You're so Vain

 

Image from Ava Sol
on UnSplash

Expressing yourself to the world as a transgender woman carries with it a certain amount of vanity.

Until you begin to relax in your new feminine world, I think you need to obsess over every detail of your exterior appearance. Since we all have such a vast amount of catching up to do to compete with other ciswomen in the world, details matter. Perhaps one of the first lessons you learn is how competitive the world is when you are a trans woman. Ciswomen are every bit as competitive as men but in certain areas not readily visible to the male gender.

For example, the major question comes to mind that do women dress for men or for each other. Sadly, we never had the input of mothers, sisters or girlfriends saying, “are you wearing that?” I know if I had that sort of input, it would have saved me a lot of embarrassment when I first began to go out into the public’s eye. It was a resounding yes for me when I learned who women really dress for…themselves. My problem was, my male self-kept getting in the way and had me dressing like a trashy teen girl. All poorly concealed in a testosterone poisoned male body. It was no wonder I was creating negative attention and getting laughed at. When all I was doing was trying to present myself well the best way I knew how.

After I began to learn and change my thought patterns concerning fashion and makeup, I began to have success in the world. So much so, that on occasion (when I was so vain and did everything right) I received a compliment or two from a cisgender woman. One thing was for sure; it takes a woman to know the work it takes to perfect a public image with makeup and fashion. Plus, I needed to be better than the average woman because I was working at the whole image after I started as a man.

It turned out, having to be better in the world worked well with my increasing source of transfeminine vanity. All I thought of was how much better I could look if I tried just the right foundation and mascara, as I haunted the many thrift stores, I went to looking for just the right piece of clothing to add to my wardrobe of feminine clothes. My personal newfound male to female femininization vanity was in full force as I was having fun. In reality, I saw nothing wrong with being vain in how I appeared as my authentic self, until I clashed with my second wife.

She rarely wore makeup or dresses at all and did not like the way I presented myself at all. On the rare occasions we went out together as women, I tried to tone down the amount of makeup I was wearing along with putting on my most conservative clothes. All because I wanted her approval, which I never got. If I wore any less makeup, I might as well say to hell with it and go out with her as my old male self. I was stuck between the rock and the hard place as far as my feminine vanity was concerned.

As I progressed with my makeup and fashion experience, I understood how much work I would have to put out to achieve the transgender goals I wanted. I knew I would never be able to transform my old male self into the prettiest girl in the room but on the other hand I could present well enough to get by. Everything that I was doing at that point just became a blur of change. Especially when I was approved for gender affirming hormones or HRT. As my skin softened, hair and breasts grew, it all was a welcome addition to all the work I had done all those years to just survive in the world. As I wrote yesterday, just not having to wear a wig anymore was a huge deal for me since I had no male pattern baldness to contend with. All of a sudden, I needed to contend with a new form of vanity when I went to beauty parlors to have my hair done just a certain way.

During all the years it took me to fully come out into the world as a trans woman. I learned the true meaning of competing with ciswomen in the appearance arena. Once I did. I needed to move ahead to the larger context of being allowed to exist in women only spaces by the alpha-female gatekeepers. In many ways, my second wife was an alpha female who never let me in, so I wonder what would have happened if she had lived long enough to see/know the person I am today. One thing is for sure; I am no longer the “pretty, pretty princess” she used to call me because I have paid my dues as a transgender woman.

All I know is I did go through my periods of extreme selfishness and vanity to arrive where I am today and I don’t know if there is any other way to go down the path, I ended up taking. Changing a gender is such an intense way to live, especially when you started with so much success as a male that it took me a massive effort to change. Not to say, all of the effort was not enjoyable but at least, it was interesting and challenging to see behind the gender curtain.

For many of us stuck in our own form of gender dysphoria, vanity is just one aspect of our larger need to survive.

 

 

 

Alone in a Crowded Room

 

Image from Bruno Aquirre 
on UnSplash.

I often refer to the days when I was first going out and seeking clues to my true identity as going out to be alone. I called it that because I had not yet met any regular acquaintances that I would have called friends on a regular basis. So, I was surrounded by a group of strangers no matter where I went. Even so, it was better than sitting at home by myself staring wishfully into the mirror.

Following leaving my painfully shy days behind me and becoming a rather social person, I did miss the interaction with the public. Going out alone was the only recourse I had which brought up several other problems. One of which was if I did present as a successful woman sitting by herself at a busy bar, always invited trouble because I was so out of place. It was during those times that I used my cell phone as a prop. In essence signaling to people, I was waiting for someone to arrive and join me. Plus, in the cold winter months, I could place my coat or jacket on the seat next to me to act like it was occupied. Both of which helped keep away any unwanted advances from mainly intoxicated men. On the other hand, other intoxicated ciswomen did not count, and I welcomed any of their advances which completely outnumbered men. Mainly because the women were so curious about what I was doing in their world.

Another problem I had was a huge case of impostor syndrome I suffered from. No matter how nice the stranger approaching me was, somehow, I felt I did not quite belong in the new exciting world I was in. It took me a while to get adjusted to the fact I was succeeding in a life that I had previously only considered a dream. I also still considered myself a rank amateur because of how I was able to conduct myself as a new transgender woman. I knew very little about how ciswomen communicated in the world away from men and it showed. For the longest time, the little nuances women use to communicate escaped me. Forcing me into shutting down and just listening to others and sometimes coming off as a standoffish bitch. Which was the last thing on my mind to happen.

I began to move away from being a stranger in a crowded room when I began to have enough confidence in myself to move forward. I was no longer just an virtual impostor just observing the world to jump in and inserting how I felt about things and people around me. A word of warning though, it took me a while to get there. Too much trial and error before I gained the confidence in my own unique form of womanhood which differed from many other women around me but at the same time, was still as complete. Sort of.

