Showing posts with label lesbian. Show all posts
Showing posts with label lesbian. Show all posts

Saturday, August 22, 2026

Keeping My Mouth Shut

 

Image from P.A.U.L.A.
on UnSplash.



As I wrote before, yesterday was one of those busy days when everything seemed to come together to get things done.

The day began innocently enough when I went with my wife Liz to two of her doctor’s appointments. I have long since stopped being anxious about going to a medical waiting room because everyone is so wrapped up in their own problems or their cell phones to notice a stray transgender woman just going about her business.

For the day, I decided to get brave and poke the bear so to speak by wearing a T -shirt I received when I was a board member of the Dayton, Ohio Rainbow Elder Care Alliance a few years ago. The shirt proudly displays a pride symbol on the front and has a “Support LGBTQ Elders” on the back, so I was prepared if I triggered any negative feedback from a stray gender bigot or TERF. Ironically, it did not matter because the waiting room was empty the entire time I was waiting for Liz to get done. In some senses, I was disappointed that I did not get a chance to show off my shirt to anyone, so I took it off when I returned home and saved it for today’s birthday lunch for my daughter and son-in-law who are coming down from Dayton for her party.

We are celebrating a little early because she is leaving for Maine to climb a mountain there on her actual birthday. She is the mother of a transgender child so I thought my LGBTQ shirt would be appropriate.

The real fun started yesterday when I went to my Veterans Administration weekly virtual LGBTQ support group meeting. That is where I could not keep my mouth shut and brought politics into the group as a new member made a snide comment when I mentioned I was getting access to a brand-new VA satellite clinic made possible under the Biden Administration. Everyone else cringed as I simply said Biden was a real improvement over the Russian asset, we have now. I was ready when the new person who identifies as a trans woman then said she never votes anyhow and I was going to say then you are part of the transgender community’s political problems. But I saw the look of panic on the moderator’s face, so I stopped. Because I care about not breaking the group’s rules and getting asked to leave.

My mouth is one thing I inherited from my mother and passed on to my daughter who is a strong ally of the transgender community. Her reaction when I came out to her was anger because why she was the last to know and kept in the dark by her mom and stepmom. She calmed down when I told her that mom and stepmom only knew me as a cross dresser and fought all the way any idea, I was a transfeminine person. One way or another, it was a great relief to get the coming out process to her out of the way and even a bigger relief to know she completely accepted me. In fact, for my birthday that year she treated me to a visit to her beauty parlor/spa for a color and cut on my hair which suddenly was getting long enough to style professionally. I don’t know if I was more scared or excited the first time I went, but I made it and loved my hair. I knew them why so many ciswomen consider a regular visit to the salon a must in life. After I was done, I thought I could probably miss a day of my Estradiol pills because of all the Estrogen in the air in the salon. I loved it.

My main problem when I first began to communicate with women on a regular was keeping my mouth shut too much. So much so that I thought I might be coming off as unfriendly or worse yet as some sort of a bitch when in fact, I was just too shy to speak. I had not practiced my feminine voice enough to have any confidence on how I sounded when I needed to switch from my old unwanted male voice into a new vocal pattern which fit the new feminine me. I even went as far as having feminine vocal lessons which taught me how to speak in a more pleasant manner and get my point across, often in a passive aggressive manner. I certainly did not achieve miraculous results from my vocal work but did enough to express the true me.

In many ways, keeping my mouth shut became impossible when ciswomen in particular began to ask for my opinion about men as they recognized the unique position, I held living on both sides of the gender border. As inherently shy as I was, it was a good way to practice my new vocal pattern to fit how I appeared to the public.

These days it is particularly difficult for me to keep my mouth shut when it comes to politicians taking away our rights as transgender women and transgender men. In my native Ohio, the state Bureau of Motor Vehicles announced they would no longer give trans people new driver’s licenses under their preferred gender and only issue one with a corrected birth certificate which is extremely difficult to do here in Ohio. I did not find any information on what they might do about renewals as my license is good for another year and a half. Here in Ohio also, having a current picture identification allows us to vote unless it is changed too by the Crook in Washington.

On a sad note, I just learned yesterday that I had lost two transgender woman acquaintances to death. One was an icon here in Cincinnati who I believed passed from Parkinsons and the other was down in Tennessee and died from unknown circumstances. Hopefully, they are both resting in peace now.

Back to a brighter side, it is time to get ready to meet daughter and son-in-law for a Mexican lunch at our favorite restaurant.

 

 

 

 

 

 

 

Friday, August 21, 2026

A Busy Day

 

JJ Hart

Today will be a busy one for myself and my wife Liz as I am going with her to two doctors’ appointments. So, I will have no time to write.

