Showing posts with label adolescence cross dresser. Show all posts
Showing posts with label adolescence cross dresser. Show all posts

Saturday, October 19, 2024

How Far will You Go?

Image from UnSplash.


I have always viewed my transgender journey as a series of upward steps. A few of the steps were short and easy to take, while others were the opposite. The steps seemed to be impossibly steep and dangerous to proceed. 

Early steps were thrilling and even exciting as I snuck behind my family's back to cross dress in front of the mirror. Even so, the risk of discovery was anything but easy because I was risking so much. In those days, discovery meant a trip to a therapist who knew nothing about gender issues and even worse being treated as if I was mentally ill. 

At that point, looking ahead, I probably knew deep down, things would not get any easier with my gender issues. But, time would tell. As I progressed during my life, it suddenly became obvious  my gender issues were not going to go away. In fact, they were only to become much more serious. Mainly because my male life was becoming so much more serious too. Once I made it through my military service, I settled in to raising my new, small family which I hoped somehow would make me more of a man, while deep down I knew it would never be the case. I wondered how far I would have to go to carve out a good life. 

Fortunately, I was able to even though the trip was difficult, I made it by deciding I would go as far as I needed to go to satisfy living as my feminine authentic self. Initially, I had several major hurdles to conquer. Such as, did I want major surgeries which were much rarer and expensive back in those days as well as how my sexuality would play out as my new self. 

Since I did not have any insurance to cover the surgeries, paying for them was out of the question so I moved on. Next was my sexuality. Since I had absolutely no experience in sexual time with men, I did not know how it would go. It turned out, I did not need to experience much time with me, I never had to move on from my sexuality with women. I was becoming a transgender lesbian. 

Of course, the further I progressed in my new world, the more I had to lose as far as family, friends and employment. I needed to prepare to lose it all if I needed to. I needed to determine if it all would be worth it. In my case, all the years of fear and struggle proved to be worth it. Thanks to my lesbian wife Liz, I was accepted for who I was. 

To arrive here, I did not have to go through extensive operations and change my sexuality. I have always thought gender was between the ears and not the legs so it did not matter to me. I guess it proves how diverse the transgender community is, if we allow it to be. None of the "I'm more trans than you" syndrome which is hurtful to us all. Especially now, in a political environment which is setting out to erase the trans population, we ALL need to be united and not divided behind a bunch of archaic labels, such as cross dresser and transsexual individuals. 

Regardless of the label, we all had to decide how far we want to go to satisfy our gender urges. Or sadly, how many risks did we want to take to change our life forever. It all proves how we never had a choice in who we are as transphobes seem to think we do. How far you go is entirely a personal decision which takes a lot of work and trial and error to accomplish. It' all depends how in depth you want to go. For example, the night I went out to see if I could meet and blend in with other single women on their own turf and survive. I did make it and knew I could never go back to the life I had before in the mirror. I wanted to go more in-depth. 

From then on, I needed the confidence to do it.

Wednesday, October 16, 2024

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. 

Wednesday, March 27, 2024

Transgender Plan B?

A Bright Idea from Diego PH
on UnSplash


In life, did you ever have to come up with a new plan if the one you were working on didn't work?

In my life, I had many "Plan B's" because I didn't think things out before I did them. A prime example was when I was engaging in all the cross dressing I was doing in front of the mirror when I was very young. If the truth be known, I didn't know what I would do if I was caught. Except to lie and promise to never do it again. Plus, what if I was caught shopping for makeup in a downtown department store close to where my Dad worked. In the vacuum I lived in, I just plowed blindly ahead, hoping for the best and expecting the worst never happened. Which it never did.

I suppose I always thought there was a "Plan B" somewhere if I was discovered. Somehow I would magically give up on my dream and keep marching ahead in a male world. In reality or not, I always thought there had to be some sort of back up if I failed at anything. There was always going to be another chance to put on a dress and apply makeup if I was careful. 

