List of ALL

ItsGonaHurt porn Videos



  1. It s Gonna Hurt Guy gets Huge Dick in the Asshole

  2. Its Gonna Hurt Latin Guy Tries a Big Dick _HD

  3. Its Gonna Hurt The big bad dick _HD

  4. Its Gonna Hurt Gay for Pay _HD

  5. Its Gonna Hurt Monster Dick in the Line Up _HD

  6. Its Gonna Hurt Cole Gets a Reality check

  7. ItsGonnaHurt Evan Likes Black Dick

  8. It s Gonna Hurt Gettin it like a Dirty Dog Izzy David Chase

  9. It s Gonna Hurt The Lumber Jack Slam Castro David Chase

  10. Its Gonna Hurt That had to of Hurt...again

  11. Its Gonna Hurt Size wins Top _HD

  12. ItsGonnaHurt He Works In A Surf Shop HD

  13. It s Gonna Hurt Shockingly Painful

  14. ItsGonnaHurt How s Your Pain Tolerance

  15. ItsGonnaHurt A Little Pain for the Holiday HD

  16. ItsGonnaHurt Return of the Rock HD

  17. ItsGonnaHurt Max It Out

  18. It s Gonna Hurt Snake Dancing

  19. ItsGonnaHurt How Bad Do You Want Them HD

  20. ItsGonnaHurt Do What You Got To

  21. ItsGonnaHurt Snake Dancing

  22. It s Gonna Hurt Cutting Class For Cock

  23. It s Gonna Hurt Wake up call

  24. It s Gonna Hurt White Boys Love Black Dick

  25. Its Gonna Hurt Tough Guy Gets Humbled

  26. It s Gonna Hurt The Big Hurt Castro and Daniel

  27. It s Gonna Hurt Big Boys Like Big Toys

  28. It s Gonna Hurt Gettin it like a Dirty Dog

  29. It s Gonna Hurt My friends are going to love me

  30. It s Gonna Hurt Fairy Tales Come True

  31. It s Gonna Hurt Gettin Hooked

  32. It s Gonna Hurt Tweetie Bird needs a break

  33. ItsGonnaHurt Jumbo Black Dick Swallowed by a White Guy

  34. ItsGonnaHurt 20 Plus Inches Of Hell

  35. It s Gonna Hurt Twenty...Scared...And Hungry

  36. It s Gonna Hurt White Boy Gets Owned

  37. It s Gonna Hurt No Pain No Gain

  38. It s Gonna Hurt Mclovin Loves Black Dick

  39. It s Gonna Hurt The Pillow Biting Heart Breaker

  40. It s Gonna Hurt Castro Is A Magician

  41. It s Gonna Hurt There s A First Time For Everything

  42. It s Gonna Hurt Sean s Anal Demise

  43. It s Gonna Hurt Screaming For Joy

  44. It s Gonna Hurt Hung Solo

  45. It s Gonna Hurt Gene Meet Castro s Big Black Dick

  46. It s Gonna Hurt Butthole Mashing

  47. It s Gonna Hurt Asshole Blasting

  48. It s Gonna Hurt Another Man Tastes The Dragon

  49. It s Gonna Hurt The Big Hurt

  50. ItsGonnaHurt Double Dick Destruction

  51. ItsGonnaHurt Can You Smell What The Rock Is Sucking

  52. Its Gonna Hurt Butthole Smash Bryan Castro

  53. Its Gonna Hurt Latino Gets A Hurtin

  54. It s Gonna Hurt Clayton was Scared

  55. It s Gonna Hurt Anal Lasagna

  56. It s Gonna Hurt Spencer the Badass

  57. It s Gonna Hurt Savage Asshole Stretching

  58. It s Gonna Hurt Youngster gets an Ass Fucking

  59. It s Gonna Hurt Back Blown Out

  60. It s Gonna Hurt Doing It Big

  61. Its Gonna Hurt 3 Pointer Chase Devin and Castro

  62. It s Gonna Hurt Steven s Ass Is Totaled

  63. It s Gonna Hurt Hanz Is Hurtin

  64. It s Gonna Hurt Super Slam

  65. It s Gonna Hurt AJ Plays the Pain Game

  66. It s Gonna Hurt Jared is a Quitter

  67. It s Gonna Hurt Hot Nuts Pierced

  68. It s Gonna Hurt Gabriel s Butthole Ride

  69. ItsGonnaHurt Kurt Wild The Average Joe Meets The Real Pro

  70. ItsGonnaHurt Giovanni The Italian Meets The Sausage

  71. ItsGonnaHurt Kirk Cummings The Castro vs the Stripper

  72. ItsGonnaHurt Danny Boy

  73. ItsGonnaHurt Brian

  74. It s Gonna Hurt Wade Plays the Pain Game

  75. It s Gonna Hurt Butthole Smash

  76. It s Gonna Hurt Goal In The Hole

  77. It s Gonna Hurt Tight Little Fucker

  78. It s Gonna Hurt One Large Deposit

  79. It s Gonna Hurt A Dream Cum True....

  80. ItsGonnaHurt A Ride On The Gravy Train

  81. It s Gonna Hurt Robbie Plays The Pain Game

  82. It s Gonna Hurt Tucker the Fucker

  83. It s Gonna Hurt Pain Stitches= Supreme

  84. It s Gonna Hurt Jaden Loves Black Dick

  85. It s Gonna Hurt Training Day

  86. It s Gonna Hurt Lance Like s Big Dick

  87. It s Gonna Hurt That had to of hurt....

  88. It s Gonna Hurt Killin That Ass

  89. It s Gonna Hurt Surfer Dude Gets his....

  90. It s Gonna Hurt Kyler s Meat Stick Ride

  91. It s Gonna Hurt The New Slugger In Town

  92. It s Gonna Hurt Ken Tanner s Ass Fucking

  93. It s Gonna Hurt It really fucking hurts

  94. It s Gonna Hurt Bon Appetit

  95. It s Gonna Hurt A Ride on the Gravy Train

  96. It s Gonna Hurt Double your Pleasure or Pain

  97. It s Gonna Hurt We got a screamer folks

  98. Its Gonna Hurt Right in the Ass

  99. Its Gonna Hurt Big Dick Hurts and Chokes the Country Boy

  100. Its Gonna Hurt Huge Black Dick

  101. Its Gonna Hurt Skinny white guy has a big black dick

  102. Its Gonna Hurt Big dick outdoors

  103. Its Gonna Hurt Latin love on a huge dick

  104. Its Gonna Hurt Big Black Dick For White Guy

  105. Its Gonna Hurt Tanner s Big Dick Ride

  106. Its Gonna Hurt Hungry German Sausage Lover

  107. Its Gonna Hurt Country White Boy Tries Black Dick


Wed, 13 Jun 2012 10:31:35 +0300

Its Gonna Hurt - Country White Boy Tries Black Dick



Its Gonna Hurt - Country White Boy Tries Black Dick

It's Gonna Hurt is back with another exciting update. Mark has no idea what he got himself into. He wants dick, but he hasn't had a dick like Izzy's. Izzy has a foot long cock thats fat like a baseball-bat. Mark was in disbelief once Izzy pulled the dick out. No worries! That didn't stop Mark from getting what he wanted. He got a whole lot of pain.

Format: mp4
Duration: 27:46
Video: 1280x720, AVC (H.264), 2910kbps
Audio: 65kbps

Its Gonna Hurt - Country White Boy Tries Black Dick Its Gonna Hurt - Country White Boy Tries Black Dick
Its Gonna Hurt - Country White Boy Tries Black Dick Its Gonna Hurt - Country White Boy Tries Black Dick

Its Gonna Hurt - Country White Boy Tries Black Dick
File size: 607.0 MB

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Tue, 29 May 2012 18:12:33 +0300

Its Gonna Hurt - Hungry German Sausage Lover



Its Gonna Hurt - Hungry German Sausage Lover

This wee we brought in this young sex crazy euro guy from Germany. He said he was bi-sexual and super open to what ever the fuck he was craving that day. On this day he was craving black dick and you can bet we obliged him by cramming 12 inches of love straight up his ass. Good-times... We hop you enjoy watching this wiener-schnitzel scream

Format: mp4
Duration: 26:49
Video: 852x480, AVC (H.264), 1453kbps
Audio: 63kbps

Its Gonna Hurt - Hungry German Sausage Lover Its Gonna Hurt - Hungry German Sausage Lover
Its Gonna Hurt - Hungry German Sausage Lover Its Gonna Hurt - Hungry German Sausage Lover

Its Gonna Hurt - Hungry German Sausage Lover
File size: 299.7 MB

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Wed, 23 May 2012 10:02:49 +0300

Its Gonna Hurt - Tanner's Big Dick Ride



Its Gonna Hurt  - Tanner's Big Dick Ride

This week on itsgonnahurt.com we slayed open this guy named Tanner's Asshole. He was super excited to get fucked and they had a great time fucking. Izzy liked it so much he busted early spraying hot glue all over Tanner's ass. This shoot went well but even Tanner said "That Shit fucking Hurt". Thats what we do bitches...

Format: lavfpref
Duration: 27:16
Video: 852x480, AVC (H.264), 1456kbps
Audio: 63kbps

Its Gonna Hurt  - Tanner's Big Dick Ride Its Gonna Hurt  - Tanner's Big Dick Ride
Its Gonna Hurt  - Tanner's Big Dick Ride Its Gonna Hurt  - Tanner's Big Dick Ride

Its Gonna Hurt  - Tanner's Big Dick Ride
File size: 305.3 MB

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Wed, 16 May 2012 09:22:07 +0300

Its Gonna Hurt - Big Black Dick For White Guy



Its Gonna Hurt - Big Black Dick For White Guy

Hello itsgonnahurt fans. This week we brought in this cat Parker Wright. Parker might have been the wrong guy for the job though. He was scared, frazzled and everything you don''t wanna be going into a shoot like this. He managed to squeal his way through the pain with plenty of breaks and ended up with a hot juicy load on his face after his savage asshole pounding. After all the sites not called its gonna be fun. This is itsgonnahurt.com and we don't fuck around here! Later bitches! Watch this video.

