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Q My boyfriend is sweet, funny and caring, but his penis is small and he does not like performing oral. He rarely goes down, and when he does it seems planned and premeditated. I’m at the point that even when he “tries’’ to go down, I tell him to stop. I hate it. His penis is small, and my dildo is becoming my best friend. We haven’t had sex in two weeks because I refuse to lie on my back and be only slightly amused. What’s a girl to do?!?

A Okay, I get it—his penis is small. Boy, you’ve got a lot of anger. Trust me, you’re not the first woman to date a cunnilingophobe, but there’s a good way and a bad way to deal with that situation. Bad way: Get annoyed to the point that you (a) don’t even appreciate it when he tries his pussy-licking best to make you happy and (b) keep telling the world how microscopic his penis is. Good way: School the puny-cocked mother-effer. Your obvious disgust with his efforts is likely making him fear the act all the more, so the next time he makes his way down there, have pity on the poor pinkie-dicked fellow, and gently walk him through the process. Guys generally don’t like to do things they think they’re bad at, so the more positive feedback you can give him when he manages to lick something that actually induces pleasure, the more he’ll want to want to give it another go. And remember: Being “only slightly amused” by the tongue of a sweet, funny, caring guy is a hell of a lot better than having your clitoris rocked by an asshole.

Q Your advice to the 43-year-old virgin who was wondering whether she should divulge her status to a potential sex partner made me wonder whether the docs who did your brain surgery left a clamp in your cranium. I am slightly younger than this woman (I just turned 40), but I’m in the same boat. I’m not religious or uptight; I’ve just never had any opportunities. Let me clue you in: There aren’t that many straight men out there who would even want to date a woman over 40, let alone a woman of that age with next to no sexual experience. Think I’m wrong? Look at the magazine that runs your column. Notice all the stuff aimed at singles? It’s a challenge to find any straight men in those pages over 35, let alone over 40. I’m willing to bet you can’t find five reasonably intelligent and financially stable male readers of this column who would be willing to date a woman that old and that inexperienced.

A Suddenly the woman from this week’s first letter seems positively cheery and easygoing. (Oh, and kudos for being the first person to question my mental capacity post-brain-surgery; whenever you end up having sex for the first time, I wouldn’t be surprised if the lucky dude finds a giant pair of balls down there.) I can’t really quibble with your arguments; it’s true, the dating scene for people over 40 is not easy, and you’re probably right about most guys freaking out about devirginizing a woman in that age range. But I’m sticking with my advice: It’s always better to be honest about who you are than to try to fake it. In fact, I would bet that a big part of the reason you and the original fortysomething virgin who wrote me haven’t had sex yet is because you’re not good at opening yourself up. Connecting with people involves making yourself vulnerable—letting them see both the great and not-so-great things about you. I’m not saying that divulging your virginity should be the first thing you tell a guy, but by the time you’re ready to have sex with him, you should be close enough to share that secret. Besides, although they may be a minority, I bet a lot of dudes out there (and I’d certainly like to hear from them) would get off on the idea of popping your cherry.

Send letters to Jamie Bufalino c/o Time Out New York, 475 Tenth Avenue, 12th floor, New York, NY 10018, or send e-mail to sex@timeoutny.com.

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