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| 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!" |
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| 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 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 no you sick fucks are gonna anyways! LOL |
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| 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 dick 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" |
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| 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 dick like Mario's you don't walk right for a week! Come watch this giant cock gape some asshole. |
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| Description: 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! |
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| 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!!! |
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| 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 ass. It's safe to say Mr.Stone was cracked open by the jack hammer. |
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| Description: Okay so this guy claims he's straight. Sure Darius may have fooled around with a couple of guys. Maybe even tasted a dick 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 ass. 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. |
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| Description: 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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| 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. |
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| 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 |
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| 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 ass 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! |
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| Description: I met up with this Hot looking French model on South Beach who was curious about getting fucked by a big dick. 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. |
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| Description: These Michigan boys sure know how to party. So one of these guys, convinces all these little freshman that their going to have an after party for the football game in his dorm. A party complete with chicks and football. Problem is when they get to the dorm room there are no girls. This doesn't stop the party. Despite the lack of chicks they start playing strip pong. A few article of clothing comes off and these horny college kids can't control themselves. |
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| Description: A very interesting video was submitted to us today by our home girls from Arizona and boy do they work over their two naive friends, Kyle and Ryan. They lure them in promising sex, if the guys mess around with each other first. Turns out, these dudes have their own party by themselves and end up forgetting about the girls. This is one update you won't want to miss. |
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| Description: 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 gruelling 40 minutes of anal stuffing, Rex got a hot load of Castro dumped on his face! Good times! Don't miss out. |
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| Description: We got this video in from some guys in the Midwest, and they seemed pretty hardcore with their frat so we decided to show the video. They drive these 3 pledges to the middle of fucking nowhere, some kind of field or something.. they have them do a 3 way dutch rudder which is pretty damn funny. WTF one of the guys licks his own cum.. ha anyways then they make the loser who couldn't cum suck off one of his brothers in the car. |
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| Description: Meet Patrick, He likes big muscles, big dicks, and putting dildos in his ass. Meet Castro, he likes putting his big dick 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 ass pounded, and then Castro finished him off with a nice glazing. |
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| Description: This shit was pretty funny. These dudes were fucking with one of their buddies who had passed out with his shoes on, putting shaving cream all over him, tea bagging him and slapping their cocks on his face giving him a mushroom stamp. Well of course this guy flips out and chases them down the hall.. he seemed really mad about the whole thing, and his friends were telling him to chill out.. I mean it's really not a big deal unless you're really gay right? So they made him PROVE he wasn't gay. Well shit.. that didn't really work out and this guy got hard as a rock.. |
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| Description: I'm with my boy Zach today and we're really just looking to get him some ass. He's horny as hell today and I'm ready to watch him get fucked by somebody! We found him a guy that seemed a bit shy at first, but he was down to mess around after we offered him some money. We had spotted this abandoned car lot across the street earlier so we all headed over there. Mickey showed us his cock like he promised, and Zach promptly put his mouth around it and sucked the hell out of it. One thing led to another and Mickey was fucking Zach against an SUV a few moments later!! These two really liked each other, and they both got a great workout in the sun! |
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| 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. |
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| Description: So the guys at one of our favorite east coast fraternity's decided to throw their annual winter party. As usual they brought their video camera's along to record the events and plenty of pledges to break in. Man when these guy's break in pledges they really break them in...lol. You got all the makings of a good hazing in this one :screaming, push-ups, jumping-jacks, dick sucking, and tacky outfits. You won't want to miss this one. Don't forget to check out the trailer by "Uncle Knuckle". |
