Playing the Short Gender Game

 

Image from Jayson Hindrichsen
on UnSplash.

During my life, I always have taken the easy way out and thought about important things such as my gender as a short-term issue.

I write often of my love for the mirror when I was young. I hated seeing my male self-reflected back at me but completely enjoyed it when the mirror came to life and I was cross dressed as a pretty girl. Perhaps it was then that I started to think of my life as a short-term basis. Would I eventually outgrow my desire to be a girl when I became older, or if I did not, what would happen to me then. To make matters worse, the Vietnam War was ramping up and I had the constant threat of military duty to think of. Normally when I did, and the coast was clear, I ran back to the mirror and escaped behind a dress and makeup.

As I wrote about yesterday on Veterans’ Day, military duty finally caught up to me when my draft lottery number was fifty-two, so all the short-term thinking and worrying I did was a waste of time. I was going to have to put all my love of being feminine behind me and survive the best I could. It turned out that all the worrying I did about my gender issues and sexuality was wasted too. As I stayed very short-term in my cross-dress thinking, destiny took over in my life, and I started to do more and more in the world to express my new feminine self. Even though I found myself living on the edge more than once, I learned to live there until the next challenge came along. These were the years of changing jobs and moving my family way too much.

As I frenetically moved through life, I was moving too fast to slow down and see what the real issue was. It was gender, and sooner or later I would have to deal with it one on one. Until I did, I would be living a lie and a very messy one at that. Out of the one transgender woman I personally know who told me she was never gender dysphoric, I would guess she would tell me also that she never encountered any messy moments in her life when she transitioned. If she did not, she is one of the few that I know who didn’t.

Many of my messy moments stemmed from me being selfish and wanting to maintain my twenty-five years of marriage to a woman I really loved when she was against me going any further as a transgender woman and starting gender affirming hormones or HRT. By attempting to have it all in my life, my mental health suffered, and I made many mistakes as I tried indirectly to out myself to the world. The biggest one was when I insisted on going into my own restaurant dressed as a woman and being immediately recognized which I could have been fired for.

By this time, I was in a downward spiral which I could see no way out of. It all led me to a suicide attempt and more dissatisfaction with life. Through it all, I had a little voice within me saying everything would be OK someday if I just followed my transfeminine instincts. But before I did, I was stubborn and had a lot of life yet to live. Just when I thought I could not go any lower, I did. I lost my wife and three out of the only four male friends I had to death. Which sent me even lower into depression. I was at a point the experts say with drug addicts who must hit bottom before they can start the path upward. Just change the wording to my male self was at the bottom of his journey and it was time to give my inner female a chance to live. Because, at this time, there was no longer time for short term solutions, my male self just had to be done.

Fortunately, I was able to salvage all the years of practice and learning I put into my femininizing projects and did not have to start from scratch when it came to working on my presentation as a transgender woman. I could look at the long-term benefits of my male to female gender transition. It was such a relief to be able to finally change my thought processes around and not play the short-term gender game at all.

United States Veteran's Day 2025

 

Female Service Person
from UnSplash.

Today is Veteran’s Day in the United States. The day we salute our numerous numbers of military veterans who served and serve our country. Especially those who made the ultimate sacrifice with their life.

As most of you know, I am a veteran myself and survivor of the Vietnam War conflict. Plus, I know I have plenty of other veterans who read and respond to the blog. To all of you, I would like to thank you for your service to our country.

In all my Veteran’s Day posts, I always make it a special point to mention all of those who were serving as they were in the closet or questioning their own gender issues when they lost their lives. It is suspected that there is a higher percentage of transgender people who try to serve but can’t or just hide it and go deep into their closets. I can’t imagine what that would feel like.

In my case, I have a couple of different positives which came from my time in the Army. First, infantry basic training taught me how to have a deeper respect for myself and the pressure I could endure. Secondly, I was able to travel the world on the military dime and learn how other cultures lived. Thirdly, I was able to come out of my gender closet for the first time and admit to close friends I was a transvestite after a Halloween party I went to as a woman. And perhaps the most important positive I gained from my time in the military was the chance I had to meet my first wife who was in the “Woman’s Army Corps” in Germany. She went on to be the mother of my only child (my daughter) who turned out to be one of my huge support systems in the future, and now. The gift that has kept on giving from the Army.

