Solving the Gender Puzzle

Christine Jorgensen. 

Many times, during my life, I have looked at my gender issues as having a big puzzle to solve.

From my earliest age of recollection, I can remember thinking that something about me was really wrong, but I could not put my finger on what the problem exactly was. Most likely, it was not until I began to have a fascination with my mom’s clothes did, I began to discover what the puzzle I had was really all about. At that point did I embark on a lifetime journey or path to figure it out. I had no idea of all the twists and turns my path would take me on until I could finally put the pieces of my gender puzzle together.

Perhaps the biggest part of the puzzle to me was the fact that I was born into a male world with no way out in sight. I lived in a rural area around the same kids growing up from kindergarten through ninth grade, so I figured no one else had the same puzzle to solve that I did. Plus, in the pre-internet days, when I was growing up, there was no easy way to access any outside information. Especially none as radical as having anything to do with gender issues. As close as I could come was sneaking a look at all the “National Enquirer” type trash rags at a friend of mine’s aunt’s small neighborhood convenience store. Every once in a while, they would run a sensationalized story about “Christine Jorgensen” or another G. I. who wanted to change his/her sex. I remember the first time I saw one of the stories, I was hooked and could not wait to go back and look for more stories.

In some ways, just looking at these stories made finding pieces to my puzzle even more difficult to do. There was just no way I could ever see myself ever arriving at the point where I could go through such drastic measures to be a woman. I would just have to rely on my dreams to give me hope of ever living my life the way I wanted. Which of course was that of a transfeminine person. Hell, the word did not even exist back then in the sixties and having any sort of gender dysphoria was still considered to be a form of mental illness. Any hope of piecing together my gender puzzle would somehow just have to wait. For a bigger problem called military duty.

As I entered my formative years of high school, the Vietnam War was still escalating and the government had to establish a military draft to fill the ranks of unwilling participants, which included me. With all the stress hanging over me, I went off to college to at least prolong the draft position I had for four more years. Surely, the war would be over by then, but it wasn’t and it was my time to serve in the Army. I had the dual problems of not wanting to experience a military career from what it might do to me along with the problems I would have expressed any of my gender issues which I was just starting to do when I was drafted. My one certainty was miniskirts on soldiers would be frowned upon in Army basic training. Any work on my gender puzzle would have to wait for three long years.

Three years later, I survived my military service much better than I ever thought possible. I got to travel the world on Uncle Sam’s dime and even was able to experience the beautiful, exotic “Lady Boys” of Thailand when I was stationed there for a year. Even though I was fascinated with their culture, I was never brave enough to approach. Much later on, when I was in Germany, I gathered my courage to go to a hospital Halloween party dressed head to toe as a woman which led me later to my first coming out piece to my puzzle. Over huge amounts of good German beer one night, I admitted to three of my closest friends that my Halloween “costume” was more than a one-time deal. I was a transvestite and was attracted to dressing like a woman. Luckily for me, no one else cared and my secret was safe for the remaining six months I had to serve in the Army.

After I had served my time in the military, piecing together my gender puzzle became a bigger priority. Initially, I needed to rely on Halloween parties every year to express my need for public exposure as a transgender woman as by that time, I was realizing I was much more than a cross-dressing part-time guy. One of the biggest “aha” moments of my life came the night I made the mental shift from cross dresser to transgender woman and went out into the world. Despite being scared to death, I made the evening a success and knew deep down there was no going back. I had found a giant piece to my puzzle and I began to wonder what took me so long.

From then on, the pieces to my giant puzzle began to come together quickly as I began to carve out a life for myself in a world of cisgender women. To this day, the path I took seemed like a blur and once I began rolling downhill towards living my dream I could not stop. I was going crazy looking for the final pieces of my puzzle until I discovered the magic of gender affirming hormones or HRT. The hormones evened out my testosterone poisoned personality and enabled me to feel emotions I never realized I had. For the first time ever, I was able to feel the feminine way I tried so hard to appear like.

I have never been good at puzzles my entire life and find them to be exceedingly boring and frustrating…except my gender puzzle. Even though I don’t think I will ever finish it in this lifetime, the amount of work I put into it turned out to be very satisfying and just what the therapist in me ordered. I was able to finish to the point where I could see myself in the puzzle and was satisfied with what I saw.

  

Fearing Change as a Gender Challenged Woman

Image from Joshua Gaunt 
on UnSplash. 

Gender change came so very slowly for me during my life.

First, I needed to free myself from the male bonds I was born into which I had no control over. Looking back, I think one of the main problems I had was fearing the changes I was looking to go through if I faced up to reality. From that point forward, life became a struggle as I feared changing it.

What I became was the best transgender procrastinator I knew. Any excuse I could come up with not to go through with living my dream, I clung to like a survivor on the Titanic. What I would do about spouses, family and employment were a few of the major questions I was asking. So, what did I do? I ran as hard and as fast as I could from the problem. I was running so hard, I even changed jobs very quickly so I would not be bored with my life as a transfeminine fugitive. Eventually, even though I grew tired of the pace, I found a stable good job and settled part of my life down. I say part of my life because during that time my gender issues were raging out of control.

