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Porn Newbz Anal Fail

Former ISIS member with gigantic, fake wonky tits does her first porn shoot ever and she's about to learn pornography isn't all smiles and blowjobs. Nope. Sometimes it's about butt-plugs and pain.

9,106,543 views 12/15/14 Mia Khalifa Favorites

BUT DADDY IT HURTS!

Backpage's finest goes by "daddy's baby anal queen" and she aspires for greatness via her butthole. The only problem is she hates anal and her possibly worm-infested colon is so tight, it's like trying to fit an elephant in a Safeway bag.

3,276,742 views 03/26/14 Broke Model LULZ

Butt Sex Sends Poor Girl to the ER

Every dirty slut should know that a slippery fuck toy plus a cavernous butthole can equal a trip to the ER. Next time save yourself the embarrassing shuffle through the waiting room and tie a string to that mother fucker.

2,923,201 views 10/07/13 Insertions

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.

5,330,545 views 06/26/13 Wrong Hole

A Different Kind of Painal

Jackass-inspired stunt involving a weapons-grade slingshot and some cactus goes horribly right when the target, (a gypsy woman's anus), is met with a direct hit. And now I'm met with a direct boner. Circle of life.

5,584,800 views 05/29/13 Favorites

How To Harass An 18 Y/O Into Doing Anal

I've heard a lot of desperate men say a lot of desperate shit just to keep their cocks submerged in teen sphincter.. but to essentially give a girl the greenlight to defecate on your penis just to avoid a 3 min. potty break? That's a level of dedication I hope to never know.

5,910,290 views 05/06/13 Painal

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 .

6,216,795 views 04/06/13 YourNextDoorWhore Painal

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.

6,767,987 views 03/26/13 Cumlouder Wrong Holes

Her G-Spot Is In Her Butthole

This actually starts off as a painal vid, but much like Cuba Gooding Jr.'s acting career, that only lasts for about 14 seconds. From there on it's all pleasure, and by 'pleasure' I mean nervous system-disabling assgasms so hot even Stephen Hawking would pop wood.

7,794,453 views 11/30/12 Double View Casting Favorites

Passion of the Painal

Whore #3 is quite adorable. She may not understand the consequences, but her facial expressions certainly have a story to tell.. namely "ouch, that hurts", "please hurry up" and "why in the fuck did I quit my job at Hotdog On A Stick for this shit". Live and learn baby.

9,571,127 views 09/07/12 Favorites

Broken Dreams, Broken Buttholes

Compliments aren't my strong point, but I must say... chick in the yellow dress is fucking stunning. I'd readily eat Honey Nut Cherrios out of Philip Seymour Hoffman's crusty asshole just for a chance to hold her hand. Someone Russian please hook it up.

6,289,195 views 08/03/12 Favorites

The Milf From Mars

Bittersweet painal, obscenity-filled ogasms, and a boob job pre-dating the birth of jesus. This ones got it all, and Ms. Big Ole Leathery Funbags earns some serious bonus points at the 2:35 mark.. Not even a fuckin rectal injury can dull her desire for ATM.

5,130,160 views 06/25/12 MomPOV Mildly Retarded

You Want To Quit... FOR REALZ

B-hole brutally wrecked at the hands of some Italians, likely won't be able to walk straight for a week. No, this isn't my review for the new Parmesan Crusted Steak @ Olive Garden. This is the infamous Rocco vs. Roxy Jezel scene, and you should watch the uncut version via the source link.

5,931,464 views 05/07/12 Painal

Teacher Of The Millennium

She's junior college educated, has a rack to premature ejaculate for, and isn't afraid to slob on the knob after her partner takes a trip to cornhole city. Superintendent Jackoff & Co can hate all they want, this angel is a keeper. Read the story HERE. See her nastiest videos in the source.

4,733,440 views 03/09/12 LULZ

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.

7,333,489 views 01/22/12 Wrong Holes

PAINAL: I Wont Give Up!

It's all fun n' games till you got a 14 inch dong knocking on the pearly gates of your anus. The pain hits her like a bag of Saved By The Bell VHS tapes, but this trooper refuses to quit. Some might call it desperation for a quick $450. I prefer the term 'integrity'.

5,827,683 views 12/19/11 Painal

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.

6,930,870 views 06/06/11 Bangbros Wrong Holes

Wrong Hole, Charlie Brown!

Persian girl gets an accidental, no-lube blow to the rectum... most likely due to her male counterpart having the gut of a pregnant woman and not being able to see what the fuck he's aiming at. Or in other words... he tried to no-scope it and failed wonderfully.

5,319,179 views 04/26/11 Totallyannette.com Wrong Holes

Porn Noob Pwns Himself

Big fat curved penis sends a fresh wad of home cooked Twinky filling right back into the face of it's creator. It's not a problem I expect to incur any time soon but I do retain faith in the bottle of Extenze my sister so kindly purchased me last xmas. Similar videos HERE & HERE.

2,828,920 views 04/19/11 Fail

Priceless O-Face

Another one of those videos where some pornstar is left flopping around like Terri Schiavo on speed after experiencing the Optimus Prime of all orgasms. This chick takes it a step further, introducing Human Bobblehead Mode at the 1:55 mark. All sorts of awesome.

4,888,218 views 01/09/11 Device Bondage Ridiculous Orgasms
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