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

Tuesday, May 27, 2025

The Inner Girl I Never Knew

 

JJ Hart, Club Diversity, Columbus, Ohio. 

As I was growing up, the girl I saw in the mirror did not seem to be quite real. Mainly because I was still caught in the male world I was born into. It seemed the more I struggled with my reflection, the more depressed I became. It did not seem fair I could not enjoy all the perceived benefits I observed from the girls around me. I say perceived, because it was not until I was able to go behind the gender curtain to see life was not always easier for the women around me.

Life moved on and I discovered always being the pursued by the opposite gender (males) was not often good. The problem was being pursued by the correct male. Not a scary, creepy or toxic one. Another problem I had learning from the females around me was I was so very shy and afraid to talk to any girls at all. So, I watched the dating scene from afar and wondered why I couldn’t be a part of it.

The main problem I had other than being shy was the gender dysphoria I was always suffering from. I was riding a dual edged sword. On one edge, I was struggling to meet the demands of my parents as their oldest son, and on the other hand, was the fact that some days when I woke up, I did not know what gender I wanted to be that day.  Problems I would not have wished upon my worst enemy. Finally, I did the only thing I knew how to do to survive, I went exploring. Or I should say, as I was growing up, I saw the girl looking back and then my transgender side went exploring.

My male self-stayed home as my feminine side attended transvestite – cross dresser mixers searching for answers to my true self. Ironically, the mixers just added more questions than answers. I discovered more layers in the cross-dresser community than I imagined existed. There was everything from male admirers at the party, all the way to impossibly feminine transsexuals I never knew existed. The biggest surprise was that my inner girl was again having a hard time fitting in.

One of the problems was, the transgender term or the knowledge around it had not been widely known at the time. When I finally heard of it, I thought it really described me, and I began to research it more. The tipping point came as I began to explore the public more and more. As I began to experience a new life I only dreamed of, the more natural I felt, and my missing girl was finally freeing herself from the confining world of my closet’s mirror. At that point, my pressure of transgender womanhood began to increase. It was less and less a fun game and became a very serious journey. The real reason why was the trip to my dream was becoming possible and was I going to risk everything my male self-had worked so hard to achieve.  

Nothing turned out to be easy as it seemed as I entered the world as a transgender woman. My focus needed to be dealing with other women on a one-on-one everyday basis. Over a relatively short space of time, I grew into the woman I needed to become to survive. Or my inner girl was growing up into a woman and I needed the gatekeepers to allow me to play in the alpha girls’ sandbox. Very soon, I reached the point of no return, and I had lost most of my past anyhow, so I had nothing to lose. My second wife had passed away along with many of my close male friends, so there was no better time to put my old male self completely in my past.

For the longest time, I never understood what my inner girl was observing and learning from. I found out when she finally had the chance to emerge into the world, she knew what to do. I thought in a small amount of time, she made a major gender adjustment and began to enjoy the dream I had attained. By I, I mean my male self was needed to propel the changes I went through. He provided many of the materialistic necessities I needed such as fashion, hair and makeup to get by. At the least, the entire process was very complex when I put my life into a gender mixer and hoped for the best.

There were plenty of times when I had the opportunity to purge my feminine belongings and return to a male life I never really wanted. When I kept coming back, I finally learned my inner girl was screaming at me to do the right thing. The right thing was to live out the remainder of my life as a transgender woman. Destiny led me to success.

Saturday, May 24, 2025

My Gender Workbook

 

Trial and error were my main learning directions when I was initially following my gender path in public. As my workbook on how to be a girl or woman was never filled out at all, I had no other recourse in which way to go. I just didn’t know, which meant I never would unless I had the courage to learn myself.

Missing the peer pressure other girls my age had when they grew up really hurt and I was jealous in so many ways. I missed sleep overs and other times girls came together and discussed so many secret issues I was not allowed to know. Which included when they compared makeup routines when I was left to experiment all alone.

Survival as a novice cross dresser became my inner motto as I struggled ahead in my male life which presented its other set of challenges. Such as dealing with sports, cars and bullies. Having interests such as sports helped to keep the bullies away, especially in my male dominated family. If I was careful in staying in my closet, no one had any idea of who I really was as I was filling in my workbook. Many times, I was in despair because it seemed I was not gaining any ground towards my dream of living as a fulltime transgender woman. First, I needed to discover if I had any possibility of success to succeed at all. Which started the so-called bucket list of things I needed to do as I pursued my workbook.

The biggest problem never changed. I never had much help when dealing with the basics of femininized fashion, hair and makeup. It seemed to me, every woman I met expected me to already know the basics and it was like a “C
atch 22” of being a woman. If I did not know the basics on my own, no one was stepping up to help me and If I did know, I did not need it. Sort of like when you cannot land a much-needed job because of no experience and you cannot find any experience because no one will give you a chance.

Perhaps, I am more fortunate than other cross dressers of transgender women because quite early in my life, I persuaded a cisgender woman to help me dress up head to toe as a woman. I thought if a woman with a lifetime worth of experience could help me, I could fill out my workbook, with help. Ironically, after the makeup was over, I was not impressed and felt all the time that I was on the right path and could do the same feminine work on myself. Of course, I need to point out I had already put years of time and effort into refining my fashion and makeup techniques.

Just when I thought I had reached a success point in my gender transition, my teen cross-dresser years set in. The problem was, I was already a testosterone poisoned thirty something man seeking change. My transition out of my teens was painful and not easy to do but I finally made it out after many tears from public abuse. On the other hand, my gender workbook gained another chapter I gladly filled out.

On another slightly different topic, I heard from “Michelle” who is working on her own gender workbook and was commenting on my “Seismic Gender” on the lesbian culture and transgender women: “I really love how you described finding your place along that femme spectrum. It makes me think about how much of this journey is trial and error—figuring out what to wear, where to go, how to be in these spaces without losing yourself. And yeah, sometimes it really does feel like the universe nudges the right people into our lives at the exact moment we need them.

Honestly? Reading this gives me hope that I’ll find my own version of that someday.

