Sizing Up the Crowd

 

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Recently, when I met friends at a local brew pub for brunch, I needed to walk the distance of what was called the "great hall" to meet the group.

Once again I needed to make sure I was standing up as straight as I could, while throwing my shoulders back and faced the reality all transgender women face, was I going to be spotted as some sort of a gender impostor and even laughed at. I didn't and even though the brief walk felt as if it went on forever, I made it to our table without incident. At that point I thought I had it made, until the young server called me "sir". Which is another sad experience I have previously written about. 

For some reason, when I transitioned into a feminine transgender world, I didn't think the public would share the same fascination with studying other women as I did. I can't tell you how many times my old guy self aggravated my second wife (and others) by trying to sneak a peek at an attractive woman. For whatever reason, I couldn't explain to them I wasn't looking because I desired the woman, it was because I wanted to be the woman. At the time, I was having a difficult time wondering if I could ever achieve my dream of cross dressing out of my old unwanted male self. There were so many working parts of a woman to duplicate, the whole process seemed impossible. I needed to fashion my own hips, breasts and hair just to arrive at a point where I could put the entire feminine package into motion. 

It wasn't until I began to leave my dark and lonely gender closet behind and attend transvestite mixers did I begin to think I could succeed. Through the help of the mixers, I was able to judge how other cross dressers were successful with their presentations...or won't. I saw everything from men in beards and dresses, all the way to beautiful transgender women who were completely undetectable as former boys or men. As I sized up the crowd, I knew which direction I was headed. Most certainly I did not want to be with the bearded crowd and wondered to myself if the transsexual group was where I needed to be. Keep in mind, this was back before the transgender label was widely understood or used. What amazed me too was how intense the pressure was to size up the crowd and fit in to where you belonged. 

Little did I know, I was just beginning my trip out of the closet and into the world and I would need to obsess on my appearance until I gained the confidence to go forward as the person I was. Deep down I knew I would never be the prettiest woman in the room, I just wanted to be the trans woman at peace with herself. So when the crowd sized me up, they recognized who I truly was and it was good enough. I learned also, the greatest majority of the world didn't care about me anyhow and they were involved in their own little worlds. My second wife was always fond of telling me it always wasn't all about me when it came to my cross dressing and she was right. It was just the ones who did care who became the problem. As I made my way along my gender path, I was fortunate to dodge most of the haters and live my life without severe incidents.

I am a firm believer in the younger generation doesn't see gender as a threat and in the future sizing up a younger crowd will be less of a threat to transgender women and men everywhere. I, on the other hand, when I chose to live a life as the high maintenance gender chose to always be on the stage of life. 

You are Such a Girl

Boho Woman from Brooke
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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.