Showing posts with label cross dressers. Show all posts
Showing posts with label cross dressers. Show all posts

Thursday, July 2, 2026

The Best Advice I Never Got

 

Image from Frame Harriak
on UnSplash. 

The best advice I never got came from no one.

There was no one there to tell me anything about what I was doing when I was doing my best just to be feminine. No one to tell me my skirts were way too short and tight and my makeup looked like I just left a circus clown drag show. And better yet, no one to tell me I was heading along a gender path which would ultimately ruin my life if I kept it up.

The only person who was screaming in my ear initially as I cross dressed in front of the mirror was my male self-telling me to hurry up and get done before I risked discovery and the end to the world as I knew it. This was the time too when my feminine side was lying to me by telling me I was a pretty girl. Maybe I could see some of my femininity in my pre-male puberty years but quickly faded with my bodily changes.

As life progressed as it always does, I witnessed the battle of my voices as once again my male side was telling me to stop cross-dressing and never do it again and my feminine side saying keep on trying and things will get better. Even though it was difficult to listen to the best advice I never got I kept deciding to pursue my feminine side and see what would happen,

At that time, I was stuck in a series of Halloween parties where I could dress as myself and not fear reprisal. Plus, I could judge how I was doing with what I wanted to wear and with how far I had come with my makeup skills or lack of them. I was aware that I was at risk for stirring up potential risks of being discovered when someone would ask who shaved my legs and applied my makeup. I just said I shaved my own legs and did not mention who did my makeup because my second wife did not wear any. I was normally Ok because it would take another ciswoman to question my makeup because if a man did, I would figure he may be part of my femininization club. I learned so much from the Halloween parties I went to that not going to them dressed as myself was the best advice I never got.

I think it is ironic that that almost everyone has advice for everyone else except when it comes to transgender women and transgender men. It seems, our situation is so unique that the only advice someone can come up with is just not do it. They have no understanding of what we are going through, and it is so much deeper than just wearing clothes of the opposite gender. Maybe that is why I never got any advice from anyone except one of my self-proclaimed gender therapists who told me there was nothing she could do about me wanting to be a woman. Like a dummy, I ignored the only good advice I could have received at the time.

It wasn’t until I started reading certain on-line computer sites did, I really encounter advice as transgender “Nazi’s” as we called them. Who continually did battle with many cross dressers, who received little or no respect from the transsexuals as they were called then. Being the cynic that I am, I enjoyed quite a few of the comments as the gender battles raged on. Seemingly, respect from some on the site was only gained by how many gender surgeries you had gone through. Why I needed to wait to receive advice I did not want from an internet site which should have been welcoming to all but wasn’t.

By the time I hit my experimental stage to judge where I should be in the world as a man or a trans woman. I was not in much of a mood for much advice, and it was the best advice I could ever get. I was very much on my own in the world as a new transfeminine person and loving it. If someone had told me to stop what I was doing, I would have said hell no as I was having the time of my life.

I think other ciswomen sensed my confidence in who I was and mostly just interacted with me out of curiosity and at the same time, without knowing it showed me the way behind the gender curtain. I needed their help to achieve my dream, and not much advice. As the curtain parted and I learned what I needed to exist in a world I had only dreamed of, the best advice I got was none because I did not seek it out.

I cannot say I did not need advice when it came to making my final gender decisions. Primarily the day when my future wife Liz saw me mentally struggling again with my gender issues and flat out told me she had never seen any male in me. Go ahead and transition into a feminine world. In all fairness, I heard the same thing from my second wife years before but could not figure out how to do it. This time I could do it and received a doctor’s approval for HRT gender affirming hormones and major changes to by external and internal body was underway.

It turned out to be the best advice I ever got. Especially when my stubborn self-listened and decided to change my life for good. To the place it should have always been. Making my way in a world of ciswomen. Now I want the time back that I lost, but it is too late. I will just have to take my own advice and make the best life I can with the time I have left.

Thanks to you all who read along with all my experiences. Hopefully they will help you with yours and of course I will offer my own advice from all that I learned when you comment. Without all of you, none of what I do would be meaningful to me.

 

 

 

Saturday, June 27, 2026

Exorcising my Demons

 

Peaches Grille, Yellow Springs, Ohio.


Yesterday I went back to my hometown to pick up copies of court paperwork I needed on my name change so long ago.

By so long ago, I mean I finally had to sit in front of a judge who I knew to be very conservative to get my final name change signature. It was one super Christmas present as it all happened December 23, 2015. Even “Mr. Conservative Judge” himself said Merry Christmas when he signed my long overdue paperwork. As I remember now, I had many hoops to jump through such as posting a notice in the local newspaper and waiting for thirty days to see if anyone would object to the change. Then I needed to petition the court for the actual name change. My future wife Liz was with me when all of this happened, and we were on cloud nine when we received the final documents.

The only mistake I made was not getting enough court copies of my change due to poor planning and I ran out. So, the only thing I could do was make the hour and a half trip back to the court clerk for more certified copies that I needed to change one of my insurance policies names over from my old name to my new name. My only advice to those of you who are going through the legal name change process is to plan ahead and get plenty of copies and then get more.

By now you may be asking which of my demons did I exorcise. The first major demon was not having to see mail from my insurance company showing up with my previous male name on it and knowing it was not their fault but mine because I did not do anything about it. The second demon was even going back to my hometown (where I was born and raised) at all. It is an old industrial town which has had its heart ripped out a couple times by companies downsizing or even moving overseas. Setting all of that aside, I remember the rejection I received there from certain friends and family members when they discovered my deep, dark “gender secret”. It seems each rejection was burned into my soul.

So much so that I could not sleep the night before Liz and I went back to the city that I think never forgot about me. Even though that is a self-centered idea because it has in almost every way possible. My ex-brother still lives there who I am separated from and is another good reason to dread going back. To take the pressure off a little bit, I tried to meet up with my daughter and son-in-law in nearby Yellow Springs, Ohio which has always been a real treat to go to and has been referred to as the gayest town in Ohio.

