KSK Sex and Fantasy Football Mailbag: Please do not encourage these people

08.07.14 3 years ago 156 Comments

"Quack quack! Put me in a vagina!"

Via The Pleasure Chest

"Quack quack! Put me in a vagina!"

As promised in the header image, we’ll eventually get down to fisting in this week’s mailbag. But first, I’d like to direct you away from this story of a 24-year-old Irishman who sat next to a cute girl on his flight, talked to her, didn’t get her last name or any contact information from her, then created a hashtag to find her.

On a Ryanair flight from Dublin to Barcelona, 24-year-old Irishman Jamie Kelly found himself sitting beside 27-year-old “Katie” from Nova Scotia, Canada. After Kelly offered up his seat to Katie’s mother—with whom she was traveling—the pair began chatting merrily, but became separated at passport control in Dublin. Despite searching, Kelly realised he’d lost her, and returned home alone.

Unperturbed by the fact he didn’t know her surname, her phone number, or almost anything about her, the enamoured Irishman didn’t give up there. Instead, he made it his mission to track her down, and—with the help of his friends—launched a Twitter campaign to find her. 

And because the media picks up on anything that sounds like a terrible rom-com scenario, of course they got in touch thanks to this idiot’s flailing around on Twitter after failing to have any guts in person. He had the entire flight to get her information! And it’s not like planes make surprise landings. It’s not like the bus or the subway where “Oh, this is my stop” can tear people apart. Make a move on the initial descent, you coward!

Anyway, it’s long-distance and they’re doomed, so that’s nice. Let’s get to your submissions.

Greetings, captain, how are you this fine week?

I’m jet lagged but good. The last four Fridays I’ve been in Los Angeles, Boston, Seattle, and Barcelona. SUCK ON THAT TRAVEL, PETER KING.

Football first: I was guilted into joining a new 16 (!!!!) team league with some former work colleagues at my last job (1 qb, 2 rb, 2 wr, TE, flex). I tried my best to influence this league into a better system, but was unsuccessful. Anyway, I’m picking last because why the hell not? So…any advice for “strategy”? The largest league I’ve ever been in was 12 players, and this blows that out of the water. I feel like by the time the 6th round comes around I’m not going to know any of the available players anymore.

Two words: Mock draft, mock draft, mock draft. Put yourself in the 16-hole of a 16-team mock draft and get a feel for what that’s going to be like. Do you need to get two running backs with your first two picks? Or are you comfortable trying to snag Zac Stacy and Bishop Sankey at 32 and 33 overall? Any time you’ve got the double-pick in a snake draft, you need to be ready to make bold moves for the guys that you want. And the best way to do that is to practice.

Sex (or not–sorry): I’ve finally adjusted to living in NY after moving here last Fall–it turns out the LES is great for drinking and not so much for going to bed before 3 on a weekend. Anyway, while I have some good friends in NY including a great high school friend that I’m rooming with, I’ve really struggled to meet single ladies who reciprocate my advances. And because there are so many people here, I then feel even worse because “YOU’RE IN NYC, WHY ARE YOU NOT MEETING PEOPLE?” 

Seriously, why are you not meeting people?

I have social hobbies that I love, and I’m actively trying to put myself in situations where I could meet the kind of people I’m looking for. I feel like I’m in good shape and am pretty happy with myself as an overall nice 26 year-old guy looking for something serious. So I guess I’m wondering, are there any glaring pieces that I’m missing? This city must be so much better with a significant other, right??
Thanks for the help, good luck with your drafts!!
-Ozamataz Buckshank, Stanford University

First of all, New York City is not substantially better with or without a significant other. Hawaii is better with a significant other, Las Vegas is better without one, and everywhere else is just a place where you can be miserable or happy in or out of a relationship.

The obvious answer, of course, is online dating — Tindr and OK Cupid are typically best for casual daters your age — which will drown you with a wealth of options, almost all of whom are looking for someone better. The way it works is this: you try online dating for a couple years, get frustrated with how it can lead to sex but never anyone you forge a deep connection with, which in turn makes you instantly fall in love with someone you meet in person.

