A Lifetime or First Times as a Trans Woman

 

Image from Mahreal Boutrous
on UnSplash. 

As humans, I know we all experience quite a few first times in our lives. However, I think transgender women and transgender men tend to have more firsts than the average human.

During my life, every time I thought I had it together and there was nothing else to learn, along came something totally different to prove to me I still had a lot to prove to get to the next level of life I was trying to reach. This happened to me as a man and as a woman. My prime example was when I was in my twenties and totally out of control trying to drink my gender issues away and my daughter came along. Causing me to change my thinking about life radically because having a child was not something that I had planned on. Let’s just say the “protection” gave out and here she was. My very own daughter that I loved and love very much.

The initial problem I had as a first-time parent was what I was going to do about my gender issues which were increasingly looking like they were not going away, ever. What did I do? I tried to hide my femininity behind a wall of false male bravado which as we all know was a short-term solution to a long-term problem. So, I needed to set out to discover how long term my “problem” was.

Using a well-known phrase that I learned at one of the places I worked at, I did not have a problem. I had an opportunity to improve. To do it I would have to have the courage to take a different approach to life which would include a series of first times. The courage I am referring to was when I hitched up my new big girl panties and went out into the world for the first time as a novice cross-dresser or transgender woman searching for her identity. In those days, my first times were filled with rejection in the public’s eye and plenty of disappointment to deal with until I understood what it would take for me to present well enough to get by in the world of ciswomen that for the first time I learned really ran the world I wanted to be a part of. If I wasn’t attempting to be validated as a trans woman by men, first I needed to be validated by women.

Once I broke limits of what I was trying to accomplish in the world as a transfeminine person, the challenges and first times came quickly rolling in. The opportunity I had was trying to understand how deep my gender urges ran or how badly did I want to sacrifice my male life and live as a woman. What I decided to do was undertake a deep dive into what I “thought” a ciswoman’s life was all about, and what it really was. And more importantly, could I ever be allowed behind the gender curtain to see for myself if I wanted to play in the girls’ sandbox.

For the most part, I was successful as I accomplished my lists of firsts such as taking feminine vocal lessons, all the way to attempting to carve out my own new life away from any vestiges of my old male existence, Often, my life was a blur as I tried to balance what was left of my male existence with my new exciting life as a trans woman. Not only did I have to do my best to blend in with other women physically in the world, now I had the extra pressure of communicating for the first not as a man, but woman to woman. The last thing I wanted to do was come off during my final test with a stranger as some sort of an evil bitch just because I did not want to talk.

For some reason, during this portion of my life I was not having any problems attracting attention from ciswomen. After a lifetime of basic rejection from women, I tried to reach as a man, all of a sudden for the first time, I was having success as my transfeminine self. Even though I did not completely understand what the reason was for my success, I did not want to jinx myself and do too much and go back to rejection and loneliness again. So, I kept up what I was doing and for the first time built a new base to my life.

I had two reasons for my success as I looked back on those days. The first was, my inner feminine self-had so long to sit back and observe what I was doing with our lives that she knew exactly what she wanted to do when she had a chance to run the show for the first time. And the second was told to me by a person much wiser than me long ago that very few human beings have the chance to stop their lives and begin again, so don’t screw it up if you do. I was able to listen to both.  

Sure, I went through two lifetimes of first times with all the bumps and bruises which normally come with such adventures. When I think back to all those early days in the malls when I was getting laughed at for my weak initial femininizing attempts, I don’t see how I made it at all. I guess something deep down inside of me kept telling me that this was just an example of the first times I would be facing my whole life if I continued along the gender path I was considering.

I was far from deciding if I could ever slide behind the gender curtain to learn if I really wanted to be there. But somehow, I knew I would never forgive myself if I did not try. When I did, for the first time I found myself off the self-destructive male path I was on and on to a rewarding and healing path I loved as a transgender woman.

 

 

My Biggest "AHA" Moments

 

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on UnSplash.

During the long gender path which I have been fortunate to live, I have had many “aha” moments to look back on.

The problem I had was realizing that the times in my life were something I would forever remember, forget immediately, or just refuse to understand what they meant after my own ignorance set in. For my first example, I have to go way back to the first times I was exploring my mom’s clothes and makeup. I knew something was up, but I did not know exactly what and how deep it would run with me. All I knew was my desire to be feminine in any way was deeply forbidden in my family and most of society which called it being mentally ill at the time. Through it all, even though I did not fully understand what was going on with me, I did think I was mentally ill for thinking it.

