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Is anal sex pleasurable for all men? Anal sex is often thought of as only being for gay men or kinky heterosexual couples who like to mix up their game a bit. Many men report that prostate stimulation can be a wonderful enhancer of their sexual pleasure, especially when they are approaching orgasm and during ejaculation. But what exactly is the prostate?
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Skip navigation! Story from Sex. My first image of pegging — as well as prostate play in the context of heterosexual relationships — involved a very binary gender swap. In my imagination, the woman embodied a fierce, dominatrix aesthetic, while the man was bound and helpless. But no matter what we call it, the limited cultural dialogues we have about sex still assume that it is defined by a penis entering a vagina.
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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. 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.
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