Showing posts with label transgender woman. Show all posts
Showing posts with label transgender woman. Show all posts

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!

 

 

Monday, August 24, 2026

Help Me Out of this Box!

 

Image from Tamara Bellis
on UnSplash. 

Since I was born “AMAB” (Assigned male at Birth) I was automatically put into a box I could not easily get out of.

Plus, I had the extra disadvantage of being born into a very male dominated, competitive family, so my box was harder to get out of. Like many of you, I had to sneak around my family’s back to even cross-dress into mom’s clothes and makeup to feel better. The worst part about it was that I did not understand why I wanted to be feminine and felt so all alone when I thought about it. Society had done a good job of building a sturdy box around me with very high sides to see the world out of.

As life went on, I learned to be self-sufficient as I hid my gender truth from the world. Very early on I learned I wanted to do so much more than just look like a girl, I wanted a chance to live their life. But I needed to escape my box somehow to do it with absolutely no help from anyone at all. There were only the girls at school for me to envy and try to copy myself after I returned home and had a chance to cross-dress again in front of the mirror.

When I first tried to take myself out into the public’s eye for the first time, it was difficult leaving my box to do it. I was safe there, and I could be the pretty girl I always wanted to be without anyone questioning me. Even though I was not surviving the world well as a novice cross-dresser walking through the malls that I knew, I was determined to keep trying until I got it right. That is if I ever could as I was very insecure in thinking I ever could come close to my dream of living as a woman.

As life always does, it got directly in my way of ever getting out of my box. The only way I could try very early was by going to Halloween parties dressed as a person who I really wanted to be in life but could never tell anyone. At least at Halloween, I could show the world the transfeminine me and hope it did not wreck my life at the time before I could scurry back to my box and hide again. The problem with Halloween was it only happened once a year and I couldn't wait for the next one to show off my feminine spirit. It all led me to gaining a greater awareness to who I really was and how much I needed to expand my world as a new transgender woman in the world.

Another problem I had was having two strong influences around me, who wanted me to stay in my box and even make it stronger. The two were my male self and my second wife who had everything to lose each time I gained more confidence as myself. They did not understand the turmoil I was going through myself and could not help me, I was on some sort of a gender roller-coaster with all its ups and downs. One of my major ups or gender euphoria came when I was mistaken for a ciswoman at a cross-dresser, transgender mixer I went to one night without my wife. That was certainly the high point, but then the lows began to hit me when I was firmly stuck back in my box with no way to experience the next high. Sadly, I did not know where my life was going to take me then. Except for the small idea that I might have the appearance part of my gender puzzle solved.

More frustration sat in when my wife told me there was so much more to being a woman than just looking like one and I was stuck with no real way to understand what she meant. I was still operating as too much of a cisman to be allowed to be behind the gender curtain to understand all the complexities ciswomen go through in life. To make up for it, I tried to adopt female mentors to learn from. Immediately I chose my mom and my wife to learn from because they were both strong, independent women whom I wanted to be like. It was a true jump for me to go from being a shy trans woman hiding in my box at home to getting out and trying to find out if I could live my life-long dream. What I did was build up confidence slowly until I could shed my male self and his privileges and just do it.

Little did I know, when I did shed my male self, I would end up bringing a big part of him with me. I made him my beast of burden when he carried what was left of him into my scary, yet exciting new world. I learned again how complex ciswomen were and if I wanted to watch sports on a big screen television with a beer in front of me I could and not feel out of place as a transgender woman.

In many ways, I was dismantling my old box and using the pieces I needed to construct the new me who had always been there but had nowhere to live. It felt great for once to feel free of all the old male constraints I had to live with. I had many, so the path I embarked on became very complex as I sorted out exactly who I wanted to be. Plus, I needed to be careful to finally judge when the best jumping off point for me to put my old male self behind me and start a new one. A unique spot that most humans do not ever have the chance to do.

If you are considering what you will do with your gender box, just be careful when you deconstruct it because it can contain many hidden problems. On the other hand, you are embarking on an exciting journey if you can make the best out of it.

Thanks for reading along with all my lifetime adventures as I attempt to bring our gender struggles into focus. Taking the time to read, and comment too are always appreciated!

 

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.

 

Monday, August 17, 2026

Figuring it All Out

 

Image from Erik McLean 
on UnSplash.  

