Monday, October 20, 2025

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.

 

Sunday, October 19, 2025

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.

 

 

Saturday, October 18, 2025

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.

 

 

 

 

 

Friday, October 17, 2025

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.

 

Thursday, October 16, 2025

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 fiancĂ© 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.

 

 

 

Wednesday, October 15, 2025

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.

 

Tuesday, October 14, 2025

Off to see The Wizard or Doctor

Today will be a relatively short post because today is the day for my annual trip to see my primary physician at the Cincinnati Veterans Administration and I have to be there soon.

Actually, for this visit, I am going to a satellite location not far from where I live. In many ways, the time I have been going to that location reflects a change in how that clinic treats transgender patients. When I first started to go there years ago, I was met with a very chilly reception. Even to the point of being ignored by one rude receptionist and one temporary doctor who I had a virtual (online) visit with. He rudely said “what’s wrong with you” after he saw me. Obviously, not the reception I was looking forward to.

Happily, that was the last time I had to deal with him and the next time I went, I was greeted by a new pleasant, female primary provider (which I think is similar to a general practitioner in the civilian world.) The best part was, she had some sort of working knowledge of what it meant to have a transgender patient. So, I did not have to educate her.

Providers turn over quickly at the VA, so I hope she is still there when I go this morning because I have several important personal health care issues to discuss. Such as getting a mammogram, settling up an eye care appointment, and most pleasant of all…is it time for a colonoscopy. I am getting a flu shot this morning, but due to the interference by our “dear leader”, so far Covid shots are not available. To people of any age. Which is important to me because I spent three days in a hospital last winter with Covid. My wife Liz and I are going on vacation about the same time as last year in January and I would really like the added protection of a vaccine before that time rolls around.

For my visit, I always try to dress light casual for my VA appointments. It is also important to wear short sleeves in case she wants blood work done. It has been a year, so I imagine she will want it done today. I  am  lucky that I have never had any problems giving blood to the “vampires”.

One way, or another, I always hope I am treated with respect which I have been on my recent VA visits.

If anything, else happens, I will let you know because I know, health care varies radically between the VA medical centers. Especially with the mandated cutbacks led by you know who. Whose motto is “If it ain’t broke, break it.”



Monday, October 13, 2025

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.

 

 

  


Sunday, October 12, 2025

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.

Saturday, October 11, 2025

National Coming Out Day

 


National Coming Out Day is today around here.

Of significance to me is the input I was asked to provide in my Veteran’s Administration LGBTQ support group. In the group, there are equal members from the gay, lesbian, and transgender communities. Yesterday, I was asked when I came out.

I said I came out when I was sixty, or sixteen years ago. Then came the questions of how I actually made the decision to come out in the world as a transgender woman. Since my time to explain was relatively short for such a complex subject. I did my best to explain all the nuances of giving up a male life I worked so hard to maintain. Then I needed to try to explain the unorthodox way I did it. I wished for the freedom of having the written word to do it, so I jumped right in and quickly started how I left the gay bar scene and went to the straight sports bar scene, just to prove I could. Making it all concise was an issue but I did the best I could.

Then the questions shifted to how or who helped me on the special day when I decided to give up all my male clothes, start gender affirming hormones and come out. That person was my wife of ten years plus, Liz. They asked how we met, and I said she literally picked me up on an on-line dating site called “Zoosk.” The lesbians in the group enjoyed the story saying it took a good woman to finally help me coming out. Which I said was true.

I appreciated the fact that the LGBTQ group wanted to hear my story, and I tried to mention all of us are different. If you are considering coming out, naturally it is one of the biggest decisions you will ever make in your life. We have to sacrifice family, friends, jobs and more to live our dreams. There is also a new transgender woman in the group who felt safe enough to explain her gender issues last week. Her story meant a lot to me and I appreciated her tears of joy of being able to talk to someone else about her coming out story.

No matter where you are on your coming out journey, hopefully you will have the support you need to achieve your goal. Remember, it is a marathon not a sprint and there may be many bumps and dead ends along the way for you.

For those of you who have come out, hopefully you are able to live your best life. Congratulations! Now with the current anti transgender climate from the orange Russian asset, we need you more than ever before.

 

 

Friday, October 10, 2025

No Addiction...Just Fact

 

Image from Yumu on
UnSplash.

Perhaps many of you went through the same misgivings about our male to female transitions as I did.