Format: lavfpref
Duration: 21:33
Video: 852x480, AVC (H.264), 1452kbps
Audio: 60kbps

Its Gonna Hurt - Big Black Dick For White Guy Its Gonna Hurt - Big Black Dick For White Guy
Its Gonna Hurt - Big Black Dick For White Guy Its Gonna Hurt - Big Black Dick For White Guy

Its Gonna Hurt - Big Black Dick For White Guy
File size: 240.2 MB

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Wed, 16 May 2012 08:34:59 +0300

Its Gonna Hurt - Big Black Dick For White Guy



Its Gonna Hurt - Big Black Dick For White Guy

Hello itsgonnahurt fans. This week we brought in this cat Parker Wright. Parker might have been the wrong guy for the job though. He was scared, frazzled and everything you don''t wanna be going into a shoot like this. He managed to squeal his way through the pain with plenty of breaks and ended up with a hot juicy load on his face after his savage asshole pounding. After all the sites not called its gonna be fun. This is itsgonnahurt.com and we don't fuck around here! Later bitches! Watch this video.

Format: lavfpref
Duration: 21:33
Video: 852x480, AVC (H.264), 1452kbps
Audio: 60kbps

Its Gonna Hurt - Big Black Dick For White Guy Its Gonna Hurt - Big Black Dick For White Guy
Its Gonna Hurt - Big Black Dick For White Guy Its Gonna Hurt - Big Black Dick For White Guy

Its Gonna Hurt - Big Black Dick For White Guy
File size: 240.2 MB

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Wed, 02 May 2012 08:45:53 +0300

Its Gonna Hurt - Latin love on a huge dick



Its Gonna Hurt - Latin love on a huge dick

This week on itsgonnahurt.com we got this guy Ram Soto. He is a Mexican Puerto Rican who love sucking dick. This guy was scared because not only was this his first interracial scene but it was his first giant dick. As mind blowing as Izzy dick seemed... Ram had no problem cramming this huge dick in his ass and all the way down his throat! Goodtimes

Format: lavfpref
Duration: 24:16
Video: 852x480, AVC (H.264), 1454kbps
Audio: 63kbps

Its Gonna Hurt - Latin love on a huge dick Its Gonna Hurt - Latin love on a huge dick
Its Gonna Hurt - Latin love on a huge dick Its Gonna Hurt - Latin love on a huge dick

Its Gonna Hurt - Latin love on a huge dick
File size: 271.4 MB

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Tue, 24 Apr 2012 22:03:10 +0300

Its Gonna Hurt - Big dick outdoors



Its Gonna Hurt - Big dick outdoors

In this weeks wild it's gonna hurt episode we have Izzy fucking this guy from Cali named Emmanuel. Emmanuel loves black dick and sucks it like he is going to the electric chair! In other words he cant get enough. We promise you won't be able to get enough either! Come watch these two men make magic!

Format: lavfpref
Duration: 27:00
Video: 852x480, AVC (H.264), 1450kbps
Audio: 66kbps

Its Gonna Hurt - Big dick outdoors Its Gonna Hurt - Big dick outdoors
Its Gonna Hurt - Big dick outdoors Its Gonna Hurt - Big dick outdoors

Its Gonna Hurt - Big dick outdoors
File size: 301.5 MB

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Wed, 11 Apr 2012 09:40:58 +0300

Its Gonna Hurt - Skinny white guy has a big black dick



Its Gonna Hurt - Skinny white guy has a big black dick

Wassup Guys?? Today we bring you Kyle, a nice young sexy city boy ready to take an asshole pounding from Izzy. Kyle seemed more less comfortable with the idea of a huge cock which he's never tried before. We chatted for a bit and he told me to bring it on with a little cockiness in his voice. Once Izzy whipped out his massive cock, Kyle swallowed his tongue and hi cockiness flew right out the window. Izzy gave him a nice breath taking ass pound he's never had in life and when we were through drilling his little asshole, we asked him if he would ever do it again and guess what this little cocky fuck said? Come see and find out!

Format: lavfpref
Duration: 40:59
Video: 852x480, AVC (H.264), 1464kbps
Audio: 67kbps

Its Gonna Hurt - Skinny white guy has a big black dick Its Gonna Hurt - Skinny white guy has a big black dick
Its Gonna Hurt - Skinny white guy has a big black dick Its Gonna Hurt - Skinny white guy has a big black dick

Its Gonna Hurt - Skinny white guy has a big black dick
File size: 462.5 MB

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Tue, 03 Apr 2012 22:19:37 +0300

Its Gonna Hurt - Huge Black Dick



Its Gonna Hurt - Huge Black Dick

Hey peeps! Here we are again with another update for itsgonnahurt.com. We brought in this guy Trace for some anal pounding and he really enjoyed himself as Izzy smashed up his tight little asshole. If this guy has a pain threshold we certainly didnt reach it today because he came to take dick and that my friends is the name of this game!

Format: lavfpref
Duration: 35:24
Video: 852x480, AVC (H.264), 1464kbps
Audio: 66kbps

Its Gonna Hurt - Huge Black Dick Its Gonna Hurt - Huge Black Dick
Its Gonna Hurt - Huge Black Dick Its Gonna Hurt - Huge Black Dick

Its Gonna Hurt - Huge Black Dick
File size: 399.3 MB

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Tue, 27 Mar 2012 20:44:32 +0300

Its Gonna Hurt - Big Dick Hurts and Chokes the Country Boy



Its Gonna Hurt - Big Dick Hurts and Chokes the Country Boy

Wassup Guys?? Today we bring you a sweet little boy from the Country side. He saw our ad in the paper and decided to come make some quick and what he taught would be easy money. Man was he wrong hahahahahahaaaa...... Izzy revealed the monster and this kid's whole attitude changed, he was scared but he got to work right away and started to suck well tried to suck the dick but it was not fitting in his mouth. After a couple of hardcore gags we get to the drilling.. This has to be the most painful episode on this site I mean this guy was screaming at the top of his lungs. But I'll let you see for yourself. Come watch Izzy drill this little sexy man and watch him squirm!

Format: lavfpref
Duration: 40:58
Video: 852x480, AVC (H.264), 1464kbps
Audio: 65kbps

Its Gonna Hurt - Big Dick Hurts and Chokes the Country Boy Its Gonna Hurt - Big Dick Hurts and Chokes the Country Boy
Its Gonna Hurt - Big Dick Hurts and Chokes the Country Boy Its Gonna Hurt - Big Dick Hurts and Chokes the Country Boy

Its Gonna Hurt - Big Dick Hurts and Chokes the Country Boy
File size: 461.5 MB

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Wed, 21 Mar 2012 14:22:17 +0200

Its Gonna Hurt - Right in the Ass



Its Gonna Hurt - Right in the Ass

I tried to play a game with our guy today and made him a pretty sweet deal. We had these darts here so I tell him if he can hit the bulls eye, we'll pay him and he doesn't have to get his little asshole stretched out by Izzy today. Of course, he says fuck yea let's do it, but he missed...HAHAHAA... He took his lost like a man and got ready to get pounded away although his hands were shaking like crazy. This guy was a pretty cool guy so I was kind of rooting for him to survive through this massive dick just drilling through him... And he did but it hurt like hell!!! Anyway guys take a look at this guy who by the way has a pretty bad ass looking body and can take 14 INCH DICK. ENJOY!!!!!

Format: lavfpref
Duration: 28:48
Video: 852x480, AVC (H.264), 1464kbps
Audio: 75kbps

Its Gonna Hurt - Right in the Ass Its Gonna Hurt - Right in the Ass
Its Gonna Hurt - Right in the Ass Its Gonna Hurt - Right in the Ass

Its Gonna Hurt - Right in the Ass
File size: 326.6 MB

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Tue, 06 Mar 2012 21:30:21 +0200

It's Gonna Hurt - Guy gets Huge Dick in the Asshole



It's Gonna Hurt - Guy gets Huge Dick in the Asshole

This young man gets put in a tricky situation with a big black dick. We meet up with Aj and basically didn't tell him how big Izzy's dick. He's in for a nice surprise when he see how big his cock is. Somehow he was able to swallow it up with his mouth and ass. Cum watch and enjoy!

Format: lavfpref
Duration: 27:09
Video: 852x480, AVC (H.264), 1464kbps
Audio: 64kbps

It's Gonna Hurt - Guy gets Huge Dick in the Asshole It's Gonna Hurt - Guy gets Huge Dick in the Asshole
It's Gonna Hurt - Guy gets Huge Dick in the Asshole It's Gonna Hurt - Guy gets Huge Dick in the Asshole

It's Gonna Hurt - Guy gets Huge Dick in the Asshole
File size: 305.8 MB

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Tue, 28 Feb 2012 10:28:57 +0200

Its Gonna Hurt - Latin Guy Tries a Big Dick _HD



Its Gonna Hurt - Latin Guy Tries a Big Dick _HD
Cast: Izzy, Malek Steel
Genres: Anal, Big Dick, Black, Blowjob, Facial, Gay Sex, Hardcore, Interracial, Latina

This weeks itsgonnahurt update is superb. We brought in this cat named Malek for some butthole surfing and as always he played the pain game where the only winner is the black Mamba. It was a valiant effort but in the end he was begging to stop and received a massive load on his face! Casual!