Even though I was slowly becoming successful at blending my feminine self in with the world of cisgender women, I still had many fears to conquer. Just when I thought life was improving for me, I would hit another roadblock and send me running back to my cross-dressing drawing board. Which was crazily marked with clownish makeup until I got it right. The fear of applying skilled makeup kept me occupied for years it seemed. On the other hand, when I got my male ego out of the way and realized I needed to dress for other women and not men, did I begin to improve my overall look and the laughter I used to receive in public began to die away. When it did, I learned the most powerful force I had to combat gender change was having confidence in myself. Surely, I would never be the prettiest most beautiful woman in the room, but a lot of other cisgender women were not either and they were surviving and even thriving just fine. There were many layers to building womanhood and I just needed to find mine.

For some reason, the more success I felt as a transgender woman, the more fear I had. I guess it was because of my old male self-starting to panic because he was losing his dominance over my life. For years, what had seemed like the impossible gender dream was now looking as if it could become a reality. As he fought his new reality, the stakes towards living a successful life as a trans woman, increased dramatically. Every step I was taking towards my dream seemed to feel as if I was walking in quicksand since at any time, life as I knew it could be disrupted beyond repair in the little backwards town I lived in. I still lived in mortal fear that any day I could be discovered and the acquaintances I had built up over the years would realize I was living a gender lie. Which I was.

I finally made it to a point where I could not procrastinate my life any longer and I began to use every spare moment to explore the world as a transfeminine person. It all meant I accepted the challenge to finally go all in with making the final preparations for my new life. The bittersweet part of it all was part of my male to female final transition was built on tragedy. In the space of a couple short years, I lost my second wife as well as all of the friends I had built up over the years to death, and I had to start all over again. Sure, I was still afraid to do it but deep down I knew transition was the only way I could go. Suddenly it was up to only me to decide if I wanted to take the ultimate step and try to get a doctor’s permission to begin HRT or gender affirming hormones. I was approved and then the changes I was hoping for began to really happen for me. The changes were so dramatic, I sometimes take an entire blog post to relate them to you.

What frustrates me now are the haters who say that because I took so long to transition, I am not trans enough for them. Normally, they are younger LGBTQ individuals who have no idea of what the world was like way back when I was growing up. We all have our own gender crosses to bear, and we need to understand each other’s journey.

Sadly, there are all those transgender women and trans men who can’t take the burden of gender change fear any longer and tragically try to take the self-harm way out. The suicide rate in our community is completely too high and could come down with proper help and understanding.

In my case, my excuse is I had a heavy dose of ignorance combined with fear and procrastination as reasons it took me nearly a half a century to come out of my gender shell and live freely in the world as a transgender woman. These days, if you can steer clear of all the online trolls and haters, you can still get valuable information on the internet concerning ideas on how to build a new life as a woman from scratch. Plus, fear for me was a powerful motivator and when I was forced into a corner because of my gender, I came out fighting because I believed I was right.

It turned out I was.

 

 

 

  

The Hustle and Bustle of Christmas as a Transgender Woman

 

Image from Clarke Sanders
on UnSplash.

Doing the Christmas shopping shuffle as a transgender woman, often takes a lot of courage and confidence to do it.

Over the past couple of weeks, I have written about my holiday adventures leading up to the big day. From taking a short trip to Clifton Mill to view their extensive, festive lighting display all the way to letting two men load my heavy purchase for me at an Oak furniture store, I stretched the boundaries of what I was used to as a new cross dresser or trans woman in public. After it was all said and done, even though I was terrified most of the time, I was happy I tried it all. I came out of doing the Christmas shuffle with much more confidence in my girl self than I had going into the season.

In fact, as I have written before, Christmas quickly outpaced Halloween as my favorite holiday. Why? There were several factors, such as the length of the season and the creativity I could put into celebrating it. Plus, for once, I was doing good for others by buying gifts for them as I shopped. I positively loved it and wondered where the experience had been most of my life.

If you are a procrastinator and last-minute gift shopper like I was, doing the Christmas shuffle as a transgender woman is ideal for you. As you can get lost in the crowds quite easily and no one pays attention to a single woman out doing her late shopping. Custom made for you to do your shuffle and head back home.

I was fortunate when my second wife left her bookkeeping job and took a managerial position at a large bookstore chain. So, at Christmas, she was very busy and worked many hours. It was easy for me to schedule my hours around hers, so I had plenty of time to get out of the house and do gift shopping. I could obsess on wearing just the right outfit to blend in with a busy world and at the same time, search for just the right gift. Along the way also, I could stop in and grab a bite to eat at a restaurant and again stretch my ability to deal one on one with the world as a transfeminine person. Yet another reason, I came to prefer Christmas over Halloween because I hoped I was not perceived as a man wearing a costume, or worse yet some sort of drag queen.

As the big day approached, the sky was the limit for me. I did my shuffle as much as finances allowed and stockpiled my gifts for my special night where I stayed home with some high-powered eggnog and wrapped my treasures to go under the tree if they would fit. Of course, my wife was close to being a professional gift wrapper and I was just the opposite. But as the eggnog kicked in, I did not care, and besides it was the thought that counted. Right?

Finally, the big day arrived and I was shuffled out. Plus, we had family connections to visit all day on Christmas day. My thoughts for once were in other places than doing my precious shuffle which I had learned so much from. After the day wound down and my wife and I were alone, we opened the final gifts from each other. Which included a gift for my feminine self. I will forever remember a nice fancy fuzzy baby blue sweater she gifted me. It was snug fitting and I filled it out nicely with my new silicone breast forms I received from a cross-dresser acquaintance of mine who was purging. Naturally, that part of our gift giving day was the part of the day which was the most anticipated for me. I was like a little kid, brimming with anticipation.

