There's no "right" way to begin exploring, but it's probably wise to start with something less ambitious than a penis. Richard and Lola* had been together for four months when he put his hand on her butt during sex. "I realized I really wanted to put my finger in her ass, but I was hesitant because we'd never done that before," says Richard, a 34-year-old physicist in San Francisco. "Without a word, she grabbed my hand and put it there for me. It was amazing."
Later, in the middle of particularly intense sex, an overzealous Richard aimed himself a bit too far south. He realized his mistake and pulled away, but Lola pulled him back. They proceeded to have first-time, undiscussed anal sex without lube—and loved it.
"I've since discovered that's not a good way to do it," says Lola, 32, a lawyer. "But that night I had the most powerful orgasm of my life. It's one of the hottest things you can do, but you definitely have to be in the mood. Someone can't just spring it on you."
Outside of MTV shows and "family" comedies, most people aren't eager to talk about their butts—especially with their partners. But it doesn't need to be a face-reddening experience. "If you and your partner speak openly and directly about sex, then be open and direct about your anal desires," Taormino says. "If you're unsure about how your partner may respond, bring it up in an indirect way."
When you decide to try it out, go very slowly. Most couples agree that anal sex only works when both people are very turned on, so spend time building up to it doing whatever gets you going—oral sex, vaginal sex, watching old episodes of Hart to Hart. And remember what Mother told you: Anything you stick up a butt should be generously coated with a heavy water-based lube like Astroglide Gel or Maximus. The Frisky: 6 Things Not To Do On A First Date
That can't be stressed enough. Unlike the vagina and much like the internal combustion engine, the anus is not self-lubricating. Insufficiently lubed, you're susceptible to tiny internal tears, which can cause pain and infection, and encourage the spread of STDs. But that doesn't mean anal sex is inherently more dangerous. As long as you use a condom and there's enough lube, you'll be reasonably safe. To avoid nasty bacterial infections, remember that it's like stroking a porcupine: You can go front to back, but never back to front.
Sex toys can augment the experience. Nonporous, easy-to-clean silicone is the best material for butt plugs, vibrators, or dildos; a flared base will prevent an awkward trip to the ER for, uh, extraction. "We started with a small butt plug we got online," says Heather, a 38-year-old New York City nonprofit executive who convinced her husband—yes, he was the wary one—to try anal. "Then we moved on to sex, and it was totally unique. I have to do it in a place where no one else is around because I'm worried about people hearing me—I'm always a lot louder."
No single position is ideal, but the receiver should be in control. Missionary works; woman-on-top lets her control the depth of penetration; and spooning allows the man a perfect angle. Doggie-style provides great G-spot stimulation, with the woman either on all fours or with her head on the bed and butt in the air (yogis call it "Foraging Anteater Pose"). To make sure the man doesn't thrust too deep, he should enter, stop, and wait for her to get used to the feeling.
Or is it the other way around?
"The ass is the most democratic orifice—we all have one," Taormino begins ominously. "What lots of men don't realize is just how good it can feel for them, because the prostate gland can be directly stimulated. In fact, every man should get f---ed in the ass at least once before he dies."
Maybe this isn't an idea everyone is totally comfortable with, but turnabout is fair anal play.
*Names in this story have been changed.
Like this? Check out related stories from our friends at The Frisky!