The KSK Sex & Fantasy Mailbag: We Got Virgin Brides & Lovesick Gays

09.27.12 5 years ago 100 Comments

Tellin’ y’all straight up: it’s a good mailbag this week. Good and long, so get comfy.

Dear KSK,
Fantasy: I am sitting pretty atop my 14 team PPR league, so things are going about as well as they could be. However, my Defense (NYJ) just lost Revis, and their complete inability to stop the run makes me nervous about holding on to them. None of my waiver wire options are particularly appealing, with Tampa Bay, Minnesota, and Denver being the only candidates to replace the Jets. So should I wait around and see how the Jets do? Does it even matter, since defenses are so flukey and low scoring anyway? Should I just shut the fuck up until I start losing games?

I’d give the Jets a week to see how they do minus Revis, but if that doesn’t work you can always scrape up something from the waiver wire. Just pick up a defense that’s playing the shittiest offense. (Lookin’ at you, Browns.)

Sex: I was recently married to my fiancé of over four years. She was a virgin when we started dating, and I respected her wishes to wait until marriage (it sucked), although I was at the end of my college career when we met and had already had several partners during that time. So now that we’re married, sexy times are on. Even though I’d had sex with numerous other girls, my (now) wife is the only person who has ever been able to get me off in any way, first with tenacious BJs, and by the time we were on our honeymoon, through sex as well.

Wait, that’s weird. You mean you didn’t have an orgasm when you lost your virginity?

I’d never had much difficulty figuring out what my partners liked, and could usually get the girl off even though I wasn’t able to get off myself.

SUPER weird.

But now the situation is reversed. My wife is obviously not very experienced, and doesn’t really know what to “look for” when trying to get herself off. I’m doing the best I can, pulling out every trick I can remember, although considering before last week I hadn’t had sex since George W Bush was still president, I’m a little rusty myself. Since the initial excitement of the honeymoon and after I got off the first few times, we both kinda get discouraged now during sex, and I tend to lose interest when I feel like she’s not enjoying herself. It’s a tricky situation, because everything that we do feels good to her, but it just can’t seem to get her over the hump. Meanwhile, I’m frustrated because I always took pride in being able to get girls off, and because I want my wife to enjoy sex with me since she has no other comparison, but I can’t help but feel like it’s a disappointment to her after waiting so long to do it. She’s the only virgin I’ve ever been with, so I haven’t ever had to show anybody the ropes before. Can you help?
First Time (in a) Long Time

Dude, she JUST started having sex. She’s not a little orgasm machine that just clicks on after you lick her clit for two minutes. She has to get used to having sex  and be comfortable with her body. Her roadblock is mental, not physical. Just enjoy having sex with her and let her enjoy it in her own way. She’ll either figure it out in time, or not. Either way, you’re the best sex she’s ever had. Be patient.

(Pssst, everybody else: this is why you DON’T wait until marriage for sex.)


Dear KSK,
Fantasy first: Who goes in the flex? Brandon Marshall (@Dal), Lance Moore (@GB) or Steven Ridley (@Buf). I still can’t decide if Steven Ridley is a real running back or not yet. Last week was tough, but it was against Baltimore. And he also has to split carries. Meanwhile, it’s hard to trust Moore since he’s not even a starting receiver, and Marshall’s been up and down.

I’d say Marshall or Ridley, and I’d probably lean Marshall just because you can’t trust Bill Belichick not to run the entire offense through Woodhead just to fuck fantasy owners. It’s a bit of a gamble, but I think B-Marsh is due for a good week.

Sex…ish: My girlfriend and I recently broke up.


We had dated for the last two years of college, and were trying the long-distance thing (I know, I know). I just started law school on the East coast and she started in a rotational program that causes her to move around for her job every 6 months for two years, with no rotations east of Chicago. We both basically admitted that there was nothing wrong with the relationship, but this wasn’t the right time for it. We’re too young to get married (22), we’re in different worlds, and we don’t really have time for each other at this point. I think we both probably knew that before trying long-distance but neither of us would have felt right if we didn’t try. Now, we’re basically just going to see how things end up, and when we’re both settled, if things are right, we can see if there’s still a spark. That being said, it’s still hard. It’s not so much as a blow to my confidence as it is just a shitty situation.