I correspond quite a bit with one of my regular readers “Bobbie” whose life and mine amazingly align up in many ways including our military service. And if my memory is correct, she also benefited from a heavily influenced lesbian set of interactions. My apologies if I am wrong with my old memory which is like a steel trap…a rusted one. Because I heavily benefited (and still do to this day) with my feminine “upbringing” with my lesbian friends.

At any rate the reason for this post I to explain how Bobbie and I diverged on our gender paths. One very important way was when Bobbie went into how precisely she planned her male to female transition. All the way down to having a supportive wife. Which I did not and I needed to work my transition around her because she flat out refused to live with another woman. But on the other hand, did not mind that I was a cross dresser. She even went as far as scraping money from our limited family finances for me to rent a motel room to cross-dress in so I did not have to go out from our house which was on a heavily traveled street.

 Another way I diverged from Bobbie was her employment as a man required her to have several backup plans for every move, which mine didn’t. I was in the fast-paced casual dining industry which required me to work in an environment which constantly changed and was very difficult to plan ahead for. All of which really appealed to me at the time. Also, for various other reasons, I have decided to stay away from all gender related surgeries. Much different from Bobbie as I will translate for you:

When the transformation began, the checklist was social first, add HRT, get the orchi and then the bottom surgery. A BA may be in the offing as my P has finally exhausted any more growth and a "Barely B" doesn't quite cut it.” Translating, “Orchi” means removal of the testicles, “BA” means breast augmentation surgery and “P” means taking progesterone hormones in addition to any Estradiol you may be also taking. Finally, “Barely B” means her breast size under the hormones she is taking, and “bottom surgery” is genital realignment surgery and is a major move.

I also decided against taking any progesterone after my endocrinologist did not like the idea at the Veterans Administration. But on the other hand, I started like Bobbie did with social and then went to the HRT or hormone replacement therapy and then went off to live my life as a transfeminine person. By this time, I was in my sixties, excited about my new life and set out to find someone unique enough to want to share it with me.

As you can tell, the whole male to female femininization path is not for the weak of heart and very much trashes the idea that transgender women embark down this extreme path out of a desire to just dress and look like a ciswoman. I get amused when I read that and think if the person saying it only knew the truth, they would certainly think differently.

Also, you can tell from Bobbie’s and I’s paths, there are many different ways to get to where we want to go as transgender women and transgender men. Even though my first dinner date as a trans woman was with a trans man, I still thought I knew the layers of the lesbian community, but I did not. Not only was I learning something totally new, but at the same time, finding out where I fit in. As the result of pure effort and observation, I learned I fit in quite well with the femmes or “lipstick” lesbians I encountered. To this day, I still benefit from my initial friendships I made with lesbians. As I have been in a relationship with a ciswoman lesbian for over fourteen years now and is going strong.

You may not have the circumstance or the ability yet to go “social” like Bobbie and I did, but the world is always changing, and you can change with it. Change is also different. You can plan ahead for six different scenarios (like Bobbie did) or pretty much just step out into the world and do the best you can like I did. I think now, I just wanted someone to realize my truth who knew me, but then it grew into carving out a whole new feminine life away from my old male one. I guess you could say I won the battle by taking an approach I never thought of taking. It was only then that I did set up an orderly “bucket list” of what I wanted to try to do behind the gender curtain in the world at large. As I was getting closer and closer to a dream life I never thought I could succeed in, for the first time in my life I needed to plan ahead and then let destiny take control of my life.

Examples of how destiny led me to successful outcomes were when I was matched up at the VA with a therapist who was knowledgeable about LGBTQ persons and specifically trans ones and was willing and able to help me with important tasks such changing as many of my legal markers that I could. She was really good and even helped me separate my depression and anxiety issues from my gender dysphoria. Maybe most importantly, she opened the door for my approval for HRT which I still cherish today. Sadly, my therapist moved on but I was lucky to have her when I did.

No matter where you are in your gender journey, I always enjoy hearing from you. As I said, remember there is no right or wrong way to discover your true self. I am always interested to hear of different paths. Humans are a very complex tribe and being transgender might be the most complex as all. Just remember you are in excellent company.

