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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.

We the people love our challenges, be they physical, intellectual, emotional or involve holding our hands on a car for days at a time. Believe me, most women have fallen for your same guy at least once in our lives. I had a crippling crush on a gorgeous Cave Thing in high school who was so introverted he'd pull his chair out into the hallway and listen through the open door to the rest of us hanging out.

What is it about that which we cannot have that is so appealing? Why does the prospect of unreciprocated oral sex and zero communication have you all hot and bothered? Because not only is it a challenge, but it confirms your feelings of unworthiness in a way that only being with someone who doesn't really want you can.

Virgin or not, if you're lying in bed next to a guy whose Mr. Johnson you've already oh boyed, he'd go for it, or at the very least kiss you if he really wanted to. (How on earth did you wind up in bed together btw- did you tell him yours broke or something?)

My advice to you is to move on and find someone who can actually push words through his throat, but when it comes to a crush that's gone on that long, with a guy who's that irresistibly shut down, that's not going to happen. So if bone him you must, you're going to have to get over your shyness and roll on top of him one night. Then you're going to have to suffer through awkward silences and endless hours of trying to get him to pay attention to you followed by a severely broken heart and years of getting over him. But at least you will have conquered him, right?

Photo by phil.thuma via flickr