Tag Archives: Jackson Fillmore

Puppy play, bondage, and vigorous tickling: Jackson Fillmore live show

November 16, 2024 Metal Leave a comment

Hot boy next door Jackson Fillmore joins Men on Edge to try out puppy play for the first time, during a live shoot.

He jumps right into the role, submitting to Christian and Sebastian as soon as the puppy mask goes on. Christian leads Jackson around on a short leash and has the pup worship his boots while Sebastian hogties him. Jackson is made to wear a rawhide bone on his balls as they edge him repeatedly, getting suggestions from the members. Jackson is even made to suck his own dick in a piledriver. Sebastian and Christian take Jackson to the bed, bending the eager pup over and toying his hairy asshole. Jackson may not be allowed to cum yet, but Christian takes the opportunity to blow a load all over Jackson’s face. Flipped over, Jackson endures an alternate between torment and pleasure as he’s relentlessly tickled. An even bigger pup tail plug is inserted before Jackson finally gets to blow his load, obediently lapping up his cum from Sebastian’s hand. Helpless to move, Jackson’s finished off with a vicious tickling and apple polishing on his sensitive, uncut cockhead.

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Male BDSM: Jackson Fillmore is tied up, tortured and fucked

September 5, 2023 Metal Leave a comment

This is a video from 30 Minutes of Torment called ‘No Mercy for Jackson Fillmore: Beaten, Electrified, Humiliated & Fucked’

In this shoot from 30 Minutes of Torment:

Jackson Fillmore is a full-time BDSM lifestyler. Is his experienced enough to help him endure 30 minutes of excruciating sadistic torment until he blows his load?

THE PIT – Strapped down to the platform, balls secured tight to the front, Jackson stands completely immobile and must face a serious torrent of corporal punishment. Van starts with open palms and fists to tenderize Jackson’s flesh before flogging it raw.

THE CHAIR – Jackson sits in the electric chair, his lower half already starting this round with a painful current through his thighs. The torment intensifies with more electrodes clamped to his balls and an electrified butt plug deep in his hole. Van zaps Jackson’s erect cock and runs electric arcs from a violet wand all over Jackson’s body and straight into Jackson’s ass. At the final moments, Van fries Jackson with the electrodes turned up to full power.

THE GIMP STATION – Jackson has to make his cock hard for the gimp’s arrival while Van lands sharp hits from the crop all over Jackson’s ass. The gimp plows into Jackson with a raging hard-on as Jackson grits his teeth and moans. With his back splattered in hot wax, Jackson rides the gimp as he jerks off. Jackson successfully blows his load, but the clock is still ticking. His face gets smothered in the gimp’s cum and Van finishes Jackson’s 30 minutes with a wicked beating.

Model in this video: Jackson Fillmore

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Jackson Fillmore learns the true meaning of pain from Sebastian Keys

June 27, 2023 Metal Leave a comment

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 him. After Jackson is released from his tape restraints, he must escape the imprisonment of his own mind. Master Keys torments Jackson with his crop while delving deep into the pain slut’s inner psyche. Jackson needs to understand his desire for pain if he wishes to continue. Jackson’s arms are suspended above him as Master Keys unleashes the full power of his flogger on him. Jackson embraces the torment, and is rewarded by being tied against the wall, and feeling his master’s hard cock fill up his asshole. Master Keys fucks Jackson, until he can no longer contain himself, and coats Jackson’s slutty ass with his fuck juice. Jackson is proud to have passed the challenge and releases a cum stream that trickles across the floor.

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Title of this shoot: Mr Keys Takes The House Slave To The Next Level

Models in this shoot: Sebastian Keys and Jackson Fillmore

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Dom for hire

May 16, 2023 Metal Leave a comment

In this shoot from KinkMen:

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 his clothes. He inspects every inch of Jackson, reducing him to only pieces of flesh. When Jackson thinks he can order Mr. Wilde around, Mr. Wilde responds with his hard leather paddle all over Jackson’s feet and ass. Jackson learns to follow orders and show gratitude as Mr. Wilde turns his body lobster-red with a belt. After choking all over Mr. Wilde’s massive dick, Jackson has whatever remaining noncompliance flogged out of him. Jackson accepts his nothingness, swinging over the ground in ropes while Mr. Wilde continues to take his time. He finally approaches Jackson and fucks his ass relentlessly before coating his face in hot cum. He unties Jackson and commands him to crawl to his throne over the sharp iron bars of the cage and lay his body at his master’s feet. Jackson complies with Christian’s order to cum, finally grateful for his master’s treatment. As Jackson gasps in relief from his orgasm, Mr. Wilde stomps on his tender cock.

Models in this shoot: Christian Wilde, Jackson Fillmore

Title: Mr. Wilde Shows Cocky Executive Who’s the Boss

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Tied up at the gym

August 3, 2022 Metal Leave a comment

At Bound Gods, Jackson Fillmore waits on the dirty gym floor, gagged and immobilized as Jessie Colter finishes his workout. Now it’s playtime, Jessie drags his captive across the floor and cuts away his underwear, exposing his hard, uncut cock. He teases Jackson’s cock right until he’s about to blow his load, but Jessie has other plans.

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Clover clamps decorate across Jackson’s hairy balls while another clamps his foreskin shut. Jessie then takes full mount and rams his cock down Jackson’s throat before stringing him up for a flogging. Jackson wriggles in the air as the flogs rain down, completely inverting himself as he tries to escape Jessie’s blows. The bound gym rat then finds himself beaten with the cane, his ass getting nice and tender before Jessie can slide his cock inside. Pounding away on his ass, Jessie milks the cum right out of Jackson’s cock and feeding him the leftovers.

Title of this video: Bound gym whore gets the cum fucked right out of his uncut cock

Models in this shoot: Jackson Fillmore, Jessie Colter

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Dale Cooper’s huge dick is wrapped in bootlaces

July 30, 2022 Metal Leave a comment

Dale Cooper, horny for his second Men on Edge appearance, gets rock hard just from the feeling of leather on his ripped body. As he’s secured to a post, Jackson Fillmore frees his dick and teases it with a deep blowjob. Dale is ready to fucking bust, but Jackson stops just in time to make Dale twist and beg. Dale gets moved to a forked cross, where his strong legs are spread apart for Jackson to admire. Dale moans as his balls are pulled to the ground with a boot tied around his sack. Strong taps onto a dildo deep in his hole send vibrations of pleasure through his whole body. Now strapped down to a wooden box, Dale sucks off Jackson as he receives increasingly painful edges. The pressure builds in his balls. Jackson blows a hot load all over Dale’s face, sending Dale into a horny ecstasy. Covered in Jackson’s cum, Dale finally gets to blow his own load. But that orgasm comes with a price: a heavy apple polishing.

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Title of this shoot: Hot leather stud with a fat cock gets edged

Models in this shoot: Dale Cooper, Jackson Fillmore, Kristofer Weston

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Deep Woods Domination: Chapter 2

April 28, 2018 Metal Leave a comment

In the second chapter of Deep Woods Domination — a three-part series at Bound Gods — Tristan Jaxx is on a camping trip with Jackson Fillmore. During a brisk walk they discuss the recent disappearances of hikers from the nearby woods. But it’s only a fleeting thought, because Tristan actually has his eye on Jackson’s smooth, fuckable ass.

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A camper gets tied up and edged in the woods

October 14, 2017 Metal Leave a comment

It’s Damien Moreau’s first time at Camp Perv-Anon. Camp counselors Jackson Fillmore and Sebastian Keys give Damien an exciting and successful first night.

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