I started teaching high school freshmen three years ago, when I was 23. I was closer in age and culture to most of my students than I was to the other teachers. That first year I bonded with a lot of the students, in particular with a small group of boys on the basketball team I coached. A couple of these boys developed crushes on me–as any horny, normal teenager would on a mildly attractive teacher. Since they were 14 I’d laugh off their advances by jokingly telling them to “ask again when you’re 18.”

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I’ve maintained a professional and appropriate relationship with these boys over the years. But what about once they’re legal and out of school? It seems like 27-year-old men hook up with 18-year-old girls all the time, while middle-aged men drool over the Olsen twins. Why can’t I make an 18-year-old’s dream come true? –Tempted Teach

But while I won’t condemn you wanting to fuck the living shit out of a pack of totally hot, completely legal, soon-to-be-former students, TT, I don’t think you should. Here’s why: You live in a small town and you like your job. When word gets out–and those boys won’t be able to resist telling their friends–your school will find a reason to fire you. School administrators in these litigious times aren’t going to look the other way while a teacher bangs her former students. They’re going to assume, perhaps rightly, that any teacher banging 18-year-old grads today may be banging 17-year-old juniors a few years down the road. At the very least they’ll worry, perhaps rightly, that you invested years in grooming these boys and that you’ll set your sights on a fresh crop of 14-year-olds.

Now, a sex-advice columnist’s opinion: Isn’t inflicting a little discomfort the whole reason your mistress is ordering you to shove tampons up your ass? If you get constipated, take some Ex-Lax; if you lose one up there, you’ll just have to ask a doc to dig it out for you. The relatively small risk of constipation or a humiliating visit to your proctologist’s office shouldn’t keep you from following your mistress’s orders, PMS. Do it, sissy.