Showing posts with label makeup. Show all posts
Showing posts with label makeup. Show all posts

Friday, July 24, 2026

It's All in the Details of Gender

 

Image from Liam Nguyen 
on UnSplash.



Quite early in life, I learned to pay attention to the details when I followed my instincts and started to cross-dress into mom’s clothes and try to put on her makeup. I thought all was good after I had snuck around and managed to shave my legs again without anyone noticing.

That was until I snagged mom’s hose on an unkept fingernail and ran yet another pair of good stockings or pantyhose. I learned the hard way to take better care of my nails as well as the rest of my body on my path to femininity. Little did I know, paying attention to just the smallest of details would rule my world as I climbed my gender path towards my dream of living fulltime as a transfeminine person.

My major problem was that I was restricted to viewing what a woman’s life was like from the outside in a male dominated family. Through it all, my mom became my mentor and role model more than she ever knew and it went way past just using her makeup and wearing her clothes. I could see how she worked behind the scenes to make sure that the family ran as smoothly as possible. Way past all the traditional female duties such as cleaning and buying groceries. She taught me all that a ciswoman could be at a young age. All the time not realizing what she was doing because she actually had a daughter, not a son.

It was not until I began to get out on my own as a novice cross-dressing transgender woman did; I really have to develop my sense of detail. It was very difficult for me because I was never a detail orientated person. When I went out initially as a trans woman, there just seemed to be so much to concentrate on and remember to do to succeed. Even if I thought I had perfected my fashion, hair and makeup for the evening, there was the problem of putting it all together outside of the mirror and getting all my movements down, so I did not look like a linebacker in drag. The details weighed on me heavily and they were all I thought about in every spare moment I had. So much so that I needed to think ahead to which gender I was at key moments in my life.

It all carried over into life events such as weddings and dances when I had to step back and wonder what I would be wearing if I ever had the opportunity to attend as a trans woman. Sadly, I did get to experience attending a funeral when my wife Liz’s dad passed away after I had transitioned. I wore my best black outfit and did the best I could to blend in properly with all the other ciswomen who attended.

The funeral was just another reality check for me as I needed to face how far I had come in my male to female femininization journey. At my age, I always knew attending a funeral as me was a possibility, but I never knew how real it was until it happened. At that time too, reality and details were becoming increasingly important as I expanded my life in the world to new and exciting groups of strangers such as in spiritual circles and Meetups of writers in Cincinnati. They were the first groups of strangers that I had ever met outside of LGBTQIA+ support groups I attended locally and at the Veterans Administration in Dayton, Ohio. Meeting new people as I said was exciting and kept me active at an exciting time of discovery in my life.

By this time, repetition replaced my need for detail as my makeup habits, along with clothing needs became ingrained as I finally knew who I was in my life. No more searching in a dark lonely closet for an answer. I had it with the help of the world of new and exciting discoveries I was in. I had brief moments of releasing my gender euphoria before but nothing like this before as all the possibilities of the world were opened to me. When I sought out and was approved for HRT or gender affirming hormones. Which I write about a lot. New emotions outweighed the need for details as I moved ever closer to being the person I always wanted to be.

One thing I never forgot as I male to female transitioned was how I was treated early on and how I needed to respond by going back to my cross-dressing drawing board time and time again until I got my details correct. There was so much more to what I was trying to do than my home mirror had told me as I tried to exit my gender closet for good. All I knew was, once I was released from my loneliness, I never wanted to go back. I spent as much time as I could out in the world working on my feminine presentation so I could overcome my testosterone poisoned body and make it.

I cannot stress enough how much of my journey has been filled with fear and or panic when I lost key male privileges such as intelligence and personal security. Details just weren’t enough to help me through all the anxiety I felt meeting strangers in my new exciting world. In fact, just yesterday, I felt the same old twinges of panic sneak in when Liz’s son and I had to take our old lawn mower into the shop for a tuneup. After all these years in the public eye and I still have the same problem is ridiculous I know, but I still do when I am entering predominantly male spaces for any reason. Again, all went well as the young person at the mower place was only interested in taking care of us. Not my gender.

All in all, the extreme work I put into crossing the gender border was worth it as I achieved my goal of living the life I wanted to live. Even though there were times when I did not think I was going to make it.

Thanks so much for joining me with my life experiences. Hopefully you can gain some insight into your life from them. Comments are always welcome!

 

Wednesday, July 22, 2026

Imagine your Dream

 

JJ Hart on left, Pic Nicking with Liz on right.

Yesterday, I went with my wife Liz to her appointment with her “vampires” to have her blood labs done.

When I did, I had a chance to sit around and watch the other ciswomen in the waiting room and see if they were watching me at all. They were not and went on as they all were too busy on their cell phones to even come close to noticing the trans woman in the room. Instead of me joining them on my phone, I thought back to a time when just going to a doctor’s appointment was not such an easy task because of all the gender paranoia I was feeling. A gigantic case of impostor syndrome to be sure.

Early in life, as I imagined my dream of living a transfeminine life, I never factored in all the mundane things a woman does during her life. I was too busy being the “Pretty, pretty princess” as my second wife always called me. And to her I would have been about the furthest thing away from being any sort of a princess in the waiting room that there was. I would have never dreamed I would have been seen in public without being dressed from head to toe as close to an attractive woman than I could.

Nobody but me cared that my dream had changed and I was alright in jeans, t-shirt and light makeup to be seen anywhere in public. I was just another person with very long hair and breasts in a doctor's office. Had I become lazy in my old age or just dressing to blend in with a public who increasingly does not seem to care about feminine appearance.

Maybe I was just being selfish in that I was OK with just dressing to blend in with the rest of the world around me who were too busy on their cell phones to notice me at all. Is that what my dream had become? Perhaps I am being too demanding in my dream that I wanted it to turn out a certain way. And, I certainly did not set out to be some sort of a leader in the ciswomen’s fashion world, I had had enough pressure on me to lead for a lifetime when I was living in a cisman’s world. I just wanted to fade into a new world and learn it totally. As I come closer to the age of seventy-seven, I think I can safely say I have reached that goal I set so long ago.

Coming up Saturday, my daughter and son-in-law are making the trip down to Cincinnati from Dayton, Ohio to bring me a scrap book of family pictures and have breakfast with Liz and I. For that visit, I will certainly attempt to dress up more for the occasion, which will include a new top I bought, along with new flats and even tying my long, long hair back also. She is the only accepting blood relation I have left, so it will be good to get out of the house and see them.

