1. It shouldn't hurt. This is where lube comes in. It should basically just feel like you might need to poop. You don't! (I hope you don't.) "Relax your muscles, and breathe," advises Dr. Emily. "Use a lot of water-based lubricant."
2. Start small. The whole point of anal play is to keep it simple before working your way up. "To prepare a bottom for sex play, start with fingers, tongue, or a very small sex toy designed for butt play," says clinical sexologoist Dr. Nancy Sutton Pierce. "An option is to purchase a Butt Plug Kit that uses several plugs, of graduating sizes, just for this training."
3. The person doing it should err on the shallow side. Everything that goes in should be "just the tip." The nerve endings you're trying to stimulate are in the anus — hence the moniker "rimming" — and not all the way up there, which is generally the painful part and also the part that makes you feel like you need to take a huge dump. Imagine it like a basketball hoop, and the ball should just be rolling around the rim of the basket, not actually making the basket. Does that help? I know nothing about basketball.
4. There shouldn't be any rapid-fire movement immediately. Vigorous jamming of fingers anywhere should not happen immediately. "So much of sex is fast — especially in porn — but anal play has to be prepped," says Morse.
5. You can vary up positions. No, not all butt stuff needs to be done doggy style. It's true it might be a little harder to get some solid eye-contact going on when face-to-anus things are happening. But! There are a variety of positions to try, like lying on your back with your hips elevated, or sitting on his face in reverse cowgirl. Move around until you find one that makes you feel most at ease.
6. Communication is key. The only way to know what works and what doesn't is to be totally honest with you partner about what they're doing. Dr. Pierce stresses the importance of always being tuned in to how the other is feeling and being vocal about your preferences.
So, what do you think? Dare to try? Anal or whatever you're doing, just don't forget to always play it safe!