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

Thursday, September 3, 2026

Loving What You Do as a Trans Woman is Never Work

 

JJ Hart Doing Transgender Outreach
Perhaps you have heard the old saying about hard work. It goes something like this... If you love what you do, it is never work. Anyway, I looked at it, the phrase really fit my life as a transgender woman or an early cross-dresser.

Even though, early on it was hard work finding one of mom’s dresses I could still fit into and not rip apart in the seams, I still tried it. As I grew into a more mature version of my feminine self, I learned my work to transform myself into the woman I was always meant to be was not going to be an easy task as testosterone poisoning was ravaging the body I wanted to have as a girl during male puberty. While the girls around me were developing the curves I wanted, all I got was a larger angled male body I hated. If I wanted to continue, my path was cut out for me, and it was not going to be an easy one to follow. I would have to make it a labor of love to ever succeed.

The first thing I needed to do was find feminine clothes that fit me, and at the same time disguised my male body with my large torso, broad shoulders and narrow hips. Plus, I had the extra problem of look really liking the feminine shape wear I need to wear to suggest I had hips when I cross-dressed as a woman. It was always too restrictive for me to enjoy and I was not careful; the restrictions went as far as hurting my chances of success in a women’s restroom setting. If you know what I mean. What I did was make extensive use of pieces of foam which I wore under my panty hose to give me the illusion of hips under the skirts and leggings I wore back in those days. I remember spending day upon day of destroying foam rubber pieces until I thought I got them just right. That solved the hip problem partially so I could concentrate on my all-important breasts.

To advance my presence in the world as a transgender woman, having the proper breasts was another labor of love and at times a comedy show. Before the advent of easily obtainable silicone breast forms, I tried a number of ill-fated ideas to give myself the proper breasts which fit the size of my body but were not too big and looked like I came from a circus somewhere. Before my first silicone breasts were gifted to me by a purging cross-dresser friend of mine who was getting rid of all his feminine belongings, I tried exotic ideas such as bird seed and water balloons. Water balloons I liked because they warmed to the temperature of my body and did a realistic job of looking like real breasts in the bras I wore at the time.

All along, I knew on the negative side, I was taking a big chance using water balloons for breast forms because they can easily break. And of course, the worst-case scenario happened to me one night when one of my balloons broke in public. Luckily, I was going to the women’s room anyhow and it was empty so I could clean up and head back home to end my love affair with water balloons as breast forms forever.

As I put all this concentration into making my transfeminine better, I was concentrating less on my male life. Although it was a labor of love for me, it was not for my second wife who grew tired of my obsession to be an attractive woman and told me I was missing the whole point of being feminine. It was not to be obsessed with makeup and clothes; it was being able to slide behind the gender curtain and see how ciswomen’s lives really play out. It did not take many times of being called a terrible woman for me to drop what I was doing, change course and try to find out what she was trying to tell me. Then I found myself in a “Catch 22” of sorts because if no one would allow me to play in the girls’ sandbox how would I ever learn to do it. It was like the job interviews I went to, where they told me I did not have enough experience but would not give me a chance to work for them and gain the experience.

I finally had to stop being the victim and head out into the world to discover what my wife was talking about. If indeed I was a terrible woman, I need to correct that and move forward. It was then I went on a collision course with myself to determine what I really wanted in life. Did I want to be the successful man I was becoming or have the chance to live out my dream living in a ciswoman’s world.

The labor of love that I entered involved me having to learn what a ciswomen’s life was all about. I knew it was going to be quite the change to learn a new scary complex world, but I was not prepared for the barrage of information I needed to deal with. It seemed that half the women I met wanted to interact with me and find out what I was doing In itself, interaction was not bad if I was ready for it. Which I was not. I had to go on a crash course in understanding my communication with women like I had never known before. I was used to listening to ciswomen the way cismen always to by hearing only what they want to hear and ignoring the rest. Woman, on the other hand, have so many nuances in their communication that I had a lot to learn. But again, it was a labor of love for me and no work at all. If I had put that much work into my college studies, I would have finished with a four-point average. It showed me where my priorities in life really were.

From the first time I tried to experiment with mom’s makeup to living the life I live today, my male to female gender transition was never any work because I loved doing it.

I also love writing for you in the hope I can help you along in your life’s journey. Thanks for reading along and any comments are always appreciated.