While I am on the topic of gifts, my continuing use of the Veteran’s Administration health care system has been a tremendous help in my life. It initially came at a time when I was financially broke and could not afford to buy my depression medications and gave me life giving hope especially when I sought out hormone replacement therapy and mental health help. So, as you can tell, I have been repaid many times for the service I gave to the country.

I am but one example of what is possible for veterans, but the fact remains that too many veterans young and old are suffering from PTSD or are homeless on the streets. If our country can afford to fight wars, it can afford to take care of those who fight them.

On this Veterans Day, please pause for a second and remember (or more importantly thank) those around you who have served our country or who are serving.

The Yin and Yang of Gender

 

Yin and Yang from Gabriel Vasiliu 
on UnSplash. 

You might ask why I would write a post explaining why I was in such a hurry to transition into my womanhood when it took me nearly fifty years to come out of my gender shell. I finally discovered I was in a classic war between my yin and yang personalities.

Today, I am writing to explain the two forces I faced as I decided when and how to transition. My own personal yin and yang of gender. I guess it doesn’t matter which of the two forces I had to deal with, or if my yin side was feminine and my yang side was masculine because both were prominent parts of my life. Yang flourished because he had to early in my life and yin did the same when she finally had a chance to live and exist. I found this description from “Wikipedia” which backs up my theory:

“In Chinese creation theory, the universe develops out of a primary chaos of primordial qi or material energy, organized into the cycles of yin and yang, force and motion leading to form and matter. "Yin" is retractive, passive, contractive and receptive in nature in a contrasting relationship to "yang" that is repelling, active, expansive and repulsive.” It described me completely.

Yin and yang caught me chasing my tail as I would run back to the mirror as quickly as I could to put on a dress, make-up, and convince myself how pretty I was. It was yang’s primary form of escaping any potentially troublesome situations. As I always explain, coming to terms with all of this caused great torment, and now I wished I had someone to at least discuss it with except the one good therapist I was fortunate to be placed with at the Veterans’ Administration in Dayton, Ohio. She was understanding and even had a basic understanding of the LGBTQ community, so I did not have to educate her at all. However, we did not ever get into the clash of my yin and yang genders. On the plus side of our therapy, she never tried to equate any of my bi-polar depression issues with my need to express my yin side of myself.

Ironically, I think my yang side was very active and expansive in pushing my yin into the world. He provided the life lessons I needed to get out and push my gender envelope by learning new things. Without him, the initial exploratory trips to the regular venues I established myself in as a novice transgender woman would have never happened. So many nights I sat in my car for what seemed like forever before I summoned my courage to go inside.

On the other hand, it was yang who did his best to ensure his male world would never be taken away and he made a strong, experienced adversary. The problem became was how I was ever going to join my yin and yang together and form hopefully a good transfeminine person. The answer was I never had to really give up all the life which yang brought to the table. It turned out, I still was able to follow my love of sports, all the way to keeping my sexuality when lesbians took over my life. Altogether the entire process of joining my yin and yang proved to be easier than I thought. I just needed the courage to do it.

It would be too easy to say all transgender women and transgender men suffer from yin and yang gender problems, but the idea may go along way towards explaining what we feel to an outsider. It is far out of my pay grade to predict what anyone may do when confronted with such complex gender problems a trans person has. In fact, when I go back to “Wikipedia”, it even mentions gender in this form:

“When pertaining to human gender, yin is associated to more rounded feminine characteristics and Yang as sharp and masculine traits”.

I don’t know about you, but the whole definition works for me, and I wonder why it has taken me so long to stumble upon it in my research. In some ways, yin and yang reinforces my idea that transgender people deserve a special place in the world. Not one of scorn and discrimination. Maybe the average person just needs to know more about us on a regular basis and not what they hear from politicians. But they can’t even govern well enough to keep our government open, so I can’t see much chance of that anytime soon.

Do "It" or Die

 

Image from Claudia Love
on UnSplash.  

I find it humorous when a gender bigot or some sort of other hater thinks transgender women or trans men had a choice when they decided to transition into the gender they should have always been.

The haters conveniently overlook the fact we trans people spend a lifetime of discontent over our gender dysphoria. In my case, the dysphoria invaded my already frail mental health and nearly destroyed it and me. I suffered from being born into the pre-internet “dark ages” where information on gender issues in particular was very hard to come by. It took years of my life before I was formally diagnosed with dysphoria and even worse, a bi-polar disorder.

