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How Do I Plow My Teacher and Get Away With It?

How Do I Plow My Teacher and Get Away With It?

by Erin Pipes,
first published: May, 2005

approximate reading time: minutes

As much as I like her, I wouldn't want her to get in trouble for doing something unethical.

Welcome to "dear girl... - OutsideLeft's version of the tried and true sex column. Erin Pipes, the girl in "dear girl... is a fully qualified expert in the field of sex - mainly because she has the most of it on the staff—so you're in good hands.

Dear Girl,

I'm a twentysomething, recently returned to school after a long hiatus. I'm enjoying it so far, but I'm having a problem with my English professor. She's cute, smart, and well-read (naturally) and we've hit it off quite well. That's my problem; I'd really like to make a move on her, but I'm not sure if it's wise. What are the rules governing teacher-student relationships? As much as I like her, I wouldn't want her to get in trouble for doing something unethical.

Ray, Boston, MA

For about, oh, two seconds there, I considered actually researching the facts in regards to student-teacher relations (by they way, they're always pretty much frowned upon.) But if you were asking me what I would do, I'd always say 'go for it.' Call me illogical. Call me an overly romantic, throbbing membrane of lust, but I'll almost always say 'go for it,' no matter which situation it is. You're hitting it off with this woman. If you're wondering about the rules, then it's already gotten pretty serious, at least potentially. And, if it's gotten so far you're wondering about the rules, you know she's thinking about you, too. Like, at night. Like, she puts aside her beat-up copy of Emily Dickinson love poems and really THINKS about you, if you get my drift. So, really, if I said "it's highly unethical, turn back now!," could you? Why not just see where it could go? Or would you really rather regret not having made a move based on what the 'rules' say? Fuck the rules, pally! I'm saying it's worth the gamble. And if something serious comes of it, THEN you can worry. Together.

Dear Girl,

How can I teach my girlfriend how to "squirt?" You know what I mean.

Thanks, Dry Dan (Dallas, TX)

Most pornos would have you believe that only the rare freak-girls can jizz, but you must've heard we all have the squirting power, eh Danny? There are quite a few books around these days that can help you and your honey learn more about the magical art of the girlie orgasm. Hell, just go over to Amazon and type 'female ejaculation' into the search bar and about a dozen or so titles come up all quick-like. With me, and what you might tell your girlfriend so she can start thinking about it, it came as a choice. When you're building on that incredible itchy deliciousness of orgasm, most girls will start to notice a particular sensation. Familiar, even, like you have to urinate. If you've already taken a trip to the bathroom before you started getting down, then that's likely not what's brewing in your nethers. I'd heard one or two things about squirting before this time when the feeling gave me pause, so rather than ride it out as I would normally, I decided a little pushing would be in order. That's really what it takes. I mean, sure, it takes a skilled partner, or a persistent pressure (not necessarily on the g-spot, but it might help). It takes an intense climb to what you know is going to be an amazing orgasm, regardless. But when you reach the peak and start feeling that aforementioned feeling-associated-with-peeing, you just . . . push. This is the hard part for most women, I'm thinking. Going against the impulse to 'hold it in.' Push like you would if you WERE peeing, if you'll allow me to get a little crass. What you'll get is a thinner, clearer version of your regular girl wetness and your chance for the dude (that means you, Dan) to sleep in the wet spot for a change.

Dear Girl,

I recently found myself a wonderful man and we've been dating for the last few weeks. We're both having a great time together. Well, almost. Premature ejaculation is not the phrase I'm looking for. All I have to do is expose my breasts in the bedroom and he's hard. Nibble on his earlobe and he's already climaxed. He claims that pleasuring me is enough to get him off - and it's always been that way for him. He's 32, and regards this as normal. (I'm 21, enjoying being the novelty girlfriend.) In my sexual experiences, hundreds upon hundreds of different men over a period of three years working as a sexworker [Jesus Christ, I hope this is an exaggeration. - Ed.], this is absolutely shocking, horrifying and well, disappointing. I'm just about chewing through his belt, I'm desperate to fuck this glorious man but I just don't ever get a chance! Seeing as he thinks all this is normal, and has done for the last 30 years, how does the new girlfriend suggest gently that, 'Buddy, you're malfunctioning.' I don't want to bash his ego. Sneaking desensitizing cream into the bedroom could just be seen as offensive if I haven't spoken to him about it first. And talking to him about it directly, in my usual tactless manner, is going to go over like a lead balloon. Please help!

Shagless in Shelbyville

Hmm. Well, of course you're going to have to find a way to mention it to your guy if you plan on keeping him around for awhile. Seems like you're pretty happy with him otherwise, so is there maybe a way to break it to him gently? I have to say, though, my initial reaction is "she's got a guy who makes sure she's satisfied and requires nearly nothing in return, lucky bitch!" But, I mean, I do feel you. Especially factoring in that you're an escort [Oh. - Ed.] your JOB is pleasure! So, naturally you're going to be peeved that you can't let your talents shine. I'm thinking, if it were me, I'd say something like "I would really love to feel you come when I'm fucking you...hat can we do about that?" Foregoing the desensitizing cream (which also tends to numb-out the vagina—- NOOO!), maybe let him fire off a couple of rounds during what would normally be foreplay, get his itchy trigger under control and THEN give it a try? There has to be a limit to his super-quick discharge. Maybe it'll take some extra work, but you're definitely licensed for that, and thus ends my clever gun/penis metaphor. Good luck to you, miss.

Gotta problem? Of course you do. Send them in email form to Dear Girl (or as we at the office call her Erin Pipes) at Our intern-monkeys will be sure to pass them on to her.



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