 

 

 

 

 

Sunday, August 30, 2026

Being Accommodating...Not Intimidating

 

Image from Billie
on UnSplash.

Being accommodating versus intimidating was very difficult for me as I transitioned from male to female.

It was all part of learning a new feminine world and escaping the male bonds I had suffered so long from. What happened was, I was thrust into a male dominated world in which if I was ever going to survive, I would have to play the intimidation game of life. That way, I could stand a very good chance of keeping the bullies away as I matured. It did not hurt that I developed into a larger slightly above average sized male person (which I hated) but again when I added sports into my life’s mix kept the doubters away from my masculinity. In fact, I needed to play that intimidation card well into life and used it before I transitioned into a transfeminine world. Intimidation became easy to use for me, and I counted it as one of my male privileges even though I stopped short of ever being a toxic male because I respected all women so much. But it worked well with the male kitchen crews I needed to manage in the busy restaurants where I worked.

The problems began with my basic personality outlook I had been forced to live so well when I began to try to join a world which was largely controlled by ciswomen, not cismen as I always thought was the case. Women just found unique ways always to work around males and their drama. And here I was in the middle of a new world just trying to find my way successfully.

I felt it most intensely when I was forced into communicating one on one in the world with other women. I found I was unprepared and initially just tried to keep my mouth shut, which turned out to be exactly the wrong move to make. Here I was trying to make new friends in a feminine world without talking? How was that going to work. It did work. In exactly the way I did not want it to. If I did not express who I was, the other woman I was trying to communicate with just assumed I was being standoffish or in some way stuck up which was the last thing I wanted to do. So, I immediately trashed my male scowl and quiet behavior as a form of intimidation to keep people away and went to a more open form of interaction with the public which invited people in. In many ways, it was one of the most intense and scariest things I ever went through in my life. I was in uncharted territory for sure and even resorted to feminine vocal lessons to help my progress.

And then there was the experience I had with a small girl who startled me in a clothing store I was in. She ran around a rack of clothes and almost hit me and went running back to her mom saying something about a “Big mean woman.” Immediately I was relieved that she got the woman part right but right then and there decided to do more about the old male intimidation factor I was obviously still carrying with me. In no way did I want to go around scaring little kids.

Life went on, and so did I as I started to feel more secure in my new role behind the gender curtain. I learned that many ciswomen were just curious about who I really was in a world in those days dominated by day-time sensational talk shows such as Phil Donahue and Jerry Springer. Here I was. The real deal cross-dresser or transgender woman right in front of them to talk to and know that I was just a normal person like them after all. It all happened because I had the courage to let them into my world and turn my old male intimidation ideas off for good.

Perhaps the most intense topic in the intimidation versus accommodation discussion came from my initial introductions to the women’s restroom. It was the exact opposite from the men in many ways except the obvious. In the men’s room, you were expected to never make contact or acknowledge another man while in the women’s room just the opposite was true when a polite smile or greeting was the proper way to acknowledge another woman. It took me a little bit of time to get used to the change, but I did it quickly because I wanted to earn my women’s room privileges desperately. For obvious reasons, I was drinking a lot of beer.

I see intimidation versus accommodation as just another step in acclimating yourself into the feminine world. But you have to do it right to be accepted. You must be yourself behind the gender curtain you choose without becoming a doormat. As an outsider to transgender men everywhere, my thoughts are it probably is more difficult to assume an intimidation role in a male world. On the other hand, accommodation in the female world I was in was always an easier path for me to take. I just had to understand and react to anyone who was setting up to take advantage of me. I came away with plenty of claw marks up and down my back from unfortunate experiences I had in a new (to me) passive aggressive ciswoman world. I learned often that a smile meant nothing in most situations when another woman was just sizing me up.

In the end, the whole experience just boiled down to very important experiences I needed to learn to finally make it out of my closet and into the world as a transgender person that other people would like to know and often my smile was the beginning of that process instead of my stay away old male scowl. The fun part often was seeing the results from the amount of learning I needed to do in my stubborn head to make it happen.

As always, thank you very much for joining me along my gender path and I hope you gained something from my mistakes. Any comments are always appreciated!

 

 

 

 

Saturday, August 29, 2026

Leaving the Male Noise Behind Me

 

Image from Vinicius Amano
on UnSplash. 
 