On top of that, I’m in my first year of law school which is the most important year, since your first year grades determine your summer position, and essentially if you can get a good job or not.

Man, people are really still going to law school? There have been no jobs for lawyers for like four years, and you STILL were like, “No, I got this, it’s cool.”

I can’t really let this set me back in terms of work, but it’s hard not to have this break up be a distraction. In addition, (and I’m sure this is going to sound douchey, so my dearest apologies) I go to a top-10 law school. It’s full of bright people, but the trade off is that a lot of them are socially awkward. I haven’t really been able to make too many friends yet because I’m not really into Japanese comics or coin-collecting. You get the picture. We just have to study all the time (and end relationships); it’s been a very isolating experience. Any advice on how to deal with a break up that’s based more on logistics and timing, rather than issues with the relationship itself? And just getting over it all in general?
All the best,
Sleepy Richardson

Well, the first thing I’d do is NOT GO TO LAW SCHOOL, but that seems to be off the table.

Life isn’t all sunshine and blowjobs. Sometimes we go through periods of months and even YEARS where all you do is bust your ass, feel miserable, and try to milk some small enjoyment from the people going through the same hardships as you. Welcome to law school. And remember: this is what you signed up for.


So what I’d recommend you do, Sleepy, is suck it the fuck up and embrace your decision. You shouldn’t have the time to pine away for Susie Rottencrotch in Chicago; time is a luxury reserved for people who AREN’T L-1’s at fancy-pants top-10 law schools. Budget your time wisely, and recognize when your brain is full and you’re just studying because everyone else is studying. Schedule exercise for yourself, and organize a bi-weekly happy hour — the social people will come out of the woodwork for a drink, and it’ll be easier to make friends with people who aren’t into coin-collecting.


Dear Captain Caveman:
I love your SBNation videos. The Kate Upton one was awesome (you lucky dog!) and I am really using your fantasy football ones to great advantage. Hopefully, that will give me a leg up on the competition this year.

Eh, that remains to be seen. But thank you. Here’s this week’s episode of Keepers, by the way.

FF: I am in a 12-person, no-keeper, one QB slot, money league with some friends. The commissioner recently traded Brent Celek (TE, Phi) and Steve Smith (WR, StL) in return for Dustin Keller (TE, NYJ) and TOM BRADY. This is clearly a one-sided trade, but since she’s the commissioner, the trade didn’t go to a vote and was automatically processed. When I called her out on it, she said that because the other owner approached her about the trade, she should be able to keep Brady and refuses to reverse it. Am I being a douche for being pissed about this? Or should I let this go? With the commissioner being shady, how can I be assured that she won’t continue to pull this kind of shit down the line?

Oh, stop being a fucking crybaby. She swindled someone in the league who’s obviously a moron — how is that HER fault?

I never understand this particular line of thinking in fantasy owners — that when there’s a lopsided trade, they get mad at the person who made their team better rather than the person who made the stupid trade. You should be pissed off at the idiot — or, if you’re smart, you’ll tell them you see the merit of their thinking, and by the way would they like Chris Johnson? He’s going to bounce back any week now!

Sex: Here is include a picture of Barbara Palvin, who is phenomenally hot.

All the best,
Brady Jealousy Guy

She really is otherworldly beautiful, and you could do a lot worse with your time than going through the Barbara Palvin tag at Suicide Blonde  And unlike most supermodels (she does lots of Victoria’s Secret and high-end fashion shoots), she’s never done artistic nudes. DAMN YOU, PALVIN! DAMN YOU AND DAMN THIS SCARF!


Capns of Cavepussy:
Football: I’m the commissioner of a league in its fifth year, we’ve got a core of 8 guys (including my best friend and his brother who I’m good friends with) who have been in from the beginning, the other 4 include 2 who joined this year, and 2 who joined in year 3.