My daughter could not be there because they were going to Maine to see my oldest grandchild who works up there as a nuclear engineer. Liz and I’s disappointment in not seeing daughter and son-in-law was short-lived because Yellow Springs was all decked out in its Pride finest as it was all going to happen the next day. We ended up stopping for lunch at a place called “Peaches Grill” for a great light lunch before we resumed our trip. “Peaches” was promoting their after-Pride party and was all decorated out in preparation. It was also the venue where I ended setting next to a “Debra Winger” look-a-like complete with the black “Urban Cowboy” movie cowgirl hat. It was a fun evening and no, she did not ask for my autograph (ha-ha). All in all, Yellow Springs is the direct opposite of my hometown which is only ten miles away.

Now, since I think I have all the papers I will need for any future demands put on me to vote by the Republicans, I am not envisioning any need to go back to my hometown since years ago now, I even sold the two properties I had left there. I don’t know why I have such a deep-seated fear of reliving all the bad moments that I had, I suppose it is just the vestiges of the life I had coming out into the world coming back to haunt me. And it speaks to the amount of suffering a transgender woman or transgender man can go through just to live their lives the way they need to.

I know too that I am one of the fortunate trans people who can get around freely in public since I present as just old now and can get by with my wife’s Liz help. I just have my age-old demons to harass me like I just went through. I dislike my old hometown so much, I even don’t want to mention it by name, but it is the one that the orange Russian in the White House keeps mentioning again when it comes to deporting the Haitians. I will let you fill in the blanks from there.

All in all, my demons are tough critters and the only survivors which still exist from my old male days. They play into my anxiety issues of always worrying ahead for seemingly any occasion. But as always, my feminine side has stood the test of time and has been successful in exorcising my demons. I guess you can say she has always had my back when the times were the darkest in the days when I was visiting Yellow Springs as a short-haired Army soldier when I desperately wanted to be one of the long-haired hippie girls I saw in their bell-bottom pants. It took me awhile, but I exorcised that demon who kept telling me I would never make it.

Most importantly we made the trip safely, even with a police detour set up on a rural highway for what looked like a potential swat situation as well as heavily pouring rain which hit us on and off. We made it past the demons and that is the important part.

 

 

 

Monday, June 8, 2026

Destination Unknown


 

JJ Hart and wife Liz on Right.

Through most of my life, I have taken the path less traveled to an unknown destination. Many times, I have thought I knew where I was headed, only to be faced with many stop signs in my way. It was like the night I took the night bus to Ft. Knox, Kentucky to begin my Army basic training. All I really knew was I did not want to be there and I would be in for more unpleasant situations than I wanted to count. All without my precious feminine wardrobe, heels and makeup to fall back on.

To make matters worse, some of the other men on the bus were not so silently crying about their fates which were coming up, quickly because before we knew it, the bus arrived at the not so beautiful, winter-time hills of Ft. Knox and we were greeted by drill sergeants and loaded from the bus into our waiting barracks. In a small way, I guess I was fortunate that I had two friends who were drafted ahead of me into the Army who told me what to expect and gave me some sort of confidence that I could successfully survive whatever was ahead.

Actually, for me, basic training went fast seeing as how I was facing an extended period of my life without the feminine fallbacks I had always known to get me by. Keep in mind too that the Army in those days was deeply gender separated and there were no women to interact with anywhere where I was at all in basic training. So, I was forced to do all my interaction with other men which I had never been good at. It turned out to be a learning experience I will never forget and even gave me extra insight about how competitive men interact with each other when there are no ciswomen to show off for.

Through it all, my inner super repressed feminine self was busily recording all of this for use later on in my life. Any spare moment I had when I was doing some sort of a mundane task in the chow hall for dinner like peel potatoes, I was given the chance to day dream off to the future and think of the new car I was going to buy with the money I was saving because of Uncle Sam taking care of everything I needed. I dreamed of buying a new wig and clothes and making it a point to slowly drive past my first fiancé who had rejected me when I was drafted into the military. She thought I should have tried to get out of serving because I was a cross-dresser. Which was close enough to being gay for her to get me rejected from duty.

When my three years of military service was up and I returned to the world I knew before, I returned almost exactly where I was with my cross-dressing when I left. The only difference was when Halloween rolled around and the newly restored Ohio Theatre in Columbus was having a costumed “Spook Out” with their newly restored theatre organ providing the background sound live for the silent version of the “Phantom of the Opera.” It was an opportunity for me to jump out of my dark gender closet and present my true self to the world for the first time since I was a civilian again. For the evening, I was the long blond-haired woman in heels and a minidress which of course included my freshly shaven legs and new panty hose. Outside of the heels beginning to bother me as the evening wore on, I had a wonderful time. Especially when I had the chance to see and appreciate the other costumes.

From there, the only problem I had was thinking about waiting another long year to be able to come out of my closet and express myself as a transfeminine person. I had just spent three years of my life waiting for my freedom from the Army and I did not want to wait anymore. My solution was to open my closet door and have the courage to come out on my own and not wait for another year. I knew in order to do it; I needed to take my feminine presentation standards way beyond what I was doing for Halloween if I was ever to make it in a world of ciswomen. Certainly, I made mistakes along the way as I stumbled out of the closet but managed to maintain the balance on my heels to get by in the world.

Thanks to previous life lessons I had learned to rely on myself, my inner female finally had her chance to come out and shine in the world when I started out evenings to go out and be by myself and ended up talking to other curious ciswomen wondering what I was doing in their world. I had learned to outgrow my shyness around strangers and become a social person, so my “plan” worked to perfection. I did not have to go out anymore to be by myself and my previous unknown gender destination was becoming clearer to me.

