Assholes Finish First (5 page)

There was another benefit I hadn’t anticipated to teaching that class: girls. Lots of cute girls want to go to law school. And most of them need help on their LSAT. I can do that. I can also have sex with them.

One of these girls was in my Oak Park class. She was Chicago-girl attractive—great face, big ass—a year out of college, and was way too impressed with my law school résumé. I guess she didn’t mind the fact that I didn’t have a real job or even enough money to pay for both food AND beer in the same week. She always stayed after class for help, and one day I suggested we go to a bar for further “instruction.” Four hours later, we closed the bar, having talked about LSAT stuff for all of two minutes. Gotta love alcohol and sex hormones.

We went back to her place, pretty far out in the Chicago suburbs. It came time to fuck, I pulled a condom out of my backpack, put it on, and we went at it. It was awesome, some of the best sex I’d had in my life to that
point. For whatever reason, this girl and I just clicked physically, so we both wanted to fuck again right away.

I started searching through my backpack and realized I was out of condoms. She didn’t have any either, which meant I had to go out and buy some.

As annoying as it is to get dressed and go out in the cold after you’ve had sex, that wasn’t my biggest problem. Here’s the thing: I don’t write about this very often, because it’s pretty embarrassing, but when I first started writing full-time, I was poor. Not regular I-can’t-afford-steak poor, I mean more like Bangladeshi slumdog poor. It’s not a big deal now that I’m rich—I can even laugh about it in retrospect—but when it was going on, it really sucked. There were many days in 2002 and 2003 where I ate nothing but ramen… that I had stolen from my roommate. And other days that, had I not been really good with women and always had girls around who were willing to take me out or cook me dinner or buy me food, I might not have eaten at all. Seriously, I was that poor.

The truth isn’t that I wouldn’t go
get
more condoms: I was too poor to
buy
condoms. If you’ve ever been poor, you know what it’s like to be at a 7-Eleven and swipe your debit card, not sure that a $3.25 charge will go through. I did not want to deal with that.

She was a spoiled daddy’s girl, so she wouldn’t go herself. I tried to get her to go with me, thinking I could play the I-left-my-wallet-at-your-place game, but she was too spoiled even to leave her house. I couldn’t ask her for money, because being that poor is embarrassing. Great. I looked for another solution.

Tucker “Can’t we just fuck anyway? I mean, what are the chances you’ll get pregnant?”

Girl “NO! Seriously, I had my period two weeks ago.”

Tucker “So?”

Girl “Don’t you know anything about women? I’m at my fertility peak right
now. These are the three days I am MOST likely to get pregnant. I really want to have sex again, but we CAN’T have sex without a condom.”

Tucker “What if I pull out?”

Girl “Pull and pray is not happening. I’m not on birth control, and I won’t have an abortion.”

Well, this fucking sucks. I rack my brain trying to think of something to do. I momentarily consider asking to use her car because there might be spare change in there. I ponder what it would take to steal money from her purse… when I look down and saw my used condom on the floor.

Tucker “Latex is pretty resilient, isn’t it?”

Girl “What?”

Tucker “Hold on.”

I go to the bathroom, turn on the faucet… and put the condom under it, careful to not tear the latex as I wash it out.

It was 3am, and there I was, a grown man washing out a used condom in a bathroom sink… because I was too poor to buy a new one. As I rolled up the wet condom to put it back on, I thought to myself: I had better end up making it as a writer, because this is about as bad as it gets.

She laughed at my ingenuity, inspected it, and gave it the thumbs-up, so we had sex. I pulled out as I came, just in case, but the condom was still there, unbroken, and caught my load without problem.

Apparently, this is a big no-no with a condom. From what I have been told since, the likelihood of a condom breaking on a second use is like 500% higher or something. Whoops. Oh well, to paraphrase Hunter S. Thompson talking about drugs and alcohol:

“I wouldn’t necessarily recommend it for anyone else, but it worked for me.”

T
HE
S
HITTIEST
H
OOKUP
E
VER

Occurred—June 2003

This girl emailed me because she liked my site, and once we got together, the conversation eventually turned to the two topics that all my conversations are about: me and sex.

