Little, constant pushes, I think are best.
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There is something called enema.
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What I suggest is, rub it yourself, or, if your partner knows how to move well with his fingers in that area, ask your companion to rub it.
Now, protection and lubrication try anal masturbation to discover what position would be more. I am 20 years-old and I have been enjoying anal sex since I was That is why again you should comfortable for you.