Dating Girls on the Offensive Line, Revisiting the Threesome, and ‘Keeping the Change’: Your KSK Fantasy Sex/Football Mailbag

05.21.09 8 years ago 118 Comments

You know the deal: you send us questions about your fantasy sex life and your fantasy football team, and we give you flippant answers when we don’t have the right answers.

Before we get into this week’s mailbag, a clarification from last week: one reader wrote in about his desire to “bang a blackie,” something that we found both offensive and out of touch (as slurs go).  While it was made obvious that the person should be ridiculed in the comments, we should have done a better job of making it clear that we don’t want your racial or homophobic or gender-biased slurs in your submissions.  Unless it’s one of the ones for Italians or the Irish.  Those dagos and micks don’t deserve any better.

Football, as always, first. Am I the only person who thinks that Cutlerfucker isn’t that much better than the neckbeard and the reason the Bears didn’t make the playoffs last year because of the defense? Also, how long until Cutler starts bitching about having Devin Hester as his number one target?

I love the city of Chicago, but Jesus Christ you people are some delusional sports fans. The reason the Bears didn’t make the playoffs last year was because they couldn’t beat a team with Tarvaris Jackson at quarterback.  Listen, just because Orton doesn’t suck as hard as the 20 previous corpses the Bears trotted out under center doesn’t mean he’s actually any good.  What you have in Jay Cutler is one of the best young quarterbacks in the league.  Kyle Orton is shit.  He’s shit that doesn’t smell as bad as he used to, but he’s still shit.

That said, the rest of the offense that isn’t Matt Forte sucks, so yeah, Cutler might still be a sad panda at the end of next season.  And I wouldn’t want it any other way.

Onto sex, I dated this chick during high school, had a bad break up, and thought that was that. Three years later, we have started talking again, and I am trying to at the very least become fuck buddies if not an actual relationship. The only issue is she somehow has gotten hotter with three years of college, and now may be way out of my league. How do I go about this and is her mind already set to a no?
Mike Hunt

Without knowing the details of your previous relationship or the break-up that ensued, I don’t think there’s a tried and true method to getting back together with her.  But I can assure you this: there’s a certain amount of magic that comes from knowing/screwing someone in high school that never goes away, so the opportunity is there.  But if she’s only gotten hotter since then, it probably wouldn’t hurt to get your ass in the gym for a few weeks.  Fatty.

Masters of Madams,
I’m the pregnant sex guy. The pregger chick moved in with her parents for the rest of her pregnancy so we are done.

So sad.  I really thought you guys had something lasting.

I have moved on. I first met this chick in college in North Dakota. We hooked up and went on a few dates. Years later our paths crossed again in the Twin Cities while I was in grad school and she was working there. She had gained weight, like 60 lbs.

Whoa!  Imagine curling two thirty-pound dumbbells.  Now imagine the weight of those dumbbells in fat cells.  That’s like an entire third-grader.  Stay away from Midwestern chicks, people.

I was nice enough to her as I’m not a total dick. We hung out a few times, but I was busy with school and she was a gargoyle. We have not talked in 2 years and I recently moved to Fargo from an internship in Boston. She now lives in Fargo too. She has dropped the 60, plus another 20. We ran into each other and hit it off again. We hooked up and then in the morning she was acting really weird and crying. She told me that my cold reception to her in the cities caused her to lose all the weight and she had always hoped of seeing me again to throw it in my face. Once she saw me she said she couldn’t do it and all she wanted to ever do was be with me.

So apparently, you WEREN’T that nice to her, and you ARE a total dick.  But I guess all’s well that ends well.

She is engaged and wants to break it off with her fiance to be with me. I have been in Fargo for 3 months. The only women here are dumb 19 year old undergrads sneaking into bars and wives of military guys that are overseas while they sit around and cheat on them at every chance. Which is terrible. It is strange that our paths have crossed 3 times in 7 years in 3 different cities, but I’m not ready to be with some crazy chick. I’ve been at my new job for 2 months now and don’t want to have to move again. She pretty much does anything I ask inside and outside of the bedroom, but I’m 28, I don’t need crazy. She wants to get engaged to me now. How do I tell her no without her killing me and the fiance? This has all happened in the last 11 days.
-Pregnant Sex Guy

flubby: More red flags than May Day in Moscow.

So basically, you’re somehow cosmically tied to this girl, she’s infatuated with you, and you have no hope of doing better while you’re in the city that you don’t want to leave, but you don’t want to be with her?  Your desire to avoid the crazy is impressive.

If I were you, and I wanted to maintain my bleak dating prospects in FUCKING FARGO, I would tell her that yes, obviously, you two have an uncanny magnetism for each other, but that you’re not in the right place to have a relationship with her (much less get engaged), and if you dated the knowledge of breaking up her engagement would weigh too heavily on your conscience to enjoy the relationship.