Every year after the intense transgender Christmas shuffle was over, I had the chance to sit back and reflect on all my experiences and what they meant. Without hesitation, I think the confidence I built up from going out in the world as my trans self was the most important aspect of what happened to me. I learned what it meant to blend in with ciswomen around me and survive better than I ever could before. I also discovered the vast majority of the world did not and does not care about having a transgender person in their midst. The biggest difference is that back then, we did not have a Russian asset in the White House leading his blind, spineless party into demonizing a small portion of the population. Back then, I was merely a curiosity to many people, especially ciswomen.

When my second wife passed away, the need to do the major Christmas shuffle went with her too. The only blood family I had left was a brother and a daughter to worry about at all during the holidays. When I came out to them, I was roundly rejected by my brother and completely accepted by my daughter and her family. So, I broke even and even did better when I considered the relationship, I was able to build up with my daughter, son-in-law and three grandchildren. I won the family coming out shuffle in a big way.

Even still, sometimes I miss the hustle and bustle of doing the transgender Christmas shuffle as over the years, I have gone nearly the entire direction in the other way. It is hard to say what I miss most but it probably having the financial resources to buy basically as many gifts as I could afford might be it.  Maybe it all came from having a guilty conscience from sneaking out of our house to join the world as my authentic true self instead of my old boring male self and breaking the pledge, I gave my wife that I never would.

Whatever the case, I was extremely selfish and was a contradiction when I did it to buy gifts for others. I guess it fit in with the whole contradiction I felt from my deep-set gender dysphoria to begin with. I dealt with it all the best I could, did my Christmas gender shuffle and moved on with my life making the most of it.

 

 

Letting Things Happen versus Making things Happen as a Trans Woman

Image from Mahdi Chaghari
on UnSplash.

Perhaps you have heard a football coach talk about slowing the game down and simplifying it for his players. Of course, I had to equate it with being a transgender woman or trans man when I heard it.

I began to think of all the stressful days I spent in front of the mirror as my perception of a pretty girl, then taking my image public and into the world. For years it never occurred to me that I was trying too hard. I was attempting to micro-manage myself to ensure every little aspect of my feminine image was correct. Here is an example of what I was doing wrong. On any given day, my makeup and fashion were on point, and I was confident about my presentation. Then as I was out trying it all in the public’s eye, I would either catch myself walking hunched over like a linebacker or worse yet, trip over my own heels and almost fall. It took me quite a while to realize what I was doing wrong and try to change it.

For me, relaxation and confidence were the key to real gender change. I was letting it happen rather than making it happen. I discovered it was so much more pleasurable for me when it happened that way. After that I could take my game to a different level such as communicating one on one with the world for once as my authentic feminine self. A key point I had to do if I was ever going to make it to my dream of a male to female femininization project.

I also established bucket lists of things I wanted to do as a transgender woman and was able to accomplish most of them except a couple of ill-thought-out visits to women’s rooms when I had the police called on me. Letting it happen surely did not work for me then, but I recovered and gained my restroom privileges in other venues I went to. Fortunately, the police had better things to do than mess with me and I went on my way without further problems. That was years ago and I haven't had any problems since. That was a good thing because the restroom privilege was something that I needed more than wanted.

I cannot stress enough about how much I had to learn during this period of my life when I was making a serious push towards transitioning from a serious cross dresser all the way to a transgender woman. When in reality, it was mostly a mental transition, it was still a very important one to make. I have a difficult time explaining it but all of a sudden, something clicked in my mind, and I knew another change was needed. I was so more than a man wanting to look like a woman.  I wanted to be a woman and feel like one as close as I could. That was when I successfully set out to socialize with cisgender women just to see if I could. I conquered my fear and found out I could add another layer of just letting it happen versus making it happen.

By this time, my muscle memory had improved so much as a trans woman that it became natural to me. So much so in fact that I had to be careful I was not too effeminate when it came to me working my male job and living with my wife. It finally became too much for me to juggle, and I needed to put it down before it was too late and I became more self-destructive than I already was. What I did was, attempt to do more things as a transfeminine person and do as less as humanly possible as my male self. It is one of the reasons I took so long to transition, because of the need to work around a disapproving wife and male self which was desperately hanging on.

You regulars know this part of my story when my wife tragically passed away. Which left only my weakened male self to resist any efforts at total domination from my inner female who had waited so long for her chance to live and write her own gender workbook. Little did I know she kept her own workbook up to date and was ready to go. If and when she had a chance to use it. Perhaps, your inner female is keeping a gender workbook also and you will not have as far to go to catch up when you get the chance to live your life.

I discovered too that letting it happen versus making it happen was mostly common sense. Even though the two main binary genders do things differently, they often operate in parallel universes which are the same and seem to be doing more so in the younger generations. I first learned up close and personal during my first girl’s nights out I went to. I was worried about what I needed to do to be able to interact with the group but then found they had just flipped the script from jobs and sports to family and friends with the women. Quickly I relaxed and started to let my inner girl flow, and I was fine with most of all the other participants except for one who I perceived as being a miserable person anyway. Who was unlikeable to me, and I left her alone.

I chuckle to myself when I think of how my football coach’s words would come back to help me in such a different way later in life. I guess it proves that you just cannot count on anything staying the same when it comes to gender. Perhaps that is a clue why the population at large knows nothing about us and we live parallel lives from both of them. Whatever it is, if you are in your path of gender discovery, you will certainly feel the change from making it happen to letting it happen.

 

                                                                                                                                          . 

