The KSK Sex/Fantasy Football Mailbag Has Sex with Chicks

10.14.10 7 years ago 64 Comments

First things first this week. I’m gonna talk about my fantasy football team for a paragraph or so. Later on in the mailbag, I’ll share a paragraph about my sex life, but for now behold:

Ouch. That right there is the final score of my Week 5 loss to flubby in the KSK Keeper League, which sullied my bid to go 5-0 in both of my fantasy leagues. I survived Jermichael Finley’s goose egg and had a narrow lead entering Monday night, but flub had Mark Sanchez yet to play. All I needed in the final four minutes of the game was a SINGLE KNEELDOWN from Sanchez for -2 rushing yards, but NOOOOOOO. Favre’s game-sealing interception had to get returned for a touchdown, resulting in another Vikings possession.

Damn you, fantasy football. Such a fickle mistress.

(On the plus side, I briefly stopped sucking at FanDuel. Nothing eases the pain of loss like gambling winnings.)

What’s that? You don’t care about my fantasy football team? Dammit, I listen to your sob stories every week, allow me this one indulgence. No? Okay, FINE. Let’s get to your questions.

Dear Sir Loincloth of Rainbow Land,
Football first, if you don’t mind. This happened two years ago, so I would appreciate a retroactive man code ruling. I sent out a trade: Hank Baskett and some crappy RB for Adrian Peterson. I don’t know why I did it, but he accepted the trade. Apparently, he did it by accident. (duh) I asked our league GMs (yes we have 2) if the trade was cool. One said yes and one said no, which was good enough for me to keep AP. The slighted owner turned nasty saying that he was in four other leagues and that this one didn’t matter to him. By that admission from him, was I technically in the right? (He ended up phoning it in the rest of the year by releasing all of his players and I barely made the playoffs, losing in the first round.)

Hmmm. I’m not sure if I have a ruling. I don’t have a problem with the trade — anyone too stupid to confuse the words “accept” and “decline” deserves to lose Adrian Peterson. And even though this other character acted like a bitch, I have to admit that I’m kind of impressed with the extent of his sour grapes. He may be a childish asshole who isn’t very smart, but I respect that kind of spite.

Its sex (or lack thereof) time. I’m 20 and I’ve never kissed a girl.

Hey, it happens.

Hell, I’ve never danced with a girl and don’t think I’ve ever had a girl as a friend.

Okay, that’s pretty unusual.

(To be painfully honest, I have never masturbated.)


I just don’t connect with girls and have never really gotten along with them. I am a heterosexual male and I have needs.

I disagree, sir. If you had needs, you would have learned to jerk off some time in the last ten years. And if you’ve never connected with a girl, never befriended one, and never wanted one so much that you touched yourself while thinking of her, how can you be so sure you’re heterosexual?

However, I see those needs waning and I know that is not healthy. I have been going to the gym to pump up my testosterone and give myself some animal instinct (that was your advice at some point).

I recommend the gym for physical fitness and the confidence it can give people. I could be wrong, but I don’t remember ever telling someone to pump up their testosterone. It’s more likely that that advice came from a commenter. Which doesn’t mean it’s bad advice — merely that I don’t stand by it.

After years of quashing my urges and general avoidance of the opposite sex, how do I even start to get into the game? How can I kiss a girl at 20 when I’ve barely had so much as conversations with girls? Sometimes it just seems easier to pack it in and become a hermit. I just feel that I am so far behind in my social-sexual development and that it is too late. I’m still not even in middle school sexually.
Thanks for reading this,
Sexually Stranded

Dude, first of all, you’re still WAY young. As previous editions of the mailbag can tell you, there are plenty of virgins in their 20s who just kind of missed out on regular sexual development. You can’t even drink in a bar legally, so there’s still plenty of time to catch up and enter mainstream sex-having America.

Second, and more importantly, you need to figure out what makes you happy. I’m more troubled by what seems to be a disconnect with your sexual identity than by your lack of experience with girls. Rather than blind guesswork (“Are you on medication that affects your sex drive? Were you molested as a child? ARE YOU GAY?!?!”), I’m going to suggest meeting with a psychiatrist or licensed therapist. (If you’re in college, most schools offer some form of free counseling.) Simply talking out your feelings with a disinterested stranger will give you more peace of mind and direction than I can possibly give you here. Good luck.

