Little Humper Diego Perez and his buddy are driving around doing some classic pranks when they spot their ex college professor, Ms. Maxx. The blonde MILF was always strict, so they decide to get her back with a ding-dong-ditch. The plan goes awry when Diego trips and his buddy ditches him, but Jordan Maxx drags him into her house and lets him suck on her big titties! This prank gone wrong worked out perfectly: with Diego balls-deep in his prof's pussy.

Little Humper Jimmy Michaels tries to crash his new stepmom's bachelorette party and look down her bestie Lilly Hall's top. After he cuts a peephole in the shower curtain and hides behind it, he gets an eyeful of Lilly's tits and sticks his big cock through his homemade gloryhole. Lilly's tempted into a bj but tells him to behave himself... and of course, that's a challenge for any self-respecting Little Humper! Jimmy decides to streak in...

Just as soon as MILF Ashlyn Peaks finishes changing the lightbulb, her stepson Johnny Love comes in and breaks it with his football! Ashlyn orders Johnny to get up that ladder and fix what he broke... but he's just the right height for her to notice his huge boner in her face. Apparently getting ordered around turns him on, so the hot stepmom tells Johnny exactly what to do as she sucks and titty-fucks him, taking charge and taking his dick

This Little Humper is worried his hot stepmom, Naomi Foxxx, will be big mad when his buddy, Conor Coxxx, air humps right behind her, then pulls down her shorts and slaps her booty as she's washing the dishes! But Naomi's got a surprise in store for the college guys, because she sharks Conor right back, pantsing him and then sucking his impressive dick. Naomi's way wilder than either of these Lil Humpers, and she proves it, riding Conor's cock...

Lil Humpers Juan Loco and his buddy are working out when they spot hot blonde MILF Andie Anderson doing some stretches, and Juan has to get a chance to hump that! His buddy starts up a conversation about form as Juan air-humps her from behind, then puts his face right under her booty as she squats. The guys follow Andie to the bathroom where she works out Juan's cock, tittyfucking him and even giving him a foot job before she rides him on the floor!

After Jimmy Michaels gets too horny in the college library and cums all over his blonde GF Krissy Knight's notes, she tells him to fuck off while she studies... so he does, starting with humping hot librarian Mandy Waters! She's impressed with his hard cock as he sneaks up behind her in the stacks, and soon she's bent over getting dicked down... very quietly, of course. Or not!

Juan Loco can't believe how hot his buddy's new MILF stepmom is! While Pristine Edge is getting heated looking for her keys, Juan finds them and puts the key ring around his big dick. Pristine calls the Lil Humper's bluff and sucks his cock while her stepson watches. After hiding from her husband and getting dicked down under the kitchen counter, Pristine takes Juan to the bedroom to sneakily use that cock till she's satisfied.

Jimmy Michaels is stocking shelves at the grocery store when one of his Lil Humper buddies points out stacked MILF Ashlyn Peaks and her big melons. Jimmy's all ready for some air humping when he espies Ms. Peaks taking a sneaky tits-out video and decides to show her his big zucchini instead, and she eagerly devours it! The horny pair hide down an aisle for doggystyle fucking, and sneak into the back. Ashlyn wraps her boobs around that cock, then rides Jimm...