Trans Bucket List

 

Image from Pepe Nero on UnSplash.

On my way to achieving my version of transgender womanhood, I started my trans woman bucket list.

It all started on the fateful night when I decided to go out and mingle with a group of professional women as an equal. Not as a man cross dressed in their company to see if I could make it in their world. There was so much else at stake that evening because I knew if I was successful, I could never go back to just living my life as a man. 

Once I was successful, I began to think of  things I could accomplish as a trans woman to add to my bucket list. Once I was accepted as a regular in one venue, could I possibly add another to increase where I could go to add variety to my evenings. For the most part I was successful in being accepted. Even to the point of being thrust into a diverse small group of acquaintances I could regularly socialize with. The group included the sister of one of the bartenders, a lesbian, a couple men and an exotic dancer to name a few. All of this occurred before I met the transgender woman and two lesbians I socialized with on a regular basis.

Also on my bucket list at the time was how was I going to handle my sexuality with men. I almost found out when I became attracted to one of the men in the group. Or should I say he was becoming intrigued with me. All the way to him seeking me out on the nights when I was there all alone. I felt comfortable talking to him and even enjoyed his company before he switched jobs and abruptly moved away. It turned out there were very few men on my bucket list but even so, there were a couple which left a deep impression on me. 

Both of the men were met through social media dating sites and happened after I sorted through an amazing amount of trash responses. Because I was careful to meet any responders in a setting I approved of, we met in my regular venues I felt safe in. Both treated me with respect and I leaned a little of how it would be to interact with an interested man as a woman as I was wined and dined. It was terrifying and exciting at the same time. I still remember both dates and how special I felt but on the other hand, I never really lost my attraction to women. As impossible at it seemed to me at the time, I was headed towards being a transgender lesbian...if I could be accepted. 

I continued my quest for a new bucket list as I learned how to be a woman from other women. It seemed nightly I was learning new ideas such as I did not need a man to be validated in my new life. The lesbians I were around were both very strong and confident in their own right, so I could be also. 

Then, there was my relationship with my wife Liz which has been going on for over thirteen years now. I never though I would find another person who would be serious enough about me to want to build a relationship at my age. But I did and amazingly, Liz found me on a dating site defying all odds. 

Just when I thought I was done with my bucket, it became filled with happiness and I hope to keep it that way. 

Trans Girl in a Furniture Store

Image from Nathan Dumlao
on UnSplash

Once I had progressed to a point where I could comfortably navigate my way around in public as a transgender woman, when Christmas rolled around I thought I could do my shopping as a woman.

Since previously I had helped gift my second wife an oak roll top desk, I thought if I could find and afford a matching oak book-case, I would buy it for her as a Christmas gift. Before I did, I needed to find a store which carried the book-cases. As it turned out, the closest one I could locate was fifty plus miles away in nearby Columbus, Ohio.

Before I made the trip, I needed to make sure I planned out when my wife would be working and not at home for the amount of time it would take me to go and buy her gift. Once I did that, I needed to add in my "prep" time to get ready to go and I was all set for yet another gender adventure into transgender womanhood. 

For the evening, I chose my favorite business professional outfit at the time. A black pantsuit with heels, my best makeup job and shoulder length blond wig. Plus, since it was cold that night, I could wear my long, wool coat to stay fashionably warm. 

As I left the house and headed for Columbus, I was nervous about how I would be received and if I was able to purchase a bookcase would it fit in my SUV and who would load it. I was so afraid of being "discovered" and shunned at the store. But as I entered the place, my fears began to dissolve as I blended in with the other shoppers as I looked for what I wanted. It turned out about that time, my first taste of feminine privilege kicked in. First of all, I did not even need to find a clerk to help me. Before I knew it, an eager guy was ready and willing to help the tall blond in her heels and pants-suit. 

He asked me if I knew what I wanted and in a soft voice I told him exactly what I wanted. In no time at all, he showed me to a cashier and I bought my precious gift with a smile and then wondered how I would ever make it to the car. Again, I should have not worried much at all as two able bodied young men quickly showed up to load my book-case. I loved it when one of them even opened the door for me as we were headed to my car. Brimming with gender euphoria and confidence, I hurried home to gently unload my gift and hide it in the garage. 

