KSK Fantasy/Sex Advice Mailbag: Bi Week Special

01.29.09 9 years ago 121 Comments

Sure they look good now, but as soon as you turn your back they’ll be fucking a guy.

Welcome to another enlightening edition of the KSK Football and Sex Advice Mailbag! After the jump we’ll delve into such topics as bi love triangles, a Rachel Maddow fetish, foodie blowjobs, and of course, the quest for anal.


I’ve been dating my girlfriend for over 6 months; she is bi-sexual. Since the beginning, she has been very upfront about her bi-sexy nature (she also has a very cute girlfriend) but has been adamant that she would never be interested in having a threesome with said sexy friend and myself. Earlier this week, she confessed that for the past couple weeks, she has been hooking-up with her girlfriend and another guy. My question is: should I stab her repeatedly with a dull knife and then set her on fire? or should I set her on fire first and then stab her?

/consults lawyer
//keeps mouth shut

Staying on the flaming topic, do you see Brady Quinn in the starters role next season, or will he be riding his gay lovers cock on the bench again?

Much Thanks-

Wow, sorry to hear that your girlfriend is a duplicitous whore. You should at least get revenge by fucking her cute little girlfriend on camera and sending her the tape. As for Brady, expect to see him under center next season, even if the play calls for a shotgun snap.


Sex: I’ve been friends with this chick, who is Bi, for about five years now (we went to school together). She has a girlfriend and has been with her for about 2 years. Anyway after a of drinking we end up going back to my place and fucked like mad. So my question is should I feel guilty for most likely breaking up their relationship?

HAHAHAHAHAHA. No, that’s just stupid. You should probably do it again. Hell, fuck both of ’em.

Football: I’m an Eagles fan living in AZ. Seeing how I loathe the Stillers, and I can’t stand the bandwagon hopping Cards fans, should I watch the Super Bowl or allow myself to be dragged to see Don Quixote at the theater?


Are you seriously considering skipping the Super Bowl to go watch some play? Fuck that, you’re a football fan, so sack up and watch the fucking game. Drinking should help rid you of these hangups.


So I get an email this week from my friend from college detailing his most recent sexual conquest. The kid lives in the Old Town area of Chicago and hooked up with a girl he met off of Craigslist. He met her at a Jamba Juice and claims that within an hour and a half he was truckin’ her at her appartment.

Is it wrong for me to hope that my friend gets herpes or some other STD simply for the humor aspect. I mean – this could provide YEARS of entertainment, but its also a dick move.

Football: Your an NFL GM and you need a running back – who are you taking in the draft? Beanie Wells or Knowshon Moreno?


You’re never allowed to wish an STD upon a friend, unless said friend just fucked your whorish ex. What you should do is mock the shit out of him for bragging about getting pussy via Craigslist. A hunchbacked leper with halitosis could get laid that way.

If I’m an NFL GM I’m not drafting any running back in the first round.

Gayest of Gay Mafia,

How prescient a monkier to have, because I am writing in to say that I have a crazy, unyeilding, Mark David Champman-esque stalking festish. I want to f*ck Rachel Maddow so hard and am proud (pun inteded) of it. That’s right – dykish hair, sport jacket, super oversized uber-hipster black horn rimmed glasses (when not on camera), quiet farm life, would not do me if I could make her Secretary of State – Rachel Maddow. If you can show me a picture of any woman out there hotter and more f*ckable than Maddow, the gauntlet has been thrown (Ed. note: see below) (hint: any pics from that dude from last week who used to video his sister in lawy might help)

Here is the problem, my girlfriend, much like every other single woman on earth, hates that I find someone else bangable. Even a lesbian. In fact, probably much more so a lesbian – because all she can imagine is me doing a 3 way with two boyish chicks. She has gotten to the point where she wants sex all the time, takes me out to eat at 9pm every night and won’t even let me have the remote. She is utterly convinced that I am going to go to a witch doctor, buy some anti-gay fairy dust, fly to NYC and try to bang the HOTTEST CHICK EVERRRRR. My girl cannot get enough of my womble snout, but all I ever think about is Maddow. Is there something wrong with me?

Football question: Any chance NBC signs a unemployed Kilby to just piss on the co-anchors for the NBC Super Bowl. I mean, the guy has no talent other than being an asshat, why not boost ratings by having him taking a giant verbal dump all over the Matt Millen Experiment? Thoughts?


I’m not sure what would repulse Maddow more, your dick or your spelling. I don’t think I want to know what a womble snout is, and I can say unequivocally that there are many many things wrong with you.

Fortunately NBC has finally run out of chairs.

Dear homosexuals who live in my computer,

I’ve been dating a girl for three months, and I’m just getting to the point where she’s starting to annoy the shit out of me (asking me to spend time with her in lieu of watching sports, yelling at me for falling asleep immediately after sex, pouting when I shoot early, blah blah blah I’m not listening). I’m ready to break up with her and get back to my twice-daily masturbatory schedule, but this week she insinuated that there might be buttsex is our not-too-distant future. As someone who has never known the pleasures of the Chamber of Secrets, I’m wondering whether it’s worth putting up with her shrill female annoyance until I can put it in her poopin’ hole.

Football: I am a lifelong Lions fan. Should I stop watching football altogether and get into some gay shit like soccer?


