I am alone in my apartment with a man I’ve only recently met, and I realize: if I were a woman, I’d probably have my clothes off by now.

“Well, I hope so,” Logan says, making himself comfortable.

I hand my guest a glass of bourbon, join him on the sofa. This is not a date. Logan has just worked another 12-hour shift at the Brooklyn hospital where he is finishing out the clinical rotations of his fourth and final year of medical school—though he looks no worse for wear: bright eyes, knit tie, khakis.

Perhaps to make up for my lack of nudity, Logan begins scrolling through his iPhone, showing me samples of the naked photographs and pornographic videos he has received from literally hundreds of women. Logan pauses on a topless photograph of an attractive 20-something. He has slept with this person.

“One problem with her,” he sighs. “Bacterial vaginosis. It’s the only one that smells uniquely fishy. And hers was uniquely fishy.”

As he is a doctor-to-be, and not an unattractive guy by any means (with a face some might call “boyish”), it should come as no surprise that Logan, at age 30, is a lady-killer. Really, he’s a Jewish mother’s wet dream. And over the past year and a half, there’s a decent chance that Logan has slept with that Jewish mother as he perfects the craft of conning women of all colors and creeds between the sheets.

“It makes sense to me, as a science guy,” Logan explains. “Your goal evolutionarily is to spill your seed in as many women as possible. As soon as you’re done, your job is to move on.”

Logan’s real name is not Logan, of course. But Logan is the name that he provides to women when he meets them online, on websites like PlentyofFish and Seeking-Arrangement—the dating service famous for connecting “sugar daddies” and “sugar babies.” Whatever else he tells them depends on his perception of what each woman needs to hear to part with her underpants. And more often than not, that means playing up a perceived socioeconomic power difference, with the implied—and sometimes explicit—promise of money and comfort to come. As he puts it, “Most of the girls I go out with expect it to be something of a sugar baby-sugar daddy relationship.”

Logan wasn’t always a sexual assassin. Growing up in a sleepy East Coast suburb, he attended Jewish day school and didn’t fool around with a girl until 10th grade, the first of his friends to do so. With no one to discuss the experience with, Logan grew confused and retreated into his religion, becoming shomer negiah, meaning he wouldn’t even shake the hand of anyone of the opposite sex (immediate family excluded) and wouldn’t have another sexual experience until marriage. He held fast throughout the rest of high school and all of college, throughout a year studying in Israel and another year abroad. He didn’t get a handshake from a woman until age 23, a hand job until 24, finally giving up the ghost of his virginity at 26 and making up for lost time ever since.

At first, Logan went the traditional route, looking for love via setups and JDate. But he never seemed to make a real connection. “None of these girls liked me. Every time, I was shocked,” he says. Then, after his first two years of medical school, Logan decided to try a different tack. He signed up for a series of new sites, all under his new name. (“I don’t know why anyone would give their real name,” he says.)

The platform he first focused his attention on was PlentyofFish, a free dating website. Right away, he noticed a difference. Presenting himself as a man of means, Logan’s inbox filled with communications from willing women. Did this new power dynamic make a difference? “Of course,” he says. “That’s what makes it so easy. Plus, they actually really appreciated a professional guy. Whereas the Jewish girls I’d gone out with, they couldn’t care less. So No. 1, it’s nice to talk to these girls because they have that look in their eye, they admire what you’re doing. And No. 2, it’s much easier to bang them on the first date.”

With that lesson learned, Logan soon decided to check out another website, the literal pay-for-play SeekingArrangement, buying a one-month introductory membership.

He put down his name: Logan.

Profession: web entrepreneur.

Net worth: $3 to $5 million.

Over the course of that month, Logan contacted as many women on the site as possible—a number he estimates to be between 300 and 500—and then steered those conversations to an alternate email account. That way, when his month was up, he could get to work.

“I just started going through their contact information like a menu,” he says. “What am I in the mood for tonight? Ethnicity-wise, it was like a Benetton commercial. Which was nice. I enjoy some variety.”

Pretty soon naked pictures were flooding his inbox, as prospective sugar babies vied for Logan’s attention—and his fake bank account. Were they all reckless fools? Maybe. But to his credit, Logan was a convincing character.