KSK Fantasy/Sex Advice Mailbag: Spying On Your Sister-In-Law

01.22.09 9 years ago 122 Comments

Welcome to another disturbingly arousing edition of the KSK Football and Sex Advice Mailbag! After the jump we’ll delve into such sensitive issues as how to explain away that tape you made of your sister-in-law undressing, teaching your adolescent son the proper way to clean up after himself, pregnant sex, and of course, the quest for anal.


Sex: My wife’s sister lived with us for a number of months a few years ago. I would consider these years to be her prime, Pro Bowl-caliber ones as she has since decided to marry, get pregnant and generally stop giving a shit about what people think. During those glorious months, I frequently wondered what she looked like getting into and out of the shower totally nude. Being a technology-inclined pervert with a raging desire to polish off to something only a few have ever seen, I procured a wireless spy cam and placed it in a fake plant near the shower. Let’s just say the sister liked to dry off while looking at herself in the mirror and my camera placement was perfect. AWESOME footage. Three questions:

1. What the fuck is wrong with me?
2. Could I ever make a case with my wife if she found the DVD/VHS (I like redundancy) that this actually enhanced our sex life?
3. Now that, due to my complacency and tape hiding skills of a 5 year old, she has found said tape, please repeat question 2.

Football: Fuck football. I’m fucked


You aren’t fooling anyone Strahan, we know it’s you! First of all, what kind of technology inclined pervert uses VHS? As Punter said, you need to store that shit on a password protected external device. Now to answer your questions.

1. You’re just curious!
2. No, but feel free to try.
3. Unless there was another house guest staying with you at the same time then you pretty much can’t deny anything. This is one of those times when you’re pretty much reduced to throwing yourself on the mercy of the court. And unless you have the coolest most understandingest wife on the planet, court is exactly where you’re headed.

And now allow me to ask some questions of you.

1. How long is this tape? Did you record her once, or over the course of several weeks?
2. Is there a surviving copy of said tape that we may analyze?
3. What kind of fucking idiot are you?


So this isn’t explicitly a sexual question (Ed. note: Boooo!), but it does pertain to my dick (Ed. note: BOOOOOO!). I noticed a while back that whenever I was about to fall asleep in a meeting I would pop a pretty resiliant boner about five minutes before I started head-bobbing. What the fuck is that about? I don’t recall it happening when I fell asleep in class.

Footballwise, I remember thinking back in the day that anyone could play QB if they were surrounded by the likes of Marshall Faulk, Isaac Bruce and Torry Holt. Warner’s second TD on Sunday could’ve been off by 15 feet in any direction and Fitzy would’ve still hauled it in easily. My question then, is Kurt Warner a really good quarterback, or just a really lucky one?

Eyeing the Bandwagon,

Doctors don’t fully understand morning wood, so I doubt anyone can tell you why you are experiencing the phenomena just before nodding off. Perhaps your dick just really loves naps. If that’s the case, we have something in common.

Kurt Warner is a very good quarterback who has been fortunate enough to play with some outstanding receivers in his career. He may be a bit of a pussy, but don’t overlook his deep ball accuracy just because he gets to throw to All Pros.

KSK Sex Team,

Sex Question: My wife is reaching the late stages of pregnancy. With her case of pregnancy gigantism, we’ve consequently had a difficult time getting it on. The logistics are just all sorts of messed up.

However, I must have sex now. After the birth, she’ll need at least six to eight weeks to physically heal, and I’ll need at least three months to mentally heal from the sights of having my son’s head come out of the sex spot. I’m not sure if I can go those many months without sex.

What sort of pregnancy sex can I engage in to fill my canteen before the coming drought?

Football Question: I’m in a keeper league. Do I keep Hines Ward or Anquan Boldin?

Thank you,

Men should be allowed to use the services of professional escorts under these circumstances. How this was never made into a “Man Law” commercial is beyond me, but I suspect that women are to blame. Keep Anquan and tell the preggo that if she loves you she’ll let you take care of business on the side*.

*Note: Do not actually go through with this, assuming you prefer your testicles to remain inside your scrotum.


