The Ultimate Gender Challenge?

 

Image from Alexander Simonsen
on UnSplash

As I was in an ambulance on the way to a strange hospital in suburban Atlanta, I was so far out of it that I did not much care about being mis-gendered. I just wanted to feel better. 

All started out well as the EMS ambulance drivers referred to me without fail as Mz. Hart or Jessie. At least their kindness made me feel as if everything would indeed turn out to be OK. Then I thought how being gendered at a medical center has to be unique transgender experience. When you have to face strangers as your most fragile self. 

For a while, I was secure in the fact I would make it through the rank-and-file medical personnel accepted me as a female patient. Until I came to the most intimate point of my admission process. It was the time I needed to strip naked and fitted for an ubiquitous hospital robe. It was then when I was fitted for one of those contraptions to enable me not to wet the bed. It turned out, initially I was given a female version then asked if I wanted a male one which fit me better later on. At that point, it was obvious to me, I was confusing a portion of my nurses and that was where my wife Liz came in. Whenever a nurse refereed to me as he, Liz would promptly correct them. 

Overall, my hospital experience went as well as could be expected. I had reached the point of no return since I had never pursued any sort of gender realignment surgeries for any number of reasons. Including my lack of financial opportunities as well as not having good enough insurance to even think about any major operations. By this time, age had set in, as well as a fairly comfortable lifestyle with a family who accepted my transgender womanhood. Plus, I always had an aversion to pain I could not overcome so I did not even pursue any beard removal work. My lazy way out worked well with close shaves over the years along with the effects of gender affirming hormones, until it didn't. Which deep down I knew I would have to face someday. 

Well, the time was upon me last week during my hospital stay when I was too weak to get out of bed for several days so I could shave. When I was finally released to be discharged by the doctor in charge of my care, the first thing I did was closely shave and apply some light foundation as I brushed out my hair. Needless to say, I could not wait to put my hospital experience behind me. In all fairness, nearly all the hospital staff was nice to us and were intrigued by the fact Liz and I were stuck in Georgia after our bus had to leave us behind. I think they were behind me regaining my strength so I could. 

One way or another, it was an extreme gender learning experience.  

I'm Back...Mostly

 

Well, my wife Liz and I's vacation to the Florida Keys was eventful, with many unexpected turns.

Since I have quite a bit to write about, I will start at the beginning of our bus trip. As we boarded a nearly empty bus way before dawn in suburban Cincinnati the morning was very cold and clear. From our boarding point, we needed to make two other stops to pick up other passengers for the trip in nearby Northern Kentucky.  Since we were nearly the first on the bus, my paranoia about being the only transgender passenger was calmed, especially since I was under the cover of darkness. 

As daylight came around and the bus filled up, the pressure for me to make a good first impression came with it. I managed to cope with a small mirror I put away into my purse, along with my foundation powder and lipstick. So instant touch ups were within my reach.

Of course, all too soon came the all-important first rest room stop. I stayed very close to Liz as we went in and there were no problems with anyone on the bus, or other strangers who were already coming or going in the women's room. I did my business, washed up and left with no interference which made me feel relieved after all the months of worry I put into thinking of what could happen. 

At this point, our bus driver deserves a strong recommendation for his work in getting us safely through very snowy and icy road conditions we encountered as we made our way south from Ohio. He also was available to help me on and off the bus when needed. 

Long story short, we made it to Georgia and spent the night in Macon. Then off to Orlando for our next stop.  By this time, I could not wait to make it to our staging destination of Key Largo. Then Liz and I began to notice how many people on the bus had bad coughs. Which is a spoiler alert for what happened to me later in the trip and would involve a trip to a hospital in Georgia. 

More on it, plus a very pleasant trip to Key West coming up when I finally begin to feel better, because I caught Covid on the bus. Even though I had been given the booster three months ago. Make of that what you will.

 

 

Expedition Transgender

 

Image courtesy JJ Hart

The half century journey I embarked on to finally come up as my true authentic self was certainly an expedition. 

As I always mention, my discovery began with going through my mom's underwear drawer and trying on nylons, bras and girdles I could still fit into before testosterone poisoning really set in. From there, I progressed into makeup and very slowly began to increase my craft. I did not really want to look like a clown in drag so I did the best I could. 

Life went by and so did my expedition. Sadly, for several reasons, I developed several coping mechanisms to mask my gender truth. I tried and tried to convince myself my desire to wear women's clothes and look feminine was just a harmless hobby and perhaps was just a phase in life I was going through. It took me years to realize the true phase I was going through was that I was a male at all. With sheer willpower, I managed to learn to play the male game fairly successfully and lived a life which shielded my feminine self from most all intrusions. I went into my dark lonely gender closet and slammed the door.

It took me years to have the courage to open my closet door and tentatively look around. When I did, my expedition took sudden and encouraging turns. The more I tested the public as a transgender woman, the more successful I was. I set out to sample as much as I could of a woman's lifestyle and discover my feelings on what would happen next. I tried going to gay and lesbian bars as well as big sports bars and found I could carve out a spot as a regular in a so-called straight venue. I also tried to go to various other places such as bookstores and other retail venues single women would go. In other words, I was obsessed with coming as close as I could on my expedition to seeing what a cis woman went through in her life. By doing so, I could make the final decision on where I wanted to go with my life, as a man or as a woman. 

As my expedition transgender progressed, I found myself in a face-to-face decision on beginning to take gender affirming hormones or not. Since my only real opposition to beginning the hormones had passed away, my ultimate path was clear, and I sought out a doctor for approval. He checked me out and determined I was healthy enough to begin HRT with minimum dosages of Estradiol and a testosterone blocker and my life changed forever. All the changes which occurred would fill another blog post themselves. Perhaps the biggest overall surprise was how quickly my body took to the new hormones. So fast, I needed to rethink how quickly I was going to have to change the timetable of when I ultimately wanted to finish my expedition and enter my own transgender womanhood.

I learned the fact of the matter was, I was always living a gender lie. I had refused to accept the fact I was always deeply feminine and was forced into a male lifestyle from some cruel twist of fate. All the time I thought I was a man attempting to be a woman was wrong. I was a woman attempting to be a man.

