The First Time

 

Image from Jon Tyson 
on UnSplash.

Like most of you, as I look back at an increasingly long life, I tend to remember many firsts I accomplished.

Of course, my gender dealings are among the top things I remember along with the first time I had sex with a girl, all the way to the first time I drove a car. I also vividly remember the first prom date I went on and how amazed I was when on the first night of basic training in the Army how many of the men around me were crying. I may have felt like crying too because the military was taking away my makeup, dresses, and wigs but I would be damned if I would cry in public about it.

Through it all, I learned the hard way to wait out the hard times and try to look ahead and not behind me for a better future. The first time I remember it happened was when we were on a long-forced march during the wintertime at Ft. Knox, Kentucky. I was feeling sorry for myself until I looked back and looked at how far I had come. From it I learned a lifetime lesson I could fall back on when I was feeling down. Which was often when I could not have any way to express myself as a feminine person by cross-dressing.

I had no idea when I resumed my civilian life after the Army how much I would have changed when I had the freedom to explore who I was. Even to the point of trying to come out to my mom. I was naïve and thought that even though I was accepted when I came out to anyone for the first time about being a transvestite (as we were called back then) while I was still in the Army, my mom would accept me also. I was wrong and all she offered was a trip to a psychiatrist rather than any understanding. So, my first time coming out to any of my family was a complete failure and the subject was never brought up again. I went back into my gender closet and slammed the door shut again. The only redeeming value I had was my closet was big enough to have a mirror to lie to me about my cross-dressing future when I needed it.

The first time I made a major step into the world as a future transgender woman was when I started to go to Halloween parties where I could express my true self. After a rocky beginning, I settled into a professional woman’s “costume” which brought me acceptance and gave me hope that possibly I could make it to make dream of living fulltime as a transfeminine person if I looked ahead and learned from my experiences.

From those humble Halloween beginnings, I began to explore a number of other firsts on my gender path. I figured if strangers were mistaking me for a woman at the parties I was going to, I would not have to wait another year to do it again and started to visit venues such as clothing stores in big malls as well as safe places such as coffee shops and bookstores. When that worked for me, I expanded my gender outreach into more challenging venues such as restaurants where I needed to interact with more people.

As I began to enjoy my time as a novice trans woman more and more, the problems of how much male baggage I still had began to cause a strain with my mental health which was already fragile. All my male life, I had tried to fight a losing battle to get rid of any possible positive male belongings that I had by moving all around to different jobs and being very self-destructive. Like runaway trains on the same track, the successes I could not wish away were coming at me from the male and female side. I could not shake the fact I had a very successful marriage, a good daughter and great job I had worked hard for so easily as I had imagined. It was the first time in my life I felt bad about being successful.

At the same time all of this was happening, I realized I was transitioning again as my transwoman self. It happened when I grew tired (again) of thinking of myself as a man who was just cross-dressing as a woman into more of a woman myself. It seemed I was facing firsts every week when I snuck out of the house to be myself. I was terrified and excited at the same time with the way my life was unfolding. I had never planned on how my life was turning out, even though I hoped that it would. I never dreamed I could carve out a new life as a transgender woman as quickly as I did.

Now I could look back on all the other first times I could remember as being important and add my series of transitions as a male to female feminized person with them. My first stable communications with other women one on one immediately come to mind as firsts. It was because I was allowed behind the gender curtain in a way I never was when I was acting to be a man. Plus, I can never leave out the impact HRT or gender affirming hormones had on my life. All of a sudden, my inside feelings and external images began to sync up, and my world softened on the hormones. Making many of my previous firsts in life seem minor in comparison. Who cares about marching at Ft. Knox when I could feel so good about myself. Truthfully though, one first led to another and made my life much fuller as I look back on it.

I never realized all the firsts were just a sign of where destiny was leading me in my life and I should have paid more attention when all I wanted to do as a kid was to be a woman when I grew up. I was always a go with the flow as a person, and the flow took me eventually exactly where I wanted to go as a transgender woman…with a lot of help from my friends.

 

 

 

We Must Be Better

 

Image from Ecaterina 
on UnSplash

Yesterday I wrote a very short post about going to the doctor with my wife Liz. During the post, I put quite a bit of emphasis on what I was wearing, just to look casual. Following the post, I received a comment from “Dana” exploring her own feelings about presenting in the world convincingly as an older transgender woman. She said (and I paraphrase) we older trans women must be better than the average ciswoman to survive in the world.

Of course, I agreed and took it a step further. Young and old, in no matter what we do, transgender women and transgender men must be better than their cis counterparts in everything they do.

It all started with me when I began to seriously get out of the mirror as a novice crossdresser and into the world. One of the first things I needed to do was upgrade my very limited fashion wardrobe. I found out the hard way; I was too heavy to attempt to find fashionable clothes for larger women like me. Immediately, I went on a diet which melted off nearly fifty pounds of weight. Which made all the difference in the world for my shopping confidence when I haunted the thrift stores for the best clothing bargains I could afford on my still limited budget.

At the same time, I concentrated on taking care of my skin by using cleansers and moisturizers every morning after I shaved. My skin did improve and I could use less makeup for a better overall effect. Through it all, I considered it a labor of love if I was ever going to present better in the world as a trans woman and not be mocked.

Finally, I did make it to a point where I could blend in with the ciswomen around me after learning many brutal lessons which sent me quickly home in tears. I found out the hard way I had to be better, just to be average and blend in with the world which was seemingly out to get me. Probably the main thing I had going for me was how dedicated I was to be staying on the gender path I was following. I always knew it was going to be rough but not as tough as it was turning out. I had a lot of dues yet to pay if I was ever going to make it to my dream of living as a transfeminine person. I thought I knew a significant amount of how women live but I had no idea of the complexity of life I was facing. Which was exactly what my second wife was trying to tell me every time she sensed me drifting away from being a cross-dresser towards starting HRT and living as a transgender woman.

What she did not tell me was, in order for me to make it, not only would I have to be average as the new person I was exploring being, I needed to be better. I was fortunate and stuck to my ideas of exploring the world around me as a trans woman mainly because I little voice in my head kept telling me I was doing the right thing because I felt so natural when I was living it. I emerged from this time in my life with a few scars from the experiences I was going through which healed quickly as I moved on to better things.

