Over the past several weeks, we’ve had a number of questions regarding anal pegging. How do I ask my partner about it? What should I do to prepare for it? How do I even do it? We’re here to give you some advice that you can use to begin your ass play journey.

When it comes to approaching your partner, our advice is don’t be shy—you should feel comfortable asking for what you want. If they’re not into the idea, that’s alright! It is just important that neither party is weird and judgemental about what the other wants. Communication is truly crucial from start to finish, and everywhere in between. None of this will be fun if either of you aren’t continually communicating.

You mentioned concerns about cleanliness. Luckily, John has the cleanest asshole on 34th Street and is here to help. First, he recommends supplementing your diet with fiber and plenty of water to try to maximize the regularity and ease of your bowel movements. If you feel like you’d still benefit from some extra cleaning, you can buy an anal douche. They’re fairly simple to use once you get the hang of it, but don’t forget that the microorganisms in our gut and butt are good for us, and excessive flushing is asking for trouble. As Jonathan Groff wisely states in the Netflix original, Mind Hunter, “If you want truffles, you’ve got to get in the dirt with the pigs.” Your prostate is a truffle, dear reader.

For further advice, we turned to Lauren, a manager at Pleasure Chest on 20th and Walnut. Before penetration, she emphasizes lube lube lube! Specifically water–based lube—it won’t stain your sheets, leave a mess, or destroy your silicone toys like a silicon–based lube. Additionally, while numbing lube might seem like a good idea, it’s not. It’s like having novacaine for oral surgery, and not realizing you bit your tongue until it’s absolutely killing a few hours later. Listen to your rectum’s pain receptors!

When it comes to the toy, Lauren urges ass–novices to work their way up to the Big Kid Dildos. First, try a finger, maybe two, to get comfortable relaxing your sphincter. Then, go for a small toy. There are models made for this that are slim enough for easy penetration and have a bulbed top specifically for prostate stimulation. There is a gradient of toys, and you can work your way up at your own pace. When you’re first getting used to anal penetration, make sure to take it slow, breathe, relax your ass, and check in with your partner frequently. One unpleasant penetrative experience can create negative associations that might keep you from knowing true pleasure in the future. 

We’ve tried to provide you with the basics here, but the best thing to do if you have any tailored or particular questions is to head on over to a place like Pleasure Chest and ask them yourself. They are the non–judgmental and omniscient sexperts, and not to mention a damn delight to talk to. If you feel awkward asking about pegging for yourself, lie and say you’re writing a sex column for a campus magazine—we’re pretty sure that that’s what the folks at Pleasure Chest thought we were doing anyway.


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