It's been awhile since our last Head Games post, but that's only because it took us three months to discern right from wrong when it comes to eating ass.

Congratulations, head enthusiast; you're about to experience Head Games, a weekly column where we discuss oral sex with people from all walks of life. Whether we're covering how to connect your mouth to someone's genitals in the most pleasing way possible, or how different cultures and species blow each other, it'll be covered here, in this fellatio-friendly corner of the internet. Welcome aboard.

Eating ass is the new sex. Suddenly, the internet and my bed is awash with butt play mania, as a wave of trendy anal fetishism sweeps the nation. In fact, anal stuff is gaining so much popularity that the high-brow CDC is doing studies on it, finding that 44 percent of straight men and 36 percent of straight women say they have had anal sex in the last six months. Another academic study found that 51 percent of men and 43 percent of women who’ve had anal sex have also participated “in oral-anal sex, manual-anal sex, or anal sex toy use.”

And once the ass is in the game, it's more likely to get played. Half of straight men who’ve had anal sex, and one in ten who haven’t, report having inserted a finger up a sex partner’s butt in the previous month.

To me, it makes sense. You're down there anyway, making magic happen with your face. So why not taste a forbidden fruit of a different flavor?

But when is it okay to eat ass? According to today's devil's advocate which is also me, there are many logistical quandaries to eating ass that keep the average human from experiencing the revelatory pleasure of anilingus. Do you just dive straight in? Do you write them a proposal detailing when, where and how you'll be licking their buttholia? How do you even eat ass?

Well, young grasshopper, that's what this column is here to tell you. In the coming paragraphs, you'll learn how to approach the topic, do the damn thing, what it feels like, and what'll happen afterwards. I'm like a sexual fairy godmother, I know.

The pre-game

When it comes to sex and slobbering butt, there's always a throbbing-hard case for spontaneity. There's something so smoldering hot about being in the moment and just going for it. Having someone do that to you is pretty much them saying they can't get enough of you; they want your whole body. They can't even bother to control themselves to the point that they enact the common social decency of asking first.

Plus, think about how awkward planning something like that would be. "I'm gonna eat your ass at 9 p.m. on Tuesday providing you've given your written consent on this release form. Please make all the poop go away beforehand."(It's actually not very awkward, but we'll get to that later.)

You see, people are very butt-sensitive. You can really only be spontaneous if you're 100% sure your partner won't dropkick your esophagus.

Rim jobs exist in this weird space between being more invasive than oral sex, but less so than fucking, so it can be difficult to know when to talk about it and when to just go for it.

The first thing you have to consider with that is gender.

Most girls won't object to you running a tongue over their assholes while you're going down on them. There's less poop-fear for girls than guys; girls already take a neurotic amount of care grooming and cleaning their various southern holes, so it's likely that if she's keeping her pussy clean and tidy enough to fuck you, she's doing the same with her butt. Of course there's an entirely different preparatory process for penetrative butt sex, but we're not talking about that right now because this is a god damn head column.

Also, if you do this to most girls, it's no sweat off their backs. They'll brush it off, wiggle away, and forget about it. Girls are used to people mistaking their butts for their vaginas, and you're probably not the first or even fifth person to try that. It's not going to ruin her weekend.

Men are different story. Poor men and their societally-mandated homo fear complex. Although a good portion of dudes are totally down for rimming and even prostate massage, you have to tread lightly around them at first because you never know which ones had a thing happen to them in third grade, or which ones ascribe to the mistaken belief that butt play = homosexuality. You and I know it doesn't, but you never know who has deep seeded anxieties about those things.

Many men have butt aesthetic anxiety too. A lot of them are insecure about the Amazon rainforest lives in their ass crack, and don't want to nauseate you with the sheer density of anal hair they have. They're worried it'll smell like a thousand rotting bodies, and they're never sure if any poop got caught in their butt bush. All valid points, but what most men don't realize is that if they've got a partner willing to play with their butts, they've already considered those factors and decided they give no fucks. As long as it's as clean as it can be, no chick or dude is going to expect it to be a pristine virgin landscape.

