Showing posts with label male to female femininization. Show all posts
Showing posts with label male to female femininization. Show all posts

Wednesday, December 24, 2025

Happy Holidays!

 

Ralphie!

Happy Holidays to you and yours!

I hope those of you who have experienced close family losses because you came out to them as transgender are able to rebuild close ties with other non-blood more accepting people. They are out there and it sometimes takes a while to rebuild trust with other people with your feelings I know. Sometimes, you can find connections within your local LGBTQ organizations. I know, around here where I live that is the case when organizations host potlucks as well as Christmas parties for anyone who wants to come and be around others.

Also, as we are preparing to put 2025 behind us, we look to the holidays to provide hope for the future. 2026 will be a huge election year for example. It seems we are building a chance to put the political tragedies heaped upon us by a rotten president leading an equally rotten, spineless political party which has used the transgender community for everything evil in our country. It will take all of us, pulling together, to make a difference which is part of the holiday spirit. That is why I urge even the most closeted cross dresser to look out of their closet to a future of freedoms they may need later in life.

Happy Holidays to me also means thanking all of you who took the time to wish me the best this time of the year.

On Christmas Day, I will be binge watching “A Christmas Story” which hits so close to home for me. Other than the time period which it is filmed in which roughly matches my life, there is the story of “Ralphie” and his BB Gun. If you have never seen the movie, Ralphie is the child star of the show who desperately wants a BB Gun for Christmas. And the movie goes through all the trials and tribulations he goes through to receive one as a gift. Just when all seemed lost, and all the gifts were opened and Ralphie was dejected, when his father pulls out a brand-new Daisy BB Gun he had been hiding and then the fun began.

My major point to all of this is, I had a major role reversal with Ralphie and the BB Gun. You see, I never wanted a gun of any sort for Christmas and would much have wanted a nice doll baby or a new pretty dress. But there I was once again stuck in a male world I wanted nothing to do with.  That is why I am so enamored with “A Christmas Story” which goes right up there with the National Lampoon’s holiday classic with Chevy Chase as one of my favorites.

I know I am so fortunate to be spending my Christmas with my wife Liz who scooped me up off the trash heap of life I was on at the time when we met online over a decade ago. She was kind enough to accept some of my off-the-wall holiday traditions as well as me accepting hers. I guess that is the basis of a good relationship but one which worked out so well for me. Hopefully, you will find yourself in the same situation or will be in the upcoming year. It happened to me when I least expected it. 

In the meantime, here is wishing you and yours a safe and festive holiday season and don’t drink all of the high-powered eggnog which I used to do! Save some for someone else…It is Christmas!

 

 

 

Tuesday, December 23, 2025

Acceptance...all that And More

 

JJ Hart.

Just a short post this morning since I was out and about with my wife Liz to medical appointments and more.

This morning, I got up early to go with my wife Liz to her doctor’s office appointment. Per norm, I did not expect much interaction with the public since we were going at such an early hour. So, I could keep my feminine prep to a minimum.

I kept my prep to a close shave and brushed my hair along with leggings and sweatshirt top and I was ready to go. With my rain boots along with the wrap my daughter got me for my birthday to keep the cold wet away. As Liz went to the receptionist at the hospital to be checked in, I grabbed a nearby seat to sit and wait, and the receptionist very much ignored me one way or another. I was off to a good start as all of the other people who followed us into the large waiting room were off in their own world and ignored me also.

As I was playing on my phone as I waited for Liz, I began to think about how far that I have come over the years when it comes to being accepted as me, as my true self. I used to obsess on my appearance when I went out and about at all, until I noticed I was the only woman doing it. Gender acceptance was as important to me then but was still somehow different. These days, my acceptance level seems to be at an all time high which is great for my continued confidence as a transgender woman.  I will certainly need all that I can get when Liz and I take off again for another extended vacation south from Ohio in the latter part of January. As always, my paranoia stems from using the women’s room in the states we travel through which frown on it.

Through it all, I keep telling myself this is the fourth or fifth tour we have been on, and I have never had any restroom problems, so why start now.

Other than that, we don’t have much going on except I have a mammogram in February.  It is hard to believe the winter will have moved on so quickly from me. Especially at my age, it is sad to see life moving by so fast. 

