Message: Girlfriend Has Done Anal Before But Won’t With Me

Anonymous: Hit 22, my question is more related to the emotions I’m having towards anal. I have been with my girlfriend for 3 years now and she has done it before with her prior boyfriend a handful of times. She let me try and it was unsuccessful and I never was able to fulfill an intimate fantasy eith my fiancé. She is persistent on not letting me do so anymore, but I feel as if it’s unfair to me. Am I selfish for feeling like that since she’s done it before? And is it weird it’s a fantasy I really want?

How was it unsuccessful? Why won’t she let you try it again? Talk it over with her and figure out the reasons she’s not interested. Tell her that you’d like to do it with her, but you want to make sure she really enjoys it as well, and if she’s willing to consider it, work to get her to the point where she is comfortable with some light anal play—either rimming or fingering—and gradually work up over time from there, with her dictating the pace. There’s a lot more information elsewhere on this blog and online about the process of preparing for anal and enjoying it, but she has to be interested in trying first. Pressuring her won’t help and will just make things worse.

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