It Was Never Easy

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 Two things amaze me when people bring up to me when they learn I am transgender. The first is when someone thinks I had a choice and the second is the entire process was at all easy. 

Since I was never a so-called natural feminine person to begin with, I needed to struggle completely to reach my goals of surviving in the public's eye at all as a woman...trans or not. The best description of my passing struggles came when my transgender friend Racquel told me I passed out of sheer will power. I knew what she was trying to say. I wasn't the best looking woman in the room but I was going to force the issue anyhow. 

Early on, I had only the mirror to do my gender battles with. I finally learned too late the mirror often lied to me. Night after night, I would think I looked great only to be immediately stared at or even laughed at in public. It was difficult learning how to try to dress myself so my feminine fashion helped me to live a life I had only dreamed of, not hurt it. At the same time, I tried to lose as much weight as I could and take care of my skin so I could wear less foundation. None of it was easy. But it was worth it.

In order to accomplish all I wanted to do on my difficult gender journey, I needed to learn something new and different. I had to learn to be my own best friend. I never liked my old male self and was just learning all the new possibilities of my feminine inner soul. She had many problems to face as she fought for acceptance from my male self who fought completely for all of his rights. At times, it was an ugly, bloody battle I never want to go through again. It was anything but easy and never a choice to go through as I was to find out later. 

I ended up suffering so much, I almost ended my life several times from various reckless self harm attempts all the way to an attempted death by pills which failed before I decided enough was enough. In order to survive I had to make a choice, so yes I guess I did have a choice and it was a very desperate one. Self survival meant I needed to pursue what measures I could and change my life forever. The final determination was deep down I felt more natural as a transgender woman and needed to find out where I would need to end up in the new pack of women in society. It was then I learned how deeply layered a woman's life could be and perhaps even more so as a trans woman. I had all the extra baggage of my previous life as a man which I carried with me to the other gender side. I knew the male gender expectations men had of women which made me extra shy of the entire gender dance between men and women. Primarily I learned why both genders often have a difficult time communicating in their relationships and wished often I could go back and do my life different. Maybe then, my second wife would have never said I made a terrible woman. Which I did and thought it only had to do with how I looked.

The final example for this post I will use was the amount of time it took me to finally face reality and come out fully as a transgender woman. Adding up the years, I struggled with my ultimate gender issues for nearly a half century. It was certainly difficult to break out of my old male chains and live the life of my dreams. I realized I never had a choice.

You Can't Buy Love

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Jessie Hart Archives

 One of the first lessons I learned when I was first brave enough to date girls was spending more money equaled to more dates with certain girls. Sadly, the plainer the girl, the less potential spending was going to happen. When I flipped my gender, I found out how evil it was.

As a transgender woman, I was or am not the prettiest woman in the room. As such, I never managed to have many dating interactions with men who most of which just saw me as some fetish object. They wanted the first date to be a motel room. I drew the line at any sketchy first dates and demanded a meeting in a public place of my choice. What happened then was a predictable amount of being stood up on possible dates. While I did have a couple meaningful dates with men, often they were unscripted moments in the regular venues I went to often. One night in particular happened with a man called Bob who treated me completely as a woman and I loved it. He lived far away and was married so there was no chance at any further involvement. 

Through that period of my life I was questioning my sexuality also so any dates with men added to my possible knowledge. The farthest I ever went was very brief episodes of heavy petting or making out. From it all, I learned I still preferred the attention and company of women. With the help of a few female friends I learned the meaning of what it meant to be to be a transgender lesbian. In order to do it, I found I didn't have to have a lot of money spent on me to be happy. I was more into spending more money on my feminine self to attempt to improve my public's appearance. I ended up saving every extra penny I had to buy that next extra wig I didn't really need to be more attractive than ever before. At least in my mind. As I acquired more fashion and makeup, slowly but surely was acquiring more acquaintances to try my new fashion out on.   

