KSK Mailbag: Welcome back, anal questions!

04.17.14 4 years ago 122 Comments

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Early in the KSK sexbag’s existence, readers seemed to only have one interest: convincing their love interest to try anal, to the point that everyone who read it was like, “ENOUGH WITH THE ANAL.” And while I hope that doesn’t return as a weekly staple, I’m pleased that today’s anal question at least has a different angle.

But let’s talk about MY gaping hole. I had a wisdom tooth pulled yesterday, and now I’ve got collagen packed into the crevasse, which the dentist secured with a couple of sutures. It was my third trip to the dentist in about three weeks, and now all I can think about is how much money you could make if you started a dental practice in which the patients couldn’t hear the sounds happening in their mouth. Like, I don’t mind the needles or blood, but the crunching and scraping makes my palms sweat. I would pay five times as much money to go the SILENT DENTIST.

None of this has anything to do with the mailbag. Sorry. Let’s get to your questions.

Heya Cap,
Fantasy: I don’t have a question. As recompense I offer a picture of Ann Margaret being a saucy minx.


Finally, a reader who gets me.

Sex: My boyfriend and I have been together 6 months and everything’s going great: he’s a caring, gentle, incredibly smart man going after his Masters and then his PhD while working full time in a super stressful job. We’re on the same page on almost everything – family, life plan, sense of humor, and the sex is through the roof. About three weeks ago I came home to find he’d downed a bottle of wine and a 6-pack in the 2 hours I was gone. This was 2 days after I’d come home to find a 6-pack in the trash where there hadn’t been a 6-pack in the house at all earlier in the day. This led to a meltdown on his part, telling me through tears that he had a drinking problem and it was getting away from him. I did what any understanding person would, I helped him get rid of the booze in the house, and I abstain from drinking as well.

“Everything’s going great, except for his drinking problem.”

Remember how I said our sex is through the roof? We have a ton of fun in bed but we both want more anal. My problem is I can’t do it unless I’m a little tipsy, which wouldn’t exactly be considerate of my darling alcoholic boyfriend. We use beads and plugs already but that’s more for my pleasure than his, and I feel bad that he’s being denied something he likes to do because I need a little help relaxing.

Technically, he’s being denied something he likes to do because you’re being compassionate about his alcoholism.

Any advice on how to have anal with my alcoholic boyfriend when I need a few drinks to do it?
I needs a drink

First of all, I need to take a moment to applaud your fast-twitch emotions; the change in direction from “I just discovered my boyfriend’s drinking problem” to “How can I give him more anal?” was a crossover that sent me flying out of frame.

If you need alcohol to physically relax for anal, then I’d guess most other relaxants would work, too: pot, Xanax, whatever happens to be your drug of choice. And of course, you can always move up a size in your plugs and beads, working your way up to something more dick-sized.

I would, however, venture that this anal question brushes over the larger problem. Alcoholism tends to be a lifelong battle requiring peer support, not something solved merely by getting rid of the booze in the house while no one around the drunk tipples. If your boyfriend broke down while admitting he has a problem, it’s a bigger problem than you alone can solve. He should seek professional treatment, so that you can confidently have a glass of guilt-free wine and give him the anal you both enjoy so much.


Dearest Mr. Ufford,
How are you on this fine post-tax-season day? I hope that this mailbag inquiry has found you quite well indeed.

I’m fine, thank you.

I am in a standard-format, standard-scoring, vanilla-by-all-accounts ESPN league, except that there are two keepers. And I had Megatron, Shady McCoy, and Josh Gordon. I’m at a complete and utter loss at which two to take. Any thoughts?

No cost relevant to which round you drafted them? That IS vanilla.

I’d recommend Shady as the must-keep, as an electric RB in Chip Kelly’s offense will continue to perform at a high level (barring injury, of course).  As for Gordon/Megatron, it depends on your inclinations — and also when you have to declare keepers. If the Browns draft a competent QB who meshes well with Gordon, I’d probably lean towards him over Johnson. Yes, yes: I know Megatron is an unstoppable football god, but Gordon’s six years younger and put out a Megatron-like season with a rotation of awful quarterbacks. Pending some very easy football decisions in the Cleveland front office (NOT a gimme, unfortunately), Gordon’s the better keeper over the long term.

Pertaining to the sexy side of things, I’m in a situation. The backstory: I’m a college student, and last semester I had a huge thing for a girl who has a shitty past with men. Knowing this, I was trying to slowly approach something with her, and it had gotten to a point where we were speaking constantly and very flirtatiously, and she had told a mutual close friend (who tells me everything) that she had feelings for me. But, before I could make a move she abruptly stopped speaking to me and began ignoring me completely, and shortly after started again seeing her ex-boyfriend who had previously cheated on her.

