Friday, March 27, 2026

Pulling Your Gender Band-Aid Off

 

Image from Possessed Photography
on UnSplash
I am sure you have encountered a time when you just had to pull a band-aid off quickly from a tender area of your body. Even worse, maybe the band-aid was in a spot where your unwanted male hair was thick, and it hurt.

After I began to realize what was going on in
my life with my gender issues, my time to remove my lifetime band-aid was coming closer to being done. I could put it off no longer once I started to get out into the world as a transgender woman and begin to live. Sure, I was scared, but my whole new life felt so real and natural to me that I just had to keep moving forward.

What helped me gather the courage to finally rip the band-aide off was that I was becoming quite successful in carving out a new feminine life were no one knew or cared about the old male me. Even with the protests of my second wife and my male self, it just seemed possible that someday I could live my dream of being a fulltime transfeminine person. On the negative side, I knew I had a lot of work to do to be able to even think I could ever rip the band-aid off and move on with my life the way I always thought it should be. Courage was always my problem, along with the possibility of causing loved ones around me pain if I made such a perceived selfish move.

Until I arrived at the point of self-preservation, I did think it was selfish the way I was living. After all, I was spending every spare moment when I was not working either living as a woman or planning the next time I was going to do it. I was completely obsessed with making the next move up my gender path and could not wait to fill out the next chapter of my gender workbook. The problem was, ignoring my path was causing me damage to my mental health all the way to me trying self-harm to myself with a suicide attempt when I thought all was lost. Until I finally regained control of myself before I did more harm. When I did, my life began to go  full circle and the future seemed brighter. If you find yourself looking down at that dark tunnel of self-harm, please remember what might be true today, may not be true tomorrow and there might are people to help you on various hotlines. Especially if you are a veteran and have Veterans Administration health care.

I am sorry I digressed from my original topic of pulling off your band-aid into suicide, but it just so happened to me that suicide helped me to make the final decision to take the gender jump from a male to female life. Was there room for me after all behind the gender curtain I so desperately wanted to explore because I felt I belonged there. If I did not make the jump (or attempt to), what reason did I have to keep living, kept sneaking into my subconscious thoughts. At the same time, I wondered what was going on under the wound I was carrying around as I tried to live a successful male life. My habit of living half and half in both genders was just not working for me. I had always heard that if takes three repetitions in a row to form a habit, so what I was doing was completely wrong when I needed to go back to my unwanted male gender after spending three days as a trans woman leading my best life.

My life finally got to the point that even I could not ignore the ignorance of how I was choosing to live. I needed to face the truth of living the male life I had since birth was false and I needed to move on to a brighter future away from all the male influences I lived under. The band-aide which had become such an integral part of my life had to go away. No matter how much pain it might cause. I was fortunate in a way because I had most of the people in my life who had mattered to me, including most of my family. When I came out to my remaining blood family, my daughter wholeheartedly accepted me and my only brother rejected me. So, I earned a fifty-fifty split when the band-aid came off.

The next big problem was averted when I was able to take an early retirement, so I would not have to worry about working a new job as my trans woman self. I supported myself by selling collectables and with my Social Security.

I guess you can say, taking the hard way out and waiting as long as I did transition worked for me. Even though I had to go through enough anguish along the way to wonder why I did it. I was doomed to life of opposites. Gender being the main one, and honesty being the second one. If I had dealt with the second one first, maybe I would have saved myself a portion of the problems which were presented to me. Certainly, emerging into the world at an early stage would have not necessarily been ideal either, but if I had just pulled the band-aid off and did it, I would have had the opportunity to build a new life earlier. Probably in a new job and with a new family because my blood family would not have accepted me.

At least, if I had done it then, I would have had more years to adjust to the radical changes I would have to go through and figure out away to do it. One way or another, we can not go back in life, so we have to live with the consequences of what we have done or haven’t. Who can say which time would have been easier to join the public as a transgender woman, twenty years ago when I was seriously exploring ways to do it, or now with all the anti-transgender rhetoric which is going on as politicians use us as a scapegoat.

