Are you Worthy, or an Impostor

 

Image from Strechath Gupta 
on UnSplash

As a transgender woman or a transgender man do you ever think you are worthy of all the contortions you put yourself through to arrive at your dream goal. What gives you the right to challenge one of a human’s most sacred basics, the gender you were supposedly born with.

To make matters worse, you have the orange felon in Washington (and his followers) oversimplifying any idea of a gender spectrum saying there are just men and women. When we know there is no such thing because we live it every day. Many of us (including me) wondered for the longest time if we are worth the time to try to handle such a inner spirit which was called a dual spirit by quite a few ancient cultures before the white Puritans got ahold of our society. Forget about being held up to be honored for our knowledge of the world, we became scorned. But that is not the subject of this post, I want to try to talk about us.

The first time when I truly faced the problem of being worthy enough to think of myself as a transgender woman was when I started to attend regular girl’s night out functions and still felt as if I was some sort of an outsider. Or, I had a strong case of impostor syndrome setting in. It took me awhile to get used to where I was behind the gender curtain, feel like I deserved to be there as much as the next woman and relaxed and started to enjoy myself. As I write about often, at this point in my life I had my second wife and male self-fighting me as hard as they could to keep me male and hurt my chances of ever achieving my dream of living as a complete transfeminine person. Without the guilt I felt and had no impostor syndrome.

What kept me going through all the resistance I was feeling was the whole femininization process felt so natural. Even with the day my wife could had left me behind in the small Cleveland, Ohio tavern venue we were visiting as two women before we went to a transgender-cross dresser social mixer. What happened was, we were sitting at the bar enjoying a drink when a good-looking man on a Harley motorcycle pulled up outside, came in and sat next to my wife and started a conversation. For the first time in my life, I felt powerless to do anything about what I was about to go through if the man offered my wife a ride on his Harley. In addition, my wife played her hand for all it was worth before she decided to not go with him leaving me behind. With no male privileges to protect me. I was taught quite the lesson about female-to-female competition when it came to men and would I ever be worthy enough to compete. Don’t be fooled into thinking that women don’t compete as much as men. They do, just on a different level of intensity at different times.

It literally took me years to accomplish what I wanted to, but I did feel I had the confidence to stand up for myself as a trans woman. In other words, I finally had been able to put the total package together on my trip out of the mirror and into the world. It felt good until I found I was not there yet and was not worthy of feeling secure in calling myself a proud transgender woman. I wanted to be more; I just wanted to be worthy of just being the me I always dreamed I could be. I wanted to be able to compete the next time my wife encountered a man she was attracted to for his attention on an equal footing. Sadly, I never could before she passed away.

To be worthy for me, also took the work of several friends I always mention who taught me so much about being a woman in the world. Primarily in the area of dealing with me. Being lesbians, they taught me I did not need a man’s attention to validate my being in the world. And I was no worse for wear after leaving the men’s club for good and greener pastures with feminine privileges such as the basic freedom to see the world like me. Being allowed to express my emotions when I needed to be a prime example.

Are you worthy can only be answered by you. I know from reading the comments I get, many of you are taking the cautious exploration methods that I took on the path to my gender goals. The method I took was certainly much slower than just tearing the bandage off saying to the world, here I am. Sometimes I wondered what that would have been like when I considered trying it as early as when I was discharged from the Army. Before I had the chance to start building any sort of male life at all. Naturally, the world was much different back in the 1970’s, early 80’s when I was discharged so I will never know what my life would have been like. All I do know was my initial exploration into coming out to my mom were dismal failures and I probably would have been disowned by my family.

Also, it is never too late to think of yourself as being worthy of going behind the other gender curtain. Male to female or female to male, it doesn’t matter. The trip is amazingly the same according to readers such as “Alex” who is a female to male transgender man. The only stable idea is the longer you wait, the more likely you are to build up more gender baggage which you will have to decide what to do with. Who knows, maybe you can find others around you who enjoy the same hobbies and interests that you do. Which is what happened to me.

The only way you can know if you feel worthy is to try.

 

 

 

 

 

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.

 

 

 

Playing on the Girl's Team

 

Image from Fa Barbosa
on UnSplash.

I am fond of calling my initiation into the world of ciswomen as being allowed to play in the girls’ sandbox. But recently, I have seen it described as playing on the girls’ team. When it comes right down to it, it doesn’t matter what you call it when you have essentially given up life as you know it to transition into the feminine world.

