The FoOl Presents - True Confessions: The Criagslist Post That Almost Made Me Gay

So you all know the game “What If?” , right?
Good.

Here's a question for the guys only -

Quickly, tell me what you would do if you were trapped in the body of a woman for a day?

(theme music for Final Jeopardy...)

Okay times up.

Now every man at some point has already thought about this shit or been asked this exact same question and the one and only acceptable answer, if you're straight, is:

Lock yourself in a room and masturbate all day.

It's a universal phenomenon. A real no brainer that transcends all divides.
You couldnt' get a room of Republicans and Democrats to agree on whether or not Lance Bass is in fact gay, but give Newt Gingrich and James Carville a pussy for a day and you bet your ass they'd BOTH be working their clits like they were the A/B buttons and they just got knocked down for the second time in Punch Out.

In the entire history of that question being asked the only person I know who ever answered differently was my buddy Pauly. He spent twenty minutes thinking it over, as though it were the final question on the LSAT's, before answering as follows:

“Well I actually think I'd want to have sex with a guy. I mean hear me out – aren't you curious about what it would be like to experience sex from a woman's perspective?”

Predictably, last I heard Pauly was tricking John's on Jarvis for meth money. His days now consist of swallowing salty anonymous loads in conveniently located and discrete parking facilities. I hear he's a big hit with the power lunch crowd and I bet he knows all he ever wanted to know about what it feels like 'from a woman's perspective'.

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It was a random day just like any other. I and I was burning down some tightly packed bowls of the sacrament with the boys when I came up with this classic “What If?” conundrum:

Would you fuck a smoking hot post-op trans man who was now fully a woman as far as the physical goes ?

The question was deeper than I even realized. Immediately everyone took notice. There was a pause and I could see that they needed some clarification. My buddy Eddie asked

Like...would he have a pussy? A real pussy?

To which I answered

Yeah. Yeah man exactly. He'd be a she in all the ways that count. In fact the only way you'd be able to tell any different from the physical point of view would be cause they mentioned to you they were trans. Otherwise you couldn't tell.

Then there was a really long fucking pause and everyone started looking at each other for a clue about what the right answer to such a difficult question might be. Eventually fear ruled the day and the first 'No!' started off an insecure chorus of 'No!'s that in a more controlled environment might have very well been 'Yes!'s. I didn't feel as though their answers were honest and somewhere inside I felt like the long silence that preceded the eventual verdict of 'No!' was where the real answer was to be found.

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When I'm at work and I want to vent my brain for fifteen odd minutes my one sanctuary is the Craigslist casual encounters forum. It's the only place on the world wide web where I can truly tune in, turn on and drop out. A pervert like me can put his mind on cruise control and surf through dozens of listings real and fake, occasionally stopping to squeeze off a desperately hopeful e-mail that never receives a reply in kind. It's a ritual for me. The one release I have during the 9 to 5.

I was just going through the motions on Craiggie's a few months back when I happened across this (click and examine this screen capture):







It was really very early in the morning so my brain wasn't picking up all the details it normally would. I was just so transfixed by the picture. As I felt a surge of Morning Wood Revival starting to take place I figured why not shoot out an e-mail and test the waters. Here's literally what I wrote:

Dear Dirty Bitch,

For the last three days there has been a swell growing in my balls; a swell without a purpose. That is – until I came across your post. I now know without a doubt that it is the destiny of my load to be shot across your slutty little face. I imagine a passionate evening for us. We start off watching romantic comedy's like Fool's Rush In and 50 First Dates, then cap off the night with me fucking you in the ass doggystyle while fish hooking your mouth from behind and calling you a whore. I know I don't know much about you, but I think I can love you. In time we cou


This is as far as I got into typing up a reply before noticing that the “W” in the “W4M” heading wasn't a “W” at all, but instead a very disturbing “T”.

FTW?!?!?!?!??!

I was devestated. I had my own personal Crying Game at my cubicle, on my knees in front of my desk, my silk tie loosened to facilitate the vomiting into my standard issue wastebin. I kept telling the co-workers who passed by my workspace that it was the poison breakfast bagel I got from Timmies and not the he-bitch I almost solicited off of Craiggie's. I'd never been so fucking low in my life.

Then the vomiting stopped. I stared at the picture on my computer screen for what could've been half an hour if it were even 5 minutes, and after realizing how long it had been since I'd last had sex, one very serious question burned white hot in my mind's eye:

How well can I lie to myself?

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When you're a single man in a slump you will find depths within your soul that you never knew existed. I have seen my friends, proud men of good stock, swear up and down that they would never sleep with a woman who wasn't at least a “6” or better, yet in the grip of a harsh singles-scene slump I have seen with my own two eyes these same men bedding women who could rate no higher than a “1”, their repulsiveness making a good case for the implementation of a decimal system.

I found my personal all time low a few months back when I picked myself up off the ground of my office floor, sat back down in my cubicle and finished that e-mail to the trans-chick.
Many days have passed since then. I've sat and wondered how my life might be different today had I received a reply. Would I have gone through with it? Would I be a different person than I am now? Would I be gay?

I guess in the end I can only wonder “What If?”