Going with her on her visits is normally not a big deal because everyone else is normally wrapped up in their own worlds or on their phones. Not enough to notice a stray transgender woman in the waiting room. Also, going dressed casual is no problem because I blend in with all the other ciswomen.

Today, I am getting radical and wearing one of my pro-LGBTQ elder care lavender T-shirts, which if anyone decides to read close enough, they will surely identify me as a trans woman. I don’t care because if I encounter a gender hater, it is their problem not mine. I relish it because of all the years it took me to have the confidence I do these days when I encounter the public.   

In addition to the new T-shirt I am wearing, I am just going to wear a pair of blue leggings along with my new tennis shoes for a comfortable walk. I am putting off a close shave until I am done with this post because I also have my Veteran’s Administration virtual LGBTQ support group meeting later this afternoon and I want to look my best for it too. These days, it almost takes me as long to brush out my long hair as it does for me to shave and apply a light coat of makeup and lip gloss.

I doubt if anything very exciting will happen, but if it does, I will write about it.

 

Thursday, August 20, 2026

Burning my Gender Bridges

 

Image from Issiac Viglione
on UnSplash. 

The first time I tried a dress on and put on mom’s makeup, I burned a couple of my gender bridges. Because deep down inside I knew I could never go back.

After a few missteps, I became quite used to it. Even though what I was doing by cross-dressing and building new bridges was quite risky to the only life as a boy I had known, I kept on burning the old bridges and building new ones. Fortunately, the new bridges I was building were the product of better construction than I had ever known before, I still had such a long way to go.

Early on, the problems I faced were simply formed by the lack of experiences I had being a feminine person at all. My gender workbook had never been filled out because I had never been allowed to hang out with the girls and have the chance to understand their lives. There were no girl’s sleepovers for me to go to get peer input into how I was dressing or ideas on how I should apply my makeup. It seemed as if I was stuck forever in my male world and I could not get out.

Another problem I had was I built too many invisible bridges that I did not need to. I was and am a worrier and I routinely build structures just to jump off of them it seemed. That has continued to be a lifetime problem of mine as we can take yesterday’s routine trip to the drugstore as an example. The store is very close to my house but yet I needed to worry about getting there and back in one piece, as well as what I was going to wear and not forget all the items I needed. Of course, I just dressed casually for the trip and it came off without a problem as I got everything, I needed including birthday cards for my daughter’s upcoming dinner my wife Liz and I are hosting her for before she heads off to Maine to climb a mountain to celebrate her 50th birthday. Already, I am stressed about what I am going to wear to the restaurant.

As I matured into a more complete transgender woman, of course I discovered more things to build bridges on or around my life. For the longest time, I refused to face the truth in my life that I was always meant to live in my femininity and leave my male life behind. It was then I started to run, move often and change jobs so I could better support my two women. My second wife and myself. All my building was doing was destroying my already fragile mental self as I desperately looked for answers which were there all along. Anyway I tried to cut it, I should never have been forced into a male box when I was born and had no power to do anything about it.  

It wasn’t until I got out of my gender closet and became familiar with the world as a trans woman, did I really have to begin to burn my old male bridges to the ground. Specifically, when I got out of the gay venues, I sought out some sort of safety and solace in and started testing myself in the real world did I discover how many bridges I had destroyed and how many more would have to go. If I was ever going to have the opportunity to live my dream. I was running as fast as I could in my high heels away from my old male privileges I took for granted until I torched them. Such as sacrificing part of my intelligence and all of my personal safety when I was allowed behind the gender curtain and out of the boy’s club.

The bridge which surprised me the most was when I needed to communicate with the world of ciswomen who let me in and wanted to know more about me. It was a shock to my system to have to actually carry on a conversation or better yet begin one because I did not want to come off as being unfriendly with another person, mainly women. The overwhelmingly group of men as a whole left me alone since they had the sense, I was a traitor to their club. It turned out that if I did not want to burn the bridges between men and myself, they did it for me and they were replaced by the ciswomen I felt more comfortable around anyhow.

When I worked on my male to female transition, the bridges I was building had to be so much stronger than they had ever been before. Mainly because I was risking life as I knew it to do it. Over the years, I had accumulated so much male baggage I needed to figure out what to keep and what had to go so my bridge would carry the load. My baggage included the usual suspects such as spouses, family and friends as well as employment. Again, I was fortunate when I discovered other women with the same interests as me such as watching sporting events.

