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Living In Sin: Vamos a la Sex With Friends!

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Every week in Living in Sin, Jen Sincero provides advice to LA's sexually confounded. Sign up for her newsletter and have it sent to you every week. Ask Jen your questions: all are posted anonymously.

Dear Jen,
My fiancé and I have been together for quite a few years and have started having a sexually open relationship. Usually we play together with someone else, but occasionally we'll let each other go solo. Well, we have a mutual friend who I've known a long time and lately I've been thinking about asking this friend if she'd like to make our friendship a more beneficial one. We talk all the time, and she always complains about never getting any sex. A few weeks ago she told me she's never had an orgasm, and I couldn't stop thinking about how I'd love to try and help her with this problem. I was thinking of propositioning her next time she complains about never getting any. There's a chance she'd say yes and it would be great, but then there's always a chance she'd say no and then things would become awkward. What do you think I should do ?
- Beneficially Wondering

Dear Beneficially,
I moved to the beach about a month ago and it's killing me. I have an unbelievable amount of work to do, and am actually excited to do it, but am finding that I'm much more excited about the sunny days, warm sand, big waves, hammock on my new roof deck and the fun, unemployed neighbors who are just as easily distracted from their responsibilities as I am. It's like I'm a drug addict and I'm surrounded by an All You Can Snort Cocaine Buffet. In case nobody noticed, today is Wednesday. For the past year, my column has come out on Tuesday afternoons, without fail, same time, every single week, no-nonsense, on the nose. But not this Tuesday. This Tuesday was spent smelling like a coconut on a long walk with the aforementioned neighbor, followed by a swim (with five dolphins thank you very much) and then a leisurely bike ride up the coast because you should have seen the sunset.

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I am in very deep doo doo.

I declared this morning the official end of my evil ways, but then the godamned sun came out and I was once again seized by the desire to splash my way into that gorgeous sea of denial at the end of my street. And I'm not going to say I didn't do it because I did, BUT I have a new plan. I'm all about the approach now. I get to spend an hour and a half swimming or bike riding or neighboring, and then I do my work. See? I just did it. I am going to beat this thing. Oh yes I am.

Same goes for you and your orgasm-free friend there. Life is too short not to seize sex when someone hot wags it in your face, but it's all about the approach. The next time she brings it up (which is indeed the perfect time to do this), inform her that you'd be more than happy to ramalan her ding dong, but keep it light and fun and no big deal. And definitely don't say "ramalana ding dong". How awkward can it be if she's already talking to you about her orgasms? Be clear, but easy-going about it, and then leave it alone. If she's into it, she'll do it, if she's not, hopefully she'll just feel flattered. Being desired is a lovely thing. The key is to be non-chalant about it, and to make sure you don't make her feel leched upon afterwards if she's not into it. Good luck! To both of us!