It all started when I spent my days off work in bed, not wanting to move at all and forcing myself to work to keep my job. Of all people, the first real gender therapist I had diagnosed my problem when I brought it up in a conversation we were having. She ended up telling me she could prescribe medications for my depression but not for me wanting to be a woman. I should have listened to her and took more action than just cross dressing when she told me that. I was still stubborn though, and my male side thought he could conquer all. Setting up an internal war I would fight for years. I was fortunate when the prescribed medications worked with my depression but not so fortunate when they did absolutely nothing when it came to me wanting to be a woman. In other words, my gender therapist was right.

In the meantime, as my gender war raged on, I was out of my closet exploring the world to see if I could survive at all. As with any other novice, I had my good days and my bad days but something deep inside kept telling me to keep going because my survival was at risk. How much so, I still had not fully grasped.

As with anyone else, the years seemed to fly by and regardless of the unlikely idea I could ever achieve my dream of competing in and surviving in a transfeminine world successfully, I slowly was making it. Ironically, many times when I did make it, the trip up was not worth the trip down mentally. A prime example was the night I went to a cross dresser-transgender mixer on Long Island, New York and was forced to show proof I was actually a man before I was admitted to the mixer. Of course, I was on cloud nine for days after that before I crashed back down into my unwanted male world. I so badly wanted to take the next step in my transition but was afraid to do it which created extra pressure on me. Sadly, I took the pressure out on my second wife who I perceived as a problem when she did not understand what I wanted to do.

It turned out, I needed a ciswoman in my life to challenge me to do more than just look like a woman. She forced me into searching for the elusive lives’ ciswomen lead, and why they were so different than men. Still, I was stubborn and thought I had already put that research in until my path took me to a whole different gender world which I was never allowed to visit before. Until I tried and finally let in to see what my wife was talking about.

By this time, I was reaching the point in my life when all my explorations into womanhood were taking me as far as I could go. I was staring ahead at reaching my sixties and knew I was not getting any younger. It was time to try to be approved for gender affirming hormones or HRT and take the next big step towards my dream life. If I did not, I may never have the chance to do it again. Plus, I was coming off the darkest moments in my life when everyone dear to me died (including my wife) and the only comfort I had was my inner feminine self. At that point, she showed me the reality of where I was in life.

As the pressure mounted to choose which direction my life would take at the age of sixty, I chose female and closed the book forever on my male self. At that point, I never looked back and took the pressure off myself. Finally, a wise move and somewhere I could hear my second wife saying I told you so. She did but I just did not listen. And, by the way, I still suffer from depression and from dysphoria but now I have learned to live with both of them by living the way I was born to be.

I did it before I died.

 

 

 

 

 

Following the Gender Breadcrumbs

 

Image from Elena Moshvilo
on UnSplash.

Following the gender breadcrumbs in my life meant finding the brief moments of gender euphoria I experienced and running with them.

Even when the mirror provided me with euphoria with the rush I felt when I saw myself as a girl, the feelings seemed to be exceedingly short and frustrating. I had yet to figure out my longing for the feminine clothes I was wearing meant very little to me. What was more important was, could the cross-dressing process ever take me closer to my dream of living a transfeminine womanhood.

Along the way, there were times when the breadcrumbs almost disappeared totally, leaving me completely lost and back into my closet. In despair, as I looked around, I did find enough crumbs to keep me moving because I was slowly learning, failure was not an option. I could take many of the hard-earned lessons I learned in the male world, adapt them and use them in my new exciting feminine world. For example, I learned that even though men compete differently than women, there was an equally intense competition going on between the ciswomen in the world that men knew very little about. Way past just being concerned of another woman looked better than them.  Since I did not have to worry about that, it took one more problem away from me. I never thought I looked better than any cisgender woman and I was not that shallow anyway.

I had more important problems to worry about as I searched for breadcrumbs to guide me along the path, I was on to transgender womanhood. Afterall, I was seeking to accomplish one of the most difficult tasks a human attempt to do which is change one of the most basic needs a person has, and that is their gender. Starting all over and carving out a new life was daunting for me, and I needed all the help I could get. For some reason, I found myself with ciswomen who spread the gender breadcrumbs for me. I could sit back and observe how they conducted their lives, good and bad. From them, I could see not all was peaches and cream as a woman then decide if I still wanted to do it. Then structure my life the best I could. My biggest problem was throwing out and ignoring all the hard-earned male breadcrumbs I had accumulated. In fact, I had almost put together the entire loaf which I kept trying to break up and throw away.

