KSK Fantasy Football and Sex Advice Mailbag: Discount Virginity, Altruistic Fornication, and Drew Barrymore

03.05.09 9 years ago 185 Comments

Welcome to your weekly Thursday afternoon treat.  In this edition of the fantasy/sex mailbag, we once again DON’T discuss anal.  I hope we’re all over that phase.  This week we’ve got a couple questions from female readers, a compelling inquiry on threesomes, the standard complaints from Bears fans, a trainwreck of distrust and betrayal, and an actual virgin (so “she” claims). Let’s do this.

Dear KSK-bags

Football:  If the Sex Cannon landed in Minnesota would that be Drew’s worst nightmare or a strange, poetic irony? [Note: this question was sent in before the Vikes landed Rosenfels]

Sex:  I am seeking suggestions for avoiding the friend zone!  Situation is Facebook oriented as I had recently added a gal whom I really, really liked in HS.  We had not been in close touch since and now, some 18 years later, she pops up and is like, “Hey I am single, want to hang out?”  I am single and do want to hang out.  SO, we start the annoying phone-tag, message, text game people now have to play just to fucking communicate a little.  And after a few conversations it is made clear that YES, she is single, but no she is “too messed up to date right now until she has a better idea of who she is”  I have no problem with those thoughts and ideas and want to respect her space but is there a way I can play supportive friend while keeping my number front and center for when the fuck gates re-open?  Or is it already too late and I am sitting in the waiting room of Friend Zone central?  Furthermore, what is it about girls and this friend shit…it always makes me want to fuck them more!?!?!  GAWD DAMMIT!

Some guy

Good Lord, man.  You failed Peter King’s First Grade Introduction to Reading Signs 101.  She couldn’t be more obvious if she had flashing runway lights going up her thighs.  For anyone else out there who is new to this planet: “too messed up to date” is code for “I’m just looking to sleep around for a while.”  Now go out there and have meaningless sex!

As for the Vikes, I think they’ve got their hands full with mediocre quarterbacks.  Unless Brad Childress is getting quarterback-collection pointers from Jon Gruden — and I hope he is.

Dear KSK,

I went on a date with a friend of a friend who I was aware was interested in me, but had never really given much thought to. He’s plenty interesting, cute enough, very sweet and what have you, and although he didn’t initially spark my interest, I figured he deserved a shot.

A few drinks into the night, this young man begins to make it clear that he — to put it mildly — is COMPLETELY FUCKING OBSESSED WITH ME. Like, runs through a litany of my photos on Facebook and tells me what he likes about the way I look in each one. Recollects nearly word-for-word entire conversations we had the night he met me. Comes up behind me and starts STROKING MY HAIR while I’m at the bar waiting for my drink. As the night progresses and he gets drunker (so do I, but who’s counting?), he starts grilling me about my relationship history. Asks how many other guys I’m dating. Wants to know what I’m looking for in a relationship (this is all said, by the way, while stroking my face). I’m drunk and completely unsure how to react, since I genuinely don’t want to hurt his feelings. At one point, he whispers to me, I shit you not: “I want to fall asleep inside you.” ON A FUCKING FIRST DATE.

There are lots of lessons to be had at this point, I’m sure (e.g. don’t shoot tequila on a first date). Here’s where I made what I think, in retrospect, was a terrible decision, but I’m unsure. Realizing how crazy this guy was about me

— and how could he NOT be, given your succinct, humble way of speaking? —

while also deciding, at that moment, that I never wanted to go on a date with him again, I decided to toss him a mercy fuck. I figured it’d probably be the greatest night of his life, I’d get my goodies played around with a bit, and we’d both be happy in the morning. So, you know, I did.

I’ve subsequently had to go to great lengths to make him understand that I’m not interested in him. So here’s my question. Was it cruel, or ultimately kind of me to give this guy a chance to bone me when he obviously really dug me? I feel like I may have led him on in the short term, but he may be grateful down the stretch. Should I just have walked away? Or is a “mercy fuck” a genuine act of altruism?

In matters of the heart (and groin), I’ve found that life is best expressed by this simple mathematical truth: having sex > not having sex.  But don’t go patting yourself on the back about it.  Jumping on a grenade to save your fellow soldiers is altruistic.  You just fucked a guy you didn’t like.

