What number is the number 18?

I'm a 27-year-old female who started teaching high school freshmen three years ago when I was 23. I was closer in age/culture to most of my students than I was to the other teachers. That first year

Jun 15, 2005 at 2:06 pm

I'm a 27-year-old female who started teaching high school freshmen three years ago when I was 23. I was closer in age/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 who were on the basketball team I coached. A couple of these boys developed normal crushes on me — as any horny teenager would have on a mildly attractive teacher. Since they were 14, I would 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 have taken to reminding me of what I used to say. I know I should laugh off these advances and see the shy, innocent boys that they were when we first met instead of the hot, virile men I have watched them grow into over the last three years. But we're talking varsity swimmer and soccer player hot, Dan. Hot enough to put 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 have maintained professional and appropriate relationships 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 up on the list would be my refusal to play along with our cultural schizophrenia when it comes to attractive 18-year-olds. The same culture that holds up teenagers or might-as-well-be teenagers as the beauty ideal — from Katie "Grin and Bear It" Holmes to Jude "Sexiest Man Alive" Law — penalizes anyone who admits to actually finding hot, legal 18-year-olds attractive. My refusal to pretend that hot 18-year-olds aren't (1) often hot and (2) fair game would no doubt cause a scandal at whatever high school was stupid enough to employ me. So it's probably for the best that I'm not a high school teacher. Instead I have a job that allows me to be honest with my employers 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 do it. 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 might 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. And if you ever did get caught fucking a 16-year-old current student, your bosses know they'll be fired too if it gets out that they knew you'd slept with former students in the past, even if they were recent grads of legal age.

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 — and send me the video — so long as she observed the Campsite Rule.

Older folks who mess around with younger folks have a special duty, TT, and it is 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 might 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 I hope you and your specialists can help. I'm a crossdresser currently going through feminization training with an internet Mistress. We're about to embark on a simulation of my getting my period. This will require that I use tampons for several days. I know of toxic shock syndrome (TSS) and the requirement 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.

— Pre-Menstrual 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 still 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'd 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.' " The headlines should have read something like this: "Pope Condemns Majority of American Heterosexuals for Private Sexual Conduct, also Gay Marriage."