Showing posts with label ciswoman. Show all posts
Showing posts with label ciswoman. Show all posts

Thursday, August 13, 2026

I Had No Idea

 

Image from Hayley Lawrence
on UnSplash. 

As we dodged yet another terrible weather bullet where we live in this part of Cincinnati, and I sit here writing, I feel a deep sense of belonging in the life I discovered years ago.

Certainly, through most of my life, I never thought I could make it this far and live out my own dream of living as a fulltime transgender woman. Possibly, it is because I got off to such a rough start when I left my gender closet and took on the world. Back in those days also I had such a simplistic view of what it would take me to live as a woman. I mistakenly thought I would just have to look as close as I could to a ciswoman. I had no idea of how wrong that would turn out to be.

What I had never really considered was how difficult it would be to truly cross the gender border and face all the everyday challenges ciswomen face in the world. Including the ones from toxic men. In that sense, I was fortunate in that I was not attractive enough to garner much attention from cismen at all and only had to deal with the new surge of attention I received from the women around me who mainly wanted to know more about what I was doing in their world. What the women never knew was when they were studying me, I was closely studying them because I was on a crash course to learn everything, I needed to be accepted into their club and be allowed behind their gender curtain.

Referring back to a recent post of mine and a comment from “Mark”, I was excited to be finding the true me and I enjoyed the excitement of being in a new world I always wanted to be in. Probably because I thought it would never be me who could do it. Thanks for commenting, Mark!

Change was slow, but eventually the confidence came that just maybe I could exist in a world where ciswomen ruled and make it. It was only then when I had any idea that it could be me that made it into the world I knew from my transgender mentors I had met at the parties I was going to in Columbus, Ohio. At that time, even though I had very few certainties of where I would end up in life, if I had my choice I rather be like the trans women I knew that the part-time cross-dresser than I was. It was my dream and I was sticking to it. Even though I knew I did not have the natural resources or the financial means to be as beautiful as my friends were. I realized that all ciswomen were not classic beauties but lived fulfilled and impactful lives anyhow. So, there was a path for me anyhow.

My new idea opened a whole new vista of being femininized for me. It meant so much more than the makeup, hair and pretty clothes I was having a chance to wear for the first time. Suddenly, I could see a path forward to where I could see the real me for a change. A person that I had no idea about was there but liked it when I discovered her.

Now is the time I always take to explain how difficult this part of my life was. It seemed nothing was coming easy to me as I struggled to find a middle point with my second wife over my gender desires and my work was making new demands on my male self. The worst part was that the idea of who I was internally was becoming clouded and I lost sight of where I needed to go to find me. As I grasped for answers, I could not wait to get back to my safe place in Columbus and interact with the diverse LGBTQ group of people who always gathered there.

It took a while, but I finally gathered the courage to set out on my own to see if my idea of making it in the world as a transfeminine person was dead. The problem was that I only had known the world of gay venues to attempt to express myself. Since I had never identified as a gay male, I never felt at home in their venues, only lesbian bars and large straight places. I needed an extraordinary amount of courage to begin to see if I could exist in both at all. When I found out I could, almost nightly if I was not working, I was trying out the new world I was carving out for myself. No matter how hard I tried to blend in with everyone else, I did not to the staff of bartenders and servers who routinely took care of me, and I was unmistakable to them and had no problems becoming a regular. A smiling face and good tips took care of the rest.

Long story short, I was finding myself as the person I had no idea I could be. Before I knew it, I needed to settle on one wig and decide on a new feminine name for me to use in every venue I was in regularly. The pressure was on to not lose everything that I had gained over the years, and this time I could just start all over again building a new woman from the building blocks of my male life. The prize I never thought I would ever get was suddenly within reach, and I needed to figure out what to do next.

That decision was made for me when my second wife as well as the only good male friends I had ever had all passed away in a short span of time. I was left by myself to decide my future which without much thought turned out to be female. Yes, the idea I never thought would come true was, just when I thought again that it never would. I am a living example of how someone’s life can change if you stay on your gender path. Especially when you don’t expect it. Sadly, I remember the dark days when all I had was two dogs to comfort me in my times of duress and I had no idea I could ever climb out of my depression to where I could find the support, I needed to live my dream life.

It turned out for me that my grand idea was a good one after all.

 

 

Tuesday, August 11, 2026

Understanding is the First Step to Overcoming Fear

 

JJ Hart (Center) on a 
girls' night out. 


Before you can overcome fear, you need to understand exactly what you are afraid of.

I know I was petrified of leaving my closet behind and heading out into a world where I knew little or nothing as a novice cross-dresser. It took me years to overcome most of my fears except the ones I never did. Such as going into male dominated spaces by myself as a transgender woman. For some unknown reason, that one thing has always been a problem for me and my anxiety issues about coming out in the world.

When I was younger, I always thought either I would grow out of my need to feel feminine in all ways or somehow, I would lose my fear of doing it. Of course, I learned quickly that anytime soon I would not be outgrowing my urges to cross the gender border into a feminine world. In fact, my urges were getting stronger which led to more fear and anxiety about the future of my life. Out of sheer survival, I had to find out why I was so scared.

The easy way out for me was just by thinking that making the gender jump into what I perceived as greener pastures, was the reason I was so scared. I was using the dresses and makeup I had acquired to hide behind and feel better in times of duress. I was too new at the gender game to consider ideas such as gender privileges which I was accumulating as a young man with out even knowing it. Privileges such as never having my intelligence questioned or having an innate sense of personal security were never questioned. I found I would not have to until much later in life when I began to present well enough as a transfeminine person to get by. All of a sudden, passing as a woman meant more than just having a man open a door for me. I had to take the good with the bad if I was ever going to be successful in making it to my dream of living as a woman on my own terms.

The more involved I became in my male to female femininization, the more I discovered there was no easy way out. Which frightened me more. I always equate it as me busily painting myself into new life corners as a trans woman which there was no easy escape from. Finally, I did see a brief escape from my unreasoning fear was when the transgender term was being popularized to gender conflicted people like me. There was a term which described people such as me who did not fit into the cross dresser-transvestite mold or the more extreme transsexual person. From the moment I saw the trans term, I immediately knew it described me. It certainly took long enough for a term to come along, which helped me, but it finally did.

