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I don't have to start as slowly anymore, usually, unless it has been a very long time. This is where lube comes in. Here's their advice for taking the stress out of first-time anal sex. It also depends on the size of his manhood. The whole point of anal play is to keep it simple before working your way up. Either way is a-okay.

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If it starts to hurt, she can stop for a second and allow the anus to relax and accommodate it at her own pace.

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You won't be surprised as much by your own, um, touch. When you're both experimenting for the first time, enjoy the thoughtful, playful aspect and take.

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