Try then Try Again

 

Early Days in my Gender Closet
JJ Hart.

When I first broke out of my gender closet and into the world, there were many cases of failure I needed to deal with.

For example, all the evenings in malls when I was singled out for abuse by groups of teenaged girls. So much so that I tried my best to head to the other side of the mall as quickly as I could in my new high heels before the girls noticed me and started laughing.  When that happened, many times I was sent home in tears wondering what I had done wrong with my presentation. One thing was for sure, I needed to go back to my cross-dressing drawing board and try, try again.

It took me a while to realize I was backwards in my public presentation thinking. I was dressing myself how a man would rather than how a ciswoman would if I stood any chance of blending in and making it in a world I only had just dreamed of. Plus, I benefitted from a crash diet I put myself on which helped me to fit into more stylish feminine clothes. It was the first time in my life that I had been so serious about anything that I could remember.

One big thing I did not realize was the total scope of the male to female femininization project I was taking on. The deeper I delved into the feminine culture I was in, the more I found I had to try to do to become successful and there were many times when I simply not a success. One time that sticks out in my mind was when I visited my gender therapist unannounced as my authentic self and sent her into obvious shock looking around to find out where her son was. I would have thought, since she advertised herself as a gender therapist, she would have been more comfortable around a person cross-dressed as themselves. But she was not. I took it as I had to keep on working on my feminine presentation to hide all the testosterone poisoning male puberty had wrecked my body with.

The more I was able to find myself behind the gender curtain as a transgender woman, the more I needed to try, try again to never stop learning more about how ciswomen spend their lives operating in the world. The circles they run in and their overall dealings with each other as well as men come to mind as I think back on my initial experiences. It was a scary yet exciting time in my life as much of the time I was still risking destroying life as I knew it, if the world discovered my deep dark secret. I had not yet concluded my secret really was that I was a woman hiding behind a man. Not the way I was living thinking I was a man trying to be a woman.

Most of the time, the world did ignore me as my presentation improved well enough to get me by but on the occasions I met the rare TERF (radical feminist) gatekeeper who did not want me behind the gender curtain, I was sent away to try, try again until I earned my way into the places I wanted to go mainly such as women’s restrooms because on my long days out I simply needed to go to the bathroom and not make it such a big deal. It took me a lot of resilience and knowledge of the feminine world to do it but I finally earned my way into the “room” also.

I have always thought that building my fragile confidence into a strong one was one of the best moves I ever made so I could relax in the world and stop trying so hard to be myself. I say fragile because there were so many times over the years when I thought I had achieved confidence only to have it shattered by an unfeeling gender bigot. By trying again and again to overcome the haters, I made it to a point where I could say to heck with them and I was going to live my own life the way I saw fit.  

When I had reached a point where I thought I had enough confidence to get me by was when something unexpected happened to challenge my path. All along, I had some sort of an idea of how complex a ciswomen’s life was than a man’s life, but until I got there as a trans woman, I did not have a real idea of how complex. It was as if every time I thought I could see a clear road ahead on my gender path, someone would throw a stop sign in my way. Making me stop what I was doing and look around. Did I really want to take all these difficult steps I was taking to be a transfeminine person after all.

Of course, once I stopped, looked around and thought about it, I discovered I was in the world which I had always belonged to and I wanted to stay in the worst way. The more I was allowed to play in the girls’ sandbox, the more natural I felt as I felt my life make a seismic shift towards becoming the person I had always meant to be. To keep trying, I needed to decide to risk losing all my remaining close friends, family and employment and embark on the road without any more stop signs.

I was not getting any younger and at the age of sixty my transgender biological clock was running out. It was time to try to see if I was still healthy enough to be approved by a doctor for gender affirming hormones or HRT and I was. Which was actually the last big gender hurdle I had to try because I had already done the social part and I did not desire any extensive facial or genital realignment surgeries. So, I could then try to discover if I could find anyone to share my unique life with.

By trying to put myself out there on dating sites and in the regular straight venues I was going to, that paid off for me too when a ciswoman lesbian from nearby Cincinnati responded to one of my on-line dating requests and we are still together fourteen years later.

All those early years of trying and failing came back to help me years later when I needed it most and my life went full circle.

Thanks for reading along and passing along all your comments and reactions! I really appreciate hearing from you.

 

 

Figuring it All Out

 

Image from Erik McLean 
on UnSplash.  

I correspond quite a bit with one of my regular readers “Bobbie” whose life and mine amazingly align up in many ways including our military service. And if my memory is correct, she also benefited from a heavily influenced lesbian set of interactions. My apologies if I am wrong with my old memory which is like a steel trap…a rusted one. Because I heavily benefited (and still do to this day) with my feminine “upbringing” with my lesbian friends.

At any rate the reason for this post I to explain how Bobbie and I diverged on our gender paths. One very important way was when Bobbie went into how precisely she planned her male to female transition. All the way down to having a supportive wife. Which I did not and I needed to work my transition around her because she flat out refused to live with another woman. But on the other hand, did not mind that I was a cross dresser. She even went as far as scraping money from our limited family finances for me to rent a motel room to cross-dress in so I did not have to go out from our house which was on a heavily traveled street.

 Another way I diverged from Bobbie was her employment as a man required her to have several backup plans for every move, which mine didn’t. I was in the fast-paced casual dining industry which required me to work in an environment which constantly changed and was very difficult to plan ahead for. All of which really appealed to me at the time. Also, for various other reasons, I have decided to stay away from all gender related surgeries. Much different from Bobbie as I will translate for you:

“When the transformation began, the checklist was social first, add HRT, get the orchi and then the bottom surgery. A BA may be in the offing as my P has finally exhausted any more growth and a "Barely B" doesn't quite cut it.” Translating, “Orchi” means removal of the testicles, “BA” means breast augmentation surgery and “P” means taking progesterone hormones in addition to any Estradiol you may be also taking. Finally, “Barely B” means her breast size under the hormones she is taking, and “bottom surgery” is genital realignment surgery and is a major move.