Back to the present, to reward Liz for getting her flu and pneumonia shots, we went through our favorite coffee shop, drive through for warm coffee drinks and a light breakfast sandwich and the girl at the drive through window said, “you girls have a nice day.”  With that comment, she made sure I did.

No matter how long I live my dream of being a transfeminine person, reinforcement from a stranger is always great acceptance and more.

 

 

 


Monday, December 22, 2025

The Hustle and Bustle of Christmas as a Transgender Woman

 

Image from Clarke Sanders
on UnSplash.

Doing the Christmas shopping shuffle as a transgender woman, often takes a lot of courage and confidence to do it.

Over the past couple of weeks, I have written about my holiday adventures leading up to the big day. From taking a short trip to Clifton Mill to view their extensive, festive lighting display all the way to letting two men load my heavy purchase for me at an Oak furniture store, I stretched the boundaries of what I was used to as a new cross dresser or trans woman in public. After it was all said and done, even though I was terrified most of the time, I was happy I tried it all. I came out of doing the Christmas shuffle with much more confidence in my girl self than I had going into the season.

In fact, as I have written before, Christmas quickly outpaced Halloween as my favorite holiday. Why? There were several factors, such as the length of the season and the creativity I could put into celebrating it. Plus, for once, I was doing good for others by buying gifts for them as I shopped. I positively loved it and wondered where the experience had been most of my life.

If you are a procrastinator and last-minute gift shopper like I was, doing the Christmas shuffle as a transgender woman is ideal for you. As you can get lost in the crowds quite easily and no one pays attention to a single woman out doing her late shopping. Custom made for you to do your shuffle and head back home.

I was fortunate when my second wife left her bookkeeping job and took a managerial position at a large bookstore chain. So, at Christmas, she was very busy and worked many hours. It was easy for me to schedule my hours around hers, so I had plenty of time to get out of the house and do gift shopping. I could obsess on wearing just the right outfit to blend in with a busy world and at the same time, search for just the right gift. Along the way also, I could stop in and grab a bite to eat at a restaurant and again stretch my ability to deal one on one with the world as a transfeminine person. Yet another reason, I came to prefer Christmas over Halloween because I hoped I was not perceived as a man wearing a costume, or worse yet some sort of drag queen.

As the big day approached, the sky was the limit for me. I did my shuffle as much as finances allowed and stockpiled my gifts for my special night where I stayed home with some high-powered eggnog and wrapped my treasures to go under the tree if they would fit. Of course, my wife was close to being a professional gift wrapper and I was just the opposite. But as the eggnog kicked in, I did not care, and besides it was the thought that counted. Right?

Finally, the big day arrived and I was shuffled out. Plus, we had family connections to visit all day on Christmas day. My thoughts for once were in other places than doing my precious shuffle which I had learned so much from. After the day wound down and my wife and I were alone, we opened the final gifts from each other. Which included a gift for my feminine self. I will forever remember a nice fancy fuzzy baby blue sweater she gifted me. It was snug fitting and I filled it out nicely with my new silicone breast forms I received from a cross-dresser acquaintance of mine who was purging. Naturally, that part of our gift giving day was the part of the day which was the most anticipated for me. I was like a little kid, brimming with anticipation.

Every year after the intense transgender Christmas shuffle was over, I had the chance to sit back and reflect on all my experiences and what they meant. Without hesitation, I think the confidence I built up from going out in the world as my trans self was the most important aspect of what happened to me. I learned what it meant to blend in with ciswomen around me and survive better than I ever could before. I also discovered the vast majority of the world did not and does not care about having a transgender person in their midst. The biggest difference is that back then, we did not have a Russian asset in the White House leading his blind, spineless party into demonizing a small portion of the population. Back then, I was merely a curiosity to many people, especially ciswomen.

When my second wife passed away, the need to do the major Christmas shuffle went with her too. The only blood family I had left was a brother and a daughter to worry about at all during the holidays. When I came out to them, I was roundly rejected by my brother and completely accepted by my daughter and her family. So, I broke even and even did better when I considered the relationship, I was able to build up with my daughter, son-in-law and three grandchildren. I won the family coming out shuffle in a big way.