I hate to break it to you, but what you’re describing is called a “girlfriend”. Break up with her if that’s what you want, just be forewarned that they are all going to annoy the shit out of you from time to time. If you think you can handle a relationship then go for the anal, otherwise just get out now and go back to jerkin’ it all by your lonesome.

You sound like the exact kind of fan the Lions deserve.


I am car-less University student and go to school a distance away from my girlfriend. For Valentine’s day though, I’m taking the trip out to see her. The day of love, her roommate will be out of town, nothing could be more perfect.

Until she informed me that she will be on her period…. What do I do? I haven’t seen her for a few months and won’t see her again for a few months after so I need some loving, but I do not want to come off as not appreciating her unless she pleases my d. Is there a way to convince her for shower sex or at least a lot of head?

Hmm for the big game… What’s your favorite Super Bowl commercial?

Thanks boys

Blowjobs, blowjobs, blowjobs, and more blowjobs.

The Orwellian nerd in me loves the 1984 ad, but the rest of me is a complete sucker for anything featuring monkeys. Of course as a football blog we have to show support for Terry Tate’s foray into office linebacking.


Two-Parter: I hold my breath while knocking one off, usually leaving me winded when the deed is done, but with a heightened O. Am I on my way to autoerotic asphyxiation and premature death ala the front man from INXS?

Also, my nips are super sensitive, so how does one manage a mouse, a nip squeeze, and the lil’ general while browsing for the latest nasty on the Interwebs? I usually just rotate righty between the mouse and the nips, but it slows down the browsing experience. I figure I should just go straight to video, but I enjoy still pics, too. What’s a lonely guy in a basement to do (and for the commenters, yes, I’m married, and we do it regularly, just not the six times a day a healthy prostate requires…plus, one needs the mental ammo, and the wife knows and doesn’t care…side note: was in New Orleans and went to gamble, came back, and she was servicing herself to pay-per-view…WTF?).

What in the name of fuck are you babbling about? Is this Buffalo Bill? Nobody wants to hear about your man-nipples. Unless of course you can milk them.

Fantasy Football: Keeper League, which QB: Cassel (not knowing his destination/situation) or Schaub (and his penchant for missing four games a season)?


Take Cassel and pray for Brady’s leg to fall off at the knee.

Dear Sirs,

What’s the most disgusting thing you can imagine Brenda Warner doing?

Taking a shit while straddling Bill Bidwell’s face while blowing Kurt Warner.

How far is too far to drive for sex? Bear in mind, I’m not talking about state line prostitute sex, I’m talking about good, consensual sex with a beautiful woman. Specifically, is three hours in a car time wasted when I could beat off and be getting drunk?

Thank you for your time.


If the sex is good, and you are sufficiently in need, then three hours is an acceptable driving distance. This is all assuming that it will not interfere with your Super Bowl viewing.


I’ll be in Vegas with my wife over Super Bowl weekend, and our team made it (I won’t say which one, to avoid being subjected to more awful fan songs). Since we actually have a horse in this race, I’m having a hard time deciding where to lay my money. Do I bet on my team, or is that bad luck? Alternately, should I bet against my team, so that if they win I’m happy anyway and if they lose I can drown my sorrows in a pile of strippers? Finally, if I want to try taking the wife to a brothel, are my odds better if our team wins (a celebratory romp) or if they lose (a grudgefuck)?

Betting the Under

Normally I leave the rules to Simmons, especially with Vegas involved, but here are two that you should probably heed.

1. Never bet on or against your team in the Super Bowl (betting the under is fine).
2. Never take your wife to a brothel.

In fact, never go to a Nevada brothel at all. Unless of course you enjoy paying four-figures to fuck an ugly prostitute. You’re in Vegas, there are plenty of crazy-hot whores you can pick up for a handful of chips.

To who it won’t concern,

Football question; Should I watch Jerry Maguire before or after the Superbowl weekend, and is it acceptable that I shed a tear when Cuba was okay after the hit?

No. What the fuck is wrong with you? It’s god damn Cameron Crowe movie, not Schindler’s List.

Sex question; What is the most effective way to lure pussy this Valentines season?

Waiting in suspense,

You sound like quite the Casanova, so I’m going to suggest Craigslist. Be sure not to mention the hunchback, leprosy, or halitosis until you’ve made the date, just to be careful.


This question would probably be best suited for Drew (Ed. note: Well too fucking bad!. It involves the two things he seems to know best: Cock and Food (Ed. note: How did you know that the rest of us are cockless anorexics?!). My wife recently decided she will only suck my cock if it involves some food wrapped/drizzled around it. We’ve done the standards (honey, chocolate syrup, whipped cream) but where do we go from there? I fucking love head and I’m not about to stop this hot streak of married blowjobs.

Football: Besides Purple Jesus, who is even worthy of a top 5 fantasy pick next year?


That sir, is a fantastic question. But remember, all that matters is what foods she likes. That being said, here’s a list of foods and condiments you may have not considered that should fit the bill.

1. Prosciutto – It’s a well known fact that everything tastes better wrapped in savory Italian ham, even your porker.

2. Peanut butter – If it’s good enough for the dog, it’s good enough for the wife.

3. Spicy mustard – It never hurts to add a little spice to the bedroom and/or kitchen, just ask George Costanza.

God speed, good sir. And to answer your fantasy question, Michael Turner.

Around The Web