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

I Haz a Breakdown

Scene's over and it's time to go home... but first this starlet has a complete mental unraveling. Her tears and plight do little more than generate awkward lulz and kill the mood for the next girl.

04/11/14 LULZ

Violated By The Elderly

Nice face. Amazing body. It's the the choice in coworkers where she starts to lose me. To each their own, but personally I would prefer my sexual fantasies to have as little to do with osteoporosis as humanly possible. Bonus lulz at the [3:28] mark when our boy almost checks out mid-nutshot.

07/15/24 Bangbros LULZ

This is Normal in Japan

If you're the kind of person that can enjoy peak sigma male behavior, then this is the video for you. I'm talking the kind of blueprint that guy who used to dress up as a latex demon and run into the woods to shove leaves up his ass couldn't follow. (seriously, email me if you remember his name. iykyk) More HERE

04/07/22 LULZ

Lost My Virginity To A Pornstar

He came packing a mullet, social-awkwardness and the body type/skin tone of a marsh mellow with prescription glasses. But that day back in 1998, he was a hero for 10 minutes at a gentleman's club in Arkansas.

10/20/13 LULZ

Awkward Guy Ruins Porn Shoot

A socially inept goober gets a job getting jerked off by a hottie and manages to fuck it up, dashing his dreams of porn stardom in the process. It's like the movie Rudy, if Rudy was thrown out the game before ever playing and never scored.

12/03/13 LULZ

Awkward Moments In Porn 3

If you haven't already, check out the rest of the series and then come back. We're going to meet a girl who has never blowjob'd before, plus a man who has a breakdown. While fucking a cake. So go get your little sister 'cause it's gonna be a really swag time.

OOPS! I Stabbed Your Cervix!

Some "feels" I am glad I will never experience in life. Driving the speed limit, menstrual cramps, bamboo fingernail torture, or when a unlubed and unwelcome penis randomly kicks open the door to the house of pain.

06/26/13 Anal

Seriously what the fuck is that

Skig tag? Krang from TMNT? Fuck if I know, but whatever it is... it totally rubbed up against the other dudes thigh at the 1.38 mark, causing a half chewed Bagel Bite to be ejected from my mouth and on to my Where's Waldo themed keyboard.

08/19/12 LULZ

Anal Virgin Almost Has A Breakdown

Meet Luciana. aka Timea Bella. aka Indisputable Liar. She claims her stink whistle has less mileage on it than the Peloton in Ozzy Osbourne's basement, yet doesn't even call a timeout when Woody goes straight to the A. But when it comes time to sample some French vanilla, she calls it quits. Stay tuned for part 2 where I'll showcase her triumphant comeback.

Porn Scenes Worthy of an Oscar 7

Saw X will be out by the time this is posted. You can't name 5 ways it's better than this. #bet

The Most Talented Girl In Russia

Moscow drug mule gets into a personal world war with her own rectum, most likely the result of an all kholodets diet (look it up). Jiggy Saw himself once said: "When there's that much poison in your blood, the only thing left to do, is shoot yourself." In other words; She attempted to no-scope and succeeded beautifully.

01/11/24 Loose

CAUGHT CHEATING

02/03/26
Type ? for random video