It was not until I began to build up my own circle of friends who happened to be mainly lesbians did, I began to relax and truly enjoy myself. I was no longer an imposter but now a full-fledged participant in my resurgent social life. Probably the only mistake I made was when I did not realize how different two of my friends were who I kept inviting to our impromptu meetings at sports bars and lesbian mixers. I was still naïve to the lesbian culture and did not realize the differences between a so-called gold star lesbian and one that had been with a man. I had one gold star friend along with another who had been previously married with three kids, so on occasion sparks did fly. In the meantime, I was off in my own little world jumping at the chance to be a wing person for one of my friends and trying to set her up with another woman at the mixer. It never worked, but I had a fun time trying.

The best part was I was no longer a stranger in a crowded room. I was becoming a full-fledged participant and loved it. The only problem I was having then was my new feminine life was starting to seriously force my hard-earned male life into an early retirement. A retirement he was so not ready for. Often the gender conflict I endured was mental and brutal. I did the only thing I knew to do and that was to internalize my feelings and move on. Which was the last thing I should have tried to do. My male self-wanted to keep me being a stranger in a crowded room so he could have his way. What he did not count on was, the more I worked on my dream gender life, the bigger and more accepting the room became.

The more I think about it, the more I think my male self-wanted to keep my female self as a kept woman. Validated by him only. Eventually, my transfeminine soul won out and he needed to face the truth. He was always part of living a lie in my life. Since my impostor syndrome was for the most part gone, it was the last remaining significant part of my life for him to cling to.

It felt so good to no longer just to be going out to be alone and know I would have the chance to meet my friends or even make new ones. Because I had hid my true self away for all those years, my transgender dream self could not wait for a chance to live and express herself in a crowded room.

 

 

The Hustle and Bustle of Christmas as a Transgender Woman

 

Image from Clarke Sanders
on UnSplash.

Doing the Christmas shopping shuffle as a transgender woman, often takes a lot of courage and confidence to do it.

Over the past couple of weeks, I have written about my holiday adventures leading up to the big day. From taking a short trip to Clifton Mill to view their extensive, festive lighting display all the way to letting two men load my heavy purchase for me at an Oak furniture store, I stretched the boundaries of what I was used to as a new cross dresser or trans woman in public. After it was all said and done, even though I was terrified most of the time, I was happy I tried it all. I came out of doing the Christmas shuffle with much more confidence in my girl self than I had going into the season.

In fact, as I have written before, Christmas quickly outpaced Halloween as my favorite holiday. Why? There were several factors, such as the length of the season and the creativity I could put into celebrating it. Plus, for once, I was doing good for others by buying gifts for them as I shopped. I positively loved it and wondered where the experience had been most of my life.

If you are a procrastinator and last-minute gift shopper like I was, doing the Christmas shuffle as a transgender woman is ideal for you. As you can get lost in the crowds quite easily and no one pays attention to a single woman out doing her late shopping. Custom made for you to do your shuffle and head back home.

I was fortunate when my second wife left her bookkeeping job and took a managerial position at a large bookstore chain. So, at Christmas, she was very busy and worked many hours. It was easy for me to schedule my hours around hers, so I had plenty of time to get out of the house and do gift shopping. I could obsess on wearing just the right outfit to blend in with a busy world and at the same time, search for just the right gift. Along the way also, I could stop in and grab a bite to eat at a restaurant and again stretch my ability to deal one on one with the world as a transfeminine person. Yet another reason, I came to prefer Christmas over Halloween because I hoped I was not perceived as a man wearing a costume, or worse yet some sort of drag queen.

As the big day approached, the sky was the limit for me. I did my shuffle as much as finances allowed and stockpiled my gifts for my special night where I stayed home with some high-powered eggnog and wrapped my treasures to go under the tree if they would fit. Of course, my wife was close to being a professional gift wrapper and I was just the opposite. But as the eggnog kicked in, I did not care, and besides it was the thought that counted. Right?

Finally, the big day arrived and I was shuffled out. Plus, we had family connections to visit all day on Christmas day. My thoughts for once were in other places than doing my precious shuffle which I had learned so much from. After the day wound down and my wife and I were alone, we opened the final gifts from each other. Which included a gift for my feminine self. I will forever remember a nice fancy fuzzy baby blue sweater she gifted me. It was snug fitting and I filled it out nicely with my new silicone breast forms I received from a cross-dresser acquaintance of mine who was purging. Naturally, that part of our gift giving day was the part of the day which was the most anticipated for me. I was like a little kid, brimming with anticipation.

Every year after the intense transgender Christmas shuffle was over, I had the chance to sit back and reflect on all my experiences and what they meant. Without hesitation, I think the confidence I built up from going out in the world as my trans self was the most important aspect of what happened to me. I learned what it meant to blend in with ciswomen around me and survive better than I ever could before. I also discovered the vast majority of the world did not and does not care about having a transgender person in their midst. The biggest difference is that back then, we did not have a Russian asset in the White House leading his blind, spineless party into demonizing a small portion of the population. Back then, I was merely a curiosity to many people, especially ciswomen.

When my second wife passed away, the need to do the major Christmas shuffle went with her too. The only blood family I had left was a brother and a daughter to worry about at all during the holidays. When I came out to them, I was roundly rejected by my brother and completely accepted by my daughter and her family. So, I broke even and even did better when I considered the relationship, I was able to build up with my daughter, son-in-law and three grandchildren. I won the family coming out shuffle in a big way.

Even still, sometimes I miss the hustle and bustle of doing the transgender Christmas shuffle as over the years, I have gone nearly the entire direction in the other way. It is hard to say what I miss most but it probably having the financial resources to buy basically as many gifts as I could afford might be it.  Maybe it all came from having a guilty conscience from sneaking out of our house to join the world as my authentic true self instead of my old boring male self and breaking the pledge, I gave my wife that I never would.

