Every Friday on the blog, I answer people’s questions about sex, love, and relationships. This week’s question comes from a male reader who wanted to know more about the topic of anal sex:

“My girlfriend and I both really want to try anal sex, but every time we do, we stop almost immediately because she says it’s too painful. Are we doing something wrong? Is there anything we can try to make it pleasurable instead of painful for her?

Thanks for this question. Let me start by saying that there isn’t one “right” way to have anal sex, just like there isn’t one “right” way to have any other type of sex. The key is figuring out what works best for you and your partner, and please keep in mind that different positions and techniques might work better for different people.

For starters, here are a few very general guidelines for mutually pleasurable anal sex: (1) the insertive partner must be patient and begin with slow, gentle penetration (perhaps even starting with a finger or small sex toy before moving on to penile insertion), (2) the receptive partner must be comfortable and relaxed, (3) both partners must communicate and listen to one another, and (4) a comfortable amount of lubrication should be applied to the anus both inside and out (lubrication can't just be applied to the outside of the body, and it may need to be re-applied a few times during penetration—keep in mind that the anus is not self-lubricating like a vagina).

Let me also caution that you probably shouldn’t use porn as your how-to guide for anal sex. Pornos may not give you a realistic idea of how much preparation was involved (e.g., how much lubricant was applied) or what feels good for most people (e.g., in porn, anal sex is often very fast, deep, and rough—and attempting to replicate that in the real world may prove quite painful). Also, it’s common in porn to see practices like going immediately from anal penetration to oral or vaginal penetration without changing condoms or cleansing the penis in between. Behaviors like these are risky and can lead to infections.

With that in mind, if you’ve followed the guidelines above and anal sex is still painful or uncomfortable, you may need to hold off on penile penetration and instead try using small sex toys for a while—this is something you might do together, but she may also want to try it alone in a more relaxed setting, such as during masturbation where she can have complete control. Fingers can be used instead of sex toys, but if so, nails should be short and you may wish to consider using latex gloves. A few other tips: extended foreplay sessions may help with relaxation, some positions may be more comfortable than others, and some lubricants might yield more pleasurable results (e.g., consider that silicon-based lubricants tend to last longer than those that are water-based).

That said, it is important to note that some people report severe pain every time they attempt anal sex (one study of heterosexual women put this number at 9%, while a study of gay and bisexual men put the number at 14% [1,2]). Unfortunately, we don’t fully understand why this is because there isn’t a ton of research on this topic; however, there are several possible reasons. For example, some people may have underlying medical conditions that make anal sex painful. Also, some people’s anuses may just be more sensitive to touch (remember that there’s a ton of individual variability in what feels good--for instance, consider that there are some folks who love having their nipples pinched and bitten and others who wince at the slightest touch). Finally, some people may have insertive male partners with particularly large penises, which may cause some degree of pain for the receptive partner no matter what precautions are taken.

Again, let me caution that there is no “right” way to have anal sex because this is an activity that may feel very different from one person to the next. It is also something that may require a lot of practice and preparation before it becomes mutually pleasurable.

For previous editions of Sex Question Friday, click here. To send in a question for a future edition, click here.

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[1] Hollows, K. (2007). Anodyspareunia: A novel sexual dysfunction? An exploration into anal sexuality. Sexual and Relationship Therapy, 22(4), 429-443.

[2] Damon, W., & Rosser, B. S. (2005). Anodyspareunia in men who have sex with men. Journal of sex & marital therapy, 31(2), 129-141.

Image Source: iStockphoto.com

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