That was the good news. The bad news was I was decades away from understanding the “aha” moment that I was living the wrong life as a man all along. Even if I was warned by a therapist that I respected very much that she could essentially do nothing about me wanting to be a woman and I was on my own to save a marriage that I really wanted to save. If I would have listened to her and started my male to female femininization earlier, I would have saved myself so much inner turmoil that it would have been amazing. But I did not and stubbornly hold on to the idea I could live as a man while at the same time cross-dress when ever I wanted as a woman.

Another problem was, I had moments when my feminine world was opening to me and I thought, “wow is that what being a woman was all about.” Like the day at the grocery store when I positively melted a young bagger who was stuttering as he shyly asked if he could take my groceries to the car. Right then I knew why I had such a difficult time talking to pretty girls in school when all my perceived smooth vocal abilities just disappeared. It was a giant “aha” moment when I had the chance to reverse course and cross that gender border so long ago.  

As I held on for dear life that I was just following my hobby as a cross-dresser, slowly but surely the idea of going through another male to female transition gained on me. I went back to the times when I was thinking that just putting on makeup and a dress was good enough. I always wanted to do more like the pretty girls around me did at school. I wanted to be the one being chased for a date in my new pretty clothes any time that I could. Which turned out to be never back then. Years flew by before they ever did as I began to test the world of ciswoman as a novice cross-dresser. Then, one night out of nowhere, the thought came to me that I was done just looking like a woman again, I wanted to inter-mix with them and see if I could be accepted. If I was, from that point forward I would change my self-gender perception from just being some sort of a harmless hobby to thinking about myself as a thriving transgender woman. A super scary, but exciting thought because once I went there and was successful, I could never go back to ever just thinking that I was just a man again. A real, enduring “aha” moment in my life.

The problem I had was once that I was becoming successful as a new transfeminine person, how could I stay there. Initially, I made up a new feminine persona to go with my new look. I wore the same wig and used my same new name every time I went out and before I knew it, I was being treated as a regular in all the venues I was testing out in the straight world I knew before as a man. Another big “aha” came when I was able to break the influence of all the gay venues I was going to which I really disliked and was accepted as me in a new world. Then I learned I could have fun doing it as I enjoyed my new feminine self so much that increasingly I did not want to go back at all to my old male world.

As I did, I began the all-important job of getting rid of all the male baggage I did not want or need anymore. At all costs, I hoped I could maintain a relationship with my daughter which I did, and if my brother did not accept me, so what. Which he didn’t and we went our separate ways as those two were the only two blood family that I had left. With all of that turmoil behind me, I was free to concentrate on my transgender future which did not include any surgeries at my age of sixty, but hopefully a chance to test out my body on HRT or gender affirming hormones. I was approved first by a doctor and then by the Veteran’s Administration to begin the hormonal treatment and positively loved it. It was as if my body was saying the hormones were an “aha” moment and were the missing ingredient to leading a fuller transfeminine life.

I am sure there were other “aha” moments which turned out to be bright light posts on my often dark and lonely gender path. Such as when my current wife Liz came into my life to love me and make me whole again by saying that she had never seen any male in me. I never realized that I had built up that much good karma to help my life along.

Thanks for reading my lifetime of gender experiences as a transgender woman. Hopefully, you can gain some insight to help you along.

 

Living the Dream before it Consumed Me

 

JJ Hart

As I crossed the six-decades portion of my life and spent at least five decades of it trying to stay under control by cross-dressing, I was trapped and had nowhere else to go.

It happened because I had embarked on such a complete path of looking like and moving like a ciswoman and my gender bucket list was shrinking due to too much use. All the trips to malls, antique stores, and thrift stores just became boring when I was passing through them with no problems. Even though I was bored, the idea of being successful as a transfeminine person still consumed me. And, to make matters worse, I was finding less challenges to undertake as I increasingly painted myself into a gender corner I had always dreamed about but never thought I could reach.

I always made excuses such as I was never going to be good looking enough to present well in the new world I was seeking when truthfully my overall confidence as a trans woman had more to do with my approval than my appearance ever did once I had went beyond the basic point I needed to be to blend in with the ciswomen around me. Life changed when I realized there were plenty of women in the world who dealt with being bigger in stature and even had broad shoulders such as I had. My realizations helped to give me the boost I needed to continue to let my so called “hobby” consume me.

