On A Gender Vacation

 

Image from PR Media 
on Ubsplash.

As I matured as a person and a crossdresser, taking a vacation from my male gender became a reality for me.

It all started when I first felt the inclination to try on articles of my mom’s clothing and moved on from there. Very soon, I spent as much time as I could in front of the family’s full-length hallway mirror imagining myself as one of the pretty girls I envied so much. Before my unwanted male puberty set in, I did not have so far to go to be on vacation from my boyhood self. Then the changes set in and I began to develop the body angles and shape of a man as the girls around me were showing off their new curves in pretty clothes.

At that point, vacations became harder to earn, as it was becoming more difficult for me to look like a girl at all and try to work my way around having no knowledge of makeup at all. That chapter of my transgender notebook (like all the others) was empty, and I struggled not to look like a clown in drag at the circus. In a very short time, I became aware that if I was to ever reach my dream of living my life as a transgender woman, I had a long, hard struggle ahead.

It did not make matters any easier when I went on family vacations and saw other girls my age in cars on the highway. One young dark-haired beauty still stands out as one I remember. As I saw her time and time again when we passed on the highway, I so wanted to be like her and put my pillow over my head and pretended to sleep. No imagined vacation for me on the real one. My gender reality was with me all the time.

One way or another as life went on, I needed to do something to survive. Somehow, I needed to break through the bonds of the increasingly complex male life I was living and start to carve out a new transfeminine existence on my own. If my reality was indeed female, I would have to do something about it. What I did was begin to mix business with pleasure on my vacation. Business was when I was learning that ciswomen ran the world I wanted into and pleasure was when I was able to finally blend in until I was allowed behind the invisible but so real gender curtain.  To maintain the lifestyle, I was trying to lead, I needed to do a lot of research and repetition to see if I wanted to be there at all. Those were the nights when I broke away from all the gay venues I was going to and started to see if I could be accepted in lesbian and straight places.

The vacations I took into the world as a new transgender woman turned out to be life changing for me. For once, I did not have to wonder what if would be like to live in the world as a woman and just do it. My time away from my old boring male world, took me into a wonderful new life as the woman I always wanted to be. I was the trans woman at the big sports bar enjoying my large beer as I watched my sports teams play on the big screen televisions. Occasionally, I received some pushback from a toxic man, but it was not enough to deter me from having a good time. Mainly, because of my confidence in who I was building every time I was successful trying out the me, I always should have been. I was not building anything new, just allowing my true self to flourish in the world.

At that point, it occurred to me that my vacations were changing drastically. Instead of believing I was taking vacations from my male self as a trans woman, I was now taking time from my feminine world to allow my male self to finish up important things such as working and keeping up a false image of a man for the world to see until I could fully complete my male to female transition. Since I had accumulated so much male baggage over the years, clean up was not going to be easy. Finally, it occurred to me that transitioning to my new life was going to be an all or nothing proposition…or was it?

A big decision I needed to make was involving my sexuality which had never been a question for me in my male life as I had never been physically attracted to another man ever. It did not help me when I got a suggestion from ciswomen to buy bananas to get ready for a new sex life that never came. Even though I had dates with several cismen, nothing ever sparked within me and we never went anywhere except kissing, Women, on the other hand were different as I still cherished their company which I found they enjoyed mine too as they went on vacation with me. Since HRT hormones took away any possibly of traditional sexual intercourse between me and another woman, by choice I took it off the table.

It all led me to wonder what I would do about sports, the one big passion left in my life. Could I still interact with the world as a passionate sports loving woman or would I have to give it all up. It turned out that no, I did not have to give up my passion, it just changed direction like so many other things in my life. For example, when my lesbian friends and I were talking sports, we did it on an equal footing. But when I talked sports with a man, often I needed to take a back seat to his sports knowledge even though I had plenty of my own. I learned my lessons and moved on.

Even though many of my vacations from life were just quick, cheap escapes, many were extensive, expensive paths to my future life. Plus, they handed out much needed respites for my often-battered mental health as I battled depression and anxiety. It all helped me to survive and make it to my dream goal I never thought I could make it to. A life as a transgender woman.