I was at the time unaware that she had started seeing him again, and would have been shocked to hear it, quite frankly. Anyway, months later and during winter break, she started speaking to me again out of the blue, which I quite weakly welcomed. Turned out she had been mistreated by him again when she started messaging me, and I stopped speaking to her when I found out about the whole situation. She obviously can’t get over this guy, whom she’s still with even though he’s cheated on her again even since I stopped speaking to her, and she wanted to jerk me around as a backup option when he was being a dick.

Hold on, lemme just break out my “email from a college guy” checklist…

☑dickhead boyfriend

☑girl who can’t stop loving him

☑nice guy she won’t date

Yep, your story checks out.

The above probably sounds like something I shouldn’t allow myself to get too upset about. Well, I didn’t – I just think she’s a disingenuous bitch.

I mean, she’s what, 19? 20? It’s not like she’s TRYING to be a bitch. She just hasn’t cycled through the range of adult romantic emotions enough to know that she doesn’t need her boyfriend or that she’s hurting you by leading you on. Same thing with that “asshole” boyfriend — he’ll probably grow into a decent human adult once he stops making out with drunk freshmen girls.

College students are powered by the dangerous twin engines of hormones and inexperience. Even those who don’t crash spectacularly end up burning a lot of people.

Anyways, it didn’t take long for me to get over her and to find a girl I think is far worthier of my time. I took an interest in a person I’ll refer to as Jess, someone I legitimately deem to be among the coolest girls I’ve ever met. We started hooking up for a few weeks, and then started dating, because college. We’ve been dating a month and a half, and I’m very happy about that.

The issue is that Jess and her roommates (who are some of my best friends on campus, going far back before she and I started dating) joined a student organization they’re now very serious about, the two top dogs of which are the girl I had a thing for (let’s call her Bitchface at this point) and her cheating boyfriend.

Stickin’ with the bitch thing, huh? Okay.

In the time I’ve been dating my girlfriend, she and her roommates have gotten very close to both of them through this organization. Also, none of them know what went on between Bitchface and me.

Probably because nothing did?

I haven’t said anything to Jess about Bitchface, because I thought it would be awkward to bring up while we’d just started dating. The organization they’re all in is a co-ed fraternity,

“It’s like a regular fraternity, but with more fucking.”

and two of Jess’s roommates (two of my best friends) recently became the respective “littles” of Bitchface and her boyfriend. Which is some forced frat thing that basically just means they are going to be heavily involved with our lives. This past week, when my group of friends has been hanging out, we’ve been joined by them on multiple occasions.

My question is: do I tell Jess about my past with Bitchface, and if so, how do I approach that? It’s an odd story to tell, for my original reasoning and because I don’t want her to be made uncomfortable; due to Jess’s and her roommates’ connection with the organization, Bitchface and Co. are here to stay. However, the continued presence of Bitchface makes me really feel like I’m keeping something from Jess, and I feel that it could be quite bad if she hears about it elsewhere before hearing about it from me. What do you think?

Thanks for any input you might have, and I’m sorry it was so long (I usually don’t apologize when saying that).

I’d say the odds are pretty good that Jess’s roommates — however close they are to you — have already gossiped to Jess about whatever connection you may have had with Bitchface. And not only have the roommates shared everything they know about you to Jess, but Jess has probably already blabbed to them about the contours of your penis and whether you’re any good at oral sex. I mean, they’re female roommates who all joined a co-ed fraternity together. What else would you expect?

Still, your past crush on Bitchface is a harmless enough piece of ephemera. If it’s weighing on you, by all means, share it with Jess. Just don’t go too overboard in slamming Bitchface — that will come back to haunt you if and  when you and Jess break up. Stick to the basics: “… I broke off communication because I wanted to put my emotional energy into someone who cared about me — and then I found you.”


Dear Caveman,
Football (soccer): With the friendly struggle against Mexico, the seemingly decreased playing time for any of our Euro players, and the coaching staff turmoil, what should I, as a USMNT fan, be most concerned about 2 months before the World Cup?

DISCLAIMER: I opened up the mailbag to topics besides sex and fantasy football a few months back, so I’m going  to field this soccer question. If you’re opposed to that, just skip down to the next bold section.

I wouldn’t stress too much about any one friendly, particularly one in which Michael Bradley looked so brilliant at the offensive tip of a midfield diamond. Bradley, of course, is one of several U.S. internationals who’ve chosen leading a team in MLS over fighting for playing time in Europe, and thus far he’s looked like the best player in the league.

