Showing posts with label ciswomen. Show all posts
Showing posts with label ciswomen. Show all posts

Monday, January 19, 2026

Setting New Traditions

 

JJ Hart bottom row, left. 
Girls Night Out Birthday Party

Establishing new traditions or routines can be difficult when you decide to finally live as the gender you were always meant to be.

In my case, the biggest moment of change was when my regular invitation to the family’s Thanksgiving feast was rejected by my brother and sister-in-law who did not have enough backbone to stand up to her rightwing Baptist family. The excuse I was given was, what would the kids think. I was fortunate that my dramatic change was by my daughter and my future wife Liz. Both of them invited me into their family gatherings with open arms and I ended up having an even better time than I would have had with my brother.

Other traditions I was invited into were girls’ nights out for various special occasions such as birthday parties. I cherished the chances I had to go behind the gender curtain and see how ciswomen interact with each other when there are no men around. Sure, I was terrified to go at first but quickly calmed down and warmed up to the experience when almost all of the women there treated me as an equal. Surprisingly to me, I ran into no problems except for one woman who acted as if she was mad at the world anyway. Plus, my most important lessons were if you take men out of the picture, women are looser acting around themselves and the only real difference in the conversation is the lack of sports and job talk. The bulk of the conversation was built around family and spouses.

I took these new learning experiences with me and ran with them into my everyday life’s interactions with other women. I subtracted any talk of employment and my major interests (sports) unless I was asked about something specific. Which surprisingly I was not and my private life which I had not merged at that time, stayed mine. No one pried, and I did not offer. Which worked well for me.

As I slowly began to build on the experiences I mentioned, life became more fluid and natural to me, and I knew I was on the right path. I felt better after spending a night with the ciswomen than I ever did when I was busy posturing with other men. It just took me time to establish new traditions, and I came to expect the occasional invitation to join other women in their celebrations. I became my own woman, just from a different background than the rest of the group. As I learned so much, most of the women never knew how much they benefitted me by just allowing me into their lives. Including the lesbian experiences, I had which went such a long way towards shaping my future.

From the earliest days of going to diverse mixers in Columbus, Ohio and ending up leaving with a lesbian I talked to, all the way to attending lesbian mixers with Kim and Nikki in Dayton, Ohio years later, I again was able to learn so much about the sort of woman I wanted to be. As many of the transgender women around me were stressing about finding a man, I learned I did not need a man’s validation to be me. It really helped me to not needing to change my sexuality while I was building new traditions in my life. I had always appreciated the company of women around me and nothing changed.

If you are considering, or are building new ones, as you know it is a major deal and one that can take a while. My advice is fairly simple, pursue as many avenues as you can and be prepared for the occasional rejection you may receive. Especially from men who may perceive you only as some sort of fetish object. And of course, be safe and meet strangers in public places initially.

Sooner rather than later before you know it your new traditions will become established and second nature to you. That is when the woman who has always been a part of you can emerge and live the life she always imagined. Jumping the gender border may be something you were always destined to do but never dreamed you would have the chance to do it like I did. I needed to wait for decades as I experimented with my gender but finally the doors opened wide for me to find myself in a do or die situation. Either try a male to female transition which was always a female-to-female transition in my world or forget it and move on with my life at the advanced age of sixty. It would have been easier just to do what I always had done and live a life with one foot in each of the binary genders.

I took the hard way out and decided to pursue the next step in my transition (it was a big one) and seek a doctor’s approval to begin gender affirming hormones or HRT. It was a huge step for me and one I did not take lightly. My body took to the new hormones like why did I take so long to do it? It fit right in with the rest of my life of waiting too long to do what was right. Establishing new traditions in a life I always should have known was just the beginning.

 

 

 

 

Sunday, January 18, 2026

Merging your Past with your Future

 

Image from Sammy Swae 
on UnSplash. 

We speak a lot around here about merging your life’s past circumstances with the future of what you may be facing.

Depending upon the number of years you have spent living as your birth gender, you may have an incredible amount of baggage to bring with you from your past. Including the input of spouses, family, friends and jobs. What to bring with you to merge with your new lifestyle as a transgender woman or trans man is often an agonizing decision. One thing is for certain you can’t bring all of your past life with you. However, no matter how you may want to cut it, the basic building blocks of your life remain. Such as how your parents raised you. My parents raised me to be a contradiction from the beginning. I was expected to stand up for what I believed to be right, as long as it did not interfere with what they thought was right. So being a childhood cross dresser was being an individual in my mind but an embarrassment in theirs. So, I had no chance of winning my gender battles.