I wish I could have a portion of my life back to re-center my expedition and start all over again.  

 

Merry Christmas

Leg Lamp from the "Christmas Story"

 Doesn't seem possible another year has flown by and here I am writing another Christmas Day blog post as the "Yule Log" plays on the television behind my wife Liz and me.

Earlier this morning, I cried tears of sorrow and joy. The sorrow came from remembering the times of my life when my family was strong, and we had festive Christmases. Plus, I am old enough to remember how much fun it was when the downtown was vibrant and glowing with its holiday decorations. Now around here at least, the downtowns have been replaced by sterile decaying malls or outside shopping centers. I even cried when I recalled the life my ex-brother and I shared. 

Now, the tears of joy. Slowly but surely as I began to think about the present, I shed tears when I thought of the love I feel for Liz and how fortunate I am to have someone to love me in a season where so many others, especially in the transgender community just don't. When my brother and his family rejected me during the holiday season over a decade ago, I found a new family with my daughter and Liz. I know I am blessed.

On this Christmas, I also make sure I watch a couple of my favorite classics such as "It's a Wonderful Life" and Ralphie's "The Christmas Story." Ralphie is especially special to me because the time period it represents is roughly the same as mine growing up. The only difference is, instead of the BB Gun Ralphie so desperately wanted, in my case I received the gun but did not get what I wanted, a doll baby. It is poetic justice, I guess.

Regardless, I hope you have a Merry Christmas with blood or chosen family and thanks for joining me!

 

Getting What you Want

 

Image from Aiden Craver
on UnSplash.

This is not really a Christmas post, even though in many ways, it fits in well with the season. 

As I was growing up, I vividly remember being asked what I wanted to be when I grew up into an adult. I also remember lying and saying something like a lawyer or doctor. Anything to make my parents happy without telling whoever asked, I really just wanted to be a girl when I grew up. An answer such as that would have landed me in all sorts of trouble.  

I progressed through life doing my best to navigate a very dark and bumpy gender road without much help from anyone except the occasional therapist. Through it all, for the longest time, getting what I wanted was a faraway dream. During my gender journey, I faced all sorts of problems such as my reoccurring issues dealing with my feminine appearance. Like so many of you, I needed to learn the fashion and makeup arts all by myself with no one to help. Back in those days, there were not the plethora of on-line makeup videos and special makeup stores to help a novice cross dresser along.

Then there were the up close and personal meetings I had with the impossibly feminine transsexual women I met. Interacting with them made me feel again how impossible my dream of becoming a full-time woman of any sort would be. However, it was about this time I began to take better care of myself, so I had a chance of becoming a better feminine version of myself. 

I dieted and lost nearly fifty pounds and began a regular skin routine which really helped with using less makeup and achieving better results. Suddenly, there was a light at the end of my presentation tunnel which was not the train. Maybe I could get what I wanted after all. At that point, I really became serious about exploring the world as a transgender woman. The rest as they say is history. When I did gather the courage to enter the world, I found I could survive. I discovered a great majority of the world did not care and a smaller percentage was just curious and amazingly enough, a smaller percentage yet respected me for living my truth. The bottom line was I survived and became better at life as a transgender woman.

When I did survive and relaxed, I saw my reality shining through. Maybe, just maybe, I could shed the shackles of my old male existence and live my gender dream. I could answer finally my own question of what I wanted to be when I grew up. A woman. To further the process along, I was able to begin gender affirming hormones which femininized me even further. My facial lines softened, my hair and breasts began to grow, and my emotions softened to the point where I could cry freely for the first time in my life. Through it all, my body was asking me what took so long to start HRT.

Looking back, getting what I wanted was the most difficult trip I had ever taken in my entire life. Pure perseverance and destiny helped me along to a full-time life away from my old unwanted male self, into a life I always wanted.   

Transgender Procrastination

 

Image from JJ Hart

During my life, I have developed with an excessive amount of procrastination. Who knows, maybe it started when I put off doing my homework until the last minute. Later on, I began to connect the dots to me pursuing a life as a transgender woman. In other words, why did it take me over a half century to finally decide to leave my male life behind and the confines of my dark gender closet.

The easy answer is I kept putting off what I did not understand or want to face about myself by cross dressing my life away. To be certain, it was a series of stop-gap measures designed to help me survive life at all. When I was able to cross dress in front of the mirror or later at transvestite mixers I attended to see for the first time, others who perhaps shared the same gender views as I did. Ironically, I found I was wrong as I found most of the others at the parties were still a bit (or a lot) different than me. I did not quite fit in with the transsexuals or the cross dressers who were seemingly still stuck with their male selves which they were still attempting to deny. 

Still, I survived and slowly began to carve out my own life on my own terms as a transgender woman. Of course, even then, I still was the mistress of procrastination. Increasingly as I began too seriously explore the world as a transgender woman, I could not procrastinate any further. The result was I needed to merge my conflicting genders the best I could. The holidays proved to be the best time for me to try to do it. 

I have already written about my adventures shopping for my second wife when it came to buying her a matching oak bookcase and my time shopping for the perfect garden accessory. As I have promised in the past, I have not written yet about my times searching the antique malls for the perfect vintage gift for my wife. The added benefit was I could complete my Christmas shopping as a woman.

It just so happens, one of the largest antiques malls in the Midwest where I lived was located in my hometown. It gave me extra time to shop since I did not have to drive far to get there to the mall. I had several favorite things to do once I arrived and made a last second check of my hair and makeup in the car mirror and went on in. The benefit of vintage shopping for my wife was at the same time I could admire myself in one of the many available mirrors of the vintage furniture for sale. 

The furniture was not in my budget but items such as vintage seed boxes were. In fact, during those days, the seed boxes were a hot item for gardeners everywhere, so they were pricey. Still, I persisted until I was lucky to find one from another company, she did not have in my price range. The other benefit of shopping in the antique malls was I could really relax and enjoy the experience. Back then, the feeling of my feminine clothes and the interaction I was having with the public was so new and exciting. Plus, I could not wait to see the look on my wife's face when she opened the gifts I found for her. Back in those days, we had three Christmas gift celebrations. Two with each of our families and one just between ourselves. The giving of gifts between us always came last and always included the gift or gifts she reserved for my feminine self. 

