In Praise of Femme Lesbians

 

Image from Alexander Krivitsky
on UnSplash.

Back in the day, femme lesbians were known as “lipstick lesbians” and were usually in heavy demand from butch and super butch women in the community.

As I write this post, it brings back many unique and even pleasant memories for me. Why? It is because during that time in my life, I was desperately seeking where I fit in on the gender spectrum. As I drifted from point A to point B, I discovered the only place I really fit in was with the lesbian community. If I could only be accepted which was far from a given.

It all started with me when I was going to several mixed, male and female gay venues in Columbus, Ohio years ago. One night I was in a very crowded venue trying to get drink when I very butch lesbian offered to buy one for me. It was the first time I felt as if I was in the right place at the right time and someone appreciated me for who I was. It all started me on a path I still am on to this day with my third wife Liz who identifies as a lesbian. She was the one person and only one who had told me she never saw in male in me, but I am getting ahead in my experiences on how I arrived here.

It all basically started seriously when I started to go regularly to two small lesbian venues in Dayton, Ohio. One I was accepted in and one I was not. The one I was not accepted in showed their dislike for me in many ways, including shutting off the juke box when I played Shania Twain’s “I Feel Like a Woman”. No sense of humor at all! The other venue was the total opposite, and I even discovered I knew one of the bartenders from my male life. It was there that I had many exciting adventures into a terrifying world I did not know much about except when I was drawn to it and it was drawn to me. Going all the way back to one of the many diverse parties I went to in Columbus, Ohio when I hit it off with another woman and we took off and visited a very popular gay night spot called “Wall Street”. Since I was still married at the time, nothing happened except again I learned where I really belonged on the gender spectrum.

Through most of it, I was playing the odds, I could explore the world as a femme lesbian and still get home and cleaned up before my wife did. One night in particular was rough when a butch in a cowboy hat demanded that I sing karaoke with her, make no mistake that I am a terrible singer and wanted nothing to do with her but she was convincing and I thought of the only song that I knew to sing to was “David Allan Coe’s You have Never Even Called me By My Name.” And here I was sharing a microphone in my blond wig and tight jeans with a butch in a cowboy hat doing my best to let her do most of the singing. By the way, “David Allan Coe” just passed away recently in his eighties, and after I was done singing, I got the hell out of there when the butch said my voice was lower than hers and I never saw her again.

Other than my brief singing career, I had many more interactions with lesbian women and even my first time I was asked out to dinner came at the request of a super butch who went on to transition completely to a transgender man. Even though I was scared to death, I still managed to have a good time which set me up for future successes when I went to lesbian mixers with my friends. They were shy but I was not and ended up in several interesting situations when one woman said she should buy me a drink and take me home with her (I got the drink but did not go home with her) and the night I was caught kissing a strange woman by the pool table in a venue we were in.

Perhaps, other than the karaoke experience, the evening I was asked by my friend to be her “wing person” and approach another woman about getting her phone number for my friend. I never got that phone number, but I did get a once-in-a-lifetime experience to remember.

Being accepted the way I was by other women saved me from having to consider my sexuality at all. In fact, I was enjoying much more attention as a transgender woman than I ever had as a man when it came to other ciswomen. I think it was because I represented an alternative to many lesbian women who had experienced men in their past and did not identify as “Gold Star” women. Gold Star lesbians identify as women who have never been with a man sexually. To all the ones that did not wear their “stars” proudly, I represented a unique gender middle ground. It helped me too, when the ciswomen I encountered did not have the same sexual hangups that most men seem to carry around with them along with their fragile egos.

Maybe the best part was that I did not have any problems fitting in with my image as a lipstick or femme lesbians and was well aware of all they had in the LGBTQ community to make societal inroads which we always desperately needed. I desperately needed it too as I searched for where I belonged in life. All along I was a femme lesbian hidden behind layers of masculinity waiting to get out and enjoy the world. It was quite the coming out process for me. As I learned I could validate myself as a person without the help of a man which was exceedingly difficult for me to do sexually or mentally. Thanks to all the women I met, I never had to do it.