Whatever the case, I was extremely selfish and was a contradiction when I did it to buy gifts for others. I guess it fit in with the whole contradiction I felt from my deep-set gender dysphoria to begin with. I dealt with it all the best I could, did my Christmas gender shuffle and moved on with my life making the most of it.

 

 

Earning my Way into the Sandbox of Women

 

Image from Juli
Kosalapova on
UnSplash.

I call being accepted in the feminine world of ciswomen around me, as being able to play in their sandbox.

Getting a chance was similar to living a dream and very difficult for me to do. To begin with, I needed to lose whatever weight I could off of my very male dominate frame and take better care of my skin, so I could use less makeup. I desperately wanted to be pretty but accomplished it as naturally as I could. Motivation to do both came easily for me because I was obsessed with doing something very well in life that I cared so deeply about. Surprising even myself, I was able to shed nearly fifty pounds as well start moisturizing daily after I shaved. Obviously, the weight loss helped more dramatically when I could shop for a better selection of stylish women’s clothes in my new size and the decrease in makeup I needed spoke for itself when I presented better in the world.

Even with those positive results behind me, I was still very naïve and had very little knowledge of what I would have to do to be let in to play in the sandbox by the alpha female gatekeepers. As my second wife was always fond of telling me after major fights, we had that I made a terrible woman. Then she added she was not talking about appearance. Which was good since I had just had situations where I was mistaken for a ciswoman to back me up. Then I was confused, if it was not my feminine appearance holding me back, what was it? What would make me a better woman after all.

From that point on, I set out on a mission to understand what she was telling me but I had a major drawback…I was still living the vast majority of my life as a man and as such, ciswomen would not allow me back behind the gender curtain. For the most part, I was stuck in my part-time cross-dressing ways until I could find a better way out. The sandbox remained a faraway dream.

The main problem remained. My male ego would not easily let me pull down my male defenses to see and learn what really went on in a women’s world which operated quite nicely with or without male influence. For the longest time, he (me) refused to listen to women the best he could to learn what they were really saying when he was stuck playing the game behind the gender border. I felt as if I was in East-Germany behind the Berlin wall of gender. I knew I wanted to escape but did not have the willpower to do it. I was a victim to my newly discovered transgender hopes and dreams. At that point, I still had not realized how far behind my gender dreams being a victim made me and I still felt sorry for myself because of all my gender dysphoric issues.

As I always point out, it was not until I began to experience my version of womanhood in the public’s eye did anything begin to change for me. All the effort I put into my appearance came back to help me get my high heeled foot in the door with other women. Then the real work began when I needed to communicate and interact with them. What happened was many other ciswomen were encountering me on a regular basis in the venues where I always went, so I needed to develop a stable feminine persona to go with my appearance. What would I call myself and what wigs would I wear every time I went out are prime examples of what I am talking about. I was getting to the point where I was staring my forties in the eye and I knew I was not getting any younger and in the back of my mind, I had a sneaking suspicion that I had lived my life all wrong up to this point.

Rather than bemoan all of the mistakes or missed opportunities I had as a male, I needed to face the fact I was wasting my time as a male anyhow because I was always meant to be female. I went home and wrote in my secret diary that I was not a man cross dressing as a woman; I was a woman doing her best to cross dress as a man and build a life on a house of cards.

The realization of my true gender status enabled me to be my real self to the public and ciswomen responded well to my truthful gender identity. Even if they were curious what I was doing in their world and why I wanted to play in their sandbox and work my way into coveted woman only spaces. Finally, I was coming to the point where I could think I achieved my own womanhood, just in a different way than most ciswomen. I was still relevant to the world and should be allowed to play in the sandbox.

Another big lesson I learned was that once I was in the sandbox, I needed to work harder to stay. One slip up back to my old male self, and I would be labeled an impostor and barred from the box. Faced with the task of starting all over again. To the best of my ability, all of my feminine mannerisms, interactions and vocalizations had to be perfect. I was so afraid most of the time until I finally began to relax and have confidence in myself.

The best part about the entire process was I survived to write about it and hopefully to inspire others in this very trying, difficult time to be a transgender woman to make it also. We all have differing yet similar paths to make it to the women’s sandbox. Just don’t expect the process to be all positive and you can make it by hopefully finding ciswomen who knowingly or unknowingly help you along. Those minor claw marks you might receive like I did down my back were just learning marks and helped me along. More than the women scratching me ever knew.

They helped me to earn my way into playing in the women’s sandbox. The claw marks just equated out to the stripes I earned when I was in the Army.

 

 

 

 

Meeting a Hero's Wife

 

Image from UnSplash.

This is a short post which basically revolves around the unexpected meeting I had yesterday with a very special person.

Nearly every Friday afternoon I attend a LGBTQ support group (virtually) at the Dayton, Ohio Veteran’s Administration hospital.

It is one of the best support groups I have ever been involved in, and it is rare that all the original attendees still come to the meetings. It is a very diverse group with everyone from gay men and lesbians to transgender women like me. Yesterday we had a full house including a new participant who I assumed to be a questioning lesbian ciswoman.

I turned out to be very wrong and as the hour meeting went on the moderator very skillfully brought it out of her why she was there. It turns out she is the wife of a hero. Her spouse is one of the transgender service persons forced to leave the military by the supreme coward who dodged the draft “Captain Bone Spurs.” Better known as president tRumpt. When she told their story, I was wowed and expressed my position that her spouse was a true hero and would she be joining the group in the future.

Since she said, they were just exploring the area for LGBTQ contacts, that would be a real possibility. And I was thrilled to have the chance to meet her. So, I will see if I have the chance after the Christmas holiday when we have our next support session. I will let you know what happens.

