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Regardless of what you’ve heard about or seen in porn, anal is not about forcing. The receiver, rather than the giver, sets the pace. If anyone is experiencing discomfort, slow it down! You also don’t need to insert the whole length of the penis or dildo. It could be that half is the perfect amount.
According to Kyla Black, a sex therapist and clinical social worker, there's really no right amount of lube: “It very much depends on the person who will have lube on or in their body,” he says. Err on the side of excess, since the anus doesn’t self-lubricate, and choose the right lube. Avoid lubes that contain parabens, phthalates, or propylene glycol, and keep in mind that silicone-based lubes generally last longer than water-based lube: “The anus is a mucosal membrane, which means that it absorbs water rapidly and will dry out water-based lubes,” Bogdonoff says.
However, if you’re using toys, make sure to only use water-based lube with silicone toys and be careful with oil-based lubes, which can cause condoms to rip or deteriorate. Bogdonoff recommends Pjur Backdoor, a silicone-based lube that contains jojoba to increase the skin’s flexibility and softness.
There are a ton of ways to prepare for anal penetration, including using vibrators, rimming plugs, anal beads, and even dildos. These will not only open the anus but also arouse you before penetration. Sex and relationship coach Charlie Glickman, PhD, author of The Ultimate Guide to Prostate Pleasure recommends using a vibrator to learn to relax the anus; be sure to use one made with a body-safe, non-porous material and a smooth, flared base to prevent it from going too far into the anus. Glickman suggests b-Vibe’s Rimming Plug, which takes the technology of the famous rabbit vibrator and adapts it for an anal toy.
Anal has long been tainted with stigma and fears — that it’ll hurt, that something will go wrong, that you'll poop in the middle of it. But the shame surrounding anal sex "assumes that anal sex is unhealthy and should be rare," Ley says. "That’s a morally-based assumption, not a scientific or medical one." The best way to bring up the idea of anal sex to your partner is when neither you nor your partner is aroused. This way, you can talk about it without feeling pressure to do things too soon or in a way that feels rushed.
With new sexual territory, boundaries are key. "It can be helpful for both partners to be aware of each other's’ 'dos and don'ts' and anything in between," says Black.
Ley suggests broaching the subject by discussing anal play as part of your sex life. "Discuss including anal stimulation in a variety of ways, with fingers, toys and tongues," he says. "This is how a couple can introduce the anus as an area of pleasure and sensation, without jumping too quickly to the theoretical finish line of penis-in-anus sex."