My procrastination always extended to shopping at the last minute. As a trans woman or not. Perhaps I was addicted to the excitement of waiting until the last minute to find and give the perfect gift. All tempered by the fact I was shopping as my true self.

All of the experience added to me not waiting any longer and finally deciding to take a huge weight off my shoulders and do the right thing. Quit trying to live a lie as a man and begin a new life as a transgender woman. Facing my truth led to the end of my gender procrastination. 

Trans Girl Shopping

 

Image from Sam Headland on UnSplash.

Many Christmases ago, in the early two thousand's I began to do most of my special gift shopping for my second wife as a transgender woman. Needless to say, I learned a lot. 

My wife was a huge gardener, so greenhouses and specialty garden stores were my first places to go to if I was to ever find the special gift, I was looking for. To find the best selections, I normally made the hour trip to Columbus, Ohio which had bigger greenhouses and even a specialty garden store in one of their upscale malls. Since at that time, I had a reasonable amount of spendable income, almost nothing was out of reach for me as a gift for her. 

Normally, I made the trip during the day and wore professional women's business attire. My hope was I could present well as a woman just on her lunch break shopping for last minute gifts. Even though, I was beginning to feel more and more at home as a woman in the world. Still, I felt I needed to work hard to be able to present the best I could as a transgender woman to avoid detection. Seeing as how I was knocking out two birds with one stone, I needed to do it well. 

I should not have worried because one way or another I was treated warmly by more than a few of the clerks I faced and at the worse with indifference by others. I found the older clerks were more apt to help me and the younger ones left me on my own to shop. Even being left alone was alright with me because I was so intensely trying to find just the right gift for my wife who did not know it was my feminine self-doing almost all her shopping. Along the way, I found all sorts of unique gifts from new garden tools all the way to vintage seed boxes in antique malls. Which is a different story for another blog post which I will write before Christmas. 

Perhaps you are wondering what I wore for these new yet scary shopping adventures I was on. Depending upon which mall I was going to, I attempted to scale up or back on my outfit so I would not appear out of place. At that time, Columbus featured two very upscale malls, and I could not miss out blending in by dressing in my finest silky black pant suit, blond wig, and heels along with my very best application of makeup. All my efforts worked well as nearly everyone ignored me, except a few men. 

Since I was being successful in my transgender womanhood, and I was able to be out in the public's eye for an extended period of time, I decided to push my boundaries and stop to eat and use the lady's room. Both were a challenge for me since I had rarely done it before. I gathered my courage and stepped into one of the sit-down restaurants in the mall and just took a seat at the bar to eat. Sure, I was scared of having any one-on-one communication with the public but on the other hand, I was so successful so far in the day, why not push my luck. 

It turned out all my fears were unfounded as I was treated well in the venue I chose and the only problem I had in the restroom was navigating my way around using the toilet in my pantsuit. I did not think far enough ahead when I chose my outfit for the day and put fashion ahead of rest room utility. Fortunately, I was able to complete my struggles successfully, take care of business and leave the lady's room before anyone else came in. 

I finished the day of trans girl shopping as a very successful experience with the added positives of finding great gifts for my wife. I could not wait to do it again.

NOT for Entertainment Only

 

Image from Alice Alinari
on UnSplash

As I went along my path to transgender womanhood, I found the journey was never a choice and was not for entertainment only.

My journey did not begin that way. Similar to many of you, I started by exploring my mom's underwear drawer and wearing what would fit. All of that was seemingly innocent enough unless I was caught. Then there would undoubtedly be hell to pay, along with a trip to a psychiatrist. Later I would wonder if my mom ever knew because her underwear was stretched out, but she never approached me at all. 

It was all fun and games until it wasn't. Slowly, I learned wearing girls/women's clothes was not for entertainment only. I was becoming increasingly serious about it. For the first time in my life, I was obsessing over how I looked. How was my makeup and very limited access to a wardrobe appearing in the mirror. I even went as far as shaving my legs when I thought I could get away with it. In addition, I did my best to study the other girls around me. I did not know it then, but I probably was wearing makeup before a few of the girls I knew were allowed to do it. At the time when I could not seem to muster the same passion for building the model cars I had and painting them well, makeup was an entirely different challenge and one I could not resist doing my absolute best at doing well. With no help whatsoever. 

I found, for the first time in my life, I was completely serious about doing one thing and it was being a girl. Not just looking like one. It took me years to learn just gazing at my reflection cross dressed as a feminine person was just not enough. I needed more. My problem was early on was having the budget to do anything such as being able to afford having a nice wig. It was not until my college days until I could buy a long blond wig I cherished for years. Spending all the money on one specific fashion accessory proved my passion to look good was not for entertainment only. I was really serious.

Of course, then I really started to step up my gender game. When I was released from my military service, I began to seriously explore the world as the feminine trans woman I was destined to become. As I write about often, my journey was filled with ups and downs and my mental health suffered. Definitely not the way I thought it would be when I looked at myself dressed as a girl in the mirror early in my life. What I never had a chance to consider was I was not a transvestite or cross dresser at all. In fact, I was a transgender woman and needed to accept it. I was never in it for the entertainment and my life depended on a successful outcome. 

What I mean is, I needed to stop all the self-destructive behavior I was exhibiting as I sought to destroy everything successful, I had ever done. Along the way, I had tried to lose jobs, drink too much all the way to trying to kill myself with pills. Never realizing how much I had to live for if only I followed my transgender path far enough. 

I wonder now, if I had realized how difficult my journey would be and not be entertaining would I have ever undertaken it at all. I also realize now, I never had a choice, and my life would have been better had I realized it sooner. I would love to get back just a tiny portion of the stress and tension I lost during my life as I worried about my gender. Outside of a few therapists who tried to help me by telling me the truth about myself, I was on my own. My life was never for entertainment only as I followed a gender path full of turns and dead ends before I discovered my truth in my transgender womanhood. 

Trans Fun?

 

Holiday Image, JJ Hart author.

Are we having any fun yet as the holidays are upon us? 

Certainly, it is a tough time of the year as transgender women and trans men face the daunting task of facing unapproving families. Too many of us face a lonely existence this holiday month. In many ways, we are uniquely qualified to face the challenge. For those of us who were ravaged by testosterone poisoning and not gifted by natural feminine features, our path is a steep one to finding any acceptance at all in our transgender womanhood. 