In many ways, the visit will prove my dream is not dead as I get to relive the fun of dressing up different as a transgender woman. Which was one of the fantasies I had when I started so long ago up my gender path. I should have known that my path would have been different as I veered away for just wearing skirts and dresses and sticking with slacks and women’s pants. Much to the chagrin of the cross-dressers around me who kept asking me why I would want to wear pants when I had to wear them all the time as a guy. My only answer was that I liked the way I looked in them, so now you can go away and mind your own business.

I guess you can say that even in my formative years as a novice transgender woman, I have always been a “tom-boy” of sorts. Which is probably another reason I fit in so well with the lesbian culture that I did in my jeans and boots. One way or another, the pieces of my lifetime dreams puzzle were coming together and even though I was too stubborn to initially accept it, the finished puzzle was all me. “Tom-boy” and all.

I was fortunate too when I discovered that and became a firm believer in my gender was completely between my ears and not between my legs. Which made feel less bad about not having any access to the early sex-change or gender realigning surgeries which were available at the time. My complex life was slowly coming into focus, and the best part was that I increasingly felt comfortable and confident with it.

Coming full circle back to Liz’s blood work appointment, I had the chance to remember the bad old days when even such a mundane trip such as that could cause me strain and paranoia. It felt so good to feel good about myself and confidently walk in proudly holding Liz’s hand. I never wanted to go back to the early days of gender dysphoria and impostor syndrome that I suffered through.

The moral to the story is that if you are on your path to a gender dream goal, there is no real unique way to get there. Ciswomen lead such complex lives that they leave you many ways to carve out your own. Way past the shallow aspects of appearance and sexuality. Which gives you more interesting sidelights of your life to explore and live. Just remember to stay safe as your personal safety privileges you had as a man go away forever. You are just learning what ciswomen have always known…stay clear of toxic men.

In the end, it is your dream to claim if you can get there, and to do it you may face challenges until the final pieces of your puzzle come together. Just remember, you are attempting one of the complex and difficult efforts a human can try and even if it so difficult to do, it can be worth it in the end.

 

 

 

 

Wednesday, July 1, 2026

The Consequences of Giving Up

 

Image from fast glass fx 
on UnSplash.


When I considered “purging” (getting rid of all my feminine makeup and clothing) the consequences felt like a double-edged sword.

For a few days, the pressure around gender lifted, and I had one less major worry. But before long, the familiar desire to live as a girl returned to my everyday life. I realized that cross-dressing—and perhaps something beyond it—would not be easy for me to give up. Even in that short time, I had learned a great deal and understood how far I still had to go before reaching my dream of living full time as a transgender woman. I was not even sure whether I could make it happen.

Then there were the brief moments of gender euphoria. The time I spent hiding from my brother and family was enough to keep me going until male puberty—and what felt like testosterone poisoning set in. I was unhappy that my body was becoming more angular while the girls around me were developing curves, but there was nothing I could do to stop it.

Even as those changes continued, I could not face the consequences of giving up. I learned to take what I could get until I was old enough to leave the mirror and closet behind and explore the world. What happened next was brutal. I discovered that the mirror had been lying to me when it suggested I looked like an attractive woman. If that were true, why was I laughed at so often when I tried to go to ordinary places, such as nearby shopping malls? Eventually, my frustration pushed me to look around and notice how most of the cisgender women I saw were dressed. Even if it meant adopting the casual styles I dreaded, I knew I needed to do it to blend in and be accepted.

The more acceptance I gained, the harder it became to return to my old life and face the thought of giving up on my dream. For the first time, I even felt excited about where my future might lead. I just had the glimmer of hope that I might be able to make it to the transfeminine life I always wanted to lead.

At that point, my male life began to creep in with a vengeance. He was becoming very successful with a small family and good job and the risk of giving it all up loomed large over everything I did. Not a day went by when I didn’t consider the consequences of what I was doing. I always say, I wish I could get back just a fraction of the time I wasted worrying about how I would be living my life if I was a woman. What would become of me if I jumped off my gender cliff for good.

What I decided to do was experiment in the world as a trans woman. My second wife called me a “terrible woman” because I had never paid any dues that ciswomen pay, and all I was concerned about was my appearance. I knew deep down she was right but I still at that point did not know how to fix the problem by paying my dues as a novice feminine person in the world. It was like if you are applying for a job, the employer says you don’t have enough experience but will not give you the job so you can get it.  I am sure my wife was right about my feminine knowledge, but I was having an impossible time getting behind the gender curtain to learn more.

As I slowly got behind the gender curtain, the consequences of giving up almost completely went away. Why would I abandon all the effort I put into being a complex transgender woman and throw it all away during a time when I was finally being successful. For a change, I was the one making sense in a gender situation which very few understood.  No longer could I be accused of being a terrible woman as I matured into my new self when I was allowed into women’s only spaces. Sure, I was still making mistakes, but they were getting smaller and smaller as time went on.

The mistakes I usually made came from when I miscalculated how complex a ciswoman’s life really was and how far I needed to go to be allowed to fit in. To eliminate all my mistakes, I needed to give up all the negative consequences of a male to female gender transition and just make the plunge. Fortunately for me, the water was not that cold, and I jumped into the deep end of the gender pool. Plus, I can never forget the soft feminine gender hands which helped me to survive the impact into the water.

I know many of are thinking seriously of making your own gender plunge and what would be the consequences of possibly losing everything you hold dear in the world. I know advice is easy to give, but the turning point for me always was how natural I felt as a transfeminine person. Something kept telling me I was born the way I ended up. And with some effort, I made it to where I always needed (not wanted) to be. Hopefully, that is a starting point for you too and the consequences of giving up become too much to consider.

If you are further along, I am sure you recognize the consequences of never giving up and somedays even being perceived as being selfish. As I was when I was headed all out to fully transition into a transgender woman, all I could think of how fast I could make it to my goal. So, I am guilty as charged. It is probably the reason my second wife called me a terrible woman. In all fairness to me, I did mature out of it and found my way into a better world.

All the purges in the world did not work for me and I put up with all the consequences I lived through. I am not a gambler, but in this instance, I played the odds and won.

 

 

 

 

 

 

Monday, June 29, 2026

Dealing with Stress as a Transgender Woman

 

Image from Ksenia Berjoz 
on UnSplash.