Oh, and is Ryan Torain worth hanging onto in exchange for an 11th-round pick in my keepers’ league?

Hard to say, what with Mike Shanahan’s Running Back Industrial Complex on the outs.  The Broncos signed Correll Buckhalter and J.J. Arrington, so I’d be inclined to take my chances with someone who has a higher ceiling.

KSK Sex Gods,

I’m a 19 year old girl.

Go on.

And I’m a virgin.

/breathes into paper bag

And pretty sick of it. Problem is, I’m picky (which I know I shouldn’t really be considering my position). I’ve been given chances, but either I realized I would have regretted screwing the guy regardless of my “situation”, or it was looking perfect and something got in the way/I fucked it up all on my own. Some of my friends say Craigslist, but I’d rather not go missing and end up in a ditch in Tijuana, and I’m not into this guy (since he’s also a virgin) who’s pretty close to a sure thing. I have one guy who I give blow jobs on occasion, but he wants it when he wants it and is never very receptive to my booty calls (he used to be, but those were times when things like roommates got in the way). I guess my question is this: should I get trashed and screw whoever happens to proposition first, make things go faster with the blow job recipient, or just be patient, keep strumming the banjo, and try not to kill myself imagining becoming Steve Carell in the 40 Year Old Virgin?

As for football, I don’t have a question for that. I mean, I’m a 19 year old girl.

– Hoping (but doubting) my question will be null by the time it gets read

So, a 19-year-old female virgin with no interest in football not only follows an often-misogynistic NFL blog, but asks it for advice?  Yeah, this is real.

However, since you brought it up, I’ve made this handy graph to demonstrate the perceived worth of a woman’s virginity:

At the top of the parabola there is Prom Night, Junior Year.  By the time you get to college (or the working world if you’re keeping it real), your virginity begins losing its appeal — both for male suitors (who begin to develop a taste for women with experience) and for you (“So WHY, exactly, am I still waiting?”).

So yes, Mythical 19-Year-Old Virgin, you are on the downslope of that parabola.  But there’s no need to rush.  Find someone you like and tell him you’d like to have sex.  I doubt you’ll get turned down.  Unless you have a harelip and club foot.  In which case: ew.

Alright let’s start with the important stuff. I know my girlfriend (of 3+ years) cheated on me. How do I know this? Rumors? Found a used condom inside her vagina? If only it were that simple. I know because i read her e-mail. It’s not like I hacked into it or anything, she just left herself logged in and I helped myself to a peek. Inside, there was an exchange with a girlfriend of hers about it. Now how do I approach this situation? Obviously this relationship is over, as we are both dishonest assholes. But how do I break it off? I don’t want her to know how I found out about her cheating, because I’d like to make her feel like shit for doing it. And if she knows I went all PATRIOT Act on her e-mail, I lose the upper hand. Remember this was a serious relationship, so I can’t just avoid her like I would a clingy one night stand. Also, is it illegal to send a mass e-mail with the naked pictures she gave me? Because that would be some sweet revenge.

Football: How great is it going to be when Dan Snyder has to sell off FedEx Field’s tiny parking lot in order to finance the Haynesworth deal? Skins fans are so fucking miserable.

Yours in the prayer cross,

Jesus.  You people DO realize this is for entertainment, right?  Like, if your life is totally fucked up, you should probably ask a REAL advice columnist or something. But whatever, I’ll take a swing at this.

You, sir, have what the experts call “an extremely fucked-up relationship.”  If one of my friends told me that he was in this situation, I would say, “You’re fucked” and buy him another drink.  However, since I’m not your friend, and I have no intention of buying you a drink, all I can say is that trying to “win” a break-up is a pointless exercise.  Break-ups are shit for everyone involved, period.  You can try to duck the issue of checking her email, but it’s eventually going to come out, so you may as well be up front about it.  If she gets pissy about it, you can tell her that if she can be calm about the email thing, you’ll try not to call her a whore for sleeping with someone else.  If you need to feel some sort of moral superiority, get it from the fact that at least you were honest with her about the violation of trust that you made.  And for God’s sake, keep the naked pictures buried (unless, you know, you want the KSK staff to review them).  Karma is real, and it’s a motherfucker.

Phew.  As for your football question: very great, and yes they are.