On the other hand, I was taught the difference between right and wrong but not enough that I could bring it with me when I needed to face the biggest battle of my life, what was I going to do about my unwanted male life. Deep down inside, I knew the right answer then just refused to face it.

For the longest time, I was guilty of putting ciswomen and girls up on some sort of a pedestal as I viewed their lives from the outside looking in. Basically, all I saw was they had the chance to wear the pretty clothes and be pursued by the men or boys in school. I so wanted to be the cheerleader on the sidelines rather than the defensive end I was on the football team. Without seeing all the work, it took to being a good cheerleader. In fact, I never saw any or all of the work needed to transition from being a female to being a woman which I found to be a huge difference. Females are born; women are socialized in the world which means not all women ever make it. If and when you are attacked by a TERF about how you were born, rest assured she has problems if all she could come up with was a so-called birthright.

Getting back to how you merge your past with your future, the first thing you have to remember is not to forget about your present. Your present is so important as you live a daily life, often between two powerful genders, male and female. Your present is often the time when you are working hard to see how your gender dreams will impact your life in the future and how much has it done for your past. In my case, all I had really learned about being in the world as a transgender woman was to apply makeup well enough, so I did not look like a clown in drag, and I learned to shop in thrift stores to find the right fashion to flatter my testosterone poisoned body. I knew nothing about putting my new improved feminine image into motion in the world.

Once I did get serious about looking around in my present-day world back then, I wondered how I was going to ever merge my past with my future. After I determined how badly I wanted to.

My main concern was how one sided my interests were. I was mainly a sports addict with the usual male preoccupation with my job. Most certainly, I would be sacrificing my job if I male to female transitioned but what about my sports hobbies? It was then I became very serious about looking around to notice who all was watching sports at the big venues I was in and I was pleasantly surprised that all those years, I had been missing the number of women who were involved. It turned out that unless I was trying to talk sports with a man, my baggage was safe with other ciswomen, and I was not out of place in my favorite team jersey. To make matters even better, when my wife Liz and I got together and began going to “Meetup” groups, I was able to go to writers’ circles to interact with a whole new set of people. I highly recommend groups such as that to expand your social horizons as a transgender woman or trans man.  The only negative experience I ever had was with a lesbian social group who refused to accept me because I was trans. Which was their loss, not mine.

Then I began to look at my future as just downsizing my life. I was leaving friends behind who did not accept me all the way to going from two wardrobes to one. As Liz once told me, it’s not often a human gets to stop a life and rebuild it, so don’t mess it up. With me, I was fortunate to have help in merging my past with my future. When I was with my new circle of women friends, I just had to learn what to needed to omit from my past which would inadvertently out me as a past male. I was able to talk about my family because I had a daughter, which was a good example, I just could not share birth stories. But in reality, I was in the room, just not doing any of the work.

Any way you cut it, when you do make the decision to cross the gender border, you will naturally have to leave part of your past behind. Just be careful, you do not leave any of the basic building blocks behind which make you the person you are. From there you can build a new and better you as your authentic self maybe you never thought you could be.

 

 

 

 

 

 

 

 

 

Thursday, January 15, 2026

Gender Lost and Found

Image from Jon Tyson on UnSplash.

I spent most of my life in the gender lost and found department.

It all started when I discovered my fascination with my mom’s clothes and was lost when I outgrew all of her wardrobe. I was fortunate when I found a elastic, stretch mini skirt in a box outside the girls’ locker room one day and managed to hide it away in my gym bag and take it home for myself. What was lost was now found.

Along the way, I ended up wishing my overall gender dysphoria could be solved as easily as finding a skirt I could squeeze into and wear. It was only the beginning of a lifelong search to finally face up to who I really was. Until I faced up to the fact that I was never male at all, I was lost in a life I did not want.

Slowly but surely, I began to find my way out of my dilemma. But before I did, I needed to gather all the courage I could to leave my mirror and experience the world, as terrifying as it was as a transfeminine person. It was only then could I see the possibilities of what my future might hold if I actually followed my dreams and was able to live a life on my terms as a transgender woman. Along the way, I found out more about myself than I lost as explored the world. Surely, initially (as I always point out) I was treated rudely in a world which was different back in those days. The world was more likely to find humor in my efforts to be feminine than today when more and more people are just mean. To a point where they will share their unwanted bigoted feelings with you. Every time I was laughed at as a novice cross dresser, I resolved to head home to the safety of my mirror and attempt to fix the problems which were holding me back.