Being able to read about other more accomplished transgender women and trans men helped me to understand my fears and why I was feeling them and the new less rigid gender spectrum terms helped me immensely. For the first time in my life, I could pinpoint why I was feeling a certain way and at the same time calm most of my anxieties. Gender diversity became my motto in life as I really began to explore the world of ciswomen for the first time. I had left the men’s club (and they knew it) and wanted to join the women’s club if they would have me. Yes, the world of ciswomen would have me which lessened my fears and anxieties immensely. Mainly because I had a better understanding of where I wanted to go.

Looking back, I do not know why I took so long to try to have a better understanding of who I really was. I could blame the usual suspects such as my old male self or my second wife who put up such a battle against me transitioning when in reality it was all on me. In the would of-should of department, I always should have faced up to the fact I was more female than male and should have not made life miserable for my wife when I did not “man-up” in her terms and become a woman. I guess I was never one to take the easy way out.

If I had taken any of the excess time I was wasting, I would have taken the time to calm my fears by understanding who I was as a person and try to build a better feminine person I learned I could be from all the male building blocks I had left behind. As I looked around at the new world of ciswomen, I was seeking admittance into, I realized they were more diverse than even I had given them credit for. And I would not be shunned for wanting to do something like wearing my favorite team’s jersey on game day in one of the sports bars I was a regular in because other women were beating me to it by wearing their jerseys It made my fears evaporate as my life became more fun again and certainly more fulfilling as I had always wondered what it would be like to cheer my favorite teams on in the venues I was used to going to as a woman and not a man.

Once I finally started to have a basic understanding of where my fears were coming from, I was able to better keep them under control. Which, in turn led me to being more relaxed with a chance to let my long hidden trans woman personality shine through.

I know it is difficult for all of you who are just getting started along your gender path to not be afraid because of what is at stake but if you are able to slow your life down to take a closer look at it…you will stand a better chance of understanding your fears and anxiety and living a better life.

Thanks for reading along and I hope my experiences can help you anyway I can!

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Monday, August 10, 2026

Stepping Out as Yourself


Image from Max Anderson
on UnSplash. 

Stepping out into the real world and leaving my closet and mirror for the first time was difficult for me. For lack of a better term, I was leaving everything I worked for in my male life behind.

As much as I hated my dark, lonely gender closet, I found it to be a safe place to be when I needed it the most. My ability to put on a dress and makeup soothed my soul, if only on a temporary basis helped until I needed to take another high heeled step into the real world where I so desperately wanted to be. To put it mildly I was scared to death when all my male privileges I had worked so hard to learn were stripped away and I was starting all over again. It was different when I could not rely on a menacing facial expression or an occasional bluster to get me by.

Stepping out into a new feminine world for me meant I needed to immediately begin to work on building a new personality which would grow with me as I worked my way towards my dream goal of living fulltime as a transgender woman. This was the same period of time that I was obsessed by my feminine appearance, so I had a lot on my mind. As I struggled day to day about what gender I was going to be. All too soon, life meant so much more to me than buying a new dress or skirt all the way to how I needed to change my old male movements when I wore them.

As I was forced by being in the public’s eye, I needed to understand exactly what I was getting myself into. So much more than the pretty clothes that I saw the girls around me wearing. If I needed to be more like them, I had miles to go on my gender path to get there. All I knew was at that time, most of the ciswomen I encountered were nice to me. Every little bit helped me learn what my future could be like if I kept stepping out and away from my old male past. Plus, problems kept occurring with my second wife and my male self who saw the changes in me as a threat to their future lives. My second wife saw her husband slipping away and my male self-saw his whole future gone if what I was doing continued.

Through it all, I was able to establish myself as some-sort of a successful cross-dresser before I transitioned into a transgender woman one fateful night when I thought enough was enough and I had to do more to continue up my gender path. Before I became lost entirely and had to reassess where I was. What I learned was that I was actually further along towards my transfeminine goal than I thought I was. I learned the hard way when I was able to be successful when I went out for the first time to enjoy a drink with a group of ciswomen from a nearby mall who just would go out and socialize after work. It was something I always had wanted to do as a transwoman, and I was amazingly accepted into their circle. I guess you could say that night I really stepped away from my old male self and loved it.

Before I knew it, my new shiny shoes (flats this time) were stuck in gender quicksand as I had stepped into a place that I never wanted to get out of. One thing was for sure, if anyone came along with a rope trying to rescue me, I would have turned them down. I was having too much fun challenging the world as my new transgender self to ever turn around and go back to a boring life as a man that I had stepped away from.

Sure, there were still many times that either I was scared to death of where I was going or was out and out rejected by the world, but those times were getting fewer and fewer apart. I was headed towards my dream goal which was slowly coming into focus as a doable project. I say project because I had never attempted such a thing as jumping the gender border to slide behind the gender curtain in my life. When I finally accomplished my goal of being allowed to exist in so-called women only spaces, I certainly was not going to give up all that I had earned.

By this time my second wife had passed away, and my old male self was seeing the writing on the wall, and his days were numbered too. Which left me all alone to make my key life choices. Still after much thought and consideration, I finally gave in totally to my feminine side, and I set out to build a different yet better life with my new ciswomen lesbian friends. All of them helped me round out and refine the woman I always wanted to be. Most of the work I had already put in, so I did not have that far to go. Mainly the only place I needed to go was with my dealings with men. Even that turned out to be relatively easy because most men left me alone because I was not attractive enough or just wanted me as some sort of a fetish object. All my problems went away when my lesbian friends taught me I did not need a man to be validated anyhow.

As stepping out as a transgender woman in the world became natural to me, a whole new universe of life came alive for me. Especially when I was approved for my long-term dream of starting HRT or gender affirming hormones. Something that my second wife always recoiled at the idea of, but on the other hand, my current wife Liz loved. The essence of being on my hormones just carried over into me stepping out into a new world with confidence I had never known before.

 

 

 

Sunday, August 2, 2026

Violating Gender Boundaries

 

JJ Hart. Pushing my gender\
boundaries. 

Very early in life I learned that violating gender boundaries could result in severe trouble.

