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.

 

 

 

Seismic Gender Shits...from Gay Bars to Sports Bars

 

My Trans Friend Racquel and Friend.

In many ways, this is only a continuation of yesterday’s post about seismic gender shifts. This time though, I am going to focus on my foray into leaving gay bars behind and beginning to go to several of the major sports bars in the area where I live.

As I see it now, going to lesbian bars was more of a learning experience but being accepted in sports bars was a dream come true. As far as the sports bars were concerned, I can break them down into two types. The smaller more diverse ones such as TGIF Fridays (which catered to single women) and the larger ones which catered to more of a beer drinking, wing consuming male crowd. I knew quite a bit about both from my male days being out and about with my drinking buddies. Not to mention, I had managed a major competitor to Fridays in the area. I only knew the number of times I was jealous of women who took advantage of going to both venues.

It was not until I seriously began to consider going to a sports venue where I enjoyed the cold beer and sports on the big screen televisions, did I begin to look around and see many other cisgender women mixed in with the rest of the patrons. I began to think, if they could do it, why could not I?

Before I even considered my adventure, I needed to insure my femininized presentation was up to the challenge of being in an atmosphere where I would be one of the very few transgender women (or cross dressers) in the venue. All in all, the process took every bit of courage I could summon and still was very scary. Even though I was scared, I pushed forward to see if I could achieve my dream. From my business experience, I knew if I could make it to the bar without being noticed, most of my risk would be averted. Bartenders are greedy creatures and are primarily focused on service and tips which would not be a problem for me.

My biggest problem was acting as if I was not a single woman in the bar area. One of my tricks was to always use my cell phone as a prop to act like I was expecting company. For the most part I think it worked until I began to meet another transgender woman for drinks and there was strength in numbers. I was fortunate too; in that I was slightly ahead of the curve of cisgender women enjoying sports as much as men. When my lesbian friends and I were together enjoying the games, no one cared, and we fit in.

Through it all, there were only a few occasions when I was called out and embarrassed. One of which occurred when I was in a red neck leaning sports bar and had the local police called on me for using the women’s room. After a brief discussion with a female cop, I was sent on my way to a venue up the road where I knew I had rest room privileges.

Probably the most glaring and potentially problematic time I had was one night at a smaller sports bar I had gone to often with no problems. That night, my transgender friend Racquel and I were sitting at the bar minding our own business when suddenly, “Dude Looks Like a Lady” by Arrowsmith comes on the juke box. Not once, not twice but four times in a row, and to make matters worse, the new manager came up to us and said it was time to go. So, we did and went up the street to a bigger venue where we knew we would be welcome. Never to come back, or so we thought.

Several weeks later, one of the bartenders from the venue we were kicked out of found me and apologized. She went on to say, the manager who had banned me had been fired for drug abuse and I was invited back. I happily went back and never had another problem except a bathroom experience which I will save for another blog post.

More than likely, all the success I had in establishing myself in sports bar venues had to do with knowing the people on the other side of the bar were there for the money as much as the store clothing clerks I used to see in my old shopping days in malls when all they cared about was my attitude and the color of my money. On the other hand, the people in the gay bars treated me much worse and often I had to wait for service altogether.

At the end of the day (or several) my transition into the big sports bars was much easier than I ever thought it would be.

Seismic Gender Shifts

Image from AC on UnSplash.

I received a response from a reader seeking more input on how I was able to integrate myself into the lesbian and sports bar cultures.

First, thanks for the question as it is a complex one to try to answer. It turned out, the lesbian culture was the most difficult to be accepted into.  I began my journey in Dayton, Ohio around the year 2005 while my second wife was still alive. Back in those days, there were still lesbian bars in business for me to go to. It is important to note, one of them was essentially a lesbian biker bar and they hated me. Especially when I played “Shania Twain’s” I Feel Like a Woman in the bar. Even still, they barely put up with me until I found a better venue to go to.