When I was allowed to play on the girls’ team, of course there were many new things I needed to learn because I was seeking admittance to a new and complex, layered feminine existence. For the longest time as I was learning what life really was like for ciswomen, I took the easy way out by thinking all I needed to do was look the part. This is when my second wife began to mock me by calling me the “Pretty, Pretty Princess.” She was right as my presentation was advancing quickly forward and I had ego trips when women at transgender socials I went to on Long Island, New York mistook me for a real woman and wanted to see a male identification before they would let me in.

Even though I was extremely flattered when they asked for my ID, deep down I knew my wife was right and all I was trying to be was a princess. That was when I tried to begin studying the lives of women around me to discover the deeper meaning of being allowed to play on the girls’ team. Which I knew my wife would never help me with. She was busy with bigger issues such as the possibility of losing her husband to another woman which was me.

Initially, the shock of playing on a different gender team came from losing all of my male privilege such as using my size to bluster my way through life. All of a sudden, my size which I took for granted became a problem for me to disguise with the best fashion choices I could. All I knew for certain was I was told I had good legs at the Halloween parties I attended as a woman, so I tried to build my style from there. All the way to putting together my own tennis outfit even though I had never played a game in my life. Eventually, I needed to back off from showing too much leg and getting kicked off the girls’ team for not blending in and attracting too much attention to myself.

It took a while, but finally I began to realize what feminine privilege was all about and it was so much more than just having men open doors for me. Privildge to me meant I could appreciate the world around me so much more deeply. I had many more avenues to explore in the world once I escaped the restrictive bonds of living in my old unwanted male world. Other women freely interacted with me once I was firmly accepted on the girls’ team and once I learned the rules of engagement and communication, I was able to have so much more enjoyment in my life. Most importantly, I knew I never wanted to go back no matter how many stop signs I faced on my gender path.

Sadly, my second wife passed away before she could see the maturation of her princess into a fully-fledged transfeminine person. Looking back, I don’t think we could have ever stayed married but hopefully we could have remained friends while I continued to fill out my gender workbook. I finally learned I did not have to rely on her assistance to gain admission to the girls’ team because she had given all she could to help me. As with any other female, I needed to find my own way to womanhood. And even though I was not born as a psychical female, I surely thought like one and fought to be one my entire life.

As a novice on the girls’ team, I needed to earn my way also which included many bumps and bruises along the way when I learned I was much more than a cross-dresser who liked to wear women’s clothes, the mental process I went through was much more complex and tougher. To quote an old popular “Kenny Rodgers” song, I had to know when to hold them, know when to fold them and know when to run when I was dealing exclusively with other women.

Fortunately, my newfound acceptance on the girls’ team meant I needed to do very little running. No one came up to me and tried to pull my wig off in public, and for the most part I had to just deal with silence, stares and glares when I encountered a woman who for some reason wanted to hate me. There was one in particular who was also invited to the girls’ nights outs I was invited to who had a problem with me being there. I was able to ignore her for the most part or try to kill her with kindness. Finally, it occurred to me that her problem may not have anything to do with me, it may have been with the world. Maybe she resented the fact that I was happy, and she was miserable.

The more I was allowed to play on the girls’ team, the more I learned from them on the nuances of the new life I so badly wanted to live. Along the way, I never imagined learning so much in such a short amount of time. I also never thought feminine privilege could mean that much to me after I left all my male privilege behind. Especially when the effects of HRT softened my world and improved all my senses,

Whatever you want to call it, playing on the girls’ team or playing in the girls’ sandbox never mattered to me. The most important part was that I made it and rarely got any sand thrown in my face as the princess grew up.

 

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.

 

 

Out in the World

 

Hair by JJ Hart. Bead work 
by Liz T Designs. 

Just a short post today due to time constraints.

I am going with my wife Liz to two of her doctor’s appointments this morning which will take up the usual time I take every day to write. Fortunately, the visits take place very close to our house, and we don’t have a long way to go to get there.

To get ready for the appointment, I need to take time for a close shave, moisturizer and pick out some casual clothes to wear. It is going to be a warm day here in Cincinnati, so I am planning on wearing a pair of leggings, along with flats and a short-sleeved top. Plus, I can’t forget to brush out and tie back my long hair.

No need to put a lot of effort into going casual to the doctor’s office where no one notices me anyhow.

Then later on in the day, Liz and I are meeting with a construction contractor assistant about redoing our upstairs bathroom. The assistant is a younger woman and one of the very few people I have outed myself to as being a transgender woman in the past several years. So once again, a nice casual outfit will be all I need to wear for her visit.

I doubt if anything exciting will happen today but if it does, I will write about it!

I've Got Someone for That

 

JJ Hart on Left, wife Liz on Right. 

Maybe you have seen the commercial on television where a group of men seemingly have an answer for a friend who can solve a certain problem. To a point, then they are all stumped on what to do.

