When My Tomorrow Became my Today

JJ Hart

My desires to always look like a pretty girl early in life led me to always be a tomorrow person.

 I always thought that somehow tomorrow I could get a real wig, nicer clothes and more makeup which would help with my feminine transformation. I guess you could say that the whole process made me into quite the dreamer as I sat in school and envied the girls around me in their pretty clothes I could not have. At least today but maybe not tomorrow if any of my dreams came true.

Soon I discovered that dreams never came true on their own and would take an enormous amount of work on my part to make a dream happen. Especially once as complex as crossing the gender border to live a transfeminine life. I often wonder if I would have had an ounce of foresight into how difficult I was going to have it; would I have ever undertaken such a crazy path to begin with. One which would completely consume all the spare energy I could use.

The first problem I had to conquer in my feminine life was my often-frustrating attempts to look like a woman and not some sort of a clown in drag at the circus. I found I was setting the bar way too high in my appearance standards as there was never going to be a day when I could match the prettiest women I envied. I just needed to blend in with the rest of the ciswomen in the world just going about their everyday lives. It took me many painful attempts at presenting properly as a trans woman before I got it right and was able to move around in the world without causing any undue attention to myself. When I did, I was happy to stay in the present until my brief gender euphoria went away. As I crashed from the euphoria of living as myself, I was bitter, nasty and tried to take my frustrations out on the world of ciswomen around me. Why could not I be like them and live in their world held me back in mine, so I kept dreaming about the next time I could I could live my dream in the world fully cross-dressed as a woman.

The good part was that all along I was becoming better in my presentation as a woman and was finding it easier to cross the gender border. The bad part was once I did it, I wanted to stay and not go back to the male I was living. It was then that my todays became longer, and my tomorrows seemed further away. My new mentors became the established transgender women I had met at the socials I was going to in nearby Columbus, Ohio. They had crossed border and were living successful lives and I wanted to learn more about how they did it. What I learned was that every trans person’s journey was different and it was rarely ever easy. All I ever knew was that every time I was accepted into their circle, I felt natural and wanted to learn more about them.

As I look back on it, the one thing the mentors had on me was their natural beauty which I never had, so I had to keep putting my tomorrow off until I found out I could do a male to female transformation my own way. Or out of sheer willpower as I had a transwoman friend of, mine tell me in a straight bar we were in one night. By this time, I had given up on any natural feminine beauty I might have and made my tomorrow become my today by using other strengths ciswomen bring to the table when they don’t happen to share the extreme passing gene that some women have. They go on to lead fun and fulfilling lives by tuning out all the demands to be beautiful they hear. That is what I had to do because for sure ciswomen come on all shapes and models and I could certainly find a group I could fit in with. Which in my case, happened to be lesbians.

I was really seeking out the company of lesbians so to speak; I just happened to stumble across their culture at a small lesbian venue I started to go to as well a through a bartender at a big sports bar I used to go to who introduced me to her mom. Through it all, I knew the next step for me was to become more feminine by using HRT or gender affirming hormones. My approval to take the hormones focused my tomorrow so much I could not wait to get there. I changed during the time I was socializing with my new lesbian friends who took me to watch sports as well as big lesbian mixers. I was having the time of my life as my tomorrow was rapidly becoming my today.

Maybe most importantly, my friends helped me to validate myself as who I was really was as the subject of my past life as a man never came up. They did not want to know, and I did not want to bring it up as I was just appreciating my spot in my new present as a transfeminine person.

The final touches in my today came when my daughter accepted me totally and I met my current wife of over a decade Liz. They helped rid myself of any lingering doubts of how I should live my life. Over my gender cliff I went into their soft arms and my gender tomorrow was gone for good.

My only passing regret was that it took me so long to face up to who I was always was as a full-fledged human being. There was no way I should have let it go as long as I did, I should have let tomorrow be my today. I was all wrong as I tried to cross-dress my pain away. My excuse is I was jinxed all along into leading a backwards gender life thinking I was a man trying to be a woman rather than the other way around. That way, I would have never let my todays and tomorrows get mixed up the way they did.

 

 

Leaving the Male Noise Behind Me

 

Image from Vinicius Amano
on UnSplash. 
 