I write often of the misadventures I had growing up as a gender I never wanted to be. Often my life seemed unbearable when I made a big error on the baseball field or missed a key tackle on the football field, causing my team to lose. When I did, the only thing I knew to do was to run home to my dresses and makeup and do my best to tune out all the noise of male failure in my head. If I could not be a good athlete, maybe I could try to be a pretty girl.

To make matters worse, the older I got, the more noise kept popping up in my head. Especially from my male side, who was increasingly watching any chance o a future he had slip away. Successes such as making it through the military, and job promotions did not help either.

As the probability of a male to female gender transition increased, the noise did too. Mainly because I noticed an increase in the male world, I was never have been a part of. Perhaps, it was because I was thinking about leaving it anyhow, so I was looking for sure if I wanted to.

One of the sounds I noticed the most were coming from the alpha-males who were posturing for a better place in the world. Since in many ways, my job forced me to be successful in my competition with the alpha’s (as well as my upbringing) I could listen to the noise and tell exactly where it was coming from and how I could compete. Which ultimately led me down a path I had no desire to be on.

The further I traveled along the transgender path I was on, the more I noticed the noise from both sides of the gender border increasing as I stopped to look around at one of the many stop signs I had along the way. Sometimes the screaming from both sides reached a pitch I could barely stand as each side was yelling, they were better. To make matters worse, my male side had most all the advantages which he used to his benefit when he stated his claim on my life. Afterall, he had been there from the beginning and had taken the time and effort to learn how the male world operated and how he could fit it. All my feminine side could do then was continue to cross-dress in front of my favorite mirror and dream of an uncertain future.

The one main thing she had going for her was she had the advantage of feeling natural when she was allowed to express herself in the world. It was a powerful emotion which at least kept the male screaming down to a minimum, for a while. What always happened was, I had a several days of gender euphoria after I cross-dressed which would sadly fade when I mentally and physically had to go back to my male world. Which was far from being a mellow existence. The gender headphones I was continually trying to wear in life never seemed to work well. Even to the point of causing so much guilt, I would purge (throw away) my feminine clothes and vowed to never wear them again. You know how ell that worked as my female side screamed louder and louder to once again be a bigger part of my world and I would be forced to give in.

The sad part about all the noise I was subjected to internally and externally by my gender dysphoria was wrecking my fragile mental health. I never bargained, ever having to deal with the stress of having to bargain with two of the main binary genders ripping my life apart. I only survived by taking advantage of finally listening to good therapists who told me that my gender issues would never just go away and would always be a part of me. I guess you could say that it was therapy which helped me cut through all the noise and essentially saved my life from being extremely self-destructive.

Finally, when the noise reached a fever pitch, I needed to take drastic measures to do something about it That is when I went on an aggressive all-out push to see what a ciswoman’s world was all about and better yet, could I ever be accepted into it. My so-called discovery tour took me out of the worlds of dark gay venues into the lights of straight places such as TGIF Fridays which back in those days was becoming a safe venue for single women to go to. To do what I wanted to do, I needed to put my extreme fear of discovery behind me and see if I could survive in Fridays. When I did, a portion of my noise suddenly made sense to me, and I realized what I needed to do to tune out the rest.

I was proving to myself that there was nothing wrong in what I was doing, and I was starting to ignore all the panic warnings I was receiving from my male side about what I would lose if I left him behind to follow a feminine road. The best part was, the more I started to listen to the feminine noise, it made me feel better about where my life was heading. Even though many of the things I was trying scared me to death, as I succeeded in each step, I was building a calm confidence I would never lose.

Of course, the more my feminine noise clamed me and made me whole, my male noise started to subside to a low whimper. Gone were the days of being lonely and searching for my gender identity when I discovered ciswomen lesbian friends who gave me mine. As they taught me more about validating my own womanhood than they ever knew they did.

Very soon I even healed from my destructive days of listening to all that male noise and was able to throw those old gender headsets aside and live my dream life.

Hey you!!!! Thanks for reading along with how I escaped my male gender noise and maybe it can help you escape yours too. In any case thanks for being here!

 

 

 

Thursday, August 27, 2026

I Wanted it All

 

Image from Sindy Sussengut
on UnSplash.

During my gender journey through multiple transitions from cross-dresser to transgender woman, I have been selfish and wanted it all.

It all started very early when I was experimenting with mom’s clothes and makeup when I had the first idea all that I was doing may go deeper than just wearing feminine clothes. I did not have the terminology or knowledge back then to work my way through it, but in reality, I was discovering I was more transgender than anything else. In the years to come, that would be a major point to think about along my gender path.