She told me she wasn’t there to hook up—in fact, she’d been with only two guys in her life. This was not because she didn’t like hooking up but rather because she was afraid of hooking up. Apparently, she had a very weak immune system, took forever to get over a sickness, and claimed that a VD could possibly kill her. Not just something like AIDS, mind you, which can kill anyone except Magic Johnson, but shit like genital herpes or chlamydia could knock her off.

I told her to immediately get away from me. I am almost certainly a supercarrier and she shouldn’t even touch me, much less fuck me. I went so far as to tell her that I wouldn’t hook up with her even if she wanted it, because even though every test I have ever taken has come back clean, I can’t have it on my conscience that I killed a girl by giving her some random VD that hadn’t been discovered yet.

I was kidding of course, but it worked: She ended up coming home with me. The harder you push them away, the more desperately they want in.

We started hooking up, she took off my clothes and her top, but refused to remove her jeans. Wait, what?

She said she had some injury or something, but she wouldn’t elaborate on what it was or why it precluded her from removing her pants. She did have a bandage on her hip and I could sort of see it sticking out of her jeans, so I just let it go at first.

We made out some more and she got more into it. After her initial reticence, she decided she did want to have sex with me, despite her “injury” and risk of death from HPV. OK, condoms work great, let’s get to the fucking, right?

Is it ever that easy for me? Well, yeah, most of the time it is… but I wouldn’t write a story about it if it was just normal sex.

As she took off her pants, she decided that this was the appropriate time to let me in on a little issue she had. She began by telling me that she had Crohn’s disease. I told her that a friend of mine has it so I knew what it was (FYI, a degenerative disease of the colon). Well, hers was pretty advanced. She kept dancing around the issue until, all of a sudden, it hit me:

Tucker “That’s not a bandage on your hip is it? OH. MY. GOD!”

Great Holy Mother of Jesus, this girl had a fucking colostomy bag.

A COLOSTOMY BAG. ON HER HIP.

[In case you are lost, let me introduce you to the Webster’s Medical Dictionary definition of colostomy bag: “A bag worn over an artificial anus to collect feces.”]

About three inches to the left of her belly button a tube stuck out of a small hole and emptied into a bag—about the size of a small Ziploc sandwich bag—that was bandaged to her hip. I shit you not, there was a BAG FULL OF POOP—LITERALLY HUMAN SHIT—TAPED TO HER HIP.

This was quite the shock for me. I tried to be cool about it. I told her it was no big deal, that everyone has issues, hers just happened to be more out in the open than most, and that I would be supportive… all right, who am I bullshitting? I laughed like a fucking hyena, right in her face.

I mean, come on, the girl had a bag of crap on her hip, like some sort of old Western shitslinger. What do you want from me? Caring?
Compassion? Sorry, we’re sold out. I immediately asked the first thing that came to my mind:

Tucker “So if you shit in a bag, can we have butt sex and not have to worry about getting crap on my penis?”

Girl “Not exactly. My asshole has been sewn shut.”

Tucker “GET THE FUCK OUT! YOUR ASSHOLE HAS BEEN SEWN SHUT?”

Girl “Uh, yeah.”

Tucker “I want to see, right now.”

I rolled her over and stuck my finger down there. Lo and behold, THERE WAS NO ASSHOLE. It was just all crack, from top to bottom!

She told me that since she never used it, her asshole was sewn shut to prevent infection. I couldn’t hold off anymore. Sex be damned, there were jokes to be made:

Tucker “So I guess opinions aren’t like assholes, at least not for you?”

Girl “Very funny.”

Tucker “If I go too hard, could I fuck your shit right into that bag. I could literally fuck the shit out of you couldn’t I?”

Girl “Tucker…”

Tucker “What happens if I’m too vigorous? Will the shit hit the fan?”

Girl “Well…”

Tucker “You’re only a two-holer! I couldn’t even three-hole you if I tried!”

She explained that as long as she was careful, she could do anything any other girl could do—except shit out of her asshole, of course. Not wanting to lose the opportunity to mark a new type of handicap off my Sexual To-Do List, I coaxed her back into a romantic mood. Just as we started hooking up again, she whispered:

“Be gentle, you don’t want this thing to break.”