 

 

 

 

 

 

Sunday, August 16, 2026

Being Better as a Trans Woman

 

Image from Donald Gianetti
on UnSplash.


Often you must be better than the world to prove yourself as a transgender woman or transgender man.

An easy example would be we have to be better with our appearance. Because of the current lack of concern over appearance with many ciswomen and cismen, it’s an anything goes fashion world when women are wearing their pajamas and slippers to shop at a big box store, I won’t mention. Because we trans persons have so far to come in the appearance department, we cannot set our appearance bar that low or even want to.

Another problem with appearance is that we have had so few natural advantages to help us along when we first take the tentative steps out of our gender closets. In the case of transgender women, very few have the advantage of escaping the ravages of puberty which gives us angles, broad shoulders and deep voices. So, unlike the curves and softness we see in the women around us and envy so much. To get by in the world as a cross-dresser, we must strive to cover our natural flaws and act like we are not doing it.

The good thing is that ciswomen provide us with a big range of fashion to work from. Some wear dresses, some wear pants, some go without makeup and others don’t as life goes by. All you have to do is grab a spot you feel comfortable in and try to maintain it in a world of curious ciswomen who want to know more about you. You notice I said try to maintain it because early on, finding the best fashion and learning hair and makeup are major challenges we face. As our old bodies do not want to cooperate with the new path you have set them on.

Since I have always felt more comfortable in pants, leggings or well fitted jeans as a trans woman, I often took in criticism from other novice cross-dressers when I went to mixers in pants. Per norm, I did not care what they said about wearing pants as a man all the time so why I would do it as a woman because I was noticing how stylish some women look in their pants. I even had a glamorous silky black low-cut pants suit I wore to prove them wrong. Plus. most importantly what I wore was none of their business if I was aiming to be as good as the world of ciswomen in public at large who were increasingly wearing pants in their wardrobes. Not a bunch of cross-dressers at a social/mixer.

The more I was out in the world and interacting with the public, I discovered that appearance was just a small part of being better than the next person. Following some rough early experiments with my presentation as a transfeminine person, I settled into noticing who was noticing me. I learned men rejected me almost completely (which was fine by me) and women on the other hand wholeheartedly accepted the new me who wanted so badly to be in their world. The percentage of gender acceptance I received totally surprised me and I had to up my game to get better when I faced the public with so much more at stake.

Suddenly, women wanted to talk to me, and I was initially surprised and had to talk back. Then as now, I am very self-conscious about my voice, and it took me what seemed like an eternity to understand my communication skills centered more around what I was saying more than how I was saying it. In fact, I needed feminine vocal lessons to learn more about how women speak to each other. Primarily when men were not around. I also leaned the power of passive aggressive speech behavior in cis women and how it could apply to me when a potentially smiling face did not equal a supportive woman who could just as easy stab you in the back. After I tended to more than a few claw marks down my back, I adjusted to the new world I was in and survived by being better than them.

All these steps led me to pursuing an expanded transgender bucket list of potential things I wanted to do as a trans woman. To learn if I would want to do them on a permanent basis. As my checklist grew, my confidence did too and I discovered how natural I felt in the new exciting yet scary world I was in stripped of all my old male privilege such as dealing with my own personal security. With the menacing male scowl being gone, I had to rely of my new feminine senses to get me by and to stay out of potentially dangerous situations. It was all a major lesson of being better in the world out of a sense of pure survival as a new transgender woman.

At that point, destiny set in for me and set my life upside down as nearly all the loved ones I new and respected passed away. Leaving me all alone. To survive, I had to quickly quit being a victim and decide which direction my life would take. I took the feminine path, was approved for HRT or gender affirming hormones and prepared myself for a bumpy path ahead. At the age of sixty, I needed all the wisdom I had learned from a predominately male life and apply it all to a new female existence and exceed my own expectations.

By taking chances in the world, I had lucked into finding supportive ciswomen friends into my new life and I give them all the credit for the ease that it happened. And it made all the prep work I had done in my life worthwhile. Even still, I found I had to be better than the average woman to find my way and stick to it so I would not slide back to my old male ways.

Before I go, I would like to thank “Grace” for inviting me to write for her group “Empowered Trans Woman” on Medium. I really appreciate it

 

 

 

Friday, August 14, 2026

There Was Never a Plan B

 

JJ Hart, Back row far left
Girls Night Out.

