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Some women say this combo feels overstimulating in the best way. The oil-based ones are also pretty annoying to get off afterward. You are being an awesome and selfless if butt sex is not on your list of must-have sex partner. Take any pressure to perform off yourself by trying penetrative anal sex alone first. Pain most commonly comes from anal fissures, or little tears in the tissue around the anus, which is very thin and delicate. Remember how much regular sex hurt at first for some of us? Get a toy and a condom for easier cleanup and go at your own pace.

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