Thanks for the comment! If it helps, at that point I had given up on ever finding another special person for the rest of my life, and the most amazing thing happened. I did find my wife Liz, or I should say she found me. It happened primarily because I gathered the courage to repeatedly put myself out in the public’s eye.

Just be careful when you do it and take your time to properly fill out your workbook and you can be successful on such a major undertaking as living as your authentic self.

 

 

 

Tuesday, May 20, 2025

What an Adventure!

Image from Phillip Rawstron
on UnSplash
 Admittedly, at the age of seventy-five, I spend a lot of time looking back at my life, attempting to look at all the successes and failures that I went through.

The end result is normally wow! Did I do all of that? I remember the adventures I went through when I first left the house in my short skirt with freshly shaven legs and felt the cool night air on my body. At the time, I felt as if there was no other feeling like it and I could not wait until I could do it again. Then, there were all of the Halloween parties I went to cross dressed as a woman from head to toe. The parties were exciting to say the least but also showed me I could possibly make it in the public's eye as a transgender woman in the near future. It is important to note, I went through the stages of trying to dress sexy as a woman to trying to encourage the others at the party I really was feminine. 

When I started to try to enter the world regularly, I found I had many adventures ahead as I went from being laughed at to my face to at least presenting well enough to blend in with the world at large. Out went the short miniskirts and in came the jeans and tops which other women were wearing on a regular basis to the venues I was going to. At the time, it was less fun for me but at the least, my new fashion choices were saving me the torment of coming home in tears. For the first time in my life, the public was not laughing at me for simply trying to be who I felt I should be. 

From there, the adventure really started for me as I made the second big transition in my life. From part time cross dresser to fulltime transgender woman, if only in my mind. The entire idea was huge in that it took me back to the earliest days of admiring my girl-self in the mirror, and thinking that was good, but there was still something missing. The missing part became evident over the years; I wanted to be the girl I saw in the mirror. Little did I know at that time; my gender path would be a long and intense process. Nearly fifty years to be exact before I was able to come to terms to who I really was as a person. 

Before I was able to build a small number of friends I saw on a regular basis, I was intensely lonely, and on many nights was just going out to be alone. Hoping no one would bother me. Fortunately, they did, and my life took an adventurous turn for the better.  I ended up being invited to lesbian mixers, the women's roller derby and even an NFL Monday Night football game. To say I was scared would be too easy a term. Excited would be another appropriate way to think about what I was going through. Where had all of this been all the time I was stuck in my closet? 

Another big adventure was evident when I discovered I had more than one gender closet to escape. There was the physical closet of fashion, makeup and presentation to overcome, and then the major hurdle of the intense mental closet I lived in. I experienced major problems with overcoming the life my male self-had built for me. He was intense and did not want to let go. By then, it was too late, and I was never going back. 

All my adventures proved to be worthwhile, and I succeeded in living my dream of transgender womanhood. Plus, for those of you who think you have waited too long to live your dream, I waited until I was sixty before I started. 



Monday, May 19, 2025

Not Ready for Public Consumption

Porsche Boxster.
 As I made my way into a feminine world for the first times, I was amazed how different it was.

My male self-had grown used to pretty much getting his own way. He was successful in the business world even to the point of buying a new Porsche sports car of his dreams, primarily through the substantial restaurant bonus checks I was earning. Little did anyone know, my female side wanted the new car as much as my male side. She wanted to be the blond in the fancy new car.

New car or not, I was not sure I was ready for public consumption as a transgender woman. After all, I was still new to the world and was afraid to being discovered and ridiculed. So, I continued on through the recesses of my mind, until I presented well enough to get by in the world. 

One of the first major moves I made was to leave the confines of gay bars behind except for the lesbian ones I enjoyed so much. As with anything else, there was a learning curve to be dealt with. I learned there was nothing much I liked about the gay bars who for the most part either shunned me or treated me as some sort of drag queen. Oddly enough, the venues I did learn I was ready for public consumption were the big sports bars I was used to going to as my old male self. It was as if I flipped the switch and was able to go and enjoy a beer and watch my favorite sports as a trans woman and not a man and I loved it. 

Very quickly, I began to also love the attention I was getting in the new venues. I fit in quickly because I was friendly, made no trouble and tipped well. Once the staff at the venue's I went to understood I was only there for a good time and not any nefarious reasons, I was embraced as who I was and all of a sudden, I was ready for public consumption. One thing I need to point out was, none of this came easy to me. I started out with very little in the way of feminine features and I was used to surviving in a male world the hard way. I needed to work hard to feminize myself. Before I began to have an idea of how to feminize myself, I needed to understand how to do it. I spent many long hours in front of my mirror trying my best to perfect my makeup and fashion before I even had the courage to leave the safety of my own house. 

Once I did summon the courage to go out in the world, I also needed to figure out exactly what I needed to accomplish.  Early on, I was just trying to see if I can make it in the world, then it became more refined. Fairly quickly, I went from a man just trying to look like a woman, to actually exist with cisgender women in the world as an equal. Needless to say, the entire idea frightened me completely. I was totally out of the only comfort zone I had ever known as I explored a new feminine world. The good news was freeing myself the toxic relationship I had maintained all those years as I gave my best effort to live as a man. 

The best part was my dream did not turn into a nightmare when I transitioned into the authentic life I always should have been living. When I was finally ready for public consumption, I was ready. 

Sunday, May 18, 2025

Not an Act, not a Phase

JJ Hart Speaking Up at a Trans Wellness
Conference.

Very early on in my crossdressing experiences with the mirror, the vast majority of feminine fashion and makeup I could find came from my mom. As I grew of course, I was guilty of stretching her clothes and ruining some of her makeup.

For some reason, she never brought up my passion for being feminine. Plus, she never found my secret hiding places for my clothes. I think now, rather than confront me about a problem so intense, she chose to ignore it, thinking it was a phase and would go away as I grew up. If the truth be known, there were times when I wished my gender issues were a phase too. Those were the times when I "purged" or threw away my feminine clothes and makeup, swearing never to cross dress again. Of course, every time I purged, the pressure would build again, and I would start all over again to femininize myself. Over the years, I came to learn my connection with the feminine gender was anything else but a phase. It ran much deeper in me. Ignorance was bliss until I began to face the reality of who I was. 

