Joseph Gordon-Levitt stars as a teenager who hustles to make his way through life. Sounds pretty standard, until you start seeing Levitt’s cock get bruised by an older guy who gets too excited while going down on him. If that doesn’t do it, watch Levitt’s face as he struggles with crabs or after he’s raped by an overzealous “client.”
No, not the Paul Haggis flick that tells you how bad racism is, but the 1996 David Cronenberg film about people who get off on car crashes. Watch for the scene where Peter MacNeill dresses up as Jayne Mansfield only to crash his car in order to reenact her fatal crash in the ultimate masturbatory act.
While not nearly as explicit as the first two films on this list, sex in Mike Leigh’s Naked is so grim that you can only walk out of the film wondering what the hell we do it for. The film opens with Johnny (David Thewlis) raping (or is the sex just rough?) a woman and ends with Jeremy (Greg Cruttwell) raping Sophie, Thewlis’s eventual love interest.
A Clockwork Orange
Alex DeLarge (Malcolm McDowell) goes on a spree of sex and “ultraviolence” in Stanley Kubrick’s bleak film about a dystopian near-future. While the scene where he rapes a writer’s wife while singing “Singing in the Rain” isn’t nearly as chilling as it probably was in the ’70s, the juxtaposition is enough to make someone that was once satisfying into something horrifying.
The painful and horrifying things Charlotte Gainsbourg does to her own and Willem Dafoe’s genitals in this film are enough to kill anybody’s boner basically forever. You’ll never look at a block of wood or a pair of scissors the same way again.