Lately, I have been receiving comments from readers who are just beginning their gender journeys and the only advice I can give from the other side is to build your bridges well to withstand the changes you will go through. And don’t forget there are many ways to achieve your goal. You can go the surgical route to transform yourself into the person you always knew you should be and go the hormonal route like I did when I was able to thrive with the help of a few ciswomen who showed me my way to build my own bridge into a feminine world. The end result should be whatever feels good and natural to you, you should go with. The one life you have to live should be yours, even if your path to doing it may be a little more different and difficult than everyone else’s. Don’t be like me and take years running from your truth before you face it and win and are able to proudly walk across your bridge.

 

 

Tuesday, August 18, 2026

Try then Try Again

 

Early Days in my Gender Closet
JJ Hart.


When I first broke out of my gender closet and into the world, there were many cases of failure I needed to deal with.

For example, all the evenings in malls when I was singled out for abuse by groups of teenaged girls. So much so that I tried my best to head to the other side of the mall as quickly as I could in my new high heels before the girls noticed me and started laughing.  When that happened, many times I was sent home in tears wondering what I had done wrong with my presentation. One thing was for sure, I needed to go back to my cross-dressing drawing board and try, try again.

It took me a while to realize I was backwards in my public presentation thinking. I was dressing myself how a man would rather than how a ciswoman would if I stood any chance of blending in and making it in a world I only had just dreamed of. Plus, I benefitted from a crash diet I put myself on which helped me to fit into more stylish feminine clothes. It was the first time in my life that I had been so serious about anything that I could remember.

One big thing I did not realize was the total scope of the male to female femininization project I was taking on. The deeper I delved into the feminine culture I was in, the more I found I had to try to do to become successful and there were many times when I simply not a success. One time that sticks out in my mind was when I visited my gender therapist unannounced as my authentic self and sent her into obvious shock looking around to find out where her son was. I would have thought, since she advertised herself as a gender therapist, she would have been more comfortable around a person cross-dressed as themselves. But she was not. I took it as I had to keep on working on my feminine presentation to hide all the testosterone poisoning male puberty had wrecked my body with.

The more I was able to find myself behind the gender curtain as a transgender woman, the more I needed to try, try again to never stop learning more about how ciswomen spend their lives operating in the world. The circles they run in and their overall dealings with each other as well as men come to mind as I think back on my initial experiences. It was a scary yet exciting time in my life as much of the time I was still risking destroying life as I knew it, if the world discovered my deep dark secret. I had not yet concluded my secret really was that I was a woman hiding behind a man. Not the way I was living thinking I was a man trying to be a woman.

Most of the time, the world did ignore me as my presentation improved well enough to get me by but on the occasions I met the rare TERF (radical feminist) gatekeeper who did not want me behind the gender curtain, I was sent away to try, try again until I earned my way into the places I wanted to go mainly such as women’s restrooms because on my long days out I simply needed to go to the bathroom and not make it such a big deal. It took me a lot of resilience and knowledge of the feminine world to do it but I finally earned my way into the “room” also.

I have always thought that building my fragile confidence into a strong one was one of the best moves I ever made so I could relax in the world and stop trying so hard to be myself. I say fragile because there were so many times over the years when I thought I had achieved confidence only to have it shattered by an unfeeling gender bigot. By trying again and again to overcome the haters, I made it to a point where I could say to heck with them and I was going to live my own life the way I saw fit.  

When I had reached a point where I thought I had enough confidence to get me by was when something unexpected happened to challenge my path. All along, I had some sort of an idea of how complex a ciswomen’s life was than a man’s life, but until I got there as a trans woman, I did not have a real idea of how complex. It was as if every time I thought I could see a clear road ahead on my gender path, someone would throw a stop sign in my way. Making me stop what I was doing and look around. Did I really want to take all these difficult steps I was taking to be a transfeminine person after all.

Of course, once I stopped, looked around and thought about it, I discovered I was in the world which I had always belonged to and I wanted to stay in the worst way. The more I was allowed to play in the girls’ sandbox, the more natural I felt as I felt my life make a seismic shift towards becoming the person I had always meant to be. To keep trying, I needed to decide to risk losing all my remaining close friends, family and employment and embark on the road without any more stop signs.

I was not getting any younger and at the age of sixty my transgender biological clock was running out. It was time to try to see if I was still healthy enough to be approved by a doctor for gender affirming hormones or HRT and I was. Which was actually the last big gender hurdle I had to try because I had already done the social part and I did not desire any extensive facial or genital realignment surgeries. So, I could then try to discover if I could find anyone to share my unique life with.

By trying to put myself out there on dating sites and in the regular straight venues I was going to, that paid off for me too when a ciswoman lesbian from nearby Cincinnati responded to one of my on-line dating requests and we are still together fourteen years later.

