I Wanted it All

 

Image from Sindy Sussengut
on UnSplash.

During my gender journey through multiple transitions from cross-dresser to transgender woman, I have been selfish and wanted it all.

It all started very early when I was experimenting with mom’s clothes and makeup when I had the first idea all that I was doing may go deeper than just wearing feminine clothes. I did not have the terminology or knowledge back then to work my way through it, but in reality, I was discovering I was more transgender than anything else. In the years to come, that would be a major point to think about along my gender path.

As I grew through my first two marriages where both wives knew of my cross-dressing desires, my first wife was far less demanding than my second and on numerous occasions during fights we were having about me, my second wife rightfully pointed out that our relationship was not all about me. Since I was in the middle of an obsession with my appearance and all things related to makeup, as I said she was right and I was needlessly selfish about our relationship. She was far wiser than I and knew even at that early time in our marriage, her husband was slipping away.

Even though I loved her dearly, I still could not stay away from the powerful draw of wondering if I could ever achieve living fulltime as a transgender woman. Deep down, I knew my second wife would never come with me on my journey as she made it abundantly clear she never signed up to be married to another woman.

With a lot of work and repetition, I did finally get better with my wardrobe and makeup and then needed to figure out how to sneak out of the house and get into the world. It basically meant my imagination had to go into overdrive as I tried to think of reasons I needed to explore the world as my new true transfeminine self. Even if I was not sure what the word meant back then. I went as far as going to the grocery store for my wife who was working on the days, I was off and combined the trip by going to a nearby big box store to shop for panty hose and makeup. My biggest takeaway came when I noticed very few people were noticing me and I started to think I wanted to experience more. My restless feminine spirit was dominating me again.

At the same time, I was doing all of this, I was still searching for my dream job in the commercial restaurant business and after switching jobs and locations several times, I finally did. As I finally broke free of my fast-food background and landed a job with “Chi-Chi’s” Mexican Restaurants in the Columbus, Ohio area where I had ties to. It was a win-win situation for me because I was back home again and could start to interact with the diverse small LGBTQ group that I had known from years previous. This was the tight knit group that had several transgender women who were on their ways to gender realignment surgeries, and I could pick their brains on what it meant to do it. Even though, I did not have the resources or the willpower to consider such a radical move for me in my future, Just being considered as an equal in their group was good enough for me…then.

I say “then” because in life everything rarely stays the same. As I continued to break the vows I had with my wife, I kept going out to venues from the house and began to actually carve out a life as a transgender woman with people who had never known my male side. Wanting it all was staring to mean so much more to me than ever before as my male life began to slip away from me and wanting it all increasingly meant an ongoing break with my long-term marriage of over twenty years. Because she was not giving into her demands, and I was discovering just what mine should be if I was willing to risk it all to live my dream life. Sadly, it would have to be all me to do it as I tore down everything I had worked for as a man to start over in a woman’s’ world.

Sure, I was scared to death as I decided to keep concentrating on the feminine me who had waited so long to live her life. But the whole process and path I was on felt so natural, I decided to be selfish and continue it. By proceeding along the path I was on, I needed to take several abrupt detours when I had problems with deciding my sexuality all the way to just basically communicating with the remainder of the world I was in. Which I discovered was made up of ciswomen not so unlike my second wife. Many were strong and sure of themselves and set up forms of communication which were totally foreign to me as I was coming from a male world. Suddenly, I needed to adjust to forms of non-verbal and passive aggressive communications which were reserved for use when cismen were around.

Perhaps my best selfish move I made was to be approved for gender affirming hormones or HRT which enabled me to come closer to my transgender mentors of so long ago. Since I had ruled out any surgeries, the changes from the hormones would be as far as I could go to sync up my female mind with my male body.

By this time, my wife had passed away and there were very few people left who knew the old me at all. So, I was mostly all-alone with my new emotions and bodily changes such as hair, breasts and hot flashes. When I reached out to any of my lesbian friends, all they would say was welcome to their world. Little did they know how badly I wanted to be there. I was rewarded by the fact that the people who knew the male me told me they thought I was much more relaxed and happy now.

Since I can now love more deeply than I ever could as a man, my life has come full circle to encompass feelings I never knew I had before. All because of my selfish one sided past to get here. I wanted it all and finally was able to find it.

Thanks for reading along and I would be remiss if I did not mention two things. Thanks to Grace Ann Hansen for publishing my stories in her “Empowered Trans Woman” site!

And sadly, I would like to mention the passing of a true icon, Dolly Parton who was a staunch ally of the LGBTQ community. She will be severely missed.

 

 

 

 

Dealing with Gatekeepers

 

Image from Ries Bosch
on UnSplash. 

Unfortunately, all the people who see it as their job to be a gender gatekeeper can run the spectrum from nice to nasty.