I saw the commercial again this morning and applied it to my path to living a transgender existence. My basic idea was, I did not ever have someone to provide guidance in all my gender issues. In the pre-internet days, which I write about often, I needed to rely on publications such as “Transvestia” or “Tapestry” for any real information on having someone to help me understand what I was going through in my life. I was overjoyed for awhile when the magazines helped lead me to actually meeting in person others at cross-dresser-transgender mixers which were close enough to me so I could attend. Surely, (don’t call me Shirley my name was Karen back in those days) I could meet someone there who I could explain my gender issues to and feel as if I had someone to confide in and help me.

In reality, even after I went to the social mixers, I still did not come away with feeling like I had someone to be my friend. No matter how you defined what the publications called me. A transvestite or a cross-dresser, I just knew I was different and still belonged in the group of men in the commercial who were stumped on what to do. That defined the new groups I was meeting for the first time.

Since I could not find a friend at the mixers, I withdrew into myself and did the best I could cross-dressing and dreaming of a better day in front of the mirror. I was stubborn and kept on attending socials until I began to be invited to smaller parties at a house in nearby Columbus, Ohio. The parties were very diverse, and I learned a lot from the others around me and even developed acquaintances who shared my gender path. Or so I thought because a few of them took a sharp curve away from me and went as far as having gender realignment surgery. Back in those days when you took such a radical step, you were expected to leave your past totally behind and start all over again and I started to drift away from them. Very soon I was stumped again and very confused on where I was going as a transfeminine person.

The only thing I knew for certain was my sexuality did not change when I entered my feminine world. I even was attracted to the very few lesbians who were attending the parties I was going to, and often we would briefly leave to visit other lesbian friendly venues in Columbus. At least it was one small feeling I knew I could count on.

Through it all, I did have someone who was my second wife. On many of the party nights, she would accompany me which sometimes was bad and sometimes it was good. She was the one who saved me from being trapped in a small hallway by a huge admirer one night, which was good, and other nights her presence hindered my ability to expand and test my feminine personality. Sadly, I learned more about myself when she was not around as I considered her my best friend most of the time. She was not the person I needed all the time though, which created huge problems in our long-term relationship. She always knew I was a cross-dresser but drew the line if I drifted towards any of the transgender women at the party.   

At that point, I did feel like I did have someone who understood what I was going through at the party but had the feelings rejected at home. The worst part of the whole thing was, I had gone too far with my transfeminine experimentations to ever turn back but I tried to have the best of both worlds. Save my marriage on one hand and live a part time life as a trans woman on the other. I still carry the guilt coming from the number of times I broke my promise to my wife and left the house dressed when she was at work. I have always described it as cheating on her, with myself.

One way or another, I was gaining confidence in my feminine self to continue to build a new life which felt so natural because for a change I had someone to lean on. For those of you who don’t know, my second wife passed away suddenly from a massive heart attack leaving me with a huge hole in my life along with a truck load of guilt which I could never make up for.

In her sudden absence, I fell back on the only person I knew who could help me as I decided to end my male life for good and live out the remainder of my life as a trans woman. It turned out all the labor of love I put into my femininized life came back to help me because I had all the hard work of refining my presentation behind me. I had a working knowledge of what to do to survive in the world of alpha ciswomen. I just had to refine my new life to a point where I could thrive with new friends. When I had reached new milestones in my life such as HRT hormonal changes, I was met with welcome to our world and knowing smiles rather than masculine scowls and glares. I loved my new life.

The only problem I had was I took too long to transition across the male to female gender border. It turned out I had someone all along to help me if I ever gave her the chance. I was stuck in the good old boys’ male privilege club way too long and it was hard to give up. Once I found someone like my wife Liz to point out the obvious to me, I knew for sure I had that special someone and I could live an authentic life as a transgender woman.

 

I Got Scammed

 

Image from Markus Winkler
on UnSplash.

Years ago, I discovered I was scammed when I attempted to climb my gender path towards my dream goal of living completely as a transgender woman.

My first mistake was believing what I saw in the mirror when I was cross-dressed as a girl was a true indication of what I really looked like. The mirror was more than capable of lying to me by telling me I looked attractive, when I really looked like a circus clown in drag. It wasn’t until I began to go out in public as a feminine person, did I find out the brutal truth of how far I still had to go to present well as a novice cross dresser in public. Rather than create attention to the way I looked, I needed to blend in with the average ciswomen around me and just get by.  I was scamming myself to think otherwise.

