Your Life is a Long-Winded, Unfunny Version of a Rom-Com: the KSK Sex/Fantasy Football Mailbag

01.21.10 8 years ago 70 Comments

“Hey everybody. So, I have this dilemma. I’m super busy with work all the time, so I hired a hooker to help me relax because I don’t have time to deal with meeting women and developing a real relationship. But then the craziest thing happened: not only did she give professional-grade head, she was also a really nice person. I wanted to see her again. So of course I bought her some new clothes, took her to a polo match, introduced her to my friends — the usual. It was all going really well until my A-hole lawyer found out about her being a hooker and put the moves on her. Anyway, I paid her for the full week, but she left without taking the money and I think it’s because we’ve fallen in love. Should I go after her?”

That sounds pretty retarded, right? Read on, there’s a submission this week that’s longer-winded and just as ridiculous.

Dear KSK,
Sex: My girlfriend and I have been doing the dirty for about 6 months now. All is well and good, however, one thing kinda sticks out- I’ve never gotten her off. Not once. As far as I know, my average sized penis has been doing just fine, and I’ve actually been blessed with pretty strong stamina regarding how long I can last. I kind of feel like an asshole after I come because I’ve never made her come. So, any recommendations? Positions perhaps?

The most important variable here is one you left out: has she been able to come with other people? If not, then the problem likely resides in her head (or possibly her choice of partner).

Listen, women have a maze of internal genitalia is difficult to manipulate. What works on one woman does nothing for another. Some girls can only come if you go down on them, some girls don’t like receiving oral. Some girls need to be on top to come, others get their best orgasms from doggystyle. And some women, due to either biology or mental block, have never had an orgasm. Whatever advice I might have for you in terms of bedroom technique will likely be irrelevant — and so will any other women weighing in on the issue, because they don’t have your girlfriend’s specific sexual makeup.

The only thing you can do is ask her what she wants and what she likes. Good sex, like a good relationship, depends on communication.

Football: I’m a Patriots fan. I hate the Colts. I would give up any potential children I have in the future to see a Colts flameout against the Ravens. No real question here.
Bitter Pats Fan

This is what happens when you send in questions before the weekend. Ouch. And now everyone’s going to pile on because you’re just one more Pats fan who can’t satisfy his girlfriend. But I bet she knows how to take a punch, eh?

Whats up,
FF first – Okay, so my high school friends and I have finished our 4th year of our league and it is fantastic. It took a while to find the right combo of 12 guys, but after kicking people out and adding people I believe we have a solid 12. The problem is is that there are 3 or 4 more people I want to be in our league. I am a control freak and have had bad experiences being in leagues that I was not the commish, but I don’t want to expand to above 12. So the options that I have are…A) start a second, keeper league. Little bit of a twist from our redraft league, get to add the new guys, but I’m worried that the regular league would not continue going strong. B) start an EPL style “league”…with relegation and promotion. Sounds awesome, but not sure if the lower league would feel like they are playing for anything since they are “lesser”. C) wait for my friends to get married and have real shit they have to take care and see if the waiting list still exists. or D) join a totally separate league with a commish that is not as good as I.

Man, are you chock-full of bad ideas. Don’t fuck up a good thing. Add the new folks if other people leave.

Sex – Nuva Rings…fuck em. I got fucked over by one because I was not expecting it and got blindsided by it. Short explanation first…first few times with the girl, no nuva ring, no sex (morals…rare thing these days), but then one evening I encounter the nuva ring, I get flustered/curious, mood gets killed, things go downhill from there. Since I hope to have a fresh start this semester, my question is how to handle it? I’m not sure if I can just act like its not there…because it is there, and its fucking weird. Having her taking it out is a mood killer…but I am wrapping up either way because I don’t want some little fucker to ruin my 20’s. What’s the best way to approach these things?
Hoping no one I know reads this mailbag

Oh, you got “fucked over” by a NuvaRing? No you didn’t. Getting fucked over by a NuvaRing is getting your girlfriend pregnant because it didn’t work (note: that is merely anecdotal, not a fact you should base your decisions on). YOU just happened to be surprised by its presence inside your woman’s plumbing.

Settle down, rookie. It’s a little rubber ring that’s preventing your woman’s baby-making capabilities, not vagina dentata.

Gentlemen (and Drew),
Sex: When is it no longer OK to knock boots with the wife when a potentially awake baby is in the next room?

