Jack the Ripper

Awkward Moments in Porn 11

Turns out 67,000 incestuous storyline porn videos lied to us after all. Dare to make contact with your bloodline after the sun goes down in rural Alabama, and one of these clips just might be the Tales From the Crypt Halloween Special you walk in on.

Safety First

Wow, being an attention whore really came back to bite this one in the taint eh? Hey 1Pac, how about next time you stick to overdosing in the laundry aisle like everyone else and save the social media challenges for likeigiveafuck.com.

Nazi Cuck Porn

I'm not sure what kind of a person scripts a pornography scene about a nazi struck by white guilt and letting a "jungle bunny" fuck his racist wife for reparations... but they deserve an award.

1 Guy 1 Mousetrap

A jackass inspired stunt gone sexual ends very badly for the LoL platinum player responsible for conceiving such an act of genius. Luckily our hero isn't concerned with things like dignity, human contact or a fully functioning penis.

Unexpected Fetish

Did flashing interns at the local 7-11 becoming a challenge or something? Apparently this miscreant prefers the orifices less traveled. Specifically the ones small enough to give Tiger Woods anxiety attacks. C-L-A-S-S-Y.

Don't Try this At Home

No, seriously don't. Every once in a while pornography life overlaps into real life lessons. Let's just be glad this learning experience was made possible without the assistance of Czechoslovakian accents, and a petting zoo. You don't want to see the things I've seen man.

How Legends are Made

The one and only JSC aka The O.G. Wzard of the Teflon Rectum. Her anal acrobatics set such a standard in the renaissance days of underground porn, you'd almost forget she used her vag recreationally. But in 1998... something magical happened...

Proof that Money Can Buy ANYTHING

There's just no hiding from your past once you pull the trigger on something like this. Their Ross Store wardrobes will be forever stained. The regret can't be washed off. And the $27 paycheck isn't enough to drink the memories away. #crankthattherapist

The Rarest Amateur Video on Earth

You'll notice a piece of this was already in BB4. Once I found out who this girl was, the deep dive had to begin. These are clipped from what's left of the only couple I've ever seen actually wipe their history off the Internet. They were masterbrookssub, and all that's left is a few tumblr remnants of them trying to market what I can only refer to as "Chris Brown Porn".

The Tallahassee Crab Trap

Consider this the advanced users only section of the Internet. And nothing spells T-A-C-T-I-C-A-L A-D-V-A-N-T-A-G-E quite like a woman that could literally use a Volkswagen Golf as a dildo. If you're not into safe spaces being invaded... this one isn't for you.

Anal Virgin Almost Has A Breakdown

Meet Luciana. aka Timea Bella. aka Indisputable Liar. She claims her stink whistle has less mileage on it than the Peloton in Ozzy Osbourne's basement, yet doesn't even call a timeout when Woody goes straight to the A. But when it comes time to sample some French vanilla, she calls it quits. Stay tuned for part 2 where I'll showcase her triumphant comeback.

NEVER USING TINDER AGAIN