Painful Moments in Anal Sex

Cringiest Porn Scenes Ever Attempted

These awful pornographic gems were all attempted with eroticism as a goal. I.E. People were somehow meant to masturbate to this shit, but what these clips lack in fap value they make up for with lulz.

10 Inch Challenge = Demolished

It seems Allie Addison's apprehension levels are at zero, giving her little trouble with broski's maximum depth potential. And by little trouble, I mean the kind of potential organ rearrangement Art The Clown would be proud of.

The DeVIRGINIZER

What's that old saying again? If a mint condition cornhole exists, Pierre Woodman will abuse it more than a penalty shot kicker from England? Unlike Snaggletooth McButtfuck over here, those three lads can sit down on a hard surface for the next month without consequence.

6 Amazing Sex Acts

Today's Menu: 1) Conor McGregor post-retirement 2) Ballin on a Budget 3) Hard Times Daddeh 4) The Mastadon Challenge 5) Contents Under Pressure 6) Always Get Your Moneys Worth

Pornhub's Biggest Deviant

That's it man. As far as I'm concerned vegans have officially jumped the plant-based shark. Not even at the height of one of my patented Acid Trip + Red Lobster Biscuit wombo combo benders did I envision something as despicable as this going behind a paywall.

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

Fear is the Weakness

Don't let the confidence in her voice fool you: This cholita's ability to withstand pain is about as real as her soggy pancakes in a pushup bra. As illustrated by his first, second and 17th attempt to keep a decent rhythm in her poo canoe. The end result? Well... you'll see.

HERE COMES THE PAIN

French Mustard: An Anal Sex Fail

"France has neither winter nor summer nor morals and has usually been governed by prostitutes... apart from these drawbacks it is a fine country." - Mark Twain

Mom's Secret Recipe

The Rectum: Some men never experience contact with it. Others, speed-run it like a 3:00AM trip through the Burger King drive-thru. But judging by this specimen's cornhole pastaroni, I think it's a safe bet she follows Gordon Ramsay on TikTok. Happy Fuckin Holiday(s).

Can't Stop The Cumshots 3

Listen: If you delinquents keep spamming your entire loadouts before the first checkpoint is captured, I'm gonna have to turn this into an official series. That kind of uncontrollable pressure reminds me of a romantic moment involving myself, a $20.00 bill and the McRib. Let's just say mom's Plymouth Vista got a new interior paint job that night. [PART I] [PART II]

Cum Haters 2024

Whole lot of tomfoolery going on here. While most girls will accept the fate of the firing squad they kneel down in front of, there's always an exception. Today there will be 14 exceptions.