Even still, sometimes I miss the hustle and bustle of doing the transgender Christmas shuffle as over the years, I have gone nearly the entire direction in the other way. It is hard to say what I miss most but it probably having the financial resources to buy basically as many gifts as I could afford might be it.  Maybe it all came from having a guilty conscience from sneaking out of our house to join the world as my authentic true self instead of my old boring male self and breaking the pledge, I gave my wife that I never would.

Whatever the case, I was extremely selfish and was a contradiction when I did it to buy gifts for others. I guess it fit in with the whole contradiction I felt from my deep-set gender dysphoria to begin with. I dealt with it all the best I could, did my Christmas gender shuffle and moved on with my life making the most of it.

 

 

Sunday, December 21, 2025

Earning my Way into the Sandbox of Women

 

Image from Juli
Kosalapova on
UnSplash.

I call being accepted in the feminine world of ciswomen around me, as being able to play in their sandbox.

Getting a chance was similar to living a dream and very difficult for me to do. To begin with, I needed to lose whatever weight I could off of my very male dominate frame and take better care of my skin, so I could use less makeup. I desperately wanted to be pretty but accomplished it as naturally as I could. Motivation to do both came easily for me because I was obsessed with doing something very well in life that I cared so deeply about. Surprising even myself, I was able to shed nearly fifty pounds as well start moisturizing daily after I shaved. Obviously, the weight loss helped more dramatically when I could shop for a better selection of stylish women’s clothes in my new size and the decrease in makeup I needed spoke for itself when I presented better in the world.

Even with those positive results behind me, I was still very naïve and had very little knowledge of what I would have to do to be let in to play in the sandbox by the alpha female gatekeepers. As my second wife was always fond of telling me after major fights, we had that I made a terrible woman. Then she added she was not talking about appearance. Which was good since I had just had situations where I was mistaken for a ciswoman to back me up. Then I was confused, if it was not my feminine appearance holding me back, what was it? What would make me a better woman after all.

From that point on, I set out on a mission to understand what she was telling me but I had a major drawback…I was still living the vast majority of my life as a man and as such, ciswomen would not allow me back behind the gender curtain. For the most part, I was stuck in my part-time cross-dressing ways until I could find a better way out. The sandbox remained a faraway dream.

The main problem remained. My male ego would not easily let me pull down my male defenses to see and learn what really went on in a women’s world which operated quite nicely with or without male influence. For the longest time, he (me) refused to listen to women the best he could to learn what they were really saying when he was stuck playing the game behind the gender border. I felt as if I was in East-Germany behind the Berlin wall of gender. I knew I wanted to escape but did not have the willpower to do it. I was a victim to my newly discovered transgender hopes and dreams. At that point, I still had not realized how far behind my gender dreams being a victim made me and I still felt sorry for myself because of all my gender dysphoric issues.

As I always point out, it was not until I began to experience my version of womanhood in the public’s eye did anything begin to change for me. All the effort I put into my appearance came back to help me get my high heeled foot in the door with other women. Then the real work began when I needed to communicate and interact with them. What happened was many other ciswomen were encountering me on a regular basis in the venues where I always went, so I needed to develop a stable feminine persona to go with my appearance. What would I call myself and what wigs would I wear every time I went out are prime examples of what I am talking about. I was getting to the point where I was staring my forties in the eye and I knew I was not getting any younger and in the back of my mind, I had a sneaking suspicion that I had lived my life all wrong up to this point.

Rather than bemoan all of the mistakes or missed opportunities I had as a male, I needed to face the fact I was wasting my time as a male anyhow because I was always meant to be female. I went home and wrote in my secret diary that I was not a man cross dressing as a woman; I was a woman doing her best to cross dress as a man and build a life on a house of cards.

The realization of my true gender status enabled me to be my real self to the public and ciswomen responded well to my truthful gender identity. Even if they were curious what I was doing in their world and why I wanted to play in their sandbox and work my way into coveted woman only spaces. Finally, I was coming to the point where I could think I achieved my own womanhood, just in a different way than most ciswomen. I was still relevant to the world and should be allowed to play in the sandbox.