The nice ones are just normally curious as to what you are doing in their world and will sometimes even help you come through their gate and cross the gender border you so desperately want. Then there are the other ones who sadly make a bigger impact in the world when they overstep their bounds and attempt to keep transgender women or transgender men from ever entering their spaces.

My problem with gender gatekeepers is who gave them the right to do what they are doing anyhow. I see the titles of woman and man as socialization words only. Meaning just because you were born female or male does not mean you are ever socialized enough to earn the title of women or men. I fear the ones who never deserved to be called a woman became the gatekeepers who are trying to stop us transgender women from ever achieving our socialization goal of at least being able to have a feminine life which includes entering spaces such as restrooms.

During my life, I have met both sides of gatekeepers. I have seen it all from being called a pervert in one women’s restroom to being helped to an empty stall in another. Then, there was the Lesbian Valentine’s Day dance Liz, and I went to years ago in Cincinnati. While Liz went up to the refreshment area to get us some appetizers, unannounced I was approached by this lesbian ciswoman who wanted to know what my “real” name was. She was nasty and naturally, I would not tell her anything about me because for some reason she took it upon herself to be a gatekeeper where she did not need to be.

Because I was completely and quickly kicked out of the men’s club when I transitioned, I did not have to worry about very many male gatekeepers. I still remember vividly attempting to join a conversation when I first came out between men when they were dealing with a subject, I knew a lot about and was quickly ignored. It reinforced in me how much I would not miss getting kicked out of the men’s club and sought out the company I really wanted which was with women. As I realized I had always felt that way and life had just got in my way as I always had been pressured to find and date a girlfriend as a male. Ironically, I was very shy and afraid to challenge the feminine dating gatekeepers to even ask a girl out. I finally overcame my internal gatekeepers with the help of friends who set up dates for me with unattached girls they knew.

As I began to explore the world increasingly, I began to meet and utilize more feminine gatekeepers to my advantage. I started to realize how much more ciswomen were secure in their sexuality than cismen and were not afraid to interact with me. Plus, when they went out of their way to do so, at the same time it gave me a chance to learn so much more from them. With men, if most of them even talked to me, they felt somehow, they were gay. Again, I was happy the male gatekeepers kept me out.

Then, let us not forget the most extreme gatekeepers of all, who are the TERFs (or Radical Feminists) who have even teamed up with groups of Evangelical Christians to keep transgender folk from crossing gender borders. There is nothing I dislike more than having a so-called Christian tell me they will pray for me as they jump on the gatekeeper’s bandwagon.  

Sadly, gatekeeping still exists in the gay and transgender community as the Log Cabin conservative Republicans have recently announced they would be taking the “T” out of their LGBT language. I always use them as an example of what will happen when the current administration grows tired of coming after a minority transgender community and comes after a larger gay one.

Even sadder yet are the transgender community members I have known over the years who have tried to exclude certain trans women for not having as many gender realignment surgeries as they have had to prove how trans they are. And they are nothing more than glorified cross-dressers. As if there was anything wrong with being a cross-dresser which most of us started their active transition to being a transfeminine person by experimenting with their mom’s clothes.  Who must say that in the future, the cross-dressing person you shunned may want to do more in their gender life and blossom into their full desired gender lives.

These days, with how divided the country is, it is so sad that so-called normal people are ready to jump into other people's business and become novice gatekeepers. Who gave the woman the right to call me a pervert or even transgender women chiding me for wearing pants too much and who needs to know my previous name except for me anyhow. I know all humans face gatekeepers in life, but it seems the trans community faces more than their fare share of people attempting to exclude us. To put it another way, I faced way too many four way stops on my gender path to finally living my dream, Seemingly, destiny had to show me the problems of living with then losing to death a disapproving wife all the way to losing friends and my brother when I transitioned across the gender border to be a happier person.

I guess I was lucky I wasn’t on a toll-road where the gatekeepers wanted a payment for passage. If I was, I would be broke by now and I was lucky to have received so much more than I lost as I carved out a new feminine life.

Hopefully, you can navigate your gates successfully as you move along your gender path.

Thanks for stopping by and sharing my lifetimes worth of experiences! Any comments are always appreciated.

 

Help Me Out of this Box!

 

Image from Tamara Bellis
on UnSplash. 

Since I was born “AMAB” (Assigned male at Birth) I was automatically put into a box I could not easily get out of.

Plus, I had the extra disadvantage of being born into a very male dominated, competitive family, so my box was harder to get out of. Like many of you, I had to sneak around my family’s back to even cross-dress into mom’s clothes and makeup to feel better. The worst part about it was that I did not understand why I wanted to be feminine and felt so all alone when I thought about it. Society had done a good job of building a sturdy box around me with very high sides to see the world out of.