In my sense, there was only brief gender euphoria moments during too many instances of rejection by the public. Every now and then, I would have moments of fun when I briefly succeeded at my goal of successfully presenting as a woman. Then, all too often I would ruin it all by not knowing how to move as a woman or more importantly having any idea how to communicate with the public as the person I had always wanted to be. 

Through it all, I did have enough fun, or at least satisfaction to keep moving forward. To be certain, there was a difference between having fun or being satisfied with what I was doing. To be satisfied meant deep down I felt natural when I was pursuing my feminine dreams. To put it another way, there was a flood of water under my gender bridge primarily in the decade after 2007 when my second wife passed away and opened the door to a total transition into transgender womanhood. If I wasn't hanging out with lesbians in their venues, I was finding my way in big sports bars as a regular. Slowly but surely, I learned I still was alone on my gender path, even though I was meeting and learning from a few of the cis women I stayed close to. It was difficult because I had always trained myself to keep everyone else at an arm's length so I would not be hurt. The difference was now I was finally at the level personally where I wanted to be as my authentic self so I could accept new friends.

If I had liked, it or not I had finally reached the bottom-line where I had always wanted to be. When I did, I began too actually relax and enjoy myself. Which means I was having fun, regardless of myself. Perhaps I was fortunate in that my path forward was complex but maybe not as complex as is the norm these days. Social media contacts were just becoming the norm and maybe it meant the tons of trash I needed to sift through to find my wife Liz was destiny and not luck since she actually sought me out online after reading my profile. Then, there was my public persona which I don't necessarily recommend because I was going out to venues as a single transgender woman. Back in those days at least, one did not have to worry about someone else putting date drugs in your drink while you were not looking. 

Looking back, I did have fun during those days and primarily it was because my confidence in my new self was increasing because of the people around me. I could copy what they did as women and do the best I could. Which was better than I had ever done before. I had paid my transition dues and was ready to face the future.  

Answering the Call

 

Image from Alexey Elfimov on UnSplash.

On occasion I am sorry to say it took me over a half a century to answer my gender call. But thankfully, I finally did take the call and listen to the urgent message. 

Please keep in mind I don't count all the years I attempted to cross dress my gender issues away. As I often write about, all cross dressing did was provide me with a quick fix. After I dressed as a girl, I felt better for a while before the same old tensions of life with gender dysphoria set in. The problem was, deep down I knew I wanted to do so much more than look feminine, I wanted to be feminine. 

One of the few good things which came from my gender struggles was practice made perfect. Even though I knew I was the only one who could see my progress with makeup and clothes, I stuck with trying to improve every time I cross dressed. It was so difficult for me since I only had the mirror to answer to when checking out my progress. The problem was the mirror was so good in telling me everything, but the truth and I tried to keep in mind I might look good, for a boy in drag. Not as an actual girl. In other words, I learned I needed to hold myself to a higher level than other cis women I observed if I was to survive among them. 

The entire process was so difficult for me since I had never been detailed orientated in my life. Just getting by was not going to be the way to go. I was fortunate when I encountered professionals in the makeup world who helped me along. One in particular came following a transvestite-transgender party mixer I attended near Cleveland, Ohio years ago. After the mixer slowed down, the organizers provided several makeup professionals to provide free tips to whoever had the nerve to ask. On that evening, I am happy I put my ego behind me and answered the call for much needed makeup assistance. The catch was I needed to remove all my makeup and wig and let the professional start over. His work and results were amazing, and I even understood all the tips he was trying to tell me. The end result was I was flooded with compliments and my gender euphoria soared to an all-time high. Furthermore, later on that evening, I was even hit on by a guy in a straight venue I went to with other transwomen from the mixer. 

That night, I did not answer the call to stay with the guy who showed interest in me. My reason was, I was in a strange town with a person I did not know, and I did not know if he realized I was transgender. Not a good place to be at two in the morning. On the other hand, I loved it when the other "A-listers" from the mixer were jealous of me for once.

Along the way, I ended up answering enough calls to barely keep myself going. There were plenty of times when I did not know if my mental health could take it, and I could keep going. It was then when I took the all-important call to begin gender affirming hormones and change my life forever. I was sixty by then and knew there would be no turning back. After I did, I learned taking the most important call of my life turned out to be a life survivor for me. I remember the evening when I decided to answer my phone for the last time. All of the sudden the voice told me I was free to live as my authentic self and the relief I felt was tremendous. All my previous misgivings were swept away. 

Gender House of Cards

 

Image from Erick Langfield on Unsplash.

Just when I thought I had my life altogether, the world collapsed on me.

For example, when I thought my makeup and hair was the best, I could do, I would walk or scowl like a linebacker and ruin my entire feminine image. Of course, then, I would have to recount my steps and see what I was doing wrong. It took me years to build a solid foundation to build my gender future on because my base was so weak.

What made matters worse was the fact at the same time, I was beginning to do so much better as a man with my career. It was like I was succeeding despite of myself. Down deep, I attempted to destroy everything I worked so hard to achieve. All the self-destruction really took a toll on me and my mental health. To make matters worse, on my worst days I would attempt to take my gender frustrations out on the people closest to me. I became so bad; I even lost a job over my actions. Perhaps the worst part was, I did not grasp what was happening to me. I kept repeating the same old stop-gap routine of cross dressing once or twice a week, feeling better for a day or two before I would revert back to my old gender frustrations again. Predictably, my frustrations would repeat, and my gender house of cards would come crashing down again. 

Finally, as I began to acquire more confidence in my transgender womanhood, I started to increasingly build a better base and feel better about the major struggles I knew were coming up ahead. Primarily, what was I going to do about my twenty-five-year marriage to a woman I loved and a successful job I would have to leave behind. And all of that just scratched the surface of all the obstacles I would need to face such as what would my sexuality be if I decided to live full-time as a transgender woman. The path ahead, at the least was very murky. 

