Duane Sherrill

It’s not every day when I walk into church on Sunday morning and the greeter flashes a picture of me dressed in drag.

“That’s hideous!” I exclaimed Sunday as I stood at the door and squinted at the photo on his phone as he and his kids laughed. “Who is …? That’s me!”

He grinned proudly. “I found the old picture a while back and thought you’d get a kick out of it,” he revealed. “I took it at a Halloween Party, um, I mean a Hallelujah Party here at the church a long time ago. Boy, you sure do make an ugly woman.”

As I stared at the picture I couldn’t for the life of me recall when it was taken or even recall dressing up as a woman for a church function. Sure, I’ve dressed as a woman before.

“That doesn’t surprise me,” I can hear you growl over your second cup of coffee. “You’re probably wearing a skirt right now, Sherrill.”

While I am known to wear a kilt on some occasions, despite my chicken legs, I have long since stopped dressing as a woman despite the fact my birth certificate had me listed as a female for 50 years. The certificate was in error by the way as those who are avid readers of my column already know.

“That dress makes my butt look big,” I commented, bringing a chorus of laughter from fellow church members who had gathered around to see the picture.

“Good thing it was Halloween,” the guy at church commented. “Because you look scarier than the ghouls and goblins and even that guy dressed up like Freddie Kruger.”

Granted, I don’t make a pretty woman. Maybe it’s the big nose or the knobby knees. While I don’t recall dressing as a woman on that occasion, I do recall a couple of other times I crossed-dressed. None of them were especially pleasing, each time giving me a greater appreciation of what women have to go through on an average day.

First off, there’s the makeup. It’s like wearing a mask. On a hot day it makes your skin sweat and your mascara run. By the end of my first dress up as a girl for Halloween, I looked like something out of a zombie flick with my makeup all smudged, my mascara running down my cheeks and lipstick all over my teeth. And then there was getting it all off. You have to practically have a sandblaster to remove all that pancake. I was finding makeup in my ears a week later and it took several days for the eyeliner to completely disappear.

This doesn’t even include the rubbing, pinching and chaffing caused by the clothes. The bra – yes I did enhance my chest for the role – cut almost to the bone, rubbing my back and shoulders raw. The pantyhose, oh my, made my legs sweat like I was in a sauna.

But the worst was the heels. How do you women walk in those? It’s like walking on stilts. Each step is a potential sprained ankle. I looked like a drunk floozy, stumbling my way everywhere, the shoes rubbing my heels raw. I literally had to put padding in my regular shoes the rest of the week to keep from aggravating the blisters the heels left.

While the pain and discomfort of dressing as a woman is enough to make me steer clear of cross dressing for Halloween, it is the gentlemen’s agreement that keeps me from resisting the temptation.

This all came from the Halloween Party where I and another friend dressed as females. We didn’t coordinate, we just came dressed that way.

“I’ll see you in my nightmares,” Greg said as he looked me up and down in the poodle dress I was wearing. Oh, I forgot to mention that I not only dressed as a woman but I was in full 1950s theme, ready to go down to the sock hop. “These sure aren’t Happy Days.”

It was at that point that Billy walked by, strutting is woman’s outfit amongst the vampires, werewolves and ghosts at the party. Oh, there was also a guy dressed as a salad. Yes. A salad. He had cut a hole in a laundry basket and put some suspenders to hold the basket around his waist. He then filled it with salad and hung some croutons over his ears. It was an interactive presentation. You could actually eat his costume. Yep. It was a wild party.

We all stood silently for a moment before Steve looked sheepishly at the rest of us. “You know,” he said with some consternation. “Billy doesn’t look half bad as a girl.”

“Gross,” we all hissed in a chorus of testosterone-fueled rejection of his comment while all realizing he was right. Now, whether they were judging Billy compared to my hideous outfit will never be known. Did I mention I make a hideous woman?

“But, he just dressed as a woman for the Halloween Party the year before last,” Steve continued. “You shouldn’t do that.”

I bit. “Why not?” I asked.

“It’s the five-year rule,” Steve said. “A guy shouldn’t dress as a woman more than once every five years.”

“Really?” I asked.

“Yes. Everybody knows about the five-year rule. If you dress as a woman more than that, guys will talk like we are right now,” Steve confirmed.

“Well, I guess Billy doesn’t. Maybe someone should tell him,” I noted.

“Nah,” Steve replied. “Let him have his moment. Besides, I’m interested to see if any of the new people at the party who don’t know Billy is a guy, try to hit on him thinking he’s a real girl.”

So, there you go. No more dressing as a girl for fun. It’s painful plus I don’t want to risk violating the five-year rule, which, thinking back and doing the math, I may have done given the photographic evidence presented to me by my fellow church member this past Sunday. And, did I mention I make a hideous woman?

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