Delinquency among teenage American boys is a major problem, but sending them to prison is just too expensive. So many young offenders are getting a taste of "The Pen" though our special program. Jacob is barely 18, but he's a tough kid, determined to take a beating and show no fear, even when we show him the whips we are about to use on him and ask if a man has ever fucked him. Next week: He'll beg.

Jacob absorbed his whipping with surprising manliness. He even survived having a cock shoved down his throat. But nothing prepared him for having a rigid, beer-can sized dildo rammed into his virgin asshole. "It's too big!" the boy screams as he's fucked for the first time. When it's finally over, he's left to jerk off his teenage cock, spewing a massive load of cum. Next week: Jared cums.

Jacob is terrified of Jared. He is even more terrified of what will happen to him if Jared's boss finds out he jerked off without permission, so he's agreed to get face-fucked once again. Jared is much rougher this time, grabbing the boy's hair and shoving his dick deep into Jacob's throat. He busts his load all over Jacob's chest, then makes the boy lick his dick clean. Next week: Punished.

After spending the night chained in his cell, Jacob is hauled out kicking and screaming. He knows his punishment has just begun, but he's still shocked when he sees what looks like an old medieval rack. He screams as Jared chains him to the device. After just a few turns of the screw, his shoulders and back feel like they will tear apart, but Jared keeps tightening the chains. Next week: Shaved clean.

"Learned your lesson yet, boy?" the man asks. "Yes, sir!" Jacob replies, still chained to the rack. "I don't think so," the man smirks, cranking the boy tight again. Then he shaves Jacob's armpits and sticks a spray bottle under his nose. Alcohol! Jacob can't believe the pain as the alcohol mist settles on his raw pits. Then the man beats his burning skin with a crop as he trashes and screams. Next week: Bull whipped.

Jacob sits on the dungeon floor, head on his knees, shaking with fear, his body scarred from earlier whippings, when Jared enters. He attaches Jacob's wrists to a winch, then hauls him up on his feet. Jacob knows he will suffer, but nothing could prepare him for this whip, a single strand of weaved leather that cuts like a knife. Jared is a machine, his rhythm unbroken by his victim's screams and pleas for mercy. Next week: Forced to cum, again.

After a few more lashes, Jared lowers his boyish victim to the ground. Jacob cries out in pain as he is rolled over onto his lacerated back. "I want you cum on command, boy!" the man barks. "Show us some cum and we'll stop hurting you." Jacob eagerly obeys, working his twink cock until he pumps out a huge load of jizz. The man just laughs. "Jared! Bring in the fuck cross!" Jacob's suffering is about to get much worse. Next week: Fuck cross.

Jacob's been whipped, beaten and racked, but nothing could prepare him for the fuck cross. He arches his back and hangs free, feeling the dildo poking his back, beckoning his asshole. After an hour or so his muscles scream in agony and he knows he must sit on the thing or dislocate a shoulder. Now the dance begins. He must choose between the agony of the cross or fucking his own ass. Next week: Army Ranger.