How Difficult Could it Be?

 

JJ Hart

When I started my transgender journey, I was very naïve and I kept thinking how hard it could be to stay on my path.

All I saw was the good side of being feminine with all the girls around me in their pretty clothes and long hair when I was stuck in all the restrictive, boring male clothes and very short haircuts. To make matters even worse, I needed to make sure I kept all of my cross-dressing activities very hidden from the family and friends who would have ridiculed me and called me a sissy boy. The worst thing I could be called in my very male dominated family.

As I said, I was naïve and for years thought that all I wanted from being feminine was looking like a woman, so I obsessed about it night and day. Eventually, I did come closer to achieving my goal while all the ignoring harassing comments from my second wife who rarely wore any makeup at all. On the rare occasions she went out with me, she constantly thought I was going too far with my makeup and hair to the point of calling me the “Princess”. When all I was doing was trying to blend in with the ciswomen around me by overcoming my old male self.  Of course, I felt the criticism was not fair and the evening was ruined. Often before it even got started. From that point forward, the fights started because she did not like the trans woman I was becoming. And I did not understand why.

I think now that she thought I had not paid my dues as a woman yet to claim the socialization title and she was right. I was still stubborn and did not know how I ever was going to have the chance to play in the girls’ sandbox if I did not want it bad enough. I was stuck between two massive changes in my life which would either involve giving up the woman that I loved for one that I was learning to love. How hard life could be was becoming a reality for me like a boulder rolling down a cliff directly at me. It was quickly becoming unbearably hard when I discovered I could indeed see a path ahead of living my life as a transfeminine person.

What happened next was that I began to step away from my wife and essentially live the life she challenged me to live. That is to begin to socialize myself as a transgender woman in the world. I started to meet strangers as a trans woman who never knew me as a man and start all over in a new life. How hard could it be? It was and the whole process scared me to death. I was terrified of being stripped of all my old male privileges and having nowhere to turn if something negative happened to me. How would I be able to react to potentially negative situations in my new life. It turned out I did not have many potentially negative problems, and I was able to grow into my new feminine person with very few problems because most of the world did not care what gender I was. They were too wrapped up in their own worlds. Especially the cismen who were so afraid of their fragile sexuality that they left me alone. Which was fine by me, since I had always had a problem with making friends with other men when I was trying to be one anyhow.

Ciswomen, on the other hand, were much more willing to let me in their worlds and even show me around. Making it less hard to be one of them as I was learning daily how to fill out my life. I always had enjoyed being around women and found I even enjoyed it more when I was made a member in good standing of the girls’ club. Being in the club entitled me to use women’ only spaces such as restrooms which made my life so much easier also.

Most likely, I made some male to female transition issues more difficult than they should have been. Such as when I first came out into the world and thought everyone was looking at me, when they were not. I even went as far as to wear a favorite pair of sunglasses I had to see if anyone was staring at me without them knowing it. They were not, I was relieved and was able to go on with my new life. With new confidence I never had before. Maybe I could achieve my dream after all. It was a scary thought because then I had to start to think about what I was going do with all the excess male baggage I had built up over the years when I was trying my best to hide my true self by being a successful man.

The entire focus of my life changed as I began to consider the new and exciting reality of being able to live out my dream I had wanted since I was a child. I was sad when I could not tell the truth when an adult asked me what I wanted to be when I grew up and I could not say a woman and earn a quick trip to therapy by my parents. At the time, being a woman seemed as far away to me as being a lawyer or a doctor. But at the same time, a dream I really wanted to live.

Along the way, two things were evident to me. One of which was every time I achieved a goal on my path, another would appear for me to consider doing. And the second thing was, every time I began to doubt myself, I would start to feel natural about my journey and it would re-energize me, so I could move forward again. Forward was always good and made me feel better about my life which brings me back to my original point of how hard it could be to cross the gender border. Exceedingly difficult at times to be sure, but excitingly natural as I was doing it.

Wherever you are on your path to a better tomorrow, I hope you can discover your truth and make it in one piece. As always, thank you for reading and comments are always appreciated!

 

Is It too Early for Halloween?

