Billy and Max' catching up was cut short by the door buzz and two trustees walking in. The boys crowded around and found out what was going on. The warden apparently had some guests, and wanted to have a rodeo. None of the boys knew what this meant, but it couldn't be good. The trustees didn't know either, but they had been told to deplug, shit and shower half the boys. Conrad and another boy who was high cuffed were told they were the suckboys for the day, both wondering how that could be since there was only one sucktable.
Billy was immediately worried about Max, he wouldn't get any time to rest. "Dude," he whispered to Max, "this could be bad, but stick with me, ok?" The trustees motioned for about half the boys to move to one side. As they were right in the middle, Eric was moved with one group, and Billy and Max with the other. They herded the other group including Eric over toward the shower. First, each boy had to bend over near the grate. They all watched with mild horror as the trustee would unlock the plug chain, pull it free, and then fairly quickly wrench the plug out of the poor boy's ass. Some gave a little yelp, and others were silent.
For most boys, who had been plugged for more than 18 hours, a fair amount of shit came out with the plug. The large round plugs created such a large space in the rectum, that all the crap backed up their butts rushed down to fill it. With their buttholes sore and stretched from the plug, it was impossible for most to stop the gurgling crud, and it plopped out irregularly from their holes as the bent forward over the grating. Max was horrified at what was going on. Hey couldn't believe the size of the black plugs that were being yanked out of these boys' asses.
Billy watched as Eric bent over and had his plug taken. It came out with an audible pop and a thick chunk of poo fell out right after it, followed by a sludgy stream of loose shit. Billy had a pang of pity for Eric, or maybe it was self pity. That magical hole between Eric's legs that had given Billy such pleasure only 18 hours ago was now a bright red, shitty, stretched out mess. True, Eric's hole had been a lot looser than your average 17 year old jock's would be, but it still was tight enough to give Billy a mind blowing orgasm that had brought them closer together. He wondered how long it would be before Eric's ass chute tightened up again. It should be soon, Eric had been in punishment for at least a week, so he had been plugged before. And this time it came out after only 18 hours, rather than 48 or more.
As Eric and the others sat on the butt washer and went back over to the grate to spill the very dirty water cleaning out all the backup from the plug, Billy took Max into his and Eric's cell to try to give him a pep talk. "Dude, I'd love to catch up and laugh about old times, but I think you can see now this is serious. When I got in here Thursday, Eric and some other guys helped me. It didn't make what happened to me any less awful. They are going to fuck you and fuck you bad. They'll give you an especially rough time too cause you're new meat, just like I was. Are you a virgin in your butt?"
"What!?" Max exclaimed, "of course."
"Just wondering, man, don't get mad. I had never had anything up there until the other day, I was just thinking it would be easier if you did."
"Well," Max said looking away, "that wasn't quite true. My cousin and I cornholed a few times back when we were kids, like 13 when we moved."
"Well that's a start, but it was a long time ago, and your cousin's dick probably wasn't half as big as what these guards are packin," Billy said thinking. "You'll have to sit on the steel dick that washes out your butt, but that only goes in a few inches, and won't do the trick. Do you want me to try to loosen you up?"
Max thought about it, it just seemed so wrong. He'd only been in here an hour or two and now his old best friend was talking about working on his ass to prepare him for getting fucked by a bunch of jail guards, this couldn't be happening. "Do you think it will help?" Max asked Billy.
"I am not sure," Billy said, "these guys are really out to hurt you. But anything should help a little. They love to find a virgin they can bust open like they did me. I actually bled out my asshole. If we can get you just a little bit loose up in there, it may make a bit of difference. It will be tough with these damn cuffs, but I think I know what to do."
Billy still sat on the edge of the bed, and had Max stand in front of him facing away. He had him bend forward at the waist, exposing his narrow ass valley. Max never really did have a butt. He was one of those skinny kids whose legs look like they are attached directly to his torso. Remembering what Eric had done for him his first day in punishment, Billy slowly stuck out his tongue and leaned into Max' crevice. He could see the area in the center of the crack where his asshole should be, but there was only what looked like a little slit. There were no asslips or wrinkles to speak of. Billy poked at it with his tongue, and a light moan escaped Max. Billy pushed a little harder and the little slit winked, revealing a smooth little hole. Billy tried to make as much saliva as he could and get the area nice and wet like Eric had done. Pushing as hard as he could, he was only able to get the very tip of his tongue in. Remembering how Eric had gotten several inches of tongue into him, he had Max part his cheeks as best he could, and was able to sink a little bit more in. Max' hole was so tight though, that each time he withdrew his tongue it was just as tight as before and just as hard to push in. Billy knew what he had to do.
"There's only one thing that's going to help you man. You gotta take a big dick before those guards rape you. Maybe then it won't hurt so bad and you won't bleed." Max, totally freaked out, nevertheless understood that his friend was only trying to help him. Billy figured the best way was to have Max sit on his dick. The only problem was that he was completely soft. He didn't know if it was because he was naked in this situation with his best friend, or because of the pain coming from the huge plug and the shit on top of it. "Dude," he said to Max, "this plug is killing me. Can you try to get me hard? Get it nice and wet too." The last part told Max exactly what he needed to do. He got on his knees in front of his buddy, and started licking and sucking on his big soft dick. Seeing Max' cute familiar face between his thighs with his dick sticking into it immediately got Billy going, and the eight and a half inch flesh tube sprung to life. Coaching Max to get it nice and wet, Billy's dick had saliva running all over it.