In the male world I did not want to be in, I had a difficult time responding to pressure except where I worked where oddly enough, I thrived.

I suppose the gender pressure I was under started very early in life when I needed to struggle mightily to even find the private time to even try to be the pretty girl I wanted to be in front of the mirror. From my early cross-dressing years, instead of growing away from feeling the pressure I was feeling, I grew into it. On one side, I had the fond thoughts of gender euphoria dominating every spare moment that I had and on the other side I had the reality of having to compete in a world I never wanted to be in. Football was a prime example of me trying to overachieve and ended up breaking two bones doing it before I just quit.

Moving forward to the time when I left my closet and started to discover the world as a novice cross-dresser or transgender woman, the pressure was on more than ever before to succeed as neither of my egos were taking getting laughed at by the public well. My feelings hurt, and the pressure as I said was building to do something about it.

The first thing I knew I could do was go on a diet which quickly slimmed my body so I could find and wear more fashionable clothing and started to take care of my skin better everyday after I shaved. All of this helped me to feel better about myself, and I kept on trying to perfect my makeup techniques to improve my public presentation. With all of this, it still took me quite a while to build my fragile confidence to a point where I could go out in public again.

Then I found myself in a spot where pressure was coming at me from different angles. On the days I thought my makeup and clothes were at their peak of success, the pressure would set in about how I was moving as a transfeminine person in the world. I needed to concentrate on two things, not moving like a linebacker in drag and making sure I put a pleasant look on my face. Replacing the male scowl I had perfected for so long. If I was enjoying my new life, I would have to make sure I showed it to the world.

As I did all of that, my inner pressure began to change once again as I began to free myself from the drag atmosphere of the gay venues I was going to (where I was considered as just another queen) and into the straight world I was used to where I could at least have a fighting chance of being treated as another woman in the world where the ciswomen ruled the scene I wanted to be accepted into. For the most part, I discovered that most ciswomen did not notice me, or if they were, they were just curious why I was trying to play with the girls’ club and leaving the universe of men.

At that point, I nearly panicked from all the pressure I was under as I desperately tried to maintain what was left of my male life which included my wife and job and at the same time try to allow my feminine transgender side to flourish also. My main reason to panic came when I needed to learn immediately how to communicate one on one with other women. To relieve the pressure, I went all out and even took feminine vocal lessons and I had to focus for the first time in my life on really listening to what someone else was telling me because I found that ciswomen were the masters at non-verbal or passive aggressive communication and used both methods to by pass the men around them. Which was the main reason men said they could not understand women. The women had set it up that way.

I did maintain that life as long as I could before the pressure increased again until the forms of relieving it, I was using, just did not work any longer. On top of that, I was becoming more and more self-destructive, and I kept putting my life in danger. Fortunately, before anything severely happened to me because of the pressure I was feeling nothing severe happened to me and I began to build a new exciting life out of the ashes of the male life I used to live. I took what I could from him and added it to my new transfeminine life I was beginning to carve out for myself.

Magically then, much of the pressure I was feeling about my male to female femininization started to drain off me. I can’t take all of the credit because I fell into the open arms of so many ciswomen who had problems of their own and took the time and effort to help me with mine. All their efforts reinforced why I wanted to be allowed behind the gender curtain to start with.

After the pressure was released, it was like the sun came out to me on a cloudy day, I can’t say how much weight was lifted from my shoulders when I finally saw the sunlight and decided to put my male self in my past and begin HRT or gender affirming hormones under a doctor’s supervision.

I can’t say before then I had any knowledge at all how to live a life without experiencing gender pressure. As I matured into a confident transgender woman, I finally realized I did not have to live that way, and I had the built the confidence to change it.

Certainly, living under pressure is no fun, and I would not wish it on anyone. Also, I know everyday humans have stress in their life, but I am biased, but I think transgender women and transgender men have more than their fair share to deal with. How we are able to handle it can define our lives.

 

 

 

Saturday, June 13, 2026

So Many Choices...So Little Time

 

Image from Drew Colins
on UnSplash.

One thing that I learned from experiencing decades of cross-dressing is that there were so many choices and so little time.

It all started when I had to scramble for any time, I could find by myself dressing as an imagined pretty girl in front of the mirror without discovery from my brother or worse yet my parents.  I was born as the eldest son into a very male dominated family, and I was expected to fit right in with that male mold. I had little idea at the time that I was destined to break that male mold during my life and it was not going to be easy.

Back in those days, I had very little income that I scraped together from doing household chores and a newspaper delivery route I had for several years. The first feminine items I could afford to buy on my own were makeup accessories but first I needed to figure out a way to get to a store undetected and then decide what to buy. After putting a lot of thought into my situation, I remembered that my grandma lived in town, fairly close to one of the old five and dime department stores that sold makeup. I used the excuse to visit grandma, then go and shop. Or try to.

The only problem with my plan was that my dad worked downtown close to the store I wanted to try to buy my first makeup in. I was tired of using my mom’s samples, That was all well and good until I gathered my courage and walked into the makeup selection of the store I was in. As I viewed the extensive selection of cosmetics, I almost panicked and walked quickly from the store. There were so many choices and so little time to choose anything that might help me during my novice beauty program. Somehow, I stood my ground and picked out some foundation and lipstick which fit in with my limited budget, gathered my courage and headed for the checkout counter. Just knowing I would get made fun of along the way. Amazingly, the person at the cash register did not give me a second look as she took my money and I was no longer a virgin in buying my own feminine supplies. I just wished I had more access and money to do more.

I would have more financial resources later in life along with the knowledge to go with it as I learned the fun of doing thrift shopping for just the right choice of clothes to add to my wardrobe.  Plus, the thrift experiences gave me a chance to be patient in many of the bigger stores with seemingly an endless supply of discarded fashion. When I took the time to try on a new item I had never tried to wear before, I had two benefits. I didn’t have to pay much for the item and two, I could see how well it either flattered my difficult to please male testosterone poisoned body or didn’t. It helped too, when I was able to streamline the shopping experience and give myself time to vary my day as a novice transfeminine person. Instead of just facing an endless amount of clothes. I actually had time to do other things like take myself out to lunch. Then, again I was faced with an almost never-ending choice of where I could eat. Since I had already tried too many fast food drive throughs with various amounts of success, I decided to step up my game and try to eat at one of the casual dining restaurants I had went to and even managed as a man. Since I was still on a gender time clock and had to be home by a certain time dictated by when my second wife would be off of work, I was still facing so many choices with so little time to enjoy myself as a transgender woman.

