Pockets of Insecurity

Girls Night Out, I am Bottom Left
Image from the Jessie Hart Archives.

 Where I live in suburban Cincinnati, it has been rare in the past decade when I have ever been harassed for being transgender. In fact, I think the only time it happened was when I first moved down here approximately ten years ago.

However, if I travel a few more miles east into a neighboring county, I always find myself in a decidedly redneck or MAGA areas. One of the most memorable occasions took place two times when the Wiccan group I was part of had garage sales in a small village in the middle of the area I am referring to. Here we were on a Sunday morning and afternoon set up just outside of a big box store selling crafts and baked goods to interested people. Yes I was scared!

I thought, how the heck did a transgender Wiccan trans woman end up in an heavily redneck area on a Sunday? One in a million I thought. Then I was wrong, there was another trans woman trying her best to come out in a hostile world who owned a house not far from where I was. We have kept track of each other over the years through social media and recently has said she has had more than her share of problems from her world. She has been subjected to everything from old ladies shaking their fingers at her at the grocery store, all the way to men yelling derogatory things from their cars. Gender bigots everywhere it seems for my poor friend. 

The frustrating part is she presents well except for the usual problems with her height and voice. Naturally, she has expressed her frustration with living in the entire Cincinnati area. Several others, including me, mentioned it wasn't the entire metro area, just where she lived. 

Sadly, in many ways, my friend is stuck in a small way in the same problems all transgender women and trans men have living in Ohio. Even though, the metropolitan areas of the state are inviting, diverse and liberal. the redneck Republican politicians are now trying their best to erase all of the gains and rights trans Ohioan's have gained over the years. Now including even the rights to gaining healthcare for gender affirming hormones and beyond. In doing so, the state is threatening to come after the very clinics which work with the trans population. If it happens, it will be scary to see if the states' intrusion into my life will reach all the way to my Veteran's Administration health care. Which, for me has been overwhelming positive when it came to my gender affirming care.

The moral to the story is, no matter where you are or how far along you are in your transition, you better be aware of what your future could hold. Even though you are deep in your closet, you need to vote accordingly for your future. 

As far as my friend goes, I hope she finds away around all the gender bigots and discovers a way to live an authentic life. 

Passing Privilege?

 

"Cheap Sun Glasses"
from the Jessie Hart
Archives

As we make it through the various stages of our gender journeys, often we are overly concerned with our appearance.

Very early on I learned my looks, or lack of them, were referred to how I presented as a feminine person. If I was a success, I "passed" and if I failed the term I most often heard from within the cross dressing community was I was "clocked" as a man in a dress. So I began to become more and more obsessed with "passing" as a woman in public. The problem was, I thought I was achieving success when I was admiring myself in the mirror and then failed miserably when I tried my best to pass in public. The process all led to my well documented years of thinking (or confusing) sexy with trashiness when I cross dressed. What maybe looked good on a teenaged girl, most certainly didn't look good on me. Undeterred, still I persisted. Finally I made it through my so called teen aged girl years and into womanhood and started to work on blending in with the other women around me. 

All of a sudden, I found I could discover just a small amount of passing privilege. In my case, it meant not being stared at to the point of even being laughed at. I could concentrate on the brief gender euphoria I was feeling by just being in the world as my feminine self.  One of the tricks I used to judge the world's reaction to me was to wear sunglasses. When I did so, I could see how others were looking at me without being obvious. My "cheap sunglasses" worked well from a fashion standpoint as well as a tool to see if I had gained any passing privilege. 

It took me years longer to discover what any sort of a woman's gender privilege was going to mean to me anyhow. When I first began to become successful as a novice transgender woman, the only privilege I could notice was when a man would stop and hold a door open for me. The more I experimented in the world, the more I learned how wrong I was about the passing privilege and/or feminine privilege's I was gaining. Nothing really happened until I was able to hold my head up in the world and quit being so shy about myself. After all, I was doing nothing wrong and if someone else had a problem with me, it was their problem. Not mine to solve or run from. 

When I first was able to be prescribed gender affirming hormones for the first time, I suddenly learned more of what feminine privilege was all about. As my initial dosage increased, I found I had a different view of the world. As my senses became more in tune of what was going on around me, my world just grew softer. I could not believe the changes. 

I think my final bout of passing privilege also came with the external femininizing results from the hormones. Since I had never been a "natural" when it came to trying a male to female gender transition, I needed all the help I could get. Most certainly hormones aren't for everyone, but they sure were for me.