The most positive aspect of my life became the nights I went out with my lesbian and transgender woman friends, and we actually enjoyed ourselves so much we began to do it more and more. My breadcrumbs became easier to follow because I was different to my friends. I was not quite a full-fledged ciswoman as they were, but on the other hand, I was far from being a man they stayed away from. I was certainly baking my new loaf as a transgender woman with the help of my inner self who had been with me all the way and was just waiting to be set free.  It seemed most all of my dark lonely nights were finally behind me again in life. This time, on the side of the gender border I so long had waited for to open.

Wherever you are on your gender path, I hope it is lit well enough for you to see your breadcrumbs and have enough gender euphoria to get you by until you face another learning experience. I know, at times, the entire experience will seem overwhelming and hopeless. But the light at the end of the tunnel does not have to be the train and again I point out what a difficult path you are trying to follow. Risking, spouses, families, friends and jobs are never easy and is intimidating to say the least.  That is why if took me till the age of sixty to take the leap of faith I always wanted to do…live as a woman on my own terms.

It is important to note, you are doing the search on your own terms and the nay-sayers who like to point out you will never be a ciswoman are right. You can’t, but you can reach a womanhood of your own making.

Best wishes to finding all of your breadcrumbs along your path, and reaching your dream.

 

 

 

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.

 

 

 

 

 

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.

 

 

 

Down the Transgender Rabbit Hole

Going down the transgender rabbit hole was difficult for me.

The hole I chose was very dark, and full of dead-end passages before I ever had the chance to see any daylight. As I pursued my long-term dream of living as a woman, I needed to go through quite a few serious changes. In my rabbit hole, there was very little to no help. Especially, any guidance initially from other girls or women around me. It took me years to quit being a victim of my gender issues and make them an opportunity, as I scrambled around my rabbit hole to make it more comfortable.

Of course, it never became more comfortable, and exactly the opposite was true. The further down I dug, the darker my life became. Out of desperation, I searched for my gender daylight. Way past the annual Halloween parties I was going to dressed completely as a woman. Once a year in the public’s eye just wasn’t going to make it for me anymore. I needed other outlets to test how I was doing as a transgender woman. Novice or not. When I was out for the longest time, I felt like the rabbit which was being circled by a hawk. I was so unsure in my new high heels, I could not have run if I had wanted to. I was forced to stay and get abused early on.

I guess I was lucky that my abuse was relatively mild in nature as compared to what it could have been. I was just stared at and laughed at for the most part, until I learned to blend in with the ciswoman world at large. As I did though, I was sent flying down my transgender rabbit hole in tears as my progress was slow. At that point, two things happened. The first was, my hole became my gender safe place where no one could reach me. I was always the pretty girl I wanted to be. The other was the unforgettable sensation of why I was attempting such a crazy journey to start with. I was fairly successful in the male life I never really asked for, so why rock the boat and risk drowning.

Another important lesson I learned was my perception of a woman's life was all wrong. It was like I was watching a slide show on the walls of my rabbit hole when I viewed women. It was not until I tested the daylight of the world, did I realize the truth of what I was about to face. The most important truth I learned was how completely women interacted with men in the world and how innately strong they were. I wondered how and when I could ever fit in as a transfeminine person. I found the only way to learn was to do it and see if I would ever be let in to play in the girls’ sandbox.

To finally make my way into the sandbox, I needed to extend my rabbit hole even farther than I ever had imagined. Since I was always inherently shy, learning to look another woman in the eye and communicate with her was always so difficult for me. It took me years to have the confidence to believe in myself and do it. The most frustrating part was when I thought I had my new life all together, something else would come along to destroy my dream. My rabbit hole had collapsed and needed to be rebuilt. Once I accepted the new challenge of transgender womanhood, I moved on and rebuilt my rabbit hole larger and stronger than ever before.

