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To begin, put a generous amount of water-based lube on one or two fingertips make sure you replenish the lube often and gently massage the area around the outer rim. 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.
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