All those early years of trying and failing came back to help me years later when I needed it most and my life went full circle.

Thanks for reading along and passing along all your comments and reactions! I really appreciate hearing from you.

 

 

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.

 

 

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.

 

 

 

Wednesday, August 5, 2026

The Vampires Approved Me

 

Image from Mike Lloyd 
on Unsplash. 

Yesterday I needed to visit the Veterans Administration vampires to have my blood labs done. Fortunately, I could just go to my local branch office to get them done and not have to go to the congested mess which is the downtown Cincinnati VA Hospital.

I chose yesterday to go because it was a beautiful early August day here in Ohio with coolish temperatures and bright sunshine for the relatively short drive I needed to make to get there. For the occasion, I decided to wear my new Libra themed tank top with leggings and my new tennis shoes. After a close shave, a lite coating of makeup, and lipstick, I brushed out my long hair and was ready to go. Actually, compared to the few other ciswomen I encounter at the VA, I was nicely dressed and ready to face the world as a transgender woman.

When I arrived at the VA, it was a very uneventful visit as no one seemed to notice me for anything other than who I was, an elderly woman who did not have to wait long to be seen and have my blood drawn. Since I was emboldened by the experience, I decided to stop by my wife’s Liz and I’s favorite coffee shop to pick up some breakfast sandwiches and coffee. My morning continued to go good as their drive-through was nearly empty and I was greeted cheerfully. Before I knew it, I had my order and was headed home. It is the coffee shop we go to which has the big LGBTQ flag on the wall, so we always try to support it.

The best part was that only a couple of hours later, the doctor who wanted the bloodwork done received the results and everything came back OK. Which means I am clear with the vampires until I have my Hematologist visit downtown this fall. It is important mainly because it is when I have my Estradiol levels checked. It is certainly no fun going downtown and having to find a parking place and walking but there is nothing I can do about it.

In the meantime, I took my brief moment of gender euphoria and enjoyed it for what it was…a brief moment to be the person I always wanted to be. I was just being me basically for the first time in my life. Now all I need to do is string together more of these moments to make them my reality.

Just a short post today to let you know where I have been and I will be back with you with a longer post tomorrow.

Monday, August 3, 2026

Letting Tomorrow take care Of Itself as a Transgender Woman

 

Image from Valentina Conde
on UnSplash.

Since I was always a person who had a difficult time living in the present, tomorrow always loomed large in my mind.

I think it all started when I began to rebel against the masculine world I was being forced to live in and always thought tomorrow could be better. It turned out that all the wishing and hoping I did for a better tomorrow turned out to be wasted time and energy, I finally needed to take matters into my own hands, stay in the present and do something about me being stuck in my dark, restrictive, gender closet with only a mirror to help me.

It took a quantum shift of thinking on my part to even thinking about how I could change my life. First of all, it was nearly impossible for me to quit daydreaming about the next time I could cross-dress in my mom’s clothes and try on her makeup. Any time I was not actively being engaged in male activities, I was hoping that soon I would be glimpsing a view of me in a favorite miniskirt I had found by accident at school outside of the girl’s locker room. If the girl who left it behind did not want it, I certainly did before a janitor found it and threw it in the trash. I was overjoyed to add it to my small but growing feminine wardrobe at home. Hopefully away from any prying eyes who may find it.

Somehow, I managed to hide my “treasures” away and add to them with my own meager funds I had earned from my rural newspaper route and from chores I was doing around the house. I will never forget the excitement I felt when I found a pair of women’s shoes that fit me in the department store where I was sneaking in to buy my makeup and panty hose. The whole process made me feel good because for once I was not relying on anyone else to help my cross-dressing along. It all was just me, and I was in the present doing it.

As I moved along in years and experience, I increasingly wanted to break out of my dark closet to see if I could exist in the world, in the present for once as the person I was coming to believe could be my true self. I learned the hard way that the public would not be as forgiving as much as my mirror was as I was treated quite rudely the first several times I went out. Even in places I should have had no problems in such as the big shopping malls back when they were popular. I couldn’t seem to dodge the giggles and stares I got from the teen girls before I learned to stay in the present, be who I was and begin to blend in with the group of other ciswomen in the mall. I learned the hard way to dress for them and not rely on some sort of trashy look that appealed to men. Which was getting me clocked as a man in drag every time.