Very early in my cross-dressing days, I always tried to have a plan b in the back of my head if danger approached in the form of my brother discovering me or my parents coming home early from work.

Seeing as how I had no effective plan to get out of what I was doing in mom’s dresses and makeup, I thought that somehow, I would have to just try to lie my way out of it and say I would never attempt it again. Knowing that was a deal with the devil I could never make and expect to keep. As I continued to cross-dress in the family mirrors, I finally had to throw caution to the wind and just go ahead and do it.

Years went by as well as the complexity of what I was doing as I tried my best to express my feminine self. At the least, I thought of better ways to hide away my resources from prying eyes and was successful all but once when I got careless on a weekend, I was away when I was waiting to go into the Army and start basic training. What happened was, I had just mixed my feminine clothes and wig in with a bunch of my male clothes thinking that one would disturb them until I returned. I was wrong and when I got back, everyone else in my apartment had not returned home for a college break leaving me all alone except for one other guy who had come over to visit.

As we sat around drinking a few beers, I decided to gather my courage and somehow asked would he like to see me dressed as a woman. Effectively, throwing all ideas of a plan b if he got up and bolted out of the apartment. To my surprise, he did not and was receptive to the idea, so I left to start the prep work needed to finally come out to another person. After I had taken the time to shower and shave my legs and face, I went into my bedroom looking for my feminine clothes, wig and makeup. Only to be shocked to learn they were all gone. Someone had stolen them when I was gone. All the plans for the evening I had were shattered as we sat around and then finished all the beer and nothing was ever said about him coming so close to meeting the true me. As far as confronting anyone about where my clothes, wig and makeup had gone, I decided to keep my mouth shut because I was so close to having to report to Ft. Knox in Kentucky for Army basic training anyhow. A final solution for a plan b during the next three years of my life. I knew I could not entertain any ideas of cross-dressing at all.

When I was discharged and Halloween parties with my friends became the only external form of feminine expression that I had, I needed to ignore any of the warning signs that I was giving away any idea I was not as masculine as I acted. I was so into going to Halloween dressed as a woman that I decided to take matters into my own hands and ignore all the plan b’s that I had thought up. Even to the point if some other person commented on my “costume” and the effort which went into it, I would just try to laugh it off. Mostly what happened was compliments from other ciswomen on my shaved legs and I even gained the nickname of “legs” with several of them which I had to act like I did not care. When deep down inside I was overjoyed and wanted more input. It took me years to understand what they were really saying was I looked good for a man dressing as a woman.

As more years went by and I became very serious about being a transgender woman and was attempting to hide it from my second wife, plan b’s became very important to me. In many ways, I had regressed to my childhood in the ways as I had to hide my femininity away from her. In addition to being very tuned in to when she got off of work, I needed to get better and better at makeup and eye makeup removal, so hopefully she couldn’t tell what I was doing when she was at work. The problem was that practice was making my femininized presentation more effective.  Success just made me want more and having a plan b at all was disappearing totally.

For the longest time, the only recourse I had was to attempt to lie my way out of whatever transgender activities I even had to resort to trying therapy to save our relationship. The gender therapist was wiser than I was and told me there was nothing she could do about my deep-seated gender issues. I was trying to buy time with my wife and save our relationship as long as I could, but the therapist was not a miracle worker and I quit going. Leaving me to wonder what I would do about finding the next plan b I desperately needed to hold my marriage together. Because I knew it would be just inevitable my wife would discover what I was doing as a transgender woman exploring the world and we would have a gigantic fight because I had promised I was going to stay home.

The problem was that I knew I was wrong and was just buying time until the next adventure I had in the world with the ciswomen that ran it.

Finally, what happened was I ran out of all needs to have a plan b when it came to me being a transfeminine person. I had learned to live freely behind the gender curtain which I had waited so long and worked so hard to do. In fact, it was the only big dream I had in my life. I then resorted to a new plan to live out my life the way I wanted.

 

 

 

 

Wednesday, August 12, 2026

All Along I was Just Me

 e

Inage from Gayatri Malhotra
on UnSplash. 

It took me decades of living to realize the simplest of all realizations…just discovering who the true me was all about.