 

 

Connecting the Gender Dots

 

Image from Beya Yurtzkuran'
on UnSplash. 

Connecting all the dots in a life when you have gender issues is never easy.

Especially so when your life’s workbook is completely blank and you have nowhere to go but to struggle. The great majority of transgender women and transgender men grew up with unapproving parents and/or no peer group pressure to shape our gender youth and help us along. At the best, the closest dots we were trying to connect were fuzzy and far away.

On the other hand, with me, my male dots were always crystal clear and easy to at least try to connect. If I was successful on a sports team, I would connect an easy dot is a great example. But if I was cross-dressing as a girl in front of the mirror, I was always confused on how I should act or feel. The only certainty I had was I knew I wanted to feel pretty.

As I progressed through life’s lessons, I learned the impact of achieving the connecting of my feminine dots while at the same time, leaving my male ones behind. Sacrifice became the ultimate name of the game. Especially when my second (out of three wives) kept calling me selfish for my complete pursuit to begin to leave my male past behind and live as a complete transfeminine person. What made matters worse was the fact that my gender dots on both sides of the spectrum were becoming clearer. I was becoming more successful as a father and as a provider as I advanced in my chosen profession, but at the same time, I became better and better at presenting myself as a convincing woman. For the longest time, my dots formed a parallel path. Heading ultimately for a collision.

I was stubborn and tried to separate the dots I was connecting until it affected my mental health so badly I could do it no longer. I was like a juggler trying to balance the two main binary genders as fast as I could and it nearly cost me my life. I was finding it harder than ever to separate my old unwanted male self from my new exciting yet terrifying new feminine self when one side began to bleed into the other. For example, when I was in a company meeting full of men, I would daydream how it would be if I was there as the only woman. Before reality would slap me down and back into the present.

Finally, I could take it no longer, and I began to give up on connecting any more of my male dots at all. I figured if I connected any more dots, it would just create more baggage I would have to deal with when I male to female transitioned. Mentally, I began to make contingency plans on what to do when I could ever connect my female dots and live out my dream. It is when I began to kick my experimentation portion of my life into high gear. I wanted to make certain as little as possible would be standing in my way as I moved forward in life. I needed to deal with the possibility I would lose contact with my wife and family then figure out what I would do to support myself financially. I was fortunate when my daughter stuck around to support me when my only remaining blood relative (brother) did not and I was old enough to support myself on an early social security retirement I earned and selling collectables my second wife who tragically passed away, and I collected over the years. So, I had connected all my obvious dots fairly well.

From there, the most challenging aspect of life I needed to face was the actual one on one daily living a trans woman has to take on. Learning the lessons a ciswoman is raised to know as she transitions from a female to a woman. Such as the shifting from white male privileges to the female privileges that I had only had the chance to dream about and not know because I had never been allowed behind the gender curtain. Once I was allowed behind the curtain, many aspects I never fully realized ciswomen actually go through became a reality to me. I was connecting my dots and maturing into the transgender woman I always dreamed of becoming. All my misconceptions about just achieving the appearance aspect of femininization faded away as I learned there was so much more to me than just trying my best to have an attractive face. It was quite the shallow existence for me as I needed to develop myself into a quality new human being that the world reacted to on a everyday basis.

As it turned out, HRT or gender affirming hormones took final care of the attractive part of my being as I went from being attractive to being the real me. Because the hormones softened my skin and facial lines and helped me to grow breasts, hips and hair. Like I said, all of which were the real me just waiting all this time for the changes to happen.

All the dots I connected were in a big circle. I went from a young boy for the first time being amazed at what he saw in the mirror (and wondering what was next), all the way to being able years later to being able to find the real me and live out my goal of crossing the gender border into a transfeminine world. I could not wait to give away all my male clothes; enjoy the new hormones I was on and live a new life. I was even able to take vacations with my third wife Liz to places I had never been before. All as my new self.

I can’t say connecting all my dots was ever fun and at times very scary, but they were always with me as I lived my life. At my advanced age of seventy-six, I am fortunate that I had the chance to find the real me before it was time for me to connect the final dot and step into the next dimension.