Staying in your Own Gender Lane

Image from Earnest Tarasov
on UnSplash.

Staying in my own gender lane may have been more difficult than I had ever imagined. Of course, it all started when I was externally born male. Then when I started to understand something was dreadfully wrong with my male existence, I needed to figure it out.

My first indication of what the problem might really be came when I discovered the thrills of wearing my mom’s clothes, since I did not have any sisters to beg for clothing off of. Sadly, even though I was thrilled to see my version of a pretty girl in the mirror, deep down I knew it was just not enough for me to stay in my cross-dressing lane.  I wanted to pull out and find myself in a more comfortable gender lane where I more than ever before to being feminine.

Before I could do that, I needed to define what being feminine meant to me. I knew just acting effeminate would get me nowhere except bullied to the point of beaten up and on the home front (which was very male dominated) I would probably earn a trip to a psychiatrist if my small stash of girl’s clothes and makeup was ever discovered. I was trapped in a male world I wanted nothing to do with, and worse yet, I was pressured to perform well in that world. I needed to be in a passing lane around as many other males as I could.

The problem was, I wanted nothing to do with that world and could not show it. And in the pre-internet era I was growing up in, I felt so all alone with no one to talk to about what I was feeling. I just knew I did not feel the so-called mental illness that gender issues were being referred to back then. All I knew was, I was having a very difficult time staying in the gender lane which was assigned to me when it felt so natural. Plus, when I woke up in tears after having such a realistic dream that I was a girl impacted my life terribly until I could get centered again where I was “supposed” to be.

Somehow, I made it through those very confusing gender days and finally made it out into the world to discover if I had any future at all in a world ruled by cisgender women. When here I was, a novice in their world trying to survive. I equated it with driving on the Autobahn in Germany. I quickly discovered when you were driving a VW Beetle (like mine) and ventured into the outside lane then you saw a car in your rearview mirror flashing its lights, you better get out of the way. My life in those days often felt that way. I was learning lessons about where I wanted my transfeminine womanhood to go but I always seemed to see lights warning me in my rearview mirror.

Through tons of trial and error, I learned I could change my gender lane to the one I dreamed of. From as young as I could remember all I really wanted to do with my life was live it as close as I could to being a woman. Of course, that meant putting all my safe male privileges behind me and set out to build new ones in my gender lane with new life experiences. Like the Autobahn I found there were no speed limits on what I could learn or experience in the new gender lane I was in. More importantly, I had no one except my old male self to tell me to slow down before it was too late and I wrecked. Here is where I make the excuse of why it took me so long to transition because I was overly cautious that I did not wreck.

As I was in the gender lane I wanted to be in for a change, it w as nice to finally wake up in the morning knowing I was coming closer to my dream of living life on my terms as a woman and not having to keep falling back on my male self for last minute support. I was one and she was me for good.

But just when I thought I had it all in my new gender lane, I discovered many small nuances the ciswomen around me use that I needed to learn and put into practice. Such as the powerful use of nonverbal communication and passive aggressive behavior. For the first time in my life, I needed to look intently at other women when I talk to them and search their eyes for what they were really telling me. Which extended into the passive aggressive areas of behavior I encountered. There were many times I fell for a smiling face or non-threatening comment which turned out to be a knife in the back when I let my guard down. They were all lessons I learned the hard way as I earned my ability to stay in my gender lane permanently.

The best part was that the more I learned, the more I wanted to learn about the lane I was in. Even my biggest naysayer, my male self, had to finally give up and get out of my way. I was in my lane for good and there was nothing he could do about it. I had served my feminine apprenticeship I was walking the path I always was destined to walk and in the short and long term I got out of the way until I could salvage was left of myself and move forward. 

Trans Girl and the Christmas Season

 

Image from Roberto Nickson
on UnSplash.

Little did I know that Christmas would pass Halloween as my favorite season when I transitioned genders to the one I wanted. There were several factors which contributed to the change I was going through.

The first one was the ease I found I could get lost in the Christmas shopping crowds when I shopped as a trans woman. As long as I followed my fashion instincts. I learned I could follow several different shopping paths. For example, one day I could dress up and go to an upscale mall, and on the second, I could dress down and go shopping at a nearby local antique mall. I enjoyed the feminine freedom of choice immensely.

The second main reason I came to love Christmas so much more was I could really get into the spirit of giving. For some reason, being my transfeminine self-slowed me down and encouraged me to choose more thoughtful gifts for the people I cared about.

The third man reason was I could get lost as a woman in the hustle and bustle of the season. I forgot all about the buy something quickly and move on person I was as a man. My second wife was a huge gardener which made garden themed gifts popular with her, so I could shop at both style of malls for her garden gifts…new or vintage. In particular, I remember finding her a vintage seed merchandising box which she ended up cherishing in her collection. Right or wrong, she never found out my male self-did not buy it at all, my transgender side did.

Reason four was shopping as a woman took all the guilt of sneaking out of the house dressed as myself to buy gifts. I told myself I was not cheating on her when I did it if I was buying her a gift. Probably not the best reason in the world, but at that time it was the best one I had.

Reason five was that Christmas was such a longer season for me than Halloween. Halloween was an intense build up just for one day, and then the let down set in. Christmas of course lasted much longer, and I had the satisfaction of knowing my feminine self-bought all the gifts under the tree.

The final reason I can think of is since my wife always had a special gift giving night for my transfeminine self, I always felt guilty when I came up short for gifts for her. She was not much into makeup and fragrances and such, so the traditional ciswoman gifts were out. She never found out all her gifts could have been given out that night because of who they really came from. Instead, I ended up letting her open a few gifts at a time before Christmas itself.

