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

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.

 

Friday, June 12, 2026

A Humbling Gender Experience

 

Image from Katherine Hanlon
on UnSplash. 

For literally decades, any thoughts I had of living a successful life as a transgender woman, were only thoughts. I was never sure if I had any chance of making it. In fact, most of the time it seemed as if I was swimming against the current in a fast-moving stream of ciswomen, I wanted to interact with so badly, on their terms.

Doing it on their terms was my problem as I had always tried my best to be a strong student as a man of how all the women around me were living their lives. The main issue always was that I was only allowed to see so much of what was going on across the gender border. Again, because I was a man and had not yet paid many dues yet as a novice cross-dresser and not even a transgender woman yet. I still thought my real issue in paying my dues to be let behind the gender curtain came from my appearance in the world. Just being able to blend in with the ciswomen around me was good enough.

It was quite a humble experience when I found my appearance (and no matter how much it was improving) was not going to be enough. Even though the mirror was being kind to me as it told me I presented well, I was still stuck behind it as I still needed to put the image into motion. I was caught in the place where I looked good as a woman…for a man trying hard to accomplish it. I desperately needed to find a place where I looked as if I wasn’t trying to dress to impress. I was just being me. The problem then became who was the me I was becoming? How deep did my feminine desires run and where would they ultimately take me became the main things I thought about in my life. Every spare moment I had was spent either actively cross-dressing in front of the mirror or making plans of going public with how I looked and making the world my mirror.

As I learned the hard way my lessons on how to blend in with the world around me, often I was brutally laughed at and rejected by the world because I was dressing to thrill and not to blend. I guess I could say, I was humbled in the worst way by groups of teen girls in the malls I was just trying to shop in. My initial goal back then was to face my teen critics one-on-one until I failed completely or succeeded after many times of going back to my cross-dressing drawing board. It was like ripping a band aid off a mental wound and saying too hell with it and trying again to be successful. Until I was.

Rather than become overconfident at that point, I decided to try to build upon my newfound success and work on things such as how I moved and walked in heels. I discovered that every little discovery helped in my male to female femininization project such as keeping the old male scowl off of my face when I was out as a transfeminine person. No more scaring little kids away who called me a woman which was good but a mean woman which was bad of course. It was the last thing I wanted to do after working so hard on the basics of presenting as a passable woman.

The more I progressed on my path to living as me, the more humbled I became. Too many nights I came home in disbelief at the lessons I had learned from men and ciswomen in public as I struggled to fill out my gender workbook which was way behind the rest of the world I was dealing with. I learned men did not value anything I had to say unless I was spoken to first and women had their own way of communicating around men even if the men thought they were in their conversation. Just as a starting point. I also learned of a whole new lesbian culture I knew nothing about and where I could possibly fit in as a femme lipstick lesbian. As you can understand, the terminology and how I fit in came at me quickly and again I was extremely humbled to be asked to go to lesbian mixers where I learned a lot.

I learned also that women lead much more layered existences than men do, often built around dealing with men themselves. I did not have to worry much about that because I was not attractive enough for men to pursue me and after my lesbian friends taught me I did not need a man for validation, my life brightened considerably.

As I progressed deeper and deeper along my gender path, it became increasingly obvious that I could indeed achieve my goal of someday succeeding in a feminine world. Even though in many ways it did not resemble my initial dreams. In no way did I think I could maintain my sense of sexuality as I never made it with a man. In my own way, I maintained my own “Gold Star” status that many lesbians I knew maintained. The closest I ever came to getting any real attention from a “GS” lesbian were a few kisses.

When my new world began to open up, I was very humbled to be there at all. Along the way, I have survived issues such as severe depression and negative attitudes towards me from loved ones to stick to my dreams and goals. Remembering where I came from helped me form the strong building blocks to complete such a diverse and difficult change in my life. Using the negatives in my male life to build a transfeminine one was one of the best moves I ever made in my life as I made a complete circle back through all my male years to be the person I always dreamed I could be.

I was back to being me. The only transition which really mattered.

