18. AMANDA SEYFRIED, AMBER HEARD, AND ANTON YELCHIN IN ALPHA DOG (2006)

We couldn’t dream up a better “first time” if we brainstormed after watching a Sasha Grey movie marathon. Alpha Dog doesn’t end well for Anton Yelchin’s character, but he does get to experience his first round of intercourse inside a pool with two incredibly hot blondes (Amanda Seyfried and Amber Heard, before either’s name was recognizable).

But that’s not all, folks. Not only does he get two-for-one, his threesome partners are a few years older, giving him something to brag to his young friends about, had he survived the film. The remainder of Alpha Dog after this chlorine-thick act of physicality ends is rather bleak and pretty tragic, but we’ll give the filmmakers credit for prefacing the darkness with the dripping wet pair of Seyfried and Heard.