As life went on, I learned to be self-sufficient as I hid my gender truth from the world. Very early on I learned I wanted to do so much more than just look like a girl, I wanted a chance to live their life. But I needed to escape my box somehow to do it with absolutely no help from anyone at all. There were only the girls at school for me to envy and try to copy myself after I returned home and had a chance to cross-dress again in front of the mirror.

When I first tried to take myself out into the public’s eye for the first time, it was difficult leaving my box to do it. I was safe there, and I could be the pretty girl I always wanted to be without anyone questioning me. Even though I was not surviving the world well as a novice cross-dresser walking through the malls that I knew, I was determined to keep trying until I got it right. That is if I ever could as I was very insecure in thinking I ever could come close to my dream of living as a woman.

As life always does, it got directly in my way of ever getting out of my box. The only way I could try very early was by going to Halloween parties dressed as a person who I really wanted to be in life but could never tell anyone. At least at Halloween, I could show the world the transfeminine me and hope it did not wreck my life at the time before I could scurry back to my box and hide again. The problem with Halloween was it only happened once a year and I couldn't wait for the next one to show off my feminine spirit. It all led me to gaining a greater awareness to who I really was and how much I needed to expand my world as a new transgender woman in the world.

Another problem I had was having two strong influences around me, who wanted me to stay in my box and even make it stronger. The two were my male self and my second wife who had everything to lose each time I gained more confidence as myself. They did not understand the turmoil I was going through myself and could not help me, I was on some sort of a gender roller-coaster with all its ups and downs. One of my major ups or gender euphoria came when I was mistaken for a ciswoman at a cross-dresser, transgender mixer I went to one night without my wife. That was certainly the high point, but then the lows began to hit me when I was firmly stuck back in my box with no way to experience the next high. Sadly, I did not know where my life was going to take me then. Except for the small idea that I might have the appearance part of my gender puzzle solved.

More frustration sat in when my wife told me there was so much more to being a woman than just looking like one and I was stuck with no real way to understand what she meant. I was still operating as too much of a cisman to be allowed to be behind the gender curtain to understand all the complexities ciswomen go through in life. To make up for it, I tried to adopt female mentors to learn from. Immediately I chose my mom and my wife to learn from because they were both strong, independent women whom I wanted to be like. It was a true jump for me to go from being a shy trans woman hiding in my box at home to getting out and trying to find out if I could live my life-long dream. What I did was build up confidence slowly until I could shed my male self and his privileges and just do it.

Little did I know, when I did shed my male self, I would end up bringing a big part of him with me. I made him my beast of burden when he carried what was left of him into my scary, yet exciting new world. I learned again how complex ciswomen were and if I wanted to watch sports on a big screen television with a beer in front of me I could and not feel out of place as a transgender woman.

In many ways, I was dismantling my old box and using the pieces I needed to construct the new me who had always been there but had nowhere to live. It felt great for once to feel free of all the old male constraints I had to live with. I had many, so the path I embarked on became very complex as I sorted out exactly who I wanted to be. Plus, I needed to be careful to finally judge when the best jumping off point for me to put my old male self behind me and start a new one. A unique spot that most humans do not ever have the chance to do.

If you are considering what you will do with your gender box, just be careful when you deconstruct it because it can contain many hidden problems. On the other hand, you are embarking on an exciting journey if you can make the best out of it.

Thanks for reading along with all my lifetime adventures as I attempt to bring our gender struggles into focus. Taking the time to read, and comment too are always appreciated!

 

Try then Try Again

 

Early Days in my Gender Closet
JJ Hart.

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

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

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

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

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

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

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

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

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

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

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

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

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

 

 

I Was Risking it All

 

Image from Leo Visions
on UnSplash.

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

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

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

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

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

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

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

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

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

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

 

I Had No Idea

 

Image from Hayley Lawrence
on UnSplash. 

As we dodged yet another terrible weather bullet where we live in this part of Cincinnati, and I sit here writing, I feel a deep sense of belonging in the life I discovered years ago.

Certainly, through most of my life, I never thought I could make it this far and live out my own dream of living as a fulltime transgender woman. Possibly, it is because I got off to such a rough start when I left my gender closet and took on the world. Back in those days also I had such a simplistic view of what it would take me to live as a woman. I mistakenly thought I would just have to look as close as I could to a ciswoman. I had no idea of how wrong that would turn out to be.

What I had never really considered was how difficult it would be to truly cross the gender border and face all the everyday challenges ciswomen face in the world. Including the ones from toxic men. In that sense, I was fortunate in that I was not attractive enough to garner much attention from cismen at all and only had to deal with the new surge of attention I received from the women around me who mainly wanted to know more about what I was doing in their world. What the women never knew was when they were studying me, I was closely studying them because I was on a crash course to learn everything, I needed to be accepted into their club and be allowed behind their gender curtain.