I also decided against taking any progesterone after my endocrinologist did not like the idea at the Veterans Administration. But on the other hand, I started like Bobbie did with social and then went to the HRT or hormone replacement therapy and then went off to live my life as a transfeminine person. By this time, I was in my sixties, excited about my new life and set out to find someone unique enough to want to share it with me.

As you can tell, the whole male to female femininization path is not for the weak of heart and very much trashes the idea that transgender women embark down this extreme path out of a desire to just dress and look like a ciswoman. I get amused when I read that and think if the person saying it only knew the truth, they would certainly think differently.

Also, you can tell from Bobbie’s and I’s paths, there are many different ways to get to where we want to go as transgender women and transgender men. Even though my first dinner date as a trans woman was with a trans man, I still thought I knew the layers of the lesbian community, but I did not. Not only was I learning something totally new, but at the same time, finding out where I fit in. As the result of pure effort and observation, I learned I fit in quite well with the femmes or “lipstick” lesbians I encountered. To this day, I still benefit from my initial friendships I made with lesbians. As I have been in a relationship with a ciswoman lesbian for over fourteen years now and is going strong.

You may not have the circumstance or the ability yet to go “social” like Bobbie and I did, but the world is always changing, and you can change with it. Change is also different. You can plan ahead for six different scenarios (like Bobbie did) or pretty much just step out into the world and do the best you can like I did. I think now, I just wanted someone to realize my truth who knew me, but then it grew into carving out a whole new feminine life away from my old male one. I guess you could say I won the battle by taking an approach I never thought of taking. It was only then that I did set up an orderly “bucket list” of what I wanted to try to do behind the gender curtain in the world at large. As I was getting closer and closer to a dream life I never thought I could succeed in, for the first time in my life I needed to plan ahead and then let destiny take control of my life.

Examples of how destiny led me to successful outcomes were when I was matched up at the VA with a therapist who was knowledgeable about LGBTQ persons and specifically trans ones and was willing and able to help me with important tasks such changing as many of my legal markers that I could. She was really good and even helped me separate my depression and anxiety issues from my gender dysphoria. Maybe most importantly, she opened the door for my approval for HRT which I still cherish today. Sadly, my therapist moved on but I was lucky to have her when I did.

No matter where you are in your gender journey, I always enjoy hearing from you. As I said, remember there is no right or wrong way to discover your true self. I am always interested to hear of different paths. Humans are a very complex tribe and being transgender might be the most complex as all. Just remember you are in excellent company.

 

 

 

 

 

 

Being Better as a Trans Woman

 

Image from Donald Gianetti
on UnSplash.

Often you must be better than the world to prove yourself as a transgender woman or transgender man.

An easy example would be we have to be better with our appearance. Because of the current lack of concern over appearance with many ciswomen and cismen, it’s an anything goes fashion world when women are wearing their pajamas and slippers to shop at a big box store, I won’t mention. Because we trans persons have so far to come in the appearance department, we cannot set our appearance bar that low or even want to.

Another problem with appearance is that we have had so few natural advantages to help us along when we first take the tentative steps out of our gender closets. In the case of transgender women, very few have the advantage of escaping the ravages of puberty which gives us angles, broad shoulders and deep voices. So, unlike the curves and softness we see in the women around us and envy so much. To get by in the world as a cross-dresser, we must strive to cover our natural flaws and act like we are not doing it.

The good thing is that ciswomen provide us with a big range of fashion to work from. Some wear dresses, some wear pants, some go without makeup and others don’t as life goes by. All you have to do is grab a spot you feel comfortable in and try to maintain it in a world of curious ciswomen who want to know more about you. You notice I said try to maintain it because early on, finding the best fashion and learning hair and makeup are major challenges we face. As our old bodies do not want to cooperate with the new path you have set them on.

Since I have always felt more comfortable in pants, leggings or well fitted jeans as a trans woman, I often took in criticism from other novice cross-dressers when I went to mixers in pants. Per norm, I did not care what they said about wearing pants as a man all the time so why I would do it as a woman because I was noticing how stylish some women look in their pants. I even had a glamorous silky black low-cut pants suit I wore to prove them wrong. Plus. most importantly what I wore was none of their business if I was aiming to be as good as the world of ciswomen in public at large who were increasingly wearing pants in their wardrobes. Not a bunch of cross-dressers at a social/mixer.

The more I was out in the world and interacting with the public, I discovered that appearance was just a small part of being better than the next person. Following some rough early experiments with my presentation as a transfeminine person, I settled into noticing who was noticing me. I learned men rejected me almost completely (which was fine by me) and women on the other hand wholeheartedly accepted the new me who wanted so badly to be in their world. The percentage of gender acceptance I received totally surprised me and I had to up my game to get better when I faced the public with so much more at stake.

Suddenly, women wanted to talk to me, and I was initially surprised and had to talk back. Then as now, I am very self-conscious about my voice, and it took me what seemed like an eternity to understand my communication skills centered more around what I was saying more than how I was saying it. In fact, I needed feminine vocal lessons to learn more about how women speak to each other. Primarily when men were not around. I also leaned the power of passive aggressive speech behavior in cis women and how it could apply to me when a potentially smiling face did not equal a supportive woman who could just as easy stab you in the back. After I tended to more than a few claw marks down my back, I adjusted to the new world I was in and survived by being better than them.

All these steps led me to pursuing an expanded transgender bucket list of potential things I wanted to do as a trans woman. To learn if I would want to do them on a permanent basis. As my checklist grew, my confidence did too and I discovered how natural I felt in the new exciting yet scary world I was in stripped of all my old male privilege such as dealing with my own personal security. With the menacing male scowl being gone, I had to rely of my new feminine senses to get me by and to stay out of potentially dangerous situations. It was all a major lesson of being better in the world out of a sense of pure survival as a new transgender woman.