Since I was a very social person, I needed to figure out how not to be so lonely anymore. I just could not keep going out to be alone. My dilemma was men did not approach me seriously and I did not know how to react if they did. My first date with a man was with a transgender man who afterwards said I was very scared. Which was true. The problem became when the only other path to being social for me came by approaching other cis women. Fortunately, I did not have a problem because more and more of them approached me. For whatever reason. Regardless, when I went out socially, I ended up at the least talking with other women. Just having the chance to practice my feminine communication helped me to build a better gender base to build from. 

From that point, life became easier, and my path became clearer. Increasingly I understood I needed to leave the male life I never really wanted behind and jump the gender border at whatever the cost. I was near the age of sixty and was so tired of living a lie and was to the point if I did not complete my transition, I would never have the chance to live my dream.

By this time, I was able to build a solid gender house of cards, so everything turned out successfully when I made the final move. Perhaps here would be a good time to quote Paula from the UK: "For some of us there is a real need not just dress as a woman, for the world to experience us, and accept us as a woman ~ it is not enough that in our mind we are women, we need to go all the way; and that is why we need to transition. I too remember my wife saying (with no intended irony at all) "It takes balls to be a woman"

Most certainly Paula our wives were right. That is the primary reason it takes a solid foundation to approach transgender womanhood. Thanks for the comment!

Who was the Problem?

 

Image from Ben White on UnSplash

Looking back at my long journey to transgender womanhood, I finally discovered I was the true problem all along.

I was in shock. All this time I was desperately seeking someone else to blame for my gender identity issues. I kept thinking I was alone in the world and why did it have to be me. Remember too I grew up in the pre-internet generation before there was much if any real information available to gender challenged people. The struggle was real.

It took me years to figure out I was not a man cross dressing as a woman but rather I was a woman cross dressing as a man. To arrive at such a major point in my life required years of trial and error in the public's eye as a novice femininized person. To advance to the life I had always dreamed of, required a lot of work on one hand and confidence I could do it on the other. 

Somehow, I needed to work through all my paranoia I was experiencing and begin to enjoy my new life. I equate it now with learning to dance with a new partner and beginning to feel at ease with it. Primarily when I tried to perfect moving as fluidly and gracefully as a natural woman. Moving like a linebacker at a dance was out. It all was a major obstacle towards moving to my dream. Or could I ever hope to be able to live fulltime as a woman like I had seen others around me do. Then if moving as a woman was not difficult, communicating came along and presented the greatest challenges of all. 

The act of communication came up on me quickly. As I started to go out in the public's eye just to get out of the house as a woman, the better I became doing it. I learned quickly, how many other women wanted to communicate with me. For the most part, they were just being nice and wanted to know what I was doing in their world. Once they found out why I was there and I did not pose a threat, they wanted to know more. If I did not learn the basics of feminine communication quickly, then I would be the problem if I came off as unfriendly or even worse, bitchy. To work on my fears, I went back to the mirror to practice talking as a woman. It was bad when at first, all I could come up with was a scratchy falsetto which just would not work. Initially, before I began vocal lessons, I started with a quiet background voice as I tried my best to mimic the woman I was talking to. 

Perhaps the biggest problem I encountered was adjusting to the basic passive aggressive spirit of women everywhere. Primarily, I needed to learn a smiling face did not always mean acceptance from another woman. I was the problem when I treated smiles as acceptance and learned the hard way when they were not. I think I still have the scars down my back to prove it.

It turned out, my basic stubbornness to leave my male self behind was the real problem. All the stress and tension he caused over the years cannot be reclaimed.  In the end, I needed to put all the blame on myself. If I could have understood all my gender issues over the years, life would have been so much more pleasant for me. I am sure it all goes back to me knowing I felt better as a girl and more natural. I have no idea now why I waited so long. Except I did not want to give up all the materialistic items I had accumulated as a guy. It took a transgender woman to whisper in my ear that all would OK if I just had followed my heart and transitioned. Then I would not have been the problem at all. 

The Double Edged Gender Sword

Image from JJ Hart. Wife Liz on left.

The longer we live as transgender women and trans men, often we find many aspects which represent a double edged sword. 

One of the edges of the sword has to be the duress we feel when at first we arrive in public for the first time. To make matters worse, we have no peer group to help us out of the mirror to be judged by the harsh eyes of the world. No one to tell us we looked clownish as we tried the makeup arts for the first time. I can't tell you how many times I hurried home in tears following being stared at at the least, or laughed out of a venue at the worst.

From it all, I learned to develop a thick skin and always go back to the drawing board as quickly as I could to help solve any presentation problems I might have had. Even when I was doing it, the cross dresser drawing board was certainly difficult to figure out. What happened was, I used the very brief moments of gender euphoria I earned and moved forward attempting to tightrope my way along the sharp edge of my sword. I was risking ridicule at the least and the loss of family, friends and employment at the worst. Failure as a transgender woman was a very real pressure.

Once I began to learn how to present in public more effectively as a transgender woman, I began to use my sword more effectively.  Then the world became much more comfortable for me in my quest to live my femininized dreams. In addition, my makeup arts became better as well as my use of hair to enhance my appearance. 

It bares mentioning also, going through the overall transgender experience, made me a more resilient person and set up to battle the more challenging times we face. I learned in my research transgender folk have always been around and always will be, no matter who tries to erase us. Battling the sword all these years helped me be more secure in my transgender identity. 

In all fairness to my sword, it started out very dull. I worked long and hard to sharpen it by going out in public which was the best indicator of my progress.  So I took all the good and bad and did the best I could with it. All my interaction with the public included the dark evenings when red-necks repeatedly kept playing "Dude Looks Like a Lady" on the juke box in a venue where I was a regular. Since management at the time would not support me, I left to find another venue and took my money elsewhere. I was rewarded months later when an employee from the venue I was discouraged from coming to, found me in another venue and invited me back. To make matters even better, the manager who would not back me up was fired for drug use. Excluding a stray bigoted woman in the woman's room, I never had any further problems there again.

Once my gender sword swung back into doses of gender euphoria, I began to appreciate all it had done for me. Transgender womanhood was finally mine to enjoy when I learned I was not a quitter and was in my transition for the long haul. 

Trans Girl in the Winter

Image from Freestocks on UnSplash.