The reason was that I was ignoring the fact that cross-dressing was much more than a hobby, it was becoming a lifestyle. The biggest problem was that nothing I did as a novice trans woman was ever good enough. Even my second wife did not like the person I was becoming when I took the time and effort to show off to her as I thought were my best feminine efforts. Even though I desperately was seeking her approval, it was becoming obvious to me that my inner feminine self and my wife were lining up to fight it out. I was left behind to pick up the pieces as I was realizing how consumed I was when I had one of my rare, sanctioned (by my wife) outings at Halloween in NYC when my wife decided she did not want to go with me. The night turned out to be a dream evening as I ended up going out with four other women dressed to thrill as I was and they all happened to be as tall as I was in our heels. The night even ended on a high note when I was asked to dance by a guy in the venue we went to. I turned him down because he had no idea that I had one basic difference from the other woman I came with.

Anytime I experienced such a wonderful evening such as that Halloween party, I wondered if the gender euphoria I felt was worth it when I came crashing down. I was consumed with the moment and wanted to re-live it time and time again, but I was tucked away in my male work world and could not get out. Looking back, I don’t see now how I survived the balancing act I was putting myself through. I needed to physically show up as the man I never wanted to be. While at the same time spend all my mental energy remembering the transgender woman, I was. If I could have cried during that time in my life, I am sure I would have cried myself to sleep many nights worrying about my gender dysphoria and how it always threatened to wreck my life. Even to the point of almost destroying my marriage to the woman I loved deeply when my frustrations would boil over into yet another fight about me. Some of the fights were so severe that my second wife told me I was not man enough to be a woman, or why didn’t I just go away and fix the problem and make both of us happier.

Perhaps, by this time, you are wondering too why I did not take her advice and do it. The main reason was, at that time, I was not ready to give up totally on the life we had together when I was a man and even though I was increasingly being consumed by the idea I could be the trans woman I always dreamed of, I was not ready to pull the cord and jump out of the plane just yet. Because I was still afraid of the new gender heights I was reaching and selfish enough to think my wife may still come around to accept me. For those of you who don’t know, she never did and died tragically of a massive heart attack at the age of fifty.

The whole experience sent me into a major negative tailspin which I had a difficult time emerging from. I think the only reason that I did was because I had let my feminine self-consume me, and she could not wait for the opportunity to take over and live. My life had come full circle, and all the time and effort I put into my male to female femininization came back to help me. I had already put the work into how I wanted to look with my make-up and fashion basics and was already out into the world actually discovering how it would be to carve out a new transfeminine life for my very own. I had gotten what I needed as I moved ahead towards beginning HRT or gender affirming hormones. Which were something I always wanted to try as part of my overall commitment to being as close as possible to being who I always was destined to be.

When life consumed me, I was always somehow able to accept it and even thrive with it. Even though it took me decades to do it with all the ups and downs of what I had to go through. At the least, it made life interesting.

 

So Many Ways to Come Out

 

Image from Nicola Dowie
on UnSplash.

Recently, I had a response from a young transgender man on how he should attempt to come out to the world.

First of all, thanks for the comment and yes there are many ways to leave your closet and enter the world of the gender you are trying to live among. I know too that I have many trans men who stop by and read my comments which flatters me because as we flip the gender script, often the worlds we must conquer are not that different. Gaining the female or male privileges when you feminize or masculinize yourself often are the biggest issues. After you come out to spouses and family.

Over the years, I have read about coming outs that have ranged from just showing up cross-dressed as your authentic self, all the way to writing letters trying to explain the way you feel. As far as I am concerned, just all of a sudden showing up as a woman (or a man) has too much of a shock value and is counterproductive when you are trying to explain how you want to live to the person sitting across from you. Writing a letter may be more preferable if you feel more comfortable expressing yourself with written words rather than speaking one on one with someone. In my case, even though I did not feel comfortable talking to family about my upcoming changes, I hitched up my new big girl panties (under my male clothes) and asked to speak privately with those family members closest to me.  My first attempt at coming out was with my only child, a daughter and as I always write about, she took it extremely well. Just to show me life could never be that easy, my coming out to my only brother went off the rails quickly and we have not spoken since about 2014.

Having said that, I do caution trans women and trans men who are just coming out to family and loved ones that you are in a marathon not a race and sooner more than later, your family might come around. Plus, there is an increasing amount of information available now to explain your desire to live as yourself. If you have the chance, you maybe able to direct them towards the positive aspect of what you are doing and away from all the negative news they may see from politicians on the media ads. In my case, the split between my brother and I ran so deep when he refused to stand up for me and invite me to our family’s traditional Thanksgiving Dinner, I just can’t forgive him for that.

