Wednesday, February 19, 2025

Someone is Paying Attention

Image from Alena Garrett
on UnSplash. 

One thing I immediately noticed when I left my mirror and went into the world as a novice transgender woman was when I was suddenly noticed more by both primary genders, male and female.

Of course, being raised in an unwanted male world, I knew how many guys made a big deal about the appearances of the women around them. What I was not prepared for was the amount of attention I received from other women. Especially, younger ones as teen girls were especially observant. I cannot or prefer not to recount the times I was stared down by a group of teenaged girls or younger. 

My primary example was the day I was out shopping in the racks of a women's clothing store when around the corner came a small child who startled me. Obviously, I startled him also because he ran back to his mother (who was close by) and said, "Look at the BIG woman!" Initially, I was relieved because he had called me a woman. Then he continued and said, "The big MEAN woman." Naturally, I learned a big lesson. The BIG mean woman should always be prepared to be friendly, which means I needed to immediately learn to wipe that old male scowl off of my face. If that was all I needed to do to not scare little kids, it was an easy lesson to learn. 

For a while, I was intimidated by all the attention I was receiving until I began to understand where it was coming from. The more I dressed to blend in with other women, the less attention I received from men. Primarily, because I just wasn't that attractive. On the other hand, the increased attention from women came from the fact most of them were just curious what I was doing in their world or were appreciative of my efforts to look the best I could. If I had a dollar for every time I was complimented on my jewelry or earrings, I would be a rich person now. 

It took me time but eventually I learned my lessons well and adjusted to the fact, my appearance as a transgender woman was a fact of life and in many ways a form of female privilege I needed to live up to. My observations made me work even harder on my feminine presentation. In other words, it was all part of my rite of passage into transgender womanhood. Plus, in many ways, I needed to work even harder to present well than the average cis-gender woman who was just getting by because she happened to be born female. Which, by the way, did not automatically allow her to be a woman. Neither gender birthrights allow them the permission to claim an automatic right to claim a title of man or woman. Which comes from socialization. 

I learned if someone was paying attention, I should make the most of it and adjust to my new surroundings. Once my confidence built to a point I could do it, I was able to project a strong feminine aura. When I did, questioning my gender became someone else's problem. Not mine.

Tuesday, February 18, 2025

Down the Rabbit Hole

 

Summer Image, JJ Hart.


Over the years, I began to sink rapidly or was stuck in an increasingly large and deep transgender rabbit hole.

Sadly, I did not have the information I needed at a young age to help me to understand I was much more than a boy who preferred to dress in girls' clothing. I just knew I was not satisfied with cross dressing in front of the mirror on the rare moments I was alone. I always had problems with what I called the gender roller coaster, or I was up when I cross dressed for a couple days before I crashed to the depths of depression and daydreamed my life away thinking of the next visit, I would have in front of the hallway mirror. 

Only one of my thoughts was for certain, I was falling down a gender rabbit hole which I could never return from. For many years, I thought I would possibly grow out of my gender issues, and they could possibly be a phase. Of course, wanting to be feminine in all aspects of my life, was never just a phase and just grew stronger as I aged. 

It turned out, the older I became, the fonder I became of my rabbit hole and wanted to stay there. When I did go out, I was like a real rabbit, cautiously surveying the world for predators. It was not until I began to arrive at a financial point when I started to build confidence in my cross-dressed presentation, did I begin to enjoy my trips out of the hole and into the world. 

It was about this time too, when I began to expand my rabbit hole. I needed more space for my wardrobe and wigs of course. Not to mention the mental room I needed to grow into the person I was becoming. Once I saw the light of my new gender day, there could be no turning back. The light felt so good and so warm; I was loving my new life. 

I ended up forsaking my gender rabbit hole for a new universe of women. To be truthful, it was the most difficult experience of my life. Since I had left my old comfort zone of white male privilege, establishing a new base was difficult in my new transgender womanhood. I had dug my gender rabbit hole so deep; it was difficult to find my way out. 

Sadly, I see too many transgender women and trans men who are stuck in their gender holes. Especially, in the current negative situations we are living in right now, I understand why so many LGBTQ people want to stay out of the public eye. It is just a shame we need to do it.

Monday, February 17, 2025

Your Personal Best

 

Image from Markus Winkler
on UnSplash.