These days, I mostly just present as old. I have a natural passing privilege.  

The Biggest Sacrifice?

 

Image compliments of Racquel.

When transgender women cross the gender border into a feminine world, we face losing many things. 

Naturally, we have to consider the three "F's" or Family, Friends and Finances. All major losses in our lives. In fact, they are so important I get a chuckle when someone says being trans is some sort of a choice. If indeed it was a choice to undertake such a radical life change, I would have certainly chosen an easier path. With easier sacrifices. 

In the early years of my life I was predictably naïve when I thought cross dressing in girls clothes was sacrificing just my male existence. It took me years of living, as well as accumulating white male privileges, to learn how much more I could lose. As far as the first two "F's" would go, I was fortunate in my results. I lost all contact with my only sibling, a brother but gained so much more through adding a bigger more accepting family through contacts such as my daughter and wife Liz. Thanks to women such as Kim, I was able to expand my friends into an accepting world of cis women who taught me so much about the life I wanted to pursue. I even had a close transgender woman friend (Racquel) who I would socialize with on a regular basis. Surprisingly, I found I had an easier time making friends as a trans woman than I ever did as a man.  In addition, Racquel and I had more than one interesting adventure at venues when rednecks played "Dude Looks Like a Lady" on the juke box eventually leading to the manager kicking us out that evening and not our bigoted tormenters. She is also the one who said I passed out of sheer willpower. 

As I progressed down my gender path to living more and more as a trans woman, I discovered more and more sacrifices I would have to make. One evening comes to mind when I was first coming out, somehow I found myself in a group of men. I found out quite early not to try to interact at all when I was ignored when I tried to talk and express my opinion. So much for maintaining my intelligence or any workable knowledge as a woman. One male privilege down to be sure but I found the biggest one was yet to come. 

The biggest privilege to lose was my access to personal security. I was always a fairly good sized man and could handle myself well enough to get by. The first time I encountered problems was when I was a cross dresser at a party of my friends in Columbus, Ohio. The attendees were normally very diverse and included anyone from transsexuals to lesbians to men who were cross dresser "admirers." One night I was cornered in my too short mini dress by a huge admirer and needed to be rescued by my highly disapproving wife. In an instant, the damage was done and I learned how easily it was for a woman to be overpowered and compromised by a much larger man. 

The other lesson I learned was the one I mentioned in yesterday's post. It happened when I left a gay venue cross dressed in my heels and hose and ran right into two men on a dark deserted city street. As I said, I was fortunate when I was panhandled for a five dollar bill and allowed to go on my way. These two happenings taught me valuable lessons on keeping myself safe in my new feminine world. All I was really doing was learning what cis-gender women grew up knowing their entire lives. 

So all in all, with a lot of help from the world and friends, my sacrifices turned out to be less severe than the process should have been. And, so worth it! 

 

Is it Sustainable?

 

Image from the Jessie Hart
Archives

When I was cross dressing for myself in the mirror, it was easy to imagine me sustaining how I felt when I put on my small stash of feminine clothes. It seemed as if the feelings could go on forever. Then all too quickly I found I couldn't sustain my feelings of gender euphoria any more than a couple of days at the most.

At that point, I began to wonder about the feelings the clothes brought on to start with. I recognized at a very early age more was going on than just appearing pretty to myself in the mirror. I wanted to be the girl I had become, rather than just look like her. If I knew then what I know now, I would know my feelings would later lead me to discovering a transgender life. Perhaps if I thought it would be sustainable, I may have transitioned earlier.

One of the main problems with sustaining myself as a trans woman was maintaining a presentable feminine appearance. I worked hard to do it and when the mirror in the women's restroom I went to one night in a gay venue where I was meeting two lesbian friends told me I looked good, my confidence soared. It was summer and I was dressed all in black that night with  a sleeveless silky top with black flowing pants. I finished the outfit off with my favorite black sparkly sandals and long straight black wig. Fortunately by this time in my life, I learned the hard way my male privilege of personal security was gone so when I left, I asked my friends to walk me to my car which was parked in a dark urban parking lot. I had been there before and had been stopped by two men seeking money. Luckily a mere five dollars got me out of the bind I was in.

Keeping the appearance issue in mind, my biggest sustainability issue came from worrying how I would support myself if I transitioned. The industry I worked in, I knew would be very difficult  to succeed in if I suddenly changed my gender from male to female. So I knew I would have to find another way of financial support. What I came up with was getting old and just taking the early retirement option of Social Security. It wasn't a lot of money but it was enough to get me by and save me the extreme potential problems of trying to come out at a new job. 