As transgender women and trans men, we all have our rabbit holes to negotiate. Some are similar, some are not but along the way, we all end up giving away something that is precious to us. Sadly too, some of us discovered our rabbit hole was too deep or built so poorly we had to turn back. I’m referring to the so-called “detransitioners” who the gender bigots and TERFS love to use us as an example of failure in the transgender community. I believe the number of people in the community is much lower than the bigots like to point out, so it doesn’t really matter that much to those of us who have carved out a new life when we left our rabbit holes and carved out a new life.

Sure, it was never easy doing all that work, but in the end, it was so worth it to achieve a dream and stay out of the old hole I had built myself forever.

 

 

  

In the Wrong Room?

 

JJ Hart ahead of first Girl's Night Out.

When I first jumped out of my dark closet and into the bright world, I wondered if I had jumped into the wrong room.

There are other words for my feelings such as impostor syndrome, but I was not far enough along in my transgender development to know them. All I did know was I was feeling ill at ease when I was with another group of women. Which was nearly fatal mistake when it came to being accepted. I discovered how perceptive ciswomen were in their world and could spot a fake miles away. So, I worked hard to show them my truth. I really wanted to earn my way into their world.

It took quite a bit of work and time but slowly I began to be invited to special girls’ nights outs. I never turned down an invitation no matter how terrified I was of going until I began to feel as if I was not in the wrong room after all. It helped when I paid attention to what the other women were doing and saying, and I tried to do the same. As I suspected, the conversations revolved around family and kids, so even though I could not share any birth stories, I could talk about my daughter as a loving parent. A door was opening for me to enter a world I had always dreamed of as an equal, and I cherished my opportunity to learn.

I discovered too that most of the other invitees accepted me easily except for a few I rather not mention. No matter how much they glared at me, I was able to ignore them and have a good time. I was learning I had as much of a reason to be in the room as they did, an invitation from the alpha female gatekeeper who I respected completely for her diverse beliefs. In her life, she was her own contradiction in terms as I saw her. Primarily a strong Christian woman who accepted me for who I was.

On the other hand, men were a completely different story. From the time I started my male to female transition, I was ushered out of the boy’s club I had become a comfortable member of. I learned relatively quickly on the few dates I went out on with men to be quiet and let them lead. No matter how mundane the subject, and how much I knew about it. It worked as I settled into a new world having a lesser IQ. My dates were so rare with men that I never had a chance to feel the chill of being kicked out into a new world I always wanted to live in.

In short, I was thriving in my world and all thoughts of being in the wrong gender room went away. I was in no way an impostor and I deserved to be there. Rather than having a fancy new handbag, I had a fancy new confidence to go with everything else good which was happening for me.

Sadly, the only remaining problems were the same massive ones I refused to face. What was I going to do about my spouse who did not want to live with a woman, all the way to how I was going to support myself financially if I decided to jump the gender border from a male life, I was successful at, to a female one which was largely untested. Helping me along was the knowledge of knowing from all my ciswoman interaction in the real world was successful. It would be difficult, but I knew deep down I could make it. Mainly because the whole process seemed so natural to me.

Finally, I realized I was living my whole life backwards. I was always fighting the idea I was a man trying to be a woman. When in fact the opposite was true. I was a woman all along trying to be a man. It was no wonder I did not feel at home in either of the two main binary genders, male and female. And until I chose the right room, my life and mental health would never improve.

It seemed destiny was on my side as I made the journey into the transfeminine gender side of life. To arrive I had the cruel death of my wife (as well as other close friends to deal with) plus closing my business to overcome. Against all odds, my wife Liz found me online of all places and helped me to rebuild my shattered life. I was able to locate the proper feminine room and stay there.

I Almost Waited too Long to Transition

 

Image from Lizgrin F 
on UnSplash.

I almost went too far when it came to not deciding to transition from male to female in my life.

During the previous half century of cross-dressing my life away in the mirror, I put off making my final decision so many times. One of the main problems was, I was sixty years old and was forced to consider my mortality, which I had always taken for granted. Plus, another issue I had was feeling just a little too comfortable with all the male privilege I had struggled to build up in my life. Often it seemed, destiny had stepped into my life to guide it a certain way because I was very self-destructive and selfish. So much so that my mom always said I had a guardian angel riding with me when I did stupid things behind the wheel. All along, of course, I was trying to hide the pain of hiding who I truly was.

