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Living in Sin: The Brown Spider

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Jen Sincero is a musician, sexpert, and the author of the bestselling book, The Straight Girl’s Guide To Sleeping With Chicks and the semi-autobiographical novel, Don’t Sleep With Your Drummer. She currently hosts a weekly sex talk radio show called Dr. Happypants on

Living in Sin is her weekly advice column for LA's sexually curious, confused and constipated. Got a question for Jen? Ask her. We promise to be discreet (all questions will be posted anonymously).

Now, let's get sexual.

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Dear Jen,
Whenever I mention anal sex to my girlfriend she claims she tried it once, it hurt like hell, and no way is she doing it again. Should I just resign myself to this sad reality or is there some way I can convince her to give it another try?

If I never hear another person whine about how much butt sex hurts it’ll be too soon. Yeah, it can be a little painful at first, but so can losing your virginity, and I’ve yet to meet a single chick who didn’t give that another whirl. I don’t know what your girlfriend’s one and only experience was like, but if the pain is really her only objection, I’m sure that with a little practice and a ton of lube, you won’t be able to remember a time when your dick wasn’t up her ass.

I suggest you start by decriminalizing it. Buy her books by anal enthusiasts like Tristan Taormino’s Ultimate Guide to Anal Sex For Women. Go to a chat room where women are talking about anal sex and show her that there are plenty of us out there who love it (and who felt a little pain the first time). Suggest she ask her friends how they feel about getting it up the poop shoot – there are bound to be one or two fans. Make her feel confident that you want to do it right, that you’ll follow the Slow, Steady, and Slippery rule, and that you’ll let her lead the way. Make a point of playing with the brown spider when you’re having sex to get her excited by how good it feels.

Leading by example is also an option. Ask her if there’s anything she wants to try and show her that you’re willing to go outside your comfort zone to please her.

If she absolutely won’t go there, leave it alone and focus on her other fabulous qualities. Pushing people to do things they don’t want to is an excellent way to screw up a perfectly good relationship. And a buttsexless life is far better than a sexless one.

Got a question for Jen? Ask her.