In essence, I found I could be better and carve out a new feminine life from scratch. A place where no one knew anything about my old male life and my present seemed to be more positive than my past ever was. In my way though I still had the usual male baggage problems such as an unapproving spouse (whom I did not blame), a family, and a very good job I knew I was going to lose if I did what I knew deep down I would have to do. Jump the male to female gender borders and finally live where I wanted to live from the beginning.

At the same time, I found the more complex my life became as a trans woman, the better I needed to become to protect it. On the girl’s nights out, I was invited to for example, it was key that I never went into my past very far and outed my deeply rooted male past. The example included the time I spent with my lesbian friends who would have not enjoyed any stories I had of my male past if I ever let my guard down and just blurred relevant details of my past. My willpower kept me going until I never thought about my past at all, except that it was a bad dream.

If you are on the fence considering coming out into the world as yourself, just remember to build yourself up to the point where you are the better person as a transgender woman. Perhaps then, you will have reached a place you were never able to find in your old unwanted male life. And key to the whole process is when you are feeling natural as your feminine self. By then, you will know that you have made it to a good place on your gender path. But if you decide not to go any farther, that is OK too. It is your life to live to its fullest, and your journeys into the feminine gender will have taught you so much about the need to be better.

I get asked all the time how I knew about my gender issues, and the simple answer is I always knew and refused to do anything significant about it. I was stuck in my male box from birth, and he was a powerful influence on me until I knew once and for all the only future for me was as a trans woman. Somehow, I just knew the truth about myself and quit fighting it. It was all for the better.

 

 

Your Gender Path maybe Different Than Mine

Image from Erik Mclean
on UnSplash. 

 

Even though many of us share similar paths to our dreams of becoming successful transgender women or transgender men, often our paths diverge and we end up going different directions.

Most of us start out on our own without the help
of an understanding sister or mother and must fill out our gender workbooks as we go along. There is no one to tell us what to wear or how to act in our younger years as a cross-dresser. We just know we have conflicting ideas on what we are doing. On one hand, we cannot wait to put on the pretty dresses we found that still fit us, but on the other hand, we felt guilty doing it. It was somehow taking away what was left of our fragile masculinity.

At that point, most of us were willing to sacrifice that masculinity for the intensely intoxicating appeal of looking at ourselves as pretty girls, especially before puberty got ahold of us and testosterone poisoning set in. We all know what happened then, our bodies grew angles instead of the curves we admired on the girls around us and life would never be the same again. From that point forward, many of our paths seem to diverge. Over the years, I have heard from several readers who put down their urges to be feminine with no problems until much later in life. While others followed a more focused stairstep path which meant meeting and learning from other cross-dressers or transgender women searching for their true meaning to life. I know when I first discovered there were others like me who shared gender issues and I could go meet them; there were many layers of people who attended the socials. Anyone from cigar smoking men in dresses still going overboard to preserve their masculinity to completely femininized transsexual women whose next stop was gender surgeries.

It was then that I began to see and appreciate the different layers of the gender community I was seeing in person for the first time. I could almost compare it to the amazing number of cosmetics I saw the first time I went shopping with my own money to buy my own. The entire idea of going to a mixer of my peers did not work for me at all. I became more confused about where I fit in on the gender spectrum than when I started. I knew I was much more than a part-time cross-dresser but was not committed enough to consider complicated and expensive gender realignment surgeries which were still fairly rare back in those days. The direction I decided to take was one of experimentation which I found set me apart from many of the other gender conflicted individuals I had met.

I certainly would not recommend the direction I took because it involved a certain amount of risk and way too much alcohol in the mostly gay venues I initially was going to. What happened was, I used the fake courage of the alcohol to allow me to take ill advised chances in places I should not have been as a single woman. Especially a transgender one. I was fortunate when I escaped unharmed in a couple of situations I should have never found myself in as I was dressed way to provocatively for where I was going and one time in particular found myself having to be bailed out by my second wife who had warned me ahead of time about my mini-dress being way to short. I attracted the unwanted attention of a cross-dresser admirer who was huge and had me trapped in a small hallway with nowhere to go when my wife grew curious and came in time to rescue me. Believe me, it took me a long time to live that incident down with her.

Even when I became a regular in the big public straight sports bars I was going to, I would not recommend my methods of establishing a path to gender freedom as a trans woman. Being a single woman in a public place can sometimes be dangerous to the point where you don’t see many ciswomen do it. They always bring a friend or two for safety which it took me awhile to finally come to the point where I could do it too. My only recommendation is to act like you have a friend coming to join you by acting as if you are talking to them on a cell phone, or “save” a seat next to you with your coat if it is wintertime. Better yet, you can solve the problem completely by sitting at a dining room table, but what fun is that?

Another way to attempt to find companionship is through the use of social media. I tried that too and had to sort through a tremendous amount of trash before I hit the jackpot with the person who turned out to be my third wife Liz. Unbelievably, she contacted me on a social media site which I was listing under woman seeking woman. Better yet, it turned out we were within driving distance of each other and began to correspond until I became brave enough to talk to her on the phone. I was so ashamed of my voice to do it. I finally jumped off the deep end and had success as we started to date. That was over twelve years ago and we married and are going strong I am happy to say.

I see and hear from so many transgender curious people who are on the gender edge in their life with no evident way out. My only recommendation is that at some point you need to take chances if you ever want answers in your life. The only certainty is if you do nothing, nothing will happen. I’m sure I don’t have to tell you that you do have to be careful though with all the scammers out there these days and all the negative people you may encounter if you decide to go public. With the political arena and anti-transgender laws which are being passed in many states such as my native Ohio.

No path is right and who is to say, your path is not right for you even if you decide to stay in your closet which is safe and not risk giving up things such as spouse, family, friends and employment. Maybe you can experiment too as you discover which path is right for you. As I said, be careful of the stop signs and bumps ahead.

 

 

What is THAT Sound?

 

Image from Jason Rosewell
on UnSplash. 

What’s that faint noise I hear far in the distance? It took me awhile to figure it out, but it was the sound of my feminine self-yearning to be set free to live. Very early on, I thought she would go away as I aged but the opposite turned out to be true. She grew stronger as the years of my life progressed.