I guess we are doomed as transgender women and transgender men to have a giant band-aid to pull off one way or another. In my case, I should have just pulled it off and got on with my life.

 

 

Thursday, March 26, 2026

Trans Girl on the High Gender Board

 

Image from Navy Medicine
on UnSplash.


I remember completely when I was a kid, intensely afraid of heights, and my mom made me jump off the high diving board at the swimming pool we were at. It was the last thing I wanted to do, and I still don’t know till this day how she convinced me to do it. But she did. I am sure she thought that once I did it, I could do it again, which I never did.

Perhaps, by this time, you are thinking what does this have to do with being transgender but of course I can connect the lines as always. Fast forward to the days when I was first gathering all the courage, I could muster to leave the house and attempt to explore the world as a woman. To do it, I needed to jump off that high diving board again and again. Plus, I would have to raise the diving board even higher every time I tried it.

As I did, I discovered little pockets of cross-dressing acceptance I could exist in. Such as the women’s clothing stores where almost everyone was nice to me. It took me awhile to realize the clerks who waited on me were not being nice just because I was another woman, they were being nice because I had money to spend. To them, my gender was not trans, it was green. Even though I took acceptance and built on it to other potentially mellow venues in malls such as bookstores and coffee shops. I was successful in them and was able to build my confidence from there and move up to a higher diving board and jump off. No matter how scared I was, I needed to force myself to climb and jump.

The next comfort zone I forced my way out of was by forcing myself to stop for lunch to see if I would be accepted. For the most part I was, because again, my money was green and I smiled and tipped well. The magic ingredients it turned out to be accepted into a challenging new feminine world. Or so I thought until I kept on climbing. It turned out the climbing part was the easiest. Once I arrived where I thought I wanted to be. I added “thought” in because once I made it to a higher board, the jumping part really scared me. Mainly because I was leaving so much behind me, along with all the male privileges I had worked so hard to gain. Such as fighting back when someone made fun of me for the way I looked. When it happened, the only recourse I had was to go back to my cross-dressing drawing board and try to determine what I was doing wrong.

Before long, my drawing board became quite littered with fashion mistakes I had made. Going through my cross-dressing adolescence was quite painful because I was a thirty-year-old male trying to do it before I learned otherwise. I was exhausting myself climbing up the high dive and then down when I discovered there was no water in the pool. Finally, I learned the hard way to cross-dress to blend with the other ciswomen around me because they ran the pool I wanted admission to.

It turned out that the pool was much farther down than I thought it was, and I had too much time to think about what I was trying to do before I hit the water. I had not made the time to build up the feminine muscle memory I would need to allow me admission to the world as a transgender woman. It did me no good at all if I vaguely looked like a woman if I could not move or communicate like a transfeminine person.

At that point, jumping off the high board became very real to me. I was rapidly coming to the point of decision about what I would do with my life. By this time, I was in my fifties and was beginning to carve out a respectable life as a trans woman. My new world knew what I was and did not care. About my present, or more importantly, my past as a man. I was able to bring what baggage I wanted from my male life without any interference. It made all the difference in the world to me when I needed support from wherever I could get it in the worst way.

As I lost my fear of the high dive, I began to consider other transgender alternatives such as taking advantage of therapy and HRT through the Veteran’s Administration health care system which I was already a part of. I wondered then what my mom would have thought (she had long since passed away), about teaching me to take the long and difficult path to the high board would come back to help me so much later in life. Especially when she was the one who was dead set about me coming out to her after the Army when I tried. Karma came back to help me when I needed it the most. I could jump off the highest diving board I could just to prove I could.

Of course, the final high board I jumped off was the one which saw me do away with all my male clothes and live life as a fulltime transgender woman. In reality, I was never a stylish swimmer or diver, but at least I made it to the point where I could make it in a woman’s world. A world which would prove to be much more complex and difficult for me to succeed in than I ever thought possible. Probably, because, for the most part (except for a few friends) I was filling out my gender workbook as I went along. Preparing myself for when I could achieve the ultimate goal, my lifetime dreams of living as a woman to the best of my ability.

At the least, I was happy I gathered enough courage to go ever higher on my gender diving board and more importantly jump.