Referring back to a recent post of mine and a comment from “Mark”, I was excited to be finding the true me and I enjoyed the excitement of being in a new world I always wanted to be in. Probably because I thought it would never be me who could do it. Thanks for commenting, Mark!

Change was slow, but eventually the confidence came that just maybe I could exist in a world where ciswomen ruled and make it. It was only then when I had any idea that it could be me that made it into the world I knew from my transgender mentors I had met at the parties I was going to in Columbus, Ohio. At that time, even though I had very few certainties of where I would end up in life, if I had my choice I rather be like the trans women I knew that the part-time cross-dresser than I was. It was my dream and I was sticking to it. Even though I knew I did not have the natural resources or the financial means to be as beautiful as my friends were. I realized that all ciswomen were not classic beauties but lived fulfilled and impactful lives anyhow. So, there was a path for me anyhow.

My new idea opened a whole new vista of being femininized for me. It meant so much more than the makeup, hair and pretty clothes I was having a chance to wear for the first time. Suddenly, I could see a path forward to where I could see the real me for a change. A person that I had no idea about was there but liked it when I discovered her.

Now is the time I always take to explain how difficult this part of my life was. It seemed nothing was coming easy to me as I struggled to find a middle point with my second wife over my gender desires and my work was making new demands on my male self. The worst part was that the idea of who I was internally was becoming clouded and I lost sight of where I needed to go to find me. As I grasped for answers, I could not wait to get back to my safe place in Columbus and interact with the diverse LGBTQ group of people who always gathered there.

It took a while, but I finally gathered the courage to set out on my own to see if my idea of making it in the world as a transfeminine person was dead. The problem was that I only had known the world of gay venues to attempt to express myself. Since I had never identified as a gay male, I never felt at home in their venues, only lesbian bars and large straight places. I needed an extraordinary amount of courage to begin to see if I could exist in both at all. When I found out I could, almost nightly if I was not working, I was trying out the new world I was carving out for myself. No matter how hard I tried to blend in with everyone else, I did not to the staff of bartenders and servers who routinely took care of me, and I was unmistakable to them and had no problems becoming a regular. A smiling face and good tips took care of the rest.

Long story short, I was finding myself as the person I had no idea I could be. Before I knew it, I needed to settle on one wig and decide on a new feminine name for me to use in every venue I was in regularly. The pressure was on to not lose everything that I had gained over the years, and this time I could just start all over again building a new woman from the building blocks of my male life. The prize I never thought I would ever get was suddenly within reach, and I needed to figure out what to do next.

That decision was made for me when my second wife as well as the only good male friends I had ever had all passed away in a short span of time. I was left by myself to decide my future which without much thought turned out to be female. Yes, the idea I never thought would come true was, just when I thought again that it never would. I am a living example of how someone’s life can change if you stay on your gender path. Especially when you don’t expect it. Sadly, I remember the dark days when all I had was two dogs to comfort me in my times of duress and I had no idea I could ever climb out of my depression to where I could find the support, I needed to live my dream life.

It turned out for me that my grand idea was a good one after all.

 

 

Your Lines in the Sand as Gender Markers

 

Image from Sonnie Hiles
on UnSplash. 

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

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

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

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

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

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

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

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

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

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

 

 

It's All in the Details of Gender

 

Image from Liam Nguyen 
on UnSplash.

Quite early in life, I learned to pay attention to the details when I followed my instincts and started to cross-dress into mom’s clothes and try to put on her makeup. I thought all was good after I had snuck around and managed to shave my legs again without anyone noticing.

That was until I snagged mom’s hose on an unkept fingernail and ran yet another pair of good stockings or pantyhose. I learned the hard way to take better care of my nails as well as the rest of my body on my path to femininity. Little did I know, paying attention to just the smallest of details would rule my world as I climbed my gender path towards my dream of living fulltime as a transfeminine person.

My major problem was that I was restricted to viewing what a woman’s life was like from the outside in a male dominated family. Through it all, my mom became my mentor and role model more than she ever knew and it went way past just using her makeup and wearing her clothes. I could see how she worked behind the scenes to make sure that the family ran as smoothly as possible. Way past all the traditional female duties such as cleaning and buying groceries. She taught me all that a ciswoman could be at a young age. All the time not realizing what she was doing because she actually had a daughter, not a son.

It was not until I began to get out on my own as a novice cross-dressing transgender woman did; I really have to develop my sense of detail. It was very difficult for me because I was never a detail orientated person. When I went out initially as a trans woman, there just seemed to be so much to concentrate on and remember to do to succeed. Even if I thought I had perfected my fashion, hair and makeup for the evening, there was the problem of putting it all together outside of the mirror and getting all my movements down, so I did not look like a linebacker in drag. The details weighed on me heavily and they were all I thought about in every spare moment I had. So much so that I needed to think ahead to which gender I was at key moments in my life.