To answer your negative question with a negative: never. Which is to say, it is ALWAYS okay to have sex with your wife with a potentially awake baby in the next room. You just need to be quieter as the kid gets older.

Football: When the NFL fines players, where does the money go? I’m specifically curious about the punt returner (Clifton Smith) who got destroyed earlier this season. Don’t know if Dante Wesley ever got fined, but if he did, does Smith see any of that money, or is it reward enough for him to get a letter from the league informing him his misfortune has led to four exciting new acquisitions to the Roger Goodell Suit Collection?
-Durham Drinks

Wesley wasn’t fined, but he did serve a one-game suspension without pay, which translates to somewhere in the neighborhood of $50K, give or take. Whether the Panthers have to fork that money over to the NFL or just enjoy the benefit of not paying a player, I don’t know.

As for your question about where actual fines go, the best I can do is WikiAnswers: “NFL fines go to non-profit organizations (i.e. cancer awareness programs etc).” I can’t verify that that’s true, but it does sound familiar, which is good enough for me to believe it. So Clifton Smith probably didn’t see any of that money, unless he started the Clifton Smith Anti-Concussion League. But at least it didn’t pad Goodell’s coffers.

Sex or really a relationship question driven by sex: Being a shy, fat guy in high school, I was a virgin till college. Hit the weights and found some self esteem but have always still been shy around girls. Now I am that guy always with a bunch of friends who are girls. Saying my first attempt at sex was bad is an understatement. It was terrible and so I just basically focused on school and then now life. Im 22, and my problem comes in as a 33 year old. This girl is awesome fun to be around smart hot and got her shit together. Which I have learned is hard to find in girls my own age. Being unexperienced when it comes to girls I was oblivious to the fact she would even look at me until a mutual buddy told me she wanted on my dick. He was correct and we started hooking up. Sex with her is phenomenal and of course I say that with nothing good to compare it to but best I can say is being with her is better than any porn sex I have seen.

I understand what you’re trying to say, but you really shouldn’t compare porn sex to real sex. Men expecting regular women to act like porn stars is similar to women expecting men to act like the sensitive hunks in romantic comedies: yeah, there’s a couple freaks out there, but it’s best to temper expectations.

FF through a few months of amazing weekly hookups

Oh, fast forward. That’s not the best abbreviation to use for a fantasy football mailbag, you know.

and she asks me to go out with her for New Years. Like a dumbass I decline because even though things have been great, it is getting that relationship vibe. This leads to a talk about how she likes me and all this is fun, but she is old enough that she knows what she wants out of life and that she is really looking for someone to be with not to just fuck. I end up telling her I dont want a relationship at all. She left with basically a no harm no foul additude

You know who else has additude? Mathletes.

no fighting or getting upset and I was left kicking my own ass. I ended up going out where she was and still getting her to come home with me but now things are akward. We are still hooking up but def not with the same frequency and same excitement and she has made it known she is dating and as soon as she gets interested in someone the hooking up will stop. So now I notice myself calling her more trying to talk to her and when she comes over doing more of the wanting her to stay. I guess my question is, am I just a total idiot for not pursuing a relationship with this girl or am I just getting that whole want what you can’t have syndrome now that I know she is dating? I just feel like I have so much to accomplish and do still before I can settle down but on the flip I don’t want to end up being that sad fucker who ends up always taking about the “one girl” he let get away.

You’re only a total idiot for acting like you want her more now that she’s put you on ice. She sounds like a great woman, but you’re obviously not ready to settle down. You need to respect the single woman in her 30s: she knows what she wants in a man, and she only has so much time to produce babies. There will be other women for you, and by the time you’re her age, you’ll want someone who’s your age now.

Football: I feel incomplete without fantasy so I guess I just really have a sex question.

Try going without both. It’s no way to live.

Freudian Fappers,
Football first: Is it ok for me to wear a jersey to a Super Bowl party when your team isn’t competing? If I’m going to be rooting for Favre to throw a pick, or for Bush to dislocate a knee, I’d like to be doing it in one of my jerseys.

I’ve seen numerous articles and blog posts about the appropriate rules for jersey wear, and very few of them agree on all the finer points. Personally, I feel like a fraud wearing a football jersey — especially an NFL one — because I’ve got the build of a kicker. But I don’t begrudge anyone else their desire to wear a team jersey. However, I also retain the right to make fun of you if you’re wearing the jersey of a team that isn’t competing, because then you’re just a third-party asshole.