That is when I started to realize just looking at my cross-dressed self in the mirror was just not going to be enough. I wanted more of the feminine life I had experienced. What I was experiencing was the idea of I had much more than a casual interest in women’s clothes and makeup. I was more into how they lived. The term transgender had not even been invented yet, so I had nothing to compare my feelings with. I did not think I was transsexual like Christine Jorgensen, but I was certainly different from other cross dressers I was seeing in my well-worn copies of “Tapestry” and “Transvestia” magazines. When all of that happened, the sound kept getting louder and something larger was wrong with me and it took me years to realize what was wrong with me was not what the sound was telling me.

I went on fighting myself searching for the truth I was looking for when it was right in front of me if I chose to see it. I ignored the advice of my handpicked gender therapist (one of the few I could find back in those days) who told me she could do nothing about me wanting to be a woman but could do something about my manic depression. Which I always had thought was something to do with my gender dysphoria. She told me it wasn’t and helped me by prescribing medications to help me in everyday life. At the time, it turned out, I was ready for help with my depression but not ready to face the facts about my gender future. I was used to loud sound from my days as a radio DJ and I was stubborn enough to want to hang on to a dual gendered life.

At the same time all of this was happening, I was beginning to explore the world as a novice transgender woman and learning every time I went out what the sound I was hearing really meant. I had life all backwards with my struggles to live a male life and the sound was telling me increasingly I was destined to be a woman all along. Not in the mold of having extensive major gender operations but doing it on my own schedule as I marched to my own drummer. Yet another sound which was growing in volume. Before I did though, I needed to undertake an extensive program of more exploration. I desperately did not want to make the move across the gender border at some point and find out I had made the biggest mistake of my life. My spouse, family and job meant so much to me, giving them up for no real reason scared me beyond belief.

Every time I began to have doubts about my upcoming gender decisions, my drumming sound grew louder as I felt more alive and natural when I was allowed behind the gender curtain with cisgender women. The work I was doing to prove myself to the world finally was paying off, for the most part. When I suffered a setback, I had the confidence and experience as a trans woman to do the right thing and move forward in my new life as I followed the sound of gender success. During this time, even though it is a blur to me now, I still remember that it all was not pleasant as I went through the turmoil of deciding which way I was going to turn next.

I know what you are thinking, what was she doing even thinking about turning her back on the gender future she had worked so hard to build. But I did as my male self stubbornly tried to drown out the sound my feminine life was making. Perhaps desperately would be a better term because of all the male privilege he had built up. He was desperate to hold off any more change.

Finally, the sound of change became deafening to the point where it could not be ignored anymore. I was not getting any younger and my transgender transition clock was ticking, loudly. As I had a huge heart to heart talk to myself, I came up with the decision to seek a doctor’s approval for HRT or gender affirming hormones as a natural progression of my feminine progress. In addition, I decided the hormones (if my body responded positively to them) would be the point of no return. I would have to come up with a different way to support myself financially, plus gather the courage to tell what was left of my family the truth about myself. As it turned out, the hormones began to feminize me faster than I ever thought possible and soon it became increasingly difficult to hide my protruding breasts, longer hair and softer skin than ever before. Long story short, my daughter accepted me and my brother rejected me as I revealed my life to them so I had the best of all worlds with the support of my daughter.

Ironically, one of the changes I went through was I had a greater, deeper appreciation of sound and music as a transfeminine person. I had gone full circle in my life understanding what that sound was and better, yet what it meant to me.

I always loved being right when it mattered most, and it did when I relaxed and listened to the sound of my gender spirit. I should give all the credit where credit is due…to the little sound inside of me who said keep trying when the going gets rough. Through the good times and the bad times, she was always there to help me survive.

 

Easter Envy

 

Image from Annie Spratt
on UnSplash. 

Once again, it is Easter and time for some ciswomen to model their new colorful, feminine dresses and accessories to the world.

Like most of you, I remember the envy I felt when once again I needed to be forced into a restrictive suit and tie for one of the rare occasions we went to church. Why couldn’t I be one of the girls in their Easter finery. All the envy in the world I felt did me no good as off to church we went. My parents thought I just did not want to go to church (which I didn’t) but did not realize the real reason. I was just jealous of the girls.

Back in those days, I had very little inkling of how my desire to look like the other girls ran much deeper than I ever thought it would. I was scratching the surface of where I would end up in life as a fulltime transgender woman. I thought it was an innocent hobby that perhaps some day I would grow out of when the opposite happened. I grew into it. If I had any idea of all the growing pains I would feel over the years as I grew into my true self, I don’t know if I would ever undertake the gender path I did.

The truth of the matter is that I did not think I had any choice. I was born into an unforgiving male world that I was expected to excel at. I knew too that if my cross-dressing or gender secret was uncovered, I would be sent to a psychiatrist and told I was mentally ill. I did not know exactly what was going on with me, but I knew I was not mentally ill for just wanting to be feminine. On the other hand, I knew my WWII/Depression era parents would have any idea of what was going on with their eldest son to take any creative measures to help. The first measure would be acceptance. In my wildest dreams, did I ever think they would buy me a pretty new dress for Easter and do away with my suit and tie forever. My parents were simply not built that way so that they could step out of their rigid parenting box to help me. I was stuck in a male world until I could figure a way out on my own.

Over the years, regardless of setbacks such as military service, I was fairly successful in my male life. Which ironically made it harder for me to give it all up and cross the gender border when the time came. One thing I never lost was the envy I felt for all ciswomen who inherited from birth what I wanted so bad. I kept remembering the girls and women in their Easter dresses, even though I rarely wore a dress as I attempted to blend into the world as a woman. It seemed fashion had gone away from the frilly feminine basics once I arrived at the point where I could take advantage of the new world I was in. For years what I did take advantage of was the fashion trend where I could wear oversized sweaters with miniskirts, flats and opaque tights. Sadly, fashion moved on, and I needed to also if I was still going to blend in with the world as a transgender woman. Not only did I have to try to equal the cis women I was around, I needed to be better. So, I went with denim mini’s with long flowing tops to attempt to hide my oversized male torso.

