Anal sex basics

Q: My only experience with anal sex was a long time ago, and it was very uncomfortable. I would like to try again, and my partner is on board. What can we do to make things more enjoyable this time around?


Hi lovely! Sexual activities tend to come with varying degrees of difficulty - just think about the difference between an orgy and a blow job. For lots of folks, anal sex ranks fairly high on the perceived challenge scale, but that doesn’t mean it’s not worth the effort - it just takes a little more preparation. And when it comes to anal sex, preparation isn’t just a good idea - it’s a necessity. Thankfully, there are a lot of ways to go about it. If the person on the receiving end is new to butt play, there’s a very good chance that you won’t even get to the main event (whether that’s a dildo or a dick) until you’ve gone through a few warm up sessions. So where do you start? 

The first rule of butt club is lube, lube, and more lube. Unlike vaginas, buttholes are not self-lubricating, so it doesn’t matter how turned on you are - you’re going to need some assistance. This is true for any type of anal play, not just penetration. The kind of lube you should use is dependent on a few things. For fingers, tongues, and un-condomed penises, as well as toys made out of glass or stainless steel, I recommend a glycerin-free silicone lube or organic coconut oil. If you are using silicone anal toys or wearing a condom or glove (yay safer sex!), then a water-based lubricant is best, since silicone and oil can wear down both latex and silicone toys. You might need to try a few brands to determine what’s ideal for you and your partner. Just steer clear of any lube with a numbing agent in it - really, for any sexual activity, but especially for anal penetration. It might sound appealing to minimize discomfort, but pain is your body’s way of indicating that you need to slow down or stop, and it’s important to listen.

Once you have the right lube, start small and work your way up. Fingers and tongues are perfect for external stimulation, and a pinkie finger or toy can be inserted at your partner’s request. Toys are especially great for warming up to anal sex, since they can loosen your anus over time, making penetration with a penis or dildo more pleasurable. (And don’t worry - it won’t stay permanently stretched!) There are various shapes and sizes of butt plugs and anal beads, so like with lube, you might need to try a few until you get the right one. Silicone, glass, and stainless steel are high-quality, non-porous, and easy to clean, making them the best toy materials. If you decide to try anal beads, make sure that the connecting portions are made of the same material as the actual beads, not something like nylon string, as that shit (no pun intended) is impossible to clean. The main thing to keep in mind when it comes to anal toys is that you MUST use something with a flared base (meaning the base of the toy is wider than the insertable portion). It may not seem likely, but the mechanisms of your sphincter are such that they can suck a toy right into your body, and nothing kills the mood like a trip to the ER. The good news is that anything marketed as a butt plug or beads will already have this design.

Now that you’ve got the mechanics down, it’s time to set the scene. Anal sex is best when you’re both feeling clean and relaxed, so share a bubble bath or steamy shower before you get going. It’s awesome to be excited, but don’t forget foreplay just because your plans are ass-focused. Sex and relationship writer Charyn Pfeuffer says that the best anal sex she had was when her partner was willing to explore and go super slow: “My partner paid a lot of slow attention to my ass and anus before penetrating me. I was used to partners going from getting me on all fours to balls deep in 2.2 seconds, so I didn’t realize how pleasurable it would be for me if anal sex was slowed down and we took a more holistic approach to pleasure.” So incorporate making out, hand jobs, oral sex, vibrators - whatever you would normally include to get each other hot and bothered. Find the position that works best for both of you. Sometimes the person receiving prefers to be on their knees or stomach - this can work especially well if they’re using a vibrator for added stimulation. Sometimes it’s better on their back with their legs in the air. A good way for the receiver to have more control is to let them back into the penis or toy, so that they can better determine the speed of penetration. 

So take a deep breath, then match your breath to your partner’s - slowly in through your nose and out through your mouth. Let your mind and your body relax. Keep it playful and exploratory. Know that anal orgasms are great (and yes, everyone can have them!) but they’re not a requirement for a good time. Now go have fun - you’ve got this!


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