Showing posts with label envy. Show all posts
Showing posts with label envy. Show all posts

Thursday, May 28, 2026

She Was Living Rent Free in my Head

 

Image from Nathan Dumlao
on UnSplash.


It took me years to realize that I had a tenant living rent free in my head all along.

I should have known from day one when I was going through my mom’s clothing that she was here to stay. In fact, she increasingly demanded more and more space in my head to justify her life as a cross-dresser or transvestite as we were called back then. I would need to wait several years for the transgender term to even become popular in our gender diverse society.

Also very early, I realized that the small closet I gave her to exist in just was not going to be enough. When she succeeded in expressing herself in the world in the smallest of occasions, she wanted to increase her space in my head. Prime examples were the days in school during study halls when I should have been actually studying. But I wasn’t as if I was having too much fun envying the girls around me who I desperately wanted to be like the next time I had the rare chance to be by myself and cross-dressed as a pretty girl in the mirror. And I realized I did not want them sexually as much as I wanted to be them physically and mentally.

It was during that portion of my life that I completely did not have any idea of how much rent-free space my evolving trans woman needed for her share of my head. Now I want back all the time my male self-spent fighting her for my life as I lived it. The gender ripping and tearing was certainly no fun, as both genders in my head fought for their right to survive. For awhile I tried the old male fallback of just try to ignore my number one problem in my life and she would somehow just disappear. When, in fact, the opposite was happening. The thrill of putting on a dress, hose and makeup would go away, and in its place, I would have a deep-seated feeling of just doing what was coming to be just natural for me. It was increasingly evident that I would need more space for my rent-free tenant to operate in as she went out to explore the world as a novice transfeminine person.

Following more than a few rough patches when she was going out in the world, my woman began to understand the sacrifice of her male ways it would take to survive. She became more serious and began to work on the basics such as presenting herself convincingly in the world. I went on a crash diet and succeeded in taking off enough weight so I could go down a size or two in the world of women’s fashion and I could find and wear stylish clothes for a change. Along with that major move, I began to take extra better care of my skin. Using a good moisturizer following every shave. Which paid off by not having to use so much foundation makeup and I could look so much more natural as if I was not trying so hard to look like an attractive woman. The trips I started to make to the department store makeup counters for guidance certainly did not hurt my progress either.

I was learning the hard way that I could not cut any corners if I was to be successful in my quest to present successfully in a world of curious ciswomen. I needed to give my rent-free tenant the opportunity to expand her space in my head and the finances to do it. I would be spotted a mile away as a man trying to be a woman if I used cheap makeup and did not do my best to shop for (and try on) clothes that fit me and even flatter my testosterone poisoned figure that I could do very little about. I did learn from my observations of the ciswomen around me that there were women of every shape and size that I could copy from and be successful. Which gave me the positive energy to carry on and pass as a trans woman friend of mine said, “Out of sheer will power.”

Even though the progress of my rent-free tenant was not moving along as fast as she wanted, there were still major obstacles in my way to deal with. Such as what would happen to my twenty-five-year marriage, my relationship with my daughter and the problem of finding a new job as a trans woman in the world. To be sure, all were major obstacles to deal with, so my tenant would have to be patient as she was beginning to understand she was the only tenant left in my head with any power. My male self was just going through the motions of life to keep a job and the outwardly show of male privilege in my life.

Finally, it was time to go on gender affirming hormones and allow my tenants to switch places. My previous rent-free tenant had earned her right to live as the dominant person in my life and my male self was left to pick up the pieces. I should say baggage more than pieces, because that is what he left me to consider in my new feminine life as a fulltime transgender woman. It was difficult to do, but I was able to keep several of my main male building blocks of my life such as my will to succeed and a deep-seated desire to bring my hobbies with me such as my love of sports. Which I learned was alright when I made ciswomen friends with the same passion for sports that I had built up over the years of my life.

While I certainly would not recommend a life like mine to anyone. Letting someone live rent free in your head for all those years was never easy. Perhaps, the only positive was, having all that time to learn the world as a trans woman gave me a stable basis to work from. That is my excuse, and I am sticking to it.

 

 

Wednesday, January 31, 2024

Jealousy Issues

Image from the Jessie Hart 
Archives.

Many times during my life, my relationship with women or even girls went from being envious all the way to being out and out jealous. Christmas was a prime example when I had to sit back and watch my girl cousins in their pretty new dresses and outfits while I was stuck in my boring shirt and tie feeling something like a stuffed sausage. Not to mention the gifts they received versus my unwanted boy toys. The best I could hope for was to receive a small amount of cash for a gift which I could use to sneak out and buy me makeup or other feminine items.

When I was younger, I always held out the hope my life would change for the better but it never did around women until much later. 

In middle school when the puberty hormones began to kick in for both genders, my feelings of jealousy began to increase also. Here I was developing unwanted angles to my body as well as extra facial hair while the girls around me were gaining curves was sometimes unbearable. Testosterone poisoning was ruining my life and every night I would go to sleep wishing I could wake up with all the attributes the girls around me had. Of course that never happened and life went on the best as possible.

On top of all my other gender envy, the Vietnam War began to be a very real risk for me. Spending time in the military away from my all too brief cross dressing time in front of the mirror was a reality I never wanted to face, until I did. In addition, how fair was it, the women around me never had to face such a bump in the road? I kept thinking why me until I was drafted and went ahead and served my time in the military the same as my Dad before me and as my friends around me. Tragically, I knew a few friends who only returned in boxes. Proving death was a very real threat.

Even though I was still very jealous of the women around me, I attempted to channel my envy in a positive manner. I say try because I know now looking back how I failed. There were so many times, I didn't bother to notice or take the effort to mention how attractive my wife looked. All the time I knew how insecure she was and I should have stepped up to help her, more than I ever did. Looking back, I was too jealous of her because she was living the life I wanted to live. Then she was gone (passed away) and I never had the chance to recoup my losses. 

In place of my jealousy issues, I tried my best to learn more and more about a woman's real life and why I never should have been as envious or jealous as I became. I never took a moment to stop and realize the other gender grass wasn't always as green as I thought it was. As I pursued a life as a transgender woman on gender affirming hormones, I discovered a new world beyond one with all the white male privileges I took for granted. Such as just having a portion of my daily respect automatically given to me because of my gender. The main privileges were job advancement and personal security. 

Cis-women on the other hand have to go through the intense hormonal changes their body goes through to prepare them for possible motherhood. Periods and later on, menopause are just a few of the problems women have to face more dramatically than men. I always thought too, it would have been better to have been the gender which was the prettier one as well as the pursued one as men always needed to be the one to ask someone out. I so badly wanted to be the one who was invited which was partially because I was always so shy around women or girls. 

Fortunately I don't think my jealousy issues ever reached a toxic level. More or less I just retreated into my gender shell and hoped for a better day to come. Which it did when at the age of sixty I finally came out full time as a transgender woman. After a lifetime of studying women, I think I took the shorter path to my gender freedom, while at the same time putting all of my gender envy behind me. In many ways each of the binary genders has their own weights to bear as they go through life. 

The best we can hope for is, the process makes us stronger. 

  

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