Awkward Moments In Porn 7

Eight times pornography actually shocked me. Okay maybe just one time. Specifically #3. While the others have come and gone, this little gem remains unexplained.

Uploaded 06/21/17 LULZ

awkward, cringe, fail, 2017

Amber Rayne, Roxy Raye
Sources: 1, 2, 3, 4, 5, 6, 7, 8
Related Videos

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.

IT LEAKED?

07/23/25

Thot Hilariously Ruins Cum Shot

This is a pretty amazing scene right up until the point when it becomes one of the best cum shot fails of all time. Imagine the glorious feeling of having your penis sucked -- now imagine that feeling being destroyed right when it counts.

09/27/14 NubileFilms LULZ

Objectionable Porn That Shouldn't Exist

Somewhere in between the 493,000 Slavic back alley ganbang videos on the Internet, exists an even more offensive brand of content. Well let me tell you something chumps; Unless you're that fucking jetski level in Battletoads, I am disoriented by no man/frog. You, tho...

01/08/24 LULZ

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.

Literally Fucked Until She Can't Walk

First-timer foolishly assumes her debut appearance is going to be a walk in the park. Emphases on the word walk, because it looks like all her future tours of Italy at Olive Garden are going to be wheelchair accessible from this point forward. What in the fuck...

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.

Sex With A Paralyzed Girl

He turned on accessibility options.

01/23/25 LULZ

Incredible Acts, Depraved Humans 12

4 out of 5 physicians would advise against this kind of behavior, especially in public venues. But a life of chronic digestive and reproductive complications doesn't really seem to concern these prodigies. Big risks = more clout. And more clout = more fashionably retarded short form content.

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-]

The 18-Second Man

My first pay-to-play happened in a Burger King toilet stall. She was more Kurt Perry than Katy Perry, Kinda foul. Not even a triple replay of Heather Graham's bush in Boogie Nights changed the mood that night. But... if I had this guy's attitude? Life... life would be different.

06/27/19 Big Dicks

cRaZy whore is cRaZy

What weighs 325 pounds, has hair worse than Phil Spector, and secretly enjoys getting karate-kicked in the appendix while ripping ass? This chick's 798th fuck buddy, and he's not even the worst of the bunch.

08/24/12 Rocco Siffredi LULZ
Type ? for random video