Oh, and start masturbating already.


Dear Richard Simmons Jr.,
Virtual Football: Brees on the road against Tampa or Roethlisberger at home against the Browns?

Brees has been disappointing this year, but he’s still an excellent QB to start. And because I’m risk-averse, I’d prefer to see how Ben plays in his first game before just rolling the dice and hoping that the Steelers turn him loose to throw a lot against a bad team (NOTE: this is also the strategy I employed in keeping Miles Austin on my bench in his first start last year — 10 catches, 250 yards, 2 TDs).

Still, I’d stick with Brees. Despite the Saints’ lackluster start, I think he’s still in the Adrian Peterson-Chris Johnson-Antonio Gates-Peyton Manning tier of star players that you start every week, no questions asked.

(Alternative question: DeSean Jackson vs. ATL or Donald Driver vs. MIA?)

DeSean. Stick with your stars.

Virtual Sex: I unwittingly met someone online, I’m 28, she’s 18, and we’re a couple thousand miles apart.

You “unwittingly” met an 18-year-old online. Man, I hate it when that happens. “Oops, here I am in the Barely Legal Chatroom again.”

Ridiculous, I know, but after 41 straight nights of video chat, our affections have grown from a flaccid Favre to a double Shiancoe all the way across the sky. Now I’m torn between either moving to her city and ramping up our relationship OR focusing on the obvious red flags and walking away from it all. She knows about (and supports) the former, but isn’t aware of the latter. Any advice?


Why does it have to be such extreme options? Why can’t you just go visit her? Oh right, she still lives with her parents. Because she’s 18.

In all honesty, you’d be stupid to pick up and move to a new place just because you had some good video chats with an 18-year-old. But you’d also be stupid not to jump on the chance to wear out that teenage ass. I mean, I love a taut young body more than most guys, but I can barely tolerate most women in their early twenties, so how on Earth you survived 41 nights of talking to an 18-year-old without blowing your brains out is a mystery to me. At the very least, you’ve earned an opportunity to enjoy her in person. Buy a round-trip plane ticket, and if she does indeed live with her parents (or in a dorm room), shell out for a weekend in a hotel as well.


Dear Lords of Dongtown,

Fantasy Football first: So through this year, my team has already been ravaged by injuries. Now Calvin Johnson, Peyton Hillis, and Aaron Rodgers are not practicing this week, stretching me very thin, and I can’t afford to have a bad or no-show QB showing and stay in contention.

I’m thinking of dumping either Spiller, Cribbs, or Mike Williams for a backup QB while Rodgers is questionable. I was hoping to not worry about that till the week 10 bye. The best options on waivers? Young (@Jac), Cassel(@Hou), Campbell(@SF), Freeman(NO), Hill(@NYG), and Kolb(Atl). Nobody in my league trades, btw. They all believe they’re just peachy-effing-keen, even at 0-5. I’m leaning towards Hill, myself, but that could just be because I’m dumb (dumb enough to believe my QB would be immune to injury, at least). I just need them to produce this week, then I can worry about the bye later.

I myself am an Aaron Rodgers in both my leagues. I’m starting VY in one league (who was already my backup), and in the other I picked up Josh Freeman on waivers. If I were you, I’d drop Cribbs for one of those two guys.

Sex: So I was engaged until about 7 weeks ago, at the ripe old age of 24. Mutually broken off, but not before she said some pretty nasty things about my capabilities as a man and as a lover. It rather shattered my confidence, sadly, made me question a lot about myself. I had about a month to “grieve,” aka put away a year’s supply of beer and liquor, and then I decided to get back out there.

I’ve been out to the bars a few times since, somehow managed to bring girls home twice, secured a date once, but I haven’t been able to get anywhere. I might be the only guy who’s slept next to a woman every other weekend since August and gotten nothing from it. I couldn’t even get a kiss on the date. I get jittery nervous, clam up, run my mouth, fumble through sentences… it’s really awkward. I used to consider myself at least moderately charming, and I’m athletic and attractive (at least, that’s what my friends keep telling me). Luckily, I have a steady job and a decent circle of friends who are willing to help me meet women. Gay wingman, by the way? Fantastic friend. He can enthrall 3 women in a group while I talk to the one that I’m interested in. Everyone should have one of their own.

