Blowing My Wad — Part 1: How I Pissed 500K on Booze and Whores


“That’s why I’m paying you, Candy.”

Two years ago, doing Greek would have been ordering a lamb souvlaki.

A little course in escorting for you laymen–’greek’ means up the ass. Greek is often spelled with a lower case ‘g’, which is funny, because you would think that putting a dick in an ass should require a capital ‘G.’

I love anal. Not the way it sounds when you say it, a-nole, but I’ve moved past that. I accept its dirty imperfections. I’m not even talking about the act. I’m talking more about the idea. The taboo. The dark hole of pleasure that people associate with something ugly. The untouchable is mine.

(I’ve also grown a fetish for feet, armpits and that little section on the back of the leg that’s below the biceps femoris, above the gastrocnemius, right behind the patella.)

I’m what’s known as an escorting hobbyist. But there’s something about the word ‘hobbyist’ that doesn’t quite express how much I enjoy burying my face in a mound of ass for two hours at $750 to $5 grand a pop, depending on the quality of ass and the current demand in the industry.

I guess a better, more appropriate term for me would be ‘lucky SOB.’

My obsession for the ass has helped improve many skills in life. For instance, I’ve acquired a solid understanding of how search engines function, which has become useful when trying to find specific anal scenes on porn tube sites. Using quotes in Google when typing words like “dirty sluts anal” comes in handy when you’ve got a hard-on to find that “dirty sluts anal” scene your bartender showed you at the Broadway Bar.

(I actually once started a video collection of porn stars doing their first anal scene. It was glorious. Then I got a girlfriend and deleted the evidence.)


This is what happened: I got hit by a truck about a year ago, and I got 500K to compensate me for my bones shattering and for the spinal fluid leaking from my ears. The truck? A Dodge. A caravan. A 1999. The 90s ran me over. Pathetic, I know.

Not being hit by something badass is one of the biggest regrets in my life. Every day I regret not being plowed by a a 1929 Ford Junkyard Dog.

But I don’t regret the escorts. Or the ass-licking. Or spending thousands on a hotel two blocks from my studio.

I don’t regret the 8 am boozing of the past 12 months. Or the grubHub ordering every day of the week. Or the limos from Los Angeles to Vegas to the Bunny Ranch and back. And most definitely not the Thursday morning trip to Bocas Del Toro last November with a mostly bald, snaggle-toothed hooker.

(She’d lost her platinum wig in the Pacific. So we rented a boat, grabbed a bottle of Balvenie and found he wig off the shores of Red Frog Beach. I got to eat out her ass for no charge as the finder’s fee.)

But that’s all behind me now. Today I’m browsing the Internet hungover from boxed wine and late-night Domino’s, searching for personal loans. After I returned the BMW Z4, I’m wondering if I can use my 2001 Saturn–the piece of shit car I was born with–as collateral for credit. It’s amazing how quick 500K goes in a year. Now I can sympathize with the lottery winners’ crash and burn stories and the bums on the corner of 8th and Broadway in downtown Los Angeles. I’m close to those people now.

I’ve burned bridges. I’ve lied about my identity. I’ve lied about where I got my money. I’ve isolated myself in a world of booze, whores and holidays. And it all seems like a giant blackout, now.

This isn’t an ‘I found God’ kind of story. Though Lord knows if I get my hands on 500K again… This is just the story of how, for one year, where I became Dennis Wilson, Bukowski and Hank Moody all rolled into one hot mess.

There’s no happy ending. There are lessons learned, but mostly not the kinds of life lessons you’d expect, like renting the private Rehab cabana Jacuzzi does not guarantee you a blowjob.

This is just the tale of how one 26-year-old fucking jerk who lived large, carried out every detail of his fantasies and had them all crash down like a burning ball of motherfucker.

CHAPTER ONE: The Beginning of My Career as a Hobbyist

Money seems like the issue at first when you’re starting your career as an escorting ‘hobbyist’. But once you dive in, quality is all you care about.

Which is why I’ve come to appreciate escort agencies–to know exactly what I’m buying. The product. The fantasy. To know what ass I will have on my face for a given amount of time at an exact price. And to pay for that ass with an AmEx card.

The first time I got an escort I was nervous. I booked a seedy hotel in Glendale, CA. Drank about half a bottle of Jameson and paced in my non-smoking- turned-smoking room, waiting for cops to barge in. They never came. But she did.

Pattaya. A petite, sexy Thai girl wrapped up in a light brown trench coat.

Definitely not the blonde college girl I’d ordered off some back pages of a website that’s the bear trap for below-average SURPRISE hookers. But I was drunk and I felt it was more important to bust my escorting cherry than to be picky. I wasn’t in a position to be picky.

Pattaya kissed me on the cheek, walked to the dresser and collected her $500. I made a bad joke about PayPal. She didn’t react.

I offered her a drink. No response.

It dawned on me that Pattaya didn’t speak a lick of English. Which I thought would be a problem since part of my fantasy is having the escort say my name and demand that I bury my face in her ass. But I improvised. My new iPhone 4 found me a translation app.

I started out slow: “You look sexy tonight.”

Pattaya giggled.

I grew more confidant: “Did you buy that underwear from Victoria’s Secret?”

She giggled.

I wasn’t getting anywhere. I downed some Jameson. You’ve paid for this service, Andy… say what you want.

Did you know that “Can you sit on my face?” looks like this in Thai: “คุณสามารถนั่งบนใบหน้าของฉันหรือไม่”?

Pattaya went to work. Slipped off her panties and positioned herself above my flushed face. I was severely smothered. I’m pretty sure she was texting her friends while my face was lodged in between her cheeks–I could hear the swooshing sound of messages being sent. After about 20 minutes of this, I grabbed blindly for my phone, typed out a message and held it up to where I think Pattaya’s head was. The translation worked. Next thing I felt was her warm little mouth on my balls as she stroked me off.

When my ear-bleeding ecstasy was over, she collected her things, kissed my forehead and left. I didn’t even help her put on her coat.

I remember my first time with an escort more than the night I lost my virginity. I realized escorts are miracle workers. No price is too high: They provide the service of fantasy.

Fifteen minutes after she left, I ordered another. And another. And then two at a time. One night at a dirty hotel turned into seven nights in heaven. I never wanted to leave.

Next time: CHAPTER TWO — Partying in Chi Town and Having Sex on Leather Sofas


Related on The Smoking Jacket:
Jenny and Her Husband Get a Whore 
Would You Give a Dog Mouth-to-snout Resuscitation?