It turned out, relatively close along the road was another small lesbian bar which had just opened, so I tried it out. Imagine my surprise when the first bartender I saw, knew me as my male self also. She saw through my femininized appearance, and I was treated very warmly, which helped me gain acceptance from the other patrons. I was able to relax and look around at the dynamics around me.

What I immediately noticed was where I fit in the layered levels of women in the bar. There was everything from very masculine butch lesbians, all the way to their femme girlfriends who came with them. I learned very quickly, with my jeans, boots and makeup, I fit right in with the femme lesbians, even to the point of attracting attention of a few of the butches. Who, on occasion, bought me beers and flirted with me. In fact, my first dinner date was with a super butch who went on to become a full-fledged transgender man. Keep in mind also, back in those days, I was much younger and could present much easier in public once I learned the basics. Such as, what I was going to wear when I went to a lesbian bar. There would be no dresses or skirts for the evening.

It is also important to note, my next foray into the lesbian culture was pure luck or destiny if you don’t believe in luck. This is where my sports bar experience comes in. Keep in mind, I had managed sports bars for a living in my past and had a basic knowledge of how I would go about becoming a regular. Again, I needed to dress to blend, stay friendly, smile and tip well. My plan worked well and soon I did become a regular at several venues where I had gone to as a man and always wondered if I could repeat my visit as a transgender woman.

On one night, one of the bartenders asked me if I would be interested in meeting her single lesbian mother and I said yes. We ended up getting along well and even ended up adding another lesbian woman by complete chance who I ended up partying with for years until I met Liz and moved to Cincinnati. As destiny would have it, Liz identified as a lesbian also, so my circle was complete. I was basically protected from the world until I could learn many of the nuances of being a transgender woman. Such as, I did not need a man to justify my existence.

I guess you could say, my seismic gender shifts just came along when I needed it, or when I was questioning my sexuality. I had always gotten along with women easier than men and their interest in me sealed my future in the world. I enjoyed immensely going to lesbian mixers and being flirted with on occasion. I always thought it was because I was hitting some level of middle gender with some women who were not intimidated by a woman who used to be a man. They were intrigued and even impressed by my honesty in how I approached my life.

Sadly today, around here at least, there are very few pure lesbian bars left to learn in, and the younger generation seems to be more accepting of the transgender world. Which is what is scaring all the politicians, shoving unjust laws down our throat. However, I don’t want to get too far off the subject and just say my acceptance into a totally new culture as a transgender lesbian came at a cost. But a good one and I had friends.  

Trans Girl at a Drag Show

 

Rubi Girls, Dayton Ohio.

Very early on when I started to explore the public, once again I felt as if I did not fit in. Specifically, when I went to gay venues, especially the venues with drag shows. 

Although I knew many of the other patrons viewed me as just another drag queen, I knew I was much different. For the most part most of the queens I had met were gay men doing their best to perform on stage as women. There were very few transgender women on stage I could identify with. Even so, the local shows were places I could go to be safely entertained. Even still, I became bored with the same old, same old and began to seek out other venues I could go to. That is when I began to go to the well documented shifts to sports bars I had frequented as a man. 

Drag shows unexpectedly became a part of my life again when I began to develop friendships with other cisgender women. Going to shows became the cool thing to do and since I was the link to the performances in their minds, I just had to come along for the girls' nights outs. Which I loved. Most of the women I went out with in the small group just assumed I had more connection with the entertainment that I did. But who was I to say they were wrong, and I went along for the ride. 

It was not until much later when I finally was able to make the differentiation to all my women friends, how much different I was than the drag queens we were watching. The first big show I attended after coming out was when I was invited to go with my daughter and all her women friends when they all were invited to go to a drag troupe called the "Rubi Girls" in Dayton, Ohio. The group of performers is very famous in the region and has even raised millions of dollars to benefit AIDS research.

