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
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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.

Gender Migration

 

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From the early days cross dressing in front of the hallway mirror to finally coming out in the world as a transgender woman, I found my gender migrating away from my masculine side. 

The migration was slow at first because my old male self was resisting any and all changes to his existence. It seemed the more I tried to cross dress as a girl, the more he hated the process. The problem quickly became more apparent after I appeared in the mirror as a girl, which would involve or invoke a fast reaction as he responded negatively to anyone else in the world. Family and friends became targets of his gender frustration. Why? Because even though he did not know it, he was fighting an impossible battle. Even though it was possible for him to win the occasional battle, there was no way he could win the entire gender war. My feminine inner soul was just too strong.  Every time she was successful in coming out to the world, she wanted more and more.

Through my life's middle years, advancing in my job and raising my daughter, my migration slowed but never went away. In fact, it showed up in the most inopportune times when I had company business meetings to go to, or a family vacation to act as if I was having a great time when all I wanted to do was go on the vacation as a transgender woman. Of course my wife always sensed I was having a problem and tried her best to pry my thoughts away from me. I became very good at hiding my emotions as any true man would. 

In my case, I found if I waited long enough and tried my best to express my true feminine gender the best I could away from my wife and friends, I could get by. Those were the frustrating migration days of sneaking out behind my wife's back and beginning to establish myself as a woman in the world. At the time, I viewed the entire process of slipping down a very steep and slippery slope which would change my life forever. As much as the process scared me, at the same time I desperately wanted it to succeed. At times, too much when I couldn't keep my mind on which gender I was day to day. I knew I had gone too far when a stranger in my restaurant would refer to me as a woman instead of the macho man I was playing that day. 

Finally, I gave up, started gender affirming hormones and started a totally serious pursuit of a gender migration. From that point onward, I let go of my old unwanted male self and re-entered the world as a transgender woman. As I always point out, friends and family were there for me to enable my final migration to be a successful one. I am not sure I could have done it without them.