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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Stephancik on UnSplash

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. 

Another Holiday?

My Favorite Valentines. Liz on left, daughter 
on right.
From the Jessie Hart Archives.

 Following the Christmas holiday season which presents so many problems for transgender women and men, here comes yet another rather traumatic holiday. 

Both of the holidays revolve around personal relationships, to which trans folk often have lost close friends or family because they set out to live as their authentic selves. When I read all the social media posts from transgender folk who are lonely, my heart goes out to them. The entire process just goes to show how much a person can lose following a gender transition. Once again it shows how much of a choice we don't have when we set out on our gender journeys. 

I am fairly sure I didn't think of losing family the first time I looked at myself cross dressed as a girl in the hallway mirror but then again maybe I did because I was so frightened about getting caught. Maybe my fears were justified so many years later, when I did lose all contact with the brother I was afraid of exposing my secret to so many years ago.

Overall, I know how fortunate I am when certain holidays such as Christmas and Valentines Day come around each year. Through a mix of work, destiny an sheer luck, I was able to find another person in the world who accepted the authentic me. My wife Liz basically picked me up off the trash heap and made me a believer in myself again. Something which I thought was impossible at my age of sixty two. In fact, I had given up on the idea of another serious relationship in my life and felt I was doomed to live alone as a transgender woman trying to make her way in the world. 

Perhaps, more importantly, I was able to rebuild family connections which were lost. Through my daughter's in laws and Liz's family, having a Christmas with family and friends became a reality again. And, even though I had never been a big believer in Valentine's Day, it is still very nice to tell Liz happy Valentines Day and I love her and for her to return the favor. Plus, I can't forget all my bonus checks which were added to because of Valentines promotions in the restaurant business I was in.

At the least, Valentines Day only lasts for one day and hopefully you can mend the hurt you may feel from having no one to celebrate with. Anyway you cut it being transgender should not deny you a chance to be happy with another person...but it does. 

It is just another holiday designed to stimulate certain areas of the economy not hurt the ones who happen to be single when it comes around. If you are one of those people, Liz gives out the best hugs and I am sending a big one to each of you.

Beautiful...Inisde and Out

 

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Archives...

As I obsessed with looking the best I could as a novice transgender woman or cross dresser, all I could think of was how I looked. Little did I know there was so much more coming up in my journey to living fulltime as a trans woman. I needed to live my looks as well as just admiring myself in a mirror. 

This morning turned out to be a prime example. Today I tagged along with my wife Liz to her mammogram appointment. Before I went, I applied my usual minimal amount of makeup, brushed out my hair and was essentially ready to go. While I was doing it, I felt it was time for a change. I thought I have been in a rut I have been in too long. I have essentially stopped working on my appearance and then being shocked when I am mis-gendered. 

Of course, nothing negative happened morning when it came to the doctors appointment because there were very few people waiting to begin with plus no one was paying any attention to anyone else. Since I had a spare moment, I went shopping on my phone for a foundation specifically tailored for older women. A group I naturally fit into. I found their on-line site and decided to give it a try. 

Currently, I am relying on the skin effects of gender affirming hormones, so I don't have to use a foundation at all. Or so I thought. It's occurring to me now the hormones have been a crutch for me to quit trying as much as I did. I ordered the new foundation and I will let you know my feelings. 

The end result is I need to work harder to make my inside and outside match up again. I learned long ago, similar to many cis-women, I will never be the prettiest woman in the room. I needed to find other ways to survive in the world as a new transgender woman. Little did I know, my biggest positive as a new person was already within me. My discovery was my inner feminine soul was actually good people. Opening up to others turned out to be one of my biggest pluses. The world turned out to like me. 

Doing my best to be beautiful to others, inside and out, turned out to be one of the most beneficial things I have ever done. Now, I feel it's time to get out of my rut, have some fun and get back in the game. Maybe to the point of treating Liz out to get our nails done and then have some dinner out at our favorite restaurant

I need to get us both out of the house.  

Dreams versus Priorities

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on UnSplash

 Seemingly forever, I had the dream of leading a feminine life. 

As I progressed along my bumpy gender journey, slowly but surely I learned perhaps I could achieve my number one dream.  Other guys I knew dreamed of having a great job or a beautiful wife while, all along, all I wanted was to change my gender. It all seemed simple enough except it wasn't. In fact, it proved to be extremely difficult. 

As I lived a reasonably successful male life, it became more and more difficult to just give it up and just walk away. To do it, my dream needed to become a priority. Around this time, was when I entered what I refer to as my second major transition. It was when I went from being a very serious cross dresser to being a transgender woman or going from just wanting to look like a woman, I wanted to be a woman. The entire process seems like semantics it probably is but I was serious and I was led into gender areas I never dreamed of. Primarily when I needed to step up my game from just concentrating on my appearance to needing to learn a whole new form of communication in the world.