My plan was to just get by and improve myself a little at a time in a world of ciswomen I was just discovering. By doing so, I discovered that most ciswomen ignored me if I was dressing to blend in with them or were just curious of why I was in their world. Of course, I did run into the occasional TERF woman who hated me and wanted me out of her world, which I did. One way or another, I was encountering far more women in my quest to be part of their world than I ever did any men because I just wanted to be out of my long-standing membership in the men’s club and they knew it. The only thing I did know was that I was increasingly not so lonely when I went out in the world to my regular straight venues. All my lesbian places had closed up and the gay venues I used to go to just brought back bad memories of me being looked at as just a drag queen so I was stuck…just where I wanted to be and I was satisfied, until I went too far and tried too hard to be accepted.

In my search for acceptance, I began to become too overconfident in my ability to succeed a began to look for more choices of where to go in such a short ill-conceived amount of time. What I did was start going to redneck themed places thinking I could be accepted when I was not and even had the cops called me one night in a venue, I was just trying to drink a couple beers then pee before I went to another place I had been to a lot. It turned out that they would sell me the beer, just not let me get rid of it.

As it turned out, I was/am able to live a long life and see many of my choices gang up on me in a very short period of time. Destiny worked its magic and gave me a full circle of life to live with. Throwing in that I was a transgender woman just added a little spice.

 

Saturday, June 6, 2026

Who Had it Easier

 

JJ Hart

The most ridiculous understatement I ever made to myself was thinking how much easier women have it in their lives than men do.

Those were the simpler days of just envying all the girls around me for their ability to wear pretty clothes when I was stuck in my usual boring male attire. As you can tell, my adolescent thought patterns about gender were much shallower back in those days. All I knew was I was having issues with going through male puberty and all its hair and added angles to my body while the girls were adding all the curves I so desperately wanted. It was about that time when I started to further torture myself by having dreams of being a pretty girl when I just had to wake up again to the same old world, I was so tired of at such an early age.

Another benefit I saw from the outside from being a girl was on the dating front. From my ultra shy vantage point, boys had to do all the work to chase a girl but gave it no thought to be a girl with no boys having any interest in you at all. It seemed all my ideas came from the problem I had for years of not being allowed to see behind the gender curtain to go through the insecurities of a girl’s puberty. As their bodies ramp up the necessities for possible childbirth later in life.  Which leads me to this, the incredibly short period of time a ciswoman has to level out their hormones and have the chance to live a so-called normal life. First, they have to go through puberty which shapes their bodies then go through child birthing years which strain their bodies and then go through menopause to reduce all the hormones again. Not to mention all the monthly menstrual periods most women must live with too.

In the days when I was busy with just being the “pretty, pretty princess” as my wife called me, she was taking me to task about never experiencing the so called downs of being a woman because I just wanted to appear as one, perfect my makeup and wear my pantyhose and heels as much as I could. For years, I went on clicking my merry way in my heels not giving much thought to what she was telling me. It was not until many years later that my heels finally led me to a path where I could finally learn what she was talking about.

Essentially, what I was able to learn from being a transgender woman and being able to live on both sides of the gender border was that both genders have their challenges. That humans are born as male and female, then get socialized (if they are lucky) into men and women. We transfeminine persons just were born into an unwanted male gender and were socialized into our chosen lives as trans women. The whole process gives us a deeper understanding of the world as we look into who has it easier in life, ciswomen or men.

Since the socialization process of being a male was what I was born into proved to be partially successful one for me, I have always thought men have had it easier. And women have it harder because they must put up with men. Even though, my gender dysphoria issues made me difficult to live with as a husband, I somehow have always found a woman to make the journey with me. Someday, I will have to write a post on the differences of my three wives during my life.

As I continued in vain to find the easy way out in my life, being a guy was the way to go as I found success in being able to bluster my way through in many situations and in others wondering how I would approach them as a transgender woman.

Finally, my gender travel took me behind the gender curtain where I could hear firsthand the experiences of all my ciswomen friends. It was not until then did I realize the grass was not always so green on the other side of the binary gender border. The only problem I did have was reversing all my experiences in the conversations we were having from male to female, so I did not out myself to my friends. I knew I was beginning to be successful when strangers outside of my circle of friends began to ask me questions on what to do about getting along with their boyfriend. I was flattered that other women had trusted me with their problems and were looking for input.

My own socialization journey had taught me that neither gender had it easier. Stereotyping here, men largely bluster and run when they can’t get their way and women are left to raise the kids and pick up the pieces. It is difficult to take such a complex subject such as gender and not stereotype something about it at some point, so I apologize.

I am sure that no matter where you are on your gender journey, you will encounter your own set of standards when it comes to the male and female genders and where you fit. It will certainly be an interesting journey with many individuals trying to tell you to stop. At that point, you must decide if maybe you have had it more difficult than either of the two main binary genders you have encountered. Many of them simply will not have the understanding it takes to approve of your journey, and you will have to move on. But, on the other hand, there could others who approve of you and even want to help. Just be careful that you know which is which.

When it comes right down to it, that girl you envied from afar in study hall, all the way to the woman whose fashion and passing privilege you admired so much both had their own problems to deal with. You just must get behind the feminine gender curtain to figure out just what they were.

 

 

 

 

Monday, June 1, 2026

Visiting the Vampires

 

Image from Mike Lloyd
on UnSplash.

Today was a rushed visit to the Cincinnati Veterans Hospital for bloodwork before they shut down for a week to switch over to a new digital system that we all know will cause new headaches.

Most all my bloodwork can be done at an off-site closer clinic to my house which does not require a trip downtown into a very congested area. Plus, with my mobility issues, it makes the entire process of going downtown for specialized work very unpopular with me and my wife Liz who must do all the driving.

The specialized test I needed to get done before the shutdown June fourth was for my Estradiol blood levels. For some reason, my levels had dropped nearly fifty points from a level they had been at for literally years. For that reason, my endocrinologist requested another test of my HRT levels. When this level comes back, if it stays low, it will be interesting to see what ideas she has, such as maybe doing away with the patch system and switching to injections which for no real reason, I have always stayed away from.  I am not afraid of needles; I am just lazy about the possibility of giving myself injections. One way or another, I will have to jump off that bridge when I come to it. I think my hormonal levels have jumped back up because of an overall increase in the fullness of my breasts, so I may be jumping to conclusions I did not have to.

