Following your North Star

 

Image from Heidi Fin 
on UnSplash. 

I define my own personal “North Star” as the basic direction I had to go to be truthful to myself. Many times, I found how valuable my star was when I was lost in my own transgender woods and couldn’t see the forest for the trees.

Along my path, there were many times I lost sight of my North Star and needed to regain it before I could continue. As I did, I spent many a very dark night searching for my life’s truth of wanting to shed my male existence for a feminine one. I would not recommend what I went through to anyone because it was a long, lonely journey. Even still, I was fortunate in that I seemed to always have just the right amount of gender euphoria to propel me forward. It did not matter if I was just gazing at my image in the mirror and thinking I was a pretty girl, or shopping for groceries in our local market, something possibly positive came along for me to see my star and wondered if it was still within reach.

Sometimes, life was cruel and dealt me roadblocks which kept me from following my dreams such as the unplanned birth of my daughter. Which turned out to be the best thing that ever happened to me in my life. At the time of her birth in 1976 I was very much out of control and needed something to ground me. Much more than the excessive amount of alcohol I was drinking at the time. All the beer did was help me to lose sight of my North Star until I could regroup and find it. I did not learn until much later how alcohol was a depressant and did not mix well with my already depressed personality. Even though I was dazzled by the miracle of birth and the rapid growth into a little person by my daughter, life was still not good as I was sliding by in a haze most of the time and losing track once again of my North Star.

Somehow, I was able to emerge from this part of my life on my feet and ready to search for my truth again. But not enough to accept what I was finding. Even though that bright light of a transfeminine existence seemed close enough for me to reach out and grab it, I just kept denying its existence and taking the route of least resistance and was existing the best I could as a part-time cross-dresser.

When I changed professions and entered the professional restaurant business, I developed a love/hate relationship with what I was doing. I loved the extra money and advancement it brought me but hated the hours and extra pressure the job brought with it. I guess the good part also was that the new profession cleared the way for me to reset my existence and locate my North Star again.

Once I located my star, I had to finally face the reality of where it was leading me. Gone were the evenings or days of going out into the world thinking I was nothing more than an innocent man trying to look like a cisgender woman. In, was a new reality that I wanted much more than to look like a woman. I was a woman and needed to see if I could live my truth, I knew all along but refused to face. Even though I was terrified of doing it, I was advancing down my gender path, and the skies were clear so I could see my star and have an idea of where I wanted to go. Better yet, once I was passing my gender mileposts of very much socializing with cisgender women as an equal in my mind, there was no going back.

As I did it, I made certain I was trying to cover all my basics such as what I would do to live in a new transgender world I dreamed of and in reality, had never seen. Such as how I would support myself because I knew my current male job would never support a mid-gender stream male to female transition. At that time, I was still several years away from an early Social Security retirement, so I needed to be careful of what I decided to do. What I decided on was a low impact non pressure job I could work just to get by for the time I needed until I retired. I found that was impossible and I had to backtrack into fast food again and work a job I hated until I could quit and pursue my star.

By this time, I had paid a lot of dues playing in the girls’ sandbox and I had a very good idea of what I was facing if I went full time into a transgender world. I don’t think it is possible to ever capture your North Star, but I do think you can come close to living it. There are many paths to get there, and no one is right. Some transition on their own while others have help like I did. I was always a social critter, and my process happened to work for me but yours could be different. Plus, destiny can often alter your path to following your personal star. Do not panic until you find it again and revive your journey.

Remember, you are in uncharted gender territory, often without a compass. When it happens to you, you need to just hitch up your big girl panties and do it.

 

 

 

A Labor of Love

 

Image from Mor Shani

Lately, it has occurred to me that possibly my posts have been a little negative when describing my journey along my gender path. Sure, my trip had its ups and downs but overall, it was a labor of love. Gender euphoria always seemed to come along at just the right time to keep me centered on my dream of living a transfeminine life. Finally meaning to me that transitioning male to female was the only way to live for me.

From that point forward, I just had to figure out a way to do it. I knew I loved the lure of women’s fashion and makeup, and how it all changed around me on a seasonal basis. So far from the male fashion I was used to. Instead of just putting on a coat when the weather became cooler outside. Now I needed to choose between leggings, boots and fuzzy sweaters to keep me warm and stylish.  Furthermore, I loved the concept of seasonal change and the desirability of going through my wardrobe to see what could stay and what had to go to the thrift store.

Even though, fashion and makeup remained a priority for me, a new love interest set in when I began to explore the world more as a transgender woman. Whole new gender vistas opened up for me relatively quickly as I needed to put my static mirror version of my trans woman self into motion. It became a labor of love to go out and start meeting new people. As I did, I came to the realization that most strangers I met did not mistake me for a cisgender woman, but on the other hand, I could be quite satisfied to be recognized as myself…a woman from a different background. I think in a couple of the venues I became a regular in; I became their token transgender woman to prove their overall diversity. Whatever the case, I loved the extra attention I was getting. Especially from the ciswomen I met who were basically curious what I was doing in their world.

All the on hands experience in the world I was getting helped me to want more and leave my male life behind. As I always say, the gender change concept seemed to be so natural for me as I went forward. The only problems came from wondering what I was going to do about all the male baggage I carried with me. I discovered I was much more than a man trying to put on a pretty face, I was a full-fledged person trying to build a life from scratch. All the nuances of doing so extended way psst making sure my shoes matched my purse, all the way to wondering how I was going to handle the woman sitting next to me when and if she tried to make conversation. In a very short period of time, I became used to the challenge, and it became part of my life and yes, I loved it.

As I increasingly loved this new life I was living, I was able to balance between the two main binary genders. Before it became too much to handle mentally for me. It became increasingly evident that if I was going to survive as a person, I was going to have to choose one of the genders pulling on me. At that point my lifetime of loving everything feminine kicked in for me. Long ago, I had realized I was much more than a casual crossdresser and made it a love affair to learn more about my dream of being a woman on my own terms. Which meant I did not necessarily need all the extensive facial or gender realignment surgeries. I just needed to present well enough in the world as a trans woman to be left alone. Mainly because of the circle of ciswomen friends who accepted me as an equal, I was able to achieve my goal. Even with the added surprise of finding a woman who loved me the way I was.