Sadly, I went through the process of returning to my male world in record time as my wife was due home at any time. Somehow I managed and was ready to act as if the evening never happened. At least this time I could tell her the truth when she was asking how my evening went. I told her I went shopping for her and to stay out of a certain area of the garage until Christmas. For once that was how the evening ended without a fight or me having to lie about going out as my femininized self.

The internal excitement of what I had accomplished that night stuck with me for quite a while and when it wore off, I had more confidence to shop for her as a woman in the world so I shopped again in other venues for gifts.

Being a trans girl in a furniture store was just the beginning. I will have more experiences to write about as Christmas gets closer.

In the meantime, thanks again for reading along. Your input means so much to me and comments are always appreciated. 

Act Fast...Think Later

Image from VT on UnSplash.

Many times as I was traversing my very long and complicated gender journey, I ran into situations where I needed to act fast and think later. Or, wow, did I really do that?

Perhaps the most impressive example was when I had an ill-advised attempt at wearing water balloons as breast forms. While I loved the feel and bounce of the balloons, deep down I knew the danger I was facing. Someday, I would go too far trying for bigger breasts and one would explode in public. Of course I kept going with the balloons until the possible happened. I had an explosion of water in one of the venues I always went to. When it happened, I needed to act fast and head for the rest room. Fortunately, I made it and there was no other women in the room so I could enter a stall and clean up. Then I was able to make a quick exit from the venue and head home. I don't know what I would have said if anyone had noticed. Maybe I was pregnant and my water broke? 

After the water balloon disaster, I needed to think about what I would do for breast forms which were not as dangerous as water balloons. At the time, silicone breast forms were just becoming popular but were still out of my budget. What happened was a cross dresser acquaintance of mine went on a major purge of his feminine belongings and gifted many items to me. Including a set of breast forms. Since we were basically the same size, the new silicone breast forms worked well and were the proper size. And, most importantly, I didn't have to worry about disasters coming up.

Perhaps you have heard the term "muscle memory" which essentially means you keep repeating an action until it becomes second nature to you. In my earliest days of entering the world as a novice cross dresser or transgender woman, I spent many of my leisure hours attempting to learn how a woman moved and walked. When I did, I am sure I provided many a stranger with a humorous look at my male self trying to move like a woman. In fact, one night when I was in what I thought was a deserted box store, I caught myself being stared at by a guy who suddenly appeared out of nowhere. He was probably a plain clothes security person getting a kick out of seeing me practice. At any rate, I acted fast and left the store and thought later about where I would do my practices. 

Acquiring the basics to present well enough as a woman was difficult for me and required hours of effort and will power. Along the way, I experienced more situations of acting fast and thinking later than I can remember now. I do remember vividly the night when a lesbian friend of mine wanted me to approach another woman at a lesbian mixer we were attending and see if I could get her name. I acted fast and said yes, when in fact I was petrified of being the proverbial "wing person" for another woman. It didn't really matter anyhow because I never got a name. But later, in another venue I got even when I was kissed by another lesbian as my friend sat by herself. 

Maybe acting fast and thinking later just came with the territory of my transgender womanhood. I had always been an impulsive person and nothing really changed except for I had a whole new platform to work with. I think too, when I began keeping company with other women as a transgender woman, my instincts needed to change. I learned quickly how mean other women could be to each other and how difficult it was to watch for passive aggression. Early on, I needed to survive many passive aggressive encounters in the world with other women. 

It was all just a part of the learning process on my gender journey and one I had to face to make it to my dream.   

 

Now What?

 

Image from JJ Hart

As I cautiously discovered I could make it in the world as a transgender woman, rapidly I kept coming to the conclusion of now what.

How would I face a whole new life without the old male standbys to fall back on. I had taken the time and effort to build a family, friends and a fairly successful job which I had to possibly give up. Naturally, I spent hours, days and weeks trying to figure out what I would do once I entered fulltime transgender womanhood. I had long since passed the point of just being satisfied with existing as a part-time cross dresser. 