As always, thanks for not taking a vacation to read and comment on my posts. Your input always means a lot to me!

 

 

If You Don't Try...You Will Never Get There

 

Image from Luis Villasmil
on UnSplash

During our lives as transgender women and transgender men, we come to many obstacles that we have no idea of how we are ever going to get around.

After many early failures in my unwanted life as a boy, it was increasingly evident to me that if I did not attempt to try harder being a girl, I would never have a chance of making it to my dream. In many ways I was stuck between a gender rock and a hard place. On one hand, I was running to hide behind any failures I might have with my dresses and makeup, and on the other, I was making myself afraid to try anything new at all.

It took me years to learn that if you don’t venture into the world outside of your little closet, nothing will be gained. I discovered after I went through male puberty, I had very little to start with as far as having any natural feminine characteristics to work with. Even still, until I got out of the mirror and into the public’s eye, I had no idea of how bumpy my gender path would be.

In the early days, my male ego took it badly and my female ego was hurt deeply when I was laughed at in public. Until I began to take matters into my own hands. In order to improve my feminine presentation, I went on a crash diet which enabled me to fit into and purchase more stylish fashion. I learned to be in the right place at the right time if I really wanted to try to blend in with the ciswomen who ran the world, I wanted to be in. It took time to try more extreme transgender bucket list items I had put together to learn how it would be to live in a woman’s world if I had to try hard enough.

It was about that time that I landed a job with a very successful casual dining restaurant chain who taught me a lot about not being a victim and if I did not try to succeed I wouldn’t. In essence the chain took what I had learned about myself in the military and improved it. Which was just what I needed to take the gender box I was stuck in and find my way out. What I discovered was that most of the world did not care anything about me once I began to learn the basics of not drawing undue attention to myself. Setting me up to try more and more gender trials on my own. Because I had no one else to help me. The mistakes I was making and learning from came from the fact that my gender workbook was blank and the women I could share my secret with left me on my own to learn my own lessons and be a better transgender woman. Once I figured out what that was and how I fit in with the terminology.

It turned out the only ciswoman with any access to me was my second wife who, for the most part, left me alone with my struggles. Only stepping in when I made mistakes causing huge fights. The problem became I had very little public output for my desire to work the world as a trans woman. I became very frustrated and depressed when I had no way to get out and live because deep down, I knew I was on the right path, and I just had to keep on trying. My only regret now is that I would have taken the steps sooner to be myself and not dragged my wife and I through all the torment I was putting us through.

It was not until she passed away, did I find my path again and began to try to actively carve out a life as a trans woman. In order to do it, I needed to have the confidence of my gender convictions that I had never had in the past. For once, I had few other distractions to slow me down and it seemed everyday I was learning and making progress towards a gender dream which had seemed so unlikely in my past. And, for once, I was not doing it on my own as I slowly build a small circle of ciswomen friends to do it. They were able to teach me more about womanhood than they ever knew as they allowed me behind the gender curtain into their world as lesbian women. Somehow, my male baggage which helped me was kept such as my basic mistrust of men since I had been forced into their circles in my life and the fact I could fit in with them image-wise because I was largely a tomboy in my tight jeans and boots.

Through it all, there were a couple of other things I needed to try to improve my world as a transfeminine person. The first was attempting to see if I was healthy enough to be approved for gender affirming hormones or HRT. I was and my life improved dramatically as I took on more and more feminine characteristics. The process was so easy, it was as if my body was saying what took me so long for such an important move. The other was the move initiated by my therapist’s permission at the Veterans Administration to have most of my legal gender markers changed. It was the best Christmas gift I ever received when I saw a judge and received my formal name change approval on Christmas Eve which got the ball rolling towards securing a new driver’s license, Social Security Card and getting my VA paperwork changed over. To the gender I always should have been.

I would never have made it through all the dark gender moments in my life. Especially with the added problems of depression and anxiety I had if I had not made it through and kept on trying to reach my dream of being allowed to live fulltime as a transgender woman. It was certainly touch and go until destiny stepped in and helped me along by pushing me back out into the world until I found other women to socialize with. I even played the online dating game and won after sorting through an enormous amount of trash, my wife Liz found me fourteen years ago and have been together ever since. If I had played my old victim cards, there would have been no way I could have ever made it out into the world.