Another big lesson I learned was that once I was in the sandbox, I needed to work harder to stay. One slip up back to my old male self, and I would be labeled an impostor and barred from the box. Faced with the task of starting all over again. To the best of my ability, all of my feminine mannerisms, interactions and vocalizations had to be perfect. I was so afraid most of the time until I finally began to relax and have confidence in myself.

The best part about the entire process was I survived to write about it and hopefully to inspire others in this very trying, difficult time to be a transgender woman to make it also. We all have differing yet similar paths to make it to the women’s sandbox. Just don’t expect the process to be all positive and you can make it by hopefully finding ciswomen who knowingly or unknowingly help you along. Those minor claw marks you might receive like I did down my back were just learning marks and helped me along. More than the women scratching me ever knew.

They helped me to earn my way into playing in the women’s sandbox. The claw marks just equated out to the stripes I earned when I was in the Army.

 

 

 

 

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.

 

 

 

Wednesday, December 17, 2025

Gender is a Basic Human Instinct

 

JJ Hart, Birthday Dinner.

One of the most basics of human instincts is gender. It comes with us at birth and is then (right or wrong) reinforced by our families. External factors kick in to put us in a tight gender box and keep us there. How we are treated as boys and girls, goes a long way in how our future is shaped. In my mind boys were always told to get out there and conquer the world while girls were coddled in a pretty world. It took me decades of interactions with ciswomen to learn that was not true. In their own ways, women face the same competitive challenges as men, just coming from different angles or perspectives. I told one of the experiences I had yesterday when I waded into the ciswomen’s world for the first time and discovered how brutal passive aggressive behavior could be.  

Examples include boys competing more physically with each other while girls learn to compete just as hard but in a more passive nature. One way or another, gender as an instinct is ingrained into us quite early in life and is difficult to change. One of the reasons transgender women and trans men are so misunderstood in the world today. Not to mention the fact that we are very rare, and very few people have ever met a transgender person. I know my parents from the “greatest generation” were not great enough with me to understand how their first-born son wanted to be their daughter. Taking a page from the great Christmas movie “A Christmas Story”, I never wanted the BB Gun that “Ralphie” wanted in the movie, but I got one anyhow. Instead of the baby doll I really wanted. All my gender instincts were kicking in although I was not sure I knew exactly what was going on, I knew something was definitely wrong.

It was not until I began exploring the public as a novice cross dresser or transgender woman, did I start to understand what was going on with my own gender instincts. Facing up to the fact I never belonged in the male world as an active participant at all never came easy for me. Mainly because I had worked so hard to survive in a gender I did not want to be. To make matters worse, I was becoming more of a success in the male world. Even though I was so self-destructive I kept tearing down all the successes I kept building up as soon as I achieved them.

In my case, I think the war I waged with my internal gender instincts was much worse than the battles I faced for acceptance as a transfeminine person in the public’s eye. Even though they were major hurdles, obstacles such as confidence and impostor syndrome were holding me back. It seemed no matter how successful I was in my new world, I still felt like an impostor or outsider looking in. It took me quite a while to overcome my doubts and feel like I had as much right as the next woman to be in the space I was in. Over and over, I felt I was growing up into the woman I was always destined to be. It was just taking me longer to do it because of many external factors such as a whole train load of male baggage I had managed to accumulate in my life.

Along the way too, I was becoming a keen observer of the public’s gender instincts. Primarily ciswomen who for some reason had no problem with me as men nearly completely left me alone. By doing so, I was able to read other women like I had never been able to do before. Slowly but surely, my life began to turn full circle. Instead of going out to be alone, I was going out to socialize with other women who were mainly lesbians. They taught me a whole different set of gender instincts, mainly revolving on where I stood with the other half of the population, men. While other transgender women I knew were struggling to be validated by a man, I was flourishing when I was validated by women. It obviously is not a world which worked for everyone, but it worked for me.

With all the help I was receiving, I made it to a point where I did not consider myself trans when I was out in the world. I was just me, and I had all the confidence to go with it. It took me over a half a century to completely figure out my gender instincts, but I did it with some powerful help such as HRT or gender affirming hormones. The meds I was approved for helped me to understand what ciswomen go through in their lives such as hot flashes and other effects of female puberty. When I tried to talk about it to my women friends all they did was laugh and say welcome to their world. What I could not say was how happy I was to be there.