That's why unless you're sure he's down, always talk about it with a guy before you do it.

Talking about it doesn't have to be robotic or clinical; it can be as simple as turning to your future partner in anal adventuring and casually saying, "What do you think about eating ass?" Or, "If you kind of licked my ass when you were going down on me, I wouldn't be bummed." Or, "It turns me on so much to think about you doing that." Even "I'll pay your rent for a month" should do the trick.

If they're not down, don't push it. If they are, congratulations, because they're probably going to come in your hair. Moving on.


Whatever approach you take to eating ass, start out light and gentle. Relax your tongue, and gently, slowly lick. Alternate between up and down and side to side. Do a circle. Draw a cloud. Sign your name. You're the Bob Ross of anal oral.

Depending on how they respond to that, you can start to flick your tongue quicker. Use your lips to kiss it.

Some people might respond to the vulnerability of you pulling their cheeks apart so they feel a stretch in their ass (probably cool it on that if you're with a guy and it's his first time). If you do, you can spit into their anus, and grab their cheeks, massaging them. They'll feel like you're really into their butt and they'll get a self-confidence boner. Great job.

If you're both into it, poke your tongue ever so slightly into it. The guise of penetration, even at such a superficial level, can be insanely hot.

Take things to pro-level by using your finger to gently massage it, making sure it's wet with salvia first. Do with your finger what you'd do with your tongue (a combo of light strokes, circles, gently pushing in), then alternate finger and mouth.

If you're as badass as that barbed wire bicep tattoo advertises you to be, use whatever free body part you have to stimulate their dick or pussy or dick-clit. Run your hands up and down their legs and torso. Lick from their ass, across their taint, to their genitals and back.

Everyone's butt is different, and has varying concentrations and potencies of nerve endings. You might find that some people go particularly insane for the area right around their actual anus, while others sexually black out when you stimulate the inner ring of it.

Experiment with different pressures and relaxation levels of your tongue, and different ways of either gently or aggressively handling it. Try to pay as much attention as you can to how they react.

What to expect

Giving: Any good butthole has a little hair around it. It's hard as fuck to shave the delicate contours of the anal region, but you might find that some people have gone to greater lengths than others to annihilate their ass forests. If they've cleaned up right, there should be no taste. It should taste like skin and your own saliva and it'll feel ridgey and smooth.You'll have to kind of spread their cheeks apart to get full on mouth-to-anus contact.

You'll probably also feel really turned on. With anilingus, if you get off on control dynamics, it's the perfectly complex sexual scenario for you. The giver is either in control and therefore dominant because they're the ones doling out pleasure, but it can also be a really submissive position to be in. You are, in a way, acting like human toilet paper, and for some people, that's the best thing they've heard all day.

Receiving: Depending on how many pleasurable nerve endings are around your anus and whether or not you were able to emotionally overcome that thing that happened in third grade, getting your ass eaten out can feel like eight million fireworks going off (in a good way, not in a Pearl Harbor Way), or it can feel like nothing more than wetness. For most people, the texture of another person's tongue combined with the silkiness of their saliva will feel great. The longer they do it, the more near-orgasmic it'll feel. The vulnerability and selflessness on the part of the giver of will make you feel like you won life.

The aftermath

Rimming is a great foray into penetrative butt sex. Getting the anal nerve endings all pleasurably worked up can both relax the exterior anal sphincter and make penetration feel much better.

Or, not. Rimming doesn't have to be a gateway drug to anal at all. It can simply be an extra flourish when you're giving or getting head. It can be an add-on to fingering or a hand job. It can be what the third person in your threesome is doing. It can be whatever you want it to. Reach for the stars.

So, back to the question posed at the beginning of this article: when is it okay to eat ass? Just about anytime you know what you're getting yourself into. But not after Indian food.

And now, I'd like to leave you with an musical homage to butts to get you excited about licking all up in them. Thank you.