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

Tuesday, December 30, 2025

You're so Vain

 

Image from Ava Sol
on UnSplash

Expressing yourself to the world as a transgender woman carries with it a certain amount of vanity.

Until you begin to relax in your new feminine world, I think you need to obsess over every detail of your exterior appearance. Since we all have such a vast amount of catching up to do to compete with other ciswomen in the world, details matter. Perhaps one of the first lessons you learn is how competitive the world is when you are a trans woman. Ciswomen are every bit as competitive as men but in certain areas not readily visible to the male gender.

For example, the major question comes to mind that do women dress for men or for each other. Sadly, we never had the input of mothers, sisters or girlfriends saying, “are you wearing that?” I know if I had that sort of input, it would have saved me a lot of embarrassment when I first began to go out into the public’s eye. It was a resounding yes for me when I learned who women really dress for…themselves. My problem was, my male self-kept getting in the way and had me dressing like a trashy teen girl. All poorly concealed in a testosterone poisoned male body. It was no wonder I was creating negative attention and getting laughed at. When all I was doing was trying to present myself well the best way I knew how.

After I began to learn and change my thought patterns concerning fashion and makeup, I began to have success in the world. So much so, that on occasion (when I was so vain and did everything right) I received a compliment or two from a cisgender woman. One thing was for sure; it takes a woman to know the work it takes to perfect a public image with makeup and fashion. Plus, I needed to be better than the average woman because I was working at the whole image after I started as a man.

It turned out, having to be better in the world worked well with my increasing source of transfeminine vanity. All I thought of was how much better I could look if I tried just the right foundation and mascara, as I haunted the many thrift stores, I went to looking for just the right piece of clothing to add to my wardrobe of feminine clothes. My personal newfound male to female femininization vanity was in full force as I was having fun. In reality, I saw nothing wrong with being vain in how I appeared as my authentic self, until I clashed with my second wife.

She rarely wore makeup or dresses at all and did not like the way I presented myself at all. On the rare occasions we went out together as women, I tried to tone down the amount of makeup I was wearing along with putting on my most conservative clothes. All because I wanted her approval, which I never got. If I wore any less makeup, I might as well say to hell with it and go out with her as my old male self. I was stuck between the rock and the hard place as far as my feminine vanity was concerned.

As I progressed with my makeup and fashion experience, I understood how much work I would have to put out to achieve the transgender goals I wanted. I knew I would never be able to transform my old male self into the prettiest girl in the room but on the other hand I could present well enough to get by. Everything that I was doing at that point just became a blur of change. Especially when I was approved for gender affirming hormones or HRT. As my skin softened, hair and breasts grew, it all was a welcome addition to all the work I had done all those years to just survive in the world. As I wrote yesterday, just not having to wear a wig anymore was a huge deal for me since I had no male pattern baldness to contend with. All of a sudden, I needed to contend with a new form of vanity when I went to beauty parlors to have my hair done just a certain way.

During all the years it took me to fully come out into the world as a trans woman. I learned the true meaning of competing with ciswomen in the appearance arena. Once I did. I needed to move ahead to the larger context of being allowed to exist in women only spaces by the alpha-female gatekeepers. In many ways, my second wife was an alpha female who never let me in, so I wonder what would have happened if she had lived long enough to see/know the person I am today. One thing is for sure; I am no longer the “pretty, pretty princess” she used to call me because I have paid my dues as a transgender woman.

All I know is I did go through my periods of extreme selfishness and vanity to arrive where I am today and I don’t know if there is any other way to go down the path, I ended up taking. Changing a gender is such an intense way to live, especially when you started with so much success as a male that it took me a massive effort to change. Not to say, all of the effort was not enjoyable but at least, it was interesting and challenging to see behind the gender curtain.

For many of us stuck in our own form of gender dysphoria, vanity is just one aspect of our larger need to survive.

 

 

 

Monday, December 29, 2025

Dark Side of the Gender Moon

 

Image from Maria Kovalets
on UnSplash.

Exploring the dark side of the gender moon for me meant a lot of work.

