"Getting the tip in hurts the most, because the head of the p..." — Anna Breslaw

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Getting the tip in hurts the most, because the head of the penis is the widest part. Once you're past that and up to the shaft, it'll feel a little better. Remember how much regular sex hurt at first, for some of us?

— Anna Breslaw

A Complete Beginner's Guide to Anal Sex

Anal Sex Pain penis

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