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| Description: There once was a tale of two Jakes who met in a night club and decided to have a little fun. They spoke about this and that but could hear nothing so they went out back. Good ol Joey explained that they like to film people doing crazy shit like pulling out cock and sucking them good. One Jake agreed and the other got in a good mood. They took it a little further when they decided to fuck right there in the clubs parking lot while people arrived for some dancing and drinking. They didn't care not a bit. They kept fucking while the onlookers looked. They felt it increased the pleasure. This is their story. This is their treasure. |
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| Description: What up all you giant dick 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 ass get ripped! ;) |
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| Description: I cant believe the some of the things these pledges will do just to be a brother. So we had these guys believeing that we were rewarding them for all the hard work they have been doing. First of all i dont consider any of their work to be hard and even if i did im not into rewarding. Tricking them into punishment now thats more my style. So we set up a glory hole and placed some prety girls around it telling the guys that its these girls that will be on the other side. Nope we had one of our resident gays back there instead. The guys loved it thinking it was a bunch of girls sucking their dick. When they found out who it really was....priceless. |
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| Description: So I hoked up with my buddy Tristan who was visiting from out of town and wanted to see South Beach. He said he wanted to go out on the town and find a hot little thing and turn him over to the dark side and we did just while crusing the beach. We me this little Guppie named Xander who was down for some public fucking. Well to make a long story short Tristan and Xander got to it on the roof top as I filmed. You won't want to miss this hot update. |
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| 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! |
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| Description: LOL... So last week we received some footage that was submitted from this fraternity out in Ohio. We kind of thought the original submission email was funny, check it out. "To whoever wants this footage, We had a little initiation for our fraternity but it was all set up for a good joke. We had these dudes doing a lot of strange things, I mean strange like jerking each other off, sucking each other off, just some really crazy stuff. I already graduated from there & I just felt like putting this footage out I did some research & decided to send it to you guys, & I'm kind of hoping you guys can do something with it. Hope to hear back form you. Thanks" You guys should enjoy this. |
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| Description: You all know how I love to watch my buds get laid by now, right? Well, one of my favorite ways to spend the day is cruising with my partner-in-crime, Lee. He came down for a visit so I took him down to the docks where he could get some sun and some dick! I knew there would be a lot of dudes hanging out on the boats and Lee wanted to find some hot boy ass. We met Jake, a sexy blonde southern guy. Lee was into this guy right away. Being a good friend, I pulled out the cash and Jake dropped his pants, showin off his dick. Lee was damn happy. He didn't care that they were outside where anyone could stumble across us, he got his hands and lips around that cock right away! Lee loved getting dicked out in the open and I love to watch my buddies get their mouths fucked in public so today was a good day for both of us! |
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| 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 ass. 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! |
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| Description: WOW, this video was submitted to us earlier in the week and we just had to get it up ASAP! Apparently this fraternity uses a ritual called "The Machine" to haze their pledges but they don't tell the pledges what "The Machine" is so they think they're in the clear as they're greeted by the brothers. but as soon as these pledges get too comfortable and one even got a little cocky they set loose "The Machine" and it was just hilarious watching these poor soon to be frat boys reaction when this mammoth of a man comes running out in his tighty whites ready for anything! |
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| Description: So turk is back in town and joey tries to go to the beach to hang out but decides to make a quick stop and get some food. They both see this guy coming out of the restaurant and decided to go "ask" for directions. Horny Turk has some great luck, this new friend they end up meeting is 18 and name is fernando. He also seems to like the cock. Joey gives fernando a treat and has turk the young "pornstar" show off his cock. Fernando and Turk end up hooking up. These 2 go to a corner of a car wash. Unbelievably nobody saw them and they suck and fuck until turk got a load on his ass. |
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| 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. |
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| Description: So these boys got creative. A couple of the elder frat brothers sent their new pledges out on a mission. They had to flash an old lady, skinny dip in a strangers pool and a bunch of other crazy shit and recorded it all on video. At the end they got a nice surprise when they opened their last challenge. Just how bad did these boys want to be frat brothers. We'll you'll find out |
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| Description: So me and my boy Dallas were heading over to our favorite dinner to get our grub on before going on the prowl for some ass when we spotted a hot little number at the counter. Naturally Dallas wanted a piece of that action so when the hottie headed for the bathroom Dallas made a B-line after him. I hung back for a while till Dallas could hook our little. I managed to walk in on them when he was giving Dallas some major head. If you wanna see what happned next your just gonna have to watch this update belive me you won't be disapointed. |
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