Winter Break vol. 6: Probing Deep
Scenes 29 min
8teenBoy

Winter Break vol. 6: Probing Deep

Cast
Milo HarperCaleb Gray
Release date
Runtime
29 min
Studio
8teenBoy
Tags
Big DickBrown HairKissingNo CondomRimmingTwinkUncircumcisedanalblowjob

This is the scene you’ve been waiting for! Our gorgeous group of high school hotties are finally packed tightly together in a cozy cabin on their senior ski trip. Caleb Gray, who's been fucking Riley, behind Riley's boyfriend's back, is having a tough time seeing his fuck buddy snuggling up with his boyfriend, Taylor. Caleb’s definitely caught more feelings for Riley than he initially thought; so, naturally the dude is down in the dumps seeing his booty buddy snuggled up to his BF. Milo Harper notices Caleb's conundrum and decides to put a smile on the sexy sulker. He starts with a mind blowing blowjob then, moves on to an erotic ass examination while stuffing Gray’s gorgeous mouth full with his massive meat. No ass exam would be complete without a tongue fucking. After working Caleb’s cock hungry hole into a "fuck me please frenzy," with his darting tongue, Harper harpoons Caleb's hot hole with his more than ample, uncut appendage. Gray’s juicy jock is hungry for some hind end action as well; so, he throws Milo a beefy bone in a raunchy, raw dirty dog. Harper takes every inch of the hottie’s hefty hog before his top tendencies kick back in; and, he can't help but saunter up behind Caleb to cock the brunette’s smooth booty and finish what he started. The raw ram-a-thon builds, bringing both boys to a firehose finale. They're rocked up rods explode; and, they both empty every ounce of ooze all over Caleb’s tight torso, covering him with a winter white coat of cum, fitting for their snowy senior ski trip. Feeling closer to Milo, Caleb confesses he’s been fucking Riley, who just happens to be Milo’s bestie..... What will Milo do with this new info? Find out in the next dick heavy, drama filled fuck-travaganza of “Winter Break.” Coming soon!

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    Sources StashDB 2026-10-04

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