I write often of the misadventures I had growing up as a gender I never wanted to be. Often my life seemed unbearable when I made a big error on the baseball field or missed a key tackle on the football field, causing my team to lose. When I did, the only thing I knew to do was to run home to my dresses and makeup and do my best to tune out all the noise of male failure in my head. If I could not be a good athlete, maybe I could try to be a pretty girl.

To make matters worse, the older I got, the more noise kept popping up in my head. Especially from my male side, who was increasingly watching any chance o a future he had slip away. Successes such as making it through the military, and job promotions did not help either.

As the probability of a male to female gender transition increased, the noise did too. Mainly because I noticed an increase in the male world, I was never have been a part of. Perhaps, it was because I was thinking about leaving it anyhow, so I was looking for sure if I wanted to.

One of the sounds I noticed the most were coming from the alpha-males who were posturing for a better place in the world. Since in many ways, my job forced me to be successful in my competition with the alpha’s (as well as my upbringing) I could listen to the noise and tell exactly where it was coming from and how I could compete. Which ultimately led me down a path I had no desire to be on.

The further I traveled along the transgender path I was on, the more I noticed the noise from both sides of the gender border increasing as I stopped to look around at one of the many stop signs I had along the way. Sometimes the screaming from both sides reached a pitch I could barely stand as each side was yelling, they were better. To make matters worse, my male side had most all the advantages which he used to his benefit when he stated his claim on my life. Afterall, he had been there from the beginning and had taken the time and effort to learn how the male world operated and how he could fit it. All my feminine side could do then was continue to cross-dress in front of my favorite mirror and dream of an uncertain future.

The one main thing she had going for her was she had the advantage of feeling natural when she was allowed to express herself in the world. It was a powerful emotion which at least kept the male screaming down to a minimum, for a while. What always happened was, I had a several days of gender euphoria after I cross-dressed which would sadly fade when I mentally and physically had to go back to my male world. Which was far from being a mellow existence. The gender headphones I was continually trying to wear in life never seemed to work well. Even to the point of causing so much guilt, I would purge (throw away) my feminine clothes and vowed to never wear them again. You know how ell that worked as my female side screamed louder and louder to once again be a bigger part of my world and I would be forced to give in.

The sad part about all the noise I was subjected to internally and externally by my gender dysphoria was wrecking my fragile mental health. I never bargained, ever having to deal with the stress of having to bargain with two of the main binary genders ripping my life apart. I only survived by taking advantage of finally listening to good therapists who told me that my gender issues would never just go away and would always be a part of me. I guess you could say that it was therapy which helped me cut through all the noise and essentially saved my life from being extremely self-destructive.

Finally, when the noise reached a fever pitch, I needed to take drastic measures to do something about it That is when I went on an aggressive all-out push to see what a ciswoman’s world was all about and better yet, could I ever be accepted into it. My so-called discovery tour took me out of the worlds of dark gay venues into the lights of straight places such as TGIF Fridays which back in those days was becoming a safe venue for single women to go to. To do what I wanted to do, I needed to put my extreme fear of discovery behind me and see if I could survive in Fridays. When I did, a portion of my noise suddenly made sense to me, and I realized what I needed to do to tune out the rest.

I was proving to myself that there was nothing wrong in what I was doing, and I was starting to ignore all the panic warnings I was receiving from my male side about what I would lose if I left him behind to follow a feminine road. The best part was, the more I started to listen to the feminine noise, it made me feel better about where my life was heading. Even though many of the things I was trying scared me to death, as I succeeded in each step, I was building a calm confidence I would never lose.

Of course, the more my feminine noise clamed me and made me whole, my male noise started to subside to a low whimper. Gone were the days of being lonely and searching for my gender identity when I discovered ciswomen lesbian friends who gave me mine. As they taught me more about validating my own womanhood than they ever knew they did.

Very soon I even healed from my destructive days of listening to all that male noise and was able to throw those old gender headsets aside and live my dream life.

Hey you!!!! Thanks for reading along with how I escaped my male gender noise and maybe it can help you escape yours too. In any case thanks for being here!

 

 

 

If You Don't Try...You Will Never Get There

 

Image from Luis Villasmil
on UnSplash

During our lives as transgender women and transgender men, we come to many obstacles that we have no idea of how we are ever going to get around.

