Ask Emily: How Do I Get My Girlfriend on the Booty Train?

Q: Dear Emily:

I’m a gay woman who can’t really get off from vaginal penetration, but I like anal penetration. Some partners might have been surprised, but most have being willing to penetrate me anally.

Now I’m dating a new woman who’s nine years older than me, and she’s having a hard time wrapping her mind around my request. She says she doesn’t want to do it because she doesn’t want to hurt me, but I keep telling her I’ve already done it and can walk her through it.

I’d hate for this to be the end of our relationship. Can I do anything to reassure her that I’ll be OK and even enjoy it?

Thanks!
Jan, 24

A: Dear Jan,

Here’s the thing about anal: while a lot of women—and I mean a lot—get serious pleasure from it, it can still be a little bit scary for those who’ve never tried it before. We all know that anal sex has gotten a bad rap in the past, including tales of pain and discomfort. Your girlfriend is probably under the impression that anal penetration isn’t something that feels good, so why on earth would she want to do it to you? Even your offer to walk her through it, while very sweet, could still be a little daunting, so communication is going to be key in this situation.

Communication is a lubrication…

Like anything new in the bedroom, it’s super important to talk about anal sex before you try it. Even more so in this situation, since there are definite steps that need to be taken to ensure the best experience possible. I would begin by reiterating the fact that anal sex is something you really enjoy and brings you to orgasm. Communicate the pleasurable aspects about anal penetration—how good it feels, why it turns you on—and continually assure her that anal sex does not hurt you, but quite the opposite. It might take some time, but the more you inform her about the pleasure it brings you, the more comfortable she’ll be in return.

Just be sure you are listening to her just as much as you hope she is to you, because pushing someone too far too fast will only cause backfire on your back door endeavors.

LEARN MORE ABOUT HOW TO GET YOUR GIRLFRIEND TO UNDERSTAND YOUR LOVE FOR ANAL STIMULATION IN MY LATEST ARTICLE FOR GLAMOUR’S SMITTEN COLUMN, “HOW DO I HELP MY PARTNER UNDERSTAND THAT ANAL PENETRATION GETS ME OFF?

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