Which leads me to another woman I don't mention much anymore who is Amy. Amy is the woman who recommended me practice with a banana to get ready for my intimate moments with men. So as you can tell she wasn't shy. One day in particular  with her comes to mind when she invited me over to her house for a spaghetti dinner with friends. I didn't really ask who else was coming, I jumped at the chance to enjoy a home made dinner. Fashion wise, Amy had only seen me in my short denim skirt days, so I decided to wear one over to her house again not thinking who else would be there. It turned out she also invited two men so the group included a cis woman, a transgender woman and two men who were seemingly ill at ease with me. I made the decision to join Amy in the kitchen and serve the men their delicious Italian dinner. I decided if the men were going to be ill at ease with me, I wasn't . I enjoyed the meal, helped clean up the mess, stopped to socialize with Amy and left the men behind. Just another learning experience.

I finally was able to slow down on expenditures on fashion and makeup and spend more on my personal interactions. My experience with dealing with both sides of the binary gender spectrum helped me to truly understand what buying love really meant. I understood both genders often expect intimacy in return for how much money you spend. The last woman I ever dated me as a man suggested to me we go to an expensive steakhouse for food before our first date. I politely saw through what she was up to and declined and we went to a more reasonably priced venue of my choice. Probably dooming our relationship from the beginning. She was quite attractive and a diva to begin with so I figured she thought she could do better than me and our brief fling ended after three or four dates.

Since we live in a money driven society, buying love is hard to do and even more difficult to resist as a transgender woman.  

Following the Path

 

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Jessie Hart
Archives

The path I followed as I chased my gender truth at times turned out to be very difficult. 

It all started with having a very unaccepting family environment and continued from there. Similar to so many of you, I needed to wait for just the right time to pull out my small stash of girls clothes and cross dress. Because of that my available times to dress up and do my best to follow my new path were few and far between. Plus, the signs I desperately were looking for were distant and difficult to read. When I came to gender cross roads, I was having a hard time figuring out which one to follow. 

This was all happening during my pre teen years so I was confused enough about my life to start with. On top of the usual questions kids had growing up, I had added problems wondering what gender I was, all the way to my sexuality. I felt as if I was attracted to girls during puberty but the how I was attracted became the problem. I was facing the sexuality issue of desiring women because I wanted to have sex with them when all I really wanted was to be them. To make matters worse, I was extremely shy around people I didn't know. Especially girls. None of it was making my path any easer to follow.

To make matters worse, when I was in high school, the political powers to be decided to dramatically expand the United States presence in Southeast Asia or the Vietnam War in particular. On top of all my other worries I needed to add possibly being drafted to serve in the military. Not a good feeling to carry with me all those years. How could I possibly serve if I didn't want to be a man at all. It turned out, I didn't have the choice after I stayed in college for four years, I was drafted anyhow and my path became very clouded. 

The best I could, I went down my path adding three years in the Army to my life experiences. At the least, I had more knowledge of the world to base my gender decisions off of. Or, at least I thought so. Not long after I was discharged from the military, I went through the life altering experience of having witnessed the birth of my first and only child, a daughter who turned out to be my biggest supporter to this day.

As I was building a rather successful life as a man, I also began to explore other cross roads on my gender path. Possibly the biggest one was when I started to think of myself as more than just a casual cross dresser and more of the newly minted transgender individual. Most certainly just thinking I was trans rather than a guy in a dress petrified me. To make up for all my gender fears, I did my best to hide my true authentic self from the world. When I did, I kept hitting more and more dead ends on my path. 

Years later, as I was stumbling along attempting to find my way, I sustained so many bumps and bruises I could take it no longer. I made the effort to see a doctor and be approved for HRT and all of a sudden my path became more of a highway to my future. I guess it was more like an interstate as I was able to easily pass more and more milestones on my journey. 

It certainly took me long enough to get to my destination but once I did, it was all worth it.