For the first time, I was able to see ahead of myself for future reference the stop signs I would face. Such as what was I going to do about all the male baggage I had managed to build up over the years against my will. If you are trans, you know what I am talking about such as spouses, family, friends and employment to begin with. Along the way, I have written entire posts about the power of stop signs and what they mean to transgender women and transgender men. I can only say, when you have negotiated all your stop signs and reached your unknown destination, you will have reached your own little utopian space because it feels so natural to you. At least it worked that way for me.

Thanks for reading along!

Any comments are always welcomed! 

 

 

Sunday, April 26, 2026

My Life's Passion

JJ Hart on vacation
last winter. 
Without a doubt, the one passion which has consumed my life the most has been my desire to be a woman.

I continually write about my youth as a confused boy wondering if I was the only boy in the world who wanted to be a girl. My desires extended all the way to what I wanted for Christmas (the doll baby I never got) all the way to when I lied about what I wanted to be when I grew up. Rather than rock the boat I always said some sort of a male profession such as a doctor or a lawyer rather than what I really wanted to be, a woman.

All I could do was take refuge in my mirror which told me I made a pretty girl out of the boy I was at the time. It became a passion for me to use as much of my free time as possible to cross-dress. At the same time, I became really good at acting like a boy by playing sports and having an interest in cars. I was so good, it kept the bullies away until male puberty invaded my body. Outside of hating the changes puberty was making to my body, I remember being intensely aware of my new masculinity and what to do with it. Even walking like a man was a chore for me to learn to do. I was so afraid of walking like a “sissy” and be made fun of by the bullies that I feared what to do. Little did I know that later in life my passion would be to unlearn all that I needed to learn at the time about being masculine.

As much as I tried and as tormented, I because of my gender passions, I could not seem to lose my desire to be feminine over my hated male image. At the time, I was in the midst of what I call the information “dark ages” before the internet and any social media input. Even the word transvestite was new to me as I struggled to find my footing in life. In other words, my gender closet was very dark and lonely, with little opportunity to have any future at all in my passion to understand and be feminine.

I stayed that way until I grew older and my passion included receiving my cherished issues of “Transvestia” magazine and I could read the “wisdom” of “Virginia Prince” whenever I could get my hands on another issue. For a while I thought it was working until I began to read about the social mixers certain chapters had to meet and greet other cross-dressers or transsexuals as they were known back in those days. Amazingly, one of the chapters in my native Ohio held mixers on a fairly regular basis that I could attend. I thought for sure, meeting others with similar gender issues could help me but I was wrong. Their passions exposed the many layers of where I could fit in (or not) with the remainder of the cross-dressing community and at the least, I hoped I could come away from the social by making a friend or two.

The only thing that really came out of the mixers was the knowledge that another chapter was coming close to establishing their own socials in Columbus, Ohio which was vastly closer for me to attend. Maybe I was too standoffish or even shy to make what I would call friends, but I continued to keep going any way and even was rewarded with invitations to smaller more diverse parties in Columbus which did not have to supposedly adhere to all of “Virginia Prince’s” archaic rules such as admitting heterosexual members only. As I said, the parties I went to were very diverse from lesbians to cross dresser admirers all the way to transgender women getting ready for gender realignment surgeries. The learning process I went through every time I went fueled my passion to learn more about my place in this new exciting world, I was becoming a part of. I could not wait to be invited to the next party.

I felt so secure from my party experiences, that I decided to do more exploring in my own in public. That is when I began to seek out the straight venues I used to go to as a man when I always wondered what it would be like to experience them as a woman. My passion for my new life exploded when I discovered I could be accepted which kept me out of the gay venues which I did not feel comfortable in at all. I was able to go out to be alone and mostly socialize by myself for the most part as I worked hard on my passion to fill out my gender workbook which was seriously lagging behind my fast-paced life as a novice transgender woman.

By this time, I had decided I had made the right decision to follow my feminine passion and try to survive in a world run by ciswomen. My path felt natural and I was rapidly coming close to the time when I was going to push all my male privileges I had earned to the middle of the table and bet my life on the transfeminine path I was on. I could not believe that my entire life’s dream/goal was suddenly within my grasp. If only I had the courage to finally follow through on my passion.

I did follow through and with the help of my future wife Liz, I went on HRT, threw out or gave away all my male clothes and never looked back on my male life except to decide which baggage to bring with me. I even went as far as taking female vocal lessons to try to teach me all important feminine communication skills which I desperately needed. It all turned out to be a labor of love as I listened and learned from the world around me.

The boy so long ago in the mirror finally had his deep-seated passions rewarded.

 

 

 

  


Saturday, April 4, 2026

Easter Envy

 

Image from Annie Spratt
on UnSplash. 

Once again, it is Easter and time for some ciswomen to model their new colorful, feminine dresses and accessories to the world.

Like most of you, I remember the envy I felt when once again I needed to be forced into a restrictive suit and tie for one of the rare occasions we went to church. Why couldn’t I be one of the girls in their Easter finery. All the envy in the world I felt did me no good as off to church we went. My parents thought I just did not want to go to church (which I didn’t) but did not realize the real reason. I was just jealous of the girls.

Back in those days, I had very little inkling of how my desire to look like the other girls ran much deeper than I ever thought it would. I was scratching the surface of where I would end up in life as a fulltime transgender woman. I thought it was an innocent hobby that perhaps some day I would grow out of when the opposite happened. I grew into it. If I had any idea of all the growing pains I would feel over the years as I grew into my true self, I don’t know if I would ever undertake the gender path I did.

The truth of the matter is that I did not think I had any choice. I was born into an unforgiving male world that I was expected to excel at. I knew too that if my cross-dressing or gender secret was uncovered, I would be sent to a psychiatrist and told I was mentally ill. I did not know exactly what was going on with me, but I knew I was not mentally ill for just wanting to be feminine. On the other hand, I knew my WWII/Depression era parents would have any idea of what was going on with their eldest son to take any creative measures to help. The first measure would be acceptance. In my wildest dreams, did I ever think they would buy me a pretty new dress for Easter and do away with my suit and tie forever. My parents were simply not built that way so that they could step out of their rigid parenting box to help me. I was stuck in a male world until I could figure a way out on my own.