Okay, I’m trying to be a good mom here, but I am at my wit’s end. I know 15-year-old boys are wont to masturbate basically non-stop, and I of course have no problem with his doing so (not that it matters if I *did*) but is there a nice way to suggest he not, um, “clean up” on pillow shams? I’ve put tissues in his room. He takes two showers a day. HE HAS SOCKS. What the fuck is going on here? Am I going to have to resort to saying, “Look. These shams have to be dry-cleaned. STOP HUMPING THEM.” I don’t want to traumatize the poor kid but damn. Isn’t there some sort of Jack-Off Etiquette you guys are born with?

I don’t have a football question other than how bad is it going to be on Ape if the Steelers lose?

Sign me,

I think I’m too old for this site

Send the boy our way, for we will teach him the ways of man.

Exactly how old is “too old” to be reading KSK?


Football: Some teams seem to believe you can put together a receiving corps on the cheap, filling the roster with like-skilled players who might not be ‘athletic’ but are precise enough route-runners/fast dudes that they can be successful. Does Larry Fitzgerald make those teams look dumber than the contents of a short bus?

Sex: I’m a virgin and so yes, my question is ‘What’s it like?’ Or it would, except I have a chance here…a chick is actually willing to fuck me (I’m pretty stunned too, she even knows I read KSK with the same religious fervor as Kurt Warner does the ‘Left Behind’ book series) but I have to be okay with two things: she’s a butch lesbian (so, unattractive lesbian…she looks like Mike Tirico, no shit) and it will be a rape – I’ll be tied to the bed and fucked repeatedly until I can no longer summon an erection. I guess two questions here, can men actually be raped, and is it worth it to lose my virginity to Mike Tirico-with-a-vagina, or should I wait and see if maybe I can score at the very least a Scott Van Pelt look-alike? I’m sort of desperate…but is that a bit too much?

Yours faithfully,


No, every other team in the NFL isn’t stupid for failing to build around a guy like Larry Fitzgerald. It’s not like other GM’s have the opportunity to sign the league’s best receiver only to say “eh fuck it, we can get by with Hank Basket.”

Yes, a man can be raped by a woman, but don’t expect them to talk about it very much. To answer your question regarding Mike She-rico, it depends. Some people are all caught up on making their first time special, which is a dumb fucking way to go through your adolescence. To give you the proper advice we really need to know a lot more about you. For instance, how old are you? How long have you been in pursuit of the poon? Do you have any other possibilities on the horizon, however remote they may be? Are you morally opposed to paying for it? If nothing else is playing out in your favor you might as well just make the leap. Hopefully you can at least upgrade to a Scott Sans Pelt.


So I just started dating this girl and we’ve had sex a few times but now she wants me to start going down on her. The only problem is that she doesn’t do the best job shaving down there. I sort of discreetly asked her why and she said her ex-boyfriend thought it was sexy so she assumed all guys liked that. How do I tell her that her ex boyfriend is flat out wrong? Also, I’m not exactly a “cunning linguist.” Any tips?

Football wise, what historically awful team (aka which Court of Fail team) do you see next making the step up to the Super Bowl ala the Cardinals?

Adam K.

Easy, just tell her you’d be able to do a much better job if she’d go Brazilian. Trying to predict the next football team to “make the jump” is a futile pursuit. Every year teams rise from nothingness to the playoffs, so it can really happen to anybody. Except of course for the Lions. They’ll still be sucking when we’re all dead and buried.

Dear Fucktasters,

Football question: given Cutlerfucker’s displeasure with the firing of the Oompa Loompa, is the safe bet on the Broncos being even more of a shitshow than they were this year? What’s the story with his contract, anyway? Does he have to stick around? I demand expert analysis here. Don’t make me email Fatsis.

Sex question: my boyfriend (yes, I’m a chick) claims that if we ever wanted to get our freak on with some voyeuristic action, he could find a willing dude at any random bar on any random night to come home with us and watch us fuck (no threesome action involved or implied, just watching/jackin’ it.) I say there’s no way, and that we’d have to turn to the internet to find someone who is specficially looking for that sort of activity. So, who’s right? Would any of you pervs go home with a random (and reasonably attractive) couple to watch some live porn? And no, that’s not an invitation.