Even with all the effort I was putting in, it never seemed to be enough to compensate myself for not being the pretty girl in her new dress at Easter. Ironically, then I found out from my wife Liz how she was a tomboy and did not like all the frilly Easter fashion she had to wear and was always under inspection from her mom on getting her new white tights dirty. I learned the view of the other gender side was not always the better one. It left the door open for a greater understanding of what females go through to be socialized into women and why some never make it.

This Easter, if you are religious, I hope you have the opportunity to celebrate the true message of the day and you don’t get hung up on what the ciswomen and girls around you are wearing. Although, I don’t see many women getting all dressed up for any reason anymore. Maybe if I attended any sort of church services at all, I would.

At any rate, celebrate Easter in your world the best you can!

 

 

 

 

 

Gender Lost and Found

 

Image from Ewoud Van Der
Brandon on UnSplash. 

On occasion, I think you must hit rock bottom in your male life before you can begin to build a new feminine one. I equate it to my own transgender lost and found in my life. Before I get into what I found when I started my path to my dreams, I decided I had to have a basic knowledge of where I wanted to go.

Seeing as how I was born into the pre-internet times when information came in magazines arriving in the mail, I was stuck in the “Transvestia” world of Virginia Prince if I wanted any information at all about transvestites or cross dressers, as Virginia called us and oh yes, we had to be heterosexual to join. Through it all, I was intrigued by the pictures of attractive men dressed as women, as well as the entire world of mixers you could go to. If you happened to live close enough to one to go which I did. Ironically, the mixers I attended did not do me much good because the only mixing which happened involved my brain when it was all over. Often, I left more confused about where I wanted to be with my gender struggles than when I started.

None of my searching was helping much and my attitude about myself was sinking to an all-time low. I felt lost and forsaken in my life and felt sorry for myself because I was the one who wanted to do away with being male and assume a feminine existence. It took me a while, but I finally backed off from being a victim and my ideas of whom I really was started to improve. I had hit rock bottom and was beginning to improve, which helped primarily my fragile mental health. My goal was to close my transgender lost and found department for good.

Sadly, I was a little ahead of my time to closing my department because I still had so much more to learn about existing and competing in a world run by ciswomen. With or without men. I labored under the impression if I could present well enough as a woman with my makeup and fashion, that would be all I needed to do to enter the world as a trans woman. I totally ignored all the layers of life a female needs to go through to be socialized into a full-fledged woman and I was painfully aware not all females make the transition. And even more aware of the path I would have to take to make my own transition because I had even farther to go to make it to my goal. I needed to be even better than the average ciswoman to be able to be accepted in the world and be allowed behind the “sacred” gender curtain which women used to provide a layer of protection from men.

On my path to going behind the gender curtain, I had at least one big stop sign I needed to work my way around. It was proving how badly I wanted to give up all my male privileges and start all over again. I just did not magically appear in the ciswoman’s world asking for admittance without paying my dues. My transgender lost department was closed as a man, and I found I had done the right thing by pursuing a feminine life. My only problem was that I was impatient about the road I was going down and constantly I wanted more. Before I knew it, I was even getting ahead of myself in the plan I had set up for my grand gender transition. Here I was busily carving out a new feminine life where no one knew me as a man while at the same time I still had a loving wife, family and good job to deal with because I knew I could lose them all when I found my transgender self completely.

My problem also was, I was filling out my gender workbook faster than I ever imagined I could and my plans were coming into focus. No longer did I have just dreams of the possibility of transition into a feminine world, I had the reality of doing it. My lost and found was gone from my male side and he had finally begun to see the reality of his situation and gave in to the feminine side of life which was taking over for better or for worse.

It was at that point in my life when I pursued my ultimate dream of pursuing HRT or gender affirming hormones as the next step in my transition to being a transfeminine person. I went to a doctor for a physical and was approved to start a minimum dosage of the precious new hormones I was taking. Almost immediately, my body began to feel the changes as if it had always been meant for them to happen. The changes always take a whole blog post to describe, but to put it simply, my internal changes such as my new emotions would fill a book. The external changes became quickly obvious too, as my hair grew along with my breasts and my skin began to soften along with the angles of my face. I can only describe the changes as amazing and magical as they made living as a man impossible to me anymore. I had to close my male life and never look back.

I can not oversimplify it enough about all the stress and work I put into to close my transgender lost and found for good. To be sure, it was a labor of love to do it, and I would have never had it any other way. If Indeed I had another choice anyhow. Once I determined I never really did, I could relax and get rid of my guilt about doing away with all the male privilege I had worked so hard to earn. In the end though, it was worth the struggle.

 

 

Living in the Real World

 

Image from Jacqueline Mungala
on UnSplash.

Living in the real world became a challenge to me as I transitioned from a male existence to a feminine world. The main problem I had was figuring out what was right and what was wrong as I followed my path through many blind curves and stop signs.

One thing I never thought of completely was how different my life would be if I had ever had the chance to live as a fulltime transgender woman. Sure, I was not totally naïve and thought my world would basically involve pretty clothes and being chased by boys. When I finally was allowed behind the gender curtain, I discovered how complex and layered lives ciswomen really live. Very quickly, trying to live in the real world as a novice struggling trans woman got me in over my head. I would be remiss if I did not bring up how I tried to present myself. I thought trying to look like a sexy teen girl was the way to go, and fortunately my time in that cross-dressing phase of my life went away quickly. Often with brutal consequences of being laughed out of any venue I was trying to visit.

In other words, I put what my male self was telling me about presenting as a woman in the real world behind me and started to look around to what I needed to do to blend in with the other ciswomen around me. The challenge was not only did I have to be as good as the next woman, I needed to be better to survive in the real world I found myself in. With success, I brought confidence I could do more.

The next problem I faced was what was I going to do about my deteriorating (already fragile) mental health. As luck would have it, I was assigned a qualified therapist within the Veterans Administration who knew what she was doing and was able to separate my Bi-polar disorder from my gender dysphoria issues. She provided me with permission to begin HRT which is something I had always wanted and made the real world more livable for a transfeminine person like me.

