Welcome louche libertines to the latest installment of the mailbag for the anally adventurous and the roving of eye. This week, we entertain a few more questions than normal because brevity be damned. Sometime the load must be blown. The usual spate of anal curious male has given way to one dealing with rectally trepidatious gent. I feel your pain, Amanda. Be sure to send your address (or, you know, same goes to people with questions for future editions) here.

Let’s get it on.

Dear KSK,

Sorry for the length of this question, but my question is, what kind of line do you draw here when it comes to an ex that she’s been friends with for a long time and with whom she’s had a child? To me, it should be strictly professional if you have to see him due to a kid. You can’t have your cake and eat it too if you’re going to get into a relationship with someone else. Hanging out with him or even having personal phone conversations where you share things doesn’t seem like what you should be doing when in a serious relationship. You agree, or am I being unrealistic? I’ve never dealt with a situation like this before.

I understand your anxiety, but she obviously has a different situation with this ex than you have with yours. It seems like she’s being very upfront with you about what’s doing. For the sake of this kid, they want to keep something of a decent relationship going. I think you can be a little less unyielding in this regard.

Football question: Does Buffalo automatically make Terrell Owens fantasy poison, similar to Randy Moss in Oakland?

Steve

See, I wouldn’t have said so up until the Jason Peters trade. Signing Terrell Owens for a year has all the makings of a last-ditch effort to make a playoff run. So what did the Bills do a few weeks later? Trade their starting left tackle to Philly for draft picks. Makes no sense. Therefore, I’m inclined to believe it’ll be a disaster. At least, even more of one than it was already destined to be.

Dear sir or madam:

My rather mundane request is for any good ways to ask this chick to prom. She’s Italian (as in foreign) and I’m looking for some ins with the mafia.

Try this: “Ragazza, ti prego, vieni con me alla prom”

/puts years of pointless Italian instruction to use.

Either that or gel the fuck out of your hair and wear tight-ass jeans. Those Eyetie women seem to go nuts for that.

Dear Gayest of all Mafias,

As Jesus once said, football first. I am the commissioner of a ten team league, consisting of close friends and family members. My cousin Lee (he reads this site) has not paid the $100 in two years. I was not aware of this until two weeks ago. Before everyone calls me a shitty commissioner, which I am, he is married and does not come to the end of the year drink fest, his brother has won the last two years, and he always said he would get Lee to pay him. I find out last week and am upset. Isn’t this clear grounds for kicking him out of the league, despite him being family?

Ab-so-fucking-lutely. Fantasy sports are one of the treasured forums in life where you can completely fuck over family relatively free of consequence.

Sex: I have liked this girl for many years, but before I knew what happened I was in the “friend zone.” I usually had a steady string of girlfriends I liked and after a while I stopped thinking of her “that way.” But, recently I was dumped by my girlfriend of two years when she rejected my marriage proposal. My female friend also just got dumped. Hard. While I know I will never be with her in a relationship, I most certainly can fuck her right now. No matter how good the sex is, will this be torture for me after?

Yes to One No to Two,
Kyle

You’re both decisively on the rebound, so the opportunity is likely there. Without context, I’m not sure why you believe a relationship with friend girl is out of the question, but you’d have to weigh how valuable a friend she is before deciding to move in for a hook up. Because her potentially shooting you down could have the same effect or be a huge ego slam to boost.

Dear exalted sex-experts,

The revenge fuck was awesome & we ended up fucking each other senseless for pretty much the entire summer. Not only was she hot as all fuck but that polite, quiet & sweet girl was an absolute animal in the sack, just a totally pornographic little pervert. The whole thing was clandestine & on the QT but it got to a point where we were talking about running away together & all that shit.

Not that you’re not bragging about it or anything.

But the summer ended & cooler heads prevailed, she got back together with my friend & they ended up settling down together. At the time I was a deviant criminal-minded narcotics salesman while he was attending business school blah blah blah so I can’t really blame her & I never did. We all remained friends & she & I just kept it to ourselves. I see them all the time & it’s all been cool. We’ve flirted here & there but otherwise I just assumed it was dead & buried a long time ago.

Sincerely,
Satan’s Hand Puppet, NJ

You know, I see the fucking deluge of ampersands in your letter and I immediately think of the capuchin monkey from Y: The Last Man.

And yet I’m the one writing the sex advice column. Veddy bemusing.

Anynerd, you also forgot D) SHE WORKS WITH YOU! Therefore you stand to royally fuck up personal, social AND professional life for a woman you admittedly don’t have long-term prospects with. My recommendation is to revert her to the spank bank and maintain a semblance of order in your life.

That is, unless you want to get back into the drug-pushing game, in which case be a dear and sell me some weed. All my connects dried up.

I have a few close friends who are complete lesbian lovers and this is how it works: there are two schools…

That, my friend, is your answer.

I’ll let you know which one I see more Caps fans doing at the Verizon Center this weekend and report my findings.

Dear Rainbow Butt Monkeys,

Full disclosure, I’m Indian. But no arranged wife, not even Indian, she’s Irish and nowhere near subservient enough.