If you have ever worked in any sort of a competitive industry, perhaps you have heard a phrase similar to keep your eye on the ball.

Many times, in my long journey to being a full-fledged out and about transgender woman, I have wished I paused to remember such a goal. One image comes to mind when years ago I was trying to pump gas into my car at a gas station along the interstate when I was traveling back to Cincinnati to meet Liz before we were actually married. 

To begin with, I was a little flustered, even to the point of panicked when I discovered I did not have much money at all on my debit card and had no cash at all. As I said, I was nearly panicked and ended up pulling up to the wrong pump to try to fuel my car. For some reason, I had chosen a diesel pump and fortunately was having no success in putting the nozzle into my gasoline powered car. As I struggled, a man pulled up nearby and came to my aid by telling me I was at the wrong pump. I profusely thanked him and moved to the correct pump but not before I needed to go in the station and pay. Exactly what I did not want to do. I had no choice due to my mistake and needed to finally go inside and confess my mistake to a clerk inside who had no sympathy for the dumb person making the mistake. 

It was just one of many times, I took my eye off the ball and barely snuck by with a little help from above. Another time I remember was one night when it was snowing quite a bit, but I decided I needed to go out anyhow. With out giving anything much thought, I figured the night would be ideal to wear my new medium heel boots to give my fashion image a personal boost. All was going well until I went into one of favorite regular venues and found a seat at the bar. All along, I was confident I could slide down off the bar stool without falling. It turns out, I was overconfident as I tumbled very a womanly fall to the hard floor. I was lucky and all I hurt was my pride. From then on, the boots remained in my closet when it was snowy or even wet outside. 

Most of the time, when I was pushing the envelope and taking my eye off the ball, it was not because I was trying to do my personal best as a novice transgender woman. Even though I had established "safe" places I could go, I kept trying to go other places where I was not welcome such as the one lesbian bar I kept trying to go to. Unlike the other lesbian venue, I was accepted in (which accepted me), the first place tried to make my visit as uncomfortable as possible. Until I finally just stayed away and gave all my money to the place where I was liked. Once I did that, I could relax and enjoy myself.

I learned also, my personal best was not exploring the limits of where I should go as a transgender woman. It meant staying off dark urban streets by myself, or even unlit mall parking lots. I had not realized yet I had lost my male security privilege and needed to add a whole new level of security to my life.

Through it all, as I made my gender journey, I slowly learned how to keep my eye on the ball and do my personal best. Anything less, and I would revert back to my old unwanted male life and find myself back to where I started. Equally frustrating, was the fact I would have wasted all the time I put into pursuing my goals. I found my path and decided to stick with it.  

Sunday, February 16, 2025

Meeting in Person

JJ Hart in a warmer time.

Do you remember the moment you met your authentic self in person?

Looking back, I can recall several profound moments when I saw the feminine person I was always meant to be. My earliest memories came when I was quite young in the days when I was first experimenting with my mom's makeup and clothing. Even though I probably looked like a clown, the mirror told me I was beautiful. No matter what I looked like, I refused to face the truth. 

It was not until much later in life, when I began to realize how much work it was going to take to really see my true self, did I get serious. If I was going to make it to my dream of transgender womanhood, I would have to profoundly change my way of thinking. The first change I made was how my male ego interacted with my appearance the public saw when I went out for the first times. 

The truth of the matter was, if I dressed "down" to blend in with public, I received very little attention, so I started to dress too trashy to please my old male self. What quickly happened was I attracted the wrong type of attention and did not pass well. Or, at all. Back to the cross-dressing drawing board I went time after time until I drove my male ego out to the point where I was successful in blending in with other women in the world. What were the women wearing and when were they wearing it became my motto. The time I spent was worth it when success as a novice transgender woman was becoming mine. 

Suddenly, my visits to the mirror became more and more friendly. I adjusted to the fact I would never be the prettiest woman in the room, but I could rely on other feminine attributes to get by. I began to closely study other women who may not be the most attractive, yet still be popular, fulfilled women. What I did was, I began to concentrate on what my new personality would be as a transgender woman. After all, I had an unique opportunity to start all over again as a human being. My new time was a scarce commodity, and I could not miss my opportunity to do it right. 