Sadly. The scamming continued unabated until I woke up to the true world around me. My life was restricted by outdated thoughts I carried through from my still very active male self who thought dressing sexily was the way to go. The only good thing that happened during this part of my life was that I went through my cross-dresser “adolescence” fairly quickly and began to attempt to dress my testosterone poisoned body the best I could to hide my flaws. I was aided by fashion styles back then which favored miniskirts, bare legs, opaque stockings with oversized sweaters. I was even able to continue a version of the fashion basics when I changed into a bohemian style denim mini along with a flowing loose top to hide my oversize male torso. For once, fashion trends were playing in the right direction for me and my scamming decreased from my male self and the public.

At that point, I shifted my emphasis on where I was going when I was learning the world for the first time.  Initially I chose more malls and safe places such as coffee shops and bookstores until I got bored and chose other venues to go to at night when I began to sneak out of the house when my wife was working. At first, I was satisfied with going to a few male gay venues in downtown Dayton, Ohio. Even though I did not like the overall atmosphere of the places, I kept going because I thought they were safe. That was until I was stopped on a sidewalk outside one night by two men looking for a handout and I was lucky I still had a five-dollar bill to give them, so they left me unharmed. I learned a valuable lesson that all ciswomen knew which was to always be careful of your surroundings and I never went back there again unless I had friends with me.

I also felt I was scamming myself and wasting my hard-earned money by going to gay venues at all. Lesbian bars for the most part were fun for me for a number of reasons. Including the attention, I would receive on occasion from a few of the other patrons. Male gay bars however just treated me like any other drag queen which I hated. I even had a hard time being served which drove me away. It was then; I decided to stop being scammed and take my business to straight sports bars where I knew I could enjoy the atmosphere if only I could be accepted.

I was surprised how quickly I was accepted at venues I used to frequent as a man, and I felt comfortable in. The difference in venues was in the straight sports bars, other women wanted to actually talk to me. Which opened up a whole new world of possibly being scammed by ciswomen and their passive aggressive behaviors. I don’t want to recall how many times I went home with claw marks on my back after I assumed another woman’s smile actually meant she was being friendly with me. That scam became old quickly and I learned to be careful in the world in a whole different way.

The biggest scam of all came when I learned I was not a man cross-dressing as a woman, I was a woman cross-dressing as a man to get by in a life she never wanted. If I had only learned that earlier in life how much easier I could have made it on myself. No such luck, as I was destined to be scammed by a world and my male self into thinking I was doing the right thing by fighting hard to keep my manhood. These days, I am older and wiser when it comes to scamming myself and have accepted the transgender truth, I always denied myself.

As I wrote in a recent post, I would not recommend the path I took towards achieving my dream because the world has changed since I did it. Harsh anti-transgender politicians have made it harder to come out in the world as well as making it harder for some of us to exist at all. (Like in my native Ohio). Hopefully though, the younger generations seem to be resistant and blind to the bigotry of their elders and there is hope for the future. That was, none of us will have to worry as much about scamming ourselves or each other about who we truly are. Just people who have been around forever and are trying to live a basic, honest life.

One way or another, the path we have chosen as transgender women and transgender men is much more difficult than the average person next door. And I can add scammers along with stop signs, blind curves and steep hills on our route to finally discover who we are with the opportunity to live it. It just makes it worse when we learn the person who was our main scammer was ourselves.

As always, thanks for joining me in my journey. Any comments, claps or subscriptions are always welcome!

 

What Kind of Man was I?

 

Image from Christian Lue
on UnSplash.

I had a good question on one of the blogging platforms I write for the other day. The person asked a simple but relevant question about what kind of a man I was before I went down the strenuous male to female femininization I chose for my life.

Here is how I replied: Thanks for the question. In my former male life, I did the best I could to be successful and hide my true self from the world. Early on, I played football and worked on cars to essentially build a wall to keep the teenaged bullies away. From there, I went off to college and earned my first degree, a bachelor’s in history before I was swept off into the Army during the Vietnam years.

After the Army which I was honorably discharged from after three years away from being able to express my feminine self, I ended up jumping back into my cross-dressing ways and eventually getting married for the first time and fathering a daughter. Once again, I was doing my best to do the all the right things to make the world think I was a “normal” male which of course I always struggled with.

From there, I jumped out of the radio business and into the tavern venue world when a friend of mine and I bought a small neighborhood bar where we lived. My dad described it best by saying it had two doors, so the flies did not have to stop when they went through the bar. He always had away with words. At any rate, the bar did not make it long, but my ownership of the building did. Initially I did not want the responsibility of property ownership but was talked into it by my dad. I think at the time, I did not want the extra pressure of owning anything I would have to get rid of as extra baggage if I decided to make the jump from one gender border to another.