 

 

 

Wednesday, March 25, 2026

It was Always in my Way

JJ Hart on Left, wife Liz on Right.
Every time I turned around, my gender issues were always in my way. When I was younger and my life was simpler, the issues manifested themselves mainly around the sports I was trying to play. Since I was never good enough to win consistently, I usually had to head home to my makeup, mirror and skirts to feel better. One way or another, I always was soothed by looking at my feminine self in the mirror.

Of course, with age came complexity in life which included a military disruption of three years during the Vietnam War. My Army training very much was in the way of expressing any of my feminine qualities. Drill sergeants frowned upon any miniskirts or lipstick during basic training. So, I needed to resort to deeply hiding my secrets away, not unlike what I had done my entire life. I kept thinking against hope that someday I would be the pretty girl in the new car I was saving up for. I did get the new car, but being the pretty girl was very much up for debate and something I was always trying to achieve.

To remove the obstacles, I faced to living the transgender dreams I had, I needed to do a lot of living I discovered. Life was never going to be as easy as just looking the part of a ciswoman. If I truly wanted to go through all the living to earn the title, I needed to get out of my shell and into the world as a novice trans woman. Sadly, as I followed my gender path, there was always something emerging to get in my way. Such as a wife, family, friends and job which I did not want to risk losing. It seemed the better I did as a man, the more I had to lose.

All along, I thought the gender curtain would be more of a gentle barrier to cross to see how the feminine half of the population lived without men. I was not prepared for all I needed to go through to earn my way to having female privileges to replace the male ones I was losing. To begin with, I was painfully shy and insecure about talking to any other woman at all. Plus, as I learned all the different forms of communication women use, adding them into my world was a challenge. Such as having to stay in the present when someone talked to me and not try to anticipate what they were going to say. I discovered it was much easier to anticipate what a man was going to say from all my years as living as one, than a woman with non-verbal (eye to eye) communication skills. Not to mention, a ciswoman’s passive aggressive behavior which I misjudged several times before I adjusted to the new world I was in.

When I was able to get communication out of my way, I could move on to other obstacles in my way. I was still having problems with putting together a complete convincing picture as a transfeminine person. I had not practiced enough to feel natural in my world of makeup and high heels to feel natural and relax. Every time I was able to relax and enjoy myself as a transgender woman, I would do something to give myself away. It was not until I quit thinking I was fooling anyone into thinking I was a ciswoman did I do better. Mainly because I was just being me. At this point, I needed to overcome another major hurdle I had when I was a man. I never thought, or was raised to think, I was ever good enough to excel in the world and if I could never make it as a man how could I ever make it as a trans woman. It was a major boulder to move from my path.

It took a while, but I did build the self-esteem as a woman that I never had as a man. I did it slowly with the explorations I took into the world. I was able to build the all-important confidence I needed slowly but surely with the help of a totally new set of friends and acquaintances I built up who had no knowledge at all of my former life as a man. As my wife Liz told me, very few people ever have the chance to start over again, so make the best of it and I was able to. Soon enough, I was as comfortable in my tennis shoes as I was in my high heeled boots, and I was able to build upon nothing being in my way as I built my female privilege.

I knew then, I had made the right choice to follow my dreams into a trans woman world because I felt so natural. The light at the end of the tunnel was not the train as it beckoned me into a new world. It turned out, the main thing that was in my way all along was myself. Once I got me out of the way and for once was truthful with myself, I was able to move forward with a mental clarity I had never known before.

It was certainly worth the struggle to make sure my second chance in life was worth it. Sure, my gender issues were a major hurdle to move but it was no big surprise when I considered how deep gender runs in all humans. In many senses, discovering the true nature of me made life that much more interesting.

 

 

 

 



Tuesday, March 24, 2026

Imagination or Knowledge

 


JJ Hart. 

In the very beginning of my transgender journey, I often wondered if it was all just part of my very active imagination. Perhaps it was all part of me secretly hoping all of my gender issues would magically go away.

