Trans Girl in the Winter

Image from Freestocks on UnSplash.

I happen to live in Ohio where there is often a weird mixture of the four seasons of weather. For example, when it seemed fall has set in, summer returns and the sweaters and leggings you have pulled out have to temporally go away. Now, around here we have made our way into winter. Which means I have had to dig a little deeper into my collection of leggings to find the lined ones. I love the soft feel of the leggings and how they keep me warm when the temperature dips well below freezing.

For my wife Liz and I's winter time walks, I usually pair my favorite leggings with my furry boots and bulky soft sweater before I have to go outside and brave the elements. These days, I need to force the issue with my walks since Liz and I are going to visit the Florida Keys in January. So I need to do my best to walk as long as I can when we go. Since there is thirty days away, there is plenty of time to write about our winter vacation before it arrives. Such as my first time swimming as a transgender woman.

If I had my choice, I would choose winter over our hot, humid summers any day. I like the fashion and the fact it is easier for me to stay warm in the winter rather than cold in the summer. I know possibly, I may be in the minority of all transgender women who value the look and feel of bare skin in warmer times. While I remember vividly the freedom I felt when I could finally shave my arms and wear short sleeved women's fashions, over the years, the feeling has somehow went away. One way or another, I have traded the feminine feeling of leggings for the sensation of shaved legs in the wind.

Either way, the entire fashion process is one of the reasons I enjoy my transgender womanhood so much. The planning ahead for the seasons means so much and winter is just a portion of the process. Of course we will see if I am just as enthused if we get any sizeable snowfall in December since I have one Christmas lunch coming up with the Cincinnati Alzheimer's diversity council as well as a Yule get together with Liz's circle of friends. During which I will have the opportunity to explain why I turned down an interview with a local television reporter after the election. 

So there is quite a bit coming up in December, including awaiting the arrival of a new laptop I thought I would go ahead and purchase before the proposed tariff's go into effect driving prices upwards. It will be interesting to see how easy or difficult the set up will be. I am not very technologically advanced. The laptop was one of the biggest purchases I have made in a long time. It was an online Cyber Monday purchase so I did not have to put up with any lines or pestering sales people. Patience, along with many other attributes will have to be my main goals following trying out a new laptop in over a decade. 

Overall, the month of December is more enjoyable with the fashion and festive Christmas lights in the neighborhood. I have respect for those who put effort into holiday decorations since all the work I put into my second wife's extensive decorations 

It all makes up for the drab months of January and February. Being a trans girl in the winter is yet another challenge. 

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.  

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. 

All I Ever Knew

Circa 1940 image
of Virginia Prince

 Every once in a while I receive the question when did I know I was transgender.

The easy answer is I always knew but I needed to figure it all out. The more complex answer is I needed to figure it out after a series of transitions during my life. Two major ones occurred when I made the jump from from a very serious cross dresser all the way to a novice transgender woman. The second problem I had was back in those days, terminology to define a transgender woman or man had not yet been invented. Basically back in the pre-internet days when all we had was the preaching of Virginia Prince and her Transvestia publication which I could not wait to receive in the mail. Seeing all the pretty cross dressers just made me want to do more to improve my feminine appearance.   

I worked harder on my appearance than any thing I had ever done before and slowly began to see improvement over my testosterone damaged male body. It was all I ever knew. 

As I entered my transgender womanhood, I felt deep down inside I was doing all the right things, even though I was jeopardizing all the facets of my male life I had worked so hard to put together. What would I do when my family, friends and bosses discovered my deep secret. It ran so much deeper than just wanting to wear women's clothing. I wanted to be a woman and live a feminine life. 

During that portion of my life, I basically went into attack mode, doing every thing I could to learn how being a transgender woman would affect me. Every free moment I had, either I was out in the world as a woman or day dreaming of the times when I could. Naturally, I learned a lot, good and bad about what life had in store for me if I kept on going towards my gender dreams. I found the grass wasn't always going to be greener on the other side of the gender border as I lost all of my male privileges but hadn't gained any of the female ones. 