 

 

 

 

 

 

 

Stopping when You are Ahead

 

JJ Hart. Girls Night Out.
I am top left. 

Somehow, I never learned to stop when I was ahead when I was growing up. Or, as my parents always said, I tried when I was given an inch, I always tried to take a mile.

That whole idea really manifested itself when I began to explore my gender desires and start to cross-dress in my mom’s clothes. As I perceived myself to be successful with one new look, I always wanted more very soon. I could not stop when I was ahead and kept on pushing the boundaries of danger when I cross-dressed at home in the bathroom. Even if my brother was home too. I was risking what I had of the young male life I thought I needed to protect.

Somehow, my guardian angel was looking over me as I never got caught as a kid with my cross-dressing activities and I simply wanted more than I could get most of the time such as a nice, fashionable wig. Rather than the Halloween store wigs I was stuck with. Due primarily to financial constraints. During this time of my life, I was stuck with just being able to dream of what my life could be like when I grew into a more complete transfeminine person. It turned out to be a long (decades) away from coming true. Take wigs for example. When I finally arrived at the point where I financially could afford it, I went overboard on haunting the local wig stores around me looking for just the right wig which I thought would be the perfect addition to my hair collection to allow me to present better in the world. As I did it, mostly all that I accomplished was acquiring quite the collection of potential drag clown wigs which I did not have the patience and/or knowledge to take care of.

At that point, I could not stop when I was ahead or behind my quest to be at least an attractive woman. Every time I experienced the least little bit of gender euphoria when I went out in public, it fired me up and encouraged me to do more. Unfortunately, that meant taking extra chances with my actions and ultimately my safety. I needed to learn the hard way what ciswomen were raised to know about not putting yourself into potentially dangerous situations. I barely lucked it out when I escaped situations with no harm to me, so I essentially did not have to stop when I was ahead as a trans woman. I just had to be wiser when my male privileges were stripped away such as the personal security privilege men inherently have.

As I emerged as a wiser novice transgender woman, the reality of what I was attempting set in and I could not stop. Even if I was ahead. I began to set up a stairstep approach to my male to female feminization process which would I hoped, give me a more in-depth look at a woman’s life behind the gender curtain. Which I had spent countless hours thinking about. I started to consider all the things I wanted to discover as a woman that I had dreamed of as a man which led me to set up my own transgender mental bucket list of things to do. Basically, I set up activities at levels of difficulty. So, when I accomplished one I did not have to stop and move to another. Using the women’s room was a prime example of sliding behind the gender curtain and using a women’s only space. I knew a little of what to expect from my days as a restaurant manager when I needed to monitor how the women’s room was kept for problems I could encounter. Not starting from scratch helped me to survive in my new world with cis women.

Fortunately, I spent much of my time in the world successfully as I learned the basics of how ciswomen live. By doing so, I simply could not quit and kept on trying new things. My bucket was quickly being worn out by the challenges I was facing. Mainly by meeting the number of women who showed interest in me. I have always thought they were just curious about what I was doing in their world and was I living my life the best I could in the girls’ club. In my case, I was different and hopefully presented the best of the two main binary gender worlds as I socialized with many different women who seemingly were happy to see me.

By this time in my life, I simply could not stop what I had started as far as chasing my femininization process. It involved doing a deep dive into how women communicate and compete with each other, among other important things. Probably, communication was the most difficult aspect of my transition to learn. For the first time in my life as a transwoman, I needed to listen closely and completely to what was being said to me for hidden meanings and nonverbal cues. Then, as far as competition as a woman was concerned, I needed to learn that women compete just as hard as men. Just on a whole different spectrum of passive aggressive actions and reactions. Believe me, I learned the hard way a number of times when I made the wrong move and needed to watch my back from a smiling face who was out to get me.

Once I succeeded in learning all of my feminine lessons, my confidence was at a all time high. Especially with the small group of lesbian friends I had build around me by sheer luck. They ended up protecting me during my fragile times I was learning the final ropes of what it would take to round myself out as a transgender woman. By this time, my inner self could take over after being buried all those years and end up running my life’s goal that she always had a hand in. After waiting all those decades to live, she no longer had to stop while she was ahead. She was home and I was a whole person.