I equate it to the first times I could experience wearing my own hair in public without the help of a wig of any sort. The satisfying part was that I did not have to worry about the style and color of the wig I selected and how hot it was going to be on my head during the warm summer months when my makeup threatened to melt off of me as soon as I put it on. On the other hand, I needed to master the art of looking at the back of my head in a mirror to see how my new hair looked. I began to think of it as the dark side of the moon. No longer would I have the ease of styling a wig on a wig stand in the back so I knew it would look good on my head.  

Also, not wearing wigs anymore opened up a new wonderful world for me of visiting women’s beauty salons. I will forever remember the first time my daughter gifted me a visit to her upscale salon/spa. I was just coming out of my gender shell and the whole prospect of having my hair done terrified me, but I hitched up my big girl panties and said yes. Little did I know what was instore for me. Thanks to my daughter, first of all I needed to walk through seemingly an endless gauntlet of women in chairs in various stages of having their hair done. I gathered up all of my courage and tried to walk as femininely as I could until I met my new stylist.

The first of many decisions I needed to make was what color I wanted my new hair to be. As my daughter and stylist hovered over me with what seemed like an endless set of examples to choose from, I chose a red/blond streaked shade and then had to pick how long or short I wanted my new hairstyle to be. I had no idea choosing the dark side of my gender moon would be this difficult. Quickly though, I chose an off the shoulder look which maintained most of the hair I had grown. All too soon, my appointment was over and I was spun around in the chair to see the new me and I loved her! All the years of frustration of not being able to afford quality wigs or take care of them faded away and the best part was I had been blessed with visits to women’s spaces such as beauty salons and I walked away from the experience knowing why so many ciswomen value their beauty visits to the hair salon the way they do. The day following my first visit to a serious upscale salon, I thought I had been exposed to so much estrogen, I could skip my daily dosage.

I guess you could say, having my hair done was just the first of dark side of the moon gender moments in my transfeminine life. When you add in all my other journeys into women only spaces, there were plenty of other experiences to mention. Like the one I rarely recall when I was invited to go out and party with a few of the servers, I met at one of the regular sports bars I hung out at. Like the experiences of having my hair done, I had been out several times on girls’ nights out invitations in my past, but never like this one. These women were all much younger and prettier than I was so I wondered how I would fit in. The answer was that even though they were all nice to me, I did not really fit in at all. The other women were too busy getting hit on by guys so there was little time for other socializing. I quietly sipped my drinks and pleasantly left with the group when most of them did. More lessons learned.

As far as any major male to female feminization process goes, there are inherent risks to be taken when you go through the process of losing your male privileges and discovering your new feminine ones. I know in my case, I was starting to know I was successful as a transgender woman when I began to be treated in certain ways. Such as when men in particular began to question my intelligence as I talked to them. I thought to myself, did I treat women this way?  I was definitely on the dark side of my gender moon as I explored a new world.

As you begin to explore your new world, there is plenty to do such as gathering the courage to use the women’s rest room. Which is a natural need when you are out and about for any length of time as your new trans woman self. Not any of the rightwing paranoia being spewed by the bigots saying we are men using the women’s room.

Actually, exploring the dark side of your gender moon can be an exciting experience and one you have waited your whole life to take. Take it far past just styling your own hair and/or wig and expand it all the way to discovering a new world you wanted to live in so badly. Just try to enjoy the discoveries you make and any aha moments you live through. There is so much to be learned when you jump the binary gender border to live on the other side. All the work I put in was certainly worth it.

 

 

 

 

 

 

 

Sunday, December 28, 2025

Fearing Change as a Gender Challenged Woman

Image from Joshua Gaunt 
on UnSplash. 
Gender change came so very slowly for me during my life.

First, I needed to free myself from the male bonds I was born into which I had no control over. Looking back, I think one of the main problems I had was fearing the changes I was looking to go through if I faced up to reality. From that point forward, life became a struggle as I feared changing it.

What I became was the best transgender procrastinator I knew. Any excuse I could come up with not to go through with living my dream, I clung to like a survivor on the Titanic. What I would do about spouses, family and employment were a few of the major questions I was asking. So, what did I do? I ran as hard and as fast as I could from the problem. I was running so hard, I even changed jobs very quickly so I would not be bored with my life as a transfeminine fugitive. Eventually, even though I grew tired of the pace, I found a stable good job and settled part of my life down. I say part of my life because during that time my gender issues were raging out of control.

