Do It Yourself

As the old adage goes, practice makes perfect. “Whether you plan on being the pitcher or the catcher, you will be a better lover if you experiment on yourself,” says Jess O’Reilly, host of the @SexWithDrJessPodcast. Regardless if you’re planning on sliding your finger into someone’s butt or want to pleasure them with toys, it’s important to try a few test rounds on yourself. Not only are you more relaxed — there’s no pressure to perform, after all—but you’ll be able to better observe your body’s responses to the stimulation, O’Reilly continues.

By exploring on your own, you’ll know what it feels like to have fingers or toys in that particular orifice, so it won't be a complete surprise when your partner goes there. “Learn how your body responds and learn how to control that response more,” Gunsaullus says. “You may get through a little bit and you feel like there’s a blockage. Hang out there, put a little pressure, relax.”

Try experimenting in the shower, Marin suggests, taking advantage of the relaxing bathing experience, warm water, and the easy cleanup.

Make It Shine

Speaking of showers, if you’re weary of the messes that potentially await, hop in the shower beforehand. Put a little soap on your finger and clean both the outside area and inside the anus to ensure no stray fecal matter gets left behind, Gunsaullus recommends. However, it’s important to note that feces only passes through the anus—and is not stored in it — O’Reilly explains, so you’re likely to only encounter residue. Experts agree to skip the enema.

And remember, this is sex: There are many bodily fluids involved. So no matter how thoroughly you’ve groomed, messes are par for the course.

Educate Yourself

While you needn’t get textbook-level deep, it’s helpful to know some of the nitty gritty of your anus to understand why anal play feels good or why it doesn’t. From the outside working in, you’ve got your anus, which is rich in nerve endings, O’Reilly says. “For some people, this is where anal play begins and ends,” she says. “You can derive great pleasure from playing on the outside, so don’t feel you have to have a particular type of sex based on what you’ve seen in porn or what you perceive others to be doing behind closed doors.”

Lubricate and Play

Remember that nugget about how the anus doesn’t self-lubricate like a vagina? This is why lube is essential. Experts recommend longer-lasting, thicker silicone-based lubes, touting brands like Sliquid, Pjur, and Astroglide.

As for toys, try some well-lubed anal beads, thin, high-grade silicone dildos and small butt plugs. Again, it’s crucial for these items to have a flared base. And if you’re concerned with mess, lay a towel down where you’re going to get busy, have wet wipes handy, and use condoms (for penises, dildos or butt plugs alike) for easier cleanup.

Take It Slow

Because there are many tight muscles surrounding your anus, any sort of penetration must be slow and gradual in order for the act to be pleasurable and not painful, O’Reilly says. Start with a well-lubed pinky finger and work up to a larger toy or penis. Be patient: It could take anywhere from 20 to 30 minutes just to warm up, Gunsaullus notes.

Don’t get hung up on penetration as the be-all-end all of anal. There’s plenty of fun to be had around the butthole itself. “A majority of the nerve endings are right around the anus,” Marin says. “A lot of people prefer just having stimulus right at the anus or around it.”

If the receiver is experiencing any pain or discomfort, toys or body parts should be slowly removed.

Try to Multitask

You want to ensure you’re highly aroused and blood is flowing to your genitals for a better anal play experience, Gunsaullus says. Pairing anal play with clitoral or nipple stimulation or engaging in dirty talk can heighten the experience all around. However, for penis-havers, stroking the penis may result in some butthole clenching, Gunsaullus continues, so it may be best to leave your member alone if you’re looking for anal penetration.

If one of the keys to anal play is relaxation, there’s no greater period of tranquility than post-orgasm. “Bring yourself to orgasm before experimenting with penetration so that you benefit from the elevated endorphin and oxytocin levels post-orgasm,” O’Reilly says.Rather than go straight for doggie style, Gunsaullus recommends the receiver lay on their back and hike their hips up (or prop them up with pillows) for easier access. “Having eye contact and them being able to see your face and get feedback,” Gunsaullus says, “you’re more likely to have that teamwork aspect.”

Don’t Double Dip

To avoid the spread of bacteria—and potential infections—anything that’s been in your butt should never be immediately inserted elsewhere without a proper wipe down. Having wet wipes nearby is great for when you want to move from anal play to other forms of penetration. If you want to avoid a pause for cleanup, Marin suggests using a condom for anal play, then removing it when you’re ready to focus on non-butt stuff.

Ultimately, butt stuff is a hell of a good time, but it does require a bit of groundwork. So wise up, prep, and play on.