I happen to live in Ohio where there is often a weird mixture of the four seasons of weather. For example, when it seemed fall has set in, summer returns and the sweaters and leggings you have pulled out have to temporally go away. Now, around here we have made our way into winter. Which means I have had to dig a little deeper into my collection of leggings to find the lined ones. I love the soft feel of the leggings and how they keep me warm when the temperature dips well below freezing.

For my wife Liz and I's winter time walks, I usually pair my favorite leggings with my furry boots and bulky soft sweater before I have to go outside and brave the elements. These days, I need to force the issue with my walks since Liz and I are going to visit the Florida Keys in January. So I need to do my best to walk as long as I can when we go. Since there is thirty days away, there is plenty of time to write about our winter vacation before it arrives. Such as my first time swimming as a transgender woman.

If I had my choice, I would choose winter over our hot, humid summers any day. I like the fashion and the fact it is easier for me to stay warm in the winter rather than cold in the summer. I know possibly, I may be in the minority of all transgender women who value the look and feel of bare skin in warmer times. While I remember vividly the freedom I felt when I could finally shave my arms and wear short sleeved women's fashions, over the years, the feeling has somehow went away. One way or another, I have traded the feminine feeling of leggings for the sensation of shaved legs in the wind.

Either way, the entire fashion process is one of the reasons I enjoy my transgender womanhood so much. The planning ahead for the seasons means so much and winter is just a portion of the process. Of course we will see if I am just as enthused if we get any sizeable snowfall in December since I have one Christmas lunch coming up with the Cincinnati Alzheimer's diversity council as well as a Yule get together with Liz's circle of friends. During which I will have the opportunity to explain why I turned down an interview with a local television reporter after the election. 

So there is quite a bit coming up in December, including awaiting the arrival of a new laptop I thought I would go ahead and purchase before the proposed tariff's go into effect driving prices upwards. It will be interesting to see how easy or difficult the set up will be. I am not very technologically advanced. The laptop was one of the biggest purchases I have made in a long time. It was an online Cyber Monday purchase so I did not have to put up with any lines or pestering sales people. Patience, along with many other attributes will have to be my main goals following trying out a new laptop in over a decade. 

Overall, the month of December is more enjoyable with the fashion and festive Christmas lights in the neighborhood. I have respect for those who put effort into holiday decorations since all the work I put into my second wife's extensive decorations 

It all makes up for the drab months of January and February. Being a trans girl in the winter is yet another challenge. 

Trans Girl in a Furniture Store

Image from Nathan Dumlao
on UnSplash

Once I had progressed to a point where I could comfortably navigate my way around in public as a transgender woman, when Christmas rolled around I thought I could do my shopping as a woman.

Since previously I had helped gift my second wife an oak roll top desk, I thought if I could find and afford a matching oak book-case, I would buy it for her as a Christmas gift. Before I did, I needed to find a store which carried the book-cases. As it turned out, the closest one I could locate was fifty plus miles away in nearby Columbus, Ohio.

Before I made the trip, I needed to make sure I planned out when my wife would be working and not at home for the amount of time it would take me to go and buy her gift. Once I did that, I needed to add in my "prep" time to get ready to go and I was all set for yet another gender adventure into transgender womanhood. 

For the evening, I chose my favorite business professional outfit at the time. A black pantsuit with heels, my best makeup job and shoulder length blond wig. Plus, since it was cold that night, I could wear my long, wool coat to stay fashionably warm. 

As I left the house and headed for Columbus, I was nervous about how I would be received and if I was able to purchase a bookcase would it fit in my SUV and who would load it. I was so afraid of being "discovered" and shunned at the store. But as I entered the place, my fears began to dissolve as I blended in with the other shoppers as I looked for what I wanted. It turned out about that time, my first taste of feminine privilege kicked in. First of all, I did not even need to find a clerk to help me. Before I knew it, an eager guy was ready and willing to help the tall blond in her heels and pants-suit. 

He asked me if I knew what I wanted and in a soft voice I told him exactly what I wanted. In no time at all, he showed me to a cashier and I bought my precious gift with a smile and then wondered how I would ever make it to the car. Again, I should have not worried much at all as two able bodied young men quickly showed up to load my book-case. I loved it when one of them even opened the door for me as we were headed to my car. Brimming with gender euphoria and confidence, I hurried home to gently unload my gift and hide it in the garage. 

Sadly, I went through the process of returning to my male world in record time as my wife was due home at any time. Somehow I managed and was ready to act as if the evening never happened. At least this time I could tell her the truth when she was asking how my evening went. I told her I went shopping for her and to stay out of a certain area of the garage until Christmas. For once that was how the evening ended without a fight or me having to lie about going out as my femininized self.

The internal excitement of what I had accomplished that night stuck with me for quite a while and when it wore off, I had more confidence to shop for her as a woman in the world so I shopped again in other venues for gifts.

Being a trans girl in a furniture store was just the beginning. I will have more experiences to write about as Christmas gets closer.

In the meantime, thanks again for reading along. Your input means so much to me and comments are always appreciated. 

Was there Ever a Plan

Image from the JJ Hart
Archives

Looking back, I needed a very definite plan to follow as I transitioned into transgender womanhood. 

Similar to so many of you, I started by "borrowing" a few of my Mom's clothing when I could still fit into them. I would have added a sister in but I did not have one. When I became old enough to do it, I took on a newspaper delivery route in my neighborhood and combined my new meager funds with the allowance I received at home from my parents and with the money, I was able to buy a few clothes and my own makeup. Since we lived in a rural area outside of town, the plan was to stay a day or two with my Grandma who lived very close to stores *downtown where I could attempt to shop for what I wanted. The problem with the well thought out plan was my Dad worked downtown too and he was the last person I wanted to run into with my new "treasures." 

After I conquered my fear of shopping for cosmetics I did not really need, I was able to buy makeup which did not make me look like a clown. Another problem I had was, the only example I had of applying makeup came when I was able to watch my Mom do it. I wonder if she noticed me watching her. She was probably so entranced in her face, she did not notice I was entranced also. 

The older I became, the more entrenched the plan became. I was able to increase my small "collection" of feminine wardrobe and makeup as I went along and managed to hide it from my brother and the rest of my family. At the same time, I wanted to become better at the makeup arts and finding clothes which fit me. 