Format: mov (QuickTime)
Duration: 28:19
Video: 1280x720, AVC (H.264)
Audio: 73kbps


Its Gonna Hurt - Latin Guy Tries a Big Dick _HD
File size: 624.5 MB

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Tue, 21 Feb 2012 09:38:12 +0200

Its Gonna Hurt - The big bad dick _HD



Its Gonna Hurt - The big bad dick _HD
Cast: Izzy, Steve
Genres: Big Dick, Black, Brunette, Cumshot, Facial, Interracial, White

Every few updates there is always the guy who's jaw drops when Izzy pulls out his Black Mamba. In this case, the Black Mamba is Izzy's huge cock, and he is going to make this guy hurt. He slides into carefully into his ass, and you can tell from his face how he feels about it. It's great until he blasts his load all over his face, which he loves too

Format: mov (QuickTime)
Duration: 39:46
Video: 1280x720, AVC (H.264)
Audio: 69kbps


Its Gonna Hurt - The big bad dick _HD
File size: 875.9 MB

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Wed, 15 Feb 2012 10:03:12 +0200

Its Gonna Hurt - Gay for Pay _HD



Its Gonna Hurt - Gay for Pay _HD
Cast: Izzy, Devin Dickson

We have another fella who seems to have no problem sucking dick for a pay check. He did have a little bit of an issue getting Izzy's huge black cock up his asshole. This sites not called itsgonnahurt for nothing. Here we make pain a reality and this young little white boy got what he came for and maybe even a little more than he wished. Cum watch this guy Devin squeal like a pig!

Format: mov (QuickTime)
Duration: 35:33
Video: 1280x720, AVC (H.264)
Audio: 67kbps


Its Gonna Hurt - Gay for Pay _HD
File size: 781.9 MB

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Tue, 07 Feb 2012 23:09:28 +0200

Its Gonna Hurt - Monster Dick in the Line Up _HD



Its Gonna Hurt - Monster Dick in the Line Up _HD
Cast: Izzy, Bryson

What do you get when you get a little white man in a room and a hung Black man in the same room? You get a 'guess which is the dick in the line up' game. Its all about the mighty black cock in his young black hole. He knew what he came here for and found it. To get man crushed in the butt! Its gonna hurt, son!

Format: mov (QuickTime)
Duration: 29:14
Video: 1280x720, AVC (H.264)
Audio: 93kbps


Its Gonna Hurt - Monster Dick in the Line Up _HD
File size: 648.6 MB

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Wed, 01 Feb 2012 23:11:24 +0200

Its Gonna Hurt - Cole Gets a Reality check



Its Gonna Hurt - Cole Gets a Reality check
Cast: Izzy, Cole McKenzie

This weeks itsgonnahurt.com extravaganza is painful. We brought in this cat named Cole and he was fucking scared. He new we were gonna be fucking him in his asshole but he had no clue how big the piece of meat was gonna be going up there. This shoot is pure soul crushing pain. I promise you will squirm watching this guy take this monstrous black dick! Enjoy!

Format: lavfpref
Duration: 37:06
Video: 852x480, AVC (H.264), 1464kbps
Audio: 68kbps

Its Gonna Hurt - Cole Gets a Reality check Its Gonna Hurt - Cole Gets a Reality check
Its Gonna Hurt - Cole Gets a Reality check Its Gonna Hurt - Cole Gets a Reality check

Its Gonna Hurt - Cole Gets a Reality check
File size: 418.5 MB

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Wed, 25 Jan 2012 19:44:44 +0200

ItsGonnaHurt - Evan Likes Black Dick



ItsGonnaHurt - Evan Likes Black Dick

Hey people... This week we bring you another painful adventure on itsgonnahurt. In this episode Izzy puts the hammer to this little white boy named Evan Eros. Evan is a stripper and he loves hot chocolate in his mouth... if you no what I mean. If your here to see pain you got it. If you like interracial you got it and if your just plain old sick in the head you got it. I think your gonna love watching this little white boy get his shit pushed in! Enjoy!

Format: lavfpref
Duration: 32:53
Video: 1280x720, AVC (H.264), 2928kbps
Audio: 69kbps

ItsGonnaHurt - Evan Likes Black Dick ItsGonnaHurt - Evan Likes Black Dick
ItsGonnaHurt - Evan Likes Black Dick ItsGonnaHurt - Evan Likes Black Dick

ItsGonnaHurt - Evan Likes Black Dick
File size: 723.8 MB

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Mon, 23 Jan 2012 22:45:08 +0200

It's Gonna Hurt - Gettin it like a Dirty Dog - Izzy & David Chase



It's Gonna Hurt - Gettin it like a Dirty Dog - Izzy & David Chase

This week on itsgonnahurt.com we brought in this guy David who is a repeat offender on this site with a craving for chocolate dick. It's a little strange how much this guy likes getting fucked by giant black cock, but we are here to please everyone, so if you like it cum get some. If you need money cum get some. If you're a sick twisted fuck that likes pain, cum gets some. This video is really good with lots of deep throat dick sucking and plenty of butt sex for all! Enjoy!

Format: lavfpref
Duration: 21:38
Video: 1280x720, AVC (H.264), 2638kbps
Audio: 83kbps

It's Gonna Hurt - Gettin it like a Dirty Dog - Izzy & David Chase It's Gonna Hurt - Gettin it like a Dirty Dog - Izzy & David Chase
It's Gonna Hurt - Gettin it like a Dirty Dog - Izzy & David Chase It's Gonna Hurt - Gettin it like a Dirty Dog - Izzy & David Chase

It's Gonna Hurt - Gettin it like a Dirty Dog - Izzy & David Chase
File size: 432.1 MB

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Mon, 23 Jan 2012 09:24:20 +0200

It's Gonna Hurt - The Lumber Jack Slam - Castro & David Chase



It's Gonna Hurt - The Lumber Jack Slam - Castro & David Chase

Hey everyone. Today we brought in this guy named Cory and it was really great watching this 6 ft 5 inch guy surrender to Castro's giant cock. This guy was a real champ cause he tried to deep throat Castro's meat! It didn't really work but it was fun watching him gag and tear up like he was crying! I think at one point he might have been crying. Seriously, watch this big lumberjack get his hole pounded!

Format: lavfpref
Duration: 36:35
Video: 1280x720, AVC (H.264), 2613kbps
Audio: 80kbps

It's Gonna Hurt - The Lumber Jack Slam - Castro & David Chase It's Gonna Hurt - The Lumber Jack Slam - Castro & David Chase
It's Gonna Hurt - The Lumber Jack Slam - Castro & David Chase It's Gonna Hurt - The Lumber Jack Slam - Castro & David Chase

It's Gonna Hurt - The Lumber Jack Slam - Castro & David Chase
File size: 723.0 MB

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Tue, 17 Jan 2012 10:43:17 +0200

Its Gonna Hurt - That had to of Hurt...again



Its Gonna Hurt - That had to of Hurt...again

Trent Diesel was one of our earlier victims when we were first starting out. Well after taking on Castro and getting his asshole gaped open, he couldn't find another man to satisfy him like that again. So then 2 years later he came back to us, because he knew we had the goods. And like an addict, he had to have is ass hole ripped wide open again. Look like this is gonna hurt...again.

Format: lavfpref
Duration: 32:53
Video: 1280x720, AVC (H.264), 2927kbps
Audio: 93kbps

Its Gonna Hurt - That had to of Hurt...again Its Gonna Hurt - That had to of Hurt...again
Its Gonna Hurt - That had to of Hurt...again Its Gonna Hurt - That had to of Hurt...again

Its Gonna Hurt - That had to of Hurt...again
File size: 729.3 MB

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Tue, 10 Jan 2012 23:47:32 +0200

Its Gonna Hurt - Size wins Top _HD



Its Gonna Hurt - Size wins Top _HD

People normally always no what there getting themselves into when they sign up to shoot with us but sometimes people are so overwhelmed by the pay they forget what they came to do. We brought in this guy Marxel and told him we weren't sure if he was gonna bottom or top it just depends if his dicks bigger than the other talent. His dick was surprisingly much smaller than Izzy's. So... He got his asshole fucked into submission. It was really funny to see his expression when...

Format: lavfpref
Duration: 31:02
Video: 1280x720, AVC (H.264)
Audio: 125kbps

Its Gonna Hurt - Size wins Top _HD Its Gonna Hurt - Size wins Top _HD
Its Gonna Hurt - Size wins Top _HD Its Gonna Hurt - Size wins Top _HD

Its Gonna Hurt - Size wins Top _HD
File size: 681.9 MB

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Fri, 06 Jan 2012 23:21:33 +0200

ItsGonnaHurt - He Works In A Surf Shop (HD)



ItsGonnaHurt - He Works In A Surf Shop (HD)

Hey peeps... here we go with another update of itsgonnahurt. Today's meat market special is a guy named Cody . Cody works in a surf shop and he is married to a female. The closest thing this guy has come to gay sex is making out with a dude in college. He was extremely tense going into this shoot and came out tenderized as all hell because Izzy didn't hold back and all Cody could do is hold-on to ride out the black anal storm. This shoot is a good example of what not to do to pay your rent.

Duration: 34mn 25s 699ms
Video: AVC at 3 000 Kbps, Aspect: 1280 x 720 (1.778) at 29.970 fps
Audio: AAC at 69.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - He Works In A Surf Shop (HD)

File size: 757.4 MB

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Fri, 06 Jan 2012 14:10:06 +0200

It's Gonna Hurt - Shockingly Painful



It's Gonna Hurt - Shockingly Painful

Hey guys and gals. We are proud to announce this week's itsgonnahurt.com featuring Izzy & Ricky McCoy. Ricky is a young white boy who has been recently become fascinated with the idea of getting screwed by a big black cock. Fortunately for you guys we have one of those here for your entertainment. This would now make it unfortunate for little Ricky because Izzy knocks that tight little butt-hole into next week. Don't miss this Man-on-Man action here on itsgonnahurt!

