It’s Gonna Hurt

It’s Gonna Hurt: Gay For Pay

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Gay For Pay at ItsGonnaHurt

We have another fella who seems to have no problem sucking dick for a pay check. He did have a little bit of an issue getting Izzy’s huge black cock up his asshole. This sites not called itsgonnahurt.com for nothing. Here we make pain a reality and this young little white boy got what he came for and maybe even a little more than he wished. Cum watch this guy Devin squeal like a pig!

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It’s Gonna Hurt: Wake Up Call

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Wake Up Call at ItsGonnaHurt

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!

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It’s Gonna Hurt: My Friends Are Going To Love Me!

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My Friends Are Going To Love Me! at ItsGonnaHurt

A super fan of Castro’s huge cock can’t wait to experience and tell all his friends how it really went down. He can’t believe how big his fucking cock is; he even takes pictures of him like he met a celebrity; I think he even tries to talk to it and say HELLO! He jumps right into to some great BJ action taking all that cock in his mouth. It looks fucking amazing; especially when he spreads his legs wide, ear to ear, and lets Castro and his partner in crime straight pound his tight asshole to make him scream like a girl! He takes as much as he can of Castro’s UNIT and totally thanks him numerous times, lol. This might be Castro’s #1 fan! Who’s next to try out the MONSTER? Maybe you…. Watch this video.

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It’s Gonna Hurt: Fairy Tales Come True

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Fairy Tales Come True at ItsGonnaHurt

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..

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ItsGonnaHurt: Gettin’ Hooked

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Gettin' Hooked at ItsGonnaHurt

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!!!!

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It’s Gonna Hurt: Mclovin Loves Black Dick

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Mclovin Loves Black Dick at ItsGonnaHurt

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!

Watch Erick, Castro & Izzy’s Video Clip | Visit ItsGonnaHurt.com

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It’s Gonna Hurt: 20 Plus Inches of Hell!

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20 Plus Inches of Hell!

We only promise one thing here on itsgonnahurt.com and that is PAIN! We brought back Castro’s partner in crime Izzy to double team this guy Jacob. Jacob is a young white guy who obviously is very impulsive because I don’t think he thought this idea through a 100%. Long story short: He gets his tight asshole cracked open by two monstrous black dicks because I guess one wasn’t good enough!?! At least he enjoyed the hot baby bath at the end!

Watch Twenty Plus Inches of Hell Video Clip | Visit ItsGonnaHurt

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It’s Gonna Hurt!: Double Dick Destruction

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Double Dick Destruction at It's Gonna Hurt

Boy oh Boy… Break out the lube ’cause you guys are gonna love watching two hung black guys stuff this little white dudes holes. I think this little dude reached his pain threshold pretty early! Fuck…I think any body would with two giant dicks in there ass! Long story short: 2 Big black dicks + one asshole = ItsGonnaHurt! Peace bitches!

Watch The Teaser Clip | Visit ItsGonnaHurt.com

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It’s Gonna Hurt: Jared is a Quitter

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Jared is a Quitter at It's Gonna Hurt

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!

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It’s Gonna Hurt: The Lumber Jack Slam!

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The Lumber Jack Slam! at It's Gonna Hurt

Hey everyone. Today we brought in this guy named Cory and it’s was really great watching this 6 ft 5 inch guy surrender to Castro’s giant cock. This guy was a real champ cause he tried to deep throat Castro’s meat! It didn’t really work but it was fun watching him gag and tear up like he was crying! I think at one point he might have been crying. Seriously check this big lumber Jack get his hole pounded!

Watch Cory & Castro Supreme at ItsGonnaHurt.com

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It’s Gonna Hurt: Castro the Impaler

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Castro the Impaler at It's Gonna Hurt

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.

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It’s Gonna Hurt: The Gym Rat

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The Gym Rat at It's Gonna Hurt

What’s up fellas.. today we got this guy Zack who is a cute young gym rat that’s in good shape.. Good shape to get FUCKED by Castro and his massive unit. Me and Zack went back to meet Castro and Zack got a face full of man meat, which he happily sucked up like a vacuum cleaner. Zack got his ass opened really wide, he moaned and whimpered a bit and in the end he got a shot right in the eye. He loved every second of it and so did I.

Watch Zack & Castro Supreme at ItsGonnaHurt.com

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It’s Gonna Hurt: Cutting Class For Cock (Castro Supreme & Josh Slyman)

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Cutting Class For Cock  (Castro Supreme & Josh Slyman) at It's Gonna Hurt

We met up with this local college guy named Josh Skyman who has a curiosity for big dicks. He has to get back to school in a couple hours so we went back to my place and let Castro Supreme unleash the beast on him! Josh got his guts smashed in and he had to make Castro slow down and stop a few times.. but at the end of the day he loved the pain.

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It’s Gonna Hurt: AJ Plays the Pain Game

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AJ Plays the Pain Game  at It's Gonna Hurt

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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It’s Gonna Hurt: Lunch Time!

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Lunch Time! at It's Gonna Hurt

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!

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It’s Gonna Hurt: Roman Goes Long

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Roman Goes Long at It's Gonna Hurt

Greeting’s People! Today we got a real nasty fucker on It’s Gonna Hurt. I found this straight guy named Roman who had a fantasy about getting some big dick in his ass. So that’s where Castro came into play! I think this guy had to go to the hospital after Castro stuffed his large man stick up his ass. Anyways it was a real fun shoot with lots of blood curtailing screams and that’s what happens when you try to stuff a baseball bat into a coin slot! Later bitches!

Watch Roman & Castro Supreme at ItsGonnaHurt.com

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It’s Gonna Hurt: Ouch!!!

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Ouch!!! at It's Gonna Hurt

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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It’s Gonna Hurt: David’s Meat Ride

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David's Meat Ride at It's Gonna Hurt

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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It’s Gonna Hurt: Aiden From Boston

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Aiden From Boston at It's Gonna Hurt

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

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It’s Gonna Hurt: Jaden Loves Black Dick!

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Jaden Loves Black Dick! at It's Gonna Hurt

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 Castro’s 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!

arget=”_blank”>Watch Jaden & Castro Supreme at It’s Gonna Hurt.com

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It’s Gonna Hurt: Tucker The Fucker!

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Tucker The Fucker! at It's Gonna Hurt

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

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It’s Gonna Hurt: Training Day

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Training Day at It's Gonna Hurt

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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It’s Gonna Hurt: Beach Day Ass Fucking

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Beach Day Ass Fucking at It's Gonna Hurt

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!

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It’s Gonna Hurt!: Ricky’s Tapout!

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Ricky's Tapout! at It's Gonna Hurt

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

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It’s Gonna Hurt: Kyler’s Meat Stick Ride

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Kyler's Meat Stick Ride at It's Gonna Hurt

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!

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