Cracking the code of human gender instincts is very difficult to do because it is so deeply ingrained in all of us and in many ways, it is a selfish thing to do. It takes a special person to understand when you have to immerse yourself in the other binary gender to just survive in life. If you are blessed to have found such a person, be sure to cherish and hang on to them because they are so rare.

In the meantime, keep your head on a swivel and be on the outlook for ways to improve your gender instincts. It is a difficult process and never one to be taken lightly. For me, at least it was a lifetime journey to finally discover something I already knew I refused to accept. I had my gender identity totally backwards and ended up paying the price for years. Just because I was afraid to face myself.

 

 

Sunday, December 14, 2025

Wintertime in Ohio

 

Hair by JJ Hart, Beadwork by
LizTDesigns.

My wife Liz sells a fairly wide range of her artistic/crafting skills on a platform called Etsy.

Yesterday, she ran into a shipping snag with an item that she sold, and we had to venture out into a very busy scene as everyone was out before a winter storm hit. We did not have far to go to get to the shipping store and then the post office, so I did not have to do any prep work for the brief trip. In fact, I did not even have to shave closely since we had gone out to eat the night before with her son at our favorite restaurant.

The bottom line was when I finished writing yesterday’s post, and Liz abruptly said was I ready to go, I was. I was in a what you see is what you get mode. I was not a transgender woman, I was me, and I am always interested to see how that attitude plays out. Because no matter how long I have been out in a transfeminine world, I still have a little voice in the back of my head wondering will I be discovered as some sort of a gender impostor.

As it turned out, the only person I encountered closely with Liz paid no attention whatsoever. I was just another face in the crowd while she worked her way through the problem Liz had and then we were off to the post office. As I said earlier, everything was crazy busy which meant the post office was going to be also. This time I took the easy way out and stayed in the car. I was in jeans, an Ohio State sweatshirt, fleece and snow boots so I was quite comfortable in the car while I waited.

For once, the weather people were dead on, on their forecast and we got between six to eight inches of snow before the temperature plummeted to below zero (F) temperatures. We have a fairly new furnace and plenty of supplies so we should make it with no problems until the temps rise back up in the middle of the week. In true Cincinnati style, the high temperature will be near fifty degrees.

In January Liz and I have another vacation planned to go south to warmer climates, and sometime I am going to venture out to our local pharmacy to get another Covid booster. Hopefully, this shot will keep me out of the hospital which is what happened last year when I caught Covid and ended up in the hospital for three days in Georgia in the Atlanta area. It’s not until the 24th of January but time flies when you are having fun and will be here before I know it.

In the meantime, I know the brutal winter weather is affecting large portions of the country, along with flooding in the Pacific Northwest so I hope you are surviving the best you can.

Friday, December 12, 2025

When a Trans Girl is Serious

 

Image from Bruce Mars
on UnSplash. 

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

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

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

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

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

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

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

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

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

 

                                                                                                                                                       

Sunday, December 7, 2025

The Rise of Transfeminine Privilege

 

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

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

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

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

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

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

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

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

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

 

 

 

 

Thursday, December 4, 2025

Is There Really a Difference between Genders?

 

Image from Pea on UnSplash. 

Yesterday, I briefly wrote about how I saw the world differently when I went out for the first time to view Christmas decorations at Clifton Mill, Ohio as my feminine self. I said something to the fact that my senses seemed to heighten as I viewed all the decorations and people around me. To me, the whole evening was brighter and more festive than when I viewed it as a man, wondering how it would be to do the same thing as a woman.

Little did I know the experience would prepare me for later life as I progressed along my gender path. Perhaps, initially, the new senses I felt were psychological in nature because I was still years away from actually changing my gender hormonal balance from male to female when I added HRT or gender affirming hormones to my system. Which means, I guess, if I was in some sort of a scientific gender study, I would not have needed the hormones to increase my femininity at all. Which would be good news to all of you who for medical or spousal reasons cannot consider HRT.

