The KSK Sex/Fantasy Football Mailbag, Featuring Newly Sugared Vaginas

07.22.10 7 years ago 85 Comments

Believe it or not, this is actually a very special edition of the mailbag. Many of the sex questions this week were fed through a panel of three women — all of them attractive, in their late twenties, and not figments of my imagination. Their input influenced many of my answers, and was extremely helpful at times (vaginal epilation) and complicating at others (the female orgasm).

But the important thing to remember is that we’re ONLY A MONTH AWAY FROM FANTASY DRAFT TIME. WOOOOOOO!!!!!

Dear KSK,
I got two questions about a couple friends in penis predicaments:

-First is pretty much dating a married woman that is gold digging the shit out of him and some other schmuck. The other schmuck is in the coast guard and is never around, but pays fully for her car, apartment, all her electronics, accessories, name it. But since this guy is always at sea, she spends all her time fucking my friend at his place. Meanwhile smoking all his weed, using his place to the max, etc. He’s clueless and doesn’t see what a crazed grip she’s got over him. He’s tried breaking it off, and she got crazier and pretty much refused. We don’t know if she’s on the brink of divorce or what, but she is a crazy bitch. At the same time, it’s his love life and he can do what he wants. When is an appropriate time, if at all, to say something to him about how fucked up it is and that he should take a good look at what is developing around him?

Now, and tomorrow, and the day after that. Since you say that she might be on the “brink of divorce,” that means she’s married, which means your friend is stupid and shouldn’t be dating her in the first place. Nobody should be dating her except her pussy-ass Coast Guard husband. And if you can’t appeal to your friend’s sense of morality, then you should make it clear that he’s clearly being used like a bitch. It’s something he should be reminded of daily until he comes to his senses.

-My other friend is a virgin at 22 with no prospects in sight. Anywhere my friends and I go with him he won’t say a word. It could be his closest friends or total strangers, he barely says more than a few sentences. A dating site would be a disaster as he’d have to spend alone time with a woman (female friends have said the silence is torture). What’s the best option for anonymous sex that requires as little to no conversation as possible? Hooker? Craigslist? Find a slutty friend?

What, does he have Asperger’s or something? If the dude can’t speak to the opposite sex, why the hell should some poor woman be saddled with having sex with him? If I had a friend like this guy, I wouldn’t set him up with a female friend of mine unless she was ugly or I hated her. But since all of my friends are attractive and gregarious, I don’t really have that problem.

Sorry, I don’t mean to be unsympathetic, but your “friend” has bigger problems than not getting laid. Teach him to walk before trying to make him run.

Football: What should we expect from Anquan Bolding now that he’s a Raven?
Best, S

Expect good things. Flacco’s a good young quarterback who’s made Derrick Mason a quality fantasy WR even though that dude is ancient. Even though Boldin is going from the #2 option behind Larry Fitzgerald to the primary wideout, I still think he’ll be a good mid-round pickup.


Dear KSK,
Football: I’m in the same league with a bunch of guys I went to college with, and we get together once a year for our draft at a central location, which is out of town for many. We’re all now about 6-7 years down the road, and that means for many of the guys, marriage and kids. I ran into some of the couples at a recent wedding, and one of the recently be-childed wives says to me, “Oh, I can’t wait for the draft this year so that all of the kids can meet each other and play!!” Uh…wait a minute. We get together at a bar and get smashed over the course of 5-7 hours. We don’t need any snot-nosed fuckers running amok. Those that had children in the past had always kept them away on draft day. There’s no douchey rule of “No Chicks at the Draft” or anything, but obviously the father of this child has not made it clear to his wife that this is not a place for children, nor is it a backyard BBQ where all of the women can exchange stories of the great deal they got on silverware at Crate & Barrel last week. Should I tell this guy to get his wife in line, or should I get one of the other mommies in the group to tell her what the score is??

The last thing you want to do is leave communication up to women. And that advice comes from women. You let someone’s wife carry a message to another wife, and there’s the distinct possibility of hurt feelings and two years of bitterness. Just set up the draft to take place at a bar — thus making it non-kid-friendly — and reiterate to your friend that his retard kids aren’t invited.

Sex: Nobody wants to be a two-pump-chump, but I seem to be having the opposite problem. I can’t seem to be able to finish with my new lady. We’ve been seeing each other for a couple of weeks now, and while the sex is mind-blowing, it’s not load-blowing. I think it started on her birthday when – wanting a little extra endurance for her special day – I jacked it before I went over there. All of a sudden I’m Julian Rios giving it to Jenna Haze in 18 different positions over the next hour-and-a-half. Since then, every time we get together, I get in the same frame of mind and haven’t been able to get one off. I mean, I go thru the whole mental roledex of past encounters, celebrities, porn stars, and I still can’t pop. To be honest, it’s not a huge deal to me because I know she’s enjoying herself, but at this point I haven’t had an orgasm in 4 days and she thinks there’s something wrong with her for not being able to get me off. It’s just a mental block, but have you ever heard of a guy giving himself blue balls??

