See the biggest, longest, fattest cocks stuffed into tight gay assholes. And yes, it's gonna hurt

Handsome Joe Cums A Thick Load

Handsome Joey is the complete package. This 24 year old calls himself “sexual”, which we think means he’s down for all kinds of cock on cock fun given the right opportunity. And with his long and delicious black dick we know there’s going to be a lot of opportunities! He works his magic on that schlong and delivers a hot creamy thick load of cum for us.

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Jaden Loves Black Dick!

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Alright you fuckin sickos! Here it is… We picked up this guy Jaden here Miami at a local college campus. It really was crazy of him to skip class but he still did after all. We went back to my place and the rest is history. Jaden was one horny little fucker when he saw Castros big black man root. It was great watching him do some slow blowing which built up to him getting his happy asshole fucked out six ways to sunday! Come watch another fall to the ass slaying of Castro Supreme!

Jared Is A Quitter

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So we got a new It’s Gonna Hurt update. This guy Jared came to test his will by taking a massive size cock up his poop chute! Unfortunately for Jared he will be shitting weird for the rest of his life. Castro literally gutted this poor man’s insides. Come all who dare to test Castro’s big black dick up their ass!

Screaming For Joy!

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This site itsgonnahurt.com is no fucking joke. We brought in this dude Tony Douglas. Tony craves black dick. He receives what he craves right up his tight little asshole. He then proceeds to scream like a bitch in heat and pant like a dog while Castro puts a blistering beating down on him until he receives his man milkshake all over his face.

Twenty…Scared… And Hungry!

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This episode of itsgonnahurt.com stars a little 20 year old white boy named Alex and of course The King of Ding-a-lings… Castro Supreme. This little fucker loves to suck black dick. He also likes being impaled with cocks and dix bigger than his limbs. He seemed to really enjoy his scene. Just kidding he screamed like a little bitch! HaHa…Peace!

Mclovin Loves Black Dick

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This itsgonnahurt shoot features this guy Erick who is a man of few words with one thing on his mind and that is big black dick that will bring him more pain than he can bare. He actually handles being double stuffed by Castro and Izzy pretty well. In the end he got what he came for : A swollen asshole and cum all over his lips. He took his savage asshole ripping like a champ! Good job Erick your pain is our reward! Peace out fuckers!

Scared Little Logan

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Here we are again with another fantastic update of It’s Gonna Hurt (itsgonnahurt.com). We brought in this scared little boy named Logan for an asshole destruction session. Logan was so scared he literally locked himself in the bathroom and had to be convinced to come out and play. After a few moments he submitted the booty and it was on, Castro had no problem stuffing his giant black dick up Logans tight little asshole. It was over quickly as Castro took it to him… slamming his ass until he sprayed nut all over logans face. Good times!

Fairy Tales Come True.

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Today we have a newbie named DJ who said he doesn’t believe in fairy tales and dragons and shit. So I ask him a few questions like what is the biggest he has every had, you know typical shit, he told me 8 or 9. So I laughed when I told he about the size of Castro’s unit and he seemed pretty nervous about the whole event. I told him its like a good fairy tale that has a GREAT ending. As soon as Castro pulls out his hook and totally puts on a fucking show worth a crowd applause. Castro shows him how myths and fairy tales are so fucking true when he unleashes his dragon with a hardcore fucking pounding, boom boom all in his fucking face..

Gettin Hooked

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What’s happening my bitches! We got a nice update for you today with Tony. He’s hungry for some cock, some dragon cock that is! Poor Tony, I’m not too sure he really knew what he was in for. He claims he was ready, but from his expression when Castro came around the corner and surprised him, he was nothing but stunned! Tony didn’t miss a beat though. He jumped on the hook right off the bat. Castro had him in all sorts of positions. Tony found out pretty quickly that It’s Gonna Hurt when you get the Hook!

Big Boys Like Big Toys

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We got another asshole slaying for you all here on Itsgonnahurt.com. We brought in this big muscle head dude named Mitch to get his b-hole beat up by Izzy’s monster dick. Mitch was completely terrified when I told him we were gonna lock the door so he couldn’t run out when he got too scared or when the pain reached its ultimate high. Anyways you should come watch this jacked white dude take some black dick!

White Boys Love Black Dick

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Hey peeps…. Here is another heartthrob white boy who can’t resist a massive chocolate cock. We brought in this boy Cameron and he came prepared. Well at least thats what he said. It seems everybody’s story changes once they get a huge black dick smacked off there forehead. To make a long awesome story short Izzy fucks this white boy until he can’t take it anymore and then drops a monster load on his face. Its gonna hurt Baby!

Snake Dancing

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Wow this guy was not ready. This week’s itsgonnahurt update is crazy. We brought in this cat Santiago for an anal pulverizing session and let me tell you all he was not ready. He said "It hurts like hell" and we said "NO shit! The site’s called Itsgonnahurt.com". The weirdest shit happens when Santiago first gets the black pipe stuffed into him. I want to tell y’all but I would hate to be a spoiler. So watch this video and dream and who knows you could be next!

Wake Up Call

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If you love big black dick then you would love to be woken up by one being stabbed in your eye. This weeks update is classic. We actually started this shoot with Izzy slapping his massive dick off this guy Alex’s face while he was asleep. As soon as Alex woke up he was in heaven and immediately started blowing the shit out of that big chocolate stick. Alex really enjoyed himself today and we think you will too. Check it out bitches!

Evan Likes Black Dick

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Hey people… This week we bring you another painful adventure on itsgonnahurt.com. In this episode Izzy puts the hammer to this little white boy named Evan Eros. Evan is a stripper and he loves hot chocolate in his mouth… if you no what I mean. If your here to see pain you got it. If you like interracial you got it and if your just plain old sick in the head you got it. I think your gonna love watching this little white boy get his shit pushed in! Enjoy!