Getting Those Digits: A Gentleman’s Guide to Fingering

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It's time to stop treating it as an afterthought.

Editor’s note: This story from Playboy author Bobby Box was originally published on Playboy.com in 2019.

Men often pride themselves on their bedroom reviews, yet for some suspicious reason we don’t care to improve because we feel there’s no need. Except there is, a big one evidenced by the menacing orgasm gap between the sexes. Considering this lopsidedness, it might be useful to know that a meager 17 percent of women orgasm from penetration alone, which means your dick can’t possibly do all the work on its own. You’ve got to help your buddy out, and an often-neglected yet effective form of play is something you probably consider fairly simple: fingering. By manually stimulating the clitoris during intercourse, a woman is four times more likely to orgasm.

Research published in the Journal of Sex & Marital Therapy analyzed the orgasm histories of more than 1,000 women to pinpoint what revs her engine and generally concludes that, in order to climax, women require a tactful mix of intercourse and outercourse. More than two-thirds of women report needing clitoral stimulation in order to orgasm and an additional 36 percent say clitoral contact enhanced their sexual experience. Two-thirds agree the best way to stimulate the clitoris is by applying indirect pressure around the clitoris (treat the clitoris as if you’re rubbing an eyeball through an eyelid), followed by gently brushing over it. The clitoris is sensitive and coated with nerve endings (more than your entire penis, in fact), so be gentle and play nicely—unless instructed otherwise.

Above all else, don’t overcomplicate things. Research has found nearly half of women prefer being touched just one way, so there’s really no point in getting too terribly creative. So, to appeal to the masses, Playboy spoke to Megan Stubbs, sexologist, who insists that in order for a fingering session to feel good, you must properly communicate. “Make sure your partner is up for one, two or more fingers, and affirm the speed and intensity of the penetration,” she offers.

Because the g-spot is located on the anterior wall of the vagina, the best way to reach it is by having her on her back and inserting a lubricated finger with your palm up. The g-spot’s tissue should feel different and engorged when aroused compared to the surrounding tissue. When you’ve found this uber sensitive spot, Stubbs recommends you perform a ‘come hither’ motion with your finger, running along the inside of the vagina, or some light tapping with the pad of your finger. “Even though the vagina is self-lubricating, it’s always great to have lubricant on hand,” Stubbs adds. “Sometimes your partner may not lubricate enough for painless penetration, and that is ok. It isn’t an indication that they are less into you or aren’t as turned on. Sometimes bodies need extra help.”

British escort and dominatrix Valerie August approaches the topic from career experience. August implores men to first examine the state of their fingernails, knuckles and cuticles pre-insertion, as unkempt areas can impede pleasure. “If a woman is enjoying [getting fingered], the interior walls of the vagina go soft and slick, more squashy and swollen,” August tells Playboy. “You can generally consider that change in texture your cue to up the ante with the internal fingering. Add an extra finger, more pressure on the g-spot and/or a little more speed.”

A common mistake men make when fingering a woman is they go too hard and too fast, a behavior learned from porn. “It can be hard to resist continuing to get faster and faster if I’m making sounds like I might come, but I cannot overstate how much I need you to hit a rhythmic plateau and stay there for the long haul until I’m done,” August adds. “When I do come, I like the motion to slowly die off from the moment I start coming and slowly coming to a halt. No emergency stops, or you’ll cut my orgasm in half.”

As you can probably discern, there is no foolproof technique when it comes to pleasing a woman manually, the orgasm is picky and subjective. All we can say is if you’re going to commit to some finger action, don’t half-ass it. “So often activities like fingering are an afterthought or just a short prelude to the main event of sex,” Stubbs adds. “Take your time and make this its own activity to be enjoyed. If given enough time and the right stimulation, you can help your partner orgasm many times over and keep the glow going for days.”

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