Ironically, every time I was successful in public as a novice trans woman, I wondered now what I  have I done and what was next in my life. The problem was, I had several major roadblocks which were looming in my life, such as helping to care for aging parents and a spouse who was totally against me transitioning any further than I was. To diminish the impact of all the gender stress I was dealing with, I did what many males try to do and internalize all of my problems. Even though I was going out as much as I could as my authentic feminine self, the fact remained I would have to go back to my old unwanted male life sooner more than later. As Paula from the UK put it in response to a previous post:

"For me it was the depression that followed "putting Paula back in her box", each time I went back to being "him" it was like a bereavement, in the end it was bowing to the inevitable. Arguably transition was the most selfish thing I have done, but like so many others I was insufferable trying to maintain my male persona, in the end it wasn't so much choosing my feminine side as choosing life."

Similar to Paula, the entire transition process for me came down to life and death for me. Like so many other transgender women or trans men, I attempted suicide to relieve myself of the brutal gender related stress I was feeling. Fortunately now, I was unsuccessful and lived to write about the experience. In fact, it was one of the reasons I began to author a blog.  In order to help others. 

Perhaps you are wondering how now what worked following my attempt at self harm. I still was not smart enough to listen to my inner female and tried to purge my fairly extensive feminine wardrobe and makeup. It was during this time too, I began to notice my second wife's health was slipping badly and she would end up passing away at the age of fifty.

Then I really entered the now what part of my life. The door had suddenly opened for me to live my dream of living fulltime as a transgender woman. I followed my soul and began gender affirming hormones at the age of sixty and never looked back.

All the days of wondering now what were behind me. All the risks I took were with it as I began to happily live an authentic life. And, by the way, Paula thank you for the comment and thanks to all of you reading along. 

I Chose Me

 

Image from the JJ Hart archives.

In an extension of yesterday's post, I decided to explore how I chose my inner feminine soul over my forced male existence I was rebelling against.

Basically, the deciding factor came down to how natural I felt as I cross dressed in the very beginning of my gender path to freedom. Very early, I remember vividly how I so desperately wanted to be more than just a boy dressed as a girl in the mirror. I wanted to be the girl. Why did I have to put up with all the male problems I had so much a problem with. 

As I embarked down a very long path to having the courage to finally living as me, as I write about often, the longer I waited, the more baggage I needed to do away with. Often I was my own worst enemy when it came to having any success as a male as it seemed every male privilege I secured someday I would have to give it away. This extended to making any new friends. It was very difficult to be close to someone who may reject me when I set out to live a new life and let the old one go. 

At the many milestones I encountered on my gender path, deep down, I needed to choose me. Especially when I learned there would be more than one major transition I would have to take. My primary go to example was the momentous evening when I suddenly decided I was done with being a cross dresser. I wanted so much more. It was the night I went out to mingle with other professional women getting off work at a bar/restaurant by the mall I always went to. The whole process was basically a mental move, in that for the first time I was going out in my mind as a transgender woman trying to be the equal of any other woman I met. I wasn't a man at all.  It meant the world to me when I was successful and knew right then I could never go back on my journey. Somehow, someway, I just had to be me.

My main roadblock was my second wife who accepted me as a cross dresser but always drew the line at any suggestion of me being transgender. Especially when gender affirming hormones were brought up. She rightfully saw her man she married slipping away and wanted no part of it.

Unfortunately for both of us, I had gone too far to turn back on my dream of living as a transgender woman. I was following my path the best I could and did not want to go back. Choosing me, over the life I had was the most difficult decision I ever had to make. The pressure was on to make my choice and for the longest time, I tried my best to live a life in both the binary genders. Plus, it seemed when I thought I had life all figured out, more and more questions arose. Like what was I going to do about my sexuality was a big one. Was I going to pursue men or become a transgender lesbian. 

Once I made my decision, the rest was easy. The pressure was off and I was free to be the me I should have been all along. What a relief!

Trans Girl Preparedness

Image from Ben White
on UnSplash. 

Since it took me approximately fifty years to fully emerge as a transgender woman, I had plenty of time to prepare.

The challenge comes when we trans women or men need to begin from scratch. We did not benefit from a gender peer group such as other girls to have sleep over parties and experiment with makeup and clothes. No one to tell me I looked like a clown in drag. I learned I needed to resort to the mirror for help but sadly ran into problems when the mirror had the habit of lying to me. I could still look like a clown and the mirror would not tell me the truth.

