Billy's stomach was grossly distended with piss. By the time the tenth or twelfth boy went, Billy felt like he would burst, and had to piss badly himself. One of the COs began lightly and then not so lightly punching him in his swollen belly, causing Billy, whose asshole was still violently winking and twitching, to erupt with a strong stream of piss. Because he was still half hard, the flow was restricted and fast and his cock was at a slight up angle so the stream hit the boy currently pissing in his mouth full on the chest. As the stream subsided, the flow went into Billy's hair and eyes and down his chest until the last drops just lazily gurgled out on his stomach. The last boy to piss in Billy was of course Evan. His cock still standing at least 11 inches in from of him, the CO undid Billy's head strap and turned his head to the side, grabbing Evan's dick and stuffing it into the opening of the mouth dildo. Evan tried to touch Billy, but because of the length of his cock, he was not able to move his hand enough with the waist chain to reach him. Billy was looking up at him, and Evan mouthed the words I love you.
When Evan was done pissing after a long time due to his raging erection, the COs unhooked Billy from the table and forced him up against the wall. Several COs forced him to bend over, kicking his legs apart. They examined his destroyed hole and made lewd comments about 'won't forget that soon,' 'that asshole will never look the same again,' 'how could your boyfriend do THAT to you,' and so on. After having their fun, including shoving a baton a foot into Billy's ass without it meeting any resistance, the COs tired of the game and uncuffed Billy's hands and waist chain.
A CO threw a pile of clothes onto the piss soaked floor by the table Billy had been on, and the youth, soaking with his own and other boys' piss, dressed himself in the pink panties, white t-shirt, sweats and slippers. The t-shirt immediately soaked through. The guards bent Billy over the table, smacked his ass a few times, and roughly cuffed him for transport to his wing. As Billy was led out of the punishment block, Evan had to fight the urge to cry. What would he do in here without Billy?
Billy was quickly marched through the halls. He had never seen any part of the jail apart from the intake room and punishment, since he had been unconscious when carried into punishment. The fast pace was tough for Billy to keep up. The sandals were ill-fitting and Billy hadn't worn anything on his feet in a week. His legs were weak and sore from being trussed up for so long, and his asshole gave him agony with each step as his destroyed ass ring was pulled with each step and cum still leaked slowly out of his cavity. Billy could feel the panties sticking to parts of his asshole that were usually well inside his body. He shuddered to think what his ass looked like, and there would be nobody at his new wing to check it for him. Finally they entered a large room with table and chairs, much larger than the day room in punishment. Surrounding the main room on two levels were rows of cells. There were boys all over.
Billy was led up the stairs and to a cell. The COs pushed him inside and bent him over the small sink. One of them roughly reached his hand down the back of Billy sweats and shoved four fingers into the gaping hole, finding no resistance. "Goddam, that pussy is destroyed," he said, bring the fingers out and wiping them on Billy's back before thinking better of it and sticking them in Billy's mouth. The COs uncuffed Billy and left without a word. Billy couldn't believe his hands were free. He felt his sore wrists, numb from days of his arms hanging from those cuffs. He squeezed up each arm feeling his muscles for the first time in a week. He swung them around and play-punched at the wall. He actually smiled.
Just then he heard someone call his name, and Conrad appeared at the door. "You're finally out!" Conrad said with a huge smile. Billy hadn't seen Conrad in three days, but it felt like a year. They hugged, the first time Billy had ever been able to do that with a boy. Billy all of a sudden needed a piss bad. "Can you piss me?" he asked Conrad.
"You dumbass!" Conrad shot back, "you're not cuffed anymore!"
Billy laughed. "Ok then funny guy, where's the grate?"
Conrad laughed again. "That's right, you've never been in gen pop. Well it sure ain't punishment. There's some toilets downstairs, but most boys just piss in the sinks." Billy stepped to the sink. He pulled down his sweats and hefted his big dick over the top of the panties. It seemed like forever since he'd held his own dick. He skinned back and started a big stream.
He started telling Conrad about that afternoon. "Dude you wouldn't believe what they did for my going away present. First, every boy but me had to wank Evan off and make him cum or else get punished. Then they gave Evan all this Viagra so his dick got a foot long and they made him dry fuck me. It took him like two hours to cum, my ass is on fire. Then they made them all piss in my mouth, it was awful." Conrad gave his condolences and insisted on seeing Billy's ass.
Conrad sat on the bed and made Billy drop trou and bend over in front of him. What greeted him shocked Conrad, even though he'd seen some awful stuff in punishment. Billy's ass was bright red and just hung open. He could see way inside the boy until it got too dark to see the swollen anal lining. The asshole in front of him was still opening and closing slowly. When fully open it was hanging probably 3 inches open, in a perfect circle. It was like a huge invisible dick was inside of Billy. Conrad wet the corner of the bed sheet in the sink and dabbed it on Billy's exposed ass lining. It felt soothing to Billy, and soon was replaced by Conrad's tongue trying to put some salve on the pooched out hole. He could feel Billy's sphincter muscle, stretched to many times its natural size, hanging loosely inside the stretched out skin around Billy's hole, like a too-big rubber band. Conrad felt bad for Billy, and was trying to help him heal like the boys did back in punishment. He knew he wouldn't be able to fix this ass, that would just take time. He could however make Billy feel better.
He told Billy to stand by the door and got on his knees in front of him. Billy felt Conrad grab his dick and stroke it a few times until the blood rushed into it. Billy may have been injured, but he was also a teen boy exposed to a day of fucking with only one cum, so he quickly got hard. Conrad took the big dick into his mouth and toyed with the head and skin. A new sensation came to Billy, who had only ever been sucked by boys who were cuffed. One of Conrad's hands was stroking the base of his shaft, while the other was tugging on and massaging his big full balls. Billy was in bliss, momentarily forgetting about his earlier torture. It was awful that they'd made Evan do that to him, but he could tell that Evan never wanted to hurt him, that they were still friends and more. Plus, the end of that fuck was like nothing Billy had ever imagined was even possible. Total surrender to that huge cock. He felt like all of Evan's being was inside his ass. He came back to his senses. His cock was all the way into Conrad, who was massaging his balls below his chin. Billy was so overcome from remembering the way Evan's cock felt a foot inside him, he bucked and flooded Conrad's throat. Conrad pulled back to savor the last six shots on his tongue, swallowed, and cleaned up Billy's dick.