First, I felt it was a simple fetish with the new feminine clothes I was trying to wear. Then, when I outgrew the fetish idea along with mom’s clothes, I needed to try to determine exactly what was going on with me and my gender issues. With no help, and stuck in a very dark closet, I felt alone with no one to talk to. Thank goodness for the “Transvestia” publication by Virginia Prince coming into my life by pure accident which gave me hope for the future. There were others like me who wanted to look like women and have mixers with each other. If only I could make it to one, maybe some of my gender questions could be answered. While entertaining, the mixers I discovered which were close enough for me to attend, did not really answer many of my deep-seated questions. Such as why I was wearing women’s clothes as much as possible. Was I addicted to the clothes or was something else going on.

It did turn out that something much deeper with me was going on. It took me years to figure out the truth. Something much deeper was going on with me and my deeply held gender issues which should not have been problems at all, if I had faced up to them. I was not addicted to looking like a woman, the fact was, I wanted to find my own version of being a woman.

Then the real search for my identity began, as I finally had the courage to open my closet door and go out. In the beginning, ever so briefly until I built up my confidence as a novice transgender woman. Ironically, back then, the term transgender had not been widely used. There were only transvestites (or cross dressers) and transsexuals who wanted to have major surgeries called sex changes. Through this period of my life, I had the uneasy feeling I did not really fit into the transvestite or transsexual mold. I was different and still confused. All the diverse parties I attended were not helping me decide where I really fit.

Still, I kept trying to find my way, and I kept meeting more and more people on the gender spectrum at the parties I went to. From cross dresser admirers to impossibly feminine transsexuals, to the occasional lesbian, I was able to broaden my knowledge of the gender world as I knew it and further research where I belonged. By meeting all of them, I was able to determine where I wanted to be in the world as a transfeminine person and go from there. Plus, I did know, once and for all, the simple act of looking like a woman was not an addiction for me. It was a deep issue which sooner or later in my life I would have to face.

At that time, my progress was slow but steady as I made a far-ranging group of acquaintances in the gender community I was visiting. On one side, I was dealing with Ed, a part-time closeted cross dresser who had a crush on Michelle. A beautiful transsexual woman we both knew. I was stuck in the middle of that strange relationship. Trying my best to be understanding. All I knew was, the interactions I was having were not helping me with my issues which once again I was internalizing. The same thing I perfected in my male life which was so bad for me. I finally came to the point where I realized I needed to be my own person as a transfeminine person. I knew for sure; I had the dream of someday living fulltime as a woman. I just had no idea of how I was going to get there. I set out to discover answers to the many questions I had.

Such as, I knew I was not a cross dresser or transsexual. I was transgender looking for my path. Was I gay? What was my sexuality going to be under the gender affirming hormones I was seriously considering taking. It took me many years of searching before I finally received some long-awaited answers. And would I ever have the courage to face who I really was.

I was fortunate as I always mention that a small group of lesbians took me in and pushed me along my transition path. My sexuality did not have to change and that was one big question out of the way. My validation came from other women, not men and that was a fact.

Once I fully escaped my gender closet, I could look around with confidence and know my new transgender life was not built on addiction that I tried to solve, but on the facts, I refused to accept. I was never meant to be a man, and I was living a lie. The problem was I became good at the lie, and it was difficult to give up. Finally, I did learn through all my searching what the difference was between addiction and lie. Not a fact.

 

 

 

 

Thursday, October 9, 2025

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.

Wednesday, October 8, 2025

Trans Girl Acceptance Versus Competiton

 

Image from UnSplash. 

As I increased the intensity of my male to female gender transition, I was under the mistaken idea that women were not as competitive as men. Very quickly I discovered I was wrong. As with many other gender specific issues I faced, women compete as intensely as men, just on their unique level.

When I grew out of my teen girl dressing stage and began to blend in with the ciswomen at large in the world, I received my first real taste of feminine competition.  As a  man, I had always thought women dressed for other men, when if fact, they were dressing for other women. Once I got that through my thick head, life as a novice transgender woman became easier for me and I could finally progress in my journey out of my closet into the real world.

As I progressed. I wasn’t totally clueless about the differences between genders. My entire life, I had made it my business to study the world of women in case I ever made it in their world. Little did I know how difficult it would be for me to gain acceptance from the alpha female gatekeepers to the world I always wanted to be part of in the worst way. Perhaps, the most important lesson I needed to learn was how ciswomen competed in life. I had always assumed one shallow fact that women only compete on an appearance level. When in fact, they compete in a very complex layered system.