The problem I have is self-confidence. I feel like if I can get over the hump, get one successful date, one successful hookup, I’ll be fine. I’m not one to go the “just get her drunk” route… it’d probably just make me feel even worse. I guess it’s more of a psychological than a “sex” question, but how do you get back in the saddle after you basically start over? It’s a first for me to go from the mentality of “I’m spending my life with this woman” to, well, shit, and I don’t know how to start rehabbing.
Proud drafter of Montario Hardesty

Three words: High. Price. Hooker.

If you’re feeling cheap or full of morals, then you’re going to have to revert to my usual advice: forget about women and work on yourself. If you invest more time making your solo life more fulfilling — at work, in the gym, in newfound extracurricular activities — then you’ll naturally become happier, more confident, and more comfortable in your own skin. You won’t need to feel nervous around girls, because your life will be fulfilling without them. Which means you’ll get laid, like, all the time. Nothing drives a woman mad with desire quite like a man who doesn’t need her.

Also: your ex-fiancée is a bitch. Forget what she said, and to prove her wrong you should treat your next lady to the world’s longest cunnilingus session. Seriously. Get some scuba gear.


Dear KSK,
Football: need advice on who to start for my two receivers and wr/rb flex. I already have Miles Austin for slot #1. Receivers availiable: Satana Moss at home vs Indy, Jabar Gaffney vs Jets, Austin Collie vs Washington, Lance Moore vs. Tampa. For the flex I have the mentioned recievers plus Benjarvis Green-Ellis vs Baltimoore, and Ryan Torrain vs. Indy. As of now only Collie is listed as “Probable”.

Collie and Torain.

Sex: I have a co-worker (female) who is making advances on me(male). She is 20 years older than me. She is not my boss, but she is friends with him. I am asking what is the best way for all parties involved for her to stop. She is a recent divorcee if this helps.

I’m sure it helps her come on to you.

By the way, she is native-Japanese and she does all the stereotypes in a Hines Wald post. Example: I carried a new fax machine to her office and she told me later “You had the powah. You velly strong!”

Step 1 is you tell her politely that you’re flattered but not interested, and you’d like to keep your relationship professional. Most people get the picture after that, but if that fails, then Step 2 is a trip to HR to file a complaint (assuming your company is large enough to have an HR dept). If there’s no HR, then you’re going to have to go up the chain.

Or you could just love her long time. She so ronery since divolce!


Hey Caveman,
Fantasy: I’m trying to unload Randy Moss because Favre is a shitty QB and I have Brandon Lloyd, Malcom Floyd, Kenny Britt and Brandon Tate as my other WR’s. Do you think I should hold on to Moss or trade him for one of the following: Michael Turner or Lesean McCoy? (My starting running backs right now are AP and Rashard Mendenhall).

Randy Moss for LeSean McCoy? I’d make that trade. McCoy’s been an absolute stud so far this season, even with the cracked rib.

Also, I have to say that that’s some pretty savvy WR drafting you did. Lloyd and Floyd didn’t go very high in drafts, but they’ve been having monster seasons. Well done.

Sex, but not really: I’ve been talking to this girl for about eight months now. She has a boyfriend and I have an on again, off again girlfriend that I am currently on with. I told this girl before that I would be willing to leave my girlfriend for her, but she said she didn’t know if she had feelings for me and/or wanted to leave her boyfriend for me. That was four months ago. I have no reason to think she doesn’t want to be with me but I also have no reason to think she wants to be with me… So should I just accept my place as a friend or make another attempt to start a relationship with her?
184 words

If you’re going to pursue other girls, sack up and break up with your girlfriend. When you grow up enough to do that, try talking to women who DON’T have boyfriends. This is all covered in the first week of my class, Don’t Be a Fucking Asshole 101.


Dear Gentleman,
Relationships first. I’m in high school and I’ve been going out with a girl for about a month now.