One way or another, I felt a real difference in my world when I entered it as a woman rather than a man. If I was cold, I could react accordingly and not have to be macho and try to ignore it is a prime example. Then, quite possibly, the biggest change of all was what I was going to wear. I had so many fashion choices I could barely make up my mind. It seemed I was only limited to what I could afford to shop for and buy. The sensory feeling of the clothes was wonderful, and I just loved the big, warm, fluffy sweaters I was able to wear because they were in fashion at the time and paired perfectly with my denim mini skirts I was able to find at my favorite thrift store. I discovered that I was perfectly comfortable when I wore a pair of tights or even leggings with my sweater/skirt combo in cool Ohio weather.

Even though the clothes did make a difference for me, the buzz quickly went away and the reality of what I was attempting set in. I have always believed that attempting to change the human gender is one of the most difficult things a person can attempt because there are so many roadblocks in the way.  Such as current misunderstandings of trans women or trans men’s lives. No matter how you cut it, it is just difficult to explain to a “civilian” what is going through our minds when we made the monumental decision to jump the gender border. What could possibly go wrong? Ha ha!

Sometimes, we end up surprising even ourselves with the gender changes we have to go through to be successful. As we begin to earn our way behind the actual gender curtain into woman only spaces, we begin to see and feel all the real differences there are. I know my first girl’s nights outs were real eye openers for me. I had no idea of how ciswomen interact with each other when there were no men around. The differences were real, and I cherished my chances to experience them. So much more than even my new one on one communication challenges with ciswomen strangers in the world.

As I approached the idea that I could actually take the opportunity to attempt to go on gender affirming hormones, naturally I knew it was a huge step forward in my transfeminine development. First of all, there were the health consequences of a sixty-year-old male starting to reverse the hormones he had lived with successfully for all those years Plus, back in those days, there were many naysayers preaching about the possible damage female hormones could cause on the body. Fortunately, I found a doctor who did not believe in all of that, and he approved my HRT. When I started the meds, I felt an almost immediate change. It was certainly what the doctor ordered, and I was rapidly increased to higher dosages of my precious new medications.

I felt great when my external changes such as breast development started to happen faster than I expected and was even more surprised at the internal changes I was feeling. Like the first night I visited the Christmas lights, when my world softened and became more perceptive, I quickly found myself in a world where I could appreciate everything more. Heat, light and sound in particular affected me more when I ventured out in public to my regular venues.

At that point, all I really knew was I never wanted to go back to the old male life I forced myself to live. I had found my new home.

Wednesday, December 3, 2025

A Trans Girl's First Christmas

 

Clifton Mills, Clifton, Ohio. 

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

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

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

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

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

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

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

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

 

 

Monday, December 1, 2025

Sealing the Final Deal in my Gender Struggle

 

JJ Hart. Key Largo last year.

Sealing the deal on my male to female gender transition was the most difficult decision I have ever had to make in my life.

It is the main reason I kept putting it off until I was nearly sixty years of age and could take the pressure no longer. The only way I kept what sanity I had was to cross-dress my way along until I could take bigger, more substantial steps.  One of the problems was, I had learned that cross dressing was not nearly enough to solve my gender issues and sooner or later, I would have to face the truth of who I really was. Also, I was very naïve and thought I could balance the influence of two genders in my world as I grew older.

As I set out to build a reasonably successful male life, at the same time, I was trying to fill out my feminine workbook with absolutely no help from other women. I was stuck being on my own for years, until I progressed to the point where I could leave my closet and explore the world as a novice. After brief successes (and a lot of failure), I was able to see portions of my future and judge if I could ever seal the deal and live my dream of being a fulltime transgender woman. Even though I was still progressing, I was still hitting roadblocks on my path to trans success and had to keep working my way forward through failure.

All I could see in my future was a life I would have to live alone with no way to support myself as a transfeminine person. My sexuality did not change, and I wanted basically nothing to do sexually with men, and I knew how incredibly difficult it would be to find a ciswoman who would accept me the way I was. I had pulled off some other seemingly impossible things in my life but accomplishing this and sealing the gender deal was too much to hope for.

Then, as I lived my new life as a trans woman, I learned that maybe my dream was not too much to hope for and one thing was for certain, if I did not try, I never would know if I could make it. I expanded my explorations with men and managed to have a couple real live dates when I enjoyed myself but nothing sexual happened, so I set my sights in lesbian bars for a ciswoman who wanted a woman with a little bit extra experience in the world. Amazingly to me, I was moderately successful in one lesbian bar where they accepted me. Which brought me so much closer to thinking I could seal the deal and live my dream.

