It’s Gonna Hurt

Where giant dicks get stuffed into tight assholes…and its gonna hurt so good!

It’s Gonna Hurt: Tucker The Fucker!

Tucker The Fucker! at It's Gonna Hurt

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 dick in his mouth and ass. Luckily for him we have lots of dick 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

Watch Tucker & Castro Supreme at ItsGonnaHurt.com

It’s Gonna Hurt: Training Day

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!

Visit ItsGonnaHurt.com

It’s Gonna Hurt: Beach Day Ass Fucking

Beach Day Ass Fucking at It's Gonna Hurt

Hey guys! Joey here, This week we hit the nude beach and met up with a buddy of mine. His name isTristan 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!

Watch Castro Supreme & Tristan at ItsGonnaHurt.com

It’s Gonna Hurt!: Ricky’s Tapout!

Ricky's Tapout! at It's Gonna Hurt

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 dick 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

Watch Ricky & Castro Supreme at ItsGonnaHurt.com

It’s Gonna Hurt: Kyler’s Meat Stick Ride

Kyler's Meat Stick Ride at It's Gonna Hurt

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 received a dose of hot man milk all over his face. Bottoms up and enjoy!

Watch Castro & Kyler at It’s Gonna Hurt

It’s Gonna Hurt: Surfer Dude Gets His…

Surfer Dude Gets His... at It's Gonna Hurt

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 grueling 40 minutes of anal stuffing, Rex got a hot load of Castro dumped on his face! Good times! Don’t miss out.

Watch Rex & Castro Supreme at ItsGonnaHurt.com

It’s Gonna Hurt: Tristan’s Dream Comes True!

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

Broke Straight Boys Superwide Banner #2

It’s Gonna Hurt: A Ride On The Gravy Train

A Ride On The Gravy Train at It's Gonna Hurt

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!

Watch Jon Estevez, Castro Supreme & Diesel Washington at ItsGonnaHurt.com

It’s Gonna Hurt: Lance Likes Big Dicks

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

Life Is Better With BelAmi 2022 – Superwide & Tall

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

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

It’s Gonna Hurt: It Really Fucking Hurts!

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

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

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

It’s Gonna Hurt: Castro’s Back Boys!

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!

Watch Castro & .. at It’s Gonna Hurt

Life Is Better With BelAmi 2022 – Superwide & Tall

It’s Gonna Hurt: Killin’ That Ass

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!

Watch Kyle at ItsGonnaHurt.com

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

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