On the positive side, the relatively few people who knew the former me notice almost immediately that I am happier now. And if you give someone the chance to calm down and see the real you, they will respect that and the real you.

Of course, as we flip back to the negative side, there are always those family members that will try to throw religion in your face. Unless you are more of a biblical scholar than I am, I usually just give up on them.

Overall, I find the different sides of transitioning between transgender women and transgender men to be interesting. Since I was raised around the male dominated world of trying to force my way through difficult situations, I never gave much thought to trans men having to adjust to not being passive aggressive so much. Then there is always the idea of using the restroom which hangs over both of us. Even though trans men are in a new world in a men’s room where no one wants to make eye contact or speak, there is always the idea of having to still find a stall to use. Which conceivably could attract unwanted attention depending upon how well you present and how long you have been on testosterone. I know I have oversimplified the men’s room process and if you are a trans man, I am always up for ideas on restroom survival.

Flipping the script again, using the women’s room as a trans woman is something I know quite a bit about. The first thing I quickly learned was I needed to make contact and speak when someone else was in “the room.” From there, much of what I learned was either common sense such as never placing my purse on the floor and making sure my stall still had toilet paper all the way to trying to pee in the bowl a certain way to mimic the ciswoman in the stall next to me. Then, no matter how much I was in a hurry to leave, I had to always stop at a sink, check my face and always wash my hands.

Anyway, you cut it, when you have desire to cross the gender border either way from male to female or female to male, you must learn so many nuances of the moves you are making. Even though there are strict rules you need to follow, often times you will find yourself making up your own rules as you go along. It is just the nature of the ultra-serious game we play. What has worked for me in the past may not work for you and often I hear from readers who have supporters and non-supporters in the same family. The only advice I can offer is to embrace your new gender allies and hope your detractors come around.

The end result always must be it is your life to live and you need to live it to be happy. Sometimes your path will lead you the wrong way, just like your GPS does on occasion but it is not time to panic until you can get readjusted. Be patient, and it will happen.

As always, thank you for the comments I receive, often they are difficult to answer seeing as how we dealt with such a complex issue such as gender. I just hope, in my small way I can help.

 

 

Feminine Power Moves

 

Image from Gayatri Mohotra
on UnSplash.

When I first began to seriously explore the world as a transgender woman, I was stripped of all my male privileges and wondered what I could do to survive if I found myself in questionable situations.

The big answer I learned was to try my best not to get myself into questionable situations to begin with. Lessons learned at an early age by ciswomen everywhere such as trying their best not to jeopardize their own personal security from toxic men. When I first came out, I was used to going where I wanted to go, when I wanted to do it which led me into several tense situations. One from a much bigger cross-dresser admirer who had me in his sights in a narrow hallway where I could not escape and another time when I was approached alone on a dark city sidewalk by two men in front of a gay venue. Neither place I should have been to by myself, and I was lucky to escape without any real problems.

By this time, I was used to the only feminine power I had was having doors opened for me by men and I knew I was missing much more in life if I wanted to pay my dues and transition into a transfeminine world basically the hard way. Since I couldn’t afford to go through any of the expensive gender surgeries of the time and did not have any insurance coverage that would cover any facial surgeries, I needed to find ways to accomplish what I wanted to face on my own. I learned the hard way that I could do anything I wanted to if I set my mind to it. Or I passed out of sheer willpower according to my transgender girlfriend Racquel. All it really meant was I was able to work my way into living the life I wanted to live through more effort on my physical appearance through better makeup skills and wardrobe basics. The same things I noticed other ciswomen doing in the world who themselves did not really have “passing privileges.” I just came into my privileges as a woman from a different way.

Another difficult phase of my male to female feminization project was the impact of woman-to-woman communication which continually goes on in the world that men are not subject to. Or the world of non-verbal communication women often use between themselves. I even went to the extent of taking feminine vocal lessons which focused more on what I said rather than how I said it. The keys I was taught were mainly built around the passive aggressive tone’s ciswomen take such as “are you sure you want to do that” rather than the traditional male “don’t do that.” I got quite a bit of valuable gender information from the course to use on my path which was always full of male stop signs. To repeat what I just said in essence instead of giving me a stop sign, my inner feminine soul was saying do you really want to do this.

