Message: How Can She Enjoy Anal More?
Anonymous: How can I get my girl to enjoy anal more? She lets me play around a little bit but doesn’t enjoy the act itself. How do I fix that?
Does she want to do it more and learn to enjoy it? Wanting it is a rather important first step, and not being that into the idea of even trying can make it a lot harder to move past that point. So I would talk with her about it first, see if she’s interested, and tell her that you’d like to get to where you can both enjoy and share it together but that you’re okay going at her pace so that you make sure she does enjoy it.
I would start by focusing on the things that she does like and not pressuring her to push too far past that for now. If she doesn’t enjoy anal sex, but does enjoy certain forms of anal play, that’s a pretty clear sign that she’s just not ready for anal sex yet. Start doing the things she does enjoy with more frequency. Rim her. Finger her or use smaller toys on her. Combine these things with other things she enjoys. Buy her a butt plug she can wear during oral, etc. Gradually work her up in size as she’s comfortable doing so, until she can comfortably fit a dildo similar to your size. It’s all about gradual, incremental increases in size. If you jump straight to anal sex with someone who easily finds it painful or uncomfortable, it’s often too much all at once. Warmup and training is important for a lot of people.
I’d also suggest reading through the Anal Advice category here, which covers a lot of similar questions.
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