It turned out I was so much more complex than the friends I had around me in how I felt about life. Which often help me back because I could not express how badly I wanted to be a woman. What I did was, I took the natural male response I inherited and internalized all my feelings. Naturally, the male response did not work and all it did was wreck even further my already frail mental health. If I could not cross-dress my anxiety increased and when I did my paranoia kicked in when I thought, I was getting caught.

As I added years to my life, the complexity of being a gender dysphoric person grew with the years. What did I do? I tried to outrun my problems. It wasn’t until the Vietnam War years and beyond did I learn that I would have to stop being a victim and stand up to living a life outside of the shadows of being a man. The idea of moving my family around and changing jobs all the time until I finally landed a job I wanted in a location, I wanted to be. That meant I climbed out of fast food and landed in a full service, casual dining chain which served alcohol which was exactly where I wanted to be.

With my dream job in place, I could concentrate on my feminine side by beginning to go to the small diverse LGBTQ parties I used to go to in nearby Columbus, Ohio. At those mixers, I was able to meet transgender mentors who would define my future. From them, I learned a path to my dream may actually be possible. The me I had always dreamed of was finally beginning to emerge. Much to the chagrin of my long-time second wife who actually went with me to a few of the parties. Probably, just to keep track of me. One thing was for sure; my wife never liked the trans woman I was becoming. Back in those days, I was still trying too hard to dress to impress and my wife was right, my dresses were too short, and my makeup was too heavy for her liking.

As she normally was, my wife was right about my appearance, and I tried my best to tone it down when she was around. Most of the time to no avail. I was stubborn and had to live out my so-called adolescence years of cross-dressing before I learned how to dress to blend in with my wife and the ciswomen around her. As I always say, sadly she passed away before she ever got the chance to meet the mature transgender me. I know we could have not stayed married but maybe at least be friends.

The question became, what was I doing with my time when I was discovering who I really was. What I was doing was exploring as close as I could what it would be like to live a whole new life behind the gender curtain. For the most part, I was successful as I made my way from the relative safety of the gay venues I was frequenting and jumping into the more challenging straight sports bars I was used to going to as a man. By never causing any trouble, always smiling and most importantly by tipping well, I was able to establish myself as a regular in several venues which seemed unreachable to me just a short time before. Most importantly, I was able to bring my love of sports from my male life into my female life with no problems. Which was a surprise to me.

As I did, I discovered the true me was not that far removed from the old me. Basically. I had just changed my appearance and gave up basic male privileges such as perceived intelligence and personal safety, and the best was yet to come as I was able to begin to move around freely as the new me in a world run by ciswomen. Quoting my second wife, I didn’t “make” a terrible woman after all. Primarily because I was not “making” anything. I was becoming me. Sure, I knew on occasions I could have done a better job, but I never allowed myself to be a victim and moved on back to my gender path. Which was beginning to change dramatically because I was beginning yet another  major gender related transition in my life.

First, there were the two obvious mental transitions I went through including the initial once when I realized I was so much more than a weekend parttime cross-dresser which went all the way to that fateful night at a local TGIF Fridays when I had had enough of that thought pattern and went out to be with the other ciswomen just getting off of work at a nearby mall.

From that moment on, I knew I could never go back to my old unwanted male self. But still, I felt as if something was missing in my life. It was because I was still missing the obvious transition of all as I finally realized I was never a cross-dresser or a transgender woman; I was just me.

I wish I could take credit for being persistent and intelligent that I kept on pushing to find me but I can’t. That credit goes to all the ciswomen who I became close to over the many years of struggle I endured. And yes, my second wife is included because she was the first to say be man enough to be a woman and make life easier on both of us. As we all know, many women are good at reading small lights inside of a person (unless you are fighting an unsupportive spouse) which is a point for another blog post.

I can’t say enough positive about all the women in my life who helped kick me out of my male nest and into the world of women. They knew me better than I knew me.

 

 

 

Tuesday, August 11, 2026

Understanding is the First Step to Overcoming Fear

 

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


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

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

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

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

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

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

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

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

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

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

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

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Monday, August 10, 2026

Stepping Out as Yourself


Image from Max Anderson
on UnSplash. 

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

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

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

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

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

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

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

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

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

 

 

 

Sunday, August 9, 2026

Your Lines in the Sand as Gender Markers

 

Image from Sonnie Hiles
on UnSplash. 