 

 

 

 

 

Wednesday, June 10, 2026

Trans Girl's Dreams...Nothing lasts Forever

 

Image from Bruce Mars
on UnSplash. 

Nothing last forever in a transgender woman’s world, or does it?

Many of my life’s earliest recollections begin with the vivid dreams I had of being the pretty girl of my thoughts, only to be shattered back to reality when I woke up into my same old male world. Sadly, I remember thinking at the time how bad it was that dreams could not last forever. Why was I stuck with the impossible dream.

At the time, I thought too, it was a possibility that I was going through some sort of a phase that I would grow out of. As many of us know, we did not grow out of any sort of cross-dressing phase, I grew into a more transfeminine one. It turns out that thinking me wanting to be a girl was just a phase was as wrong as thinking I was truly crazy because of my gender issues. I did not really think I was crazy for just wanting to be who I was, but it remained a thought in the back of my head which back in those days was reinforced by the mental health community.

As life moved quickly forward as it always does, in my thirties and early forties, I began to really entrench myself in the physical world of newly found cross-dressers and transgender women around me. For the first time in my life, I discovered I did have role models in the community I could learn from. In their lives, they were approaching the world as if they were never going back to their male selves, so why couldn’t I. My impossible dream may not be so impossible after all as I improved my feminine presentation to the point to where I could blend in with the majority of ciswomen I encountered when I started leaving the mirror at home and heading into the world.

From there, I began to set up small bucket lists for myself. Once I completed one task as a novice transgender woman, I immediately set up another. Basically, I set my tasks up on what my observations of women were anyhow and how much I wanted to try them in my new world I was experimenting in. An example was when I began to go to the big bookstores as me to see if I caused any negative attention. When I didn’t, I began to visit their in-house coffee shop and even began to use the restroom of my choice. The women’s of course. I would have looked very silly using the men’s room the way I was dressed.

Another problem I had was focusing on my dream. Just exploring the world without a plan was not getting me anywhere. In order to progress towards my goal, I purposely chose a few of the most trying experiences a ciswoman could have. Like going to an auto parts store to see how I was treated. The scariest experience I ever had was going to a pick it yourself junk yard with my wife Liz to pick up a side mirror for an old car we had. It was a very hot and humid Ohio day, and I was worried about melting in front of the guys at the junk yard, but no one gave me a second look, and we were off with our mirror before I knew it. But to this day, I am still shy of going into male dominated spaces because I know of how women can be taken advantage of from my old days as a male.

By the time all of this was happening, I was having a sneaking suspicion that my desire to live full-time as a transfeminine person was never just going to go away. In fact, it was just going to become more intense.

As my third wife Liz became more serious, she wanted to travel to a few places she had never been to and some that she had. The easiest way to do it was to sign up for tours with a local Cincinnati based tour bus company. Over the years, we traveled from Boston and Maine and New Orleans to Mardi Gras and Florida in the south. The challenge for me was always using the restroom with a bus who majority of passengers were women. I had some adventures along the way such as one elderly woman commenting that I was using “their” restroom, all the way to being afraid of confronting two agitated women in an Alabama restroom and being afraid of being arrested by a “good ol boy” southern sheriff for just wanting to pee. To add insult to potential restroom drama, matters just got worse when I became non-mobile to where I needed to use a handicapped stall where there was one available. But through it all, I learned to be resilient, and the world was not such a bad place after all.

It was about this time that my gender life flipped, and I knew my male life was not going to last forever but my female one would last as long as I did. It was during this period I survived two trips to the hospital. One for Covid and one for pneumonia which were the most gender numbing experiences of my life. When the nurses asked questions about my gender status since I was still biologically a male and I had to put up with all the nudity which went along with my visits. From it all I learned that being nice to the staff was the best way to go and they would be nice to me.

I am sure that kid in the mirror would have never thought his life would have taken so many twists and turns if he chose the gender path that he did. Would he have done it? Sure, but would he ultimately have a choice, no. Being transgender was simply something that was built into him from the beginning and he never would have a choice in the matter. As soon as he could come to that conclusion, the better off he would be when he discovered nothing lasts forever.

