Message: How Can I Help My Girlfriend Not Be Afraid of Anal?

Anonymous: So, when my girlfriend and I first started dating, she was very anti wanting to try anything anal. But recently, she let me finger her anally, and was surprised that she actually enjoyed it. However, she’s still timid about trying full anal penetration, even though I know she’s the kind of really freaky girl who would really love becoming an anal slut. What are some things I can tell her/do with her to make her realize how much she will enjoy it, and that it’s not anything to be scared of?

Don’t be pushy and try to get her to do something she’s afraid of and thinks will be painful—chances are it will be if she’s really worried about it. Rather, discuss that you’d like to slowly work towards being able to do that, but going at whatever pace is necessary for her to feel comfortable trying it and confident that it won’t hurt.

And then, just keep including anal play—fingering, butt plugs, etc.—in your sex life, gradually working up in size over time. If anything hurts, stop doing it, take a break, and try again smaller for a while. At some point she’ll be able to comfortably fit things the size of your penis (whether it be a toy or multiple fingers), at which point you may consider anal sex.

The two of you should both read up on proper and safe anal sex practices from a variety of sources, and she should experiment on her own at her own pace as well, to become familiar with her body and how it responds.

The key points: always use lube; always stop, take a short break, and try again smaller if something hurts; and she should play with herself during anal penetration both to relax and to help develop the connection between anal stimulation and pleasure.

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