It was obvious to me that the male dominated family I was born into would ever accept a son who wanted to be a daughter. So, I had no choice but to turn inward with my developing feminine senses in the male world I was trying to be a part of. I was born way too early to take advantage of the forthcoming online information world with the advent of computers and social media. Again, I was trapped into trying to cross-dress my feelings away anytime I had the chance.

The other main problem I had was that the gender boundaries were so rigid and demanding I could not see any way out of my dark, lonely gender closet. I lived in a rural area with mostly boys and no girls to have a point of reference from. I only remember one occasion when the only girl in the neighborhood was persuaded by a couple of the boys to show her naked genitals to the group, and I was not excited but embarrassed for her at the time. Just another example of how my sexuality was developing away from the “normal” male’s. I had no need to see her private parts and wondered why I was so different. Little did I know, it was just the beginning of challenging my gender boundaries during my life.

As far as the rest of my life went, I wasn’t much of a challenger of anything. It wasn’t until I reached my college years and was drafted into the military during the Vietnam War, did I begin to challenge the system. At the same time, I was starting to challenge the war and the politics around it, I was pushing my cross-dressing boundaries by starting to leave my house more dressed as the person I wanted to see if I could become. I even made what turned out to be a huge mistake by coming out to my fiancé as a transvestite or cross-dresser back in those days. I say huge mistake because she wanted me to tell the draft board I was gay to stay out of the military service. Even then, I knew a lot about myself and did not have to push my gender boundaries so far to lie and tell someone I was gay. As a side note, then and now I did not have anything against the gay community, but I just knew there was a real difference between them and me.

Of course, the military stopped any gender challenging I was thinking of doing dead in its tracks for nearly three years of my young life. The only challenge I could do was mental in nature as I imagined how life could be better for me as a transfeminine person when I was discharged from the Army. Even then, I was restricted in my gender thinking to the reality in life. What I almost did was send a letter (remember them?) to my future first wife explaining it maybe a transwoman picking her up at the airport when she arrived for the first time. She was in the Army too and was discharged about nine months after I was.

Little did I know, if I had decided to test my gender boundaries then it may have been one of the better times to do it because I did not have the chance to build up all the troublesome male baggage I would acquire later in life. On the plus side, I had a very new car that I had shipped home from Germany, my stereo equipment and a sizeable bank account to start a new life with. On the negative side, I thought I had a good chance of losing my family, friends and job if I started all over as a woman.

Long story short, I did not have the courage to push my gender boundaries any further than they were at the time. Except for a few Halloween adventures, and the occasional night out, my life as a trans woman was mundane. It was not until I could not take it any longer the annual yearly adventures at Halloween, did I start to really push my luck by going out more often. My early explorations were rough to say the least until I settled down and learn how to blend in with the ciswomen who I found really ran the world I wanted to be a part of.

As the world let me in as a transgender woman and/or I finally learned the truth of who I was, I kicked and pushed until my gender boundaries came down. It was like the steep slope I write about as I slid down trying my best to hold on to what was left of my old male life but failing miserably. As I continued to gain my new feminine ground behind the gender curtain, which was hidden from me for so long, I had pushed by gender boundary so far, I was too far gone. I was no longer afraid of the fall and knew I was too far gone to ever go back to being my old male self.

From then on, gender boundaries did not mean much to me except from my former history as a man, I could see both sides of the border from where I lived as a trans woman. Leaving the man’s club scared almost all of the cismen away but attracted as many of the ciswomen that I needed to set up a new boundary. The new boundary was one which validated myself as a woman for the first time in my life and it seemed I was learning daily how to adjust to my new situation.

From that point forward, I changed my legal name and became extra serious about my physical and mental well being by being approved for HRT or gender affirming hormones. It just seemed by that time, I was just doing what came natural in solidifying my new gender boundaries. Sure, they were all big moves in my life, but good ones that I had always dreamed of making.

As always. Thanks to all of you who read along with my lifetime worth of experiences. Your responses and comments make it so worthwhile for me!

 

 

 

 

Monday, July 27, 2026

Staying in the Present as a Trans Woman

JJ Hart at Trans Ohio.
Staying in the present has always been a difficult task for me. Perhaps it all started when I was a very young gender distracted person and could not seem to stop daydreaming about being a pretty girl. The daydreams were nearly always a great escape from my everyday boring male world where I was always competing for the same rights to be recognized at all.

Overtime, I was rarely successful as a boy and just put in the amount of effort to get by. The only thing I was moderately successful on was hustling on my newspaper route and doing extra chores around the house to make extra money. Which in turn, I used to buy my own feminine articles such as makeup, and pantyhose for when I was able to shave my legs. Overall, my plan worked and eventually I was able to build up my own collection of cross-dressing essentials. As I discovered I could get away with shopping at a couple of small local department stores for everything I needed to shatter my dream of doing it and stepping into my own form of reality.

The older I got, the more I did not grow out of my cross-dressing gender desires. In fact, I grew into them when the world became more and more accessible to me. I was building an increasing sense of confidence in my new self and going out briefly into the world as a novice when the Vietnam War and the persistent military draft caught up with me. For the first time in my life, I could not daydream of something as major as a war going away. It was as real as my draft card. Which I resented having because none of the ciswomen around me needed one. Why should I be forced into an unfair war when they were not was what fueled my resentment. A resentment which just made me feel worse as I wasted my time worrying about the war which was staring at me in the face.

To make matters even worse was the fact my fiancé who knew I was a cross-dresser told me we would break up unless I told the draft board I was gay. Which, there was no way that was going to happen, so we did end our relationship just before I headed out to Ft. Knox, Kentucky for Army basic infantry training. Even though I fought military service as long as I could, in many ways it did me good because I needed to stay in the present most of the time when I was going through basic. If I was not, I would feel the wrath of the drill sergeants which was not a place I wanted to be. I guess you could say, I was going through a whole different basic training by teaching me to stay in the present.

After I had served my time, I tried my best to pick up where I left off by trying to join the world as a transgender woman. A new life was just starting to come to me with the realization I was much more than a part-time cross-dresser and needed to experience more of a woman’s life to satisfy me. Change was upon me with the birth of my daughter and a new wonderful world of mall shopping experiences to explore. After a rough start, I was able to present well enough to enjoy being out in the world. In other words, the teenaged girls who made me a target suddenly left me alone. The rest of the mall time was easy because I discovered that my money was green and that was more important to the store clerks who waited on me than my potential gender.