Over the years, regardless of setbacks such as military service, I was fairly successful in my male life. Which ironically made it harder for me to give it all up and cross the gender border when the time came. One thing I never lost was the envy I felt for all ciswomen who inherited from birth what I wanted so bad. I kept remembering the girls and women in their Easter dresses, even though I rarely wore a dress as I attempted to blend into the world as a woman. It seemed fashion had gone away from the frilly feminine basics once I arrived at the point where I could take advantage of the new world I was in. For years what I did take advantage of was the fashion trend where I could wear oversized sweaters with miniskirts, flats and opaque tights. Sadly, fashion moved on, and I needed to also if I was still going to blend in with the world as a transgender woman. Not only did I have to try to equal the cis women I was around, I needed to be better. So, I went with denim mini’s with long flowing tops to attempt to hide my oversized male torso.

Even with all the effort I was putting in, it never seemed to be enough to compensate myself for not being the pretty girl in her new dress at Easter. Ironically, then I found out from my wife Liz how she was a tomboy and did not like all the frilly Easter fashion she had to wear and was always under inspection from her mom on getting her new white tights dirty. I learned the view of the other gender side was not always the better one. It left the door open for a greater understanding of what females go through to be socialized into women and why some never make it.

This Easter, if you are religious, I hope you have the opportunity to celebrate the true message of the day and you don’t get hung up on what the ciswomen and girls around you are wearing. Although, I don’t see many women getting all dressed up for any reason anymore. Maybe if I attended any sort of church services at all, I would.

At any rate, celebrate Easter in your world the best you can!

 

 

 

 

 

Friday, April 3, 2026

A Labor of Love

 

Image from Mayur Gala

Once I stopped being a victim thinking I was the only male in the world who wanted to be feminine, I quit being so negative about my life as a whole. That is when I started to enjoy wearing my mom’s clothes and experimenting with her makeup. All I really knew was that the process of cross dressing took away the problems I was experiencing in everyday male life to the point of even relaxing me. The only real issue I had was when the next time was I could find the privacy to do it.

I even went to the point (in warm weather) of stashing a small collection of clothes and makeup in a hollowed-out tree in a woods next to our house. I was in my own world and enjoyed the privacy I had to feel the clothes and dreaming that I was one of the attractive girls I saw at school and envied very much. At that time, I did not understand how I would take on a lifetime of work to pursue my labor of love.

The first task I needed to accomplish was when I was financially able to do it, was shop for and acquire a whole new set of clothes so I could present better in a world of ciswomen I needed to compete with in many ways. The first task I needed to complete was to slim down my male body as much as I could so I could fit into more stylish clothes I was suddenly finding in all the thrift stores I was shopping at. I liked the stores for two main reasons, the first of which was price of the items displayed and secondly, I never had any problems using the changing rooms to see if the items I was looking at actually fit. Plus, the challenge of doing so much shopping was something I loved. The only problem was where I was going to store away all my fashion treasures from the prying eyes of my wife who would wonder where they came from. Fortunately, we had a huge old house with plenty of places I could store my clothes.

After I began to dramatically improve my worldly presentation and use the public as my mirror, I found myself in a position where I could blend in with the public. To test myself, I even did tricks such as wearing sunglasses where I could see the eyes of the public when they could not see mine. That way, I could tell if they were staring at me or not and I was overjoyed to learn I had passed the test, and the public was ignoring me. From there I could widen my horizons on where I was attempting to go as a novice transgender woman. I was in love!

My love ironically did not last long because very soon, I discovered the public actually wanted to interact with me. Suddenly, I needed to work on a presentable voice so I could attempt to basically communicate mainly with other women since men did not want to have anything to do with me since I left the men’s club, I used to be part of. The fact remained; I did not miss male interaction at all. It was something I never had in my male life either as I always preferred the company of women. Surprisingly to me, as I transitioned, I was having no problem gaining feminine company. Probably because ciswomen for the most part were curious about what I was doing in their world. Plus, the women did not carry the paranoia about their sexuality that men had, they were not scared of me. Finally, I was showing the ultimate honesty about who I was which many women appreciated. For any number of those reasons, I loved the interactions I was having and being able to learn more from them about being a woman than ever before.

The fact I was loving my life at this point as a transfeminine person led me to realize that for the first time, my life was headed in the right direction. I felt so natural and even happy when I followed my gender path to a point where I was allowed behind the gender curtain to see if I really wanted to give up all my male privileges and keep moving forward to my ultimate goal of starting gender affirming hormones or HRT. If I could be approved by a doctor to do it. As I always say, I was approved and the changes were magical and I was in love again.

Before you begin to think my love revolved just around me and not another human being, my future wife Liz came into my life over a decade ago and changed everything. I was in my sixties and was thinking about spending the rest of my life alone when Liz and I met on an online dating site. We got along and she turned out to be the final push I needed to leave the male world behind. She was the missing link I needed to turn my transgender life around, and I love her very much.

It feels good to say that I love someone else more than I love myself or my gender transition for the first time in my life. According to my second wife who died many years ago. It would be interesting to see now what she would have thought about the feminine person I have become.

My final point is it is said you must love yourself before you can truly love someone else. Maybe I needed to learn my true self as a transgender woman before I could love someone else. It certainly took me long enough to love myself, a lifetime for me which spanned over half a century. Once I realized my path was a long labor of love, I learned the hard way I needed to be patient. Which was difficult for me, but I made it through and learned from my labor of love.

 

 

 

 

Thursday, April 2, 2026

Gender Lost and Found

 

Image from Ewoud Van Der
Brandon on UnSplash. 

On occasion, I think you must hit rock bottom in your male life before you can begin to build a new feminine one. I equate it to my own transgender lost and found in my life. Before I get into what I found when I started my path to my dreams, I decided I had to have a basic knowledge of where I wanted to go.