 

Sunday, June 7, 2026

Hey You!!!! Meeting Myself in the Middle

 

Image from Adam Winger
on UnSplash. 

For me, meeting myself in the mirror was never easy to do. While the group of boys I grew up around were blissfully doing boy things without a problem, I was struggling with the idea that I wanted to be a girl.

Sadly, for the longest time, I thought that someday I would have the chance to outgrow what would become for all to call gender dysphoria. For me, I was just a kid with problems I had no idea of how to conquer. Through all this time of my life my favorite quote to pass along was when some adult asked me what I wanted to become when I grew up, I could never tell the truth and say a woman as I lied and said a doctor or a lawyer. The only thing with certain that I knew was I would get an immediate trip to the psychiatrist if I had ever told the truth compliments of my parents. 

As I always say, age entitled me to a chance not to outgrow being a cross-dresser but did give me the opportunity to meet myself in the middle and start to mature into the transgender woman I am today. Before I did though, I needed to come up with an understanding of what the middle of being me really meant. What made it all so difficult was that my male life when it was going well it was very good, but when it was bad, I wanted out immediately. As I ran to my makeup, dresses and heels for comfort in the mirror.

The middle began to be harder and harder for me to find when I left the home mirror, gathered my courage and headed into the world as a transfeminine person. Many times, I could almost see and sense my middle person in the public mirrors I was still using to build myself up in places such as clothing stores in the malls and changing rooms I had started to use in all the thrift stores I was shopping to discover the latest fashion item I could wear. I was never any good shopping for women’s clothes as a man, as my feminine self-wanted to do it all and make all the final choices for herself.

In addition to fighting for the middle with my male self, I needed to fight my second wife for the rights to her husband. Like my male-self, my wife was a formidable opponent to any idea of me transitioning any further into the feminine world I increasingly wanted to live in. In many ways, she held all the gender cards because she knew I was a cross dresser when we met but never/ever agreed to me going past that point as she said she did not sign up to live with another woman. For whatever reason she never liked the transgender woman I was becoming and passed away before she could meet the finished product I had become. I don’t blame her because she just got caught in the middle of me not wanting to admit to what I always knew deep down…there was actually no middle point to me, I was destined to eventually live my life among ciswomen as an equal transgender woman.

The problem was, getting to the point of realizing all of this was easy to write about and harder to do. The biggest mistake I made was thinking my gender balance between male and female was so good that I could live as both in the world. While I maintained a long-term marriage and a good job. Trying to go all in on both genders cost me my already fragile mental health as I was still trying to do my research in the public eye about which gender direction I wanted to go. Long story short, I found without too much trouble I could carve out a new feminine life without the world questioning anything about my old male life. As I surveyed the world suddenly, I could see gender possibilities opening for me that I never thought possible before.

During this time in my life, I think I met myself in the middle too fast and tried unsuccessfully to slow my progress down until I could figure out what to do about the rest of my life. Primarily my second wife and my very lucrative job. Plus, on the other hand, I had put this gender teeter totter in motion, and it increasingly looked as if I could not get off. I kept up the old male charade I was forced to live as long as I needed to, and with the help of a few ciswomen friends, I was able to find a new middle point in my life as a trans woman. Which seemed to work well, until HRT or gender affirming hormones came my way, and the balance of my life was changed forever.

I had always viewed the possibility of me taking the gender altering hormones as a line of demarcation of me never going back to my old male life and it was. From the obvious growth of my breasts and hair to the overall softening of my skin and facial lines the changes came fast and furious and again I was forced to move up my timeline to discard (or give away) all my old male clothes and set my sights on a new bright future. Away from all the uncertainties of going back and forth between the two main binary genders of womanhood and manhood. My lifetime of juggling identities went away, my mental health improved as I entered the world I had always dreamed of my entire life that I had finally earned my way into.

The “earn” word is important here because of all the trial and error (mostly error) I put into finally facing the reality of my true gender and forever stopped meeting myself in the middle. Was it worth it? Sure, because I ended up not having any choice after all.

 

 

 

 

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.

 

 

 

 

Thursday, June 4, 2026

When Nothing Else Mattered

 

Image from Klara Khokhlova
on UnSplash. 

