The 29-Year-Old Virgin, Flo from Progressive Commercials, Friendly Strippers, and Reformed Craigslist Sluts: the KSK Sex/Fantasy Football Mailbag

03.18.10 8 years ago 86 Comments

Sweet Jesus, people, that was a lot of questions! I left more questions out of the mailbag this week than ever before, and it was still more than I could really handle. I’ll try to get to some of the leftovers next week, assuming we don’t suffer another tidal wave of submissions. As always, my apologies to not getting to everyone.

Let’s get straight into it, shall we?

Dear KSK,
Sex — The giant elephant in the room is that I’m a 29 year old virgin.

As Riker and Picard would say, *sad trombone* NOOOOOOO!

I was incredibly shy early in life (a lot of it comes from my height. Being 6’8″ and insecure is a bad combo) and by the time I got to college when I should be experimenting with women I was put on anti-depressants that killed my libido. So I missed the golden window to be inexperienced with women. Now, we could go over the many things I’m doing wrong in my life, but I know these and am working on addressing them.

All right! I can skip the self-improvement lecture this mailbag!

Now that my sex drive is back in life after 10 years, I’m dating a lot more. While I have a guilt problem with one-night stands, I have no problem with pre-marital sex (Catholicism is only slightly effective). I’ve been dating this girl for about a month now and things are going well. I like her, and we’re nearing the point where she wants to take the next step. My question is should I tell her I’m a virgin as a pre-emptive strike for my impending mediocrity? She knows about the anti-depressants so do I say something like “listen, the anti-depressants I was on zapped my libido so I haven’t had sex in a long time”? Or do I just go through with it, have a minute of horrible sex and hope she forgives me and continues to want to sleep with me?

Yowza. That’s kind of a tough one, because there’s a chance that she doesn’t want the burden of being The First, and/or she could get skittish if her retard friends get in her head about “Why is this guy a virgin at 29?”

However, as a rule of thumb, I preach honesty, and ideally, your girl will be understanding of your transition from awkward teen giant to depressed adult on boner-killing meds. You have a much better shot at enjoying better and more frequent sex (and developing some skills) if she understands where you’re coming from, as opposed to you finishing after a minute and shouting, “Score! Not a virgin anymore, SUCKA!”

Football — my team blows goats. No question, just me pondering trying to resist the urge to kill our coach & GM.
— Anonymous

You’re better off killing the owner. You kill the coach and GM, well, the owner’s just gonna find someone else who sucks.

Dear KSK,
Sex question: I am married with child. I live near my in-laws, who blatantly prefer other grandchildren to my daughter.

Is she ugly? Maybe a little slow?

This angers my wife and me. I was helping the mother-in-law with her computer when I innocently came across an email where she confirms not liking our daughter as much. I then not-so-innocently found another email where she refers to me as a “freaking idiot.”

Background on MIL: she is an ignorant, hypocritical, uneducated, Christian/Republican extremist. Her opinion is tainted. Still, gatherings are now awkward, if only for me.

The question: whether to explain to my wife what MIL is saying to others about us, given that (1) I violated MIL’s trust by reading the second email (but I tend to prefer full disclosure with the wife) and (2) this will almost certainly sever wife/MIL’s relationship. And this involves sex because I feel like I’m fucked either way, and if mishandled I may lose privileges for some time.

Well, for starters, there’s nothing wrong with being Christian or Republican. And being uneducated isn’t necessarily a bad thing, either; I’ve met plenty of people without college diplomas who have a better understanding of the world than people who’ve spent the decade after high school with their heads in books. However, ignorant and hypocritical is no way to go through life, and those traits should never be rewarded or tolerated, even by family members.

Before I jump into my advice, a bit of a disclaimer here: I come from a family where both of my parents have rocky relationships with their parents, and my sister’s in-law situation with her husband is less than ideal. I’ve seen the maddening stress people go through to try to please their in-laws (or their own parents), and I’ve rarely seen the kind of catharsis — the mental revelation — that comes from standing up for yourself and saying, “Fuck you, that’s not okay.”