So with all the help I discovered from my Veterans Administration health, doors opened for me which I never thought possible. The prime one was all the help I received when I finally decided to begin gender affirming hormones or HRT. A therapist was provided as well as my medication co-pay for all the meds I needed to really change my life. With those meds, at a price I could afford, my long term sustainability was secure. 

Perhaps the tragic aspect of all of this is almost all of my friends and close family had passed on. Leaving me with fewer and fewer people to come out to. However, times of potential gender trauma were greatly reduced and new doors were opened to me I never dreamed of as a transgender woman. The sustainability was there and so was I.  

My Eyes are Up Here

 

Image from UnSplash

As I increased my knowledge of male to female cross dressing, I immediately learned the power of how my breasts appeared to the world. If I could attract the eyes away from my big shoulders to my breasts, I was successful. 

At that point I began to seriously experiment with how I could make my breast forms be as attractive as I could while on the very limited budget I was on. As I remember, stuffing my Mom's bra with socks was the only way I could go. Since my only feminine interaction was with the mirror in the hallway, having realistic breasts was mostly just in my imagination. It was about this time too, when I discovered and was very jealous of the teen aged girls around me who were suddenly sprouting their own breasts and wearing brand new training bras under tight sweaters. It was so unfair to me. So I set out to do much better with my own breast forms.

If my memory serves me correct, the next object I tried to use for breasts were foam nerf balls which were cheap and easy to come by. I still was far from satisfied with the results but it still was an improvement over rolled up socks. I needed to figure out what should be the next step in figuring out what to do about developing a better set of fake breasts. Along the way, I tried many ideas I read about mainly in the "Transvestia" magazine I received every couple of months. I know some of the cross dressers in the publication somehow were fans of using birdseed. Which I never ended up trying. Instead I went the water balloon route which went well until the predictable disaster happened to me when one broke. I really liked the balloon idea because they were cheap and I could use lukewarm water in them and approximate as close as I could to what I thought a real breast would feel like. Plus, I loved the way the balloons moved and bounced when I wore just the right bra. 

All was good with my new breasts until one night when I was headed to the women's room in one the venue's I was a regular in and unexpectedly one of my water balloons broke in the hallway leading to the restroom. The only good thing which came from it was no one else was in the hallway so I didn't have to explain to them I was pregnant and my water broke. I was able to pay my bill and quickly head for home. Finished with water balloon breasts forever.

My next step forward in the breast form department came when a cross dressing friend of mine in nearby Columbus, Ohio decided to purge all of his feminine belongings which included a nice set of silicone breast forms. I eagerly accepted the gifts and immediately stepped up my breast game. I ended up using the forms until I finally had the opportunity to join the women around me and have my own breasts thanks to gender affirming hormones. 

These days, even though I think my bigger body shape could support bigger breasts than I have been able to grow with the hormones, I think at this point in my life, I will stick with what I have in the breast department. 

It's interesting to me how much breast surgeries are being done these days for transgender and cis-gender women. In fact, I see big billboards around Cincinnati for plastic surgeons who will do the procedure completely for less than seven thousand dollars. I have the money saved but I think I could use it in better ways.

As it stands now, when someone looks me in the eye, they really do it.

Trip Number One

 

Hair after salon image 
Jessie Hart
Archives...

Way back when, one of the first priorities I had was coming out to my only child, a daughter. Of course I was properly scared to death the morning I told her at breakfast. 

It turned out all the paranoia I felt was unfounded when she wholeheartedly supported me. Which she does to this day. Outside of my wife Liz, she is one of my biggest transgender allies. Especially since her oldest child came out to her as trans, so she had some experience with the entire situation. 

When I came out to my daughter, I had a chance to let my hair grow out to the point where it could be styled professionally at a beauty salon. Which at the time seemed to be the impossible dream. It also was close to my birthday so as it turned out my birthday gift was a trip to her (daughter's) very upscale salon for a color and trim. 

Even though the entire idea of going to a women's beauty salon  really scared me, how could I refuse such a wonderful gift. Before I knew it, the time to meet her and go through with the visit was upon me. For my first visit my daughter came with me to essentially hold my hand, because I was almost ready to panic and run out the front door. But I didn't. As I nervously sat and waited with a cup of coffee, I wondered what was going to lie ahead and what color was I going to choose for my new hair. Since I had retired, I didn't have to worry about any negative responses from employers or fellow employees. Freed up from all that worry, I was able to worry about my choices.

