FAIL: Teacher Attempts Double Anal

4,741,230 views

Deleted scene from Un-Natural Sex 20 involving an ex-teacher looking to sacrifice the health of her colon in exchange for fame & fortune (aka $728 and maybe, just maybe, a Q&A with Swank magazine). Epic spoiler: things don't go as planned.

Uploaded 08/31/11 Fail

anal, fail, funny, pain, shit talk

Tiffany Six
Related Videos

YOU'RE DOING IT WRONG

Here's some wisdom I picked up while watching an infomercial for Tony Little's Gazelle Sprintmaster - always maintain good form. Sloppy form is how people get Christopher Reeve'ed. Don't think the same is applicable to sucking dick? Neither did she.

3,441,939 views 03/15/12 EvilAngel Fail

Random Guys Try to Fuck a Pornstar

Do their porno dreams come true? Fuck no. Instead, four average-ass mother fuckers attempt to make sex with the prestigious Christy Mack, and each and every one of them brutally embarrasses themselves.

5,365,704 views 03/10/17 Bang Bus Bang Bus Chronicles

The Absolute Worst of Pornhub V

A rousing assembly of women that don't believe teh night is over until their clout levels have reached unmeasurable proportions. Reminiscent of a reoccurring dream I keep having involving Brock Lesnar and Long John Silver’s Cocktail Sauce.

1,454,160 views 06/15/23 The Worst of Pornhub

The Legend of Saint Petersburg

Congratz! Local Russian folklore states that if you are visited by the naked battle gypsy of St. Pete you will be forever blessed by good fortune. Don't look directly at her vagina though, or they say she'll curse you with impotence.

1,258,104 views 12/18/14 Exhibition

Cucked by a Pornstar

Arnost and his 1 inch mosquito bite take a nosedive into humiliation whilst trying to perform in front of a live studio audience. Sorry friendo, but I think it's best you take that CHUD haircut and make your way back to the subreddit you done crawled up out of.

2,632,599 views 10/11/17 Mea Melone Challenge Fail

Wallflower Fucks Up Orgy

You ever show up for the orgy but just jerk off by yourself? Or have you ever managed to be cringier than a wannabe white rapper with a pick in his ginger afro? Yea... me either. YAY!

2,796,142 views 04/04/17 Bangbros Fail

The Future of Fucking

One country's quest for sexual satisfaction reaches it's peak, courtesy of a build-a-bear workshop for egg-drop rice boxes. It's hard to turn a blind eye to this actually being possible in 2020, but make sure this technology never makes it's way to Florida and you got yourself an investor.

1,437,751 views 10/23/20 Asians

Passion of the Painal

Whore #3 is quite adorable. She may not understand the consequences, but her facial expressions certainly have a story to tell.. namely "ouch, that hurts", "please hurry up" and "why in the fuck did I quit my job at Hotdog On A Stick for this shit". Live and learn baby.

9,418,816 views 09/07/12 Favorites

O MY FUKING GAWD

OMFG

3,442,221 views 06/26/16 HardX LULZ

Public Degeneracy Volume 6

Turns out there's absolutely no shortage of individuals that consider teaching their penis the macarena a societal norm. A Superb technique no doubt, but probably not for beginners. Chances are you'll misjudge one 360 no-scope and catch a local in the crossfire. It's called "The Ben Roethlisberger" and it'll make you wish you kept the half boners at home.

2,484,146 views 09/05/22 Public Degeneracy

A LITTLE TOO REAL

32,679 views 04/28/24

Quitting is Not an Option

I've seen this configuration before. Okinawa birth certificate, Chevy-Silverado endurance. I'd refer to Alexa for a proper translation, but Amazon hasn't released the Aspergers DLC yet so you're just gonna have to fill in the blanks yourselves, compadres.

2,173,455 views 11/16/19 Asians
Type ? for random video