Christmas at my house and my restaurant became a major holiday from the point of decoration. My wife had quite the collection of animated holiday figures, some new and some vintage which I was expected to find a way to display. As I did, I was put in a festive Christmas mood and made me more impatient to join the masses and do more shopping. Or at least all my finances could stand. Through it all, I was gaining the all-important confidence I would need to consider if my transgender dreams could become a reality after all. I could only discover if I was on the right gender path by the trial-and-error method. By attempting to stay out of the mirror and let the public tell me if I was right or wrong. I don’t know if the public was kinder at Christmas or not, but for some reason I was getting by and enjoying myself as a transfeminine person even more.

All these Christmas holiday positives did not leave me like the Halloween ones did. They became ingrained as I built my new life. A trans girl at Christmas soon became a trans girl period. All my learning gave me a new foundation to stand on when my life hit the skids, and I nearly lost everything. I lost my wife, what close friends I had, and my restaurant within a two-year period to death and recession. As it all crumbled before me, my feminine self-stood strong and ready to help. All I needed to do was let her with no strings attached. To ensure I could make a living until I could retire, I sold all the vintage items I had accounted for and was able to make enough to pay my back taxes and then retire from a job I hated. It worked because then, I would not have to worry about transitioning to a new job.

Now, since my second wife and her love for Christmas has long since departed, my daughter has converted to the Jewish faith and my wife Liz is wiccan, my overall interest in Christmas has waned. However, I will forever remember the festive seasons I went through in my past which helped me along so much in my male to female transition. I developed the instincts I needed to survive in a scary, exciting new feminine world. Being a trans girl at Christmas really worked out for the best for me.

 

Tiny Ripples of Gender Hope

Image from Rosie Kerr on UnSplash.

During the overwhelming sense of darkness I felt when I began to come out of my gender shell, were moments of gender hope and euphoria. More than anything else, they kept me moving slowly towards living my ultimate dream. All I could think of was the possibility of living as a woman later in life.

Having to run and hide my small “collection” of feminine clothes and makeup every time I tried to get in front of the mirror and cross dress did not help. I resented the fact I could not be free to do what I wanted, no matter how radical it was…like being a girl. I could not imagine the pain and suffering I would have if I was caught. What saved me was the vision of a pretty young girl which came peeking on through when I was able to be alone and try on my precious clothes. Even though I was depressed I had to go back to being a boy, the brief moment of femininity carried me through the dark days and gave me a ripple of hope.

Fast forward through the difficult days of puberty and adolescence everyone goes through, I needed to deal with my gender dysphoria also. There were so many dark days when I just went through the motions of life that I did not know what was going to become of me. When I did, I desperately needed to find refuge behind my dresses and makeup to give me hope. Perhaps the only good thing which was happening was that I was slowly perfecting my use of makeup. When all my friends were showing off their painted model cars, I was stuck not being able to show off my new eye makeup. I had to internalize my feelings of hope and euphoria when I saw my new pretty eyes. Sadly, I needed to become good at removing all traces of the makeup so my brother and parents would not notice.

I guess you could say I was in the dark through my college years and beyond until I began to be able to enter the world for the first time as a novice cross dresser or transgender woman. These were the days of attending transvestite mixers and small parties in nearby Columbus, Ohio. Being around like minded people who were searching for their gender answers almost made my search seem normal for the first time in my life. I was so protected from the world in the pre-internet days that I thought I was the only one like me stuck in their own personal hell. I was experiencing ripples of hope for the first time in my life on a scale I could appreciate. I even upped my appearance game when I went to Columbus from trashy woman to hopefully a passable ciswoman. One of my favorite outfits to wear was what I called my knit black out. I paired a loose fitting black wide knit top with a black leotard, shorts, tights with a pair of black flats and my red wig and was ready to go. After makeup of course.

For me, the whole outfit helped me to tone down and refine my look and it worked so well that I had my first ever encounter with a lesbian from the party when we left and went to a big lesbian venue for a break. I learned many valuable lessons that night which provided me with ripples of hope for the future. Mainly, if I could not be as feminine or beautiful as the transsexuals who were there, I still could be attractive myself to have a good time and most importantly, learn to be just me. Developing the future, me gave me real hope for the future as I learned it would be possible to achieve my transgender dreams if I worked hard enough. I had to learn the new transfeminine me meant so much more than the ripples of hope I had gained in the past went way past how I looked and into how I acted.

Suddenly, acceptance became my main goal, as my interior feminine self-stepped forward in my life. I knew who I wanted to be but still was not quite sure how to get there. For example, I knew for sure I did not want to be like the “Trans Nazi’s” as we called them or the bitchy trans women who thought they were better than anyone else simply because of their appearance or the number of gender surgeries they had undertaken. I suppose I should owe them a debt of gratitude for showing me what not to do to be a gracious, friendly transgender woman.

All of this came together for me when I began HRT or gender affirming hormones when I was sixty. I had spent enough life in the dark to appreciate the light and grasp a ripple of hope when I saw it. The hormonal medications proved to be a natural success when I began taking them. My body seemed to be saying again what took you so long. But on many levels I don’t think even I understood the basic limits I went through back in those days to salvage my life through the brief ripple of hope I received way back in the days when I lived for the mirror.