Nor sober

Sex Question: She’s four months pregnant and I’m worried about having sex now. Are there positions I should avoid? Maybe suggest anal? But then again I wonder if a baby can feel the psychic pain of a plowed rectum. What do you think?

Not unless she plans on shitting the kid out. If that’s the case, buy a Browns jersey now. Otherwise, you should be fine with the ol’ missionary in-and-out.

Football Question: So I’m from Boston. An Indian with a Boston accent (you want a fackin’ Slurpee?) So clearly I’m an awesome sports fan and did masturbate to the thought of Papelbon running the Wildcat. Do you think Patrick Chung will be subjected to hazing that includes doing the dry cleaning of the veterans and endless Happy Ending jokes? And will he get out of the huddle, run a circle around it and then get back in?

Raghead

Nah. None of that. Though Belichick may make him his eunuch.

Hey Douches,

Football first: Did the Cowboys royally fuck up the draft, or did JJ actually make the right move by deferring to the later rounds in a talent thin suckfest?

It was a pretty weak draft at the high end. And I’ve heard reports that the players they were looking at in the 2nd were off the board right before their pick, so that made some sense. Considering how much they overpaid for Roy Williams, it couldn’t hurt to get a few more picks.

Sex: I’ve been fucking this girl who’s a veritable minx in the sack, she loves anal, gives toe-curling blowjobs, loves porn, great tits, nicely manicured snatch etc. My only problem is that our sexual escapades seem to revolve around cocaine. She loves doing blow (who doesn’t?) and every time we get together, she wants to do lines. I have a few problems with this, not the least of which is the cost of these evenings, and the fact that we’re typically up all night and I’m cored out and useless for a couple of days afterwards. What the fuck? Is this just the cost of doing business?

Fucking Elvira Hancock

Maj: “God gave us Xanax for a reason.”

How’s this for brevity, sir(s)?

Sex: I just started going out with a woman that I have been really close friends with for the past four years. What is the maximum number of dates we can go on, without engaging in any sort of physical contact, before I must accept the fact that I am stuck with a really good friend that just so happens to possess a vagina? The second date is this week.

Football: Should I be encouraged by the fact that the Eagles finally realized that their top priority should be to get McNabb some offensive help, or discouraged because it took them nearly a decade to figure that out?

Thank you for all the free entertainment you provide me with, each week – it really helps me get through the insanity that consumes my workday. Do you gentlemen have some sort of donation PayPal account available, which I am apparently too dumb to find? Or, at the very least, is there a P.O. Box set up so that I can send this token of my esteem to BDD:

P.S. I apologize if that last part veered off the brevity path.

Signed,
Reggie20×6

The Eagles got them another rookie receiver, running back and a Pro Bowl left tackle. All signs point to Donovan McNabb preseason career-ending injury.

Gayest of Mafia:

ANYway, this was months ago now, and she hasn’t brought it up again. I’m not sure she’s forgotten, but I’m still not fucking two chicks, so something went awry. My question: how do I get her to make this fantasy a reality without expressly saying “Hey, how about you go get me some other hot chick to bang?”

Should have showed more initiative when she first posited the menage, but then I’m not adroit at avoiding female relationship traps.

Football: How do you think Moreno will fare in Denver?

Disappointed in Denver

Probably not as well as he would have faced if the Broncos didn’t have a quarterback opposing defenses could line eight in the box against.

Hello there,

1. I notice a lot of emphasis on anal sex in this column. Here is my issue: I love anal sex and want it all the time, however, my boyfriend has no desire to engage in this act. I’ve even gone as far as to climb on top of him and try to do it myself. At that point, he tells me to stop, I get pissed off and have no desire to do anything further. This gets better though – the other week, I went on his computer and saw him downloading shemale porn. What kind of a guy downloads shemale porn but doesn’t want to do what what in the butt? Of course, when I asked him about it, he told me he must have clicked on it accidentally. Accidentally? You accidentally downloaded a movie called Shemale Sex Party? Right. Anywho, what should I do? Should I dump this guy and find someone who will do it how I want? Should I just ram a dildo up my ass instead? Help!

Dumb the shemale lover and prepare to get stalked by 20,000 other guys who read this site. Or head on down Christmas Ape Way.

2. I think I may have just answered my own question, but, is there anyone in the free world who actually likes the New York Jets? Shemale Porn Lover (mentioned above) does…and I’m wondering if this is one more reason to cut my losses and find someone else.

Amanda

He’s saving himself for Johnny Damon Mark Sanchez.

Punter: “Seriously, the Jets have been a homo team since their inception. No one denies this.”

Dear Flip-Flop Fanatics,

Ok, first the football: Do you think the Giants’ receiving core, as currently constructed, can take enough pressure off of the running game to restore balance to the offense (you know, now that we don’t have what’s-his-name around anymore)?

No.

If so, do you see a return trip to the Super Bowl this year?

Nicks isn’t gonna solve shit in his rookie season, but it’s still entirely possible for the Giants to make it to Miami next February. The NFC looks to be fairly wide open in ‘09.