If online dating isn’t your thing and you’re looking for an actual relationship, then hit up your network of friends and co-workers. Some of them are bound to have girlfriends, and those girlfriends have friends. Voilà, instant date! And you didn’t even have to talk to a stranger in a bar! 


Dear KSK,
Relationship: I previously wrote in as a 29 or 30 year old virgin self-diagnosed with Asperger’s syndrome who thought he was going to be Forever Alone. Since then, a woman who I thought I had previously blown my chance with came back into my life, and we navigated the stages from texting to going on dates to serious dating to sex partners to cohabiting and sharing a joint checking account to being engaged, with marriage and children in our future plans. So that’s good.

That IS good! I’m filing you under “mailbag success stories” even if I had no impact on your life whatsoever.

But …

Twice now we’ve had a disagreement where she expresses disappointment that I won’t say that I love her/our cat. 

/removes from “success” file

Now, as cats go, he’s pretty nice. He’s quite social for a cat, he doesn’t bite or pee on things or spend half the night yowling. He’s sitting on my lap right now as I type this. I’ve included a picture of how we found him sleeping one day (we know he’s overweight, we’ve got him on diet food). 


Yup, that’s a cat all right.

That said, maybe I’m a psychopath, but I can’t imagine expressing love for a non-human. I tell her that I like him a lot, but she says that’s not good enough. That he is very important in her life, and he needs to be important in my life too.

As I see it, I have two choices: (1) Decide this isn’t worth fighting over and do what she wants, or (2) Try to find some way to get her to at least respect my opinion and point of view, even if she can’t necessarily agree with me. The first time it happened, I hoped it would blow over and be forgotten, but of course that was folly. And both times she’s brought up right before bed and I have to work early in the morning and what the fuck are we even talking about?!

Number one of those two choices is certainly the path of least resistance, but it sets a bad precedent for a relationship that you want to last the rest of your life. That’s going to sow resentment on your part, because you’re going to feel that she forced you into a position where your only choice was emotional dishonesty. And there WILL be times in your relationship where you have to say things she needs to hear rather than the things you want to say (like when she complains about work), but I don’t think this is one of them.

So you get Stock Mailbag Response #2: sit down and communicate as honestly and tactfully as possible. I would go with something along the lines of, “I’ve never been a cat person, so I don’t think I’m really programmed to love a cat. But I’ll always pet it and feed it and show it affection, and if you got hit by a bus I would definitely care for it the rest of its life as an avatar of our relationship. I’ll always love you, and I want to make you happy, so I’ll keep doing the best I can to love the cat, but I’m not going to SAY that I love it just to make you happy, and it’s unfair of you to put me in a position where the easiest option is to lie to you about my feelings.” I would also suggest talking to her about not having “important” discussions like this just before bed on a weeknight.

It’s a fucking cat, man. You’re in the right not to love it. (Do not tell her this.)

Football: I’m lucky that she’s way into football (when I suggested that we might have one of our early dates going on a tour of Lambeau Field, she thought it was the best idea ever), and she wants to participate in my hobbies, including fantasy football. So I’m going to let her co-own a team with me in a family league I’m in. Looking at projections I trust, I’m seeing a big drop-off from Manning/Rodgers/Brees to whoever you think is 4th best. ESPN has all 3 of them going in the first 12 picks, with Stafford not going until 33. What do you think of getting whichever of them is left (most likely Brees) in the 2nd round?
Like Not Love

I think Brees is the best of the big three quarterbacks this year, with Rodgers a close second — although if you live in Wisconsin and it’s a family league, one of your homer kin will snap him up WAY early. Manning still has a terrific ceiling, but I don’t want to be the guy holding the Peyton Manning Injury Grenade in the big game of fantasy hot potato. I say all of this and more in my QUARTERBACK RANKINGS EDITION OF KEEPERS!

To answer your question more directly: ESPN is garbage, all three quarterbacks should go after the first round, and getting Brees later in the second round is a good deal. 


