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Clayton Was Scared!

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LOL… I always think it’s funny when people cum to take Castro’s Dick in there ass. There facial expressions say it all. This guy Clayton came to us and during the beginning of the shoot he was literally shaking. I would assume he was scared but you never know he could have been penis withdrawals or some shit like that. You just never know with some of these sick fuckers. Cum watch Castro gut this fool!
Its Gonna Hurt RSS Feed  Mar 8 Big Cocks, Interracial gay

No Homo Bro!

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All in the name of money i say and well these dudes send in their submission video, which i have to say was rather entertaining. Pledges are made to suffer and what better way then to have a pretty gay photo shoot. This frat was low on funds and needed to find a quick and easy way to make some money. And that's exactly what they did. having their pledges pose for the cam and do pretty questionable things was just the thing they needed to win their 10G's Congrats guys keep up the good work!
Haze Him RSS Feed  Mar 3 Big Cocks, Interracial gay, gay college boys

Spencer The Badass

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Greetings Fans! LOL…On this episode of itsgonnahurt this guy Spencer had no concerns about Castro’s Horse dick being crammed up his poop hole. Well at least that was his theory before the shoot. After the shoot we saw was a scared individual who had just received an intestinal rearrangement! Come laugh… Cry… and Cum.
Its Gonna Hurt RSS Feed  Mar 1 Big Cocks, Interracial gay

Savage Asshole Stretching

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A lot of people ask… "Is this Real?", "Is Castro’s Cock that Big?" Well, my friends… go ask Noah Brooks, the latest victim on It’s Gonna Hurt. Noah always wanted to try a big black dick. Now he has, and I’m pretty sure he will never do it again. He received a savage asshole stretching with a side of cream sauce. We warned him… It’s Gonna Hurt!
Its Gonna Hurt RSS Feed  Feb 22 Big Cocks, Interracial gay

Simon Says…

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So we all remember the timeless classic Simon says right? well this week we received a very interesting version of the game. these frat boys had their pledges play it naked and Simon was telling them to do some very questionable things. i guess Simon grew up and became a perv anyhow this one is pretty entertaining and just down right wrong lol enjoy.
Haze Him RSS Feed  Feb 17 Big Cocks, Interracial gay, gay college boys

Youngster Gets An Ass Fucking

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So let it be known that Castro Supreme’s cock is no fucking joke. This guy’s job is to destroy assholes and plumbing systems. We got another anal victim named Jacob; this guy had tears of joy blowing Castro’s fat dick. Here is another video for all you sick fucks who love to watch young men get their assholes ripped open! Enjoy, Fuckers!
Its Gonna Hurt RSS Feed  Feb 15 Big Cocks, Interracial gay

Back Blown Out!

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Alex Hilton is excited to see Castro Supreme’s boomerang cock. Not only will he get a chance to witness a cock of that caliber, but he’ll also know what it feels like having a monstrous cock shoved up his ass. Alex Hilton was all smiles once Castro stood in front of him with a 13-inch cock gazing into his eyes. All he could do was jump for joy, wrapping his lips around the cock without hesitation. Barely fitting it in his mouth, Alex decided to see if his ass can do better. Ouch! Bad move dude. No worries though; Castro is a gentle giant. Enjoy!
Its Gonna Hurt RSS Feed  Feb 8 Big Cocks, Interracial gay

The Tailgate

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It's the biggest game of the year and this frat decided to embarrass their pledges by taking them out on their tailgate shenanigans. Not only did the pledges have to cook the food, serve it and dispense beverages, they had to do it all naked, and every time the home team scored a touchdown they had to streak down the parking lot chanting "touch down pants down!" It sure as hell was an amusing sight. Then things got a little out hand once the action moved into the RV; check this one out!
Haze Him RSS Feed  Feb 3 Big Cocks, Interracial gay, gay college boys

Doing It Big!

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Payton’s a bit nervous about interviewing for It’s Gonna Hurt. Who wouldn’t be! Having a cock shoved up your ass that’s big as a bat isn’t easy. Especially when Casro Surpreme’s dick hooks to the left. It’s going to hit each wall in Payton’s asshole. Hope he knows what he’s getting himself into. The only thing I can advise him is to think happy thought because It’s Gonna Hurt. Enjoy!
Its Gonna Hurt RSS Feed  Feb 1 Big Cocks, Interracial gay

Steven’s Ass Is Totaled

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OMG… This guy Steven Waye gets his asshole torn apart by Castro’s massive cock. Much to my surprise he enjoyed every second of it. Steven loves sucking big black man dick. I think anyone who loves watching dudes get fucked by big gnarly black cocks will deeply enjoy this episode of It’s Gonna Hurt. Cum watch Steven get a hot cum bath. Enjoy, you sick fuckers!
Its Gonna Hurt RSS Feed  Jan 25 Big Cocks, Interracial gay
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