First-Time Anal Sex Tips: How to Do Anal Guide

First-Time Anal Sex Tips: How to Do Anal Guide

Curious about the pleasure-potential of your bum? Or, at least, been wanting to understand all the hoopla around anal hanky-panky? There’s much to know about anal sex—and even more to gain (read: orgasms) by knowing it!


We called on three anal play experts to help us put together this fool-proof, pleasure-guaranteed guide to exploring your backside– whether you have a partner or not.

If you’ve never ventured back there during "me time", or had a lover graze your hole with a tongue, finger, or sex toy, you might be wondering what the point is. So, before we get into the “how” of anal play, for anal-play newbies and skeptics, let’s address the “why”.

The answer is simple: pleasure.

With 4,000 nerve endings— that’s the same amount as what’s in the tip of a penis—the anus is a highly-sensitive erogenous zone. You don’t even have to go inside the butt to start experiencing moan-making pleasure. “Even tracing the entrance of the anus with a finger or toy can feel incredibly pleasurable,” says Sociologist and clinical sexologist Dr. Sarah Melancon Ph.D, with The Sex Toy Collective. (Pro tip: Add a lube like Tush Cush and this will feel like rimming).

For many folks, the sensation of something being inserted into the ass is what’s pleasurable. “There’s a very specific sensation of stretch that occurs that can be arousing,” she says. And for penis-owners, the experience of being filled during sex can be as psychologically thrilling as it is physically stimulating.

Butt (had to) the pleasure doesn’t stop there. Go even deeper into the canal and you’ll discover nerve-dense hot-spots that respond well to pressure. Dr. Melancon explains: Vulva-owners have two nerve-clusters in the vaginal canal that can be stimulated through anal penetration: the G-spot (which is towards the entrance of the vagina) and the A-spot (which is deeper back).

And people with penises have the prostate, which is often described as the male G-spot. “The prostate is a super-sensitive walnut-sized gland that responds well to consistent pressure,” she says. Some folks can even have an orgasm from prostate stimulation alone. Prostate play can be especially thrilling for folks with erectile dysfunction because prostate orgasms do not require an erection or any additional genital stimulation.

How to Explore Anal for the First Time


anal masturbation

Even if you have the most caring, loving, communicative partner in the world (think: sexually active Mother Teresa), anal masturbation should be your introduction to anal sex. Dr. Melancon explains: “Solo anal makes you both giver the pleasure and receiver, so you’re able to easily adjust and maneuver [your finger or the toy] based on what feels good and what feels less good,” she says.

As clinical sexologist Dr. Megan Stubbs, Ed.D puts it, “When you’re on your own you can immediately call the shots. But with a partner there’s a bit of a delay between when you’re experiencing discomfort, communicating that to them, and them adjusting.”

Plus, playing on your own is going to make partnered play even better. “You’ll be able to use what you learned while masturbating to guide your partner,” says Dr. Melancon.

use your fingers

Experts recommend starting your anal masturbation journey with your own (well-manicured, hangnail-free, very, very clean) fingers—as opposed to toys. Why? Because it’s helpful to be able to feel what’s going on inside the canal, says Dr. Melancon. Those aforementioned hot-spots, for example, are spongier than the rest of the anal canal, which means you’ll be able to suss them out with your finger.

To try anal fingering, sex toy guru and pleasure expert Carly S., founder of Dildo or Dildon’t recommends grabbing a hand mirror and one of the best anal lubricants (like Tush Cush), and massaging the entrance of your hole. “Make circles, play around the outside, massage the opening, spank your own ass cheeks if you enjoy that, etc.,” she says.

If this feels good, stay there! “If you like the sensation of pressure against your sphincter feels good, you can start to bend the muscle down and slide a lubed-up finger in,” she says. (If you’re using a mirror, the butt hole will pucker when it’s ready to be penetrated).

Once you get that first knuckle inside, squeeze your butt hole around the finger for ten to thirty seconds, and then relax it. “By doing this, you’ll bring more blood flow to the area, which will increase arousal while decreasing discomfort,” says Dr. Melancon.

Once you’re in, there’s no wrong move! Does thrusting in and out feel good? Do that! Does going deep and wiggling your digit around feel good? Have at it! Craving even more girth? Fill your hole up!

add in a sex toy

Now that you know what you like, add in a sex toy. As Carly S explains: “A toy can replicate the sensation while freeing up your hands so that you can also stroke your genitals, nipples, and other erogenous zones.”

When shopping for a backdoor toy there are two important things to remember: You should never ever stick anything up your butt that does not have a flared base and is not made of a non-porous material.

Dr. Stubbs explains. Unlike the vaginal canal which has a stopping point (the cervix), the anal canal keeps going up the digestive tract. “You need a toy that has a flared base that keeps the toy firmly rooted outside the body,” she says.

You should also opt for a non-porous material (like silicone, stainless steel, glass, or ABS plastic). That way you’ll be able to get the toy completely clean when you wash it (with warm-water and fragrance-free soap)—something you definitely want, considering the toy is going in where poop comes out.

try it with a partner

For those of you looking to expand your backside hanky-panky horizons, partnered anal play can be a fun next step. But you don’t want to test the waters with just anybody. “Pick a partner who respects you, who listens when you communicate your needs and wants, and who you trust to go slow,” says Dr. Melancon. (TBH, this is probably a good rule across the boning board).

Have a partner who’s equally excited to get down and dirty? You can’t just stuff their penis or dildo right in. Doing so (especially without lube) puts you at risk for anal tearing and injury. Instead, prepare your bod for penetration by using the techniques you mastered during your solo-sessions: anal fingering, anal massage, or anal toys. And if your partner is up for it: rimming.

Next, Dr. Melancon recommends using a lube applicator to lubricate the interior lining of the anal canal with one of the best lubes for anal sex. Then, if one of you has an STI or you have not talked about your STI-status, have the person slide on a condom before placing their penis or dildo against your entrance.

Take big breaths as they press against you. You might try rider-on-top so that you can lower down onto your partner at a depth and speed that feels good to you. Or, get on all fours for doggy, which naturally opens your hole for easier entry.

“Go nice and slow, communicating every millimeter of the way about what feels good and what doesn’t so you can both be enjoying it,” says Dr. Melancon. And if at any point what you’re feeling is pain, stop! “Anal should never hurt,” she says.

the bottom line on bottom play

So long as you and your partner remember the unofficially motto of anal play: “slippery is a must, nice and slow makes it better,” anal sex can be a welcome addition to your sex life.

If you’re on the market for lube for anal sex? Check out Tush Cush: a thick water-based jelly with aloe vera, which Dr. Melancon is great at keeping the anal canal well-moisturized. You might even apply some to the entrance of your bum when all is said in cum as a treat.

On your marks, get slippery, go slow!

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