What I found was, I was not trying hard enough to blend in with the ciswomen around me. I needed to lose my male ego which was telling me to run from the criticism I was receiving and for the first time, pay attention to what the world was trying to tell me. Get out of the teen girl fashions I was trying to be seen in and start trying to determine my strengths and go from there.

The more I learned about presentation as a trans woman, the easier my life became as I began to test the boundaries of what I could do. For the most part, I was successful in building the basics of a new feminine life other than the times when I tried to go too far into venues I should have never considered trying. Ironically, one of the biggest set of venues I needed to lose were the gay bars I was going to. Even though, for the most part I found I could express myself there, my growth as a person was slowed dramatically. I tired of being rejected as just another drag queen and wanted to find something more. Losing the gay bars except on certain occasions was the best move I made except when I found acceptance in a small lesbian tavern I went to regularly along with the bigger sports bars, I found that I could be a regular in also.

As I expanded my feminine horizons, I lost more and more of my male self who had always wondered what it would be like to go to his favorite venues as a woman. I found I was right and enjoyed myself even more as a transgender woman. Especially when I went there enough to be recognized as a person, not some sort of a man in a dress. My golden rules of being accepted almost always worked for me as there were three. Number one, be friendly and not be a bitch. Number two never cause any trouble, and number three always tip well.

The only problems I found were when I needed to separate who I was in the real world when I needed to go back to being a man and existing in my working world, I increasingly wanted nothing of. It was a fast-moving pressure packed macho world which I could never see myself doing a male to female transition in, so I was lost in limbo much of the time. It was the only major problem I found I could do nothing about and had to give up a well-paying job when I retired to a fulltime transgender woman’s world. At least, I found my knowledge of competition carried me over quite well into the women’s world I was in. Of course, I needed to lose all my male privileges’ I had gained over the years and start all over again and often I learned the hard way that women compete just as hard as men. Just in different arenas.

Once I learned the new rules, I was learning quickly and even enjoying my feminine world even more than I thought I would. Probably because I was dealing from a position of gender strength because of all the time I had spent in a male world. Many times, I found I knew what potential problem would be coming at me before it even appeared. One of the gifts of being a transgender person.

Of course, now I feel that I have found much more than I had ever lost. I look back at my all too lengthy male life as the chance I had to learn the basic building blocks of life which I would need later to succeed at being a woman. From there I needed to take all the benefits I found as a new feminine person and use them wisely. To squander all that I had learned would have been a tragedy as I wasted all my time in the gender lost and found.

 

 

 

  


Saturday, January 10, 2026

When What You See is Not What You Get

 

By request, Liz on right at a summer picnic.


Most all of this post comes from the early days of me being out in the world as a novice transgender woman.

Early on, when I was hanging out in the gay men’s venues, I had a difficult time separating myself from the drag queens in the room. While I appreciated their artform, I certainly was not a part of it. The only time I had tried to ever perform on stage was at a crossdresser-transgender mixer I had went to years ago in the Cleveland, Ohio area. I was a dismal failure, and my performing career was over, for good. But I walked away from the experience in my high heeled shoes with a newfound respect for what good drag performers go through.

Life really began to change for me when I left the gay venues and began to see if I could make it in a more normal universe in the big sports bars, I was used to going to as a man and wondering how it would be to experience them as a transgender woman. Surprisingly, I found less resistance to me being there than I did in the gay bars where I sometimes had to fight to get a drink. Not unlike the clerks I met in mall clothing stores, I found I was no more than a dollar sign to most all the servers and bartenders I met. As long as I followed the basic rules of smiling, never causing any trouble and tipping well, I was cool to most all of the employees I faced and for the most part, just another face in the crowd. Which is exactly what I wanted.

In the venues I went to, it did not take me long to become a regular and I took advantage of perks such as restroom privileges. Plus, when the bartenders knew me so well, it helped me with other new patrons who may question my existence. I wanted anything but them thinking they were encountering a man in a dress.  To preclude that happening, I worked hard at blending in with the other ciswomen around me. I knew exactly what most of them were going to wear so I could wear the same thing. When I did and my makeup and hair were on point, it gave me the confidence to try new things as a trans woman.