Of course, the answer always came back to me one way or another that I was on the right path, and I felt so natural doing it that I just had to keep exploring what was ahead around the next blind curve. It was at this point that I began to discover what I had suspected all along those ciswomen had more going for them than having doors opened by men. With the help of HRT or gender affirming hormones, I opened my world to a whole new universe of emotions and senses I never knew (or allowed) myself to have. I was the one who could reach for her coat without shame when she was cold when my thermostat went crazy with hot flashes at the same time. And I became the one who could cry a happy tear at the drop of a dime. If I needed to or not. It was all part of who I was as I began to explore my feminine power base I was developing.

As I always do, I cannot give myself much of the credit for doing more than just surviving in the new women’s world I was as I began to thrive and enjoy my new power base. As my new friends kept telling me, welcome to their world. I needed to be careful how I responded because I did not want to give up much about myself and shield my male past.

Thankfully, by this time I had given up all my male privileges and was excited to be settling into my new life as a transgender woman preparing to go fulltime into the world. By doing so, I needed to prove to myself that I was no longer afraid of being rejected as a trans woman. Primarily by men who resented that I had left the boys club behind to slip behind the gender curtain to play in the girls’ sandbox. Thanks, in no small way to my lesbian friends who showed me how to validate myself.

Somehow, I managed to give myself extra time to drain the remnants of my old male life drain away before I went all the way and gave up all my male clothes. Which was the symbolic way of me finally severing my male past altogether. As difficult as it was to give up all those decades of struggling in a life I did not like, the relief of doing it was amazing.

Before I knew it, I was enjoying everything I could in the new transfeminine life I had only ever dreamed of. I was fortunate that I was able to live through several severe gender-based self-destructive incidents that I paid my dues on and was able to move on to find a whole new set of powers.

It turned out that I was simply giving too much trust to male powers I was born into and never had a chance to do anything about it. When I did, I seized control of my true powers and never looked back.

 

 

 

 

 

The Power of Pride

Image from Brian Kyed
on UnSplash.

Once again, it is Pride month. Time for celebrations around the country and sadly also time for all the transphobes and homophobes to come crawling out from under their rocks to try to protest.

Over the years, I was a regular participant in Pride marches in Ohio. Primarily the large ones in Columbus and Cincinnati. Very early on, I did not feel as if I had a substantial place to celebrate the “T” in the LGB celebrations. The closest I came to who I was when I saw a group of drag queens or weekend cross-dressers painfully trying to navigate the sidewalks in their sky-high heels. I did not have anything against any group; I just didn’t fit.

Fortunately, over time, things began to change for the better as I began to see more representation from all aspects of the transgender community all the way to parade grand marshals instead of the usual collection of drag queens. It was then I began to enjoy people watching to see all the many layers of rainbow life come together at a big party.

I had different things happen along the way too, like when my future wife Liz made me a shirt that said, “I was a transgender soldier, I fought for your right to discriminate against me.” I wore it into a Veterans Administration exhibit and received too many uncomfortable looks to be happy at the reaction, so I moved on.

Then there was the time that one of the main restrooms was out of order at a Cincinnati Pride which funneled all who needed to go into one restroom. I thought it was funny that all the TERF’s in the crowd who were anti men (and trans women) had to use the same restroom as everyone else. Everyone else except a stray hornet or two took it all in good humor and even went to the extent of passing extra toilet paper up and down the line. For once I was happy that if I was forced to, I could still use a hated urinal since I still had the proper equipment. I did not have to because the men’s room was the one that was closed.

That was the year Liz, and I went on a Pride Pub crawl when there were many more gay venues in the Cincinnati metro area. For a small fee, we were able to ride on a bus to quite a few venues and had a great time. Especially since by the time we finished the route it was raining. Since it was the summertime of the year, I decided to wear my blue tank top, denim mini-skirt and sparkly flip flops (because it was so hot and humid) I was ready for the weather. By the time we were done, we were drunk, soaked and happy we let someone do the driving for Pride as we finished up in a gay country themed bar doing Jello shots. It was one of the Pride evenings I never wanted to end.

I had other fun times when I went to Ohio’s biggest Pride with my lesbian friends in Columbus. Again, I enjoyed my company and the people watching I was doing and I did see other transgender women in the vast crowd. For effect, I wore the trans military themed shirt Liz made me again, but I just wore jeans and flip flops to go with it because I certainly wanted to be comfortable for all the walking I knew was ahead. Ironically, I could have worn much less since by this time, the HRT gender affirming hormones I was on had provided me with a well-formed set of feminine breasts and I could have bought me a set of pasties and joined the lesbian “tit’s out” crowd. But I did not go to that extent to expose myself to the world.

