The Thin Gray Line: Moral Ambiguity and the KSK Sex/Fantasy Football Mailbag

05.26.11 6 years ago 93 Comments

First of all, a huge thanks to PUNTE for tackling last week’s mailbag. I think it’s important for us to change things up every now and again — both at KSK and in life — and should I ever succumb to a tragic death by blood clot because I spend too much time sitting down at my computer, you all would be lucky to have PUNTE wax on about bestiality every week.

Let’s get to your questions.

Dear KSK,
I recently got married to a wonderful woman. Like many married men, I carry some regrets about how I only get to sleep with ONE woman for the rest of my life, but it’s not a big deal – I take my vows seriously and I’m not going to cheat on my wife. I’ve got a perfectly good imagination I can use whenever I start feeling like I’m missing the variety of partners (or at least, the perception of variety) that I used to enjoy when I was a single. Which brings me to my fantasy question.

I have a female friend named Dawn that I have known for about as long as I have known my wife. Dawn was a gymnast at a Division I university and definitely qualifies as my “type.” We’ve never been (and never will be) anything more than friends, but at some point – I think it was after I got married – Dawn mentioned to me that she has taken nude photographs. I would like to see these photographs. I would like to see them very much. I figure Dawn would not have mentioned them to me if she were particularly shy about showing them. My question: on a scale of 1 to 10 (1 being a disinterested shrug and 10 being a scorched earth divorce), how big of a deal would it be if I took a gander at these photos? I browse porn occasionally, and while I try to be reasonably discreet about it, my wife wouldn’t be particularly surprised or upset if she “caught” me. However, since it’s somebody we both know, this seems like it would be different. Especially knowing that there’s a good chance I will be fantasizing about a naked Dawn the next time I am intimate with my wife.
-Fantasy Semantics

Oh, hello there, gray area. Welcome to the mailbag.

Your dilemma is the difference between the letter of the law and the spirit of the law. Would accepting and looking at pictures of a naked Dawn violate your marriage vows? No, not unless you exchanged some crazy specific vows. But acquiring these photos, in my opinion, is the first step on a slippery slope: if you say yes to these photos, what’s to stop Dawn from some flirty G-chatting at work? Or maybe some friendly drinks the next time your wife’s out of town? None of that is cheating, but it’s not being a good husband, either.

Listen, as a horny male, I absolutely want you to get your hands on those photos, if only so you can forward them on to me. But being a man of integrity sometimes requires your brain to triumph over your cock. And frankly, I’d rather say a small, easy “no” to a friend’s nude pictures than attempt a big, difficult “no” after three drinks and her hand in my pants.


Dear Captain Crunch (-ing Box),
FF First: I have the usual issues with paying dues that many other posters have, but I want to ask about draft location. My league is a bunch of guys recently out of college, with some starting careers, some in grad school, some working dead end jobs, some doing nothing. That said we want to organize a draft event that everyone can get into. We live in the greater Philadelphia area, so Atlantic City usually comes up, but I feel the economic restrictions for some members are prohibitive enough to stray away from that because I don’t want people worrying about money when they should be getting drunk and messing up their picks. Do you have any suggestions for a smaller scale event that we could make a weekend of?

I don’t see why A.C. should be out of the question. If you guys are young and just out of college, then you’re used to living in filth and tight quarters, so it shouldn’t be too much to put eight guys into two hotel rooms (financially soluble guys can get their own rooms if they want). Or get one big suite — excellent for hosting a draft party — and have the poor guys sleep on couches or in sleeping bags. Whatever the case, there’s probably an affordable combination of hotel rooms as long as the poor dudes are willing to share quarters. I mean, it’s Atlantic City, not Dubai.

If you want to keep it local, just host it at the home of whoever has the biggest open space. Buy a keg and order pizzas. If you have any friends on the Eagles cheerleading squad, see if they’ll serve the beer and give out lap dances for free. Hey, it can’t hurt to ask.

Sex: I have been dating a girl who I love for the past few months, but we (shockingly) live 2 hours apart. We talk on the phone every day for 30 – 60 minutes and I see her probably 3 out of every 5 weekends.

Whoa whoa whoa. Someone missed the memo that there’s a four-month moratorium on questions regarding long-distance relationships. I’ve done myself and everyone who reads this column the favor of deleting the rest of your question.