Billy, although wishing the bj could continue, knew there were more important things at hand. He stood Max up, and turned him around, bending him over. He spit right at his hole a few times till he ran out of spit, then told Max to sit down slowly. The angle of his dick was troublesome, but as Max slowly lowered, Billy was able to maneuver his cock so that Max' hole made contact with the soft pink head still half covered by skin even though Billy was raging hard. There was a lot of force between Billy's dick and Max' hole. Billy was afraid his cock would snap. He told Max to push like he was shitting and to wiggle around. With a lurch, the first three or so inches of Billy's dick slid into Max' butthole. Max was obviously startled, but kept his downward pressure. Inch by inch, all of Billy's meat was sliding into Max. The last inch or two were the hardest, and required Max bouncing a little until the full length of Billy's dick busted through some tight spot or inner sphincter and he bottomed out in his buddy.
Billy let Max work himself up and down his dick for about 20 minutes. He could feel him loosening up, and the resistance growing less. It probably had to do with the constant stream of pre that Billy's dick made when he was this horny. Billy decided that Max needed some more vigorous stretching, so keeping inside of him he kicked his legs up onto the bed keeping Max with him. Max was on top, so Billy rolled them onto their side, with Max facing the wall. He sort of kicked Max' top leg up into the air, Max understanding he needed to keep it there. Max' waist chain wasn't as tight as the other boys, and Billy was able to grab onto one side of it. By putting his chin over the slightly shorter boy's shoulder, Billy was able to get him into a pretty good hold. Billy started thrusting powerfully into Max. With his strong stomach and abs, he was able to make his dick travel hard about six inches in and out of Max' increasingly loose hoop. After a while, Billy maneuvered Max onto his belly, legs together. The boys small buttocks, and very open asscrack let Billy re-penetrate him in this fashion. Using his body weight now, Billy could lever on his knees, on the outsides of Max' knees, and get full hard penetration.
Max was breathing hard, apparently feeling the full force of his first man-sized cock. Whatever he and his cousin had done, Billy thought, it was nothing like in here. He wondered about this cousin. Had he met him? Wouldn't it have been strange to know Max was doing that the last summer they were neighbors. He wondered how it had begun. But now it was he who was railing the little ass beneath him. How big was Max' cock that summer they were 13? He couldn't remember, but it was pretty small. His cousin's probably too. Nothing like the 8.5 inch torpedo he was ramming into Max now, he thought with a little pride, before remembering the reason he was doing this. Billy was getting close. The pain from the plug was outmatched by the tight ass his cock was embedded in, and the guilty pleasure of deflowering his former best friend. With a few final thrusts, Billy tensed up and blew seven or eight jets of cum full depth inside the kid.
He pulled out and saw his red raw dick covered in brown streaks and a few little clumps of shit. Max probably hadn't gotten to use the toilet in a long time. He wasn't planning on making Max clean him up so he asked him. "Hey buddy, you ok? I was just going to ask you, and you don't have to do it if you don't want. The guards here always make you suck them off after the fuck you. It can be pretty nasty, especially if they want to cum again and ram the thing down your throat. You only got the head in before, do you want to practice, or just take it as it comes?" Max looked at his crap on his buddy's dick. He knew he was in a world of shit, this last indignity could hurt any, especially if it helped later on. Max got back on his knees in front of his buddy Billy, and took the stinking penis cautiously into his mouth. "You gotta open up your throat. It feels like your suffocating at first, just try to relax. Remember, these COs are just going to shove it down there." Max pushed more aggressively onto the re-stiffened dick. Billy felt his head hit the back of Max' mouth by the throat tube and Max choke a little. He gave words of encouragement as Max impaled his throat with the big dick log. Pretty soon Billy could feel his nutsac pressed against the boy's chin. He had done it. Max tried a few more times, and was surprisingly able to smoothly slide the entire dick into his throat, like Eric did.
Max got off of Billy's dick without making him cum again, slightly disappointing Billy. "Well stud, you may be ready after all," he said to Max. "We better get back out there." He was surprised that Eric hadn't come back to the cell, but he probably had some idea of what was going on. They walked out into the day room and went to where some of the guys were. Eric forgot he had a stiff dick, but boners weren't too uncommon in punishment, especially when the guys were plugged. Billy looked around. The other high-cuffed boy was strapped down to the suck table on his back as Per had been. It must've been uncomfortable on the hard table since the plug chain coming up from between his legs to his waist chain confirmed he was still plugged. Billy looked over at the other wall where he saw Conrad sitting on a very low stool with his legs splayed out straight in front of him. He was secured tightly to the wall by a chest strap under his arms, with a loose chain around his neck, over his regular neckchain. It looked awful, and Conrad still sported the tell-tale plug chain meaning he was supporting his entire weight on the plug sitting on that foot-high stool. The trustees were finishing showering the last boy. Just as Billy was about to walk over to Conrad, the trustee who had been toweling boys walk over, hiked his sweats and panties down, and just shoved his junk into Conrad's face.
The trustee's dick didn't look too enormous, but he facefucked Conrad pretty violently. The boys could hear his head hitting against the wall from the force of the boy's thrusts. Even if his cock was only eight inches or less, that still meant a portion was in Conrad's throat, and his throat tube was getting pretty roughed up. After just five minutes or so, the trustee grunted and dumped his load in Conrad's mouth. The last two shots he pulled out for, shooting one right in Conrad's eye, the other on his forehead. Once the trusted shoved his junk back into his panties and walked off, Billy and Max went over to Conrad. "You ok man?" Billy asked. Conrad nodded and closed his eyes, probably trying to get the nut juice out. Billy leaned over and licked the cum out of his eye, and then the gob running down his forehead towards his other eye. "Thanks," Conrad said looking up with a smile.