In the meantime, my wife Liz and I will not be attending any concerts by the Cincinnati Symphony Orchestra this season. Years ago, I tested my courage and even found a sequined formal dress to wear to a holiday concert with Liz. Even though, it was not my favorite form of music, I managed to calm down and enjoy the show when I learned not everyone else was looking at me.

We even stopped for drinks on the way home (in an Uber) so we would not have to drive and had a great time. Since Liz is a Wiccan, we don’t celebrate Christmas as such, we celebrate Yule instead which is close since the Christians “borrowed” Christmas from the pagans in ancient times. Plus, my daughter converted to Judaism years ago, so I am pretty much left out of the Christmas holidays altogether which is a total change from the years with my second wife who was a fanatic. Poetic justice, I guess.

Even though those days are past me, I am fortunate to still have Liz’s family to feel the holiday warmth from. I know many in the transgender community are not so well off this time of year.

For me, just the chance to meet a hero’s wife in person was a huge gift unto itself. As I said, I hope she comes back for more interaction and brings the hero with her.

 

 

Letting Things Happen versus Making things Happen as a Trans Woman

Image from Mahdi Chaghari
on UnSplash.

Perhaps you have heard a football coach talk about slowing the game down and simplifying it for his players. Of course, I had to equate it with being a transgender woman or trans man when I heard it.

I began to think of all the stressful days I spent in front of the mirror as my perception of a pretty girl, then taking my image public and into the world. For years it never occurred to me that I was trying too hard. I was attempting to micro-manage myself to ensure every little aspect of my feminine image was correct. Here is an example of what I was doing wrong. On any given day, my makeup and fashion were on point, and I was confident about my presentation. Then as I was out trying it all in the public’s eye, I would either catch myself walking hunched over like a linebacker or worse yet, trip over my own heels and almost fall. It took me quite a while to realize what I was doing wrong and try to change it.

For me, relaxation and confidence were the key to real gender change. I was letting it happen rather than making it happen. I discovered it was so much more pleasurable for me when it happened that way. After that I could take my game to a different level such as communicating one on one with the world for once as my authentic feminine self. A key point I had to do if I was ever going to make it to my dream of a male to female femininization project.

I also established bucket lists of things I wanted to do as a transgender woman and was able to accomplish most of them except a couple of ill-thought-out visits to women’s rooms when I had the police called on me. Letting it happen surely did not work for me then, but I recovered and gained my restroom privileges in other venues I went to. Fortunately, the police had better things to do than mess with me and I went on my way without further problems. That was years ago and I haven't had any problems since. That was a good thing because the restroom privilege was something that I needed more than wanted.

I cannot stress enough about how much I had to learn during this period of my life when I was making a serious push towards transitioning from a serious cross dresser all the way to a transgender woman. When in reality, it was mostly a mental transition, it was still a very important one to make. I have a difficult time explaining it but all of a sudden, something clicked in my mind, and I knew another change was needed. I was so more than a man wanting to look like a woman.  I wanted to be a woman and feel like one as close as I could. That was when I successfully set out to socialize with cisgender women just to see if I could. I conquered my fear and found out I could add another layer of just letting it happen versus making it happen.

By this time, my muscle memory had improved so much as a trans woman that it became natural to me. So much so in fact that I had to be careful I was not too effeminate when it came to me working my male job and living with my wife. It finally became too much for me to juggle, and I needed to put it down before it was too late and I became more self-destructive than I already was. What I did was, attempt to do more things as a transfeminine person and do as less as humanly possible as my male self. It is one of the reasons I took so long to transition, because of the need to work around a disapproving wife and male self which was desperately hanging on.

You regulars know this part of my story when my wife tragically passed away. Which left only my weakened male self to resist any efforts at total domination from my inner female who had waited so long for her chance to live and write her own gender workbook. Little did I know she kept her own workbook up to date and was ready to go. If and when she had a chance to use it. Perhaps, your inner female is keeping a gender workbook also and you will not have as far to go to catch up when you get the chance to live your life.

I discovered too that letting it happen versus making it happen was mostly common sense. Even though the two main binary genders do things differently, they often operate in parallel universes which are the same and seem to be doing more so in the younger generations. I first learned up close and personal during my first girl’s nights out I went to. I was worried about what I needed to do to be able to interact with the group but then found they had just flipped the script from jobs and sports to family and friends with the women. Quickly I relaxed and started to let my inner girl flow, and I was fine with most of all the other participants except for one who I perceived as being a miserable person anyway. Who was unlikeable to me, and I left her alone.

I chuckle to myself when I think of how my football coach’s words would come back to help me in such a different way later in life. I guess it proves that you just cannot count on anything staying the same when it comes to gender. Perhaps that is a clue why the population at large knows nothing about us and we live parallel lives from both of them. Whatever it is, if you are in your path of gender discovery, you will certainly feel the change from making it happen to letting it happen.

 

                                                                                                                                          . 

Staying in your Own Gender Lane

Image from Earnest Tarasov
on UnSplash.

Staying in my own gender lane may have been more difficult than I had ever imagined. Of course, it all started when I was externally born male. Then when I started to understand something was dreadfully wrong with my male existence, I needed to figure it out.

My first indication of what the problem might really be came when I discovered the thrills of wearing my mom’s clothes, since I did not have any sisters to beg for clothing off of. Sadly, even though I was thrilled to see my version of a pretty girl in the mirror, deep down I knew it was just not enough for me to stay in my cross-dressing lane.  I wanted to pull out and find myself in a more comfortable gender lane where I more than ever before to being feminine.

Before I could do that, I needed to define what being feminine meant to me. I knew just acting effeminate would get me nowhere except bullied to the point of beaten up and on the home front (which was very male dominated) I would probably earn a trip to a psychiatrist if my small stash of girl’s clothes and makeup was ever discovered. I was trapped in a male world I wanted nothing to do with, and worse yet, I was pressured to perform well in that world. I needed to be in a passing lane around as many other males as I could.

