Every time I Looked Around...

Image from Mahrael Boutros 
on UnSplash

Until I began to become used to the new feminine world I was beginning to navigate as a transgender woman or cross dresser in those days, it seemed as if everyone was looking at me.

I was not used to the fact that both main binary genders look at women. Even though they do it through vastly different lenses. Men of course have the tendency to add a sexual aspect to how they view a woman and other ciswomen often compare other women to how they look and how much work did the woman put into her presentation. As any beginning cross-dresser learns early, it takes a lot of work and effort put into a quality feminine look. Especially when you are making the leap from presenting looking like a man with your testosterone poisoned body, all the way to being able to blend into the world of ciswomen effortlessly.

I know with me, before I could begin to blend in with my new world, I needed to shake all the cobwebs of male feelings I had about doing it at all. For the longest time, I listened to my male self on how he perceived women in the world as sexual objects and tried to influence the way I was presenting myself. What happened was, I was dressing too tight and too short in my clothes and attracting too much unwanted attention. Not only was everyone looking closely at me, I received negative feedback because I was doing it all wrong. I was fighting a losing battle with the age that I was and the body shape I had to stubbornly realize I could not go on that way and hope to ever try to live my dream of being a fulltime transfeminine person.

Then, I went back to my cross-dressing drawing board to set out a whole different way of trying to present myself. Out went the way too short skirts and dresses and in came more manageable denim skirts and oversized flowing tops designed to cover my broad shoulders and lack of hips. I even went to the extent of going on a crash diet so I could find clothes in the thrift stores I was haunting that fit me. Along the way too, it is worth mentioning, I started to take much better care of my skin after my daily shave which helped me to wear less makeup. If everyone was going to look at me, I needed to give them my best effort.

One thing I could not hide was I was a big woman, and I needed to not be ashamed of it but to understand there were plenty of other ciswomen in the world who were the same size as me. So, I began to look for them to see how they moved about in the world. Even though I was right around the six-foot tall mark, I could still wear my cherished high heels. Even with jeans and a tight top which accented my new properly proportioned silicone breast forms I was gifted by a cross-dressing friend who was purging all his feminine belongings at the time.

Amazingly to me, my life as a newly realized transgender woman begin to come together for me. I started to be able to move around in society without causing undo attention while at the same time completely enjoying myself. I even went to the point of buying sunglasses which hid my eyes so I could watch others to see if they were watching me. It was a great way to judge how well I was doing in my ongoing challenge of who was watching me and who was not. I learned I was not attractive enough to attract much cis male attention but attractive enough to be sized up in the public by the ciswomen I encountered. Most importantly, I was getting used to the attention I was receiving and often I wondered where it was if I did not receive it.

The way I began to see the attention I was receiving was I craved it because of all the hard work I had put in to being an attractive woman anyway I could. Positive attention was feedback that I was doing something right and the very little negative feedback I encountered could be overcome easily because of my new overall confidence. Which became my number one accessory I needed when I found myself in shark (human) infested waters with potentially dangerous people. My new training as a trans woman taught me to look ahead and do my best to not put myself in dangerous situations in the new world I was in stripped of my old male privilege of personal safety. Very quickly, I learned the problems of being a lone woman in a poorly lit deserted area.

I was able to test my passing privileges when I transitioned away from the gay venues I was going to and tried my best to become a regular patron in many of the very same big sports bars I used to go to as a man. It turned out to be easier than I thought it would be and I was not noticed much at all by cismen or ciswomen. Even though, on occasion, another woman at the bar would take the time to talk to me. I think more than anything else out of curiosity. Why would an ex-man such as me want in her world was the major point women of all sorts were trying to find out.

As I said, I began to crave and even expect the attention I was getting as the only transgender woman in the venue. Except on the nights that my trans woman friend Racquel met me there. We ended up having about five venues we went to that accepted out business with no problems. I also went to monthly lesbian social mixers with my two friends in many of the same places and I was overjoyed when another lesbian approached me. I guess you could say I was causing the right kind of attention.

Getting out and learning how to know and appreciate the right amount of attention even carried over to an on-line relationship I stumbled into with my future wife Liz who contacted me from an ad I had placed on a woman seeking woman dating site. Fourteen years later we are still together, so I guess I looked in the right place for attention.

Thanks for giving me your attention for my experiences! Any feedback or responses is always welcome.