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Theo Ross

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William Seed gets fucked by Theo Ross while playing video games with Cayden Solano in “Owned and Boned”

Men.com, Drill My Hole, William Seed, Theo Ross, Cayden Solano

Toned and tattooed Theo Ross is furious when he finds William Seed and Cayden Solano playing video games instead of cleaning up the house, but decides that their distraction might be used to his advantage. Theo teases William and Cayden with his thick cock while they play their games, then slides right into their tight asses without them even noticing. When the boys realize what’s going on they make up for their dereliction of duty by letting Theo use their holes in a hot and heavy fuck fest.

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Hairy bottom Teddy Torres gets fucked by Theo Ross in “Work Life Balance” + SAVE 80%

Men.com, Drill My Hole, Theo Ross, Teddy Torres

Jacked, tattooed stud Theo Ross is a workaholic who is not taking his company mandated time off seriously, but mustached, black-haired hunk Teddy Torres is dead set on making sure Theo gets some much needed rest. It becomes clear to Teddy that the only way he’s going to get Theo to stop thinking about work is by giving him something better to think about, slowly and sensually sucking Theo’s thick cock then taking it deep inside his perfectly hairy ass.

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Theo Ross fucks Jack Kross hard and deep in Drill My Hole’s “Watching You”

Men.com, Drill My Hole, Jack Kross, Theo Ross

Slim stud Jack Kross breaks into chiseled beefcake Theo Ross‘ house while he’s out for a run. When Theo comes home and catches Jack intruding, he gives the sneaky slut an up-close look at what he came to see. Theo rams his thick cock down Jack’s eager throat then deep in his ass to teach him a lesson about the importance of asking permission, fucking him hard and deep until he can’t take any more.

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Jay James gets his ass drilled by Theo Ross in “Screaming VS Moaning”

Men.com, Drill My Hole, Jay James, Theo Ross

Horny and hung Theo Ross finally has some time to jerk off, and relieve some tension. His slender, tall roommate Jay James thought he heard screaming so he bursts into the room, and interrupts tattooed Theo halfway through stroking his thick cock to climax. Cute Jay can’t seem to think of anything else, and borrows Theo’s dildo so he can play with his tight ass. Good-looking Theo hears screaming, and this time he’s the one who bursts into Jay’s room. Jay invites Theo over to show him how to play with his toy, and to let him feel the real thing too!

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Dustin Holloway gets tag-teamed by Pierre Fitch & Theo Ross in “Not Exactly Marriage Material” + SAVE 80%

Men.com, Str8 To Gay, Dustin Holloway, Pierre Fitch, Theo Ross

Brown-haired jock Dustin Holloway recently went through a break-up, and in an effort to make his ex jealous, he decided to start looking for a new man! He answered an ad from sexy, chiseled Theo Ross, and agreed to marry him so he could stay in the country, but was disappointed to find out he was straight. Or at least blond-haired Theo made it seem that way! Dustin got home early one day and caught him making out with athletic, tattooed Pierre Fitch. Theo couldn’t risk losing him, so he invited Dustin’s massive cock to join them for a sex-filled threesome.

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Theo Ross gets his smooth ass fucked by Damien Stone in “Renovate My Hole” at Str8 To Gay

Men.com, Str8 To Gay, Damien Stone, Theo Ross

A couple of beefy construction workers, dark-haired Damien Stone and tattooed Theo Ross, show up to renovate a kitchen. Muscular Damien in giving detailed instructions, but horny Theo, who is supposed to be taking notes, is getting distracted. Clearly, chiseled Theo only has one thing of his mind! Luckily, boss Damien knows just what he needs, a hard dick in his tight, disobedient hole! Renovations will have to wait because this is one hole that needs to be plugged immediately!

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Ethan Chase gets fucked by Theo Ross in “Renting from the Nudist” at Drill My Hole

Men.com, Drill My Hole, Ethan Chase, Theo Ross

Cute, athletic Theo Ross decided to get away for a few days, and opted to rent a room for his accommodations. Upon arriving, a naked and fit Ethan Chase opened the door to welcome him. Tattooed Theo is taken aback at the sight of his nudity, and realizes after the fact that he rented a room from a nudist! Slender Ethan can’t wait to sit on his thick cock, and comes up with a plan to get him stripped down, and sliding his dick between his eager cheeks in no time.

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Kit Cohen gets his ass fucked by Theo Ross in “Holiday Humpday” + SAVE 80%

Men.com, Drill My Hole, Theo Ross, Kit Cohen

Handsome, muscular Theo Ross is home for the holidays, and extremely horny! He heads up into his room for some quiet masturbation time before dinner. Theo is so horny that he starts fucking the macaroni that his brother brought him, and is caught mid-way. He ends up downstairs, and fucks all the food that is on the table including a pie underneath the table. His family catches him, and freaks out over the ruined dinner! He’s about to stuff the turkey when slender and fit Kit Cohen walks in to save the day! He finally gets some real live action, and his thick cock can finally stuff something!

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William Seed fucks Theo Ross hard in “Attack of My Clone, Part 3” + $69.99/year SALE!

Men.com, Drill My Hole, William Seed, Theo Ross

Athletic hunk Theo Ross just broke up with his sexy boyfriend, William Seed, and he’s already missing his ripped body and thick, uncut cock. He has the brilliant idea to create a clone of his ex, and he’s overjoyed when he gets an exact replica! He doesn’t waste any time testing out the goods, and sampling his new cock via both of his wet holes.

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Nikko Russo takes a ride on Theo Ross’ cock in “Dick Swap, Part 1” at Drill My Hole

Men.com, Drill My Hole, Nikko Russo, Theo Ross

Tattooed cutie Theo Ross just wants to get his dick wet, but his roommate slender Nikko Russo really isn’t having it. Muscular Theo devises a plan and purchases a 3D dildo sex doll so he can at least get off watching him ride it, but has an even better idea and swaps places with the doll when Theo gets off it to answer the door. He places himself in the same position with his erect dick, and waits for Nikko to come back, and slide onto his cock. How long will it take Nikko to notice?

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