For the longest time, I set new lines in the sand as I progressed along my path as a novice transgender woman.

Sometimes, the lines were very faint, and I had a difficult time seeing them. All the way to deep trenches I needed to leap across. It all depended on what I was doing at the time. For example, when I was just dressing in mom’s dresses and putting on her makeup, the lines were very faint and easy to cross. In my mind, I was a boy one moment and a girl the next. A very black and white way to view myself, or so I thought until I grew older.

Instead of growing away from my cross-dressing years, I ended up growing into them by finally coming to a better mastery of the feminine clothes I wanted to wear and maybe more importantly, the artform of applying makeup which was a very deep line to cross for me. If I had worked as hard on my studies and sports than I did on my femininization projects, I would have certainly made the dean’s list every year and starred on the school’s football team. I was mentally built differently because of my gender dysphoria and could not decide for the longest time which gender path I wanted to follow because the feminine path was primarily there for an escape. When my male life became too stressful, I could shave my legs, slide carefully into my pantyhose which I had purchased myself from jobs I had worked and put on a dress and feel better instantly.

Even though I did not want it to happen, I began to build male privileges from doing a good job raising my daughter as a father and working jobs I was promoted at. When I did, I knew I would have a lesser chance of having just a small line in the sand to jump across if I ever needed to. Little did I know, how much both of my efforts would come back to help me in my later years when I encountered severe gender obstacles as I went behind the gender curtain as a transgender woman. I should say finally went behind the curtain since it took me decades to do it.

The problem arose with drawing more and more lines in the sand that my life as a transfeminine person became more complex quicker than I ever imagined. Often, I have described what I went through as sliding down a deep slope grabbing onto whatever I could to maintain the male life that I had. Just to watch it slip away. It led me to falling off the deepest cliff I could have ever imagined when I put away all my male clothes for the last time, went on HRT or gender affirming hormones and put my male life behind me for the last time.

By this time, even my stubborn old male self was admitting he had made a mistake by holding on as long as he did. All the covering lines in the sand I was about to cross with his own ideas did not work, as I was able to negotiate all the challenges thrown at me by ciswomen in the new world I was in. In many ways, I had come full circle when I learned how valuable all the building blocks, he had given me, just gave me more resolve to be a better trans woman. The daughter I mentioned earlier came around to be my earliest and strongest supporter so all the time I put into being with her when she was young came back to help me. Then there was my employment in the restaurant industry which turned out to be very lucrative for me in several ways. The first was with money and the second was with the opportunity to work closely with groups of varied ciswomen. In many ways, I learned what they faced in their lives gave me insight into what I was going to face when I joined their world.

For example, I learned what alpha females meant to the group of women as a whole, and if I could gain their support after I transitioned and joined their world, it would be very valuable to me. In many ways I found that good strong alpha ciswomen from super butch lesbians on down could do to help me erase my lines in the sand. I can’t begin to say how much they helped me. Even my second wife who was an unapproving alpha woman to me was a role model and taught me more about her life than she ever knew. Before she passed away tragically at the age of fifty from a massive heart attack. So, she never got the chance to meet the mature transgender me after I had crossed all the lines in the sand I needed to cross to just survive.

From all sorts of ciswomen, I learned that women come in all shapes and sizes with various levels of support of the transgender community. Many support us from afar and it would be different if it was their husband seeking to make his own line in the sand and become a transgender woman. On the positive side, there is now more information available to spouses of trans women to understand what seemingly a glaringly selfish path is to go down for their husbands. Especially with the husbands who have gone to great lengths to hide their gender passions from their wives for many years. When I step back and look at all the relationships which have ended over the years because of gender dysphoria, I try to wonder what would have happened if my wife was the one who wanted to draw his line in the sand and said enough is enough. I can’t take it any longer.

Of course, now I am biased and think I would have accepted my former wife bringing home another woman to get to know. How would my old male ego react? I am ashamed to say it now, but my old male self would have had to force the issue and solve it once and for all in his favor. Drawing his own line in the sand.

If you are at the point of drawing a new line in the sand for yourself, make it an achievable goal so you do not get discouraged. Finally, stay flexible with your lines as you know some will be deeper than others. If you do, you will stand a better chance of success.

 

 

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 l...