#719: Dressing up in women's clothing and hangin' round in bars

My best Halloween ever happened a long time ago, around 1994 in Rawlins, Wyoming -- very much a "Wild West" sort of town.
My family was visiting my then-wife Cyndi's best friend Deb, a former newspaper co-worker of mine ... and between the two of them, the two women I trusted and loved most in the whole world, they hatched a plan for me to compete in a Halloween costume contest at the bar where Deb worked.
Cyndi dressed up as an Old West schoolmarm -- not far from what she was in Real Life. Deb went as a bar floozie -- again, not far from what she was in Real Life.
When they were done putting themselves together, they turned to me. And you could almost see the lightbulbs go on over their heads simultaneously. They whispered between themselves briefly.
I thought I was going to stay home, or at most be their Designated Driver. I was wrong.
"Do you trust me?" Deb asked. Of course I did.
"How do you feel about dressing up as a woman?" Cyndi asked.
I took a deep breath. I could use a good laugh. Work had been a non-stop stress-a-thon, and I could use a good hilarious Night Out With The Girls.
"If we're gonna do this," I said, "let's go all the way out. Let's not hold back. Let's make it something we can look back on and laugh our asses off about."
Suddenly I was Into It. I went to Deb's closet. There I found a garish purple number cut off above the knee, with some thin spaghetti straps to hold it up. Deb pulled out a wild brunette wig with hair splaying out everywhere.
They started laughing. Nobody would believe it. Nobody would be able to take it seriously. It was perfect.
I was gonna be a white, flat-chested Tina Turner.
They started working on my lips and my eyes. Deb slathered on the purple eye-shadow. They lined my eyes in thick black and put on mascara to enhance my eyelashes. All that stuff's a pain in the ass. They gave me the reddest lipstick Deb could find.
They gave me two handfuls of Kleenex for my fake "boobs" -- I had to have them to hold up the front of the dress.
They slapped on the wig, and teased it up and out even more.
When they were done, I looked in the mirror. And I couldn't stop laughing. I was gonna win that damn contest just from comedy effect.
When I was done, my kids looked me over.
"Dad, you look ... funny," said my then-8-year-old son Andy. But he wasn't laughing. I'll bet my then-6-year-old daughter Alicia was even more confused.
We headed for the bar. When we got there the place was packed and rowdy. Deb got us a table, and the ladies started doing tequila shots and other stuff that's beyond my experience. Good thing I was driving.
I settled in, and except for constantly having to pull up the front of my dress, I started getting fairly comfortable.
Until I started attracting ... admirers....
A rugged cowboy type, probably in his mid-30s, sat down at the table right next to me. He was hammered.
"Wow ... you're really something," he slurred.
"Thanks," I said in my normal voice.
Then he started buying me drinks.
I turned to my wife the schoolmarm, who was sitting on my other side -- for protection if nothing else.
"Do you think this guy realizes I'm not a woman?" I asked her.
She gave the cowboy a long look-over.
"If I were you, I'd go for it," she said.
After the contest was judged, we somehow got out of the bar alive -- and to push the ante even higher, we headed for a nearby Truck Stop for breakfast.
I learned some interesting things while climbing in and out of the car on the way there. Like how women in skirts climb in and out of vehicles without showing off all the goods. It ain't easy!
And I had to keep ... readjusting my "boobs" because they kept trying to fall down to my stomach ... which I hear can happen as you get older....
We pulled up a table at the Truck Stop and ordered breakfast. The Truck Stop staff seemed to take it all in stride -- it was Halloween, after all. But halfway through the meal, the Ultimate Challenge appeared.
I was gonna have to head for the restroom. This was a disaster waiting to happen.
So I walked through the Truck Stop, massive hair, slumping boobs and all, and turned the corner to head for the Men's.
From the bar, one of the truckers called out: "Hey, are you sure you've got the right room?"
In my deepest, most manly voice, I said: "Oh. Yeah, right. Thanks."
And kept on going. Faster.
Somehow got out of there without getting the crap kicked out of me. And when we got home we laughed about it a lot. When I looked in the mirror at the end of the night, I didn't look half as "good" as I had earlier. But I was still laughing.
Oh, the contest? Well, I placed sixth. My wife, who's schoolmarm-in-cowboy-boots costume took absolutely no fashion risks whatsoever, placed fifth. And the floozie placed third. Sometimes it's best to go for the obvious.
When I got back to work, I wrote about the experience in a weekly column I did for the newspaper. Nobody knew quite what to make of THAT, either -- whether they should laugh ... or what. And I thought that was pretty funny too....