Halloween Comes in Many Flavors!

Over the years, I have approached Halloween from many different angles, many depended on my goals for the evening, where I was in my transition and who I was with.

The very first Halloween I went all out cross dressed was the one I have written about extensively here in Cyrsti's Condo.  It was 1974 in Germany, I was in the Army (of all places) and ended up with me coming up to several people as a transvestite not long after that.

Of course, wearing a short skirt in everyday Army life was not beneficial to earning a honorable discharge-so back I went into the closet.

During the next several years, I shied away from going to parties where I knew several people-opting for bigger venues.  I agonized for literally months on a costume that in my mind was sexy, somewhat passable and creative.  I was never as creative as Pat and  her "Monica Lewinski" costume.

Looking back at the "impossible dream", I think I made it a couple of times-that's it.  I'm not saying though I didn't have fun.

As I see it, here are a few of the Halloween party dividing points.

Will the cross dressed Sarah Palin please reveal himself?

1. Are you going to a party at a friends or with friends?
2. Do you want to be passable, comical, trashy or creative?
3. Is your costume based on a current well known woman? Example, Lewinski, Sarah Palin, Elvira in her prime, etc.
4. How "detailed" do you plan to be?  Shaved legs, nice wig, etc?
5. Depending upon how "accomplished" you are-how will you handle comments? (Which will come.)

In later posts we will take a closer look at all of these!

Trey BOO!

This Cyrsti's Condo Halloween epic involves a Victorian House, a coffin, a real skeleton and a politician.

I was working as a DJ on a local radio station here in town and one of the news women got an invite to go to a Halloween party at a local Victorian Mansion which was being restored.  She told me about it and asked if I wanted by chance to go too.  After she twisted my arm for about three seconds, I said yes!

For a change, my "costume" for this party was more in the "well dressed woman" category. I can't really remember what I wore but when we got there in the entrance foyer was an antique coffin with a skeleton.  I casually asked if the skeleton was real and was told yes!

The rest of the house looked like a scene from the Addams Family, just a perfect Halloween setting.

The party featured more than it's share of socializing and of course I was receiving my usual amount of "is that a..." attention.

Later on the fun started for me when an up and coming politician and his wife asked me if I would leave with them and go to another party. I was shy and backwards for a change and for some reason said No.  Later on he actually served quite a few terms in Washington.

It seems I destroyed my chances to move up in the political world that night.  Maybe Monica Lewinsky wouldn't have had so much on me after all!

I ran the "Monica" impersonator on the left picture not long ago but you just have to respect the attention to detail with the dirty knees!

Monica, Where Art Thou?

I love this idea/story from Halloween:

Unknown Lewinsky Impersonator

"My first Halloween outing, in fact one of my first ever outings, was in the late 1990s when the cosmos came together and I was by myself and able to dress and get out. I had a favorite blue chiffon dress with its own nylon inner slip. I wore it with black pumps and hose, a black wig, a black beret and I brought a box of cigars and went to a Halloween event at a straight bar/restaurant as Monica Lewinsky. I had a great night and there were a lot of girls there that were interested in chatting me up."  submitted by Pat.

Perhaps just mentioning Bill Clinton does bring up the idea, when you wear a themed unique female costume to a straight bar, it is a great way to meet women!
Also, if the idea was still current, have the woman in your life dress up as Clinton!