The problem was, I wanted nothing to do with that world and could not show it. And in the pre-internet era I was growing up in, I felt so all alone with no one to talk to about what I was feeling. I just knew I did not feel the so-called mental illness that gender issues were being referred to back then. All I knew was, I was having a very difficult time staying in the gender lane which was assigned to me when it felt so natural. Plus, when I woke up in tears after having such a realistic dream that I was a girl impacted my life terribly until I could get centered again where I was “supposed” to be.

Somehow, I made it through those very confusing gender days and finally made it out into the world to discover if I had any future at all in a world ruled by cisgender women. When here I was, a novice in their world trying to survive. I equated it with driving on the Autobahn in Germany. I quickly discovered when you were driving a VW Beetle (like mine) and ventured into the outside lane then you saw a car in your rearview mirror flashing its lights, you better get out of the way. My life in those days often felt that way. I was learning lessons about where I wanted my transfeminine womanhood to go but I always seemed to see lights warning me in my rearview mirror.

Through tons of trial and error, I learned I could change my gender lane to the one I dreamed of. From as young as I could remember all I really wanted to do with my life was live it as close as I could to being a woman. Of course, that meant putting all my safe male privileges behind me and set out to build new ones in my gender lane with new life experiences. Like the Autobahn I found there were no speed limits on what I could learn or experience in the new gender lane I was in. More importantly, I had no one except my old male self to tell me to slow down before it was too late and I wrecked. Here is where I make the excuse of why it took me so long to transition because I was overly cautious that I did not wreck.

As I was in the gender lane I wanted to be in for a change, it w as nice to finally wake up in the morning knowing I was coming closer to my dream of living life on my terms as a woman and not having to keep falling back on my male self for last minute support. I was one and she was me for good.

But just when I thought I had it all in my new gender lane, I discovered many small nuances the ciswomen around me use that I needed to learn and put into practice. Such as the powerful use of nonverbal communication and passive aggressive behavior. For the first time in my life, I needed to look intently at other women when I talk to them and search their eyes for what they were really telling me. Which extended into the passive aggressive areas of behavior I encountered. There were many times I fell for a smiling face or non-threatening comment which turned out to be a knife in the back when I let my guard down. They were all lessons I learned the hard way as I earned my ability to stay in my gender lane permanently.

The best part was that the more I learned, the more I wanted to learn about the lane I was in. Even my biggest naysayer, my male self, had to finally give up and get out of my way. I was in my lane for good and there was nothing he could do about it. I had served my feminine apprenticeship I was walking the path I always was destined to walk and in the short and long term I got out of the way until I could salvage was left of myself and move forward. 

When a Trans Girl is Serious

 

Image from Bruce Mars
on UnSplash. 

When I first came out of the closet, I wondered how I was ever going to convince the world I was serious about jumping the gender border into my transfeminine world.

Probably, before I started to convince any strangers of who I was, I needed to totally convince myself. Was I a cross dresser, accomplished drag queen or what. The last thing I wanted to come off as was some sort of a clown putting on a dress and makeup for laughs. I think, all the time I spent practicing in front of the mirror attempting to learn the art of appearing as a woman paid off. Because in a fairly short time, I was presenting as a convincing transfeminine person in the public’s eyes. I was far from being the most attractive woman in the room but at least I was making do with what I had to work with and getting by and the public perceived me as being serious also.

At that point, I was not getting the negative feedback I used to get when I left my male self and traveled to the feminine side of life. The worst that was happening to me was when other ciswomen gave me a knowing smile. Showing that they knew I was attempting to play in their sandbox or world. Even better was when I began to see the same people over and over again and they knew I was serious about where I wanted to be in their world.

As I gained more experience and began to understand all the layers which existed in a ciswoman’s life, I knew I had a long way to go if I was ever to be successful in pursuing my gender dreams. Then I purposely set out to try to experience new situations as a transgender woman because my feminine workbook was given to me blank. I did not have the same benefit other women had by growing up out of a female birth into a woman. I was doing it exactly opposite as I was trying to leave my male birth rite behind. Something that I had never asked for. Each time I successfully conquered something new in life I tried to experience, I looked for other things to do that I had never done. An example would be, once I conquered just going to bookstores and searching for books on gender, then I gathered the courage to stop at their coffee shop for a cup o joe. After that, I took it a step further and used the women’s room to wash up and check my makeup.

By now, you probably are getting the point of how I was branching out and expanding my life as a new trans woman. The world was becoming so new, exciting and scary that I was like a kid in a candy store and could not stay away. Even if I wanted to, which on certain days I did when I felt all my gender issues were out of control and my male self along with my second wife were aligned against me pursuing a transgender life any farther. The problem was that my inner woman was telling me the path I was on felt so natural and deep down I knew it was the right way to go.

Still, I tried to stick it out and try to maintain a presence in both my old male world and my new transfeminine one. By doing so, I certainly did myself and those around me more harm than good. Very simply, the stress was too much for my already frail mental health, and I took it out on myself and those around me. I needed to figure it all out and get very serious about how I was going to run my life before it was too late. Internally, I was out of control while externally I was just trying to hold on to my wife, job and family as I knew it. I would have not wished what I was going through on my worst enemy.

Thankfully, destiny stepped in and showed me the way.  My wife of twenty-five years tragically passed away leaving no major hurdles for me to move ahead with my plan to start gender affirming hormones or HRT. Amazingly, at the same time the Veterans Health Care System which I was/am part of approved a program of affirming hormone therapy along with a therapist to go along with it. Which I took advantage of immediately. Under her care, I became ultimately serious about the direction my gender transition should take, and I even went to my therapy visits as my authentic self. Even better, my therapist helped me change my legal gender markers within the VA and provided me with the documents I would need to change my other legal markers such as my driver’s license.

