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It's Gonna Hurt: Where giant dicks get stuffed into tight assholes...and its gonna hurt so good! Guys love having things fill their asses, and every guy thinks he can take the largest object inside of them. Visit It's Gonna Hurt!

It's Gonna Hurt! Video Collection

Fairy Tales Come True

Fairy Tales Come True Castro Supreme, DJ Mann by: It's Gonna Hurt! Oct 11, 2019 83%

Gettin Hooked

Gettin Hooked by: It's Gonna Hurt! Oct 11, 2019 78%

Scared Little Logan

Scared Little Logan Castro Supreme, Logan White by: It's Gonna Hurt! Oct 11, 2019 92%

Twenty Plus Inches of Hell!

Twenty Plus Inches of Hell! Castro Supreme, Izzy James, Jacob Durham by: It's Gonna Hurt! Oct 11, 2019 93%

Double Dick Destruction

Double Dick Destruction Castro Supreme, Izzy James, Brycen Cox by: It's Gonna Hurt! Oct 11, 2019 71%

My Friends Are Going To Love Me!

My Friends Are Going To Love Me! Castro Supreme by: It's Gonna Hurt! Oct 10, 2019 71%

Wake Up Call

Wake Up Call Taylor Reign, Izzy James by: It's Gonna Hurt! Oct 10, 2019 98%