BOOM! Your Ass Is Busted!

What happens when you put a huge cock and a tiny asshole together and shake it up a whole bunch? Prolapsicus maximus, that's what. I never finished med school but it's my professional suggestion that she pick up a pack of band-aids on the way home.

Uploaded 12/12/08 Fail
Related Videos

Incredible Acts, Depraved Humans 10

Time to get acquainted with another horde of beatniks that have managed to monetize the kind of performances that once only existed behind the locked doors of a Berlin basement. Big points for that Mitzuwana breakdancing at the 6:12 mark though. Should have taken home Paris gold. More: [-1-] [-2-] [-3-] [-4-] [-5-] [-6-] [-7-] [-8-] [-9-]

Probably the Most Dangerous Sex Tape Ever Made

Commit to a blind date in the state of Florida, and I'd say you got about a 98% chance of matching up with a person that dispenses more threatening fluids than a Mountain Dew vending machine. And today my friends, you're gonna learn that the hard way.

Pornstar Accidently Pukes on Fellow Actress

The pharyngeal reflex AKA laryngeal spasm AKA gag reflex exists to prevent us from dying, but it also makes it much harder to shove dicks down our throats.

07/24/16 EvilAngel Fail

Butt Sex Claims Another Victim

Every girl should know that a slippery fuck toy plus a cavernous butthole can equal a trip to the ER. Next time save yourself the embarrassing shuffle through the waiting room and tie a string to that mother fucker.

10/07/13 Insertions

Breakdown BEFORE The Anal?

We're about to document the dream of a girl that's had more sexual partners than Tom Brady's 2022 passing yards, or create the gentleman's guide to recreational pharmaceutical use. Either way: NO REFUNDS.

18YO TRYHARD

03/03/26

The Caught Compilation 14

4+ minutes of public debauchery so misunderstood, you'll wonder how long it will be until Amber Heard drags them in front of a judge. Especially that duo clapping cheeks arm's length away from the bratwurst dujour around the 0:49 second mark. Just marvelous.

Hilarious Oral Sex Fail

College level alcoholism and risk seeking behavior has led them to a ratchet motel, wasted off vodka red bulls and making a quick $100 each. Shouldn't be any surprise that these girls never did porn again.

01/23/15 NebraskaCoeds Fail

Stacked and Socially Awkward 18-year-old

Admittedly the carb walrus she's costarring with may have her beat in the embarrassment department, but she's not far behind in this race. If anything at all for offsetting what may be the greatest set of natural tits ever documented by having the face of Jaden Smith. It can not be unseen.

Safe Sex FAIL

Gloryhole rookie "Emma" unequivocally accepts defeat after Stewart's Magnum XL ventures into deeper waters. In other words: The flex went wrong HAHA

100-Man Gangbang Doesn't End well

Nevermind the fact that she talks like a slightly upgraded version of Stan's sister. What I really want to know is where this current trend of bodily fluids being used as a sole protein source started from. And I want to know now.

Type ? for random video