Oh good God. People in high school read KSK? I’m not sure if that’s heartening or a sign of the apocalypse.

She’s always been pretty shy and innocent, but recently things have taken a turn for the better. I slip the finger with great frequency, along with a bunch of other high school relationship bullshit, but she has yet to even touch the Big Piece (yes, that’s the nickname I gave my penis). Not even an accidental brush while we are going at it. I have a terrible case of desert dick, and I would really like to get a nut off in the near future. Should I wait until she does it herself, or sack up and ask her?

The next time you’re hooking up, take her hand and place it on your boner — OVER the clothes. It’s a pretty minor step, but it should be a nice gateway to handjobs. Keep in mind that the “shyness” likely comes from inexperience — as you move forward, you’ll probably have to coach her on how to touch you and what feels good. Take that responsibility seriously, as those will be important tools as she goes on to give other guys handies and BJs throughout the rest of high school and on into college.

Fantasy: I can only start two of these guys: Michael Bush vs. San Fran, Frank the Tank vs. Oakland, or Ahmad Bradshaw vs. the Lions?

Respectfully Yours,
The Blind Squirrel Who Can’t Find His Nut

Gore and Bradshaw.


Earlier tonight, I walked away from a surefire ménage à trois between a 23-year old married woman and her very willing 17-year old babysitter. By ‘surefire’, I mean that the three of us were alone in a bedroom and clothes were starting to come off when I had a sudden pang of consciousness and bolted out the door. Would you consider this a commendable display of virtue or a colossal fucking mistake on my part?

Both. I mean, I’m duty-bound to commend your virtue, but now you’re going to spend the rest of your life regretting what might have been. Sorry.

Anecdote time: When I was a young second lieutenant in the Marines, I made a brief return to my college to teach a couple of classes at my old ROTC unit. Before I left, I MAY OR MAY NOT have hooked up with two teenage female ROTC students at the same time. This may or may not have been discovered when a spurned ex-girlfriend broke into my email and found evidence of the details, and that ex-girlfriend may or may not have printed that email out and taken it to the commanding officer of the ROTC unit.

But what DID happen for certain is that I got the ass-chewing of a lifetime for it, and it resulted in agonizing letters of apology and all the sexy individuals involved suffering professional setbacks.

And you know what? Totally worth it. I’d do it again ten times out of ten. Of course, in my case, nobody was married and everybody was legal. But in your case that would have made the threesome EVEN HOTTER.

I’m not helping, am I?

I’m so conflicted that I just spent the past 45 minutes blankly staring at my fantasy roster in order to ask you this: Sanchez @ Mile High or Brady vs. the Ravens?
-Stroking It With My Moral Upper Hand

Brady. Duh.


Dear KSK,
Fantasy:Who to play as my 2nd WR: Wes Welker (@ Bal) or Davone Bess (@GB)?

Welker. True, it’ll be a little tougher for him without Randy Moss stretching the field, but that little dude is slippery. He’ll still get his looks.

Sex: Say a guy buys you dinner repeatedly and takes you out on what can only be considered dates. There is some physical contact, but nothing too major. Then, when you go over to his house and he invites you to spend the night, you get in bed and he puts on Leno and doesn’t make a move. Obviously, the Leno alone is a dealbreaker. But even if I was willing to stick it out, I’m totally wasting my time here, right?


Jesus, when I write it out in under 150 words, it’s even more depressing.

Another satisfied customer!


Dear Pussytubers,
FF: 12 team league, non-ppr. Need some trade advice. I have D.Williams, L.McCoy, Forte, Tomlinson, and Hillis at RB and badly need to upgrade at WR (Mark Clayton was my #1 until now). I’ve been trying to spin off Hillis for a top-WR but no one is biting (best offer is R. Williams for Hillis). Question is basically this: Do I continue to hold off on dealing Hillis until someone gets desperate, accept a fringe #2 receiver for him, or trade any of the other RB’s (I’ve got an offer of McCoy for Fitty)? I can also package any with Neckbeard (PeyPey is my starter).

Even though Hillis has been putting up great numbers right now, he isn’t perceived as a top-tier RB. Roy Williams is probably the best you can hope to get for him, which is why you should be content to just keep riding him to victory for now.

