First Time Anal Ends In Tears

4,323,466 views

AKA "How to fuck teenagers for 60% off." So a little burnout QT3.14 thought she could get some extra weed money for some anal. Only problem is she's never done anal and has no idea the hurtin' she's in for.

Uploaded 05/06/17 Painal

anal, cry, fail, pain, shittalk

Related Videos

HERE COMES THE PAIN

2,278 views 05/05/24

Bad Boyfriends 1

The upside to being treated like the exhaust pipe of a Chevrolet El Dorado? Literally nothing. All you have to do is breath and the alpha male fantasy fan fiction will magnetize to you like a herpes outbreak at a Playboi Carti concert.

2,751,558 views 03/21/22 Bad Boyfriends

Bad Boyfriends 2

Dude at the 2:00 mark must have went as Apocolypto for Halloween in 2006 and forgot to take the costume off, and I have no doubt our Scottish socialite's rectal contractions look like they just graduated a course in sign language. Go ahead and tell me nice guys actually do win again?

2,302,545 views 11/10/22 Bad Boyfriends

The Caught Compilation 17

Introducing you to another gaggle of misfits that have managed to find active railroads, public highways and stranger's garages erotic enough to keep the erections at maximum stiffness. Extra points on that last clip, for our hero having enough restraint to not set anyone on fire.

1,574,028 views 01/26/23 Caught Compilations

CAMTASTROPHES #12

I was going to surreptitiously tag one of these girls as "Funky Town" to see how many newcomers Google "funky town porn" themselves right off the Internet for a while, but I choose a more honorably path at the last moment. So what did we end up learning today? Sharp objects and SNES soundtracks work extremely well together. That's what.

441,141 views 05/02/24 CAMTASTROPHES

Prostitute Lasts Only 28 Seconds

Technically she lasted closer to 10, but this guy isn't very fluent in "NOOOOOOOOOOOOOOO", so that mahogany-stained browneye got pounded for a few more Missippi's than desired. Emphasis on mahogany-stained .

6,109,020 views 04/06/13 YourNextDoorWhore Painal

HURRY UP and CUM!

UPDATE: this girl actually emailed me, here's the background story - she lives in a KKK-laden town where 12 inch black wangs are the forbidden fruit. Undeterred, she sought salvation on blackplanet.com and ultimately bit off more BBC than her vagina could chew.

9,670,381 views 02/17/12 Amateur

Sit Your Whore Ass Down!

Original video HERE.

3,313,926 views 02/21/12 Exhibition

Anally Destroyed French Milf

Another edition of "anal goes wrong", featuring the perforation of a fuckable milf's blown out colon. The city of love probably hasn't seen this much blood since someone made some cartoons last year.

3,008,384 views 11/13/16 Painal

18 Year Old's First Scene Ends Horrifically

It's not like Woodman sending 18 year old girls to the Depends section at Super Walmart is some sort of secret, so one has to question the motives at this point. Is it an act? Are they sadomasochists? And most importantly: If Ronda Rousey were to crowbar her vagina open, would it be comparable to the consistency of pulling apart a peanut butter sandwich?

505,939 views 04/29/24 Woodman Casting X Teen

High Maintenance

Her claim to fame is deplorable... but when the clothes come off her barbarian hips look like they can survive giving birth to Danny Devito and it's fuckin' beautiful. 5/5 Yelp stars, would eat again.

3,036,785 views 12/17/18 Vintage

18 Year Old Suffers O-Ring Blowout

Don't worry, in a few days she'll be sitting and shitting normally. Just gotta put some icy-hot on her hurt butt and eat a lot of fiber. No worries.

5,654,913 views 08/28/16 Painal
Type ? for random video