All this new reality was teaching me I could indeed enjoy the present when I was out in the world. But not enough to keep me there when I was back in my unwanted male world. I have always wished I could get back just a portion of the time I wasted daydreaming of how it would be if I was the only ciswoman in a business meeting I was in. I know I could have been more effective…if I could have been accepted. Which I would not discover how difficult that would be until I got out further in the world as a transgender woman. I will always remember how I was shunned by a small group of men I somehow became involved in a discussion with when I first came out of my shell. Quickly I discovered, as a woman among cismen, I would have to fight for my right to be heard on an equal basis.

The more I was out in the world, the more I was forced to stay in the present. If I did not, I could find myself slipping back into old male habits which would give my past away much sooner. Such as not employing my old “stay away” male scowl and replacing it with a much more pleasant feminine look which said I was happy to be here. Which got me by. Other areas of just being a woman I needed to concentrate on was how I moved around in the world when I was still trying to juggle being in both worlds of male and female. One day I needed to be feminine, and the next masculine ended up taking a real toll on my mental health as I did not know somedays what present I was supposed to be in.

Plus, the one aspect of being in the now as a transgender woman was the one I always mention, communication. As I was blissfully (sometimes) going along my gender path, suddenly more and more ciswomen wanted to know about me and were curious why I would be in their world. I was totally blindsided when I needed to start and participate in entire conversations with other women who appeared in my world. I discovered communication went way past just how my voice sounded into exactly what I was saying and how fast I could pick up two uniquely feminine communication aspects. Non-verbal communication and passive aggressive behavior. The normal ciswomen who interacted with me ended up using all their skills to size me up and often it turned into quite the contest that I needed to stay on my toes to get through.

Eventually, surviving all the gender wars I went through, made me a better, more well-rounded trans woman who could hold her own in the world. Primarily because I had built up the confidence to do it, and it became my number one accessory. So, what if my makeup or walk wasn’t exactly correct, I knew who I was and it showed. There was no blood in my water for the human sharks around me to come after.

All those years of trying to get into my present and stay there finally paid off for me, but only after I had paid all my dues.

 

 

 

 

 

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.

 

 

 

 

 

 

Monday, July 13, 2026

Gender Binges

 

Image from Andy Arjun
on UnSplash.  

Binge cross-dressing happened a lot to me when I was quite young.

Once I was able to scrape together my meager finances to put together a small wardrobe of feminine clothes that barely fit me, I could not stay away from wearing them more and more. In fact, I was able to come up with two main hiding places away from the prying eyes of my family and most importantly, my slightly younger brother. It was about that time that I really became involved with binging in my new clothes which I felt made me look like a pretty girl.

Very soon, regardless of the risk involved with me cross-dressing as a girl, I was doing it as much as I could get away with. I think now that my mom had to know something about my cross-dressing but was either afraid to say anything about such a complex subject or thought it was a phase that would go away. Obviously, the joke was on her. My wanting to be a woman never did go away; I just matured into it. Plus, back in the late 1950’s and early 1960's, there was very little good information about gender issues to deal with, so we were on our own as gender issues were called mental illnesses. Which even I knew at such a young age was not true. For all I knew at the time, I really liked experimenting with mom’s clothes and makeup and binge dressing was becoming routine.

As I said, once I began to mature into being a more accomplished cross-dresser (even before I considered myself transgender) I managed to dress more and more. I was even able to buy a beautiful long blond human hair wig that she hated and I loved. Finally, after I changed girlfriends, she went away and I kept the most important part of the relationship to me which of course was the wig. It brought me to a whole other level of cross-dressing away from Halloween wigs into the real deal. Back in the 1960’s when miniskirts were in, I could not wait until I could find a chance to slide on pantyhose and miniskirt and top it all off with my blond wig. Yes, I did binge any chance that I got!

Sadly, my binge dressing needed to come to a complete halt during my military years in the Army. Instead of worrying about how short I could wear my miniskirts, I had a more immediate and important problem of how to deal with weapons and drill sergeants in Army basic training. How I survived was that I put all my fond memories of cross-dressing in the back of my head and daydreamed about the future I knew I could have shaving my legs again and binge dressing as a woman.

After I served my time in the military, the only immediate release I had from all the tension I felt to be feminine at all was with all the many and varied Halloween parties I went to. During that time, I went from being a French woman with my blond hair, black outfit, tights and beret, all the way to professional woman one year when I was mistaken for a ciswoman just getting off work. The good news was I was learning a lot, and the bad news was Halloween only came about once a year. I needed desperately to find another way to binge with a purpose and express myself as a transgender woman. A term I was beginning to accept as my own.

Once I began to accept who I was, I needed to set out to prove it to myself and the world that I could live my truth. It was then that my binging took a whole different direction from where I was before. Thanks to the basic acceptance I gained from successful Halloween parties, I had the confidence to know I could look the part and blend in with society as another ciswoman. Little did I know then, the hardest part of my male to female femininization project was yet to come.

