21 Tips for First-Time Anal Sex

If this is your first time trying anal sex, spend some time relaxing—take a hot bath, ask your partner to give you a sensual massage, heck, you can even meditate. To prepare for anal sex, you can also focus on specifically relaxing the muscles of your anal sphincter. To see what that feels like, tighten your butt muscles and then release.

2. Explore on your own.

Suzannah Weiss, resident sexologist for Biird and author of Subjectified: Becoming a Sexual Subject, recommends playing with yourself first to learn what you like and don’t like before including a partner in the mix. “The easiest way to begin would be with your finger,” she says. “First, warm yourself up with clitoral stimulation. Then put a water-based lube on your finger and start gently inserting it while combining it with the clitoral stimulation. That will make it more enjoyable.”

If you enjoyed that experience, she suggests moving up to a butt plug. Look for a set with multiple sizes so you can start small and work your way up as you gain confidence and experience.

“I would recommend doing those things before you attempt anal sex with a partner,” Weiss says. “You want to know that it is something you can enjoy and how you enjoy it, so you can communicate that to your partner. If it’s something you’re not enjoying on your own, it’s unlikely that you would enjoy it with a partner.”

3. Communicate openly.

Figuring out how to do anal sex with your partner starts with communication. “Talk about it first. As with all types of sexual activity, anal sex is something that should be discussed beforehand,” says Rachel Needle, PsyD, a licensed psychologist and certified sex therapist. “Communicate your fears and expectations with your partner, and make sure that you are both on the same page about things like speed, depth, etc. Trust me, this is one area in which you do not want any surprises.”

4. Establish boundaries.

Throughout the experience, it is your job to pay attention to what you are feeling, and communicate this to your partner. If something feels uncomfortable or painful, let them know. You may choose to establish a safeword to let your partner know you’re not comfortable moving forward or that you want to move a little slower.

5. Lather up.

“Many people’s fear of first-time anal sex stems from a fear of what goes on back there (naturally) and how that’s going to play into the action,” says Needle. “To cleanse yourself (literally) of such mental roadblocks, take a nice, steamy shower first.”

6. Engage in plenty of foreplay.

One of the best ways to ease into anal play is to make sure you’re extremely aroused beforehand. “The number one mistake people make is rushing,” says Taormino. Start with foreplay, vaginal sex, oral sex, or whatever turns you on. (Being one or two orgasms deep before you try any anal penetration helps.) “The more aroused you are, the more relaxed your sphincter muscle will be, and that’s going to make for a hotter and easier experience,” she says.

7. Use lube. A lot of it.

The key to really enjoying anal sex? Lube, lube, and more lube. Unlike the vagina, the anus does not produce its own lubricant. The more lube you use, the more comfortable and enjoyable anal sex can be, explains Needle. (It also helps prevent bleeding after sex.) If your partner is using a condom, don’t forget to make sure to apply a water or silicone-based lubricant (oil-based lubricants aren’t compatible with condoms). Weiss recommends sticking to a water-based lubricant if you’re using a silicone toy, as silicone lube can cause the material to degrade.