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Video Updates

Drill My Hole – Bet Your Ass: Phenix Saint fucks Trenton Ducati

May 20, 2012

Training buddies Trenton Ducati and Phenix Saint are having a little competition….and the loser gets fucked! Trenton loses all of the 3 competitions so lucky Phenix gets to fuck his tight ass hard! Trenton rides his buddy’s cock then busts his nut all over his own chest while getting his ass pounded.

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Video Updates

Drill My Hole – Weekly Appointment: Phenix Saint fucks Marc Dylan

May 17, 2012

Businessman Marc Dylan likes to be submissive now and then… So he hooks up with escort Phenix Saint to get bossed around and thoroughly fucked in his office. Phenix fucks the sex pig very hard then he shoots his load all over Marc!

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Video Updates

Drill My Hole – Crazy for Cock: Race Cooper fucks Jessie Colter

May 13, 2012

Race Cooper is a psycho being held in asylum. His nurse Jessie Colter tries to feed him with sausages, but instead of eating, Race lick and sucks them! Jessie get him out of the straitjacket and when he looks away, Race grabs him and starts pulling of the nurse’s pants. He starts sucking Jessie’s cock and licks his ass until it’s ready to get fucked! Race pounds the nurse hard and they both cum all over Jessie’s abs!

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Video Updates

Drill My Hole – The Badge: Spencer Reed fucks Connor Chesney

May 10, 2012

Spencer Reed is listening the music really loud, so officer Connor Chesney knocks on his door, because they’ve already gotten dozens of complaints about the loud noise. Spencer tries to escape, but Connor gets him…of course Spencer is a lot bigger so he gets on top and power fucks the cop’s tight ass first with his viper then with his own huge cock!

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Video Updates

Drill My Hole – Mechanic Meltdown: Johnny Rapid and Hayden Richards

May 6, 2012

Hayden Richard is pissed at the car mechanic Johnny Rapid, because he put some stuff into his car that he didn’t ask for…Hayden pounds Johnny’s tight hole until both of them cum all over the place!

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Video Updates

Drill My Hole – Bounty Hunter DP: Johnny Rapid and Boston Miles fuck Travis Irons

April 29, 2012

The Drill My Hole site has just been updated with a hot 3some called “Bounty Hunter DP” starring Johnny Rapid, Boston Miles and Travis Irons. Johnny and Boston are bounty hunters and Travis is their latest catch. They handcuff him and take Travis to a hotel room, where they can fuck the shit out of him! You will see face fucking, double penetration and more!

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Video Updates

Drill My Hole – Time Shared: Sebastian Young fucks Tony Newport

April 26, 2012

Sebastian Young fucks Tony Newport on the new Drill My Hole video called “Time Shared“! Watch Sebastian’s big dick get sucked and fuck Tony’s tight hole really hard. Another great video by Men.com!

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Video Updates

Drill My Hole – Spencer Fox fucks Sebastian Keys in Hotel Break-In

April 22, 2012

Spencer Fox is on his hotel room taking a shower, then suddenly he is hearing noises coming from another room. There is a thief in his room. Sebastian Keys gets caught and Spencer wants to punish him with getting his huge cock sucked and jackhammers Sebastian’s tight ass!

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Video Updates

Drill My Hole – My Bitch: Tyler St. James and Dereck Fox

April 8, 2012

Tyler St. James and Dereck Fox are long-time friends, typically working together a few times a week at least but Tyler hasn’t been around lately. During todays session Tyler won’t stop talking about the club chick he met who is also the reason that he has been missing workout sessions with his friend. Dereck tells Tyler that he fucked her too not thinking it was a big deal, but it turns out to be a HUGE deal sending Tyler into a rage. Tyler pushes Dereck telling him that the only way to make this up to him is to let Tyler fuck him….

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Video Updates

Drill My Hole – Sloppy Seaman: Adam Killian fucks Marc Dylan

April 5, 2012

Seaman Marc Dylan isn’t use to all the rules and regulations in the Navy and unfortunately forgets to cleanup his lunch tray leaving it right in-front of Lieutenant Adam Killian – big mistake. Lt. Killian wastes little time in letting Marc know his mistake and mashes the lunch leftovers all over Marc’s white shirt before ordering him to report to Adam’s quarters. Marc reports to the Lieutenant and is immediately ordered to suck the LT’s dick for having a dirty shirt!

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