Professional hole-stretching specialist Ryan Bones is out for a jog when he spots Drill My Hole model Skyy Knoxx trying … and failing … to back his arse onto a dildo stuck on his window. Ryan goes in for a closer look, then offers his assistance. Skyy isn’t sure about this handsome hole-stretching stranger until he sees the big dick poking out of Ryan’s shorts! The horny bottom wants a taste, but first Ryan puts him through his paces, leading him in squats and stretches, then stretching his hole out with his fingers. Skyy really starts to open up, so Ryan has him try the dildo again, and this time Skyy can take the whole thing as he swallows Ryan’s cock too. Ryan fucks Skyy doggy-style and has him ride his big cock. Skyy’s never been so open, and he lays back and jacks off as Ryan pounds him mish till he cums, then the top blows his load in Skyy’s mouth.
Dedicated masseur and Drill My Hole model Jason Vario takes every precaution to keep his clients safe, wearing a face shield and gloves as he sterilizes his table before inviting Shane Amari to lie down. Shane isn’t jazzed about wearing a face mask, but he’s really excited for some human contact after months of waiting for a massage. Jason oils up Shane’s back and gives him a sensual rubdown, moving his strong hands lower to work Shane’s arse and slide a finger inside. Shane makes a hole in his mask so he can suck Jason’s cock without even taking it off, then the strong top penetrates him missionary. Shane rides Jason and strokes his dick till he cums on the masseur’s face shield, then Jason fucks him doggy-style and gives him a creampie.
Nate Grimes asked his polyamorous boyfriends and fellow Drill My Hole models Pierce Paris and Johnny B for a double facial, but at the last second, he dodged it! Johnny and Pierce resolve to get Nate next time, but he keeps eluding all their attempts, while sneakily jizzing on both their faces when they least expect it. After blindfolding the cum dodger with his own underwear, the guys finally give Nate what’s been cumming to him, then celebrate with a threesome. Johnny fucks Nate doggy-style as Nate sucks Pierce’s cock, then it’s Johnny’s turn to get pounded in pile-driver by Pierce as he sucks Nate’s dick before Nate fucks Johnny doggy-style. Pierce and Nate take turns stretching Johnny’s tight hole, then Nate lies back to take the double facial he deserves before cumming all over himself!
Jeremy London is late for an important video meeting, so he hurriedly puts on his boxers and a shirt as he looks for his laptop. His boyfriend Drill My Hole model Markus Kage chuckles as Jeremy tries to use the vibrator lying on the table as a mouse, activating the vibrations with his phone. The toy gives Markus an idea: As Jeremy tries to stay professional in a video conference with his boss, the naughty top crawls under the table, rips a hole in his man’s under-drawers, and slips the vibrator into his hole! When Markus turns up the toy, Jeremy has to log off as he cums hard all over his webcam. Jeremy starts sucking Markus’s cock, then rides it on the floor before the top picks him up and puts him on the table to fuck his arse missionary. Jeremy bends over for some doggy-style till Markus pulls out to cum all over the vibrator. Jeremy slides it back inside, then gets back to work!