As I grew through my first two marriages where both wives knew of my cross-dressing desires, my first wife was far less demanding than my second and on numerous occasions during fights we were having about me, my second wife rightfully pointed out that our relationship was not all about me. Since I was in the middle of an obsession with my appearance and all things related to makeup, as I said she was right and I was needlessly selfish about our relationship. She was far wiser than I and knew even at that early time in our marriage, her husband was slipping away.

Even though I loved her dearly, I still could not stay away from the powerful draw of wondering if I could ever achieve living fulltime as a transgender woman. Deep down, I knew my second wife would never come with me on my journey as she made it abundantly clear she never signed up to be married to another woman.

With a lot of work and repetition, I did finally get better with my wardrobe and makeup and then needed to figure out how to sneak out of the house and get into the world. It basically meant my imagination had to go into overdrive as I tried to think of reasons I needed to explore the world as my new true transfeminine self. Even if I was not sure what the word meant back then. I went as far as going to the grocery store for my wife who was working on the days, I was off and combined the trip by going to a nearby big box store to shop for panty hose and makeup. My biggest takeaway came when I noticed very few people were noticing me and I started to think I wanted to experience more. My restless feminine spirit was dominating me again.

At the same time, I was doing all of this, I was still searching for my dream job in the commercial restaurant business and after switching jobs and locations several times, I finally did. As I finally broke free of my fast-food background and landed a job with “Chi-Chi’s” Mexican Restaurants in the Columbus, Ohio area where I had ties to. It was a win-win situation for me because I was back home again and could start to interact with the diverse small LGBTQ group that I had known from years previous. This was the tight knit group that had several transgender women who were on their ways to gender realignment surgeries, and I could pick their brains on what it meant to do it. Even though, I did not have the resources or the willpower to consider such a radical move for me in my future, Just being considered as an equal in their group was good enough for me…then.

I say “then” because in life everything rarely stays the same. As I continued to break the vows I had with my wife, I kept going out to venues from the house and began to actually carve out a life as a transgender woman with people who had never known my male side. Wanting it all was staring to mean so much more to me than ever before as my male life began to slip away from me and wanting it all increasingly meant an ongoing break with my long-term marriage of over twenty years. Because she was not giving into her demands, and I was discovering just what mine should be if I was willing to risk it all to live my dream life. Sadly, it would have to be all me to do it as I tore down everything I had worked for as a man to start over in a woman’s’ world.

Sure, I was scared to death as I decided to keep concentrating on the feminine me who had waited so long to live her life. But the whole process and path I was on felt so natural, I decided to be selfish and continue it. By proceeding along the path I was on, I needed to take several abrupt detours when I had problems with deciding my sexuality all the way to just basically communicating with the remainder of the world I was in. Which I discovered was made up of ciswomen not so unlike my second wife. Many were strong and sure of themselves and set up forms of communication which were totally foreign to me as I was coming from a male world. Suddenly, I needed to adjust to forms of non-verbal and passive aggressive communications which were reserved for use when cismen were around.

Perhaps my best selfish move I made was to be approved for gender affirming hormones or HRT which enabled me to come closer to my transgender mentors of so long ago. Since I had ruled out any surgeries, the changes from the hormones would be as far as I could go to sync up my female mind with my male body.

By this time, my wife had passed away and there were very few people left who knew the old me at all. So, I was mostly all-alone with my new emotions and bodily changes such as hair, breasts and hot flashes. When I reached out to any of my lesbian friends, all they would say was welcome to their world. Little did they know how badly I wanted to be there. I was rewarded by the fact that the people who knew the male me told me they thought I was much more relaxed and happy now.

Since I can now love more deeply than I ever could as a man, my life has come full circle to encompass feelings I never knew I had before. All because of my selfish one sided past to get here. I wanted it all and finally was able to find it.

Thanks for reading along and I would be remiss if I did not mention two things. Thanks to Grace Ann Hansen for publishing my stories in her “Empowered Trans Woman” site!

And sadly, I would like to mention the passing of a true icon, Dolly Parton who was a staunch ally of the LGBTQ community. She will be severely missed.

 

 

 

 

Wednesday, August 26, 2026

On A Gender Vacation

 

Image from PR Media 
on Ubsplash.



