The Pit - Hot pain slut, Dakota Wolfe stands in the pit as he’s bound with leather belts before Van gets his cock hard. Heavy clamps are tightly screwed onto Dakota’s nipples as they’re tormented with the sting of the cat-o-nine tails whipping against his tender skin. Dakota pushes through the pain of his nipples before enduring an extreme flogging. - The Chair - Our pain slut moves onto the next challenge as he’s bound tightly in the chair, with medical clamps pinching all over his torso and tied off to the wall. Dakota endures some CBT as electricity torments his aching balls. Each clamp is removed from his tender skin, Dakota screaming at the top of his lungs each time the clamped skin gets whipped with the crop. - The Gimp Station - Finally, Dakota moves onto his third and final challenge. He’s bent over, with his hands strung up behind him as his ass endures a heavy caning. The gimp shoves his hard cock down the boy’s throat before jamming it up his ass for a rough fuck. As reward for successfully completing his three challenges, Dakota finally blows his hot load all over the floor.