At the same time, I became comfortable with how I looked in the mirror and increasingly had thoughts of expanding into the world. I did try to come out fully dressed to one of the very few male friends who lived close by in the neighborhood but was quickly rejected and I scurried back into my dark, lonely gender closet. I stayed in the closet until several Halloween parties began to bring me out. From then on out, my plans really began to change.

During the parties, I learned how much I enjoyed my time out of the closet and I just knew I needed to figure out a way to live as a transgender woman without waiting for a whole year to go by. To do it, I knew I would need to start by telling my spouse what I was up to. So the plan was to find out what wife number one and two thought about me being a cross dresser before we were even married. It turned out wife one did not care and wife two was supportive to an extent which helped me along. 

The main rule I had with wife two was to never leave the house dressed as a woman. I started innocently enough before I veered off course and threatened our marriage of twenty-five years. I began going to women's clothing stores and malls where acceptance was easy to come by. Money was certainly more important than gender. I also would go to bookstores and even antique malls where I could browse with no problems to build my confidence. When my spirits went up, I planned ahead for my next big adventure which usually meant beginning to interact with more of the world as a transgender woman.

To do it, I began to stop and eat at restaurants along the way to make sure I had to communicate one on one with a server or bartender. Since I had an extensive background in the restaurant/bar business, I knew basically what I needed to do to survive. Just be nice, do not cause any trouble and tip well and I could be successful. 

From then on, I endlessly planned on what I was going to to next and how I could challenge myself in the feminine world. Sometimes I was successful, sometimes I was not but I always learned from the experience. In my life as a man, I had never really planned ahead on anything, so this was a big difference. Perhaps it was because I could not wait to try again to live out my dream of transgender womanhood.

*Those were the days of strong vibrant downtowns in many cities, including mine. Before malls took over and they tore the downtowns apart. 

It is In Your Nature

Image from Hannah Popowoski on 
UnSplash

Following my fifty year battle with my gender issues, I just gave up and went with what felt so natural to me and completed my transition into transgender womanhood.

It was certainly a long drawn out journey of self discovery. It was full of ups and downs as I gained my footing along with confidence as I learned to just be myself. Looking back, I don't know what took me so long. Perhaps I can blame it on my male self wanting to hold on to the lifestyle he worked so hard to survive in. He put up quite the battle before giving in. But give in he finally did. 

When I finally began to explore the world, I learned how much of it was run by women and in order for me to survive, I needed to get along one on one with the other women around me since men rarely showed me any interest as a person. Women on the other hand were curious why I was in their world and I was somehow valued for being there. Perhaps it was my honesty showing through, which I gained from jumping the gender border into their world. I don't know for sure but I loved the attention I was getting. 

It was in my nature, because I had always valued the women friends I had over the very few men friends I ever was capable of having. I just did not fully ever recognize why until I was fully allowed to play in the girl's sandbox. Before I was allowed in though, I needed to earn my way in. I had to show my true nature was feminine and I needed to learn the rules of a brand new gender game. For example, I found myself in a world where passive aggressiveness ruled and a smiling face did not mean it was a friendly face. Much different in the world of men I was used to. It all was more of a mental game than I was used to also as I tried to anticipate where another woman was coming from. Especially when I came down to interacting with their men. On a few occasions, I came too close and felt the claw marks down my back for doing so.

The whole process just made me stronger and more confident in the woman I was becoming. Quickly I felt as comfortable in the new world I was in as I learned how the gender game was played. Women are more apt to form cliques than men who form teams and instead of finding the alpha male for acceptance, I needed to find the alpha female who was running the clique and I was in. 

Once I was in, my life became so much easier. Primarily because I did not have to fight being two genders anymore and the inner woman I was hiding for so long had her chance to run the show. She took to the process naturally. The only thing she did not do was harass me about why it took me so long for her to take over. Which she had every right to do. More importantly, I found she was a good person and got along with people including the all important world of other women. Essentially I found I good set and enjoy the show.

Of course before I could enjoy the show, I needed to understand the process of how to blend in with the world as a transgender woman. It was difficult putting my old male ego aside and realizing I was never going to be the most attractive woman in the room, I could present well enough to survive if I had the confidence to do so. 

What I really learned was, it was all in my nature to do so and if I relied upon it, I would be fine.

Finding your Happy Place

 

Image from Priscilla du Preeze
on UnSplash

These days you may think finding any sort of happiness as a transgender woman or trans man may be impossible but it is not.

Take this morning for me as an example. As I was getting dressed and viewed my bare thighs before I put on my pants, I had forgotten how nice it is to view their increasingly femininized form thanks to the use of gender affirming hormones. In other words, I have developed my own hips, finally following years of hormonal usage. In many ways I took the slow cautious route when I started down the medical transition path on the advice of my doctor. He advised me to take minimum dosages until we could judge the effects on my body.

At the age of sixty, my body took to the new feminine hormones wonderfully and naturally. Soon I was put on higher doses of HRT and bigger changes began to take place rather quickly. I had set up a semblance of a timetable of when I wanted to shed all my male clothes and live fulltime as a woman but it turned out the timetable was a waste of time. What happened was I became very androgynous looking in a very short period of time. While I was developing an increasingly noticeable set of breasts, my skin began to soften which in turn softened the lines of my face. So much so that anyone who knew me from before would notice the difference.

Even though I was shocked at the rapid exterior transformation of my body, the whole process felt so exciting and natural I could not wait to do more and more as I accessed my new transgender womanhood. It all meant setting up new plans and timetables on who I was going to tell and when. By this time in my life I had outlived most of my family and close friends, so telling many people was not going to become a problem. I had even retired so I did not have to worry about transitioning at a job. All of this left me with two main people to come out to. My only daughter and only slightly younger brother. 

I knew at the time, I had a better chance of succeeding at telling my daughter the truth about me than my brother. My daughter was much more liberal while my brother's in-laws were right wing Baptists and I figured he would sell me out to appease them. It turned out I was right on both accounts. I found my happy place when my daughter totally accepted me and was down when my brother did not. I took my fifty fifty win/loss record and moved on.

To this day my happy place continues with my daughter and her extended family. In fact, my wife Liz and I just accepted an invitation to Thanksgiving dinner at my daughter's Mother-in-Law's house which makes up for the decade long snub from my brother. 