Of course, my gender dysphoria never went away until much later in life when I faced up to it and all I was doing as I viewed myself in the mirror cross-dressed as a girl, was slowly instill the knowledge my trans desires were not going anywhere. In fact, back in those days, the transgender term had not even been invented to use at all. I was living in the pre-internet “dark ages” of information. All I had was the well-worn issue of “Transvestia” from Virginia Prince to connect me at all to the world of people who had the same gender issues as I did. Closets were impossibly dark and lonely back then.

It took the knowledge of my situation to finally break into the light and see the world as a small part of who I really was. I finally used my issue of “Transvestia” to locate nearby mixers which were headlined for heterosexual transvestites only. If that was true or not, I found a diverse mixture of people attending which ranged from beginning cross-dressers all the way to impossibly feminine transsexual women heading for gender surgeries. The frustrating part for me was that even with the choice of individuals I felt close to, I could not find a group to hang out with. I was frustrated that I had come this far to still feel this completely different. The light was there, but it was very dim due to my complete misunderstanding of who I really was.

The one fact I was waking up to was that none of what I was feeling was my imagination. My gender issues ran very deep and would be very difficult to solve. As I always point out, since I was so busy being an active man at the time, the conflict was real. Once I realized what I was really battling. On the plus side, about this time, the internet became part of my life, and I was able to see and even reach out to others like me. It was all well and good until my second wife, who was more computer savvy than me, caught on to what I was doing and tried to stop me. After I used my imagination to find ways around her, I was still able to build knowledge of what it would look like if I was actually able to enter the world as a transgender woman.

Once I began to really explore the world as a novice transfeminine person, I really had to use my imagination to succeed in getting out every spare moment I had from work. I would purposely schedule myself off from my work on the days I knew my wife was going to be working late just so I had free time for exploration, is a prime example. In that case, imagination became knowledge as I actually began to explore what I needed to explore behind the gender curtain. Even to the point of making new friends who had no knowledge at all of my previous male life which I was trying hard to do away with.

More importantly, as I sat myself up for success in venues I really wanted to be in as a woman, imagination further faded as knowledge sat in as I was able to fill out my gender notebook. No more gay venues for me where I was treated as a drag queen and even ignored when I tried to order a drink, all the way to be treated as a regular where I wanted to be was the knowledge that I needed to succeed further.

During this time also, I spent a lot of time soul searching about if I was doing the right thing about attempting to femininize myself even more with my new lifestyle and going even further my seeing it I could be approved for HRT. Mainly because I felt so natural as my feminine self among ciswomen, I thought I would take the path of least resistance and continue building knowledge of taking the gender leap I was considering. In essence, I was taking all the imagination that the young girl in front of the mirror away and replacing it with the knowledge of what I could expect living as a fulltime transgender woman. I needed all the knowledge I could get because the risks in jumping the gender border were so great. It all meant saying goodbye to all the male privileges I had worked so hard to build up. Not to mention the extra pressure of the possibility of giving up spouse, family, friends and employment as I knew it. I needed to be prepared to burn it all and start over.

What I ended up doing was, hedging my bets a little by making new friends in a new feminine life which I hoped would soften the fall if I decided to jump off the cliff and never go back to my male self. At this point, I always mention all the women who helped me along but somehow, I miss the most important one, my inner female who came through in a big way when she was allowed to run my life for a change. Once I gave her the platform to flourish, there was no imagination of the path she was going to take.  She took the highroad without all the evilness you see in some fulltime transgender women. She just wanted to enjoy her life and be an active part of the world and the LGBTQ community. And she wanted to help others by writing about her experiences.

Which brings me full circle to where I am today. No imagination, just the knowledge of experience to get me by in the world.

 

 

 

Monday, March 23, 2026

Is Your Life Running Away

 

Image from Zac Ong
on UnSplash. 

Running more and more over the years described my life on so many levels. Most all because of my desire to be a woman. Over the years, I have moved many times, mostly because of a search for better jobs along with cross-dressing opportunities. I thought moving from my conservative smallish Ohio town to the huge metro New York City area would provide me with a more liberal base of people to work with. Which just wasn’t true, I found for the most part, I was still hiding my desire to go public in my skirts and makeup most of the time.

