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Living in Sin: Vacation on Three-Way Island

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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 killradio.org.

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).

Dear Jen,
I'm going to Jamaica in a couple months with my boyfriend and I'm very interested in having a threesome with another woman. I just don't feel that I have the confidence to go up to a stranger and propose one without scaring her away! Any suggestions?

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I love the idea of stepping out of your sexual comfort zone while on vacation. You're more open when you're in unfamiliar territory, more likely to strike up a conversation with strangers, explore the terrain, stick your face between some sweet girl's legs while your boyfriend watches. And luckily, so are a lot of other vacationers!

There are lots of ways to approach another woman, but whether or not you scare her off is kind of up in the air. And who cares anyway? It's not like you're going to have her over for book group if the threeway thing doesn't work out. You’re on vacation, you’ll never see her again.

Your best bet is to put yourself in her place, think about what you'd want to hear if some couple wanted to make a bone sandwich out of you. Don't forget you're a woman too - you know what you like to hear, which compliments work and which don't, so take advantage of this insider's knowledge. Also, use the fact that you're flirting as a team with your boyfriend. Send her a drink while both of you wave from across the room. Have your boyfriend get the ball rolling before you saunter up and nuzzle him, cooing something suave in her direction about what excellent taste he has in women. Stand next to a cute girl and start discussing something sexy with your boyfriend, then ask her opinion on the topic.

I'm also a big fan of just blurting out the ever-subtle "we think you're cute - wanna come home with us?" Because as far as I'm concerned, we all take the flirting thing way too seriously. Why get so freaked out and horrified? (We all do, but why? Why? WHY?) Life is short, don't spend it placing some hotty stranger's opinion in front of your own. Even if you get rejected, you should rejoice in the fact that you had the cojones to approach her at all, and that's really all that matters.

Plus, everyone is usually wasted on vacation. Especially in a place like Jamaica. Just pass the joint, mon, sit back, and watch it unfold.

Got a question for Jen? Ask her.

Previous Sins.