Soon I learned, it was truly all I ever knew. Somehow I was born to be feminine and not masculine. Which meant years of struggle to right the gender wrongs I was living. The struggles on occasion were crushing and keeping going was very difficult but I did. Probably because I was behind before I even started. I was born into a very male dominated family which had very few girls to play with. Plus, I never had any feminine characteristics myself to begin with. Add it all up, then include me never having any girl time with anyone all teamed up for a rough start for me on my gender journey.

Even still, my gender path was all I ever knew and staying on it finally made me successful. 

Trans Girl Passing Privilege

 

Witches Ball Image. Tom on
left.

Passing privilege has been one of my biggest gender paranoia's over the years. Many because I did not begin my journey with any feminine characteristics I could see. Testosterone poisoning had essentially ruined my life when it came to establishing passing privilege. 

As I began to add angles to my body along with unwanted body hair and muscle mass, I began to think ever presenting well as a cross dresser / transgender woman would be impossible. In order to make my gender dream possible, I needed to look around at the other women my age and try to blend my style with theirs. The whole process was difficult and I made many fashion mistakes along the way. Even though I did, I managed to survive in the world as a novice transvestite on my own and move forward. Mainly thanks to brief moments of gender euphoria which always propelled me forward. To do so, I learned how important for me it was to blend in with other women. All I knew was, I enjoyed it immensely when other women would take the time to talk and communicate with me as an equal.

Through it all, I learned that even if I was not the most beautiful woman in the room, many other cis-women were not either. Since women operate on a more layered existence than men, there were many other possibilities to be successful in the world other than just being attractive. In fact, being transgender gave me an extra quality to my existence which many women were drawn to. As I crossed the gender frontier into a new feminine world, ironically I found I had more interest from women than I ever did when I was a man. 

Probably, one of the more profound statements I was ever told was when my transgender friend Racquel told me I passed out of sheer willpower. Which I took to mean (again) I was not the best looking woman in the room but went out into the public's eye anyhow. Together, we went to many so called straight venues together and had a great time with very little public push back, Even if I was passing out of sheer willpower, I was doing it successfully. Which was all that mattered. 

It mattered even less, when I was able to expand my small circle of lesbian friends who put the icing on the cake so to speak when it came to passing privilege. We were able to attend several lesbian mixers in Dayton, Ohio at several different venues. Even though I was initially very scared to go, I was quickly put at ease when I found I could blend in with the group in the venue. Sometimes the venue would be gay and sometimes straight which added to the excitement. All I know is one night, I was asked to be a lesbian wing person for my friend who was too shy to approach another woman and ask for her name. I even was able to steal a few kisses on the side one night from another woman I met. Willpower passing was great. 

I don't have enough power to do it but I think "passing" should be changed to "blending". With blending, you have the choice to dress with the other women you are going to be around and you have the choice not to if you like. In my case, I always wanted to do the best I could to enter the world as a transgender woman and blend in with the other women who were going to be around me. On the other hand, I understand also it is a trans woman's privilege to go to the grocery store in her heels and hose to do her shopping. It is all part of the fun of entering the women's world. 

The biggest problem with trans girl passing privilege is the amount of stress and attention put into appearance by the media and the outside world. The competition to look better seems to get stronger with each generation with the internet and social media being the major culprits. When the stress goes up for ordinary women to look better, it follows the pressure to be even better is real for transgender women and their quest to blend in with the public. 

At least now, there are plenty of self help makeup videos to help the novice trans girl along plus several of the big makeup stores offer advice and products too. Many more places than transgender women such I had when I was first coming out. Maybe it all equals out. 

Being Prepared for a Transgender Future

Image from Chad Walton
on UnSplash.

For nearly a half a century, I hid behind the idea I was nothing more than a cross dresser who liked to wear women's makeup and fashion. What harm was I really doing? The answer is, the only harm I was doing was to myself.  