Okay, let me stop you there. Timeout from the mailbag, everybody.

I work on the internet, okay? My work cycle has three steps: (1) Absorb media. (2) Process media. (3) Produce media. This can happen in several different ways. I can watch a football game for three hours, write up a game recap, and then shoot a YouTube video where I recite that recap. I can read a news story, think of a joke, and then publish that joke on Twitter. Whether it’s video, blog post, essay, or tweet, the process is the same. For the mailbag, I read your emails, I think of responses, and then I write them down or make Photoshops or search out GIFs. The faster I can absorb the media, the sooner I can get to processing the information and producing my take, which means I can get the fuck offline, turn my brain off, and start drinking. As such, I have developed a sincere, appreciative fondness for media that uses smart economy of language because it’s saves me time.

What I’m saying is, WHY THE FUCK SHOULD I CARE THAT YOU’RE FRIENDS WITH YOUR BEST FRIEND’S BROTHER? Here’s your first sentence again:

I’m the commissioner of a league in its fifth year, we’ve got a core of 8 guys (including my best friend and his brother who I’m good friends with) who have been in from the beginning, the other 4 include 2 who joined this year, and 2 who joined in year 3.

Here’s your sentence edited for pertinent information:

I’m the commissioner of a league that has a core of eight original members and four others who have joined more recently, including two this year.

I look at both versions of that sentence and get sad about the hours of my life that I’ve spent inside reading email instead of outside breathing fresh air. People who don’t edit their writing are assholes. Just look at Peter King.

One of the latter group is a huge whiner who always complains and is opposed to anything cool, like keepers – he is also prone to send me panicked e-mails at the 11th hour asking for explanations on how waivers work. I want to ditch him, but am wondering how to do it considering that he: always pays on time, may just be prone to whining, is best friends with my best friend’s younger brother (and I suspect they might be more than friends, hint hint). Any advice on how to diplomatically get rid of a guy who is a pain in my comissioning ass without pissing off some key members of the league?

If he pays on time, he stays on the league. If he sends you panicked 11th-hour emails, ignore them. If you don’t like his whining, be a man and tell him to shut the fuck up.

Quasi-sex Related Work Relationship Question: I work in a large corporation at a job I really enjoy that requires regular travel. One of my co-workers is a woman who is married and slightly older than me. I really like her as a co-worker, she brings a very Pittsburgish attitude to our white-color office; her husband works in the same company, different division. Over the last few months, she’s regularly engaged in behavior with me that I thought was flirting, but I shelved it since she’s from the south and I figured that southern people are just very friendly (Everyone is mean here in Northeast Liberalville). Naturally we went on a business trip a few weeks ago and she made it clear that she was indeed flirting all this time and wanted more. Thankfully, I did the right thing: nothing (her Pittsburgishness also extends to her face). While that whole dynamic is certainly awkward, but it doesn’t change the fact that I admire her as a co-worker, she’s a great teammate and very sweet person.

Complication: I just got back from a separate trip with her husband, who I don’t know well, but who is clearly a douche as I saw him chasing tail every night we hit the bar.

My quandary: what do I do?

Well, you can start by telling shorter stories.

While I shot her down, she still flirts with me all the time – I don’t have the heart to be a total dick to her since I like her as a person. However, after seeing her husband in action, I feel really bad for her, I’m sure he’s not treating her right. Do I sit down with her and tell her what I saw, do I tell him what she did? Do I just ask for a transfer and get away from these weird people?

If you work in a large corporation, then there’s HR. If there’s someone you trust in HR, tell them what happened ask what the best thing to do is within your corporation’s policies.


Dear Captain,
Fantasy: Do I play Ben Tate or Mikel LeShoure in my PPR Flex spot this week. (Foster and Charles are my starters)? I played Tate weeks 1 and 2 to great success and then played LeShoure last week, also to great success. The Titans D is not good and I can see Tate getting a lot of carries when they are up 2 TD’s, but Detroit looks like they want to ride LeShoure and the Min D isn’t special either. The projected points have me up 50 so I hope if I choose wrong it really won’t matter.

