Its Gonna Hurt

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Enormous Dick in the Line Up

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Surfer Dude gets his share of big dick

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. 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, her said yes. Have a great time watching this fresh update and don’t forget that you can find similar gay sex scenes inside the blog, so check it out and have inside!


Watch this surfer dude getting ass plowed by a huge cock!

Pool side ass ride with Castro the impaler

In today’s Castro its gonna hurt update our black stud found himself fucking a tight ass by the pool. It all started as a joke when Castro told the guy he was nicknamed the impaler, awakening the curiosity of the guy. So Castro just whipped out his humongous cock, and the guy? well he spared no time and just went down on it like a hungry wolf. Enjoy him getting cum blasted all over his ass in this sweet update.


Watch Castro nailing his new partner and jizzing his ass!

Its Gonna Hurt – Roman goes long

Roman is today’s poster guy for its gonna hurt . Castro picked him up at a bar too and it seems Roman never tried his luck at having some serious black cock fuck his ass. And this was his lucky chance to try it out and see what it feels like. And surely enough he enjoyed all of Castro’s cock as he was moaning in pleasure while the big black rod was stretching his ass.

sttraight guy has his first ass fucking

Watch this straight guy experiencing his first ass fucking!

David goes crazy for this huge cock

In today’s itsgonnahurt update, Castro gets to fuck another tight white ass in what we like to call one of our best galleries so far. This white twink guy thought he should try out a black cock for the first time and see if he likes the feeling of a humongous cock stretching his ass. And boy did he. Enjoy him sucking Casto’s huge cock and watch him be a anal virgin no more in regards to black cocks. For similar content, join the site and see some slutty t-girls sucking and riding big cocks!

david gagging on the larges cock he ever seen

See this cock lovin guy gagging on Castro’s monster dick!

Tucker the fucker

Castro as you know is the protagonist in all of the its gonna hurt adventures. For this one in particular, he went to a local all males club to try and pick a guy that he fancied up. And he succeeded bringing him home to have him ride his huge meat rod this evening. The guy was ecstatic as Castro pounded away at his tight ass through the night. Enjoy!


See this slutty dude having his holes filled with cock!

ItsGonnaHurt – A creamy reward

Itsgonnahurt had another tight ass for Castro to destroy this week. Yet another white guy wanting to try out if the saying, “Once you go black you never go back” is true even in guy on guy action. And boy was he totally convinced after Castro took his ass for a wild ride stretching that tight ass of his to it’s limits. Until next time, we hope you enjoy!


Watch Castro stretching this white ass to the limits!

Butthole smash

Castro is back along with his big black cock in today’s free its gonna hurt videos . He’s always ready to fuck tight white asses and today was no different. See him get to work on Garry’s ass as the poor guy bit more than he could chew. Literally. So have fun with this update in which Castro thoroughly rams Garry’s ass balls deep. Enjoy!


See this mature guy getting punished by Castro’s snake!

A dream cum true

As always its gonna hurt brings you big black monster cocks in thight white asses. And today’s white twink was also curious about how good a big black rod of meat feels as it’s fucking up your ass. Castro was on duty again for this one as he demonstrated just how good a bog black dick can fuck a tight ass. And the white guy was in heaven for the whole duration of the sex scene.


Watch this horny twink getting ass fucked and facialized!

Its Gonna Hurt – The Gym Rat

Castro puts his fresh recruit in today’s its gonna hurt galleries to work on his humongous cock. The two met at a gym and this skinny guy always wanted to try taking a huge black cock up his ass. Well Castro satisfied that wish today as he rammed his ass hard core in this awesome gallery. Until our next update we hope you enjoy this one. Bye.


Watch this skinny twink taking Castro’s cock all the way!

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