Format: lavfpref
Duration: 24:53
Video: 852x480, AVC (H.264)
Audio: 125kbps

It's Gonna Hurt - Shockingly Painful It's Gonna Hurt - Shockingly Painful
It's Gonna Hurt - Shockingly Painful It's Gonna Hurt - Shockingly Painful

It's Gonna Hurt - Shockingly Painful
File size: 281.4 MB

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Wed, 28 Dec 2011 16:55:16 +0200

ItsGonnaHurt - How's Your Pain Tolerance



ItsGonnaHurt - How's Your Pain Tolerance

This week on itsgonnahurt.com we brought in this cat named Austin. He said he had a pretty high pain tolerance but it seems he did not... because he was squealing like a pig about to get its head cut off as Izzy's massive black cock entered his alimentary canal or (asshole). On scale of one-to-ten, ten being the high side I would have to rate this guys pain tolerance as a viewer 2! Cum watch this great demonstration of interracial man love! Peace out!

Duration: 29mn 2s 409ms
Video: AVC at 3 000 Kbps, Aspect: 1280 x 720 (1.778) at 29.970 fps
Audio: AAC at 70.5 Kbps, Infos: 2 channels, 44.1 KHz


ItsGonnaHurt - How's Your Pain Tolerance
File size: 639.2 MB

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Wed, 21 Dec 2011 09:16:44 +0200

ItsGonnaHurt - A Little Pain for the Holiday (HD)



ItsGonnaHurt - A Little Pain for the Holiday (HD)

Hey peeps... This weeks its gonna hurt update is a present from us to you. We brought in this "straight Guy" to suck dick and get fucked in the ass. Hmmmm..... Anyways he screamed and shouted and the next thing you knew he had a huge load from a monster black cock all over his face. Tis the season and it's gonna hurt bitches! Cum watch this savage anal adventure of pain and enjoy!

Duration: 29mn 27s 434ms
Video: AVC at 3 000 Kbps, Aspect: 1280 x 720 (1.778) at 29.970 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - A Little Pain for the Holiday (HD)

File size: 648.5 MB

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Wed, 14 Dec 2011 08:46:35 +0200

ItsGonnaHurt - Return of the Rock (HD)



ItsGonnaHurt - Return of the Rock (HD)

Hey people this weeks It's gonna Hurt update is the tits. We had this jacked diesel broski named Rock return for his second time here on its gonna hurt. Last time he was here he had the pleasure of getting his asshole ripped open by Castro. This time he fucks Izzy and my friends its not pretty and I think he had to leave the shoot wearing a depends cause his shit got pushed the fuck in! Watch and drool

Format: mov (QuickTime)
Duration: 26:26
Video: 1280x720, AVC (H.264)
Audio: 63kbps


ItsGonnaHurt - Return of the Rock (HD)
File size: 580.5 MB

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Wed, 07 Dec 2011 16:30:41 +0200

ItsGonnaHurt - Max It Out!



ItsGonnaHurt - Max It Out!

Like all "it's Gonna Hurt" updates, we here love to put regular guys through the stress of stretching their bum hole to their limit. Today's Max Gunnar and Izzy is no different. The boys did not disappoint! There's hardcore ass fucking, and cock munching and all the pain that comes from shoving and huge cock into an unsuspecting ass hole. Max truly took all of Izzy and love every moment of if. IT WAS AWESOME! Check it out and shoot us emails telling us if you were as excited about this shoot as we are. Enjoy!

Format: mov (QuickTime)
Duration: 23:42
Video: 1280x720, AVC (H.264)
Audio: 65kbps


ItsGonnaHurt - Max It Out!
File size: 520.6 MB

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Sun, 04 Dec 2011 19:30:41 +0200

It's Gonna Hurt - Snake Dancing



It's Gonna Hurt - Snake Dancing

Wow this guy was not ready. This week's itsgonnahurt update is crazy. We brought in this cat Santiago for an anal pulverizing session and let me tell you all he was not ready. He said "It hurts like hell" and we said "NO shit! The site's called Itsgonnahurt.com". The weirdest shit happens when Santiago first gets the black pipe stuffed into him. I want to tell y'all but I would hate to be a spoiler. So watch this video and dream and who knows you could be next!

Format: mov (QuickTime)
Duration: 25:27
Video: 852x480, AVC (H.264)
Audio: 70kbps


It's Gonna Hurt - Snake Dancing
File size: 287.5 MB

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Wed, 30 Nov 2011 14:15:15 +0200

ItsGonnaHurt - How Bad Do You Want Them (HD)



ItsGonnaHurt - How Bad Do You Want Them (HD)

In this weeks It's Gonna Hurt were out trying to find a lucky winner for my friend izzy he has been dying to get some ass so I came up with an idea and I used the fact that there was a big event going on tonight and used it to my full advantage.So were out doing our thing and this guy out of nowhere comes up to us asking for tickets like a fiend or something but luckily I did have some spair tickets in hand but in order for him to get these tickets he has to do my friend Izzy I mean literally he as to suck his cock and let him fuck him in the ass and all and be hold he took the exchange if you may lol my boy let this little white boy have it,let's just say he earned them tikets lol Stay Tuned!

Format: mov (QuickTime)
Duration: 17:40
Video: 1280x720, AVC (H.264)
Audio: 62kbps


ItsGonnaHurt - How Bad Do You Want Them (HD)
File size: 387.8 MB

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Wed, 23 Nov 2011 15:30:51 +0200

ItsGonnaHurt - Do What You Got To!



ItsGonnaHurt - Do What You Got To!

Today we have a dude that is totally trying to get into the porn game. So he was told that in order to get in he had to do gay porn first. So we run through everything that he is supposed to do on his first shoot. What he does know is that he is not fucking or getting his dick sucked today. So we tell him that the way it is determined who fucks who is, who ever has the biggest cock gives and and the smaller cock takes it all. It obvious we they both pull out who wins. He doesn't seem too disappointed, but is very afraid of our friend's large black snake. This guy can barely take his cock at all. Constantly complaining and to be the trooper that his is, he takes a huge load all is his face. We tell him good job and good luck on the next one.


ItsGonnaHurt - Do What You Got To!
File size: 652.4 MB

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Wed, 16 Nov 2011 15:40:09 +0200

ItsGonnaHurt - Snake Dancing



ItsGonnaHurt - Snake Dancing

Wow this guy was not ready. This week's itsgonnahurt update is crazy. We brought in this cat Santiago for an anal pulverizing session and let me tell you all he was not ready. He said "It hurts like hell" and we said "NO shit! The site's called Itsgonnahurt.com". The weirdest shit happens when Santiago first gets the black pipe stuffed into him. I want to tell y'all but I would hate to be a spoiler. So watch this video and dream and who knows you could be next!

Format: mov (QuickTime)
Duration: 25:27
Video: 1280x720, AVC (H.264)
Audio: 70kbps


ItsGonnaHurt - Snake Dancing
File size: 560.4 MB

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Thu, 10 Nov 2011 14:33:35 +0200

It's Gonna Hurt - Cutting Class For Cock



It's Gonna Hurt - Cutting Class For Cock

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.

Format: avi
Duration: 40:34
Video: 852x480, DivX 5, 1565kbps
Audio: 125kbps

It's Gonna Hurt - Cutting Class For Cock It's Gonna Hurt - Cutting Class For Cock
It's Gonna Hurt - Cutting Class For Cock It's Gonna Hurt - Cutting Class For Cock

It's Gonna Hurt - Cutting Class For Cock
File size: 506.1 MB

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Mon, 31 Oct 2011 21:09:56 +0200

It's Gonna Hurt - Wake up call



It's Gonna Hurt - Wake up call

If you love big black dick then you would love to be woken up by one being stabbed in your eye. This weeks update is classic. We actually started this shoot with Izzy slapping his massive dick off this guy Alex's face while he was asleep. As soon as Alex woke up he was in heaven and immediately started blowing the shit out of that big chocolate stick. Alex really enjoyed himself today and we think you will too. Check it out bitches!

Format: mov (QuickTime)
Duration: 26:12
Video: 852x480, AVC (H.264)
Audio: 70kbps


It's Gonna Hurt - Wake up call
File size: 295.7 MB

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Sun, 30 Oct 2011 20:56:14 +0200

It's Gonna Hurt - White Boys Love Black Dick



It's Gonna Hurt - White Boys Love Black Dick

Hey peeps.... Here is another heartthrob white boy who can't resist a massive chocolate cock. We brought in this boy Cameron and he came prepared. Well at least thats what he said. It seems everybody's story changes once they get a huge black dick smacked off there forehead. To make a long awesome story short Izzy fucks this white boy until he can't take it anymore and then drops a monster load on his face. Its gonna hurt Baby!


It's Gonna Hurt - White Boys Love Black Dick
File size: 271.8 MB

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Wed, 26 Oct 2011 22:08:25 +0300

Its Gonna Hurt - Tough Guy Gets Humbled



Its Gonna Hurt - Tough Guy Gets Humbled

Greetings itsgonnahurt.com fans. This update is outrageously great. We brought in this surfer dude named Jackson. He was very cocky/confident that he could take Izzy's dick in his butthole. He had claimed he'd had comparably sized cocks and wasn't worried in the slightest. Needless to say the tables abruptly turned when Izzy stuffed his giant black cock up Jackson's asshole. LOL... Its not called it's gonna hurt for nothing!


Its Gonna Hurt - Tough Guy Gets Humbled
File size: 558.3 MB

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Sat, 15 Oct 2011 14:32:52 +0300

It's Gonna Hurt - Shockingly Painful



It's Gonna Hurt - Shockingly Painful

Hey guys and gals. We are proud to announce this week's itsgonnahurt.com featuring Izzy & Ricky McCoy. Ricky is a young white boy who has been recently become fascinated with the idea of getting screwed by a big black cock. Fortunately for you guys we have one of those here for your entertainment. This would now make it unfortunate for little Ricky because Izzy knocks that tight little butt-hole into next week. Don't miss this Man-on-Man action here on itsgonnahurt.com!