Leshoure. Guaranteed touches.

Lady Troubles: My girlfriend has been super pissed at me lately, but we are working on the issues. Though it feels like everything we need to work on is with me (listen better, pay attention, be romantic, have some passion, etc.). We have been together 3 years and she moved into my house in the spring. Since we have been together she has quit smoking cigarettes and started back to school. I never asked to her to quit smoking, but was encouraging when she did. I did want her to go back to school but never pushed the subject (however, when I would try to bring up the future it was not for me worry about)

That last parenthetical doesn’t make sense, but okay.

But here is the real trouble for me: She told me “I love you” first on New Years almost 3 years ago. I said “I love you, too” and meant it at the time, also she made the first move the day we meet (yeah not the most courageous or confident when it comes to the ladies). Now during fights she brings this up and throws it in my face. “I had to tell you I love you” “why do I always have to bring these things up”.

I think I’ve figured it out: your girlfriend is awful.

To make matters worse, several, of hers and mine friends have gotten engaged in the last 2 months.

That syntax…. I…

Particularly my best friend who has only dated his fiancé for about a year and half. And now she wants to know why I can’t commit or what I am so afraid of, and worst of “what’s wrong with me”. I try telling her I love her and want to be with her and plan to ask her to marry but am really terrible at expressing this in a way that she finds acceptable. Short of asking her to marry me, how can I get her to understand it’s really hurtful that she continues to throw that she made the first move and said I love you in my face when we fight?

Really? You want to spend the rest of your life with that person? Is that how you feel, or is that what she told you to feel?

In your girlfriend’s defense, your friends getting engaged just makes the ticking in her head louder. ANECDOTE: I had originally planned to propose to my wife by the end of the summer last year, but I procrastinated because holy shit are diamonds crazy expensive. And then in the span of ten days in late August/early September, FOUR couples we know got engaged. And I was like “SHIIIIIIIIIIT” and got my ass to, because as cool as my wife is, she is also a woman, and women have certain needs. These needs include but are not limited to: food, water, compliments, and winning unspoken life competitions with their closest female friends.

ANYWAY. Regardless of whether you should get engaged to your girlfriend, you need to stand up for yourself. As much as I want to call your girlfriend a controlling harpy, I can’t help but feel that you exacerbate the problem by being a lump on the couch who needs to be told what to do (my apologies if I’ve inferred too much). In the olden days, a lively backhand across her cheek would deliver the message efficiently, but you’ll have to calmly sit her down and explain to her that it’s really hurtful the way she brings that up in fights — that she uses the first time you expressed your love to each other as a weapon against you. (That is SERIOUSLY fucked up, by the way.) You said you’re working on being more communicative, being more romantic, etc. — and she needs to change, too, by being more patient and forgiving. If she can’t meet you halfway, then you need to jettison that broad.


Hey Paisanos!
Fantasy first: Finally rode to my first victory of the year last week on Jamaal Charles’s finally-unfucked knee (which I’m sure will now summarily explode). Want to keep that momentum into week 4, so help me pick one RB one Flex (not a PPR league): Ryan Williams@Mia; Stevan Ridley@Buf; Nate Washington@Hou and Jerome Simpson@Det. I’m thinking Ridley and Williams, waiting a week on Simpson.


Sex: Recently married, everything (read: sex) is great, but we’re both really busy during the week with work (she’s writing a thesis from home and every coffeeshop in a two-mile radius; I’m in a research lab that can keep me until 9-10pm some nights). A couple friends of ours have talked about their setting aside a ‘date night’ to make time for each other – not just for sex but for regular facetime during the week. My first instinct was Fuck No because it sounds like so much middle-aged-save-our-boring-marriage claptrap and our sex & frequency thereof has us both quite happy thankyouverymuch, but the more I think about it, the more it makes sense. My wife has specifically suggested that we use it as time to spend with each other and with our mutual friends, which is honestly a great idea. I’m just afraid it will make us Old and Lame instead of Young and Fun and Spontaneous. Ugggggghhhhhh. Thoughts?
Probably Old and Lame

Are you presently being Young and Fun and Spontaneous now? No. So schedule some time to hang out with friends.

