Dickaholics, Flirty Flight Attendants, and the Restorative Power of the KSK Mailbag on Your Erection

07.01.10 8 years ago 61 Comments

It’s that time of the week again. I don’t have much to add in the way of exposition here, but I’d like to point out that next week I’ll be vacationing in Mexico, so be sure to send your queries for next week’s mailbag to the KSK hotline, not to me personally.

Now, on with the show!

Dear Sugartits,
Sex: I had a one-night stand with a girl at her college when I was visiting my buddy. It involved copious drinking, erectile dysfunction and the redemption of awesome hot tub sex.

Few can deny the redemptive power of hot tub sex. What, you think Mother Teresa got that popular by washing feet?

Luckily for me, the girl lives sorta close to me during the summer. But as I tried to make moves, she mentioned that she has just started dating somebody.

She still, however, wants to hang out. In her message, she seemed to throw mixed signals concerning whether or not she’d be willing to let me sow my oats. So I ask you, what is a proper way to gauge the situation without seeming like a dick? Should I just show up with two bottles of cheap wine and try to dictate the pace of the game? Or is the noble thing to back off until she’s completely single…I mean she mentioned it for a reason right?

Hrm. She could have any number of motivations, none of which are particularly great news for you. Just off the cuff:

  1. She mentioned the boyfriend because she’s sober and she feels it’s the right thing to do, but she wants to hang out because a few drinks could make her forget that.
  2. She mentioned the boyfriend because she really likes him, but you’ve shown that you like her so she’ll happily accept your attention.
  3. She doesn’t want to hurt your feelings, so she’s given you an insincere “Let’s still hang out.”
  4. She just enjoys fucking with dudes’ heads.

So the best-case scenario, I suppose, is that she sees you, decides you’re better than her new boyfriend, and ditches him to spend the summer with you. That’s not entirely implausible, but it’s unlikely. Slightly more likely: she cheats on her boyfriend with you, then goes back to him because she’s only near you for the summer. But the most likely outcome: it’ll be a huge blue-balling waste of your time.

If it were me in this scenario, I’d probably say something along the lines of, “Thanks, but I’m really interested in dating you, and trying to be your platonic friend would just fuck with my head.” But consider the source of that advice: I’m kind of old. I abhor getting entangled in drama, and I’d rather sit at home and masturbate than roll the dice with another guy’s girlfriend.

The important stuff: My dad offered me two free tickets to a Raiders pre-season game he got at work. On one hand, I’d love to get hammered before and during an NFL game. On the other hand, its the pre-season and since I dislike the Raiders and would likely be drunk, I’d be a prime candidate for their fans’ violent behavior. What should I do?

It’s the preseason. Not even Raiders fans can get worked up enough over a preseason game to knife a guy. I think.


I have no sex question, just fantasy football. I am in a PPR keeper league and am having trouble deciding which players to keep. We can keep 2, it costs you a draft pick 2 rounds higher than they were drafted (3rd round in 2009 would be 1st round in 2010), unless they went undrafted, which costs a 12th round pick. Here are my options and cost: Jamaal Charles (12th), Marmalard (6th), Percy Harvin (7th), Kenny Britt (12th) and Mendenhall (11th). I am leaning towards Marmalard and Harvin, but Charles is tempting.
Keeper Konundrum

Rivers is as close to a sure thing as you’re gonna get, and for the cost of a 6th-round pick is a great keeper. Harvin had a great rookie season and will still be a threat, but I wouldn’t be surprised if he went through a little sophomore slump. Sidney Rice, Visanthe Shiancoe, and Adrian Peterson are all more likely to get chances in the red zone, and that offense becomes a huge question mark if the 41-year-old man running it gets hurt. Assuming the 41-year-old man DOES return to play another season, which of course he will.

So what about Jamaal Charles? In the back half of the 2009 season, only Chris Johnson put up better stats. Charles finished with over 1100 yards rushing in what was essentially half a season of work. Granted, Thomas Jones will siphon away some carries this season, but I think the difference in picks (7th versus 12th) gives Charles the edge over Harvin.


Dear internet wise men,
Sex: I am very happily in a quite serious relationship. We have even discussed the timeline for engagement and that kind of stuff. I was chatting with my brother about her one day and I don’t recall how it came up or why I said it, but I made the mistake of telling him that “she seems like the type that might pull out a dildo and tell me to drop my pants…” So… here is the part that brings me to you for advice. I never once mentioned this to her or made any sort of remark that would give her the slightest clue that I said that. One night while fooling around I tickled her a bit (she really hates being tickled) and out popped a threat. She said “if you do that again, I am going to shove an umbrella up your ass…” She later called it “Mary Poppins-ing.” I am quite sure it was all in jest, however, the scary part is that she had a nickname for it. Should I be concerned for my anal sanctity?