At that point, destiny set in for me and set my life upside down as nearly all the loved ones I new and respected passed away. Leaving me all alone. To survive, I had to quickly quit being a victim and decide which direction my life would take. I took the feminine path, was approved for HRT or gender affirming hormones and prepared myself for a bumpy path ahead. At the age of sixty, I needed all the wisdom I had learned from a predominately male life and apply it all to a new female existence and exceed my own expectations.

By taking chances in the world, I had lucked into finding supportive ciswomen friends into my new life and I give them all the credit for the ease that it happened. And it made all the prep work I had done in my life worthwhile. Even still, I found I had to be better than the average woman to find my way and stick to it so I would not slide back to my old male ways.

Before I go, I would like to thank “Grace” for inviting me to write for her group “Empowered Trans Woman” on Medium. I really appreciate it

 

 

 

I Was Risking it All

 

Image from Leo Visions
on UnSplash.

In many ways this post is an extension of yesterday's explanation of me never really having a plan b as I traveled up and along my gender path to transgender womanhood. The essence of what I wrote was I did not have a real plan if suddenly it was evident I was not going to make it to my dream.

I was taught to be a dreamer by the unrealistic expectations my parents put on me. Whatever I did was never good enough and often sent me back to hide in my dresses, hose, and makeup. The only place that my impossible dream of being allowed to be feminine could become a reality. If only for a short time. I don’t know exactly why, but the gender dream I was pursuing so well was the only dream I wanted to become a reality as I did just enough to have good grades in school and played just enough sports to keep the bullies away.

Cross-dressing was always a risk because back in those days (the 1950’s and early 1960’s) gender issues were considered to be mental health problems, and I knew that did not describe me. On the other hand, I did not want an impromptu visit to a psychiatrist to tell me about myself and how I should be treated. Fortunately, that mental health visit never happened as I continued to risk my existence on some sort of a high-wire act which if I ever fell, life as I knew it would fall with me.

Of course, as it always does, life became much more complex as the years flew by. As my cross-dressing became more presentable, at the same time, I had college demands and a military service I never asked for to deal with during the Vietnam War years. All this time, I was learning what it meant to risk it all in my life and somehow still succeed. As even though my gender issues were put on hold for a long three years, I learned valuable lessons from the Army on how to attempt to deal with my dream which was on hold. At the least, I learned from the military how to deal with a structure I had never had before as well as other issues that would take another blog post to deal with.

When I was discharged from the Army, I gained my first and only child and my life became even more complex. What could I do with a child to deal with if I wanted to risk it all to run away and live a transfeminine life. Dealing with everything else for me became easy when I had a family to provide for. Any alternate plans I had for my future were delayed again along with any hope of ever making it to my dreams.

What suddenly came along to help me was when the internet took hold of the world and I was introduced to people just like me I could reach out to and even meet. All because of the first in home computer my second wife and I purchased. By participating in the first chat rooms of the time, I had my first taste of what it meant to be a transgender woman and not a parttime cross-dresser as well as sampling my many layers of the gender spectrum I never knew existed. The one big thing the computer did for me was that it taught me how badly I wanted to test out the new world I had discovered for myself and see where it took me.

I also learned quickly that it was easier said than done. Mainly because when I left my safe closet mirror and jumped into the harsh reality of being a trans woman in the world was not going to be as easy as I thought. I needed to quit dreaming of what I thought I should look like and begin to expend all my time and money working on how to survive in a world where ciswomen run the show. Sometimes up front and most of the time behind the scenes which I came to call the gender curtain. I found out the hard way, that to not be rejected in my quest to make it behind the curtain I would have to eventually risk it all in search of the new, exciting world I wanted to live in.

I am not a poker player at all, but I knew I would have to push all my chips to the center of the table to see if I could ever win my goal. The problem remained that my male side was still acquiring more chips with his new more demanding job. Here I was stuck between two genders trying to rule each other and the male side was materialistic, and the female side was more natural and felt like I was doing the right thing for the first time in my life. All the turmoil resulted in was destroying my already frail mental gender spectrum health. It tore me up as I had to constantly be aware of which gender I was on any given day.

As I said, eventually my feminine side won out as I chose feeling more natural in the world than I ever had as a man. He had been reduced to a shell of his former self by being able to shed his male privileges he earned but never wanted. In its place I gained the greatest female privilege of all…the freedom to experience the world as a trans woman myself. It took a while but all the dark downtimes I experienced on my bumpy gender path made me a more resilient trans woman with a unique understanding of both sides on the main gender binary.

I cannot imagine what would have happened if I had lost that gender poker game so long ago because I was living such a miserable life. Plan a was to always live as close as I could to a woman. It took me decades of life (5) to get there, but I made it.

 

There Was Never a Plan B

 

JJ Hart, Back row far left
Girls Night Out.

Very early in my cross-dressing days, I always tried to have a plan b in the back of my head if danger approached in the form of my brother discovering me or my parents coming home early from work.

Seeing as how I had no effective plan to get out of what I was doing in mom’s dresses and makeup, I thought that somehow, I would have to just try to lie my way out of it and say I would never attempt it again. Knowing that was a deal with the devil I could never make and expect to keep. As I continued to cross-dress in the family mirrors, I finally had to throw caution to the wind and just go ahead and do it.

Years went by as well as the complexity of what I was doing as I tried my best to express my feminine self. At the least, I thought of better ways to hide away my resources from prying eyes and was successful all but once when I got careless on a weekend, I was away when I was waiting to go into the Army and start basic training. What happened was, I had just mixed my feminine clothes and wig in with a bunch of my male clothes thinking that one would disturb them until I returned. I was wrong and when I got back, everyone else in my apartment had not returned home for a college break leaving me all alone except for one other guy who had come over to visit.

