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It might take several sessions for him to learn to relax enough for you to penetrate him more deeply. Once he's comfortable with your finger inside of him, experiment by wiggling it back and forth, sliding it in and out, or moving it in a circular pattern. If you really want to blow his mind, play with his prostate - a chestnut-sized pleasure center about three inches up the front wall of his anal canal - by making a "come here" gesture with your finger.

Pull this move when he's about to orgasm during intercourse, or while giving him manual or oral sex, and you just might send him into orbit. Type keyword s to search. Today's Top Stories.

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Getty Images Getty Images. My guy likes it when I touch his anal opening. Should I go deeper and, if so, how do I go about it?

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For some men, the backside is strictly taboo territory; for others, it's a turn-on that can intensify their pleasure. Since your guy likes what you are doing so far, he may want you to explore this nerve-packed area further.

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