More importantly, I found myself in a situation where I could pay forward my experiences to helpfully help others. Especially those of you who are struggling to find answers on how to escape your dark gender closets and find your own ripple of hope. 

The Rise of Transfeminine Privilege

 

JJ Hart (Middle) wife Liz (Left)
daughter (Right)

When I began to seriously leave my closet and mirror and attempt to join the world as my true self, I quickly lost all my male privileges and gained very few feminine ones. In fact, early on, the only privilege I felt was having doors opened for me by the men around me.

On the other hand, the most extensive male privileges I lost were my intelligence and my personal security. When I was around men, I learned to keep my mouth shut until I was spoken to, which was not very often because I think most all men knew I was transgender and wanted no part of me. And as far as personal security went, I needed to learn what ciswomen know from an early age to keep themselves out of possible bodily danger by being in the wrong place at the wrong time.

All along, during this time, I was wondering when and if the gender teeter-totter I was on would balance itself out and I would see the positives of what I was doing. It took a combination of things happening before I ever did. One was seasonal around Christmas, and the other one was when I decided to give up on men all-together and concentrate on knowing other women. A preferred topic in my mind, since I did not have to consider changing the focus of my sexuality, which had always leaned exclusively towards women. But I digress, the meaning of Christmas and what it meant to me as a transgender woman, is the real reason for this post.

To begin with, Christmas was always a major holiday for me and my second wife especially. Finding an exceptional, unexpected, rare gift was always the priority for me and even my brother’s family. The difference became to me was when I decided the Christmas shopping, I had been doing as a man would be much better accomplished as a woman. If I was able to pull it off, I could accomplish so much more during the Christmas rush I was in the middle of.

First of all, I needed to up my crossdressing game to give me the best possible chance to succeed in my shopping conquests. I went through my closet and pulled out my fancy, sleek, black pants’ suit for trips to upscale malls and my leggings, boots and sweaters when I combed through the huge local antique malls for just the right gift for my wife. I knew if I was to succeed, I had to be better than the average Ciswoman so I would not be potentially embarrassed. Also, the right makeup and hair was a priority because of all the up close and personal time I would be spending in the public’s eye. Through it all, I wondered where the magical feminine privilege would kick in for me.

The first major time it did was when I was shopping for a matching oak bookcase for my wife’s roll-top desk. One night, I found one which worked beautifully in an oak furniture store in nearby Columbus, Ohio. It just so happened I was returning from a shopping trip to a local Columbus upscale mall when I stopped into the store on the way home. After I found the bookcase I wanted, my old male self-wondered how in the world would I get it in my truck/SUV. Would anyone come to the aid of a tall blond in a black pants suit and heels? After I paid, I found out they would because for the first time in my life I was able to sit back and watch two young men load the bookcase carefully into my vehicle and finished their job off with a nice thank you mam. Because I had finally discovered a dose of feminine privilege, the half hour trip home went quickly, and I wanted to do more shopping, but I was out of time and money.

Sadly, once I returned home and had safely unloaded my prize gift, it was time to return to the place I did not want to be…my old male self. On the plus side though, the whole experience taught me (and provided the confidence) to move forward to my dream life of being a fulltime transgender woman and would not have to return home every night in a hurry to switch back into a gender I wanted nothing to do with. My feminine privilege was being established in the newfound senses I was feeling. Especially when I was doing something for others, such as buying gifts.

The experience made all the learning and trial and error experiences I went through during my male to female femininization process deeply worthwhile. There were other Christmas stories to share as I will do later. Such as when my wife decided we would have a special gift giving time for my feminine self.

 

 

 

 

Stopping was Impossible

 

Image from Edward Howell
on UnSplash.

For years as I followed my early cross-dressing path, I labored under the impression that someday I could actually stop and return to my male existence. Of course, the older I became I learned that stopping was going to be nearly impossible. The reason being, when I was forced out of the mirror and into the world, I began to have success.

To me, success was measured in the public reaction I received. Very early on I suffered scorn when I went out without the knowledge to blend in with other ciswomen. When I became successful, it took so much pressure off and stopping became less and less an option. Mainly because something clicked in my head that I did not want to ever go back which was different than wanting to. For example, there was the night at TGIF Fridays when I went into the venue with the mindset, I actually wanted to be a woman with other women, not some sort of an impostor. When it happened, I knew for sure stopping was never going to be an option again. I was firmly on the path to achieving my dream of possibly living fulltime as a transgender woman.

The more I decided not to stop, the quicker the pressure mounted on me on what to do with my old male life. He had dug in deep and was refusing to go away easily. The worst part was he made good arguments such as what was I going to do about my spouse, family and employment. Just as a start. What did I do? I continued to internalize my inner woman and keep researching my future. Since my gender workbook was blank, I had a long way to go. Primarily when I needed to learn how to communicate one on one with other women when I was exceedingly shy to start with. To arrive there, I went to excess of taking feminine vocal lessons to attempt to learn to communicate better. As I was slowly succeeding in my efforts, again I knew for sure I could never go back.

Another main thing I learned was that I needed to control my emotions, not let them control me. Or when I hit the valleys of my journey (which there would be many), I had to pick myself up from being a failure and continually go back to my gender drawing board to figure out what I was doing wrong. I knew I had a testosterone poisoned body. I needed to work around but I dedicated myself to somehow doing it. I discovered from all the trips I was making to thrift stores; I could find the fashion I needed to make myself look the best I could under the circumstances I was working with. It all added up in my mind to I could never stop.