It certainly was not a phase in my life which made my cross dressing anything but an act also. My experiences helped to reinforce the fact I was not trying to fool anyone when I first entered the world as who I labeled as a novice transgender woman. 

So, if I was not in a phase, or just acting like a woman to fool the public, who was I? I was in a personal struggle to search for any idea I could latch on to until I finally had to face the reality of my transgender womanhood. Yes, I went through all the questions of just being in a gender phase, all the way to thinking I was just trying to fool the world when I attempted to present myself as an attractive woman. 

Once I did come to the point where I truly accepted myself as who I really was, the entire process helped me to establish myself in the world and make new friends. My worst fears of being viewed as just a man who put on a dress and makeup as a part time basis were never realized. On the other hand, I played upon the fact I was different from the rest of the public as a transgender woman. If I was to be unforgettable, I most certainly needed to make sure I was making a positive impression. I spent much of my time listening to other women. Trying to pick up the smallest nuances of a ciswoman's life and how I could apply it to myself. 

As I advanced along my long gender path, I needed every small boost I could get to get me by with several close calls in an unfavorable world. It took me years to understand my gender issues were anything, but a phase and I was not a glorified drag queen in the world. It just took me more time to prove it to others. Basically, because I was scared of the knowledge of who I really was and feel secure in my transgender womanhood.

Friday, May 16, 2025

The Forgotten Woman

Image from UnSplash.

 Over the years of gender infighting, I needed to carefully sustain my transgender womanhood because she often was the forgotten person.

To begin with, she began life as a second-class citizen in my world when I was born as a male in a male dominated family. Essentially, she had two walls to climb immediately to survive at all.   First of all, she did not have any on hands guidance from mom or girlfriends to show her the way through life and secondly, my male self was successful at all in the world, she was completely forgotten. The fragile complement between my genders had to be maintained at all times or she would disappear. Many times, I asked myself why I wanted her along to begin with, but the answer kept coming back, I needed her.


I discovered the hard way, the occasional trip to the hallway mirror dressed as a girl with full makeup, just was not going to cut it. I just needed more. If I could manage to look like a girl, why couldn't I be a girl, if only in my mind. The problem became, when I had to return to my male reality, I needed to forget my girl self altogether. Many days, it seemed like cruel and unusual punishment. when the only true punishment came at the expense of my already frail mental health. All too often, depression would set in when I forgot my feminine self and could not least appease her by cross dressing in the mirror. 

Another problem was, the more I appeased my forgotten woman, the more my male self-hated it. He fought hard when any portion of his life was threatened. He tried his best to make it easier in life by gaining white male privileges which were difficult to give up. I became successful as a male, but try as I might, I could not forget my inner woman. Who, at the time, was learning more and more how to establish herself in the world. Many times, my male self would win the battles in our life when along he was losing the war. A typical female move he was too blind to see as he blustered along in life. 

When my forgotten woman became less forgotten and more accomplished, my male self-started to panic as he could see the end in sight. Without being a winner. Basically, he teamed up with my second wife to attempt to save what they could of my life. At that point, decisions needed to be made in the worst way. My so-called forgotten woman had learned she could indeed live a life on her own terms. The ability to stand on her own two feet after all those years in a closet was so liberating, she knew she could never go back and, on the other hand, my guy knew deep down he was defeated. 

Living a transgender life she had always dreamed of was suddenly all that mattered. She dictated I start gender affirming hormones to feminize my body outside and inside and that was just the start to being accepted in the world. At that point my forgotten woman was not forgotten anymore, and she got her just due for all the years she waited for control. She loved every bit of it.

Tuesday, May 13, 2025

In the Passing Lane

JJ Hart.

Early on in my life as a very serious cross dresser before I came out as a transgender woman, I obsessed about my presentation as a woman. Or, in other words, was I "passing."

At first, I went overboard and tried to appease my male side and dress sexy. Naturally, I was a dismal failure with my choices and ended up attracting too much negative attention to myself. After too many disastrous evenings in the public's eye, I finally learned my lesson and began to blend in with the cisgender women around me.

The problem was, still trying my best to slip behind the gender curtain and survive as a transgender woman was very difficult. At the time, a transgender woman friend of mine said it best when she told me I passed out of sheer willpower. She was correct, and I knew I was never the most attractive woman in the room but none of that really mattered as I was beginning to live the life I always had dreamed of. If others somehow resented it, they would just have to get over it. 

Being the keen observer of women, I always was, I found out not all cisgender women passed in the classical sense either. The skillful ones worked around their physical appearance issues with fashion and makeup choices which flattered them. I figured if they could do it, so could I. Finally, my fashion and makeup became second nature to me. At that point, I was not passing out of willpower but more out of inner confidence in myself as a novice transgender woman exploring the world for the first time. Once I found myself in the passing lane, it became easier and easier to stay there.

Even though I had fewer and fewer accidents in my quest for transgender womanhood, I still suffered minor bruises along the way. Mainly from cisgender women who completely did not want me in their world and went out of their way to show me.  Many of the attacks I suffered from were passive aggressive in nature and they took me awhile to get used to, but I did. I developed the extra sense most women have for the world around them and went on with my life as a better person. Secure, I was doing the right thing in my life and did my best to stay in the passing lane. 

These days, I have the benefit of age on my side. The genders naturally blend with age, so with long hair and a little makeup, I can survive in the world. Also, I don't have the vanity about my feminine self I used to have. Plus, I am so fortunate to have my staunch ally and wife Liz by my side the overwhelming amount of the time. An example was the vacation we went to the Florida Keys on a tour bus. If you are not familiar, one way or another on a tour bus, you get to know others. On the trip, I knew I had it made in the passing lane when a couple of women asked if we were sisters. I immediately relaxed for the remainder of the trip.

Overall, since finding my way into the passing lane was a matter of sheer will power. I had always believed if you wanted something bad enough, you could achieve it. Deep down inside, I never had wanted anything more than to be a woman. To arrive at my dream, I needed to get into the passing lane and stay there. Using whatever feminine tricks, I could find and use.

