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Teen blonde slut Eats Cum from Pussy. Once he's riled up, test the waters by gently sliding just the tip of your middle finger inside. If he clenches his sphincter muscles, which encircle the anal opening, pull your finger out and continue rubbing the outer area to help reduce his tension.

Then, try to insert your fingertip again. If he likes how this feels and is up for trying more anal action, gradually move your finger in deeper, taking care not to scratch the delicate tissue inside.

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.

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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My guy likes it when I touch his anal opening. Should I go deeper and, if so, how do I go about it? 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. Just make sure you take it slowly so you can suss out his boundaries.

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