Dr. Goldstein’s Guide to Anal Sex

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How do you have anal sex? Let’s get to the bottom of it…

The key to successful anal engagement requires the application of proper technique, science, and an overall understanding of what comprises the truest bottom. Is that you? Whether that’s you now or who you want to be, we can help. But before we get to the real deal, we should start at the *bottom* and work our way up.

You could say I’m really anal. I am the founder of Bespoke Surgical, which caters to gay men’s sexual health in New York and Los Angeles. Patients appreciate my frank talk about gay sex, ass prep, and the proper way to bottom. Sexperts have weighed in on all the common questions about anal, but my experience goes real deep.

Pregame Warm-up

Let’s begin with getting your booty primed and ready for action. The key is dilation, practice, and patience. Even though some of us might want to sit right down on the first penis we see, it’s critical to train your anal sphincters to accommodate, and that takes time. Your anal sphincters are muscles just like your biceps or deltoids and as such, they need periodic exercise in order to increase their flexibility and overall distensibility. This recommendation might sound like something you’d expect from your personal trainer, but practice is key. Remember, with the butt always in contraction mode, deliberate muscle relaxation is key for getting your hole into tip-top shape.

Butt Plugs 101

Invest in an anal kit with three gradual dilators. Next, use tons of lube with gentle play until you feel pressure amongst the anal sphincters. Note: Silicone lube can ruin silicone toys, so either use a condom on the toy or stick to water-based lubes. Try to consciously relax to accommodate and then slowly remove—all in one continuous motion. Re-lubricate and insert again with a similar technique of slowly in, meeting resistance, and then slowly pulling out. One should not feel pain at all and most may require this technique to be done 4-6 times before complete insertion. If it’s too much, it’s OK to end that session and then try again another day.

I instruct most clients to use the small plug for two weeks, then both the small and medium plugs for the following 2 weeks, and then finally add the large plug two weeks after that. Here are some tabú-recommended options for plugs and trainer sets. Once you’ve gotten to the point where you can accept all three sizes with ease, pat yourself on the back (or the butt) for completion of this dilation accomplishment. And now, onto the next!

Under the Sheets

Now that you have perfected dilation, the key to mutual gratification requires relaxation, good communication, lots of lube, and the proper position(s). Don’t forget to use a condom to prevent STIs. When first starting out, I recommend pre-dilating before the first show, all the way up to the large plug, not only to accomplish muscle relaxation, but also to lubricate the entire canal. The best initial position is the bottom on top, so that the bottom is in complete control. It’s much easier to dictate the depth and speed that feels comfortable. Once the bottom feels themselves opening up and there’s no longer any discomfort, feel free to switch things up—change positions, increase the depth, and adjust the speed.

Everyone’s internal map, if you will, is different, so you might find certain positions work better than others based on the length, girth, and curvature of your partner’s penis and the overall position of the bottom’s pelvis. Feel free to experiment and don’t be afraid to let your partner know what works and what doesn’t. The goal is for the both of you to get off, after all.

Stay on Top of Bottoming

Even a somewhat seasoned bottom can take a few pointers. If you are a true bottom, then the key to continued success is to not only bottom, but bottom often—doctor’s orders! Though if you are like the rest of us and it’s more of a periodic anal party, then anal dilation is key during the dry spells or downtime. Remember: the asshole is in contraction mode for almost 24 hours a day and if it is not periodically dilated, it will never be able to fully relax, especially when the demands are present. It is a “use it or lose it” muscle. So be consistent!

[Minor] Injury is Inevitable

Anyone and everyone will at some point have an injured hole—it’s bound to happen and that’s OK. Some expected injuries may be an anal tear (called a fissure), dilated or clotted veins (called external or internal hemorrhoids), and/or extra skin folds (called anal skin tags). Symptoms can include bleeding, pain, discharge, or a generalized swollen opening—none of which is pretty. The general principle, if this occurs, should be to stop anal play until fully resolved, add stool softeners, drink plenty of fluids, take Epsom salt baths, and use suppositories like Calmol 4 or Prep H.

For fissures, you’ll need a prescribed compound medicine, while for hemorrhoids, you should use steroid creams. Since we poop regularly, it may take a week or so for complete healing and sometimes there are some setbacks, which is definitely frustrating, but should be expected. It may seem simple, but it’s important to stay the course. If complications are persisting beyond two weeks, then it’s time to see a specialist. Earlier medical interventions may prevent surgical necessity. Regardless of any localized issues, a better understanding of the above mentioned will help minimize overall trauma.


The key to better bottoming is using the art and science of anal sex to subscribe to better practice. Full comprehension of anal dilation, initial penis entry, and proper positioning of anal play are essential whether you’re taking fingers, a toy, a penis, or a fist. And if your full desires have not been met yet with success, then see a gay medical specialist who truly understands not only the science of anal sex, but also harnesses the sensitivities of sexual identity.

Long live the bottom!

Related article: How to Clean for Anal Sex


Header image illustrated by Marcy Gooberman

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