 

 

 

My Life's Passion

JJ Hart on vacation
last winter. 

Without a doubt, the one passion which has consumed my life the most has been my desire to be a woman.

I continually write about my youth as a confused boy wondering if I was the only boy in the world who wanted to be a girl. My desires extended all the way to what I wanted for Christmas (the doll baby I never got) all the way to when I lied about what I wanted to be when I grew up. Rather than rock the boat I always said some sort of a male profession such as a doctor or a lawyer rather than what I really wanted to be, a woman.

All I could do was take refuge in my mirror which told me I made a pretty girl out of the boy I was at the time. It became a passion for me to use as much of my free time as possible to cross-dress. At the same time, I became really good at acting like a boy by playing sports and having an interest in cars. I was so good, it kept the bullies away until male puberty invaded my body. Outside of hating the changes puberty was making to my body, I remember being intensely aware of my new masculinity and what to do with it. Even walking like a man was a chore for me to learn to do. I was so afraid of walking like a “sissy” and be made fun of by the bullies that I feared what to do. Little did I know that later in life my passion would be to unlearn all that I needed to learn at the time about being masculine.

As much as I tried and as tormented, I because of my gender passions, I could not seem to lose my desire to be feminine over my hated male image. At the time, I was in the midst of what I call the information “dark ages” before the internet and any social media input. Even the word transvestite was new to me as I struggled to find my footing in life. In other words, my gender closet was very dark and lonely, with little opportunity to have any future at all in my passion to understand and be feminine.

I stayed that way until I grew older and my passion included receiving my cherished issues of “Transvestia” magazine and I could read the “wisdom” of “Virginia Prince” whenever I could get my hands on another issue. For a while I thought it was working until I began to read about the social mixers certain chapters had to meet and greet other cross-dressers or transsexuals as they were known back in those days. Amazingly, one of the chapters in my native Ohio held mixers on a fairly regular basis that I could attend. I thought for sure, meeting others with similar gender issues could help me but I was wrong. Their passions exposed the many layers of where I could fit in (or not) with the remainder of the cross-dressing community and at the least, I hoped I could come away from the social by making a friend or two.

The only thing that really came out of the mixers was the knowledge that another chapter was coming close to establishing their own socials in Columbus, Ohio which was vastly closer for me to attend. Maybe I was too standoffish or even shy to make what I would call friends, but I continued to keep going any way and even was rewarded with invitations to smaller more diverse parties in Columbus which did not have to supposedly adhere to all of “Virginia Prince’s” archaic rules such as admitting heterosexual members only. As I said, the parties I went to were very diverse from lesbians to cross dresser admirers all the way to transgender women getting ready for gender realignment surgeries. The learning process I went through every time I went fueled my passion to learn more about my place in this new exciting world, I was becoming a part of. I could not wait to be invited to the next party.

I felt so secure from my party experiences, that I decided to do more exploring in my own in public. That is when I began to seek out the straight venues I used to go to as a man when I always wondered what it would be like to experience them as a woman. My passion for my new life exploded when I discovered I could be accepted which kept me out of the gay venues which I did not feel comfortable in at all. I was able to go out to be alone and mostly socialize by myself for the most part as I worked hard on my passion to fill out my gender workbook which was seriously lagging behind my fast-paced life as a novice transgender woman.

By this time, I had decided I had made the right decision to follow my feminine passion and try to survive in a world run by ciswomen. My path felt natural and I was rapidly coming close to the time when I was going to push all my male privileges I had earned to the middle of the table and bet my life on the transfeminine path I was on. I could not believe that my entire life’s dream/goal was suddenly within my grasp. If only I had the courage to finally follow through on my passion.

I did follow through and with the help of my future wife Liz, I went on HRT, threw out or gave away all my male clothes and never looked back on my male life except to decide which baggage to bring with me. I even went as far as taking female vocal lessons to try to teach me all important feminine communication skills which I desperately needed. It all turned out to be a labor of love as I listened and learned from the world around me.