I stayed in my male mode and managed to turn the failed bar into a successful pizzeria until I was drinking too much and lost it too. I was trying to over medicate myself as I ran from my depression and anxiety issues, along with the major problem I had which was of course I wanted to be a woman more than anything else. During this time also, I managed to sneak in another degree, an associates in business, from a local college to take advantage of my veterans’ benefits.

By this time, you can see the theme of my life was not a good one. Anything successful I did, I managed to destroy because of my gender issues. I even lost our house I bought off the GI bill.

Ironically, my life began to turn around when I met the first of the two most influential women in my life. The woman I met worked at a radio station I worked for after I was discharged from the Army and was trying to run the pizzeria successfully. I was literally swept off my feet and ended up divorcing my first wife and marrying the second woman. By the way, both women knew of my cross-dressing desires before we were married. It turned out I was man enough to stay married to her for twenty-five years before she suddenly passed away, wrecking my life for several years before I could rebuild it.

During the twenty-five years I went through with my second wife, I began to really learn I was not the man I used to be as I felt myself transitioning again from cross-dresser to transgender woman. In the meantime, I had thrown my old baggage caution to the side and had built a successful career for myself in the restaurant industry. By the time she passed on, I had built was too much spousal support, family, friends and jobs to casually risk it all and transition. Although it was always my dream to do so. Being the man I was meant I would have to give up the positions I held with civic organizations in town too. I felt flattered to be a part but at the same time never felt really at home there.

After I had given up any hope of ever finding anyone else to be with the rest of my life, I met my future wife Liz, and she was instrumental in pushing me into pursuing HRT by telling me she had never seen any male in me to start with. Her gentle push was all I needed to give away all my male clothes and stop the charade I was living life as a man.

I guess you could say that although I tried hard to be a successful man, I kept trying to destroy any success I had. It took a series of good women to show me the way to where I should have been all along, living my dream of being a transfeminine person fulltime.

My first wife went with the flow and did not seem to care what I did, my second wife approved of my cross-dressing but totally disapproved of HRT and any idea I was transgender, and my third wife totally helped me along. Out of the manhood I never wanted. The only woman left to mention was my internal one who (not so patiently) had to wait for her turn to do more than survive as she needed to thrive for a change.

I hope this answers the question of what kind of man I was before a jumped out of the man’s club and into the girl’s sandbox. I led a complex life of failure and success as a man but never felt as if I was doing the right thing. I was fortunate when good people came along to save me from my self-destructive self. Without them, I doubt if I could have ever made it to the place, I am today.

Thanks for the question! I appreciate any response I get from all of you plus any claps and subscriptions you send my way.

 

 

 

 

 

I Had to do Something Right

 

Image from Mark Farias on Unsplash 

In my dark days of confusing cross-dressing, I vaguely knew I was doing something right. Or at least I thought so because I could not wait to try it again.

Looking back, it was the brief moments of gender euphoria which clouded all my doubts about my gender and kept me going. Even through the nights when I was the laughingstock of teen girls in malls, a little voice kept telling me to keep going and eventually I would improve my overall feminine presentation so that I would blend in and not get noticed. Along the way, I even needed to lower the expectations I was putting on myself to keep going. I was never going to be the most attractive woman in the room, but at least I could still be like most ciswomen I saw and live a decent life. Even though I started to feel this way, I never gave up the idea I could do better with my makeup, fashion and hair so I could survive. Simply because I was enjoying the experience so much.

Later on in my life, doing something right extended to my interaction with the world as a novice transgender woman. I was surprised when I attracted more attention from ciswomen than men and just thought they were curious about me and were welcoming me into their worlds, while men were just the opposite. Most resented the fact I was leaving all of the male privilege behind (along with the good old boys’ club) and moving to the other side of the gender border. I did not care because my need for companionship was being satisfied and I had always gotten along with women easier than men most of my life. Increasingly I found I never wanted to go back to the male life I was attached to by a spouse, family, friends and jobs. It seemed the longer I waited, the more male baggage I was building up when I really did not want to.

The next problem I ran into was the impostor syndrome I was feeling. Specifically on the girls’ nights outs I was invited to. It never failed that right in the middle of me enjoying the evening, I had suspicions sneaking up on me that I did not belong there at all. I was an impostor in a scene made up of women who had worked their entire life to get there. It took me awhile to come to the conclusion that I had worked my entire life also to make it to my own version of womanhood, and I deserved as much as the next woman to be attending. Fortunately, I received very little negative feedback from other women attending the get-together, so I did not have to face my impostor syndrome at all. I was doing something right for a change to even be invited to such special women only events.

