Doing The Deed
If you take nothing else away from this portion of the proceedings, let it be this: Start slowly. Make sure your partner is comfortable. 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!)
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.)