At the same time, I was trying to take every spare moment away from work to explore different venues as a trans woman. I was attempting to accomplish trying out (as much as possible) everything I would have to go through if I ever followed my dream into womanhood. What was a ciswoman’s life really like and how was it different than what I had already lived as a man. I was entering the scariest yet most exciting time of my life as for the most part I was successful when I went out. The biggest issue which eluded me, was being able to communicate effectively with the world of women I encountered. Learning all the nuances of non-verbal communication women use was the biggest challenge for me. For the first time in my life, I needed to really listen to what was being said to me and watch the other woman’s eyes at the same time to see if I could catch a clue of what she really meant.

Through this portion of my life, I had a powerful motivation to succeed as a woman in the real world. My second wife of twenty-five years had unexpectedly passed away to leave me completely alone with my gender issues. I had no spouse to worry about how to tell my truth about wanting to be a woman. Yet another terrifying yet exciting time of my life. What was I going to do about my newfound freedom. Since you are reading this post, you know what I decided to do. I started making plans to finally make the leap off the gender cliff I had thought of for some time and throw caution to the wind for the remainder of my life. I figured why not because my confidence was at an all-time high with my small circle of friends I had built up. Along with factoring in all the time and effort I put in exploring the real-world ciswomen live in because for once, I had earned my way (or forced my way) behind the so called “sacred” gender curtain.

Once I had made it to this point, after another stop sign on my transgender path, I found I still had more learning to do to really be ready to live in the real world. That is where my ciswomen (lesbian) friends came in which is a subject of another blog post. I will say, they taught me how to be validated as myself in the real world. It was another main transition to go from thinking I was a transgender woman to knowing I was just me. Which took me from cross-dresser to trans woman, back to a secure me during my lifetime. A long, often brutal journey which had a happy ending. I learned the person I had been running from much of my life was not such a bad person after all.

Maybe, most importantly, I discovered the one aspect of my life I never thought I could experience and that was having the ability to be happy. I never had a chance to learn it from my family, and I spent so much time trying to deny myself any satisfaction I could have had from a successful career as a man, there was no time to ever be happy. It turned out that when I turned the corner back to just being the true me, I allowed happiness to be part of my existence.

I had survived all the lessons I had learned as I followed my path to a brighter, more authentic gender future. Living in the real world was not such a bad thing after all. My only regret is that it took me so long (all the way till sixty) to have the courage to face my truth so I could live as I truly was.

 

 

 

In the Snake Pit

 

Image from Jeff Turnale
on UnSplash.

Before I made my male to female transition, I always assumed men were the fiercer competitors, mainly because of work and sports.

Once I made it behind the gender curtain to play fulltime in the girl’s sandbox, I found that my idea of gender competition was not true at all Ciswomen compete every bit as hard as men just in different ways and about different things. A well-worn example could be that women compete in the visibility arena all the time, and that may be true to an extent as ciswomen lay down certain fashion perimeters women have to live by to not cause undue attention. Such as wearing skirts and dresses too short or having non-age-appropriate hair (which I have) for my advanced age. At my age, I have decided to keep my hair the way it is because number one, I like it, and number two, I don’t really care what other ciswomen think of me.

Over the years, I have discovered that ciswomen compete as much as men for the chance to be attractive and attract male attention. In fact, I have a couple of examples where I was caught on the wrong side of female wrath. One of which occurred one night when my wife Liz and I were out in a LGBTQ friendly venue in downtown Cincinnati. During our visit, I needed to use the women’s room which happened to be downstairs in the ancient building the venue was located in. When I made it to the room, I found it to be a crowded two stall affair with several other women already there. As I went in one woman in particular glared at me as I made my way to the only open stall which was left. I excused myself as I went around her and took care of business, feeling better about myself.

As I came out of the stall and headed for the sink to wash up, I needed to almost move the woman who glared at me. She took her time moving and I noticed she ended up slouching below the electric hand blower/dryer on the wall, and I saw my chance for revenge. After washing up and checking my makeup and hair, I took my time moving to the hand dryer and casually turned it on which ruined the woman’s hair completely. After my payback, I gave her a little smile and left to tell Liz what had happened.

The next example I have of an irate ciswoman, took me totally by surprise in a venue in Dayton, Ohio where I was a regular. That night, my friends were not with me, so I was by myself when a couple sat down beside me. Before long, the woman started up a conversation the usual way, complementing me on something I was wearing. We struck up a little conversation about life without much input from the man she was with. I could not tell if they were married or not. Anyway, before long she excused herself to go to the woman’s room leaving just the man and I together and he started a conversation with me by the time she returned. For some reason, she must have been extremely jealous and thought I was competing for her man because the smile went away and the claws came out. To make a long story short both the man and I had claw marks up and down our backs before they quickly finished their drinks and left. I learned the hard way to make sure I never got between a ciswoman and her man.

The most profound level women compete on is with their passive aggressive behavior. They can be competing just as hard as men, just with a smile on their face. It is a learned attitude most ciswomen learn from their youth because of not being able to physically compete with men. Although I think some of that attitude is changing in some cultures where I see many girls fighting among themselves these days. But for the purpose of most all transgender women, our view of the feminine world does not change as we do when we go from aggressive male worlds to passive aggressive female worlds.

Outside of confronting two women in a rest stop woman’s room a couple years ago in Alabama, I don’t think I have ever found myself in a feminine snake pit ever. The two women I encountered were studying me way too closely and talking aggressively between themselves after they saw me, so I washed up and quickly headed for the exit before I had any other problems.

My best advice is to look ahead at your surroundings to not get caught in a feminine snake pit. My worst-case scenario happened when I had to go one on one with a woman in a bathroom in a venue where I had never been questioned before. She was screaming at me that I was a pervert. When I finally could get a word in, I asked her by chance what she did for a living and I saw my chance for revenge creep in. She said she was a hairdresser, so I asked her for a card so I could report her to the very powerful local LGBTQ establishment in Dayton. With that she stormed out and left me alone.

Even though being in the snake pit with other women was no fun, I looked at the entire experience as a rite of passage into the girl’s sandbox. If I could not survive the pit, how could I ever survive my chance to play behind the gender curtain. All my years as a man had taught me to beware of where the frontal attacks were coming from, and if I was ever going to make it as a transgender woman, I had to expect not everyone would accept me and be ready for it. I just never realized how close together the snake pit and the sandbox were going to be.