Mainly, it was a learning experience until I began to get older and all of a sudden saw time was moving away from me. Maybe you could call it my transgender biological clock. No one lives forever, and I still needed a chance to live out a chance to live life as a transfeminine person before I died. My new attitude added a certain importance into learning what I could about living as a woman. Or what I like to call, slipping behind the gender curtain to see how the other half really lived alongside a world of men who thought they ran the show. After several attempts of running straight ahead into failure in the public’s eye, I began to get it right with my presentation. Allowing me to explore more the true world of ciswomen who had carved out successful lives for themselves.

When I did all of that, I ran directly into communication problems. I will forever remember the first night when I attempted to add my thoughts to a group of men, I somehow found myself a part of. Suddenly, I found myself being totally ignored in the conversation and I needed to leave. There were pros and cons to what happened I found because the positive was I had presented as a woman well enough to be ignored but the negative was the whole affair marked the first time; I felt a major part of my intelligence along with my male privilege was being taken away from me. For the longest time, I felt the impact of running directly into a gender wall.

Happily, I did not receive any black eyes I needed to cover up with makeup from the running collisions I was having with the public as I set my high heels in motion to conquer my little part of the world. The personal stubbornness I had to succeed came back to hurt and help me when I moved forward in the feminine world of ciswomen. It hurt me when what was left of my old male self-tried his best to dictate how I should look for the world, which led to many fashion disasters. It helped me when I needed to pick myself up after getting knocked down again and again as I was trying to see what I would have to do to be a successful transgender woman. When I was able to put all my old self behind me was when I was able to finally see my future and run to it successfully.

The whole process of male to female gender transition was very exhausting as I tried to live in both major gender binary worlds for a short while. I always mention it to pass along a warning to all you who are thinking of trying it too. In the short term, painting yourself into a gender corner you cannot get out of is no fun unless for some reason you want it to be. For me, all it did was wreck my already fragile mental health situation. Since I already had been diagnosed as being Bi-Polar, I was already trying to keep one clinical depression controlled when I had another creeping up on me when I could not express my feminine self. I needed a lot of good therapy to separate the two potential huge problems. When I was doing it, I was still running as fast as I could to continue to chase my dream of living as a successful trans woman. Which would ultimately lead me back to just being me.

The frustrating part was the running target I was aiming for kept moving on me. Once I thought I had all I needed to play in the girl’s sandbox safely, I discovered another aspect of a woman’s life I never considered. Mainly because I was naĂ¯ve and knew a woman’s life was different than a man’s, but I was not prepared to find out exactly how different. All the varying layers of a ciswoman’s life really got to me for a while until I began to get my gender workbook filled with relevant new ideas on how I was supposed to live. In other words, all the doodling in my workbook started to make sense and I could see all the running I was doing to catch up coming to an end.

Either way I was getting into shape from all the running I was doing, or I just began to give it all up as I began to become much more successful in the world as a transgender woman. At this point too, the HRT or gender affirming hormones I was approved to take helped to calm me down and sync up my internal and external selves. Internally I began to feel emotions I never knew I had and externally I was helped along by softer skin, longer hair and my own breasts. Among all the other changes the hormones brought about. I just wished I could have started HRT earlier in my life because the changes felt so natural and I would not have to spend my whole life running from an invisible foe, myself.

Now in my advanced senior years, I am finishing out my workbook on its final pages. My final transition is just being the true me I always was meant to be. Deep down, I was never meant to be a runner after all.

 

 

 

Sunday, March 22, 2026

In Touch with Nature

 

Image from Brice Cooper
on UnSplash.

The “Ostara” ritual came off yesterday as expected with the usual suspects attending.

The weather cooperated with all the other plans, and it was a beautiful spring day here in southwestern Ohio. The only gender drawback did not even come because of me because there was a young very androgynous child there too. I could not tell the gender of the child and of course I did not pry. All went well until one of the other older women in the circle just could not leave the matter alone and said something to the child which elicited a loud response. Suddenly I heard “I’m a girl!”, and I thought the woman just could not leave it alone and had to go where she should not have been. Other than that, the woman sat next to Liz and I when we ate lunch and persisted on lighting up some sort of a cigarette after she ate which did not go over well with Liz and I who are confirmed non-smokers. The only good thing was after she smoked if was time for us to leave the ritual.