Now I was to the point where I had to really see where I wanted to take my life. I was an executive general manager of a large casual dining restaurant which I had put in years of hard work to arrive at. If I transitioned, all the work I put into my career would be gone (along with the money) and I would have to start all over again. Behind the world as a transgender woman. Naturally, the whole situation was a major roadblock.

It finally came to the point where I faced sealing the deal like I was jumping off a cliff into nothingness. At that point destiny set in for me and made my final decision so much easier. Tragically, I lost my second wife and almost all of the close friends I had to death and could start with a clean slate in life. Plus, the restaurant I owned was failing and I was losing it also, leaving me a couple of years to work before I could retire early on Social Security which would give me enough income to get by. As You can tell, the doors to transition were opening wide and I would have been a fool not to walk through them.

Most importantly, my mental health was suffering and my self-worth as a man was at an all time low, so it was time to end the torture I was feeling and jump off the cliff and seal the deal. It was during this time too, that the Veterans Administration health care system, which I was already a part of, approved veteran’s care for gender dysphoria with mental health counseling and HRT if approved. I was quickly approved and ended up taking another giant step towards achieving my dream and sealing my lifetime goal.

What did I have to lose? I was leaving a male life I never really felt comfortable in to jump off a gender cliff and land in accepting women’s arms as I joined their world. When I did, I tried to take every little bit of advantage I could from all the learning experiences I put in over the years. Landing on my feet in high heeled shoes was a challenge but I managed to make it in fairly good shape. I came out fully at the age of sixty when I finally decided to seal the deal and never looked back. I could not take balancing two genders any longer and took the easy way out into the world of women where I should always had been.

As always, thanks for reading along, and any comments are welcome! I always do my best to respond.

 

Sunday, November 30, 2025

If Your House of Cards is Broken, What Then

 

Image from Nik Korba on UnSplash.




If your house of cards is falling, what then?  Is something many transgender women and transgender men face as they transition to the gender of their choice.

The problem is, we hide our flaws so well over the years that many of the friends and family we associate with never had a chance to see the true selves we are internalizing. In my case, I knew very early on I had deep flaws that eventually I would have to adjust to. Somehow, I carried the misconception that age would solve all my gender problems which I hoped magically would just disappear. In the meantime, I set out to build a stable male existence on a house of cards.

The longer I built my house of cards, the harder it became to rationalize tearing it all down and starting over. As I started my path towards achieving my dream of living my life as a transgender woman. What I ended up doing was, trying to explore the world in stages as a novice cross dresser or transgender woman, to see if I had any chance of making it at all. Very early on, I had my doubts as my futile attempts to blend in with the world were met with scorn. I knew without a shadow of a doubt what I was doing was breaking my male and female self and I needed to discover ways to fix it.

It was then I began to shove my male ego aside and begin dressing for the segment of the population I wanted to blend in with, cisgender women. I began to re-study all I had ever thought of women as a whole and started to fix the way I was trying to look. I was certainly not making it as a teen girl dressed to thrill and settled in on a more mature scaled back look I could handle with my testosterone poisoned body. I immediately began to see dividends as I started to successfully blend in with the world.

The problem I discovered was I was beginning to be too successful in my exploration. Suddenly I realized I was not a casual weekend cross dresser at all. I fit in with the new up and coming term transgender almost perfectly and I began to change my mindset from thinking I was a man trying to be a woman to I was actually a woman trying my best to be a strong, successful man. When I discovered this, my life in some ways changed for the best, but in other ways turned out to be problematic. It was easy to accept my changes, but it was hard to decide what to do about them because of the seismic problems they caused. My house of cards was shaking and becoming broken, and I did not know (or want to face what I needed to do about it.)

