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Drill My Hole Galleries
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Personal Trainer (Tyr Alexander & Tyler St. James)
by Drill My HoleTyler St James has money problems; his parents recently passed away and left him a beautiful cabin in …
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My Bitch (Tyler St. James and Dereck Fox)
by Drill My HoleTyler St James and Dereck Fox are long-time friends, typically working together a few times a week at …
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Obsession (Topher DiMaggio & Marc Dylan)
by Drill My HoleMarc Dylan is obsessed with Topher Di Maggio Marc has constantly been finding any excuse to be near …
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Striker (Adam Killian & Matt Cole)
by Drill My HoleAdam Killian is a hustler, a bona fide pool shark always looking for the next mark Matt Cole thinks …
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Fight For My Hole (Spencer Reed & Jessie Colter)
by Drill My HoleEvery time Jessie Colter finds a real man that can please his needs, it seems so do the cops Jessie …
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Shoplifters Beware (Phenix Saint & Jackson Lawless)
by Drill My HoleJackson Lawless is a shameless thief with sticky fingers, but he's ripped off the wrong guy this time …
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Prison Shower (Rafael Alencar and Johnny Rapid )
by Drill My HoleRafael Alencar may or may not be one of the first people you would want to meet in the showers on your …
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Paintball (Rafael Alencar & Leon Knight)
by Drill My HoleWhat started as fun and games soon turned into a wild display of Rafael Alencar's fury Leon Knight did …
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Sparring and Groping (Cliff Jensen & Chris Tyler)
by Drill My HoleCliff Jensen and his buddy Chris Tyler have a very competitive friendship, constantly pushing each …
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Room Service (Ricky Sinz and Johnny Rapid)
by Drill My HoleRicky Sinz is looking forward to getting his holiday week started, but after a long day of traveling …
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Caged (Ricky Sinz and Leon Knight)
by Drill My HoleLeon Knight is hanging around a local den looking for a real man to fuck him, lucky for him Ricky Sinz …
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The Other Guy (Trevor Knight, Tyler Sweet & Micah Andrews)
by Drill My HoleTrevor Knight comes home to find his boyfriend Tyler Sweet naked and in their bed Tyler says that he …
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Cumpensation (Phenix Saint & Mitch Vaughn)
by Drill My HoleMitch Vaughn is on his way back to LA from a fun weekend in Vegas when he starts to run low on gas …
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Fucked For A File (John Magnum & Emanuel Brazzo)
by Drill My HoleJohn Magnum has been working on this case day and night, finally against all odds it looks like he's …
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Bottoms Up (Trent Diesel, Dylan Roberts and Marc Dylan)
by Drill My HoleMarc Dylan has a boundless need for pleasure and when his boyfriend leaves for the afternoon without …
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Gay Instinct (John Magnum & Kirk Cummings)
by Drill My HoleJohn Magnum interrogates Kirk Cummings basic instinct style in this scene parody!
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Housepet (Jessie Colter, Kyle Quinn and Trey Turner)
by Drill My HoleJessie Colter and Trey Turner have a problem with their housepet Trey Turner It seems that every time …
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Training the Rosso Twins (Ricky Sinz & The Rosso Twins)
by Drill My HoleThe Rosso twins hire Ricky Sinz to coach them in the boxing ring When the twins fail to take Ricky …
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Impatient Patient (Jacob Durham & Sebastian Young)
by Drill My HoleSebastian Young is in distress, he's now into hour four of having a never-ending, blood pressure …
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The Butcher (Adrian Toledo, Manuel Lopez and Goran)
by Drill My HoleNacho Vidal (cameo) in his Men.com directorial debut crafts a gritty and dark tale about a man (Adrian …
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Sloppy Seaman (Adam Killian and Marc Dylan)
by Drill My HoleSeaman Marc Dylan isn't use to all the rules and regulations in the Navy and unfortunately forgets to …
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Bounty Hunter DP (Johnny Rapid, Boston Miles & Travis Irons)
by Drill My HoleBounty Hunters Johnny Rapid & Boston Miles have their guy in custody and decide to give him a …
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Mechanic Meltdown (Johnny Rapid & Hayden Richards)
by Drill My HoleJohnny Rapid is a shady mechanic who tries to charge Hayden Richards for some work that he didn't ask …
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Bashed and Furious (Paddy O'Brian & Issac Jones)
by Drill My HoleSpeed is the name of the game in this sexy adventure UK hotties Paddy O'Brian and Isaac Jones star in …
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Fucked By Security (Bryce Star & Tony Paradise)
by Drill My HoleBryce Star is making a phone call when Security guard Tony Paradise notices him in an illegally parked …
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Cold Shower (Johnny Rapid & Ryan Rockford)
by Drill My HoleRyan Rockford is busy jerking his meat in the shower when thoughtless Johnny Rapid flushes the toilet …
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Deep Tissue (Jimmy Johnson & Logan Vaughn)
by Drill My HoleMassage therapist Jimmy Johnson is working over Logan Vaughn's ass but gets curious what would happen …
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Custodian's Fury (Alexsander Freitas & Tyler Sweet)
by Drill My HoleTyler Sweet is left to pay the price when the school janitor Alexsander Freitas decides to fight back …
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The Movie Star (Tommy Defendi & Tony Newport)
by Drill My HoleTommy Defendi is a frustrated star wrangler having a hard time with Tony Newport's diva behaviour Fed …
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Wood (Colby Jansen & Marcus Ruhl)
by Drill My HoleA woodcutter isn't amused when his junior puts a cold water bottle against his bare back, so he teaches …
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Paparazzi (Issac Jones, Harley Everett & Marco Sessions)
by Drill My HoleShady Paparazzo Marco Sessions is caught photographing private information about the star he is …
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Bashed And Furious 2 (Paddy O'Brian & Marco Sessions)
by Drill My HolePaddy waits patiently in his car while his criminal colleague is in the throws of a heist With a …
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Drag Race (Jason Goodman & Haigan Sence)
by Drill My HoleJason Goodman & Haigan Sence are so cocky the wage their cars on a single drag race Jason loses …
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Security Breech (Tommy Defendi & Andrew Stark)
by Drill My HoleSecurity Guard Andrew Stark catches Tommy Defendi getting blown in a warehouse and rushes into to put a …
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Handling The Hose (Jessie Colter & Andrew Stark)
by Drill My HoleSexy poolboy Andrew Stark isn't watching what he's doing and knocks Jessie Colter (and his phone!) into …
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Twink in a Box (Tyler Sweet & Topher Di Maggio)
by Drill My HoleTopher Di Maggio wins an auction bid that has an unexpected bonus inside: Tyler Sweet! Topher wastes …
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