I was able to take my experiences with girls’ nights out to my everyday life primarily because it built my confidence as a transfeminine person so much. With my newfound feelings, I worked even harder on my makeup, fashion and hair to appear more feminine than ever before. Primarily, I learned the power of contouring and colors on my face from professional makeup artists I met at the cross dresser-transgender social mixers I went to. One in particular, took the time to explain what he was doing in terms I could understand and repeat on my own. It was a powerful experience when I had to set my makeup ego aside and learn better results from a professional. From that point on I worked on taking weight off, so I had a better opportunity to find and buy more fashions that flattered my male figure at the many thrifts stores I frequented. When I arrived at that point, the problem then became getting out of the mirror and started putting my new improved feminine self into motion in the world. It proved to be the most difficult part of me doing something right.

Suddenly I had to consider how I was moving as I tried to mimic the unique way ciswomen move and put all my male linebacker moves behind me along with the scowl on my face I was used to wearing as my male defense mechanism. And the most difficult issue of all was learning to communicate one on one as a woman. I knew with certainty I would have issues with my communication, but not to the point that I did. I even went to the extent of taking vocal classes to improve my feminine basics and be able to talk easier in the world with women and men. It just made sense to do if I was continuing to do something right.

It turned out, the more I did right and received positive feedback, the more I wanted to do to refine my feminine approach as a transgender woman. Because I always had the belief, I needed to be better than the average ciswoman to just survive behind the gender curtain. When I was just trying to do something right, on occasion I paused to reflect on how far I had come along my gender path to arrive where I was. I did remember that scared little boy dressed in his mom’s clothes in front of the family’s hallway mirror, wondering what was next. For the most part, back in those days, there was very little to let the young boy know he was doing anything right.

Somehow, I survived all the negative feedback and impostor syndrome problems and continued forward to a better world. One I wanted to be in and dreamed of my entire life. As I love to say, as with any woman, I needed to socialize myself into the world. Being born female does not automatically make you a woman, you must learn to be one. The same was true for me. I just took a radically different path to earn my womanhood. I needed to do many things right to arrive at my dream.

 

 

 

 

My Gender Woes were Always Pending

 

Image by Samual Regan Asante
on Unsplash. 

From the earliest days of my life, my gender always seemed to be “pending” as the bank likes to call my most recent on-line deposit.

In my cross-dressing days, when I could afford it, I jumped daily into different wigs, clothes and makeup styles. I was desperate to find the next best thing which would help my feminine presentation along and I was always waiting for the public to acknowledge me. Positive or not, I was always pending their approval in my life.

Along the way, I did get better with my looks and became better at blending in with the ciswomen in the society around me. But I never lost my desire for approval. It became key to my survival as a novice transgender woman, long before I discovered there would be so much more if I ever wanted to slip behind the gender curtain and live my dream life. By then, I was lapsing back into my brainwashed family idea that nothing was ever good enough which carried over to my male to female femininization activities. My confidence was so low, and fragile that the smallest negative comment would send me back to my cross-dressing drawing board as I wondered if I would ever make it.

At that time, I survived in my world by listening to a little voice in my head which was telling me all this turmoil was pending if I just stayed on my path. To do so meant negotiating many blind curves, bumps, and stop signs along the way. Before I knew it, my path was littered with failed fashion choices, wigs and drag style makeup. I needed to choose wisely what I would need to keep before I attempted to move on.

One of the most dramatic pending issues I had was when I made the jump from gay to straight venues. When I did it, I had no idea if I could, so I had to gather the confidence to do it. I needed to be better at blending my style so I would fit in but not too flamboyant to attract unneeded attention as a single woman by herself in a bar. I became very good at using my cell phone as a prop to act like I was saving a seat in the venue for a friend. Among other things I was doing to present and blend in as a transgender woman. I was not concerned so much about being read as trans but was concerned about not being a distraction. Even though I became successful and was able to become a regular at a couple venues, my relaxation was always pending as I needed to stay on guard for any crazy reactions to my being there at all.

The whole process helped me to heighten my senses to where ciswomen normally operate on a daily basis. Since I was primarily dealing women in my new life, it was key that I was able to read my gender cues correctly because the cues were coming from a different angle than they ever were when I was a man. Women primarily were curious what I was doing in their world and was I projecting an honest view of myself. When I passed their tests, I was allowed in to play in their sandbox. There was room for me after all and my dreams of living in a feminine world suddenly became so much more feasible. Something which was always pending before I was able to get out into the world and experiment as a transfeminine person.

The problem became; I was forced to remain pending in my life at a time of extreme gender discovery from me. As the world of ciswomen were exploring me, I was exploring them and learning tons of information on what I would have to do if I ever chose the final male to female transition. In other words, I was able to turn their curiosity around to satisfy my own.