Eventually, more reality than daydreaming set in with my life. I was becoming so successful in carving out a new transfeminine life I knew that I had gone too far to ever turn around on my gender path to ever go back. Sure, I was scared but a voice in the back of my head kept telling me this was so natural that my new world deserved to be the reality I always sought and I needed to stay in the present to do it.

I discovered as a transgender woman, the present was a very great place to be. For once, I had access to the gender I wanted to be with which were all the ciswomen who showed interest in what I was trying to do in their world. I had always had a difficult time making friends with other men when I was acting like one and I finally figured out why…I should not have been in the boys’ club to begin with. Living a lie was a total mistake which should never have happened. I was not interested in a club where I never belonged, and that was OK.

Old habits are hard to break, and maybe even more so for transgender women and transgender men. Primarily because we have to decide what baggage we are taking with us or leaving behind as we journey along our gender journey paths. Bring too much, and you can’t carry it all or don’t bring enough and end up losing all of your building blocks you need for a new life are all things to consider. And most of all, it is important you stay in the present, so you don’t forget where and who you are and slide back into your old self. It is frustrating when something as small as the look on your face can destroy all that you have worked so hard to perfect. That old male “stay away” scowl may have worked in your old world but in your present one, it certainly doesn’t.

It was difficult for me to find my present. Determine if it was the right choice and then stick with it. As I went through my male to female feminization efforts, I needed to finally decide on a wig to wear on a regular basis and quit looking for the miracle wig which would instantly make me attractive. Why? Because people were starting to recognize me as a person, and I needed to build on that. Instead of just carving a new person, I was blasting one and having the time of my life doing it.

I just wish I could have stayed in the present earlier in my life, which I know would have given a better understanding of who I was at the time. I almost did more after I served my time in the Army, but it was in the mid 1970’s and the world was different, and I did not have the courage to do it. Instead, I played my status-quo cards and thought I could help my life along by just cross-dressing. By doing so, I just ended up losing so much of my life when I ignored living in the present. One way or another, it is much too late to cry over time that was wasted and remember the good time when I discovered my present and lived it.

Thanks for reading along with me. Hopefully my insights can help you with yours and comments are appreciated.

 

 

 

 

  


Thursday, July 16, 2026

Finding Comfort in your Own Skin

 

Image from Ayesha Rosley
on UnSplash.

I believe the way to finding comfort in your own skin as a transgender person is having the confidence to do it.

Just think of all the time you may have spent in front of your mirror as you gathered the courage to take on the public and work from there. Like many of you, I experienced severe gender dysphoria every time I looked in the mirror and saw a man dressed as a woman and was afraid to go out into the world and face the public. To this day, on occasion, I still suffer from my lack of confidence in who I really am when I look in the mirror in the morning. I do my best to just ignore it and move on and take on my day knowing I am doing my best with what I have to work with. Or as a transgender woman friend once told me, I pass out of sheer willpower.

My willpower was tested during the many times that I failed in public and needed to start all over again. At that time, I had very little confidence that I was doing the right thing with my life. I had to go through years of trial and even more error before I began to build the confidence I needed to succeed in the world as a transfeminine person. When it came right down to it, many times I was excited about the prospect of going through another trial to learn if I could be successful. When I was a success as a trans woman, I wanted to do more on my transgender bucket list of things to try in the new exciting world I was in.

Most the major changes for me came when I began to really look around at what all the ciswomen in the world were wearing and I needed to put away the stubborn attitude of what I thought I should look like. As I began to successfully blend in with the world at large, my confidence began to rise, and I could relax and feel more comfortable in my own skin. It was the beginning of a life-changing gender experience which I discovered I was along for during a very bumpy ride.

In many ways, the ride to being comfortable was like my favorite roller coaster ride at a big nearby amusement park. Often the ride up was slow and uncertain to the top but was made up by the rush of going down the gender hill. It did not take me long to appreciate the rush of coming down my own personal coaster. Even though I feared climbing the heights I was climbing (as well as the threat of falling) the risk was worth it as I began to carve out a small life as a trans woman. Which I always wondered if I could do at all.

I found I could do it thanks to the welcoming embrace of several ciswomen I was introduced to. It was scary yet powerful when I began to receive invitations to special girls ‘nights out. Once I figured out what I was going to wear, then I needed to figure out what I was going to add into the conversation with the other women who I had never met. I desperately did not want to act standoffish and worse yet bitchy by not joining in with the other women who I had a chance to make friends with. Looking back, I think I was successful because outside of one woman who kept glaring at me, I was treated well by everyone else. All this sudden attention led me to a newfound confidence in being in my own natural skin that I never had before in my old male life where I always needed to be on the outlook for someone trying to take away the life I had. I was always competing for what I had earned in a what you had done for me recently world.

The reverse was true in the transgender woman’s world I had found my way into. As I became more confident and successful in just being the me, I always wanted to be, the only competition I ever felt was when I needed to use the women’s room in a venue, I was not a regular in. And even that began to fade when I learned the proper etiquette to use in the typical women’s rest room. There was no thrill in doing just what came naturally, just the relief of being allowed in women only spaces to do it. Taking away any sort of a transphobe’s argument against me using the restroom of my choice.

In my case, becoming comfortable in my own skin was a constant problem which started with the way I was raised. My parents were long on material support and short on any emotional needs I may have had. Which led me to be alone with my gender dysphoria. It was a very lonely, confusing place to be and left deep scars on my internal confidence as I had no deep connection to what my true gender skin really was. The male world I was forced to live in, and the female world I wanted to be in. So, for me, the process of gaining any sense of who I really was a difficult and time-consuming process. Plus. My confidence was so fragile that the slightest problem could send me back to my cross-dressing drawing board to look for solutions.

Over the years, I flat out wore that old cross-dressing drawing board out until I began to figure out my problems were right in front of me. All I had to do was have the courage to do something about them. One of the problems was  they were so much deeper than just trying to look like a ciswoman. I was tired of thinking I was fooling anyone into thinking I was a ciswoman and settled into trying to build myself into the quality new feminine me I wanted to be as I had earned my womanhood from a difficult, unique path.