Along this way too, I quit purging for good. I had learned my lesson about the previous purges I had attempted. The lesson was, I could never go back to my old male self again. I was tired of throwing out all my hard-earned clothes, shoes and makeup only to have to replace it all again as soon as a month later.

What helped me was, I was learning over and over again how wrong I was fighting my instincts to be a transfeminine person at all. I always point out how wrong I was when I was fighting my true feminine self at all. I suffered from the brutal pressure I put on myself. So, stopping my transgender advance was never an option. I should never have waited as long as I did to go after my gender dreams.

I was fortunate that my basic personality never lent itself to stopping my search for my dreams. All my life, all I wanted to be was a woman and I just could never visualize myself not working hard to achieve my goal. I just never in a million years understood how difficult it would be for me to do it. I should have listened to my wife when she tried to tell me I was on the wrong path to achieving my goal. In a way, I did but not nearly enough until I did not stop until I was allowed to exist behind the gender curtain. Once I got there, stopping was never going to be an option again.

Then HRT and new feminine hormones shifted my mental thinking to match my external appearance which was improving all along. I never expected the changes to be so dramatic so quickly. I am glad stopping my male to female feminine transition was never a reasonable option.

 

Is There Really a Difference between Genders?

 

Image from Pea on UnSplash. 

Yesterday, I briefly wrote about how I saw the world differently when I went out for the first time to view Christmas decorations at Clifton Mill, Ohio as my feminine self. I said something to the fact that my senses seemed to heighten as I viewed all the decorations and people around me. To me, the whole evening was brighter and more festive than when I viewed it as a man, wondering how it would be to do the same thing as a woman.

Little did I know the experience would prepare me for later life as I progressed along my gender path. Perhaps, initially, the new senses I felt were psychological in nature because I was still years away from actually changing my gender hormonal balance from male to female when I added HRT or gender affirming hormones to my system. Which means, I guess, if I was in some sort of a scientific gender study, I would not have needed the hormones to increase my femininity at all. Which would be good news to all of you who for medical or spousal reasons cannot consider HRT.

One way or another, I felt a real difference in my world when I entered it as a woman rather than a man. If I was cold, I could react accordingly and not have to be macho and try to ignore it is a prime example. Then, quite possibly, the biggest change of all was what I was going to wear. I had so many fashion choices I could barely make up my mind. It seemed I was only limited to what I could afford to shop for and buy. The sensory feeling of the clothes was wonderful, and I just loved the big, warm, fluffy sweaters I was able to wear because they were in fashion at the time and paired perfectly with my denim mini skirts I was able to find at my favorite thrift store. I discovered that I was perfectly comfortable when I wore a pair of tights or even leggings with my sweater/skirt combo in cool Ohio weather.

Even though the clothes did make a difference for me, the buzz quickly went away and the reality of what I was attempting set in. I have always believed that attempting to change the human gender is one of the most difficult things a person can attempt because there are so many roadblocks in the way.  Such as current misunderstandings of trans women or trans men’s lives. No matter how you cut it, it is just difficult to explain to a “civilian” what is going through our minds when we made the monumental decision to jump the gender border. What could possibly go wrong? Ha ha!

Sometimes, we end up surprising even ourselves with the gender changes we have to go through to be successful. As we begin to earn our way behind the actual gender curtain into woman only spaces, we begin to see and feel all the real differences there are. I know my first girl’s nights outs were real eye openers for me. I had no idea of how ciswomen interact with each other when there were no men around. The differences were real, and I cherished my chances to experience them. So much more than even my new one on one communication challenges with ciswomen strangers in the world.

As I approached the idea that I could actually take the opportunity to attempt to go on gender affirming hormones, naturally I knew it was a huge step forward in my transfeminine development. First of all, there were the health consequences of a sixty-year-old male starting to reverse the hormones he had lived with successfully for all those years Plus, back in those days, there were many naysayers preaching about the possible damage female hormones could cause on the body. Fortunately, I found a doctor who did not believe in all of that, and he approved my HRT. When I started the meds, I felt an almost immediate change. It was certainly what the doctor ordered, and I was rapidly increased to higher dosages of my precious new medications.

I felt great when my external changes such as breast development started to happen faster than I expected and was even more surprised at the internal changes I was feeling. Like the first night I visited the Christmas lights, when my world softened and became more perceptive, I quickly found myself in a world where I could appreciate everything more. Heat, light and sound in particular affected me more when I ventured out in public to my regular venues.

At that point, all I really knew was I never wanted to go back to the old male life I forced myself to live. I had found my new home.

Gender Professionals

 

Image from Alysha Rosly
on UnSplash.

On occasion, I can just sit back and observe other women. Through my observations, it has occurred to me that some ciswomen are better at being women than others. For example, they walk straighter with their shoulders back and are proud of their femininity.

It has also been my theory that all females do not have the right to claim their femininity or the right to be called women just because they were born that way. Transgender women in particular know that becoming a woman can take many paths and we have can claim our own womanhood when our gender workbook is filled out.

Does it make us gender professionals? No, not in its own right but it does give us a leg to stand on when we are out in the public eye just trying to live our lives. It could be argued that transgender women and trans men must be better than our gender counterparts to get by and stand a chance of becoming gender professionals.

