Blowing My Wad — Part 2: Chicago Whores


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. Since then, I’ve burned bridges. I’ve lied about my identity. 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, I became Dennis Wilson, Bukowski and Hank Moody all rolled into one hot mess.

A MAN’S TWENTY-SIXTH BIRTHDAY usually means shit. But when I turned the big 2-6 I’d just gotten out of a three-year relationship. I’d like to say the breakup was mutual, but I’d be lying to you if I said that. The love of my life ended things due to my inability to control my drinking. She gave me chances. A lot of them. But I failed every time.

Maybe it wasn’t just the drinking. It could be my intense interest in anal sex freaked her out. (For my ego’s sake, it’s important to note that I did have breakup anal sex with her. Actually — I’ll go one step further — I’ve made every girlfriend I’ve ever had lick my ass. That way, when the relationship inevitably ends, I know that her face has been in my ass. Some of these women are married now. With kids. Photos of ex-girlfriends kissing their husbands on Facebook makes me smile. These are the small victories in my pathetic life.)

Anyway, as a newly single free man flush with a load of cash (see Chapter 1 for the details on how I landed my cash), I was going to celebrate my birthday right. New York may be Woody Allen’s town, but Chicago? That’s my town. It’s everything I love about a city.

Chicago’s restaurants range from the slop to the overpriced. Plenty of booze. Sports fans that are borderline suicidal. Money. Architecture. Art. Rough neighborhoods. Rock ‘n roll. Jazz.

And women.

The women of Chicago are probably my favorite women in the world, other then Texas girls. The women of Chicago tend to be gorgeous, round-bottomed, hot dog-eating, booze-chugging chicks who are classy yet not afraid to suck your balls.

The Sax Hotel & Queen Latifah

The Sax Hotel

I’d planned to stay at the Sax Hotel for four nights and five days; then find another place. The Sax is a great location: It’s next door to the House of Blues, and it’s got gorgeous views of the Chicago River.

Sporting a fancy trench coat, an overpriced bowler cap, and fake geek glasses, I approached the front desk.

“Welcome to the Sax Hotel, how may I help you?”

“I’d love to check out the furniture in my master king suite, please.”

I always like to see what the layout of the hotel room provides. What couches will bottles be chugged back on? Can the bathtub fit only two, or up to three petite models? Are the foot benches comfortable enough for a woman to bend over on? And is there a leather ottoman nearby to watch any girl-on-girl action occurring on the bed? After examining the room, I told the bellboy to bring up some Balvenie and Goose. I tipped him generously. I have a lot of respect for bellboys. Maybe it’s because I used to deliver pizzas.

I’d planned ahead for my activities. After about three drinks of Balvenie, a fake-breasted blonde entered my room accompanied by a pigtailed brunette. I gave them each a glass of Goose and told them it was my birthday. Not like that information even matters to an escort. They can care less, and they won’t go the extra mile just because you were fucking born. But I told them anyway.

They asked for a refill. I made it a double.

As the Facebook birthday notifications rolled in, I was drinking my Scotch from the bottle and getting a blowjob from both gorgeous women.

The movie “Just Wright” was playing in the background. Queen Latifah was really killing my arousal. I flipped it off and focused on my Scotch and getting the girls to look up at me from time to time while they worked.

See for yourself what a buzzkill this movie is:

And that’s pretty much the way I spent the next three days in Chicago: I cycled through drinking, passing out, ordering room service and getting it on with hookers.

And then I got to feeling a little edgy and anxious. So I popped some Xanax, stuck a flask of booze in my trench coat, and headed out to see the town.

The year before I’d gone to Chicago for a vacation with my girlfriend. Whether it was the booze, the Xanax, or my mind playing tricks on me, as I walked the city I kept stumbling across places we’d visited together.

I found myself at the Art Institute of Chicago, where her 90-year-old grandma works. I made my way to Hot Doug’s where I re-ordered what I had with her: The Brigitte Bardot. I walked in Grant Park where we’d hung out at the Pitchfork festival. I looked at the gorgeous shoes at Fluevog in Wicker Park where I’d bought my ex open-toed lace-up boots. Lastly, I hit up the famous Green Mill in Uptown and watched a drowsy jazz act drone on to a sad, essentially empty house. Seemed fitting. My body was about ready to break. I made it back to Sax and passed out.

Wrigley & The Big Z

The next day I mellowed out. I had a few beers, got a massage, went to the spa. I was preparing for my Saturday adventures with my good chubby buddy, Jake. I should clarify what I mean by ‘good chubby buddy.’ Basically, he tolerates, forgives, and puts up with my antics.

I checked out of the Sax hotel. I hopped into a whiskey-stocked limo and picked Jake up. We headed out to Wrigley Stadium. I’d gone to a Cubs game with my ex-girlfriend the year before. It was magical.