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

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

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

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

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

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

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

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

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

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

 

 

Sunday, May 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.

 

 

 

Friday, May 22, 2026

Letting the Light Into my Trans Closet

 

Image from Sahin Kalijii
on UnSplash. 

Growing up, I had what I considered to be a very dark and escape proof gender closet.

I was part of the pre-internet/social media generation so I could not find the latest online tutorial on improving my makeup skills. And of course, I could not run to my mom or girls’ peer group for any information either. I was stuck with no light in my closet all by myself it seemed.

I stayed that way for years until gender pioneers such as “Virginia Prince” began to shine her faint light into my closet. I had little to no knowledge that individuals such as me even existed in the world. Once I did, I was very relieved I was not the only transvestite as Virginia called us then in the world and I set out to meet others. Before I could open my closet door even a little, I had to convince my second wife that it would be OK to do it. She had known from the beginning of our relationship that I was a cross-dresser but did not like it when I began to let others know of my so called “hobby.” It actually marked the beginning of me opening my closet door to the world and proclaiming I was a transgender woman, not a part time man putting on a dress and makeup.

Along the way, another problem I had was deciding when to take the chance to open my closet door and to which person. I did myself no favors when for the most part, I tried to internalize all my feminine feelings which made me an impossible person to get along with when I was looking in the mirror at my male self and hating what I saw. All the times I ventured out of my closet only to have to hurry back in was wrecking most of my life as I knew it. Not to mention the life with my wife who I envied because she was a ciswoman, and resented because she would not let me explore a feminine side which was trying to see the light of day.

I found my male self-had installed a powerful spring closer on my closet door which was designed to keep me in. Deep down he knew his part of my life was in danger every time I was able to escape the closet and get out into the world. I felt so enlightened and natural when I did, I never wanted to return to my male life and all its drudgery. I was so sick of wearing the same old collection of ties to work every day when better/brighter fashion choices awaited me in my closet at home.

I discovered that the more I outfitted my closet with brighter lights and bigger mirrors, the more I wanted to test my new fashions, wigs, and makeup in the world. Away from my mirror which had the tendency to lie to me. I can’t tell you how many times the mirror told me I looked great only to be rejected quickly in the public’s eye. It took me years to realize that I was expecting too much on just looking like a ciswoman, I had not yet paid my dues on becoming myself and then having the ability to relax and enjoy myself even more.

It helped me too when I began to venture further away from my closet as my confidence as a transfeminine person began to grow. To get there, I needed to be able to look another woman in the eye and communicate one on one with her about the world around us. Men entered the picture too but briefly since most of them did not want to have anything to do with me anyhow. More and more, I did not have to scramble back to my closet following a bad day or night out into the world because I was doing better in my feminine life. All my male could do was sit back and helplessly watch as his hold on me slipped away and all he ended up being was a provider because of his good job.

I arrived at a point when I needed to expand the small dark transgender closet, I had always lived in. It all began with me having to accept who I really was and had much more to do than just expanding my closet for all the feminine clothes I was buying. I was making a huge lifestyle choice that I had spent way too long deciding to make. All of this moving things around in my life led me all the way to leaving my closet totally behind and looking for a transgender house to live in. I had taken my time (decades) to make my decision, and it occurred to me that I had taken too much time but by then there was nothing I could do about re-winding the clock. I took the good and lived on until I was able to carve out a new transfeminine life.

As I look back, it does not seem possible to me that I have come from the lost, lonely boy staring longingly at himself dressed as a girl in his closet’s mirror to the person I am today. But none of would have been possible had I not been able to embrace the help of several key ciswomen around me to make it happen. I wonder what would have become of me if I was not able to meet them. On the bright side, stepping out of my closet (as scary as it was) enabled me to meet all of them to start with. So, destiny was on my side as my life went full circle from a dark closet to the bright existence I live with my wife Liz now. I was just fortunate as my hunches that everything would work out if I stayed on my gender path. I just had the super strong hunches that they would.

Thanks very much to all of you who read and interact with my writings. All comments are always welcomed!