 

 

 

Set in Stone?

 

JJ Hart

When we are born, we are assigned a gender which is arbitrarily based on our genitals the doctor sees. Often, at that point, gender reveal parties are set up by new proud parents. Of course, the problem is what if the child does not agree with how the reveal was going but had no say in the process. That was exactly where I found myself.

I was born as a first son into a male dominated family, so as I grew, I learned what was expected of me. Be a success, compete for it and earn my male privilege was my only path. I was caught with no way out, seemingly, I was stuck in stone. My only path to sanity was the very limited time I had to cross-dress in front of the mirror and try to transform myself into the pretty girl I always wanted to be.

The first time I saw a glimmer of hope in my future as a transgender woman was when I started to go to Halloween parties dressed as a woman, just to see how I was perceived. Overall, I felt as if I got a fair reception and could not wait for Halloween to roll around again. I found I could not wait and began to come up with other ways to test my feminine presentation in the public’s eye by simply going out to malls and women’s clothing stores. Looking back, some of my adventures were just OK and others were brutally bad as I learned what I was doing. One of the main things I learned was presenting as a woman was not set in stone. Often, I could take advantage of the seasonal variations in women’s fashion to change up my own look, which made the fashion process so much more challenging and fun. I needed to up my diet game to fit into more stylish clothes I hunted down at the thrift stores I shopped at. I liked many of them because I could try on my potential treasures in the women’s dressing rooms with no problems.

All of this led me to believe that maybe my gender situation was not set in stone, perhaps I could find my way out of the life I was given. I just needed to be sure that escaping the stone I was in did not put me in quicksand. Or was the transgender frying pan worse than the fire. With my newfound confidence, I set out to discover the answer to as many of my gender questions as I could. I knew I felt an energy in life I had never felt before and it felt so natural that I wanted to experience more. But even with all of that, it wasn’t enough to keep me satisfied with my slow transition. The basic question remained that could I ever gain the courage and where with all to live my dream of existing as a full-time transgender woman on my own terms. Sadly. I was not going to learn that answer for years because my male life kept getting in the way.

By in the way, I mean he kept setting up major roadblocks of my proposed path such as what to do about my wife of twenty-five years and the very successful job I had worked so hard to get. I cherished both of them and did not want to let them go. I am sure, this sounds familiar to many of you in the same situation. Especially when you think your male situation is set in stone and you can’t get out.

I thought the same thing for years as my mental health deteriorated as I drank way to much trying to self-medicate my problems. The part I never understood was how I could think what was true today would be true tomorrow. Destiny for me completely turned me around during the dark days when my wife and almost all of my close friends passed away, leaving me almost completely by myself. Except for my daughter and my brother. On top of all of that, the Veterans’ Administration healthcare system, which I was a part of suddenly approved the use of HRT or gender affirming hormones for qualified veterans who were approved through a therapist to receive them. I was approved and prepared myself for my second puberty and the greatest most profound changes of my life.

Suddenly, everything I thought was set in stone, was not. I was free to live the way I had prepared for all my life had come true. I could even dare to be happy for the first time in my life. It was always set in stone that happiness could not be part of my life. Thankfully I was wrong about that. It was just a matter of learning where I truly belonged and then getting rid of that giant roadblock I was born with. My so-called gender because it turned out to be true, I was never supposed to live a male life after all. All the years of struggle and emotional pain were wasted on a fight that I was never destined to win.

As I always say, I was not a man cross dressing as a woman, I was a woman cross dressing as a man to just get by in life. I was fortunate in that my gender destiny was not set in stone no matter how determined my family around me was to keep me male, I always found a way to sneak around their backs and keep that feminine flicker of hope alive. Now it is able to burn brightly due to no small help from mainly new friends and family. Roadblocks were moved and now the path is straight and smooth as I am able to live the dream I always wanted.

As I said, remember that today does not dictate what tomorrow may bring. I always say, life can change on a dime. If you can find the dime.

 

 

 

Honesty was Always the Best Policy

 

Image from Jon Tyson on 
UnSplash. 

Very early on in my life, I thought my default mechanism to anyone challenging my masculinity would be to lie about it. Fortunately, I did not have to take that route often because of all the elaborate ways I utilized to hide my feminine desires. Examples were the times I was competing in sports or working on cars. People close to me just assumed I was a “normal” male.

It wasn’t until much later in life when I began to get serious about dating women, did honesty become a real priority when it came to explaining my life. My first experience with telling a woman I was serious about, has been relayed several times here as recently as in the last several days. She is the one I coerced into dressing me head to toe as a woman which was the first time a ciswoman had attempted to do it for me. The whole plan turned out to be a disaster because of so many things. As I have mentioned before, I just wasn’t that impressed with the outcome she presented to me as she applied my makeup and the long blond wig I so desperately wanted. By then, I had spent years doing my own makeup and I thought I did a better job.

Little did I know that disappointment would only be the beginning of many with her. Being honest in our relationship early on led to an engagement but then a total break up because of a date I had with Uncle Sam and the Vietnam War. Rather than support me as I served, my then fiancé insisted I tell the draft board and the world I was gay to try to not get drafted which would have been a total lie. I knew I was a cross dresser but also had a pretty good idea I was not gay. Instead of wrecking my personal life as I knew it, we broke the engagement and went on our not so merry ways. I knew where I was headed, the US Army for three years. It was not the most pleasant time I ever spent in my life, but at least I was honest with myself.

Time went by in the Army until I found myself in a place to exercise some of my cross-dressing desires by going to a hospital Halloween party I was invited to by friends. By doing so, I through caution to the wind and decided to go all out dressed as a woman. I only had about eight months or so to go in the Army, so I was willing to risk getting in trouble to satisfy my need to cross-dress after such a long time of being denied.

All three of my closest friends that I socialized with all the time were at the party too, and as luck would have it, several weeks later, the subject of our “costumes” came up after a long night of enjoying very good German beer. When my turn came to talk about how I had went to all the effort to femininize myself for one night (including shaving my legs), I finally just was honest with my friends and told them I was a transvestite and the Halloween party was far from being just a one night deal of seeing what it would be like to dress as a woman. It was the first time I had ever admitted to anyone that I had a fondness for being a woman, so it was quite the liberating experience.