What I don’t think I realized was until after I received a comment from “Alex” who is transitioning from female to male was how much the opposite path of my gender male to female gender transition has meant to me. Now I can really feel the power of nature is a small example of how much more the Ostara ritual meant to me than I ever thought it could be when I was a man and too busy thinking about guy stuff such as work and sports to be overly concerned about my inner connections with Mother Nature. I credit the power of HRT or gender affirming hormones with unleashing a new appreciation for the world around me as I progressed with the hormones. All of a sudden, I was more in touch with the world around me with senses such as temperature and smell. I was very appreciative of permission I was given by the doctors I saw to go down the gender path I did, and I worry that the orange pedo in Washington and his followers will take it all away from transgender people of all ages today. Already it is happening here in Ohio, and I fear for my next estradiol prescription which is due to be renewed early in May.

It comes through the Veteran’s Administration health care system for me, and hopefully I still will be protected from outside political influence since I have been taking the hormones for nearly a decade now. Maybe I can fly under the radar at the VA and tie it all into my mental health (which is true) and something the VA is ultra-sensitive about. Fortunately, I have an appointment set up soon for a new psychiatrist who I hope will be sensitive to my entire situation. With that, maybe I can explain the power of the ritual I just went through on my overall mental well being and he will be behind me.

I think in many ways, getting back in touch with nature during “Ostara” takes me back to the innocent days of my rural childhood when my brother, friends and I had our run of the fields and woods around us. Growing up that way, with the freedoms we had, set in motion a lifetime of appreciation of nature that somehow got away from me as I grew into a false sense of manhood. Where “camping” out during Army basic training in Kentucky was as far as I got into nature. What a relief it was for me to make all the positive contact I had missed at least for a hour or so during the intense ritual experience.

I had no idea that my sense of gender was so intertwined with the world until I began to reach out to others and live it. And I am sad that mankind has managed to abuse the only world we have to call home, but that is another subject altogether. It all came back to me yesterday as I remembered the love I had for the woods which surrounded our house when I was growing up. I guess it took a jolt to my system which included a male to female gender transition, to bring myself back to a full circle experience with the world and back in touch with nature.

 

 

 

 

Saturday, March 21, 2026

In the Circle

 

In celebration of Ostara.

Today will be a beautiful day to get together with spiritual friends and celebrate “Ostara” which is the Pagan/Wiccan celebration of the Spring Equinox. The circle part comes in when the group is called together to start the ritual. It is supposed to be dry and near seventy-one degrees (F) today in the park we go to for the ritual, so you could not ask for a better day.

Meeting the group carries a deep meaning for me which goes past the ritual. Joining my wife Liz as she went first to the rituals and being accepted was just one aspect.  It was like I was adding a whole new barrier between my new feminine self and my old male one. I felt as if I was climbing a set of stairs to just becoming a complete me because in addition to attending the rituals, Liz and I were also going to Cincinnati area meetups for writers and craft people. I was meeting strangers for the first time when I was just me then surviving. I was proud as well as being happy about it. 

It was like I transitioned for the third time in my life as I went in a big circle. I started out as a cross dresser, moved to a transgender woman and then back to me. I cannot say enough about the confidence I was able to build up as I traveled my path from one stopping point to another.

In addition, I was curious about how going to the rituals would affect how I viewed the world spiritually. I knew I had always been a somewhat spiritual person without being a part of any specific religion. If I was made to have a choice, I would always say I was Buddhist because of my days in Thailand and how much I respected the gentle ways of the people. Anything but Christianity which rejected the very basis of being transgender in not all but several cases I had encountered. One way or another, religion is not a subject I want to get into here. It is a point of no return and easy to get stuck in stereotyping religions if I attempt to explain myself. So, I will leave it at that.

As I said, I am really looking forward to seeing old friends at the ritual again except for one who asks me what the transgender community thinks about what is going on today. Finally, I quieted him down by asking what he thought about what was happening to us. Fortunately for both of us, he said he hated it. If he did not the circle may have been broken.

