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.”

Well, these boys are now seniors, and as their 18th birthdays approach they’ve taken to reminding me of what I used to say. I know I should laugh off their advances and see the shy, innocent boys they were when we first met instead of the hot, virile men I’ve watched them grow into over the last three years. But we’re talking varsity-swimmer-and-soccer-player hot, Dan. Hot enough to be worth putting up with the gossip that would seep through this small community. And it’s not just physical attraction–these model-quality guys have killer personalities too.

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

Without a doubt there are lots of reasons I would make a terrible high school teacher, but high on the list would be my refusal to play along with our cultural schizophrenia when it comes to attractive 18-year-olds. My refusal to pretend that hot 18-year-olds aren’t (1) hot and (2) fair game would no doubt cause a scandal at whatever school was stupid enough to employ me. I’m glad I have a job that allows me to be honest about why I took a day off last week to watch 19-year-old Spanish tennis star/superbabe Rafael Nadal win the French Open.

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.

Let me make one thing perfectly clear:

I think it’s totally fine for hot 27-year-old women to sleep with hot 18-year-old guys. If they’re old enough to go get limbs blown off in Iraq, they’re old enough to get blown stateside. But sleeping with 18-year-old former students carries too many professional risks, TT, for me to give my blessing.

But let’s say I got a letter from a 27-year-old high school teacher who was spending a couple of weeks in, say, Cancun, where she met some recent high school grads who were totally hot and totally legal and totally not her former students. I would definitely tell that teacher to fuck those boys’ brains out so long as she observed the Campsite Rule. Older folks who mess around with younger folks have a special duty, TT, and that’s to leave ’em in better shape than they found ’em. You don’t make babies, you don’t give ’em diseases, you don’t lead ’em to believe that anything lasting is going to come of this. You answer their questions, correct any misconceptions they may have about sex, show them where the clit is, make sure they know that birth control is their job too, and impress upon them the importance of being good, giving, and game.

Are you with me, TT? There are ways you can scratch your itch for a guy, or a few guys, or a few dozen guys who are varsity-swimmer/soccer-player/Spanish-tennis-star hot without risking your job. I mean, you get to go on spring break too, right?

I can’t ask my doctor about this one, and hope you and your specialists can help.

I am a cross-dresser currently going through feminization training with an Internet mistress. We are about to embark on a simulation of my getting my period. This will require that I use tampons for several days. I know about toxic shock syndrome (TSS) and the need to change tampons frequently, but are the risks greater for anal use of tampons?

Looking at various Web sites, it’s clear there are lots of sissies doing this. I want to be sexually smart and not harm myself. Please help. –Premenstrual Sissy

First, a medical opinion: “A search of the medical literature turns up nothing to guide us,” says Dr. Barak Gaster, Savage Love’s long-suffering medical go-to guy. While there are no cases of death from men putting tampons up their butts, Dr. Gaster nevertheless thinks it’s a bad idea. “I’d still be worried about constipation from excessively dry stool or the tampon getting lost up there,” he says. “So even though there’s not much risk of infection, I’d recommend he wear pads instead.”

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.

Are you ever going to run the column you promised with advice for gay and lesbian 15-year-olds? I’m a gay high school junior, and I’m dying for the advice people wished they had when they were my age. –Colin

Tune in next week, Colin, for all the advice a 15-year-old gay kid could ever need.

In other gay news: last week the pope condemned divorce, masturbation, birth control, in vitro fertilization, living together before marriage, and same-sex marriage. According to Bennie, all of the above add up to “anarchic freedom.” The headlines the next day? “Pope Condemns Gay Marriage as ‘Anarchy.'” They should have read something like this: “Pope Condemns Majority of American Heterosexuals for Private Sexual Conduct, Also Gay Marriage.”