Even though I was slowly becoming successful at blending my feminine self in with the world of cisgender women, I still had many fears to conquer. Just when I thought life was improving for me, I would hit another roadblock and send me running back to my cross-dressing drawing board. Which was crazily marked with clownish makeup until I got it right. The fear of applying skilled makeup kept me occupied for years it seemed. On the other hand, when I got my male ego out of the way and realized I needed to dress for other women and not men, did I begin to improve my overall look and the laughter I used to receive in public began to die away. When it did, I learned the most powerful force I had to combat gender change was having confidence in myself. Surely, I would never be the prettiest most beautiful woman in the room, but a lot of other cisgender women were not either and they were surviving and even thriving just fine. There were many layers to building womanhood and I just needed to find mine.

For some reason, the more success I felt as a transgender woman, the more fear I had. I guess it was because of my old male self-starting to panic because he was losing his dominance over my life. For years, what had seemed like the impossible gender dream was now looking as if it could become a reality. As he fought his new reality, the stakes towards living a successful life as a trans woman, increased dramatically. Every step I was taking towards my dream seemed to feel as if I was walking in quicksand since at any time, life as I knew it could be disrupted beyond repair in the little backwards town I lived in. I still lived in mortal fear that any day I could be discovered and the acquaintances I had built up over the years would realize I was living a gender lie. Which I was.

I finally made it to a point where I could not procrastinate my life any longer and I began to use every spare moment to explore the world as a transfeminine person. It all meant I accepted the challenge to finally go all in with making the final preparations for my new life. The bittersweet part of it all was part of my male to female final transition was built on tragedy. In the space of a couple short years, I lost my second wife as well as all of the friends I had built up over the years to death, and I had to start all over again. Sure, I was still afraid to do it but deep down I knew transition was the only way I could go. Suddenly it was up to only me to decide if I wanted to take the ultimate step and try to get a doctor’s permission to begin HRT or gender affirming hormones. I was approved and then the changes I was hoping for began to really happen for me. The changes were so dramatic, I sometimes take an entire blog post to relate them to you.

What frustrates me now are the haters who say that because I took so long to transition, I am not trans enough for them. Normally, they are younger LGBTQ individuals who have no idea of what the world was like way back when I was growing up. We all have our own gender crosses to bear, and we need to understand each other’s journey.

Sadly, there are all those transgender women and trans men who can’t take the burden of gender change fear any longer and tragically try to take the self-harm way out. The suicide rate in our community is completely too high and could come down with proper help and understanding.

In my case, my excuse is I had a heavy dose of ignorance combined with fear and procrastination as reasons it took me nearly a half a century to come out of my gender shell and live freely in the world as a transgender woman. These days, if you can steer clear of all the online trolls and haters, you can still get valuable information on the internet concerning ideas on how to build a new life as a woman from scratch. Plus, fear for me was a powerful motivator and when I was forced into a corner because of my gender, I came out fighting because I believed I was right.

It turned out I was.

 

 

 

  


Saturday, December 27, 2025

Resolutions

 

Image from Nik on UnSplash.

I am a firm believer that most new year’s resolutions are made to be broken. Statistics say that nearly eighty percent of people never keep resolutions.

On the other hand, in my formative transgender years, I ended up making several resolutions that I intended on keeping. But by now you might be able to guess which ones I am talking about. The further I was going towards being able to live the feminine life I always dreamed of, the easier it was for me to set new resolutions to conquer in the upcoming year ahead.

Very early in my gender journey, it was easy to set easier goals such as getting out of my dark closet and into the world. I figured from there I could look around and see what was next. What was next proved to be terrifying, natural and exciting all at the same time. More and more I felt bored by the old idea that all I wanted was a chance to be a woman on my own terms. It got to the point where I did not have to make any resolutions which I would have to break. I was doing a good job at living out the ones I had already made. Ironically, I missed several resolutions I should have made but did not. Such as when I did not see my second big gender transition coming at all. It was when I shifted gears mentally and began to think of myself as being transgender and not a cross dresser at all. To this day, I have nothing against all cross dressers (since I was one for years) but my gender needs took me deeper.