Hey man! Football is almost here, I’m so excited!
Football – In my 0.5 PPR keeper league I had the option to keep all three of Forte (R1), Le’veon Bell (R15) and Andre Ellington (R14). All pretty OK options. I was out drinking with one of my league-mates and we made a deal to trade some of my RB depth for his WR depth. The deal ended up as Ellington for Crabtree (R14- I also could have had Percy for the same round cost). I knew at the time Ellington’s ADP was probably right around, if not higher than Crabtree’s, but I was OK with it since I’m high on Crab/Kaep and think Ellington’s a little hyped up. I’m starting to have 2nd thoughts on this deal now that I’m sober and worried that Ellington might turn into a PPR monster in the mold of Forte/Shady, and Crabtree is already banged up, never mind recovering from an achilles tear. What do you think?

Ellington’s an electric player, but he only had 118 carries in his rookie season. His season-high in a game was 15 carries, and he averaged about 2.5 receptions per game. Not exactly PPR monster material. And while he no longer has Rashard Mendenhall stealing carries from him, he IS an undersized speed back in the NFL’s most physical division. I’d say he’s as much of an injury risk as Crabtree, who probably has a slightly higher upside. Anyway, it’s a 14th-rounder. Don’t sweat it too much.

Not so sexy wedding stuff – For a while now my fiancee and I have been looking for a fun wedding venue. We finally found something we really, really like, but its a little smaller than our current guest list…(literally doesn’t have the space for more tables, cost isn’t the problem) its a rent the hall and do it yourself kind of place, so its cheap and they’ll let us do whatever we want…we have it all night and will bring the our own food and booze and lock up when we’re done. We both have big families that live in the area and will definitely be attending, so we don’t expect a ton of no’s, but a lot of the family won’t be hanging out really late because they’re from the suburbs and scared of the scary, scary city. SO what we’re thinking about doing is for our friends who we can’t fit in for dinner and ceremony is to invite them to show up late and drink and party with us after some family leaves. 

It sounds really hokey writing this out, but in my head it sounded a little better. I like to think the friends who would be in that second group will understand the logistics of it all, we’d explicitly tell them not to bring gifts, just come and have a couple drinks and enjoy the fun part of the wedding. We’ve had a good number of couple in our friend circle married this last year so I’m banking on everyone being over the fancy traditional shit and just looking for a good time.

How would you feel if you we’re invited to a wedding like that? I’ve been stuck in wedding planning mode for a while and need an outside opinion.
Weddings Are Hard

As an easygoing person who likes free drinks, I’d probably be okay with being invited to a wedding like that. But as a married person, I would definitely have a conversation with my wife about what the fuck is wrong with WAH and his fiancée, and why they didn’t just invite fewer people.

You have to make some hard decisions when you plan a wedding. Sometimes that means not inviting beloved family members; sometimes it means choosing a date that conflicts with a dear friend you wanted in your wedding party. Seating charts, arguments with parents — it’s all kind of a gigantic headache just to throw a kickass party.

So, I won’t tell you this is a bad idea, because planning a wedding sucks and the last thing you need is someone saying “Well don’t do THAT!” to something you think is a solution. What I WILL suggest is that if you plan it out a little more thoroughly. Don’t expect Uncle Darryl and Aunt Mae to cut out early just because they’re afraid of Metropolis after dark — you’d be surprised how many old folks will kick it late into the night for a wedding. On a similar note, don’t give your friends an informal invite to come drink your booze “around 10ish, I guess?” because some will take that as an insult — “Well, you didn’t make the cut to attend the wedding, but come have a drink when the actual invitees leave.”

If you’re going to do this, give the suburbanites a clear exit time and include it on the invitation:

Ceremony: 3:00 p.m.

Cocktail hour: 6:00

Dinner and dancing: 7:00-10:00

After-party: 10:00 until we run out of booze

This way, you can send your friends a different invite that’s all, “COME DANCE AND DRINK AT OUR WEDDING AFTER-PARTY.” That will make them feel like they’re actually invited to a real event, and not just drinking the spillover rum.


Greetings good sir – are you having a nice summer?

I am, thank you.

This is another story of heartbreak and of a hard lesson that we need to follow your breakup plan to the absolute letter. 

