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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!

Watch Jared & Castro Supreme at ItsGonnaHurt.com

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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: 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: 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: 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: Tristan’s Dream Comes True!

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Tristan's Dream Comes True! at It's Gonna Hurt

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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It’s Gonna Hurt: Lance Likes Big Dicks

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Lance Likes Big Dicks at It's Gonna Hurt

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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It’s Gonna Hurt: We Got A Screamer Folks!

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We Got A Screamer Folks! at It's Gonna Hurt

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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It’s Gonna Hurt: It Really Fucking Hurts!

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It Really Fucking Hurts! at It's Gonna Hurt

As we all know Castro’s 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 Castro’s 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

Watch JJ & Castro at ItsGonnaHurt.com

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It’s Gonna Hurt: Double Your Pleasure or Pain?

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Double Your Pleasure or Pain? at It's Gonna Hurt

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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It’s Gonna Hurt: Castro’s Back Boys!

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Castro's Back Boys! at It's Gonna Hurt

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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It’s Gonna Hurt: Killin’ That Ass

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Killin' That Ass at It's Gonna Hurt

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!

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It’s Gonna Hurt: Ken Tanner’s Ass Fucking

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Ken Tanner's Ass Fucking at It's Gonna Hurt

Hey Guys… Today we brought in this young pup for little bit of ass cracking. He was a nervous little bugger and friends I think we all would be if we had to be standing in line to take a10 inch cock up our rears. Anyways… This update is great! The victims name is Ken Tanner and this mother fucker has been officially cracked in half! Peace Out!

Watch Ken Tanner’s Ass Fucking at ItsGonnaHurt.com

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