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Living In Sin: Neighborly Nookie

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Sex is something that drives us, empowers us and gets us into really stupid situations with people we have no business seeing naked. Jen Sincero is the bestselling author and sexpert with the carnal knowledge you need. Ask her your questions (all are posted anonymously). Cuz there's no such thing as being too good in bed.

Dear Jen,
I’ve been in love with my neighbor since we were 6 (we’re both 21 now). We recently hooked up a couple of times - he kissed me for the second time (the first time was 8 years ago, my first kiss) and I blew him twice. The problem is that he's a virgin and is CLUELESS, meanwhile I've been in two long-term relationships since I was 16. I don't want to force myself on him, but I really wanna fuck him! Or at least make out, but I’m very shy around him.

I've been sleeping in bed with him every night for the past three weeks and he never makes a move. Can you give me some advice on how to move things along, or if I even should? By the way, he's a man of few words, it would be a very tricky subject to approach verbally.
- Silently Suffering

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Dear Silently,
My friend’s husband is a tri athlete who was recently in a race where they drop a bunch of guys off on some island with nothing but a bike and a bag of nuts. Then they run, pedal, climb, crawl, limp and swim for 2 weeks from one end to the other. He lost all his toenails, ate bugs, ripped open his face on a tree branch and rode five miles on nothing but metal rims when the tires on his bike blew. And he did it purely for the challenge, not because he was being chased by a rhino.