After many early failures in my unwanted life as a boy, it was increasingly evident to me that if I did not attempt to try harder being a girl, I would never have a chance of making it to my dream. In many ways I was stuck between a gender rock and a hard place. On one hand, I was running to hide behind any failures I might have with my dresses and makeup, and on the other, I was making myself afraid to try anything new at all.

It took me years to learn that if you don’t venture into the world outside of your little closet, nothing will be gained. I discovered after I went through male puberty, I had very little to start with as far as having any natural feminine characteristics to work with. Even still, until I got out of the mirror and into the public’s eye, I had no idea of how bumpy my gender path would be.

In the early days, my male ego took it badly and my female ego was hurt deeply when I was laughed at in public. Until I began to take matters into my own hands. In order to improve my feminine presentation, I went on a crash diet which enabled me to fit into and purchase more stylish fashion. I learned to be in the right place at the right time if I really wanted to try to blend in with the ciswomen who ran the world, I wanted to be in. It took time to try more extreme transgender bucket list items I had put together to learn how it would be to live in a woman’s world if I had to try hard enough.

It was about that time that I landed a job with a very successful casual dining restaurant chain who taught me a lot about not being a victim and if I did not try to succeed I wouldn’t. In essence the chain took what I had learned about myself in the military and improved it. Which was just what I needed to take the gender box I was stuck in and find my way out. What I discovered was that most of the world did not care anything about me once I began to learn the basics of not drawing undue attention to myself. Setting me up to try more and more gender trials on my own. Because I had no one else to help me. The mistakes I was making and learning from came from the fact that my gender workbook was blank and the women I could share my secret with left me on my own to learn my own lessons and be a better transgender woman. Once I figured out what that was and how I fit in with the terminology.

It turned out the only ciswoman with any access to me was my second wife who, for the most part, left me alone with my struggles. Only stepping in when I made mistakes causing huge fights. The problem became I had very little public output for my desire to work the world as a trans woman. I became very frustrated and depressed when I had no way to get out and live because deep down, I knew I was on the right path, and I just had to keep on trying. My only regret now is that I would have taken the steps sooner to be myself and not dragged my wife and I through all the torment I was putting us through.

It was not until she passed away, did I find my path again and began to try to actively carve out a life as a trans woman. In order to do it, I needed to have the confidence of my gender convictions that I had never had in the past. For once, I had few other distractions to slow me down and it seemed everyday I was learning and making progress towards a gender dream which had seemed so unlikely in my past. And, for once, I was not doing it on my own as I slowly build a small circle of ciswomen friends to do it. They were able to teach me more about womanhood than they ever knew as they allowed me behind the gender curtain into their world as lesbian women. Somehow, my male baggage which helped me was kept such as my basic mistrust of men since I had been forced into their circles in my life and the fact I could fit in with them image-wise because I was largely a tomboy in my tight jeans and boots.

Through it all, there were a couple of other things I needed to try to improve my world as a transfeminine person. The first was attempting to see if I was healthy enough to be approved for gender affirming hormones or HRT. I was and my life improved dramatically as I took on more and more feminine characteristics. The process was so easy, it was as if my body was saying what took me so long for such an important move. The other was the move initiated by my therapist’s permission at the Veterans Administration to have most of my legal gender markers changed. It was the best Christmas gift I ever received when I saw a judge and received my formal name change approval on Christmas Eve which got the ball rolling towards securing a new driver’s license, Social Security Card and getting my VA paperwork changed over. To the gender I always should have been.

I would never have made it through all the dark gender moments in my life. Especially with the added problems of depression and anxiety I had if I had not made it through and kept on trying to reach my dream of being allowed to live fulltime as a transgender woman. It was certainly touch and go until destiny stepped in and helped me along by pushing me back out into the world until I found other women to socialize with. I even played the online dating game and won after sorting through an enormous amount of trash, my wife Liz found me fourteen years ago and have been together ever since. If I had played my old victim cards, there would have been no way I could have ever made it out into the world.

I learned firsthand, if you never try, you will never make it to your dream.

 

 

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

 

 

 

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.

 

 

Every time I Looked Around...

Image from Mahrael Boutros 
on UnSplash

Until I began to become used to the new feminine world I was beginning to navigate as a transgender woman or cross dresser in those days, it seemed as if everyone was looking at me.