Of course, going deeper into my transgender rabbit hole, brought out the need for new resolutions. The old shallow ones such as could I exist in a ciswoman dominated world no longer were making it. I was way past all of that and needed to find out once and for all if I could carve out a new life for myself that I had only dreamed of. You might say, reality of life began to outstrip my dreams as well as the need for more resolutions. At that point, I quit making them all together.

It was easier to go free form in my transfeminine pursuits and do the best I could. It turned out that for the most part I was successful and continued on feeling good about myself. Until the usual problems arose with my unapproving wife and a male self who continued to dominate a big portion of my everyday existence. As I thought more and more about them, I wondered what I would ever do about setting up more resolutions about changing my life for good and jumping the male to female femininization border.

I don’t think until you have walked a mile in our high heeled shoes as a transgender woman would you understand the relative importance of making new year’s resolutions. While others are thinking about losing weight or cutting back on their drinking, you (on the other hand) are wondering what in the world are you ever going to do about becoming a full-fledged transgender woman. It is especially difficult when someone you know asks you what your resolutions are and you don’t want to lie.

At that point, I just went back to my default position I used when anyone asked me about my future. When I was a kid, instead of saying one day I wanted to be a woman, to please my parents I just said I wanted to be a lawyer or doctor. Seemingly, nothing changed later in life when I was asked about my resolutions, I would just say to lose more weight or make more money. So, I lied and took the easy way out. There was one way I could tell the world the truth at that point in my life. Then I started to wonder how many other people who spoke of their resolutions on new year were fudging their answers too. All those people who rushed out to join a gym never really meaning to go like I did once. As I think about it, going to workout in any shape or form was yet another gender smokescreen I threw up to disrupt anyone who was sensing my transgender issues.

Overall, I wonder how many other trans women or trans men have had to try the same method and any sort of a public call for a resolution or two is just another way to hide while you are on your path. One of the statistics which I have read on resolutions said that only twenty percent of people making resolutions keep them anyway, so I don’t feel so bad about not making them anymore. And who knows how many of those making resolutions are closeted transgender people anyway?

Looking back, the only advice I could give to a trans person still in the closet thinking about the new years and making resolutions is to try to make yours doable and don’t try for too much. Failure only leads to disappointment and a deeper return to your closet.

Anyway, you cut it, a new year is on the way, and we have a chance to sweep away a very disappointing 2025 out the door. Just keep your head high and hope for the best in 2026. At the least we will have a chance to vote and change a very crooked regime in Washington. Something you can do from the privacy of your closet, and no one will have to know and if you do make resolutions and don’t keep them you will be in the majority of the population for a change. A real rarity.

 

 

 

 

Friday, December 26, 2025

Alone in a Crowded Room

 

Image from Bruno Aquirre 
on UnSplash.

I often refer to the days when I was first going out and seeking clues to my true identity as going out to be alone. I called it that because I had not yet met any regular acquaintances that I would have called friends on a regular basis. So, I was surrounded by a group of strangers no matter where I went. Even so, it was better than sitting at home by myself staring wishfully into the mirror.

Following leaving my painfully shy days behind me and becoming a rather social person, I did miss the interaction with the public. Going out alone was the only recourse I had which brought up several other problems. One of which was if I did present as a successful woman sitting by herself at a busy bar, always invited trouble because I was so out of place. It was during those times that I used my cell phone as a prop. In essence signaling to people, I was waiting for someone to arrive and join me. Plus, in the cold winter months, I could place my coat or jacket on the seat next to me to act like it was occupied. Both of which helped keep away any unwanted advances from mainly intoxicated men. On the other hand, other intoxicated ciswomen did not count, and I welcomed any of their advances which completely outnumbered men. Mainly because the women were so curious about what I was doing in their world.

