Hipster Slut Gets Unexpected Anal

OOPS! Wrong Hole!

I'd be pretty amazed/disappointed if that didn't at least cause a little internal bleeding. Emphasis on disappointed.

THIS WON'T LAST 24HRS

The 18-Second Man

My first pay-to-play happened in a Burger King toilet stall. She was more Kurt Perry than Katy Perry, Kinda foul. Not even a triple replay of Heather Graham's bush in Boogie Nights changed the mood that night. But... if I had this guy's attitude? Life... life would be different.

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.

OOPS! I Stabbed Your Cervix!

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

The Rarest Amateur Video on Earth

You'll notice a piece of this was already in BB4. Once I found out who this girl was, the deep dive had to begin. These are clipped from what's left of the only couple I've ever seen actually wipe their history off the Internet. They were masterbrookssub, and all that's left is a few tumblr remnants of them trying to market what I can only refer to as "Chris Brown Porn".

I don't remember this in RoboCop

Turns out the 1987 original was supposed to be even more violent. With the new remake getting a PG-13 rating, with it comes the almost certainty to destroy the ultra-violent badass awesomeness of RoboCop and change him into a safe for kids metal pussy. Source: Ourrobocopremake.com

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.

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.

Wrong Hole - OOPS!

Pee Wee needs to bring a flashlight next time so that he can better navigate the path to her vagina.

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.

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.