To attempt to hold my broken world together, I kept trying to apply the strongest male glue available. All I ended up doing was hurting my mental health more in the process of trying to save myself. All the ripping and tearing of my gender dysphoria was literally killing me. Finally forcing me into action to save myself. As I struggled, I continued on my not so merry way, exploring what it would really mean to me if my house of cards collapsed and I had to fix it. The only thing I had going for me was all the experiences I had built up as a transfeminine person in my life. So, I did not have to start from ground zero when I decided to go after my male to female transition for the final time. I was secure in my feminine appearance and communication skills, and I had major hurdles behind me. Then all I needed to learn was what would happen when I lost all of my male privileges which were a major part of my house of cards. In many ways, losing things such as my security and intelligence as a trans woman were breaking all the remaining chains I had to my old male life.

The bottom line was I took a male life that was not broken and broke it anyhow. Giving up nearly everything I knew as a man. Gender affirming hormones or HRT put the finishing touches on everything I had ever known and shifted my knowledge of gender privileges to the feminine side of the gender spectrum. As my testosterone decreased and my estrogen level increased, I was free to build a new life. Which for once was not broken or flawed. No more house of cards for me, nothing was broken.

 

 

Saturday, November 29, 2025

A Trans Girl and her Football

 

Ohio State versus Michigan. 

When I seriously began to think of pursuing my male to female gender transition, I wondered what I would do about all my male baggage in my new feminine life.

Since I was nearly sixty years of age, I had plenty of baggage to consider what I was going to keep and what had to go. By far, my sports baggage was the largest piece of baggage I needed to wonder about was my love of sports. Especially football and baseball.

Ultimately, I found I did not have to worry about anything because ciswomen around me were catching up to me in their love of sports. To make it clearer, as I looked around during the big games I was watching in the sports bars I was hanging out in, I was beginning to notice more and more women in their football jerseys around me. All of a sudden, I did not feel so out of place. I knew some women were into sports, such as my second wife, but not to the level I was.

Also, what helped me was the customer/regular relationships I built with the bartenders I saw on a regular basis. It even got to the point when my beer was always waiting for me when I sat down in front of a big screen television to watch a game.  When all of this was happening, I was deciding I could take my love of sports with me as I transitioned into transgender womanhood. It was just part of my inheritance.

Little did I know, the best was yet to come, and I could bring my sports baggage with me. It turned out, my wife Liz and other ciswomen friends I had made along the way were all as passionate as I was about watching sports. I even was living life large when I was invited to go to a women’s roller derby match one day in Cincinnati by my lesbian friends. It was also a dollar beer night which also added to the fun.

The whole focus of this post is “The Game” is today. Or in other words, the Ohio State/Michigan football game. I make no secret of my love for the Ohio State Buckeyes as Liz is also so we will be tuned into the game. Ironically, the game was one of the main days out of Thanksgiving and Christmas we ever got together. The good news is, I have a better person to watch football with (my wife Liz) who helped me build my life as a transfeminine person, rather than tear it down like my brother did.

No matter how the game goes, I will forever be grateful to all the cis women in my life who encouraged me to be me which included bringing along my love of sports. It probably all came from playing sports (primarily football) which kept the bullies away at the same time. So, it worked well, even though I made it through a couple broken bones. One funny story I have about broken bones was when I broke my collar bone. The doctor who examined me said he would not reset the bone, and I would always have a lump where the break was. Then, the doctor said it would not matter since I would not be wearing a strapless gown in my life. I thought, if he had really known, he would not have said such a thing. Of course, I was worried from then on about that lump on my collar bone and always remember what the doctor said.

Any piece of advice I may have for anyone considering a gender transition of their own, is to look at your baggage closely and then what the ciswomen around you are doing. The world of women is always evolving with the world and is never staying in one place. It happened to me with sports and can happen to you too with some of your questionable baggage. It could be a chance for you to be a leader rather than a follower. If you follow your heart, others will find no problems with you. People are like sharks and have the tendency to circle the wounded ones quickly. Don’t give them the chance to see you bleed.

I know it is impossible to bring all your male baggage with you. Afterall, he had a hand in making you who you are today. Possibly, it all could make you a better person as a trans woman. You already are because of the understanding you have of the two main binary genders and you can build on that success.

Maybe you can be a trans girl with her football too, and GO BUCKEYES!

 

Happy Holidays!

  Ralphie ! Happy Holidays to you and yours! I hope those of you who have experienced close family losses because you came out to them as ...