› email@example.com 
Since I can't write this week, I thought I could at least rerun a letter germane to recent discussions.
I met a guy through his very explicit and fun Craigslist ad describing the weird-ass kinky sex he wanted. So we e-mailed, met, and had a great time. He's handsome, intelligent, artsy ... totally my type. We end up in bed, he gives me some quality oral sex, and then he ejaculates within two minutes. He makes no move to get me off either, just makes some remark about that being "my random Craigslist hookup." I'm too flabbergasted to ask for more oral sex. And then he wants to spend the night and cuddle. I'm frustrated and confused, but let him, and don't comment on his premature ejaculation for fear of damaging his ego. Later we have sex again, and again he ejaculates within minutes. What do I do when he calls? What should I have said at the time?
I once sat on a panel with Craig from Craiglist and I'm imagining him being mortified by this entire story. He's a shy boy. I would also dearly love to link to the offending ad, but it seems faintly unethical, although it's often said that once you post something on the Web, it's public, period, and ripe for linkage. He's probably taken it down by now, anyway. I can attest that the ad was lengthy, floridly descriptive, occasionally inept ("Bring your noble breasts"), and kinky in a cutely sophomoric, let-me-mash-grapes-in-you kind of way. It certainly did not read it as an offer of a two-minute, one-night stand complete with sexual frustration and dismissive jokes.
What to do if he calls? Doesn't that depend on whether you wish to see him again? If you do, you will have to say, "But I want to do the stuff you said in the ad! Not five minutes of sex and then goodnight. OK?" If you don't want to see him again, you say "no thanks."
There are ways to ask for more without bruising a boy's ego some boys, anyway. The ones to whom one is not allowed to say anything but "Wow! That was the best sex ever!" are not worth playing with. Yours doesn't sound at all like the brutally macho type, more like your typical under-experienced urban dweeb-boy, so you would be quite safe in expressing an opinion, especially if you're upbeat about it: "That was hot! I'm still hot! C'mon, let's do some more." Not: "Well, that sucked. In fact, you suck." I can't see the point of accusing him of premature ejaculation specifically, nor was that his greatest offense. What was, then? False advertising, of course. He proposed lengthy, goofy, sexy fun to ward off the looming, glowering gloom of autumn. Did he deliver any of that? No, he did not, and you would have been within your rights to point this out. On closer reading of his ad, though, I notice that he included an escape clause: "Not looking for mind-blowing, end-of-the-world sex."
I fear we shall all end up bringing our lawyers with us on first dates. End-of-the-world sex, indeed.
I recently hooked up with an inexperienced 23-year-old man. Sex has not been great for him in the past. With his ex, he always initiated, she never seemed to enjoy anything he tried, she refused to offer suggestions, they both became resentful, and now he's afraid of sex. He told me he's nervous and insecure, and when we finally got to it, he lasted about 15 seconds.
I find this guy unbelievably hot. I wouldn't have guessed he was so inexperienced, and I get turned on thinking about how some really great fucking could rock his world. So far I've tried to not judge him and to be patient. I'd like to show him how great sex makes life worth living. But I don't want to coddle or condescend to him. I also have no experience dealing with quick ejaculators. (It only happened once, but I'd like to know some techniques for keeping it from happening again.)
He is, for your purposes, a babe in the woods. Coddle all you want. I wouldn't suggest actually condescending to him, if only because condescension, unlike, say, humiliation or scorn, lacks essential hotness. Assume that he is attracted to you at least in some part for your worldliness, and play it up. He is a tender, pink-eared schoolboy. You are Jeanne Moreau.
There is no instant technique applicable to premature ejaculation (and yes, 15 seconds is premature); it's all longer-term stuff. If interested, he can apply himself to his studies and gradually train himself out of coming so quickly, especially since it is likely nothing but nerves. Far simpler, though, is the magical solution available mostly to very young men and their partners: do it again. And again. And again.
Don't forget to read Andrea at Carnal Nation.com.