Another problem I had was a huge case of impostor syndrome I suffered from. No matter how nice the stranger approaching me was, somehow, I felt I did not quite belong in the new exciting world I was in. It took me a while to get adjusted to the fact I was succeeding in a life that I had previously only considered a dream. I also still considered myself a rank amateur because of how I was able to conduct myself as a new transgender woman. I knew very little about how ciswomen communicated in the world away from men and it showed. For the longest time, the little nuances women use to communicate escaped me. Forcing me into shutting down and just listening to others and sometimes coming off as a standoffish bitch. Which was the last thing on my mind to happen.

I began to move away from being a stranger in a crowded room when I began to have enough confidence in myself to move forward. I was no longer just an virtual impostor just observing the world to jump in and inserting how I felt about things and people around me. A word of warning though, it took me a while to get there. Too much trial and error before I gained the confidence in my own unique form of womanhood which differed from many other women around me but at the same time, was still as complete. Sort of.

It was not until I began to build up my own circle of friends who happened to be mainly lesbians did, I began to relax and truly enjoy myself. I was no longer an imposter but now a full-fledged participant in my resurgent social life. Probably the only mistake I made was when I did not realize how different two of my friends were who I kept inviting to our impromptu meetings at sports bars and lesbian mixers. I was still naïve to the lesbian culture and did not realize the differences between a so-called gold star lesbian and one that had been with a man. I had one gold star friend along with another who had been previously married with three kids, so on occasion sparks did fly. In the meantime, I was off in my own little world jumping at the chance to be a wing person for one of my friends and trying to set her up with another woman at the mixer. It never worked, but I had a fun time trying.

The best part was I was no longer a stranger in a crowded room. I was becoming a full-fledged participant and loved it. The only problem I was having then was my new feminine life was starting to seriously force my hard-earned male life into an early retirement. A retirement he was so not ready for. Often the gender conflict I endured was mental and brutal. I did the only thing I knew to do and that was to internalize my feelings and move on. Which was the last thing I should have tried to do. My male self-wanted to keep me being a stranger in a crowded room so he could have his way. What he did not count on was, the more I worked on my dream gender life, the bigger and more accepting the room became.

The more I think about it, the more I think my male self-wanted to keep my female self as a kept woman. Validated by him only. Eventually, my transfeminine soul won out and he needed to face the truth. He was always part of living a lie in my life. Since my impostor syndrome was for the most part gone, it was the last remaining significant part of my life for him to cling to.

It felt so good to no longer just to be going out to be alone and know I would have the chance to meet my friends or even make new ones. Because I had hid my true self away for all those years, my transgender dream self could not wait for a chance to live and express herself in a crowded room.

 

 

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.

 

 

 

 

Saturday, December 20, 2025

Meeting a Hero's Wife

 

Image from UnSplash.

This is a short post which basically revolves around the unexpected meeting I had yesterday with a very special person.

Nearly every Friday afternoon I attend a LGBTQ support group (virtually) at the Dayton, Ohio Veteran’s Administration hospital.

It is one of the best support groups I have ever been involved in, and it is rare that all the original attendees still come to the meetings. It is a very diverse group with everyone from gay men and lesbians to transgender women like me. Yesterday we had a full house including a new participant who I assumed to be a questioning lesbian ciswoman.

I turned out to be very wrong and as the hour meeting went on the moderator very skillfully brought it out of her why she was there. It turns out she is the wife of a hero. Her spouse is one of the transgender service persons forced to leave the military by the supreme coward who dodged the draft “Captain Bone Spurs.” Better known as president tRumpt. When she told their story, I was wowed and expressed my position that her spouse was a true hero and would she be joining the group in the future.

Since she said, they were just exploring the area for LGBTQ contacts, that would be a real possibility. And I was thrilled to have the chance to meet her. So, I will see if I have the chance after the Christmas holiday when we have our next support session. I will let you know what happens.

In the meantime, my wife Liz and I will not be attending any concerts by the Cincinnati Symphony Orchestra this season. Years ago, I tested my courage and even found a sequined formal dress to wear to a holiday concert with Liz. Even though, it was not my favorite form of music, I managed to calm down and enjoy the show when I learned not everyone else was looking at me.