Changing my legal name and gender markers finally proved to myself as well ss my inner female how serious I could be about my future. Even still, with all I was doing with my life, a little voice kept telling me I should not have taken the easy way out and tried to get serious earlier in life about who my true self really was. Of all people, my second wife told me to do it on several occasions during the fights we had about what I was doing along the way on my gender path. It turns out I was going to travel it with or without her and it was my duty to make the call that I had to do it alone.

Sadly, I think most transgender women and trans men have a lonely path to follow before they are fortunate enough to find someone to share their path with. It is surely difficult to negotiate alone, and you certainly have to be serious enough to do it.

 

                                                                                                                                                       

Transgender Game Changers

 

Image from Andre Fonseca
on UnSplash.

One of the positives to being able to live a long life is to be able to look back on all the key moments in my life when a decision one way or another could have made a huge difference in my life.

Perhaps the biggest moment was when I discovered the enchantment of looking at the pretty girl in the mirror where my boy self was just standing. Sadly, the moments were fleeting as my life was calling me.

As I grew up and my life became more complex, so did my dealings with my transgender issues. One of the most important lessons I learned came early when my second wife and I encountered a handsome Harley motorcycle rider at a tavern we were at one day in Cleveland, Ohio waiting for a transvestite mixer we were going to, to start. I was very new  to being out in the world as a cross dresser and was completely surprised at my reactions when this guy came into the bar and started flirting with my wife. Then, I was even more concerned about my wife when she started to flirt back, completely ignoring me. What was I going to do since I was stripped of all my male reflexes of what to do when another man was flirting with my wife. I had to just sit there and be quiet and hope she did not go for a ride on the Harley with the man. Of course, my wife sensed my concern but let the situation play itself out to teach me a lesson in feminine competition. One I never forgot.

Another evening, I never forgot and could have been a bigger game changer than it was, was the night I had my makeup done by a professional makeup artist in Columbus, Ohio at another transvestite-transgender mixer I was attending. After the makeover, I was stunned at all the positive changes the artist made for me. I was flattered with all the compliments I was receiving and decided I did not want the evening to end early. I wanted to join the so called “A” listers who always went out on the town and show off my new look. Plus, for some reason, my wife decided not to go to this mixer, so I was free and on my own. We ended the evening at another tavern which I could not tell was LGBTQ friendly or not but one way or another I bought a beer and headed for one of the unoccupied pinball machines. When I did, amazingly I was approached by a younger good-looking man who wanted me to stay and play pinball with him. By this time, the rest of the “A” girls were ready to leave, and I needed to make a split-second decision on if to stay or go. Since I had no idea if the man knew my true gender or not, and I was in a strange city, I decided to go with the “A”’s who were jealous of me because I was approached by a man and they were not.

I never knew what would have happened if I had stayed and would the evening change my life forever, which also happened the night I went on a date with Bob. By this time, my wife had passed away, and I had not met Liz yet (my future wife) so I was free to explore my own boundaries. Bob was not from my area of the country and on occasion passed through the Dayton, Ohio area on business where I lived. On one of those nights, I knew he wanted to meet me in person at one of the venues I was a regular at. I had never partied with a man at a sports bar before, so I did not know what to expect. What I did not expect was the great time I had. It was the first time in my life that I had been treated completely as a woman, and I loved it. It was even a karaoke night, and he sang for me. And yes, Bob did know I was transgender. We shared a rather passionate kiss together and the night was over. Never to be repeated again.

There were other trans game changers such as girl’s nights outs and the conversations I shared with a man who I thought I could have gone farther with if he had stayed around. The “what if’s” remain big questions for me as I grow older, and I know you can’t have it all. In many ways I crammed a lot of life into my years which I am grateful for.

I should not be selfish though because I have been blessed during my life with people who have loved me, and I did my best to love back in return. Sadly, my gender issues were in my way through most of them and if I had faced reality, I could have been a better transfeminine person. Which is a topic for another blog post altogether.

 

 

The Rise of Transfeminine Privilege

 

JJ Hart (Middle) wife Liz (Left)
daughter (Right)

When I began to seriously leave my closet and mirror and attempt to join the world as my true self, I quickly lost all my male privileges and gained very few feminine ones. In fact, early on, the only privilege I felt was having doors opened for me by the men around me.

On the other hand, the most extensive male privileges I lost were my intelligence and my personal security. When I was around men, I learned to keep my mouth shut until I was spoken to, which was not very often because I think most all men knew I was transgender and wanted no part of me. And as far as personal security went, I needed to learn what ciswomen know from an early age to keep themselves out of possible bodily danger by being in the wrong place at the wrong time.

All along, during this time, I was wondering when and if the gender teeter-totter I was on would balance itself out and I would see the positives of what I was doing. It took a combination of things happening before I ever did. One was seasonal around Christmas, and the other one was when I decided to give up on men all-together and concentrate on knowing other women. A preferred topic in my mind, since I did not have to consider changing the focus of my sexuality, which had always leaned exclusively towards women. But I digress, the meaning of Christmas and what it meant to me as a transgender woman, is the real reason for this post.

To begin with, Christmas was always a major holiday for me and my second wife especially. Finding an exceptional, unexpected, rare gift was always the priority for me and even my brother’s family. The difference became to me was when I decided the Christmas shopping, I had been doing as a man would be much better accomplished as a woman. If I was able to pull it off, I could accomplish so much more during the Christmas rush I was in the middle of.

First of all, I needed to up my crossdressing game to give me the best possible chance to succeed in my shopping conquests. I went through my closet and pulled out my fancy, sleek, black pants’ suit for trips to upscale malls and my leggings, boots and sweaters when I combed through the huge local antique malls for just the right gift for my wife. I knew if I was to succeed, I had to be better than the average Ciswoman so I would not be potentially embarrassed. Also, the right makeup and hair was a priority because of all the up close and personal time I would be spending in the public’s eye. Through it all, I wondered where the magical feminine privilege would kick in for me.

