Help! Buttfucking hurts unbearably! It didn’t hurt so bad the first couple of years, but now, 5 years later, it does. It has never been my favorite thing, but it is my partner’s. He feels deprived and almost desperate. We’ve tried Anal-Ease and Anal Easy, but no luck! There must be something a girl can try. Could I use OraGel? Could I stretch my anus by using butt plugs daily? Would stretching exercises work? Please help!

–Kimberly, Spokane, WA

There are so many elements which you need to have a pleasurable, pain-free anal sex experience: lots of foreplay and warm-up, plenty of lubrication, and communication and trust between you and your partner. Anal sex should never, ever be painful. If it hurts, stop. Pain is your body’s way of telling you that whatever you’re doing isn’t working. You should always listen to your body. Your butthole knows what is best for you. At the first sign of pain, you may want to stop all activity or simply slow it down: maybe use one finger only, change to a smaller butt plug, decrease the depth of penetration, or switch to external anal stimulation only. Work your way back up, but never force anything. Go as slow as you need to, continue to add more lube, and talk to your partner so he knows exactly what does and doesn’t feel good.

I’d also like to address your mention of using products like “Anal Ease” or even OraGel. Anal Ease is the brand name of a lubricant (of which there are several) marketed for anal sex which contains a numbing agent. I absolutely do not recommend using products like Anal Ease ever. Because they have the effect of numbing your anal area, you cannot feel your ass literally and you are in danger of hurting yourself. Using products like these often lead people to go farther than they normally would, take something bigger in their ass than they should and the result is a sore ass, possible tearing and damage to the delicate lining of the anal canal and rectum, and pain after the fact that isn’t exactly going to want to make you rush right out and try anal sex again. There are plenty of great water-based lubricants that are thick and work well for anal sex (like I-D, Maximus, and ForPlay Lube de Luxe Cream), so use one of those. As for the OraGel, common sense and warnings on the label should let you know the answer: no. Just don’t go there.

Using butt plugs on a daily basis is a good way to get your butt used to having something inside it. Butt plugs don’t actually “stretch” your butt; they simply help you learn to relax your pelvic and sphincter muscles. In terms of exercises, many women find that Kegel exercises (which exercise your PC muscles) are very helpful. In order to locate your PC muscles, pretend that you are trying to stop peeing (or while you are peeing, you can actually stop the flow of urine). The muscles you contract to stop the flow are your PC muscles. If you put your finger on your perineum — the area between your vagina and your anus — while you do this exercise, you can feel the contractions.

Kegel exercises (named for the scientist who studied PC muscles and popularized the theory of exercising them) can help you to become more aware of your sphincter and PC muscles and learn to control and strengthen them. They will help you get in tune with the feelings in your pelvic area, increasing your sensitivity and responsiveness. The exercises will also tone the pelvic muscles, making them more flexible and more receptive to pleasurable sensations; when you exercise the PC muscles, other muscles in the area also are exercised and strengthened.

Women who regularly exercise their PC and pelvic muscles report some very positive benefits: heightened pelvic sensations and greater anal sensitivity; increased pleasure during clitoral stimulation, vaginal and anal penetration; more control over orgasms; and better, more intense orgasms. For more information on Kegel exercises, check out Anal Pleasure and Health by Jack Morin and The Complete Guide to Safer Sex from the Institute for Advanced Study of Human Sexuality. There is also a masturbation tool called the Kegelcisor, designed like a barbell for your pussy, which works wonders on those muscles!

But there is another crucial ingredient to great anal sex, the most important one — which may be missing for you, according to your letter: desire. You really have to want to be fucked in the ass.

First, you may want to think about why you don’t enjoy anal sex. Many people have fears and anxieties which, when kept to themselves, can result in tension and a butthole that just won’t let anything inside. Meditate on your feelings about and associations with anal sex, your past experiences with buttfucking, what you liked and disliked about it. Share your thoughts with your partner — sometimes talking about things can help you assuage your fears and relax. If you come to the conclusion that you don’t want to do it, then don’t do it. All the exercises, butt plugs, and lube in the world won’t do a damn thing if your heart’s not in it.