Awkward Moments in Porn 14

American History XXX

Awkward Moments in Porn 15

A baffling assortment of eccentric freaks so confusing out of place, you'll think you're watching the new Scream movie. There's a time and place for everything... except tag teaming a $1,000 dollar Queen's Blade figurine. That's a permanent no from me dawg.

Stacked and More Socially Awkward 18-year-old

You clicked the original one so many damn times, I had to dive deeper into her discography. Unfortunately it turns out all her roads lead to this evolutionary cul-de-sac using her as the only form of exercise he's seen since Jock Jams was a thing. Don't look that up. [-PART I-]

Insane Clown Pussy

Most erections flatline after muttering the letters "ICP". Maybe even translate into an episode of syphilis or three. But not here. Enjoy this one slowly... for today Holly Hendrix proves without a shadow of a doubt that everyone with her last name is a natural-born musician.

THAT DIDN'T END WELL

Cop Porn is Hilarious

From the creators of Bang Bus come's a new ride along porno trip. Witness angry female cops hunting the city of Miami to sexually exploit the black population. #BlackCocksMatter

Finga La Pinga

Hank Hill, I think your problems have been solved.

Stacked and Socially Awkward 18-year-old

Admittedly the carb walrus she's costarring with may have her beat in the embarrassment department, but she's not far behind in this race. If anything at all for offsetting what may be the greatest set of natural tits ever documented by having the face of Jaden Smith. It can not be unseen.

The Show Must Go On

Playstation One-levels of animation and someones first experience with Windows Movie Maker goes horribly... right? In other words, I only ejaculated twice. And that's coming from a man whos seen Sarah Silverman naked. My voice matters.

Shit T-Girls Say

If attempting to monetize your most private confessions is any sign of a recession, I'd say we're at the tip of an iceberg that would make the dotcom bubble look like like an afterthought. I'll be expecting a lot more of this until Jim Cramer capitulates.

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.

Awkward Moments In Porn 16

There's a lot to digest here. But nothing is as concerning as whatever rodeo clown, double-wide uncle sister bullshit is going on around the 3:11 mark. Axe body wash isn't going to clean this feeling off me tonight. Time to dip into the disaster emergency kit.