Alfonso has trolled these listings more times than he can count. The Harvard sophomore even recently wrote an essay for the Harvard Independent, a weekly student newspaper, about the gay-sex Ivy League underground on Craig’s List. “This place is perfect,” he explained in the piece. “Anonymous, discreet, plenty of choice, no pressure to respond. Don’t have to worry about ruining my future in politics.”
“My love life has been centered around sex more than anything else,” Alfonso says later. “I talk to friends who’re dating people, and they’re like, ‘Oh, we haven’t had sex yet.’ For me, it’s sort of like the reverse. I’m like, ‘I really don’t know who he is, or what his name is, but ...’ ”
Alfonso wasn’t out in high school, so his predominant outlet for exploring homosexuality was the Web, where he found not only porn, but leads to real sex outlets at bathhouses and in public places. He now admits that his adventures from age 17 to 19 were a little reckless — “I could go out, pay $5, stick around for two hours.” — and started to feel like a “sort of double life. Like ‘Who was that? Did that really happen?’ You wonder.”
There have been a few awkward experiences. “There was one time I was horny to the point of losing my mind. And [I] decided just to place an ad and go with the first person who answered. It ended up being an older man — someone I would not have been into had I not been in that frame of mind. I just decided to go along with it. Afterward, I was wondering what the hell I did. But, you learn.”
Although Alfonso defines a sexual partner as “someone I’ve had sex with” (“Thirty? Thirty-five? At least?”), he confesses that if he’d measured that number by “people I’ve dated and had sex with,” the number would be much smaller. Like, five. But he’s in a relationship right now that has actually lasted for two months. “Recently, I’ve been trying to meet people more through other friends, or parties, and not, like, rush things too much. But it’s not as exciting.” On the whole, he’s been rethinking sex’s role in his life. “I’m wondering, what is sex about? What should it be? Should it be entertainment, should it be recreation, should it be something more?” In the end, he thinks it’ll probably be something more. “It will become exciting when you find that person in real life who makes it as thrilling as finding God-knows-who online.”
The freedom of “Queer Space”
Genderqueer, 37, 34+ previous partners (“Not including random hookups at sex/play parties, back alleys”)
Lia is a she but feels sorta like a he, even though the Boston resident has the anatomy of a biological female. She prefers the pronoun s/he, dresses in a “retro old-man” style, and tends to be attracted to more-masculine personalities, yet doesn’t plan on altering her/his organs anytime soon. “If I was going to change my body, I’d get a better ass,” s/he says, laughing in a high pitch that’s undeniably feminine. So Lia identifies as genderqueer — a flexible description for someone who doesn’t fit neatly into any sexual-orientation category.