The question could be also, what does being gender professional really mean. I am only one gender conflicted person of course but for me to understand what a gender pro really meant, I needed to go into the world and live it. First, I tried to go to gay venues to see if possibly I was attracted to other men, or would they be attracted to me as a transgender woman. They were not attracted to me in any way and considered me no more than another drag queen on their turf. Which I wanted nothing to do with. Next, I tried the few lesbian venues I could find in the Dayton, Ohio area. There were three, and I found I was hated in one, had a neutral reception in another and was warmly accepted in a third. From the experience I mainly learned the different levels within the lesbian community and was it possible to work my way in at all.

The third and final venues I ended up at were the big sports bars I frequented as a man. In them, I was surprised to learn how quickly I could establish myself as a regular if I did not cause any trouble, learned to smile and then tip well. I learned too, to try to carry myself as a gender professional. Leaving no question of who I really was. I had to learn also carrying myself as a gender professional was completely different from being a gender professional. It meant I could carry myself well if I was wearing a fancy sweater and slacks, or my favorite team’s football jersey with a pair of jeans and boots. I discovered, more than anything else, I needed the confidence to do it and the rest of the world be damned if they did not like me. I was just having fun in the world as my self and taking advantage of all the fashion perks of being a woman.

Even with all the learning I was doing at the time, I still made learning from the ciswomen around me a priority. I figured they held the secrets that I needed to complete myself as a professional woman. The times to talk and communicate and the times to keep quiet and shut up and learn come to mind. You might say, I was exploring all the nuances of being a woman and trying to improve myself at the same time. I was fortunate in that almost all of my friends came from the lesbian community, so I came up with a unique view of the world. Especially around men which I learned did not validate my womanhood.

As you can tell, pursuing my quest to be a gender professional overtook much of my thinking. There was so much happening when I met my wife Liz, and I started to accompany her to her meetings she went to for various reasons. What happened was I had no choice but to expand my horizons again and meet a whole new set of people. When I did, I fell back to all the lessons I had learned about communicating with strangers. Not as a transgender woman but as just me.

Most Importantly, I had built back a portion of the self esteem I had lost as a gender professional growing up. I lost the inferiority complex I had put myself through during the rocky days of coming out earlier in life. Believing in myself for the first time as a transgender woman was all it took to get me by and enable me to become a true gender professional.

 

 

Falling Asleep in my Heels

Image from Toa Heftiba
on UnSplash.

Falling asleep in my new high heels turned out to be a very dangerous thing for me to do.

There was a time when I was in my early formative cross-dressing years that I thought wearing high heels was a fashion necessity I could not do without. Instinctively I knew the heels made my legs shapelier and longer. But what I did not realize was how much power the shoes gave the ciswoman wearing them. Have you ever noticed how men follow the sound of heels when a woman enters a room? Plus, the power extends from men to other women, who at the least responded to the expertise it took to wear a pair of high heeled shoes.

So, where did the danger come in for me? Actually, in. several different ways. First came the pure challenge of wearing heels. I had never experienced anything like it in my entire life but only knew the shoes made me feel so deliciously feminine. Through sheer effort, I conquered my fear of wearing heels so much that I forgot I was wearing them and ended up with another big problem, looking like a linebacker in drag, in heels. So much so that one night as I was trying to negotiate the stairs at home, my wife barked at me with a feet forward command. I never forgot that night and resolved to walk better in the future.

There were times in my past when heels went out as a fashion accessory and flat shoes were in with over-sized sweaters and short mini skirts for ciswomen everywhere. I was overjoyed with the idea of showing my legs off in tights and opaque pantyhose but again found myself in a situation where I needed to really concentrate on how I walked femininely without the heels I had come to rely upon. It seemed one of my favorite female privileges was taken away just when I was getting used to them. As with anything else in the fashion world of women, if you don’t like something, just wait because change is just around the corner.

That corner for me turned out to be a long way away. My fashion sense turned into a strong urge to blend in with other women in the world. Which meant where I was going, the women around me never wore heels. Especially all of my lesbian friends. Like them, I went for comfort in my footwear and blended right in, especially at all the lesbian mixers I went to.

My caveat to all of this comes from the transgender women such as “Stana” at the “Femulate” blog who have fabulous legs. Years ago, I had the pleasure of meeting her in Dayton, Ohio. Stana is tall to begin with and makes a striking beautiful woman when you meet her in person. Where we met, there were a group of men waiting for a ride when the elevator opened and out stepped Stana in all her long-legged glory. From where I was waiting, I could see everyman in the lobby turning to admire her. As you can tell, I have never forgotten the moment years ago when Stana took every advantage of her legs and heels as a transgender woman.

As I grew older, unfortunately, I had an old football injury destroying my ability to wear any heels at all. I broke my left ankle twice in the same place and wearing heels just became unbearable. To compensate in my own way, I try to buy stylish shoes and boots with no heels that I can walk in.

Regardless, I still remember the days when I felt the power of wearing my high heels gave me. Even after I went through the paranoia of feeling I was so much taller in the shoes. I decided to stand tall and be proud of myself, even though I was barely six feet tall. I had the opposite effect of going to sleep in my heels. I was wearing them proudly when I could. As I said, time has passed for me and I need to go for total comfort in my footwear, and it makes me sad. I feel I have lost a portion of my transfeminine self which will never be reclaimed. In the meantime, I can sit back and admire any woman I see negotiating the world in her high heeled shoes. As I know what she is going through, so I appreciate it.

As for you, if you haven’t checked out the “Femulate” blog yet, try it and you will see several transwomen and cross dressers in their heels and hose. Then you can go home and practice. Till you have your walk down and attempt in the public’s eye and watch out for sidewalk cracks which can cause you problems. Which I know from personal experiences.