It's Gonna Hurt - Shockingly Painful It's Gonna Hurt - Shockingly Painful
It's Gonna Hurt - Shockingly Painful It's Gonna Hurt - Shockingly Painful

It's Gonna Hurt - Shockingly Painful
File size: 281.4 MB

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Thu, 06 Oct 2011 08:44:27 +0300

It's Gonna Hurt - The Big Hurt - Castro and Daniel



It's Gonna Hurt - The Big Hurt - Castro and Daniel

Hey peeps! We got another itsgonnahurt for ya. This guy Daniel gets his shit pushed in pretty good. I think he was crying at one point during his asshole destruction. Castro didn't mind his soft lips on his massive meat hanger. Cum watch Castro destroy another little white dude!

Length: 284 MiB Duration: 31mn 7s 334ms
Video: AVC at 1 199 Kbps, Aspect: 720 x 404 (1.782) at 29.970 fps
Audio: AAC at 69.8 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - The Big Hurt - Castro and Daniel

File size: 283.8 MB

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Thu, 22 Sep 2011 10:02:23 +0300

It's Gonna Hurt - Big Boys Like Big Toys



It's Gonna Hurt - Big Boys Like Big Toys

We got another asshole slaying for you all here on Itsgonnahurt. We brought in this big muscle head dude named Mitch to get his b-hole beat up by Izzy's monster dick. Mitch was completely terrified when I told him we were gonna lock the door so he couldn't run out when he got too scared or when the pain reached its ultimate high. Anyways you should come watch this jacked white dude take some black dick!

Length: 284 MiB Duration: 25mn 11s 411ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Big Boys Like Big Toys

File size: 284.2 MB

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Sat, 17 Sep 2011 16:09:54 +0300

It's Gonna Hurt - Gettin it like a Dirty Dog!



It's Gonna Hurt - Gettin it like a Dirty Dog!

This week on itsgonnahurt.com we brought in this guy David who is a repeat offender on this site with a craving for chocolate dick. It's a little strange how much this guy likes getting fucked by giant black cock, but we are here to please everyone, so if you like it cum get some. If you need money cum get some. If you're a sick twisted fuck that likes pain, cum gets some. This video is really good with lots of deep throat dick sucking and plenty of butt sex for all! Enjoy!

Length: 476 MiB Duration: 21mn 37s 809ms
Video: AVC at 3 000 Kbps, Aspect: 1280 x 720 (1.778) at 29.970 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Gettin it like a Dirty Dog!

File size: 476.2 MB

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Sun, 11 Sep 2011 10:53:31 +0300

It's Gonna Hurt - My friends are going to love me



It's Gonna Hurt - My friends are going to love me

A super fan of Castro's huge cock can't wait to experience and tell all his friends how it really went down. He can't believe how big his fucking cock is; he even takes pictures of him like he met a celebrity; I think he even tries to talk to it and say HELLO! He jumps right into to some great BJ action taking all that cock in his mouth. It looks fucking amazing; especially when he spreads his legs wide, ear to ear, and lets Castro and his partner in crime straight pound his tight asshole to make him scream like a girl! He takes as much as he can of Castro's UNIT and totally thanks him numerous times, lol. This might be Castro's #1 fan! Who's next to try out the MONSTER? Maybe you.

Length: 323 MiB Duration: 28mn 42s 990ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 66.15 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - My friends are going to love me

File size: 323.2 MB

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Sun, 28 Aug 2011 11:30:05 +0300

It's Gonna Hurt - Fairy Tales Come True



It's Gonna Hurt - Fairy Tales Come True

Today we have a newbie named DJ who said he doesn't believe in fairy tales and dragons and shit. So I ask him a few questions like what is the biggest he has every had, you know typical shit, he told me 8 or 9. So I laughed when I told he about the size of Castro's unit and he seemed pretty nervous about the whole event. I told him its like a good fairy tale that has a GREAT ending. As soon as Castro pulls out his hook and totally puts on a fucking show worth a crowd applause. Castro shows him how myths and fairy tales are so fucking true when he unleashes his dragon with a hardcore fucking pounding, boom boom all in his fucking face.

Length: 301 MiB Duration: 26mn 24s 692ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 85.4 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Fairy Tales Come True

File size: 300.8 MB

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Fri, 19 Aug 2011 07:31:52 +0300

It's Gonna Hurt - Gettin Hooked



It's Gonna Hurt - Gettin Hooked

What's happening my bitches! We got a nice update for you today with Tony. He's hungry for some cock, some dragon cock that is! Poor Tony, I'm not too sure he really knew what he was in for. He claims he was ready, but from his expression when Castro came around the corner and surprised him, he was nothing but stunned! Tony didn't miss a beat though. He jumped on the hook right off the bat. Castro had him in all sorts of positions. Tony found out pretty quickly that It's Gonna Hurt when you get the Hook!!!!

Length: 484 MiB Duration: 21mn 59s 799ms
Video: AVC at 3 000 Kbps, Aspect: 1280 x 720 (1.778) at 29.970 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Gettin Hooked

File size: 484.1 MB

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Sat, 13 Aug 2011 09:08:19 +0300

It's Gonna Hurt - Tweetie Bird needs a break!



It's Gonna Hurt - Tweetie Bird needs a break!

Why oh why do you all keep doing this? This week's itsgonnahurt update is funny. It seems to be a trend of quitters here on this site. Maybe it's a coincidence or may it's because these guy's are all taking a Louisville Slugger up there Wahzoo. This little white boy Jesse played the pain game and lost horribly. Everything should be fine when they reattach his guts to a colostomy bag! Just kidding but god damn that shit has got to hurt! Peace out bitches!

Length: 331 MiB Duration: 29mn 31s 148ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 63.1 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Tweetie Bird needs a break!

File size: 331.3 MB

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Tue, 02 Aug 2011 22:45:40 +0300

ItsGonnaHurt - 20 Plus Inches Of Hell!



ItsGonnaHurt - 20 Plus Inches Of Hell!

We only promise one thing here on itsgonnahurt.com and that is PAIN! We brought back Castro's partner in crime Izzy to double team this guy Jacob. Jacob is a young white guy who obviously is very impulsive because I don't think he thought this through a 100%. Long story shor...

Length: 242 MiB Duration: 31mn 26s 987ms
Video: AVC at 1 000 Kbps, Aspect: 720 x 404 (1.782) at 29.970 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - 20 Plus Inches Of Hell!

File size: 242.5 MB

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Tue, 02 Aug 2011 22:45:40 +0300

ItsGonnaHurt - Jumbo Black Dick Swallowed by a White Guy



ItsGonnaHurt - Jumbo Black Dick Swallowed by a White Guy

Welcome to Its Gonna Hurt!
ItsGonnaHurt - Jumbo Black Dick Swallowed by a White Guy
Where giant dicks get stuffed into tight assholes...and its gonna hurt so good!

Length: 262 MiB Duration: 23mn 11s 425ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - Jumbo Black Dick Swallowed by a White Guy

File size: 261.7 MB

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Sun, 31 Jul 2011 08:58:02 +0300

It's Gonna Hurt - Twenty...Scared...And Hungry!



It's Gonna Hurt - Twenty...Scared...And Hungry!

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!

b]Length:[/b] 443 MiB Duration: 33mn 5s 352ms
Video: AVC at 1 798 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 66.15 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Twenty...Scared...And Hungry!

File size: 442.5 MB

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Sun, 31 Jul 2011 08:58:02 +0300

It's Gonna Hurt - White Boy Gets Owned!



It's Gonna Hurt - White Boy Gets Owned!

This update of It's Gonna Hurt features Castro Supreme and some little white dude that's trying to prove something to his prostate. This little fucker gets cracked in half by Castro's mammoth sized cock and then he gets mother fuckin loads dropped on his face. That shit will always hurt! Peace out, bitches!

Length: 353 MiB Duration: 26mn 20s 514ms
Video: AVC at 1 798 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 69.3 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - White Boy Gets Owned!

File size: 353.0 MB

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Sun, 31 Jul 2011 08:58:01 +0300

It's Gonna Hurt - No Pain No Gain!



It's Gonna Hurt - No Pain No Gain!

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'll ease his way inside that little asshole of yours until that anaconda is balls-deep. Ouch! It's Gonna Hurt!

Length: 334 MiB Duration: 24mn 54s 294ms
Video: AVC at 1 798 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - No Pain No Gain!

File size: 334.3 MB

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Sun, 31 Jul 2011 08:58:01 +0300

It's Gonna Hurt - The Pillow Biting Heart Breaker!



It's Gonna Hurt - The Pillow Biting Heart Breaker!

So... This broski answered and ad of mine. I figured Castro's Dick is so famous I would start charging people to put it in there mouth. To make a long story short he paid and then he got his tight little asshole bored out until Castro Supreme dropped a motherfucking load on his face. Enjoy boys!

Length: 270 MiB Duration: 23mn 58s 839ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 67.9 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - The Pillow Biting Heart Breaker!

File size: 270.3 MB

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Sun, 31 Jul 2011 08:58:01 +0300

It's Gonna Hurt - Mclovin Loves Black Dick



It's Gonna Hurt - Mclovin Loves Black Dick

This itsgonnahurt shoot features this guy Erick who is a man of few words with one thing on his mind and that is big black dick that will bring him more pain than he can bare. He actually handles being double stuffed by Castro and Izzy pretty well. In the end he got what he came for : A swollen asshole and cum all over his lips. He took his savage asshole ripping like a champ! Good job Erick your pain is our reward! Peace out fuckers!

Length: 358 MiB Duration: 31mn 49s 710ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 66.15 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Mclovin Loves Black Dick

File size: 358.0 MB

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Sun, 31 Jul 2011 08:58:00 +0300

It's Gonna Hurt - Castro Is A Magician!



It's Gonna Hurt - Castro Is A Magician!

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!

Length: 407 MiB Duration: 36mn 9s 903ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 69.8 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Castro Is A Magician!

File size: 407.4 MB

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Sat, 30 Jul 2011 09:09:13 +0300

It's Gonna Hurt - There's A First Time For Everything!