It all carried over into life events such as weddings and dances when I had to step back and wonder what I would be wearing if I ever had the opportunity to attend as a trans woman. Sadly, I did get to experience attending a funeral when my wife Liz’s dad passed away after I had transitioned. I wore my best black outfit and did the best I could to blend in properly with all the other ciswomen who attended.

The funeral was just another reality check for me as I needed to face how far I had come in my male to female femininization journey. At my age, I always knew attending a funeral as me was a possibility, but I never knew how real it was until it happened. At that time too, reality and details were becoming increasingly important as I expanded my life in the world to new and exciting groups of strangers such as in spiritual circles and Meetups of writers in Cincinnati. They were the first groups of strangers that I had ever met outside of LGBTQIA+ support groups I attended locally and at the Veterans Administration in Dayton, Ohio. Meeting new people as I said was exciting and kept me active at an exciting time of discovery in my life.

By this time, repetition replaced my need for detail as my makeup habits, along with clothing needs became ingrained as I finally knew who I was in my life. No more searching in a dark lonely closet for an answer. I had it with the help of the world of new and exciting discoveries I was in. I had brief moments of releasing my gender euphoria before but nothing like this before as all the possibilities of the world were opened to me. When I sought out and was approved for HRT or gender affirming hormones. Which I write about a lot. New emotions outweighed the need for details as I moved ever closer to being the person I always wanted to be.

One thing I never forgot as I male to female transitioned was how I was treated early on and how I needed to respond by going back to my cross-dressing drawing board time and time again until I got my details correct. There was so much more to what I was trying to do than my home mirror had told me as I tried to exit my gender closet for good. All I knew was, once I was released from my loneliness, I never wanted to go back. I spent as much time as I could out in the world working on my feminine presentation so I could overcome my testosterone poisoned body and make it.

I cannot stress enough how much of my journey has been filled with fear and or panic when I lost key male privileges such as intelligence and personal security. Details just weren’t enough to help me through all the anxiety I felt meeting strangers in my new exciting world. In fact, just yesterday, I felt the same old twinges of panic sneak in when Liz’s son and I had to take our old lawn mower into the shop for a tuneup. After all these years in the public eye and I still have the same problem is ridiculous I know, but I still do when I am entering predominantly male spaces for any reason. Again, all went well as the young person at the mower place was only interested in taking care of us. Not my gender.

All in all, the extreme work I put into crossing the gender border was worth it as I achieved my goal of living the life I wanted to live. Even though there were times when I did not think I was going to make it.

Thanks so much for joining me with my life experiences. Hopefully you can gain some insight into your life from them. Comments are always welcome!

 

Finding Comfort in your Own Skin

 

Image from Ayesha Rosley
on UnSplash.

I believe the way to finding comfort in your own skin as a transgender person is having the confidence to do it.

Just think of all the time you may have spent in front of your mirror as you gathered the courage to take on the public and work from there. Like many of you, I experienced severe gender dysphoria every time I looked in the mirror and saw a man dressed as a woman and was afraid to go out into the world and face the public. To this day, on occasion, I still suffer from my lack of confidence in who I really am when I look in the mirror in the morning. I do my best to just ignore it and move on and take on my day knowing I am doing my best with what I have to work with. Or as a transgender woman friend once told me, I pass out of sheer willpower.

My willpower was tested during the many times that I failed in public and needed to start all over again. At that time, I had very little confidence that I was doing the right thing with my life. I had to go through years of trial and even more error before I began to build the confidence I needed to succeed in the world as a transfeminine person. When it came right down to it, many times I was excited about the prospect of going through another trial to learn if I could be successful. When I was a success as a trans woman, I wanted to do more on my transgender bucket list of things to try in the new exciting world I was in.

Most the major changes for me came when I began to really look around at what all the ciswomen in the world were wearing and I needed to put away the stubborn attitude of what I thought I should look like. As I began to successfully blend in with the world at large, my confidence began to rise, and I could relax and feel more comfortable in my own skin. It was the beginning of a life-changing gender experience which I discovered I was along for during a very bumpy ride.

In many ways, the ride to being comfortable was like my favorite roller coaster ride at a big nearby amusement park. Often the ride up was slow and uncertain to the top but was made up by the rush of going down the gender hill. It did not take me long to appreciate the rush of coming down my own personal coaster. Even though I feared climbing the heights I was climbing (as well as the threat of falling) the risk was worth it as I began to carve out a small life as a trans woman. Which I always wondered if I could do at all.