Finally, I arrived at the point of no return when I had done enough experimentation as a novice trans woman to know where I wanted to go to live my dream and I knew I could if I played my cards right. I knew in many ways, this final transition I was planning on making would be the most difficult to do. I would have to try to wrap my male life up the best I could. Which involved deciding what baggage I wanted to bring with me following nearly a half of century of living.  As far as family went, I was down to only two who were still living and I knew I really wanted my daughter to accept me, which she did and my brother who I figured would be a problem and he was. He rejected me and we ended up going our own separate ways over a decade ago.

I knew too, I would have to find another way to financially support myself because my employers never would. For once, age came to my rescue as I was close to being able to take an early social security retirement and augment it by selling the numerous amounts of collectables my second wife and I had collected over the years. With the two sources of income, I calculated I could not have to work another job as I transitioned.

With those two major potential problems behind me, I had very little pending to stop me from moving ahead to the hormonal world of HRT which proved to be immensely satisfying and something I should have done years before. Rather than making the process another pending idea I wanted to try.

By now, you probably know the rest of the story. I am seventy-six and the remainder of my life is shorter than what I have previously lived. Even though I am immobile, I am fortunate to still get around and have someone who loves me. I just hope good health is not pending and I can live peacefully with myself. Which at times during my life has been an issue, including my mental health. I am meeting with my new therapist this week and will have more to share later.

 

Everything Was Fine Until It Wasn't

 

Image from Danny
Messina on UnSplash

Many times, when I was sailing along thoroughly enjoying my feminine self out in the world, I would come to a rude awakening that something was not right. As I experimented as a novice cross-dresser fresh out of the mirror at home, I learned any number of things could be wrong. Including the cruel imposter syndrome which haunted me. A great topic for another blog post.

Or maybe my makeup was not on point, and I looked like a clown in drag, or I had that old male scowl on my face instead of a pleasant little smile which gave away the fact I was not enjoying myself the way I should. But something was wrong as I was doing what I wanted to do for a change, and I needed to show it. Not revert to my old male ways of trying to scare people off before they even started to interact with me. It is something I work on to this day as it is easy for me to fall back into old gender habits. I needed to work hard to put my entire new feminine image into play when I was out or no matter how good my makeup and fashion looked, I was not going anywhere in my development as a transgender woman.

A quick example of the problems I was facing with my face happened one day when I was out shopping in a woman’s clothing store. When I came around a rack of clothes, I was startled by a young girl staring up at me. Worse yet, I was prepared for the worst when she took off looking for her mother. I was semi-relieved when I heard her say, look at the BIG woman, and I thought she had that part right. Until she said, the BIG MEAN woman, and I immediately felt bad that she thought I was mean. From that point forward, I put a slight feminine smile on my face as my final touch of makeup. Everything was right with the world that day (including the little girl who thought I was a woman) until it wasn’t.  Lesson learned.

Changing the way, I looked at the world with my face was just the beginning of improving my overall presentation in the world of ciswomen, young and old. Early on, I paid quite a few brutal dues when it came to encountering groups of teen girls in the malls I went to. We all were in the process of discovering our femininity, and the girls took their humor out on me vocally and it hurt but the process helped me to develop myself to a point where I could better blend in with the new world I was trying to conquer. I just had to learn to conquer in a different way than I had ever had to before. I could not just hope to bluster my way through life as a man which I had gotten used to, I needed to finesse my way through until I began to feel the benefits of female privilege past the occasional man who opened a door for me.

Everything was fine, until I learned I was just getting started on my dream to live a transfeminine future. I had no idea how complex a woman’s life could be with a passive aggressive future in store for me. Plus, a future where for a change, to survive with other women I needed to completely listen to what they were saying and make sure I looked them straight into the eye, so I did not miss any nonverbal communication which was coming my way. Several times, I was helped out of potentially dangerous situations with toxic men by paying close attention to the nonverbal cues being given to me by concerned women with much more experience than me.

For the most part, this time of my life, in my thirties and forties , everything was fine with the gender juggling act I was attempting until I pushed myself too hard, challenged my mental health and continually got in trouble with my second wife who caught me trying to sneak back into the house after a night of living as my newly thriving feminine self. At that point, massive fights occurred which ended with me trying to promise I would never go out again. Which I knew would never happen. Once I had seen the world from my vantage point of a trans woman, deep down I knew I could never go back to a completely male life. I think my wife knew that too and that is why the fights we had became so vicious. Particularly when she told me I made a terrible woman because (in my words) my gender workbook was not filled out, and I had not paid my dues. Which was exactly what I was doing when I went out to live. I was sad I couldn't share my new knowledge with her but it was just not meant to be before she suddenly passed away.

