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How to Perform Anal Masturbation. To begin, take a finger and place it at the very opening of the rectum. Slowly insert the finger into the rectum. You don’t want to go too far on your first try to prevent any discomfort. You can then slowly move your finger in and out of your rectum to become used to the sensation.

Pair anal play with stimulation in another area, like the nipples or genitals. Try different speeds and motions. Shallow thrusts, deep thrusts, gentle tapping, circular motions, the “come hither ...

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