Be up front with your wife. Tell her everything. She’s your life partner, after all. Sure, you shouldn’t have gone into the mom-in-law’s email, but I think it’s within the boundaries of normal human temptation given the circumstances. Besides, what would be so bad about not having to deal with your mother-in-law any more?

[Witty Title]

What is your opinion on college bars? I’m near graduation at a very respectable, highly competitive private university (yes, I’m an elitist douche) and every time that I go to our one local bar, my initial, somewhat buzzed optimism inevitably turns into dismay. It seems like the majority of female patrons are more concerned with social, and secondarily, financial status than anything else and seem preconditioned to look for certain status symbols like wealth and greek standing, as opposed to intellect and fantasy football championships. Shocking, I know. Anyway, my question is basically the following: Is the post-collegiate landscape any friendlier to people like me, i.e. intelligent, thoughtful types, or am I doomed to constantly have to validate myself in terms of arbitrarily valued accomplishments like which frat I allowed to sodomize me or what I-bank my dad works at? Basically, how much does social and financial status matter after college when girls are no longer allowed to be so picky?

Girls will ALWAYS be picky. Until about their 30th birthday.

And no, I’m not an awkward, afraid-to-approach girls type, relatively speaking, I’m just sick of having my conversations end at which frat I didn’t join or what BMW I don’t drive. And yes, I know I might sound bitter, but I’d like to hear that maybe the rest of the world beyond where I’m stuck at isn’t always this way.

Well, well, well. Mister Fancypants McPrivateschool came running to the sound of the elitist clarion call, but didn’t like it when everyone there turned out to be elitist assholes. Arizona State doesn’t look so bad anymore, does it?

Anyway, there’s good news and bad news. The bad news is that all women, to some extent, care about financial status. And generally speaking, the hotter the woman, the more likely she is to care; it’s why stock traders have sexier wives social workers. But it’s not necessarily a bad thing: pretty girls are a nice incentive to turn off the Xbox and make something of ourselves.

The good news is that we all fit in somewhere. I’ve lived in ten different states in every region in the country, from cities to college towns to suburbs to the middle of fucking nowhere, and I never felt like I fit in anywhere until I moved to Brooklyn. Sure, I can complain about annoying hipsters and bookish pussies and some entitled douchebags who’ve lost perspective of the world outside their bubble, but it works for me. There are other writers, other bloggers, other people who share my sense of humor. It’s friendly to dogs and bikes. The whole borough is casual. I belong here.

There’s somewhere like that for you, too — and it’s likely not a specific, unique-in-the-world place. Whatever societal niche you’re seeking, you can probably find it within 75 miles of any major American city. Find some people you like (or admire, or want to emulate), and follow them.

Football: No real question, I win every two or three years–thats paying off with the ladies! That being said, how do you think Anquan Boldin will help Flacco progress? I think hes a top 10 QB with the right weapons, but what do I know, I’m just a Baltimoron.
-Signed, Switch Hitting Jesus (Thats a baseball reference ’cause its baseball season)

I would think Boldin can only help the Ravens. Keep in mind, however, that high-profile #2 receivers, when they make the jump to another team to be the #1 guy, often experience a drop-off when, say, Larry Fitzgerald isn’t getting double-covered on the other side of the field. Regardless, given that Derrick Mason — who’s solid, but certainly not electric — was seemingly Flacco’s only non-Ray Rice target, you can probably expect your QB to continue to improve.

As for ranking him in the top 10, who cares? There are people who think Eli Manning’s a top-10 quarterback, and they might even be right. Having a guy in the 70th percentile isn’t all that exciting.

1. Football: I’m convinced that there will be a lockout in 2011. The very thought gives me hives. That said, now that the players’ union have an actual qualified labor attorney running the show, I suspect that they won’t roll so easily and we’re fated for armageddon. My question: should I turn to drink now, or just live in denial and try to catch up once it becomes a fait accompli?

