Sex Advice

The 11-Step Anal Fingering Guide You Didn’t Know Your Pleasure Routine Needs

Gabrielle Kassel

Photo: Getty Images/Voyagerix

Last year, sexual-health experts named anal pleasure the next great frontier sexual exploration. And while it’s great that many folks are familiar with (or getting familiar with) tricks and toys to enjoy rimming, plugging, and pegging, that’s hardly the edge of what butt stuff has to offer. 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. According to certified sex educator Alicia Sinclair, CEO of anal-play-product company B-Vibe, the anus is rich with nerve endings, and stimulating them can be pleasurable. (Some folks even have anal orgasms.)

As far as benefits from from trying anal fingering, the most obvious is that you already have the tools you need in order to get started, well, on hand. Furthermore, anal fingering is an incredibly intimate experience. “When one partner fingers another, both partners get to enjoy the tactile sensation and sensuous of that experience,” says Sinclair—and the same isn’t necessarily true when a dildo, string of anal beads, or dildo is used. Now for the fun part: The anal fingering guide you need in order to start enjoying.

Scroll down for your 11-step anal fingering guide

1. Touch yourself before bringing in a partner

“Masturbation is a fantastic place to start exploring any kind of sexual activity, and anal fingering is no different,” says Sinclair. To start, get yourself turned on with external genital stimulation. Then, if you’re a vulva-owner, Sinclair recommends that before you slide a finger or toy into your vagina, to do the same for your backdoor (but use a different finger or a different toy, so as to not spread bacteria).

“Masturbation is a fantastic place to start exploring any kind of sexual activity, and anal fingering is no different.” —Alicia Sinclair, sex educator

“When you’re ready, lube up your entrance and finger, spend some time making circles around the opening,” says Sinclair. Then, while breathing, apply some pressure to the opening. As your body relaxes into the pleasurable sensation, you’ll be able to slip a finger in. From here, let what feels good guide you.

And according to Evan Goldstein, DO, CEO and founder of Bespoke Surgical, a sexual-wellness company specializing anal-related health agrees adding, practicing anal self-pleasure will help you enjoy anal fingering more moving forward—both receiving and giving.  “It’ll be easier for your body to relax while you’re being anally fingered if you’re experienced the sensation before, and likewise, you’ll be a better anal finger-er if you know how it feels.”

2. Have the anal fingering talk

When you’re ready to move toward partnered play, gaining consent is a must before any action takes place. “You should walk away from the conversation with a clear understanding about what you both hope to get out of the experience, and who’s going to be the receiving partner,” says Sinclair.

3. Understand the deal with poop

First things first, know that poop is rarely an issue. Dr. Goldstein, says feces is stored in the upper bowels, which is separated by your internal sphincter. For the sphincter to relax and release feces, your body has to send a signal to your brain that you need to go to the bathroom. Only then, once you’re aware, does your internal sphincter relax, and then you consciously relax your external sphincter. “Poop does not just come out without warning,” he says. “The reality is that unless your partner has really huge hands and fingers, a finger is not capable of reaching up to the internal sphincter, and past that to where the poop is.”

“Unless your partner has really huge hands and fingers, a finger is not capable of reaching up to the internal sphincter, and past that to where the poop is.” —Evan Goldstein, DO

Now, can there be a small bit of fecal matter still hanging in the rectum? Sure, maybe a little. But Sinclair assures a shower or bath are adequate for cleaning the area.“If feeling nervous about poop is keeping you from enjoying the experience, you might use a water enema rinse an hour before hand,” she says. But before going this route, make sure to consult a medical professional first.

4. Consider using finger cots

Finger cots are condoms for your digits that are made of either nitrile or latex, and they make post-play cleanup easier in addition to smoothing the surface of the finger for easier glide.

They’re also something that nail-biters, acrylic-nail-havers, folks with chronic hangnails, and people sporting finger calluses especially should consider wearing, says Sinclair. At best, too much texture to can over-stimulate the anal nerves, and at worst, nail roughage can actually cause micro-tears to the sensitive and thin anal tissues.

5. Ramp up arousal

Just as you did during the anal masturbation step, make sure to get in the mood first with partnered anal fingering. There’s no wrong way to do this, but kissing, manual sex, mutual masturbation, and sensation play are all good places to start.

6. Grab the lube

Unlike the vagina, the anus is not self-lubricating, which makes lube an absolute must for anal play. “Without lubrication, there’s too much friction. You’ll feel like you’re getting a rug burn,” says Sinclair, who prefers oil-based lube because it’s long-lasting. (Just know that because oil can degrade latex and is not effective for protecting against disease transmission—which shouldn’t be an issue with anal fingering completed with effective cleanup.)

7. Move on to anal massage

Sometimes, the terms anal fingering and anal massage are used interchangeably, but according to Sinclair, they’re not the same. Fingering refers to internal stimulation, while massage refers to external rubbing. Massage, though, is great prep for fingering. “Apply circular motions to the nerve-dense muscles at the opening of the anus for pleasure, and to help those muscles open up so you can slide inside, if you want to,” says Dr. Goldstein.

8. The anal fingering guide main event

“When your body is relaxed enough to go from external play to internal play, you’ll be able to tell,” says Sinclair. “The hole itself will pucker a little bit.” Once you get this invitation and the green light from your partner, ease your finger in, up to the first knuckle.

Next, “hold here for 3, 2, 1 seconds, then take it out, and relubricate if needed,” says Dr. Goldstein. “Go in again and repeat, going just a smidge deeper, if your partner’s body allows.” So long as it feels good for your partner, continue this pattern of slowly moving in and out until you’re able to get the anal sphincter muscles to fully relax.

Once the muscles are relaxed, experiment with different types of touch, asking your partner questions like, “How does this feel?” and “Do you prefer this [insert finger waggle #1 here] or this [finger waggle #2 here]?”  Some people enjoy light thrusting, others like tapping. “If your partner has a prostate, they may enjoy having you curl your fingers up towards their penis and making a come hither motion,” says Dr. Goldstein. This will help stimulate their “p-spot” (the male g-spot), which can lead to what he calls, a full-body orgasm.

9. Don’t double dip

“The vagina and anus both have their own ecosystems and bacteria,” says Sinclair. “And while the bacteria in the anal canal is good for the health of your anal canal, if that bacteria is transferred to the vaginal canal, it can mess with the pH.” And that’s when issues like urinary tract infections, yeast infections, and bacterial vaginosis happen. So before engaging in vagina play after anal fingering, either have your partner change their finger cot or have them wash up during an intermission.

10. Talk about how it went

“Enjoying each other and pillow talking after sex is a thing couples should be doing after sex, in general,” says Sinclair. “But after a new sexual activity—in this case, anal fingering—it’s especially important.”

Did you love feeling your partner accept your fingertip? Did you enjoy feeling full of your partner’s finger? Share the good news! Trying new sexual activities can be intimidating, so making sure your partner feels cared for is a must.

11. Try again, and adjust as necessary

“I recommend waiting three or four sessions before adding a second or third finger, but eventually you can increase the width of what’s being used,” says Dr. Goldstein. And, even if you didn’t love it anal fingering on the first try, Dr. Goldstein urges you to not give up on anal play completely. “Some people don’t like anal fingering but love butt plugs, because a butt plug is smoother, and rather than moving in and out of the body is designed for a sensation of fullness.”

Oh hi! You look like someone who loves free workouts, discounts for cult-fave wellness brands, and exclusive Well+Good content. Sign up for Well+, our online community of wellness insiders, and unlock your rewards instantly.

Our editors independently select these products. Making a purchase through our links may earn Well+Good a commission.

Loading More Posts...