It’s Not Cheating If You Aren’t Dating: the KSK Sex & Fantasy Football Mailbag

05.23.13 4 years ago 125 Comments

Yay, it’s time for another sexbag! This week’s topics include but are not limited: some real assholes, some people who play fantasy with assholes, and some assholes who are haughty about not playing fantasy football, and a Kate Upton GIF. Thank God. Read on:

Dear KSK,
Football first. I’ve been in a 12-team league with friends from grad school for a few years now. As people have moved on (realized that having a ponytail and making $600/year is bad), our numbers have dwindled to eight last year, and now to six for this upcoming year. I’m the only one remaining who doesn’t want to play in a six person league. (Only eight teams was bad enough) I’ve suggested inviting other friends or even making it a public league to get random competition but have been overruled. A six team league is just ridiculous right?

Yes. Drop out and let them play in a five-team league, let them see how fun that is.

Also, this bears repeating at regular intervals: you don’t have to be poor and pony-tailed to play fantasy football. Fantasy isn’t some weird Dungeons & Dragons for sports fans to play in basements with their greasy loser friends; it’s a legitimate way to enjoy the NFL through an additional lens of competition (or, if you prefer the more honest word, gambling). It’s also not a necessary facet to maintain friendships, but in our ADHD-riddled world of social media, a fantasy league produces an extra wrinkle of shared experience that isn’t just a Facebook update. I, for one, play in an 8-team league with lousy settings just because it keeps me in touch with some of my old Marines.

The other common refrain: “I don’t have time to play fantasy football because I [am married/have kids/work for a hedge fund] now.” It’s bullshit. You can be competitive in most leagues by spending ten minutes on your lineup before the games start on Sunday. Everything else that fantasy geeks do — the web research, the waiver-wire-hunting, the obsessive scrutiny of Yahoo’s predictions — all just serves an addiction. Everyone has time for fantasy football. If you’ve moved on in life and don’t WANT to play, then don’t play. But shove that “I don’t have time” excuse right back up your ass where it came from.


Sex. Started a long-distance relationship with a girl four years ago. Two years ago, broke it off (long distance sucks…obviously), and agreed to meet up casually for sexy fun time whenever schedules aligned. We only set up a ground rule- let the other person know if you’ve been sexually active with anyone else…and if so get the appropriate tests in advance. I should mention at this point, we don’t use protection, with the explicit understanding that any pregnancy will be terminated.

So… she’s not even on the pill? Do I need to tell you how stupid that is, or would you like a doctor or lawyer to tell you how stupid that is? Because they can hit you from a couple different angles there.

A couple months ago we went on a trip to Asia together with some other friends. I knew she had started to see a guy, but she claimed no sexual activity with him at that point. Long story short, sexy fun time ensued, I felt something was off, went through her phone, texts confirmed she had been riding her new guy bareback too.

Three things.

1. Bad on her for lying to you.

2. An all-caps FUCK YOU for thinking you have the right to go through someone else’s phone.

3. How, exactly, do texts confirm unprotected sex? “Baby, last night’s condomless sex was so hot!”

Confronted her with evidence and she tearfully admitted it. I broke off all communication and after six weeks of worrying, got the news that my HIV test was negative.

My question- I got her new guy’s contact info when I was going through texts.

Again: that is not something that a decent human being does.

Do I tell him about what happened? I won’t pretend it’s because he has a right to know, but more because I’d like to inflict some hurt on her after she lied to me. Or should I just forget it?
Shel (not Silverstein)

Listen, it’s great news about your negative test, but your whole “let’s fuck whenever we’re nearby and never use protection as long as we’re not having sex with anyone else” is a heaping mound of naïve bullshit. I can’t defend your lover’s tactics here, because she was in the wrong under the completely moronic rules you had set for each other. What I CAN do is tell you that you’re a snooping piece of shit who had no business going into her phone, regardless of motive or evidence retrieved. The end does not justify the means.

I’d like to think that in an an alternate universe, a much less annoyed version of Matt Ufford is congratulating the alternate-universe Shel (not Silverstein) for having the sense to always wear protection for any sexual encounter that isn’t part of a monogamous relationship — instead of this crap world where I’m trying to feel sympathy for a vindictive clod with no foresight.


Dear Captain Uffsides,

I wrote to you back in February regarding drafting rookies and girls with mono. An update on the mono girl- it didn’t end well. She refuses to seek help for some depression she’s been experiencing, but you can’t help someone who refuses to help themselves, so I made the decision to cut her out of my life.