I discovered at that time, my own little rating system I used with the public. I felt a high percentage of the world was just going on about their business and did not care about me one way or another. Then another percentage who did notice me were curious (not evil) women who wondered what I was doing in their world, and finally there was the group of haters who had sensed I was different and wanted to confront me. Fortunately, they turned out to be the smallest group I needed to face when I was out in the world because I was certainly not what they thought they were getting when they saw me in public. I was more than a fearful spineless person trying to act like someone they were not. I was rapidly becoming more comfortable as my authentic self.

Perhaps the biggest learning experience I had was when I did know I had the confidence to be myself and what the world saw of me was all true. No drag queen, no parttime cross dresser, just me a transgender woman. Since the great majority of the world had no idea of what a transfeminine person was, I knew I would have to educate anyone who needed to know more about me. On occasion, I needed to answer insensitive questions from people who had known better. Like the nurse at one of my mammograms years ago, who blurted out something to the effect did I still have all of my equipment down below. Like it was any of her business. But, for the most part, people treated me with respect. It was all in how I treated strangers. If I acted as if nothing was wrong with me, most people went right along with the program and did not ask me any invasive, personal questions.

Then came the portion of my life when I began to be able to surround myself with people who never knew anything about my old male past. Amazingly to me, they accepted me as I was and never asked any probing questions. The only outliers were my transwoman friend Racquel who told me I passed out of sheer willpower and my wife Liz who sent me down a permanent path to transition when she told me she had never seen any male in me at all. She was particularly profound at the time because I was still trying to live part-time in both of the main binary genders. Liz knew what she saw was what she was going to get when I went through my male to female transition and even started HRT or gender affirming hormones. In fact, I took my first doses (I was on pills then) when we celebrated New Years Eve together one year when we first met over a decade ago.

I desperately wanted the world to see in me what they saw in all women, just a feminine person trying to live her life as easily as possible. It took me years to build the confidence and courage to shed my old male self and do it but certainly it was finally worth it to live my truth. My motto became, what you see is exactly what you get and if you for some reason don’t like it, it is your problem. Not mine.

 

 

 

 

 

 

Thursday, January 8, 2026

A Labor of Love

 

Image from Mor Shani


Lately, it has occurred to me that possibly my posts have been a little negative when describing my journey along my gender path. Sure, my trip had its ups and downs but overall, it was a labor of love. Gender euphoria always seemed to come along at just the right time to keep me centered on my dream of living a transfeminine life. Finally meaning to me that transitioning male to female was the only way to live for me.

From that point forward, I just had to figure out a way to do it. I knew I loved the lure of women’s fashion and makeup, and how it all changed around me on a seasonal basis. So far from the male fashion I was used to. Instead of just putting on a coat when the weather became cooler outside. Now I needed to choose between leggings, boots and fuzzy sweaters to keep me warm and stylish.  Furthermore, I loved the concept of seasonal change and the desirability of going through my wardrobe to see what could stay and what had to go to the thrift store.

Even though, fashion and makeup remained a priority for me, a new love interest set in when I began to explore the world more as a transgender woman. Whole new gender vistas opened up for me relatively quickly as I needed to put my static mirror version of my trans woman self into motion. It became a labor of love to go out and start meeting new people. As I did, I came to the realization that most strangers I met did not mistake me for a cisgender woman, but on the other hand, I could be quite satisfied to be recognized as myself…a woman from a different background. I think in a couple of the venues I became a regular in; I became their token transgender woman to prove their overall diversity. Whatever the case, I loved the extra attention I was getting. Especially from the ciswomen I met who were basically curious what I was doing in their world.

All the on hands experience in the world I was getting helped me to want more and leave my male life behind. As I always say, the gender change concept seemed to be so natural for me as I went forward. The only problems came from wondering what I was going to do about all the male baggage I carried with me. I discovered I was much more than a man trying to put on a pretty face, I was a full-fledged person trying to build a life from scratch. All the nuances of doing so extended way psst making sure my shoes matched my purse, all the way to wondering how I was going to handle the woman sitting next to me when and if she tried to make conversation. In a very short period of time, I became used to the challenge, and it became part of my life and yes, I loved it.

