Hipster Slut Gets Unexpected Anal

6,866,877 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 HOLEZ: 2023

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

1,457,574 views 11/23/23 Wrong Holes

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.

7,196,602 views 01/22/12 Wrong Holes

Luckiest Guy at the Strip Club

In the bowels of Brazil a.k.a. the other other Mexico, a local stripper gives a drunk and weary traveler an experience he'll never forget... if he can remember. He goes home with a dildo souvenir so he'll definitely know something went down that night. #YOLO

3,237,267 views 05/08/14 Public

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.

5,241,802 views 06/26/13 Wrong Hole

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.

1,737,557 views 10/24/22 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.

3,669,308 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.

4,088,339 views 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.

6,626,661 views 03/26/13 Cumlouder Wrong Holes

MARRIED MEN DESTROY ESCORT

8,498 views 05/05/24

Awkward Moments in Porn 13

Pork sword bros break the first rule in Ghostbusters 101, clown horn honking gets a new identity and whatever the fuck fight the girl at 1:12 is practicing for is something I feel should be featured on this site in the future. Somebody fetch my finest Walmart polyester linen, I wish to ejaculate.

2,106,875 views 06/16/22 Awkward Moments In Porn

Unacceptable Devices VI

Before you ask why the mutant at 1:05 is included, I want you to take a good long look at that weapon of mass destruction. With those dimensions you'd think his question mark lookin ass would be too busy fighting Peter Pan instead of driving the female community to abstinence.

1,976,767 views 05/25/23 Unacceptable Devices

I Got A Husband

From the bowels of world star hip hop comes a little gem that's straight outta Compton! Staring a wild wildebeest that has been caught fellating a local hoodlum in the middle of the street. Some real ratchet shit yo!

3,016,756 views 02/28/15 Amateur
Type ? for random video