I seized the opportunity to finally be comfortable in my own skin.

 

 

 

 

 

 

Thursday, June 25, 2026

Luck or Destiny makes a Trans Girl Tick

Image from Maia I 
on UnSplash

Along with my regular blog postings, I am writing I book about my life through a company called “StoryWorth.”  My daughter purchased it for me, and it only goes to selected members of the family, so it is intensely personal and made to read in my opinion, after I have passed away. This week’s question was based on what I have done in my life, which was the most difficult to accomplish and what were the lessons learned and did they happen due to luck or destiny.

My answer was an easy one the two biggest accomplishments I had in life which surprised even me were when I was able to be accepted into the American Forces Radio and Television Service as a broadcaster during the Vietnam War. And the other was when I finally kicked my old male self to the curb and started to follow my dream of living my life as a transgender woman. For the longest time, neither seemed to have any chance at all in coming true, but the slimmest of hopes kept my dreams alive.

Along the way, I learned to not believe in luck during my life, however I became a firm believer in destiny. I need to make the point that destiny only found me because I made the effort to put myself out there in the world and try. I would never have made it to AFRTS without all the time and effort I took to write letters to my congressman, and I would have never made it to a transfeminine existence without leaving my closet and experimenting in the world. It was like I needed to scream destiny here I am, now find me. None of it was ever easy as I was swimming upstream against what society said I should or should not do. I should have quietly went about my way and let the Army recruiters have their way without question or had done the same when I rebelled against being in the restrictive gender box I was born into. I just couldn’t do it.

By far, the greatest act of rebellion happened when I went about seriously crossing the gender border. Presenting as a convincing ciswoman never was easy for me as I had very few natural characteristics. Like many of you, I have the prototypical male body with the thick torso and broad shoulders which I needed somehow to cover up if I was ever going to make it in the world as a trans woman. In fact, the shape of my body always threatened to derail all the work I was doing with my makeup, hair and clothes before I ever got started. I don’t think I ever would have made it without me finally taking the time to look at all the different shapes and sizes of the ciswomen that were around me. Like many of them, I would never be thin and attractive but just maybe with the right padding and wardrobe, I could be a presentable thick woman. By “padding” I meant I needed the right size of breast enhancements as well as hip padding until much later in life, I could add my own “padding” through the help of gender affirming hormones or HRT.

Then I started to realize that maybe I could do this and become a fully functional transgender woman, if I worked hard enough at it. That meant I needed to overcome the bumps and bruises I encountered along the way when I refused to stop at stop signs along my gender path. To do it, I needed to build up much deserved confidence in what I was attempting to do. Which was stop my life and start it all over again. It was as if I was packing for a trip and only had so much space to take things along. I had to decide what could stay (if anything) from my male past. Again, I needed to look around at the ciswomen I was close to and notice what their interests were. A major example was when I began to think I would have to lose my passion for sports, I began to notice many women with their favorite team jerseys watching games and drinking beer on the big screen televisions in the venues I was going to as a man. It didn’t take a genius to figure out if they could do it, so could I.

Destiny, in all its glory began to show me I wasn’t building anything new when I crossed to going behind the female gender curtain. I was just going to where I always should have been. I started to see that I could be accepted in lesbian circles as a sports loving femme (or lipstick) lesbian and I was relieved I did not have to institute some sort of a forced sexuality change I never wanted to do. Even though I kissed several men to see if there was any real attraction, there wasn’t so I happily moved on to where I was comfortable.

Believing in myself was certainly difficult to come by and took a lot of learning to do as I switched my life from a fairly successful man to a new transgender woman. Because at times, I thought I was in over my head until my confidence stepped back in and I started to move forwards towards my dream goal once again. I just had to remember how far that I had come from that scared, excited boy in a dress and make-up in the family mirror.

If I had it all to do all over again, I am sure I was given a bad deck of cards when it came to dealing with my gender and for the longest time, I played the victim card to delay the obvious. I was a male only because my genitals told the world I was. It took a while for me to mature into the trans woman I am today. But with the help of destiny, I put myself out into the world and made it. There was no luck to it.

 

 

 


Saturday, June 20, 2026

Memories or a Dream?

Image from Ian Dooley
on UnSplash

Too many times, when I went out into the world for the first time as a new transgender woman, I wondered if I was making a memory or living a dream.

Sadly, most of the time I was working so hard to succeed for the first time in a new exciting world, I did not have the time to know if I was making memories or working my way towards a lifetime dream. There was simply not enough time to do all I wanted to do, such as present well enough to blend in with the ciswomen around me. It was like I was driving a new car, and I did not know all the new features I was trying to master. How was I ever going to stop being a man with all the male looks such as a scowl and how I walked and turn myself into a pleasant looking feminine person as I camouflaged all the testosterone damages male puberty had caused me.

There turned out to be a way after I worked my way through not dressing like a teen girl which just drew negative attention to me. Certainly, creating more negative memories than positive ones and my dream of living as a full-time transfeminine person, remained just that. A far-off dream. At first, I had many memories to make and learn from as I followed my dark and lonely gender path. Perhaps my biggest problems came when I realized I was trying too hard when it came to expressing my own brand of feminization because I was working so hard to catch up with my own gender workbook and decide where I wanted to be.

The only dreams I was having during this time of my life were the rare occasions when I went to sleep and dreamed that I was the attractive woman I always wanted to be and the pressure was off to look a certain way as a woman which I had always lived with. I was obsessed with trying to try any beauty secret I could to improve my appearance in the world. This obsession very much was with me until I began to settle into my own beauty routine

 The dream took a giant step towards materializing when my daughter took me to her up-scale beauty/salon and spa to color and style my hair for the first time when it had grown long enough to do it. Even though I was scared beyond belief to do it, I knew this was a golden opportunity to go behind the gender curtain into a female dominated space I had never dreamed of going before. It was amazing as I wrote about several posts ago, and I knew right then why ciswomen were so adamant about having their hair done a certain way. I could not wait until I could scrape up the extra money so I could afford to go back. Plus, with my new hair, there was no way I could keep on presenting male in the world as I knew it.

