 |
| Description: 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 cock in his butt. 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 butt. 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! |
 |
| Description: Meet Patrick, He likes big muscles, big dicks, and putting dildos in his butt. Meet Castro, he likes putting his big cock in little tight assholes, and terminating them. What a perfect match these two are. Both these guys are in great shape, and watching Castro fuck Patrick as he stroked himself was quite a sight. Patrick came a couple times while he was getting his butt pounded, and then Castro finished him off with a nice glazing. |
 |
| Description: 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! |
 |
| Description: 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 cock in his mouth and butt. Luckily for him we have lots of cock 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 |
 |
| Description: 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 stuff's his giant cock in a nice tight asshole and it was painfully sweet with a great big load on the face. Enjoy! |
 |
| Description: Today I bring to you the sexy Boston native "Giovanni" a 20 years Italian/Puerto Rican little thing who came down here without a clue of what to expect from us. So we chatted for a little bit & to my surprise Giovanni likes his men very tough, very masculine, to take control, thuggish, etc.... Sounds like someone I know. He wasn't too much of a fan of huge dicks but one of big dicks, so I brought him inside to meet the Supreme & let me tell you, he was excited to meet him but when Castro pulled out that thing, his whole face changed. Come see what happens. Enjoy..... Hasta La visto |
 |
| Description: What's good everyone? Today we stopped by this kid Caleb's house and Castro laid down the supreme right up the old brown eye. This new fresh meat had no clue he would be receiving a cock up his butt the size of a baseball bat. Needless to say he was hurtin pretty good towards the end. All in All it was a swell day for Caleb and I think he will recover just fine! |
 |
| Description: Hey guys! Joey here, This week we hit the nude beach and met up with a buddy of mine. His name is Tristan 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! |
 |
| Description: Meet our friend Isaac Coon. He's a real corn fed country boy. He came all the way from Georgia looking for a man with some "good equipment". And that's exactly what he got. This newbie had never seen anything like the tool Castro was packing. After the disbelief wore off he got right down to business. He swallowed Castro's giant like gravy and biscuits. We sent this kid back to Georgia with a couple dollars and a lesson. Be careful what you wish for. |
 |
| Description: 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 |
 |
| Description: Hey boys... 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!" |
 |
| Description: 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 butt it was time to head to the clinic to get his holes stitched shut! Don't miss out on this crazy update! |
 |
| Description: Today I present to you "Kirk Cummings" a sexy little stripper who is too excited to be here completely in the dark about who he will be working with today. He's a little show off, but let me tell you that boy can move. So after Kirk showed me a few moves we chatted for a bit then I brought him to the kitchen to meet the star of the show "Senor Castro Supreme" He couldn't believe how big Castro's cock was but he sure was willing to try it out. After Kirk blew Castro away with an amazing blowjob it was time for some damage. Enjoy!!!! As I quote Senor Castro "Hasta la Visto" |
 |
| Description: So Castro & I decide to ride up to Fort Lauderdale beach to find a new victim for today. That's where we run into the sexy Shane Frost, man let me tell you Castro was more excited then Shane was!!!! The Supreme found a little something he was very interested in today. So after we chat for a bit we end up at my apt up there & then......... You need to see what happens I can't explain it.. HOT!!! Hasta La Visto.... ENJOY |
 |
| Description: Today we bring you Danny, a sweet little country boy who apparently loves big cocks, this kid was fired up the whole time I mean he was pre cumming before I even handed him the dildo to play with!!! Anyway he was thrilled about the idea of meeting the Supreme so after he got off on the toy I brought him to the real deal. Cum see what happens. Hasta La Visto!!! |
 |
| Description: 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 cock taking abilities. Considering he had a baseball bat sized cock jammed up his butt with a smile on his face impressed the fuck out of me. I would say to watch this but I no you sick fucks are gonna anyways! LOL |
 |
| Description: He shoots, he scores! It was a nice day for a little basketball in the park with Castro and a couple buddies, but it was an even nicer day for some big cock 3 way sex back in a nice cool house. Chase was one happy camper when he got a face full of cock from Devin and Castro. At first he didn't even know what to do with these huge cocks, but he got warmed up to them pretty quickly and once the action moved to the sofa, he got not one but two huge cocks in his butt. He was pretty worn out at the end of it all, but his smile is worth a thousand words. |
 |
| Description: After our success story at the beach last week, we decided to hit the beach up again today to find us a victim, but this time Miami Beach. We find this cool dude Brian just hanging out by himself we're not too sure what's up with him but he made a comment about Castro giant cock so we invite him over the apt for some drinks. So we talked for a bit & I convince him to try the Supreme out & he went for it. Cum see what happens.... ENJOY!!! |
 |
| Description: What up creepos? Today we brought in this bashful volleyball player off the beach. He was a fan of It's Gonna Hurt until he felt the pain. I think Castro might have fucked this dude straight -- but then ya never know! Maybe all that screaming and begging to stop was all for show! LOL ... Doubt it! But anyways, cum watch this little white boy get his anus blown out by Castro's monster shlong! |
 |
| Description: o this kid thought he was a pro. Today we were shooting with our friend Kurt Wild. He's a newbie in the business and has a little bit of a following. His moderate fame may have gotten to his head a little. He was slightly over confident before we got him upstairs. That quickly changed when Castro pulled out the supreme. Kurt's a little guy. He's got a cute little frame and a tight little body. Castro's supreme gave him a introduction into the business. Kurt took it like a champ. |
 |
| Description: We picked up a cute latino guy who isn't sure if he's gay, straight or bisexual.. but really who cares? He may not be too sure on his sexual preference but he sure is excited about getting to suck and fuck on Castro and his giant meat snake. The monster made his jaw drop when he whipped it out, and it stayed locked open for some nice slurping action and then Castro put this latino boy through a nice sweet hurtin' |
 |
| Description: Hey fans! Today on It's Gonna Hurt we brought in this kid 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 cock like Mario's you don't walk right for a week! Come watch this giant cock gape some asshole. |