Also in the argument: Clint Dempsey, who leads the league in goals despite serving a two-game suspension for nut-punching an opponent. He’s scored five goals in the last two games (both away), with three of those in the final five minutes to salvage four points from what looked like two losses. Regardless of where you fall in the MLS versus Europe debate for developing American talent, it’s great to see the team’s best players in top form going into this summer.

As for the players in Europe, I think it’s a wash. I certainly had higher hopes for Jozy Altidore at Sunderland this year, but Aron Johansson’s been excellent for AZ. Jermaine Jones has been declining for a while, and I don’t think additional playing time in the Bundesliga would have changed that. A year after many called for Brad Guzan to replace Tim Howard, Timmy elevated his game and has helped Everton flirt with a Champions League berth.

The coaching staff changes: I’m not too concerned about Martin Vazquez’s demotion; since he’s a Klinsmann acolyte (and not an American or a Bob Bradley holdover), I wouldn’t presume that it would affect the players much. The promotion of U-20 coach Tab Ramos reflects Klinsmann’s focus on developing younger talent, and Berti Vogts has managed Azerbaijan against Portugal — the U.S.’s second opponent in Brazil — twice in the last 18 months.

So, that’s the good news. The bad news is that our back line is thin as shit. Brad Evans, a midfielder who looked like a starter at right back, suffered a calf injury that’s kept him out of the last several matches. DaMarcus Beasley — also a natural midfielder — is old as shit and playing at left back. Centerbacks Matt Besler and Omar Gonzalez seemed to provide some quality, but Gonzalez looked terrible in the second half of the friendly against Mexico. That’s the best-case scenario; the guys behind them on the depth chart are glaring holes that Ghana, Portugal, and Germany will happily exploit.

But I don’t want to be the doomsday prognosticator. The U.S. has an enviable midfield, solid attacking players, and a world-class goalkeeper in Howard (plus another one behind him on the bench). The draw was a stomp in the balls, but as Spencer Hall wrote in December, that was just act one of the underdog movie. And there’s fun to be had in believing in an underdog.

Okay, back to football and sex.

FF: Please talk me out of taking Matt Stafford before the 3rd round in our standard, no-keepers league. He’s not going to have enough accuracy or weapons to exceed our expectations, right, even if the Lions draft Watkins or Evans?

Actually, I think the Lions already have an excellent second receiving option — finally — in Golden Tate. I think Stafford will have a great season (I see his ceiling as a top 3 fantasy QB), but his perceived value doesn’t warrant the early pick. I don’t think I’d go for him in the third round unless there was a run on quarterbacks and I was worried about not having a viable starter.

Other: My wife and I went to see Broken Bells in concert the other night. The band Au Revoir Simone opened for them. Video below for your context:

During Au Revoir Simone’s set, my wife leans over to me and asks, “You can think they’re cute, as long as you don’t think they’re beautiful.” I appeased her by saying something like, “My eyes are only for you.”

My question is this – is this standard-issue batshittery, or is this beyond the pale of what I should expect someone I love to say?
Guy Remaining Obstinate Under Pressure In Eardrums

Maybe your wife’s just making sure you have good taste. Those girls are cute, but they ain’t beautiful.

That said, any person on a stage performing with talent and confidence instantly becomes thirty to fifty times sexier, so I think we should all — as a society — accept our attraction to musicians, even the ones that aren’t THAT cute.


Dear KSK,
Fantasy football – I don’t play it. I don’t want to have to root for players on teams I can’t stand. I’d rather spend my football Sundays rooting for my team that I know is always going to let me down in the end.

Cool start to the letter. “Hey, fuck what your readers like! Anyway, here’s what’s going on with me…”

Sex – Been married 8 years, two kids now. Got no real complaints in the sex department, my wife is pretty much down to bang whenever I want.

My question concerns whacking off. Despite the fairly healthy sex life sometimes a guy likes to look at a little strange after the same vadge all the time.

I read a fantasy football/sex advice column on my favorite football blog this week and they showed a porn girl they pixellated out & didn’t give her working name. I now want to rub one out to this chick badly. Reverse Google search didn’t help AT ALL. Thanks a lot fuckheads at Google. I don’t care about outing her real identity at all, that’s for shitheads. Can you help a brother out here?
Thanks, Jack Mayhoffer

I absolutely can. But I won’t, because your email was abrasive and inconsiderate. Have a great day, and may the wide world of porn offer something to satisfy your tastes.

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