Settle down, Chicken Little. What the hell does worrying accomplish? Will there be a lockout? I dunno. What can I do about it? What action can I possibly take that would make the billionaire owners and millionaire athletes to stop and take my desires into consideration? Nothing. There is nothing that I can do about it. The possibility of an NFL lockout may as well be the weather, or an earthquake, or the possibility that I get killed by a falling construction crane or drunk driver. I can’t affect whether it happens, so the only thing I accomplish by worrying about it is raising my blood pressure and shortening my life in little fear-stained increments.

2. Sex: I get turned on by the woman in the Progressive Insurance commercials. (Yes, really.) I think she’d be kind of crazy in bed and, unlike most women I’ve encountered over the past few years, au naturel down below. Everyone I mention this to thinks I’m a lunatic. Am I?

Ah, Flo, also known as actress Stephanie Courtney. Are you crazy for wanting her? Well, yes. But you’re not alone; I once talked to a girl who said that “every” guy she knew wanted Flo.

It’s the crazy eyes. The bright expressions, the enthusiasm, and those wild, untamed eyes that guarantee a woman fucks like a banshee and comes like the wave pool at Typhoon Lagoon. They’re the kind of traits that make you look past her clinginess and weird baby talk because her Kegel muscles milk your cock every so hard every weekend that by Sunday night your ejaculate is just a little puff of smoke.

It’s all fun and ‘gasms until your pet bunny gets boiled.

Dear Counts of Castle Dingleberry,
Sex: I had a drunken threesome with 2 girls at work after a team outing. None of us were really that drunk, but I was buzzed enough that my judgment lapsed. Neither girl is particularly good looking (I know, I know: descriptions are worthless without pics, but at least I’m not claiming they were 9’s) and the sex was not nearly as cool as it looks in porn, but it was something to do on a Thursday night after a bit of a dry spell.

You heard it from this guy first. Threesomes: an okay way to pass the time if you’re bored.

Going into it, we all agreed that it was just going to be a fun, onetime, non-committal thing. Since that night one girl (we’ll call her Rebecca) has acted the same as before. In other words, she’s cool with it. The other girl (we’ll call her Amy) has proceeded to go bugshit crazy. She cornered me in the lunchroom and claims we had some kind of connection and that it was fate, etc…etc. She is openly hostile to Rebecca whenever she sees the two of us chatting and it has completely disrupted a perfectly good 3 way friendship (I suppose sex will do that every time, huh?). It hasn’t disrupted our work yet, but if Amy continues to claim we should be together, that we’re soul mates, etc, etc, I’m afraid it might. I really enjoy my work and where I work, and the people I work with, and I don’t want to quit, but I don’t know what to do if Amy continues with all this crazy relationship talk.

And this is why you DON’T want to have to sex with Flo. Good luck, buddy.

Fantasy Football: I’ve been in multiple FFLs per year for 5 years running. I spend maybe 1 or 2 hours a week maintaining my rosters. I’m thinking about running a league this year – how much more time will I need to invest to run a successful league (and not have my friends get pissed off at me for being an absentee commissioner)?
Fuct at Work

I’ve never been a commissioner before, but it doesn’t seem like it takes some huge amount of time. Set up the league, organize the draft, and mediate the occasional dispute. The biggest headaches will be the draft and getting everyone to pay (try locking their lineup before Week 1 until you get a check, that usually helps). It’s not like it’s a second job.

Hi guys,
So I guess I’ll start with the fantasy question. I don’t really watch much football and I never played fantasy before, but my friends from school all make fun of me so I’ve started reading this blog and I am going to play next year. Go Lions! Anyway, I am from outside Detroit and I was wondering if you thought there would be any Lions players worth picking up next year so that I could root for them.

Kevin Smith and Calvin Johnson are good Lions to have for fantasy purposes, but I’d advise against being a homer in fantasy. You’re already going to be in enough pain when the Lions lose, you don’t want to be doubly pissed at Johnson for getting tackled at the 2-yard-line instead of scoring.