 |
| Description: 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 butt slaying of Castro Supreme! |
 |
| Description: 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 cock 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 |
 |
| Description: Welcome, fellas! Today we have a longtime fan of Castro's, David from New York, taking a ride on the ole Castro's bologny pony! He's been dieing to meet Castro and see if he can hang with us Miami boys. So we picked David up at the airport after he had missed his first flight and right away he's got Castro's huge cock in his mouth! This kid was no joke he took in the butt like a champ in all the positions Castro put him into. In the end he thanked us for bringing him over and letting him meet Castro. This is one one update you guys won't wanna miss! |
 |
| Description: 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. |
 |
| Description: 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 butt 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 |
 |
| Description: 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 cock. In fact I'm not really sure he likes big black cock 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! |
 |
| Description: William is a nice little school boy. He even has a girlfriend. What his girl doesn't know is that Willy loves the cock. We picked him up in front of his campus. He was a little shy at first but once we got him back to the apartment he started opening up. He told us all about his repressed sexual escapades. He loves sex but there was something missing in his love life. That something was Castro's supreme cock. So being the nice guys that we are we decided it was time to let Willy have it. He was mesmerized and terrified at first. After the initial shock at Castro's scale tipping monster he got right to work. Cramming the supreme into his under used regions wasn't easy, but as always we made it work. Like the saying goes no pain no gain. After we were finished William said he would never downgrade again. |
 |
| Description: Hey people... Today we stopped by this guy Park Wiley's outrageous mansion. He is some rich fucker that apparently craves Big Black cock. So to do him and you guys a favor... Castro jammed his 13 inch sausage down his throat. I hate to dis appoint but this guy loved it without one complaint! He still squilled like a pig getting it's throat slit. People always ask me if Castro's cock is really that big? My answer usually is... come find out for your self! Peace bitches! |
 |
| Description: Hey Guys... Today we brought in this young pup for little bit of butt 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! |
 |
| Description: 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 massive member in his mouth and butt. It was a fun day for this adventure seeker and you can bet it hurt like hell. Who knows maybe you'll be next? |
 |
| Description: We met up with this local college guy named Josh 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 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. |
 |
| Description: 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! |
 |
| Description: 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 |
 |
| Description: 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 butt 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 cock light a fire in some asshole! |
 |
| Description: What up all you giant cock lovin fans? Today Castro and I ; went cruzin a local college campus to meet with this kid that was dreaming of Castro's cock. He claimed he was straight but after you see this video you might think otherwise. Anyways... this kids name is Trent and he gets his organs rearranged by Castro's Supreme! Come watch some butt get ripped! ;) |
 |
| Description: Guys do I have an update for you! We've been putting some ads in the local paper to see if there were any takers(get it..lol) out there for Castros's big black cock. Well guess what? We got one..and he's straight! As if that wasn't enough, he has a wife and kids at home!!! It turns out our boy Ari always fantasized what it would be like to take Castro's ginormous cock inside his virgin asshole. Well Castro did good by our boy Ari and pounded his butt good and hard and he loved every second of it. Ari even gives a shout out to his wife and kids at the end. You guys do NOT want to miss this ground breaking episode! |
 |
| Description: 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 butt. Much to our surprise, Kyler handled it pretty well - with a little kicking and screaming of course - until he recieved a dose of hot man milk all over his face. Bottoms up and enjoy! |
 |
| Description: 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. |
 |
| Description: The lovely Mr.Stone (John Stone) came out to do a little video shoot with us. He wasn't entirely sure what he was getting himself into. The promise of big cock enticed him. This kid was freaky from the get-go. We weren't ten minutes into the video before he started shoving didlo's up his tight little bunghole. Needles to say Castro's monster scared him. And rightfully so. Castro conquered this kids butt. It's safe to say Mr.Stone was cracked open by the jack hammer. |
 |
| Description: Okay so this guy claims he's straight. Sure Darius may have fooled around with a couple of guys. Maybe even tasted a cock or two. But he is not gay. No sir, he's even got a girlfriend to prove it. Sure, he admits he lets her put on a strap on and put it in his butt. But he is not a homosexual. Till he met Castro. This Texas boy found out the slogan everything is bigger in Texas dosen't apply to Castro's supreme. |
 |
| Description: This weeks It's Gonna Hurt update is great! We brought in a porno virgin to see what was up. I think he shit himself when he saw that Castro was hung literally like a horse. The guys name is Roni and he gets his butt-hole pummeled by some big black cock! It had to of hurt! LOL Watch this Video! |
 |
| Description: 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 massive cock in his butt. 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 cock cause he literally sucked castro's cock clean! To make a long story short... Its gonna hurt BITCHES! |
 |
| Description: I met up with this Hot looking French model on South Beach who was curious about getting fucked by a big cock. I thought he was full of shit but he's the real deal, he showed me some modeling pictures and we chit chatted a bit about what he likes while fucking. Castro really liked this one, and he even spoke some french to us while Castro man handled him. Enjoy watching this pretty boy getting reamed. |
 |
| Description: The name is Bond, Braxton bond. And he's a dirty boy. Braxton our blond LA surfer boy by way of Maine has a thing for cock. He really loves the supreme. He loved it so much he got on his knees and deep throated the shit out of Castro's monster in a back alley. This kid was game from the get-go. As soon as he saw Castro's monster it was on. By the time we got him back to the apartment he couldn't wait to drop his pants and take the supreme. |
 |
| Description: Hey big cock 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! |
 |
| Description: 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 butt 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. |
RSS