Hi Cockubuses,
This combines football and ladies so not a seperate question. The girl I’m dating plays JV football wtih me on the O-Line (we’ve been dating for 2 years). We’re usually called the ‘hulk couple’ because we’re 6’5/280 and 6’1/230 respectively and she’s a great gal–loves sports like I do, honors student, all of that, but the Varsity razzes us constantly. She wants to try out for Varsity with me but I know they’ll give her a hard time (the only girl we’ve ever had on the Varsity team was a kicker) even though she’s more than qualified. She tells me she’s going to go through with it anyway, because she has something to prove to those asshats and its good training for when we deploy after school. Is there anyway you fellas know of a good way I can try to talk her out of it? Call me a sap but I don’t want to bust skulls over this and her.

So you’re a 280-pound badass who’s comfortable enough with himself to date a woman over two bills, but you don’t want her to pursue her goals if it means other kids make fun of you?  Sorry brutha, but you’re being a selfish asshole here.  Look at it this way: at least you’re big enough to kick people’s asses.  Some of us didn’t have that luxury in high school.

Dick Joke Jockeys,

[I had a college relationship with a girl who] lives an hour’s drive from our University town, while I live much farther, so when Graduation time rolled around it was time to end things. Which was tough, she was everything I wanted in a girl, except for her hometown, which is far, far away from my current location. So there has been lots of that uber gay webcam stuff going on,

Actually, assuming you’re a male, I believe that’s the opposite of gay.

and I am flying back to said University for the convocation ceremony in a couple weeks. Obviously the opportunity for some “I haven’t seen you in months oh my god I missed you so much never leave me again” sex is going to arise. But I really don’t want to go through the whole emotional process of parting ways again, or get trapped into a long distance relationship which I think are ridiculously stupid. Considering I still do care about the gal a lot, yet all the while am very horny since I haven’t had any play in between, what’s the best course of action here.

Easy.  You go there, you start hooking up, and just as the clothing starts to come off, you say, “Wait.”  From there, you tell her that you really care about her, you still want her so bad, but you can’t offer her a real relationship because long distance is just too hard for where you’re at right now.  Assuming you’ve done your job and she’s turned on too, she’ll agree to the conditions and you can get back to what you both want anyway.

As far as football is concerned, what are your thoughts regarding the CFL?  Being Canadian, I was wondering if you American ass-hats had ever seen a game/enjoyed it. Personally, I prefer the NFL, just because the greater number of teams makes for a more competitive league, but Chris Berman seems to dig our brand of pigskin up here.
-Snoop (abundant-amounts-of) Doggy Style

You’re correct in that the NFL is a vastly superior product.  I’ve never cared much for the CFL — three downs just feels wrong to me — but Punté says that he likes it okay.  It’s kind of like frottage that way: it will always have a small group of freaks who like it.

Brotherhood of Bukkake,
I asked my wife if given a choice would she rather “keep the change” aka swallowing or receive a facial, she said facial.  Now how do I talk her into letting me give her said facial?

Three steps: (1) Be nice to her.  For, like, a solid week.  Flowers for no reason is always a nice move.  (2)  Booze.  (3)  Talk to her during sex.  If you drop “I wanna cum on your face” after three minutes of silent thrusting, that’s not gonna do it.  Tell her she looks hot, tell her you love fucking her, tell her which body parts make you hot, etc.  Then, when it’s getting close, say, “I wanna cum on your pretty face.”  That way, you’re letting her know that you want to demean her, but also, hey, you complimented her!  You think she’s pretty!

Also, should I keep Reggie Bush in my keeper league or try to trade him?  I don’t think I’d trade him for anything less than a second round pick.
I’ll hang up and listen,

Ugh.  Fucking Reggie Bush.  Such a pain in the ass. Will he or won’t he play?  Twenty-seven combined yards because Pierre Thomas gets his carries, or 200 all-purpose yards and two touchdowns?  I know your pain.  If it’s a PPR league, I’d consider keeping him.  Otherwise, I think a third-round pick might be worth not having him as a weekly headache.

Dear Masturs of the Batorverse,
FOOTBALL: I am headed to Vegas in June and was thinking about laying a $50 long shot (>20 to 1) Futures bet for Super Bowl Winner. I’ve narrowed it down to 3 long shots. Which would you take of these 3, or if I am totally off base, which have I overlooked?
Dolphins 25 to 1
Bills 30 to 1
Chiefs 40 to 1

Ooh, tough one.  Maj is the gambling “expert” around here — please note the sarcastiquotes — but judging from this list, there’s pretty slim pickin’s beyond 20-1.  The Packers, Vikings, and Saints are all decent bets at 18-1 (especially the Saints), but among your choices I’d lean towards the Dolphins or Chiefs.  I may be a bit of  a homer, but I think the Seahawks are a better 30-1 bet than the Bills.