We even stopped for drinks on the way home (in an Uber) so we would not have to drive and had a great time. Since Liz is a Wiccan, we don’t celebrate Christmas as such, we celebrate Yule instead which is close since the Christians “borrowed” Christmas from the pagans in ancient times. Plus, my daughter converted to Judaism years ago, so I am pretty much left out of the Christmas holidays altogether which is a total change from the years with my second wife who was a fanatic. Poetic justice, I guess.

Even though those days are past me, I am fortunate to still have Liz’s family to feel the holiday warmth from. I know many in the transgender community are not so well off this time of year.

For me, just the chance to meet a hero’s wife in person was a huge gift unto itself. As I said, I hope she comes back for more interaction and brings the hero with her.

 

 


Thursday, December 18, 2025

Letting Things Happen versus Making things Happen as a Trans Woman

Image from Mahdi Chaghari
on UnSplash.

Perhaps you have heard a football coach talk about slowing the game down and simplifying it for his players. Of course, I had to equate it with being a transgender woman or trans man when I heard it.

I began to think of all the stressful days I spent in front of the mirror as my perception of a pretty girl, then taking my image public and into the world. For years it never occurred to me that I was trying too hard. I was attempting to micro-manage myself to ensure every little aspect of my feminine image was correct. Here is an example of what I was doing wrong. On any given day, my makeup and fashion were on point, and I was confident about my presentation. Then as I was out trying it all in the public’s eye, I would either catch myself walking hunched over like a linebacker or worse yet, trip over my own heels and almost fall. It took me quite a while to realize what I was doing wrong and try to change it.

For me, relaxation and confidence were the key to real gender change. I was letting it happen rather than making it happen. I discovered it was so much more pleasurable for me when it happened that way. After that I could take my game to a different level such as communicating one on one with the world for once as my authentic feminine self. A key point I had to do if I was ever going to make it to my dream of a male to female femininization project.

I also established bucket lists of things I wanted to do as a transgender woman and was able to accomplish most of them except a couple of ill-thought-out visits to women’s rooms when I had the police called on me. Letting it happen surely did not work for me then, but I recovered and gained my restroom privileges in other venues I went to. Fortunately, the police had better things to do than mess with me and I went on my way without further problems. That was years ago and I haven't had any problems since. That was a good thing because the restroom privilege was something that I needed more than wanted.

I cannot stress enough about how much I had to learn during this period of my life when I was making a serious push towards transitioning from a serious cross dresser all the way to a transgender woman. When in reality, it was mostly a mental transition, it was still a very important one to make. I have a difficult time explaining it but all of a sudden, something clicked in my mind, and I knew another change was needed. I was so more than a man wanting to look like a woman.  I wanted to be a woman and feel like one as close as I could. That was when I successfully set out to socialize with cisgender women just to see if I could. I conquered my fear and found out I could add another layer of just letting it happen versus making it happen.

By this time, my muscle memory had improved so much as a trans woman that it became natural to me. So much so in fact that I had to be careful I was not too effeminate when it came to me working my male job and living with my wife. It finally became too much for me to juggle, and I needed to put it down before it was too late and I became more self-destructive than I already was. What I did was, attempt to do more things as a transfeminine person and do as less as humanly possible as my male self. It is one of the reasons I took so long to transition, because of the need to work around a disapproving wife and male self which was desperately hanging on.

You regulars know this part of my story when my wife tragically passed away. Which left only my weakened male self to resist any efforts at total domination from my inner female who had waited so long for her chance to live and write her own gender workbook. Little did I know she kept her own workbook up to date and was ready to go. If and when she had a chance to use it. Perhaps, your inner female is keeping a gender workbook also and you will not have as far to go to catch up when you get the chance to live your life.

I discovered too that letting it happen versus making it happen was mostly common sense. Even though the two main binary genders do things differently, they often operate in parallel universes which are the same and seem to be doing more so in the younger generations. I first learned up close and personal during my first girl’s nights out I went to. I was worried about what I needed to do to be able to interact with the group but then found they had just flipped the script from jobs and sports to family and friends with the women. Quickly I relaxed and started to let my inner girl flow, and I was fine with most of all the other participants except for one who I perceived as being a miserable person anyway. Who was unlikeable to me, and I left her alone.