 

Early fall Image
JJ Hart

As I look around the neighborhood I live in, I see people putting up their Halloween decorations already.

Then I began to think of the supposed “good old days” when about this time in September that I was starting to seriously consider what “costume” I would wear and how could I maximize its use by going to as many parties as possible. It just did not seem fair to me that I had to wait for a once-a-year party to express my feminine side without the fear of retribution. The worse that could happen to me were the other women at the party asking me who helped me with my makeup and did I really shave my legs for one night.  I was learning a valuable lesson about how curious ciswomen could be when you cross the gender highway into their lane.

Basically, my biggest decisions came as I thought about which theme I would follow year to year if I was going to the same party. And how creative could I be with my “costume” Ironically, my first big attempt at dressing feminine at a Halloween party came when I was still in the Army in Germany, when I was invited by my future wife to go to a hospital’s party. I had a couple of other wild friends who had their costumes already picked out and were coming as various forms of the male and female anatomy. So, I thought it would be an ideal time to fall from my cross-dressing wagon that I had been forced to be on for two and half years and come as a trashy prostitute.

I do not remember now how I got the clothes I needed to complete my outfit, but I was able to put together a short mini dress, long blond wig, hose and heels for a very effective costume. Since I still had approximately six months to go in the Army at the time, I was happy that no one seemed to care that I was dressed as a woman at the party.

When I was discharged from my military duty, and Halloween rolled around, I had a different challenge to face with all the newfound freedom I had. One thing I did was get away from the prostitute look and try to find a way to find a “costume” like what a ciswoman would wear.  In other words, I wanted to go to the party and try to pass as another woman enjoying herself. During the first multi-party Halloween night I went to, I think I did well. I went as one of the French girls I had seen in Paris when I was in the Army and brought the look home with me. I paired a all-black outfit which featured black tights, mini skirt and leotard with my blond wig, red lipstick and topped it all off with black flats and a black beret.

I was having a very good time entertaining myself in one of the big local clubs I went to which was having a Halloween party when a guy in a full mask approached me and simply said “I know who you are.” At first, I needed to recover from his comment before he went on to say, “I know because you look just like your mom!” Then I knew who he was and did not know whether to be flattered or not before he did not say anything else and went on his way. I did know I looked like mom but not that much.

From then on, I began to build my Halloween “costumes” from scratch and only used my many trips to thrift stores to help me with items for what I was going to wear. All I really knew was that I enjoyed my self immensely in my new world as a transgender woman and wanted to see if I could take it past the party scene and into reality. There would be other significant parties I will write about later, for now I had to learn if the build up to Halloween was totally worth it. I learned it truly was because of all the early lessons I would need to learn if I was ever going to decide to try to cross the gender border and live full-time as a transfeminine person.

I also realized that Halloween would be just the briefest thrill in what would be a long life of gender discovery. Would the overall gender euphoria of making it through the parties successfully be worth it when I had to crash back to reality and my increasingly boring male life. Plus, I found it was unbearable for me to just wait a whole other year to experience my feminine side again without me going out in public. I took my gender life into my own hands and began to explore the world in malls and outside in different venues such as bookstores which helped me build my confidence as a novice trans woman.

I went further, quicker than I ever thought I could and forever put Halloweens behind me as a necessity in life and more of a fun pursuit. In its place, I would be trying to carve out a brand-new feminine life of my own. It was the beginning of the most terrifying yet exciting time of my life. Mainly because I was stripped of all my old male protections and had to start all over again in a world where I did not know who to trust. Including myself because everything I knew was changing when I left the good old boys’ club for good and applied for membership in the girls’ club that I had so long waited to join. I was just at a point where I needed to convince ciswomen around me that I was serious and brought different qualifications to the feminine table. I had to suggest I was a woman too but just had been socialized a different way than they had been.

In many ways, Halloween was the earliest part of my socialization process thanks to the early interactions with ciswomen (and men) that I experienced. Immediately, I found that men I had known for years ignored me as a potential cross-dresser or whatever they thought I was. It did not matter. I was out of the club.  While at the same time, women I had known for years were curious about me. Lessons that had carried with me well in the learning years to come.