Seeing as how I was born into the pre-internet times when information came in magazines arriving in the mail, I was stuck in the “Transvestia” world of Virginia Prince if I wanted any information at all about transvestites or cross dressers, as Virginia called us and oh yes, we had to be heterosexual to join. Through it all, I was intrigued by the pictures of attractive men dressed as women, as well as the entire world of mixers you could go to. If you happened to live close enough to one to go which I did. Ironically, the mixers I attended did not do me much good because the only mixing which happened involved my brain when it was all over. Often, I left more confused about where I wanted to be with my gender struggles than when I started.

None of my searching was helping much and my attitude about myself was sinking to an all-time low. I felt lost and forsaken in my life and felt sorry for myself because I was the one who wanted to do away with being male and assume a feminine existence. It took me a while, but I finally backed off from being a victim and my ideas of whom I really was started to improve. I had hit rock bottom and was beginning to improve, which helped primarily my fragile mental health. My goal was to close my transgender lost and found department for good.

Sadly, I was a little ahead of my time to closing my department because I still had so much more to learn about existing and competing in a world run by ciswomen. With or without men. I labored under the impression if I could present well enough as a woman with my makeup and fashion, that would be all I needed to do to enter the world as a trans woman. I totally ignored all the layers of life a female needs to go through to be socialized into a full-fledged woman and I was painfully aware not all females make the transition. And even more aware of the path I would have to take to make my own transition because I had even farther to go to make it to my goal. I needed to be even better than the average ciswoman to be able to be accepted in the world and be allowed behind the “sacred” gender curtain which women used to provide a layer of protection from men.

On my path to going behind the gender curtain, I had at least one big stop sign I needed to work my way around. It was proving how badly I wanted to give up all my male privileges and start all over again. I just did not magically appear in the ciswoman’s world asking for admittance without paying my dues. My transgender lost department was closed as a man, and I found I had done the right thing by pursuing a feminine life. My only problem was that I was impatient about the road I was going down and constantly I wanted more. Before I knew it, I was even getting ahead of myself in the plan I had set up for my grand gender transition. Here I was busily carving out a new feminine life where no one knew me as a man while at the same time I still had a loving wife, family and good job to deal with because I knew I could lose them all when I found my transgender self completely.

My problem also was, I was filling out my gender workbook faster than I ever imagined I could and my plans were coming into focus. No longer did I have just dreams of the possibility of transition into a feminine world, I had the reality of doing it. My lost and found was gone from my male side and he had finally begun to see the reality of his situation and gave in to the feminine side of life which was taking over for better or for worse.

It was at that point in my life when I pursued my ultimate dream of pursuing HRT or gender affirming hormones as the next step in my transition to being a transfeminine person. I went to a doctor for a physical and was approved to start a minimum dosage of the precious new hormones I was taking. Almost immediately, my body began to feel the changes as if it had always been meant for them to happen. The changes always take a whole blog post to describe, but to put it simply, my internal changes such as my new emotions would fill a book. The external changes became quickly obvious too, as my hair grew along with my breasts and my skin began to soften along with the angles of my face. I can only describe the changes as amazing and magical as they made living as a man impossible to me anymore. I had to close my male life and never look back.

I can not oversimplify it enough about all the stress and work I put into to close my transgender lost and found for good. To be sure, it was a labor of love to do it, and I would have never had it any other way. If Indeed I had another choice anyhow. Once I determined I never really did, I could relax and get rid of my guilt about doing away with all the male privilege I had worked so hard to earn. In the end though, it was worth the struggle.

 

 

Sunday, February 22, 2026

Did I Believe in Magic?

 

Image from Delphian Lacub
on UnSplash.


It is rare, but on occasion, I still hear the question of when I knew I had gender issues.

The truth of the matter is, I always knew I was transgender. I just did not know how to express it until I was older. It was after my early explorations into my mom’s clothes did, I realize the potential magic I was holding when I carefully tried on her clothes knowing fully it would not be long until I would outgrow all her wardrobe and I would be in never-never land when it came to finding feminine clothes to wear.

Somehow in the near future, I made do with stretching elastic girl’s clothes I found in the lost and found box at the school I went to. I had a short skirt I managed to squeeze into that I cherished forever it seemed. Around that skirt I managed to build the basics of my style with the money I earned from allowances and stray jobs I found. I delivered newspapers and even mowed a cemetery for a dollar a hour in the hot summer sun, just so I could sneak out to a store and buy more feminizing items. Through it all, I believed in the magic which made me who I truly was.

It was always difficult for me to hang on to my trans truth because at the same time I was experimenting with being a girl, my male self was actually able to establish himself successfully in the world. Which just served to tear up my fragile mental health enough. Until you must wake up in the morning wondering if you are a boy or a girl, you don’t know what I am talking about. I would not have wished it on my worst enemy.

On certain occasions, my magic was strong and I felt like a girl when I looked at myself in the mirror. On other occasions, life was hell when I could not find the time to sneak around and cross dress as the girl I was. It was during those times; I had to rely on just that small amount of magic to get me by. One of the problems was I was so envious of the other girls around me at school in their pretty clothes and admiring looks from all the boys. I dreamed of being just like them.

It wasn’t until I began to explore the world as a novice transfeminine person, did I finally realize what my magic was all about. All of the doubts I had on where I was headed in my life began to dissolve when I began to feel so natural in my progression. Life was a blur as I was going out to be by myself in the world as a transgender woman. By doing so, I was able to meet strangers who accepted me for who I was. For the first time in my life, I was able to shed the long shadow of the remnants of my male past.  Every night, I was able to find my way out to one of my regular venues, be it lesbian or straight, I never wanted to return to my male self at all and lose my magic.

It turned out, my magic never went away, it just became stronger. So much so that I made the move to forever give up my male ways and start gender affirming hormones or HRT. The hormones just reaffirmed and strengthened my belief that magic could happen and I could indeed be the transgender woman who could forever lose her male past and survive. I could change my life from being married, with friends, family and a great job into a much more mellow existence.

