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The person doing it should err on the shallow side. Log in Sign up with Facebook. It prevents bacteria from the bowels spreading anywhere. The whole point of anal play is to keep it simple before working your way up. If you try it a few times and hate it, don't keep trying it because you think it'll eventually be tolerable. Type keyword s to search.
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An easy way to start is by having your man start with a little penetration, either during sex or cunnilingus, using a small or bullet vibrator turned off, if that's easier. Water-based lubricants work great. All kinds of lube are used for anal sex; spit, Vaseline and high-tech silicone-based lubes.
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