That is why I will forever miss the early excitement I felt around my early Halloween parties and why I still feel the fun I felt when I see the neighbors putting up their decorations early. Who knows, there may be a person in the family with gender issues also.

 

 

 

 

 

Deep Gender Frustration

My attempt at formality.
From the Jessie Hart Archives.

One of the first deep seated internal  frustrations I felt with my gender dysphoria was when I first encountered the challenge of attending my junior-senior prom in high school. 

I was very shy and nervous when it came to being around girls of any type. I didn't have any sisters or any girls in the neighborhood I grew up in, so I had no experience. When I made it to the time when my first prom came up in my junior year, I was stuck in a new high school with very few friends period. Especially no female ones. So I had no one to even summon up the courage to invite to the prom. It turned out, the problem was going to take care of itself without much effort on my part. 

What happened was a group or clique of popular girls noticed one of their group did not have a date to the prom. At that point, they reached out to me to find out if I was interested in attending the event. I nervously said yes and the planning began. Little did I know what I was getting into. As the male part of the date (back in those days) I was expected to provide everything from transportation, to dinner to flowers for my date.  My deep problem was I was the one who wanted to wear the fancy gown and be given a corsage then dined and danced with. I was deeply frustrated. The only good parts of the entire night were my parents were proud and probably a little relieved I was finally going out with a girl. On my part I was interested to see how I would finally find out how I would react to a real live date.

As predicted, my first prom did absolutely nothing to relieve any of my deep seated gender frustrations. In many ways, the whole process just made it worse. At  the least at that point I had began the process of learning what dating a girl was all about. In my senior year I actually met and stayed with another girl until I went away to college. The time included another prom in my senior year which I needed to suffer through since once again I wanted to be the girl, not the guy. I hated the tuxedo I had to wear all the way (again) to not being the one in the glitzy dress. The only revenge I ever received came years later, the supper club we went to eat at prom became a large gay venue and I was able to use the same women's room my date used. A small amount of retribution but meaningful none the less.  

When I went way to college, the initial months on campus provided one of the few gender respites I ever experienced from my transgender life. But to make a long story short (as you know) my desires to love everything feminine never went away. In fact, years later my jealousy re-surfaced in a major way. During my years working for a major restaurant chain franchisee, the company threw lavish Christmas parties for the store managers and upper level assistants.  The parties were semi formal  so once again I was thrown in to being downright jealous of the women who would be attending. Several were very attractive and needed to try to negotiate getting in and out of the limousine the company provided  for transportation in the fancy gowns. As the other men admired the women and their attempts to stay modest when they entered and exited the limo, I on the other hand, wanted to be one of the women in the beautiful dresses. 

It wasn't until fairly recently when I came even remotely close to achieving close to the same feeling cis-women feel when they are able to dress up. During recent Christmas's and other banquets I have managed to come up with a semi formal dress up look. It provided me a respite from a little of the gender frustration  I experienced over the years.  I also discovered women all along were aware of their own insecurities of semi formal events. Often the grass is not always greener on the other side of the gender fence. 

Still a Mystery

Photo from the Jessie Hart
Collection

 When I went to the breakfast meeting yesterday, I was able to take a very small sample of how transgender women and trans men are being accepted in the area of the country around me. The meeting drew approximately one hundred people. Mostly younger professionals.

Before the speaker took the stage, there was a time for networking with others around us. Since I was still basically shy, I decided to stay back and see if anyone tried to reach out to me. No one did, so now I regret my decision. I am sure there will be a next time, so I will have a chance at a re-do and do better. After all, the last thing I want to do is come off being unfriendly. What kind of a transgender ambassador would I be? 

One thing I will always question is how my first impression is received, or what are people really thinking about me,  Yesterday the process began early when I needed to sign in and then find my breakfast, so like it or not, I needed to interact with the world. Everybody I saw gave me a big hello and a smile, which made the overall process so much easier. Long ago, I gave up on my egotistical desire to be viewed as a cis-woman and I settled for being noticed as an attractive (I hope) transgender woman who blends in with the other women. By "working the room" I will have a better idea of what the other attendees think of a trans person. 