The boy so long ago in the mirror finally had his deep-seated passions rewarded.

 

 

 

  

Burning my Gender Bridges

 

Image from Kellen Riggin 
on UnSplash. 

Sadly, following  my gender path included burning many bridges behind me which connected me to my old male past.

I think the problem stemmed from the self-destructive behavior I always exhibited when I did anything remotely successful as a man. I still had not yet faced the fact that I wanted nothing to do with being a guy, and everything that came with it. Including the potential of living with the white male privilege that was an automatic addition to my life.

Then, there was always the part of relief if I was ever caught cross-dressing early in life. Finally, I would be exposed as the deeply feminine person I really was. Life was much simpler back in those days, and I wondered how bad it would be to go to a psychiatrist and try to explain to him or her how I was not mentally ill; I just wanted to be a girl and my ultimate goal in life was to grow into a woman someday. The only way to get there was to risk everything and not get caught, but I never did and did not have to burn any bridges to find my way into early forms of conversion therapy.

It was not until much later in life did, I really began to torch my bridges behind me. The problem was, I needed to build my bridges longer and stronger to carry all the increased male baggage I had accumulated. Most of which was against my will. This was when my male life was outpacing my female life and I was building a small family and a very good job while at the same time managing to hang on to a long-term marriage where my wife was learning about and fighting against any thoughts of me sliding towards leading a transgender lifestyle. I desperately did not want her to be on any bridge that I burnt, and the pressure built on me not to light the match on my life if I took the huge step and decided to keep femininizing myself.

As I reached deeper and deeper into myself looking for an answer, I felt increasingly natural when I was attempting to put together my feminine self. No matter how risky burning my previous gender bridges behind was, I could not shake the idea I was doing something right by transitioning my old male life away.

The next big problem I faced was letting the world I was in know I was switching from my male club membership to the girls’ club. As I was being increasingly successful in carving out a new secret life as a trans woman, I did not want it to be secret any longer. So, I did the natural thing for me, I tried to make it impossible for me to turn back on my gender path. I started to go into my own restaurant dressed as me to see if I was recognized which I quickly was. I could have lost my executive general manager’s job immediately if I was but I was prepared to burn that bridge when I came to it. Looking back, it was not the smartest decision I ever made in my life but one I was desperate to make as my female self was crying out for attention.

When I progressed to a certain point in my male to female transition plan, burning bridges became just an automatic part of the plan because I did not need the male part of my life anymore, I was getting rid of. The prime example as I always point to is the night that something had changed in my thinking that I was not cross-dressing to go out and socialize, I was finally trying to formally join the world as a full-fledged transfeminine participant. The evening was a resounding success, and I knew from that point forward that I could never go back to being a man again. I could see my bridge burning over a not-so-distant horizon and it actually was scary and good at the same time.

I probably would have burnt more bridges earlier in my life if it was not for my second wife and my male self who was hanging on for dear life but still refusing to give up his hold on me. They put up a formidable fight to the point of putting out the fires I started on purpose. It lasted until my wife passed away, leaving only my weakened male self to fight me.

The final bridge to burn was when I was approved for HRT or gender affirming hormones. It was an all hands-on deck torching when my external and even internal body began to change. My sudden change in skin tone, slightly protruding breasts and longer hair which I refused to cut gave my external transition away and the part no one saw, but I felt, such as my emotional growth made itself known to me.

Following years of gender turmoil and change, having nothing in my way felt very good and I loved the hormonal changes I was going through with my new wife Liz. Which was well over a decade now. As I said, burning bridges in my life was always a scary idea but one I needed to do to get to where I wanted to go as a transgender woman surviving in the world of ciswomen everywhere.

I was fortunate in that I did not get burned as much as I did along the way in the process. I must have been quicker than I thought as my trans destiny showed me the way during the darkest nights. Who knows? Being caught on one of my bridges may have been for the best when I needed to work my way out of danger, but it never came to that with me. I became quite good at burning my bridges…or lucky.

Thanks to all of you who have taken the time to comment, clap or subscribe and just read along with me.

Without you, it means nothing!