I learned firsthand, if you never try, you will never make it to your dream.

 

 

The Consequences of Giving Up

 

Image from fast glass fx 
on UnSplash.

When I considered “purging” (getting rid of all my feminine makeup and clothing) the consequences felt like a double-edged sword.

For a few days, the pressure around gender lifted, and I had one less major worry. But before long, the familiar desire to live as a girl returned to my everyday life. I realized that cross-dressing—and perhaps something beyond it—would not be easy for me to give up. Even in that short time, I had learned a great deal and understood how far I still had to go before reaching my dream of living full time as a transgender woman. I was not even sure whether I could make it happen.

Then there were the brief moments of gender euphoria. The time I spent hiding from my brother and family was enough to keep me going until male puberty—and what felt like testosterone poisoning set in. I was unhappy that my body was becoming more angular while the girls around me were developing curves, but there was nothing I could do to stop it.

Even as those changes continued, I could not face the consequences of giving up. I learned to take what I could get until I was old enough to leave the mirror and closet behind and explore the world. What happened next was brutal. I discovered that the mirror had been lying to me when it suggested I looked like an attractive woman. If that were true, why was I laughed at so often when I tried to go to ordinary places, such as nearby shopping malls? Eventually, my frustration pushed me to look around and notice how most of the cisgender women I saw were dressed. Even if it meant adopting the casual styles I dreaded, I knew I needed to do it to blend in and be accepted.

The more acceptance I gained, the harder it became to return to my old life and face the thought of giving up on my dream. For the first time, I even felt excited about where my future might lead. I just had the glimmer of hope that I might be able to make it to the transfeminine life I always wanted to lead.

At that point, my male life began to creep in with a vengeance. He was becoming very successful with a small family and good job and the risk of giving it all up loomed large over everything I did. Not a day went by when I didn’t consider the consequences of what I was doing. I always say, I wish I could get back just a fraction of the time I wasted worrying about how I would be living my life if I was a woman. What would become of me if I jumped off my gender cliff for good.

What I decided to do was experiment in the world as a trans woman. My second wife called me a “terrible woman” because I had never paid any dues that ciswomen pay, and all I was concerned about was my appearance. I knew deep down she was right but I still at that point did not know how to fix the problem by paying my dues as a novice feminine person in the world. It was like if you are applying for a job, the employer says you don’t have enough experience but will not give you the job so you can get it.  I am sure my wife was right about my feminine knowledge, but I was having an impossible time getting behind the gender curtain to learn more.

As I slowly got behind the gender curtain, the consequences of giving up almost completely went away. Why would I abandon all the effort I put into being a complex transgender woman and throw it all away during a time when I was finally being successful. For a change, I was the one making sense in a gender situation which very few understood.  No longer could I be accused of being a terrible woman as I matured into my new self when I was allowed into women’s only spaces. Sure, I was still making mistakes, but they were getting smaller and smaller as time went on.

The mistakes I usually made came from when I miscalculated how complex a ciswoman’s life really was and how far I needed to go to be allowed to fit in. To eliminate all my mistakes, I needed to give up all the negative consequences of a male to female gender transition and just make the plunge. Fortunately for me, the water was not that cold, and I jumped into the deep end of the gender pool. Plus, I can never forget the soft feminine gender hands which helped me to survive the impact into the water.

I know many of are thinking seriously of making your own gender plunge and what would be the consequences of possibly losing everything you hold dear in the world. I know advice is easy to give, but the turning point for me always was how natural I felt as a transfeminine person. Something kept telling me I was born the way I ended up. And with some effort, I made it to where I always needed (not wanted) to be. Hopefully, that is a starting point for you too and the consequences of giving up become too much to consider.

If you are further along, I am sure you recognize the consequences of never giving up and somedays even being perceived as being selfish. As I was when I was headed all out to fully transition into a transgender woman, all I could think of how fast I could make it to my goal. So, I am guilty as charged. It is probably the reason my second wife called me a terrible woman. In all fairness to me, I did mature out of it and found my way into a better world.