I was fortunate in that I already had a women friend who was ready to help me. She had been there all along, just waiting for her turn to lead my life. She was the feminine inner me. It turns out she was a nice person who saw the best in others. When I met her in person, I was excited and knew I was in good hands.

I was in good hands and began to expand my small circle of friends in the world. My wife Liz and I started to go to small and medium sized "Meet Up" groups in Cincinnati where I learned the benefit of a different group of strangers accepting me. None of us knew each other previously, so I was on an even level with them. The great equalizer. 

All of the process was extremely beneficial when it came to meeting myself in person until I became used to it. Perhaps the best part of the entire process was the time I realized I had really expanded myself as a woman, transgender or not.

Saturday, February 15, 2025

Not Scared? In the Wrong Room

 

Image from Alexandra Gorn
on UnSplash.

I cannot begin to tell you how terrified I was to interact with the public when I first began to attempt to live in the public's eye.

One night in particular always stands out in my mind. It was the evening when I had pre-determined my cross-dressing days were behind me and I was going out as a transgender woman. Furthermore, I knew if I was successful, it would change my life forever. As I prepared for my big night out, I took extra care with my outfit, makeup and hair. I wanted to make sure I blended properly with all the other women I would be interacting with at an upscale bar I was going to which was heavily frequented by professional women who worked at a nearby mall.

Once I made the short trip to the venue and found a parking spot relatively close to the front door. As I sat in the parking lot, the pressure to go in increased dramatically. As I nervously checked and adjusted my makeup in the car's rearview mirror, again and again the fact was not lost on me I could be changing my life forever. By the time I gathered my courage to actually enter the venue, I could barely breathe and was gasping for air. 

It took me awhile to gather my courage and enter the front doors of the place and interact with the hostess stand. Deep down, I was hoping the hostess would be busy seating other patrons so I could sneak on through and find a seat at the bar. The short distance from the hostess stand to the bar seemed to be miles to me but I made it and luckily found a corner seat at the bar by myself. Plus, the bar itself was supported by two large thick pillars. I figured if I found a seat next to one, I could blend in and hide if I needed to. I did not need to hide as I was approached for my order by a friendly bartender. 

Immediately, my fears began to melt as I ordered my first drink and even started to relax a bit and watch all the other women who had begun to arrive at the bar to enjoy each other's company. As I observed the group, I saw no one was noticing me. So far, so good. No one noticed a very scared novice transgender woman in their group. 

Of course, this evening was only the beginning of my new transgender journey. I knew my life had changed forever. I could never go back to the old unwanted, boring male life I was living. To move forward, there would be many nights when I would be very scared. Somehow, I learned to feed off my fear to propel me forward. No longer was I a weekend cross dresser, I was reborn as a very serious transgender woman.

My end game was using fear to refine my push forward by putting extra time and effort into my fashion and makeup. That way, when I needed to walk past a crowd of strangers in a new venue I was in, I could do it without any issues. 

I finally decided, if I did not feel any fear at all, I was in the wrong room. Especially, in today's climate, it pays to always be aware of your surroundings. Maybe fear is a strong word, but awareness is not. 

Friday, February 14, 2025

Happy Valentines Day

 

Happy Valentines Day Liz!!!

Admittedly, I have never been much of a romantic, as a former man or a woman. Over the years, I have started to change as I entered transgender womanhood. 

After my wife passed away, I was intensely lonely and began to look around for company. At first, I started by going on-line under various platforms. For example, one week I would list under woman seeking woman, then the next week, I would list under woman seeking man. In total, predictably, I received very few responses. None, I considered quality except one and her name was Liz who contacted me under woman seeking woman. She was from nearby Cincinnati.

In the meantime, I did make a couple other lesbian friends out of sheer will power by forcing myself into going out and being social. The first friend was introduced to me by her daughter at one of the sports bars I was a regular in. The daughter noticed I was always alone and thought it would be fun to do a little matchmaking.  The great part is, we still are friends to this day. 

Then one night when I was out to be alone, another woman came in to pick up a to go order and ended up sliding a note down the bar to me. We ended up meeting and she became part of a small group of women I partied with almost nightly. Plus, as I always say, these two women taught me so very much on what it would be like to live life as a woman, more than they will ever know. 