It was also a far-reaching experience because included in my group of friends was a woman who I got to know quite well. So, well in fact that later on we went on to be married and she became the mother of my only daughter who I cherish to this day and is one of my biggest supporters. Obviously, from day one in our relationship, she was aware of my feminine desires and accepted them.

Much of the same happened with my second wife, who was much more strong willed than wife number one. Even so, I felt honesty was the best policy and I nervously told her again I was a transvestite or cross-dresser before we were married. Ironically, the problem came with me not cheating on her with myself. What I was increasingly doing was doing exactly what I had sworn not to do. Leave the house dressed as a woman. By doing so, I broke one of the main bonds of our marriage which was not lying to her about what I was doing all the time.

Needless to say, like any other ciswoman, my second wife had keen instincts of what I was doing and was constantly on the outlook for things like extra forgotten makeup on my face when I was out and about as a novice trans woman. Since I prided myself in the rest of my life on my honesty, the constant lying I was doing to the woman I loved broke my heart. Especially when I could not stop doing it.

My heart was further shattered when she passed away quite unexpectedly from a massive heart attack and I was on my own after twenty-five years of marriage. The only redeeming thing I did was completely purge my feminine side for six months before she died. Even to the point of growing a beard. It was the only thing I could do to try to redeem myself.

Ironically, her death forced open the biggest door to my honesty there was, being honest with myself. When I looked deep, I found that all along I had been just wasting my time trying to be a man with all the privilege that came with it. I had learned to play the male game effectively but did not want any thing to do with my gender prizes after I won them. Being honest with myself for a change was the best feeling of all except I did feel guilty about all the stress and tension I had put others through because of my inner weakness. Total honesty certainly would have been the best policy in my life.

 

 

 

 

The Return Home

 

JJ Hart, on a chilly
Florida beach night.

The return home from a rather lengthy vacation always presents a bittersweet time for me. While the trip to Florida went well and for the most part exceeded my expectations, our return to our home in Cincinnati and to our very lonesome cat was welcome. Similar to being able to sleep in our own bed again.

During this trip we played hide and seek with several major weather systems. In order to stay ahead of the foot of snow, which was heading for our native Ohio, the bus tour company decided to leave a day early and take a different route South to Florida. It proved to be a masterpiece of planning because we faced just a tiny piece of snowy weather around Knoxville, Tennessee and none of the dreaded ice. Which went Southeast of us.

By nature, I have become a worrier in my old age, so on top of thinking about all of the weather issues we would be facing, I had to put the restroom anxiety I always feel in the back of my mind. Which was a good thing because outside of a few startled looks I received from other women on the tour, I had no problems with my choice of restrooms I used. In fact, the biggest issue I faced was trying to wait for a handicapped accessible stall to use which really helped me with my mobility issues, I was able to not use my cane at all and rely heavily on my walker with wheels.

Past the restroom issue, I had to adjust to using my most feminine voice again. An issue because I don’t have to think about it as much around home because I don’t interact with strangers much. Day one proved to be more challenging on my part because I was so shy with the others on the tour, and I was afraid I was coming off as unfriendly or bitchy. I was fortunate in that we had two experienced tour guides who helped me find handicapped accessible ramps and restrooms.

As past trips and experiences have taught me, when I take the first step with a smile and friendliness on my part, most people respond the same way. So, by the time the tour of Florida was over, several of the other travelers made it a point to tell me how nice it was to meet me. I couldn't believe how good it made me feel. It was enough to warm me up even in the record Florida cold spell they were suffering through.  It was so cold and windy for them that they canceled one of the Everglades boat tours we were on. It all worked out for the better for Liz and I because we got extra time to explore the beach which is why we went in the first place. Plus, the leisure time helped me to recover from all the days we spent which required lots of walking. In fact, one day when we went to the Hollywood Beach area of Florida, we ended up walking over seven thousand steps, well over what I was used to.

Overall, I had a very good time on this trip even though it was to a part of the country I don’t agree with as far as politics are concerned. But my native Ohio is rapidly trying to become just as backwards as far as transgender rights are considered.

What did I wear? The whole trip was casual themed and all I took along was my best leggings and jeans, along with a solid pair of tennis shoes for walking. Other than that, I wore sweatshirts. With a daily shave and a liberal dose of my favorite foundation powder. I was ready to go for another day of cold Florida.

As I said, we made it home safely and had a good enough time that my wife Liz is planning the next trip which may include something to do with train travel. Plus, I will be writing more about other in-depth events on the trip.

Merging your Past with your Future

 

Image from Sammy Swae 
on UnSplash. 

We speak a lot around here about merging your life’s past circumstances with the future of what you may be facing.

Depending upon the number of years you have spent living as your birth gender, you may have an incredible amount of baggage to bring with you from your past. Including the input of spouses, family, friends and jobs. What to bring with you to merge with your new lifestyle as a transgender woman or trans man is often an agonizing decision. One thing is for certain you can’t bring all of your past life with you. However, no matter how you may want to cut it, the basic building blocks of your life remain. Such as how your parents raised you. My parents raised me to be a contradiction from the beginning. I was expected to stand up for what I believed to be right, as long as it did not interfere with what they thought was right. So being a childhood cross dresser was being an individual in my mind but an embarrassment in theirs. So, I had no chance of winning my gender battles.

On the other hand, I was taught the difference between right and wrong but not enough that I could bring it with me when I needed to face the biggest battle of my life, what was I going to do about my unwanted male life. Deep down inside, I knew the right answer then just refused to face it.

For the longest time, I was guilty of putting ciswomen and girls up on some sort of a pedestal as I viewed their lives from the outside looking in. Basically, all I saw was they had the chance to wear the pretty clothes and be pursued by the men or boys in school. I so wanted to be the cheerleader on the sidelines rather than the defensive end I was on the football team. Without seeing all the work, it took to being a good cheerleader. In fact, I never saw any or all of the work needed to transition from being a female to being a woman which I found to be a huge difference. Females are born; women are socialized in the world which means not all women ever make it. If and when you are attacked by a TERF about how you were born, rest assured she has problems if all she could come up with was a so-called birthright.