Fantasy Football: We all know Tavon Austin is FAST! I’m wanting to draft him for my fantasy team. In our league, we agreed to start doing 2 keepers. One normal keeper and one rookie keeper, with the stipulation that you can only keep the rookie if you drafted him in his rookie year (i.e. you cannot pick him up off waivers then try and claim him). My question is 2-pronged: Who should I keep between Arian Foster & Peyton Manning, and how early or late should I draft Tavon Austin?

Foster. You have a better chance of getting a good quarterback later.

As for Austin, I think there’s a very good chance he’ll be an impact player. But I have no idea what round people will target him — last year, Doug Martin was a second- or even first-rounder, while RG3 seemed to go in the fifth or sixth rounds. Ask me again when training camp comes around and I have my player rankings set.

Relationship: I was sent on a 2-week business trip on the other side of the state for a short-term oil & gas project back in mid-March. While there, the girl working with me was a smokin’ hot blonde, and the nicest ass I’ve ever laid eyes on (and, I’m not even an ass guy), and single. Anyway, nearly every day, we would go to lunch and dinner together, we got to know each other, yada yada yada… anyway, she was always busting my chops (she said, “I’m calling you out on your shit.”), but, she also gave me advice on how to make a potential relationship with mono girl work. On one hand, she terribly annoyed me and was always busting my chops, but, on the other hand, it seems like she really wanted to help me and we had a lot of great conversations. A month later, we both moved on to different companies, but we still keep in touch. After I ended shit with mono girl, I decided I needed some time away from town and went to see my friends in Myrtle Beach. Fun times, got my mind off mono girl, flirted with some hotties and enjoyed the beach.

Sounds awesome, Mr. Unnecessary Boring Details.

I made a decision at the beach that I want to go for this blonde girl in the future. If I were to right now, she’d know I was damaged goods and it wouldn’t go well. I figured the immediate future should be used focusing on my self-improvement. I’ve already lost 28 lbs this year due to eating smarter and working out twice a day with DDPYoga since mid-March. I’ve been seeing a therapist since mid-March to improve my mindset and work on some deep issues of my own I’ve had. Oh, and this girl lives 2.5 hours away from me.

With this new company I work for, I’m up near her area a lot for work (and, in my line of work, I drive on average 2-3 hours a day to and from the job site),

Sounds awful.

and several months down the road, I’d like to be able to use the dating advice she gave me on her. However, I’m also being mindful of not keeping all my eggs in one basket and I am talking to other girls as well. Question: What’s the best way to approach her about getting together next time I’m in or near her area, several months down the road?

Call or text her and say, “Hey, I’m in town. Wanna get a drink?”

P.S. Since this e-mail was a bit lengthier than I had intended, here’s a GIF of Kate Upton having water squirted on her.

And that, ladies and gentlemen, is how your long-winded question gets in the mailbag.


Dear KSK,

Sex: Whenever I play with my wife’s asshole (even without penetration), my finger ends of smelling pretty strongly.

I realize some of this is pretty par for the course, but it takes washing my hands like three times before the smell is gone. This normal? If not, any thoughts on what I could/should do? I can’t imagine my wife is going to take kindly to suggestions about that kind of bodily hygiene.

Feces comes out of your wife’s anus every day. Sometimes two or even three times a day, I’d guess. Rubbing your finger on skin that touches a lot of shit will make your finger smell like shit.

Aside from the Captain Obvious answer, I would imagine that you can lessen the poop-smell of a butt by (a) eliminating hair and (b) scrubbing thoroughly. For the former, you can suggest a Brazilian wax if she doesn’t already do that, although many women aren’t too keen to have their assholes tweezed, a position I can respect. Regarding the latter, there isn’t a exactly a gentle way to say, “Scrub your ass better.”

In general, though…

Don’t want your finger to smell like shit? Don’t stick it in assholes.

Fantasy: My group is considering converting to an auction league. What amount of money should each team start with (I realize there’s no substantive difference)? I feel like $100 seems like a good amount. Anything less seems too insubstantial and anything more just seems like it would have too many zeros. Thoughts?


Also, people like round numbers, and pieces of $100 translate directly to percentages. Less math is always better.


Hello there,
Football: None I’m a Jets fan, THIS is the fun part of the season for me just speculation and imagining that our first round pick will save the franchise (Note: We’re going to draft an offensive guard)

This was written before the Jets drafted Geno Smith, obviously. So… yay?

On to Sex or aftermath of my sex-capades: Well I’m in a pretty ridiculous situation. I dated a girl a year and a half ago who was seeing someone else. Long story short she left him for me and we dated for almost a year. I was 22 at the time and she would stay over my house (parent’s house) for weeks at a time. She was kind of poor and my mom felt for her so she took her in. We were really serious despite being young.

