Transgender Halloween

My Halloween is coming up tonight. It's finally here after a years worth of planning...the Cincinnati Witches Ball.

I am wearing a modified witches costume. Made up of a long layered flowing dress and a glittery witches hat. Not really a radical costume idea but then again, it fits the theme.

Every year at this time, I think back on all the bittersweet Halloweens I had during my cross dressing days. Sweet because I was able to spend at least one precious evening (a year) cross dressed as a girl and bitter because it ended so soon.

I did all of the usual sleezy costume ideas but later on always migrated to costumes which hopefully helped me to look like what a real woman would wear. I would hope other party goers would mistake me for a woman. Which did actually happen a few times.

For some reason though, the whole process just frustrated me more.  Instead of following up on the idea of blending when I cross dressed, I had a tendency to over do it. I became the cross dresser in the mall stuffed into a mini shirt and heels.

Fast forwarding to the present, Halloween for me has become a time to look for possible cross dressers and their costumes. Much of the fun is gone too, because I actually have a job to do at the party.

I guess the true scary meaning of Halloween for me was always replaced by the pressure of choosing a feminine costume and having the courage to wear it.

As the actual Halloween date comes closer, I will post a few of my past experiences!