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!

Watch Jared & Castro Supreme at ItsGonnaHurt.com

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I met up with Alejandro who is in town for a bit visiting his parents. We met up in the afternoon and his went back to his parents place since they were at work. We set up shop out by his pool and introduced him to Castro's cock which we warmed up to pretty quickly and began sucking the shit out of it. The two of them fucked like crazy and sweat their asses off in the hot sun. Alejandro couldn't take it towards the end begged for Castro's hot nut.

Watch Alejandro & Castro Supreme at ItsGonnaHurt.com

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This week on its gonna hurt we brought in this Guy AJ. Unfortunately for him... I brought Castro's supreme ding-a-ling. It wasn't very long til' AJ really started screaming. I would have to say this looks like it might be one of the most painful episodes I have ever filmed as the director for this site. In the end Castro dropped a big hot gluey load all over AJ's face and that was a wrap! Cum and check this shit out!

Watch AJ Irons & Castro Supreme at ItsGonnaHurt.com

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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!

Watch Matthew & Castro Supreme at ItsGonnaHurt.com

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Hey people! We brought in this guy Tyler this week for It's Gonna Hurt. Tyler has a girlfriend which doesn't no he likes big black dick. In fact I'm not really sure he likes big black dick anymore after Castro got done with him. This guy was having all sorts of issues gagging and screaming like it was his first time with a giant piece of man meat. But as usual he got a creamy hot load of man paste splattered all over his chinny chin-chin!

Watch Tyler Ford & Castro Supreme at ItsGonnaHurt.com

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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!

Watch David & Castro Supreme at ItsGonnaHurt.com

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Hey peeps... Last time I was home in Boston I met this guy named Aiden. We were drinking and I told him what I did for a living and he was ecstatic. All he could talk about was Castro's cock. After I gave him my email... wouldn't you know this mother fucker got at me the next day cause I guess he wanted his insides rearranged or something. Needless to say Castro tears this little fuckers ass up and dumps a hot load of milk all over his nuts. Looked painful but I guess he loved it and he would do it again. Crazy fucker! -Joey

Watch Aiden & Castro at ItsGonnaHurt.com

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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

Watch Tucker & Castro Supreme at ItsGonnaHurt.com

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Here's the deal... We brought in this guy Alexander for this weeks it's gonna hurt update. Alexander is a really fit Jacked dude who wanted to suck on a big fat black cock. Luckily for him I know Castro! Castro had no problem dropping his draws for a good looking guy to slob on his knob. After a filthy cock sucking Castro stuffs his giant cock in a nice tight asshole and it was painfully sweet with a great big load on the face. Enjoy!

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Hey guys! Joey here, This week we hit the nude beach and met up with a buddy of mine. His name isTristan and my people his little butt hole is in for a pounding. I presented him the Castro Supreme! Right from there we went to my apartment and they hit it off from there. When Castro revealed his Foot-long Supreme, he knew it was GONNA HURT!

Watch Castro Supreme & Tristan at ItsGonnaHurt.com

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Well my friends... Not every one can bite there lip and take Castro's supreme ding-a-ling up there keaster. Today we brought in this tall model named Ricky and he was in trouble from the start cause Castro's dick barely fit in his mouth. It was quite the experience for this youngsters tight little asshole and I would be willing to bet that this was his first and last visit to ItsGonnaHurt.com! LOL

Watch Ricky & Castro Supreme at ItsGonnaHurt.com

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Hey guys... Got a real treat for y'all today on It's Gonna Hurt! We brought in this guy Kyler and I'm not gonna lie. I was pretty sure he wasn't ready for Castro to put his massively huge cock in his tight little ass. Much to our surprise, Kyler handled it pretty well - with a little kicking and screaming of course - until he received a dose of hot man milk all over his face. Bottoms up and enjoy!

Watch Castro & Kyler at It's Gonna Hurt

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Hey people... There are no waves in Florida! So don't bring your surf board to the beach or you'll have nothing to do except get a big black cock shoved up ass and cum all over your face. LOL! Today we picked up this little surfer dude at the beach. His name was Rex and he wanted Castro's Supreme in his you know where. After a grueling 40 minutes of anal stuffing, Rex got a hot load of Castro dumped on his face! Good times! Don't miss out.

Watch Rex & Castro Supreme at ItsGonnaHurt.com

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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.

Watch Tristan & Castro Supreme at ItsGonnaHurt.com

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Once upon a time there was a young boy named Jon Estevez. Jon had a fantasy of two big black dicks double teaming his little asshole. In his wildest dreams he never imagined it would come true until one day he ran into Castro Supreme and Diesel Washington and it was all history after that because Jon got his insides rearranged. then followed a big hot shower of man gravy all over his face. Dreams do come true!

Watch Jon Estevez, Castro Supreme & Diesel Washington at ItsGonnaHurt.com

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Hey there It's Gonna Hurt fans... This weeks update is real solid. We brought in this young fresh meat named Lance for an anal pounding and I must say we were all impressed by his dick-taking abilities. Considering he had a baseball bat sized cock jammed up his ass with a smile on his face impressed the fuck out of me. I would say to watch this but I know you sick fucks are gonna anyways! LOL

Watch Lance & Castro at ItsGonnaHurt.com

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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 Castro's 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?

Watch Dareian & Castro at ItsGonnaHurt.com

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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!

Watch Castro, Mario & Derek at ItsGonnaHurt.com

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Word up yall! You will be happy to no Castro is back and he brought his monster black cock to fill your fantasy's or mouths which ever you prefer. In this update an 18 yr old boy by the name of Sam Casey gets his insides rearranged by the supreme ding-a-ling. I promise all you guys out there will drool watching this big black sausage cracking some butthole open!

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Hey People! Today on Its gonna hurt we brought in this young buck named Kyle. Kyle told us "the biggest dick I ever had was 8 inches". Dick size is like dog years every ich is like 10 years sooooooo...... Needless to say he got his shit split in half. And I shit you not he screamed like a Bitch it was great! You gotta watch this video! It is very stimulating!

Watch Kyle at ItsGonnaHurt.com

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