Anal play, as you likely well know by now, is having its moment. Hell, even Vogue is writing about it, and Harvard is, like, teaching classes about the basics of butt-banging. But we can't all go to Harvard (and thank God for that), which means that the 101-type stuff that a lot of curious folks might benefit from isn't readily available. We thought we'd fix that.

Broaching The Subject

The fact that doing it in the butt is all over the news is great for those among us who maybe want to try it but maybe haven't tried it, and maybe haven't the foggiest notion of how to bring it up to their partner. This presumes, of course, that you're a person who wants to demonstrate that you're a bit more smooth than a simple, "Hey babe? Wanna do it up the butt?" would indicate. In which case, use the news as a hook. "Hey babe? Did you see that article in Vogue about anal sex? I thought it was interesting—any chance that's something you're up for trying?" And, look, if the answer is no? Drop it. Don't be the guy who whines and wheedles his way into backdoor action. Or worse: The guy who sneak-attacks his lady. Do not sneak-attack us with your wang. If you sneak-attack us with your wang, it seems fair that we should be able to sneak-attack your wang with a machete in response.

Gettin' Ready

If you will be receiving, there are a few preparatory acts you might want to perform. If you'll be doing the giving, it's not a bad idea to take a look at these tips anyway so that, if need be, you can offer them to your partner.

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The first is rather obvious, but still worth stating: Go sit on the pot and clear your bowels. You may also want to wash; a washcloth and mild soap are best for this, and employing your fingers to clear debris out of your butthole is also suggested. Somewhat related to this: Avoid foods that tend to cause gastric distress.

Some people chose to perform an enema to clear their pipes; if you go that route, here are a few best practices:

  • Perform the enema a few hours before anal sex.
  • Swap out the enema solution for plain warm water.
  • Don't hold the water in you, which is suggested when using an enema to treat constipation, but can lead to accidents later.
  • Don't overdo it.

Using condoms will help to make cleanup easier and is absolutely recommended for partners who are not exclusive to ensure that your sexually health remains, well, healthy.

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Regardless of whether or not you use a condom, lube is an absolute must, because the anus doesn't produce natural lubrication the way a vagina does. It's also worth trying out a few different kinds of lube to find the one you like best—many brands offer sample-sized packages of lube, often free of charge, which are great for experimenting. If there's a sex shop in your area, definitely ask if they offer free samples or sell individual-use packages. Asking (or, let's be honest, Googling) for recommendations is a good idea, too, but remember that the choice of lube is a very personal and individual thing, so take recs with a grain of salt. Some people will swear up, down, and sideways that Astroglide is far, far superior to, say, KY Jelly, while others vastly prefer the latter over the former. And on and on and on with all the other options out there.

In terms of applying the lube, fingers work quite nicely and can also serve to warm the area up, so to speak, for the larger insertion that's about to come. If you're finding that the lube is making a mess of your sheets and such (we'll talk more about clean-up soon), a Lube Shooter Lubricant Delivery Device (yes) (I have gone to some dark, dark places on the internet in service of bringing you this information) is a thing that exists in this world to address that very problem.

Doing The Deed

Go slow.

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If you take nothing else away from this portion of the proceedings, let it be this: Start slowly. Make sure your partner is comfortable. Anal sex shouldn't be excruciatingly painful, or even mildly painful. It might be a bit uncomfortable at first, and that is normal, but there shouldn't be any significant unpleasantness involved. Once insertion is complete, you can start picking up speed, but be really (really, really, really) sure throughout to stay extra (extra, extra, extra) aware of how your partner is doing.

In terms of managing both pleasure and pain, try out different positions. Oh, sure, there are a bunch of them! Most people think of doggystyle, which is quite common, but there's also bottom-flat-on-stomach, and good old missionary. This illustrated guide to 20 different anal sex positions is pretty nifty, so have a looksee through that for more ideas. (NSFW, obvs!) (Editor's note: Do not attempt the position depicted in the photo.)

And finally, even if you and your bottom are seasoned pros, on some occasions, anal might just not be in the cards. For whatever reasons, there may be times when it just hurts—you should know that that happens and be ready to move on to an alternate act if and when that is the case.

Finishing Up

This is among the more important pieces of information I can provide, so do whatever you need to do to commit it to memory: When it's time to finish, don't assume it's okay to do inside of your partner. That's probably true of all sexual acts (R-E-S-P-E-C-T), but it's especially important with backdoor play, because semen can have a laxative effect, which can lead to accidents. (If you're using a condom, this advice is non-applicable for obvious reasons.)

The Aftermath

Speaking of condoms! If you've used one, you should be ready for it to come out looking a little poopy. It might not! But you should anticipate that it will, and do that whole "expect the best, but prepare for the worst" thing. If the idea of that doesn't make you flinch, great. You're fine; bang away. If the thought of a shit-stained used condom makes you want to die, though, consider using a black rubber. Lifestyles makes them, and probably a few other brands too. (Got a fave? By all means tell us!)

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The mention of that condom brings us nicely back to the promised discussion of cleanup.

I mentioned the lube shooter, which can help to cut down on the amount of mess caused by lube. But if you do find yourself with a set of lube-stained sheets, here's some info for you, courtesy of me, writing in Redbook. (I know! Redbook, who knew?)

Personal lubricants can enhance solo and partnered sex, but can also create a huge mess. Water-based lube stains should come out with regular laundering, but to be on the safe side, it's not a bad idea to use a stain treatment product if you've got one. Silicone-based lubricants are trickier, so bear that in mind when making purchasing decisions. If you do find yourself with a silicone-based lube stain on your sheets or clothing, try to treat it as soon as you can, as fresher stains will be more likely to come out than set-in ones. As for what to treat those stains with? Citrus degreasers are one good choice, as are carburetor treatment products. Yes, we're serious.

If backdoor play leads to leakage or an out-and-out accident, first and foremost, remain composed. Shit, as they say, happens. And you should know going in that shit happening is a very real possibility with anal, so if you can't handle it if shit does happen, maybe anal isn't the sexual act for you. That is okay! Just know and be honest with yourself so you don't wind up making someone feel bad and gross. (I'm sorry that I even need to say this, but, you know, people are terrible: Don't make someone feel bad and gross before, during, or after a sex act, unless that's part of the sex act, and they've requested and consented to being made to feel bad and gross.)

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Small messes can be spot-cleaned. Here, dish soap and a sponge (but not the one you use to do dishes, because poop!) are really all you need to execute a quick cleanup. If you don't clean up the staining immediately, hit it with a laundry pre-treatment product like Zout before laundering. Borax is another product that is swell at eliminating fecal stains—in the event that you wind up with a bigger mess to clean up, go ahead and soak the sheets in hot water and a quarter-cup or so of Borax before laundering to help remove the stains.

Now let's get out there and fuck some butts.

Background and further reading [NSFW]:
Porn Star Aurora Jolie's Sex Etiquette
Unzipped: The Proper Etiquette of Anal Sex
How to Avoid a Shitty Bottom: Anal Sex Etiquette


Jolie Kerr is the author of the book My Boyfriend Barfed in My Handbag … And Other Things You Can't Ask Martha (Plume); she can be found on Twitter, Kinja, and Tumblr.

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Image by Jim Cooke.

Adequate Man is Deadspin's new self-improvement blog, dedicated to making you just good enough at everything. Suggestions for future topics are welcome below.