By now, you may be thinking, were there any men in my life? Yes, there were a few including all the ones who would stand me up on dating sites. I did have a couple memorable dates with guys which never went beyond the kissing stage. Even though I enjoyed being on the other side of the dating spectrum, I still much preferred the company of women. Especially when I was accepted for me. I was satisfied on where I was in my dating preferences and saw no need to change. Plus, when I went to lesbian mixers, I found I could further my preferences as a transgender lesbian.

Perhaps my biggest discovery was how many lesbians were not of the "gold star" variety which meant in their past they had some dealings with men. With me, they found a curious gender middle ground which the majority of insecure men were afraid to pursue. During this learning portion of my life, I ended up enjoying myself immensely.

What I have left out of all of this on purpose was my interaction with Liz. Through it all, we had continued to talk back and forth. Once I was brave enough for her to hear myself on the phone. We finally arrived at the point where her and a group of women friends from work were going to a drag show near Cincinnati. The drag show ended up being our first date nearly fourteen years ago. Obviously, everything went well and ten years later, we were married. 

On this Valentines Day, I credit Liz with being the only woman who ever told me she never saw any male in me at all. In many ways, she helped me back on my feet after some rough years of my life. Happy V-Day, Liz!

Thursday, February 13, 2025

The Gender Envelope

 

Image from Alexandru
Zdobau on Unsplash.



Sure, I spent or waisted far too many years before I fully transitioned into transgender womanhood.

I was too slow for such a long time actually pushing my personal gender envelope when I was busy telling myself I was no more than part-time cross dresser. I saw no harm in just doing my best to look like a woman until it just wasn't the answer I was looking for. The more I cross dressed and improved my feminine presentation, the more I pushed the envelope and looked for more. Very quickly, my yearly Halloween adventures just were not enough.

I began to wonder if I made a good impression at Halloween, could I make the same impression if and when I tried to go out in public as a novice transgender woman. Following many trials and error experiences, I found I could survive a public which largely did not care about me. The big error I always point out is when I was not receiving any attention to speak of as a woman, I began to dress trashy to attract the wrong sort of attention. I was mistakenly pushing my gender envelope the wrong way. When I finally began to understand the best ways to dress my male body and apply the proper makeup, did I begin to be successful and blend in with other women in the world. 

Once I had accomplished all of the fashion, hair and makeup necessities, I allowed myself to further push my gender envelope. When I did, I found myself needing to understand how women exist in the world. Or how do they communicate with other women and men. I had a quite a bit of catching up to do since I was attempting to catch a moving train heading down the tracks. I did not have the benefit of growing up female with a mother or peer group to guide me. I always point out; the passive aggressive system of interaction most women operate under was the most difficult for me to learn. Since childhood, I was always used to the full-frontal confrontational world men operate in so I was attempting to survive in a whole new world.

Once I did survive, I began to push even harder, ignoring warnings from my wife on what would happen if I was ever caught. I put the male gay bars behind me and moved on to big sports bars and lesbian bars where I could actually be myself. I thought I had reached my peak when a dear friend of mine invited me to a trip to a NFL Monday Night Football game in Cincinnati. Even though I was very scared at the thought of going, I could not turn down a chance to empty my envelope and lay my gender cards on the table. Since I am not really a gambler, I hoped the lifetime of preparation I put into this moment would serve me well. 

The moment did serve me well. As always, I survived and became a better woman for it. Plus, I learned the game was only the beginning. The life in my transgender womanhood I was going to experience, would be extremely fulfilling and everything I thought it could be when I started pushing my gender envelope.

Wednesday, February 12, 2025

Transgender Destiny?

 

Image from Marvin 
Kuhn on UnSplash.

When some unknowing person says something like I had a choice to be transgender, I just laugh and say being trans was simply my destiny.

I believe my journey began before birth when my mom was prescribed the D.E.S. medication which was popular at the time for women who had a history of experiencing problem pregnancies. Since my mom had undergone three still births before me, it seems to me, she would have been a prime candidate for the drug when I was born in 1949. 

From the very brief studies I have seen on D.E.S., it was supposed to flood the mother's womb with estrogen. Which of course affected the fetus also. 