I was so obsessed with putting myself out into the world, I needed to think of different ways to do it and build more memories such as when I started to meet the ciswomen and lesbians who would form my circle of friends and help me slip across the gender border and behind the gender curtain where I desperately dreamed of being.

At this point, I always mention the good and the bad that happened to me along the way to validating myself as a transgender woman. It took a lot of confidence I didn’t have to make it happen. Too many nights of rejection when I attempted to push the gender envelope too far and was sent home in tears with my new dreams shattered. When it did happen, I needed to rely on my deepest inner feminine self to assure me everything would be OK and these were just memories which happened to be unpleasant to add to my dream. She told me that the roughest dreams you ever had are the ones you had to work extra hard to achieve.

Sooner more than later, I began to have more pleasant memories than bad ones and my ultimate dream again began to come into focus. If I tried hard enough to accomplish all my feminine goals, I could join the others ahead of me in the transgender community I was familiar with and leave my male past behind me forever.

Surely, there is a big difference between memories and dreams. I consider memories a less than physical form of dreams. Meaning memories are easier to come by and dreams are something a human should always have to keep their lives headed in a more positive direction.

Depending upon where you are on your gender path, maybe you are just in the dream phase of where you want to be and that is fine. It is when you begin to build memories of your journey do you start to build the blocks you will need to make it through. During Pride month, no matter what you may read from haters, TERF’s and bigots, you should be proud of the gender dreams you have.

You are worth it and often there are more silent allies and developing transgender women and transgender men that you know who are ready to join society. Just look at your memories and dreams as what you had to go through to arrive where you are today. Someday you may be able to become that confident trans woman you only were when you were asleep.

When it comes right down to it, it does not matter if you are clinging to memories (past and present you are making) or the life you are dreaming of living, The most important thing is the self-love you are able to give yourself. Without it, you have a difficult time loving anyone else.

Thanks for reading along with me and thinking of your own memories and dreams. Any of your comments are always appreciated!

 


Thursday, June 4, 2026

When Nothing Else Mattered

 

Image from Klara Khokhlova
on UnSplash. 

Perhaps, similar to many of you, you have been described as selfish when you pursued your gender desires. I know, I was by my second wife as she told me many times my desire to be a pretty cross-dresser in my life was not all about me.

During this time of my life, sadly or not, all my spare thoughts and time dedicated to my cross-dressing activities, so yes, it was all about me. I did my best not to be that way, but I was failing miserably. Especially when I figured it out, I could leave the house as me and do a portion of the household chores such as grocery shopping. I figured by doing so, I was helping my wife and at the same time helping myself.

The more proficient I became at doing my new portion of some of the weekday household chores, the more I felt that nothing else mattered to me than my quest to explore my inner femininity. Increasingly, I broke the rules and made excuses to leave the house and explore the new, natural and exciting world I was experiencing.

As years always do, mine flew by in a blur as I became more proficient in perfecting my feminine appearance and it began to be more apparent to me that the life as I was living as a man would have to be sacrificed at some point if I wanted to pursue my dream goal of living as a transfeminine person. That is when I began to fall back on my ill-fated male habits of internalizing all my feminine feelings. Hoping that eventually, they would just go away. Compliments of my latest purge of my cross-dressing belongings.

Very soon, it became evident that all the purging in the world would not rid me of my deep-seated gender issues and nothing else began to matter, not even the massive fights my second wife and I were having when she caught me out of the house as myself. I would go to any extent possible to try to mend the wounds from my breaking the promises not to ever go out again unattended, all the way to promising I would go to a therapist in Columbus, Ohio who specialized in gender care to attempt to solve my “problem.” Even then, I would not listen to the therapist who told me that my gender issues were not a “problem”, and there was nothing she could do about them. I made the mistake again of thinking there was something radical I could do about how I was attempting to live my life. I could keep trying to sneak out of the house and try to learn more about my possibilities of living life as a transgender woman, while at the same time continue to live with my wife. She always know I was a cross-dresser but was completely dead set against me going any further towards being approved for gender affirming hormones (HRT) and living as my authentic self.

Perhaps the biggest problem was I was not sure what my authentic self really was. I knew I loved my second wife as much as the day I married her years before, but I really was not sure of how deep my transgender issues were going to run. Plus, all the research I was doing into a new life, jeopardized my old life which at times was not so bad because I was accumulating all the male privileges such as wife, family and job that I did not necessarily want to get rid of. The whole situation just mentally tore me up as I did not know what gender I was going to be from day to day. Was I going to try to be my true self or go out into the world again and “act” like the strong man I was not.

It all led me to feeling completely detached from the world and wanting to end it all because I felt so worthless to everybody. Fortunately, after I hit rock bottom, I got help from a good therapist and was prescribed medications which helped my on-going Bi-polar disorder and anxiety. It turned out my anxiety was triggered in many ways by my gender issues so that was easier to solve, but my depression was not so my new meds really helped. Giving credit to where credit is due, my help came through the Veterans Administration health care system and as luck would have it, I was teamed up with a therapist who knew what she was doing when it came to depression and LGBTQ care.

By this time, my second wife had tragically passed away from a major heart attack leaving me totally alone with my thoughts. Quickly, since nothing else mattered, I took the path of least resistance into my own form of womanhood. All those dues I was paying as a cross dresser working with my appearance came back to help me when I could hit the ground running in my heels (not really) and concentrate on rounding out my persona of the trans woman I wanted to me in the world of alpha cis women around me. I was able to see and learn from what they did to make their lives more fulfilling as women, and I wanted to do that too. I was having fun while at the same time was secretly learning everything I could from the ciswomen around me.

Most certainly, nothing else mattered when I sought out approval for my gender affirming hormones from a doctor I found in an LGBTQ newspaper. Along with the hormones, I was putting my new life together by legally changing all the gender documents I could with the VA and in the civilian world. Very soon, my old male life was in my past and my “dead” name faded away.

The only thing that did matter was building a new life with my third wife Liz, a lesbian ciswoman who accepted me for what I was. I could not let a second chance such as that pass me by.

 

 

Sunday, May 31, 2026

More Serious Stop Signs

 

Image from Steve Lieman
on UnSplash.