Past that, we were able to beat the rush this morning at the VA because the vampires (blood lab people) open up at six thirty and we were able to get an early start and be there before seven. For the appointment, I chose a three-quarter sleeve feminine lace trimmed blouse, leggings and flats. Along with a light application of makeup which seemed to work because I was not misgendered at all and was actually smiled at by several men who passed me by on the way to the second-floor labs. I will take that as a win everyday since I have had mixed results over the years at that hospital. Usually, the smaller clinic I go to is better because they know and remember me, but they just could not do the specialized Estradiol test because they needed to send it out for testing.

Now I play the waiting game (which if you were in the military, you know what I am talking about) before I can get the results back. I doubt if it will be very soon because of the overall system disruptions which are coming up.

This is a short post today because it is my transgender grandchild’s birthday today who is working up in Maine and I have to send them birthday wishes plus a small gift. Happy Birthday “A.”

 

  

Sunday, May 24, 2026

You Never Know until You Try

 

Image from Leo Visions
on UnSplash.


You never know until you try was drilled into me as a kid by my WWII generation parents whenever I was facing a potential difficult situation. Little did they know, their insistence on me trying to do the improbable would come back to haunt them in a very different way. Back in those days (in the 1950’s) gender issues were referred to as mental illness and any reference to their eldest son being mentally ill would have been frowned on, so I was stuck wondering if I was really a boy who wanted to be a girl.

The only thing I knew to do was to keep cross-dressing in front of the family’s full length hallway mirror. Imagining I was one of the pretty girls I desperately wanted to be. At the time, I had no idea my gender issues would last the better part of fifty years and take up huge portions of my life. Not that I could have done anything about it if I had tried which I did a number of times when I purged nearly all my feminine belongings swearing never to pick them up again. I was stuck being a male and somehow, I needed to make the best of it. Like so many people I knew with gender issues, purging never worked. The pressure built until I could take it no longer and again, I was accumulating women’s clothes again and wearing them.

At the least I tried to go back to mentally being male full-time and failed miserably at it. All I knew was when I was not thinking about getting out of my dark, lonely gender closet, I was not happy at all and when I at least tried to be me in the mirror it took the pressure off. Even if it was only for a while. At the same time, I was acutely aware that I was doing the best I could to see if I could improve my appearance as a pretty girl. How I never got caught doing all of this, I will never know, and I even resorted to taking plastic bags of clothes and makeup into the neighboring woods so I could escape the prying eyes of my slightly younger brother and family.

My mentality of never knowing you could do something until you try really came to the forefront when I was drafted into the Army during the Vietnam War. Instead of taking the two-year plan with a ticket to Southeast Asia, I took a chance and signed up to try to get a job I wanted in the American Forces Radio and Television Service. With a lot of luck and the help of a congressman whose radio station I worked for, against all odds, I got one of the sixty job slots in the Army for AFRTS. It turned out the whole process turned my life around and taught me that anything could be possible. If you went out of your way to try. Probably the most valuable lesson that I could have ever learned as I looked ahead at my path to becoming a successful transfeminine person. If it had worked for me once, why couldn’t it do it again.

As I set out to leave my gender closet behind and improve my life, I know I took on a journey I would not readily recommend to others. When I started to leave the mirror and join the world as a trans woman, I used a tool that I had already used effectively as a man in my previous life. It was alcohol, and I knew I could use it to build up much needed courage to be in the world as a transgender woman and not get myself into more trouble as I was presenting as a single woman in an establishment which served alcohol. Gay, straight or lesbian, it did not matter. I found I could get by if I stayed out of the redneck leaning venues. I was also well schooled in the artform of driving while buzzed from all my days in the Army when I did all the driving. More than anything else, this was back in the days before the major crackdowns on drunken drivers, so I was safer, and in NO WAY do I recommend what I did.

Also, what I think is tougher these days than when I was intensely lonely and looking for companionship is the world of on-line dating. When I was seeking a date, I played both sides of the gender coin, because I was in the unique position of being a transgender woman who favored lesbians. Looking back, I think I got the most attention from men seeking men dating sites. But just knowing that the amount of trash I would receive was at its best humorous and at its worst, a disaster because I refused to meet anyone in a public place which was not of my choosing. I was stood up more times than I would care to count or remember because my life was destined to change forever when I met my future wife Liz on a woman seeking woman dating site.

Liz responded to my picture saying I had sad eyes which was entirely possible at that time of my life. Amazingly, she lived relatively close to me in a town (Cincinnati) that I had always admired. From there, I began to become involved in her friend’s girl’s nights out and I was able to do more to learn what was behind the gender curtain than I had ever thought possible. The entire on-line dating world for me proved again you never know what you are going to get until you try.

These days again it is more problematic to find someone online with all the scammers out there, but destiny can never find you if you never venture out of your dark lonely closet and light up your path to a brighter future.

I wonder what my deceased parents would think now of what they taught me so long ago.

 

 

 

Saturday, May 23, 2026

Being Hyper Focused as a Trans Girl

 

Image from Maxim Tolinisky 
on UnSplash.

As I followed my path into transgender womanhood, I found several times that I was too focused on my goal of presenting successfully as a woman when I went out and tried to join the world.

Essentially, what I mean is I was trying too hard to mimic the way ciswomen look and how they move about in the world. I had not yet had the time out in the world to develop the muscle memory I needed to be at my best with others. I so badly did not want to slip back into my old male ways and look like a linebacker in drag in high heels in the mall. In the meantime, I was spending every spare moment I had by myself to try to practice my best feminine walk.

The problem became when I was practicing too much and forgot where I was. Looking feminine in the least at work would not have been good for my macho career. I did the best I could with the time I had to work with just was not enough to create the habits I needed to progress the way I wanted to towards my transfeminine dream. Every time I went out, I would do something wrong and destroy the image of being female that I was trying to portray. If I had my makeup, clothes and hair to a point where I was satisfied, something would come along like catching one of my heels in a sidewalk crack to hurt me. I was very frustrated at the time until I finally began to relax and began to enjoy the new world I so badly wanted to be part of. As I did it though, I was totally surprised at how complex the entire scope of what I wanted to do as a potential successful trans woman would be. My life was like one of those huge “Bloomin Onions” you get at steakhouses. Every time you peel back a layer, you find another layer to surprise you.

