You are Such a Girl

Boho Woman from Brooke
Cagle on UnSplash

Jen recently responded to my comment about walking in heels on stairs while being slightly intoxicated. 

Jen, who I have known for years happens to be a cis-gender woman and said she has never mastered the art of walking in heels. I have always appreciated knowing Jen because of her acceptance of me as my authentic transgender self from the first time we met. As far as me judging her for not wearing heels, it never happened. 

Perhaps, I quit judging women from their footwear came primarily because all of the women I socialized with were not the girly-girly types and never wore heels. At that time, I still could wear heels but decided not to because of adding to my height as a trans woman. All my friends were shorter than me and I did not want to tower over them. 

Being such a girl, did not reach all the way to wearing makeup and the feminine clothes I wore. In order to stand any sort of a chance to present well as a novice transgender woman or cross dresser, I needed to take advantage of all the benefits which makeup gave me. In fact, when my second wife was alive, she used to call me the "pretty, pretty princess" in response to all the time I took to apply my makeup. When she wore little to none. Obviously she didn't have to worry about the benefits of fashion to just exist in the world as a feminine person. 

As my life progressed and changed, my knowledge and application of makeup needed to also. While it was obvious I still needed to take advantage of cosmetics, the new pressure was on to look natural while I did it. In other words, to appear as if I wasn't trying too hard. I desperately needed to blend in with my group of cis-women friends who again did not wear any makeup at all. It was during this time in my life when I really began to step up my skin care routine. I made sure I was able to apply a good moisturizer after everytime I exfoliated or shaved. The entire process enabled me to use less foundation and achieve a more natural look. I was also given a positive head start on when I started gender affirming hormones (HRT) which naturally allowed my skin to soften and smooth out. 

Of course, my basic fashion sense came into play and I was given a head start by my feminine preferences in clothes. Growing up, I had always admired all girls, tomboys and all. They were the women who were able to show off their so called masculine side without anyone questioning their basic gender or sexuality. While I had to play the same old male game of never showing a softer side. I took it in stride the best I could and later on became a big fan of women in "Boho" fashion and bell bottom jeans, In fact, I loved them so much, I was harassed at several transvestite mixers I went to when I wore my pants. Comments were why don't you wear a dress because you can wear pants anytime were common. I politely told the other attendees to mind their own business and went on about my own. 

Wearing pants before my HRT hormonal days involved extra attention given to how my hips and rear appeared in woman's clothes. Similar to so many others, I resorted to using foam rubber inserts in my panty hose to give me the illusion of hips. Depending on the top I was wearing, I pulled off the illusion fairly well without having to resort to wearing restrictive undergarments such as girdles which to me took away much of the sensory pleasure I was feeling at the time. 

I guess you can say, compared to many of the other cross dressers or transgender women I knew at the time, I went rogue in my approach to being feminine. For whatever reason, I always admired the women who could take a tomboy look and work it into a fabulous fashion statement. 

I hope I provided Jen with a little feedback on the way I feel about her never wearing heels and how much I appreciate her (along with all you others) for reading and commenting on the blog. Thank you! 

    

Gender Expectations

 

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

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

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

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

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

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

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

Catching the Trolley

 

The Trolley Stop, Dayton, Ohio

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

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

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

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

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

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

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

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