It's Gonna Hurt - There's A First Time For Everything!

We all know that Castro Supreme has a huge monster cock that destroys everything in its path. Today we have Derrick stepping up to the plate to see what the hype is all about. He wouldn't believe it until he seen it in person. This guy is in for a rude awakening. Once Castro whipped his log of a cock out, Derrick's jaw dropped in disbelief. Next thing you know Derrick had a mouth full of man meat. Castro wasted no time and gave him what he wanted to witness: an ass pounding like non before. Poor guy! This is really gonna hurt. Good Luck!

Length: 390 MiB Duration: 29mn 6s 246ms
Video: AVC at 1 798 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 68.5 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - There's A First Time For Everything!

File size: 390.0 MB

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Fri, 29 Jul 2011 12:11:21 +0300

It's Gonna Hurt - Sean's Anal Demise



It's Gonna Hurt - Sean's Anal Demise

Here we are again with another anal ravaging by Castro Supreme. This week's update features Sean Slater, a beefy looking cock swallowing dude that just can't live with out a big black dick in his asshole. Cum watch Castro fuck this dudes booty hole until he cries! Peace out Bitches!

Length: 254 MiB Duration: 22mn 32s 978ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Sean's Anal Demise

File size: 254.2 MB

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Fri, 29 Jul 2011 12:11:19 +0300

It's Gonna Hurt - Screaming For Joy!



It's Gonna Hurt - Screaming For Joy!

This site itsgonnahurt.com is no fucking joke. We brought in this dude Tony Douglas. Tony craves black dick. He receives what he craves right up his tight little asshole. He then proceeds to scream like a bitch in heat and pant like a dog while Castro puts a blistering beating down on him until he receives his man milkshake all over his face. LOL

Length: 426 MiB Duration: 31mn 45s 772ms
Video: AVC at 1 798 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 69.2 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Screaming For Joy!

File size: 425.7 MB

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Fri, 29 Jul 2011 12:11:18 +0300

It's Gonna Hurt - Hung Solo



It's Gonna Hurt - Hung Solo

Hey people... Castro breaks this guy Joey Baltimores Ass in half. Joey is a pretty ripped dude that has a fat ass and loves getting his ass packed with big black salami. This guy loved every second of the anal scene with Castro Supreme. He screamed with joy as Castro savagely fucked him until he blasted his face with hot cum. Winning!

Length: 327 MiB Duration: 29mn 1s 341ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 69.3 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Hung Solo

File size: 326.6 MB

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Fri, 29 Jul 2011 12:11:17 +0300

It's Gonna Hurt - Gene Meet Castro's Big Black Dick



It's Gonna Hurt - Gene Meet Castro's Big Black Dick

Attention all you sick twisted fuckers. This week we brought in this Midwesterner Gene to pleasure Castro's big hard meat pipe. It seems that Gene might have bit off more than he could chew. Castro buries his huge dick deep into Genes tight little asshole. I promise your gonna love watching these two boys love on each other! Later fuckers!

Length: 221 MiB Duration: 20mn 23s 599ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: AAC at 70.1 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Gene Meet Castro's Big Black Dick

File size: 220.9 MB

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Fri, 29 Jul 2011 12:11:16 +0300

It's Gonna Hurt - Butthole Mashing



It's Gonna Hurt - Butthole Mashing

So this week on Itsgonnahurt.com we put another white dudes asshole through a savage pounding from Castro Supreme's monster cock. Castro comes work to crack asses in half for all of your entertainment. Christopher Daniels came here to try something new and exciting. I guess his of exciting is getting his asshole smashed up. Cum all who dare. Castro's got enough to go around for seconds and thirds. Enjoy!

Length: 318 MiB Duration: 28mn 12s 860ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 69.9 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Butthole Mashing

File size: 318.5 MB

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Fri, 29 Jul 2011 12:11:14 +0300

It's Gonna Hurt - Asshole Blasting!



It's Gonna Hurt - Asshole Blasting!

Hey guys... This weeks itsgonnahurt update is wonderful. This guy Alex came to us to get his insides rearranged and my friends Castro was more than happy to share the love with his massive cock. After about 20 minutes Alex Taps out only to get a warm load of white cum smeared across his face. Watch and cringe!

Length: 238 MiB Duration: 21mn 56s 66ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Asshole Blasting!

File size: 237.9 MB

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Fri, 29 Jul 2011 12:11:13 +0300

It's Gonna Hurt - Another Man Tastes The Dragon!!!



It's Gonna Hurt - Another Man Tastes The Dragon!!!

When you sign up to do your first gay scene on tape you might wanna think twice. This guy Ben came to test Castro Supreme's Dragon. For those of you who are unsure of what that it is.... Its a big black dick that looks like a club you would use on baby seals. Unfortunately or fortunately for some of you sick fucks its a tool we use around here to crack assholes open. This little fucker gets split wide open with a smile on his face. Check it out and love it. Later bitches!
Length: 262 MiB Duration: 23mn 11s 425ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Another Man Tastes The Dragon!!!

File size: 261.7 MB

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Thu, 28 Jul 2011 22:15:30 +0300

It's Gonna Hurt - The Big Hurt



It's Gonna Hurt - The Big Hurt

Hey peeps! We got another itsgonnahurt for ya. This guy Daniel gets his shit pushed in pretty good. I think he was crying at one point during his asshole destruction. Castro didn't mind his soft lips on his massive meat hanger. Cum watch Castro destroy another little white dude!

Length: 351 MiB Duration: 31mn 7s 267ms
Video: AVC at 1 500 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: AAC at 69.8 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - The Big Hurt

File size: 351.1 MB

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Tue, 19 Jul 2011 09:22:22 +0300

ItsGonnaHurt - Double Dick Destruction



ItsGonnaHurt - Double Dick Destruction

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!

Length: 245 MiB Duration: 26mn 51s 144ms
Video: AVC at 1 198 Kbps, Aspect: 720 x 404 (1.782) at 29.970 fps
Audio: AAC at 72.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - Double Dick Destruction

File size: 245.5 MB

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Mon, 18 Jul 2011 16:19:46 +0300

ItsGonnaHurt - Can You Smell What The Rock Is Sucking!



ItsGonnaHurt - Can You Smell What The Rock Is Sucking!

Can you Smell what The Rock is Sucking! This week on itsgonnahurt we brought in The Rock who is this big jacked gay dude that always fantasized about taking a big black dick in the ass. He was kinda scared but handles him self well. I was glad to because it would have been scary to see this huge dude crying and screaming! LOL... Good shoot here... you don't want to miss it.

Length: 216 MiB Duration: 27mn 57s 878ms
Video: AVC at 1 000 Kbps, Aspect: 720 x 404 (1.782) at 29.970 fps
Audio: AAC at 66.15 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - Can You Smell What The Rock Is Sucking!

File size: 215.5 MB

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Sun, 05 Jun 2011 09:15:30 +0300

Its Gonna Hurt - Butthole Smash! (Bryan & Castro)



Its Gonna Hurt - Butthole Smash!  (Bryan & Castro)

This Tuesday's It's Gonna Hurt update is great! We brought in this guy Bryan to get his face and ass smashed in by Castro's obscenely large dick. Unlike most updates, this guy could barely finish. Bryan was in so much PAIN it was kinda funny. I really felt bad for this one but like the sign said: "It's Gonna Hurt!" Enjoy, you sick fucks!

Length: 351 MiB Duration: 33mn 47s 245ms
Video: WMV2 at 1 259 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

Its Gonna Hurt - Butthole Smash!  (Bryan & Castro)

File size: 351.1 MB

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Tue, 24 May 2011 14:07:11 +0300

Its Gonna Hurt - Latino Gets A Hurtin



Its Gonna Hurt - Latino Gets A Hurtin

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'

Length: 536 MiB Duration: 1h 33mn 19s 34ms
Video: VP6 at 699 Kbps, Aspect: 852 x 480 (1.775)
Audio: MPEG Audio at 64.0 Kbps, Infos: 2 channels, 44.1 KHz

Its Gonna Hurt - Latino Gets A Hurtin

File size: 536.5 MB

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Mon, 28 Mar 2011 18:09:05 +0300

It's Gonna Hurt - Clayton was Scared!



It's Gonna Hurt - Clayton was Scared!

LOL... I always think it's funny when people cum to take Castro's Dick in there ass. There facial expressions say it all. This guy Clayton came to us and during the beginning of the shoot he was literally shaking. I would assume he was scared but you never know he could have been penis withdrawals or some shit like that. You just never know with some of these sick fuckers. Cum watch Castro gut this fool!

Length: 672 MiB Duration: 34mn 14s 333ms
Video: MPEG-4 Visual at 2 604 Kbps, Aspect: 852 x 480 (1.775) at 30.000 fps
Audio: MPEG Audio at 128 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Clayton was Scared!

File size: 672.2 MB

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Thu, 10 Mar 2011 09:20:31 +0200

It's Gonna Hurt - Anal Lasagna



It's Gonna Hurt - Anal Lasagna

We got a big boy for you guys this time. Damien is a huge dude, and he's ready to get piped by Castro's massive cock. He's a little curious, and this will be his biggest dick ever. He cautiously sucks on it, and then takes it in his ass, ALL-THE-WAY. Did he make it out alive? Come find out.

Length: 362 MiB Duration: 33mn 23s 418ms
Video: WMV2 at 1 320 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Anal Lasagna

File size: 362.3 MB

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Sat, 05 Mar 2011 20:34:49 +0200

It's Gonna Hurt - Spencer the Badass



It's Gonna Hurt - Spencer the Badass

Greetings Fans! LOL...On this episode of itsgonnahurt this guy Spencer had no concerns about Castro's Horse dick being crammed up his poop hole. Well at least that was his theory before the shoot. After the shoot we saw was a scared individual who had just received an intestinal rearrangement! Come laugh... Cry... and Cum.