As "Stana" from "Femulate" once said, make sure you properly signal before you get in the passing lane. Once you make it, you will love it.

Sunday, May 11, 2025

A Complex Day

 

JJ Hart. (right) Mother's Day 
last night. Liz on left.



Another Mother's Day is here and as always, it presents me with many complex emotions.

First of all, as I was growing up, my mom was many times the dominant parent in the family, I remember vividly watching her apply her makeup, heels and hose. She was from the WWII generation where a woman's appearance was very important. I think she did a wonderful job maintaining a family of males immersed in boyish struggles. Dad was always present, and was often the deciding factor in our family disputes but mom ruled in all the other areas such as day-to-day discipline between my younger brother and I.  

My mom and I were much alike in many ways. I resembled her except I was close to six foot tall, and she was only five foot two, which made it quickly impossible for me to squeeze into her clothes. Over the years, she never let me know that she knew anything about my cross-dressing habits. Looking back now, I do not think I could have hidden all my feminine collection of clothes and makeup so well from her. She was somehow just ignoring me and my gender issues as just a phase. 

My life as a "transvestite" (as it was known back then) stayed hidden as a topic between mom and I until I was back home after being discharged from the Army. The sit-down did not go well and ended with her offering psychiatric care. From there, the subject of me wanting to be a woman was never brought up again during her life. For years, I held her feelings against her but then started to slowly change after I started to mellow within my own transition. I began to realize, mom was just dealing with life under the only circumstances she had ever known, and change was not in the cards.

What I ended up doing, was honoring her when I legally changed my name. I femininized my maternal grandfather's name as my first name and used my mom's first name as my legal middle name. It was my way of honoring her for all of the sacrifices she made for me.

Then, there was the complex problem on what the kids in my life were going to call me on Mother's Day. Initially, my daughter referred to me as her "parental unit", then began to slowly change over the years. Several years ago, I wrote a blog post which mentioned the first Mother's Day when my daughter referred to me as Mom. Even I was embarrassed to refer to myself as a mom, but I was surprised and flattered my daughter did. 

Now, both my daughter and my wife Liz's son both refer to me as mom on Mother's Day. One way or another, the day will forever bring complex emotions to me. I did receive many negative reactions to my Mother's Day posts, so I will temper this one by saying whatever you believe and however you are referred to, have a wonderful day. 


Tuesday, May 6, 2025

Primary Voting Day

 

JJ Hart Speaking out.

Today is the day to vote in the Ohio state mid-term primaries and is one of the voting days I cherish so much.

I cherish voting so much for several reasons. The main one of course is it is it's my duty as a citizen to vote. Another big one always comes when I have to show my driver's license to receive my ballot. I will forever remember the first time I had to present my new license with my gender marked with an "F" for female. I am sure no one in the crowded line was prouder than I was. Probably even more so than the first time I ever voted. 

After my wife Liz and I vote, tradition has it that we go out to eat at a nearby diner style restaurant. So, I will have to step up my feminine appearance a little. I am picking out a different pair of leggings and shoes to wear along with a light sweater, since it still a little chilly and rainy in the Cincinnati area. Of course, I will also shave and apply a light coat of makeup so I can look as presentable as possible. 

Sadly, if the current administration gets its way, my path to voting will be much more difficult under the so-called "Save" Act. As I understand it, I may need to present a birth certificate as a second form of identification to prove I was born in this country. The problem is that my name on my birth certificate had never been changed and does not match my new legal name anymore. To make matters worse, it is nearly impossible in Ohio to have a birth name changed on a birth certificate. I would be stuck between a legislative rock and a hard place along with so many other women, trans or cisgender and my precious right to vote would be gone. I guess I will have to face that challenge when I come to it. 

Speaking of challenges, tomorrow, I have a long-awaited appointment with my Endocrinologist. I say long awaited because my virtual visit with her has been postponed before. I get my hormonal medications through the Veterans Administration; she is my gate keeper and has to approve my all important gender affirming hormones. Perhaps all of you remember, recently the new administration in Washington at first dictated no more HRT for veterans through the VA. Then they partially reversed their edict to cover only new vets which is bad enough but obviously did not include me. 

My next problem could be coming up soon with my Endo herself. The word is, the Dayton, Ohio VA hospital where I receive part of my care will be cutting three hundred fifty of its staff. Which means I could lose access all together to the staff responsible for dispensing and monitoring my meds, Again, we will see what happens with her and the moderators who run the LGBTQ support group I go to virtually every Friday. 

It turns out voting maybe the least of my problems thanks to many circumstances I cannot control. Thanks to a convicted felon who is destroying the country. 

Sunday, May 4, 2025

Reality

JJ Hart, middle, with Min and Kathy



 It took me years of denying my true gender identity to finally face the reality of who I was really was.

To do so, I needed to transition more than once to my surprise. I was naive and thought when I just put on a dress and makeup I was done transitioning. When in truth, I was only beginning my gender path. Deep down I knew there was something deeply wrong with how I viewed the world in all ways. Did I view it as male or a female. The only fact I did know was I was completely alone with my gender issues. There was no one else to talk to. 

Reality was a dark closet with no doors I could escape from. My only outlet was admiring my image in the family mirror growing up. I even went to the extent of taking on a rural newspaper route to add to my meager allowance to buy my own makeup and panty hose. By doing so, I could stay out of my mom's makeup and stop risking the possibility of snagging or running her hose. If you remember the panty hose which came in an plastic egg, I was a huge fan. The difference between just dressing in the clothes I found or bought was growing huge. No matter how much I cross dressed and admired myself in the mirror, the reality was, it was just never enough. Whatever I was doing, I could do it better. 

One of my biggest problems or dreams was to have my own glamorous wig. I grew up in the era of crew cuts or shorter hair for boys so there was nothing I could do to style what hair I had into anything resembling a feminine style. I was caught for many years, college in fact, before I could manage to sneak around and buy myself a wig I loved. It was long and blond, and I cherished it. I viewed the wig as one of the final pieces of my cross dressing puzzle. Maybe then, I could actually try to enter the world as who I was actually beginning to perceive as my authentic or true self. Little did I know, I was just spreading the seeds of my gender future.

