How Crossdressing has made me a better person

I was raised in a family that was very strict. Everything had to be done correctly. Everything you bought, had to be the best. If you wanted to try something new, you bought the books, took the lessons, and otherwise did everything you could be sure you weren’t “that guy” that showed up to the gunfight with a slingshot.

I am grateful for this set of values. The emphasis on quality and the goal of doing things well has been a huge blessing in my life.

It’s also made a snob.

Maybe that’s a bit of an exaggeration, but I can be judgmental. It’s incredibly hard for me to be satisfied with anything I do, and I can be demanding of others. It can also be hard for me to have fun. When I ski and get tired, I go down to the easy slopes and work on drills to improve. Sometimes I focus so hard on being good at things, that I have a hard time enjoying them.

When I dress up, it’s fun in a way that few things are. Some people might say that it’s because I have a psychological problem, addiction, or a fetish. I don’t think so, at least not entirely. . . Maybe it’s because when I look at myself in the mirror, I am forced to enjoy something in which I will never achieve the ideal. I can work hard to become a perfect skier, but I will never look like any kind of feminine ideal.

Cross dressing makes me better because it creates a space in which I don’t have to be perfect. Sure, looking nice and finding great fitting clothes is part of the fun, but dressing up forces me to enjoy something without being good at it. My desire to always be the best at things gets pushed aside by the need to be bold and wear something weird out in public. There’s a kind of self-acceptance I find with few other things. I can look good, but I also look a little goofy, and accepting that is a powerful tonic. While this helps me relax, it also helps me accept others. Because I dress, when I hear of people struggling with anything, my feelings are compassionate, rather than condescending. I am much more able to forgive and allow others space for their weaknesses and struggles.

Dressing up also makes me more open to others. I tend to be pretty closed and introverted. I like to work and play alone and I have few friends. Since gaining the courage to come to work en femme, I’ve made connections with others in the office I may never have otherwise. Sure, they may just be curious to talk to the weird guy in the dress, but that’s ok. Because I’m willing to be weird, I am more willing to talk, I am more willing to share, and I am more willing to listen. I am more approachable.

Maybe these are all things that women do naturally (or culturally). Maybe putting on a skirt and heels has helped me tap into “feminine” strengths that men have been taught to ignore or suppress. Even when I’m back in drab, I am a different person because of my time spent on the other side. That different person is more open, more caring, more compassionate, and more fun.

Apparently, the transformation isn’t just on the outside.