The other week, my wife and I hung out with a group of our married friends and played board games, and you know what? We had a blast. There was booze, and we brought our dog to the apartment, and the music wasn’t too loud, and Settlers of Catan is a hell of a lot of fun. I am a million years old. I don’t care.


Hey Captain

Football first: I have a pretty serious QB issue. Namely, that my QB is Romo. He had a very solid week 1, but has been underwhelming to pathetic in the past two weeks. My back up is Luck, who is on a bye. Ponder and Fitzpatrick are my best waiver options. Should I pick up one of them? Or drink a double of bourbon and watch Romo throw for 150 yards against a tough chicago D?

Romo will be fine. Might be another tough week with the Bears, but stick with him — he’s a good fantasy quarterback.

Relationships: I have a pretty negative mindset about dating. My last serious relationship ended when my fiancee let me know that she was seeing a mutual friend and that she was choosing him over me. The last girl I dated texted me that she was down for lunch on saturday. Two weeks later, I found out that she moved to Korea. That was 3 years ago, and I haven’t been on a date since. I think I want to start dating again and I know I want to at least take a shot at finding someone else to share life with. But I’m 28, fairly overweight and holy crap, am I a nerd. Fantasy football might be the coolest thing I do.

Yeah, I know.

I’ve started doing yoga to help get me more physically fit, but mentally I’m still kind of a mess. If I do find a woman attractive, I’ll usually come up with a reason why she wouldn’t be interested or why it’d be stupid for me to talk to her. I used to be good with women, and I’m still a pretty good conversationalist. I know when to listen and when to lighten the mood and I’ve got a wide circle of friends and a pretty active social life. But I’ve noticed that my lack of confidence is devastating my dating life and now it’s affecting my social life. I invent reasons not to go out to places where I know women will be, even if they’re friends or the wife of a friend. Any advice for getting over this esteem/confidence issue and getting back on the right track to a more healthy mindset?

Your life is what you make of it. Some people get dealt great hands: they are attractive and have parents with money, so they go to expensive schools and get good jobs and meet other attractive wealthy people. Those people suck.

Everyone else — which is to say, almost everyone on the planet — has to scratch and claw for everything they get in their lives, up to and including happiness. I don’t know what your religious views are, but I have serious doubts about the afterlife and reincarnation, which means I have only this life. One chance. If things go well, I have seventy-five, maybe eighty years on the planet, and I want to spend as much of it doing the things that I love the most: laughing, spending time with people I love, having orgasms, challenging my mind and body, learning new things, and seeing new places. Because at the end of it, when death is coming — and it can come any day — I want to know that I gave life my best shot.

So fuck you for wasting three years of it. I know too many bright and talented people who never saw their 25th birthday who would have GLORIED in three more years: they would have gone running on mountain ridges, told hilarious stories in bars that attracted strangers, flown across the country to make love to women they barely knew, inspired others to greatness. And you’re all, “Wah, I’m not confident.” Goddammit, go out and fucking LIVE! Who gives a shit what anyone else thinks?


I’m a 36 y.o. successful, professional guy. I’m gay, but I’m not out to everyone or even most everyone. Friends and a few co-workers, mainly. Not currently dating, and haven’t dated seriously in a while. This spring I met a guy (Ennis) on Twitter. He lives in Manchester, England (I am in middle America). He and I hit it off immediately as friends, and eventually added some light sexting/sexy phone chat, usually but not always when one or both of us was drunk. At the time, he had a boyfriend, but they broke up in June. I made a detour on my vacation in early July to meet him, though he was going out of town on his own vacation the next day, so we only got to spend a few hours hanging out. It was not a date by any stretch; just two friends, who happened to have done some silly sexting, meeting for the first time. He took me to his favorite pub for dinner with a couple of friends, then back to his place for some more drinking w/ one of those friends. Some fairly chaste hand-holding and a kiss, but that’s it, and that was fine.