The first major time it did was when I was shopping for a matching oak bookcase for my wife’s roll-top desk. One night, I found one which worked beautifully in an oak furniture store in nearby Columbus, Ohio. It just so happened I was returning from a shopping trip to a local Columbus upscale mall when I stopped into the store on the way home. After I found the bookcase I wanted, my old male self-wondered how in the world would I get it in my truck/SUV. Would anyone come to the aid of a tall blond in a black pants suit and heels? After I paid, I found out they would because for the first time in my life I was able to sit back and watch two young men load the bookcase carefully into my vehicle and finished their job off with a nice thank you mam. Because I had finally discovered a dose of feminine privilege, the half hour trip home went quickly, and I wanted to do more shopping, but I was out of time and money.

Sadly, once I returned home and had safely unloaded my prize gift, it was time to return to the place I did not want to be…my old male self. On the plus side though, the whole experience taught me (and provided the confidence) to move forward to my dream life of being a fulltime transgender woman and would not have to return home every night in a hurry to switch back into a gender I wanted nothing to do with. My feminine privilege was being established in the newfound senses I was feeling. Especially when I was doing something for others, such as buying gifts.

The experience made all the learning and trial and error experiences I went through during my male to female femininization process deeply worthwhile. There were other Christmas stories to share as I will do later. Such as when my wife decided we would have a special gift giving time for my feminine self.

 

 

 

 

Stopping was Impossible

 

Image from Edward Howell
on UnSplash.

For years as I followed my early cross-dressing path, I labored under the impression that someday I could actually stop and return to my male existence. Of course, the older I became I learned that stopping was going to be nearly impossible. The reason being, when I was forced out of the mirror and into the world, I began to have success.

To me, success was measured in the public reaction I received. Very early on I suffered scorn when I went out without the knowledge to blend in with other ciswomen. When I became successful, it took so much pressure off and stopping became less and less an option. Mainly because something clicked in my head that I did not want to ever go back which was different than wanting to. For example, there was the night at TGIF Fridays when I went into the venue with the mindset, I actually wanted to be a woman with other women, not some sort of an impostor. When it happened, I knew for sure stopping was never going to be an option again. I was firmly on the path to achieving my dream of possibly living fulltime as a transgender woman.

The more I decided not to stop, the quicker the pressure mounted on me on what to do with my old male life. He had dug in deep and was refusing to go away easily. The worst part was he made good arguments such as what was I going to do about my spouse, family and employment. Just as a start. What did I do? I continued to internalize my inner woman and keep researching my future. Since my gender workbook was blank, I had a long way to go. Primarily when I needed to learn how to communicate one on one with other women when I was exceedingly shy to start with. To arrive there, I went to excess of taking feminine vocal lessons to attempt to learn to communicate better. As I was slowly succeeding in my efforts, again I knew for sure I could never go back.

Another main thing I learned was that I needed to control my emotions, not let them control me. Or when I hit the valleys of my journey (which there would be many), I had to pick myself up from being a failure and continually go back to my gender drawing board to figure out what I was doing wrong. I knew I had a testosterone poisoned body. I needed to work around but I dedicated myself to somehow doing it. I discovered from all the trips I was making to thrift stores; I could find the fashion I needed to make myself look the best I could under the circumstances I was working with. It all added up in my mind to I could never stop.

Along this way too, I quit purging for good. I had learned my lesson about the previous purges I had attempted. The lesson was, I could never go back to my old male self again. I was tired of throwing out all my hard-earned clothes, shoes and makeup only to have to replace it all again as soon as a month later.

What helped me was, I was learning over and over again how wrong I was fighting my instincts to be a transfeminine person at all. I always point out how wrong I was when I was fighting my true feminine self at all. I suffered from the brutal pressure I put on myself. So, stopping my transgender advance was never an option. I should never have waited as long as I did to go after my gender dreams.

I was fortunate that my basic personality never lent itself to stopping my search for my dreams. All my life, all I wanted to be was a woman and I just could never visualize myself not working hard to achieve my goal. I just never in a million years understood how difficult it would be for me to do it. I should have listened to my wife when she tried to tell me I was on the wrong path to achieving my goal. In a way, I did but not nearly enough until I did not stop until I was allowed to exist behind the gender curtain. Once I got there, stopping was never going to be an option again.

Then HRT and new feminine hormones shifted my mental thinking to match my external appearance which was improving all along. I never expected the changes to be so dramatic so quickly. I am glad stopping my male to female feminine transition was never a reasonable option.

 

Is There Really a Difference between Genders?

 

Image from Pea on UnSplash. 

Yesterday, I briefly wrote about how I saw the world differently when I went out for the first time to view Christmas decorations at Clifton Mill, Ohio as my feminine self. I said something to the fact that my senses seemed to heighten as I viewed all the decorations and people around me. To me, the whole evening was brighter and more festive than when I viewed it as a man, wondering how it would be to do the same thing as a woman.

Little did I know the experience would prepare me for later life as I progressed along my gender path. Perhaps, initially, the new senses I felt were psychological in nature because I was still years away from actually changing my gender hormonal balance from male to female when I added HRT or gender affirming hormones to my system. Which means, I guess, if I was in some sort of a scientific gender study, I would not have needed the hormones to increase my femininity at all. Which would be good news to all of you who for medical or spousal reasons cannot consider HRT.