Yes, absolutely. No matter how much you love a woman or think that you two share a common vision that makes you life partners, what she really wants more than anything is to anally violate you. It’s true. The reason you don’t hear more about it is because married men are too ashamed. It’s like prison rape.

My advice to you: get rid of anything remotely phallus-shaped in your home: shampoo bottles, candles, zucchinis, ax handles, remote controls, power strips — really, anything with a diameter smaller than that of, say… an orange. Because she’ll stuff it in your ass when you aren’t looking. Sleep with a knife under your pillow so she knows you mean business.

Football: I am in a very competitive 12 man league where there are kick return incentives attached to players to give a bigger pool of starters. Eight of the twelve teams were above .500. I am having some troubles deciding on keepers although I have a pretty solid pool to pick from. The roster for this league goes like this: QB, RB, RB/WR, WR, WR, TE, OP(any offensive position), D, K. I included last season’s positional rankings to give a measure of where players rate given our scoring. Pick four, Drew Brees(2), DeSean Jackson(1), Reggie Wayne(10), Sidney Rice(13), DeAngelo Williams(16), Beanie Wells(35). The current four I have the keeper tag attached to are Brees, Jackson, Wayne and Williams. I have to determine who to keep by July 14th, and that makes Rice a pretty scary option because of the Favre situation.
-The perplexed Packer fan

Hmmm. I’m not sure how Rice’s situation with Favre is any less of a scary option than DeAngelo Williams, who’ll be sharing time with Jonathan Stewart in an offense led by either Matt Moore or — wait for it — Jimmy Clausen. But your other three keepers are solid. I suppose I’d lean towards Williams over Rice just to guarantee a decent RB in my lineup, but don’t be surprised when he fucks you. That dude LOVES fucking over fantasy owners.


Hello there Gentleman Caveman,
Let’s get the important queries done first. I’m the token chick in 2 fantasy leagues. (I must say placing second and third was a HUGE deal because they thought I was gonna be easy money) League #1… came in 3rd (won’t bore you with the bad beat scenarios)….should I keep MJD or Ray Rice? Been checking the strength of schedule and I think it’s a coin flip. LEAGUE #2…Schaub, Cedric Benson, or ‘I done broke my arm’ Steve Smith. Will totally comply to your superior acumen regarding my keepers.

I’d pick Rice of over MJD for two reasons: he’s younger, and the Ravens are a better team. I just see Rice getting more touches at the goal line and in the second halves of games. As for your second league, I’d take Schaub, but that decision is partly because Ced Benson has burned too may fantasy bridges in his time, and the recent assault charge may cost him a game or two. And I think the days of the Panthers’ Steve Smith being the “good” Steve Smith are over. Hold on to the guy throwing to Andre Johnson.

OK. For the sex aspect…..I have this friend. He is a bit younger than me. (7-8 yrs) I recently coerced him into ‘benefits’.

Did you wear a low-cut shirt? That shit works every time.

Knew he was intelligent, funny, and talented. He enlightened me to your site, actually! The problem is I have become addicted to his dick.

Oh no! You’re a dickaholic!

Not only is he the biggest dude I have ever been with, he is skilled. It’s like I need a 12 step program for my desire to perform fellatio. He totally has opened my mind about things I fantasize about…(anal…another chick in the mix…) Realizing, as I do, that there is no future with this dude in the long run, how stupid will future suitors see my behavior? My girls give me hell CONSTANTLY for not entertaining other offers……………. Hope I wasn’t overly verbose, just needed a male opinion!

Steel Cougar

You were not too verbose. But I will say: that is a FUCKLOAD of periods. That last collection is something like 15 periods. That’s an ellipsis squared plus two more ellipses. That’s five seasons for the female body.

Anyway, your question was, “How stupid will future suitors see my behavior?” That depends. If your behavior is going down on those suitors all the time, they will probably appreciate it. On the other hand, if your behavior is a lackluster response because the suitors’ penises aren’t as big as the one you crave now, then it will be annoying and they won’t like you. The last thing a man EVER wants to hear is that some guy who fucked you first had a bigger dick.

So yeah, best you wean yourself off the younger guy now. The longer you coerce him into sex when there’s no chance of a real relationship, the longer you’re putting off moving forward with your own life.