 

 

 

Friday, March 20, 2026

All Along, I was just Becoming Me

 

Image from Pea on UnSplash. 

As I always point out, becoming me was a very difficult concept to adjust to.

First of all, I needed to understand who the true me really was and work my way to the light out of my dark closet. Sadly, it took me decades to face the truth about who I really was. I was never the male I was seemingly born to be. I was born to be a feminine person, no matter what it took to get there. Which turned out to be the key term over the years, as I risked everything to discover who I truly was. As my male self was busy building a wall to his world by becoming successful in his job, my novice transgender self-needed to take a back seat and watch the clown show.

The problem was that often the clowns were not funny and just needed to stop before they caused complete damage to my life as I knew it. I was living the male dream in many ways with a good job, small family and a close knit group of friends and it was difficult to even thinking about giving it all up, but I did. Male privilege was very real to me and preparing to give it up was intimidating to say the least. Somehow, I needed to find the true me and quit being so self-destructive when my gender dysphoria hit me. In most cases, my morning mirror was to blame when I looked in it for the first time everyday and saw a woman lurking behind my male self-shaving.

I did not really begin to understand who I truly was, until I put my cross-dressing world behind me and started to explore the world as a transgender woman. Before I did though, I needed to draw an invisible line in the sand when I went out and see if I could cross it. When I did, I felt a deep sense of gender euphoria and wellness. When I did not I had to force myself to go back home, return to my cross-dresser drawing board and try again. Which I needed to do many times before I started to get it right. The important part is that no matter how down I felt on the days I was abused in public, there always seemed to be the slightest spark of hope which came from feeling good and natural as my feminine self. Suddenly, finding my true self did not seem to be so far away, if I could find the time out of my busy life to do it.

That is when I started to use every moment of my spare time in my transfeminine explorations of a terrifying yet exciting new world of cis women. Plus, if I was not exploring, I was busy thinking about it when I was working as a man. I wish I had back all the excess time I wasted in those days when I could have put the energy into my family, spouse or work. It would have made such a difference in my life. As it was, my life consisted of slowly sliding down a gender cliff. Not knowing what awaited me when I finally let go of my male self and headed towards a feminine world for once and for all. At that time, I did not realize I would have a team of gentle womanly hands to soften my fall. I still had a lot to learn about going behind the gender curtain.

Even though I was becoming accomplished as my authentic me, I found I still had many years ahead of me to continue my journey. I still had to round myself out as a new person very much from scratch. It was difficult to not automatically out my male self when I was talking to a new woman who turned out did not care about him anyhow. It was time to put him in the background and pick and choose the highlights of what benefitted me as a trans woman creating a new life. It was a different way to live and took a lot of getting adjusted to. Far beyond just worrying about my appearance and if I could use the right rest room. I needed to be on my toes all the time because just the wrong response about my past could give my whole male life away.

Once I separated the forest for the trees, I was allowed behind the gender curtain or rather followed my woman friends back there. For once, I was on the gender ride of my life. The same one I had paid so many dues over the years to be on, and once I got there, there was no way I wanted to give it up. So, as you can tell, I had a lot of help finding the real me. Women like Liz, Kim and Nikki showed me the way with their knowledge of playing in the girl’s sandbox. They all helped to bring out the true me in ways they never knew as my male past faded into my rearview mirror for good. It was the only time in my life that a mirror made the right call for me.

Needless to say, finding my true self after all those decades really opened the world up for me and made life so much more pleasant. Since I was not suffering from all the gender in-fighting I was going through, my mental health improved along with everything else. It did not hurt that the HRT gender affirming hormones I was on were making serious in-roads on how I felt internally as a trans woman and how I was viewed by the public. I felt better all around.

The only problem that I see now is how long it took me to come up with my own gender truth. If I had faced the facts long ago, I could have saved myself and the people I loved around me all the emotional stress I caused. Finding the true me cost me the most precious commodity I had. My time.

 

Thursday, March 19, 2026

How Much Discipline do you Need

 

Image from Brett Jordan
on UnSplash.