Sex: My girlfriend of over three years has been saving it for marriage (which is not coming for a few more years). I’m fine with that because I love her, and the no-sex thing doesn’t rule out oral (oh, Catholic girls). That being said, its easy for her to add variety to a bj – just switch up the angle/location/direction and you’re set. However, the options a guy has for eating girls out is limited… or so I think. I was wondering if there was a tome that men could consult to find this shit? Sorta like the kama sutra but for cunnilingus.
Thanks for your ridicule (and perhaps, advice).

Man, we’re getting lots of letters from people waiting to have sex until marriage lately. What an awful trend.

Have you tried having her sit/kneel on your face? That gives you a better angle to stimulate her G-spot (if it exists) manually while your mouth is focused on the clit. It gives her a little bit more freedom of movement, too. Or there’s the go-to porn favorite of having her bent over, which gives you access to the famed third hole. If you’re into that.

Bandwidth Barons,
Football: Can you please rank these mid- to low- tier QBs in order for 2010: Garrard, Sanchez, Cassel, Flacco.

I assume you mean for fantasy purposes. I’d put Flacco at #1 for consistency and the added running threat, Garrard at #2 for his freak big games, Cassel at 3 and Sanchez at 4. I think the Jets are going to be running a helluva lot more next year now that Big Rex has finally let Shonn Greene run loose.

Sex: I’m in a happy 3-year relationship, my gf is hot (5’9″ 130lbs, blonde, 34D), the sex is frequent and good.

Once again: we don’t give a shit about descriptions of girls unless they’re accompanied by photos. Without that, the following statement is just as true as your unproven assertions: Your girlfriend’s face is BUSTED. Somebody set her face on fire and put it out with acid. She’s the Elephant Man in a skirt.

We were both pretty keen on experimenting with another couple we know (no male-male business) for some 4some action.The other girl is also hot, the gf and I know her well, we agreed she’d be great for this kind of thing and I was pumped. Unfortunately, her fiancee

Her fiancee is a woman?!?! Best. Foursome. EVER.

lives in another city. He was back in town two weeks ago and he has gained a fair amount of weight.

Wait, “he”? Dammit, people. Fiancee with two E’s is a woman, with one E is a guy. You’re killin’ me here.

My gf also got to know him more and finds him kind of weird (I wasn’t out with them, but I had thought so too when meeting him before, but I was willing to make that sacrifice).

She now doesn’t want to have a 4way with that couple but it still interested in the idea itself. She brought up the subject in bed the other night and said “There MUST be someone else who would be into that sort of thing..”. What would be the best way to approach finding another interested couple? I’ve thought about approaching friends, but if I misread the situation and they were offended or shocked, I wouldn’t want my entire group of friends to hear about this. On the other hand, trying to find random people via personal ads, Craigslist, etc. seems sketchy, and the gf has voiced that she isn’t too keen on that (perhaps rightfully so). Thoughts?
Relationship by Committee

If she doesn’t want to do Craigslist, then you’ll need to get hotter friends. If you wanna dabble in the fringes of sexual experimentation, you may have to come to grips with the realization that those weirdos generally find each other online.

Dear KSK,
First, fantasy. I’m in a 12-team fantasy league, which I won this year for the first time. Sweet. It’s a keeper league, though – and I can keep three. The candidates:

Ray Rice
Thomas Jones
Jamaal Charles
Randy Moss
Hines Ward

I’m leaning towards Brady, Ray Rice, and Randy Moss. I figure Brady/Moss aren’t done yet, and I think Thomas Jones is getting a little old (and the Jets will have a three-headed monster next season once Washington is back). Am I being a total dickbag here?

Eh, I’d keep Brady, Rice, and Charles. With Brady and Moss so inextricably linked, you risk bombing on two-thirds of your keepers if just one of them gets hurt or shows a career downturn. By picking Charles over Moss, you minimize that risk and get a young stud on a team that doesn’t operate on running back by commission.

Second, sex. I actually don’t have any sex questions, but I saw the mailbag was slow so I thought I’d ask about fantasy.

Hey man, sometimes the mailbag goes slow. Sometimes it goes fast. Whatever you need, baby, the mailbag can give you.

