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!

Impossibly High Heels

Connie commented on a recent Cyrsti's Condo post which involved high heels, beer, and coffee:

"So, you don't need high heels to be impossibly high, just a couple of micro brews! Actually, some of those beers have a lot more alcohol content, so a couple of them could be like drinking a six-pack of Bud Light.

I've noticed that wearing "impossibly high heels" could give reason for a couple free beers, bought for me by men (gay or not?). I don't know that my makeup is perfect, but it is perfect for me! I do think about my presentation, and how striving for perfection may be outing myself more easily. Still, when the occasion is fancy enough for it, I will go ahead and doll myself up - and lift myself up, too. Five-inch heels are no problem for me to navigate any room! For me, the daily blend gets boring, and I relish those few times a year when I can throw caution to the wind. I wasn't too tall in my 5" heels that time when Sean Kemp sent over a drink and an invitation to join him at his table! I've always joked about that incident, in that Sean had so many children by so many different women, he must have felt I would be a safe and cheap date. :-)

I'm glad to hear that your foot is better, by the way. Not that I expect to also hear you're wearing impossibly high heels, though. ;-)"

For sure, high heels have a mystical erotic value. Even a sense of power for men and women. Sean Kemp surely would agree!

The beer I was drinking was a bourbon barrel stout which carried an 8% alcoholic content. By comparison, when I worked in the bar business years ago, we had to make sure Coor's Light wasn't buried in the cooler where it would freeze. The alcoholic  content was so low. 

I felt bad that even if I can't wear high heels anymore, I couldn't even drink more than two stout beers. I don't feel too badly about not being able to wear high heels anymore, self preservation at my age is a priority!

Could You Just Quit?

After getting flat out smoked by several cross dressers about my comments about a fetish orientated predatory CD a couple weeks ago, I have a tendency to be a little more careful on what I say. or write.

What I said was misconstrued to mean I was better than them because I am transgender, which is so far from the truth. The truth is, I can't do what cross dressers do and just dress up a couple days a week. It nearly killed me.

All of this brings up a question from a comment I received from Connie, could you give up your cross dressing?

" A few months after I had ventured out of the closet, I attended a fancy cross dresser event. The "Grand Dame" of the group had taken a prominent seat, and her attendants were bringing food and drink to her. I noticed her obvious limp when she got up and headed for the ladies room (in her heels). I asked her, later, what was wrong. She told me that she had developed a foot problem, and that the doctor had told her she'd have to give up wearing heels altogether. So, she told me, this was going to be her final outing - because it would be no fun if she couldn't wear high heels. Although I was pretty sure, even at that time, that I was not a cross dresser, I knew enough that she would not be able to quit cross dressing*. I told her that, but she was adamant that decades of cross dressing was now coming to an end - just because she couldn't wear her heels. I think she may also have had a shoe fetish, but it was unbelievable to me that one could give up such a large part of their life for something as small as a pair of shoes. All the time I was talking with her, by the way, I was distracted by her nose hair that was curling up from her nostril at least an inch. Now, that may well be reason enough to give up trying to present oneself as a lady - not to mention a Grand Dame!

This was just one of the "I know I'm not a cross dresser if..." I added to my list, in preparation for my impending transition. No, I would not be happy if I had to wear a boot, or even have to give up wearing heels, but it would not change who I am. Whether it be from an old football injury or from wearing very high heels too often, there's no need to put oneself on injured reserve when you know this trans life is not merely a game.

*I heard later, after I had left the group, that the Grand Dame had made a reappearance - hobbling in her heels."

Thanks for the comment! I know it would be impossible for me to give up my feminine lifestyle.  

I assume it would be just as difficult for a cross dresser to quit doing it too.  Sort of like the "Grand Dame" and her heels.

A REALLY High heel!

Here you go girls. Especially those of you who love to "sky scrape" with those heels of yours:


 This shoe is on Etsy by Bruce Gray.

Check out the second picture:

Oh, by the way you better be well heeled for this shoe- 24 grand!
I wonder what the pair costs?