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.

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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.

01/22/12 Wrong Holes

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.

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 Caught Compilation 14

4+ minutes of public debauchery so misunderstood, you'll wonder how long it will be until Amber Heard drags them in front of a judge. Especially that duo clapping cheeks arm's length away from the bratwurst dujour around the 0:49 second mark. Just marvelous.

She Fucks Moolionairs

Fangirl shits pinecones after overhearing pornstar Brian Pumper refer to her as a 'bitch'. Blows are exchanged & shit gets ugly, but the real battle is all verbal, with ego-busting insults like "u think i wud tweet about u? I FUCK MOOLIONAIRES NIGGUH". Fucking brutal.

05/15/12 LULZ

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.

12/18/14 Exhibition

HUMILIATED By An Anal Virgin

Our boy successfully pulls off one of the audibles taught in Bang: More Lays in 60 Days, but the tables quickly turn on him. From then on it's a battle of egos as this greenhorn frolics through her first rear admiral'ing like it's a full body massage. There won't be a sequel.

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

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.

WRONG HOLEZ: 2023

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

11/23/23 Wrong Holes

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.

06/26/13 Wrong Hole
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