All the purges in the world did not work for me and I put up with all the consequences I lived through. I am not a gambler, but in this instance, I played the odds and won.

 

 

 

 

 

 

Memories or a Dream?

Image from Ian Dooley
on UnSplash

Too many times, when I went out into the world for the first time as a new transgender woman, I wondered if I was making a memory or living a dream.

Sadly, most of the time I was working so hard to succeed for the first time in a new exciting world, I did not have the time to know if I was making memories or working my way towards a lifetime dream. There was simply not enough time to do all I wanted to do, such as present well enough to blend in with the ciswomen around me. It was like I was driving a new car, and I did not know all the new features I was trying to master. How was I ever going to stop being a man with all the male looks such as a scowl and how I walked and turn myself into a pleasant looking feminine person as I camouflaged all the testosterone damages male puberty had caused me.

There turned out to be a way after I worked my way through not dressing like a teen girl which just drew negative attention to me. Certainly, creating more negative memories than positive ones and my dream of living as a full-time transfeminine person, remained just that. A far-off dream. At first, I had many memories to make and learn from as I followed my dark and lonely gender path. Perhaps my biggest problems came when I realized I was trying too hard when it came to expressing my own brand of feminization because I was working so hard to catch up with my own gender workbook and decide where I wanted to be.

The only dreams I was having during this time of my life were the rare occasions when I went to sleep and dreamed that I was the attractive woman I always wanted to be and the pressure was off to look a certain way as a woman which I had always lived with. I was obsessed with trying to try any beauty secret I could to improve my appearance in the world. This obsession very much was with me until I began to settle into my own beauty routine

 The dream took a giant step towards materializing when my daughter took me to her up-scale beauty/salon and spa to color and style my hair for the first time when it had grown long enough to do it. Even though I was scared beyond belief to do it, I knew this was a golden opportunity to go behind the gender curtain into a female dominated space I had never dreamed of going before. It was amazing as I wrote about several posts ago, and I knew right then why ciswomen were so adamant about having their hair done a certain way. I could not wait until I could scrape up the extra money so I could afford to go back. Plus, with my new hair, there was no way I could keep on presenting male in the world as I knew it.

I was so obsessed with putting myself out into the world, I needed to think of different ways to do it and build more memories such as when I started to meet the ciswomen and lesbians who would form my circle of friends and help me slip across the gender border and behind the gender curtain where I desperately dreamed of being.

At this point, I always mention the good and the bad that happened to me along the way to validating myself as a transgender woman. It took a lot of confidence I didn’t have to make it happen. Too many nights of rejection when I attempted to push the gender envelope too far and was sent home in tears with my new dreams shattered. When it did happen, I needed to rely on my deepest inner feminine self to assure me everything would be OK and these were just memories which happened to be unpleasant to add to my dream. She told me that the roughest dreams you ever had are the ones you had to work extra hard to achieve.

Sooner more than later, I began to have more pleasant memories than bad ones and my ultimate dream again began to come into focus. If I tried hard enough to accomplish all my feminine goals, I could join the others ahead of me in the transgender community I was familiar with and leave my male past behind me forever.

Surely, there is a big difference between memories and dreams. I consider memories a less than physical form of dreams. Meaning memories are easier to come by and dreams are something a human should always have to keep their lives headed in a more positive direction.

Depending upon where you are on your gender path, maybe you are just in the dream phase of where you want to be and that is fine. It is when you begin to build memories of your journey do you start to build the blocks you will need to make it through. During Pride month, no matter what you may read from haters, TERF’s and bigots, you should be proud of the gender dreams you have.

You are worth it and often there are more silent allies and developing transgender women and transgender men that you know who are ready to join society. Just look at your memories and dreams as what you had to go through to arrive where you are today. Someday you may be able to become that confident trans woman you only were when you were asleep.

When it comes right down to it, it does not matter if you are clinging to memories (past and present you are making) or the life you are dreaming of living, The most important thing is the self-love you are able to give yourself. Without it, you have a difficult time loving anyone else.