“Tia” wrote in yesterday and commented on my recent “Stop Sign” post. She wanted further insight into what my biggest stop signs were and how did I get through them.

First, thanks for the insightful comment, Tia and here are the answers as I remember them now.

By far, my biggest stop sign was put directly in my path by my second wife. As I was stuck between the rock and the hard place with her because of the transition I was slowly making from cross-dresser to transgender woman and my wife. Rightfully so, my wife pointed out I was breaking the marriage covenant we had and she did not want to be married to another woman. The last thing I want to do here is make her the bad person in all this gender turmoil because she knew and accepted my cross-dressing before we got married.

She even went as far as attending the social activities I went to in Cleveland and Columbus, Ohio and supported my efforts to leave the house to explore the world as a transfeminine person for the first time by backing me with money for motel rooms to get ready in. The only real stop sign I had was to agree to never leave the house dressed as me. Was it enough for me? No. I blew right through the stop signs and started to throw caution to the wind and go out into the world like the authentic me. Regardless of the heavily populated area of town, we lived in.

I kept on doing this until I was caught time and time again by my second wife and could not lie my way out of me breaking our agreement. I resorted to even going to therapy for help which never actually came. Mainly because I was not doing anything wrong in my struggle to just be the inner female I always thought I was. I even had a therapist I respected totally tell me that and I just ignored her. Thinking I could balance my gender issues and fight on to maintain the status quo. By ignoring the stop signs I was facing, I was just making my life worse and not helping our relationship in the long term which I will get back to later. Because, as it turned out, there would not be a long term relationship anyhow.

In the meantime, as I became more serious about the possibility of living out my life as a transgender woman, I began to see other stop signs ahead. They were major signs too such as how I would support myself in the world without my wife and perhaps the rest of my family. Obstacles which face nearly all transgender women and transgender men as we attempt to cross the gender border and live out our lives as normal everyday citizens. It is difficult to end one life, pick up the pieces and start over again. Something I wish all the transphobes who try to attack us would try to understand but that is a whole other topic.

Pure destiny helped me to negotiate the other major stop signs I faced with the attitude that if others could complete a male to female transition, why couldn’t I. Life became a circle for me as I went through the darkest period of my existence before I was able to pay my dues and take advantage of the new world I was in. The most tragic part was losing my wife to a major heart attack. I never ever thought she would ever die before me with the stressful lifestyle I was leading but I did, which led me to wonder what I would do about the biggest stop sign of all in my life. In the new darkness as I searched for my new path which had existed so long. All I needed to do was remove the stop sign and continue to live.

I also found I needed to do a quick look into who was important to me in my life and who I could afford to lose if I crossed the gender border. In my darkness I guessed my daughter who would support me and my only brother would not. Which was exactly what happened. It has been over a decade since I have talked with my brother, and my daughter has become one of my biggest supporters. My parents had long since passed on so I did not have to worry about coming out to either of them. Even though I did try to come out to my mom years ago and was rejected. I took that stop sign down and forgot about it.

It seemed, once I got used to taking down my gender stop signs the easier it got. Although that was not necessarily the case. Destiny stepped in again and provided me with an age excuse when it came to how I was going to support myself. I was fortunate to have worked a good job with a good wage which helped my Social Security retirement payments. I turned out if I was able to sell the collectables my wife and I had collected over the years, I could retire and support myself. Which saved me having to look for a job as a new transgender woman.

Of lesser importance was when the Veterans Administration started to provide care for gender conflicted veterans such as me. I jumped at the chance for lower cost HRT meds and the mental care to get them. The mental care provided me with a qualified therapist who helped me with the legal documents that assisted changing my legal gender markers within the VA and the public sector.

Perhaps removing the biggest stop sign of all that remained was discovering a loving relationship which I could cherish for the rest of my life. That person of course was my wife Liz who discovered me on an online dating site. I was always a social person and had resigned myself to a life of being alone before I met Liz and we are still going strong over fifteen years later.

I hope all of this answers the questions Tia and all of you may have had about my transgender stop signs and how I handled them. Some stopped me for years while others I simply rolled through or ignored altogether but one way or another I made it. As always, all of your comments are appreciated!

 

 

 

 

Friday, May 29, 2026

No Participation Awards for a Trans Woman

Image from Brett Jordan 
on UnSplash.



As I traveled up my very long gender path with all its stop signs, I realized there were no awards for just participating coming my way. In fact, just the opposite was true.

Every time I was able to cross dress in front of the family mirror and not get caught, I experienced major gender euphoria but no awards because I knew I would just have to go back to my boring male life which I wanted no part of. Since my feminine self was deeply hidden from the world, there were no awards when I mastered a certain make up look or did not run my panty hose. On the other hand, I could expect some sort of gratitude when I achieved good results as a boy. I hated the total imbalance of the system I needed to live under with no available choices coming my way soon.

It wasn’t until much later in life did, I began to experience any participation awards at all. In the very beginning after trips to the big malls I was going to, even on the nights I was laughed at and scorned for my appearance, I felt at least I had tried and needed to go back to my cross-dressing drawing board to come up with ideas about what I was doing wrong. After setting aside my stubborn ideas of trying to dress sexy like a teenaged girl, and dressing age appropriate I was able to blend in with the ciswomen around me and not cause any undue attention to myself. I gave myself a bigger reward when I reached that major milestone in my life back then as a part-time cross-dresser.

Then, I became frustrated because it seemed the awards began to become harder and harder to come by as I started to overachieve as a transfeminine person seeing the world for the first time. Those were the days of trying to overcome a portion of my guilt for sneaking out of the house dressed as me by trying to do things which helped the household such as grocery shopping or better yet, trying to find my wife a garden gift at one of the nearby antique malls I went to. She was a huge gardener, and I thought an occasional gift would please her but probably pleased me more because it helped soothe my guilty conscience and gave me an imaginary award to put up on my mantle. I wish I could say I had a lot of awards, but they were very difficult to come by. Plus, my collection would be destroyed every time my wife caught me out of the house, and I became discouraged and decided to purge all my feminine belongings only to have to start all over again. Until I realized purging was fruitless and my desire to be a woman ran too deeply than just having the clothes, shoes and wigs that I had collected.