The reality was, suddenly I was realizing I was following a life's path I wanted to be on. Each time I attempted to jump off of it, by purging all my feminine possessions. When I did, I could barely live with myself and could not wait to return to the protective confines of my transgender womanhood. Even though the path was bumpy and often threatening, the alternative of going back was even worse. The path allowed me to enter an oasis from life for me to judge where I was and where I wanted to go. As I always say, I was careful and took my time because I had so much to lose in my male life. I needed to make sure I was doing the right thing before I entered the world of women fulltime. 

Reality showed me the way; I finally put aside everything I had which screamed male and never looked back. As I said, the path I took was long and dark and I made my share of mistakes when I ran into the walls. The powder keg which was me needed to be de-fused so I could live a free life in a very pleasurable environment. I can't say the wait was worth it since I had no choice. I was stuck in a male world of my own making and did not have the courage to realize I had the power to break out and live my truth...or reality. 

Saturday, April 26, 2025

Every Eye was on Me

JJ Hart

 When I was first entering the world as a novice cross dresser or transgender woman, I felt as if every eye was on me.

For the most part, most eyes were on me. Especially from other women. I vividly remember the times I was looked from head to toe by another woman. Slowly but surely, she was undressing every aspect of my fashion and making no secret of it. I thought at the time, I was just being introduced to the aspect of womanhood and to just get used to it.

At the same time, I was working on my overall femininized presentation, I was trying my best to mimic the way women move so I would not appear as a linebacker in drag. My adventures took me as far as trying to walk like a girl in large box stores late at night. I wonder now how many security cameras I made it on trying to perfect my walk. Through it all, I needed to be careful I was not walking the wrong way at the wrong time. Or for example, remember to not try to walk like a woman when I was working as a man. The entire process became more difficult the more I began to split down my time increasingly in favor of being a woman. I started with just cross dressing when I could a few days a week and ended with splitting my time four days a week in a feminine world versus three as a man. The whole process became even more complicated because I was still working my full-time job as a man. Especially when it came time to getting a new pair of glasses and I wanted to change over to feminine frames. 

The most difficult aspect of what I was attempting to do was the mental aspect of trying to juggle both main binary genders. I needed every moment to work on my transition and get used to all the nuances of it. A big portion of the process involved being looked at. At the least, no matter how well I applied my makeup, styled my hair and picked the right clothes for the occasion, I was still a big woman and would naturally attract attention. I attempted to conquer the size issue by losing weight. I responded by losing a significant amount of weight which helped in two ways. I could fit into better fitting women's clothes and at the same time look better when I went through another woman's inspection.

Of course, I was inspected by men too, but the inspection was much simpler, and I knew what it would involve. Women on the other hand, had more to look for since they had experience in the fine points of putting outfits together. At some point in their life, they had to put together everything from shoes to wardrobe to hair to put an outfit together. Since I needed to do it too, I knew what they were looking for and tried to plan for it. My accessories needed to match the rest of my hand-picked outfit to succeed. Even still, the times I went through helped me to prepare my future life as a transgender woman. 

If every eye was going to be on me, I was just going to have to adjust and do the best I could. If it was possible, I would try to thank all those women who looked me up and down. They taught me what I needed to do to succeed in my future. 

Friday, April 25, 2025

Opening Your Eyes

 

Image from Jesper Brouwers
on UnSplash.



I found I needed to be careful as I tried to negotiate a difficult gender path to transgender womanhood. 

Most likely, my eyes were open for the first time when I explored my mom's wardrobe for clothes and makeup I could try and see myself in the family's full length hallway mirror. When I saw myself, my eyes somehow were opened, and I knew I could never go back. Being a so-called normal boy was not going to cut it. 

From my humble beginnings, a small fire within me grew to a point where I knew I could never turn back from at least trying to set feminine goals and living up to them. The problem was, I had no workbook to rely on when the going got rough. I had no girls sleep overs to go to, or a mom to council me on my appearance. It came down to my relying on the mirror to tell me everything I needed to know about my femininized life, and it turned out the mirror could easily lie to me. It would tell me I was pretty, when in fact, I looked like a clown.

Following being rudely rejected by the public, my eyes were finally opened to the fact I needed to make changes in what I was doing if I was ever to survive. Soon I was haunting every nearby thrift store I could find for just the right feminine wardrobe items to add to my closet. It took a while, but I began to turn the corner and began to work my public presentation to a point where I could blend in with the cisgender women around me. My only real problem came when I did not have the finances to purchase the rare item, I thought I needed in the worst way. An example I still remember was a full-length wool powder blue coat I found at a discount coat store. It was in my size, went with my blond wig and I desperately wanted it. Long story short, no matter how many times I went back to the store and admired myself in the mirror, there was simply no way I could buy it. The main problem outside of affording it, was where would I hide it from my wife when I got it home. I needed to give up and move on to a cheaper alternative to keep out the Ohio cold. 

My eyes were really opened when I was allowed behind a rather formidable feminine curtain which women use to protect themselves from men. First of all, I needed to earn my way into their inclusive club by proving I was much more than a casual observer of women and most of all, not another drag queen. Step by step as I earned my way into a new and exciting gender world, I knew I was making the right move away from a male life. Mainly because I felt so natural in my experiences I was having. I cannot say my life was easy back in those days because I was stuck between two genders but on the other hand, each time I reached a new point of success, then I could not ever turn back. Again, because I was feeling I was headed in the right direction. 

Another problem I had during my journey was making sure my vision was correct. It was easy to have 20/20 vision when I was looking at myself in the mirror, but much harder when I was having a conversation with a strange woman. I was burnt many times when my vision of what was going to happen was blurred. 

Each time my eyes were opened, deep down I knew I could never go back. 

Thursday, April 24, 2025

Wishes were not Enough

 

Image from Delphina Iacub on UnSplash.




In yesterday's post, I wrote about the amount of time I spent wishing I was a girl as I went about attempting to live a male life.