Finally, it was my turn to be called back to my new stylist. Predictably, the salon itself was long and narrow with a single line of women in chairs being styled. Walking in front of all of them and feeling their eyes on me did not do me any favors when it came to my nervousness. After greetings were exchanged, the first priority was picking a color to change what was left of my dark hair which was my natural color. By mutual agreement between the stylist, my daughter and myself, we decided to go with a streaked light red and blond look. Plus, since my hair is naturally wavy, the stylist straightened it out. Which later on I found I didn't like.  

By the time all of this was happening, I thought I was getting a contact buzz from all the estrogen in the room. Through it all, I quickly discovered what I was missing by never being able to go to a woman's only space such as an upscale beauty salon. Before I moved, I ended up going back several times before I moved away to Cincinnati. Plus, the more I went, the more I relaxed and enjoyed the experience. 

It took awhile but I found and set up many appointments with a new stylist here in Cincinnati who happened to have a transgender son. Again she was very good at her craft and I enjoyed going to her for hair advice and stylings before she retired due to problems with her hands. With her though, the experience was singular because there were no gauntlet of women to walk past everytime I went. She had her own little cubical. 

I will forever be in debt to my daughter for her birthday gift so many years ago which brought me into the  world of beauty salons. From that point forward, I began to understand why women spend so much time and money on their hair.

Making Lists

Image from UnSplash

 Every once in a while I receive a question about how I transitioned into a different transgender world. 

For a time I made mental lists, outlining where I would go and what would I do. Before I became involved with lists, I needed to decide once and for all I was indeed a transgender woman and had transitioned from being a very serious cross dresser or not. Once I did, my existence became so much more complex. In essence I had to decide a new path for the rest of my life. What would I do about my family, friends and finances. It was all so easy and fun and games when my only worry was how I looked in the mirror. After I decided to do so much more, I really needed to make my mental lists for the gender challenges I was suddenly facing.

The first lists I made involved where I was going in the world. I needed to challenge myself and do extra trips away from the usual women's clothing stores and seemingly safe gay venues I was going to. My expanding life was all too predictable and provided me no chances to expand my new feminine perspectives. Clerks in stores were just interested for the most part in my money and the gay venues just mistakenly thought I was a drag queen. One big exception were the lesbian bars I discovered. I went primarily to two of them. I was hated in one and accepted in another. The lesbians in the second bar were intrigued by me and I was even asked one night to sing karaoke by a large butch who wouldn't take no for an answer. Since I am a terrible singer, I sang in a low background voice and somehow made it through my musical challenge. I crossed the evening off of my lists and made a mental note to attempt to never see her again. Which I did not. 

On occasion, my activities collided head on with me hiding all of this from my wife. When my wife needed to work her retail job at night, many times I would use the time to head out the door and explore knowing I would need the time to be home, take my makeup off and appear as if nothing happened when she returned. Many times I was not successful and a huge fight would ensue when she saw vestiges of eye makeup left behind. Somehow we were able to make it through the skirmishes and most of the time I made it home before her.

Many nights it was difficult to pull myself away from my list to keep from getting in trouble. I remember vividly the night another butch said to me she should take me home. I had no idea if she knew the truth about me and what she was bringing home but I was out of time and couldn't wait around to find out. I couldn't imagine what excuse I would have had to come with for my wife if I had explored the evening farther. I had to rip up my list and forget it, for a time. 

From the confidence I had built up in the lesbian venues I went to, I then listed sports bars as my next challenge. I had always enjoyed going to sports bars to drink beer and watch the big screens when I was a guy and wanted to see if I could do the same as a transgender woman. Fairly quickly I found I could and I needed a new list of goals to conquer. 

By this time, I was ready to try gender affirming hormones and plan ahead to the strong possibility of being able to discover a fulltime life as a trans woman. During this time, I was checking skills such as public communication off of my check lists and set out to try to conquer a brave new feminine world. Finally, my new life became second nature and I didn't need any more lists at all. 

Supporting Casts

 

Girls Night Out. I am on the Left.
From the Jessie Hart Archives

One aspect of my gender journey, I don't mention enough is the importance of the supporting cast I had around me to help me along.

They clearly helped me during the times of my life when I was down and almost out when it came to me going any farther as a transgender woman. A prime example was when I started gender affirming hormones and was wondering if it was the right move to make. By just being a part of my life and understanding what I was going through brought about a significant need for moral support. Another example was when I began having hot flashes and my women friends (cis-gender) just smiled and said welcome to their world. Which is exactly where I wanted to be. 