Whoa, hey! Sorry, my eyes rolled back so far in my head that my co-workers thought I was having a seizure. I’m back now.

After about a year of dating she lost her job and I offered to get her a new one in my town. She got the job and then dumped me two weeks later. Turns out she started dating a local loser in my town (works at a fast food restaurant, used to carry knives everywhere and pull them out on people, shitty tattoos).

“I mean a REAL loser, not just some 22-year-old living with his parents and dating a trashy girl that started out as an affair.”

Real embarrassing, all my friends who knew her as my girlfriend would see her with this douche and it made me look ridiculous. I was devastated but used it as motivation (got in incredible shape, stopped drinking, starting dating hotter women) so the actual getting over it isn’t so bad.

What is bad though is that she now lives with this kid and his family in my small hometown. It’s presented a bunch of awkward situations. My mother will bump into her at the grocery store, I run into them when I’m getting food, etc. On top of that, my friends tell me they’ve seen her at bars and when shes drunk and not around her new bf she’s rambling on about how much she misses me.

My first instinct was to try and fuck her again….I know this is retarded and I won’t but it is a charged situation. I keep running into them and it just makes me feel awkward in my own town. Any advice on how to not let it affect me or if I should say anything?

The first thing you need to do is dispel this notion that you’re somehow “better” than her just because your family’s better off or you have a job. You and her and the douche with bad tattoos are all sitting in the same dead-end town, and for some reason you give a fuck when people bump into this skank you dated.

You know how to escape small-town bullshit like this? Move. Move somewhere that forces you out of the same places and circles of people that has dictated your entire life. Make new friends, get a new job, see new places.  Sample a life that’s challenging and even scary, and when you come back home for a holiday, you’ll have forgotten the names of people you thought mattered. THAT’S what you should do. Get the fuck out.

BUT, if you’re dead-set on being a salamander who never leaves his little stream, there’s nothing I can do about that. All I can say is this: things are only embarrassing if YOU feel embarrassed. It’s completely on you. So if your mom or your friends tell you they saw your ex, then you tell them, “Why the fuck should I care? I don’t care about her bad decisions or her shitty life.”


Oh Captain my Captain,
I’m too successful to waste time on man-boy games, so I don’t have a fantasy football question for you.

“Hello, I’m too successful to engage in a pastime that tens of millions of people play and has helped make the NFL the sporting juggernaut that it is today. Now please, person on the internet I’ve never met, help me with my sex life.”

As for sex, I’ve been married for 10 years to the woman of my dreams. We have a great life together. She’s my best friend and I love her more now than I did when I married her. However, the one issue we’ve had is that she doesn’t really have a sex drive. We’ve tried various solutions over the years, but nothing has worked. At this point, we’re both ready to accept that this probably isn’t going to change. So, after many honest conversations, my wife recently suggested I hit up an escort every few months for sex. Of course, there would be some rules: always use protection, don’t become emotionally involved, don’t sleep with too many women, etc.

Are you Andrei Kirilenko, perchance?

I think this would be a workable solution; however, there is one little issue. Over the past few years, I’ve gotten into transsexual porn.

Not Kirilenko: BUZZ BISSINGER!

My wife knows I look at porn, but she doesn’t know the specifics. If I’m going to hook up with an escort, I’d like to try fucking (and getting fucked by) a t-girl.

lol “one little issue” ok

I would never do this without first being honest with my wife, and so my question to you is should I broach this possibility? I don’t want to freak her out and cause her anxiously to wonder whether or not her husband is gay (I’m not). She’s not homophobic or anything, and she’s not a prude, but sex with transsexuals isn’t exactly a “normal” thing here in the states.

So there’s somewhere it IS normal?

What should I do?
Dr. $uave

Okay. So, even though this sounds too balls-out insane to be a real problem from a KSK reader who’s too successful to play fantasy football, I shall treat your query seriously, though not so seriously to actually try to find out what transsexual porn looks like or where to even find it, or how to go about finding a sex worker that scratches your particular itch.

My advice to you, from one straight married male to another, is to get your head out of your ass. You have a wife who has given you a green light to sleep with prostitutes — “just not too many,” you know, because this is a real letter from a real person whose wife is SO not into sex with her husband that she’s cool with him shopping around the sex industry. So, definitely real person not making weird stuff up to get included in the mailbag, maybe just appreciate the freedom you’ve been given without going to extremes. Maybe see if your wife can satisfy some of your desires by strapping on a dildo. Maybe honor your marriage vows instead. And maybe — just maybe — don’t shit on my hobby if you want me to be sympathetic to your sexless marriage and newfound kink. 

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