Living In Sin: Neighborly Nookie

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

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?

Comments

[Mrs F]

Or you could do the old sleepwalking stunt...PRETEND to be asleep, roll over onto him, make wild passionate love or if he's not interested act asleep and presto, no one has to wake up feeling like there is rejection hanging between them!

[Bill]

Just once, soon, give Mr. Johnson half an oh-boy and then climb on and give him a ride. If he doesn't respond, drop him immediately and move on.

That way you won't always be wondering what might've been.

[Katie G]

Yeah. She tried to make me sound like an average 21 year old pathetic soul, where I am a little more hip(wise) than she thinks! SHE TRIED TO LUMP ME! SHE TRIED TO FUCKING LUMP ME! I'm in for the challenge my FUCKING ASS! I was curious what she had to say, and that's what I get! I'm NOT looking for a man. I'm NOT looking for a fuck. I want to make love to him. I truely care about this person and we talk all the time! He's easy to talk to! For anybody! But it's just foreign for him with these certain topics. (maybe I worded it wrong in a lot of ways, especially when I said he was "clueless". I meant as far as how and where to touch me, what I like and how to please me sexually.) By the way, after each time when we sorta "hooked up" the next day was extremely pleasant and not awkward in any way. (we're not stupid) And I would NEVER do anything if I didn't think he wanted to do or was ready for it. I'm NOT trying to conquer him. I truely care about this person more every day and more than I ever have anyone else and she, You (Jen), tried to cheapen it to a pathetic high scool crush! I'm not just looking for anyone, like, "oh he's my neighbor, that's convenient" I do NOT want to just be in a relationship to be in one. (I may never be in one again actually, because I'm not willing to waste my time!) I may date, but I'm not looking or finding. I do not want to have sex just to have sex. (I have hands and fingers!) I like that I'm shy around him with certain things. It's genuine. I like that he has an innocence, and I'm not looking to ruin that. Sure I'll spice up his life with some good lovin! - But that's not the sole goal. We love to be around one another. That's how we wound up in the same bed. (by the way, it all began because we were trashed one night and he pushed me in to the pool and it was 3 in the morning and my clothes were soaking wet, so he gave me some boxers and a shirt to wear and I stayed the night.) Then it evolved into most nights. I've always loved this boy and always will. No matter the outcome. So wise up and stop being so fucking sinical! Not everyone is out to ruin other people days or lives. Thank you however for your attempt to riun mine. Put that in your pipe and smoke it! Sincerely, "Silently"

[Jen]

Easy killer! You asked for my opinion, and I gave it to you. Sorry if it wasn't what you wanted to hear, but when someone tells me she's in love with someone she doesn't feel she can talk to, and who doesn't seem all that interested in having sex with her, I see a red flag. Maybe you'll live happily ever after, who knows? But yeesh, loosen your bone, Wilma. It's just my opinion!

[Cleo]

I think he may be really shy and he lacks confidence/has fears about doing it "right" since he is still a virgin. He has managed to communicate that he hasn't had sex before so either he has been waiting for the love of his life, or is completely passive. She will most likely be the initiator from here on out.