Assholes Finish First (28 page)

One of the first girls I ever fucked from my website told me she had two tattoos. One was right between her breasts, her initials in Celtic.
Whatever. During foreplay, I asked her where the other one was. She hesitated, then said:

“Oh well, I might as well show it to you, you’re going to see it anyway.”

She pulled her pants off to reveal a long string of words right above her vagina, stretching all the way across her pelvis. Set inside alternating blue stars and pink hearts, like a slutty Lucky Charms leprechaun, were the words:

“Aren’t you lucky?”

I looked at it for a second.

“That depends on how many guys have been asked that question before me, doesn’t it?”

L
UCKY
+ Y
OU

Occurred—November 2007

A stripper I was fucking had this tattoo right above her pussy that said, “Lucky + You.” At first I just assumed it was another of the various ways you could phrase something about being lucky to get her pussy (why do women have such issues understanding probability?), but then I thought about it: What the fuck is the + for? She explained it to me:

Girl “My pussy’s nicknamed Lucky. The plus is because you and Lucky are now together.”

Immediately, I was reminded of the old joke: “LOST DOG, one eye missing, mangled ear, paralyzed hind leg, crooked tail. Answers to the name Lucky.”

I made double sure to wrap it with that one.

T
IME
F
LIES
W
HEN
Y
OU’RE
F
UCKING
T
ATTED-UP
W
HORES

Occurred—October 2007

This girl had been emailing me to fuck for months, and since I wasn’t going to be anywhere near her city anytime soon, one day she decided just to take it upon herself to drive 18 hours. Not fly—drive. 18 hours. To fuck me.

I can understand 4 or 5, even up to 8 hours—after all, I’m awesome. But to DRIVE for TWO days, just for my dick? I wouldn’t even drive that far to masturbate.

As could be easily predicted, she was a hot fucking mess. Great body with nice fake tits? Yes. Everything else a disaster? Yes. I later described her to a friend as “someone who would chase her birth control with warm Natty Light.” I mean, for fuck’s sake, she walked into my place wearing a thin white halter top over a leopard print bra. This is the type of girl I would expect to find passed out in the men’s bathroom of a biker bar.

When I meet new people, especially girls who want to fuck, I usually like to talk to them about themselves, probe into their lives and figure out their personality. It’s always interesting to see if I can get them to open up and discover the thing they try to keep hidden. Sex is only one part of the enjoyment of another person, after all. If I didn’t learn about all their hidden dysfunction, how else would I know how to manipulate them?

Well, this was a rare exception. I could tell just by the crazy, desperate look in her eyes that there was nothing but pain and misery in her past. And not the funny, network sitcom–type pain that you can guiltlessly laugh about; this was the bad kind that wins the Pulitzer Prize for
literature. I had no desire to open that Pandora’s box of awful parenting leading to a series of abusive boyfriends and culminating in some demeaning job in the sex industry. It was bad enough to almost make me not want to fuck her. Almost.

But what would you do if an attractive woman—even one with crazy eyes—was standing in your living room, massive tits beckoning you from behind leopard-print lingerie, asking you to “beat up my pussy”? If you’re a guy and ultimately respond with anything other than “fuck her,” you’re either happily married, gay, or a liar. You should probably make her shower first, but the point stands.

As she came out of the shower, I pulled her into the living room and pushed her down on the sofa. I was right about to fire it in her, when I saw some dirt or something on her thighs. I stopped to investigate; small black spots around a woman’s crotch are not something you can just file under “worry about later.”

I looked at them, got confused, then went in for a closer look. I couldn’t believe my eyes. It was kinda dark in my place, so I turned on every single light. Yeah, there is no question what it was.

It wasn’t dirt or sores. The dark spots were permanent ink. Four little tattoos on her inner thighs. They were flies, buzzing around her vagina. And then two longer tattoos, maggots, made to look like they were crawling out of her vagina.

I literally gagged when I realized what they were.

Tucker “Are those flies… and maggots?”

Girl “Yeah.”

Tucker “Why the hell are those there?”

Girl “I don’t know. I thought it was appropriate at the time.”

Appropriate?!? Flies and maggots congregate in two places: stinking piles of excrement and fetid, rotting corpses. Which, exactly, did she think her pussy most closely resembled?