As it turned out, at the time I was peeling back more gender layers much quicker than I had ever imagined. I was dodging all the stop signs that I thought I would have and was able to look around my world and enjoy what I saw. Most importantly, I was becoming the me I always wanted or destined to be. Again, I was being blindsided in that I would have to go through yet another transition as my life was coming full circle. I was not becoming someone different at all. I was just becoming me.

The one remaining aspect of my transgender being I did have to remain hyper focused on was when I began in depth communication with other women. I was always paranoid that I would give away too much of my old male past when I was talking with another woman. I worked so hard to be in the world as I was, I did not want to out myself as an intruder. Quickly, I made strides to learn the different way ciswomen communicate that men just don’t understand such as non-verbal cues about danger and happiness. All the way to the power of passive aggression that women use so effectively. To aid in my efforts, I even took feminine vocal lessons to learn key terminology I would need to complete my communication efforts in the world.

As I followed this new direction on my gender path, I did slide back into being hyper focused in my quest to be me. I was intently watching all my new ciswomen friends to see how they lived their lives and how I could fit in. In essence, the new me needed a new place to live and they gave it to me without ever realizing what they were doing because they took their lives behind the feminine gender curtain for granted and I never could. And still don’t to this day since I spent so long trying my best in the dark to get there. I guess I was paying my dues as I learned what my second wife meant when she called me a terrible woman. Back then I was, but I did not want to make that mistake again. So, I became hyper focused on a new goal…earning a spot behind the gender curtain.

My confusion set in because I learned early in life what it took to survive behind the male gender curtain, but I had no clue at all what it would take to survive as a trans woman. Because I knew I would never be able to have such life altering experiences such as carrying and birthing a child such as ciswomen have but on the other hand, I still had a very unique way to my womanhood which still counted. I just had to wait and earn my way back to being me. Furthermore, I did not want to completely throw away everything that I learned for fifty years living in a man’s world. I just wanted to take the building blocks I learned and use them so I would be able to be a quality transfeminine “me” person and never be told again I made a terrible woman. If I was “making” anything from scratch, I wanted it to be presentable to the world.

Once I was able to stop being hyper focused on my early experiences with makeup, hair and appearance, reality in the world set in which meant I would have a chance to live my dream of throwing out or giving away all my male clothes and starting all over again. I hope being a hyper blend of the two main gender binaries helped me along once I finally sensed the true path I wanted to be on.

The ups and downs of life on the journey I took was never easy, but worth it when I made it to the surprise location I was heading for that I never realized. All along, I was just focused on being me.

 

Tuesday, May 19, 2026

Are We Having Fun Yet?

 

Image from Katie Treadway
on UnSplash.

Having fun as a transgender woman or transgender man can be difficult to define. First, let’s define fun as something that provides mirth and amusement. Which comes from “Dictionary.com.”

In my case, I cannot remember finding much “mirth and amusement” when I was cross dressing as much as I could to present as an attractive girl. All I can remember was that I was experiencing deep satisfaction when I thought I had succeeded. As I began to search for a better term, I went back to the “Dictionary.Com” to look up the definition of happy. Because happy is how I felt when I thought I had succeeded into transforming myself into a pretty girl. I was right when the definition of happy was “delighted, pleased or glad” when something was accomplished. It fit me totally because it worked in all aspects of what I was trying to do. Actually, it was all three of the delighted, pleased or glad definitions which fit me exactly.

The problem I was having was getting to the point where I could be happy about trying to cross the gender border. I severely struggled to find the fine line where I could disguise my broad shoulders and narrow hips of my testosterone poisoned body. I certainly was not happy or having any fun when I was brutally laughed at by the way I was trying to present myself as a woman in the world. As I always point out, back then teenaged girls were the biggest test I faced when I went to the malls and they seemed to be attracted to me like magnets, for all the wrong reasons. It took me a while to realize I was trying to dress like teenagers, which brought me completely undo attention. There was no way I could be happy.

What I also did not understand was that fun or being happy was a fleeting thing for me. Sort of what had you have done for me recently, type of thinking which I was very used to from how I was raised. For the most part, I was never allowed to be happy, so I did not miss it at all. I also say for the most part because slowly I began to discover I could feel happy when I was cross-dressing as a man into my true feminine self. When I was able to find the proper clothes, shoes and wigs which helped me with my appearance with my makeup, I could relax and enjoy a new world I had only dreamed of.  Fun became to me when I could escape the male world, I was forced to spend so much time in and explore all the new facets of being a confident transfeminine person. It made me happy to discover who I really was destined to be in life.

As I headed past the fun and happy part of discovering myself as a transgender woman, I needed to mention the satisfaction I felt when I had reached the point where my diet had kicked in and I could buy more stylish clothes in my own size for the first time ever in my life. I was ecstatic in my pre-hormonal HRT days when a cross-dresser friend of mine purged his feminine belongings and gifted me a set of silicone breast forms that I needed to run out and size just the right bra for.

Those were the early days of my explorations in Columbus, Ohio when I could attend very diverse by invitation only parties where I could see everyone from lesbians to transgender women considering gender realignment surgeries so I could have a idea of how I might want to live my life in the future. Almost every party I went to was to be a fun learning experience, and I could not wait for the next one. At the same time, I was thinking if I was having this much fun, how could it be wrong to have it.

The only negative I experienced was the night I was cornered in a narrow hallway by a huge admirer of crossdressers and almost learned the hard way about what ciswomen learn at an early age. To not put yourself in compromising positions with men which could possibly overpower you and get yourself into deep trouble. I was lucky that my wife came along to bail me out of the situation I unknowingly put myself into.  It was no fun hearing her, I told you so’s all the way home. Mainly because she did not approve of what I was wearing.

As my life progressed towards the ultimate goal of leading a fulltime life as a transgender woman, unfortunately, my wife stood right in my way of progressing.  Which meant I needed to cheat on her with another woman which was me. Every time I slipped out of the house in my heels, jeans or boots, I normally had a good time as I was finally having fun as a trans woman and did not want to ever give it up,  I had gone too far to ever look back to an old male life I never had a choice on living to start with. Like it or not, my life had put me on a collision course of having to decide what I was going to do about my marriage. The course was disrupted when my wife unexpectedly passed away from a massive heart attack leaving me tragically alone after twenty-five years of marriage.