What I did was go out to into the public's eye and receive an honest feedback on my appearance. In the beginning, the experience was brutal as I was met with stares and even laughter. Many times, I could not wait to go home to the safety of my own room to start over again. I kept thinking, regardless of all the negative feedback I was getting I could do better. For the first time in my life, I needed to decide what I wanted worse, to hide in my closet and not advance toward my dream of ever living a feminine life, or advance and begin the learn the basics of makeup art and fashion which at the least fit me. I found the entire process to be exceedingly difficult for me. 

Spoiler alert. I did learn the hard way what I needed to do to blend in with the rest of the women around me. It was a powerful lesson to learn when I found out how women ruled in their own worlds and how I could join in.  In the meantime, I was learning how to erase my male past and start over. To make matters worse, my male self naturally fought against the gender change to transgender womanhood he was facing. 

Through it all, I was naïve to think I was progressing towards my gender dreams. I thought that just doing my best to look like a woman was all I had to do. When I entered the wild and wonderful world of women, I was excited yet terrified of my future. After all, I was risking all of my male life as I had known it. What would become of my family, friends and income? To arrive at the point of knowing all my gender questions, I just had to be better prepared.

At that point, I started to go out into the world with a purpose to learn if I could make it as a transgender woman at all. Primary issues remained such as communication problems. Plus, I went the distance to try to stair step my way into an increasingly active public community. I purposely tried out more and more challenging situations. Away from the no challenge opportunities I was facing in clothing stores and malls. I even tried to avoid the book stores and antique malls I had become fond of but never presented any sort of a gender challenge to me. I needed to feel OK with who I was, where I was before I was able to move on. 

At the same time, my male life was successful and was pushing me to stay the same and not transition into a women's world even farther. All the struggle did was wreck my mental health. What I did not recognize yet was my feminine self was my dominate personality and needed to be freed. The harder she fought, the harder he fought. Finally, he gave up and I found a deep seated relief I had never known before.

Primarily, after all the time and effort I put into changing my exterior gender to what my inner self was always telling me, was the reason I felt better about my life. Sure, the gender affirming hormones I began to take made the transition easier also but bottom line, I was just prepared to do what came naturally and live it.  

Re-Approval

 

Bar Mitzvah image with wife Liz on left
and my daughter on right.   

In previous posts I have referred to my recent Thanksgiving trip to my daughter's in-laws. 

Fortunately the one hundred mile round trip went without issue and we even arrived just a bit early. For the first time in several years, there were several people there I did not know. For some reason, meeting new people is always a challenge to me. 

This Thanksgiving one of my hopes was my transgender grandchild and their partner would be at the dinner. They were (they is their preferred pronoun) and visiting with them was fun and interesting. It turns out they are just weeks in graduating from "The Ohio State University" with a degree in nuclear engineering. Most certainly, NOT a chip off the old block because I can barely add and subtract. On the other hand, I never set out to ever be a role model in the transgender world. It has been exceedingly beautiful to me to be a role model for my transgender grandchild. 

Also fun was when a group of women at the dinner gathered around me after they helped clean up. Being accepted in women's only spaces is always special. Of course much of the conversation revolves around children and my first wife was even in the group. Since everyone knew my daughter was in the group, there were very few questions of me. I was too busy just enjoying the feelings of acceptance around me. Which for whatever reason was missing in my earlier years of coming out. Very few people knew me before I transitioned and many of them were in the room where I was. 

It was a difficult time transitioning in front of my daughter's in laws but not as difficult as trying to come out to my ex-brothers right wing Baptist family. I was accepted so completely in my daughter's world and beyond, I was invited to stand up and speak before a crowd of people during another of my grandson's Bar-Mitzvah.  I was very nervous but did my best and again I was impressed with the acceptance I felt from the Jewish Temple where the event occurred.

All of this helped me develop who I wanted to be as a novice transgender woman. I thought I knew but until I did it, I did not really know all it would mean to me. I needed to go so far past just presenting as a woman the best I could all the way to creating a whole new person. When I did, most certainly, I had my ups and downs with the entire process and I needed all the acceptance I could find. Included was all the re-approval I could get. 

That re-approval came recently at our Thanksgiving dinner. As with so many other women, they don't know how much they have done with me to help me along. It meant so much to have the chance to  recharge myself for the future.  

