Not Fooling Anyone

 Early in my days as a novice cross dresser, I was obsessed with "fooling" the public into thinking I was a cis woman. As proof, when I look back at my earliest blog posts, I see a trend. I am almost completely into my appearance and not much to do with the feeling associated with being out in the public eye as a woman at all.

While we are on the subject, Mark sent in a question asking why I separated my time as a cross dresser with my time as a transgender woman. In essence Mark my idea of being a cross dresser was the process of looking like a woman. Being transgender to me was the process of coming as close as I could to becoming a cis woman of different upbringing. I have always believed females are not born as women. It's a process of socialization they go through to claim the title. Of course men go through the same process. So transgender people can too.

Photo by Daniel Lincoln on Unsplash

 I guess I could say my time as a cross dresser enabled me to learn and see if I wanted to take the next step to being a transgender woman. The point of no return for me was when I started hormone replacement therapy. Which brings up the question of why it took me so long. The answer is very complex and varies from person to person. In many ways I am very envious of the young transgender girls and boys who are able to come out and live as their authentic self at a young age. In many ways, at my age, I see myself as sort of an unwilling pioneer because times were so different and difficult to come out in as I was growing up in the 1950's and 60's. 

So, who was I fooling? Sometimes quite a few people when I started to try my hand at going out into a feminine world. At the time I thought the world was primarily a masculine one with women being around to look good and to birth/raise children. I was completely wrong. Once I started to dress for the approval of or to blend in with the rest of women in society I started to be accepted for at the least a transgender woman. I found also, most of the people didn't really care. They were in their own little worlds. Stay out of their way and they would stay out of mine. 

All of a sudden I didn't care anymore if I was "fooling" anyone into thinking I was feminine. After I quit fooling myself, my gender puzzle came into focus. 

My entire life, I had been trying to fool myself into thinking I was male orientated at all and the process hurt me deeply. I was the biggest fool of all.

My Moral Compass

 As probably with  many transgender women and/or men of any age, our moral compasses have been tested. Of course I am no different. As I look back, there were so many chances I had to ignore my personal compass and set a vastly different course in my life. 

Photo by Ahmed Zayan on Unsplash

I learned the hard way my compass had several different settings other than the North, South, East and West. I found I could easily add an N" for no and a "M" for maybe. Very early in my feminine development I learned also how many others were crossing the line as far as their compasses were concerned. My first example was from the so called hetero cross dresser mixers. It seemed odd to me the number of attendees would pair off in couples and disappear to one of their rooms. My evil mind considered the "hetero" part of attendance was  not mandatory after all.

As it happened, I had a chance at my own encounter with a guy after one of the mixers when I had begged my way along with the group I called the "A" listers.  To make a long story short, we all ended up in this local neighborhood tavern  and I was the only one who was approached by a stranger and asked tf he could buy me a drink. My moral compass wavered quickly in the second I had to react and said no thank you. Of course I was married at the time and as my compass wavered to "M" for maybe.

Over all years it turned out I had plenty of chances to use my compass. Most of them turned out positive. You notice I said most. 

My biggest problem came when I really started to explore my possible life in a feminine world when I was still married to my second wife who passed away. Very quickly  I started to break the agreements we had concerning ne going out in the world as a woman. She always knew I was a cross dresser but was completely against any suggestion of being transgender. So, I used any time that I could to get out of the house and learn if I could indeed cross the gender border. Fairly quickly I learned I could and the whole process felt so natural. 

The problem became my moral compass told me I was cheating on her with myself and I felt terrible. The last thing I wanted to do was to hurt her and ruin our relationship but I had gone too far to turn back.

This was also the time I could have changed what the "S meant on my compass from South to Self Harm. The guilt I felt was so intense I felt the only way out was suicide. 

These days of course I have had plenty of time to reset my internal compass and live my authentic life as a transgender woman. It certainly wasn't easy.  

Playing in the Girls Sandbox

Very early in my transition into a feminine world. I discovered all was not all it seemed behind the scenes, Or what I called playing in the girls sandbox. In the beginning all seemed rosy. Sales clerks eager for my money met me with a smile. Plus, the servers where I went to eat and drink were happy to see me because I was nice and tipped well.

The deeper I went into how the sandbox really worked, I found flaws in the system. For example, it was re-enforced with me how women work in cliques while on the other hand, men form teams. Taking the example a step further, I found how I dressed could help me to fit in with a certain group of women.

Before I drifted into the Boho fashion craze, I found I could present convincingly as a professional woman. In fact, one of the first nights out I ever had was when I dressed in a professional woman's attire and went to an upscale bar frequented by other similarly dressed women. Looking back, I consider the night as the tipping point on my journey from being a cross dresser all the way towards being a novice transgender woman. Also I should point out I was terrified and sat in the parking lot for nearly a half hour before going in. I guess something was telling me this was going to be a key moment in my life.

Photo by Marcus Spiske
On Unsplash.

As it turned out, it was only a civilized introduction to the sandbox. As I drifted away from the upscale bar, I drifted into sports bars where I was often the only single woman at the bar watching sports or participating in games such as trivia. All went fairly well until I met up with several couples I began to be on a first name basis with. I learned the hard way to reject even the smallest amounts of acceptance from the men. When I did the smiles were replaced by claws or worse yet, knives in my back. Very quickly I learned where my place in the sandbox was.

As I did all of this, I was drinking copious amounts of beer which led me of course to needing to use the women's room. Or should I say, the litter box. The amount of alcohol I was drinking had the effect of being a double edged sword. On one hand it emboldened me to try to explore living as my authentic self but on the other hand, forced me into using restrooms I wasn't welcomed in. 

Of course I have written before about some of the more unpleasant experiences I had in the restroom. Overall, I was amazed how I could be seemingly accepted and socialized with until I had to use the litter box.

I was fortunate in  that I survived my early days in the girl's sandbox relatively unclawed. Perhaps it was becuase the feminine clique I landed in was unthreatening to most women. I didn't fit in with the cheerleading types. I tried my best just to be social and it must have worked.