Had I known all I was doing was to prepare myself to transition into a transgender woman later in life, I may had approached the process in a different light. The problem was, everything seemed to be so life and death serious. Primarily since I was locked into a very lonely, dark gender closet. I had no role models around me to prepare for a highly uncertain future. No one to tell me my make up looked clownish and my skirt was way too short. I only had my old male ego and a mirror who were teaming up to make my life miserable. 

I really learned how miserable I could be when I began to leave my closet and explore the world.  Being stared at and laughed at to my face taught me the mirror could lie to me and the way my old male self was telling me to dress was all wrong. I was going back to my cross dressing drawing board too many times before I learned what I had suspected all along, becoming a part of the feminine gender was going to take a lot of work. I needed to go so far to finally understand all along I was a woman cross dressing as a man and not the opposite. 

The more I began to understand where I was in life, the more the future came into focus and preparations for major upcoming decisions became important. As I was exploring and building a new life as a novice transgender woman, it became clear to me I could indeed live my dream of living as a woman. Before I could arrive there, I still had heavy preparation work to do. There were major issues of coming out and telling what was left of family and friends I was a trans woman. Once I did, there would be no more running home and hiding in the mirror wearing a dress, The first person I told was my only child (my daughter)  went very well and I was emboldened to tell more people such as my only sibling ( a brother). He accepted my transness terribly so I ended up with an even split in salvaging any of the family life I had left since my parents had long since passed away.

The next crossroad I needed to navigate was what was I going to do about supporting myself in my new world. Following quite a bit of planning and preparation, I decided I was close enough to being able to take an early Social Security retirement which back in those days was sixty two. To get there, all I had to do was work another two years. Ironically, during the two years, I was able to prepare even further for my future when the Veteran's Administration Health Care System I was part of suddenly began to accept HRT or gender affirming hormones for veterans. So, the extra two years gave me the time to further prepare for a future which included changing all the legal gender markers I could including a new legal name. 

Since I was newly single again following my second wife's sudden passing, I really could use the time to prepare for the final transgender transition into a new life I had been preparing for since I was born.  

You Can't Buy Love

Image from the 
Jessie Hart Archives

 One of the first lessons I learned when I was first brave enough to date girls was spending more money equaled to more dates with certain girls. Sadly, the plainer the girl, the less potential spending was going to happen. When I flipped my gender, I found out how evil it was.

As a transgender woman, I was or am not the prettiest woman in the room. As such, I never managed to have many dating interactions with men who most of which just saw me as some fetish object. They wanted the first date to be a motel room. I drew the line at any sketchy first dates and demanded a meeting in a public place of my choice. What happened then was a predictable amount of being stood up on possible dates. While I did have a couple meaningful dates with men, often they were unscripted moments in the regular venues I went to often. One night in particular happened with a man called Bob who treated me completely as a woman and I loved it. He lived far away and was married so there was no chance at any further involvement. 

Through that period of my life I was questioning my sexuality also so any dates with men added to my possible knowledge. The farthest I ever went was very brief episodes of heavy petting or making out. From it all, I learned I still preferred the attention and company of women. With the help of a few female friends I learned the meaning of what it meant to be to be a transgender lesbian. In order to do it, I found I didn't have to have a lot of money spent on me to be happy. I was more into spending more money on my feminine self to attempt to improve my public's appearance. I ended up saving every extra penny I had to buy that next extra wig I didn't really need to be more attractive than ever before. At least in my mind. As I acquired more fashion and makeup, slowly but surely was acquiring more acquaintances to try my new fashion out on.   

Which leads me to another woman I don't mention much anymore who is Amy. Amy is the woman who recommended me practice with a banana to get ready for my intimate moments with men. So as you can tell she wasn't shy. One day in particular  with her comes to mind when she invited me over to her house for a spaghetti dinner with friends. I didn't really ask who else was coming, I jumped at the chance to enjoy a home made dinner. Fashion wise, Amy had only seen me in my short denim skirt days, so I decided to wear one over to her house again not thinking who else would be there. It turned out she also invited two men so the group included a cis woman, a transgender woman and two men who were seemingly ill at ease with me. I made the decision to join Amy in the kitchen and serve the men their delicious Italian dinner. I decided if the men were going to be ill at ease with me, I wasn't . I enjoyed the meal, helped clean up the mess, stopped to socialize with Amy and left the men behind. Just another learning experience.

