Search results for amateur anal fails

Reset Search Page

Sexually Inexperienced And Terrified

True Blood's Sukki has a ratchet doppelganger that attempted porn and totally hated it. Her debut goes about as smoothly as a psoriasis break out... But unlike psoriasis she never came back and wasn't seen again.

3,936,204 views 12/22/13 Backroom Casting Couch LULZ

Ratchet Sex Tape Fails

Ratchet is what you get if a "ghetto hood rat" and a "chicken head" have a fatherless child that becomes a stripper or aspiring rapper with Tupac quotes for tattoo's and eight ratchet kids of their own.

2,300,733 views 11/18/13 LULZ

Ass to Mouth with Consequences

You gotta admire commitment in anything. This young lady was so devoted to the scene that when it came to anal, she soldiered through it. When it came time for the cum shot, she fellates his fecal flavored ram rod without hesitation.

4,303,029 views 08/31/13 Woodman Casting X LULZ

Hey Daddy, look what I can do!

Any college girl can pull off a DP, but to pull off near mythical feats of penetration you need a chick that's on a whole other level of promiscuous. Take Malibu Barbie over here, she can't even tell how many cocks are in her at any given time.

4,523,617 views 08/05/13 Elegant Angel LULZ

How To Harass An 18 Y/O Into Doing Anal

I've heard a lot of desperate men say a lot of desperate shit just to keep their cocks submerged in teen sphincter.. but to essentially give a girl the greenlight to defecate on your penis just to avoid a 3 min. potty break? That's a level of dedication I hope to never know.

5,910,459 views 05/06/13 Painal

Accidental Anal Devirginization

Unlucky Spanish chick gets bashed in the butthole - full force, no lube! Prepare yourself. The level of agony herein is second only to Adele handcuffed to a stair-master.

6,768,788 views 03/26/13 Cumlouder Wrong Holes

It's Only Smellz

Never have I seen a man do something so incredibly vile with such charm. Where there's tension, he provides laughter. Where there's pain, he provides comfort. And where there's feces on the tip of his penis... he provides dinner.

8,451,370 views 12/19/12 LULZ

Her G-Spot Is In Her Butthole

This actually starts off as a painal vid, but much like Cuba Gooding Jr.'s acting career, that only lasts for about 14 seconds. From there on it's all pleasure, and by 'pleasure' I mean nervous system-disabling assgasms so hot even Stephen Hawking would pop wood.

7,795,157 views 11/30/12 Double View Casting Favorites

14 Incher Causes Gianna To Quit

I've never seen Gianna cave before, no matter how big the cock. It's as if her vaginal canal is made of Teflon, with more square footage than James Van Der Beek's forehead. But after watching this, I'm not so sure.

12,061,535 views 04/10/12 Favorites

OOPS! I Accidentally Sodomized You!

If there's one thing that never fails to get a fuckload of clicks - it's videos of unexpected butt love. So here's 8 of em. That's right, EIGHT, as in the number of times I defecated after eating crab wontons at P.F. Changs. Enjoy.

7,334,714 views 01/22/12 Wrong Holes

YIKES! Chick Has Crazy Breakdown!

Poor chick. Freshly brainwashed by a 24 hour marathon of Pimp My Ride, she actually thought getting anally gangbanged by Jamal, Jamal, Jamal and Donatello would be fun. Thanks be to hemorrhoids, the reality check comes with the quickness.

3,594,243 views 12/05/11 Breakdowns

Asian Stoner Has Epic Ass

She's half Korean, half Mexican. That means she's pro at math and will have around 17 kids by this time next year. Not really. This girl actually just likes to smoke weed and take pictures of her massive ass - both of which are combined today in ways you cant even fathom. OOOOH YEAH.

4,196,955 views 11/23/11 LULZ

LOL: Dude Kills Fly During Rough Anal

I recognize the lisp. It's the same jolly fucker from 'HARDER! Or I Cant Cum' with the unhealthy obsession for rimjobs. Glad to see he's still living life to the fullest - I.E. using your penis to bait, trap and murder insects up some hot chick's asshole.

3,280,126 views 11/02/11 Fail

Gangbanged, Then Tears Of Joy

This is a scene from GANGBANGED 2. Blacks and whites combine penile forces for the greater good of ensuring Dana DeArmond's asshole will be forever loose. The interview that follows is quite interesting / fucking ridiculous.

3,329,636 views 09/28/11 Elegant Angel LULZ

FAIL: Teacher Attempts Double Anal

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.

4,778,344 views 08/31/11 Fail

Good Idea, Bad Idea

This one's a crowd pleaser. Not only get to see a massive-titted pornstar unwittingly suck a shit covered wang ... but you also to get hear three seconds of my real voice. Boner inducement on all fronts.

2,838,713 views 08/29/11 Fail

Anal Orgasms DO Exist

No stimulation of the clit. No vibrator in the pussy hole. This is a woman that can legitimately cum her brains out from nothing more than a good ol' ass pounding. God bless.

5,112,099 views 07/26/11 MyMilfStory.com Orgasms

Asian Girl Got Talent

She's blessed with the rectal capacity of Richard Simmons. Obvious perks: 1) balls deep penetration with Wesley Snipes 2) forgo any and all defecation for years at a time and 3) you get to be epic drug mule. Perk #2 is where it's at. Check out her myspace in the source link.

3,737,381 views 06/13/11 Asians

Did I Just Do Anal.... IDK

There's only 2 people in the world that cant tell when they're being anally penetrated. Stephen Hawking.. and this girl. She's 19, anti masturbation and dumber than a Billy Goat crossbred with Tila Tequila. She also wants to be a pornstar. God bless.

5,300,938 views 06/08/11 Backroom Casting Couch Fail

Hipster Slut Gets Unexpected Anal

Rylie Richman says she never does anal. IMO, that's about as probable as Amy Winehouse hosting the Indy 500 inside her vagina but okay. In this clip, she puts her internal organs to the test by fucking a black guy who's got a cock the size of an ewok. An already bad situation is made worse when said Ewok cock slides up the wrong orifice.

6,931,213 views 06/06/11 Bangbros Wrong Holes
Type ? for random video