Hipster Slut Gets Unexpected Anal

6,870,094 views

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.

Related Videos

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.

5,245,829 views 06/26/13 Wrong Hole

The Most Beautiful Breakdown Ever

These two carpet munchers soul mates engage in dikey lesbo sex make passionate love and after cumming her brains out, she breaks into happy tears.

3,383,217 views 11/05/13 Elegant Angel Breakdowns

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.

7,203,032 views 01/22/12 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.

6,632,863 views 03/26/13 Cumlouder Wrong Holes

WRONG HOLEZ: 2023

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

1,471,699 views 11/23/23 Wrong Holes

First Sex Toy In Space

We as humans are at the fuckin' highest point of civilization we've ever achieved. Our technology is more advanced than ever before in history and recently, we put a dildo in orbit... Welcome to the new age.

1,055,191 views 10/23/13 Bizarre

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.

1,746,418 views 10/24/22 Wrong Holes

The Only Olympics I'm Watching in 2024

I wasn't intending on the ambiguous crossover of Tokyo and The Kentucky Derby to make my boner list... yet here we are.

1,021,337 views 02/23/23 Asians

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.

3,675,419 views 01/24/18 HeavyOnHotties Wrong Holes

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.

4,097,235 views 06/19/20 Wrong Holes

THIS WON'T LAST 24HRS

9,576 views 05/16/24

Don't Care, Had Sex

There's just no going back after making a video like this. She'll be forever known as the degenerate that got famous for rawdogging a South Park character. She's essentially a walking, talking Twitter activist for borderless sexuality... and yet stays in semi-boner material territory. An enigma, if you will.

3,665,044 views 10/08/19 Mildly Retarded
Type ? for random video