I chuckle to myself when I think of how my football coach’s words would come back to help me in such a different way later in life. I guess it proves that you just cannot count on anything staying the same when it comes to gender. Perhaps that is a clue why the population at large knows nothing about us and we live parallel lives from both of them. Whatever it is, if you are in your path of gender discovery, you will certainly feel the change from making it happen to letting it happen.

 

                                                                                                                                          . 


Tuesday, December 16, 2025

Staying in your Own Gender Lane

Image from Earnest Tarasov
on UnSplash.
Staying in my own gender lane may have been more difficult than I had ever imagined. Of course, it all started when I was externally born male. Then when I started to understand something was dreadfully wrong with my male existence, I needed to figure it out.

My first indication of what the problem might really be came when I discovered the thrills of wearing my mom’s clothes, since I did not have any sisters to beg for clothing off of. Sadly, even though I was thrilled to see my version of a pretty girl in the mirror, deep down I knew it was just not enough for me to stay in my cross-dressing lane.  I wanted to pull out and find myself in a more comfortable gender lane where I more than ever before to being feminine.

Before I could do that, I needed to define what being feminine meant to me. I knew just acting effeminate would get me nowhere except bullied to the point of beaten up and on the home front (which was very male dominated) I would probably earn a trip to a psychiatrist if my small stash of girl’s clothes and makeup was ever discovered. I was trapped in a male world I wanted nothing to do with, and worse yet, I was pressured to perform well in that world. I needed to be in a passing lane around as many other males as I could.

The problem was, I wanted nothing to do with that world and could not show it. And in the pre-internet era I was growing up in, I felt so all alone with no one to talk to about what I was feeling. I just knew I did not feel the so-called mental illness that gender issues were being referred to back then. All I knew was, I was having a very difficult time staying in the gender lane which was assigned to me when it felt so natural. Plus, when I woke up in tears after having such a realistic dream that I was a girl impacted my life terribly until I could get centered again where I was “supposed” to be.

Somehow, I made it through those very confusing gender days and finally made it out into the world to discover if I had any future at all in a world ruled by cisgender women. When here I was, a novice in their world trying to survive. I equated it with driving on the Autobahn in Germany. I quickly discovered when you were driving a VW Beetle (like mine) and ventured into the outside lane then you saw a car in your rearview mirror flashing its lights, you better get out of the way. My life in those days often felt that way. I was learning lessons about where I wanted my transfeminine womanhood to go but I always seemed to see lights warning me in my rearview mirror.

Through tons of trial and error, I learned I could change my gender lane to the one I dreamed of. From as young as I could remember all I really wanted to do with my life was live it as close as I could to being a woman. Of course, that meant putting all my safe male privileges behind me and set out to build new ones in my gender lane with new life experiences. Like the Autobahn I found there were no speed limits on what I could learn or experience in the new gender lane I was in. More importantly, I had no one except my old male self to tell me to slow down before it was too late and I wrecked. Here is where I make the excuse of why it took me so long to transition because I was overly cautious that I did not wreck.

As I was in the gender lane I wanted to be in for a change, it w as nice to finally wake up in the morning knowing I was coming closer to my dream of living life on my terms as a woman and not having to keep falling back on my male self for last minute support. I was one and she was me for good.

But just when I thought I had it all in my new gender lane, I discovered many small nuances the ciswomen around me use that I needed to learn and put into practice. Such as the powerful use of nonverbal communication and passive aggressive behavior. For the first time in my life, I needed to look intently at other women when I talk to them and search their eyes for what they were really telling me. Which extended into the passive aggressive areas of behavior I encountered. There were many times I fell for a smiling face or non-threatening comment which turned out to be a knife in the back when I let my guard down. They were all lessons I learned the hard way as I earned my ability to stay in my gender lane permanently.

The best part was that the more I learned, the more I wanted to learn about the lane I was in. Even my biggest naysayer, my male self, had to finally give up and get out of my way. I was in my lane for good and there was nothing he could do about it. I had served my feminine apprenticeship I was walking the path I always was destined to walk and in the short and long term I got out of the way until I could salvage was left of myself and move forward. 


Monday, December 15, 2025

More Downs than Ups on the Gender Roller Coaster

 

Image from Pietra K. 
from UnSplash.