The tragedy probably was I did not realize the depth of the love affair I was having until much later in life. I would have preferred to have spent more time living as a transgender woman in a world I created. Rather than sharing it with a man I started a life with and had very little control over.

I will never know (of course) what life I missed and maybe the course of destiny I was on would have stayed the same anyhow. Just being able to acknowledge the lifelong love affair I was on is just enough to rationalize where I ended up. So if you are just starting or contemplating starting your journey, try to look down deep inside of yourself to see where your love affair has taken you. It may save you problems later on your journey.

 

 

 

 

Gender Euphoria equals Black Friday Fun

 

Image from Markus Winkler
on UnSplash.

Yesterday’s Thanksgiving feast at my daughter’s -in-laws proved to be everything I thought it would be.

To begin with, all the usual suspects were there, including my trans grandchild who drove back from Maine with their partner for the dinner. Of course, my daughter and son-in-law were there also, with my first wife who I remain friends with today. Even though she slips up on occasion and calls me by my dead name. I forgive her because she is the mother of my only child and is getting a little forgetful in her old age. As I am.

To be surrounded by family who knew me before and to be accepted the way I was, always means a lot to me. Giving me a family to fall back on when my blood family rejected me, which I wrote about in my last post. I have never forgiven them for what they did and have kept my distance for over a decade now. If you missed my post, my bitterness stems from when my brother and sister-in-law asked me not to come to our Thanksgiving dinner when I came out to them as transgender.

As I have mentioned several times, my new chosen family has more than made up for my blood family loss. Especially in times such as yesterday when I am supplied with plenty of gender euphoria. Which brings me to the second part of this post, my first “Black Friday” shopping experience as a transgender woman.

The whole “Black Friday” woman’s shopping experience was always one I wanted to experience on my own as a transfeminine person and finally I had the chance because my second wife worked retail and would be busy. I knew if I played my cards right, I could set my work schedule up so I did not have to be at work until later in the afternoon, so I could pull my dream off. I knew what I was going to wear and knew where I was going to wear it, so I was set for an early morning departure as I pulled up my panty hose and picked out a big fluffy sweater, mini denim skirt and comfortable walking shoes. Just in case I could not find a close spot in the parking lot at the mall I chose.

As I found a parking spot and entered the crowded mall, I could not believe I was living out one of the big bucket list items on my gender dream. I was actually shopping for Christmas bargains with many other ciswomen who were oblivious to having a trans woman among them. The only problem I had was time. I did not have very much of it before I needed to head home and get ready for work in my old boring male clothes. Even still, I managed to walk away from the experience with the knowledge I could, indeed, make it in the public’s eye as a woman going about her everyday life.

Little did I know, my experience on “Black Friday” set me up for other bucket list activities and ones that required me having more skill in my new exciting yet scary gender. By going down the path I was on, I slowly realized I could never go back. Even if I had wanted to. As I always point out for me, my biggest problem was communicating with other women. I was always shy to begin with and the whole idea of talking to strangers as a transgender woman was staggering. Life became more than just interacting with clerks in clothing stores when I set out to learn how I may be treated in my male to female gender dream world. I even went as far as taking voice lessons to improve my vocal quality of life.

What proved to be the deciding factor was every time I was accepted in the world as my true self, I felt the flood of gender euphoria and wanted more. I felt so natural in my dream life, it did not feel like a dream anymore. It felt like I was living the life I always should have lived.

To get there, I needed to cross many bridges, some of which were very steep. Since I was afraid of heights, many times I was afraid to climb them and needed all the internal encouragement or gender euphoria to keep going. Thanksgiving dinner proved to be a big help as I was able to gain the confidence of a group of people I knew before I transitioned. It was the bridge I needed to do a lot of holiday shopping which I will write about more as Christmas approaches.

 

 

Following the Gender Breadcrumbs

 

Image from Elena Moshvilo
on UnSplash.

Following the gender breadcrumbs in my life meant finding the brief moments of gender euphoria I experienced and running with them.

Even when the mirror provided me with euphoria with the rush I felt when I saw myself as a girl, the feelings seemed to be exceedingly short and frustrating. I had yet to figure out my longing for the feminine clothes I was wearing meant very little to me. What was more important was, could the cross-dressing process ever take me closer to my dream of living a transfeminine womanhood.

Along the way, there were times when the breadcrumbs almost disappeared totally, leaving me completely lost and back into my closet. In despair, as I looked around, I did find enough crumbs to keep me moving because I was slowly learning, failure was not an option. I could take many of the hard-earned lessons I learned in the male world, adapt them and use them in my new exciting feminine world. For example, I learned that even though men compete differently than women, there was an equally intense competition going on between the ciswomen in the world that men knew very little about. Way past just being concerned of another woman looked better than them.  Since I did not have to worry about that, it took one more problem away from me. I never thought I looked better than any cisgender woman and I was not that shallow anyway.

I had more important problems to worry about as I searched for breadcrumbs to guide me along the path, I was on to transgender womanhood. Afterall, I was seeking to accomplish one of the most difficult tasks a human attempt to do which is change one of the most basic needs a person has, and that is their gender. Starting all over and carving out a new life was daunting for me, and I needed all the help I could get. For some reason, I found myself with ciswomen who spread the gender breadcrumbs for me. I could sit back and observe how they conducted their lives, good and bad. From them, I could see not all was peaches and cream as a woman then decide if I still wanted to do it. Then structure my life the best I could. My biggest problem was throwing out and ignoring all the hard-earned male breadcrumbs I had accumulated. In fact, I had almost put together the entire loaf which I kept trying to break up and throw away.

The most positive aspect of my life became the nights I went out with my lesbian and transgender woman friends, and we actually enjoyed ourselves so much we began to do it more and more. My breadcrumbs became easier to follow because I was different to my friends. I was not quite a full-fledged ciswoman as they were, but on the other hand, I was far from being a man they stayed away from. I was certainly baking my new loaf as a transgender woman with the help of my inner self who had been with me all the way and was just waiting to be set free.  It seemed most all of my dark lonely nights were finally behind me again in life. This time, on the side of the gender border I so long had waited for to open.

