Despite what you may have heard '- or experienced, if you've ever made a fleeting attempt to try it '- anal sex isn't supposed to hurt. "If it hurts, you're doing it wrong and you need to stop," explains Taormino. In addition to a lack of lubrication, the mistake people often make during anal sex is starting with penile penetration. "You can't go from zero to sixty in five seconds flat," she says, "You really have to go slow and warm up to it." In other words, don't race to the finish line; take your time for a more pleasurable and positive experience. So don't even try full penetration the first time. Instead, massage the anus using one or two well-lubricated fingers or a small vibrator. "Start by stimulating the anus with your partner's fingers to increase arousal, which makes you desire it more, which in turn helps relax your muscles," explains Hutcherson. "Your body's natural reaction is to clamp down to prevent penetration, so going slowly gives you enough time for your body to relax and for you to gain some control over those muscles." A week or so later, use more fingers to build on the positive experience, setting the pace you're most comfortable with before going on to full penetration with a penis.
When you're ready, choose a position that doesn't allow for the deepest penetration '- in other words, don't do doggy style (sex from behind). "When men get excited, their natural tendency is to go faster and deeper, and that's not what you want when you're first being introduced to it," notes Hutcherson. She suggests trying anal sex in a "spooning" position where you're both lying on your sides and your partner's front is against your back. You can make the experience even more sensational by having your partner reach around and stimulate your clitoris with his hand or a vibrator during anal sex, offers Taormino.
Good communication is key in any relationship '- and especially in the bedroom. "The woman needs to be in control, saying how slow, how fast, how deep or how shallow she wants it," says Taormino.
Talking things over is also important if you're uncomfortable or scared to try anal sex and it's something your partner wants to try. "Be honest with your partner," says Brame. "Know if you are saying no because you think it's bad and dirty '- and you're not giving yourself permission to enjoy it '- or because the mere idea of it turns you off and it's not your thing. There's usually no harm in trying anal sex at least once, and even if you start, you can still stop anytime you want to."
Some women have nixed anal sex off their list after having a bad experience in the past. "For them, it's important that their partners reassure them and say, 'We're going to go really slow, we'll stop if it hurts and we'll use lube,' which probably didn't happen the first time," says Taormino.
If anal sex is completely out of the question, let your partner know that you don't want to try it, and then offer another option, such as a new sex position. "Usually the man is looking for something new and exciting '- a change '- when he suggests having anal sex," says Hutcherson. "Rather than saying, 'No way,' and making him feel like he's a pervert or that you're rejecting him, say, 'Let's try something else.'" And go exploring from there.