Will masturbating my anus days before penis penetration help reduce the pain? Or will it help only if done directly before anal sex?
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You really can't stretch out your anus. Masturbating it can help you learn to relax enough to let it happen and actually enjoy it. You don't want to go from never trying anything all the way to penetration from a penis. I like to use Sharpies because they don't have any sharp parts or caps on the smooth end. Just make sure you wash whatever you use first. Good luck!
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