As we sat around drinking a few beers, I decided to gather my courage and somehow asked would he like to see me dressed as a woman. Effectively, throwing all ideas of a plan b if he got up and bolted out of the apartment. To my surprise, he did not and was receptive to the idea, so I left to start the prep work needed to finally come out to another person. After I had taken the time to shower and shave my legs and face, I went into my bedroom looking for my feminine clothes, wig and makeup. Only to be shocked to learn they were all gone. Someone had stolen them when I was gone. All the plans for the evening I had were shattered as we sat around and then finished all the beer and nothing was ever said about him coming so close to meeting the true me. As far as confronting anyone about where my clothes, wig and makeup had gone, I decided to keep my mouth shut because I was so close to having to report to Ft. Knox in Kentucky for Army basic training anyhow. A final solution for a plan b during the next three years of my life. I knew I could not entertain any ideas of cross-dressing at all.

When I was discharged and Halloween parties with my friends became the only external form of feminine expression that I had, I needed to ignore any of the warning signs that I was giving away any idea I was not as masculine as I acted. I was so into going to Halloween dressed as a woman that I decided to take matters into my own hands and ignore all the plan b’s that I had thought up. Even to the point if some other person commented on my “costume” and the effort which went into it, I would just try to laugh it off. Mostly what happened was compliments from other ciswomen on my shaved legs and I even gained the nickname of “legs” with several of them which I had to act like I did not care. When deep down inside I was overjoyed and wanted more input. It took me years to understand what they were really saying was I looked good for a man dressing as a woman.

As more years went by and I became very serious about being a transgender woman and was attempting to hide it from my second wife, plan b’s became very important to me. In many ways, I had regressed to my childhood in the ways as I had to hide my femininity away from her. In addition to being very tuned in to when she got off of work, I needed to get better and better at makeup and eye makeup removal, so hopefully she couldn’t tell what I was doing when she was at work. The problem was that practice was making my femininized presentation more effective.  Success just made me want more and having a plan b at all was disappearing totally.

For the longest time, the only recourse I had was to attempt to lie my way out of whatever transgender activities I even had to resort to trying therapy to save our relationship. The gender therapist was wiser than I was and told me there was nothing she could do about my deep-seated gender issues. I was trying to buy time with my wife and save our relationship as long as I could, but the therapist was not a miracle worker and I quit going. Leaving me to wonder what I would do about finding the next plan b I desperately needed to hold my marriage together. Because I knew it would be just inevitable my wife would discover what I was doing as a transgender woman exploring the world and we would have a gigantic fight because I had promised I was going to stay home.

The problem was that I knew I was wrong and was just buying time until the next adventure I had in the world with the ciswomen that ran it.

Finally, what happened was I ran out of all needs to have a plan b when it came to me being a transfeminine person. I had learned to live freely behind the gender curtain which I had waited so long and worked so hard to do. In fact, it was the only big dream I had in my life. I then resorted to a new plan to live out my life the way I wanted.

 

 

 

 

All Along I was Just Me

 e

Inage from Gayatri Malhotra
on UnSplash. 

It took me decades of living to realize the simplest of all realizations…just discovering who the true me was all about.

It turned out I was so much more complex than the friends I had around me in how I felt about life. Which often help me back because I could not express how badly I wanted to be a woman. What I did was, I took the natural male response I inherited and internalized all my feelings. Naturally, the male response did not work and all it did was wreck even further my already frail mental health. If I could not cross-dress my anxiety increased and when I did my paranoia kicked in when I thought, I was getting caught.

As I added years to my life, the complexity of being a gender dysphoric person grew with the years. What did I do? I tried to outrun my problems. It wasn’t until the Vietnam War years and beyond did I learn that I would have to stop being a victim and stand up to living a life outside of the shadows of being a man. The idea of moving my family around and changing jobs all the time until I finally landed a job I wanted in a location, I wanted to be. That meant I climbed out of fast food and landed in a full service, casual dining chain which served alcohol which was exactly where I wanted to be.

With my dream job in place, I could concentrate on my feminine side by beginning to go to the small diverse LGBTQ parties I used to go to in nearby Columbus, Ohio. At those mixers, I was able to meet transgender mentors who would define my future. From them, I learned a path to my dream may actually be possible. The me I had always dreamed of was finally beginning to emerge. Much to the chagrin of my long-time second wife who actually went with me to a few of the parties. Probably, just to keep track of me. One thing was for sure; my wife never liked the trans woman I was becoming. Back in those days, I was still trying too hard to dress to impress and my wife was right, my dresses were too short, and my makeup was too heavy for her liking.

As she normally was, my wife was right about my appearance, and I tried my best to tone it down when she was around. Most of the time to no avail. I was stubborn and had to live out my so-called adolescence years of cross-dressing before I learned how to dress to blend in with my wife and the ciswomen around her. As I always say, sadly she passed away before she ever got the chance to meet the mature transgender me. I know we could have not stayed married but maybe at least be friends.

The question became, what was I doing with my time when I was discovering who I really was. What I was doing was exploring as close as I could what it would be like to live a whole new life behind the gender curtain. For the most part, I was successful as I made my way from the relative safety of the gay venues I was frequenting and jumping into the more challenging straight sports bars I was used to going to as a man. By never causing any trouble, always smiling and most importantly by tipping well, I was able to establish myself as a regular in several venues which seemed unreachable to me just a short time before. Most importantly, I was able to bring my love of sports from my male life into my female life with no problems. Which was a surprise to me.

As I did, I discovered the true me was not that far removed from the old me. Basically. I had just changed my appearance and gave up basic male privileges such as perceived intelligence and personal safety, and the best was yet to come as I was able to begin to move around freely as the new me in a world run by ciswomen. Quoting my second wife, I didn’t “make” a terrible woman after all. Primarily because I was not “making” anything. I was becoming me. Sure, I knew on occasions I could have done a better job, but I never allowed myself to be a victim and moved on back to my gender path. Which was beginning to change dramatically because I was beginning yet another  major gender related transition in my life.

