In this second chapter of a 3-part series, "Deep Woods Domination", Tristan Jaxx is on a camping trip with his stepson Jackson Fillmore. During a brisk walk they discuss the recent disappearances of ...
Jackson Fillmore waits on the dirty gym floor, gagged and immobilized as Jessie Colter finishes his workout. Now it's playtime, Jessie drags his boy across the floor and cuts away his underwear, expo...
Master Sebastian Keys just found his newest contender for house slave: Jackson Fillmore. First Jackson must endure days of confinement in full duct tape bondage, while Master Keys beats and toys with...
Skating over to the Armory on a hot summer day, Jackson wants impromptu edging session, and Van is more than happy to oblige. Jackson melts into the bed as Van and Joshua James take him to the edge o...
Two lean studs collide today on Top Cock: For red team, it's Scott DeMarco promising to knock and fuck Jackson Fillmore all over the mat like a ragdoll. Jackson Fillmore represents blue team and is r...
Jackson Fillmore impatiently sits in a cage, wondering why the dom he hired, Christian Wilde, hasn't started yet. Mr. Wilde finally gets up to silence the ungrateful bitch, barking at him to remove h...
It’s Chris Burke’s raw muscle versus Jackson Fillmore’s limber, flexible physique on today’s Top Cock. Both these dudes are chomping at the bit to humiliate their opponent...
Jackson Fillmore is a full-time BDSM lifestyler. Is his experience enough to help him endure 30 minutes of excruciating sadistic torment until he blows his load? THE PIT - Strapped down to the platfo...
Hot boy next door Jackson Fillmore joins Men on Edge Live to try out puppy play for the first time. He jumps right into the role, submitting to Christian and Sebastian as soon as the puppy mask goes ...
Jackson Filmore is passed out at home when Sebastian and Jesse decided they need a boy to torment and edge. After taking Jackson out of his home they bring him to their underground Boiler Room and ti...
Jackson Filmore is changing into his workout clothes without realizing that the Creepy Handyman, Trenton Ducati is looking on. Jackson catches a whiff of his sneakers and gets aroused, doing his work...