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

Pain+Stitches= Supreme

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Fuck man! Today this guy Jake Taylor came to visit us! Well he actually came see Castro. I think the day went pretty well for him. He got a big fat cock down his throat and his asshole blown out by a ten inch monster cock. Wow if you love seeing big dicks in tight little asses then your gonna love this video. It’s gonna Hurt Mother Fuckers! LOL

Officially Cracked In Half!

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Hey fans! Today on It’s Gonna Hurt we brought in this guy named Ryan for his yearly dose of cock. When I say yearly I mean this is all his asshole will be able to handle for the year! Mario Costa literally cracks this guy in half. Ryan liked it rough so he got it rough. And my friends when you get rough from a dick like Mario’s you don’t walk right for a week! Come watch this giant cock gape some asshole.

Double Your Pleasure Or Pain?

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Listen up… We figured you guys wanted to see it so we did it! Castro and Mario sharing a mouth and asshole. This shit is crazy and we think your gonna love it. These two monster cocks do some serious asshole boring and my friends this shit had to of hurt! In this update we brought in some fresh meat named Derek and I’ll say "I don’t think he was prepared. When the guys were done pounding his mouth and ass it was time to head to the clinic to get his holes stitched shut! Don’t miss out on this crazy update!

It Really Fucking Hurts

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As we all no … Castros cock is massive and in today’s update he really does some asshole punishment on this guy JJ. JJ is a youngster who always had a fantasy of a big black cock getting shoved up his crack. I don’t think JJ thought it fully through. He takes Castros huge man meat for a while. I think this shit really really hurt but fuck it and just watch the update. Oh yeah this guy also eats used condoms! lol

We Got A Screamer Folks!

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Everyday we receive phone calls to ads we post in locals all over, you might read " Looking for young men who want to play with a big black cock." After receiving tons phone calls, we found a candidate for y’all. His name is Dareian and his all time fantasy is to get a black cock shoved up his asshole. I say this very delicately but the actions of this process are not so ginger. Much to are surprise Dareian loved every second with Castros enormous member in his mouth and ass. It was a fun day for this adventure seeker and you can bet it hurt like hell. Who knows maybe you’ll be next?

Tristan’s Dream Comes True!

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Calling all sicko’s to watch this video. If you like big black cock then your gonna love this movie. Today on itsgonnahurt.com we brought in this guy Tristan to have a taste of Castro Supreme’s juicy black man meat. Tristan was a real go getter and I would say he gave it all he had but…. Castro’s cock ate him alive once again we had a tapout. Tristan’s little asshole could not handle it but he was a good sport and he got a milky load he deserved poured all over his face.

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!

Tucker The Fucker!

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Hey guys… Cumming back at ya with this weeks update of its gonna hurt. It was a rainy day here in Miami but that didn’t stop us from our weekly asshole stuffing. Castro and I met up with this cat named Tucker. Basically to make a long story short: Tucker likes dick in his mouth and ass. Luckily for him we have lots of dick to accommodate those two little holes. He wined like a bitch but like I told him before we start "Dude, It’s Gonna Hurt!" HAHA -Joey

David’s Meat Ride

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Sup fucker’s? We got a real sweet It’s Gonna Hurt update this week. I brought in this guy David from one of the ads and this little fucker was a freak. Here I thought taking a forearm sized cock up your ass was on the wild side but seemed that it was just another day at the office for little David. David was telling us how he has been gang banged by 30 dudes in one sitting. All I thought was "well I guess your ready to meat your maker!". After all was said and done he kinda whined like a virgin being cracked for the first time. It was great! Cum watch Castro’s Monster dick light a fire in some asshole!

Lunch Time!

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Attention all sicko’s! This week’s itsgonnahurt.com update is painfully delightful. We got this guy Matthew who was dieing to get Castro’s enormous cock in his ass. Today was his lucky day and he received all 5 pounds of meat straight up his asshole! I really think he liked it too. Matthew also liked nursing on that dick cause he literally sucked castro’s cock clean! To make a long story short… Its gonna hurt BITCHES!

Cristin Gets A Meat Stick

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Wow… another day, another asshole. We brought in this guy Cristin today for another exciting episode of itsgonnahurt.com. Cristin was a man of few words but that was okay cause we new why he was here. This guy was in desperate need of an asshole jam session and, people, he got what he was asking for cause I honestly have never seen an asshole swell up like this! Cum see for yourself as this skinny little minion gets his ass torn apart!

Super Slam!

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Hey people… We got another one for ya! His name is Adam and it’s gonna hurt. Adam was all excited to get his asshole reamed until the time came. Then Adam was a screamer begging for Castro to take his giant cock out of his asshole but Castro wasn’t havin any of that noise. So this guy got his ass swelled up! Cum watch this guy Adam get his shit pushed in!

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!

High Rise Hunks – Jordano Santoro & Krave Moore

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High up in a luxurious skyscraper, lovers Krave Moore and Jordano Santoro get cozy above the bustling metropolis. As Krave takes in the myriad sights and sounds from the balcony, Jordano joins him, nuzzling up from behind. They both become very turned on, and retire to the bedroom. This is where Jordano unsheathes Krave’s large, swelling cock. Sucking it slowly and gently at first, Jordano works into a fervent rhythm, bobbing up and down, deep and long on the erect dick. Krave turns Jordano around and licks his sweet hole. Jordano’s lamentations of ecstasy fuel Krave’s ravenous desire. After fucking Jordano’s plump ass with his tongue, Krave allows Jordano to slurp some more on his fat dong. Then Krave takes control again by spreading Jordano’s tight asshole and sliding his massive member deep inside. Watch these penthouse lovers exchange intense passions while suspended high above the city.