T
UCKER AND
H
IS
F
IRST
M
ILF

Occurred—April 2002

At this point, the majority of my friends are married. Most of their weddings were in places like Vegas or the Outer Banks. One of my boys decided to buck the trend and get hitched in Akron, Ohio. Really. If marriage is hell, I guess he figured it was fitting to have the ceremony at its gates.

He’s a college friend, so I meet up the day before the wedding with my other college buddies and we head out to find the “nightlife” in Akron. What an awful experience. It was like looking for a clean spot in a dirty ass. Leaving some bar, an attractive girl with two other girls and a guy walk by me. I give it a shot:

Tucker “You want to go to a wedding with me tomorrow?”

Girl [
stops, looks me up and down
] “Maybe. Where are you going right now?”

Tucker “Wherever you are.”

Girl “You can come with us.” [
motions to her friends getting into a taxi
] “We’re going to get something to eat.”

Tucker “Don’t offer if you’re not serious.”

Girl “I’m very serious. Come with me.”

I wish I could bottle the seductive look she gave me so I could sniff it when I jack off.

I hop into the car with them, don’t even say good-bye to my friends, and head off. We go to some shithole bar/restaurant, but actually have a great time. The girl who invited me is very into me, and I’ve got the perfect amount of alcohol in me, so I’m lighting up the table with jokes about any and everything: our obviously coked-out waitress, the Akron night-
life, and the other single girl at the table, who told me, and I quote, “My boyfriend is with his wife tonight.”

Eating time over, we go back to her place, she puts on Indigo Girls or something, lights about six candles, and we have all kinds of great sex.

The next morning, I wake up at 9am and call one of my college buddies to find out when and where the pre-wedding golf game is supposed to be that morning. He gives me directions, and I wake the woman up to drive me there. As she is getting ready, she asks me to write down my number so she can call me that night to meet up again.

I cannot find a pen in her room, so I venture out to the other rooms on the top floor. No pens, but the rooms are filled with toys, coloring books, very small beds, Powerpuff curtains… oh, no.

Tucker “Do you have kids?”

MILF “Yes, but they’re with their dad this weekend.”

Relieved, I search the rest of the house and cannot, for the life of me, find anything normal to write with.

I end up writing my number on a piece of yellow construction paper… with a red crayon. That I found in her daughter’s room. So I could fuck her mommy again that night, in the butt.

Sometimes I disgust even myself.

N
OT
A
NOTHER
T
EEN
H
OOKUP

Occurred—January 2005

One of my teenage fuck buddies (yes, she was 18) calls me at 1am:

Girl “I’m at a party and it’s lame and I’m baked and my genitals are burning for sex. Can I come over?”

The only thing that shocks me about this is that she uses the voice line instead of texting. When she gets to my place I’m busy with something important, so I make her wait.

Girl “UH! Come on, let’s fuck.”

Tucker “Not until this is over.”

Girl “This is
IRON CHEF
?! WHO CARES? I am offering you PUSSY!”

Tucker “I know. And your pussy will wait. Chairman Kaga doesn’t wait for shit. The man takes bites out of raw peppers for fuck’s sake.”

She huffs and pouts. And waits. The funny thing is that I had a TiVo at the time, but fuck her if she can’t take a joke. Teenage girls need to learn patience, anyway.

We eventually have sex and it is great—for me, because I cum. Afterward she is still baked and wants to hang out and talk or eat Sour Patch Kids or whatever it is young stoner girls do. I don’t. I want to go to sleep. She keeps annoying me.

Tucker “You need to shut up before I call your parents and tell them that you just fucked a 28 year old.”

Girl “You know, you don’t have a big dick, so I thought you’d make up for it by being good in bed. You aren’t good in bed, so I thought you’d make
up for it by being a nice person. You aren’t a nice person, so I don’t think there is any reason for me to hang out with you.”

Tucker “AAHHAHAHAHAHAHAHA. Awesome! That means you can go. Bye.”

Girl [
after a long pause
] “Uh… that did not go the way I intended.”

Tucker “It never will. You aren’t as smart as me. Just admit defeat and submit.”

B
URN
, B
ABY
, B
URN!

Occurred—March 2005