I was in shock when I learned how quickly my white male privileges could be swept away leaving me with very little to fall back on. My previous "hit and run" approach to facing the public needed to change if I was going to survive and keep my dream alive. 

For the longest time, I was by myself in the world as a man and a woman. My male self had lost almost all of his friends and family to death leaving him mostly all alone. Plus my trans woman self had not had the chance to establish herself as a person in the world. I was stuck in a gender limbo, until my life started to change for the better as I began to set priorities for myself. Since I really had nothing to lose, I went all out on on-line dating sites which predictably I had very little success with. Partially I think because in those days there were no sites which catered to transgender women who were not fetish items. It was complicated but I went on regular sites under different listings such as everything from woman seeking woman to woman seeking man. After sorting through tons of being being rejected, my wife Liz responded to an ad I ran asking for a woman seeking woman and we have been together ever since.

Destiny at that point intervened more completely in my dreams when my regular trips to straight venues ended up with me meeting two different lesbian women on separate occasions and quickly we became a tight knit small group. My dreams quickly became my priorities at this time of my life because I needed to step my gender game up to learn and understand what the other cis-women in my life were showing me. If they knew it or not. 

When I started gender affirming hormones (HRT) around this time, there was no turning back. I faced an all out priority to live a life I had only dreamed of. For the first time, it was so close I could reach out and touch it. Even though my life turned out to be different than I ever imagined it would be, I still couldn't conceive of living it any other way. My dreams had turned into the priority of allowing my inner feminine soul a chance to live. 

Regrets?

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Jessie Hart Archives

I would suppose, similar to anyone who has reached the stage of life I have reached, may have a few regrets.

As far as I am concerned, I don't have many. Along the way, I have been fortunate to have loved and be loved by several different women. Three of which married me. In each of my marriages had their own special ups and downs. One of the regrets I do have was when I needed desperately to be the one who cheated on my first wife so I could marry my second wife. I wasn't proud of being the cheater in the relationship but I see my first wife (and mother of my only child) approximately twice a year and we get along well. We both moved on to other long term relationships which proved out to be for the best. 

I was with my second wife for over twenty five years before she tragically passed away from a massive heart attack. My regrets with her primarily revolved around me not knowing the full reach of my transgender feelings and I ended up dragging (no pun intended) both of us through the gender mess I created as I transitioned. It would have been easier if I had just pulled the band-aid off and just let the dust settle where it may. But I was selfish and still liked part of what I had accomplished as a guy. So much so, I didn't want to let it all go which was a major mistake. One which almost killed me. I would not wish attempting to live convincingly between the two main primary genders on anyone. From day to day, just to get by, I needed to concentrate which gender I was that day. I found myself in some sort of a gender twilight zone trying to figure out daily was I a man or a woman.

I did know I loved being a woman, I loved the clothes and the challenge of facing society daily as my increasingly feminine side. Sadly, as with anything else you love, many problems come with the process. Life at once became exciting and terrifying. I didn't know what I was doing as a novice transgender woman but I learned fast. At the least, I gave myself the latitude to make mistakes and keep discovering a new world. Regrets? Sure, I made many mistakes along the way as I presented myself to the world. Plus I was lucky too when I got away with more than I should ever been able to. The main ones occurred when I went behind my second wife's back to cheat on her. With another woman who happened to be me. I had always thought I was a honest person, so the whole deal proved to be excruciating to me. The more success I felt on one hand felt so natural but at the same time I was cheating on the person I loved.

I suppose everyone has regrets but destiny has softened my challenges I have experienced from the challenging idea I wanted to change my gender. Ironically, it was my third wife (and current one)who came along and saved me from myself in my darkest days. She made me a believer in myself as a person and convinced me I should have live fulltime as a trans woman. She sealed my belief in her when she told me she had only seen the feminine in me. That was over a decade ago and we have never looked back and our relationship remains strong.

It doesn't do much good to have any regrets anyhow. Life moves fast and if you didn't take the opportunity to seize it when you had the chance, it may never come around again. I am just fortunate in I have been blessed with a long life to try not to repeat my mistakes and have regrets. 

Fear of Gender

New Alzheimer's Pride Shirt

I have always thought those who protest too strenuously over the LGBTQ community as a whole or the transgender community in particular are very afraid of their own gender feelings or sexuality.