I found I could do it thanks to the welcoming embrace of several ciswomen I was introduced to. It was scary yet powerful when I began to receive invitations to special girls ‘nights out. Once I figured out what I was going to wear, then I needed to figure out what I was going to add into the conversation with the other women who I had never met. I desperately did not want to act standoffish and worse yet bitchy by not joining in with the other women who I had a chance to make friends with. Looking back, I think I was successful because outside of one woman who kept glaring at me, I was treated well by everyone else. All this sudden attention led me to a newfound confidence in being in my own natural skin that I never had before in my old male life where I always needed to be on the outlook for someone trying to take away the life I had. I was always competing for what I had earned in a what you had done for me recently world.

The reverse was true in the transgender woman’s world I had found my way into. As I became more confident and successful in just being the me, I always wanted to be, the only competition I ever felt was when I needed to use the women’s room in a venue, I was not a regular in. And even that began to fade when I learned the proper etiquette to use in the typical women’s rest room. There was no thrill in doing just what came naturally, just the relief of being allowed in women only spaces to do it. Taking away any sort of a transphobe’s argument against me using the restroom of my choice.

In my case, becoming comfortable in my own skin was a constant problem which started with the way I was raised. My parents were long on material support and short on any emotional needs I may have had. Which led me to be alone with my gender dysphoria. It was a very lonely, confusing place to be and left deep scars on my internal confidence as I had no deep connection to what my true gender skin really was. The male world I was forced to live in, and the female world I wanted to be in. So, for me, the process of gaining any sense of who I really was a difficult and time-consuming process. Plus. My confidence was so fragile that the slightest problem could send me back to my cross-dressing drawing board to look for solutions.

Over the years, I flat out wore that old cross-dressing drawing board out until I began to figure out my problems were right in front of me. All I had to do was have the courage to do something about them. One of the problems was  they were so much deeper than just trying to look like a ciswoman. I was tired of thinking I was fooling anyone into thinking I was a ciswoman and settled into trying to build myself into the quality new feminine me I wanted to be as I had earned my womanhood from a difficult, unique path.

I seized the opportunity to finally be comfortable in my own skin.

 

 

 

 

 

 

On a Gender Vacation without a Passport

 

JJ Hart

I saw on the news this morning that shortly after the Fourth of July holiday is the busiest time to travel during the year. It got me to thinking about my own major vacations when I shed my male self and began my life as a transfeminine person.

Mainly, I remember the times when I just needed a passport to go past my natural fears, put my cross-dressing past behind me and step into the world of a transgender woman. That invisible passport was difficult for me to come by since I needed to overcome my fragile confidence to step out of my gender shadows to get it. It was difficult because my earliest days of going public as a trans woman were often brutal when the public got ahold of me and I was laughed at routinely. It literally took me years of work in my cross-dressing workbook to get to the point where I could go out into the world and make a good effort to blend in. When I did, I began to earn my vacation away from my male self.

The more vacations away from him that I had, the more I began to appreciate the new world of ciswomen I was allowed into. As rock and roll idol “Billy Idol” was singing, the more I did, I wanted “More, More, More.” (Rebel Yell, 1984) Early on, I was naive and did not realize what I was getting myself into and partially thought my need for a gender passport would eventually burn itself out and go away. But of course, the need to have a passport just burned brighter in my soul. It seemed because of the need for femininity increasingly felt so natural to me.

It turned out at that time, when I was out in the world as a trans woman, either I was getting it very right or very wrong. Mainly because I did not know what I was doing such as how to move the best I could as a woman or how I communicated with other women at the time. Because they were overwhelmingly the only people who were interested in talking to me at all as nearly all men shunned me. I was amazed at how many women in their own unique way wanted to see my gender passport and let me in behind the gender curtain.

It all led me to finally legally change my name with the help of my daughter. We came up with a family name which honored one of my grandparents and my mom too. Who never supported her new daughter, but I forgave her and took her first name as my new middle name anyhow. As a plus, my new initials were easy for my three young grandkids to remember me by, so the name was well accepted by all.

Since I had my new permanent name in place, I could start building a new permanent feminine persona every time I went out to try to carve out a new life as a trans woman. As I was carving, sometimes I hit very hard granite and had to stop and start over until I could find the sandstone softer rock and keep moving towards my gender goal of living fulltime as a transfeminine person. As I carved, I needed to make certain I was always on the outlook for cave-ins which could cause havoc with my male life. Which was still very much in the picture. Because he still controlled most of my life the public saw as well as life with my second wife (who wanted no part of losing a transgender spouse) and a very good job I had at that time too.

