FAIL: Teacher Attempts Double Anal

4,741,994 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

Spitters and Quitters 2

So, what exactly are we witnessing here? First attempts at delivering the beat down in meat town? Nervousness? I don't know for sure... but think of all the value meals this skill could unlock if practiced with the right discipline. 5 seasons of Cobra Kai taught me that. [PART I]

1,210,016 views 11/17/22 Cum Haters

Public Degeneracy Volume 7

I gotta emphasis the "sOcIaL eXpEriMeNt" you're gonna see at the 2:00 mark. Normally this attempt at public depravity would be immediately thrown into the compost pile for wasting our time. But I'm told this lunatic is legit, and has a history of freebasing randoms along her journey. You and your Zappos membership can be the judge of that.

2,409,948 views 12/19/22 Public Degeneracy

"I WONT TELL YOUR WIFE"

8,241 views 05/05/24

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.

3,205,230 views 01/23/15 NebraskaCoeds Fail

CAMTASTROPHES #1

This is all but guaranteed to exterminate any story you've been led to believe that everyone in the webcam community is living life on easy mode. Snap back to reality with 5 disasters even FEMA won't pick up your phone calls for.

2,522,574 views 07/29/21 Chaturbate CAMTASTROPHES

Anally Destroying a Mentally Disturbed Teenager

This whole glorious scene is a beautiful train wreck and I can't fucking wait to hear a epic drum and bass remix of this. EDIT: [Remix #1] [Remix #2]

9,687,558 views 05/21/15 Teen Fidelity Favorites

Cucked to Tears

First time I've seen a wife rental video where the girl and her hired gun are left more humiliated than the husband. 7 1/2 inches of New Orlean's finest essentially left them completely mute, save for some sobbing that is usually reserved for the customer service desk at Lululemon. Hilarious.

4,022,690 views 02/07/20 Cuckold

The Caught Compilation 19

Everything in life has a proper explanation if you open your mind. Except the homie trying to scrub daddy his dirty walnut on a Tuesday afternoon in broad daylight around the 1:45 mark. NORAD will hear about this.

1,412,577 views 07/27/23 Caught Compilations

8 Uncomfortable Moments

Consider this an open letter to the content creators out there: I will donate the $13.75 I made trading Krypto Kittys with down syndrome to a charity of your choosing, in exchange for promising to never use condiments on your wiener ever again. The balls are in your courts.

1,020,310 views 05/18/23 Fail

My 400lb Life

Most erections won't make it past the fact that this Snorlax shovels in 5,000 calories per day - and trust me, it doesn't get better. Congratulations Tammy you've officially outdone Game of Thrones for most offensive climax of 2019. Fire up one of those burrito milkshakes, today we celebrate.

2,291,797 views 09/21/19 WTF

Condemnable Sex Tapes

If it wasn't for the guy getting his hot dog caramelized I was going to say society has gotten too soft on sperg-like sex acts that belong behind closed doors or in a WNBA locker room. I expect nothing less from citizens that look like Buc-ee's is their favorite restaurant.

1,075,509 views 10/19/23 Bizarre

Fan of the Year: You're Doing it RIGHT

Carl Sagan said it couldn't be done. Mythbusters ignored our requests to do an episode on it. But thanks to NEGATIVE DOLL we finally have definitive proof that fan videos can be fucking awesome #REACHFORTHESTARS

2,091,600 views 08/19/18 Teen
Type ? for random video