First, there were the two obvious mental transitions I went through including the initial once when I realized I was so much more than a weekend parttime cross-dresser which went all the way to that fateful night at a local TGIF Fridays when I had had enough of that thought pattern and went out to be with the other ciswomen just getting off of work at a nearby mall.

From that moment on, I knew I could never go back to my old unwanted male self. But still, I felt as if something was missing in my life. It was because I was still missing the obvious transition of all as I finally realized I was never a cross-dresser or a transgender woman; I was just me.

I wish I could take credit for being persistent and intelligent that I kept on pushing to find me but I can’t. That credit goes to all the ciswomen who I became close to over the many years of struggle I endured. And yes, my second wife is included because she was the first to say be man enough to be a woman and make life easier on both of us. As we all know, many women are good at reading small lights inside of a person (unless you are fighting an unsupportive spouse) which is a point for another blog post.

I can’t say enough positive about all the women in my life who helped kick me out of my male nest and into the world of women. They knew me better than I knew me.

 

 

 

Understanding is the First Step to Overcoming Fear

 

JJ Hart (Center) on a 
girls' night out. 

Before you can overcome fear, you need to understand exactly what you are afraid of.

I know I was petrified of leaving my closet behind and heading out into a world where I knew little or nothing as a novice cross-dresser. It took me years to overcome most of my fears except the ones I never did. Such as going into male dominated spaces by myself as a transgender woman. For some unknown reason, that one thing has always been a problem for me and my anxiety issues about coming out in the world.

When I was younger, I always thought either I would grow out of my need to feel feminine in all ways or somehow, I would lose my fear of doing it. Of course, I learned quickly that anytime soon I would not be outgrowing my urges to cross the gender border into a feminine world. In fact, my urges were getting stronger which led to more fear and anxiety about the future of my life. Out of sheer survival, I had to find out why I was so scared.

The easy way out for me was just by thinking that making the gender jump into what I perceived as greener pastures, was the reason I was so scared. I was using the dresses and makeup I had acquired to hide behind and feel better in times of duress. I was too new at the gender game to consider ideas such as gender privileges which I was accumulating as a young man with out even knowing it. Privileges such as never having my intelligence questioned or having an innate sense of personal security were never questioned. I found I would not have to until much later in life when I began to present well enough as a transfeminine person to get by. All of a sudden, passing as a woman meant more than just having a man open a door for me. I had to take the good with the bad if I was ever going to be successful in making it to my dream of living as a woman on my own terms.

The more involved I became in my male to female femininization, the more I discovered there was no easy way out. Which frightened me more. I always equate it as me busily painting myself into new life corners as a trans woman which there was no easy escape from. Finally, I did see a brief escape from my unreasoning fear was when the transgender term was being popularized to gender conflicted people like me. There was a term which described people such as me who did not fit into the cross dresser-transvestite mold or the more extreme transsexual person. From the moment I saw the trans term, I immediately knew it described me. It certainly took long enough for a term to come along, which helped me, but it finally did.

Being able to read about other more accomplished transgender women and trans men helped me to understand my fears and why I was feeling them and the new less rigid gender spectrum terms helped me immensely. For the first time in my life, I could pinpoint why I was feeling a certain way and at the same time calm most of my anxieties. Gender diversity became my motto in life as I really began to explore the world of ciswomen for the first time. I had left the men’s club (and they knew it) and wanted to join the women’s club if they would have me. Yes, the world of ciswomen would have me which lessened my fears and anxieties immensely. Mainly because I had a better understanding of where I wanted to go.

Looking back, I do not know why I took so long to try to have a better understanding of who I really was. I could blame the usual suspects such as my old male self or my second wife who put up such a battle against me transitioning when in reality it was all on me. In the would of-should of department, I always should have faced up to the fact I was more female than male and should have not made life miserable for my wife when I did not “man-up” in her terms and become a woman. I guess I was never one to take the easy way out.

If I had taken any of the excess time I was wasting, I would have taken the time to calm my fears by understanding who I was as a person and try to build a better feminine person I learned I could be from all the male building blocks I had left behind. As I looked around at the new world of ciswomen, I was seeking admittance into, I realized they were more diverse than even I had given them credit for. And I would not be shunned for wanting to do something like wearing my favorite team’s jersey on game day in one of the sports bars I was a regular in because other women were beating me to it by wearing their jerseys It made my fears evaporate as my life became more fun again and certainly more fulfilling as I had always wondered what it would be like to cheer my favorite teams on in the venues I was used to going to as a woman and not a man.

Once I finally started to have a basic understanding of where my fears were coming from, I was able to better keep them under control. Which, in turn led me to being more relaxed with a chance to let my long hidden trans woman personality shine through.

I know it is difficult for all of you who are just getting started along your gender path to not be afraid because of what is at stake but if you are able to slow your life down to take a closer look at it…you will stand a better chance of understanding your fears and anxiety and living a better life.

Thanks for reading along and I hope my experiences can help you anyway I can!

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Stepping Out as Yourself

Image from Max Anderson
on UnSplash. 

Stepping out into the real world and leaving my closet and mirror for the first time was difficult for me. For lack of a better term, I was leaving everything I worked for in my male life behind.

As much as I hated my dark, lonely gender closet, I found it to be a safe place to be when I needed it the most. My ability to put on a dress and makeup soothed my soul, if only on a temporary basis helped until I needed to take another high heeled step into the real world where I so desperately wanted to be. To put it mildly I was scared to death when all my male privileges I had worked so hard to learn were stripped away and I was starting all over again. It was different when I could not rely on a menacing facial expression or an occasional bluster to get me by.