Wherever you are on your gender path, I hope it is lit well enough for you to see your breadcrumbs and have enough gender euphoria to get you by until you face another learning experience. I know, at times, the entire experience will seem overwhelming and hopeless. But the light at the end of the tunnel does not have to be the train and again I point out what a difficult path you are trying to follow. Risking, spouses, families, friends and jobs are never easy and is intimidating to say the least.  That is why if took me till the age of sixty to take the leap of faith I always wanted to do…live as a woman on my own terms.

It is important to note, you are doing the search on your own terms and the nay-sayers who like to point out you will never be a ciswoman are right. You can’t, but you can reach a womanhood of your own making.

Best wishes to finding all of your breadcrumbs along your path, and reaching your dream.

 

 

 

Gender Awakenings

 

Image from UnSplash.

Gender awakenings came early and often for me. I say early because from my earliest days of conscious life, I knew something was not right about me. As I always point out, this was in the 1950’s in the dark days of the pre-internet era when any gender information was difficult to come by. To make up for it, I experimented wearing my mom’s clothes and trying to apply her makeup the best I could. Then I would wear out the carpet in front of the hallway mirror admiring myself. Somehow, I convinced myself I was a pretty girl ready to go out into the world.

When I finally broke out of my closet and tried out the real world as a novice cross dresser, I received a rude awakening. Initially, it came from groups of teenaged girls I encountered in the malls I went to. They were brutal and not shy about laughing at me. Too many times, I was sent home wondering what the problem was with my image or presentation as a woman. One thing was for sure; the mirror was lying to me when it told me I could pass with no problem. I just had to do better if I was to survive in chasing my dream of living as a woman. In fact, at times it looked as if I had no chance of ever making it at all.

Fortunately, as dreams went by, I found I had an achievable one as the years went by. But achievable never meant easy. I had many negative transgender awakenings mixed in with just enough gender euphoria to keep me moving. It could be as little as encountering a group of teen girls with no reactions, all the way to having lunch when I went out to shop. What I was slowly doing was replacing my mirror in the hallway with the world. Maybe this male to female transition trip was not going to be so difficult after all.

At this time, over confidence got to me on several occasions when I had left the relative safety of the gay bar scene and tried to move to more familiar venues such as sports bars and even lesbian taverns. The problem was, I became too comfortable when I was accepted and had a tendency to slip too far back to old unwanted male roles. Keeping track of where I was in my new life and taking too many chances. I was guilty of being in the wrong place at the wrong time and nearly suffered from it until I learned my male privilege of safety no longer applied. I also was not prepared for how fast I lost part of my intelligence when I was dealing with men. Very early on, I found myself being completely ignored when I ended up with a group of men. Even though, I knew more than they did.

As I learned I would have a much easier path to acceptance from other women than men, I discovered the hard way that was not always the case. The well documented times when I had the police called on me for using the women’s room at one venue, all the way to being called a pervert in another place come to mind. Those were deep wounds to overcome but somehow, I did and found stable places to go to which accepted me for who I was. Even to the point of protecting me as their token transgender woman. The basics of smiling often, causing no trouble, and tipping well did wonders for me.

Even still, I had to be careful because I had a wife, family and job to come home to after my dream evenings as a transfeminine person. Soon, the delicate gender balance I was trying to maintain became too much to bear. I was to the point where I was just waiting for the next high heeled shoe to fall, or the next gender awakening to occur. I just knew I had come too far to turn back now, and my dreams were within reach. Only my big three stood in my way and destiny was coming along to take care of them.

My wife suddenly passed away, leaving me free of anyone except myself to answer to when it came to my gender awakenings. Plus, the only person I really cared about in my family (my daughter) became my staunchest ally when I came out and I took an early retirement, so I did not have transition on a job of any sort.

Once my gender awakenings started to come, they came fast and furious like a runaway train. The best part was, the whole process felt so natural, I never wanted to turn back.  Somehow, I kept the train on the track.

 

 

 

 

 

 

Dressing for Success

 

Image from Mohammad Nadir
on Unsplash. 

During my earliest days when I was forced into being a boy, anytime something negative or even challenging happened to me, I would run home and seek solace in my soft and colorful feminine clothes.

Soon I called the cross dressing I was doing, dressing for success. Mainly because I felt better as I did it. The sad part was, very soon the feelings of gender euphoria went away, and I was back in my unwanted male world where I was expected to succeed. During that time in my life, I was able to barely keep my head above water and still slowly improve my feminine basics in such things as the makeup arts. I guess all those hours of watching my mom apply her “face” as she called it, came back to help me. This was the 1950’s when women took their appearance much more seriously than today. All women were expected to dress for success.

As I barely stayed afloat with my cross-dressing challenges, it soon became more evident to me that there was much more going on with me than met the eye in the mirror as I tried to appreciate myself. It was about that time, when the internet showed up, and I was able to research terms such as gender dysphoria and transgender. Suddenly, I discovered who I might be and certainly found I was not all alone. It all started to make sense why my urge to cross dress never really seemed to go away. It was always with me in the back of my mind.

Soon, as I joined the world as a novice transgender woman, dressing for success largely depended on if I could go out into the world and blend in. I began the easy way by trying my hand with shopping mall clerks who for the most part were only nice to me for the money I needed to spend so I could be more fashionable and feminine. From there, I branched out to challenge myself by stopping to eat lunch and face servers one on one to see how I did. I did well, and very rarely did I have to run home and wonder what I did wrong and go back to my gender drawing board. I did not realize it but what I was doing was replacing my mirror time with time in front of the public. A very valuable learning experience as I discovered venues such as coffee shops, bookstores and even antique malls where I could shop and relax.

Each experience helped me to learn more about myself as a transfeminine person and then dress for success from it. To quit being so flamboyant with my wardrobe and wigs became my new goal as I was settling into my new life. People began to know me quicker, so I needed to be better in my approach to dressing for success. I learned I did not have to lose any of the enjoyment I experienced as a trans woman; I just needed to follow the lead of the cisgender women around me. I did not necessarily have to dress down for the grocery store and up when I mixed with the professional women out for a drink, but it helped me to feel better and relax. Plus, heels and hose would have certainly not worked when my lesbian friends, and I got together.