Length: 628 MiB Duration: 32mn 19s 252ms
Video: MPEG-4 Visual at 2 576 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: MPEG Audio at 128 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Spencer the Badass

File size: 628.1 MB

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Thu, 03 Mar 2011 18:49:14 +0200

It's Gonna Hurt - Savage Asshole Stretching



It's Gonna Hurt - Savage Asshole Stretching

A lot of people ask... "Is this Real?", "Is Castro's Cock that Big?" Well, my friends... go ask Noah Brooks, the latest victim on It's Gonna Hurt. Noah always wanted to try a big black dick. Now he has, and I'm pretty sure he will never do it again. He received a savage asshole stretching with a side of cream sauce. We warned him... It's Gonna Hurt!

Length: 543 MiB Duration: 36mn 33s 909ms
Video: WMV2 at 1 856 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Savage Asshole Stretching

File size: 542.6 MB

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Sat, 19 Feb 2011 14:23:39 +0200

It's Gonna Hurt - Youngster gets an Ass Fucking



It's Gonna Hurt - Youngster gets an Ass Fucking

So let it be known that Castro Supreme's cock is no fucking joke. This guy's job is to destroy assholes and plumbing systems. We got another anal victim named Jacob; this guy had tears of joy blowing Castro's fat dick. Here is another video for all you sick fucks who love to watch young men get their assholes ripped open! Enjoy, Fuckers!

Length: 337 MiB Duration: 29mn 4s 854ms
Video: WMV2 at 1 421 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Youngster gets an Ass Fucking

File size: 337.5 MB

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Sun, 13 Feb 2011 18:07:19 +0200

It's Gonna Hurt - Back Blown Out!



It's Gonna Hurt - Back Blown Out!

Alex Hilton is excited to see Castro Supreme's boomerang cock. Not only will he get a chance to witness a cock of that caliber, but he'll also know what it feels like having a monstrous cock shoved up his ass. Alex Hilton was all smiles once Castro stood in front of him with a 13-inch cock gazing into his eyes. All he could do was jump for joy, wrapping his lips around the cock without hesitation. Barely fitting it in his mouth, Alex decided to see if his ass can do better. Ouch! Bad move dude. No worries though; Castro is a gentle giant. Enjoy!

Length: 252 MiB Duration: 28mn 14s 472ms
Video: WMV2 at 1 059 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Back Blown Out!

File size: 251.5 MB

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Mon, 07 Feb 2011 08:28:49 +0200

It's Gonna Hurt - Doing It Big!



It's Gonna Hurt - Doing It Big!

Payton's a bit nervous about interviewing for It's Gonna Hurt. Who wouldn't be! Having a cock shoved up your ass that's big as a bat isn't easy. Especially when Castro Supreme's dick hooks to the left. It's going to hit each wall in Payton's asshole. Hope he knows what he's getting himself into. The only thing I can advise him is to think happy thought because It's Gonna Hurt.

Length: 492 MiB Duration: 41mn 13s 358ms
Video: WMV2 at 1 465 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Doing It Big!

File size: 491.8 MB

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Sat, 05 Feb 2011 16:51:27 +0200

Its Gonna Hurt - 3 Pointer! Chase, Devin, and Castro



Its Gonna Hurt - 3 Pointer!  Chase, Devin, and Castro

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 ass. He was pretty worn out at the end of it all, but his smile is worth a thousand words.

Length: 624 MiB Duration: 1h 48mn 37s 0ms
Video: VP6 at 699 Kbps, Aspect: 852 x 480 (1.775)
Audio: MPEG Audio at 64.0 Kbps, Infos: 2 channels, 44.1 KHz

Its Gonna Hurt - 3 Pointer!  Chase, Devin, and Castro

File size: 624.3 MB

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Mon, 31 Jan 2011 09:34:31 +0200

It's Gonna Hurt - Steven's Ass Is Totaled



It's Gonna Hurt - Steven's Ass Is Totaled

OMG... This guy Steven Waye gets his asshole torn apart by Castro's massive cock. Much to my surprise he enjoyed every second of it. Steven loves sucking big black man dick. I think anyone who loves watching dudes get fucked by big gnarly black cocks will deeply enjoy this episode of It's Gonna Hurt. Cum watch Steven get a hot cum bath. Enjoy, you sick fuckers!

Length: 375 MiB Duration: 37mn 36s 738ms
Video: WMV2 at 1 200 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Steven's Ass Is Totaled

File size: 374.6 MB

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Sun, 30 Jan 2011 15:26:36 +0200

It's Gonna Hurt - Hanz Is Hurtin!!!



It's Gonna Hurt - Hanz Is Hurtin!!!

If you're reading this... most likely you love watching little tight assholes get ripped open by big black cock, so you are in the right place! Today we brought in this little euro dude named Hanz gets who his guts wrenched by Castro's big black cock. I will say, this little fucker took it like a champ and then caught a nice warm load on his chin! Happy Humping!

Length: 349 MiB Duration: 36mn 29s 859ms
Video: WMV2 at 1 147 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Hanz Is Hurtin!!!

File size: 349.1 MB

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Tue, 18 Jan 2011 12:46:11 +0200

It's Gonna Hurt - AJ Plays the Pain Game



It's Gonna Hurt - AJ Plays the Pain Game

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!

Length: 774 MiB Duration: 37mn 47s 951ms
Video: MPEG-4 Visual at 2 722 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: MPEG Audio at 128 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - AJ Plays the Pain Game

File size: 774.1 MB

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Sun, 19 Dec 2010 08:56:09 +0200

It's Gonna Hurt - Jared is a Quitter



It's Gonna Hurt - Jared is a Quitter

So we got a new It's Gonna Hurt update. This guy Jared came to test his will by taking a massive size cock up his poop chute! Unfortunately for Jared he will be shitting weird for the rest of his life. Castro literally gutted this poor man's insides. Come all who dare to test Castro's big black dick up their ass!

Length: 313 MiB Duration: 30mn 3s 80ms
Video: WMV2 at 1 261 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Jared is a Quitter

File size: 312.9 MB

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Sat, 11 Dec 2010 15:55:37 +0200

It's Gonna Hurt - Hot Nuts Pierced!



It's Gonna Hurt - Hot Nuts Pierced!

Me and the big homie Castro Supreme meet up with this tall slender hottie at the beach. Lance is tall but I'm sure Castro can knock him down to size. We all know size doesn't matter. Castro invites on all takers that want to have his boomerang cock shoved up their man cave. That's exactly what happens once back at the condo. Castro whipped his cock out and sure enough Lance got on his knees and sucked the fuck out of the cock. Castro was turned on the minute Lance clamped his plump lips on the dick head. Things got even more exciting for Castro once he saw Lance had piercings along his nut sack. After that, it was on. There was a lot of fucking and a lot of legs being thrown in the air. In result, a massive pounding for Lance. Poor thing. It's Gonna Hurt!

Length: 518 MiB Duration: 39mn 44s 911ms
Video: WMV2 at 1 614 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Hot Nuts Pierced!

File size: 518.4 MB

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Fri, 03 Dec 2010 13:03:47 +0200

It's Gonna Hurt - Super Slam!



It's Gonna Hurt - Super Slam!

Super Slam!
Hey people... We got another one for ya! His name is Adam and it's gonna hurt. Adam was all excited to get his asshole reamed until the time came. Then Adam was a screamer begging for Castro to take his giant cock out of his asshole but Castro wasn't havin any of that noise. So this guy got his ass swelled up! Cum watch this guy Adam get his shit pushed in!

Length: 535 MiB Duration: 38mn 51s 971ms
Video: WMV2 at 1 712 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Super Slam!

File size: 535.1 MB

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Mon, 29 Nov 2010 20:20:58 +0200

It's Gonna Hurt - Gabriel's Butthole Ride!



It's Gonna Hurt - Gabriel's Butthole Ride!

Hey y'all... Today we picked up this guy Gabriel who was dying to get Castro's large member inside of him. Gabriel had no problem sucking on Castro's big Tootsie Roll but when it came down to taking it up his ass it got a little tight! Kinda like when you try to stuff a baseball bat in a slot machine -- it just doesn't work! Enjoy!!

Length: 451 MiB Duration: 35mn 24s 814ms
Video: WMV2 at 1 574 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Gabriel's Butthole Ride!

File size: 451.3 MB

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Tue, 16 Nov 2010 08:38:09 +0200

ItsGonnaHurt - Kurt Wild - The Average Joe Meets The Real Pro



ItsGonnaHurt - Kurt Wild - The Average Joe Meets The Real 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.

Length: 570 MiB Duration: 1h 39mn 13s 0ms
Video: VP6 at 699 Kbps, Aspect: 852 x 480 (1.775)
Audio: MPEG Audio at 64.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - Kurt Wild - The Average Joe Meets The Real Pro

File size: 570.5 MB

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Tue, 16 Nov 2010 08:38:09 +0200

ItsGonnaHurt - Giovanni - The Italian Meets The Sausage



ItsGonnaHurt - Giovanni - The Italian Meets The Sausage

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

Length: 642 MiB Duration: 1h 51mn 36s 0ms
Video: VP6 at 699 Kbps, Aspect: 852 x 480 (1.775)
Audio: MPEG Audio at 64.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - Giovanni - The Italian Meets The Sausage

File size: 641.7 MB

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Tue, 16 Nov 2010 08:38:09 +0200

ItsGonnaHurt - Kirk Cummings - The Castro vs the Stripper



ItsGonnaHurt - Kirk Cummings - The Castro vs the Stripper

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

Length: 556 MiB Duration: 1h 36mn 46s 0ms
Video: VP6 at 699 Kbps, Aspect: 852 x 480 (1.775)
Audio: MPEG Audio at 64.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - Kirk Cummings - The Castro vs the Stripper


File size: 556.4 MB

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Tue, 16 Nov 2010 08:38:08 +0200

ItsGonnaHurt - Danny Boy



ItsGonnaHurt - Danny Boy

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 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!!!