As I pointed out yesterday, I finally arrived at a point where every spare second, I was becoming dedicated to my pursuit of becoming a girl. Which included watching the girls around me closely at school. I was desperately jealous of their fashion and lifestyle. 

As I became older, in order to survive in the world, I put less time wishing I was feminine and adding more time into actually doing it. Which meant of course I needed to unlock the door to my gender closet and try to enter the world as a novice cross dresser or transgender woman. Back in those days, I took a lot of rejection, as I thought I looked like a clown in drag. Stubbornly, I persisted until I could find the right mixture of makeup skill, fashion and wigs. Once I did, my life across a new and exciting gender border became much more satisfying and fun. So much so, I was fooled into thinking my feminized wishes were coming true. 

It was about that time when I hit a gender wall as I found out what my wife was telling me all along, I had a long way to go on my path to transgender womanhood past just looking like a woman. I needed to quit wishing and find out what she was talking about. 

The more I explored the world as a trans woman, the more the world opened to me as gender curtains were pulled back. Of course, I knew cisgender women had their own world to exist in but I did not know how strong and in-depth that world was. For the longest time, my head was spinning as I tried my best to absorb the daily lessons I was learning. Primarily about communication and co-existence with other women on their playing field. Certainly, wishes were not enough when it came to surviving in a woman's world. I found I drew the curiosity of other women who wondered what I was doing in their world, and I had to be better than the average ciswoman just to get by. 

It was about this time; I decided to take a shortcut in my external femininized appearance and research doctors to see if I was healthy enough to begin gender affirming hormones (or HRT). I was, and the hormones almost immediately went about making changes such as softening my skin and producing breasts. All of which helped me to help my presentation skills. Especially, since I did not have any male pattern baldness and quickly was able to grow my own hair out and go wigless. 

I found by this time, wishes did not have to be enough, and I could move up my final transition timeline. Finally, my long-awaited dream could become a reality, and I could put my hated male clothes away forever. Perhaps the best part was, I never wished for him to return.

Tuesday, April 22, 2025

The Ultimate Confirmation

 

Image from George Pagan III 
on UnSplash.


My ultimate confirmation in life came when I arrived at a point when I knew without a doubt, I needed to live out the remainder of my life as a transgender woman.

My journey took me to the age of sixty when I finally put my male clothes away and live my dream. Along the way of writing the blog, I have received many interesting comments. Many concerning why I took so long and equating my time as a very serious cross dresser as somehow meaning I was never actually transgender at all. The best all time comment I received was, I was just another old guy on hormones. The comment came so long ago, I do not even remember how I responded.

I can make many excuses as to why it took me so long to transition completely such as I had a wife, I dearly loved who was against it, and a job I worked years to get which paid me well. While those are the given reasons, my ultimate confirmation came from the fact, I just did not have the confidence in myself to do it. For years, I was still being laughed at any time I went out in the world as my femininized self. Before I became very serious about my presentation and lost nearly fifty pounds off my masculine frame and began to take better care of my skin so I could wear less makeup. At that point, the laughter stopped, and I began to acquire the all-important confidence I needed to live my new transgender womanhood. 

Without confidence, I had nothing and little by little, I began to acquire it by doing trips into the world which took me away from the easy malls and clothing stores I was accepted in for my money, to the restaurants which presented me with whole new challenges to overcome such as having to communicate with servers and bartenders one on one. I even went as far as to stop going to the gay bars I thought were safe and going back to the big sports bars I was used to going to as a man. At that point, my ultimate confirmation was establishing myself as a regular at a couple of key venues where I was even given restroom privileges. Obviously, my confidence skyrocketed to a point where it never had been before. I could not wait to do more and more. 

Even with my newfound confidence, a fulltime life as a transgender woman eluded me. There still were huge life questions such as what would I do to support myself, all the way to how I would tell my friends and family. It was about this time in my life when destiny stepped in and answered nearly all my problems. In the space of a couple tragic years, my wife passed away, along with nearly all of my close friends. Leaving me all alone to guide my life in any direction I wanted to. The direction it took me was straight to gender affirming hormones which the Veterans Administration health care system was just starting to prescribe. Since I already was a VA health member, I went through the approval steps and was approved for the HRT program. 

My male self was stubborn about letting to but even he could not fight the ultimate confirmation he was facing. He should have never been in my life to start with and once he got there and established himself, he was difficult to remove. 






Friday, April 18, 2025

Forever Dancing

 

Image from Alexa Posteraro
on UnSplash.

During my long gender journey, I often thought there were times when I had finished my trip and made it to my goal of transgender womanhood.

It was during those occasions when life laughed at me and said I better begin dancing once again. As always, I was a terrible dancer and needed to try harder than the average woman to succeed. If I did not, I knew I would never make it.

Earlier in my journey, I thought I was doing enough dancing to get myself by and then hit a solid gender wall when I failed. Any gender euphoria was very brief and fleeting as I went out in public as a novice transgender woman for the first time. On too many occasions, I needed to hurry home in tears after being laughed at (or worse) by the public. Fortunately, I was somehow able to pick myself up and get back to dancing the best I could in my gender game. At whatever cost I needed to do, my first priority was to improve my overall femininized presentation. 

I started by losing weight. In fact, I shed nearly fifty pounds which enabled me to better fit into a wider and more fashionable style of women's clothing than I ever had before. From there, I began to work more diligently on my skin. So, I could wear less makeup. Then I added better wigs to my dance list and finally began to notice a difference in how I was perceived in the world as a transgender woman. By that time, I thought I was ready to dance but I was far from it. All I had really done was carefully craft a feminine image which I needed to put into motion. 

As I continued to enter the world as a transgender woman, many times, the world pushed back at me. I had problems with how I moved and how I communicated with the public before I could ultimately relax and really learn to dance. As I tried and tried to improve myself, most of the push back came from my second wife and my old male self. Both of whom had stakes in my success or failure in my new world. I have written often of the times when my wife rightfully said I made a terrible woman. Mainly because I was still putting my woman together and was making mistakes. At that point, I did not have the lived experiences as a trans woman to do better and anytime she caught me out of our agreement to explore the world, all hell would break lose. Afterall, she understood more than I did how she was losing my male self to another woman. Who happened to be me.

