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Horse Fucker

These porn producers, always so preoccupied with if they could, but never stopping to wonder if they should. I can't even imagine how awkward this scene must of been to film for everyone involved.

5,679,753 views 09/10/15 Bizarre

Goober Tries Not To Cum

It's only 10 minutes into the all night sex party and this douche is about to bust his nut after a 30 second blowjob. Not wanting to end the night early, he awkwardly death grips his penis attempting to cease climax.

3,520,755 views 08/30/15 DrunkSexOrgy Premature

Awkward Moments In Porn 5

Special shout out to clip #12. For those of you that have never had the luxury of riding a San Fransisco BART train between the hours of 12:00AM and 11:59PM, you just got second hand experienced special delivered by Aunt Jemima herself.

5,317,310 views 06/23/15 Awkward Moments In Porn

Awkward Boner

108,036 views 05/21/15

Pornstars Read Hatemail

I'm not totally convinced that all these girls have reached stardom. Also, I think Tabitha Stevens now qualifies for senior benefits, and one girl looks homeless, but whatever.

1,806,336 views 03/15/15 LULZ

18 Year Old Manlet VS Pornstar

An awkward 120 LB man-child thinks he has what it takes to make his porn debut with a pornstar that can't math. But even with the deer in headlights look in his eyes, he somehow pulls off the incredible.

12,237,367 views 01/02/15 Bang Bus Bang Bus Chronicles

Awkward Moments In Porn 4

If you haven't already, check out the rest of the series and then come back. We're going to meet a girl who has never blowjob'd before, plus a man who has a breakdown. While fucking a cake. So go get your little sister 'cause it's gonna be a really swag time.

4,395,809 views 11/07/14 Awkward Moments In Porn

The Emotional Limits of Pornstars

If you look closely you can see the very moment they realize that getting slapped around, tortured, humiliated and/or face fucked just isn't as much fun as it sounded when they signed up.

2,930,286 views 10/18/14 LULZ

Awkward Moments In Porn 3

"Fuck me in the ass based god", reluctantly said the state puff marshmallow woman, as he thrusted his black penis deeper into her gooey marsh-mallowy hole.

4,528,768 views 05/16/14 Awkward Moments In Porn

Pornstars Sexually Destroy Newbz

Watch these little engines that just fucking couldn't get a new hold on reality as God tier pornstars turn their sexual fantasies into humiliating nightmares.

3,929,879 views 05/11/14 FuckTeamFive Premature

Mindfucking the Delivery Man

The story of a hungry naked teen, an awkward handshake and a condom full of money. More of the blonde getting railed in the source link.

3,458,767 views 04/25/14 Broke Model Exhibition

I Haz a Breakdown

Scene's over and it's time to go home... but first this starlet has a complete mental unraveling. Her tears and plight do little more than generate awkward lulz and kill the mood for the next girl.

2,230,436 views 04/11/14 Breakdowns

OOPZ, LOST TEH DILDO

Losing an 8 inch dildo in in a girls ass can have some consequences beyond fecal flavoring. If you can't get it out, the shoot is over and it's an awkward trip to the hospital with an unhappy porn star.

3,678,052 views 02/04/14 21Sextury Fail

Awkward Moments In Porn 2

Like when you can't think of a description, cuz you realize everything you post is awkward... fuck.

5,671,301 views 01/17/14 Awkward Moments In Porn

Awkward Guy Ruins Porn Shoot

A socially inept goober gets a job getting jerked off by a hottie and manages to fuck it up, dashing his dreams of porn stardom in the process. It's like the movie Rudy, if Rudy was thrown out the game before ever playing and never scored.

2,839,769 views 12/03/13 LULZ

Lost My Virginity To A Pornstar

He came packing a mullet, social-awkwardness and the bodytype/skintone of a marsh mellow with prescription glasses. But that day back in 1998, he was a God for 10 minutes at a gentleman's club in Arkansas.

3,565,862 views 10/20/13 LULZ

Shit Pornstars Say 1

Lulz tier verbal diarrhea from the worlds top whores. It's a good thing emotional scars aren't visible on the outside or some these girls would look like Freddy Krueger.

3,551,450 views 10/09/13 Shit Pornstars Say

The Socially Awkward Teenager

When it's a girl's first time doing hardcore porn and she's too nervous on camera to put two syllables together, you get what I imagine to be the closest experience to fucking a corpse you can have without taking a trip to the morgue. Luckily the awkwardness only makes me harder.

5,987,426 views 08/13/13 Teen

Shy, Scared & Fucking Beautiful

Hot chicks + social anxiety. It's a phenomenal combination, second only to Mr. Pibb w/ Koala Yummies. Add a degree of sexual inexperience into the mix and you got yourself GF material, provided that they don't first end up in porn like this tard.

9,541,882 views 10/04/12 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.

5,130,120 views 06/25/12 MomPOV Mildly Retarded
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