Thanks for reading along with me and thinking of your own memories and dreams. Any of your comments are always appreciated!

 

My Life's Passion

JJ Hart on vacation
last winter. 

Without a doubt, the one passion which has consumed my life the most has been my desire to be a woman.

I continually write about my youth as a confused boy wondering if I was the only boy in the world who wanted to be a girl. My desires extended all the way to what I wanted for Christmas (the doll baby I never got) all the way to when I lied about what I wanted to be when I grew up. Rather than rock the boat I always said some sort of a male profession such as a doctor or a lawyer rather than what I really wanted to be, a woman.

All I could do was take refuge in my mirror which told me I made a pretty girl out of the boy I was at the time. It became a passion for me to use as much of my free time as possible to cross-dress. At the same time, I became really good at acting like a boy by playing sports and having an interest in cars. I was so good, it kept the bullies away until male puberty invaded my body. Outside of hating the changes puberty was making to my body, I remember being intensely aware of my new masculinity and what to do with it. Even walking like a man was a chore for me to learn to do. I was so afraid of walking like a “sissy” and be made fun of by the bullies that I feared what to do. Little did I know that later in life my passion would be to unlearn all that I needed to learn at the time about being masculine.

As much as I tried and as tormented, I because of my gender passions, I could not seem to lose my desire to be feminine over my hated male image. At the time, I was in the midst of what I call the information “dark ages” before the internet and any social media input. Even the word transvestite was new to me as I struggled to find my footing in life. In other words, my gender closet was very dark and lonely, with little opportunity to have any future at all in my passion to understand and be feminine.

I stayed that way until I grew older and my passion included receiving my cherished issues of “Transvestia” magazine and I could read the “wisdom” of “Virginia Prince” whenever I could get my hands on another issue. For a while I thought it was working until I began to read about the social mixers certain chapters had to meet and greet other cross-dressers or transsexuals as they were known back in those days. Amazingly, one of the chapters in my native Ohio held mixers on a fairly regular basis that I could attend. I thought for sure, meeting others with similar gender issues could help me but I was wrong. Their passions exposed the many layers of where I could fit in (or not) with the remainder of the cross-dressing community and at the least, I hoped I could come away from the social by making a friend or two.

The only thing that really came out of the mixers was the knowledge that another chapter was coming close to establishing their own socials in Columbus, Ohio which was vastly closer for me to attend. Maybe I was too standoffish or even shy to make what I would call friends, but I continued to keep going any way and even was rewarded with invitations to smaller more diverse parties in Columbus which did not have to supposedly adhere to all of “Virginia Prince’s” archaic rules such as admitting heterosexual members only. As I said, the parties I went to were very diverse from lesbians to cross dresser admirers all the way to transgender women getting ready for gender realignment surgeries. The learning process I went through every time I went fueled my passion to learn more about my place in this new exciting world, I was becoming a part of. I could not wait to be invited to the next party.

I felt so secure from my party experiences, that I decided to do more exploring in my own in public. That is when I began to seek out the straight venues I used to go to as a man when I always wondered what it would be like to experience them as a woman. My passion for my new life exploded when I discovered I could be accepted which kept me out of the gay venues which I did not feel comfortable in at all. I was able to go out to be alone and mostly socialize by myself for the most part as I worked hard on my passion to fill out my gender workbook which was seriously lagging behind my fast-paced life as a novice transgender woman.

By this time, I had decided I had made the right decision to follow my feminine passion and try to survive in a world run by ciswomen. My path felt natural and I was rapidly coming close to the time when I was going to push all my male privileges I had earned to the middle of the table and bet my life on the transfeminine path I was on. I could not believe that my entire life’s dream/goal was suddenly within my grasp. If only I had the courage to finally follow through on my passion.

I did follow through and with the help of my future wife Liz, I went on HRT, threw out or gave away all my male clothes and never looked back on my male life except to decide which baggage to bring with me. I even went as far as taking female vocal lessons to try to teach me all important feminine communication skills which I desperately needed. It all turned out to be a labor of love as I listened and learned from the world around me.

The boy so long ago in the mirror finally had his deep-seated passions rewarded.