How can I get my girlfriend to let me do anal with her? She says she tried it once with another boyfriend and didn’t like it. I’ve been with other women who thought they didn’t like it, but the guy they’d done it with just hadn’t been very good at it. I think that if she just let me show her how nice it could be, she’d be into it. How can I convince her to give it another try?
You can’t. Getting to fuck someone in the ass is not an inalienable human right. Even if you think she’s wrong and she’s missing out on the best thing ever, it’s her butthole and she is allowed to say no.
Which isn’t to say that I don’t sympathize with your plight. Butt sex is great when it’s good and terrible when it’s bad, and I can completely imagine that if the person she tried it with before was inexperienced or impatient or unwilling to do it right, it would be enough to make a person write off anal for the rest of eternity.
I do think there are some ways that you could help her see the potential of butthole pleasures, whether that means full-on anal sex or other stuff, but I think it’s very important that you go into it without an agenda and without lots of pressure. The way your question is worded, it makes me think you’re really pushing her to let you stick your dick in her ass, and I’m sure that alone makes her unwilling to even consider it. Which is why I suggest you approach her with the understanding that she never, ever has to consent to anal, and you truly need to be ok with that. If every time you try and put a finger in her butt she tenses up because she thinks you’re trying to trick her into anal sex, you’re never going to show her how lovely butt play can be.
Rather than convince her to “let” you, you need to convince her that she wants to be pleasured by you in that way. Imagine the act of anal sex as a metaphor for your argument. If you go into it acting like the pleasure will be all yours and she just has to grit her teeth and take it, or if you push her boundaries before she is ready, rushing, trying to just jam it in there, it’s going to be disastrous. Her letting you do something to shut you up is not enthusiastic consent, and it’s never going to result in a relaxed and pleasurable experience.
On the other hand, if you go slowly and make her feel good, if you put her in the position of power and let her control what’s going on, if you make the entire thing about her pleasure and her pace and her level of comfort, then she’s going to want it. Work on showing her how some anal stimulation can be pleasurable while you’re going down on her or fingering her. Make it clear that you aren’t going to do anything she doesn’t want, and check in with her to make sure she is enjoying what you are doing. Once she sees how hot anal stimulation can be for a lady, she will likely be willing to try penetration. Just make sure you do it right, because you’re only going to get one shot!Sex@TheLMagazine.com for questions or comments