Maybe you have heard the term “Mama Bear?” It refers to women who intensely support their kids and family as one example of how women compete outside of just looking good. My daughter is a great example of a “Mama Bear” as she goes out of her way to protect her transgender child. There are plenty of other examples I have of women competing on a level which includes appearance. My company I managed a unit for used to throw lavish holiday parties which the women managers would go all out for in their gowns. Of course I was jealous as I was stuck in restricting, boring men’s clothing when I would have loved to have been in one of the fancy gowns. But I missed my opportunity again.

I found out too how women compete to keep their man. In yesterday’s post, I recounted an encounter I had with a less than pleasant woman who came back from the restroom and found me talking to her man. They left the venue quickly and I was left with claw marks down my back. Somehow, she thought I was competing for her man, and I never made that mistake again.

Another example could be the number of ciswomen who have no problem with transgender women or cross dressers as a group, UNTIL gender issues invade their own family and their husband comes home and opens up that he wants to be a woman. Then the real work begins from both man and wife as they try to discuss a gender transition. Afterall, what would the wife tell her friends and family.

The flip side of feminine competition is the wonderful world of cisgender woman acceptance. Depending on who you are asking for acceptance, expect a long journey of approving yourself as a worthy candidate for womanhood. As my wife told me so many times that I made a terrible woman, I needed to find out what she meant because I was beginning to have success in my feminine appearance. In her defense, she was right and until the gatekeepers let me behind the curtain to learn the world from a woman’s perspective. I did make a terrible woman.

Maybe you have known that one special ciswoman or two who have had that seemingly unlimited ability to love and accept the world. It is true that nothing can replace a woman’s love. And I have benefitted from them my entire life. Starting with my own mom, who after three still births kept trying until I came along. Plus, I can’t forget the wives who had loved me in their own unique way while I was on my solitary often selfish journey to transgender womanhood. It was not their fault I refused to face my gender truth.

Finally, it was an assortment of women such as Liz, Hope, Kim, Nikki and others who believed enough in me as a person to let me in to their world. They were my gatekeeps who showed me I didn’t have to compete with other women to be successful in my new life. Acceptance from them was all I needed. When I needed to compete, I could do it on a woman’s level because I had been there and done it.

 

Tuesday, October 7, 2025

I Never Missed a Beat

 

JJ Hart


Once I started down or up my long gender path, I never missed a beat, even though on occasion, the beats were far apart.

The beat started when the first time I experienced the thrill of experimenting with my mom’s clothes, I knew I was hooked as much as the garters I learned to use way back then to hold up mom’s hosiery. From then on, I went in as many spurts as I could to try to achieve my ultimate dream of being a girl, rather than just looking like one. The problem was I was restricted to hiding my gender ambitions from a totally unforgiving world. Primarily, an ultra-curious slightly younger brother who seemingly was always around. Locking myself away in the bathroom away from him only had the chance of working so many times as the instances I had of being totally alone were rare.

Even so, I managed to perfect my makeup routines in the rare moments I had. Perhaps the days of watching mom put “her face on” did me good. At least I had a working knowledge of how makeup should work, even though I struggled to improve my efforts and not look like a clown in drag. I wanted desperately to look like the other girls around me I saw at school. So much so, I daydreamed my life away wanting to be them. Luckily, at the time, I did not know how many beats I would have to make to reach my feminine dreams.

It turned out the biggest obstacle to my transgender dreams turned out to be the looming possibility of military service in the Vietnam War. It lasted so long in my youth, I literally started to worry about it when I was fourteen. At the least, my worst-case scenario of being drafted and sent off to war would wreck any ideas of fast forwarding my gender goals for years. Three, to be exact when the worst case happened, and I did get drafted. Then I took the option of serving an extra year to try to work in an Army vocation of my choice. As destiny would have it, everything turned out the best it could. Even to the point of seeing the world and coming out to very close friends that I was a transvestite. Which, in the long term, set up another problem.

The problem turned out to be that I was not being honest with myself or anyone else. I missed a beat in the worst possible way. I was not so much a transvestite or cross dresser, I was something much deeper than just having an innocent desire to wear women’s clothes. Deep down inside of me, a little voice was beginning to be heard that I wanted to again be a woman in my own right. The clothes I resorted to calming my desires meant little to nothing to me in the long term of my life. Worse yet, I missed many crucial beats of my life, as I ignored the little voice which was threatening to grow into a loud roar.