It just took me too long to realize how deep my magic went in my life, and how backwards I had my whole existence and how much pain it caused me. It was my fault because I did not believe in my own magic enough to do something about it rather than be a part-time cross-dresser. I always point out I have nothing against cross-dressers at all because I depended upon it to live my life for so long.

Did I believe in magic? No. Should I have, absolutely.

 

 

Friday, December 19, 2025

More Gender Dreams

 

Image from Robin Edqvist
on UnSplash.

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

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

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

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

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

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

 

 

 

Thursday, November 20, 2025

Five Million

 

Original image. 
JJ Hart writing.

Recently, I reached a milestone as far as my blogging “career” goes.

This week, I reached and went over my five millionth hit to the blog which was amazing to me when I considered the humble way this all got started. I actually started blogging a long time ago when I barely even knew what the term meant. And I did it mainly because of the discussions I had with “Connie” an online transgender woman friend I had met from Seattle. Along the way, on another site we were on, we discovered a mutual dislike for what we called “trans-nazi’s” or transsexuals who based their worth on the number of gender operations they had undergone. Somehow, they felt better than the rest of us and were not shy about letting us know it.

From there, I had started to relay the experiences I was having as I initially began the trip out of my closet and into the world. “Connie” thought my experiences would be worth sharing and here we are so many years later. In many ways, both of us share the same sarcastic sense of humor, so we matched up well.

On a much deeper level than just harassing the “trans-nazi’s”, I hoped sharing what I went through in my lifelong gender journey would be a great way to pay forward my experiences and help others. Every time I receive a comment or two from a person in need of guidance as a beginning cross dresser or transgender person, I feel honored that they reached out to me. While all our trips are different, at the same time we are similar and have all have the same opportunities to learn from each other.

Five million hits later, I now realize the strain of finding subjects to write about on a daily basis really takes it out on me until I run across a comment or two which keeps me going. It fulfils the original idea I had when I started writing something I did not know I could keep on doing for any length of time. When the comments kept rolling in, I knew I was on the right track because I thought the audience I was writing to represent is a very narrow part of a potential audience. Then I thought, if I was reaching just one person out of the vast majority of readers on the internet, I would be doing my job. I learned to be more satisfied with being more of a niche blog, designed for the transgender audience or those that were questioning being trans and would their life look similar to mine. Because switching your main binary gender is so difficult and intimidating to do.

The bottom line is, I would not have all those hits if it was not for you and I cannot comprehend how many of you come from around the world to visit the blog. My deepest thanks go out to all of you no matter where you are.

Even though now I write on two separate platforms, I still write for free because I feel it is the right thing to do. It just makes me feel better.

Once again, I cannot thank you enough for joining me in my gender journey and I should do it more. Just be assured, it means a lot to me when you read along and even take the time to comment!

May we continue on to many subjects together in the future. 

 

Tuesday, November 4, 2025

Falling Asleep in my Heels

Image from Toa Heftiba
on UnSplash.

Falling asleep in my new high heels turned out to be a very dangerous thing for me to do.

There was a time when I was in my early formative cross-dressing years that I thought wearing high heels was a fashion necessity I could not do without. Instinctively I knew the heels made my legs shapelier and longer. But what I did not realize was how much power the shoes gave the ciswoman wearing them. Have you ever noticed how men follow the sound of heels when a woman enters a room? Plus, the power extends from men to other women, who at the least responded to the expertise it took to wear a pair of high heeled shoes.

So, where did the danger come in for me? Actually, in. several different ways. First came the pure challenge of wearing heels. I had never experienced anything like it in my entire life but only knew the shoes made me feel so deliciously feminine. Through sheer effort, I conquered my fear of wearing heels so much that I forgot I was wearing them and ended up with another big problem, looking like a linebacker in drag, in heels. So much so that one night as I was trying to negotiate the stairs at home, my wife barked at me with a feet forward command. I never forgot that night and resolved to walk better in the future.

There were times in my past when heels went out as a fashion accessory and flat shoes were in with over-sized sweaters and short mini skirts for ciswomen everywhere. I was overjoyed with the idea of showing my legs off in tights and opaque pantyhose but again found myself in a situation where I needed to really concentrate on how I walked femininely without the heels I had come to rely upon. It seemed one of my favorite female privileges was taken away just when I was getting used to them. As with anything else in the fashion world of women, if you don’t like something, just wait because change is just around the corner.

That corner for me turned out to be a long way away. My fashion sense turned into a strong urge to blend in with other women in the world. Which meant where I was going, the women around me never wore heels. Especially all of my lesbian friends. Like them, I went for comfort in my footwear and blended right in, especially at all the lesbian mixers I went to.

My caveat to all of this comes from the transgender women such as “Stana” at the “Femulate” blog who have fabulous legs. Years ago, I had the pleasure of meeting her in Dayton, Ohio. Stana is tall to begin with and makes a striking beautiful woman when you meet her in person. Where we met, there were a group of men waiting for a ride when the elevator opened and out stepped Stana in all her long-legged glory. From where I was waiting, I could see everyman in the lobby turning to admire her. As you can tell, I have never forgotten the moment years ago when Stana took every advantage of her legs and heels as a transgender woman.

As I grew older, unfortunately, I had an old football injury destroying my ability to wear any heels at all. I broke my left ankle twice in the same place and wearing heels just became unbearable. To compensate in my own way, I try to buy stylish shoes and boots with no heels that I can walk in.

Regardless, I still remember the days when I felt the power of wearing my high heels gave me. Even after I went through the paranoia of feeling I was so much taller in the shoes. I decided to stand tall and be proud of myself, even though I was barely six feet tall. I had the opposite effect of going to sleep in my heels. I was wearing them proudly when I could. As I said, time has passed for me and I need to go for total comfort in my footwear, and it makes me sad. I feel I have lost a portion of my transfeminine self which will never be reclaimed. In the meantime, I can sit back and admire any woman I see negotiating the world in her high heeled shoes. As I know what she is going through, so I appreciate it.