Through it all, I still on occasion think, why me? What trigger switch was thrown when I was born to always question the male gender I was born into. The closest I have ever come to thinking I found a culprit was when I began reading about the medication DES which was given for years to women which had experienced problem pregnancies in their past. My Mom had several problem pregnancy's and I was born in the period of time the drug was used, so I naturally was intrigued. Much more so when I read DES flooded the uterus with estrogen when the mother was pregnant. So maybe, that was the reason I always questioned which gender I was born into.

None of that helped me yesterday when I basically retreated myself instead of being a  quality ambassador for the transgender community when I could. I was proud of myself with negotiating the morning Cincinnati rush hour traffic and still utilizing a spotty GPS system on my phone to even find the venue. I thought the difficult part was behind me but I was wrong. I, for whatever reason, couldn't seal the deal and be a quality transgender representative. I will have other chances though and I will do better. One thing I am going to try to have changed is my name tag which correctly identified my legal female name but also said I was "retired" which is also true but I think restricts whomever wants to network with me, I am going to try to get it changed to writer or blogger. Either of which would at the least open potential lines for communication. 

Once I accomplish all of my future goals, I will have to set new ones and hope my life is not such a mystery to others.

Trans-Sisterhood

Image from Manuel Cosentino
on UnSplash

 It is a powerful feeling being a part of the transgender community, or, the chosen ones (which I will explain in a later post). Recently I had a great comment through the Medium writing platform.  It comes from fellow writer "PL James":

".I always find I beat a drum. This drum is about embracing my trans-ness. I did always want to be pretty and slight like a lissome girl, but I am not. I have had too much of life dominated by testosterone...but like you, I lost a ton of weight, and am super-happy about the results of diet and exercise...and can be happy that I am beautiful...not in a classic way, but in a unique and transgender way...and that is fine because we are different...and our own experiences as trans people make us a tribe of our own...and that is the tribe whose standards I wish to be measured by. Yours in "transterhood"

First of all, it's a pleasure to be a part of your "trans-sisterhood" and thanks for the comment. I so agree many of us in the trans community have adjusted to our own standards of beauty as we present ourselves to the world. Years ago, I was invited to participate in a photography project which focused in on the differences in women. Even though I was scared to death to do it, I hitched up my "big girl panties" and went forward with the project. I felt even though I was far from the prettiest woman in the collection, at the least I would have the chance to represent an entire different look at women. Even though I don't have the final picture to post, it was quite the experience and I was honored to be chosen for another unique once in a lifetime experience.

Another very relevant comment came from the same post from another Medium reader "Ann Williams":

"I was recently invited to participate in a women's group, by one of the leaders. I was very flattered, and I would certainly love to do it. But I won't, and this is why. Because I know that none of the women there will see me as a woman, they will necessarily see me as an interloper. My presence will change the energy of the space. They will not feel as uninhibited to be themselves. They will not feel safe.

If I didn't know this, things would be different; but I do. I don't see this as a matter of rights; I see it as a matter of courtesy and kindness. The last thing I want to do is turn a place where women feel safe to be women into a place where they have to put their guard up. That's thoughtless, selfish and unkind --at least, I would find myself to be so, if I ignored their feelings by invading their space.

The fact I believe I am a woman doesn't matter. The problem is they don't believe it. And I cannot disregard the effect my presence will have on their experience."

Thanks Ann for the wonderful comment and I can only say, my experiences with being invited to "women's only" spaces have only worked out for the best. Maybe I am spoiled but I have had so many cis-women embrace me in their spaces, I was shocked on the rare times it didn't happen. I was even embraced and learned what I needed to do to be a more complete version of my new rescued feminine self.

I dare say, being accepted into the "transgender-sisterhood" has been more problematic for me.

Fake it Till you Make It

 

photo courtesy Jazmin Guaynor
on UuSplash

I heard this comment from an unknown cis woman on a television show I was watching last night and it brought back so many memories. Some were pleasant, some not so pleasant. Similar to so many of you, I share many days and even years of living in the mirror as a young cross dressing girl. During these formative gender years I worked diligently on my makeup. While my other male friends became proficient at painting model cars, I increasingly became better at applying my own makeup. Even to the point of being able to buy my own makeup supplies with my meager allowance and earnings from delivering newspapers. Even though I did become fairly good at applying my own makeup, I still thought I was a pretender until my second wife began to ask me for help with her own cosmetic usage. 