After she died, nothing was fine as I was intensely lonely and needed a shoulder to grieve on. I found that shoulder in a predictable place and she was there all the time, my transgender self. When failure was not an option in my life, all the lonely nights I spent exploring the world around me with other women proved to be an invaluable experience when I learned I did not “make” a terrible woman after all. It turned out, I did not “make” anything at all, I just found my way to a place I always should have been, and everything turned out of be fine and I could take the wasn’t away from it.

I was even happy for the first time in my life as the heavy expectations of a male life I wanted no part of were removed for good. Being free to be the true me was the best move I ever made and my only problem was I did not do it sooner. Everything was fine, it was just hidden from me by myself. When revealed, I was free to never look back.

 

 

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.

 

Facing my Deepest Fears

 

Image from Tonik on Unsplash. 

Over the decades I have found that my gender desires have produced the biggest fears and anxiety I have ever felt.

Prime examples came from the times I was first testing the world as a transgender woman. The number of occasions I needed to sit in my car making endless tries at adjusting my hair and makeup until I felt everything was right to attempt going into whatever venue I was going to. You would think from the number of times I had to face my fears; I would have at least become used to it. But I never did. In fact, I developed my own form of trans PTSD from the number of times I was rudely rejected by the public. I could not get it out of my mind that if I was laughed at once, I could be laughed at again. Which I discovered just was not true after I learned to dress for the public of ciswomen around me.

Finally, a little confidence began to creep in, and I did better for the most part, but it seemed the fear of being myself just would not go away. Maybe I can blame my old male self who in his own way was as strong willed as my feminine self and did not want to give up all the male privilege he worked so hard to earn. His reluctance to give up pointed to a deeper problem I had. The fear of facing myself. At the same time, my dreams of even trying to become a fulltime transgender woman in the world seemed to be a far-off dream.

What I decided to do then, even though I still was experiencing deep fears about my future, was experiment by going out into the world a little at a time. I started in what I perceived as safer spaces such as shopping malls and gay venues. If and when I was successful (or grew tired of) in those places, I would try more challenging places. Lessons I learned included money overcame gender problems in the malls and I was just considered another drag queen in the gay bars and made to feel completely out of place. I discovered to enjoy myself more I would need to try to frequent the same sports bar venues I went to as a man. Where I could drink draft beer and watch my favorite team on the big screen televisions. Sure, I was scared to do it as I knew how single women were viewed in sports bars, but I had to try.

Desire overcame fear and I was successful as long as I followed my three basics of smiling, never causing problems, and tipping well. Before I knew it, I was a regular and gained the backing of the bartenders who even saw to it that I had restroom privileges. Before  I knew it, I had built a small circle of lesbian friends who shared my love of sports, as well as another transwoman. Loneliness became a thing of the past for me, and my fear of being seen as a woman was going away too.

Just when my trans confidence was at an all time high, obstacles such as drunk guys would come along and ruin my evening. The night I remember the most was when a bunch of drunks noticed my trans friend and I at the bar and started playing “Dude Looks Like a Lady” time and time again until the manager asked us to leave. We did, temporarily, because a month later when I was in a nearby competing venue, I was surprised to see one of the bartenders who was there when I was asked to leave approaching me. I was astounded to learn the manager who had kicked me out had been fired for drug use and I was invited to come back. So much for the drunks who had played that song over and over and I had put my fears to rest. To this day though, when I hear that song, I cringe.

Sadly, even though I have been in the public’s eye as a transgender woman, I still look over my shoulder when I do things like use the restroom. Fortunately, I have Liz to help me out when I have to go and mainly these days, I don’t present as trans as much as I do as old and partially immobile. I am happy these days when I can find a restroom with a handicapped stall to take my fears away.

My deepest fears now revolve around the number of ridiculous restrictive anti-transgender bills currently in the Ohio legislature. One bill would make it illegal for anyone to wear makeup different than their birth gender. Which I guess would mean the orange felon or his sidekick Vance would be arrested if they come to Ohio. I am lucky that age and years of HRT have softened my facial lines to a point of where I don’t wear much makeup at all but what about the younger transgender population. Hopefully, none of this will actually happen or the courts will strike it down.

These days, I have managed at least to calm down my fears of what will happen to me if I have to go into assisted living or if I develop dementia like my dad had. I finally came to the conclusion not to worry about something I have no control over.

I don’t know why I waited so long to be paranoid over what has made my life worth living over the years and decades. I used to be a go with the flow type of person and if I got myself into some sort of a mess, I could get myself out of it. Probably now it is because I have to depend on my wife Liz for so much. Fortunately, most of my deepest fears came from pursuing my gender truth and when I came out to myself, I proved that I was the most important person of all to be truthful with. It was not until then did my life began to change for the better and I could live without all the fear I was experiencing.