Trans Girl at Black Friday

Woman Shopping on UnSplash.

As I advanced on my feminine path to transgender womanhood, at certain points I needed to do more and more traditional feminine activities which cemented my claim to be a trans woman.

One of those was joining all the women in the world who were out and about shopping for the bargains bright and early on "Black Friday" or the day after Thanksgiving. My second wife for years was part of the crowd and made sure she was one of the early shoppers. 

Of course, I always wondered what the attraction was to go out and battle all the crowds, except for saving a little bit of money. Finally,  many years of wanting to shop with my wife as another woman came to an end but suddenly, on the other hand, I had the chance to shop on "Black Friday" as a woman by myself. Along the way, my second wife became the assistant manager of a large bookstore and of course "Black Friday" was one of their biggest days. So, I knew in advance she would have to work and I arranged my schedule so I did not. 

On the morning of shopping, I was excited as I prepared myself for a morning I had only ever dreamed of. First I did all the shaving preparation, including face and legs. I needed to calm down before I dressed in my favorite bulky sweater along with my best denim skirt and comfortable flat walking shoes. Then I began the more crucial part of applying my makeup and wig after I had calmed down...somewhat. After I reached what I considered to be a good presentation which would blend in with all the other women shoppers I would encounter, I gathered my courage to leave the house and head to a nearby upscale mall which I was very familiar with.

Unbelievably, in a very crowded parking lot, I found a space close to one of the entrances. As I checked my makeup and hair for the final time, I thought back to all the times I wondered what it would be like to shop with the other women on "Black Friday" and here I was and into the mall I went. My initial reaction was one of calm because no one was watching me, they were on a mission to find the best bargains and complete their shopping lists to bother about a transgender woman in the crowd. 

Since I wasn't really there to shop anyhow, I just browsed a few stores and bought a few small gifts for my wife before my shopping came to an end. After all, I had accomplished my goal of experiencing "Black Friday" shopping up close and personal as my authentic self. It was another item I could check off of my transgender woman bucket list.

Time flew by and  I needed to be back home to change back into my old boring male clothes to go to work, I needed to bring my dream day to an end earlier than I liked. 

Possibly the biggest lesson I re-learned that exciting day was the power of blending in with the rest of the women around me. As long as I could accomplish looking similar to everyone else, I could present well enough to get by. My first Trans Girl at the "Black Friday" shopping experience was certainly worth it.

Happy Thanksgiving?

As I sit here watching the Macy's parade, it brings back all sorts of bittersweet memories. 

Looking back, Thanksgiving and Christmas were the two biggest days of the year for my second wife. She went all out for both, often feeding up to twenty people for Thanksgiving. Our door was never closed to anyone who needed a place to socialize and eat. The day also marked the beginning of a very serious stint of putting up all of her extensive decorations for the season. 

At the time, I took it all for granted and thought it would go on forever. As I grew older, I learned the hard way nothing lasts forever. I am fortunate in that I still have an extended family to celebrate  Thanksgiving with. If not for my daughter and my wife Liz, I would be joining no one for the holiday.

I used to have blood family with a brother. A decade ago I came out to my only brother and sister-in-law. I was naïve and thought I might receive the same positive reaction I had from my daughter. I was wrong and was told they did not want me at the family Thanksgiving Day dinner. Naturally, being  shunned  because I was coming out as my authentic self hurt me deeply. My brother and I have not spoken since. 

However to make up for it, I was invited to my daughter's in laws for the holiday. Plus I made up for the slight from my brother when I was invited to small get togethers in Liz's family when her Dad was still living. 

In the transgender world, sadly I am often not the example, as so many in our community have no family remaining to socialize with. Mainly because they were not accepted by their families. It is especially cruel when you have to remember times with the family by yourself.

On this Thanksgiving, I hope you have someone to socialize with. Even if it with a local LGBTQ organization. Many in our area often offer dinners you can participate in. 

Regardless, I hope you have a good turkey day!   

Trans Girl in a Wig Store

 

JJ Hart Blonde Look.

Perhaps I should say trans girl in as many wig stores as she could find. 

Once I arrived at the point where I could even afford a nice hairpiece, I was like a kid in a candy store. So many styles of wigs to choose from and so little time to try them all on. I wish I could say I quickly became better at the process of choosing my crowning glory. Sadly, similar to the rest of my outfits or fashion, I was going too trashy to blend in with the women in public. I was telling myself since I needed to overcome a large head and body, I needed large hair to do it.