Overtime, with all the purges I attempted, I became better at keeping key items of my wardrobe I would need if (ha-ha) the urge to be a trans woman hit me again. I was not the sharpest tack in the box and still had not realized being trans was apart of me and would never just go away.

In the meantime, I continued to go out at night in the world and collect my participation awards as I learned what it really meant to be myself. To do so I needed to leave the gay bars behind that I was frequenting where they only thought I was a drag queen and try out the real world for a change where at the least I could be accepted as a woman from a different past. To do so, I needed to hitch up my big girl panties and do a deep, scary dive into the world I wanted so desperately to be in. I was growing increasingly tired of living a lie as a man and wanted out. In the beginning, I still took what I thought was the easy way out. By going to venues, I frequented often as a man and had wondered how it would be to live it as a transgender woman. It also helped that I was able to see how single women were treated in the straight places I was considering going. The last thing I wanted to do was to feel unwanted or afraid being a single woman in a venue full of couples.

After much thought and caution, I tossed my misgivings aside and considered what was the worst that could happen. My frail ego would be destroyed, and all my participation awards would be destroyed was my first thought. Then, I relied on all my new-found confidence as a transgender woman to succeed at my first big moves in straight venues in the world around me. To my amazement, I was treated well in my new world, and no one laughed at me or treated me with disrespect as I left my unwanted male privileges behind to learn what all the female privileges were all about.

I learned immediately one of the benefits was just being treated nicer. Even to the point where I was invited to staff girls’ nights out when the bartenders were concerned, I was lonely. Which I was. Better yet, one bartender set me up with her single lesbian mom whom I remain friends with to this day. Ten years later. There would have been no way that I could have made friends as easy as I did as a woman than I ever did as a man. A major reward for all the years of work I had put into succeeding on my gender path to my dream.

Another major reward I have received over the years comes from all your comments and feedback to my experiences. Originally, the idea was to write a blog (before I even knew what was one) to help others with similar gender differences so they could learn from them. Thanks to you, the idea has grown way past my expectations.

Thank you!

 

 

  

Thursday, May 28, 2026

She Was Living Rent Free in my Head

 

Image from Nathan Dumlao
on UnSplash.


It took me years to realize that I had a tenant living rent free in my head all along.

I should have known from day one when I was going through my mom’s clothing that she was here to stay. In fact, she increasingly demanded more and more space in my head to justify her life as a cross-dresser or transvestite as we were called back then. I would need to wait several years for the transgender term to even become popular in our gender diverse society.

Also very early, I realized that the small closet I gave her to exist in just was not going to be enough. When she succeeded in expressing herself in the world in the smallest of occasions, she wanted to increase her space in my head. Prime examples were the days in school during study halls when I should have been actually studying. But I wasn’t as if I was having too much fun envying the girls around me who I desperately wanted to be like the next time I had the rare chance to be by myself and cross-dressed as a pretty girl in the mirror. And I realized I did not want them sexually as much as I wanted to be them physically and mentally.

It was during that portion of my life that I completely did not have any idea of how much rent-free space my evolving trans woman needed for her share of my head. Now I want back all the time my male self-spent fighting her for my life as I lived it. The gender ripping and tearing was certainly no fun, as both genders in my head fought for their right to survive. For awhile I tried the old male fallback of just try to ignore my number one problem in my life and she would somehow just disappear. When, in fact, the opposite was happening. The thrill of putting on a dress, hose and makeup would go away, and in its place, I would have a deep-seated feeling of just doing what was coming to be just natural for me. It was increasingly evident that I would need more space for my rent-free tenant to operate in as she went out to explore the world as a novice transfeminine person.

Following more than a few rough patches when she was going out in the world, my woman began to understand the sacrifice of her male ways it would take to survive. She became more serious and began to work on the basics such as presenting herself convincingly in the world. I went on a crash diet and succeeded in taking off enough weight so I could go down a size or two in the world of women’s fashion and I could find and wear stylish clothes for a change. Along with that major move, I began to take extra better care of my skin. Using a good moisturizer following every shave. Which paid off by not having to use so much foundation makeup and I could look so much more natural as if I was not trying so hard to look like an attractive woman. The trips I started to make to the department store makeup counters for guidance certainly did not hurt my progress either.

I was learning the hard way that I could not cut any corners if I was to be successful in my quest to present successfully in a world of curious ciswomen. I needed to give my rent-free tenant the opportunity to expand her space in my head and the finances to do it. I would be spotted a mile away as a man trying to be a woman if I used cheap makeup and did not do my best to shop for (and try on) clothes that fit me and even flatter my testosterone poisoned figure that I could do very little about. I did learn from my observations of the ciswomen around me that there were women of every shape and size that I could copy from and be successful. Which gave me the positive energy to carry on and pass as a trans woman friend of mine said, “Out of sheer will power.”

Even though the progress of my rent-free tenant was not moving along as fast as she wanted, there were still major obstacles in my way to deal with. Such as what would happen to my twenty-five-year marriage, my relationship with my daughter and the problem of finding a new job as a trans woman in the world. To be sure, all were major obstacles to deal with, so my tenant would have to be patient as she was beginning to understand she was the only tenant left in my head with any power. My male self was just going through the motions of life to keep a job and the outwardly show of male privilege in my life.

Finally, it was time to go on gender affirming hormones and allow my tenants to switch places. My previous rent-free tenant had earned her right to live as the dominant person in my life and my male self was left to pick up the pieces. I should say baggage more than pieces, because that is what he left me to consider in my new feminine life as a fulltime transgender woman. It was difficult to do, but I was able to keep several of my main male building blocks of my life such as my will to succeed and a deep-seated desire to bring my hobbies with me such as my love of sports. Which I learned was alright when I made ciswomen friends with the same passion for sports that I had built up over the years of my life.

While I certainly would not recommend a life like mine to anyone. Letting someone live rent free in your head for all those years was never easy. Perhaps, the only positive was, having all that time to learn the world as a trans woman gave me a stable basis to work from. That is my excuse, and I am sticking to it.

 

 

Dealing with Gatekeepers

  Image from Ries Bosch on UnSplash.  Unfortunately, all the people who see it as their job to be a gender gatekeeper can run the spectrum ...