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Hint: Make sure your fingernails are smooth. Give him some time to adjust to the way your finger feels. Whatever you do, don't force it.
If you feel resistance, ease up. 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.
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