastly different background to do it. Almost none of trans women had the benefit of peer pressure and a mom to guide us through the initial makeup process. Our workbooks were blank when we started our gender journeys. Playing catchup was not a fun game to play for me as I found making up my face was different than painting model cars. Most certainly, dressing for success was a lifelong experience for me.

 

 

Gender Dreams

 

Image from Greg Pappas 
on UnSplash.

This morning when I woke up, I took a moment to remember the sadness I felt when I got up in the morning and I was not a girl. I had the same sad realization, I was still a boy and nothing had changed. Plus, it is important to point out that I had no other dreams when I was young such as being a professional athlete or a doctor. All I wanted was to be a girl. I figured I was the only boy in the world who felt that way.

It was on those mornings when I needed to realize I was still male, and I had a long trip to make if I ever was going to change it. As my life became more complex, so did my gender dreams. Sometimes, I could not wait until I went to sleep to see what sort of dreams, I would have that provided me a respite from the days activity of being a man.

It was not until I decided to come out of my closet and test the world as a transgender woman, did my nights began to change. Replacing dreams with action was often a very scary proposition. But it was one thing I had to do if I was ever going to see if I could make it to a new transfeminine world at all. Would the public ever come to a point where they would accept me as more than just a man in a dress. Out in the world to be laughed at. If I could never make it past that point of being a cross-dresser, did I want to go on any longer and forget all the dreams I had. I finally discovered there was much more to being a woman than appearance and it was just my male ego trying to influence me.

Still, as I struggled along in my novice cross-dressing years, my gender dreams began to change with it. Instead of just wanting to be a woman, I started to dream of how it would be to live as an attractive woman and not have to worry about my presentation so much. I think it was because I was becoming more confident in myself, and my subconscious self was adjusting to the new me. More or less, I was reacting to the kinder, gentler world I was in as a transgender woman, and I loved it.

My main problem then was, could I make it to my dream when it became a reality. I was frustrated when I thought I could see the finish line and it was taken from me due to unknown transitional experiences such as what would I do about supporting myself if and when I made the decision to go from a male world to a female world. And would I need to prepare to be lonely the rest of my life because the possibility of someone loving and accepting a trans woman were exceedingly rare at my age of sixty. I was fortunate and exceeded all my dreams when I was financially able to take an early retirement and support myself and found my wife Liz (or she found me) on an online dating site. At that point forward, I had painted myself into a corner and I had no real reason to not follow my dream of being a transgender woman full time. Because I had finally faced up to myself and realized I had always been trans parttime, even though I could not share it fulltime with the world. 

As I faced up to reality, my nighttime dreams began to change also. Slowly my old male is disappearing from my subconscious too, He is being replaced by new dreams with me living as my true, authentic self. Maybe it is because he was pushed out of his final hiding place in my mind. Whatever the case, I was not sad to see him go.

I wonder now, what my childhood boy would think if he could see me now. Doing much more than just hiding in a gender closet waiting for brief moments to escape and explore. I am sure he never thought he would have the ability or confidence to be who he always wanted to be. Not an athlete or a doctor, just myself…a woman. I certainly had to come a different direction to claim my prize but maybe by doing so, I appreciate it more because it was never just given to me.

The boy I was would have never known his dreams would have never turned out like this, and being happy would not have been so far away also when she was playing with the girls. Where she always belonged.