Regards and stuff,


Invitation or not, Ufford’s on his way.

As for Cutlerfucker, he’s three seasons into his rookie contract that goes for a total of six. With a hot young coach in Denver the future actually looks pretty bright, at least right up until you remember that said coach is a former Belichick coordinator. Don’t let that lack of obesity fool you, he could be every bit the fuckup as his predecessors. Hell, Josh McDaniels has already hired his 28 year-old brother as an offensive assistant. Who needs real coaching experience when you’ve spent three years as a quarterbacks coach at a couple of Ohio high schools? I’m sure Cutlerfucker can’t wait to benefit from that turd’s experience.


As impartial observers, who should we be rooting for next Sunday? Will it be worse to hear Steelers fans have more bragging rights, or to see the creation of a Cardinals bandwagon?

I live in an apartment building that’s apparently made out of paper. Anytime my girlfriend and I are doing the deed, it’s obvious that the neighbors who share a wall (and especially those downstairs) can hear everything. No one wants to hear their neighbors having sex; is the onus on me to try to keep things quiet, or is it just tough shit for the neighbors?


How can you not root for the Cardinals in this situation? Their fans are delightfully apathetic and they’re all neatly tucked away deep in the southwest.

If the walls really are that thin then you at least owe it to your neighbors to make an effort to keep the volume down, but fuck, they’ll probably hear you no matter what. Give ’em something to complain about and grunt like Maria Sharapova taking it up the ass.


Football – My FF league is getting very lazy and this year they decided to not have any money involved. Do I ditch? Or give them another chance to shape up and put some fucking money in?

Sex- My wife doesn’t really let me play with her breasts that much since we had a kid. She is scared that she is going to leak milk while I’m playing with them. The thing is she stopped producing milk MONTHS AGO. I think its unfair for me not to be able to have access to them. Plus…I like tits. I mean….I really like tits. And she has nice big ones (no picture available….yet). How can I get her over her fear so that I can get the motorboat going again?


The only thing worse than fantasy football with nothing at stake is women who don’t let you fondle their breasts. Simply remind your wife that you put up with that stupid wedding idea of hers, so now you own those milky fuckers.

Dear KSK,

I’m going to Vegas in about a month. It’ll be the first time I’ve been. All I really know about the place is from those Simmons columns which only really teach you that if it wasn’t for those “Asian closer dealers” that he’d be a millionaire. My question is, how much should I budget out for strippers/whores? Normally I’d budget out a lot because I’m painfully single and live in one of the many states that has strict “no touching” laws (but hey, it beats Utah’s “they can’t get naked at all” law). But I’m going for the bartender’s convention which means numerous hot chick bartenders loaded up on free booze. So should I budget out a little and take my chances with a bunch of women with impaired standards or just hit up the titty bar? Or both?

My football question is, how do I make it the next week and a half without wanting to attempt every one of Drew’s suggested methods of suicide? If I have to hear about how Fitty was a ball boy for the Vikings one more time I’m jumping into a tank with Nazi Shark with a fishhead belt.

-El Duke

Your best bet for dealing with the bye week is to take a dry run through Vegas. It never hurts to be too prepared, and this way you won’t be overwhelmed by loud noises physically impossible tits during your bartender gathering. If you do jump in Rolf’s tank make sure the fish head belt is made entirely of smoked fish heads.

Your budget for strippers and whores depends on your overall budget for the trip. The rule of thumb says to only spend what you win at the tables, but I say take your overall gambling budget and triple it. Your best bet is to take one (or more) of those bartenders to Cheetah’s and show them what kind of tipper you are.

Of course you’ll probably lose all of your money playing blackjack against JONATHAN FAHKIN’ PAPELBON! and crying yourself to sleep with your dick in your hand. But hey, at least you’ll always be able to tell everyone how you scared Norv Turner away from your table!

/high fives Hench


1 football – am i the only one thinking that the weather is going to suck and when its cold (compared to AZ), windy, and possibly raining (a la bears/ colts SB) that the cards are going to get totally exposed after these 3 long weeks and get destroyed big time?