Stepping out into a new feminine world for me meant I needed to immediately begin to work on building a new personality which would grow with me as I worked my way towards my dream goal of living fulltime as a transgender woman. This was the same period of time that I was obsessed by my feminine appearance, so I had a lot on my mind. As I struggled day to day about what gender I was going to be. All too soon, life meant so much more to me than buying a new dress or skirt all the way to how I needed to change my old male movements when I wore them.

As I was forced by being in the public’s eye, I needed to understand exactly what I was getting myself into. So much more than the pretty clothes that I saw the girls around me wearing. If I needed to be more like them, I had miles to go on my gender path to get there. All I knew was at that time, most of the ciswomen I encountered were nice to me. Every little bit helped me learn what my future could be like if I kept stepping out and away from my old male past. Plus, problems kept occurring with my second wife and my male self who saw the changes in me as a threat to their future lives. My second wife saw her husband slipping away and my male self-saw his whole future gone if what I was doing continued.

Through it all, I was able to establish myself as some-sort of a successful cross-dresser before I transitioned into a transgender woman one fateful night when I thought enough was enough and I had to do more to continue up my gender path. Before I became lost entirely and had to reassess where I was. What I learned was that I was actually further along towards my transfeminine goal than I thought I was. I learned the hard way when I was able to be successful when I went out for the first time to enjoy a drink with a group of ciswomen from a nearby mall who just would go out and socialize after work. It was something I always had wanted to do as a transwoman, and I was amazingly accepted into their circle. I guess you could say that night I really stepped away from my old male self and loved it.

Before I knew it, my new shiny shoes (flats this time) were stuck in gender quicksand as I had stepped into a place that I never wanted to get out of. One thing was for sure, if anyone came along with a rope trying to rescue me, I would have turned them down. I was having too much fun challenging the world as my new transgender self to ever turn around and go back to a boring life as a man that I had stepped away from.

Sure, there were still many times that either I was scared to death of where I was going or was out and out rejected by the world, but those times were getting fewer and fewer apart. I was headed towards my dream goal which was slowly coming into focus as a doable project. I say project because I had never attempted such a thing as jumping the gender border to slide behind the gender curtain in my life. When I finally accomplished my goal of being allowed to exist in so-called women only spaces, I certainly was not going to give up all that I had earned.

By this time my second wife had passed away, and my old male self was seeing the writing on the wall, and his days were numbered too. Which left me all alone to make my key life choices. Still after much thought and consideration, I finally gave in totally to my feminine side, and I set out to build a different yet better life with my new ciswomen lesbian friends. All of them helped me round out and refine the woman I always wanted to be. Most of the work I had already put in, so I did not have that far to go. Mainly the only place I needed to go was with my dealings with men. Even that turned out to be relatively easy because most men left me alone because I was not attractive enough or just wanted me as some sort of a fetish object. All my problems went away when my lesbian friends taught me I did not need a man to be validated anyhow.

As stepping out as a transgender woman in the world became natural to me, a whole new universe of life came alive for me. Especially when I was approved for my long-term dream of starting HRT or gender affirming hormones. Something that my second wife always recoiled at the idea of, but on the other hand, my current wife Liz loved. The essence of being on my hormones just carried over into me stepping out into a new world with confidence I had never known before.

 

 

 

Your Lines in the Sand as Gender Markers

 

Image from Sonnie Hiles
on UnSplash. 

For the longest time, I set new lines in the sand as I progressed along my path as a novice transgender woman.

Sometimes, the lines were very faint, and I had a difficult time seeing them. All the way to deep trenches I needed to leap across. It all depended on what I was doing at the time. For example, when I was just dressing in mom’s dresses and putting on her makeup, the lines were very faint and easy to cross. In my mind, I was a boy one moment and a girl the next. A very black and white way to view myself, or so I thought until I grew older.

Instead of growing away from my cross-dressing years, I ended up growing into them by finally coming to a better mastery of the feminine clothes I wanted to wear and maybe more importantly, the artform of applying makeup which was a very deep line to cross for me. If I had worked as hard on my studies and sports than I did on my femininization projects, I would have certainly made the dean’s list every year and starred on the school’s football team. I was mentally built differently because of my gender dysphoria and could not decide for the longest time which gender path I wanted to follow because the feminine path was primarily there for an escape. When my male life became too stressful, I could shave my legs, slide carefully into my pantyhose which I had purchased myself from jobs I had worked and put on a dress and feel better instantly.

Even though I did not want it to happen, I began to build male privileges from doing a good job raising my daughter as a father and working jobs I was promoted at. When I did, I knew I would have a lesser chance of having just a small line in the sand to jump across if I ever needed to. Little did I know, how much both of my efforts would come back to help me in my later years when I encountered severe gender obstacles as I went behind the gender curtain as a transgender woman. I should say finally went behind the curtain since it took me decades to do it.

The problem arose with drawing more and more lines in the sand that my life as a transfeminine person became more complex quicker than I ever imagined. Often, I have described what I went through as sliding down a deep slope grabbing onto whatever I could to maintain the male life that I had. Just to watch it slip away. It led me to falling off the deepest cliff I could have ever imagined when I put away all my male clothes for the last time, went on HRT or gender affirming hormones and put my male life behind me for the last time.

By this time, even my stubborn old male self was admitting he had made a mistake by holding on as long as he did. All the covering lines in the sand I was about to cross with his own ideas did not work, as I was able to negotiate all the challenges thrown at me by ciswomen in the new world I was in. In many ways, I had come full circle when I learned how valuable all the building blocks, he had given me, just gave me more resolve to be a better trans woman. The daughter I mentioned earlier came around to be my earliest and strongest supporter so all the time I put into being with her when she was young came back to help me. Then there was my employment in the restaurant industry which turned out to be very lucrative for me in several ways. The first was with money and the second was with the opportunity to work closely with groups of varied ciswomen. In many ways, I learned what they faced in their lives gave me insight into what I was going to face when I joined their world.