All of it set me up to escape my gender closet and begin to seriously explore the world as a transfeminine person. I needed to see if I could make it at all. When I did, the beat of my life began to totally pick up and I discovered I could make it as a transgender woman…if I wanted it bad enough. Plus, I needed to figure out what was I prepared to lose if I made the major step and transitioned into my version of womanhood. A long-term marriage, family, friends, and job potentially could all be gone if I followed the beats of my heart.

In what now seems like a blur, I was able to put less than desirable transition decisions behind me and then struck gold. Which was my experience with on-line relationships. After being stood up on countless (dates) my wife Liz of over a decade reached out to me saying I had sad eyes, and we have been together since. Never missing a beat.

Needless to say, that inner voice I mentioned deserves praise also. When given a chance, she led the way into a new exciting world of ciswomen I had only dreamed about. Even though I had gone down such a long gender path to arrive where I am today, it still does my soul good when a neighbor calls Liz and I “ladies” on our walks when we meet up. After all, I am just making up for lost time and missing many beats.

 

 

 

Monday, October 6, 2025

Can a Trans Girl Achieve Gender Parity

 

Image from Buddha Elemental 10
on UnSplash.

The main question I have is, have I ever achieved gender parity as I have gone this far in my male to female transition.

During my earliest days in the world as a novice transgender woman, I learned the hard way when I presented as a woman properly, I lost a portion of my intelligence immediately. Especially when I had the rare occasion to interact one on one with a man. My tow truck driver, for example, is my best one when one night when I first decided to go out on my own, my car broke down on a fairly busy road. Much to my chagrin, my problem attracted a well-meaning policeman, so I had him and the tow driver to deal with.

The first thing they did was huddle together and decide which route was the best way to get my car back to my house…without me. Who was I anyhow? Just a blond that needed help finding her way home, I guess. Then, when I was forced to ride back with my car in the cab of the truck, I found how much intelligence I had really lost. I was forced to act like I knew nothing about how his tow truck worked when in fact I did know a wheel was round and the cables on the truck were very strong. Before the short trip was over, I even found out what lunch his wife had packed him for work. I suppose I should have been happy, nothing out of the ordinary happened and he never seemed to let on he was helping a trans girl.

Through all of my early days of learning the gender parity I was experiencing, I needed to learn to keep my mouth shut around men and try to soothe their egos and the exact opposite around ciswomen. I threatened men and for the most part they ignored me, and women were curious and wanted to know what I was doing in their world. In my life as a man, I had never attracted so much female attention. While I was flattered, I tried my best to learn from all the new interactions I was having because often, all was not at it seemed with other women. When I played in their sandbox, I needed to learn all of their rules to achieve any amount of parity. Quickly I learned a smiling face did not always mean an accepting woman when passive aggression set in. I had one brutal night when I was caught just talking to a woman’s husband when she went to the rest room. When she came back, she was not happy with me and soon after the couple left the venue and I was left with claw marks down my back. Lesson learned.

The older I get, the more I think the reaction from toxic men in society is a reaction to gender parity. More than ever before, women are trying to step up and be the quality leaders we so desperately need. I can use my trans grandchild who uses the they and them pronouns as an example as they just started a job as a nuclear engineer following a graduation from The Ohio State University. They got a job as a civilian with the Navy so I hope they can be successful before the current batch of felons in Washington catches up with them. But that is a topic for another blog post.

One thing is for sure, when you jump the binary gender border from male to female, you will feel an instant change. I could no longer rely on size and bluster to get me by in the world with my male privilege. In order to be successful in the new feminine world I was in, I needed to be better as a transgender woman. I had to study and be comfortable I all the feminine areas such as restroom etiquette. Out were the days of just going to the men’s room and ignoring everyone else and in were the days of looking other women in the eye and smiling. For the most part, gender parity at that time meant being accepted in the world of women. How to start or continue a conversation beginning with an innocent compliment became important to me.

Right or wrong, any gender parity with men faded in importance with me as my lesbian friends taught me how important self-validation was without a man. I knew and my friends knew I was a valued person in their eyes, even though I had come to my womanhood from another path.

As society tries to minimize our importance as women, especially transgender women, it is time to realize the unique circumstances that brought us to the place we are today. And what we can add to our broken society in the future. So, I have achieved gender parity in my own way.

 

 

                                                                             

Sunday, October 5, 2025

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.

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, Hallow...