As I increasingly loved this new life I was living, I was able to balance between the two main binary genders. Before it became too much to handle mentally for me. It became increasingly evident that if I was going to survive as a person, I was going to have to choose one of the genders pulling on me. At that point my lifetime of loving everything feminine kicked in for me. Long ago, I had realized I was much more than a casual crossdresser and made it a love affair to learn more about my dream of being a woman on my own terms. Which meant I did not necessarily need all the extensive facial or gender realignment surgeries. I just needed to present well enough in the world as a trans woman to be left alone. Mainly because of the circle of ciswomen friends who accepted me as an equal, I was able to achieve my goal. Even with the added surprise of finding a woman who loved me the way I was.

The tragedy probably was I did not realize the depth of the love affair I was having until much later in life. I would have preferred to have spent more time living as a transgender woman in a world I created. Rather than sharing it with a man I started a life with and had very little control over.

I will never know (of course) what life I missed and maybe the course of destiny I was on would have stayed the same anyhow. Just being able to acknowledge the lifelong love affair I was on is just enough to rationalize where I ended up. So if you are just starting or contemplating starting your journey, try to look down deep inside of yourself to see where your love affair has taken you. It may save you problems later on your journey.

 

 

 

 

Wednesday, January 7, 2026

Reflections on a Theme

 

Image from Alexsandra King
on UnSplash. 

Reflections on a theme could really go several ways.

The first one goes all the way back to my earliest days of gazing in the mirror at my new girl-like figure. Since I did not have much to work with as far as clothes and makeup went, I needed to use a lot of my imagination when I looked at myself. All I remember is, every article of clothing I could wear was cherished and I hoped I did not destroy it and clue my mom into someone had been into her clothes.

On the other hand, makeup was a little easier to hide, since mom had a whole drawer full of used makeup and samples for me to experiment with until I arrived at the point where I did not think I looked like a circus clown doing drag. As I said, imagination played heavily into my girlish pursuits back in those days until one fact came in loud and clear. Just dressing like a girl fell far short of meeting my expectations of how I wanted to feel. More than just looking like a girl, I wanted to know how it would be to feel like one. It turned out to be an idea I would carry with me throughout my life. Little did I know I would be writing about the same theme some fifty years later as I still struggle to understand all the aspects of the gender dysphoria I went through before I just gave up and went to my dominant side which was OK because in her own way my mom was a dominant woman and had to be to survive in the world of men she was in.

I guess you could say mom was the first feminine role model I had. As I reflected on her, I saw a person who worked hard to get a college degree during the depression years then ran off with a man her parents probably did not totally approve of. In other words, she was strong-willed and often got her way. Except for the daughter, she never knew she had who was watching more than just the way she applied her makeup. I was watching how she navigated the world. In my own way, I went through my own great depression as I learned how difficult it was going to be to be a transfeminine person. Long before the term was ever used.

During this time, I spent a lot of time reflecting on who I was and why I was this way. Surely, I was one of a very few boys around me who wanted to be a girl. One of the many ideas I reflected on was the fact that I was simply afraid to go out and compete with the other boys. Which even though was probably true to an extent, I knew I had to do it anyway, so I had no choice but to make a half-hearted attempt at doing boy things to throw gender doubters off my path when they realized what an effeminate boy I really was. Since I was not athletic enough to hang with the jocks or smart enough to hang with the brains, I ended up taking some sort of a middle path with a group of troublemakers which at least kept me away from the bullies. Sadly, there was no group for boys who wanted to be girls.

As I stayed in the mirror for years and years, I built up quite the love for my reflection as I went along. So much so that I caught my reflection lying to me. No matter how ridiculous I looked, the reflection I was seeing told me I looked great which hurt my overall feminine approach to life, out of the mirror. It was not until I gathered all my courage and began to explore the world as a novice crossdresser ot transgender woman, did my reflection begin to change. What happened was, for better or for worse, I traded out my home mirror for one in public. As strangers began to notice me, I very quickly received feedback on my reflection from them. Was I convincing the world that I was a serious transgender woman and not some sort of a joke or someone up to no good that was all the craze back in those days on television and in the movies.

All of this reflection on a theme quickly became very important to me since I had finally made the move to get out of my closet and see the world through the eyes of a very serious trans woman. Soon I reached the point of no return and just had to rely on my home mirror to apply my makeup and fix my hair. The rest was up to me to do in the public’s eye, where my true reflection always was. My theme always should have been I was a feminine based individual all of my life with strong ties to woman role models. My goal never was to be the, “Pretty, pretty princess” as my wife called me. I was just going through a phase so get to a point where I could become a strong independent trans woman. I did not know at the time how much the world would change and I would need every bit of my new self to survive under a corrupt president who wants to erase the LGBTQ community.