For example, I learned what alpha females meant to the group of women as a whole, and if I could gain their support after I transitioned and joined their world, it would be very valuable to me. In many ways I found that good strong alpha ciswomen from super butch lesbians on down could do to help me erase my lines in the sand. I can’t begin to say how much they helped me. Even my second wife who was an unapproving alpha woman to me was a role model and taught me more about her life than she ever knew. Before she passed away tragically at the age of fifty from a massive heart attack. So, she never got the chance to meet the mature transgender me after I had crossed all the lines in the sand I needed to cross to just survive.

From all sorts of ciswomen, I learned that women come in all shapes and sizes with various levels of support of the transgender community. Many support us from afar and it would be different if it was their husband seeking to make his own line in the sand and become a transgender woman. On the positive side, there is now more information available to spouses of trans women to understand what seemingly a glaringly selfish path is to go down for their husbands. Especially with the husbands who have gone to great lengths to hide their gender passions from their wives for many years. When I step back and look at all the relationships which have ended over the years because of gender dysphoria, I try to wonder what would have happened if my wife was the one who wanted to draw his line in the sand and said enough is enough. I can’t take it any longer.

Of course, now I am biased and think I would have accepted my former wife bringing home another woman to get to know. How would my old male ego react? I am ashamed to say it now, but my old male self would have had to force the issue and solve it once and for all in his favor. Drawing his own line in the sand.

If you are at the point of drawing a new line in the sand for yourself, make it an achievable goal so you do not get discouraged. Finally, stay flexible with your lines as you know some will be deeper than others. If you do, you will stand a better chance of success.

 

 

Loving the Skin You are In

 

JJ Hart.

Loving the skin, you are in is often difficult for a transgender woman or transgender man. In fact, we often come to hate the skin we are in. 

We start early in our lives boxed into a gender we were born into but never felt comfortable with. Many of us go through times of discomfort as we try to sort out who we really are. We have many questions such as are we going through a phase, is it just a fetish and someday will we somehow outgrow our desire to be the gender we always wanted to be.

In my case, it took me decades to accept the skin I was in and to learn to live it in the world as a transgender woman. Recently, I was reminded of my past when I attended a virtual LGBTQ support group meeting at the Veteran’s Administration. Normally it is a very tight knit group of the same people who come every week, but this week we had a new person who joined us who was coming out of her gender shell and slowly learning to live a life as a transgender woman. During the session, she asked if anyone had any advice on dealing with public in general and the police in particular when you are out in the world.

I am not good at giving much advice in situations such as that, so I mainly kept my ideas to myself. Such as the fact that I have had few interactions with the police over the years and those have been mostly positive. Even the ciswoman who called me a pervert once in a women’s restroom, did not call the cops on me. Leaving me with the time I was in a venue I was not a regular in and two women at the bar made it a point to call the police on me after I had used the women’s room. All that happened was I was stopped on the way out by a female cop who told me not to do it again and I went a short distance up the road to one of my regular venues where I knew I would not have any troubles. To make a long story short, I was sorry, but I did not have much of any ideas on a magic cure to dealing with a potentially unaccepting public. You just must develop a thick skin and complete confidence that you are doing nothing wrong and you can make it.

Another problem I have with giving any trans person advice is that I came out seriously so long ago and times have changed. You see reports of so many toxic men harassing ciswomen these days which were barely seen in the days when I was trying my hand at being a single woman at a big sports bar. Plus, I am lucky to live now in a fairly liberal part of Cincinnati where the public at large does not notice me, or care. I am allowed to exist in the world as my true self in my own skin for the first time in my life.

I was fortunate to be one of those trans women who could get out of her gender closet and exist in a stable world where I could flourish and share my ideas about my femininity. Hopefully the new member of the support group will stick around long enough so that I will be able to share thoughts with her about appreciating her own skin. Another problem too is that the group time is at a premium, so I am reluctant to take too much up with my thoughts. Such as, if she is already out enough to wear feminine clothes and paint her nails, what is she waiting for. Maybe she is waiting for someone to come along like I was and kick me out of my closet for good. Which is what happened to me when I was miserable trying to juggle living in both genders, and my future wife Liz told me that she had not seen any male in me at all

Destiny really set in with me when my daughter came on board with knowing the true me by saying among other things that I looked so happy. I mentally added, because for the first time in my life I was having the chance to live in my own skin.

Even with all the positives I was dealing with, I still had to get out into the world and live my new reality. I always had some sort of an idea that ciswomen live more of a complex life than men do, but I had no idea of what I was walking into in my new high heeled shoes. Primarily learning to deal with curious ciswomen and their passive aggressive behavior and potentially drama-filled toxic men filled my evenings when I was going out in my new skin in the world as I knew it. Through it all, I needed to adjust my way of thinking quickly and radically away from the old male way I viewed the world.

What kept me going was the fact that I felt so good and natural in my new transfeminine skin. Deep down I felt this new life I was living was always the way things should have always been for me until the cruel joke of being born a biological male set in. It was something I would have to battle for my entire life.

As far as the physical part of having a new skin, it was way past time for HRT or gender affirming hormones to set in and help me. When I was approved for my life improving hormones, it was like my body was telling me I should have been on them all along. As my overall body skin softened dramatically, along with bigger breasts and longer hair.

The best part of adding hormones to my body was the fact that my emotions set themselves up to better appreciate the whole process. For the first time in my life, I could cry tears of joy which I did when I began to live my life in my own skin. I certainly loved it.

 

 

 

 

 

The Vampires Approved Me

 

Image from Mike Lloyd 
on Unsplash. 

Yesterday I needed to visit the Veterans Administration vampires to have my blood labs done. Fortunately, I could just go to my local branch office to get them done and not have to go to the congested mess which is the downtown Cincinnati VA Hospital.