Most certainly, those days of my life were no fun, and not filled with happiness. On the other hand, they were filled with uncertainty and loneliness until I could find my way home again. Thanks in no small part to my inner feminine self who took over my life and others such as my daughter and future wife Liz. Who helped to pull me from my major pity party. When that happened, life became fun again as I was able to lead a life in the feminine world I always wanted to be part of.

 

 

                               

 

 

Friday, May 15, 2026

When Every day is Day One

 

JJ Hart

We all know how difficult being a transgender woman or transgender man can be. For years, it seems as if you are starting on day one when you are trying to catch up with ciswomen who have lived a feminine existence their entire life.

For me, my journey started when on certain mornings when I did not know if I was going to be a boy (physically) or a girl (mentally) that day. My thoughts often came from vivid dreams I had from the night before that I was living a life as a pretty girl. I just couldn't shake the idea that something was wrong in my life, and I couldn't do much about it except occasionally cross dress in front of the mirror in mom’s clothes and makeup. When I did, early on I needed a lot of help with my makeup and everyday when I tried something new on my face, I was starting all over again. Plus, it did not help that most every time I cross-dressed, it was an adventure in not getting caught. Between my parents and my slightly younger brother, earning my private time to be on my own and be a girl was difficult.

It took me years to shake the idea that every day as a transwoman was still day one in my life. Mainly because, I was still learning so much from all the ciswomen I was around in my new world. I had plenty of stop signs on my gender path I needed to negotiate as I made my way towards my dream of living full-time as a transfeminine person. Some of the stop signs were busy four way stops when I really needed to stop, look both ways, and make the difficult decision to proceed. Looking back now, I don’t know how I managed not to have any major collisions with anyone but my second wife who unfortunately had a front row seat in my transition from just cross-dressing on a part-time basis all the way to considering HRT or gender affirming hormones as a transgender woman.

What kept me going was my deep-seated knowledge that what I was doing was right. All the cross-dressing I was doing was just practice towards a bigger, brighter future as a trans woman. Looking at it that way was certainly difficult, but it was all I could cling to if I was to keep my fragile mental health intact. As my wife told me when we were fighting about my gender that I made a terrible woman. So, I needed to find out what she meant because she added that she was not talking about appearance which I thought I was doing better with.

I set out at that time to re-dedicate myself to understanding a woman’s life. I was naĂŻve at the time and thought I could learn more while I was still presenting as a man fulltime. Years later, when I had crossed the gender border publicly as a trans woman, I finally was invited back behind the gender curtain so I could learn a lot and not be a terrible woman. For most of you who do not know, my wife unexpectedly passed away from a massive heart attack after twenty-five years of marriage to me and she never was able to see the better woman I had become. Mainly because my time behind the curtain enabled me to start all over again and mold the new woman, I wanted to be. Including most of all the nuances and the layers a female must live through before she becomes a woman. My inner female was forced to stay back and be dormant for all those decades before she could claim her ultimate gender prize also. She just had to take a vastly different path to get there.

At that point in my life, everyday was day one again when I donated all my male clothes and vowed to never look back again at my male life. Which I ultimately found impossible to do. Male influences built me into the person I had become as a transgender woman and made me stronger in the process. I even brought experiences from the most male dominated part of my life to my gender table as I remembered the days I went through in Army basic training. There was no need to throw away valuable experience I could use in my new life.

It turned out to be the most exciting time of my life when I could finally live my truth in the world. And I was able to forget the dark days of my youth when I began to deeply question what gender I was. Having all the help I did to finally begin to fill out my gender workbook helped me too, even though I was rejected on occasion and needed to start all over again. I urge all of you who are considering a journey in life the way I did, is to be resilient and expect many ups and downs along the way. Most are just learning experiences anyway and can be valuable as you are allowed to play in the girls’ (or boys for you trans guys) sandbox. It takes time and experience for your confidence to grow as you navigate one of the most difficult paths a human being can take.

Slowly but surely, every day will not feel like day one as you get used to living a full-time life you have always dreamed of in a gender world you want to be a part of. For me, it was like taking a great deep breath of fresh air when I was finally checked out and was able to begin the long-awaited HRT which would transform my body outwardly and more intensely, inwardly. My entire being was telling me what took me so long when the male to female feminizing hormones hit my system. But I did not need the hormones to tell me who I was, they were like the icing on my transgender cake and made every day a better day.

 

 

Wednesday, May 13, 2026

Who You Going to Call as a Trans Girl

 

My friend Raquel 

One of my biggest problems when I decided to test the world as a new cross-dresser or transgender woman was having no one to ask about my issues. For example, why was I getting “clocked” or read every time I left the mirror and went to the mall. It turned out that the issue was just tied into how I was dressing my male contoured body by not doing my best to blend in. Ciswomen everywhere were laughing at me from my cross-dressing mistakes and ruining my all-important confidence.

As I said, I had absolutely no one to go to, to discuss the problems I was having in the world. I had no mom to try to rein me in in my trans-teen years or a peer group of girls my age for me to copy. As it was when I was mom’s phantom daughter, I ended up wearing makeup and shaving my legs before most of the girls my age were allowed to do it. Mom, for some reason, never looked for the tell-tale signs of being a curious girl from her oldest son.

Skipping ahead quite a bit, my closet was truly dark in the years before the internet when all there was, was Virginia Prince and “Transvestia” or the “Tri-Ess” social mixers I used to attend every time I could. My hope was that I could find a friend or acquaintance that I could get to know to understand our unique gender issues, but it never worked out that way and I still did not have anyone to call with my cross-dressing problems. The only thing I walked away with was I came away with being more confused than ever before. I did not know how many layers of individuals I would be able to meet at the social mixers I was able to attend. Many more levels than the publications I was reading from “Virginia” led me to believe that existed when she was calling her group as one for heterosexual men only. She probably needed to turn a blind eye and ignore all the activity going on beyond the hotel room doors where the mixers were being held. There was most likely different kinds of mixing than Virginia and the “Tri-Ess” groups would have approved of.

All sexuality aside, there was a diverse group of people who attended, all the way from men in dresses with cigars and cowboy hats trying to hide their femininity to the ultra-feminine “A” listers who were on their way to gender alignment surgeries. Neither of which did I fit in with. I was somewhere in between once again with no one to call or hang out with and exchange trans-girl talk.