At times I even took my dressing for success to the extremes to be able to judge what the public was thinking of me. I used to wear my best sunglasses so that strangers could not see my eyes and tell I was looking at them, but were they looking at me? And one of my favorite “props” to use when I went out to be alone was my cell phone which I always had handy when I turned out to be the only woman at the bar. That way, I was trying to show anyone else I had someone else on the way, and I was saving their seat.

To be sure, dressing for success as a transgender woman was always a more complex process than doing it as a man. From undergarments to accessories such as jewelry, wigs and purses, women naturally lead a more layered life which can be reflected in the way they dress. I certainly had many more compliments on my outfits as a woman than I ever did as a man. Primarily, it was because it was something men never do and often, many cisgender women used compliments as simple conversation starters when they were curious about me.

As with all cisgender women, dressing for success is something transgender women must learn. The problem being we come from such a vastly different background to do it. Almost none of trans women had the benefit of peer pressure and a mom to guide us through the initial makeup process. Our workbooks were blank when we started our gender journeys. Playing catchup was not a fun game to play for me as I found making up my face was different than painting model cars. Most certainly, dressing for success was a lifelong experience for me.

 

 

The Same Old Road

Image from Danijel Skabic
on UnSplash. 

Quite early in life, I grew tired of the same old gender path I was on. Although I could not exactly put a finger on what was wrong with me, I knew something was. What is that definition of insanity? When you do something over and over again and have the same results, I think it is.

Also quite early, I thought I was the crazy one because of my deep-seated desire to be a girl when I was being forced into being a boy from birth. Little did I know, I was destined to become a late gender transitioner in life and must deal with my own form of insanity for fifty years, before I had the courage to do something about it and get off the same old gender road I was on.

As I traveled, it seemed like I was getting better than ever at finding every bump, curve and pothole along the way. Possibly, I was attempting to make my male to female journey even harder, just to prove I could do it. As I like to say, my gender workbook was blank and everyone around me could tell it. Plus, when I first began to get serious about trying out my feminine self in the world, the only outlet I had were the annual Halloween parties I went to. Early on I tried to dress sexy/trashy and then after a couple of years built myself up to trying to present as a cisgender woman at the party. Which surprisingly I was able to do way back when I was still into Halloween as my outlet from the same old gender road.

The best part was, I was able to locate side roads along the way as I was able to present better in the world as a transgender woman. The side roads enabled me to explore different rabbit holes and dead ends to see if I could survive in a new exciting environment. When I had the courage to do it, the road actually smoothed out for me, and I enjoyed myself more than I could ever dreamed I could. Even with all new gender euphoria I was experiencing, I still had to be more careful than ever that I did not crash and burn my male life…yet. I still needed him and what he could provide such as all the male privileges he had worked so hard to earn.

One way or another, I was definitely not on the same old road as I continued to experiment with living as a transfeminine person. I made mini bucket lists of the new things I needed to accomplish each day as a transgender woman and set out to do them. The list could be as small as working on a more feminine walk, all the way to going to a new venue I had never been to before as a trans woman. More often than not, I found the world accepted me as just another woman and did not really care. The whole experience was a confidence booster and enabled me to travel roads which were not the same old ones I was experiencing as a man. One of the main road twists I always mention was when I was able to escape the gay venues I was going to and finding other lesbian or straight venues which supported me.

Suddenly, I was having so much fun choosing all the new roads I found, I had a difficult time deciding where I was going to go. I never thought I was any good at road building until those exciting days when I was finding myself in the world. Some nights, I even felt like I was on some sort of a feminine interstate highway with all the interaction I was having with cisgender women I ran into. Sadly, I finally needed to slow down before I wrecked and burnt myself out, but not before I experienced more than I ever thought I could. My dream life was right down the road, if I could just reach it. I stopped, looked around and I found, all those years thinking I was crazy because of my gender issues were wrong, and I should have listened to myself long ago and I would not have to gone down all the rabbit holes I went down and then being stopped at dead end streets to prove to myself I was still the man I never was.

I was never good at auto mechanics as a man, and it showed when I tried to keep driving down the same old gender roads. As a transgender woman, I was able to take the pressure off driving down the same old roads.  

 

  

It's Just Life...Not a Joke

 

Image from Engin Akyurt on UnSplash.

It took me awhile before I finally came to the point in my gender transition when I gave up and thought the whole process was just life and not some sort of an evil joke.

I had struggled enough through the years when my male self-put up quite the struggle to exist at all. It was as if he was on a slippery slope towards losing his life altogether. To make matters worse as I always point out, my male side’s life was not always that bad. I had a long-term marriage, close friends and a good job to fall back on when I needed it.

Through it all, I thought it was only the draw of the feminine clothes which kept me longing for another trip to the mirror. I did not realize my feelings went much deeper than that. I was feeling life itself. It took me many years and even decades traveling a very curvy and bumpy gender path to realize where I was. Plus, many times, when I realized where I was, I became scared of losing everything. Falling off a gender cliff became a real possibility.

No matter how frightened I became, somehow, I kept on moving forward thanks mostly to the brief moments of gender euphoria I was feeling. The interludes helped me to determine if my dream goal of living a transfeminine life was possible at all. Back in those days, I was immersed in the struggle to present well as a woman and not much else. In fact, when I go back and read my earliest blog posts, I cannot believe how much they emphasize fashion and makeup. It all happened long before I needed to learn the layers of life a woman goes through to live her life. It was like my wife told me be man enough to be a woman. In those days I was not as I made weak attempts to live in both main binary genders.

In the short term, I did not understand what my wife meant as I became semi successful in presenting well in the world as a woman, but I had not paid my dues. I found I would have to wait until my wife had passed away before I could earn my way behind the feminine gender curtain to be allowed in by the ciswoman gatekeepers. It was about that time too when I began to understand my dream of ever becoming a fulltime transgender woman could be possible. It was much more than a hobby or part-time profession; it was my life. Then my realization led me to understand what my wife was talking about. I needed to set off on an all-out journey to live my best life as a transfeminine person. I even needed to understand questions about my own long held sexuality. If I lived as a woman, would I suddenly have to like men sexually? I just didn’t know until I set off to experiment.