I chose yesterday to go because it was a beautiful early August day here in Ohio with coolish temperatures and bright sunshine for the relatively short drive I needed to make to get there. For the occasion, I decided to wear my new Libra themed tank top with leggings and my new tennis shoes. After a close shave, a lite coating of makeup, and lipstick, I brushed out my long hair and was ready to go. Actually, compared to the few other ciswomen I encounter at the VA, I was nicely dressed and ready to face the world as a transgender woman.

When I arrived at the VA, it was a very uneventful visit as no one seemed to notice me for anything other than who I was, an elderly woman who did not have to wait long to be seen and have my blood drawn. Since I was emboldened by the experience, I decided to stop by my wife’s Liz and I’s favorite coffee shop to pick up some breakfast sandwiches and coffee. My morning continued to go good as their drive-through was nearly empty and I was greeted cheerfully. Before I knew it, I had my order and was headed home. It is the coffee shop we go to which has the big LGBTQ flag on the wall, so we always try to support it.

The best part was that only a couple of hours later, the doctor who wanted the bloodwork done received the results and everything came back OK. Which means I am clear with the vampires until I have my Hematologist visit downtown this fall. It is important mainly because it is when I have my Estradiol levels checked. It is certainly no fun going downtown and having to find a parking place and walking but there is nothing I can do about it.

In the meantime, I took my brief moment of gender euphoria and enjoyed it for what it was…a brief moment to be the person I always wanted to be. I was just being me basically for the first time in my life. Now all I need to do is string together more of these moments to make them my reality.

Just a short post today to let you know where I have been and I will be back with you with a longer post tomorrow.

Letting Tomorrow take care Of Itself as a Transgender Woman

 

Image from Valentina Conde
on UnSplash.

Since I was always a person who had a difficult time living in the present, tomorrow always loomed large in my mind.

I think it all started when I began to rebel against the masculine world I was being forced to live in and always thought tomorrow could be better. It turned out that all the wishing and hoping I did for a better tomorrow turned out to be wasted time and energy, I finally needed to take matters into my own hands, stay in the present and do something about me being stuck in my dark, restrictive, gender closet with only a mirror to help me.

It took a quantum shift of thinking on my part to even thinking about how I could change my life. First of all, it was nearly impossible for me to quit daydreaming about the next time I could cross-dress in my mom’s clothes and try on her makeup. Any time I was not actively being engaged in male activities, I was hoping that soon I would be glimpsing a view of me in a favorite miniskirt I had found by accident at school outside of the girl’s locker room. If the girl who left it behind did not want it, I certainly did before a janitor found it and threw it in the trash. I was overjoyed to add it to my small but growing feminine wardrobe at home. Hopefully away from any prying eyes who may find it.

Somehow, I managed to hide my “treasures” away and add to them with my own meager funds I had earned from my rural newspaper route and from chores I was doing around the house. I will never forget the excitement I felt when I found a pair of women’s shoes that fit me in the department store where I was sneaking in to buy my makeup and panty hose. The whole process made me feel good because for once I was not relying on anyone else to help my cross-dressing along. It all was just me, and I was in the present doing it.

As I moved along in years and experience, I increasingly wanted to break out of my dark closet to see if I could exist in the world, in the present for once as the person I was coming to believe could be my true self. I learned the hard way that the public would not be as forgiving as much as my mirror was as I was treated quite rudely the first several times I went out. Even in places I should have had no problems in such as the big shopping malls back when they were popular. I couldn’t seem to dodge the giggles and stares I got from the teen girls before I learned to stay in the present, be who I was and begin to blend in with the group of other ciswomen in the mall. I learned the hard way to dress for them and not rely on some sort of trashy look that appealed to men. Which was getting me clocked as a man in drag every time.

All this new reality was teaching me I could indeed enjoy the present when I was out in the world. But not enough to keep me there when I was back in my unwanted male world. I have always wished I could get back just a portion of the time I wasted daydreaming of how it would be if I was the only ciswoman in a business meeting I was in. I know I could have been more effective…if I could have been accepted. Which I would not discover how difficult that would be until I got out further in the world as a transgender woman. I will always remember how I was shunned by a small group of men I somehow became involved in a discussion with when I first came out of my shell. Quickly I discovered, as a woman among cismen, I would have to fight for my right to be heard on an equal basis.

The more I was out in the world, the more I was forced to stay in the present. If I did not, I could find myself slipping back into old male habits which would give my past away much sooner. Such as not employing my old “stay away” male scowl and replacing it with a much more pleasant feminine look which said I was happy to be here. Which got me by. Other areas of just being a woman I needed to concentrate on was how I moved around in the world when I was still trying to juggle being in both worlds of male and female. One day I needed to be feminine, and the next masculine ended up taking a real toll on my mental health as I did not know somedays what present I was supposed to be in.

Plus, the one aspect of being in the now as a transgender woman was the one I always mention, communication. As I was blissfully (sometimes) going along my gender path, suddenly more and more ciswomen wanted to know about me and were curious why I would be in their world. I was totally blindsided when I needed to start and participate in entire conversations with other women who appeared in my world. I discovered communication went way past just how my voice sounded into exactly what I was saying and how fast I could pick up two uniquely feminine communication aspects. Non-verbal communication and passive aggressive behavior. The normal ciswomen who interacted with me ended up using all their skills to size me up and often it turned into quite the contest that I needed to stay on my toes to get through.

Eventually, surviving all the gender wars I went through, made me a better, more well-rounded trans woman who could hold her own in the world. Primarily because I had built up the confidence to do it, and it became my number one accessory. So, what if my makeup or walk wasn’t exactly correct, I knew who I was and it showed. There was no blood in my water for the human sharks around me to come after.

All those years of trying to get into my present and stay there finally paid off for me, but only after I had paid all my dues.