Feel free to submit your question again in September. (And if it’s a different question because you got out of the long-distance relationship, even better.)


Dearest Internet Advice Man;
Relationship Advice: This, fortunately is not a traditional long distance relationship issue.

Thin ice, pal.

I graduated law school on the East Coast two years ago, and moved back to the Midwest. Over the last year I started communicating with a girl that I sort of knew through school through the Facebook. She graduated last week and is heading back to the town where I live at least for the Summer, and maybe longer. I would characterize our interactions over the last few months as flirtatious, but I’m really not good at identifying exactly what is flirting. We even hung out and had a few drinks a couple times when she was back for Winter Break, but we were both seeing people at the time, so it didn’t lead anywhere (besides a lot of fun and laughing). I’m well aware of the Caveman rule of “She Only Wants Attention,” (and have been burned by it before) so I never really thought it was going anywhere, until I realized she was coming back to town. She’s really, really funny, loves Hawkeye football, cusses almost as much as I do, hates all the same people I hated in law school, and is way out of my league beautiful. So, yeah, I’m interested.

Two parts to my inquiry:

1) Are there any keys I can look for in our past communication that would indicate genuine flirting, and not attention-seeking behavior?

Yep: physical contact. If she touches your arm or leg when she laughs at your joke, that’s flirting. If she isn’t touching you, try touching her arm or leg (keep it friendly, not creepy). If she reciprocates sometime during the conversation, that’s a green light for more flirting and possible kissing.

I can’t believe I have to write this down for an adult. This is like Flirting 101, dude.

2) Do you have any suggestions for delicately exploring a potential relationship? Important things to consider: we have an extensive network of mutual friends (we started talking because her best friend in law school is dating my friend from law school) and serious issues may arise if I misread some signals or act too aggressively.

So rape is out. Got it.

/crosses “rape” off list

She’s going to be studying for and taking the Bar Exam this summer, and I’m working two jobs, so time is going to be an issue. I’m relatively poor. She may have to leave town after the summer. The only thing I can think of is A) Trying to get shit faced drunk and hooking up, or B) just coming right out and telling her what I want, but the fear of rejection is high.

I think there’s a happy medium somewhere between A and B. You can have a couple drinks with her, try out your newly learned flirting tricks, and if that goes well you can be obvious about admitting you like her without being awkwardly direct. Saying things like “It’d be a shame if you leave after the summer, because I really enjoy hanging out with you” gives both you AND her more options than “I really like you and want to date you.” The former allows her to reciprocate and move forward OR, if she’s not interested, to gracefully back away without rejecting you outright. The latter approach puts her in the potentially awkward position of saying, “You’re a nice guy, but…”

Come on, you went to law school! You have to be able to read people better than you’re letting on.

Football: I don’t play fantasy, but I’d like to share this football related story:

I went to a D3 school to play offensive line. Our running back my Freshman year was Fred Jackson (now of the Buffalo Bills). The night before our homecoming game, our school did the coronation of the homecoming court at the pep rally bonfire. Fred was named king. When they described his future plans, the MC read: “Fred plans to play football at the next level after graduating from college.” When I heard that, my inner monologue said: “Dude, give it up, you’re an RB at a D3 school.” I liked Fred, and he’s a great guy, but I was predisposed to being more pragmatic in my goals. I’m so glad Jackson proved me wrong. For those of you that are unaware of his journey to the NFL, it’s amazing, and you should look into it. (His Wikipedia page is a good place to start)

Jackson inspired me to say “fuck it” and do what I love. The reason I have to work 2 jobs over the summer is because from August to May I make an underwhelming $15,000 a year as a D3 college offensive line coach, and I love every second of it. Thanks Freddy!
Broke-ass Lawya

Wow, that was all heartfelt and sincere. You’re weird, but you seem nice. Good luck with everything.


