Hugo Milano

Hugo Santiago Jacks Off New Release | 21 minutes Rating Rating Rating Rating Rating

Hugo Santiago Jacks Off

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Description: HITS THE FUCKING SPOT. Have you ever cum so hard that the jizz goes places you never expected? Whether you’re a shooter or not, sometimes the cum just flies – usually when you’re having a great fucking orgasm. Juan brought Hugo by my loft, and I got a raging hard on the minute I saw him. He’s got a hot little Latin body and a GREAT ass. You want to bend him over the minute you see him. We introduced ourselves, and I asked Hugo if he’d be comfortable jerking off on camera. He smiled, stripped naked, and started stroking his cock right in front of me. I was like – whoah! I cancelled my beach plans and we all went up to a friend’s villa in the Hollywood Hills. We swam for a bit to chill. Then Hugo got out of the hot tub with his hard cock bulging through his speedo, and I took [more....]

Watch Hugo Fucks Skyler

Hugo Fucks Skyler New Release | 13 minutes Rating Rating Rating Rating Rating

Hugo Fucks Skyler

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Featuring: Hugo Milano & Skyler Caine

Description: The scene opens with Hugo and Skyler already shirtless, showcasing their beefy, tatooed upper bodies. Skyler pins Hugo and begins licking and sucking at his nipples. Next thing you know, Skyler's hard in Hugo's mouth. Hugo licks frantically up and down the shaft of Skyler's cock and covers it in his spit. He fingers Skyler's asshole and we see his body clench around Hugo's finger. The scene jumps to Skyler deep-throating Hugo's enormous wang. Skyler sucks down hard, pressing his nose to Hugo's belly. Next, a close up shot of Hugo inserting his wet cock into Skyler's ass. His balls slap against Skyler's cheeks as Skyler groans, "Yeah, fuck that ass." Hugo is a true fuck machine, with his perfect round balls and even pelvic thrusts. The guys kiss as Hugo rams Skyler's ass, spreading his [more....]

Watch Hugo Fucks Tyler

Hugo Fucks Tyler New Release | 18 minutes Rating Rating Rating Rating Rating

Hugo Fucks Tyler

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Featuring: Hugo Milano & Tyler Ford

Description: Hugo & Tyler start the scene off making out on the stairs, kissing and licking each other's bodies all over. Then Hugo peels his pants off and whips out his hard cock so Tyler can show off his oral skills. Then Hugo returns the favor and gives Tyler a mean blow job while he jerks himself off. When it's time for the ass fucking to begin Tyler bends over the bannister while Hugo gives him a hard fast fucking from behind. He REALLY gives it to Tyler's ass - just listen to him groan as he grits his teeth, trying to take it all. After Hugo's done pummeling him from behind, Tyler lies down on the stairs while Hugo drills him from on top. I can't tell if Hugo's fucking him or punishing him...or both. After Tyler's ass is completely spent the two sit down on the stairwell and jerk out their loads [more....]

Watch Robert Fucks Hugo

Robert Fucks Hugo New Release | 26 minutes Rating Rating Rating Rating Rating

Robert Fucks Hugo

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Featuring: Hugo Milano & Robert Christian

Description: Well hell must have frozen over or somewhere out there there's a pig flying through the sky because I managed to convince that hot fuckin' top stud Hugo Milano to bottom out for the first time ever! I knew I couldn't partner him up with just any ol' top so I matched him up with that hot ripped stud Robert Christian. The two begin in an intense make out session on the edge of a hot tub. It's not long before both of these muscle gods are hard and ready to go. Hugo is the first to go for some cock as he drops down to work Robert's big dick and when I say he works that dick I mean he WORKS THAT DICK! As a reward for being such a good cock sucker Robert returns the favor and gives Hugo a nice wet blowjob. Then the two head inside for the main event. Hugo lays down and lets Robert fuck him on [more....]