The whole reality of gender bigots coming out of their shells in public has happened because they have been emboldened by a certain former president and his party supporters. While, at the same time wealthy MAGA financers have made it possible for them to pursue their bigoted goals at the state political levels. My native state of Ohio is a prime example. A fundamentalist Baptist preacher has been leading the charge to erase all transgender care in the state. In response, the state legislature has already passed bills restricting any care for transgender youth under the age of eighteen. To make matters worse, they have plans to try again to expand the bill to all transgender women and men in the state in the future. So far they have failed and the ACLU has promised to take the state to court over it's bills. 

As I put my anger aside for a moment, I paused and wondered what skeletons the Baptist turned politician had against me. Similar to all of the other transgender people I know, we are just trying to lead a quiet life. The better we are at staying out of the public eye, the better. Plus, don't get me started on what I feel about churches who do more than dabble in partisan politics. 

I shouldn't be surprised with a Baptist preacher leading the anti-trans charge here in Ohio since my brother's in laws are all fundamentalist Baptists and he chose them over me when I came out to him. As much as it hurt, I got over it and we have not communicated in over a decade.

All ranting aside, I am a firm believer in the power of gender to transcend and take over any other paranoia a human may have. From birth we largely have our gender chosen for us. Like it or not, using me as an example, I was obviously born a boy or male but I grew up to be a transgender woman. Not completing the gender journey I was assigned would have led me to an early death. It is my opinion, the most oppressive of the gender bigots have a fear of their true selves. They protest too much as many are clutching their crosses while they are doing it. It is tragic when people hate so much. I don't expect the public to understand me  but I don't expect hate either.

I am lucky to live in a fairly liberal part of Ohio, far away from the area where the ultra anti transgender preacher lives. So my activism comes primarily from my writings, my out-reach attempts with groups such as the Alzheimer's Association and participating in Veterans LGBTQ groups. It is essential for me to let them know how urgent the anti-transgender situation is in Ohio. Sadly I can only do a very little to financially support candidates I knew will help our cause. 

I don't suppose I will ever understand why anyone who wants to harm a person in the LGBTQ community because if you are gay and or lesbian you can't think eventually the gender bigots won't come for your rights also. They are using the weaker transgender community as a starting point. Even if you are a cross dresser deep into your closet, you need to consider your gender future and vote accordingly. 

We all need you!

Sizing Up the Crowd

 

Image from Roberto 
Nickson on 
UnSplash

Recently, when I met friends at a local brew pub for brunch, I needed to walk the distance of what was called the "great hall" to meet the group.

Once again I needed to make sure I was standing up as straight as I could, while throwing my shoulders back and faced the reality all transgender women face, was I going to be spotted as some sort of a gender impostor and even laughed at. I didn't and even though the brief walk felt as if it went on forever, I made it to our table without incident. At that point I thought I had it made, until the young server called me "sir". Which is another sad experience I have previously written about. 

For some reason, when I transitioned into a feminine transgender world, I didn't think the public would share the same fascination with studying other women as I did. I can't tell you how many times my old guy self aggravated my second wife (and others) by trying to sneak a peek at an attractive woman. For whatever reason, I couldn't explain to them I wasn't looking because I desired the woman, it was because I wanted to be the woman. At the time, I was having a difficult time wondering if I could ever achieve my dream of cross dressing out of my old unwanted male self. There were so many working parts of a woman to duplicate, the whole process seemed impossible. I needed to fashion my own hips, breasts and hair just to arrive at a point where I could put the entire feminine package into motion. 

It wasn't until I began to leave my dark and lonely gender closet behind and attend transvestite mixers did I begin to think I could succeed. Through the help of the mixers, I was able to judge how other cross dressers were successful with their presentations...or won't. I saw everything from men in beards and dresses, all the way to beautiful transgender women who were completely undetectable as former boys or men. As I sized up the crowd, I knew which direction I was headed. Most certainly I did not want to be with the bearded crowd and wondered to myself if the transsexual group was where I needed to be. Keep in mind, this was back before the transgender label was widely understood or used. What amazed me too was how intense the pressure was to size up the crowd and fit in to where you belonged. 

Little did I know, I was just beginning my trip out of the closet and into the world and I would need to obsess on my appearance until I gained the confidence to go forward as the person I was. Deep down I knew I would never be the prettiest woman in the room, I just wanted to be the trans woman at peace with herself. So when the crowd sized me up, they recognized who I truly was and it was good enough. I learned also, the greatest majority of the world didn't care about me anyhow and they were involved in their own little worlds. My second wife was always fond of telling me it always wasn't all about me when it came to my cross dressing and she was right. It was just the ones who did care who became the problem. As I made my way along my gender path, I was fortunate to dodge most of the haters and live my life without severe incidents.

I am a firm believer in the younger generation doesn't see gender as a threat and in the future sizing up a younger crowd will be less of a threat to transgender women and men everywhere. I, on the other hand, when I chose to live a life as the high maintenance gender chose to always be on the stage of life.