Sir Sultan of Twat,
Sex first: About two months ago, I met an awesome girl via a close mutual friend. I spent a couple weeks concentrating on befriending her – going to yoga class, out for jogs, etc – but it was evident from the start that we had excellent chemistry. After a couple dates we finally hooked up and even though we tried hard to take it slow, things got serious pretty quickly. She would say things like, “I can picture you as my best friend” and “it feels like I’ve known you forever,” and it’s fair to say that I was equally smitten (oh yeah, and the sex was the best I’ve ever had, too). We spent about a month in this dream-like world, and in my opinion it just kept getting better. However about a week ago I noticed she was acting a bit cold. When I asked what was wrong, she basically told me that she was in a pretty fucked-up mental state and was “emotionally unavailable.” She tried to dampen the blow by telling me that I was the perfect guy and that I had said & done everything right, but that she just couldn’t see anyone right now. I reacted calmly, offering my consolation and understanding, and even said that we could try to be friends for the time being (stupid, I know – but I was pretty shocked & trying to salvage something). Now obviously I want more, but I know that stating this desire will only repel her further. My current plan is to tell her that I have no real expectations for commitment and that I just want to enjoy our time together in the present moment… but should I give her some time/space to get herself in a better place? Tell her how I feel when I see her next week? Or am I fucked, perpetually relegated to the dreaded ‘friend zone’?

I’ve been in your position before, and I’ve also been the person who put the out-of-left-field brakes on like that. In every case, there was someone else in the picture: I started dating someone else, or she was still tied to an ex-boyfriend but didn’t want to disclose details. It sucks every time.

Part of the burn in a situation like this is that you just don’t know why the fuck it happened. And I think you’d be justified in trying to get an explanation out of her if you phrase it the right way: “Hey, I thought we had something special, and I think I deserve a better explanation of why it happened. Whatever it is, you can tell me, etc.” Maybe you’ll get an answer. Maybe she found another, better-looking person. Maybe it’s family trouble she doesn’t want to entangle you in. Maybe it’s herpes.

Or maybe you’ll never know. Some mysteries go unsolved. Personally, I think you have the best chance of getting her back if you just cut her out and give her the cold shoulder. NOTE: this is also the best way to start getting over someone.

FF: I have a pathetic circle of friends. Every year they tell me they’re interested in playing but inevitably a couple miss the draft, beginning the downward spiral and the league is basically dead by October. Can I entice them to actually care by instituting a buy-in, or are these dudes pretty much hopeless? Should I just find a better group of friends who actually care about fantasy football?
Salacious in SF

Hell yes you need a buy-in. For some players, it will make them care a little bit more and make your league more fun. Others will still slack off, but fuck them: you have their money, and you stand a better chance of winning it if they don’t field a competitive team.



I do not have a fantasy question. I do, however, have a sex-related question that I would like a man’s perspective on.

Ooohhh, lady reader!

/combs hair

I have been dating a guy for a couple of months, and I like him a lot.

/messes hair back up

He is attractive, funny, and nice without being a pushover. We recently progressed to the sober (work night) sleep over, and this is where the problem comes into play. We had sex the first two times we had sober sleep overs, and both times, he finished within 2 minutes.

/combs hair again

After the first two sober times occurred, we have still been spending the night together sober, but not having sex. (We still have great sex when not sober.) I think that he is embarrassed about the quick finishes. I am willing to work with him on this — to be explicit, if he needs to have sex once quickly and have a longer second time, I am OK with that, or if he needs to beat off in the bathroom first, I am OK with that, or if he needs me to blow him first, I am OK with that. I know the key to this is clear communication, but I need some advice about how to start the conversation without embarrassing him further. Any advice you could give me would be much appreciated.

Thank you & please keep me anonymous.
-Janet P. Kozlowski
498 Grand Avenue
Alliance, Nebraska 69301

I’d keep two things in mind: (1) actions speak louder than words, and (2) the best time to talk about sex is immediately after sex. Allow me to flesh those ideas out, so to speak.

First, you say that you’re okay with various different things, like blowing him first or going for a second round of sex after the quick trigger. So just do it. The next time sober sex lasts two minutes, give him a minute to enjoy his orgasm, then grab onto his cock and don’t let him get soft. Pump that thing like a butter churn. Get on top and use him. Maybe it’ll work, maybe it won’t, but if it doesn’t, you can say, “Sorry, I just love your cock and want more of it.” Which leads us to:

Point #2: the nice little post-sex glow is the best time to make the little rudder adjustments that keep the USS Coitus on course. With all the endorphins pumped into his brain will make him happy and receptive to a conversation about pleasing you a little more before he finishes.

And a final note: some men just have quick triggers. If that’s the case with your man, he’s likely to be self-conscious about it, so tread softly and compliment frequently. And make he gets you off orally first when he’s sober.

(images via the excellent glasscaseofemotion; and yes: that’s a fake name and address for Janet)

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