To Whom It May Concern,
I’ve been chasing this girl for a year. I moved here last year and became completely enamored with our very attractive receptionist here at work. She was in a relationship at the time so I played the good friend role. We go on smoke breaks together and go to lunch and what not. So she and her boyfriend come to an end because he’s and alcoholic dickbag or whatever. I didn’t pry, and she didn’t talk about it much. We start hanging out more and she’d come over to my place and we be playing around so I made a move and kissed her. That led to some excellent shirtless making out, but she put the brakes on when I went for the pants. Ok, cool, no rush. Over the months we’ve been good friends and I’d get the occasional invite up to her place (she lives about 45 minutes away) and once I’m there she’d ask if I’d want to stay the night. So of course I do. Nothing ever happens during the nights I’d stay up there. She show no signs of wanting anything intimate and I was too nervous to press it without some sort of hint of what she wanted. When it comes time to sleep she would ask if I wanted to come to bed. There’s a perfectly comfortable couch, but she’d always ask if I’d want to sleep in the bed. So of course I do. She strips down to a tank top and panties to sleep. Again no action at night. When the morning comes though, I just said fuck it and went for it. Success. Everything is great. She’s affectionate and giving and all in all a very good time. But once fun time is over and she (or we, sometimes) get out of the shower, all that affection is gone. No hugs or anything. So this goes on for a while. It seemed like every third weekend or some random day I’d be invited and the same story unfolds. She’s even invited me to houses she is house sitting to stay over and same story there as well. All this time we keep a very good friendship going, which is great because we get along, enjoy each other, smiles, laughs, sunshine, puppies, and rainbows.

The last time we got together she had mentioned that she doesn’t think she wanted a fuck buddy. We then fuck. At this point, I’m feeling like more than a fuck buddy, and that’s what I want. You know, companionship and all that. But no go for her. She explains how she really likes me and has some feelings for me, doesn’t regret anything we’ve done, but doesn’t want a boyfriend at the moment. She feels she needs to get her life together and whatnot. She works two jobs and doesn’t have a lot of free time. So I do the most obvious thing and TALK TO HER about how I feel, and what I want, and how flexible I am to work around her schedule. Well too bad for me it seems. No girlfriend for me and no more sex. I tell her that something has to change then. I can’t be her best friend and joke and laugh with her and see her smile without wanted to be more with her. She just wants to keep being best buddies like nothing ever happened. So I told her I’d need some time to figure things out and have been relatively quiet to her up until recently I started talking to her again and trying to just be a friend (seeing as I don’t have many of my own in the first place, and we are the only two in our age group at work). Its ok now, but I still have that yearning.

Ok, so the actual question I have is: Now that I’ve gone from “Friend Zone” to “Fuck Buddy” and now back to “Friend Zone”, is there any hope to get back to the promised land, ideally a relationship and if not that, just some fun weekends without any clothes on? I’m fairly sure I know the answer to this, maybe I just needed to vent. Do I just wait it out as a “friend” until she is ready, if ever? I feel like a tool being her clown and feeling like I’m just kept around to amuse her when she is feeling down. I just can’t help that I feel so strongly about her, and its hard to put it aside when I see her looking so good everyday. If being forced to move on is the way to go, how do I go about not picturing her naked doing naughty things to me everytime I see her?

Wow, that was the longest and most boring description of (500) Days of Summer I’ve ever read. My advice: go cut yourself — if not for your situation, then at least for your atrocious inability to self-edit.

As for football… well, the season is over and all I have to look forward to is a shitstorm of media induced QB controversy, and endless complaining about our lack of commitment to a running game of any resemblance, again. On top of that, an 11-5 season (which would be quite an acheivement for about half the league) is completely nullified by being utterly dominated and embarrassed by the fucking Cowboys. Two fucking weeks in a row. Add that to the loss earlier in the season will make for extremely insufferable encounters with Cowboy fans in the near future. It was better when all they could come back with was “We have 5 rings!!!”. I swear if they win another one this year I’m going to go batshit insane. 44-6 feels like so long ago…. It hurts to root for Favre, but hopefully the Vikings can erase that smug, cocksucking, shit eating grin from Romo’s face. No real question, unless you can tell me the proper way to cut myself…..
As Emo As I Seem

Oh, you’re an Eagles fan. Just a little hint for future communiques: when you write in an email that you moved “here” and call your team “we,” other people don’t automatically know what the fuck you’re talking about.

Also, you’ll bleed out fastest if you cut the femoral artery. But don’t do that. Your tears are far too delicious and nourishing.


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