I’ve never heard of guy giving himself blue balls, but then I’m not a sex expert. From time to time, it’s good to remember that I’m not licensed to give advice or anything.

It seems to me like you just need to relax. Accept that you might not come, and you should be able to. If that doesn’t work, and you feel really comfortable with her, ask her if you can masturbate to orgasm with her. Maybe if you can touch her body with your free hand while you get yourself off with the other, your body will get the hint that it’s supposed to get off with your girlfriend.


Sexx: My girlfriend and I have been dating for a little over a year. We’re really close and things are going pretty well for the most part, except there’s an aspect of our sex life I can’t get over: she’s never had an orgasm and won’t let me go down on her. It’s not like she’s super self-conscious or timid in bed otherwise, but she’s very anxious in general and seems to have a hard time letting go and fully getting into it. She claims that everything’s fine and she enjoys herself and it feels good, but she’s never been able to finish the job — neither with me nor anyone else. We’ve fooled around with sex toys a little bit, but she always backs out at the end, forcibly taking it off her and claiming that she’s scared to finish. I’ve tried to go down on her, because I think that might help (maybe?), but she has an insecurity issue about that and doesn’t want me to. Obviously, because I’m not a rapist, I don’t force it. I want to be able to make her cum, but I also want to trust her that everything’s fine.

What do I do? Just get over myself? She knows I feel this way and gets bummed that she can’t finish, so I don’t want to keep harping on it, and I don’t want to pressure her more into letting me go down on her. I know that it’s her decision, and I’m sure a lot of guys would be thrilled that they never needed to hold out until their girl finished or had to go down on her, but it makes sex feel lopsided to me. Advice?

Oh, these are always the worst scenarios. When I was 22, I had a 19-year-old girlfriend who had the same problem (although she at least let me go down on her). You know how we solved it? We broke up — although not for that reason — and went about our lives. When we hooked up again five years later, she had an orgasm. Somewhere along the line, she had let go of the mental block. Problem solved!

Seriously, if a woman has never gotten off before, the female orgasm can be more elusive than a greased unicorn. Even if you’re doing everything right physically (which you may not be), if she doesn’t feel confident enough or relaxed enough, then it’s never going to happen. For what it’s worth, the female panel suggested getting her really high and propping up her back with a pillow to help you hit her G-spot.

Pretend sports: Any fantasy football advice I’ve ever received has always neglected the defense, and relegated it to a late-round, relatively meaningless pick. In my experience, though, a good defense with a consistent ten or so points can stabilize a team on a weekly basis. It won’t save you, but it will definitely give you a solid bump. How stupid is it to put some priority on D? Not in any of the first rounds, of course, but somewhere in the middle, when no stars are left and after you’ve got a solid core of RBs, a QB and a WR or two? And which teams are looking best on that end of the ball?
Thanks, -JH

Well, you want sacks and turnovers and (ideally) touchdowns from your defense. If you correctly guessed that the Saints defense was going to score, like, 40 touchdowns last year, then bully for you. But I hope you didn’t waste anything higher than a 15th-rounder on them, because nobody else saw that coming.

In general, your best bet is to go with defenses with strong lines. Pressure comes from the D-line, and that causes the offensive panic and errors that get you sacks and TOs. The Jets, Ravens, and Vikings are all obvious choices, but I’ve gotten by just fine picking up defenses off the waiver wire. Just pick up whoever’s playing the Browns.


Dear KSK,
Fantasy first, since let’s face it, women aren’t going to matter in about a month. Two-part question, too. Keeper league, pick two, where they cost a pick two rounds higher than last year. I snagged both Miles Austin and Vernon Davis, undrafted, so it would cost me my 9th and 10th. My only other ‘viable’ options would be Roddy White (would cost me my first), Matt Ryan (2nd). I figure it makes no sense to do anything else, since those guys are definitely not worth a first or second.

That’s not a question. But congratulations on getting Austin and VD undrafted.

Secondly, I’m looking at the 5th pick this year. Both Ray Rice and Cthulhu (whom I piggy backed on to win my other league) will undoubtedly be keepers (undrafted and 9th round, respectively).

You got Chris Johnson in the 9th round? Your league sucks.

So according to Yahoo’s Big Board right now, I’m looking at… well guys I don’t really trust taking with my first pick. Should I say fuck the RB, until the 2nd round, and go with someone like Andre Johnson or Breesus, or give Gore/Jackson/who the fuck is Ryan Mathews/etc a shot?

