FAIL: Teacher Attempts Double Anal

4,743,856 views

Deleted scene from Un-Natural Sex 20 involving an ex-teacher looking to sacrifice the health of her colon in exchange for fame & fortune (aka $728 and maybe, just maybe, a Q&A with Swank magazine). Epic spoiler: things don't go as planned.

Uploaded 08/31/11 Fail

anal, fail, funny, pain, shit talk

Tiffany Six
Related Videos

Cornholin in Kentucky

A couple of yahoos get caught mashin potatoes during happy hour. Not very conspicuous about it either. Remember that one weirdo in school that always dropped his pants to the floor in front of the urinal? This is what happens when he grows up.

931,034 views 05/15/23 Busted!

Stacked and More Socially Awkward 18-year-old

You clicked the original one so many damn times, I had to dive deeper into her discography. Unfortunately it turns out all her roads lead to this evolutionary cul-de-sac using her as the only form of exercise he's seen since Jock Jams was a thing. Don't look that up. [-PART I-]

1,648,831 views 08/28/23 HeavyOnHotties Awkward Moments In Porn

THIS WON'T LAST 24HRS

7,479 views 05/16/24

The Accidental Anal Compilation

Not much is worse (or funnier) than an unexpected penis bashing some hoer O-ring with little forewarning or lube. Ideally, zero forewarning and zero lubes.

6,257,405 views 04/09/17 Wrong Holes

The Purge

She seems like a nice girl. The type that would throw herself off a post office rooftop if you missed her text, or fuck the mailman's chihuahua if your Instagram pic got 0 likes. But her taste in recreational activities? Shit, I've seen happier faces cleaning toilets at the Renaissance Fair.

1,849,386 views 02/01/19 Fisting

Pornstar OD's on Set

Ever wonder how these girls are able to accommodate penises large enough to legally require airbags? HINT: They take painkillers. Lots of 'em. And I'm not talking about the kind that leave you looking like the cover of Alison Arngrim's “Heeere's Amy". (look it up)

2,803,807 views 09/02/17 Fail

Dying for the Pussy

Anyone know what Twitch girl he moderates for?

1,449,413 views 11/21/19 Asians

Creme Fraiche'd

Epic poker face @ .57 mark. I call this one the 'i totally just nutted in my own mouth but i dont even give a fuck cause i have a 6.7 inch penis and listen to Rage Against The Machine on vinyl' look. Dude's got that shit mastered.

4,250,983 views 05/11/12 TeenBurg Fail

Safe Sex FAIL

Gloryhole rookie "Emma" unequivocally accepts defeat after Stewart's Magnum XL ventures into deeper waters. In other words: The flex went wrong HAHA

2,048,263 views 07/09/21 Gloryhole Swallow Fail

Shit Pornstars Say 4

I imagine this is what happens when all of your knowledge of the English language comes from Pizza Hut commercials and TikTok. In fact, I may have just uncovered a form of communication so useless that California colleges might start offering 4-year degrees in it.

1,811,279 views 10/13/20 Shit Pornstars Say

The Discomfort Zone

You know the deal: It's the height of the pandemic and funds are circling the drain. So you hit up the local videographers and offer your services to the highest bidder. I_CUM_HELLMANS hits up your DM's on Reddit and now the smell never washes off. GG NO RE

2,300,016 views 08/02/21 HeavyOnHotties Fail

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

2,158,200 views 06/01/19 Ridiculous Orgasms
Type ? for random video