One way or another, I felt a real difference in my world when I entered it as a woman rather than a man. If I was cold, I could react accordingly and not have to be macho and try to ignore it is a prime example. Then, quite possibly, the biggest change of all was what I was going to wear. I had so many fashion choices I could barely make up my mind. It seemed I was only limited to what I could afford to shop for and buy. The sensory feeling of the clothes was wonderful, and I just loved the big, warm, fluffy sweaters I was able to wear because they were in fashion at the time and paired perfectly with my denim mini skirts I was able to find at my favorite thrift store. I discovered that I was perfectly comfortable when I wore a pair of tights or even leggings with my sweater/skirt combo in cool Ohio weather.

Even though the clothes did make a difference for me, the buzz quickly went away and the reality of what I was attempting set in. I have always believed that attempting to change the human gender is one of the most difficult things a person can attempt because there are so many roadblocks in the way.  Such as current misunderstandings of trans women or trans men’s lives. No matter how you cut it, it is just difficult to explain to a “civilian” what is going through our minds when we made the monumental decision to jump the gender border. What could possibly go wrong? Ha ha!

Sometimes, we end up surprising even ourselves with the gender changes we have to go through to be successful. As we begin to earn our way behind the actual gender curtain into woman only spaces, we begin to see and feel all the real differences there are. I know my first girl’s nights outs were real eye openers for me. I had no idea of how ciswomen interact with each other when there were no men around. The differences were real, and I cherished my chances to experience them. So much more than even my new one on one communication challenges with ciswomen strangers in the world.

As I approached the idea that I could actually take the opportunity to attempt to go on gender affirming hormones, naturally I knew it was a huge step forward in my transfeminine development. First of all, there were the health consequences of a sixty-year-old male starting to reverse the hormones he had lived with successfully for all those years Plus, back in those days, there were many naysayers preaching about the possible damage female hormones could cause on the body. Fortunately, I found a doctor who did not believe in all of that, and he approved my HRT. When I started the meds, I felt an almost immediate change. It was certainly what the doctor ordered, and I was rapidly increased to higher dosages of my precious new medications.

I felt great when my external changes such as breast development started to happen faster than I expected and was even more surprised at the internal changes I was feeling. Like the first night I visited the Christmas lights, when my world softened and became more perceptive, I quickly found myself in a world where I could appreciate everything more. Heat, light and sound in particular affected me more when I ventured out in public to my regular venues.

At that point, all I really knew was I never wanted to go back to the old male life I forced myself to live. I had found my new home.

Sealing the Final Deal in my Gender Struggle

 

JJ Hart. Key Largo last year.

Sealing the deal on my male to female gender transition was the most difficult decision I have ever had to make in my life.

It is the main reason I kept putting it off until I was nearly sixty years of age and could take the pressure no longer. The only way I kept what sanity I had was to cross-dress my way along until I could take bigger, more substantial steps.  One of the problems was, I had learned that cross dressing was not nearly enough to solve my gender issues and sooner or later, I would have to face the truth of who I really was. Also, I was very naïve and thought I could balance the influence of two genders in my world as I grew older.

As I set out to build a reasonably successful male life, at the same time, I was trying to fill out my feminine workbook with absolutely no help from other women. I was stuck being on my own for years, until I progressed to the point where I could leave my closet and explore the world as a novice. After brief successes (and a lot of failure), I was able to see portions of my future and judge if I could ever seal the deal and live my dream of being a fulltime transgender woman. Even though I was still progressing, I was still hitting roadblocks on my path to trans success and had to keep working my way forward through failure.

All I could see in my future was a life I would have to live alone with no way to support myself as a transfeminine person. My sexuality did not change, and I wanted basically nothing to do sexually with men, and I knew how incredibly difficult it would be to find a ciswoman who would accept me the way I was. I had pulled off some other seemingly impossible things in my life but accomplishing this and sealing the gender deal was too much to hope for.

Then, as I lived my new life as a trans woman, I learned that maybe my dream was not too much to hope for and one thing was for certain, if I did not try, I never would know if I could make it. I expanded my explorations with men and managed to have a couple real live dates when I enjoyed myself but nothing sexual happened, so I set my sights in lesbian bars for a ciswoman who wanted a woman with a little bit extra experience in the world. Amazingly to me, I was moderately successful in one lesbian bar where they accepted me. Which brought me so much closer to thinking I could seal the deal and live my dream.

Now I was to the point where I had to really see where I wanted to take my life. I was an executive general manager of a large casual dining restaurant which I had put in years of hard work to arrive at. If I transitioned, all the work I put into my career would be gone (along with the money) and I would have to start all over again. Behind the world as a transgender woman. Naturally, the whole situation was a major roadblock.

It finally came to the point where I faced sealing the deal like I was jumping off a cliff into nothingness. At that point destiny set in for me and made my final decision so much easier. Tragically, I lost my second wife and almost all of the close friends I had to death and could start with a clean slate in life. Plus, the restaurant I owned was failing and I was losing it also, leaving me a couple of years to work before I could retire early on Social Security which would give me enough income to get by. As You can tell, the doors to transition were opening wide and I would have been a fool not to walk through them.

Most importantly, my mental health was suffering and my self-worth as a man was at an all time low, so it was time to end the torture I was feeling and jump off the cliff and seal the deal. It was during this time too, that the Veterans Administration health care system, which I was already a part of, approved veteran’s care for gender dysphoria with mental health counseling and HRT if approved. I was quickly approved and ended up taking another giant step towards achieving my dream and sealing my lifetime goal.

What did I have to lose? I was leaving a male life I never really felt comfortable in to jump off a gender cliff and land in accepting women’s arms as I joined their world. When I did, I tried to take every little bit of advantage I could from all the learning experiences I put in over the years. Landing on my feet in high heeled shoes was a challenge but I managed to make it in fairly good shape. I came out fully at the age of sixty when I finally decided to seal the deal and never looked back. I could not take balancing two genders any longer and took the easy way out into the world of women where I should always had been.

As always, thanks for reading along, and any comments are welcome! I always do my best to respond.