Along the way, I did manage making it to smaller Prides in places such as Yellow Springs, Ohio a very mellow, liberal diverse village who always manages a wonderful celebration of the LGBTQA+ world. One night in particular, I really wanted to see a famous local drag troupe (The Rubi Girls) perform. As luck would have it, I found a seat at the crowded bar next to a ciswoman who was dressed as “Debra Winger” from the “Urban Cowboy” movie, complete with the black cowgirl hat. Through our conversations, I never did find out if she was the real “Debra Winger” or not. Who knows, maybe I should have asked for an autograph but did not want to embarrass myself. As it was, I stayed through the show and donated what I could afford to the “Rubi’s” who at that time had raised over a million dollars for Aids research.

These days, the world has shrunk for me, and I must watch and envy the Pride celebrations from afar because our LGBTQA+ community has a lot to celebrate such as our resistance to and visibility from the politicians who want to crush us. It is sad that Pride encourages all the keyboard cowards to come out of the woodwork in their mom’s basement to harass us. I just hope my writing in such a small way keeps me visible when I can’t be because when I was younger and healthier I enjoyed the Prides I went to.

I also hope the crazies are kept under control wherever you go to celebrate your Pride because you deserve the chance to do it. In Cincinnati alone, later this month, they are expecting a turn out of three hundred thousand people.

I have resigned myself to the fond memories I have of Pride with the close friends I made around me. Together, they made the celebration so much better than they ever knew. Even if you are just beginning on your gender journey, you can celebrate Pride too. Since you are starting to face the long and difficult process of answering many highly personal questions. As you do, your Pride may become a better place to express yourself with others who accept you. I found it to be an amazing experience.

 

  

So Many Choices...So Little Time

 

Image from Drew Colins
on UnSplash.

One thing that I learned from experiencing decades of cross-dressing is that there were so many choices and so little time.

It all started when I had to scramble for any time, I could find by myself dressing as an imagined pretty girl in front of the mirror without discovery from my brother or worse yet my parents.  I was born as the eldest son into a very male dominated family, and I was expected to fit right in with that male mold. I had little idea at the time that I was destined to break that male mold during my life and it was not going to be easy.

Back in those days, I had very little income that I scraped together from doing household chores and a newspaper delivery route I had for several years. The first feminine items I could afford to buy on my own were makeup accessories but first I needed to figure out a way to get to a store undetected and then decide what to buy. After putting a lot of thought into my situation, I remembered that my grandma lived in town, fairly close to one of the old five and dime department stores that sold makeup. I used the excuse to visit grandma, then go and shop. Or try to.

The only problem with my plan was that my dad worked downtown close to the store I wanted to try to buy my first makeup in. I was tired of using my mom’s samples, That was all well and good until I gathered my courage and walked into the makeup selection of the store I was in. As I viewed the extensive selection of cosmetics, I almost panicked and walked quickly from the store. There were so many choices and so little time to choose anything that might help me during my novice beauty program. Somehow, I stood my ground and picked out some foundation and lipstick which fit in with my limited budget, gathered my courage and headed for the checkout counter. Just knowing I would get made fun of along the way. Amazingly, the person at the cash register did not give me a second look as she took my money and I was no longer a virgin in buying my own feminine supplies. I just wished I had more access and money to do more.

I would have more financial resources later in life along with the knowledge to go with it as I learned the fun of doing thrift shopping for just the right choice of clothes to add to my wardrobe.  Plus, the thrift experiences gave me a chance to be patient in many of the bigger stores with seemingly an endless supply of discarded fashion. When I took the time to try on a new item I had never tried to wear before, I had two benefits. I didn’t have to pay much for the item and two, I could see how well it either flattered my difficult to please male testosterone poisoned body or didn’t. It helped too, when I was able to streamline the shopping experience and give myself time to vary my day as a novice transfeminine person. Instead of just facing an endless amount of clothes. I actually had time to do other things like take myself out to lunch. Then, again I was faced with an almost never-ending choice of where I could eat. Since I had already tried too many fast food drive throughs with various amounts of success, I decided to step up my game and try to eat at one of the casual dining restaurants I had went to and even managed as a man. Since I was still on a gender time clock and had to be home by a certain time dictated by when my second wife would be off of work, I was still facing so many choices with so little time to enjoy myself as a transgender woman.