A lot of people would say you should be bold and take Aaron Rodgers, but I don’t have the sack to take a QB that high. I’d probably go with Gore at #5 and try to convince myself that the Niners finally have a consistent enough offense and weak enough opponents to justify it, because Gore is TOTALLY DUE to have an injury-free season! (I really hope I don’t pick 5th.)

Sex: I really got nothing pertinent. I’m in an incredible relationship right now, so it’ll be interesting to see how she reacts to her first season of dealing with my fantasy football. We didn’t start dating until December, so she missed the meat of the season. Any tips on this?

Set your lineup Friday afternoon at work. You don’t want to be the manager who forgot about the bye week and didn’t start a QB because you were having Sunday morning sex (or brunch or whatever). It will also make you seem like less of a desperate addict if you DON’T jump out of bed on Sunday morning to check your lineup.


Hey man…
This is not precisely about sex, but i would like to hear an unbiased opinion. My wife and I want to get kids, but long story short I think i’m shooting blanks. They have to make a biopsy of my testicles to see if there’s a sperm around, and if there is…. then we can go the in vitro way.

Thing is, if there’s not… we might have to go to a sperm bank for another dude’s sperm. I cannot grasp the idea of having a kid from another dude….even if it’s an anonymous donor. I love my wife (she’s the real deal for me) and we want to have kids, but it’s just hard knowing that naturally, it won’t be my kid.
Thank you

That’s tough. The important thing to remember here is that if you can’t get your wife pregnant, then you’re not a real man, and your wife will probably find someone else who can fulfill her needs.

No, I’m kidding. Listen, I could quote every touchy-feely movie moment about fatherhood and cite any number of friends who have become parents, but that would be a huge, cheesy waste of time. The bottom line is this: being a parent isn’t about providing the raw genetic material that makes a fetus. It comes from loving for a tiny, helpless human being who NEEDS YOUR CARE TO SURVIVE. It comes from being patient with someone who can use words but doesn’t listen to reason, from reading to them before bed, blah blah blah — all that shit parents are supposed to do. I suspect you’ll forget all that “not my natural kid” bullshit the minute your wife gives birth and you have a brand new human being to love and protect.


Dear All-Pro Poon Prognosticators,
Football: I recently moved across the country, but I want to stay in my old fantasy league. Last year, before I moved away, it was decided that I would be commissioner this year. Can this long-distance relationship work, or should I resign as commish? I am definitely the most active GM, but I’ll be Skyping in for the draft, don’t know a couple of the new guys, and there’s the time zone issue (still not sure if I’ll be able to wake up by 10AM after a night of binge drinking).

None of that seems like a big deal to me. Give it a try this year, and if it doesn’t work out, then resign as commissioner next season.

Sex: OK, so as I said, 6 months ago I moved cross country. And I haven’t gotten laid since. This is the longest I’ve gone since…I lost my virginity 6 years ago, and It’s really starting to affect my psyche and behavior. I’m 23, I’ve never had any trouble getting girls before, and I’m living in freakin’ LOS ANGELES. It shouldn’t be this hard. But the pressure of the record dry-spell has shot holes in my game. Where I would normally be outgoing and engaging, I’ve been hesitant and awkward. I don’t know many people in LA, and my roommates all have girlfriends. Money’s tight, and wingmen are hard to come by, so I only go out to bars about once a week, twice max. Back east, after college I mostly hooked up with girls I met through work…but my new job is 95% dudes. How do I get this monkey off my back!?
-Missing friends and booty-calls, but loving sun and eye-candy

Your problem is you’re going out to bars. Bars are terrible places to meet women. I blame college for not teaching us that. In college, you can get shitfaced on dollar pitchers AND hook up with a Pi Phi you met five minutes before last call. In the adult world, you’re just a potential rapist racking up an eighty-dollar bar tab.

The simple solution here is to try online dating. It streamlines the process for you: no wingman necessary, and you can always tell yourself it’s because you’re new to the city and you’re trying to meet people. You could feasibly be having sex with someone you met on Nerve or OK Cupid tomorrow.

If, however, you don’t like the stigma of telling your friends “We met online,” then you need to try other things. Do any of your co-workers have attractive girlfriends or wives? If so, then have sex with them ask them to set you up. Or you can try expanding your social circle. Volunteer, or join a running club, or take a cooking or wine-tasting class. All of those things not only improve you as a person, they’re also a great way to meet new people.


Dear Rex Ryan’s Blogging Faggots,
FOOTBALL: Is there any chance in hell I should draft Devon Aromashadu from the Bears this year? He put on some gaudy numbers last year and being a homer I think in Mike Martz’s pass happy offense he could be a sleeper.