On the other hand, I was basically an impulsive person who felt all rules were temporary and could be worked around. Such as my time in the Army when I was able to land a job with the American Forces Radio and Television Service (AFRTS), which was nearly impossible to do. In the meantime, I was facing the biggest struggle of my life as I needed to figure out what I was going to do about my gender issues. It was always the elephant in the corner of every room I was in.

What I decided to do was research as much as I could my dream goal of living a life as a transgender woman. When I did, my very real struggles began. Early on, nothing came easy on my gender path. I was being laughed at when I went out in public as a novice until I got it right. As I fortunately exited that portion of my life, I was able to see more clearly what I was up against, and it was daunting. I had very little idea of the layered lives ciswomen lead as compared to men. When I realized what I was up against, I needed to set my transition timetable back. And to make matters worse, my male self was becoming increasingly successful in his life. Building up a solid base of marriage, family, friends and job. How could I ever replace all of that and when could I do it.

The only recourse I had at the time was the worst one I could consider. Internalize my deepest gender thoughts and keep trying to attempt to do the best I could to survive a life caught between the two main primary genders. Three days as a trans woman and three days as a man was killing me and I tried to no avail to take the extra day off to relax. It turned out I could not because all I thought of on my supposed day off was what I was going to do the next time I went exploring the world as a transfeminine person. Which brings up a good point, during this time of my life, any thoughts I had that I was just a cross dresser were slipping away. Only to be replaced by the fact that I refused to accept. I was more a woman of my own making than I ever thought.

One way or another it was in my fifties when I began seriously researching the word transgender and what it meant to me. I was happy when I finally found the terminology which applied to me but again what was I going to do about it. I was not getting any younger. I still made the worst of all possible choices and continued my path of least resistance. At least that is how it appeared to the outside world which I was effectively hiding my efforts of femininizing from them. I had won my award as a strong male role model with a good marriage, family and job, and now I wanted to give it all back for a radical gender change into womanhood.

When my sixtieth birthday rolled around, I finally decided I needed to make a major change before it was too late. I went to a doctor and took the steps to be approved for gender affirming hormones or HRT and the real changes started. As good as I felt though, I could not shake the sorrow I had from moving permanently away from my male life. Even after my mental health improved.

Finally, I realized I had waited too long for the change and should have had the courage to do it long before I did. But at least I managed to make the major gender change I did before it was too late. And what about my elephant who was my constant companion? I set it free.

Trans Girl on a Cliff

 

Image from Majestic Lukas
on UnSplash. 

A few years ago, sixteen to be exact, I found myself at the ultimate crossroad in my long gender journey.

I was sixty at the time and I had pursued all the mini gender bucket lists I could to see if a complete male to female gender transition was possible, and it certainly was. More precisely, I was becoming successful at carving out a completely new life as a transfeminine person with people who never knew anything about my old male past.

For some reason though, my old male self-refused to let go, causing me undue stress and tension. He kept arguing that there was simply too much hard-earned male privilege to just throw away for good. Plus, once I went down the final path to trans-womanhood, there could be no turning back. The cliff I kept sliding towards was increasingly steep every time I looked at it.

Through it all, I managed to turn a deaf ear to him and looked ahead to a new exciting life which felt so natural. Which is one of the main reasons I did not back down into my previous world of serious cross-dressing adventures. At that point, I needed to assure myself that my new feminine life would be more than adventure, it would be a heavy dose of reality with no turning back to the male clothes still in my mental and physical closet. More than anything else, the new Estradiol hormones I was on helped me mentally to prepare for the new life I was to face, while the clothes in my closet were just waiting for a visit to my local thrift store to give away. It was an emotional day when I severed ties with the last of my male clothes, but I did it anyway and the only thing I saved was my old Army uniform.

Ironically, when I did all of that, I was between serious relationships and all alone in the world to make and live with my serious gender decisions. There was nobody else to discuss my decision with. Just me, all by myself, which gave me wonderful clarity of thought. As the fog of the regular world dissipated, I was able to see clearly down the cliff and determine what the future held for me if I followed my ultimate dream of being a woman. Finally, after the umpteenth time of worrying over my decision, I decided to make it and take the weight of worry off of my shoulders. To ignore the cliff, I was facing, and jump was liberating to say the least. It was like I could breathe again.