It took me finally getting out of the gay bars I regularly went to for some sort of validation I never received and into being accepted as a regular in many of the straight venues I went to and enjoyed as a man. My validation as a regular gave me the confidence to keep trying to improve myself as a transgender woman rounding out her life in the world. As I achieved goal after goal I set up on my trans bucket list, I really binged out every chance that I got which put me into a direct collision with my second wife who did not want to live with another woman and my male self who was dead against giving up his life all together.

By all out gender binging, I had set myself up for an internal war I was fortunate to survive. It took me all I could do to keep all my lives together as the years progressed. All I knew was I was able to carve out a dream existence as a transfeminine person. No one knew of my male past, and I loved experiencing every moment of my new life. Deep down, for once I felt I was fighting my self when I was binging as a trans woman and expressing my true self.

By turning back, the clock the best I could, I tried to take the best that I learned from my male life and apply it to building a solid base for my female life. I think it worked because I was able to decide which of my male baggage was important enough to bring along and I benefitted from being blessed with a long life, so I can see a number of important things come full circle (which is another blog post.)

The bottom line is I have always been an impulsive person which helped me all the times I just had to binge to satisfy my needs. Dealing with my gender issues was just an integral part of that.

 

 

 

 

 

 

Sunday, July 12, 2026

A Want...or a Need

JJ Hart Discovering her Needs
I am in the first row on the left.

When a want turns into a need, sometimes you can feel it. Other times, not so much as if it sneaks up on you from behind.

As I began to wear dresses and makeup as a young boy, for the most part, it was because I wanted to do it. Cross-dressing just relieved the pressure of my unwanted everyday male world. It did not take me long to figure out my want was much more than just a casual appreciation of women’s fashion and makeup.  I did not know it then (and the term had not yet been widely used) that I was transgender more than a cross-dresser. I could not feel the change because I did not have the gender knowledge to do it.

Life began to change for me when I started to cross-dress for the thrill of it and attend Halloween parties. The parties ended up teaching me the basics of being a woman in public around people I knew, and I wanted to take it a step further by not having to wait another year to try again to get out of my dark closet and into the world. That is when my story turned out to be dark as I was not met with many positives by the public as a novice trans woman, cross-dresser or whatever you would like to label me as. To too many people, I was simply a man in a dress and clown makeup. I learned the hard way to get back to my drawing board and work harder on my feminine craft to find out if I was ever going to be able to succeed at all at my dream.

I also learned that if I was ever going to find success on my gender path, I was never just going to make it by just thinking it was just a want. It had to become a deep-seated need. I went back and dieted, worked on my skin and did everything I could to improve my testosterone poisoned body. All it really taught me was how much deeper I needed to travel along my gender path to make it at all and I needed to do it very badly. As the pounds melted off, I was able to find more stylish feminine wardrobe items to fill out my fashion needs and dress for success to blend in with the rest of the ciswoman crowd. Who I learned the hard way, were the people who ran the world I was attempting to be a part of. Or I could go casual if I needed to and a more polished business look when I needed to upscale my appearance. Fashion-wise I was learning that looking the best I could and blending in with the public at the same time was a definite need not some sort of a frivolous want just to justify something I wanted.

The more I tested the world as a transfeminine person, the more I needed to do to help myself along in the learning process of just belonging in the world I always should have been a part of to begin with. It was a real chore just to put the mirror image I thought I had perfected into the public and into motion to see how it worked. For the most part, I was improving to the point where I needed to start trying to communicate with the world as a more complete trans woman. As I always point out, the communication challenge to me was immense because I had always been a lazy communicator in my life. By that I mean, I had never really had to listen closely to what another man was telling me. I knew instinctively how to respond to another man but was clueless when it came to woman to woman talk. Which I always had known was different but how different I did not know until I was made aware of it. For example, for the first time ever in my life I needed to really stop and listen to whomever was talking to me. Were they trying to point out danger to me or just being friendly as a ciswoman who was curious of me or a toxic man who just viewed me as some sort of a fetish object.

Quite possibly, the communication aspect of my male to female femininization need passed my desire to be as attractive as I could as a transgender woman in the world. Instead of just wishing and wanting to be accepted as an equal by the other ciswomen I met, I needed to make it a priority. I even swallowed my pride and took female vocal lessons to make the process easier. It was difficult, but I think I gained enough confidence to help with my overall presentation and life.