As life moved on for me, I discovered brief moments of gender euphoria which kept me going through the dark days of my male to female femininization. Such as when I was able to leave the gay bar venues which I felt uncomfortable in and set out to be accepted in straight sports bars which I knew so well as a man. I was in my gender heaven when I worked my way into regular status in several of the venues I coveted. Once I was accepted by the staff, I could be accepted by their customers also and I thought I had it made. Sadly, by that time the one lesbian bar I used to go to and was accepted in closed its doors and that outlet for me was over.

These days, the closet thing that I have (so far) to an actual passport is my drivers license which has a “F” for female on it and my relocated copies of my name change documents I recently went with my wife Liz on the three-hour round-trip journey to my hometown to pick up. With all the turmoil caused by the idiots in Washington DC it seems in the future I may need a real passport to vote. So, I am getting ready for that if I need one.

Other than that, I am satisfied with the lifetime of progress I have made by having a suitable passport which allows me to live a public life mainly with the acceptance and help of the ciswomen around me. I was able to ignore the occasional hater like the pharmacist long ago when I started HRT who insisted in a crowded pharmacy in screaming loudly did, I know what the Estradiol medications would do to me. Not that she cared, but I promptly took my business elsewhere. It was no business of hers to judge me anyhow and try to out me to the world.

The passport I earned allowed me to open fantastic gender doors that I never thought I could do and the one I need to get will allow me to vote I am afraid here in backwards Ohio. I am not planning to ever travel outside of the country again in my life, so I won’t need a passport for that. Just the one I have already earned the hard way along my gender path.

I would like to take this opportunity to thank all of you who take the time to read along with my writing! It always means so much when you take the time to read and comment.

 

 

 

 

 

The Consequences of Giving Up

 

Image from fast glass fx 
on UnSplash.

When I considered “purging” (getting rid of all my feminine makeup and clothing) the consequences felt like a double-edged sword.

For a few days, the pressure around gender lifted, and I had one less major worry. But before long, the familiar desire to live as a girl returned to my everyday life. I realized that cross-dressing—and perhaps something beyond it—would not be easy for me to give up. Even in that short time, I had learned a great deal and understood how far I still had to go before reaching my dream of living full time as a transgender woman. I was not even sure whether I could make it happen.

Then there were the brief moments of gender euphoria. The time I spent hiding from my brother and family was enough to keep me going until male puberty—and what felt like testosterone poisoning set in. I was unhappy that my body was becoming more angular while the girls around me were developing curves, but there was nothing I could do to stop it.

Even as those changes continued, I could not face the consequences of giving up. I learned to take what I could get until I was old enough to leave the mirror and closet behind and explore the world. What happened next was brutal. I discovered that the mirror had been lying to me when it suggested I looked like an attractive woman. If that were true, why was I laughed at so often when I tried to go to ordinary places, such as nearby shopping malls? Eventually, my frustration pushed me to look around and notice how most of the cisgender women I saw were dressed. Even if it meant adopting the casual styles I dreaded, I knew I needed to do it to blend in and be accepted.

The more acceptance I gained, the harder it became to return to my old life and face the thought of giving up on my dream. For the first time, I even felt excited about where my future might lead. I just had the glimmer of hope that I might be able to make it to the transfeminine life I always wanted to lead.

At that point, my male life began to creep in with a vengeance. He was becoming very successful with a small family and good job and the risk of giving it all up loomed large over everything I did. Not a day went by when I didn’t consider the consequences of what I was doing. I always say, I wish I could get back just a fraction of the time I wasted worrying about how I would be living my life if I was a woman. What would become of me if I jumped off my gender cliff for good.

What I decided to do was experiment in the world as a trans woman. My second wife called me a “terrible woman” because I had never paid any dues that ciswomen pay, and all I was concerned about was my appearance. I knew deep down she was right but I still at that point did not know how to fix the problem by paying my dues as a novice feminine person in the world. It was like if you are applying for a job, the employer says you don’t have enough experience but will not give you the job so you can get it.  I am sure my wife was right about my feminine knowledge, but I was having an impossible time getting behind the gender curtain to learn more.

As I slowly got behind the gender curtain, the consequences of giving up almost completely went away. Why would I abandon all the effort I put into being a complex transgender woman and throw it all away during a time when I was finally being successful. For a change, I was the one making sense in a gender situation which very few understood.  No longer could I be accused of being a terrible woman as I matured into my new self when I was allowed into women’s only spaces. Sure, I was still making mistakes, but they were getting smaller and smaller as time went on.

The mistakes I usually made came from when I miscalculated how complex a ciswoman’s life really was and how far I needed to go to be allowed to fit in. To eliminate all my mistakes, I needed to give up all the negative consequences of a male to female gender transition and just make the plunge. Fortunately for me, the water was not that cold, and I jumped into the deep end of the gender pool. Plus, I can never forget the soft feminine gender hands which helped me to survive the impact into the water.

