Awesome Fail

I don't know whats more fucked up: the fact that he's boning a woman older than dirt or how the enjoyment he gets from it leaves him socially retarded and unable to saying anything more than "AWESOME!". This is what happens when you use Craigslist to get your dick wet you dirty motherfuckers.

Uploaded 07/26/10 LULZ

fail, funny, home made, nasty, old

Related Videos

Stronger than Viagra

Found this gem in the Italian film "Capodanno in Casa Curiello", which roughly translates to "New Years at Grandpa's House". Think combining the gothic undertones of The Adam's Family with the threatening erections of Boogie Nights wouldn't work? You thought wrong faggit.

07/17/17 LULZ

Awkward Moments In Live Streaming

It's that time once again to highlight some special times in webcam hookerdom. Witness e-prostitutes having breakdowns, getting attacked by small reptiles and other awesome wtfness.

Awkward Moments In Porn 4

Special shout out to clip #12. For those of you that have never had the luxury of riding a San Fransisco BART train between the hours of 12:00AM and 11:59PM, you just got second hand experienced special delivered by Aunt Jemima herself.

Porn That Shouldn't Exist: 7

If anything at all this should educate you on what shouldn't be considered a sex toy. Like, ever. More here: [1] [2] [3] [4] [5] [6]

12/04/25 WTF

OOPZ, LOST TEH DILDO

Losing an 8 inch dildo in in a girls ass can have some consequences beyond fecal flavoring. If you can't get it out, the shoot is over and it's an awkward trip to the hospital with an unhappy porn star.

02/04/14 21Sextury Fail

Awkward Moments in Porn 9

Today we're rounding third on a baker's dozens worth of boner-deflating cringe collections so bleak, you'll wonder what the point of sexual intercourse even is anymore. Just load up one of those Choose Your Own Adventure Hentai VR fantasies, and fuck the Hamtaros out of a face-swapped Charizard until you feel alive again.

Her First Squirt

A heart warming moment when a pretty camgirl who happens to sound like MadTV's Stuart, drops jaw and flips her shit when she unexpectedly squirts for the first time in her life.

Societal Decay Episode 2

Round #2 in a series that showcases the authentic side of some of our most interesting citizens. I'm not exactly sure what life choices have to be made to end up here, but it probably has something to do with blue checkmarks and whatever they put in those Impossible burgers.

02/18/21 LULZ

Crushed Dreams Of Porn Stardom

These guys thinking they have what it takes to be porn stars makes as much sense as the story line for "Sharknado".

07/18/13 FuckTeamFive LULZ

Heavy Fucking Metal

GWAR has been real quiet since this dropped...

01/05/26 Beef Curtains
Type ? for random video