As I made the final tumble down my gender path, I remembered all the twists and turns I made to make it. All the times I was laughed at or worse as I learned my lessons I would need to survive if I ever decided to make the final transition. Of course, I knew little to nothing about what I was doing so I was caught making up my woman’s world as I went along, with no help for the longest time. Once I got the help I needed, I was far along in my transgender development in the world, and I used the help I received from my cisgender woman friends to round out my personality and make my jump off the cliff seem easier to take.

With everyone’s help, I jumped and felt as if I could fly in the new feminine world I had chosen. There was no unexcepted crash and burn that I had feared for so many years. I had done plenty of prep work in the major areas I needed such as appearance, communication in the world, and so much more such as what I would do to support myself since I knew coming out on my old job would be impossible. The nights I spent going out in the world by myself as a transgender woman were behind me and I could look forward to a new future. I worked hard to jump from that gender cliff and have a safe landing.

My friends helped me to socialize more at lesbian mixers than I ever thought possible and I was able to retire early on enough of an income, so I did not have to worry about going back to work again, so my main bases were covered. It turned out, all those years of worrying what would happen if I jumped the gender border were wasted as I went all out to make sure I could make it as a transgender woman in the world.

Who knows, maybe all the extra work I did in the world just helped me make the landing I went through a little less intimidating and softer.

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.

 

  

Gender Awakenings

 

Image from UnSplash.

Gender awakenings came early and often for me. I say early because from my earliest days of conscious life, I knew something was not right about me. As I always point out, this was in the 1950’s in the dark days of the pre-internet era when any gender information was difficult to come by. To make up for it, I experimented wearing my mom’s clothes and trying to apply her makeup the best I could. Then I would wear out the carpet in front of the hallway mirror admiring myself. Somehow, I convinced myself I was a pretty girl ready to go out into the world.

When I finally broke out of my closet and tried out the real world as a novice cross dresser, I received a rude awakening. Initially, it came from groups of teenaged girls I encountered in the malls I went to. They were brutal and not shy about laughing at me. Too many times, I was sent home wondering what the problem was with my image or presentation as a woman. One thing was for sure; the mirror was lying to me when it told me I could pass with no problem. I just had to do better if I was to survive in chasing my dream of living as a woman. In fact, at times it looked as if I had no chance of ever making it at all.

Fortunately, as dreams went by, I found I had an achievable one as the years went by. But achievable never meant easy. I had many negative transgender awakenings mixed in with just enough gender euphoria to keep me moving. It could be as little as encountering a group of teen girls with no reactions, all the way to having lunch when I went out to shop. What I was slowly doing was replacing my mirror in the hallway with the world. Maybe this male to female transition trip was not going to be so difficult after all.

At this time, over confidence got to me on several occasions when I had left the relative safety of the gay bar scene and tried to move to more familiar venues such as sports bars and even lesbian taverns. The problem was, I became too comfortable when I was accepted and had a tendency to slip too far back to old unwanted male roles. Keeping track of where I was in my new life and taking too many chances. I was guilty of being in the wrong place at the wrong time and nearly suffered from it until I learned my male privilege of safety no longer applied. I also was not prepared for how fast I lost part of my intelligence when I was dealing with men. Very early on, I found myself being completely ignored when I ended up with a group of men. Even though, I knew more than they did.

As I learned I would have a much easier path to acceptance from other women than men, I discovered the hard way that was not always the case. The well documented times when I had the police called on me for using the women’s room at one venue, all the way to being called a pervert in another place come to mind. Those were deep wounds to overcome but somehow, I did and found stable places to go to which accepted me for who I was. Even to the point of protecting me as their token transgender woman. The basics of smiling often, causing no trouble, and tipping well did wonders for me.

Even still, I had to be careful because I had a wife, family and job to come home to after my dream evenings as a transfeminine person. Soon, the delicate gender balance I was trying to maintain became too much to bear. I was to the point where I was just waiting for the next high heeled shoe to fall, or the next gender awakening to occur. I just knew I had come too far to turn back now, and my dreams were within reach. Only my big three stood in my way and destiny was coming along to take care of them.

My wife suddenly passed away, leaving me free of anyone except myself to answer to when it came to my gender awakenings. Plus, the only person I really cared about in my family (my daughter) became my staunchest ally when I came out and I took an early retirement, so I did not have transition on a job of any sort.

Once my gender awakenings started to come, they came fast and furious like a runaway train. The best part was, the whole process felt so natural, I never wanted to turn back.  Somehow, I kept the train on the track.