Thinking of experimenting with anal play, or perhaps your partner has suggested you give it a try? Done safely, anal play with fingers and sex toys can be very pleasurable for men, women and people of all genders and sexualities. So why might someone want to try anal fingering? Anal stimulation has the potential to be pleasurable for anyone who has an anus, but for men and people with penises, it can be especially enjoyable thanks to the prostate or P-spot. And as Knight points out, as well as feeling comfortable, you should both be excited and enthusiastic about exploring anal fingering. The anus needs a little more care than fingering a vagina, Knight explains.
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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.