Dear KSK,
You might (definitely not) remember my email from several months ago about my embarassing problem with the ol’ flaccid penis.
This was the mailbag it was posted in.

I am happy to say that for the past few months my penis has been making me proud.

The KSK mailbag: it fortifies your cock.

I met a girl last Christmas with whom things are getting serious. The first three or four times we hooked up Limpy reared his ugly head and I was left feeling inadequate and with no confidence. I was sure she would stop calling, but lucky for me she didn’t. Being fed up with the situation I decided to take matters into my own hands, no not by masturbating. Viagra is surprisingly easy to get from Canadian pharmacies. The next time we got busy I popped one before we went to my house and sure enough I was strong like bull. She even told me the next day that she was sore downstairs.

Yeah! Way to hurt her vagina, bro! Mash those guts! High five!

The relief that washed over me was great until the question arose of whether I’d need the blue diamonds the rest of my life. After maybe five times juicing my wiener my question was answered. Following a night of great sex the next morning she wanted to go again, but I was afraid of Limpy presenting himself without the Viagra. I was elated to see that I was at full salute with no chemical help!

Okay, the story’s starting to get too long now.

My problem was because of a few things. A very long dry spell made me unsure of myself. Relying heavily on porn I think desensitized me to a normal and healthy sexual relationship. By cutting back on the porn and instead thinking of my girl helped too. Lastly, this is the first time I’ve been in love and it really is a whole different ballgame when you love the person you’re sleeping with. Her patience and understanding were a huge help as well. My mind is now at ease, I’m in love and on cloud nine.

That’s great news! Fag.

Sorry for the lengthy follow up, just felt like I had to get it out.
Kind Regards,
(NOT) Limpy

Yeah, yeah. The only reason I published your lovey-dovey swill is because you included an important lesson: don’t get addicted to porn, it’s bad for your sex life.


Hi Caveman.

No fantasy football issues. Just a general question of smoothness.

Well, you’ve come to the right person!

*sits at bar by self, drinking silently and avoiding eye contact*

So I’m on a plane back from some sort of business trip a few months ago. Oddly, one of the stewardesses was actually quite hot. Even more oddly, she was sort of flirting with me.

An attractive, flirtatious stewardess? What airline was that? Were you on a Pan Am flight back to 1963?

Now, let’s be clear about three things:
1. She was not flirting with the other passengers (and you can bet your ass I was doing listening.)

Were you on the aisle? Or did you get stuck in a middle seat between a unicorn and a leprechaun?

2. I can, on occasion, be halfway charming.
3. I don’t, deep down, think she was actually interested in me. That’s not the point though.

But here is the important point:
Every ounce of common sense in my body says “picking up a stewardess is impossible, and you’re just going to make this poor woman who has a job to do very uncomfortable if you even try. Unless You’re George Clooney or Jon Hamm. In which case… bathroom sex!”

So while I could care less about THIS stewardess, I am interested in knowing, in general terms… have you ever, in your life, even heard of someone successfully pulling a stewardess’s phone number? I suspect that this move may have the highest degree of difficulty of any of the “picking up someone who’s being paid to be nice to you” scenarios (other similar situations include waitresses, strippers, the woman at the department store telling you how good that suit looks on you, and of course, that annoying GreenPeace chick who wants you to help her save the world).

Oh – the other obstacle being that I think that men should, in general, have a conscience and remember that women deserve the chance to do their jobs without being propositioned by strangers in an environment where they’re being forced to be pleasant / friendly / vaguely flirtatious. Unless they’re call girls. In which case, there’s no need to think too hard about any of this.

-John Draper

Despite my glibness, you’ve raised some interesting points. Assuming that attractive stewardesses DO still exist somewhere, I’d concur that they represent the greatest challenge for a successful, non-awkward pick-up. Consider: you are almost always confined to your seat, in tight quarters, and surrounded by other people within easy earshot of you. Small talk is almost impossible. Even at a restaurant, you can catch the waitress standing by herself at her station on your way to the bathroom. Try to catch the flight attendant on your way to the bathroom, and she’s in the back with the other two attendants, and you’re STILL standing right next to the people in Row 28.

But yes: I do know ONE person who picked up a stewardess. It was my company commander from the war. How did he do it?  Well, he has broad shoulders, two Bronze Stars, always travels in a suit, and kind of looks like Ed Harris. So basically, he’s like a non-famous George Clooney or Jon Hamm.

And yet: the flight attendant he picked up was a grandmother. No joke.

Stick with Match.com.

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