 

Wednesday, May 20, 2026

A Special Kind of Crazy

 

JJ Hart

In my youth and even later when I was struggling with my deep-seated gender issues, the thought entered my mind that I may just be a little crazy to think that way. I even went as far as telling others I was not the well-adjusted person they thought I was.

Looking back now, I think I was just preparing in my own way to tell others I met that I wanted to be a woman. Which I never did for decades when it became obvious to strangers I met at cross-dressing, transgender socials I went to that I wanted to be feminine, or I would not have been there.

The first time that I told anyone that I liked to wear women’s clothes was after a Halloween party I went to in the Army of all places. Weeks later, over way too much good German beer, the topic came up with friends about how realistic my “costume” was, all the way to my shaved legs. Since I was among a few very close friends, I took a big chance with risking the remainder of the time I had in the Army and told them I was a transvestite (the term used back then) and I liked to dress as a woman. I said nothing about being crazy, and I just liked to do it.

Of course, at that time in my life, I was busy running from the fact of how deep my gender issues went. I was hiding the fact from myself that no I was not crazy, I just wanted to be a transgender woman in the days when the term was first being used. “Running” for me back in those days meant changing jobs and locations frequently to keep my mind off what I was truly running from, my gender issues. Even with all the moves I was making, I could not outrun my life and occasionally the term “crazy” snuck into my thought pattern.

To compensate, I began to do “chores” which I considered feminine in nature such as doing part of the grocery shopping for my wife dressed as a ciswoman. When I succeeded with no problems, I started to feel so natural that I continually wanted to do more. So, I began to combine my grocery shopping adventures with new visits to big shopping stores to pick up small items I could afford such as a pair of panty hose, or new makeup. Amazingly, no one bothered me or shouted, “There is that crazy man in a dress.”

As the years went by, I learned that the ciswomen around me did not think I was crazy. They thought I was more curious than anything else as they wondered why I would leave the men’s club to play in their world. Ironically, as they were taking care of their curiosity, at the same time, I was learning from them. I had always envied girls (then women) so much as I followed them from afar, and now I had the chance to go back behind the gender curtain and learn first hand about the pluses and negatives of a ciswoman’s life and did I want to be a part of it or was I just following a crazy path off a cliff.

I learned quickly that I was following the right path, no matter how crazy it seemed at the time. The more I explored the world as a trans woman, I found the more exploration I needed to do but that was OK with me because again, my life for a change did not feel forced and so natural because I was not fighting to be something I was not…a man. All of a sudden, my life made sense and a was a special kind of crazy, a transfeminine person. At that point, I knew I would have to lose for good all the formidable white male privileges I had earned over the years. Even I was surprised to say “buh-bye” to all privilege I had built up.

Not all benefits I had living as a man were so easy to give up such as part of my intelligence and my personal security. I did not have many interactions with men one on one, but I learned the process of letting the man take the lead in most all situations. Especially when it came to sports, where I knew a lot about what was going on. The other privilege or benefit I needed to give up quickly was when it came to my personal security. I was not prepared for the world I was facing now in which I was fair game for any toxic man. I was fortunate to have escaped injury a couple of times when I broke the rules that ciswomen grow up with such as not finding your self in a compromising position on a dark city street all alone. I thought at the time, I was crazy to do it and never did it again.

Most recently, the craziest thing I have done is to let my precious Estradiol prescription run nearly all the way out. In fact, I am down to my last applications of patches this week as I am waiting for another refill which I have been notified is coming today. I have written in the past a couple of times about the paranoia I felt when I had a recent appointment with my endocrinologist who prescribes my HRT medications. It turned out that that all my crazy paranoia about the far reach of the orange felon in the White House rejecting any ideas of me receiving gender affirming care through the Veterans Administration would ever happen again. Instead, I received a prescription which will last me through another year until our next appointment.

Once again, it was proven that I am a special kind of crazy which I wish I had learned to embrace earlier in life. It would have made life so much richer just knowing I had the chance to experience life on both sides of the binary gender border.

 

 

 

 

 

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.

 

 

                               

 

 

Monday, May 18, 2026

There was Never a Maybe

 

Image from Marija Zaric 
on UnSplash. 