As for you, if you haven’t checked out the “Femulate” blog yet, try it and you will see several transwomen and cross dressers in their heels and hose. Then you can go home and practice. Till you have your walk down and attempt in the public’s eye and watch out for sidewalk cracks which can cause you problems. Which I know from personal experiences.

 

  

Friday, October 24, 2025

Growing Like a Weed

 

Image from Marya Volk 
on UnSplash.

I was devastated when I outgrew all my mom’s clothes and I had no sister’s closets to raid for clothes. Where would I ever be able to find the feminine accessories, I needed to cross dress in front of the mirror. So, I had to rely on a little luck and a whole lot of creativity to get by. For example, I found a discarded cute stretch mini skirt just outside of the girl’s locker room at school which fit me, and I had it for years. The rest of my “collection” came from being able to do work around the house, and a rural newspaper route I had delivering papers. My parents loved the fact that I was so industrious without ever knowing the real reason why.

As I continued my ascent towards unwanted puberty and testosterone poisoning, sadly I continued to grow like a weed, making it less probable I could find any clothes to fit me. Somehow, I did by being very creative with my meager funds and having the courage to sneak out of my grandma’s house to secretly go shopping for clothes and makeup. As I always point out, we lived out of town, and the only way I had to get around was by my bike, unless I spent the night at grandma’s. Who lived close to downtown where we lived. I survived the clerks in the stores I went to and slowly became better at what I bought.

Through it all, I thought I would outgrow this portion of my life when all I wanted was to be a girl. Like a weed, it kept on growing in me and refused to go away. I went through the usual phases of gender dysphoria many of us go through. The heights of euphoria when I crossed dressed, and the lows when I was not able to. The pressure on me continued to build up until I took chances and dressed in a locked room with my brother around. Certainly, if I was discovered, my parents would have treated me with enough weed killer at a psychiatrist appointment to do me in. My parents’ eldest son wanting to be a girl would not have been tolerated.

Either I was better in hiding my cross dressing from them, or they chose to ignore it, because nothing was ever said to me, and I dodged any trips to therapy where they knew nothing about gender dysphoria and would refer to me as being mentally ill.

The older I became, the more my weed sprouted and refused to go away. In fact, when the internet era began and we bought our first computer, it gave me the chance to research what sort of a weed I had. Very quickly I learned my early ideas were correct and I was much more than a weekend cross dresser who was more or less wanting to look like a ciswoman as some sort of a hobby. In fact, I was transgender which was a new term back in those days. For the first time in my life, I found a label which fit me. I was not a cross dresser at all, nor was I a fully-fledged transsexual who wanted to run off and have genital realignment surgery. Through the computer I was even able to meet others similar to me for the first time in my life.

At that point, I began to realize my weed was not a weed at all, it was turning out to be more of a late blooming flower which had to be explored and nurtured. As  I began to explore the new feminine world I was in, I discovered how complex ciswomen had it in their lives and what affected them. I can use my second wife as an example of how badly a woman could feel when her husband wants to run off and be a woman. Often without having the knowledge to do it. I felt sorry for my wife, and we fought often, but there was nothing I could do about my new flower in my life. It was not out of control as much as it was me and I refused to confront it. Long story short, she did not live long enough to experience the transfeminine person I had become and that was a shame because like it or not, she had a lot to do with the new feminine me.

Now I feel sorry for all those toxic men and ciswomen who can not seem to find their way out of their weed patch. Growing a beautiful new flower is the only way to go as you live your life as a transgender woman. Now I know why my old male self never liked flowers.

 

 

Wednesday, September 10, 2025

Change was Coming

 

JJ Hart

As I grew into myself, I learned the truth. Change was coming if I liked it or not.

Change was one of the reasons I loved the fall season so much. As the weather cooled off and football came on, I could go through my feminine wardrobe and see what I could keep and what had to be discarded. Plus, I can’t forget Halloween which of course is the cross dressers’ national holiday in October.

Sadly, as the leaves began to change and fall from the trees, the whole time was bittersweet for me. The worst fall I could remember was when I was on a six-month delay to join the Army and I was working at a small radio station in Bowling Green, Ohio. If you are not familiar with that part of northwest Ohio, it is very flat to the point that any hills are manmade. One night, I was just driving around feeling sorry for myself as I looked ahead to Army basic training and I was so sad as the leaves blew in front of me. If I could have cried, I would have, but tears were nearly impossible for me in my male pre-HRT days. Similar to everything else in those days, I internalized my feelings and tried to move on as deep down I knew change had to happen.

During that time, I almost outed myself to my roommates in the apartment I was staying in until I left for basic. On one trip home, I brought back one of my favorite outfits along with a wig and makeup to Bowling Green. One day when I left, I assumed I had hidden my belongings well enough to not be discovered but I was wrong, and one night when I was preparing to surprise a male visitor to the apartment, after I went to work of shaving my legs and face, I checked for my clothes, and they were gone. I certainly thought, for a while change was coming then it was not. No one said a word to me and very soon, I was off to play soldier anyway so nothing else mattered.

Back in those Vietnam War days, basic training was an intense team building experience when a few drill sergeants needed to try to get a bunch of raw recruits ready for possible combat. During this time, the only way I could keep my girl self-alive was to bury her deeply in my subconscious mind, So, when we were on long forced marches around Ft. Knox, I made sure I thought about the well-being of my girl and the changes we would go through after my military service was finished.

Looking back at the three years I served; the time now seems like a blur and when I was discharged, I came really close to making a big change then by picking my future wife up at the airport cross dressed as my transfeminine self. I even went as far as hinting as such when I wrote her a letter. (Remember those?) Again, my male self-won out and I decided not to, and my big change had to go back to coming again. I did not have the courage yet to face my gender truth and took the easy way out and went back to accepting all the male privileges I had earned.

