Beautiful...Inisde and Out

 

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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

 

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Nickson on 
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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! 

    

Gender Expectations

 

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Jessie  Hart
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Early in my transition to a fulltime transgender woman, I thought my expectations would be relatively simple. 

My simplistic approach led me to believe achieving perfection in my knowledge of makeup and acquiring the feminine clothes would be all I would need to survive. Little did I know, when I went public with my cross dressing, I would encounter so many other issues to solve. 

Another problem I had was my cross dressing theory all  was wrong and directly backwards.  All along, I was a woman cross dressing my life away as a man, plus I had no idea how my new time as a transgender woman would put me so completely on a public stage with men and women. The time I spent trying to cross dress for my male self proved to be totally wasted for the most part. Those were the days of trying to dress sexy and failing miserably. 

As with any female who grows into womanhood (all don't), I needed to learn to play in the girls sandbox. As I came closer to perfecting my appearance the best I could, each time I thought I reached a milestone, I found there were many more to come to achieve my goals of living my own version of womanhood. Even though I may not be the prettiest girl in the room, I still could rely on other aspects of my personality to succeed. Similar to any other woman I had met in my life. Like my transgender friend Racquel told me I passed the public out of sheer willpower. I was just being the authentic me.

One part of the entire coming out process which really intimidated me was how I needed to present differently to each binary gender. As I always mention, men had the tendency to steer clear of me and women had a tendency in their own ways to challenge me. Communication in the world to survive became key to me. As far as men went, I think there were very few who were secure enough in their own masculinity to approach me. Plus, since early on I was usually alone, I would try my best to give the impression someone else was coming to join me. One of my favorite "props" was my cell phone. I used it to act as if a friend was on the way and I was saving a seat where ever I was. Then, when I did develop a small group of women friends, I did my best to blend in and not stand out of the crowd so to speak. 

Through it all, I can't write enough on how insecure I felt for years in public when I first came out into the world. When I couldn't wear my sunglasses to judge the public's reaction to me, I tried to perfect my peripheral vision to see the best I could if I was creating an impact by just being my authentic gender self. The whole process turned out to be a multi-layered experience. Similar to what my second wife told me about absorbing the life skills women need to survive. For years I was naïve and didn't understand what she meant since I had literally obsessed studying the world of women around me I so admired. I never considered all the ramifications of coming out as a transgender woman would mean. 

Once I did discover my truth, I did have others around me to assist in my journey. Together they all helped to make my expectations more realistic and achievable.      

Catching the Trolley

 

The Trolley Stop, Dayton, Ohio

Since one of my college degrees is in History, I always have been a fan of historical restoration.

When I was considering my male to female gender transition, a portion of the baggage I was looking at bringing along was my love of history. All the way to the point of where I lived, an 1860's brick building I restored myself in my home town. To do it, I taught myself many of the basics of plumbing and electricity. 

One of my inspirations in my restoration was in close by Dayton, Ohio in a area known as the "Oregon District". Home to many beautiful Victorian homes. Included in the many residences was a commercial strip of businesses along a brick street which had been there for years and years. Plus, it just so happened, many of them were old taverns. 

I know I write often about my fondness for going to the large sports bars when I transitioned since they provided me with a more pleasurable experience than the local gay bars did. While it's true I did go to the sports venues quite a bit, there was another place I went to also. It was called the "Trolley Stop" located on the strip I was telling you about in the Oregon District. The "Stop's" building was constructed in 1839 and is believed to be the oldest continually operating tavern in Dayton. As well as being known for it's drinks, the kitchen features cooking made from scratch. 

Since I was a customer before I transitioned, I knew what to expect and thought with a little work I could be accepted at the "Trolley" without much problem. I was right and in no time at all, I became a regular with one of the fulltime bartenders. With that accomplished, I was awarded with restroom privileges and others in the tavern being nice to me. I rarely had any problems. I could enjoy two of my passions, history and living a life as a transgender woman. 

My fondness for the venue grew except for the fact the restrooms were upstairs and when I consumed a few cocktails, navigating the steps became quite the challenge for me in my heels. Until I quit wearing them when I knew I was going to the "Trolley." 

Along the way, I ended up meeting my small group of friends there. Including my transgender friend Racquel. To the casual observer, I am sure we seemed to be quite the group. On occasion also, the venue hosted lesbian mixers which were always quite fun for me. In fact on several occasions I was able to steal a kiss from an admiring lesbian woman. 

Now, since I moved fairly far away to Cincinnati from the Dayton area where I lived, I have not been back to the "Trolley Stop" for years. Hopefully the venue and all it's fond memories will out live me. 

Never Give Up

Image from Amin Rk 
on Unsplash

 Similar to so many transgender women or men, I live a fragile existence. Or I should say for the most part I lived a fragile life as a cross dresser.

These were the times I was fighting totally any feelings of being feminine. Naturally, my ingrained male self fought the entire idea completely. Several times when I was caught cross dressing in front of the mirror, I gave up and decided to "purge" (or throw out)  almost all of my feminine belongings. I say almost because every time I stopped purging, I stopped just short of throwing out my favorite wigs or dresses. I guess deep down inside I knew I would need the clothes or wigs again. And I did because I never gave up on my dream to live as a fulltime transgender woman. 

By never giving up, I had several obstacles to overcome along my gender path. Everyone goes through tough times in their lives and looking ahead, I could see many more on my horizon. Mainly because, I was far from a natural when I looked at myself in the mirror. How could I ever turn a rather gruff bearded overweight man into a presentable trans woman. 

First things first. As soon as I could the beard had to go along with the weight. The first part was easy but the weight wasn't. Fortunately, I was able to cut back on a few fattening items and let my still robust male metabolism do the rest. In no time at all, I was able to lose nearly fifty pounds which helped completely in finding women's fashion in my size. At the same time, I started to concentrate on my skin. After shaving, I made sure I used a good moisturizer to aid in the process. I learned how much better my foundation looked on my face when I cared for my skin, plus by shaving daily, I was exfoliating my skin very effectively. In my case, along with practicing "extreme" shopping methods for fashion, I was able to do better in presenting my feminine self to the world. I suppose you could say, the whole process was a labor of love.

On occasion, I am amused when someone thinks my gender journey into trans womanhood was an overnight success. They never saw or understood the "error and trial" methods I went through when I first began to explore the public as a novice cross dresser or transgender woman. The most important moral to the story is I never gave up. No matter how difficult and bumpy the path became. Why? 

The easy answer is no matter how hard life became, deep down I knew what I was doing made me feel so natural. I felt if I lived long enough, I could leave my old male self behind and finally live in the world as a trans woman. 

Destiny proved me right and I was able to fit into a life in the world, I had always only dreamed of. I learned the hard way to achieve any goal in life, you never can give up.