The Mad Men Star Who Had Sex With Her Gay Friend

Alison Brie already shines on Community and Mad Men. Turns out she’s a hilarious, ballsy writer too, as Nerve’s excerpt from an upcoming anthology on bad sex attests. Her subject: an aggressive bid to sexually initiate her gay male friend.

Let’s set the scene. Art school. The young Ms. Brie is, shall we say, feeling the experimental vibe:

Exploring my newfound sexuality, there was, of course, the girl-on-girl action, the crazy threesome with the afros and whips, and the surreal ‘shrooms experience where I thought the tree was fondling me but it turned out to be my creepy male roommate with calluses on his hands… gross. You get the picture. I developed this (possibly misplaced) sexual pride, based solely on the quantity of penetrations of my vagina… and not necessarily the quality of the acts therein.

When she learns that her gay friend answers “None, ewww” when asked if he has sex with men or women, Brie decides it’s a good idea to convince him to have sex with her, despite his evident discomfort. “And what if he were to discover he was actually straight? I would have saved him from a life of dysfunctional penetration. Literally my vagina would have been his road to salvation!”

On the bright side, Brie was not infatuated with her friend, as some women who have vainly hoped to “turn” a gay man have been. On the her-poor-friend side, he really, really did not see her vagina as the road to salvation. He didn’t want her to touch his penis. He wanted to get stoned first. He asked if they could drag the mattress into the closet (“I failed to see the irony at the time,” Brie writes). He wanted to hook up to Madonna’s “Erotica.” He panicked and thought the condom had broken, simply because of her natural lubrication.

Brie is an engaging, funny writer, and she is still on friendly terms with this guy (and he is still gay.) But, although I know they’re not exactly the same thing, it was hard not to imagine the queasiness one might feel if this were a story about Al, the horny college guy, trying to convince his confused, possibly asexual lesbian friend that his cock is her salvation.