In my life, there were never any maybe moments about having gender issues, only a resounding yes, because I had them.

Time fades the memory, but I think the first inkling of the issues I had was when I began to experience very vivid dreams that I was indeed a pretty girl. That is when I went the only route, I knew how to go and secretly began to raid my mom’s clothing drawers and closets for her clothes I could still squeeze in to at the time. Before I knew it, I had somehow acquired my own “collection” of feminine clothes and makeup I used to practice my new artform. While the boys around me were practicing putting together model cars, I was busy practicing being a girl. At the time, all the practice flustered me, but would come back to help me later in life when I would not have to work so hard on the basics of presenting as a ciswoman.

The more I accomplished in my cross-dressing pursuits, the more I wanted to do because I felt so natural. Which was a huge clue to me that I was on the right gender path, and this part of my life had always been a deep part of me. If I had followed the clues and not ignored them, I would have been much better off in the long run. By putting my deep instincts off, I ended building up a successful but deeply destructive male life. Every time I built something up as a man, I needed to somehow destroy it because I did not want it to interfere with my possible upcoming male to female femininization project. I guess I could say the possibilities intrigued me as much as they terrified me. How would I ever be able to live as a transgender woman dominated most of my everyday life as I envied the lives of the ciswomen around me.

At the time, all of this was happening, all I was trying to do was experiment if my gender dream could ever come true and I could give up all my male privileges I had built up to try it. If I could do it, I could live it became my goal. Which was easier said than done because I was still living most of my life as a transfeminine person only in front of the mirror and not the world where I belonged. At times, making my way from the mirror was a brutal experience for me because the world treated me in ways that I really deserved when I did not dress myself in the proper way to hide the best I could my testosterone poisoned body and attracted undue attention. Not dressing to blend in with the other ciswomen around me was hurting me badly until I finally learned my lesson.

Probably what I suffered from the most was not having the role models I needed to help me in my male to female transition. It was very lonely in the pre-internet days with no social media tutorials to help new struggling trans women or cross dressers along. It was just me and the public to provide feedback on my progress because I discovered the mirror was quite OK with lying to me about how I looked. It would tell me I was attractive, then I would get immediately laughed back home by a group of teen girls was a prime example of what I was going through. I remember vividly the days when I began to seek out the girl’s attention to measure how well I was doing in the world, rather than running from it. I figured if I could succeed in passing my toughest tests anything was possible.

As I began to pass more and more feminine tests, my confidence began to grow, and I started to face my deepest dreams and fears that I could conceivably leave my old male path behind and carve out a life as a transgender woman. On my own in the world. All of this had its good and bad points. The good was that I was finally realizing after all this time I could live my dream and the bad was, what would I do about the remainder of my male life. At that time, I still had a very good marriage to deal with, as well as a family and successful job to consider. It was as if I was painting myself simultaneously into two gender corners which would be hard to get out of. I found wanting the best of both binary gender worlds was impossible to do and coming up soon I would have to decide which way I was going to have to go.

The decision I made turned out to be the easiest one and one I should have made long ago. I certainly had the gender issues I worried about endlessly and would have them as long as I lived. I had always thought that tomorrow would be the day I could figure it all out, but all the tomorrows started to become years and decades and I still hadn’t done anything about it. Gender procrastination at its finest, or its worst. Bottom line was the procrastination I was doing ended up hurting me in ways that I never imagined such as with my mental health which really paid the price of living the pressure of life in two genders. I needed to finish painting the gender corners I had put myself into and do it fast.

On one of the nights, I went out to try to be by myself, I ended up really socializing as a trans woman and enjoying myself. Right then, I decided I had made my final decision to pursue HRT and finally put what was left of my old male self to a permanent rest. It occurred to me then that the decision had always been made for me from those earliest days in the mirror I went through.

All the maybes were in my past. I could succeed as a trans woman, and I had a bright future ahead.

 

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 naïve 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.

 

 

Friday, May 8, 2026

Working Smarter not Harder as a Trans Girl

 

Image from Erik Mclean 
on UnSplash.