Along the way, I did manage a couple dates with men which led to kissing but not much else and I did not feel much of a spark of any kind. On the other hand, I was surrounded by curious ciswomen (including lesbians) who wanted to socialize with me, so I was happy, I had always been a contradiction in terms socially, meaning I always enjoyed company even though I was shy and I could continue to feel that way. My life was beginning to come together in ways that I never imagined possible.

For example, I never imagined I would have been able to enjoy a small closely knit group of women friends who taught me more about life than they ever knew. Without any pressure, I was able to sit back and live vicariously through them and primarily how they lived their lives without the validation of men. It was not too long until they began to invite me along to their lesbian mixers, which I loved. I was even approached by other women and kissed. Which provided me with a huge amount of validation.

With my sexuality and life coming together, I could concentrate on enjoying my life on my new gender affirming hormones or HRT. The hormones went a long way in syncing up my internal and external self. Along with softening my skin and facial lines, my whole world was changing too. My emotions heightened as well as my senses as the world around me was softening. A perfect match to my rapidly expanding social life.

I will never know if waiting so long to transition into a feminine world was worth it or not because I had so many excuses why I never had done it. All I really know is, I did it before it was too late and have never looked back. That’s life.

 

 

What a Rush!!!

 

Vintage Transvestia Magazine

I encountered a real problem when my cross-dressing urges went from being a real adrenaline rush, all the way down to what I experience now.

I do remember the process did not take so long for me and I should have known then my cross-dressing activities were much more than a harmless innocent hobby I was involved with. If I had the information available to me then which became available later, I would have had an idea I was transgender. Of course, back in those days, the internet had not been invented along with all the social media rooms which came with it. I was in the dark ages of information and was very sure I was alone in the world with my gender desires. I always give credit to “Virginia Prince” and Transvestia Magazine for initially opening my closet door and showing me there were others in the world called transsexuals and transvestites.

During times of depression with my life, I could always fall back to my well-worn issues of Transvestia to lift my spirits. Plus, I discovered groups hosted transvestite mixers in Ohio I could attend with the proper preparation. I was ecstatic! I finally had a chance to meet others like me. Little did I know, I did not get that completely right, but that is another story all together.

In the meantime, I read my brief moments of adrenaline rushes were really called gender euphoria. Regardless of the label, I still had a difficult time controlling mine. Most of my examples come from the time my wife and I moved to the New York City metro area. For some reason, she left me out on my own one night to go to a mixer out on Long Island. Much to my surprise, I had a difficult time being admitted to the mixer by two cisgender women running the door. I asked why I was not being allowed in and they said no real women were allowed and I needed to show them an identification card with a male picture on it to get in. I was shocked and promptly showed them my old male drivers license and had a great time…until the buzz wore off days later. Then, I became mean and difficult to live with because I was feeling sorry for myself because I felt increasingly sure of myself as a transfeminine woman.

About that time, Halloween rolled around again which gave me an excuse to leave my closet and explore the world as a trans woman. This Halloween, I was getting better at “costuming” to present well as a woman and not to thrill as a cross dresser. Again, I was able to be out on my own because my wife was not a fan of Halloween and by pure chance, I ended up in the middle of a group of cisgender women all as tall as I was and dressed about the same way. Again, I had a great time and was even asked to dance by a man who I wondered knew about me.

All I knew was gender euphoria was great, until I crashed and burned. Then I always slipped back into my usual gender dysphoria problems. It seemed I needed the constant reassurance of me being able to present well as a transfeminine woman just to get by. Which was no way to live.

In order to live, I needed to make difficult life changing choices such as exploring the world increasingly as a feminine transgender person. I needed to weigh the difficulty in what I was doing with my life with what would happen if I was discovered. To accomplish my dream, I began to make small mini “bucket lists” of things I needed to do, most to just see if I could and increase my gender euphoria or adrenalin rush. Surprisingly, very quickly again my bucket lists did not provide much euphoria but in their place, a deep sense of stability in my life. For the first time in my life, I even felt I could be happy as a person. Whatever I was doing as a transfeminine woman, I was doing it right. Or so I thought.

Naturally I was afraid to make the final move to sever all ties with my male self. I found myself wasting precious time as I was able to expand my own new world as a woman of my own making. I had successfully gone through transitions from innocent cross dresser, all the way to full time transgender woman with bumps and bruises I had earned along the way. But I learned from them and moved on to a better life. If I only lived once, I wanted to live what was left as a woman.

Sure, my initial doses of adrenaline did help until everyday life came in and rescued me. Now I have smoothed out my life with fewer peaks and valleys of euphoria and when I do experience the negative gender dysphoria, I am able to live with it much better.

 

 

 

The Big Risk

 

Image from Joshua Rawson Harris
on UnSplash.

When you jump from one of the main binary genders to the other. In my case of course it meant leaving all my hard-earned male privileges behind and move into a largely unknown world.

The risk was tremendous the farther I went along. Mainly because I was accumulating an increasingly amount of male baggage. Such as family, house and good job. At the same time, I was perfecting my transfeminine appearance, which encouraged me to move forward in the world. To be sure, I was involved in being tested with a double-edged sword. Or which way should I go? I spent many wasted hours trying to obsess over my future, which was still very vague. At that point I did not even know if I could even exist in a fully transfeminine world. On nights I was accepted by the public, gender euphoria told me I could. Then, on the nights I was rejected by the public, I thought there was no way I could ever live my dream, and it would remain just that…a dream. A dream which never would go away. 

Through it all, the idea of risking all my existence remained with me and naturally scared me to my bones. I was hiding away my biggest secret and even though I did internalize it well, it was a drain on my mental health. Which is a side story I tell often because it is something I think more transgender women and trans men can learn from. At least I hope so.

Something else, I don’t think the average person understands about us, is this is not a casual joke to us, and we just cannot stop putting on a dress on a whim. We are ready to risk it all to live an authentic life as our true selves. Free from our closets. The problem was at the end of a day out, most of us must go back to our old unwanted male selves (or female selves for trans men). For me, it was always a heart-breaking experience as I tried desperately to maintain my male façade for my wife and work.  The only alternative I had was to attempt to live part of my life as a trans woman and the other half as a macho man. It tore me up.