A good start to any mailbag submission: tell me I am right.

Breaking off all contact is an absolute must as I was beginning to move forward with everything and she contacts me out of the blue with a text near my birthday. Of course I want to re-initiate conversation and that closeness again because June has both of our birthdays and the anniversary, but found out her feelings were more of: I do miss you and am lonely but still feel we aren’t right for each other. But hey, maybe we can try being friends. 


That totally fucks with your head and after all the progress I made I’m kinda back to square one with the grieving process as I type this email. I’ve sent my “goodbye” email and told her to not contact me unless it was about us getting back together. I took measures to block her number and to prevent ME from texting/calling her. It feels good to have a measure of control in your life and I’ve been finding a lot of success on Match.com. It feels like you’re cheating at first talking w/ these girls, heck I was sick to my stomach at the thought of seeing someone else, but that fades just over a week or so.

A bit of background: Been going out with a woman, we’re both in our 30’s and each had kids from a previous marriage. We dated for a year plus, were introduced to each other’s kids, etc. There are a few items I have questions on as I go through this split:

1. We were happy and committed and because neither of us owned a vehicle that could transport 6 total people, we moved forward with purchasing an SUV that fit those needs. Well her credit wasn’t great and so I put the loan in my name with her making payments and her driving the vehicle/routine maintenance/etc which was always the agreement all along. Then we broke up a few weeks ago. She doesn’t have issues making payments but when the time comes that my car is toast, well I basically need to take that vehicle back since I can’t get another vehicle loan. There was never a discussion beforehand what should happen (because we were in love and get married- we’d always be together right?). Obviously there is now some disagreement about what I would owe her when/if my car dies. I don’t want to screw her over because she is a decent person, but I need to look out for my best financial interests. What do you think is fair in a situation like this?

Fuck fair. The car is yours. Lawyer up.

2. I started deleting pictures of her from my camera- anything relating to her and her kids, I just couldn’t stand to see them anymore. I also started hiding posts that included her on Facebook and she’s already begun untagging me too. Will I look back and regret I deleted those pics years from now? What the procedure in the digital age? I remember people having hard copy pictures of their ex’s and just putting them in a shoebox up in the attic, probably never to be looked at again.

The only difference between untagging yourself in your ex’s photos and keeping them up in the attic is that the former isn’t a fire hazard. BONUS: your new love won’t see them while cleaning out the attic and be all, “Why do you still have these?”

3. Last item involves the dagger she plunged into me with this breakup. Now understand we had issues for a few months: said we’d take a break, said we’d be just friends, etc but always went back to being lovers. She finally dropped the bomb and when she did I initially resisted but agreed that this just isn’t working out for all parties involved. She said she needed space and maybe we could reconnect when she figured out what she wanted in a relationship; the typical “it’s not you, it’s me” mantra. 

There is a reason there’s no “slowly remove the Band-Aid” theory.

After really hurting for a couple hours I sent her a text and said I’m letting you go and good luck, no hard feelings. Well me being nosey I went on match to see if she was there. Well lo and behold there she is. 

Dude, knock it the fuck off.

Captured in pictures that I had taken myself and with a profile describing her perfect match exactly who I thought I was. I guess I could understand after a week goes by a profile would go up, but to have your credit card whipped out and be on there already really fucking hurt. 

GOOD. You need to get the message that SHE DOESN’T WANT YOU.

I went temporarily insane and texted her: “So you seeing someone?” 


My jealousy got the best of me. I asked her about the profile and she said she was just curious and not seeing anyone. This was the absolute last person on earth I would expect this from, completely abnormal behavior to be deceitful like that when she said she would try and be open to working on us. Unfortunately for my psyche I’m the type of person who always wants to know “why” and she never gave me a straight answer why she would do that.

Donald the Doofus

I know it hurts, but you aren’t OWED an answer. You aren’t owed anything. A break-up is a break-up and nothing more. It means only that you must now move in a new direction, and the best direction is forward. Don’t look back; you’ll get turned into a pillar of salt.