Well, he put up some gaudy numbers for about four weeks. He’s a sleeper, yes — but he’s everybody’s sleeper. He could very well have a breakout year, but that doesn’t mean he’s more than a mid- to late-round pick.

SEX: I am a HORRIBLE person. I was married for 5 years and got divorced because she was cheating on me. I then fell in love with two women one was a cheater and the other was a cheater and coke/crack addict who kept it hidden from me until she broke it off. I’ve given up on relationships.

What you should give up on is falling in love with shitty people.

Now, WHY I am a horrible person? Being a facebook person I come into contact with A LOT of old friends. Most women I talk to are married and “looking”. I recently realized that any woman who is married really just wants the attention she got when she was single. Nothing more nothing less. And wedding vows aside they will GLADLY rerurn that attention. Fish in a barrel so to speak. So I am a terrible person because I am doing what some other asshole did to me. The only way I can justify it is to say I will not break up a family because it’s always a one or two night stands. Can I keep rationalizing this as they get what they want and so do I?

Sure, you can rationalize it all you want. It won’t make what you’re doing any less shitty. A one- or two-night stand can still break up that family if a guilty wife fesses up, or if she stays logged into Facebook when her husband gets on the computer. And then you’ve got a pissed-off cuckold looking for you in a country with pretty lenient gun laws. I’m not saying any of that will happen, but karma’s a bitch. It’ll find you.

BTW, one of your staff’s wife is AMAZING IN BED guess which one?!? … Ok It’s Drew.
Hypocrite MILF Hunter

The feeling isn’t mutual. She was just telling me the other night how lousy you were. And how you needed a cat in the room to keep an erection. Very strange.


Gentlemen…and I use the term loosely,
Fantasy first: I’m in a league with my buddies from HS (I’m 28) and we have a good group of 8-10 guys that play every year. But we’re getting to the point where the same 2-3 guys are dead weight ghost teams and the other 2-3 ‘outsiders’ don’t bring much to the table as far as trash talk and general camaraderie are concerned. What’s the best way to tell the guys who are from our HS group to kick rocks if they won’t take the league seriously (as seriously as one takes fantasy football) so we can get some new blood in?

I’d pull them aside individually and give them a sincere, slightly worried, “Hey man, do you still want to do this? You haven’t really been into it lately. I know some guys at work who wanted in on the league, but I told them no because we go back so far…” If they respond to the guilt trip, then you need to make it clear that from now on, they have to be more active in your pretend-sports league. If they STILL suck this coming year, then that conversation will be the groundwork for kicking them out.

Sex second: I’m in a great relationship with a girl that I’m crazy about (attached).

Everything is great and we’ll be getting engaged as soon as I save enough scratch to for a ring. She’s perfect and I couldn’t be happier. But there are two things I’d love to get her to do. She sugars herself instead of waxing or shaving (fine)

Hold on a second. I had no idea what “sugaring” was, and neither did the three women in the room with me. And these are three women with well-groomed vaginas. Or so they tell me.

Anyway, sugaring is similar to waxing, supposedly less painful, and completely inessential information in your letter. Let’s move on.

and she leaves a nice little landing strip. Is there a way to coax her into getting it all removed without sounding like a jerk that wants his gf to look like a porn star?

If she’s already getting most of her pubic hair removed, she’d probably be open to getting it all removed. The next time she talks about going to get sugared (or the next time you get a freshly sugared vagina), just ask her if she’s ever considered going hairless. Tell her that you think she’d look really sexy like that, and it should be fine. Rule #1 with women: when it doubt, phrase it in the form of a compliment.

Second (and on the same wavelength), she’s in very good shape and works out pretty regularly but she’s my age and so doesn’t weigh what she did in college. Is there a way to encourage her to push a little harder to lose the 5-8 lbs she keeps threatening to? I haven’t figured out how to do it without her hearing “you’re fat and should lose some weight pronto”. Thoughts?
-Looking for smoothness

Well, most women will never look the way they did in college, although the temporary panel assembled were happy to point out that they all look better now than they did in college.

There are only two ways you can justifiably ask your girlfriend to get in better shape: (1) You are on the cover of Men’s Fitness, and (2) you offer to make the lifestyle change with her. Now, 5-8 pounds isn’t much. Most people can do that with some small changes in diet while maintaining their workout schedule. So you could try telling her that you want to try to eat healthier, and see if she’d be willing to join you in cooking your own meals for the rest of the summer. Or challenge her to see who can lose five pounds first — winner gets 20 minutes of uninterrupted oral sex. Either way, you’re going to need to get off your ass, too.

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