As I matured as a person and a crossdresser, taking a vacation from my male gender became a reality for me.

It all started when I first felt the inclination to try on articles of my mom’s clothing and moved on from there. Very soon, I spent as much time as I could in front of the family’s full-length hallway mirror imagining myself as one of the pretty girls I envied so much. Before my unwanted male puberty set in, I did not have so far to go to be on vacation from my boyhood self. Then the changes set in and I began to develop the body angles and shape of a man as the girls around me were showing off their new curves in pretty clothes.

At that point, vacations became harder to earn, as it was becoming more difficult for me to look like a girl at all and try to work my way around having no knowledge of makeup at all. That chapter of my transgender notebook (like all the others) was empty, and I struggled not to look like a clown in drag at the circus. In a very short time, I became aware that if I was to ever reach my dream of living my life as a transgender woman, I had a long, hard struggle ahead.

It did not make matters any easier when I went on family vacations and saw other girls my age in cars on the highway. One young dark-haired beauty still stands out as one I remember. As I saw her time and time again when we passed on the highway, I so wanted to be like her and put my pillow over my head and pretended to sleep. No imagined vacation for me on the real one. My gender reality was with me all the time.

One way or another as life went on, I needed to do something to survive. Somehow, I needed to break through the bonds of the increasingly complex male life I was living and start to carve out a new transfeminine existence on my own. If my reality was indeed female, I would have to do something about it. What I did was begin to mix business with pleasure on my vacation. Business was when I was learning that ciswomen ran the world I wanted into and pleasure was when I was able to finally blend in until I was allowed behind the invisible but so real gender curtain.  To maintain the lifestyle, I was trying to lead, I needed to do a lot of research and repetition to see if I wanted to be there at all. Those were the nights when I broke away from all the gay venues I was going to and started to see if I could be accepted in lesbian and straight places.

The vacations I took into the world as a new transgender woman turned out to be life changing for me. For once, I did not have to wonder what if would be like to live in the world as a woman and just do it. My time away from my old boring male world, took me into a wonderful new life as the woman I always wanted to be. I was the trans woman at the big sports bar enjoying my large beer as I watched my sports teams play on the big screen televisions. Occasionally, I received some pushback from a toxic man, but it was not enough to deter me from having a good time. Mainly, because of my confidence in who I was building every time I was successful trying out the me, I always should have been. I was not building anything new, just allowing my true self to flourish in the world.

At that point, it occurred to me that my vacations were changing drastically. Instead of believing I was taking vacations from my male self as a trans woman, I was now taking time from my feminine world to allow my male self to finish up important things such as working and keeping up a false image of a man for the world to see until I could fully complete my male to female transition. Since I had accumulated so much male baggage over the years, clean up was not going to be easy. Finally, it occurred to me that transitioning to my new life was going to be an all or nothing proposition…or was it?

A big decision I needed to make was involving my sexuality which had never been a question for me in my male life as I had never been physically attracted to another man ever. It did not help me when I got a suggestion from ciswomen to buy bananas to get ready for a new sex life that never came. Even though I had dates with several cismen, nothing ever sparked within me and we never went anywhere except kissing, Women, on the other hand were different as I still cherished their company which I found they enjoyed mine too as they went on vacation with me. Since HRT hormones took away any possibly of traditional sexual intercourse between me and another woman, by choice I took it off the table.

It all led me to wonder what I would do about sports, the one big passion left in my life. Could I still interact with the world as a passionate sports loving woman or would I have to give it all up. It turned out that no, I did not have to give up my passion, it just changed direction like so many other things in my life. For example, when my lesbian friends and I were talking sports, we did it on an equal footing. But when I talked sports with a man, often I needed to take a back seat to his sports knowledge even though I had plenty of my own. I learned my lessons and moved on.

Even though many of my vacations from life were just quick, cheap escapes, many were extensive, expensive paths to my future life. Plus, they handed out much needed respites for my often-battered mental health as I battled depression and anxiety. It all helped me to survive and make it to my dream goal I never thought I could make it to. A life as a transgender woman.

As always, thanks for not taking a vacation to read and comment on my posts. Your input always means a lot to me!

 

 

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.

 

 

 

 

 

See and Being Seen as Me

  JJ Hart (center) with Liz (left) and  daughter (right)  Yesterday was one of those rare days when I needed to get out in the world and do ...