Before we get started on today’s post, here is a little background on my annual visit to the endocrinologist yesterday at the Veteran’s Administration in Dayton, Ohio.

It turns out, I was just wasting a lot of mental time and effort as I was worried about this appointment. I was worried that she would not renew my Estradiol prescription for the next year. But she did with no questions asked. The only other real problem I asked was why my Estradiol blood levels dropped as much as they did on my last visit to the vampires to have them checked. She did not know and thought I should have them checked again and see where they checked out. So, that is where we left it.

In the same vein, I had a great question from reader “Morgan” asking me if I could sense any differences in my moods when my levels went down since we both are older and on the hormonal patches. I told her no, I did not see any difference except in a new infuriating amount of hair I needed to get rid of on my arms. Since that time, the hair seems to be retreating, so hopefully that signals my levels returned to where they usually were. And, as far as moods go, normally I do feel an overall sense of wellness on the days I change my patches as well as a welcome swelling of my breasts.  I hope that covers the question Morgan, and thanks for asking.

As far as the deeper problem of feeling so much paranoia that I felt before the appointment, I think it goes back to my entire progression on the gender path I took to my transfeminine womanhood. It always seemed I was working harder not smarter as I attempted to fill out my feminine gender workbook as fast as I could. It was because I did not have the benefit all the other girls had growing up in a world of ciswomen where I was excluded. Every gender stop sign that I faced deepened my paranoia that I could ever have a chance of making it to my dream goal of crossing the male to female gender border and settling in as a successful transgender woman.

The first part I faced was just working to blend in with the ciswomen public I was around. I wanted to live the old saying that if it walked like a duck and looked like a duck, then it was a duck. My problem was even when I thought my clothes and makeup were on point and looked good, here I was walking like a circus clown in drag in my high heels. Putting my transfeminine persona into motion presented a real problem for me. It seemed like it was not so long ago that I was having the problem learning how to walk like a man out of puberty so I would not be called a sissy by the bullies and here I was trying to reverse the process. It took me a while to try to perfect my version of a woman’s unique style of movement but with a lot of practice I calmed my paranoia when I entered a room full of strangers and did the best I could. Then, I needed to work smarter, not harder trying to remember which gender I was on which day I was presenting. I worked in a pressure packed male dominated industry and it was as if the clock had been turned back and I was worried about being called a sissy again.

Another problem I was having was keeping my mind on whatever gender I was. An example would be all the time I wasted at work wondering what it would be like to live the life the ciswomen around me were living. Or better yet, daydreaming of the next time I could try when I could flip the switch and sneak out of the house again as a convincing transgender woman. If I could reclaim just a portion of the time I wasted, I worked harder not smarter as a person caught between two genders, what a relaxing, extra successful life I could have led. I was stubborn though and persisted through the decades just getting by thinking I could juggle being a parttime woman and a parttime man. Finally, it all became too much for me to handle mentally, so I needed to make a choice. But even then, I had to make certain that I was making the right decision, so I set out to change my path into a more challenging direction.

What I did was to throw caution to the wind and try to experience situations I always wondered what it would be like if I was an actual ciswoman. To do so, I had to finally earn my way behind the gender curtain and really attempt what my own unique path to trans womanhood really required of me. Essentially, the whole process required total commitment from me, and I needed to start making future decisions which would dramatically change the rest of my life. I was nearing sixty and my transgender biological clock was ticking loudly in my mind. If I was ever going to make my move to live fulltime as a woman, I better do it and it was time.

Better yet, I had a circle of women friends to help me socialize into the feminine community and I set out to secure a doctor’s approval to start HRT or gender affirming hormones. The timing was all right for my big move, and I no longer had to work harder more than smarter to do it. Most importantly, my paranoia about doing it all was at an all time low as for a change, destiny was on my side. Against all odds, I was able to meet a stable loving woman online as well as my daughter came on to accept me when I told her my deepest secret about wanting to be a woman my entire life.

Karma was coming around to pay me back for all the paranoia I experienced when I was working harder more than smarter. For the first time in my life, I allowed myself to be happy.

 

 

 

 

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 choic...