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Here’s how to get started. “Apply circular motions to the nerve-dense muscles at the opening of the anus for pleasure, and to help those Enter: anal fingering, which involves using a finger (or two or five) to penetrate, thrust into, or apply pressure to the anus for the sake of pleasure. 3 Tips for Fingering Someone Who Has a Penis Like any sex technique, fingering the anus takes practice. The world of sexual pleasure is vast and varied, and exploring different avenues of pleasure can lead to exciting and Anal fingering is a type of anal stimulation that includes inserting fingers into the anus, applying pressure to the anus for pleasure. Done safely, anal play with fingers and sex toys can be very pleasurable for men, One sex expert explains why anal masturbation is the best way to try anal fun and butt play — here's how to anal masturbate, plus tips to keep in mind. Seuss Nearly half of you told us you LOVE a finger in the bum during sex! 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