Length: 458 MiB Duration: 1h 19mn 43s 0ms
Video: VP6 at 699 Kbps, Aspect: 852 x 480 (1.775)
Audio: MPEG Audio at 64.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - Danny Boy

File size: 458.3 MB

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Tue, 16 Nov 2010 08:38:07 +0200

ItsGonnaHurt - Brian



ItsGonnaHurt - Brian

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!!!

Length: 662 MiB Duration: 1h 55mn 4s 0ms
Video: VP6 at 699 Kbps, Aspect: 852 x 480 (1.775)
Audio: MPEG Audio at 64.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - Brian

File size: 661.6 MB

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Sat, 13 Nov 2010 07:24:47 +0200

It's Gonna Hurt - Wade Plays the Pain Game



It's Gonna Hurt - Wade Plays the Pain Game

Greetings you sick fuckers! Today we brought in this guy Wade. He is an older businessman with a big cock craving. I really think you will all love how he says "it won't be a big deal" to take Castro's Mammoth-sized cock up his ass. I will have to be short by saying "it was!" And he nearly started crying! Fucking />
Length: 341 MiB Duration: 28mn 27s 984ms
Video: WMV2 at 1 472 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Wade Plays the Pain Game

File size: 341.0 MB

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Sat, 13 Nov 2010 07:24:47 +0200

It's Gonna Hurt - Butthole Smash!



It's Gonna Hurt - Butthole Smash!

Hey people. This Tuesday's It's Gonna Hurt update is great! We brought in this guy Bryan to get his face and ass smashed in by Castro's obscenely large dick. Unlike most updates, this guy could barely finish. Bryan was in so much PAIN it was kinda funny. I really felt bad for this one but like the sign said: "It's Gonna Hurt!" Enjoy, you sick fucks!

Length: 351 MiB Duration: 33mn 47s 245ms
Video: WMV2 at 1 259 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Butthole Smash!

File size: 351.1 MB

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Tue, 02 Nov 2010 08:24:55 +0200

It's Gonna Hurt - Goal In The Hole!



It's Gonna Hurt - Goal In The Hole!

Castro Supreme is back on the prowl! Looking for his next victim. Castro was in the mood for an athlete's booty hole. Someone that has an amazing physical endurance. Castro's basically looking for ass that can take his monster meat. Luckily for Castro he found this cute little white boy by the name of James. Playing soccer all by himself. Castro preyed on him as he ran across the field like a gazelle. Kicking the soccer-ball in the goal. That just excited Castro even more. He just had to have that sweet piece of ass. All that came to his mind was putting his cock in James' goal. More like his butt-hole. We all know Castro gets what he wants. Once back at the house. It was game over! You better believe It's Gonna Hurt. Castro flipped this boy in every position imaginable. Slaughtering his pretty little bum-hole. Until Castro dropped a huge load of nuts on his face. Amazing I tell you! Cum check this crazy shit out. Peace!

Length: 347 MiB Duration: 38mn 3s 83ms
Video: AVC at 1 198 Kbps, Aspect: 720 x 404 (1.782) at 29.970 fps
Audio: AAC at 69.6 Kbps, Infos: 2 channels, 44.1 KHz

It's Gonna Hurt - Goal In The Hole!


File size: 346.9 MB

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Mon, 25 Oct 2010 13:21:53 +0300

It's Gonna Hurt - Tight Little Fucker!



It's Gonna Hurt - Tight Little Fucker!

Hey people... We have got another gut wrenching episode of of It's gonna Hurt. Today's victims name is Val and Castro literally nails his tight little asshole to the wall. It was a good day for Castro and not so good for Val or at least it seemed. In the end Val came out smiling which was a real shocker cause for a minute I thought I was gonna have call the ambulapse. LOL... Its always gonna hurt with Castro's Supreme! Watch and Love it!

Length: 345 MiB Duration: 36mn 7s 694ms
Video: WMV2 at 1 145 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - Tight Little Fucker!

File size: 344.8 MB

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Tue, 12 Oct 2010 08:02:51 +0300

It's Gonna Hurt - One Large Deposit



It's Gonna Hurt - One Large Deposit

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 Castro'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!

Length: 464 MiB Duration: 46mn 40s 889ms
Video: WMV2 at 1 199 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - One Large Deposit

File size: 464.3 MB

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Tue, 12 Oct 2010 08:02:50 +0300

It's Gonna Hurt - A Dream Cum True....



It's Gonna Hurt - A Dream Cum True....

Derek's always dreamed of meeting Castro Supreme one day. Well, Derek's dream has finally come true. We met Derek at his job so he can meet Castro Supreme in person. To his amazement, Castro is what he's always imagined. A buff black guy with a very large cock. Derek was in such a hurry to see what Castro was packing. All he wanted to do was get in his jeans. So Castro whipped his large penis out. Sure enough without hesitation. Derek wrapped his juicy lips around Castro's massive meat, sucking away. After giving Derek a taste of Castro's monster cock, we headed back home. Once back at the house it was lights out for Derek. Castro beat the hell out of Derek's tight little bum-hole. Fucking him in multiple positions. Man was Derek in pain. He tried to run, but Castro had a tight grip on his waist. All I have to say is: It's Gonna Hurt!

Length: 490 MiB Duration: 38mn 45s 322ms
Video: WMV2 at 1 559 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz

It's Gonna Hurt - A Dream Cum True....

File size: 489.5 MB

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Wed, 06 Oct 2010 07:40:41 +0300

ItsGonnaHurt - A Ride On The Gravy Train



ItsGonnaHurt - A Ride On The Gravy Train

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!

Length: 422 MiB Duration: 37mn 36s 252ms
Video: VP6 at 1 499 Kbps, Aspect: 852 x 480 (1.775) at 29.970 fps
Audio: MPEG Audio at 64.0 Kbps, Infos: 2 channels, 44.1 KHz

ItsGonnaHurt - A Ride On The Gravy Train

File size: 421.9 MB

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Thu, 16 Sep 2010 07:33:36 +0300

It's Gonna Hurt - Robbie Plays The Pain Game



It's Gonna Hurt - Robbie Plays The Pain Game

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!
It's Gonna Hurt - Robbie Plays The Pain Game
Length: 393 MiB Duration: 32mn 34s 783ms
Video: WMV2 at 1 481 Kbps, Aspect: 852 x 480 (1.775) at 23.976 fps
Audio: WMA at 128 Kbps, Infos: 2 channels, 48.0 KHz
It's Gonna Hurt - Robbie Plays The Pain Game

File size: 392.7 MB

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Wed, 09 Jun 2010 09:56:18 +0300

It's Gonna Hurt - Tucker the Fucker!



It's Gonna Hurt - Tucker the Fucker!

It's Gonna Hurt - Tucker the Fucker!

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

Video: Flash Video 4 864x480 [Video]
Audio: MPEG Audio Layer 3 44100Hz stereo 64kbps [Audio]

It's Gonna Hurt - Tucker the Fucker!

File size: 534.9 MB

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Wed, 09 Jun 2010 09:46:24 +0300

It's Gonna Hurt - Jaden Loves Black Dick!



It's Gonna Hurt - Jaden Loves Black Dick!


It's Gonna Hurt - Jaden Loves Black Dick!

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 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 ass slaying of Castro Supreme!

Video: Flash Video 4 864x480 [Video]
Audio: MPEG Audio Layer 3 44100Hz stereo 64kbps [Audio]

It's Gonna Hurt - Jaden Loves Black Dick!

File size: 380.4 MB

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Fri, 28 May 2010 10:51:40 +0300

It's Gonna Hurt - Pain+Stitches= Supreme



It's Gonna Hurt - Pain+Stitches= Supreme

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

It's Gonna Hurt - Pain+Stitches= Supreme

It's Gonna Hurt - Pain+Stitches= Supreme

Video: Flash Video 4 864x480 [Video]
Audio: MPEG Audio Layer 3 44100Hz stereo 64kbps [Audio]

It's Gonna Hurt - Pain+Stitches= Supreme

File size: 541.4 MB

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Thu, 27 May 2010 08:16:18 +0300

It's Gonna Hurt - Training Day



It's Gonna Hurt - Training Day


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!

Video: Flash Video 4 864x480 [Video]
Audio: MPEG Audio Layer 3 44100Hz stereo 64kbps [Audio]

It's Gonna Hurt - Training Day

File size: 393.1 MB

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Sat, 22 May 2010 01:53:30 +0300

It's Gonna Hurt - Lance Like's Big Dick



It's Gonna Hurt - Lance Like's Big Dick

It's Gonna Hurt - Lance Like's Big Dick
It's Gonna Hurt - Lance Like's Big Dick

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!

Video: Flash Video 4 864x480 [Video]
Audio: MPEG Audio Layer 3 44100Hz stereo 64kbps [Audio]

It's Gonna Hurt - Lance Like's Big Dick

File size: 516.3 MB

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Sat, 22 May 2010 01:48:04 +0300

It's Gonna Hurt - That had to of hurt....



It's Gonna Hurt - That had to of hurt....


It's Gonna Hurt - That had to of hurt....
It's Gonna Hurt - That had to of hurt....
What up all you giant dick loving 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 Supreme! Come watch some ass get ripped!

Video: Flash Video 4 864x480 [Video]
Audio: MPEG Audio Layer 3 44100Hz stereo 64kbps [Audio]

It's Gonna Hurt - That had to of hurt....

File size: 467.6 MB

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Thu, 20 May 2010 08:44:42 +0300

It's Gonna Hurt - Killin That Ass!



It's Gonna Hurt - Killin That Ass!


It's Gonna Hurt - Killin That Ass!
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 inch 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!

Video: Flash Video 4 864x480 [Video]
Audio: MPEG Audio Layer 3 44100Hz stereo 64kbps [Audio]

It's Gonna Hurt - Killin That Ass!

File size: 252.7 MB

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