But this time I didn’t give a fuck about magic or history. It was about paying for the most expensive, two-rows-off-the-field seats, and pounding back as much booze as possible. The game was between the Pirates and the Cubs. The pitching matchup: Paul Maholm vs. Carlos Zambrano. The Cubs won 5-3. I know all of this – not because I was at the game – but from the newspaper box score the next day.

During the game, we got friendly with one of the high-up Cubs executives, let’s call him Mr. X. Mr. X was a well-known man, infamous for his public playboy experiences and antics. I knew about his reputation; we clicked from the start. He was entertaining his rich hedge-fund friend–let’s call her Mrs. X, and his high-school-aged nephews. While we chatted it up, my alter ego took over. I lied and told them I wrote for Family Guy and that I had Hefner’s number on speed-dial. I showed them. Indeed, it did say “HUGH HEFNER” in my contacts… But there was no number. Those two simple lies allowed me to scream, heckle, vomit and say whatever the fuck I wanted without getting thrown out.

After the game, Mr. X took us to the locker room to meet the winning pitcher, Carlos Zambrano. I was about 18-20 drinks deep by this point. Probably more. I don’t know. Mr. X introduced me to Zambrano, a 6′ 5″, 260-lb Venezuelan man who I imagined worked out in the Amazon in the off-season. Mr. X told him I wrote for Family Guy, which Zambrano loved. I couldn’t stop staring at the guy and the only thing I could think to Zambrano was, “Mr. Zambrano, how big is your cock?”

Jake and I were immediately escorted out the stadium. I still want to know what the Big Z is packing.

The Dana Hotel & The Bellboy

The Dana Hotel

I checked myself in the lovely Dana Hotel near Chicago’s North Side. The room wasn’t as big as I would’ve liked, but the skyline views were amazing. I decided to spend the remaining days with only one hooker. I didn’t want some glossy, polished escort. I wanted to sift through back pages looking for something different. I wanted someone dirty and broken.

I found her: Veronica. Cheap rate. Girl-next-door type. Not in great shape. Not terrible, either. Young, confused. A gutter girl with punk rock in her blood. Exactly who I wanted.

We drank and fucked and talked and sat in silence. We covered everything from post-punk to Doctor Who to gangbangs. This went on for a while.

The bellboy brought us our oysters. A good looking young man. Probably 19. At this point, I was open for anything. I told Veronica to flirt with him and invite him back once his shift ended. The bellboy seemed confused but intrigued.

Veronica fed me what seemed like an overdose of Viagra and rode me. We feel asleep. The knock on the door two hours later woke us up. It was the bellboy – now in street clothes clearly bought at Hot Topic. I told Veronica to stroke him off on the bed. I sat in a corner chair near the window that overlooked the busy street below. I drank my Balvenie as quickly as Veronica pulled out his dick.

I will admit I was jealous. He was pretty hung for a white bell boy. Veronica hickeyed his neck like a vampire nymph. Two minutes later he came from the handjob.

We tipped him a hundred and kicked him out.

Los Angeles & “Pour Man”

Morning of my flight back to LA, I was alone. Veronica was gone. She’d left her number and told me to call her with a bunch of XOXOs and shit. She wrote she’d see me in LA.

But there was no way I was going to see her again. I have a way of falling in love with hookers. I find them as flawed as I am. Veronica was by no means a pretty escort. She was a dirty, slightly overweight punk girl whore. But that also made her beautiful. She was smart. Opinionated. And funny. And she could fuck. These are the type of whores I fall in love with.

I took a limo back to Midway for the flight back to LA. The sun streaked in through the back window on my strung-out, weathered face. My mind started to think back to all the fun I’d had on the trip. Most of what I remembered was just black with purple dots of memories flashing here and there.

It then hit me.

I realized what I would miss most about this Chicago trip was the Chicago trip I’d taken the year before. The birthday I’d spent with a loved one. The sober, lavish brunches I’d spent in silence and grins with my girlfriend. Watching Close Encounters in Millennium Park. The cooking jazz rhythms that played at the Green Mill when I was there with her. For a moment there, I felt regret and shame.

I almost wished I’d blown my money on big purchases. Like a Porsche. Or a boat. That way, when the money went, I could sell the assets and recoup some cash. But when you blow your wad on hookers and booze… there is no refund.

I think my worst fear is probably that my landlord will find me dead, naked in bed with come on my belly and a Shemale video blaring on my laptop. My poor Catholic mother’s face.

We hit a bump in the road and I noticed Lee Hazelwood’s “Pour Man” playing on the radio.


Coming soon…

CHAPTER 3: My Two-Week Pornstar Girlfriend, and Oprah’s Favorite Hotel  

Related on The Smoking Jacket:
Blowing My Wad: How I Got Hit By a Dodge Minivan and Pissed 500K on Booze, Whores, and Designer Furniture