Dearest Captain of my Stone Age Condo Inhabiting Ancestors,

Fantasy First: I’ve been the Commissioner of my University Football class’ league for the past two seasons, however decided to step down this year due, in part, to the whining of a specific member of our league, but mainly to try and cut the fat off my schedule to focus on my masters thesis. 

Well la dee dah mister high education

In a moment of calculated spite towards him, the league moved to install our resident whiner as the Commissioner for the coming season. As I have happily and willfully given up my role in running the league, I hesitate to proactively contribute in order to allow the commish to find his feet and also acknowledge my new position, advising instead only upon request (offering reasons as to why a 14 – 16 man league is generally a bad idea, etc.). 

Nevertheless, when going over the scoring system, alongside the slightly QB heavy but otherwise reasonable 1pt/20 yards 5pt TD passing (rather over balanced by a -2 sack score [Tannehill’s out then]), 1pt/10yard 6pt TD rush/receiving I noticed the following bonus point setup: 

300+ passing/100+ rushing/receiving: 4 pts

400+ passing/200+ rushing/receiving: 5 pts

40+ passing/rushing/receiving TD: 4pts

50+ passing/rushing/receiving TD: 5pts

I’m sure these settings will infuriate you as much as they do me. (Brees to Graham on a 60 yard bomb: 30 points. Plus another 9 points for their respective customary 400/100 yard games. Great.) 

My question, then, is thus: how do I handle this? Do I just smile sadly and no longer take my just-pleasantly-competitive-enough league seriously? Do I step in and inform him of the idiocy of this setup that rewards arbitrary yard totals buckets of extra points, and risk being accused of stepping down but not actually stepping down? Do I get a bit underhanded and conspire with other members of the league to hide the source of criticism? 

The last option is really not my way, preferring open consultation, and I do not want to destabilise our new Commissioner… Nor do I want to no longer take my favourite league seriously. Your advice on dealing with the matter, and how to explain the stupidity of these rules, would be much appreciated. 

A league should typically have the same settings year to year. Changes to scoring and keepers should be made with the consent of the members. Being commissioner isn’t carte blanche to be fantasy dictator. And if your commish doesn’t understand that, then overthrow him: organize a new league with everyone in the league BUT him, and this time maybe don’t put the whiny shithead in charge of your league. Dummy.

Sex: I would consider myself a reasonably well experienced sexual deviant, having a love for experimenting and being blessed with enough opportunity to do so. Fisting, however, has always been one of those things I – and many of my male friends, it appears – believed to be a porn thing that never really happens in real life due to it not being especially possible or pleasant. 

However, it perchance came up in conversation with my current bedmate, who was not only surprised I’d never tried it, but then revealed she actually rather enjoyed the practice. Not one to shy away, one thing led to another later that evening and I experienced the strange sensation of having the vagina of an otherwise tiny young lady completely enclosing my wrist, my fist clenched inside of her. 


Having zero further experience of this particular sexual act, I’ve been asking my male and female friends for thoughts and advice. The males were unanimous in their surprise that this was actually possible and enjoyable. The females, to my surprise in turn, responded positively, with three saying they had tried and enjoyed being gently and carefully fisted, two declaring their intentions to try it, and two reacting in much the same way as the boys. The one difference I noticed was that the girls who thought favourably on the idea also admitted to liking the idea of being “filled up”, whereas those who disliked the idea admitted to being a bit too sensitive to imagine such an experience. 

My question is two fold: firstly, as an intrepid sex-advice mailbag operator what is your reaction to the practice? And secondly: do you have any ProTips beyond the gentle pumping and rotating I’ve managed to acquire from google? 

Yours sincerely,

Erect Dicker

I confess that fisting isn’t something I’m particularly interested in or curious about.  But, because I’m a mensch, I Googled “fisting advice” — at work, no less — and I found two thoughtful articles: the Crash Pad Blog and The Pleasure Chest both have thoughtful tips on the basics (“LUUUUUUUBE!”), execution, and finer details you might not have thought about (trim your nails, for example).

As for what other people think: fuck ’em. Do what pleases your lady. As long as everyone’s getting off and no one’s getting hurt, I’m happy for both you and your stunt-vagina girlfriend.

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