Not necessarily the weirdest, but the one that weirded me out the most at the time: Me and my best mate/jerk buddy in early HS before the age of "tube" sites, we got all our porn via p2p. We're like "let's check out what this gay porn is all about" ...

Nice

We dl it and it's a dude somehow taking thigh sized dildos on a fuck machine. I think it broke both our conception of the laws of physics and minds for a good several minutes We later settled on a tried and true straight blowbang video we'd nutted to countless times already