This story is adorable. I wanna hug it like a little corgi puppy.

We’ve continued to tweet/chat/etc. pretty consistently since then, and I have come to realize that I am madly in love with him. I know, rationally, that I can’t be in love with someone I’ve met once, but that’s how I feel. I want to marry this boy. He’s 28 y.o., funny, charming, incredibly kind, and quite sexy, and we have a lot of common interests. I’ve told him that I like him “like that,” and we have had a few chats on the subject, but I have not pressed the issue. At one point, he tweeted (publicly, not DM) that if he were ever going to get married, I’m the person he’d want to marry, but I am sure I’m taking a lighthearted tweet way too seriously. We have continued to occasionally sext and have also shared some pretty intimate secrets with each other (fetishes/fears/dreams/etc.) On the other hand, he continuously flirts with another guy on Twitter (who I also am friendly with) and I know he has actual amorous feelings for this other guy. In fact, I wonder if the way I feel about Ennis is the way Ennis feels about the other guy, sometimes.

I never realized that Twitter was so social like that. I thought it was just for dick jokes and sharing breaking news.

Ennis travels a lot – as do I; it’s one of the things I like about him – and he planned a trip to Tierra del Fuego and Antarctica for next March. After he’d booked his own passage, he encouraged me to join him (at my expense, of course), which I readily agreed to do.

You’re eight years older and have never put out. I don’t think anyone assumed Ennis was going to pay for your trip.

We’re going to spend a few days in Buenos Aires, then nine days on an ice-breaking cruise/expedition ship in and around Antarctica. It’s going to be a helluva great adventure. We’ll be sharing a hotel room in B.A. and a cabin on the boat, but I don’t read too much into that, because he travels often with friends-without-benefits and rooms with them.

So I really want to date him, but I also really want to remain friends with him even if we never date. Do I wait to see how the trip in March goes before suggesting that we attempt an actual long-distance relationship (to say nothing of actually contemplating a move to England)? Am I reading too much into what has occurred so far? Or am I being too worried about reading too much that I’m actually underestimating his interest in me? Should I have a conversation with him about all of this now? I don’t want to do anything to put the friendship at risk, but at the same time I don’t want to do anything to let what may be the man of a lifetime slip by. I’ve never felt quite like this about anyone, but I just can’t tell whether it’s an infatuation/crush or if it’s “real.” I am an emotional wreck at the moment. Being mostly closeted doesn’t help. I am committed to coming fully out the next time I have a boyfriend, and I’m going to come out to my sister next month come hell or high water. I should do that, right?

I don’t play fantasy football.

Whoa, okay, that was a lot of questions in a row. First of all, I just want to say IN YOUR FACE, DAN SAVAGE! I got a gay reader! As for your questions:

Do I wait to see how the trip in March goes before suggesting that we attempt an actual long-distance relationship (to say nothing of actually contemplating a move to England)?

Of course. You need to walk before you can run, and right now you’re still crawling.

Am I reading too much into what has occurred so far?

It certainly seems possible.

Or am I being too worried about reading too much that I’m actually underestimating his interest in me?

Should I have a conversation with him about all of this now?

I do think you need to know where you stand before the trip, but hitting him up over chat with “Hey, are we gonna gay sex it up or what?” doesn’t seem the right way to go about it. In fact, I don’t like the medium of Gchat/IM for any serious discussion — it’s too easy to lose someone’s meaning or take something the wrong way.

You said you’re a successful professional, so I assume you can spend some money to travel — why don’t you see if he wants to spend a long weekend in London with you? (Or New York or some other city, but I was thinking about minimizing his travel.) Have him show you the city, have dinner together, and see if the romantic spark is really there — I think you’d really benefit from spending some time together before your Arctic adventure. And for God’s sake, keep the L-word under wraps. You don’t want to scare him off.

I am committed to coming fully out the next time I have a boyfriend, and I’m going to come out to my sister next month come hell or high water. I should do that, right?

Yes. Life’s too short to be anyone but yourself. Good luck.

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