I didn’t want to know the answer to that question. This was too much emotional dysfunction for even me to deal with. Before that exact moment, the list of things that would have stopped me from fucking a conscious, willing woman who was lying naked and freshly cleaned on my sofa was four items long:

1. She has open sores or infections

2. She is actively shitting herself

3. She is actively pissing herself

4. She is actively puking on herself

That was the whole list. Well, not anymore. Thanks to Polly Rottenpuss, you can add one more thing to it:

5. Tattoos of flies and/or maggots around the vagina

N
EXT
-L
EVEL
S
HIT

Occurred—December 2005

The month before I moved to NYC, I decided to spend some time in the area looking for an apartment. It’s about a 13 hour drive from Chicago to NYC, and since there were some cute girls from Pittsburgh who had been emailing me, I decided to stop and hook up with a few of them.

There was one girl in particular who I wanted to hang out with, Jess. She had good pics, wrote intelligent emails, made it very clear she wanted to fuck the shit out of me, and was a big drinker. But it was something else that really clinched it for me. A week or so earlier she posted this on my message board under a thread about road head:

“One of my very best friends, a guy I dated for about 4 hours in high school, found out his girlfriend was cheating on him, with
a 17 year old baby daddy named Daeqwon. I cannot explain in writing how livid we both were to learn this. I also cannot explain in writing how vengeful and twisted he and I both are.

Instead of immediately dumping her and letting me tear her to pieces, he took her out on a huge date. Kind of like Tucker’s butt sex story—he buttered this bitch up. Dropped $250 on dinner and took her to the fucking ballet. All because he knew that a little romance and a little Dom would get her to open wide and give him a slob job on the ride home. And slob she did—he later said it was some of the best head of his life.

His life, not hers.

Before their date (immediately before) I ran over to his apartment really quickly—and let him fuck me. In the butt. Seriously, we are strictly friends, totally platonic. He didn’t come. Just a few in-and-outs to make sure his wang was nice and tasty. After he put it in my ass for a few minutes, he very carefully stuck his dick back in his boxers, saying he didn’t want to let anything rub off.

Two hours later he let his raging whore of a (now ex-) girlfriend suck on his penis for about 20 minutes. He claims at one point, she almost stopped, because he was laughing so hard he swerved off the road.

See you in hell.”

This was clearly a girl I needed to party with. Right before I got to Pittsburgh I called her to make a few things clear:

Tucker “I like to fuck before I go out drinking, so are you up for a quickie or two before we hit the bars?”

Jess “Yeah, of course, definitely.”

Tucker “Excellent. And one more thing: Just because I fuck you before we
go out does not necessarily mean that I will go home with you. I’m not saying that I’ll be going out with the intent of hitting on other girls, but I never know what is going to happen. If you are not cool with me fucking you early and then potentially going home with some other girl, let me know now. I don’t want you to get pissed and stab me in my sleep.”

Jess “Oh no. I’ll even help you pick them up, maybe we can have a threesome.”

This girl is going to make someone a great ex-wife someday.

I get to her place and she looks just like her pictures: cute face and a really good body. I am so happy that she sent me honest pics. I have no idea why, but some girls seem to think that when I meet them in person, I won’t notice that they put on 40 pounds and 20,000 miles since their last good picture. Even better, though, there is also a bonus that her pics did not show: an amazing ass. To be honest, I am more of a tit guy than an ass guy, but hers is a piece of art.

We hang out for a while, she seems like a pretty cool girl, and we fuck. It’s cute: She is kinda nervous at first, but eventually she relaxes and we have pretty good sex.

Afterward, I notice a tattoo on her right hip. It is the initials R.H. with this weird design in between them. Obviously, I assume the worst.

Tucker “Who is that? Ex-boyfriend?”

Jess “No, fiancé.”

Tucker “He dumped you? Hahahaha, that tattoo doesn’t seem like such a good idea now, does it?”

Jess “No… he didn’t dump me.”

Tucker [
joking around
] “What, you dumped him because you caught him fucking your friend?”

Jess “No. He died. I got this after his death.”

Tucker “What, he couldn’t just break up with you? He was so sick of your shit he went and died?”