Once I broke through and decided transgender womanhood was the only dance for me, I began to do better. Physically, I never made it to being a better dancer, but mentally I did. Primarily because I needed to survive in the feminine world or sandbox, I chose. By nature, I found cisgender women operate on a whole different level than men. Which I already knew of course but not to the point of survival I found myself in the midst of. To oversimplify, men came at me from at the most two angles, and women from many more. I was ambushed by several passive aggressive women on many occasions before I learned to protect myself from perceived lesser threats. 

To this day, I am still dancing. Primarily because it is what it takes to be a transgender woman in todays' world. Plus, I would be remiss if I did not mention the small group of women friends, I had who were instrumental in helping me with my dancing lessons.   

Tuesday, April 8, 2025

When too Much Wasn't

 

JJ Hart (Middle) with two friends.




As I continued along my long and winding gender path, I (on occasion) ran into situations when the public seemed to be too much. 

Examples were the times I was approached in public by strangers when I did not want to be. Very quickly I needed to judge their motives. Did they see me as a man in a dress on one hand, or as a woman on the other. Naturally, it made a big difference when I returned home and rated my experiences as a novice transgender woman out in the world for the first time. How did I do? Was I too much for my own good and did I need to tone it down, or attempt to do more?

There were the times when I managed to thrive in situations where women dominated and times I could not and ran home. Back to my gender drawing board. There seemed to be so much to learn, I was overwhelmed by the task ahead of me if I was ever to achieve my dream of living a femininized life as a transgender woman. 

In the end result, normally I found too much just was not when I was trying to get ahead in a new world I was just getting used to. The problems occurred mainly in the areas of fashion and makeup, as well as where I was trying to go when I went out. Once I got them under control, I was able to build a stable new life in the girls' sandbox. Once I earned my way in. Often earning my way in, had its own set of challenges. Mainly I had to find out how to play correctly to be accepted. On the other hand, even though it was difficult to do, I had to play to learn a life's full of lessons in a hurry. As I always say, my women's workbook was blank to this point, and I needed to write it. 

I found as I struggled to fill out my workbook, I needed to be extra vigilant in how I viewed other women, since I was totally on their turf. For the most part, I did my best to hold back on my opinions and speak mainly when I was spoken too. It worked well enough until I could get my feet on the ground, and I could move forward as a transgender woman. My goal was to build my new life as a confident, intelligent woman in society, but I needed to prove to myself my goal was not too much and would destroy my dream of transgender womanhood. Fortunately, throughout my life, I had several strong positive feminine role models to work from and add to my workbook. When I was able to add their influences to the inner female, I already knew was there, the women formed a strong bond to guide me through my struggles.

Overall, I discovered rarely too much just was not. What was happening was, I was just paralyzed by fear to move on with my new life. Once I got over most of my fears, I was able to move on and be free to live a better life. A better mental health life waited for me when I quit fighting two genders to survive. 

Thursday, April 3, 2025

Authenticity

Transgender flag flying at 
Cincinnati's City Hall.



 In order to just get by in the world, transgender women, or trans men need to be authentic. Which is always easier said than done. 

First of all, you need the confidence to try out your new self in an exciting yet scary different world. Maybe, a person smarter than me has an idea on how to provide yourself with confidence other just by just doing it. For transgender women, among other things, it means putting aside all the hard-earned male privileges we came to be used to. In order to be truly authentic in our transgender womanhood, everything male had to go. 

It took me years, or even decades to get around to living authentically as a trans woman. Before I was able to, I needed to adjust my thinking to what a woman really was, and what she had to go through during her life. As my second wife kept trying to tell me, there was so much more to womanhood than just looking like one. Finally, I started to realize what she meant, but it was not until I made it out into the world as a novice transgender woman, did I realize what she really meant. For me, it meant the girls nights out I was invited to, along with everyday communication helped me to discover my true feminine self. 

Even still, all those nights I went out to be by myself were not helping me with my authenticity. I learned the difficult way all females were not women because they were never socialized into womanhood. Through it all, I wondered where the whole process would land me. For years, I feared a hard fall in my life if I had fully transitioned into transgender womanhood, but it never happened for me. I think, the more I learned in my new life helped strangers to interact with me easier, one on one. 

Perhaps the biggest discovery in my life came when I learned firsthand how powerful my internal feminine self was. Once she sensed she had control in my life, she effortlessly took over and guided me to a soft landing when I slid off my gender cliff. One of the main things she did was making me how total the femininization process was once it got started. I guess the first thing she changed was how I looked at my life. For example, she made me realize I was never a man cross dressing as a woman, I was a woman cross dressing as a man. All of a sudden, my early life made sense as to why I could never satisfy the deep craving I had to dress as a woman, only to discover a couple days later, I would be depressed if I could not dress again and find the nearest mirror. I needed constant reassurance I was on the proper path to my own form of transgender womanhood.

I guess, authenticity can only be earned the hard way through lots of work and even experimentation.  When you do experiment, and are successful, gender euphoria and confidence set in and you are ready to move forward in your life.   


Monday, March 31, 2025

Transgender Day of Visibility

 

Transgender Day of Visibility
poster from my
hometown. 


Today is the annual transgender day of visibility on March 31st. 

It is a time such as never before to attempt to stand up and be counted as a transgender woman or transgender man. Sadly, it is also the time we trans people take the most risks to do so. Stakes are becoming higher and higher against us coming out in many areas of the country, especially, here in my native Ohio. Where an overwhelmingly republican legislature in the state capital of Columbus has passed bill after negative bill against us. 

To me, my visibility is an ongoing deal. Since I live fulltime in my transgender womanhood, long ago I decided to never run and hide my feminine nature. Back when I did not have so many mobility issues, I was more of an active participant than I am today. In place of being active at all, I have tried to pick up my pace with my writing and protest with my keyboard and votes. 

Plus, I know I am so fortunate to have found and married an accepting/encouraging spouse who helped usher me into my transgender womanhood. I know so many others in the community who are so lonely. 