Over the years, there was only one woman who held my gender issues against me. She was my first fiancé who in the past, one time cross dressed me head to toe as a woman. The whole process turned out to be a bittersweet experience. For the first time in my life I had tried to share my deepest secret with another person and turned out to be less than impressed with the entire outcome. When she had finished with my makeup, I saw no real improvement over my efforts which ended any ideas I had that women had an edge over cross dressers when it came to makeup applications. So, the sweet part was limited and doomed to fail to begin with. The bitter part came later on when my fiancé broke up with me after I refused to say I was gay in order to not be drafted into the military during the Vietnam War. Lesson learned and I went back into my deep dark gender closet for years until I met my first wife. Even though she always knew I was a cross dresser or transvestite, she never made a big deal about it. 

Around that time of my life the biggest support I received ironically came from a man. A stranger who was doing makeovers at a cross dresser mixer I attended. I put on my big girl panties, removed all my makeup and let this stranger work his makeup magic on my face. When he was finished, I couldn't believe the transformation. Plus, I was actually able to understand and redo the makeup steps and repeat them. The entire process takes me to my experiences with my second wife. Similar to my first wife, she knew I was a transvestite from day one in our marriage and even supported me...to an extent. Keep in mind, we were married for twenty five years and during this time, I was slowly transitioning more and more into the transgender woman I am today. Before my wife's untimely death, we had numerous fights over my desire to be a woman and begin gender affirming hormones. Her stance until the end was she didn't sign up to be with another woman. To make matters worse, I don't think she ever liked my inner feminine self and the two women battled continually.

After she passed on, it took me a few years for me to recover from the shock and get on with my life. One positive I carried with me was how affirming the presence of my feminine side turned out to be. As it turned out, destiny led me to other groups of women who essentially adopted me into their tribes and helped me to flourish. 

I can never say enough how much I learned from all our girls nights out together. Without all of them I can never imagine how much longer and which direction my transgender transition would have taken.  

Empty Houses

Photo from the Jessie Hart
Archives

 As I grew up in a male world, I naturally adopted many male dominated activities and hobbies which I stored away in my house I had to build as a guy. 

Mainly because I was frantically chasing
my desire to be feminine, I sometimes jumped from activity to activity rapidly. Plus none of this was accounting for the traditional male things I was doing such as building a family and trying my best to provide as good of a house I could. As far as actual house goes, I was trying to follow in my Dad's shadow and come as close as I could to either remodel or build my own house. He built his own house while I worked hard to renovate an 1860's era brick tavern in the town I was from. I came close but I don't think he understood why I did it. 

Bu it wasn't easy. I needed to teach myself the basic's of plumbing and electricity among other important things associated with remodeling an old structure. The end result was my second wife and I were able to live comfortably there in the years before her death. Then, I was all alone with a couple dogs and a cat in this huge empty house. At that point, I needed to decide which direction my life would take physically and mentally. What I mean was, was I going to continue to try to live in the house I remodeled with all it's memories or try to move on. With all the animals of course. What I decided to do was make the house even emptier by selling all my wife and I's vintage collections on line and using the money to augment my Social Security money I was making. In doing so, I managed to keep the house going for awhile as I sought out the possibility of taking an early retirement. Eventually, years later, I was able to move us all in with my current wife Liz in nearby Cincinnati, Ohio. 

As it turned out, the physical aspect of having an empty house was much easier than the mental part. Since during my life, even though I started out shy, I became a rather social person with deep ties to my home town. Sadly, those ties had nothing to do with my increasingly dominant feminine self. With no one to stand in my way, I was actually able to pursue if I was indeed transgender or not. Or just a serious crossdresser who wanted to their best to look like a woman. Since I had the options and inspirations to discover my true self further, I finally gave in to my inner female and set out to attempt to build a new life.   

Surprisingly, leaving behind my old male life was easier than I anticipated. Destiny (and effort) led me to meeting a new group of cis-gendered women friends I could be social with and learn about a new house at the same time. Plus, all the years I dreamed about decorating a new empty gender house came to pass as I adopted relatively easy to my new gender affirming hormones and life as a fulltime transgender woman. Then my relationship with Liz, who I met on line flourished, and we were married years later after my daughter suggested we finally do it. She made sense, we married and moved on to a new chapter of building my feminine house and making it much less empty.

I am sure, when one discusses genders, not many humans get the chance to empty one house and start all over again in a new one. It is a scary yet exciting journey.