Stewart's Guide to Anal Sex

The Mike Itkis Sex Tape Actually Happened

2022 continues to be the year of "If the Internet Didn't Archive it, I Wouldn't Fucking Believe it". Not only did an actively campaigning politician pay for, produce and release a sex tape with less penetration than Meryl Streep's last gynecologist visit, but he thought it was going to be secret weapon to his victory lap to boot. [NEWS STORY] [PORNHUB] [THE GIRL'S INSTA]

18-Year-Olds are Complicated

This example of why you should periodically review your fiber intake, goes by the name Baby Swabery. Due to her age, I'll be approaching this description accordingly: no cap the jumbo deluxe chimmichanga lunch special was a mf mistake, fr the situation is NOT bussin.

My First 18-year-old Escort

Some real memorable facial expressions in this one. Almost as if she can't believe someone would pay good money to hookup with a person possessing less sexual prowess than a New York City hotdog, and still achieve climax. 4/10; would penetrate again.

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.

After The Tijuana Donkey Show

What happens in Mexico Chile gets filmed with a potato by cartel members drunk off corona lights. For some guys that love beheading the locals and smuggling drugs in their butts, they sure have weak stomachs.

"TAKE IT OUT NOW!"

Cam Whore Left Speechless

Paying some skank on the internet to watch you jerk off on webcam seems pathetic and sad overall, but this cam slut has to hold back laughing when she see's this fuckin guys dick.

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]

The Worst Male Orgasms EVER 1

Door Dash your chimichangas and fire up the Demi Lovato playlist, for you are about to witness the pinnacle of peak male performance. Not since the 2017 inauguration have I heard this many vegan-powered war cries go unanswered lol

Prostitute Never Saw it Coming

I don't think that title and/or thumb truly convey the crossover that's about to happen here. But if it costs $50,000 to get an 8 pack of Oscar Mayer's uncured wieners into a female's dung funnel, then life is no longer worth living. Inflation did this.

Cute Teen With Hidden Talent

Don't even lie to yourself. This bitch is so hot you wouldn't mind her magical Stretch Armstrong vagina at all.

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.