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 [nature] of that experience,” says Sinclair—and the same isn't necessarily true when a dildo, string of anal beads, or vibrator is used.
Now for the fun part: The ultimate anal fingering guide to teach you, once and for all, how to finger your butt.
12 Steps on How To Finger Your Butt
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.
FYI: 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—but it is a possible encounter while exploring anal fingering. 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 can over-stimulate the anal nerves, and at worst, nail roughage can actually cause micro-tears to the sensitive and thin anal tissues.
Additionally, it’s just more hygienic. Nails tend to harbor germs, so keeping them covered is an easy way to prevent the spread of bacteria. That said, if you don’t want to use a finger cot, you can always pay extra special attention to your nails. “It is best to keep nails filed, trimmed, and short,” says Tim Lagman, a certified sex educator and coach from Toronto, Canada, host of the podcast Sex Ed With Tim, and featured user on the MŌN app. “An ideal length would be when you look at your fingers from the fingerprint side and you do not see the fingernail arching above the curve of your fingertip."
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.
All this to say, you should never dive straight into penetration unless the receiver is adequately prepared.
Instead, Lagman says to work slowly. “Massage the ass cheeks by giving them a light squeeze,” he says. “Play around the area of the hole by lightly grazing it with your fingertip. Draw circular patterns like a flower around the hole. Press on the hole like a doorbell. All this will help with arousal and warms up the sphincter muscles to get ready for play.”
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 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,” he says.
12. Clean-up and aftercare
No matter how many fingers you use or whether or not you stop at anal massage or take a full foray into anal fingering, clean-up is a must. “Getting up to wash your hands and bringing her a warm washcloth enhances the moment, not ruins it,” says sex expert Susan Bratton. “Just keep your whole sex experience as sanitary as possible, never cross-contaminating the hand you use for anal fingering with the hand you use to touch elsewhere. Any partner who lovingly focuses on cleanliness is a partner who makes you feel safe. You can snuggle after a quick clean up. That way you can really relax and bask in your afterglow. If you’re lying there with one hand that’s been up a butt, you can’t embrace your partner.”
7 Anal Fingering Positions and Techniques To Try
1. One finger
As tempting as it may be to try to wiggle in more than one finger, Sinclair reminds us that you can do a lot with a single digit. “You can keep your finger stiff and press outward from the center of the anus to gently massage in different directions,” she says. “Then try moving your finger in different ways. For example, you can vibrate your hand to create a sensation like a vibrator or slowly slide your finger in and out.”
2. Two or more!
Once the receiver is comfortable with a single finger, consider adding more digits to the fun.
“As your partner relaxes, they might be ready for a second or even a third finger,” Sinclair says. “Slowly slide the first one out, apply more lubricant on both fingers, and then slide back in together.”
3. Slow and steady
No matter how many fingers are in the bum, the speed should remain the same.
“Fingering is often depicted as a strong, fast movement [in porn],” Bratton says. “However, for the average person who wants to explore their back door, using gentle, slow movements is much better. The outer anus needs to relax and get to the point where it is almost slurping the finger inside. When you press your finger in, it will pop into place. That can feel like a lot at first, but it has to simply clear the first knuckle to stay in.” Once inside, Bratton points out that the sphincter doesn’t want a lot of forceful in-and-out movement, as it can be triggering. Over time, however, she says that you can slide the finger in more deeply—so long as you’ve communicated it first.
4. Reverse cowgirl
Hoping to add anal fingering into your full act? Bratton says that accompanying reverse cowgirl with a little backdoor action can be a real hit. “This position has a woman on top facing her partner’s feet with her back to them,” she explains. “This is a sweet way to explore your backdoor while receiving pleasure from a strap-on or penis in your vagina at the same time. [Plus,] this gives your partner a great view so they can carefully take their time to ease their way into your buns of love. Since the anus is chock-full of nerve endings, but it’s a timid little rosebud, slow warm-ups are vital. There is as much pleasure playing with your sweet cheeks, your perineum, and your butt hole as there is up inside your rectum.”
5. Target the P-Spot
For prostate owners, anal fingering can be even sweeter. “The P-Spot is a seat of male orgasmic pleasure,” Bratton says. “It’s the equivalent of the female G-Spot and when stroked can deliver explosive pleasure.” To find it, she says to ease your finger inside and crook your finger up toward the belly. “[Consider] palpating and kneading the prostate as you pleasure his penis with your other hand,” she adds. “This is called a Blended Orgasm and can generate a powerful ejaculatory response for a male partner.”
6. The TriGasm
To give a vulva-owner a blended orgasm, Bratton says to take a “multi-faceted frolic into anal land.” To do so, she says to simultaneously stimulate the clitoris, G-spot, and anus.
“For maximum vantage, put a solid pillow under her butt with a towel on top,” she instructs. “Butterfly her legs open and support each with another pillow. Put a pillow under her head. Cover her belly and breasts with a blankie if it’s cold, so she can completely surrender to the trigasmic pleasure. The more relaxed she is, the more she’ll be able to slip into orgasmic bliss.”
7. Consider restraint
To really kick up the heat, Bratton says to consider tying the receiver up to play with their bum. “Restraint can add a naughty aspect when you explore your back door,” she says. “Sex wedge cushions with arm and leg restraints make a novel fingering experience. Lie [them] face down over the wedge and clip [them] into the cuffs. Blindfolding [them] with sensory deprivation can make [them] come even harder. Add a little sexy talk to the experience. Tell [them] how beautiful [they] are. Describe how pretty [their] butt is. Tell [them] what you’re doing to [them]. All of this will heighten [their] arousal and intensify [their] pleasure.”
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