The problem I had was, or one of many, I still didn't realize I had the entire gender situation backwards. All along I thought I was a cross dressing male but in reality I was a girl cross dressing as a guy. Not realizing this basic fact cost me decades of torment as I struggled to find my way out of a very dark and lonely gender closet. The only good which was coming out of the entire process was, the better and more I faked it, the more I slowly began to make it. 

The making it came in stages. I needed to grow out of my girlish adolescence and be able to dress my male body the best I could so I could make it better in the public's eye. Once I was able to accomplish this difficult task with little or no feedback, I was able to begin to sync up my overall feminine appearance and be successful. Or so I thought. I thought if I applied the lessons I learned the hard way in the public's eye and didn't get too outlandish, I could present fairly well as a woman. I did so well on a couple of occasions in New York when I was mistaken for a cis-woman at transvestite mixers, I went on a giant gender ego trip. I was so excited with my results making it a woman, I couldn't wait to do it again and again. It was all good until my wife stepped in and interrupted my ideas of further expanding my feminine pursuits and we began to have massive fights. One in particular which I have mentioned in my previous writings was when she told me I made a terrible woman. 

Of course I finally told her I wasn't trying to make anything but I still didn't have the courage to tell her what I really thought. I loved it when I could try new things as a woman. As it turned out, after she calmed down, she told me her comment didn't have a thing to do with how I looked. It was how I acted and the comment changed the trajectory of my life forever. What could I ever do to understand exactly what she was telling me. I was finally making it on appearance but still faking it as far as feeling good as a woman. It didn't come over night but after many years of trying I finally came to understand what she was talking about. In fact it took the presence of estrogen in my hormone replacement therapy for me to learn the effects of both male and female hormones. Sadly my wife passed away before she ever had the chance to see the complete transgender woman I had become. I don't labor under any ideas we could have stayed together but maybe we could have remained friends.

Age played a role in me being able to fake it until I made it as a transgender woman. I had enough time to make all the gender mistakes I made and still learn and survive. I most certainly faked my gender as a guy until I made it as a woman.  

Dating Myself

 This post goes back to my intensely lonely days following the loss of my second wife and several dear friends. Throughout my life I had plenty of acquaintances but very few people I could call friends. Perhaps it was because deep down inside I did not want very many people close to me in case someday I would follow my dream and come out as a transgender woman. I just didn't feel many of my friends would remain with me, or would I want them to as I went through such an extreme lifestyle change such as changing a gender. Personally, I knew of all the stress and tension caused by crossing the gender frontier myself and couldn't imagine anyone else understanding. As it turned out, this wasn't the first time in my life I decided to go it alone (so to speak) when I was attempting a major life change. The same thing happened when I had to go away and serve my military duty. When the time came to go away to basic, I had done away with any possible serious girlfriends and barely communicated with anyone at all. The only mail I received came from my Mom. 

Early Acquaintance on Right
from the Jessie Hart Collection 

So, all in all, I had experience dealing with extreme loneliness but I didn't really want to face it again. What happened was I ended up falling back on my inner feminine self for comfort. It turned out in times of extreme duress, she was the strong one who comforted me and kept me going. It was no different as I entered yet another lonely period of my life. This one totally unexpected when my wife passed away with no warning suddenly at the age of fifty. 

Rather than stay at home every night with my dogs, I packed them up and headed out to one of my favorite venues, dressed as my feminine self. My problem was I knew I would be attracting attention as a single woman where I went so I had to be careful. I was not in anyway trying to pick anyone up. On the other hand, I did not want to be ridiculed. Ironically the venues I chose to go to I had gone to as a guy to check out to see if my feminine self would be safe. Once I decided they were, I started dating my new self there, 

As it turned out, I couldn't stay by myself long. I started to interact with other people if I wanted to or not. First I had to learn how to communicate with the world as my authentic self. It was quite the growing process but surprisingly an easy one. Because it felt so natural. I wondered why it took me so long to do it. I fortunately became on speaking terms with one of the bar tenders at a venue I was going to. In turn she introduced me to her Mother (lesbian) and we hit it off. Then, there was the night another woman came into and ordered a to go order and in the meantime slid me a note down the bar showing interest in me. Over a relatively short space of time, the three of us became party buddies and I didn't have to worry about spending nights alone. What happened was, once I finally freed up my inner girl, she established herself in the world fairly quickly. 

