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Having Problems Bottoming? 

If you are unable to enjoy anal intercourse, there could be a few factors at play. When bottoming hurts, it could be that your anus is anatomically too tight or you are unable to relax, which is oftentimes a psychological response. Many people have had negative bottoming experiences in the past or simply have a fear of the unknown, rendering them unable to relax their anus and enjoy safe and pain-free anal intercourse. Some people are simply tighter than others — and some penises are larger than others — which can make anal intercourse more painful. 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. 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 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.