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It's Gonna Hurt - A Little Pain for the Holiday


It's Gonna Hurt - A Little Pain for the Holiday


Hey peeps... This weeks it's gonna hurt update is a present from us to you. We brought in this "straight Guy" to suck dick and get fucked in the ass. Hmmmm..... Anyways he screamed and shouted and the next thing you knew he had a huge load from a monster black cock all over his face. Tis the season and it's gonna hurt bitches! Cum watch this savage anal adventure of pain and enjoy!
Format: mp4
Duration: 29:27
Video: 1280x720, AVC (H.264), 2928kbps
Audio: 70kbps
File size: 648.5 MB

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It's Gonna Hurt - White Boy Gets Owned


It's Gonna Hurt - White Boy Gets Owned


This update of It's Gonna Hurt features Castro Supreme and some little white dude that's trying to prove something to his prostate. This little fucker gets cracked in half by Castro's mammoth sized cock and then he gets woman fuckin loads dropped on his face. That shit will always hurt! Peace out, bitches!
Format: mp4
Duration: 26:21
Video: 1280x720, AVC (H.264), 3511kbps
Audio: 67kbps
File size: 691.8 MB

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ItsGonnaHurt - Tight little Fucker


ItsGonnaHurt - Tight little Fucker


Hey people... We have got another gut wrenching episode of of It's gonna Hurt. Today's victims name is Val and Castro literally nails his tight little asshole to the wall. It was a good day for Castro and not so good for Val or at least it seemed. In the end Val came out smiling which was a real shocker cause for a minute I thought I was gonna have call the ambulapse. lol... Its always gonna hurt with Castro's Supreme! Watch and Love it!
Format: mp4
Duration: 36:09
Video: 1280x720, AVC (H.264), 3512kbps
Audio: 67kbps
File size: 949.7 MB

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ItsGonnaHurt - It's Still Gonna Hurt


ItsGonnaHurt - It's Still Gonna Hurt


Hey big dick lovers... Today we brought in a new big cock by the name of Mario Costa. This guy is a cool ten inches with girth the size of this guy Seth's forearm. Needless to say this weeks victim is in for some pain. Let just remind you it's not Castro but it's still gonna hurt! Enjoy!
Format: mp4
Duration: 33:38
Video: 1280x720, AVC (H.264), 2928kbps
Audio: 66kbps
File size: 739.2 MB

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It's Gonna Hurt - White boy gets big black dick


It's Gonna Hurt - White boy gets big black dick


This week on its gonna hurt we brought in this cat Ty Tucker. Ty was scared as fuck when Izzy pulled out his black Mamba. This guy gets his mouth and asshole banged out and its a real treat for all of you sick fucks! We hope you enjoy! Later Bitches!
Format: mp4
Duration: 26:54
Video: 1280x720, AVC (H.264), 2909kbps
Audio: 67kbps
File size: 588.4 MB

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It's Gonna Hurt Part 3


It's Gonna Hurt Part 3


Genres: Interracial
These guys thought they could take a monster cock. Find out if they can in It's Gonna Hurt pt. 3. Check out these asses getting reamed by the biggest dick they've ever seen. The best part is they love every second of it." So say the notes. Some boys like big dicks, some boys like huge dicks, and some boys like it when It's Gonna Hurt. Castro Supreme is back again for another installment, and I'm pretty sure his dick is getting bigger every time I see him. Lucky for me, Big d. Video somehow has an endless supply of little white guys for him to split wide open. I've been told that there's a fine line between pleasure and pain; I don't think that's true in this case, as these boys are (clearly) only feeling the pain.
Format: mp4
Duration: 1:51:27
Video: 720x404, AVC (H.264), 1136kbps
Audio: 151kbps
File size: 1.0 GB

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It's Gonna Hurt - Curious Guy Takes The hammer! - Izzy and Seth Haas


It's Gonna Hurt - Curious Guy Takes The hammer! - Izzy and Seth Haas


Seth is trying to convince us that he's not gay. He only likes to get nailed by them just out of curiosity. Well Seth. Today is going to be your lucky day. You get to experience another non-gay encounter. What an idiot!. Izzy doesn't care. Gay or not, your going to get your ass-hole rearranged in many ways than one. All we know is that Izzy's huge penis is going in there balls deep. looks like It's Gonna Hurt. Enjoy!
Format: mp4
Duration: 25:03
Video: 1280x720, AVC (H.264), 2906kbps
Audio: 64kbps
File size: 546.5 MB