Dating myself proved to be a process which taught me a lot in a short period of time. But again I have several other women to thank for my journey. I learned so much from Liz, Kim, Nikki and Hope on how to socialize myself successfully as a woman. In all of their own ways, they were strong, successful women in their own rights. By allowing me to tag along, I learned so much about my true self. Most importantly, they looked past my gender issues and saw the real me. They built me into the woman I am today. So much so, I can't imagine dating myself ever again.  

Medicine and the Speed Wrench

For years the mere thought of the comment "Take your medicine" had negative connotations. From Mom's not so pleasant reminders to meetings with bosses over the years following terrible sales or profit periods.

Now the whole idea is not so negative as I am finally back into my HRT groove. Again I'm busy lining up all the little guys, aided by different shapes, sizes and colors. A few, I wonder if I can even swallow and others are so small I can barely believe they do anything at all.  Plus the really good news is I can afford any of it at all.

Ironically,  my biggest struggles now are the containers themselves.  I almost had to take a screwdriver and speed wrench (hammer) to a very tough little pill container which looked like one of the old birth control containers. All in all a very male response to a very female problem.  But then I did calm down and actually read the instructions, figured it out and opened it correctly.  Maybe the hormones or socialization is working?

It's true that life is a circle from birth to death.  Perhaps the transgender circle isn't perfectly round? If it isn't, I can fix that.  Get me my "speed wrench! No, bring me the small one. The original one became entirely too heavy!

"Taking my medicine" must be working!

Socializing

When I really started to learn what a feminine existence was all about, I went through several learning experiences early in the process.
Of course I learned my IQ dropped with men , I didn't know what I was talking about and people quit listening to me. Truth of the matter is everyone pretty much knows all of that.
What I was searching for was more of a true feminine socialization process. Such as:
What do genetic females really think about the world around them? Sure, a certain segment of the female population are victims. They want to blame men or whomever for their so called station in life.
I never felt I was a victim because I was transgender and I wanted to learn from genetic women who weren't victims either.
I ran across such a site and thought I would pass it along to you.
It's called xoJane .. Go here to it check out!

Transgender and your Bucket

Is your bucket list half empty or half full? Certainly before we all know it and we are fortunate enough to make it- it's time to start looking ahead to the force calling your number. Poof! "You be Gone!"
I started my transgender Bucket List approximately five years ago. I began to see how much living I could do as a woman or maybe I should say- a trans woman.
I found I could live and more importantly wanted to live as my chosen gender. Ironically I got hammered from within the trans community for waiting so long. Even being called just "another old guy on hormones". The big bad outside world on occasion was more accepting.
To make a long story short, my bucket became very full.
Here's my point: I could have made the move to a full time feminine existence two very specific times in my life-basically at the age of 30 and 40 and didn't. If you are younger (I'm 62 now) and considering the move, I can say time will slip by before you know it.
I can't and won't tell anyone to transition but I do recommend checking the waters if you can. It just confuses me when someone writes me or I read somewhere a person is going to try to go through SRS without living the life! It's a problem created by places like Thailand who really don't care about much more than the cash.
Sure it takes quite a bit of courage and a whole lot of trial and error to experience the feminine socialization process.
Don't think you have to be old to have a bucket list. Do think you don't want to be living a regret later in your life when the bucket has a huge hole in it.
I've known fully changed transsexuals and cross dressers justifying life in the closet who have gotten really bitter over the experience.
Certainly, we all have only one life to live and we all have responsibilities to others.
Just as certainly we all have the responsibility to be true to ourselves.  You may consider starting a transgender bucket list to discover what your truth might be.