Watch Hugo Fucks Travis

Hugo Fucks Travis New Release | 17 minutes Rating Rating Rating Rating Rating

Hugo Fucks Travis

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Featuring: Hugo Milano & Travis Kane

Description: Hugo Fuckin' Milano. I tell ya, it doesn't get any hotter. And he's paired up for this scene with that hot inked up stud Travis. The two kick things off making out furiously with their shirts off. It's not long before Hugo rips Travis's pants down and starts licking him all over until he makes his way to his cock and starts blowing him. For a top Hugo really knows how to work a dick! Then Travis gets on his knees and services Hugo's fat cock. Hugo really gets into it and pushes Travis's head all the way down onto his dick until he chokes him with it. Then it's time for the real action to start as Hugo lays down on the ground so Travis can lower himself onto his hard cock and ride him. Props to Travis for actually being able to take that monster dick. After Travis gets loosened he bends [more....]

Watch Hugo Fucks Scottie

Hugo Fucks Scottie New Release | 15 minutes Rating Rating Rating Rating Rating

Hugo Fucks Scottie

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Featuring: Hugo Milano & Scottie Brooks

Description: The last time Scottie Brooks was on our site he was slam fucking Tory Mason's tight hole. But, as we all know, you can't be a real CockyBoy unless you can take it as good as you give it. To pop his bottom cherry I paired him up with that big slab of Italian meat Hugo Milano. Almost immediately Scottie makes his way down to Hugo's thick cock. Hugo pushes Scottie's mouth down onto his shaft as he orders him to "suck that dick" and to "choke on it" - which Scottie is more than happy to do. After Hugo is nice and hard he starts eating Scottie's ass, getting it wet and ready as he fingers it. Hugo's nice enough to blow Scottie for a bit but what he really wants is ass. Scottie climbs on top of Hugo's hard cock and bounces up and down, struggling to take all that dick. Next Hugo bends Scottie [more....]

Watch Hugo Milano Strokes Off

Hugo Milano Strokes Off New Release | 12 minutes Rating Rating Rating Rating Rating

Hugo Milano Strokes Off

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Featuring: Hugo Milano

Description: Hugo starts off shirtless, showing off his perfectly built, inked up body. Rubbing himself hard, Hugo pulls out his beer can thick dick and jerks his fat shaft as he rubs his balls. I have a feeling Hugo may be the only person I know who isn't a dentist who has to say "open WIDE" so often. Working his nipples and licking his bicep, Hugo strokes his thick hard cock with his spit lubed fist for a while before turning around and bending over as he works his meat, pulling his ass crack open and teasing his hole with his fingers. Then he sticks his slicked up fingers inside his ass to show off his sweet hole for the camera. Hugo turns back to the camera so he can jerk off some more while he sucks on his fingers. The taste of his own ass gets him so worked up that after a little more cock [more....]

THE MANIFESTO

Be proud!

You are not a type. You are you.

“Cocky” does not mean rude.

Gay sex is not shameful. It is a blessing like a fine wine, a great meal, or a roller coaster ride. It is part of life and should be enjoyed.

Be safe. Be smart in all that you do. When in doubt, use the head holding up your ears!

Negativity only invites and creates more negativity.

Mutual respect is the path to true power. Power = pride. Pride = loving yourself. Love yourself and you can love another.

Gay is good.

CockyBoys are proud, confident men. At times funny, goofy, sometimes crazy, and shy.

They have dark days along with good. They like being admired. They do not succumb to cowardice.
They love and want to be loved.

I am a CockyBoy!

Please check your high horse at the door.

There is nothing wrong with being a “porn star.” It may not be your choice. Choice is freedom. So choose.

When having a bad day… stop. Think of five things you are grateful for….feel better?

Oscar Wilde said it best – “Humanity takes itself too seriously. It is the world’s original sin. If the caveman had known how to laugh, history would have been different.”

Love Always & Be Nice,

Jake Jaxson

There is something about the CockyBoys aesthetic that gets porn wheels turning—an ironic touch that’s light enough not to compromise the simple pleasures of whacking off.

— New York Magazine