My plan was to just get by and improve myself a little at a time in a world of ciswomen I was just discovering. By doing so, I discovered that most ciswomen ignored me if I was dressing to blend in with them or were just curious of why I was in their world. Of course, I did run into the occasional TERF woman who hated me and wanted me out of her world, which I did. One way or another, I was encountering far more women in my quest to be part of their world than I ever did any men because I just wanted to be out of my long-standing membership in the men’s club and they knew it. The only thing I did know was that I was increasingly not so lonely when I went out in the world to my regular straight venues. All my lesbian places had closed up and the gay venues I used to go to just brought back bad memories of me being looked at as just a drag queen so I was stuck…just where I wanted to be and I was satisfied, until I went too far and tried too hard to be accepted.

In my search for acceptance, I began to become too overconfident in my ability to succeed a began to look for more choices of where to go in such a short ill-conceived amount of time. What I did was start going to redneck themed places thinking I could be accepted when I was not and even had the cops called me one night in a venue, I was just trying to drink a couple beers then pee before I went to another place I had been to a lot. It turned out that they would sell me the beer, just not let me get rid of it.

As it turned out, I was/am able to live a long life and see many of my choices gang up on me in a very short period of time. Destiny worked its magic and gave me a full circle of life to live with. Throwing in that I was a transgender woman just added a little spice.

 

A Humbling Gender Experience

 

Image from Katherine Hanlon
on UnSplash. 

For literally decades, any thoughts I had of living a successful life as a transgender woman, were only thoughts. I was never sure if I had any chance of making it. In fact, most of the time it seemed as if I was swimming against the current in a fast-moving stream of ciswomen, I wanted to interact with so badly, on their terms.

Doing it on their terms was my problem as I had always tried my best to be a strong student as a man of how all the women around me were living their lives. The main issue always was that I was only allowed to see so much of what was going on across the gender border. Again, because I was a man and had not yet paid many dues yet as a novice cross-dresser and not even a transgender woman yet. I still thought my real issue in paying my dues to be let behind the gender curtain came from my appearance in the world. Just being able to blend in with the ciswomen around me was good enough.

It was quite a humble experience when I found my appearance (and no matter how much it was improving) was not going to be enough. Even though the mirror was being kind to me as it told me I presented well, I was still stuck behind it as I still needed to put the image into motion. I was caught in the place where I looked good as a woman…for a man trying hard to accomplish it. I desperately needed to find a place where I looked as if I wasn’t trying to dress to impress. I was just being me. The problem then became who was the me I was becoming? How deep did my feminine desires run and where would they ultimately take me became the main things I thought about in my life. Every spare moment I had was spent either actively cross-dressing in front of the mirror or making plans of going public with how I looked and making the world my mirror.

As I learned the hard way my lessons on how to blend in with the world around me, often I was brutally laughed at and rejected by the world because I was dressing to thrill and not to blend. I guess I could say, I was humbled in the worst way by groups of teen girls in the malls I was just trying to shop in. My initial goal back then was to face my teen critics one-on-one until I failed completely or succeeded after many times of going back to my cross-dressing drawing board. It was like ripping a band aid off a mental wound and saying too hell with it and trying again to be successful. Until I was.

Rather than become overconfident at that point, I decided to try to build upon my newfound success and work on things such as how I moved and walked in heels. I discovered that every little discovery helped in my male to female femininization project such as keeping the old male scowl off of my face when I was out as a transfeminine person. No more scaring little kids away who called me a woman which was good but a mean woman which was bad of course. It was the last thing I wanted to do after working so hard on the basics of presenting as a passable woman.

The more I progressed on my path to living as me, the more humbled I became. Too many nights I came home in disbelief at the lessons I had learned from men and ciswomen in public as I struggled to fill out my gender workbook which was way behind the rest of the world I was dealing with. I learned men did not value anything I had to say unless I was spoken to first and women had their own way of communicating around men even if the men thought they were in their conversation. Just as a starting point. I also learned of a whole new lesbian culture I knew nothing about and where I could possibly fit in as a femme lipstick lesbian. As you can understand, the terminology and how I fit in came at me quickly and again I was extremely humbled to be asked to go to lesbian mixers where I learned a lot.

I learned also that women lead much more layered existences than men do, often built around dealing with men themselves. I did not have to worry much about that because I was not attractive enough for men to pursue me and after my lesbian friends taught me I did not need a man for validation, my life brightened considerably.

As I progressed deeper and deeper along my gender path, it became increasingly obvious that I could indeed achieve my goal of someday succeeding in a feminine world. Even though in many ways it did not resemble my initial dreams. In no way did I think I could maintain my sense of sexuality as I never made it with a man. In my own way, I maintained my own “Gold Star” status that many lesbians I knew maintained. The closest I ever came to getting any real attention from a “GS” lesbian were a few kisses.