She actually laughed at that joke, but I did feel legitimately bad. Well, not really, but I sensed that a good person would have felt bad.

We went to a place called Fat Head’s for beer and wings. The bar was filled with what is apparently the unofficial mascot of Pittsburgh: the loud, drunk blue-collar idiot. These two older guys were sitting next to us in their Greg Lloyd jerseys and Harley-Davidson bandannas, screaming at the Penguins game on TV, when we sat down.

Yinzer “So, yinz two aren’t gonna argue like that last couple, are you? He spent two hours yelling at her ’cause she wouldn’t fuck him, and she was pissed because he was never home.”

Tucker “No, sex is not a problem in this relationship. In fact, right now she has a bunch of my cum in her. And even a little on her. You can probably smell it if you get close.”

His eyes got all big and he leaned back and elbowed his buddy.

Yinzer “You hear this guy, Dale? He’s talkin ’bout shooting cum at her!” [
turning to Jess
] “You don’t mind him talkin’ like this?”

Tucker “She’s lucky I’m even here.” [
Jess nods in agreement
]

Yinzer “DAMN! I wish I had your balls!”

Tucker “I wish you had a breath mint, but I guess we don’t always get what we wish for.”

After that, they left us alone.

The place had like 40 beers on tap and another 40 in bottles, most of which I had never heard of, but Jess confidently recommended Arrogant Bastard Ale. It was quite good. Not only is this girl bisexual, good in bed, a huge fan of mine, and cool to hang out with, but she really knows her beer.

At this point I started to get excited; when you reach in the ho grab-bag, you never know what you’re going to get. Well, it looked like I had picked a winner. So of course I did what only a fool would do: I looked the gift whore in the mouth.

Tucker “I know you like girls. What about threesomes with guys? You ever do that?”

Jess “Oh yeah.”

Tucker “You do know that girl, girl, guy = awesome, but guy, guy, girl = gay, gay, whore.”

Jess “I know, but this was kinda different.”

Tucker “How? You were in love with both and couldn’t decide so you had a fuck-off?”

Jess “No… this threesome was more about the guys.”

Oh no.

Tucker “What?”

Jess “Well, my boyfriend and this other guy and I had a threesome, and they kinda focused on each other—”

Tucker “You fuck gay guys? Are you telling me I just fucked a fag hag?”

Jess “NO! It’s not really like that, you see my boyfriend—”

Tucker “You do know that virtually all AIDS cases are transmitted three ways: IV drug use, sex with prostitutes, and SEX WITH GAY MEN! If you don’t fuck those risk groups, you are probably going to be fine, yet here I am, fucking a girl who screws homosexuals. This is just fucking great. Where is the closest clinic?”

Jess “NO WAIT! It wasn’t like that, listen. My last boyfriend is gay now, but the first time he ever hooked up with a guy was that threesome. And it wasn’t really a threesome. We were drunk and high and this kid got blacked-out drunk and passed out and my boyfriend sucked his dick.”

Tucker “That was his first time with a guy? Yeah right, and you are the first girl I’ve ever fucked.”

Jess “NO! IT WAS! I’ve known him since he was 6! He is gay now, but that was the first time he’d done anything with a guy. He talked about it a lot before then, but that was the first.”

Tucker “Did you fuck him after he started putting random dicks in his mouth?”

Jess “NO! That’s pretty much the reason we broke up!”

Tucker “Pretty much! What are the other reasons? Murder? Arson? You
mean raping a guy who was passed out wasn’t enough, there had to be other reasons?”

Jess “Did I mention that the blacked-out guy was 17? And a virgin?”

Tucker “I am going to take a wild guess and say that this ex-boyfriend is the same guy who you let fuck you in the butt right before he had his cheating whore girlfriend go down on him?”

Jess “Uhhh… yeah…”

Tucker “This just keeps getting better. Please tell me that incident was before he started fucking dudes?”

Jess “YES, of course!”

Tucker “That is the first good news I have heard since this conversation started.”

Jess eventually calmed me down by plying me with beer and promises that she knew her ex very well and that even though he is a big gay slut now, that really was his first time. I didn’t believe her and was still going to get tested, but I felt much better.