Now, sex: If this gonna be that kind of party, should I stick my dick in the mashed potatoes?

Warm Regards,
Moishe Alou

Only if you do it first.

Attention Chris Mortensens of Cock,

Football: I want to wager on football games online, but don’t know what sites are legit. I have no access to bookie / casino.

Quitcher bitching.

Maj: “I’d just recommend Bodog. They’re easy to use, but they can be difficult if you try to withdraw large sums. So go with Bodog, but if you start winning make frequent withdraws in smaller amounts (a few hundred at a time).”

Also make sure to have multiple credit cards, as I was using my sole debit card and my banked blocked that shit from depositing in my Bodog account. Another reason we need to let banks fail and stuff all our money in a mattress.

Sex: I like to do facials on wife, but she refuses. What to do?

-AG

That’s a tough one, as it is pretty humiliating and most women would give anal a shot before facials. If it means that much to you, try on a whore. Or do it to the wife once and deal with a year without sex.

Dear Cum Dumpsters (and I mean that in the most endearing way possible),

Andy

Drew: “Jesus brutha, we can’t even tolerate Ape in his non-native environment.”

WE’RE FROM THE TOWN WITH THE GREAT FOOTBALL TEAM
BOM BOM BOM BOM
WE CHEER THE PICKSBURGH STILLERS

Have fun, buddy.

Also, my downfall last draft was drafting the same players as in my championship team the year before. Needless to say I came in last. Who is a good, solid, middle of the first round pick who I can lead off my revamped team with?

Hard to say to without knowing how many teams are in your league, but if Slaton falls to you, take him.

Dear Seamen of the great Lake: NFL knowledge,

Are we doing some Gilbert and Sullivan shit?

Football first: I’m some sort of sad hack who’s studying to become a journalist in Britain. I maintain a huge interest in the NFL and wanted to ask your opinions on the NFL draft for a project I’m doing. Basically who did the best? The worst (Raiders don’t count they didn’t draft, they simply chucked darts at a wall and took whichever name they hit)? Steals and reaches? Anything along those lines basically.

So many people base draft grades on the first two rounds, because it’s players they recognize. In reality, it’s a pointless venture and we won’t know for sure for years. That said, people seem to think the Giants, Bills and Patriots (stockpiling 2010 2nd rounders ftw!) had a good showing. Despite misgivings about character issues, shockingly enough I think the Bengals had a pretty decent draft as well.

Sex: I’ve been with a girl for the last 5 months and the subject of earning a brown belt has turned up. In fact we’ve even given it one go on a drunken night, but thing is, it was too painful for her. She’s a dirty little girl and wants to give it another go, but wants some way to “loosen things up” as it were. And no, not in the X-lax sense. Any suggestions on how to make it slightly less painful, more enjoyable for her?

Deuchars is the Best

Ever tried a giant bottle of lubbbeeee?

Connoisseurs of Cock,

Bathroom Jack

Ufford: “Completely pathetic kinda says it all right there.”

Domestic work must rate highly for you if you’re willing to overlook constant blue balls for the sake of having clean kitchen tiles. That said, you’re not married to this girl yet, however much she wants to act like it, so there’s still time to threaten to leave if she doesn’t get her libido together. Because it’s only getting worse if you go ahead as planned.

Peyton won’t be entering the season injured this year (presumably, though one can hope) so I’d say he’s still among the top fantasy QBs, though possibly no longer a late first round fantasy draft pick. Even when Addai is healthy for a full year, he only gets about 250 carries. Brown may work out as a good counter, but Addai should still put up similar numbers, though I’d say he’s at the back half of the top 20 overall.

Sex: The girl I’m currently fucking around with is not very good looking. She’s chubby and usually dresses bummy (sweats and a t-shirt). I still like her a lot because she’s not insane, very low maintenance, unselfish, good sense of humor, and also a sports fan. I feel like a dick because I never bring her around my friends. She has brought it up jokingly a few times that I’m embarrassed to show her off, which I am. So, do I bring her around and fuck if my friends give me shit or do I just continue keeping her away from them?

So I’m assuming all your friends are banging super models. Fuck those twatwaffles if you like the girl.

Football: I need 6 keepers – regular fantasy league statistics and starters (+ 2 rb/wr/te spots) and I don’t drop or lose any picks no matter who I decide to keep. We have individual defenders (TK=1 pt, sack=3, ForFumble/RecFumble=4, Def TD=6).

Here are the guys I am considering keeping: McNabb, Tomlinson, McFadden, Thomas Jones, Sproles, Cooley, Greg Jennings, Jon Beason, Karlos Dansby. I’m also being offered Larry Johnson for the 11th overall pick, so that would mean I would only get to keep 5 of these – I don’t think it’s worth it.

It most certainly is not.

Also: How early would you draft Mark Sanchez in a keeper league (regular settings and statistics, 12 team league)?

- Lil’ Wayne Chrebet

No earlier than the seventh round, you shemale porn lover.