Help! I'm Sleeping With an Almost-Monk

Dear Dategirl,

I just started seeing (well, dating and trying to have good sex with) this new guy. He finally deigned to do it recently, and we have a couple of times now, but there's a problem. He was training to be a monk and just left the monastery, so he's a little, well, restrained. I can guarantee you that he enjoys sex, but he feels guilty for doing anything. He never initiates, only infrequently touches me, and so on. What can I do that won't scare him but will make him more satisfying for me? I mean, he left the monastery because he didn't want to be "without women."

But what the hell?? I need mildly experimental sex or at least sex that I'm not always in charge of. Is there anything you can tell me to do besides get rid of him? I like the guy. I also like that I get to corrupt him....Dissatisfied Sinner

Ooh, does he still have his burlap monk robes? What about the funny 'do? Would he be pissed if you showed up in a nun outfit? Maybe you could play priest, and he could be your naughty altar boy in a homemade confessional! The pervy possibilities for your situation are seemingly endless—too bad he's so uptight about it.

After I was done concocting various Catholic school–inspired scenarios in my head, I realized I was entirely too excited by the idea of defiling a monk (!!!!) to come up with any rational advice. So I asked writer Rachel Kramer Bussel—the editor of two new and very hot anthologies: He's on Top and its companion, She's on Top (both Cleis Press)—what she would advise. My thought was that since he's so passive, maybe you could get a copy of He's... and take turns reading each other stories from it.

"A lifetime of being made to feel guilty about sex can certainly leave its mark, so if you want the sex to sizzle with him, you have to go slowly," she advises. "Emphasize that sex should feel good—for him and for you. You don't need to make over-the-top screaming noises, but let him know how much pleasure you are feeling before you go to the next level."

Good point. Sound effects are key. But remember not to go too far into the shrieking department, or he might start thinking Linda Blair instead of Linda Lovelace—and you know how freaky those religious types get about the devil.

Rachel goes on to say, "If you want rough sex, or even slightly kinky sex, you're going to have to guide him down that road. You can start with your mouth."


"No, not like that—by talking dirty," she clarifies. "Try to verbalize what you want, but without comparing him to past lovers. Instead of, 'I loved it when my ex tied me up,' you could say, 'Hold down my arms'; and when he does it, encourage him to keep moving in that direction."

Rachel makes an important point here; even the most experienced, suave luv-uh men don't like to be compared to those who've gone down that road before. Since your boyfriend likely hasn't had a whole lot of partners, he's probably extremely intimidated at the prospect of measuring up.

"As you slowly reveal your turn-ons, hopefully he'll do the same in turn," she adds. "You might want to also take some time—either post-sex or in the morning, when doing it isn't the first thing on your mind—and simply whisper something absolutely filthy in his ear, then coax him to share the same. Separating dirty talk (or smut reading) and the act of sex may make him more comfortable. The less pressure he feels—from you, and from his own internal moral compass—the easier it'll be for him to enjoy sex."

If all the hand-holding and porn-reading (you might try watching some, too) don't work, whip out everyone's favorite John Waters quote: "I thank God I was raised Catholic, so sex will always be dirty." As a lapsed Catholic myself, I can attest to the fact that knowing I'm going to hell makes even a furtive feel-up that much hotter. You've just got to convince him to embrace (and, perhaps, sodomize) his inner sinner.

Dating dilemmas? Write Dategirl at or c/o Seattle Weekly, 1008 Western Ave., Ste. 300, Seattle, WA 98104.

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