• Zale Flip Flops with Armani in First Bottom Scene

    Zale Flip Flops with Armani in First Bottom Scene

    Site owner Bryan Ockert and has been trying to get Zale to bottom. Zale first filmed with Chaos Men back in January, and he returned in February for a blowjob, then he disappeared. When he surfaced again last month, he fucked two guys. Ockert says that Zale was never flat out opposed to bottoming, he just wanted to fully appreciate a guy's butt, you know, since he normally fucks girls. But when both of his bottoms said that getting fucked wasn't that bad, and that their orgasms were more intense, Zale's interest was piqued.

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  • Jackson Fillmore & Jimmie Slater Flip-Fuck

    Jackson Fillmore & Jimmie Slater Flip-Fuck

    San Francisco otter Jackson Fillmore loves cock. He's cute and lean. He is paired with Jimmie Slater at Lucas Entertainment for this flip-fuck scene which includes a cameo from Pedro Andreas, who is happy to fill both boys with greedy holes using a double-ended dildo!

    3 day trial at Lucas Entertainment here!

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  • Pierre Fitch Flip Fucks Darius Ferdynand

    Pierre Fitch Flip Fucks Darius Ferdynand

    Pierre Fitch was really supportive of Cocky Boys after they took home five trophies at the CyberSocket Awards in January. Pierre had his eye on one Cocky Boy in particular and that was Darius Ferdinand, who he spent the entire night flirting with. Darius flew to Montreal to hang out with Pierre and here's the scene that resulted! Pierre tops Darius first and then flips to take Darius' cock.

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  • Palmer Gives Brannon A Good Breeding on Chaos Men

    Palmer Gives Brannon A Good Breeding on Chaos Men

    Palmer is an ideal scene partner for Brannon on Chaos Men with his sculpted body and similar height. Both guys had just finished a physique show and Brannon has a bit of a glow from his spray tan! When fully naked and with their cocks rock solid they quickly get into some 69 action. There's some body worship going on and although neither guys are that experienced at sucking cock, they know just how to fuck! They flip fuck each other bareback ending with Palmer dumping his man seed up Brannon's cute butt hole.

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  • Sean Cody's Curtis and Tanner Flip Flop

    Sean Cody's Curtis and Tanner Flip Flop

    I had forgotten how much fun it was watching Curtis getting fucked. The ginger stud filmed a couple of dozen videos for Sean Cody, then he disappeared for a couple of years. But recently he returned to film a comeback video with newcomer Forrest, and this week Curtis is flip flopping with Tanner. Neither one of these guys lets the other off very easy, they both pound hole pretty hard. You'll love seeing Curtis curling his toes when he's getting ready to spunk, and Tanner drills him right over the edge.

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  • Tyler and Zak Flip Fuck Raw

    Tyler and Zak Flip Fuck Raw

    Experienced young straight hottie Tyler White leads newbie Zak Parker thru his first bareback flip fuck video over with Broke Straight Boys this week. The guys are both eager to please the waiting fans, and after some horny mutual dick sucking, Tyler impales Zak's butthole bareback - then later they flip and Zak returns the favour!

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  • Zach Fucks Max, Then They Flip and He Bottoms For The First Time

    Zach Fucks Max, Then They Flip and He Bottoms For The First Time

    It's always been a sexual fantasy of mine to be in a gym shower and some hot straight spectacularly gorgeous hunk joins me - he asks me to soap his back - naturally I oblige. He turns around and is sporting a major boner and things just get hotter and hornier from there! Well, it seems someone over at Gay Hoopla have had the same fantasy, as this is the premise for their recent update starring Max Summerfield and Zach Douglas - and I can tell you, it's a raunchy one too - totally got me hooked, right from the get-go!

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  • Damien Gunn and Lukas Grande Interracial Flip Fuck

    Damien Gunn and Lukas Grande Interracial Flip Fuck

    Cocky Boys does it again - they just do flip flop fucks so well - and to top it off today, it's also a raunchy interracial flip fuck too! Super-hot twinks Damien Gunn and Lukas Grande are both relative new-cummers to the site and were both equally thrilled to be partnered with each other, as both enjoy a big cock - either in their mouths or up their butts - just as much as the other!

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  • Cocky Boys: Justin Matthews and Max Carter Flip Fuck

    Cocky Boys: Justin Matthews and Max Carter Flip Fuck

    Max Carter is eager to blow Justin Matthews 7.5 - 8 inch cock (Cocky Boys weren't 100% sure). Max is the first to get fucked in this flip flop scene, but it doesn't last all that long. It seems Justin Matthews is the bigger bottom, because for most of the video Max Carter is fucking him.

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  • Jake Bass and Justin Matthews Passionately Flip Fuck Outdoors

    Jake Bass and Justin Matthews Passionately Flip Fuck Outdoors

    Cocky Boys, the 2014 XBIZ Gay Studio of the Year winners, are hard to fault. Their productions are always first rate, professional, both sexy and sensual, and highly erotic - all at the same time! And this latest release, starring the gorgeous Jake Bass and the equally handsome Justin Matthews in a passionate outdoor flip fuck, is just about as good as it gets!

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