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ItsGonnaHurt - Butthole Smash


ItsGonnaHurt - Butthole Smash


Hey people. This Tuesday's It's Gonna Hurt update is great! We brought in this guy Bryan to get his face and ass smashed in by Castro's obscenely large dick. Unlike most updates, this guy could barely finish. Bryan was in so much pain it was kinda funny. I really felt bad for this one but like the sign said: "It's Gonna Hurt!" Enjoy, you sick fucks!
Format: mp4
Duration: 33:49
Video: 1280x720, AVC (H.264), 3511kbps
Audio: 67kbps
File size: 888.1 MB

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Big Daddy – It's Gonna Hurt Vol.3 (2012)


Big Daddy – It's Gonna Hurt Vol.3 (2012)


Release Year: 2012
Cast: Castro Supreme, Junior
Genres: Oral, Blowjob, Anal Sex, Condom, Big Dick, Cum Shots, Interracial
These guys thought they could take a monster cock. Find out if they can in It's Gonna Hurt 3. Check out these asses getting reamed by the biggest dick they've ever seen. The best part is they love every second of it." So say the notes. Some boys like big dicks, some boys like huge dicks, and some boys like it when It's Gonna Hurt. Castro Supreme is back again for another installment, and I'm pretty sure his dick is getting bigger every time I see him. Lucky for me, Big Daddy Video somehow has an endless supply of little white guys for him to split wide open. I've been told that there's a fine line between pleasure and pain; I don't think that's true in this case, as these boys are (clearly) only feeling the pain.
Format: mp4
Duration: 1:51:27
Video: 720x404, AVC (H.264), 1136kbps
Audio: 151kbps
File size: 1.0 GB

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ItsGonnaHurt - Savage Asshole Stretching


ItsGonnaHurt - Savage Asshole Stretching


A lot of people ask... "Is this Real?", "Is Castro's Cock that Big?" Well, my friends... go ask Noah Brooks, the latest victim on It's Gonna Hurt. Noah always wanted to try a big black dick. Now he has, and I'm pretty sure he will never do it again. He received a savage asshole stretching with a side of cream sauce. We warned him... It's Gonna Hurt!
Format: mp4
Duration: 36:36
Video: 1280x720, AVC (H.264), 2929kbps
Audio: 62kbps
File size: 803.8 MB

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It's Gonna Hurt - White Boy Gets Big Black Dick - Ty Tucker HD-720p


It's Gonna Hurt - White Boy Gets Big Black Dick - Ty Tucker HD-720p


Release Year: 2016
Cast: Ty Tucker
Genres: anal, hung, interracial, porn
Video language: English
This week on its gonna hurt we brought in this cat Ty Tucker. Ty was scared as fuck when Izzy pulled out his black Mamba. This guy gets his mouth and asshole banged out and its a real treat for all of you sick fucks!
Format: mp4
Duration: 26:54
Video: 1280x720, AVC (H.264), 2909kbps
Audio: 67kbps
File size: 588.4 MB

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ItsGonnaHurt - No Pain No Gain


ItsGonnaHurt - No Pain No Gain


Castro Supreme is back with another cock throbbing update of It's Gonna Hurt. He's going to love who we have for him today. Jr's petite but has enough junk in his trunk for Castro Supreme's liking. Jr was amazed at how huge his cock was. He's never seen anything like that before. All he could think was. How the fuck is that monstrous cock going to fit in my little bum-hole. There's no need to worry Jr. Castro Supreme is going to make sure it fits. He'l ease his way inside that little asshole of yours until that anaconda is balls-deep. Ouch! It's Gonna Hurt!
Format: mp4
Duration: 24:54
Video: 1280x720, AVC (H.264), 2931kbps
Audio: 70kbps
File size: 548.7 MB

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Davids Meat Ride


Davids Meat Ride


Studio: Its Gonna Hurt
Sup fuckers? We got a real sweet Its 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 Castros Monster dick light a fire in some asshole!
Format: avi
Duration: 34:32
Video: 852x480, XviD, 2621kbps
Audio: 125kbps
File size: 698.1 MB

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ItsGonnaHurt - That had to of Hurt again