Now onto the sex, which is the real reason I am writing in. I have been dating my girlfriend for a little over a year. She is really nice and I like her a lot. Before her, I had never had a girlfriend, and my sexual experiences consisted of two drunken nights with big girls. A couple months ago, my girlfriend and I both got really drunk. We got home, and she told me she really had wanted to experiment with something, and she took out a strap on. At first I thought it was a little weird, but I like her a lot and was pretty drunk so I went along. Also, I had kind of been thinking that might be fun too, but I was a little scared to ask until she brought it up. Anyway, it hurt a little at first but I kind of liked it, and she seemed really into it. The problem is, since then that’s all she wants to do. Don’t get me wrong, it’s a lot of fun, but I feel kind of emasculated and would like to be able to have sex with her too. What do you think I should do?
Thanks guys,
Bob in Arizona

Wow. Just… wow. First — and this is important for the unenlightened masses — a woman fucking you with a strap-on is NOT gay. It doesn’t fall within the realm of my tastes, but the gender of the people involved, not the act, determines whether something is homosexual or heterosexual.

Now then. Assuming that this email is not fabricated, what’s more emasculating than you getting pounded in the ass by your girlfriend is your unwillingness to get what you want in the bedroom. Even men looking to score anal from their girlfriends don’t expect to get it every time they have sex — why should it be that way with you? Try saying, “Not tonight,” and work from there.

Dear KSK,
FF: As far as fantasy goes, what is proper etiquette for breaking up a long running league? I have been playing fantasy with the same guys since high school. Last year 2 of our regular crew dropped out and one being our long running commish, but he assured us he got someone who would be “better” than him at it. Both new guys turned out to be douches, and I still have yet to see my winning payout. There are about 4 of us who want to either start up on our own or kick the newly appointed commish out. Unfortunately he happens to be the brother of a wife of one of the guys, so it wouldn’t be well received to vote him off the island. Any thoughts?

Does no one vet candidates any more? Christ, why would you let a guy who’s new to the league be the commissioner? That’s just stupid.

Sounds like this is a problem for the guy who’s married to the commissioner’s sister. Make him do the dirty work.

Sex: Back to the previous situation I had written before around January-ish.

See: This mailbag, in which our 22-year-old protagonist struggled with his uncertainty of committing to a relationship with a 33-year-old woman he really liked. Let’s take a trip in the way-back machine to see what advice I gave after he started having second thoughts about backing out of the fledgling relationship:

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.

Basically was with a down awesome older chick phenomenal sex great girl but who wanted more and I tried to let go cause I thought it was not what I wanted. I didn’t think I wanted a relationship with her but was wavering because she really is great and even though there is a big age difference after comparing her to girls my age in all aspects she still just takes the cake. We have a ton of common friends and factors put us in the same places and after seeing her start dating a guy who was a total toolbag and her getting closer to him, in an awesome fit of drunkenness pulled her aside to try and tell her how I felt but ended up started a fight with toolbag before I could even hear what she had to say. Got busted up thrown out of my favorite bar forever and a nice refreshing night in jail. Acting like that is out of character for me but I still did it and own it. Thinking more and more I have made a mistake with this girl. I am not going to find someone like her and compounded with my liquid courage of the night the situation just got way out of hand. Now, she won’t talk to me take my calls doesn’t say anything about the situation to any mutual friends or anything after I acted like a moron so any good advice of how to get her to even acknowledge me again would be appreciated.

She SHOULDN’T acknowledge you. You passed on the opportunity to be with this woman, then you acted like a drunk young dumbass. Then you followed that up by being desperate and needy. Leave her alone, and apply the lessons you’ve learned to your next relationship.

Another thing to apply? Some commas in your sentences.

I’ll try to keep this brief. I’m 30 and single, and I have a solid career and a house. I’d like it if the next relationship I’m in at least has the possibility of working out long term. I’ve been on a bit of a dry spell lately, and my only previous long-term relationship (2 years) involved a girl with some fairly serious drug problems and resulting sanity issues. The current story involves a bachelor’s party and a strip club,

There was one dancer there that caught my eye, so I asked her for a table dance for the group, which was great. I then asked her for a lap dance, which of course turned into three. It was by far the most attentive & enthusiastic lap dance I’ve ever had (out of maybe 10 in my life), and it included some kissing and titty-sucking, which I assume strippers don’t generally do. (She told me as much). She also wanted me to choke her, which I did, just right apparently. I tipped her well

Rightfully so.

and acted warmly and appreciatively in general. I thought we had established a good rapport, at least as far as the stripper/client relationship goes, and I thought she seemed like a genuinely cool person. At the end of the night, I was ready to go home to jerk off and try to put the girl out of my mind, but she gave me her number as I was leaving (without my solicitation).