As the holidays approach, I hope all of you can find a happy place to celebrate with family, blood relation or not. In the transgender community, often we find the best family in non traditional situations. It is a wonderful time of the year to discover or re-discover a new happy place for yourself.

Finding your Happy Place as a Trans Girl

Image from Trans Outreach, JJ Hart

As I negotiated my way through the gender wilderness I was in, I needed to reach out at times to find moments of gender euphoria or happiness. 

As I have written about in the past, happiness was a learned trait which was difficult to come by in my family. Being good was not good enough, there was always time to be better. Little did I know, I was seeking to enter a world where being better than the average cis-woman was not going to cut it. Being better meant survival. 

As similar to most of you transgender women and/or cross dressers, I started out innocently enough as I raided my Mom's clothes and tried to admire myself in the mirror before my family came home. The whole process worked well for awhile until I grew restless and wanted to increasingly explore the world as my femininized self. Sadly, most all of this occurred when I approached puberty and all the unwanted male changes to my body began to happen. Very soon, I found wearing any of Mom's clothes was impossible as I gained unwanted hair, bulk and angles I hated but were stuck with. It was the infamous testosterone poisoning setting in which I battle to this day.

Rather than be unhappy, the mirror and my mind helped me to battle my way through severe bouts of gender dysphoria. I worked hard on acquiring the proper clothes and makeup I would need on a very limited budget. Of course with no guidance, I experienced many disasters on my journey before I settled in on an appearance which could get me by in the public's eye. I needed to disguise all my testosterone poisoning. Still, I persisted without much help and slowly learned the art of makeup which finally I did get some assistance with. At one of the cross dresser - transgender mixers I went to, I put my ego away and sought help from one of the professional makeup artists they had giving free advice. In language even I could understand, the guy doing my makeup guided me through a truly amazing transformation. Even I thought I looked so good I was happy with the results. 

Even still, the transformation was fleeting and all too soon, I needed to go back to my boring unwanted male life and the happiness I felt went with it. Leaving me in a state of depression. I did not realize having a feminine appearance was only the beginning and achieving any standard of looks went only to the upper levels of feminine achievement for me. Beauty was fleeting and very skin deep for me as I continued on my gender journey. I was told several times by my second wife I made a terrible woman and in no way was she talking about my appearance. She was right and it took me years to put my male ego behind me and learn what she truly meant. 

I also had a close transgender friend who told me one time I passed out of sheer willpower. Which I took as a backward compliment. Meaning I was going to engage the public and do my best to be happy even though I was not the most attractive woman in the room. When I did, I made a huge step forward towards becoming my authentic self. It was not until then did I begin to gain new friends and become happier. 

Sadly, my second wife passed away before she ever had the opportunity to meet the new improved me but I did have several friends who did. Their main comment was how much more happier I had become. I guess I never realized how much my gender issues had shown through to others in my male life. 

When I reached this point, I knew my family and upbringing was wrong. I could be happy in life and appreciate it. Along the way, I learned the truth that all the money and beauty in the world could not buy me happiness. I spent way too long living in the mirror to keep doing it. The friends and wife I made when I put my male self behind me proved happiness was not impossible for me. 

Hitting the Transgender Wall

 

Image from Selin 
on UnSplash

There were so many times during my journey to finding my authentic self that I hit a wall or two or more. 

The easy walls came when I was younger and was trying to find makeup and wardrobe items to admire myself in the mirror. During that time and into the future, finances were a major set back. As much as I admired the pretty clothes the girls around me were wearing, I just did not have the money to afford any of them. There was no way I could go to my parents and ask for a pretty dress for my birthday or Christmas. Plus, I was stuck at a major point of my overall femininized image when it came to my hair. In those days, I was stuck with very short hair cuts such as burr or crew cuts and there was no way I could afford a wig. A major wall, to be sure as I think having the first wig I cherished did not come around until my college years in the late 1960's till the early 1970's when my military days took over. Of course I was against the wall again when my hair needed to be kept very short.

After I had served my time in the Army, I was able to secure the finances to afford a more update feminine wardrobe and my walls began to take on a more mental aspect with me. The more I was able to sneak out of the house and into the public, the more I knew I had little or no knowledge of where I wanted to go as a novice transgender woman. It seemed everything was being thrown at me at once and my mental health crumbled after I was hitting many walls at once. My male life was becoming more and more demanding as I became successful at my job and I discovered the more I explored the female world, the more I liked it. 

Even so, climbing the feminine walls were difficult. It seemed everytime I mastered one aspect of being a transgender woman such as walking, I would catch my heel in the crack of a sidewalk and ruin my whole day. As I continued along my bumpy gender path, I found mishaps with walking in heels were indeed minor in the scope of my transgender life. On the horizon loomed much more serious walls such as communication with the public and with women in particular. Overwhelmingly, men ignored me and women were curious about what I was doing in their world, I discovered quite quickly I was interacting with more women than I had ever done as a guy which was scary in many ways, including what would I say and how would I say it. 

I wondered what had I done when I was forced to actually talk the talk of the person I had become. I resorted to what had worked for me in the past as I had encountered tough trans walls to climb. I basically tried to shut my mouth and observe what was going around me. It worked to an extent until people (women) began to warm up to the new person I had become. I even was giving other women advice on how to understand their boyfriends or spouses. 

Anyway you cut it, I guess for me, gender affirming hormones created the last major wall for me to climb. At the time, I was doing my best to appear as a woman and communicate as one to the world. Beginning the hormones in many ways was a selfish move because I did it for myself. When I did, instead of more walls crashing down, they melted. HRT, when I was approved for it was a magic potent stimulant my body had been craving for years. Very quickly, I knew I had made the right move as I was able to tear the final walls down and make my way into fulltime transgender womanhood. 

Surely, I was bruised and battered by hitting all the transgender walls I needed to scale to live the life I wanted but I made it. When I look back on all the terrifying yet exciting steps I took to get to where I am mow, I wonder how I made it. First there was my appearance and battling testosterone poisoning then overcoming the problems of male behavior which also effected my life that all made for a rough journey. Surely there were too many walls to count.