I was helped too when the pressure to succeed was relieved here and there by the new success I was having in the world carving out a new life which on one hand to be terrifying and on the other feeling so natural like I was coming home to the self I always should have been.

I found I did not discover all my true self until I could step away from me for a minute to look at how far my gender path had taken me. After years of experimenting and trying different things, I finally achieved my need to be allowed to play in the girls’ sandbox and I was not disappointed with what I found there. Even though I had to put up with the occasional hater or TERF who wanted me out, but the majority of women made me feel welcome in their world and that was all that mattered to me.

The sandbox provided me with firm lessons and reassurance in what I was trying to accomplish in life. The want I always felt was always a hidden need which took me years to realize was my true problem in life to solve.

I hope you can realize your true wants and needs on your gender path also and life becomes easier for you if you are searching like I always was.

 

 

 

  

Saturday, July 11, 2026

It's a Lonely World

 

Image from Jarle Johnasen
on UnSplash.

It is a lonely world for many transgender women and transgender men as we journey along our dark gender paths.

As I always point out, like so many of you, I got a late start on filling out my gender workbook on how I was even going to begin a transfeminine life. Before the word was even invented. I was not invited to any overnight stays with the girls I admired so much to take advantage of early make-up tips and even feminine peer pressure on the clothes I was wearing to do a better job of looking the best I could in front of the mirror. Ironically, I was probably ahead of most girls age-wise when I started wearing makeup and shaving my legs, but I did not know that because I was not allowed behind the gender curtain to play in the girls’ sandbox.  

Looking back, I thought for a while there was always a chance I was going through some sort of a phase and I just could not be the only boy in the world with a strong desire to be a woman someday.

To make matters worse, I was always exceedingly shy back in those days which made me an introvert, and I had a tendency to not trust others. That would manifest itself much later in life when I had a very difficult time making close friends. Especially with other men. Who I thought would never understand my deepest darkest secret which by then I knew was no innocent phase in life I was going through. Not surprisingly after a while, I lost most of my shyness around ciswomen and enjoyed my time with them even more. Even though my true motives were never revealed that I just wanted to be like them in the worst way possible and I was just trying to see what it took to live their lives.

Even though I was still married to a couple of very different women through this portion of my life who knew of my cross-dressing desires and did the best I could to surround myself with other women, deep down inside I was still lonely. It never occurred to me why and what I could do about it for years. I just never realized for the longest time that I was living much of my life completely backwards. I was never meant to be a man and was forced into it by a cruel twist of fate I could do nothing about. Being a woman trying to live as a man put a terrific strain on me and caused me to constantly dwell on what I was doing wrong to feel so lonely.

When I finally made it out of my gender closet and into the world, my loneliness amazingly began to go away when I started to interact with other women. While men shunned me, ciswomen were curious why I was in their world. When they found out I was not some sort of fraud and a honest human being, it was OK to talk on a shallow level. Which was fine with me because I was so lonely after my second wife unexpectedly passed away. Her death taught me to never take anything for granted again and I set out to live more deeply as the transgender woman I was becoming. Just breaking down the gender barriers I was doing was never enough to get behind the gender curtain. I needed to do more.

Primarily, I needed to learn all over again how to talk to people. Mainly women but also men. Women I found came at me from all different directions and practiced a lot of nonverbal communication. I needed to practice the art of passive aggressiveness also when I found a smiling woman was not necessarily a friendly one. Until I proved to be up to the gender communication challenge, life became very interesting. Perhaps you have noticed that for the most part I left men out because for the most part, they left me alone. Which was fine by me, because with most of the men I did encounter, all I did was soothe their ego. Payback I guess from all the time I spent in the male world.

By this time in my life, I was looking at being sixty directly in the eye and could see very few avenues available to me to combat the extreme loneliness I felt at the time and had just figured I would have to spend the rest of my life by myself. As someone once said, the darkest hour is always right before the dawn and that is what happened to me. I already had my casual lesbian friends who met with me several times a week to watch sports and drink beer until my current wife came along online of all places and we cemented a wonderful relationship. Firat of all, Liz made me a believer in myself again. A confidence I had always had as a man but never as a trans woman.

Unbelievably, destiny had worked its magic, and I found someone to love in the world again and we lived close enough to make a romance work. As long as we are together (over twelve years now), we will not have to experience any lonely days in a cold world ever again.

For those of you who want to know more about how I did it was the only way I made it out was putting myself out there in that same cold world. I had to battle my fears by going out in big straight sports bars and becoming a regular. And, beat all the long odds to find a romantic partner on an online dating site. My big break came in the sports bars when a bartender I knew as a regular set me up with her single lesbian mother who I am friends with to this day. My moral to the story was I needed to put myself out there before I could reap the benefits, but I know the world has changed and you have to be careful.