Now, when I see myself in the mirror, the only reflection on a theme that I see is me. I am a survivor of my internal gender dysphoria wars and external problems along the way too. Some were interesting, some I learned from and most were quickly forgotten as life intervened. All I know is, I would never have found out if I had been stuck in my reflection on a theme. Which was being a woman. Being stubborn enough to keep pushing ahead was what kept me going. Deep down, I knew I was right.

 

 

 

 

Friday, January 2, 2026

Practice, Practice, Practice

 

Image from Mor Shani
on UnSplash. 

Sometimes I wonder if some people don’t take the time to understand how much practice I needed to do as I became my authentic self. I guess I could say I went through nearly a half century of work to become who I dreamed of being. It was far from easy.

Starting at the beginning, I never had much to work with as far as being an effeminate boy. Not to mention, I was born into a very male dominated family. Very early I learned I was going to have to work hard to not look like a clown in drag when I tried my best to look like a pretty girl in front of the family mirror. I always equated putting on makeup with painting the plastic model cars I had. Which I was always very bad at doing.  

It did not help when I earned my own meager amount of money working around the house or delivering newspapers in the neighborhood. Then I used the money to try to shop for makeup. I still remember to this day, the first time I was confronted by the sheer number of various makeup brands and variations to try. I finally selected several products out of desperation and hoped for the best as I was trying not to use my mom’s makeup anymore. Now, I don’t remember how successful I was, but I kept on trying to practice on my face until I got it right. Or so I thought. It wasn’t until years later that I visited a true professional makeup artist that I discovered I was not working on the true potential of my makeup to its maximum effectiveness. I was merely making the same basic mistakes over and over again.

I was fortunate to have the makeup artist who was able to explain to me in terms of understanding what he was doing, so I could repeat the process later. Practice for once made perfect. I was able to paint my model cars in a way that my friends admired them. But this time, I was actively admired at the crossdresser-transgender social mixer I was at, and this time when I tried to hang out with the “A” listers (as I called the beautiful, more advanced crowd of attendees) I was accepted. The best part of the whole evening was I then had a basis of where I needed to be as far as being an accomplished cross dresser but on the other hand, I was presented with a deeper set of questions about what I was going to do about my male life as I knew it.

What I decided I had to do was take my transfeminine show on the road so to speak and see if it would play at all in the public’s eye. Away from all the safety of mixers and gay or lesbian mixers. That is when the real practice set in. I needed to stop all of the hard-earned male muscle memory I had learned and start to learn the best that I could the graceful, fluid moves of a cisgender woman. Naturally, the whole process was difficult to do. Especially when I was switching back and forth between the two main binary genders almost daily. Constantly, I needed to remind myself of who and where I was so I would not end up at the wrong place at the wrong time.

Through it all, when I thought I was being successful in going down my transgender path, roadblocks always emerged which sent me back to my drawing board and started setting up more practice. Those were the days of taking every spare moment I had to sneak out of the house and begin to carve out a new life for myself as a trans woman. Once I made it successfully out of the gay venues I was going to and into a few of the big sports bars I was used to going to as a guy, I started to relax and enjoy my new exciting life even more.

No matter how much I try to gloss over this part of my life, the fact still remained I was essentially cheating on my wife when I went out as myself. Deception was never my strong suit, and I was never proud when I needed to lie about what I was doing. By this time, I had reached the point of no return but still was afraid to face it. I hid it by staying in the so-called practice mode I was in. If I could have just one more experience being a transfeminine person, it would make it so much easier when I decided to permanently put my old unwanted male self behind me for good.

Finally, I quit kidding myself, and I was doing so much than practicing over and over again to live a transgender life. I had always dreamed of doing it, so it was time to do something about it and live it. Who knows, maybe all that practice at living a feminine life saved me in the end as I finally learned to move and communicate my way around in a ciswoman’s world.

 

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.

 

 

 

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.

 

 

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.

 

                                                                                                                                          . 


Her Way or the Highway

  Image from Joshua Rondeau on UnSplash.  Very early on, it became evident to me that my feminine self was very demanding. Who knows, maybe...