Getting back to how you merge your past with your future, the first thing you have to remember is not to forget about your present. Your present is so important as you live a daily life, often between two powerful genders, male and female. Your present is often the time when you are working hard to see how your gender dreams will impact your life in the future and how much has it done for your past. In my case, all I had really learned about being in the world as a transgender woman was to apply makeup well enough, so I did not look like a clown in drag, and I learned to shop in thrift stores to find the right fashion to flatter my testosterone poisoned body. I knew nothing about putting my new improved feminine image into motion in the world.

Once I did get serious about looking around in my present-day world back then, I wondered how I was going to ever merge my past with my future. After I determined how badly I wanted to.

My main concern was how one sided my interests were. I was mainly a sports addict with the usual male preoccupation with my job. Most certainly, I would be sacrificing my job if I male to female transitioned but what about my sports hobbies? It was then I became very serious about looking around to notice who all was watching sports at the big venues I was in and I was pleasantly surprised that all those years, I had been missing the number of women who were involved. It turned out that unless I was trying to talk sports with a man, my baggage was safe with other ciswomen, and I was not out of place in my favorite team jersey. To make matters even better, when my wife Liz and I got together and began going to “Meetup” groups, I was able to go to writers’ circles to interact with a whole new set of people. I highly recommend groups such as that to expand your social horizons as a transgender woman or trans man.  The only negative experience I ever had was with a lesbian social group who refused to accept me because I was trans. Which was their loss, not mine.

Then I began to look at my future as just downsizing my life. I was leaving friends behind who did not accept me all the way to going from two wardrobes to one. As Liz once told me, it’s not often a human gets to stop a life and rebuild it, so don’t mess it up. With me, I was fortunate to have help in merging my past with my future. When I was with my new circle of women friends, I just had to learn what to needed to omit from my past which would inadvertently out me as a past male. I was able to talk about my family because I had a daughter, which was a good example, I just could not share birth stories. But in reality, I was in the room, just not doing any of the work.

Any way you cut it, when you do make the decision to cross the gender border, you will naturally have to leave part of your past behind. Just be careful, you do not leave any of the basic building blocks behind which make you the person you are. From there you can build a new and better you as your authentic self maybe you never thought you could be.

 

 

 

 

 

 

 

 

 

No One Way is Correct

 

Image from Gabor Kaputi
on UnSplash. 

Even though we transgender women and trans men often follow similar gender paths to get to our goals or dreams, it is still true that one path (the one you are on) is the only correct one. Plus, don’t forget there are so many side trips to take such as surgeries and hormones to help us along.

For example, I read about and hear from other transgender women who have elected to undergo major and costly gender surgeries (like Amber) which they deeply feel they need to feel whole, while me, on the other hand have decided to steer clear of any surgeries. Mainly because they don’t define me as a trans woman. I know what my brain is telling me gender-wise and just don’t need the corresponding equipment between my legs to improve my overall being. Although let me say I understand why somebody else would and if I was younger, I might have considered the surgical route. It just took me too long to figure out who the true me was.

Other than surgeries, I took the same path as many of you. I experimented with my mom’s clothes and makeup since I did not have any sisters, all the way to service in the military from those of you who are approximately the same age as I am such as Bobbie W. who even served on her version of the American Forces Radio and Television service as I did, although she was in the Navy. It amazes me how small the world has become because of the internet that many of us did not have in our formative cross-dressing years. Besides Bobbie, over the years, it has amazed me how similar some of our paths have been and it would not have surprised me if we had not met along the way. Except if you were like me, you were desperately attempting to hide your true self from everyone else in the world.

Then there were the evenings when I did see another transgender woman in one of the venues, I was a regular in, other than Racquel who was a trans friend of mine. One in particular was at a TGIF Fridays I went to quite a bit. I watched this well-dressed large woman step up to the bar and order a red wine, then before I could even attempt to introduce myself, she was gone and I never saw her again. So, on that occasion, I did have my path crossed by another transfeminine person since I could not attach a label to her such as a very accomplished cross dresser. Outside of a few “women” I saw shopping in the grocery store over the years, I learned how rare our tribe really is.

One of the reasons we are so rare is that all of those still in the closet due to their gender issues have not had the chance to be out and be counted. Mainly because of all the male baggage they have fears of losing. It is terrifying to think of losing baggage such as spouses, family, friends and jobs to name a few of the bigger ones. At least it was for me as I went through life frustrated with the amount of male baggage I was accumulating.

Even though, when I started blogging years ago to pay forward and help others similar to me in the closet, it occurred to me my plan had backfired to an extent, and I became a role model to some of my readers. Some even wrote in and called me some sort of a hero to them which humbled me because I never set out to do anything like that as I was just trying to live my life the best I could. Writing about my life was Now adays I keep trying to say I am no hero but merely someone who was terrified to leave her closet and live in the world as I knew it. Certainly not a hero by any sense of the word.

Recently, another point that I have been trying to make is there is no right way to achieve leaving your closet and living an authentic feminine life. Sure, it takes a lot of work and effort to achieve doing something the greatest majority of humans have never considered trying. Especially when we live in a negative atmosphere where a certain melon felon and his political party are trying to demonize us. Hopefully, that all will stop happening when the population finally tires of us and seizes the opportunity to vote on the real issues. Which makes it so important that even if you are in your closet, you vote your true conscience this coming midterm. So much for my political rant which is urging you all to get on the right gender path and stay there through the elections and beyond.

In the meantime, always hope for the best when you are out as your authentic transgender self. Your confidence will keep many of the middle of the road haters and bigots away because humans are like sharks, they sense blood in the water. How you get there is determined by many factors, but the main one is you can only gain confidence by going out into the world in your heels and doing it. Other than that, a disarming smile will take you a long way too. Keep in mind that most people don’t care about you, they are only concerned about themselves, and you will be ok.

As you do it, don’t worry about making the big mistake and you will be much freer to be you. You are on the right gender path because you are on it. Sure, it will have many curves and roadblocks but sometimes all of them make the journey much more worth it.