 

 

 

 

My Gender Workbook was Blank

 

Image from Marcus Winkler
on UnSplash. 

Somedays, I prefer explaining the trip up my gender path as filling out my gender workbook. Of course, the problem I had doing it was I had absolutely no help. No mother or peer group pressure to tell me if I was doing right from wrong when it came to cross-dressing myself as a girl or applying makeup.

Ironically (as I said in a recent post), knowing my mom the way I did she would have been against me shaving my legs and wearing makeup as early as I did as her secret daughter. I was only trying to get a head start on writing my own gender workbook and trying to catch up with all the girls around me who also were sneaking around wearing makeup and wearing panty hose.

It was fairly easy for me to make up my own workbook rules when it was just me and the mirror to deal with. No matter what I did as far as my feminine presentation was concerned was accepted by my mirror which kept lying to me and telling me I was a pretty girl. Which was much easier before I hit the curse of male puberty and all the changes my body was going through. I was seeing unwanted growth and angles while the girls I envied around me were getting curves. When I went to bed every night, I dreamed of my life being different but of course it never was. I would not get the curves I wanted until decades later in life when I was fortunate to have good health enough to be able to start HRT or gender affirming hormones.

There turned out to be tons of effort I needed to put into my workbook before I could arrive at the point where I could even think about starting hormones. The shortcuts I kept trying to make never seemed to work and usually got me in trouble. When I did find trouble by trying to do too much with poor fashion choices, finally I gained some sense, rewrote my gender workbook and went on to successfully try to blend in with the world of ciswomen as a transgender woman. Looking back, I think that page of my book had so many erase and start over marks that I could barely read it.

When I really began to get serious about seeing if I could be successful as a trans woman was when I desperately needed my gender workbook to help me, but it just couldn’t because I had not put the time and effort into filling it out. I had never given enough thought to how different the lives of men and women really were. Perhaps you remember the book “Men are from Mars and Women are from Venus” which when I read it, I wondered where trans people came from. I did not know yet we transgender women and transgender men get to occupy a special planet all our own with our unique knowledge of both men and women.

As I first began to mature into a more complete transfeminine person, I sometimes discovered my mental gender notes became overwhelming, and I needed to head back home to go over in my mind about what just happened to me. Good or bad, it did not matter. What was most unexpected to me was the amount of acceptance I received in the new world I was in. I had become used to the glares and abuse I took when I went out of the house in my early days and learned the majority of the world did not care about me one way or another. All the way to those other women who encouraged me to be in their world. Nowhere in my gender workbook did I ever imagine such a thing ever happening to a person like me just trying to find a new foothold in the world as my authentic self after all the years of struggling.

Sadly, there were still times when I ran out of ink to write in my gender workbook, and I attempted to purge everything I had accomplished and go totally back to my old safe male world. As most of us know, purges never work, and before I knew it I was out buying more feminine clothes and makeup to femininize myself all over again. By doing so, I finally came to the point of stopping obsessing over how I looked and settled into just being the person I was meant to be all along. I just did not want anything to do with me being a privileged male anymore, I just wanted to live out the long-held dream goal of mine to live as close as I could to a woman.

Even at that point, my gender workbook was different than other trans women friends I had known when I made the decision to live my life without all the major gender realignment surgeries and facial surgeries the others had gone through. I had two comments which described me the best when a transwoman friend of mine said I passed out of sheer willpower and another which came in on a comment and said I was just another old guy on hormones. Both were right in their own ways, and I wrote a mental note in my workbook that I would never be the prettiest woman in the room, but I could be the nicest. As far as the comment on me being an old guy on hormones, I wondered if the commenter was just jealous and it did not matter anyhow because I had always considered my gender to be between my ears and not between my legs and I had made it through life as far as I did with no surgeries at all, so there was no need to risk damage when I was older.

Also, I was fortunate to have been able to have other ciswomen around me help finish my gender workbook to where it is today. More than they ever knew, they taught me how to validate myself as a trans woman and welcomed me into their world. A major accomplishment in my life.

 

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.

 

 

 

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.

 

 

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.

 

 

 

 

 

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.