The entire process just became worse and worse when I began to carve out an all-new life in a feminine world. The more success I felt, the less I wanted to go back to my old life and began to research the prospect of living my lifetime dream. In fact, all I can remember all I really wanted to be when I was young was, I wanted to be a woman. Which of course, I needed to keep to myself. I was miserable as I felt as if I was the only boy in the world who felt that way. It took me years to learn I was not the only male in the world who wanted to be female and was prepared to take the risk to do it.

I was able to find a couple of real live acquaintances who took the risk, almost, so I could judge what it meant for me if I decided to follow in their footsteps. I say almost because one the transsexual women I knew was a very attractive retired firefighter in Columbus, Ohio and had a very good pension to live on. The other trans woman I knew was even more attractive in her own right and a very accomplished electrical engineer and would always find a job. I had a good job but not one which would carry over to a gender transition. So, I had much more to consider, not to mention neither of the women I mentioned were in a serious spousal relationship and I was. Right in the middle of a twenty-five-year marriage. I would later come to know how similar yet drastically different our transgender community is.

The pressure I was feeling to take the final risk continued to build. Aided by the success I was having in dealing with the public, I was encouraged to take the final risk in my life. At this point, destiny stepped in to show me the way. My two major stopping points were my second wife and what I would do for an income after I transitioned.

My wife tragically died, leaving me with one to speak of to object to me leaving my old life behind and beginning a new one. Then, by that time, I was in reach of being able to retire on early Social Security income plus what I could sell online. In many ways, the lightning did come right before the rain for me and then the sun came out. When it did, I could see my dream life had arrived and I could live how I wanted to.

 

 

 

Preparing to Lose

 

JJ Hart speaking at a Cincinnati Trans Wellness 
Conference.

When I first began to explore my transgender womanhood in public, I was rejected so much, I was totally dejected by the whole outcome.

The only thing which kept me going was a deep feeling I was doing something right in my life for a change. Plus, I did experience very brief moments of gender euphoria when for once, I had my feet on the ground and was able to blend in with other women in the world. One night I remember in particular was when I dressed in my best oversized fluffy sweater and short black mini skirt and set out to do a portion of the family's grocery shopping. After shaving my legs and brushing out my favorite wig, I set out for the store which was not too far away. 

Once I arrived at the store, it was early, and I was relieved to see it was almost empty when I went about doing my shopping. Just to prove I could, I picked out a few items I thought we needed and headed for the checkout line where one woman and a young male bagger was working. As I was unloading my cart, I slyly caught the bagger looking me over and when I looked at him, he quickly blushed and looked away. Then I looked at the checkout lady who just gave me a knowing smile and asked if I needed any help taking my items to the car. It was the first time in my life I allowed myself a brief moment to think I looked good enough to fluster a young man. I carried the experience forward with me for weeks because it gave me such good confidence in my new feminine world. 

As we all know, confidence is so important to those of us working our way down our gender paths. It does not matter if we are experienced cross dressers or transgender women, having a healthy sense of confidence in ourselves helps our progress in the world immeasurably. People are like sharks and can spot a weakness in another person a mile away. Even though my newfound confidence was still very fragile, I could feel it growing. Which was all that mattered to me. 

From there, I tried to experience living more of my life as a novice transgender woman doing things a cisgender woman would do. Again, doing a portion of the grocery shopping was an example. Looking back on it now, I am surprised my second wife did not question what I was doing but she never did. Through it all, even though I was being successful for a change in my cross dressing or transgender experiences, somehow, someway I still prepared myself for failure. I suppose it was because I experienced so much failure earlier, I still expected it. 

Then, I began to think about what I was doing and came up with what I was really prepared to lose. Since I had advanced to the point of passing in my presentation, was I prepared to lose more and more of my male world. As much as I did not like it, through out and out effort, I was able to carve out a decent male life, and I needed to decide if I could make it without my spouse, extended family, friends and job. What was I prepared to lose?

Long story short, I decided I felt so good in my new transgender womanhood, I decided what I could lose, and it was everything. I should say, I risked it all for a better life and I had very few things to lose when I tried it. My wife and close friends all had passed away and it turned out my all-important daughter came all out to accept me. So, I was very fortunate. 

All along, I was still prepared to lose, it never really happened to me. I can't take much of the credit because I put myself out in the world and good women responded. They were all I needed to restore more of my inner confidence and start a new life.  

Gender House of Cards

 

Image from 
Nathan Dumlao
on UnSplash.

As I progressed along my gender path, I regularly built houses of cards.

I became used to showing my cards regularly when I was a novice cross dresser. Sadly, I was coming off too often as the joker. I can't mention enough how I was the victim of the beginning cross dressers' curse. I was trying to dress as a teen aged girl when I was a wide-bodied male just trying to survive in a new exciting yet scary new world. My life existed by taking a step forward and another two steps back. Gender euphoria was very rare in my life, so I needed to cherish it when it came about. 

In order to make up (no pun intended) from the long lapses of gender euphoria, I needed to step back and try to build my house of cards with a better, more solid foundation. Every time I was rejected, I had to resolve myself to go back to my cross-dressing board and work harder on something like I had never worked so hard on before. Finally, my efforts paid off and I began to blend in with the public with less effort. I was ecstatic and I readied myself to move forward play more cards. Did someone say success breeds success? If not, I will, and it happened to me. I gained the all-important confidence I needed and headed on up my gender path.  

I proceeded to keep building my house of cards against all odds, I realized who I truly was. Much more than a relatively innocent parttime cross dresser and much more of a transgender woman. It seems like such a small difference in thought pattern could make such a huge difference in my life. Suddenly, it seemed the world opened up for me and I thought I had found the missing card I had always been looking for.  

Having said all of that, I knew I would have to set out to build a whole different house of cards. No longer did I want to just look like the women around me, I wanted to be treated as an equal. Which seemed to be an impossible dream. When I was successful in hanging out with other women, I developed a whole new set of confidence and began to relax and enjoy the experience. I was at home with myself for the first time ever. Perhaps the best result was, my house of cards was being built so much stronger and more resilient to the outside world. 

From then on, the race was on to enable my inner feminine self to play her own cards. When she finally did, she was extremely successful and made the best of her situation. Plus, she was able to build upon the mistakes of her male counterpart and never having to play the joker. Then my wife Liz came along and re-enforced my new transgender womanhood, while at the same time rapidly building my house of cards. When I experienced a collapse, Liz was there to catch me. 