Dear KSK,
I used to have such good taste in celebrities I would jerk off to (Halle Berry, 18 year old Britney Spears, etc…) but over the last two months my cock brain will not let me jerk it to anybody but Drew Barrymore. I can’t even go near the shampoo/toiletries aisles for fear of seeing her on a rouge covergirl box and having to jerk it in the store. The fuck is wrong with me?

Ah, you fucking pervert!

Oh, you meant this:

There’s nothing wrong with jerking it to celebrities — in fact, any adult male who ISN’T using Internet porn to masturbate is that much further away from a crippling addiction.  Just try not to do it at CVS, okay?  You’ll scare the children I’m trying to pick up.

My football question is less disturbing. If your favorite team’s top three receivers going into the season were Devin Hester, Rashied Davis and Earl Bennett and the GM consistently keeps talking about how he doesn’t want to bring in anybody else, how would you best rid your body of your eyes to avoid having to see that piece of shit offense?

Melon ballers are effective and inexpensive, so that may be the quickest route.  However, if you can handle the experience, you can probably make a couple bucks off it by offering up a skull-fucking on Craigslist.

Dear KSK,

Sex: The high school kid last week who said he bragged about having a seven inch dick inspired this question: If you were to brag about your dick, what length would you give?  Or another way of asking is what would you consider a below average, above average and enormous dick?
Football: So how soon until the Broncos trade for Wes Welker?

AK in Fort Collins

Hey, the Broncos already have Brandon Stokley!  Don’t hog all the white wideouts!  (Whiteouts?)  Other fan bases need to buy jerseys they can identify with, too, y’know.

As for your penis, the best way to brag about your dick is not by length or girth, but by feat. “I don’t know how long it is, but when I’m flaccid I use it as a belt.” “I broke a piece of granite with it once.”  Et cetera.  If you need a more specific answer, I’ve always heard that six inches erect is the median.  But you should ask the broad who’s offering mercy fucks.  She can give you a better answer.  Plus, she’ll sleep with you, assuming you can sit through her monologues about how great she is.

Gentlemen with Tendencies Towards Penile Literary Devices,

I guess I’ll kick things off with the football question. It’s actually a three part question all having to do with next year’s fantasy draft. 1) Which rookies will even be worth drafting? 2) Which perennial studs are due for a shitacular year? 3) Which players, mired in the throes of mediocrity, are due for break-out years?

(1) Wait until after the draft.  (2) That would be Mr. LaDainian Tomlinson.  Other guesses from across the Gay Mafia included Brian Westbrook, Brandon Jacobs, Purple Jesus (that’s Drew hedging his bets), and T.J. Houshmandzadeh (Nooooo!).  (3)  Your breakout stud guesses: Derrick Ward, Braylon Edwards, Matt Schaub.

Now on to my sex question. It is really more of a theoretical question and again has multiple parts, yet I feel it deserves attention all the same. Let’s say you are dating a girl, and said gf has an incredibly attractive friend who you’ve had your eye on for some time. Let’s say the friend in question is at least a 9 and you’ve had enough interaction with her to make an educated guess that she would be an absolute beastette in the sack, and you also know that she would have no problem getting down with the gf because of their established friendship.  If you are looking to broaden the bedroom horizons by asking the gf to add this friend into the mix, is it ok to agree to a threesome with another dude (no gay shit, no crossing of swords, just a straight up double team) if that’s the only way the gf will agree to dive on her friend’s muff? If so, how do you go about picking the guy for the eiffel tower? Do you pick one of your boys or do you let the gf have complete control over it? If you are going to pick one of your boys do you go with a casual friend or a close friend?

Bix Weedmann

Journalistic integrity requires that I mention Mr. Weedman sent along photo evidence of the “incredibly attractive” friend (sorry, he denied us the right to run it), and let’s just say that this is a threesome worth pursuing.  But at what cost?  It seems your girlfriend didn’t get the memo about the Great Threesome Double Standard (AKA “One Dude Is Plenty”).

Personally, I don’t know.  I’m not enough of a libertine to go for the guy-guy-girl threesome — What if I liked it?  I might be gay!  Shit! — so it comes down to what you’re comfortable with, and what limits you’re willing to push so you can get it on with a hot piece while your girlfriend watches.  Nothing comes for free.  Get it?  “COMES”????

Whatever.  This mailbag is over.

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