When my new world began to open up, I was very humbled to be there at all. Along the way, I have survived issues such as severe depression and negative attitudes towards me from loved ones to stick to my dreams and goals. Remembering where I came from helped me form the strong building blocks to complete such a diverse and difficult change in my life. Using the negatives in my male life to build a transfeminine one was one of the best moves I ever made in my life as I made a complete circle back through all my male years to be the person I always dreamed I could be.

I was back to being me. The only transition which really mattered.

 

 

 

 

 

Stepping off a Gender Cliff

 

Image from my first salon
visit 12 years ago.

As I slowly began to become part of the world as a transgender woman, I felt as if I was sliding down a steep slope towards a deep cliff which I could not see the bottom.

Not being able to see the bottom of the canyon I was facing was probably the scariest part of coming out as my authentic self and being allowed to be behind the gender curtain with ciswomen around me. Along the way, I worried about the smallest things such as my appearance, all the way to how I sounded if I had needed to talk to someone else. Many times, in an emergency only because I was so unsure of myself as a novice transfeminine person. Sadly, I learned the hard way that as weak as my communication skills as a trans woman were, not communicating at all with other women was worse. Because not saying anything made me come off as being somehow stuck up or worse yet, bitchy.

Through it all, I came off sliding slowly down my gender path as I ignored several stop signs thrown up by my male self or my second wife who knew she was in danger of losing her husband altogether. For most of my journey at this point of my life, I was in the dark and used that as an excuse of why I had just ignored or run the stop signs I was facing. Whatever the case, I was living an exciting yet scary time of my life.

When I came out to my daughter nearly a dozen years ago, I finally had lost my grip on the small trees and vines I was holding onto during my steep descent into trans womanhood.  She surprised me by promptly supporting me and her only question was why was she the last to know, when in fact she was the first to know I was much more than a part-time crossdresser (as my first wife and her mother thought), I was actually a transgender woman who was afraid to admit it to the world.

Since my birthday was right around the corner, my daughter volunteered as a gift to me to take me to her hair salon/spa for a haircut and color makeover on my hair which had become long enough to work with. Even though the whole idea scared me to death, I took her up on the offer and she made the appointment which would forever change my life.

Before I knew it or could even entertain any thoughts of backing out the day was upon me and the next thing I knew I was with my daughter and her stylist looking at seemingly endless color and style combinations that I needed to choose from. Plus, I had to walk past a endless line of women in chairs who had nothing else to do but give me their undivided attention as I walked by, nervous as hell and trying my best not to show it. Fortunately, I had a complimentary glass of wine to calm me down as I chose a highlighted blond/red cut which all of us thought suited me the best.

Once I was done and allowed to see myself, I have to say I was impressed and knew why ciswomen everywhere put so much emphasis on taking care of the hair through salons everywhere. As I left, I felt as if I could skip my daily dose of gender affirming hormones because the estrogen was so thick in the air in the salon. As I said, it all added up to a day I will never forget thanks to my supportive daughter I could never thank enough over the years as she helped me pick out a new legal name change that my three grandkids could easily grasp. Ironically, the middle grandchild who was in the fourth grade had a teacher who was an out gay teacher in the school system and had my grandchild as a student. Then my daughter needed to explain the difference in their gay teacher and their transgender grandparent. As you can tell, diversity ruled in their house and went full circle when my oldest grandchild came out as trans.

As it turned out, I had nothing to fear from sliding off my gender cliff because it turned out I had built such a group of supportive people to help me when I fell. Of course, I always have to mention my future third wife Liz who along with my daughter turned out to be my best allies during my male to female feminization project. In fact, it turned out they knew me better than I knew myself and showed me the way to success. Liz in particular always told me that she never saw any male in me at all. Which in many ways provided me with the powerful shove down my gender cliff into a world I always should have been part of in the world of ciswomen. I don’t know what I would have done without the guidance of women such as Kim and Nikki also. I just know I probably would have kept up the male charade I was living longer than I did.

Perhaps the ironic part of them providing me a safe landing was when all the ciswomen refused to take any credit. The only response I ever got was welcome to our world when I tried to share stories about my first hot flashes, so I learned to keep quiet and learn how to protect myself when the expected gender crash happened. Because of women such as Min and Kathy, their initial invitations to their girls only nights out helped me to learn what life behind the gender curtain was really all about.

If I had known all I had learned earlier about being a transfeminine person, I would have definitely taken the plunge down my cliff earlier than I did. Not much I can do about it now as I am very much where I wanted to be and the plunge was not too bad after all.