Wherever you happen to be in your gender transition, these troubled days present a troubled challenge to being visible. Challenges such as your presentation provide sometimes insurmountable hurdles to being more visible. Similar to a "Catch 22" of passing. In other words, you need to be seen in public to learn if you present well enough to stay out of personal danger, but it is scary to even start to get the experience to begin with.  Again, I was lucky when my time to come out meant at the worst you were laughed at and not beat up. Plus, I was able to put years of practice into makeup, fashion, and wigs when I cross dressed in my closet. If the times were reversed, I often wonder what I would have done differently, if anything. All in all, it is just another one of those life's questions I will never know.

On this transgender day of visibility, I hope all of you find your own way to be visible. Anything from marching in a parade, all the way to looking at yourself in the mirror, find a way to celebrate the rare, beautiful self which is you! 


Saturday, March 29, 2025

Nothing but a Reflection

 

Woman in Mirror from Darius Bashar
on UnSplash.



It seems for some reason, recently, I have been obsessed with thinking about my earliest days of admiring my girl, cross dressed reflection at home in the mirror. I hope in this post I will be able to take my obsession a step further. 

I believe women have a head start over transgender women when it comes to the basic concept of being viewed in the public's eye. To begin with, women are faced with more appearance scrutiny than men. Women have to put up with the reality they are viewed more closely by both genders. Whereas men don't have to face nearly as much scrutiny. Then, being a transgender woman takes even more work to survive in the world. 

Then there is the reality of reflection between genders. Women traditionally resort to makeup, beauty spas and fashion to reflect the best version of themselves to attract men and to a lesser extent, impress other women. It is at least a multibillion dollar a year business. Now, back to me, and where I was on my path to transgender womanhood. 

Where I was on my path, was I was still struggling with even having the beginners' basics on how I could reflect woman to the public at large. With the help of continued work on my makeup and me attacking the nearby thrift stores, I finally began to reflect feminine to the world. When I did, I could begin to refine my approach and relax in the world as a transgender woman or more advanced cross dresser. Mostly, that meant putting my mirror's reflection in motion. It was very difficult in the beginning, as I needed to look the women and men in the world in the eye and be myself. Humans have the tendency to explore the world through their eyes and I quickly became used to having other women look at me totally head to toe. 

All too soon, I was ripped from my mirror and living a very scary but exciting life in a new world. Very quickly, I was able to put my fears behind me and understand who was really looking at me. Men paid me very little attention because I always assumed I was not attractive enough, but on the other hand, I was really receiving much more attention from cisgender women than I had ever had before. Obviously, for whatever reasons, my reflection with other women was working well and I loved it.

I was on a remarkable gender journey as I left the mirror behind and joined the world. As I refined my feminine outlook, I needed to accomplish a couple major goals. The first was, to never not refer to myself internally as a man again. I was a she and that was it. The second was, I needed to concentrate on establishing my own feminine aura. I started to really begin to zero in on whom ever I was talking to into knowing they were interacting with a woman. If it worked or not, remains to be seen, but I kept on trying.

Projecting my aura was the last stop in my progression out of the mirror and into the world. I viewed it as taking the last vestiges of any light I had ever seen in the mirror and turn it into a bright light of hope. It was scary because I was not used to being in a such a new world as a transgender woman. Along the way, I took on my share of setbacks but kept on moving forward.

Now, the reflection I see in the mirror, is only the one I need to apply my makeup and closely shave before I go out. I have also worked hard to do away with any remaining gender dysphoria I may still have. When it does hit me, it normally happens in the morning when I first look at myself in the mirror. I finally have come to the conclusion I don't look as bad as I think or as good, I think I do with my makeup.  The middle point has become good enough for me, and the mirror has again become nothing but a reflection.

Wednesday, March 26, 2025

The Light in the Mirror

 

Image from Alessandro 
Bianchi 
on UnSplash.

I spend quite a bit of time here attacking my mirror when I was growing up.

Recently, I have come to the conclusion some of my negativity could have been wrong. First of all, I was fortunate to have a beautiful full length mirror dad installed at one of the ends of the hallway in our house when I was growing up. When no one else was home, I would spend as much time as I had admiring myself in the hallway mirror. As I did, I could always see a brief dim light in the mirror when I viewed my feminine self for the first time. Even when I knew, the light would have to be extinguished soon, and I would have to go back to my unwanted male world. 

As I grew up and began to explore the world for the first time as a beginning cross dresser, I made plenty of mistakes the mirror did not tell me about. In fact, the mirror light shone brightly and told me I looked great when in fact, I looked just the opposite. I was presenting as a clown in drag with no one to warn me. For a long time, the light in the mirror nearly went completely out as I was rejected in public time and time again resulting in a deep depression for me.

I kept trying though, and the light began to come back on. I lost weight and began to find styles of women's fashion which flattered my body shape and finally began to present better. Especially when I was making the mental transition to novice transgender womanhood from cross dresser. To do it, I needed every break I could muster. Plus, I needed to turn up my light in the mirror, and let my femininized light shine through, so I could see her better. 

The extra light turned out to be all I needed to become more skilled at my makeup art and do the best I could with my testosterone damaged male face. With a little help from a professional makeup person, my light in the mirror grew even brighter, and more importantly, I could trust it. With trust came confidence which equated to more acceptance as a transgender woman in the public's eye. All of a sudden, my lifelong dream to lead a feminine life was within reach. If my light in the mirror stayed on. 

It did and I was even able to turn up my light to a brighter level with the addition of HRT or gender affirming hormones. Among the many other positive changes I went through was when the overall texture of my skin softened. Which meant the male lines in my face softened and I could use less makeup. Specifically, foundation. I quickly learned with more femininized skin and being able to wear my own hair, I was suddenly more presentable to the world. 

Looking back, I may have been too quick to judge my light in the mirror. It just took a little longer (along with the rest of me) to become more situated with living a new life away from my old male self, and perhaps it was my fault for not switching to a brighter bulb sooner. Plus, I was fortunate in that my light in the mirror did not burn out altogether. 















 

The Gender Comfort Zone

Image from Thomas Vitali on UnSplash.   It took decades to reach a point where I could say I was comfortable with my gender issues. The poin...