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!

Confidence

One of most recurring themes here in Cyrsti's Condo over the years, has been the fact "confidence" is your number one accessory to any outfit. Not your dress, not your purse or your makeup. If you carry yourself as if nothing is wrong, most people will think that too. Essentially you will have perfected your own feminine mystique.

Of course, if you go overboard and wear a micro mini spandex skirt to the grocery next time, you will be certain to get your fair (and unfair) share of stares. Seemingly, something all of us novice cross dressers or transgender women have to go through on our paths to wherever we want to get to.

Personally, one thing that drives me crazy is when I see the mini skirt I mentioned above over ill disguised foam padding. The mirror must have been really lying to the cross dresser that day. I know, because I have done it myself. Over the years though, I learned from my mistakes, the stares and snickers (or Milky Way's) lessened and my confidence increased.

One of the hardest things for me to do was believe in myself that I could do this woman thing. As time went by, I hid my small feminine presentation mistakes with having the confidence to be who I was.

As you develop your transgender confidence, you will find slowly but surely you will have more bright days than dull ones!