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Dear Ashley,

I am looking for tips on how to make anal sex more comfortable. My husband is bigger than average. He’s less than eight inches in length and like six inches circumference. We’ve tried dozens of times and it’s too painful for me. We’ve tried everything—lots of foreplay, fingering, lots of lube, butt plugs, taking our time and trying to ease into it. No matter what we try, it doesn’t seem to help when he goes in. I swear we’ve tried every position imaginable, but when I get more than a couple of inches, the pain becomes too unbearable and I always need to stop. Any advice?


Ms. Painful

Dear Ms. Painful,

Anal sex just might not be for you. I honestly feel that anal works best with smaller packages. Your husband’s package isn’t small and anal with a larger package requires a lot of preparation. But even with preparation, it may not physically be your thing if you are experiencing pain. Sex of any kind isn’t supposed to be painful unless you want it to be. The pain you feel during anal is your body’s way of letting you know that something is off.  

Maybe try shallow strokes. Deep strokes especially with a larger penis are not the answer. The best tip is to find a depth that works for you and keep it there. Another trick is using a sex toy on your clit while being penetrated from behind. Stimulating your clit during anal sex can help you relax and make it easier for rear entry. Other than these two suggestions, you have already tried pretty much everything I would suggest. I think it’s important to point out that anal play doesn’t always have to involve a penis. There are several ways to enjoy anal play that you’ve already tried such as anal beads, plugs, fingers, etc. If using anal props are more pleasurable than a penis, I would honestly stick with the toys.

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Dear Ashley is a weekly sex column where Sexpert Ashley Cobb answers your intimate questions. Nothing is off-limits! Have a sex question, Ashley, “Your Favorite Friend In Filth,” has an answer. Email Ashley at

Ashley Cobb is the millennial microphone that brings the conversation of Black women’s pleasure to the forefront. Creator of digital platform Gossip And Gasms, her work and words have been featured in Cosmopolitan, Men’s Health, Shape Magazine, Business Insider, and Huffington Post. Follow her on Instagram and Twitter via @sexwithashley

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