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.