The gender rollercoaster of life was very real to me.

That is the reason I attempt to mention all of the ups and downs I have experienced over the years as I battled gender dysphoria. For me, the trip up the coaster was not often worth the trip down as my depression set in. Until I received the proper care for my depression, I would often not want to even get out of bed for days at a time. Of course, I could not do that, and life would have to go on. That life included an increasing interest in cross-dressing. When I was on an upswing, life was better and I thought I was even making strides towards possibly living my future dream of living in and competing with a world of cisgender women. All of which had a very large headstart on me towards possibly achieving their womanhood before I could.

All this turmoil sent me down the rollercoaster of life and right back to where I started from…deeply frustrated. It was not until I began to leave my closet or shell and explore the world, did I begin to experience any relief. In the world, I discovered that not everyone noticed me and it was true what my second wife told me that it was not all about me. I was relieved when I learned that most of the world was just living life on their own terms and outside of few haters, I could live my life too. It was when I discovered that I was able to ride the level part of my dysphoric roller coaster, for a while.  

It never failed that when I started to come off the flat spot of my coaster, I needed to fight my depression again. Nothing I was doing was good enough as a man or a woman. I was so involved in wanting a transfeminine future, I could not maintain a good solid relationship with my long term (25 years) wife. The only things I was doing was keeping my head above water at work as I carved out the beginnings of a new transgender life. While I did all of this, I managed to make myself miserable as well as those around me. If I could not live with myself, how could anyone else, was my main thought pattern as I rode the roller coaster of life. All I knew was, I needed to hang on tightly for the ride ahead.

Of course, you all know I did manage to hang on, or I would not be here writing this today. Many times, it was because deep down inside I had this unmistakable idea of what I was doing was right. I had waited a long time in line to ride this gender rollercoaster, and I was not ever going to give up my spot. Once I came to this conclusion, I was able to stand in line with other ciswomen and not be so intimidated. And they were less intimidated by me and the rollercoaster hit another exhilarating turn as it headed into a tunnel. This time though, coming out of the dark did not mean I was heading into so much depression. Still, I knew I had a lot of work to do before I could reach my goal or dreams of living a fulltime transgender life.

Every time I thought I had finished a ride on the roller coaster, I found I needed to turn right around and get right on. A ciswoman’s life was so much more complicated than I had ever planned for, there were more challenges ahead. I still had key decisions to make concerning how I was going to live my new life. Such as how I was going to support myself and what was I going to do about telling my remaining family and friends that all along I had been living a lie. Last but not least, I would take the major step of seeking out approval to begin HRT or gender affirming hormones.

Amazingly, each time I jumped on the roller coaster, my rides became shorter and less eventful. I had taken the time and effort to set myself up as a regular in certain venues I went to all the time, so I did not have to go out just to be alone. I was always a social animal as a man and now I was too in my new exciting feminine world. Most importantly, I was able to develop a small circle of ciswomen friends who unknowingly boarded the coaster with me. They showed me the final steps I would have to take to get off my lifetime ride permanently. Maybe the best part was they never knew what they did for me. Eventually, what came out of it all was my marriage to my third wife Liz. A lesbian ciswoman who was instrumental in kicking me off my roller coaster permanently.

Even though I was ultimately successful in reaching my transgender dreams, I am not so sure I would recommend how I did it to anyone. I took too many chances and consumed too much alcohol along the way. Often, I used alcohol to give me a false sense of security when I was riding a scary coaster. Those were the days when I had to internalize my emotions and fear and “be a man.”

Finally, and thankfully, the world around me changed and I stepped down off my roller coasters all the way to less intimidating merry go rounds. Even they didn’t last as I decided to leave the gender amusement park altogether. Truthfully, I never got much of anything which was amusing anyway, and on some occasions, bigots and haters even put me into the freak category. Sadly, I never won any prizes for the most rides on a roller coaster or had a chance to reach for the ring on the merry go round. I was at least a survivor. I did not have to be a man at all.

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.

You're so Vain

  Image from Ava Sol on UnSplash Expressing yourself to the world as a transgender woman carries with it a certain amount of vanity. Unti...