The first time I encountered a situation where the only back up plan was applying myself in the system was when I enlisted in the Army during the Vietnam War to evade the draft. When I went through the human machine called basic training, the threat of failure was real. The drill sergeants made it clear if you failed at something you could be recycled back to the beginning and have to start all over again. No one wanted to face that "Plan B." The result of going through basic built my confidence in that if I was forced into a situation I certainly did not want to be, I could still survive. The main problem I had was I couldn't (of course) cross dress at all and had to put my gender issues aside. During the several years which occurred before I could indulge in cross dressing again, my back up plan was to do quite a lot of daydreaming about when I finished my military service and could resume my life as I had lived it before. 

When I did finish, I found myself needing a whole new set of "Plan B''s." What happened was, I started to go all out at Halloween parties dressed as a woman. Where I learned the basics of surviving in a new exciting world as I was slowly growing up as a novice transgender woman, which was my dream. Of course the problem was Halloween only came around once a year and what was I going to do the rest of the time about my gender dysphoria. What I decided to do was sneak out of the house and into the world as my new transgender self. When I did it, I needed plenty of "Plan B's" if I was caught. My rule of thumb was to be as careful as I could and deny anything which happened if I was caught by my second wife. Not the best plan. 

As my femininization presentation improved, I found I needed a whole new plan to survive in the world as my authentic self. Primarily I needed a way to communicate with women I was meeting who were curious why I was in their world. Initially, I tried to mimic who I was talking to as far as using their vocal pitch and then even moved on to taking voice lessons to sound more like a woman. Finally, I moved to a point where I was half way comfortable with the way I sounded and I did the best I could.

I am biased of course but I feel the back up plans we transgender women or trans men face are far more impactful than those of the average person. We trans folk often face the possibility of losing almost everything as the "Plan B" we have when we enter the world. All too often, I read the sad, tragic stories of trans women losing their entire families, jobs and even friends when they made their way out of the closet. 

Hopefully, in the future, society will come around and we won't have to rely on severe "Plan B's" to survive.

Saturday, August 7, 2021

The "Flip" Side

Liz and I at Cincinnati Pride 
 The second part of my post I started recently which mentioned  being envious of missing the life I lived as a young boy who desperately wanted to be a girl.

All in all, my story isn't much different from most of yours. Where we all differ is how far we went to conceal hiding our authentic selves in the closet.


During my youth in the 1950's, information on any or all gender differences was out of reach to me. I felt all alone. I wanted a doll for Christmas, not the BB gun I was gifted  As it turned out, Christmas was just the beginning of my problems, Another example I remember like it was yesterday was when our family was on a vacation to Ontario Canada from Ohio. One day, as the trip was at it's most boring we pulled up even and passed a car in which a young dark haired girl approximately my age was riding. Almost immediately I wanted so bad to be her. So badly I put my pillow over my face and pretended to go to sleep.

My desire to be a girl went far beyond going on vacation. During junior high school (7th thru 9th) grades where I went to school, I ended up setting close to the same girl in many classes and study halls. As I slowly began to develop a crush on her, I started to notice I was somehow different. I didn't desire her sexually at all. I wanted to be her. So much so, I adopted her name when I hid behind my families' back and dressed as a girl, 

Somehow I thought I would outgrow it, the ugly idea the whole idea was some sort of an evil phase. Still, I felt so alone in my cross dressing closet. 

Alone I would stay through high school until I finally shared my not so minor secret to the woman who was destined to be my first finance, In return for a couple nights of passion when she helped be to dress up she later was the person who rejected me when I was drafted and had to go in the Army, At the time the whole process was devastating to me but later turned out to be one of the best happenings of my life. 

Sure I had to put my feminine clothes away for my first two of three years in the military, ironically I was still in the Army when I came out to the first people in my life who accepted me. Including the woman who was to become the mother of my very accepting daughter. 

My life after the Army was an alcoholic blur for years until I slowly realized I was in reality a member of the new transgender group of people. More on that later. 

Mountain of Hope...Mound of Ash

  Image from JJ Hart On occasion when I was following my very long path to transgender womanhood, I did experience enough hope to keep movin...