How ironic would it be that the initial dose of estrogen I received in the womb would later on come back to help me. It took me fifty years, but eventually I discovered when I went on HRT or gender affirming hormones, how natural I would feel. No adverse effects at all, just a warm feeling I was finally doing what was right. In other words, I was coming home. The only problem was my life was filled with the gender torment of fighting my basic will to be feminine. What if I had just given in to my instincts so much earlier. Would life had been more pleasant?

The problem was though, gender was never cut and dry with me. I was cursed with a male body which on one hand kept the bullies away but on the other, made it very difficult to obtain a feminine look when I found the secret time to cross dress as a girl. I had to take one or another which caused me considerable stress to my mental health. Waking up every day wondering if I was a boy or a girl, was certainly no fun. 

Plus, there was absolutely no one I could explain my gender issues to. I grew up in a male dominated family and knew there would be no way I could be accepted. I knew, even being caught in girls' clothes would earn me a trip to a psychiatrist. Deep down, I knew there was nothing mentally wrong with me, so I did want not any part of a visit. Remember, this was back in the 1950's when there was little to no knowledge of gender issues. In fact, gender issues were labeled as mental disorders. All that happened was, I was driven deeper into my feminine gender shell.  

As time went on, I developed a very thick shell which when I finally ready to do so, was difficult to escape from. In other words, I needed to establish too many levels of feminine escape before I made the final jump to the other gender frontier. I needed to slowly discover if the other gender as a transgender woman would provide me what I had been missing all of my life. I felt as if I was sliding down a slippery slope into a valley, I knew very little about. 

As I slid down the slope, I saw bit and pieces of my old life go by as I mourned some of the pieces and I rejoiced at others. As I felt more and more comfortable in my new transgender womanhood, I knew the landing would be as soft as possible. I found my gender needs had changed, for the best. I finally took my chance at the age of sixty to forever change my life and live fulltime as a transgender woman.

I finally had my chance to fulfill my D.E.S. destiny. I could not reclaim the time I had lost but I could lead a better life going forward.

Tuesday, February 11, 2025

Transgender Lines

 

My friend Racquel.

During my journey to transgender womanhood, I often went past gender goals without even realizing it. Or, I was too busy living my life, I could not slow down enough to enjoy where I was.

Along the way, I was careful to set goals for myself such as not being satisfied to present successfully in mall and clothing store situations where people were more into my money than gender. What I started to do was go to lunch or an early dinner when I was cross dressed to judge the reactions I was getting. Even though I was not totally successful in my feminine presentation, I was learning. I found employees at restaurants were more apt to accept me when I was pleasant, minded my own business and of course, tipped well. Plus, I was easy to remember and became a protected regular quite easily when I made wise decisions on where I decided to go.

In other words, stay out of the redneck venues so prevalent where I lived in southern Ohio. I learned the hard way in one place I went when I had the police called on me as I tried to use the bathroom. After it happened, I gathered myself and went a short distance up the street to another venue I knew I would be accepted in. I certainly should have seen that line coming up before I tried to step over it. The stubbornness which I carried over into my transgender struggles, served me well as I kept trying to succeed.

At the same time, I had a new set of confidences set in. I encountered a diverse set of acquaintances which I write about often. The give and take I went through as a brand-new trans woman helped me to stabilize who I was searching to be. Before I knew it, there were many new lines I was crossing. Since the groups I was socializing with were very diverse, I needed to confront lingering questions about my sexuality. One group had a man I was getting along with wonderfully and on the other side, I had several lesbians I was getting along with too. Mixed in also, was Racquel, a transwoman who often joined our group, and who to say, any of them really liked me.

It was about this time all the lines I was attempting to cross started to blur. Was I into the man, I liked, the lesbians I liked or even the transgender woman I knew? I knew I had quite a bit to consider so I kept going out and researching to hopefully come to a better understanding of who I was in my new life. 

Finally, I was able to sort it out, or it sorted itself out for me. The man I knew, and Racquel moved away and I was able to maintain my relationship with several lesbians. In essence, my decision was made for me. Choices have consequences and with a little help I made mine. 

All the lines I did not see did not trip me up. I was more flexible than I ever imagined possible, and I made my way into my transgender womanhood. 


Someone is Paying Attention

Image from Alena Garrett on UnSplash.  One thing I immediately noticed when I left my mirror and went into the world as a novice transgender...