I am sure you agree, building your own gender house of cards is not an easy task to complete. You need to show an uncommon level of patience when your cards collapsed, and you needed to start all over. It shows how difficult a transgender life can be. Especially in these difficult times.  

Master of Myself

Transgender Flag from Lena Balk
on UnSplash. 

Or would have it been proper to say, Mistress of myself?

Probably so, as one way or another, I really struggled to arrive at where I needed to be to achieve my goal of transgender womanhood. Often, I write about how many nights when I came home in tears following being laughed at by an unfeeling public. Looking back now, I have a difficult time wondering what kept me going along my gender path. 

I suppose the little flashes of gender euphoria I experienced kept me going. Such as when I was accepted in malls and clothing stores before I realized all the clerks were seeing was my money, not my gender. Before long, the more experience I put behind me as a cross dresser or novice transgender woman, slowly the path was smoother and the happier I was becoming.

Then there were the small mixers I went to in nearby Columbus, Ohio. When I attended, I was able to see and meet all levels of the LGBTQ community. From admirers to transsexuals to lesbians, they all were there. It was one of the mixers where I was cornered by a much larger crossdresser admirer who was trying to take advantage of me and could have until I was rescued by my second wife. It was also there when I had my first encounter with a curious lesbian, and we left the mixer to visit a bigger lesbian bar. At that point, I was still heavily questioning which way my life would go. What kind of a path was I on and did I control it at all. 

In order to gain control, the only thing I could do was try to gain more and more experience as a transgender woman to learn if I was headed in the right direction with my life. So much was at stake and the pressure was on to make the right decision. In the meantime, I continued to follow my path and learn if I could indeed flip my gender script and attempt to be truly happy for the first time in my life. Perhaps, discovering the truth about myself, would finally provide me the missing link I was seeking. Of course, just dressing to appear as a woman did not solve the problem. As I gained confidence in the world, the world wanted to know more about me. The whole process opened up a whole new range of life opportunities. Such as how was I going to learn to communicate as a woman, all the way to adjusting to a whole new world of passive aggressive women. 

Again, it took a while for me to regain control of my life. Of course, attempting to change genders into my authentic self was a seismic shift in my life. On one hand, my authentic self-felt so natural but on the other, the entire process was so scary. So, I took my time before I started taking gender affirming hormones, so I burned all my gender bridges behind me. Looking back now, I wish I had done it all sooner and taken better control of my life.

I did not however and ended up not transitioning until I was in my sixties. Once I did, there was no looking back and I became the mistress of myself. Finally.  

 

Pain

Image from Tony Frost
on UnSplash

Looking back, I don't think I write enough about the pain I felt during my life which was closely related to my gender issues. 

First of all, I was living in a world where nothing was ever as it seemed. Life had wedged me into living a male pattern I never felt a part of, and I could not escape. One of the problems was I was privileged in so many ways and was told constantly about it. After all, I was white, middle classed male child and all I needed to do was find a way to fit in. The pain was considerable when I learned I just couldn't. I did not have a choice, all I really wanted to do was be a girl.

Much later in life, when information began to become more available, my problem began to be known as gender dysphoria. Having a term was good enough but did nothing to relieve my pain. The only cure was to cross dress in front of the mirror and try to imagine how it would be to be a girl. I was successful in blissfully thinking I was headed in the right direction, until I started to head out of my closet and explore the world. When I did, the public took the mirror's place, and I was judged (sometimes very harshly) by an unforgiving world. Unless you happen to be a natural as a transitioning male to female person, perhaps you have been in the same circumstance of having to learn to present well as a woman. At times, the entire journey I was on seemed to be a steep insurmountable path. 

Still, I learned from the days and nights of pain I endured and kept on trying to improve my feminine presentation. My tears finally subsided, and gender euphoria set in. Maybe I could achieve my dreams of transgender womanhood. What I did not realize was how far I still needed to go. No matter how far along I thought I was with my makeup, hair and fashion, there were still hurdles to jump with communication and interaction in the real world as a trans woman. Plus, there was the very painful life I was leading as two genders when I needed to hide what I was doing from my unaccepting second wife. I always considered myself a very honest person, so being dishonest with her about my truth caused me great sorrow and pain but at that point I could not turn back.

Before I knew it, she passed away and a new pain such I had never known set into my life. It seemed I learned again how death was forever, and loneliness would follow. What I did not realize was how life could go full circle if you are fortunate enough to live long enough as I was. Slowly but surely, the fleeting wisdom of age taught me life offered both joy and pain along the way. It just so happened in my life; gender played a very important part. 

Also, life taught me feeling gender dysphoria or pain helped me to appreciate gender euphoria or joy even more. Regardless, I need to point out my gender journey was never easy and required my utmost attention. So, I could survive all of my pain.  

Ditching Good for Better

 

JJ Hart with Ohio River.

As I made my way along my gender path, I was always looking to go from just good to better. 

I always wanted to present better as a girl my age all the way to moving like one and even doing my best to act like one. I did my best to be a keen observer of what the feminine gender around me was doing at all times.. If they were wearing mini-skirts, so should I was a prime example.

Sadly, I was hindered by my meager financial situation until I grew older and could afford more fancier accessories such as clothes and wigs. Even still, nothing was stopping me from pursuing my gender dreams of living as a woman. If only I could. That is where my path became more and more important. For example when I finally broke out of my closet and did all my own shopping, I learned the hard way what looked good on me and what did not. From there I could build on to my success and go from good to better.

I became especially good with my feminine business attire wardrobe. At thrift stores I managed to find a black pant's suit which paired nicely with heels or flats and my should length blond wig. I even had a wool full length coat to go with it for the winter time when I went shopping. For the warmer times of the year, I found a lime green business suit with a shorter skirt which I paired with pastel green opaque panty hose and matching kitten heels. I found I went from good to better either time of the year and presented relatively easier for the first time in my life. Gender euphoria at it's finest.

All of my fashion advances did not prepare me for face to face encounters with other women in the world. Chance encounters with store clerks were easy until I began to stop at restaurants to eat. I needed to order from a menu while at the same time doing my best to sound like another woman just having lunch away from her job. Until I gathered the confidence to practice it, the entire idea of talking like a woman was once of the most difficult things I had ever attempted.  I even went as far as going from good to better by taking vocal lessons to usher me into my transgender womanhood. 

