See the biggest, longest, fattest cocks stuffed into tight gay assholes. And yes, it's gonna hurt

Prepped & Pounded – Nubius & Sam Swift & Jay Black

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Nubius waits, chained to a dungeon cross. He knows his masters will soon descend upon him with electric razors at the ready. He can only tremble in anticipation, for he knows even the preparation will be sheer ecstasy. But what Jay Black and Sam Swift have planned for the main course will be a heavenly punishment. They indeed shave him and unchain him. His first order is to suck both Jay’s and Sam’s cocks at the same time, providing adequate pleasure to both raging erections. Nubius knows he can accommodate these men. As a submissive, Nubius has dealt with multiple throbbing dicks in his face. Then it’s time for a good, proper ass pounding. first, Jay is having his way. To prep even further, Jay licks Nubius’s hole, tenderizing the warm pocket. Then he slides his pulsating cock inside while Nubius slurps on Sam’s behemoth dong. After an unremorseful fucking, Jay and Sam switch sides so Sam can slam. Watch this dungeon trio exercise their right to enjoy raunchy, underground sex in this twisted, subterranean fuck party.

Jin Powers – Jin Powers

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Let the sexual vibrations titillate every centimeter of your body as you indulge in the unique sensuousness of Jin Powers. He’s a lean, handsome young man, excited about sending you pictures of his fat cock, still resting in his underwear. In fact, he’s taking shots of his large dong while it’s tucked inside various pairs of undies. It won’t be long before Jin unleashes his anaconda. His personal photo session has him turned on and in need of some sexual relief. Jin is laying out on the couch to stroke his stiff, erect cock. Watch as he tugs his well-oiled meat, shooting you intense, deep looks as he lets his imagination take him to a special place. Go with him to that place as Jin builds toward an explosive peak where ecstasy is religion.

Tug Shack Treatment – JP Richards & Carlos B

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It’s a chance for Carlos to relax. After a long week of intramural football practice, the young man not only deserves some tender attention, he craves it. Stopping by a little hole in the wall downtown, known as the ‘Rub House’ to the unsuspecting public, Carlos explains to proprietor, JP Richards, that his muscles are tense. JP knows exactly what Carlos needs. You see, to familiar customers, this small establishment is better known as ‘JP’s Tug Shack!’ Carlos can’t believe how magic JP’s hands are, right off the bat. Plenty of oil goes all over Carlos’s skin as JP manipulates the sore spots. When JP has Carlos turn over, JP’s hands find their way to Carlos’s nice cock. Soon JP is sucking Carlos’s dick and stroking his own boner. JP then instructs Carlos to stand up so he can flick his tongue in and around Carlos’s sensitive asshole. See Carlos relieve some of his stress from football practice as he gives his masseur, cum-hungry JP, exactly what he wants.

Double Monster Dick Destruction

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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!

Twenty…Scared… And Hungry!

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This episode of itsgonnahurt.com stars a little 20 year old white boy named Alex and of course The King of Ding-a-lings… Castro Supreme. This little fucker loves to suck black dick. He also likes being impaled with cocks and dix bigger than his limbs. He seemed to really enjoy his scene. Just kidding he screamed like a little bitch! HaHa…Peace!

Castro Is A Magician!

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This weeks It’s gonna hurt is a doozy. We brought in this little Spanish fucker to get his prostate examined unfortunately for him this routine check up might have caused more damage than it was worth. Castro buries his brown log balls deep in this little Princesses Asshole. This shoot was definitely one sided in the pleasure department. Enjoy watching this guy get stuffed!

No Pain No Gain!

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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!

Swing Shift – Sam Swift & Astengo & Tyson Tyler

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They’re a couple of sexy wolves on the loose, looking for a hot hookup with somebody who’s ready for action. Tyson Tyler and his fuck buddy, Sam Swift, have ducked into a popular nightclub to find what they want. But it’s the middle of the day and they’re hoping to spot a prime specimen who’s casually enjoying his Saturday. The last guy they figured would join them is sexy bartender, Astengo. But this barkeep is always down to get wild! When Astengo returns from the back room, he finds Tyson and Sam getting warmed up with some deep kissing. When their large dicks come out, Astengo goes right in for a taste. Both Sam and Tyler are very well hung men, just how Astengo likes his random bangs. The fat cocks these guys pump into Astengo’s mouth is a lot to handle, but just the thing to break up his usual bar routine. Tyson moves around to Astengo’s ass and flicks his tongue around the tight hole. Then Tyler slides his stiff cock into Astengo’s delicious hole. Sam loves the feeling of Astengo’s mouth slurping his erect dong while he gets fucked simultaneously by Tyson. Sam switches to the other side and Astengo takes to his back to allow Sam to pound his sweet ass. Even in the middle of the day, one never knows what kind of interesting situations can be found in the City downtown. Join this steamy threesome as they explore the excitement of a random, public hookup.