ItsGonnaHurt - That had to of Hurt again


Trent Diesel was one of our earlier victims when we were first starting out. Well after taking on Castro and getting his asshole gaped open, he couldn't find another man to satisfy him like that again. So then 2 years later he came back to us, because he knew we had the goods. And like an addict, he had to have is ass hole ripped wide open again. Look like this is gonna hurt...again.
Format: mp4
Duration: 32:53
Video: 1280x720, AVC (H.264), 2927kbps
Audio: 93kbps
File size: 729.3 MB

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ItsGonnaHurt - That had to of Hurt


ItsGonnaHurt - That had to of Hurt


Trent Diesel was one of our earlier victims when we were first starting out. Well after taking on Castro and getting his asshole gaped open, he couldn't find another man to satisfy him like that again. So then 2 years later he came back to us, because he knew we had the goods. And like an addict, he had to have is ass hole ripped wide open again. Look like this is gonna hurt...again.
Format: mp4
Duration: 40:40
Video: 1280x768, AVC (H.264), 2929kbps
Audio: 93kbps
File size: 902.2 MB

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ItsGonnaHurt - The new Slugger in Town


ItsGonnaHurt - The new Slugger in Town


We brought Mario Costa back by popular demand. Mario has an insane cock that all the guys can't keep out of there mouths. Today he puts another hurtin on this kid Travis. I'll say the kid took all ten like a champ but it still had to fuckin hurt! Watch this young buck get his bowels rearranged. And never forget "It's gonna hurt!
Format: mp4
Duration: 36:20
Video: 1280x720, AVC (H.264), 2930kbps
Audio: 65kbps
File size: 798.9 MB

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ItsGonnaHurt - White Boy Gets Owned


ItsGonnaHurt - White Boy Gets Owned


This update of It's Gonna Hurt features Castro Supreme and some little white dude that's trying to prove something to his prostate. This little fucker gets cracked in half by Castro's mammoth sized cock and then he gets woman fuckin loads dropped on his face. That shit will always hurt! Peace out, bitches!
Format: mp4
Duration: 26:21
Video: 1280x720, AVC (H.264), 3511kbps
Audio: 67kbps
File size: 691.8 MB

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ItsGonnaHurt - Surfer Dude gets his share of big dick


ItsGonnaHurt - Surfer Dude gets his share of big dick


Hello there eager guys! We are back just how we promised and we have some new amazing its gonna hurt scenes just for you! In what follows we are going to give you the chance to see as this surfer guy is gonna her his tight ass destroyed by this chocolate guy and his extra large cock! Castro went to the beach today to see if he can find any hot guys roaming around. And for today’s its gonna hurt update he sure lucked out. He got his hands on a skinny little man slut surfer. Are you eager to see what happened after that with this guy? Have a seat and watch also training day! What a great day to have you time spent at the beach right? Well, our dude was not only enjoying this beautiful day but also seeking for some dude that he could stuck his large cock into! Lucky for Castro he was into having cocks fuck his ass and when Castro asked him if he may stuff his tight ass with his big black cock, he said yes. Soon after that they headed to this place, where right in the living room this guy stuffed his tight ass from behind, until he had the chance to cum deep into this guy’s anus! And what an awesome time they had!
Format: mp4
Duration: 36:14
Video: 1280x720, AVC (H.264), 2929kbps
Audio: 67kbps
File size: 797.1 MB

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ItsGonnaHurt - Pain+Stitches=Supreme


ItsGonnaHurt - Pain+Stitches=Supreme


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 woman Fuckers! LOL
Format: mp4
Duration: 47:05
Video: 1280x720, AVC (H.264), 2929kbps
Audio: 68kbps
File size: 1.0 GB

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It's Gonna Hurt - The Big Hurt - Daniel HD-720p


It's Gonna Hurt - The Big Hurt - Daniel HD-720p


Release Year: 2016
Cast: Daniel
Genres: anal, hung, interracial, porn
Video language: English
Hey peeps! We got another itsgonnahurt for ya. This guy Daniel gets his shit pushed in pretty good. I think he was crying at one point during his asshole destruction. Castro didn't mind his soft lips on his massive meat hanger. Cum watch Castro destroy another little white dude!
Format: mp4
Duration: 31:07
Video: 1280x720, AVC (H.264), 2929kbps
Audio: 68kbps
File size: 684.6 MB

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