Oh snap!

Here’s the question. Am I fucking batshit insane for thinking that there’s any remote chance that she could be a good woman to me? Has something like this ever worked out non-catastrophically in modern history? On one hand I think it’s worth a shot, but on the other hand I see potential for the situation to blow up in my face.
Burt Reynolds

Realistically, is it a wise investment of your time for a long-term relationship? No, probably not. Do you need to explore the possibility of dating her? Yes, absolutely. You owe it to yourself and the rest of mankind. End of discussion.

KSK Brothers,
I started dating my girlfriend about 11 months ago I’m 27 and she is 26. Her job causes her to travel 2 weeks out of every 6 weeks and we both become pretty sexually frustrated. A few weeks ago while I was at work she innocently sent me a pic of her enormous breasts. They are 38 DDD. She is a not a model, but neither am I and I like big women. This escalated all the way up to the point of an all out picture trade and mutual masturbation over the phone. I had never done that before.

Ah, congratulations on smashing a bottle of champagne against the hull of the USS Phone Sex.

So she came back home and I was over at her place messing around on her computer when I found a folder containing about 300 pictures of her in sexy lingerie, playing with her tits, and fucking herself with various toys. I was blown away and when I brought it up later she proceeded to tell me that it is how she made a living during college. She would sell pics of herself on Craigslist to various men. Maybe Falco? I feel like I should not have a problem with this because it was over 2 years ago, but its like I’m dating a fucking porn star or something.

No, not at all. Porn stars are sex professionals, and much better compensated. Your girlfriend’s more of an amateur fetish model. About on par with a phone sex operator, I’d say.

I feel like I’m having sex with 100 random men when I’m having sex with her.

Okay, quit being a bitch.

I love her very much and things were going so well up until this point, but now we have not had sex since this happened. I feel like I don’t know her anymore. She assures me that she only took the pics to sell and she never shows her face in any pic. I asked her to delete them and she did as far as I know. Am I blowing this out of proportion?


Up until 2 weeks ago I was sure this was the girl I was going to marry. Maybe I’m a pussy? She says she has only had 7 sexual partners before me. I don’t know if that is a lot or a little for a woman.

She’s 26. Let’s say she lost her virginity at 18. Is one guy per year a lot?

Listen, I don’t want to side with your girlfriend’s skeevy exploitation of perverts, but you need to sack up and enter the 21st century, Nancy.

I have had 11, but yet I feel like I’m fucking a whore whenever we do get intimate and then I lose interest. Do I need help? Do I need to end it? My buddy I mentioned it to thinks I have trust issues and I should see a shrink. I don’t know anymore. I’ve hardly slept or ate since this happened. She told me she would wait until I got over this because she wants to be with me doesn’t think it is a big deal. She said that I would be surprised by how many college girls earn money by selling pictures of themselves online.

So not only have you had more sexual partners, you’ve had them at a faster rate, and yet she’s the whore because her acts — which, a couple weeks ago, opened the door to your first phone sex — don’t fit into your definition of morality? Frankly, I don’t want to recommend anything that might heal your rift. I don’t think it’s fair to subject your girlfriend to your self-righteous attitude.

Just so you know I was not snooping on her computer. I was installing new tax software for her and she wanted it in a certain folder.

A decision I’m sure she regrets. Even if you guys work something out, you’ve now established that openness and honesty can lead to you punishing her with your judgment. Way to fuck it up, pal.

Fantasy: Better keeper, Forte or Benson?

And this is why I love the mailbag. An epic, worrisome sex dilemma punctuated with a simple fantasy football question. Fantasy may be a constant mindfuck filled with lose-lose scenarios, but it’s got nothing on life.

Go with Forte.

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