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For either problem, I suggest trying dilators. Available in medical supply stores, dilators provide a safe and secure way to become more comfortable with anal sex. Start small, leave the dilator in place for 10 minutes three times a day, and use the same size for a week. Increase to the next size on a weekly basis until you reach the size of your partner’s penis.

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After foreplay, lubricate the outside of the anus and your partner’s penis. It’s important not to stimulate the bottom’s penis while attempting penetration. During penetration, if the bottom’s penis is stimulated, he is likely to experience the bulbocavernosus reflex, or the involuntary contraction of the anal sphincters. This reflex is more pronounced in uncircumcised men, and will make bottoming more painful and difficult. If for any reason anal sex remains painful or you notice the appearance of lumps, bleeding, or an ongoing itch, see a healthcare professional immediately for a thorough anorectal examination. Find Bottom Friendly Medical Support If your anus is too tightly contracted when you are first penetrated, you’ll run the risk of tearing skin or damaging your sphincter. That’s why it’s important to relax your anus before penetration using various foreplay techniques and to keep your anus relaxed and well-lubricated while bottoming. Richel, O., De Vries, H. J. C., Dijkgraaf, M. G. W., Van Noesel, C. J. M. & Prins, J. M. Risk Factors for the Presence of Anal Intraepithelial Neoplasia in HIV+ Men Who Have Sex with Men. PLoS ONE 8, e84030 (2013).

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Next, start with something smaller than a plug: Lube up your finger, or ask your partner if you can borrow theirs. Circle the anus with the finger, glide it gently in and out of the anus, then add another finger.

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Dilators help with psychological fears by preparing you more for what to expect, giving you total control over your body, and erasing any fear or embarrassment in the eyes of a partner. Physically, they allow the sphincter to accommodate a penis over time and should help bottoming get easier Rimming can provide some lubrication and helps the anus relax before sex. That said, rimming can put both partners at risk for STIs, so be careful. Dental dams may be used as a protective barrier to minimize the risk of infection, but can obviously be awkward to use.

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If you have a vagina, the butt plug is also a wonderful way to experience double penetration: Slide one in after applying lube and wear it during vaginal sex with a penis or dildo. You can also simultaneously stimulate your clit with fingers or a vibrator. Many people love receiving oral while they have a butt plug in. That said, you don't need a partner to enjoy butt plugs — they make for excellent masturbation companions. In fact, solo sex is a lovely way to explore anal play. The bottom line is that anal pleasure through butt plugs is something anyone can enjoy. What should I know about lube? It’s also helpful to consistently eat a high fiber diet that includes foods such as whole grains, broccoli, and beans — as this regulates bowel movements and decreases the likelihood of soiling during sex. Fiber helps bulk up stool and decreases liquidity, further minimizing the chance of a mess. In general, men should consume 30-40 grams of fiber per day, and women should consume 25-30 grams of fiber per day.