The Accidental Anal Compilation

Not much is worse (or funnier) than an unexpected penis bashing some hoer O-ring with little forewarning or lube. Ideally, zero forewarning and zero lubes.

Uploaded 04/09/17 Painal

anal, fail, funny, pain

Kapri Styles
Sources: 1, 2, 3, 4, 5, 7, 8, 9
Related Videos

WRONG HOLEZ: 2023

The only appropriate video to post on a day where the family gathers to stuff orifices.

11/23/23 Wrong Holes

INCREDIBLE: 3 Orgasms in 90 Seconds

A truly beautiful ballad about a girl that makes pterodactyl sex noises and a man that pulls off one of the most amazing sexual achievements ever filmed. I think we all wish we had a little Jimmy in us.

Lana Rhoade's Biggest Regret

Contrary to appearance, leading role in the 2017 cornhole apocalypse was not her specialty. Now that she's retired, you could say her talents were more wasted than season 5 of The Walking Dead. Regrets are temporary. Mike Tyson uppercutting your sphincter in the 3rd round is forever.

07/05/21 Painal

Prostitute Lasts Only 28 Seconds

Technically she lasted closer to 10, but this guy isn't very fluent in "NOOOOOOOOOOOOOOO", so that mahogany-stained browneye got pounded for a few more Missippi's than desired. Emphasis on mahogany-stained .

IT LEAKED?

07/23/25

101 Asian Stripper Tricks

Welcome to the far east, a place where vaginas are never shaved but always multi purpose. A place where a nice business man can get a sake and light a cigar off a strippers vagina. Fun times.

02/29/16 Asians

WRONG HOLEZ: 2020

It took years, but we finally have another worthy entry for the museum of unintentional rectal breaching. I'm talkin 3.5 nonstop minutes of backdoor bruising that white people should only experience inside the CHAZ zone. Only difference is the people in this video actually put meat inside their bodies lol.

06/19/20 Wrong Holes

First Time Anal Ends In Tears

AKA "How to fuck teenagers for 60% off." So a little burnout QT3.14 thought she could get some extra weed money for some anal. Only problem is she's never done anal and has no idea the hurtin' she's in for.

05/06/17 Broke Model Painal

Wrong Hole... LIKE A BOSS

Lulu Love gets an unexpected, unwanted invite to a Turkish bike ride. Likely due to this rectal romeo giving more fucks about where his third supper is coming from than what he's aiming at. In other words: he tried to find da wey and it failed beautifully.

The Anal Full Nelson

When an Azn teenager is reluctant to finish getting ass fucked, it's this guy's cue to utilize a pro-wrestling style submission maneuver and ride it home. Featuring acting so good Kirk Cameron would shed a single tear.

01/23/14 Favorites

WRONG HOLEZ: 2022

So you think Dr. Phil has covered all the bases of marital disasters? Well it's time to reevaluate bitch. These pioneers of female empowerment do it all. And by all I mean everything except give us the long awaited sequel to Karen's Krapper: Volume 27. Alexa, play Big Bottom by Spinal Tap.

10/24/22 Wrong Holes

The Cum MASTER

Real? Deceptive editing? The Goku of premature ejaculation? I don't have the answer this time. But just imagine if he went even further with this talent. Plan-B's entire industry would need emergency funding.

Type ? for random video