I often think I inherited my drive to always do better from my parents. Nothing was ever good enough for them. If I had received a B in a class, why did not I get an A was the routine I grew up with. Imagine the irony my parents would have felt when they found I applied the same thought pattern to a gender issue they were very against. All I ever wanted was to be a woman, transgender or not and needed to work very hard to overcome my male bonds to do it. Plus I always felt if I was going to be successful as a transgender woman, I would have to try harder than the average woman to succeed. 

So along the way, I needed to not accept good and kept trying to achieve being better and better as a transgender woman. I wonder what my parents and my second wife would have thought of me now. Hopefully they would be happy for me, since I have arrived at the place I have always wanted to be in life. If I had done it sooner, I would have undoubtedly been an easier person to live with. 

Trans Peaks and Valleys

Image from the
Jessie Hart Archives.

Lifetime as a whole presents us with many peaks and valleys to negotiate.

Since I am transgender and always wanted to be a woman, my peaks and valleys often revolved around times when I came out as my authentic self in the world. Very early on, sadly, there were more frequent valleys than peaks as I learned to survive in the public as a novice cross dresser or transgender woman. I vividly remember too many times when I came home sobbing when I was laughed at. I don't remember now how I survived the dark times and continued to move forward. 

As I did move forward, there were other peaks in my life such as when my only child was born. When she arrived, my existence changed forever. Plus, I wondered how having a new person in the world would effect my gender desires. In many ways, I thought it was poetic justice when I had a girl. For some reason, deep down, I thought I could understand a girl better than a boy.  Since my daughter turned out the way she did, maybe I was right.

A big problem I had with my peaks and valleys was staying in one place long enough to actually understand if I was doing anything right. As I constantly changed jobs and moved my small family, I gave my second wife a hard way to go when I tried to chase myself. I am amazed we made it through twenty five years. 

Another problem I had was when I needed to come down off the gender peaks when I encountered them. Gender euphoria was so rare, I wanted to hang on to it as long as I could. When I couldn't I would become frustrated and ultimately mean around my family and co-workers. 

The more I progressed in my gender transition the more extreme the effort to climb out of the valleys became. The major problem was I didn't feel increasingly secure in my old male role and at the same time, I was feeling more and more natural as my femininized self. Which again caused me great frustration when I fell deeper into my valley. At several points I was so deep, I needed therapy to help me restore my mental health. Therapy on occasion did help me climb up to an acceptable level of a peak. When I was smart enough to actually take the therapist's advice. 

It turned out my fear of heights carried over to my transgender issues. The better I became at existing as a woman in public, I was scared. Primarily because for the first time in my life it seemed to be a real possibility I could reach my dream of actually living as a transgender woman. As I looked down on my previous male life, leaving it scared me. What would I do about  losing all of my white male privileges and then having to start all over again. At the time, the only female privilege I could see was a man opening a door for me. Which I later found to be false as there were other feminine benefits I had yet to experience as I climbed my gender peak. 

Finally, at the age of sixty, I could take the pressure of the climb no longer and I decided to stop all aspects of my old male life. I was taking gender affirming hormones to take me to the next step, my mental health was improving and for once I could see my life clearly as a transgender woman. So even though I needed to take a leap of faith off a cliff and transition, I found I had others around me who provided a soft landing. It turned out, I hadn't lost anything at all. 

My up and down life of trying to live as both binary genders was difficult at times to say the least. Near the end I found I made the correct decision on which peak to climb and it was not the male one.

A Breath of Fresh Air

Out to eat with my wife Liz on the left.

Even though we are among the millions of other Americans stuck under the infamous "Heat Dome" and temperatures near one hundred, last night I was able to take a breath of wonderful fresh air.

To do it, I needed to get out of the air conditioned house long enough so Liz and I could make the short trip to our favorite Mexican restaurant. Fortunately, the venue's air conditioning was working fairly well and we were seated under a ceiling fan. So we were comfortable even though the place was very busy. 

For the evening out, I chose a lacy pink and black top I have not worn in ages. Along with my dark blue leggings with tennis shoes so I was very much at ease. It was also fun to shave very close and apply a light foundation coat of makeup before I did my eyes and contouring finally finishing up with lipstick before I brushed back my hair. My goal, which I think I achieved, was a soft feminine look. I helped myself by clipping my hair loosely in the back, allowing long straight strands to fall on both sides on my face. The whole effect, served to lengthen and femininize my face.  

At any rate, the most important part was how the public perceived me. Even though I wasn't dressed in the shorts and light dresses the other women were wearing around me, I thought my flowing outfit fit in well. It helped too I was with my wife Liz and her son who has accepted me since he was a teenager. I was set up for success. 

The best part was, no one gave me a second look and I was able to feel as if I was the "normal" woman out into the world. Even little kids ignored me. Along the way, I did have the opportunity to pause in my mind and think back to all the work it took to come to this point of gender acceptance in my life. All the times I was stared at or worse as I tried to make my way in a new uncertain world out of the mirror. In many ways my dreams were answered. All it took were years of struggle to finally achieve the success I found last night. 

After we finished our drinks and dinner, the three of us decided to try a different venue the next time we go out. Which presents another challenge when I present to the world. Plus, I know both my wife Liz and I need to get out of this house and everytime we do, it seems to improve our mental health for any number of reasons. Every time I am "ma'amed" at the table automatically adds to the tip and sends my brain soaring.  I was last night and the tip reflected it without the server (a man) even knowing why.

Perhaps the best point is the resultant gender euphoria I felt after we arrived back home and into the next day. Today I still feel the pleasure of finally arriving more or less where I wanted to be years ago when I was a confused kid. Of course I know there will still be many challenges ahead in my gender journey, I feel satisfied so far with my long term progress. I even call the transgender process, working at my craft. It is the only way I can look at all the gender changes I needed to make to jump across the gender border to see if the grass was indeed greener. For me it was and I decided to never turn back into an unwanted male life. 

Nights such as last night are always a re-enforcement of all the work and effort I put into my transition.  I need all I can get.