Hipster Slut Gets Unexpected Anal

6,864,673 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

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.

3,664,737 views 01/24/18 HeavyOnHotties Wrong Holes

Extreme Foot Fetish

Visit the dark side of podiatric porn. A dark, shitty basement with a custom made fuax floor complete with a penis hole. No one should have such a crazy thing, but this is no normal human being we are dealing with.

1,720,735 views 08/24/15 Extreme

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.

6,621,793 views 03/26/13 Cumlouder Wrong Holes

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.

1,731,173 views 10/24/22 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.

4,082,276 views 06/19/20 Wrong Holes

WRONG HOLEZ: 2023

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

1,447,161 views 11/23/23 Wrong Holes

SHUT UP AND FUCK MY FRIEND!

167 views 04/28/24

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.

5,238,729 views 06/26/13 Wrong Hole

Elena Koshka Overloaded

Symptom #67 that you've graduated from pornstar to full blown drama queen: 3 pumps from Manuel Ferrara's ham hog makes her tap out faster than the Frank Shamrock/Kevin Jackson fight (look it up). Like my reaction after hearing Oprah Winfrey wants to run for president, you can literally see fear in her eyes.

1,856,095 views 11/01/21 Manuel Ferrara Fail

POWER OF CAWK

I feel like this has some deeper meaning than a porn parody of the exorcist. I just awed at it like it was a Salvador Dali painting or some shit, trying to figure out how my existence had brought me to this point.

1,851,706 views 09/18/17 Parody

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.

7,191,945 views 01/22/12 Wrong Holes

Greatest Amateur Sex Tape Fuck Ups

I don't know why anyone would post such things of themselves onto such a terrible place as the internet, but whatever! Come ride the shit train with me on a journey into the awful side of amateur pornography.

6,012,892 views 06/10/16 Amateur
Type ? for random video