SEX: My wife and I have been trying to pop a Mini-Me in the oven for almost a year now with no success. (No, I don’t want your fertility advice). In the beginning of this venture, it was great. She was supplying it more than ever and it was the same quality sex as the prior four years. The problem is that our lack of success has really changed things. Now that we have ovulation kits, temperatures to take, and blah blah… These scheduled sex sessions have become, well, scheduled. It is more like a visit to the Dentist Chair than a roller coaster ride through Poon Town. Frankly, my performance is suffering due to this.


When I told her that she needed to “liven it up some”, her act came across faker than a bulimic’s D-Cups. It is almost worse for me now that she is faking her interest than it was before. I need some suggestions on how to genuinely spike her interest in our baby making time, and it can’t include porn. She still hasn’t totally gotten over the MILF evidence I left on our laptop one day. I wouldn’t describe her as particularly adventurous, but neither am I really. But I wouldn’t call her a prude.

Any suggestions welcome.

P.S. I already know that the commenters are going to suggest I find out what her fantasy is. I asked. She doesn’t really have one.
Some Guy

She’s faking interest?  Pretend she’s a hooker.

Your priorities are backwards.  You’re supposed to have sex for the orgasms, and pregnancies are supposed to be the unwanted, accidental result of it.  As soon as you get too focused on making a baby, then it just becomes work.  And I think I speak for us all when I say, “Fuck work.”  Take a couple days off.  Stop worrying about making a baby, build up some aggression from not ejaculating, and take it out on her.*

*with sex, I mean.  Not with hitting.

This question was inspired by the fact that last Thursday’s mailbag was on Matron Saint Day: Assuming there were no consequences, i.e. your wife/girlfriend would not find out, would you “kiss” suzy kolber (read: bang her).

Yes.  Absolutely.  But then, I don’t have a wife or a girlfriend.  Oh, I know: it’s hard to imagine a blogger without a girlfriend, but it’s true.

Football: Ignoring the obvious off-the-field factor, where do you think Michael Vick as a quarterback would best be suited? Again, I don’t care about which team might take a chance on signing him, but where would he be the most help. (This instead of what would his fantasy impact be since that’d be hard to say without knowing which team he’d be on.)

Vick would be the most help on the teams with the shittiest quarterbacks.  In that sense, the Raiders and Lions (if they want to give Stafford some learnin’ time on the bench) seem like excellent choices.  Other opinions from the gay mafia included the Vikings, Dolphins (Wildcat!), and Toronto Argonauts.

Dear sirs,
My girlfriend wants to have a threesome (wahoo!). But only with a girl.

Oh no, what a terrible problem.

In fact, we both have set our sights on one lovely lady in particular, a good friend of ours and a nice piece who has been known to have been interested in girls in the past. The three of us are all very close/comfortable, she makes out with my girlfriend all the time and came on to me hardcore when we first met before she knew I had a girlfriend, so I know there’s mutual attraction there. We were all set to make our fantasies come true a little over a year ago, but about an hour before our “date”, she canceled because some dude asked her to be his girlfriend and she accepted. They’ve been dating ever since (fucking dude has no idea how lucky he is), but yesterday they broke up (finally!). Yesterday was also the day that my girlfriend and I graduated college (do threesome problems ever happen outside of college?),


so we moved our separate ways about 15 minutes after hearing this news. FML. Horrible timing aside, we are going back to campus in June for a weekend, where this girl will be. Any advice as to how to make the crazy college threesome happen (yeah, I know, booze), as well as your thoughts on whether my girlfriend and I are shitty friends for caring more about fulfilling our elusive sexual fantasies than our friend’s heartbroken state?

As long as you’re not hurting anyone emotionally or physically, fulfilling your sexual fantasies NEVER makes you a shitty person.  I’d say that a wild threesome is just the kind of noncommittal rebound most people look for after getting out of a relationship.  Now go get drunk and nail those girls.

As for football, I’m a Steelers fan, so I have nothing to complain about. Is Bill Cowher a douche for cheering for Carolina against his native Penguins? Do former iconic coaches/players have a responsibility to support the other teams of the cities in which they are beloved? I say yes. Fuck those guys.

All the best,
The Annoying [Former] College Kid Who Can’t Just Be Happy With One Hot 22 Year Old And Wants Another

Really?  You need your FORMER coach who lives in Carolina to root for the hockey team from Pittsburgh, not Carolina, just because he used to coach a team from Pittsburgh in a different sport?  THIS is the thing that’s bothering you during the off-season after your favorite team won its NFL-record sixth Super Bowl?

I hope that threesome never happens.  Ass.

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