It turned out, I only made one significant trans friend and that was Raquel before she moved away from our native Ohio to Dallas, Texas. Even if we were on slightly differing transition paths, we still had enough in common to get along and socialize. She was headed towards gender operations and attracting men while I was on the path of staying the same physically and hanging out with lesbian women. Opposites do attract too in the world of transgender women when we keep an open mind about who is on the right path. The whole situation with Raquel briefly gave me a person to call, and I truly appreciated it even though we have not seen each other in person for years as she is still in Dallas and I am with my wife Liz in Cincinnati.

As I bring up Liz and other ciswomen who were instrumental in bringing out my best as a transwoman, my interactions with them brought on an entirely different dynamic. It was not as if I was calling them for advice on my male to female femininization project, they were always there if I needed them. I was still embarking on an intense learning project as I crossed the gender border for the first time. So, I needed their input like how my lesbian friend Kim handled a man harassing her in a sports bar about her “Pittsburgh Steelers” leather jacket. I did not have to call her for her knowledge; it was right there for my taking. Learning is always easier if you are having fun, and I was having a blast.

We transgender women (no matter where you are on your path) begin our lives as adults on the outside looking into to the world of ciswomen we so completely want to be a part of. In my life I went full circle of having my first fiancé dress me head to toe as a woman when I took the time and effort to call her. She ended up holding it against me for the rest of the time we were together and worse yet, I was not that impressed with her makeup job anyhow. In my circle, she was actually the only ciswoman I sought out for help. The rest, I learned the art of femininity by osmosis or by just observing everything my friends were doing and thinking I could do it too.

The main big problem comes when our frail confidence is shattered when someone says we can’t succeed and major setbacks occur. Unless you are fortunate enough to have an understanding spouse or friend to help you through the rough patches, it still is hard to find someone to call. My suggestion at that point is to seek out help from a local LGBTQ group you can interact with. In person or even virtually until you can regain your confidence about your authentic transfeminine self. Where there is a will, there is a way out of the darkest gender closet.

When you do, maybe you can reach the best step ever and be able to pay forward your confidence in life to help others in need. Which is my main goal for writing this blog. I don’t want to see anyone suffering needlessly in their dark closet.

 

Tuesday, May 12, 2026

Success is no Accident in the Trans World

 

Image from Priscilla du Preeze
on UnSplash. 

Success is definitely no accident in the world of transgender women and transgender men. Very few of us survive our puberty by having no natural characteristics of our authentic selves that we want to be.  I know I wanted nothing to do with the size and angles my male body was willing me to have without my permission.

It was not until I became very serious about my male to female femininization project did, I take the necessary steps I needed to take to begin to ensure my future successes were no accident. The first step I took was to try to make myself smaller for I could fit into more stylish feminine clothes. Naturally, all I could do to make me smaller was to go on a diet. I was successful in a short period of time because I had a very active job and my high male metabolism was still working well. I ended up losing nearly fifty pounds quickly and had the fun job of going back to the thrift stores and searching for new clothes in my size and trying them on.

The next step I took to improve my work to become more feminine to the public was to take better care of my skin. Every day I was careful to moisturize my face after I shaved to make it easier for me to use less makeup because I knew less was more when it came to using makeup. It was a start but was all I could do without the public and my wife beginning to notice a major change in me. Even so, I was proud of the beginning steps I was taking towards my overall femininization.

It proved to me that over the long haul, none of this path I was on would be easy to navigate as I sought to cross the gender border. Also, what I did not know was how much more difficult my life would be because just looking like a ciswoman would not be the end result of the process. It would just be the beginning when I left the mirror and challenged the world as a novice cross-dresser or transgender woman. I never realized the depth and scope of the world women use to run their lives. With or without the help of men.

By accepting the challenge of femineity I was seeking, I was also challenged to move like a woman and more importantly communicate as a woman because I discovered quickly how many other women wondered what I was doing in their world. From the ease of dealing with clothing stores clerks to having conversations with women at restaurant/bars I was at, I found I was dealing with much more interaction than I ever had as a man. My new success was no accident, but I needed to work hard to keep it and always stay aware of my new surroundings. One slip up and the setback could be tremendous and discouraging to my dream goal of being able to live full-time as a transfeminine person.

Many times, my frustration grew over the decades that I struggled with my gender issues. Was I going too fast by going out into the world, or not enough to keep learning what I needed to know to progress along my gender path which kept showing me infuriating stop signs along the way. Particularly from my male self who was becoming very successful in his business world. He was making it difficult to choose between his growing male privileges and living the life I had always dreamed of. Ironically, it was lessons he learned at work which were carried over to my female life that proved that success was no accident. If I wanted my goal bad enough, I could achieve it.

As I progressed with carving out my new feminine life as a trans woman, I found that my successes were painting me into corners which were difficult to get out of. I had nights when butch lesbians were flirting with me and buying me drinks until I ran out of time and had to be back home before my wife was take my makeup off then calmly try to wind down by watching television. I was on the gender rollercoaster going from one high to another and eventually it was too much to take.

Before I broke for the final time and had to make a decision between staying with my wife as a man and deciding to live my life as a woman, she took my decision away and suddenly passed away. Leaving me all alone with my other woman who happened to be me. It took a while for the shock to wear off, but when it did, my internal female took right over and claimed her territory in my life. She thought success was no accident and she had claimed hers by paying for those dues all those decades when she was hidden for the most part. In the light of day, she flourished and never looked back. Especially when HRT or gender affirming hormones were introduced into her old male system.

The ultimate measure of success is coming around and transitioning ourselves from transgender into just being ourselves. Many of us have to go through extensive gender realignment surgeries to do it, and some not but that is OK. Whatever makes you whole as a person is the final key to the lock or piece to the puzzle. I am sure that whatever the case, everyone who succeeded in finding themselves would agree that success was no accident. They had to work hard to achieve it.

If you are on your path, just keep up the hard work you are doing, and you can find success also. Pursuing such a complex journey will never be easy but as the saying goes, if it was easy, would it be worth it.

Thanks to all of you who read along with my posts! All your thoughts, comments, claps and subscriptions are always welcomed.

 

 

 

 

Understanding is the First Step to Overcoming Fear

  JJ Hart (Center) on a  girls' night out.  Before you can overcome fear, you need to understand exactly what you are afraid of. I kn...