I think you should be able to get a top WR plus an extra cog by packaging one of those backs with Orton. Frankly, I’d look to unload LaDainian during this miraculous (and certainly small) window of speed and good health he’s enjoying.

Sex: No personal questions (have a great relationship) so a general interest question: How awesome would it be to be a psychologist who specializes in dealing with porn stars? I would love to ask some of these girls questions like “What led to you shoving a baseball bat up your anus?” or “Do you feel that your early childhood experiences contributed to you having 12 dudes blow a load on your face at once?” I need to know these answers (in case I ever have a daughter).
Best Regards,
Too Many RB’s

I know I shouldn’t take your question too literally, but I have to point out that psychologists don’t usually ask specific loaded questions like that. It’s more “… and how did that make you feel?” and “Why do you think that is?” Other than that, yes, I’m sure it would be awesome, assuming you like hearing about sexual abuse and broken families. High-five, bro!


Hey Uff,
FF: With Rodgers likely out I need to grab one of the following QBs off waivers: Favre vs. Dal (ZOMGHEHAZMOSS!!!11!) , Cutler vs. Sea, McNabb vs. Ind (they have no safeties left), Big Ben vs. Cle, Kolb vs. Atl, or V. Young @ Jax.

I’d go with Big Ben or VY. Roethlisberger is obviously the more proven fantasy option, but VY showed some throwing skills last week, and the Jacksonville pass D is Swiss cheese.

Sex: I actually don’t have a sex question but since you’re the only Seahawks fan I’ve ever come across I thought I’d take the opportunity to ask your opinion of Hasselbeck. How many more years of productivity do you think he has?

Negative two?

Can you see him being comfortable hanging around the Seahawks when they draft or trade for some young up-and-comer?
Boring dude with normal healthy relationship.

I really like Hasselbeck as a person, but I no longer care what he does with the rest of his career as a player. As far as I’m concerned, the JAKE LOCKER FOR SEAHAWKS QB campaign starts here and now.


Meine fotze Führer,
Football first: after Ray Rice and Jamaaal, I have no idea what to do with my WR and Flex spots (two WR, one Flex). I’m working with NYG Steve Smith (vs Detroit), Santana Moss (vs. Ind), Donald Driver (vs. Miami), Eddie Royal (vs. NYJ), BenJarvus Green-Ellis (vs. Baltimore), Ricky Williams (@ GB), and I just picked up Danny Amendola (vs. SD) off the waiver wire. It’s a half PPR and–because our commissioners a douche–a half point per carry. Any suggestions on who start/strategy going forward is appreciated.

I wouldn’t give Driver the nod with Matt Flynn starting. I don’t love Royal’s matchup, but you should probably start him. I like Amendola in a PPR league, so give either him or Santana Moss the other WR spot. And I guess Ricky Williams can go in the flex.

(NOTE: None of your options there are very good.)

Sex: I’m decently in shape, but christ, I just get tired during sex way sooner than a 26 year old should. I’m in a committed relationship, and I don’t have trouble getting her off or getting myself off, but still, my energy level seems off. I generally feel this way whether or not I’ve been drinking or smoking or getting enough sleep. I’m a distance runner, so I would have thought I’d have that going for me. Any tips, suggestions, or new ways to work out that might help? Maybe I’m just lazy.

As any triathlete can tell you, cardiovascular fitness does not translate across specialties. Which is to say: you can run a marathon but get exhausted by a 500-meter swim. Sex requires a lot of effort from your lower back and core muscles near the hip, so you should develop them. Olympic lifts like the snatch, clean, and deadlift can all give you more strength in that department. Anaerobic workouts with kettlebell swings will also help in that department. If a lot of the words in the last couple of sentences are foreign to you, make friends with a personal trainer or seek out the nearest CrossFit gym. Or if you’re allergic to weights, yoga and pilates also develop core strength well.

Lastly, if it’s not a muscle issue — that is, you find yourself tired sooner than you should be in activities besides sex — have a doctor do some bloodwork. You might be iron deficient or entering the final stages of cancer. Probably cancer.

(NOTE: I am not a doctor.)

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