Also, to find a wig store I had not been to, I needed to drive long distances. Primarily from my medium sized hometown which had no stores which specialized in wigs all the way to Dayton or even Cincinnati which had several. 

Once I made the trip, I needed to learn several of the shop owners were not really interested in how I presented in new hair but were very interested in how much I had to spend. The owners could not do much to direct me in the proper direction of what I needed to look better as a transgender woman. Being fair to them, my male ego was in the way, telling me how to choose because he thought I would look better. Many times, I ended up buying what I today call clown wigs which were guaranteed to get me recognized or clocked as a cross dressed man. The wigs were good for Halloween and not much else.

All in all, the choices were bewildering. I felt as if I was back in my beginning days in the makeup department when I was attempting to figure out what product I wanted to try. In the wig store, I had to choose a color of hair I wanted, style I wanted and even which hair I wanted, human or synthetic. The possibilities were endless. 

In the beginning, my default color was always red or auburn before I started to shift away to other shades. For years I rotated between dark colors and blond which became my favorite. I was enjoying the changes in my appearance until I needed to settle down into one look when people began to recognize me. No more changing my name with my wigs. Settling down was difficult but something I needed to do as I followed my path to transgender womanhood. 

Through the magic of gender affirming hormones and good genetics, I arrived at the point where I did not need to wear a wig at all. In fact, one of the best gifts I had ever received came from my daughter when she provided me with a visit to her own upscale beauty salon. Even though  the experience was terrifying at first, I ended up loving it and could not wait to go back. Almost immediately I understood why cis women spend so much time and money at their salon. 

Most certainly, I cannot overstate the importance of hair to our outfits and fashion as transgender women or cross dressers. Hair demands all the effort we put into it. 

Ditching Good for Better

 

JJ Hart with Ohio River.

As I made my way along my gender path, I was always looking to go from just good to better. 

I always wanted to present better as a girl my age all the way to moving like one and even doing my best to act like one. I did my best to be a keen observer of what the feminine gender around me was doing at all times.. If they were wearing mini-skirts, so should I was a prime example.

Sadly, I was hindered by my meager financial situation until I grew older and could afford more fancier accessories such as clothes and wigs. Even still, nothing was stopping me from pursuing my gender dreams of living as a woman. If only I could. That is where my path became more and more important. For example when I finally broke out of my closet and did all my own shopping, I learned the hard way what looked good on me and what did not. From there I could build on to my success and go from good to better.

I became especially good with my feminine business attire wardrobe. At thrift stores I managed to find a black pant's suit which paired nicely with heels or flats and my should length blond wig. I even had a wool full length coat to go with it for the winter time when I went shopping. For the warmer times of the year, I found a lime green business suit with a shorter skirt which I paired with pastel green opaque panty hose and matching kitten heels. I found I went from good to better either time of the year and presented relatively easier for the first time in my life. Gender euphoria at it's finest.

All of my fashion advances did not prepare me for face to face encounters with other women in the world. Chance encounters with store clerks were easy until I began to stop at restaurants to eat. I needed to order from a menu while at the same time doing my best to sound like another woman just having lunch away from her job. Until I gathered the confidence to practice it, the entire idea of talking like a woman was once of the most difficult things I had ever attempted.  I even went as far as going from good to better by taking vocal lessons to usher me into my transgender womanhood. 

I often think I inherited my drive to always do better from my parents. Nothing was ever good enough for them. If I had received a B in a class, why did not I get an A was the routine I grew up with. Imagine the irony my parents would have felt when they found I applied the same thought pattern to a gender issue they were very against. All I ever wanted was to be a woman, transgender or not and needed to work very hard to overcome my male bonds to do it. Plus I always felt if I was going to be successful as a transgender woman, I would have to try harder than the average woman to succeed. 

So along the way, I needed to not accept good and kept trying to achieve being better and better as a transgender woman. I wonder what my parents and my second wife would have thought of me now. Hopefully they would be happy for me, since I have arrived at the place I have always wanted to be in life. If I had done it sooner, I would have undoubtedly been an easier person to live with.