Effectively, it was my first girls' night out with my daughter and I did not want to let her down. I was scared and prepped overly well for the evening, as I knew I had to blend in with what my daughter's friends were wearing. Since I was just coming out as a transgender woman, my daughter decided only a select few of the attendees would even know I was her parental unit. Once my fear went away, I was able to talk to a few of the other women around me and immensely enjoyed the show. The whole evening proved to be one of the best drag experiences I had until my first date with my future wife Liz. 

This time, the group of women I went with was much smaller, as was the venue which was approximately halfway between Cincinnati and Dayton, Ohio. It meant the drive was easier for both of us since we had not moved in together yet. Again, I was careful not to overdress the other cisgender women in the group and attempted not to be so scared. Afterall, it was just another drag show in a gay venue. Everyone seemed to have a good time, including me when I put away my bias against drag performers and was just being me. All the women around me realized I was much different than the talent we were watching. I was closer to them than the drag women who were gay men. 

Overall, the date with Liz was very successful. So much so, our next date was a non-drag event when we went to the regional Renaissance Festival with her son and again had a great time, so we further solidified our relationship more and more. 

When I look back, I owe my contact to drag more than I give it credit for. At the least, going to drag shows even encouraged me to walk in heels with more confidence. Plus, all the credit for helping to start my public life with my daughter and future wife goes to drag and the confidence it gave me to know I was secure in my transgender womanhood and not in some never/never land which was my knowledge of a world I never really understood. Or felt a part of. I guess you could say, being a trans girl at a drag show still worked out for me. 

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. 

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. 

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.

The End Result?

 

Picnic time with my wife Liz on the right with
JJ Hart. 

Even though I write often about reaching my dreams of living as a transgender woman, sometimes I wonder if I had made it at all.

One of the problems I faced was thinking once I made it to my goal, there was always something else which was challenging me on my gender journey. When I was younger and so naive, I labored under the impression, looking like a woman should be my main goal. After I made it to the point where I could successfully blend in with the other women around me, I found there was so much more to do. I grew impatient with mediocrity and continually looked for more. There had to be so much more for me to discover around the next corner of my life. My prime example always was when going to the malls and clothing stores became too easy for me to do, I sought out other more difficult releases for my transgender challenges. I began to stop at restaurants to order lunch which forced me to interact one on one with employees. It all taught me the basics of communication with the public. 

I say the basics, because communication became the longest and most important part of transition which led to the end result of living my dream. How could I ever hope to live a fulfilling life as a transgender woman if I could not even talk to anyone else. I was also paranoid about anyone wanting to talk to me at all when I was out and about. First of all, I needed to relax and quit putting words in the mouth of the people I met and sit back and listen carefully what they were trying to say. For the first time in my life. The end result was I began to be able to interact with the over-whelming majority of the cisgender women who were curious about me. On the other hand, the majority of men I met wanted little to nothing to do with me, and vice versa. 

Once I arrived at a point when this transgender woman thought she had it all, something else would come along and proved me wrong. I learned the hard way; I needed to be careful where I went on my own as a woman in the world when my male security privilege was taken away. Navigation in a new world proved to be difficult for me. My theory of going out to be alone was at times dangerous as I actively sought out someone to be with. Overall, I was intensely lonely as a man and as a transgender woman. A complex difficulty to be sure in my life dealing with two genders. Primarily, I needed to choose what stayed and what went in my life. All I knew was, I was receiving more positive attention when I was out as a single transgender woman than when I was out as a single man. So, my choice became increasingly easier. 

The end result was, I made it to my goal of living as a fulltime transgender woman, I thought. Even though I was living my dream I never thought was possible, I found I had several other issues to conquer. All of a sudden, with all my male clothes gone and, in my past, I had to plan on what I was going to wear daily in the world. A big difference from the old days when I could look ahead a couple of days to my fashion choices. After several false starts, I made it to the world I always dreamed of, and none of it let me down.  Happiness was always fleeting in my life, but I finally found a slice of it. At times it was quite the adventure as I made my way from cross dresser to transgender woman. 

Even though my adventure had its ups and down to be sure but looking back there were more ups than downs as I made my way (or I should say, learned my way) to my ultimate end result.

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.