I finally was able to slow down on expenditures on fashion and makeup and spend more on my personal interactions. My experience with dealing with both sides of the binary gender spectrum helped me to truly understand what buying love really meant. I understood both genders often expect intimacy in return for how much money you spend. The last woman I ever dated me as a man suggested to me we go to an expensive steakhouse for food before our first date. I politely saw through what she was up to and declined and we went to a more reasonably priced venue of my choice. Probably dooming our relationship from the beginning. She was quite attractive and a diva to begin with so I figured she thought she could do better than me and our brief fling ended after three or four dates.

Since we live in a money driven society, buying love is hard to do and even more difficult to resist as a transgender woman.  

Transgender Validation?

 Over the years and especially in the very beginning, I worked very hard to achieve my validation as a transgender woman. Or, better yet, being validated as a woman at all. To arrive at where I desperately wanted to be, I had to go through many steps...literally.  My example is was when I would practice walking femininely when I perceived I was reasonably alone in larger venues such as big box stores. Even though I was fairly certain I was not being observed, I am sure I probably made a security person's night on occasion. Regardless, I was obsessed with all things feminine. 

My obsession's of course led me into all sorts of clothes and fashion accessories. Money became the biggest concern before and after my wife's death. Before she passed away, I saved all the change and extra money I could to sneak out and shop for new clothes which I was certain would enable me to become the desirable feminine person of my dreams. I became very good at shopping discount racks at stores and going to thrift stores hunting for bargains. The mirrors in more than a few of these stores became my instant friend, for better or for worse. Another example was a powder blue wool coat I fell madly in love with at a certain  coat warehouse store. I went back so many times to try it on I am surprised I didn't get asked to leave. Sadly, I was never able to afford the coat.

Once I was able to afford a few cherished articles of feminine attire, I had to decide how "cherished" they really were and where I was going to hide them from my wife at home, It took me awhile to gather up the courage to use the women's dressing room, so even though I was getting better at sizes, it was still basically taking chances on which clothing's sizes would actually fit. What I mean is, one company's large would be another companies' medium. Plus, I had to go through my "teen girl" years when I tried to wear everything too short or too tight. It was no way to be validated anywhere but in the mirror which was lying to me. 

Now, lets get back to where I could actually put the items I purchased. Fortunately we lived in a big two story 1860's brick I was restoring, so we had plenty of storage space in out of the way closets. Closets that for some reason my wife never looked in. If she had, I am sure all hell would have broken loose if she had discovered the short, flirty tennis outfit I had put together to wear to the mall. All in all I think I probably ended up with three storage closets for my ever increasing wardrobe. 

Photo Courtesy
Jessie Hart

Looking back, I suppose all my obsession with women's fashion was a natural progression in my search for validation as a novice transgender woman. Today, I am more utilitarian in my approach to fashion. With the condition of my ankles there is no way I can wear heels of any height. So my charcoal boots with the one inch heel is the best I can do. The boots go well with my leggings, jeans and sweaters. Now with spring and summer approaching of course I have to shift wardrobe gears back to my collections of tank tops, t-shirts and blouses. I also have two soft maxi dresses which I adore. I save them for the hot summer months. 

 For me, a large part of my transgender validation now comes from the fact my breasts, hair and hips are all mine, From hormone replacement therapy of course. 

I still believe the tipping point for me in my validation came when I discovered I should be dressing for other women, not men. By doing so, I could blend in much easier with society and be accepted. Once I reached that point, my life as a novice transgender woman became clearer. 

Being human (I think) the fascinating part of all of this comes from the fact we are all different. More and more I am learning about couples staying together as one of them transitions. Yet, there are so many others who are forced to face the task of crossing the gender border to play in the sandbox  by themselves. Thus the points of validating your transgender self can be a highly fluid process. 

It's too bad the path to transgender validation can't be easier and more enjoyable. Not one of the most difficult journeys a human can take.