Stewart's Guide to Anal Sex

Hooker of the Year 2019

Poor prosti gets sandbagged by a local gentleman who's only sexual experience involves Walmart's checkout line & Colt 45. But apparently her dugout is built for the major leagues, cause despite his John McLane ingenuity... she still walks away with a smile. Fucking amazing.

HERE COMES THE PAIN

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

18 Year Old Anal Virgin Risks It All

Great body. Classic look. Even has the courtesy to scrub daddy her dirty walnut before doing the coney island cha cha. There were definitely a couple moments of genuine concern on her face, but now you know why wedding rings exist. [song]

WRONG HOLEZ: 2020

It took years, but we finally have another worthy entry for the museum of unintentional rectal breaching. I'm talkin 3.5 nonstop minutes of backdoor bruising that white people should only experience inside the CHAZ zone. Only difference is the people in this video actually put meat inside their bodies lol.

The Worst Casting Couch Video Ever

The downside to dating a girl with the self-awareness of a TikTok investor? Literally nothing. Not even an unannounced visit to vegemite valley is enough to send her running. Either we have a cold-blooded liar on our hands, or that pudding hatch is spring-loaded.

The Caught Compilation #20

Semi-homeless degenerate gets caught 4 strokes away from superstardom only to be met with the full force of a Starbucks-fueled Karen, ultimately sending his hardon to the boner graveyard. We've all seen it before. BUT, the big game hunter at the 2:15 mark? That predator deserves it's own week on The Discovery Channel.

I Want HIV

A "scared straight" look into a small portion of the gay community that has fetishized and even glamorized HIV/AIDS. [Documentary]

The Single Greatest Blowjob of ALL Time

We had to go back, way back and deep into the pornography archives of the 1970's. All those hours of sifting through pale, over exposed bodies and bush was worth it to uncover this beautiful forgotten gem.

Butt Sex Sends Poor Girl to the ER

Every dirty slut should know that a slippery fuck toy plus a cavernous butthole can equal a trip to the ER. Next time save yourself the embarrassing shuffle through the waiting room and tie a string to that mother fucker.

Semen and Strife

See that pretty face? Well, that's all you get because she's too busy getting seizure-fucked in the face by a cock raging french guy the entire clip to look at the camera. #rekt

Broken Dreams, Broken Buttholes

Compliments aren't my strong point, but I must say... chick in the yellow dress is fucking stunning. I'd readily eat Honey Nut Cherrios out of Philip Seymour Hoffman's crusty asshole just for a chance to hold her hand. Someone Russian please hook it up.