I was not used to the fact that both main binary genders look at women. Even though they do it through vastly different lenses. Men of course have the tendency to add a sexual aspect to how they view a woman and other ciswomen often compare other women to how they look and how much work did the woman put into her presentation. As any beginning cross-dresser learns early, it takes a lot of work and effort put into a quality feminine look. Especially when you are making the leap from presenting looking like a man with your testosterone poisoned body, all the way to being able to blend into the world of ciswomen effortlessly.

I know with me, before I could begin to blend in with my new world, I needed to shake all the cobwebs of male feelings I had about doing it at all. For the longest time, I listened to my male self on how he perceived women in the world as sexual objects and tried to influence the way I was presenting myself. What happened was, I was dressing too tight and too short in my clothes and attracting too much unwanted attention. Not only was everyone looking closely at me, I received negative feedback because I was doing it all wrong. I was fighting a losing battle with the age that I was and the body shape I had to stubbornly realize I could not go on that way and hope to ever try to live my dream of being a fulltime transfeminine person.

Then, I went back to my cross-dressing drawing board to set out a whole different way of trying to present myself. Out went the way too short skirts and dresses and in came more manageable denim skirts and oversized flowing tops designed to cover my broad shoulders and lack of hips. I even went to the extent of going on a crash diet so I could find clothes in the thrift stores I was haunting that fit me. Along the way too, it is worth mentioning, I started to take much better care of my skin after my daily shave which helped me to wear less makeup. If everyone was going to look at me, I needed to give them my best effort.

One thing I could not hide was I was a big woman, and I needed to not be ashamed of it but to understand there were plenty of other ciswomen in the world who were the same size as me. So, I began to look for them to see how they moved about in the world. Even though I was right around the six-foot tall mark, I could still wear my cherished high heels. Even with jeans and a tight top which accented my new properly proportioned silicone breast forms I was gifted by a cross-dressing friend who was purging all his feminine belongings at the time.

Amazingly to me, my life as a newly realized transgender woman begin to come together for me. I started to be able to move around in society without causing undo attention while at the same time completely enjoying myself. I even went to the point of buying sunglasses which hid my eyes so I could watch others to see if they were watching me. It was a great way to judge how well I was doing in my ongoing challenge of who was watching me and who was not. I learned I was not attractive enough to attract much cis male attention but attractive enough to be sized up in the public by the ciswomen I encountered. Most importantly, I was getting used to the attention I was receiving and often I wondered where it was if I did not receive it.

The way I began to see the attention I was receiving was I craved it because of all the hard work I had put in to being an attractive woman anyway I could. Positive attention was feedback that I was doing something right and the very little negative feedback I encountered could be overcome easily because of my new overall confidence. Which became my number one accessory I needed when I found myself in shark (human) infested waters with potentially dangerous people. My new training as a trans woman taught me to look ahead and do my best to not put myself in dangerous situations in the new world I was in stripped of my old male privilege of personal safety. Very quickly, I learned the problems of being a lone woman in a poorly lit deserted area.

I was able to test my passing privileges when I transitioned away from the gay venues I was going to and tried my best to become a regular patron in many of the very same big sports bars I used to go to as a man. It turned out to be easier than I thought it would be and I was not noticed much at all by cismen or ciswomen. Even though, on occasion, another woman at the bar would take the time to talk to me. I think more than anything else out of curiosity. Why would an ex-man such as me want in her world was the major point women of all sorts were trying to find out.

As I said, I began to crave and even expect the attention I was getting as the only transgender woman in the venue. Except on the nights that my trans woman friend Racquel met me there. We ended up having about five venues we went to that accepted out business with no problems. I also went to monthly lesbian social mixers with my two friends in many of the same places and I was overjoyed when another lesbian approached me. I guess you could say I was causing the right kind of attention.

Getting out and learning how to know and appreciate the right amount of attention even carried over to an on-line relationship I stumbled into with my future wife Liz who contacted me from an ad I had placed on a woman seeking woman dating site. Fourteen years later we are still together, so I guess I looked in the right place for attention.

Thanks for giving me your attention for my experiences! Any feedback or responses is always welcome.

 

 

 

 

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.