2 sex – so after a dumb 4.5 year relationship i finally got out of it. she was hot, but it wasnt working and plus the sex was boring. the rebounds were all 7s to 9s so i wasnt bitching, but the first real girlfriend after that was roughly a 9.99 give or take .01 depending on whether it was a monday or a friday, and the sex was absolutely awesome. of course she went back to her ex-boyfriend who i want to stab with a soddering iron in his pee-hole. anyways, how long is the appropriate time to mourn? and since apparently i can pull decent strange in still (no clue how), what is the appropriate level on the hottie scale that i should go after for revenge sex (aka crying sex)?
hail the matron saint,


How the fuck do you know what the weather in Tampa is going to be like?

A 9.99? Really? Go fuck yourself with a soldering iron.


Jim Mora was recently introduced as my favorite team’s new coach while the Rams hired a superior coach, do I give up now and wait for the Coors commercial or pretend that he had nothing to do with the atrocious secondary and will be a fine head coach?

That whole Rod Tidwell speech from Jerry Maguire about shoplifting the pootie was a joke right? Something put in the movie to please all the single mothers who loved Say Anything so they could sell more tickets? I should be able to bang single moms and never call them again if I want to.


Ufford answers:As a Seahawks fan, I admit, I’m somewhat less than confident in the skills of Jim Mora. But let’s not panic yet. The Rams hired a superior coordinator, not necessarily a superior coach. Remember when Romeo Crennel was a defensive genius sure to lift the Browns the heights of the AFC Central?

The NFL is a fickle bitch. Most of the actual coaching in the NFL comes not during the three hours we watch on Sundays, but during the rest of the week, when the head coach manages a staff of coordinators and coaches. Mike Holmgren sucked at running a 2-minute drill, but that fat walrus could turn anyone reading this into a capable D-II quarterback. So let’s wait and see what Jim Mora, Mike Singletary, and Steve Spagnuolo can do over the course of an entire season before anyone’s ass gets crowned.

Okay, now back to me. Go rent a movie that isn’t a poorly disguised chick flick and maybe you can get your balls back.


Who is your favorite porn star?

What is it that you actually DO once the Super Bowl is over until the beginning of the next season?


1. Your mom.

2. See 1.

And now, for some anal emails.


Football: If the Cardinals do anything to catch the Steelers off guard, do you think The Edge will have a bigger role running the ball, or the Buzzsaw will throw in the trick play towel and just heave it to Predator Larry Fitzgerald all day?

Sex: So I’ve been dating/banging my girlfriend for over three years now, but she won’t hand over the anal sex until “there’s a diamond ring on my finger.” Does that seem fair to you? We’ll probably be married in the next few years, but how long does she think I can wait?

Waiting For Anal

That’s just preposterous in every way imaginable. Try to calmly explain to your wife that if she wants a god damn ring then she’s going to have to earn that shit the hard way.

Oh, and fuck The Edge. And Bono. The Buzzsaw need to spread the ball around quite a bit if they want to get Fitzy freed up in single coverage. This will mean giving the ball to Edge (no “The”), Anquan, Breaston, and anybody else on the field who can manage to get open before LaMarr Woodley rips Warner a fresh new asshole.

For the rest thinking of knocking at the backdoor, read this.

And finally, here’s a follow-up from a previous edition of the ‘bag…


That’s right gay mafia, your advice was taken, and it turned out to be terriffic.
If you can recall, I e-mailed a few months ago about a current girlfriend that enjoyed the blowjob-on-a-regular-basis routine. She then decided to start sticking a finger in my ass while performing that made me uncomfortable to say the least. Well taking your “tread lightly” advice on this very delicate subject, I parlayed it into something spectacular. I decided to suck it up and not be a pussy about a small female finger in my ass, and told her it would turn me on as well if I could, in exchange, explore her anal region. This has led to my first (and now regular) anal encounter! What a fucking trade off!!

Thanks KSK, you really changed my life.
/Middle-aged woman infomercial voice.

I keep 2 of the 4 for next year: LT, Cutler, Rowdy Roddy, Gore

Is there some sort of drawback to keeping the running backs? Will you lose picks later in the draft for keeping high draft picks? If not keep the backs and pray, otherwise stick with Cutlerfucker and Roddy.

Around The Web