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

 

Image from the Jessie Hart 
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

Image from Marcos Paulo Prado 
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. 

You are Such a Girl

Boho Woman from Brooke
Cagle on UnSplash

Jen recently responded to my comment about walking in heels on stairs while being slightly intoxicated. 

Jen, who I have known for years happens to be a cis-gender woman and said she has never mastered the art of walking in heels. I have always appreciated knowing Jen because of her acceptance of me as my authentic transgender self from the first time we met. As far as me judging her for not wearing heels, it never happened. 

Perhaps, I quit judging women from their footwear came primarily because all of the women I socialized with were not the girly-girly types and never wore heels. At that time, I still could wear heels but decided not to because of adding to my height as a trans woman. All my friends were shorter than me and I did not want to tower over them. 

Being such a girl, did not reach all the way to wearing makeup and the feminine clothes I wore. In order to stand any sort of a chance to present well as a novice transgender woman or cross dresser, I needed to take advantage of all the benefits which makeup gave me. In fact, when my second wife was alive, she used to call me the "pretty, pretty princess" in response to all the time I took to apply my makeup. When she wore little to none. Obviously she didn't have to worry about the benefits of fashion to just exist in the world as a feminine person. 

As my life progressed and changed, my knowledge and application of makeup needed to also. While it was obvious I still needed to take advantage of cosmetics, the new pressure was on to look natural while I did it. In other words, to appear as if I wasn't trying too hard. I desperately needed to blend in with my group of cis-women friends who again did not wear any makeup at all. It was during this time in my life when I really began to step up my skin care routine. I made sure I was able to apply a good moisturizer after everytime I exfoliated or shaved. The entire process enabled me to use less foundation and achieve a more natural look. I was also given a positive head start on when I started gender affirming hormones (HRT) which naturally allowed my skin to soften and smooth out. 

Of course, my basic fashion sense came into play and I was given a head start by my feminine preferences in clothes. Growing up, I had always admired all girls, tomboys and all. They were the women who were able to show off their so called masculine side without anyone questioning their basic gender or sexuality. While I had to play the same old male game of never showing a softer side. I took it in stride the best I could and later on became a big fan of women in "Boho" fashion and bell bottom jeans, In fact, I loved them so much, I was harassed at several transvestite mixers I went to when I wore my pants. Comments were why don't you wear a dress because you can wear pants anytime were common. I politely told the other attendees to mind their own business and went on about my own. 

Wearing pants before my HRT hormonal days involved extra attention given to how my hips and rear appeared in woman's clothes. Similar to so many others, I resorted to using foam rubber inserts in my panty hose to give me the illusion of hips. Depending on the top I was wearing, I pulled off the illusion fairly well without having to resort to wearing restrictive undergarments such as girdles which to me took away much of the sensory pleasure I was feeling at the time. 

I guess you can say, compared to many of the other cross dressers or transgender women I knew at the time, I went rogue in my approach to being feminine. For whatever reason, I always admired the women who could take a tomboy look and work it into a fabulous fashion statement. 

I hope I provided Jen with a little feedback on the way I feel about her never wearing heels and how much I appreciate her (along with all you others) for reading and commenting on the blog. Thank you!