It was not until I became a parent and had reached my thirties did change to me become a real priority. I will always remember my thirtieth birthday being my hardest because I still hadn’t decided what I was going to do with my life. Sure, I had employment and financial issues to be aware of but again the underlying big elephant in the room was what changes would have to happen with my gender. I knew it was never going to be easy to present well as a woman, and I needed to work extra hard to earn whatever passing grades I could achieve in the public’s eye. Once I made the mental changes to proceed, much of my work became cosmetic in nature.

I was able to move the elephant aside and set about learning what it would take me to really live life as a transgender woman and not just be the “Pretty, pretty princess” my second wife called me. As change set in, I learned very few trans women or women at all live the life of a princess and I had a lot of work to do to put my male life behind me.

The last major change I put myself through was the hormonal one when I started gender affirming hormones. The HRT allowed me to sync up my external and internal selves and live a more productive life as a transfeminine person.

Sunday, August 17, 2025

When Who You Are is Against the Law

 

Kim Davis wants YOUR Rights.

Yesterday, the spineless governor of my native Ohio agreed with the felon/pedo in chief tRumpt to send national guard troops to Washington DC.

The move was a stark reminder to me of how close we are as a nation to a fascist state with a dictator in charge. And, on the battle lines are transgender women and transgender men who at least here in Ohio have watched as our rights have been taken away by a heavily gerrymandered Republican legislature who prefers doing its dirty work under the late-night cover of darkness.

I am extra paranoid because I vividly remember the gay/ cross dressers being rounded up in police buses when I was young in Dayton, Ohio. I certainly don’t want those times to return for myself or especially for my transgender grandchild.

Especially horrific are the Caitlyn Jenners of the world who insist on supporting the regime in Washington. Obviously, they never really learned how it was to have their rights taken away. Perhaps you noticed, I refused to refer to Jenner as “she.” Recently, on a popular social media site I am on, a rather spirited (to say the least) discussion about cross dressers and transgender women. The moderator waded in with some sort of a statement that cross dressers cannot be transgender women and tied the discussion all in with the male privileges CD’s refuse to give up the way trans women have. Then used Jenner as an example. Being smart for a change, I stayed completely out of the fray. Almost.

I did use the example of the cross dressers and/or transgender women I knew who were strong orange felon supporters. I will never understand how they could throw themselves or the trans community under the bus and keep doing it. Their excuse was, he couldn’t be that bad. Well, he was.

Then there are the comfortable gay and lesbian tRumpt supporters who sat back in their shells and thought all the misery being brought upon the transgender community couldn’t happen to them. Now Kim Davis is back asking the corrupt supreme court to formally destroy the same sex marriage ruling the gays and lesbians celebrated so many years ago. Now their refusal to get totally behind the transgender community in our time of need is coming back to haunt them. It could and would be coming around again.

I know one of the problems with this post is I stereotyped too many people along the way. I know many in the gay, lesbian, and cross-dressing community who don’t support the sick felon and do support the trans community and that is powerful because we need everyone behind us in these desperate times.

Just imagine if you are a novice crossdresser trying to decide if you want to attempt to jump out of your gender closet and are afraid of being arrested. It’s uncomfortably close to happening in states such as Ohio. The midterms are coming and make sure you vote from your closet for the right candidates.

On the bright side (and there always is one), there are pockets of support in major cities around the country. If you are struggling, try to find a LGBTQ support group to help you come out. In the meantime, buckle up for a rough ride and stay safe.

Sorry for the rant, sometimes I just have to vent.

Sunday, April 13, 2025

The Darkness

 

Transvestia Magazine 1960.




The darkness in my transgender closet was intense and complete. I had no windows or doors to let any light in at all.

One of the problems I had was I lived in the pre-internet era when there was little to none gender information to learn from. I needed to wait for my monthly issue of "Virginia Prince's" Transvestia Magazine for so called heterosexual cross dressers only to learn there were others like me struggling with gender issues in the world at all. Even with the brief glimpse into the lives of others, I had very little of light in my dark lonely closet. I was very far away from knowing there was absolutely nothing wrong with being me. 

With guidance from the back pages of Transvestia, I managed to gather the confidence to attend a relatively close by mixer, blending cross dressers of every sort (or transvestites as they were known back then) with transsexuals. Remember, the transgender term was not used at the time. At the time, I was very naive and thought going to a mixer or two would help me out of my gender closet.  I was wrong and all I learned was I needed to go back to my dark closet until I learned more concerning others who might share gender issues with. 

What I did learn was there was no easy way to fit in with the transvestite community. I was too much of a woman for the parttime cross dressers and not enough to fit in with the transsexuals I met who were waiting for gender realignment surgery. Deep down I knew, I was not prepared for the surgeries needed to change my genitals and gender was not between my legs for me anyhow. It was between the ears in my brain. All the process did at the time was enable me to look for a brighter light in my closet. 

Sometimes I believe that unless you have experienced a dark closet yourself, it is impossible to explain to a person who never had to go through it. I know also, there are many of you who read the blog are hopelessly stuck in your own closets. Especially, with an increasingly politically charged anti-transgender world around us. Hopefully, you live in an area which is more liberal and welcoming to those with gender issues. 

I write often about how my life slowly changed through several transitions as I deluded myself as to who I really was. I internalized my true gender for nearly fifty years. Early on, I told myself I was a man cross dressing as a woman, when the opposite was true. I was a woman cross dressing as a man the best I could. At the same time, I was nearing one of the most important transitions of my life, when I began to think of myself as a transgender woman and not a cross dresser. It was only at that point, when the darkness began to lift from my life, and I could live again. 

Hopefully, your gender life as a cross dresser or transgender person is not ruled by darkness and the light at the end of the tunnel you see is not the train.

On a Gender Vacation without a Passport

  JJ Hart I saw on the news this morning that shortly after the Fourth of July holiday is the busiest time to travel during the year. It got...