I know many of are thinking seriously of making your own gender plunge and what would be the consequences of possibly losing everything you hold dear in the world. I know advice is easy to give, but the turning point for me always was how natural I felt as a transfeminine person. Something kept telling me I was born the way I ended up. And with some effort, I made it to where I always needed (not wanted) to be. Hopefully, that is a starting point for you too and the consequences of giving up become too much to consider.

If you are further along, I am sure you recognize the consequences of never giving up and somedays even being perceived as being selfish. As I was when I was headed all out to fully transition into a transgender woman, all I could think of how fast I could make it to my goal. So, I am guilty as charged. It is probably the reason my second wife called me a terrible woman. In all fairness to me, I did mature out of it and found my way into a better world.

All the purges in the world did not work for me and I put up with all the consequences I lived through. I am not a gambler, but in this instance, I played the odds and won.

 

 

 

 

 

 

I Was Afraid of the Truth

 

Image from Brett Jordan
on UnSplash, 

It took me a while to understand that facing the major truth in my life was not possible early on for me.

As I cross-dressed in front of the mirror in my early years, I could not believe it would be a part of my permanent existence. Even though, it was screaming at me that it was. I learned quite early, just looking like a pretty girl (or so I thought) for just a quick moment in time never held up and very soon I would be wondering what it would be like to live among the girls around me as one of them. In other words, I did not know I was much more than a casual cross-dresser attracted to feminine makeup and clothes, I was so much more. Later I would learn I was a transgender woman when the term began to be popularized.

Even when I realized, for the first time in my life, I had found a term which described me, I did not totally accept it. My truth still evaded my consciousness.  I was afraid to face it and lose all the male privilege I had built up.  All along, I resisted building up those benefits, but then again took them when they were offered. Which deep down made me feel like some sort of a gender hypocrite. Regardless of my guilt, I needed to work my way through my gender issues all alone and I had no gender workbook to follow. No all-nighters with girls my age to learn what it meant to play with the essentials of makeup and clothes all the way to learning the foundation of what it would take to build me into a mature transfeminine woman someday. If I worked hard enough on my goal.  

I was frustrated even more when I got the tiniest bit of gender euphoria when I was able to go out in the world for the first time as a trans woman and do my own clothes shopping in women’s clothing stores. Even to the point of being emboldened enough to use the changing rooms to make sure my selections fit me as well as could be expected before my weight-loss program. Increasing my shopping confidence was the fact that the clerks did not really care about my gender as much as they did about my money. Another truth I needed to learn the hard way and not be so naïve.

The deeper I got into the world of cisgender women, the more I wanted to stay. As my time behind the gender curtain was beginning to feel so much more natural every time I did it. Sometimes, the whole process felt so good, I almost panicked because I did not know if I was ready yet to give up all my male existence. I had too much vested in him to just give him away, so I continued to explore my new world as a transgender woman.  

My bottom line at that time was again what was I going to do about an unapproving spouse who was still my best friend and major problems about what I was going to do about finding work as a new trans woman. I was intimidated and forced to deny my gender truth for many more years. I tried all sorts of ways to do it. I tried everything from therapy, to trying to drink it away, to trying to outrun my truths by changing jobs and moving my family many times. Of course, none of it worked and still I refused to face the facts that were staring me down in the mirror every morning that I was not meant to be a man at all. It was like life was playing a cruel prank on me because on occasion I could still be a success in a male life without really wanting to. It seemed that every time I did enjoy myself as a man, my woman self would come along and do him one better.

Finally, I had reached the point of no return and just had to begin the series of moves I would have to make to put my male behind me forever. Tragically, my wife passed away leaving me alone to do whatever I wanted, and I was old enough to retire early and sell collectibles online to scrape up enough money to survive, so destiny all of a sudden was opening doors for me to live my inner gender truth. And to make matters even better, I even gained approval from a doctor to start on HRT, or gender affirming hormones that I had always dreamed of taking. The changes I went through under the new hormones proved to be miraculous for me. As all the external and internal emotional changes took effect were worth the wait. Even though I waited until I was sixty to start them.

Perhaps the HRT hormonal shift was the final straw in me having to face the biggest truth of my life. I was a woman pretending to be a man all along.

Truth was always hard to face for me as I did my best to run from it or just ignore it…it never went away proving my transgender womanhood was the only way could go if I wanted to respect myself in the end. Plus, the end of my life was not getting further away at my age. If I was going to act, it was a now or never situation.

One night when I was out to be hopefully left alone in one of my favorite venues to watch sports and drink beer, the blinding realization that my male life was over came to me. The only future for me could be feminine if I was going to be able to live my truth. It was when all the disastrous gender wars I had lived with over the years came to an end and I all sudden, was on the right path.

Most importantly, I had worked hard to know it was the right one.