Painful Moments in Anal Sex

Anal Virgin Didn't Come Prepared

LIFE LESSON #27: If you have worse rectal control than one of the golden girls; seek out another hobby. Last time I saw someone pay for skidmarking this abusive he was ultimately banned from Chipotle at the corporate level. (me, it was me) [song]

BALLS DEEP

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.

Unacceptable Devices V

If there's one thing that never fails to get me questioning the future of this whole human race experiment; it's what the most unassuming person will consider a sexual accessory. So here's about 6 of them. That's right, six. As in the number of times I replayed the noise that Pringles can made when ricocheting off her head.

Imagine Getting Caught Doing This

The soundtrack was so bangin, I had to fulfill your request(s). Wanna know what's not though? Whatever the fuck must have happened to this girl earlier in life to make her like this. Probably haven't seen that kind of wreckage since the great crave crate challenge of '97.

Married Woman vs. Anal Casting

Think your marriage is in trouble? Time to reevaluate things, Ham Hock. Today we have a pioneer of female empowerment that does it all. And by all I mean a.) buttsex b.) buttsex while wearing her wedding ring and admitting it on camera. yikes = big

20-year-old "Sex Pro" Can't Anal

Not old enough to leave Food Lion with a 6-pack of Bud Light, but she's already carrying a body count that would make a frat house blush? You'd think by the semi-centennial cock that went 1v1 with DM-TrainTrackFace she would've learned to fertilize the backyard. But... nope.

Public Degeneracy Volume 6

Turns out there's absolutely no shortage of individuals that consider teaching their penis the macarena a societal norm. A Superb technique no doubt, but probably not for beginners. Chances are you'll misjudge one 360 no-scope and catch a local in the crossfire. It's called "The Ben Roethlisberger" and it'll make you wish you kept the half boners at home.

Blame it on the BBC

I guess this is what happens when your Netflix and Chill night turns into a solo adventure and you start organizing the "Foreign Girls That Like WuTang" sub-folder in your NUT directory. I don't know, I see more reasons you shouldn't cornhole wild life thanks to her constant deer-in-headlights reaction than I do sitcom legends. Thoughts?

REAL TWIN SISTERS GO ASS-TO-ASS

We aren't talking about your traditional hole-to-hole, human centipede sausage link simultaneous penetration here. But someone ramming their jelly bean into you immediately after pulling it out of a sibling is just as reprehensible, so it still counts. I've been appointed to the head of this committee and those are the rules I've outlined.

Anal Rookie Can't Keep Up With Her Friend

"I'm very sad that anal isn't as enjoyable as I want it to be."

GIRL HAS DELAYED ORGASM

We're all too familiar with premature ejaculators, but what about latent ejaculation? Watch as Sum Dum Ho starts cumming an entire minute after intercourse is completed without even being touched. WTF?