One way or another, we transgender women and trans men live in a potentially very lonely world which is a shame because we have so much more to offer than the average human because we have seen so much in our lives.

Thanks for reading along and contributing with claps and comments! Hopefully I can come up with something meaningful to you.

 

Friday, July 10, 2026

It's Your World to Live In

 

Image from Gabriel Silverio
on UnSplash. 

When it comes down to it, it is your life to live and no one else’s. But life comes in the way.

The problem is often for transgender women and transgender men, it is easier said than done to live our own lives. Especially for those of us who had to wait until later in life to go after our dreams of transitioning into a feminine world. Perhaps, you were like I was and called selfish for my one-sided obsession about even seeing if my male to female dreams could ever become a reality. My second wife was fond of telling me my cross dressing should not be all about me.

The longer I pursued life on my new transfeminine gender path, I realized she was right. In order for me to move ahead in a world which felt so natural to me, I had to be selfish. It was the only way I could make the difficult decision to take a leap of faith and try to jump the gender border.

Back in those days, the only thing I could hang my pantyhose on were the annual Halloween parties I was going to dressed in my feminine finest. During these early parties, I learned a few of the basics I would need to survive as a trans woman later in life. Such as how visibly trained the human animal is to the genders, and if I was to go to the feminine side, everyone (male and female) would be noticing me. My new visible role in the world took some time and effort to get used to, but I did finally do it when I learned to dress to blend with the other ciswomen around me. It was my life to live, and I was coming closer and closer to deciding how I wanted to live it.

Before I did, I discovered I still had a whole lot of living to do before I made my decision. The problem was my male life on occasion was not that bad. Which gave me false hope that I could save it. All it did, as I juggled two genders at once, was to make my life a mental health hell as I struggled to maintain any sort of life I wanted. On one side, I had the increasingly financially successful male self-making it harder to give up all that he had earned and the male privileges which came with it. Struggling with my feminine side which felt she was in a more natural position to thrive. The end result was whatever decision I made just had to be the right one. With so much at stake in my life, I needed to go back to being very selfish with myself to make it.

In the meantime, I went into a heavy experimentation period of my life as a novice transgender woman. My goal was to try to live every moment that I could discover what a ciswoman has to go through in her life. So, I could tell if I wanted to do the same thing. I wanted to be more than the “pretty, pretty princess” that my second wife always called me when she was trying to make fun of my femininity to learn what she was really talking about. It was a struggle, but eventually I did by setting up my own version of a transgender bucket list of things to do. What did a ciswoman know that I did not became my main goal in life when I shed my male clothes and went out in the world as a trans woman. Overall, my plan worked well for me except the times I tried too hard and ended up in redneck bars where a single woman should have not been to begin with.

I did so much, I wore out my bucket list of obvious things to do and began to examine the difference between male and female privilege in society. Losing my male privilege brought about no real surprises such as having my intelligence challenged and learning to be more careful with my personal safety. While the main feminine privilege I felt was the freedom to be myself in the world and went way past just having doors opened for me by men. Needless to say, I was in love with the whole path I was on as a transfeminine person and could not wait to get back to it anytime I had to leave and go back to my increasingly unwanted male life.  I was stubborn but then again, I slowly realized I could never go back to the life I had lived before. No matter how successful it was.

As I reached the age of sixty, I could put it off no longer no matter how stubborn my male self-had become. When my second wife passed away from a massive heart attack, he was left with no allies in my life to fight with and was done. I had paid my cross-dressing dues by doing the best I could with what I had to work with appearance wise and had gone out of my way to experiment with how ciswomen live by putting myself in actual situations in life which I could expect to happen. After all of that, I just needed the final push off my gender cliff, and land in a world of my own choosing. Without a perpetual balancing act.

In other words, I guess you could say I went too far in paying my own dues during the approximately fifty years it took me to lead a life to discover who I always was. I decided long ago tt was too late to cry over what I did or did not do and to look forward to the time I have left in the world. At the least, I found living a life on both sides of the binary gender border was as scary as it was interesting. How many other humans get to experience what a transgender women or transgender man gets to see in one lifetime.

Sure, we experience our ups and downs but so does everyone else and we can have such an interesting path to claim a life which was always meant to be ours.

HEY YOU! Thanks for joining me in my journey and commenting or clapping for my posts. You make it all so worthwhile.

 

Keeping My Mouth Shut

  Image from P.A.U.L.A. on UnSplash. As I wrote before, yesterday was one of those busy days when everything seemed to come together to get ...