One thing I learned the hard way in my transgender travels from male to female was that it took an intense level of discipline to do it. In fact, cross-dressing as a girl was the first thing I ever did in my life which took a large amount of discipline. School was easy enough and sports were something I always tried at but never excelled at.

Growing up, I was always under pressure from my parents to finish any projects that I started and do them right. That is when the struggle began. I have written fairly extensively about how I struggled with the makeup arts when I first discovered all the makeup samples my mom had stashed in a drawer beside her sink in the bathroom. Using the samples meant I would have less chance of discovery when and if she discovered someone was in her makeup.

The only parallel I always use was how I tried miserably to paint all the plastic model cars I put together. My cars never seemed to come out as well as my friends and I really did not want my makeup to be the same failure as my attempt at modeling cars was. For the first time in my life, I developed the discipline to do something about wearing makeup and I set out to become better at it. Which included being able to purchase the right supplies with the meager amount of money I had to work with. I was under a lot of pressure when I did my own shopping for feminine accessories, so I needed to make sure I did not make a mistake and buy something which made me look like a clown in drag going to the circus.

Little did I know, developing discipline in my feminine pursuits was just the beginning of a lifetime search for a transgender future. Every time I turned around, I faced a new challenge, it seemed like I first went out in the world of ciswomen. Where I needed to be better to just survive. A prime example was early in my life as a novice transgender woman, I had a difficult time of getting out of the mirror and putting a complete feminine image together for the world to see. It seemed as if every time I thought my makeup and fashion looked good, my movements and voice were totally off, and I would ruin the whole image. I just had to develop the discipline to do it all and complete myself as a transfeminine person.

Experience was the only way it happened. The more I went out into the world, the more I learned about if I could ever achieve my trans woman dreams. It was very important to me to explore all my options before I made such a huge and important decision in my life. Before long, I was sneaking out of the house every spare moment I had to live the new life I was carving out as a transgender woman. The problem was, the whole experience was terrifying while at the same time, it felt so natural. Further confusing me on which way I should go with my gender issues.

One way or another, I was developing the discipline to conduct myself in the world of women with my own set of standards. I learned to dress and makeup myself to blend in where I was going and more importantly how to communicate with others around me when I got there. It took tons of discipline to do it. Especially when I was making the mistake of trying to live in both binary genders at once. I needed to force myself to make sure I was projecting the right gender at the right time mainly when I was at my job as a successful man. I can’t tell you how many times customers tripped up and called me “mam” when I was going about my male business. Secretly I was pleased but could not show it. The bigger problem I always mentioned was that the gender ping-pong I was playing took a tremendous toll on my mental health. Switching back and forth was terrible.

The only positive was that I developed more discipline than I had ever had before. When I was a man, I knew I was temporarily holding on to a lifestyle I no longer cared about and when I was a woman, I totally had bought into where I wanted to go with the rest of my life. The only thing left to do was to seal the deal and do it. And learn the fine little nuances ciswomen know how to exist in their world. Like figuring out who the alpha female is and going after her approval. Through it all, I was building layer upon layer of confidence in myself. Which I would need later when the dark period of being extremely lonely set in. The intimidating thought of finding anyone remotely able to partner with again looked very dim until all of a sudden it was not. That is when I found my current wife Liz over a decade ago and she made a believer out of my self again and I could drop all my personal defenses to ever loving someone again.

It turned out that all the work I put into disciplining myself into being a totally different person worked out for the best. I emerged from my work with a newfound lease on life as the transgender woman I had always dreamed of becoming. I proved my parents wrong. I could take on a project and see it through successfully. Just not the one they had chosen for me. I tried once to come out to my mom and was rejected and never to my dad, so I doubt they would have ever approved of what I did. Even though what I did was save my own life by shattering my gender shell.

It took a lifetime worth of work to improve my feminine discipline. Mainly because I was blindly entering a world of ciswomen I knew nothing about as my gender workbook was blank when I started. After making up for lost time, I fairly quickly caught up and entered the world as myself.

 

Pulling Your Gender Band-Aid Off

  Image from Possessed Photography on UnSplash .  I am sure you have encountered a time when you just had to pull a band-aid off quickly fro...