The Orphanage Boys Chapter 39
by Chadlad

copyright 2010 by Chadlad, all rights reserved
[email protected]

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This story is intended for ADULTS ONLY It contains explicit depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Chapter 39: 39th Floor: Challenging Games

Jake and Sam cautiously opened the door to their dorm. The girls who'd stripped and humiliated them had been met at their own dorm door and herded in by stern nuns, putting an end to games of "grabass" and "get his pecker," and "grab his balls" that they'd been playing all the way back. Jake felt trepidation of the most major sort as he did so—he feared that more torment awaited them. The boys had been sent to the dorm early, with no play time after dinner, and he and Sam had been named as the reason. But the lights were on through the shades of the few high windows, so the boys were clearly up. And he and Sam were certainly not dressed for a confrontation—they wearing dresses, for one thing, and shiny black girls' shoes, and knee stockings, and even had panties on under the dresses. Worse yet, their scant hair had been bound with rubber bands out either side of their heads, so that Jake had two brown, short pigtails sticking up like antenna, and Sam had two shocking red but similar pigtails. If he looked as ridiculous as Sam did, he looked ridiculous indeed.

But there was no delaying—a nun was already moving purposefully toward them as they delayed, so Jake took a deep breath and opened the door, ready for the assault he was sure would come when he entered the room and all the boys turned to look at them. He hunched his shoulders, preparing for anything.

And stopped, surprised, just inside the door. No one was looking their direction. None of the boys were sitting on beds talking, or standing around the walls, or moving to and from the toilets. The outer walls were completely deserted. Instead, the boys were gathered in a tight knot in the center of the room, near his and Sam's bunks, all intensely focused on something in the middle of their circle. Or someone. Jake eased the door shut, and he and Sam crept forward cautiously, both driven by curiosity over what was going on. As they got to the back of the crowd of boys, they could hear Pip speaking, in a deliberate, yet taunting voice.

"...and don't try to deny it," he was saying as they eased closer. "You were doing it again. You were touching it under the covers. You think I didn't see? You think I don't have spies everywhere? You were doing it, and you know what the penalty is."


"I... I never!" a high-pitched voice whined from the center of the group. Jake eased forward and looked over the shoulders of the crowd. Tommy, the short, fat boy with the huge butt who bunked next to him and Sam was standing in the tight circle of boys. Jake noticed he was in just boxers, then he realized that all the boys were in boxers, briefs, or faded, worn pajama bottoms in the case of the few boys who had them. The boys must have already been in bed, but risen when whatever incident this was had started. Tommy was flushed to his shoulders and looked frightened, perhaps near crying. Pip was regarding him with a superior smirk, two of henchmen standing over either shoulder.

"You were," Pip said. "You were playing with it. Don't try to deny it, or you'll get punished for lying, too. "

"I'm not lyin'!" Tommy insisted. "I never touch it. Ever! Not even to go...to
number 1!" He looked at Pip pleadingly.
"Really?" Pip said. "Prove it. Take 'em down and show us that your baby nub is soft. If you're
soft and I'm wrong, we'll all go back to bed. But if your hard, and we all know
you will be, you get the whole treatment. I punish you, and then you get reported to Sister Grace. And you lose your undies, of course. Again."
Tommy looked almost ready to cry, his fat cheeks quivering. "It's not fair," he
whined. "I wasn't playing with it. I was just scratching my stomach—above it! I never touched it!"
"Ha! So you admit you had your hand down there," Pip retorted. His henchmen looked gleeful.
"No! Not there. Not on my thing. Just my tummy. Scratching. I get itchy," he added nervously.

"Yeah, we know what kind of itches you little boys get," Pip replied. His henchmen chortled. Jake, forgetting about how he was dressed, moved closer, right up to the shoulder of the boy behind him.

"No, I wasn't! Please! They'll put me in a box!" Tommy whined.

"Tough titty," Pip said, making his and several of the other boys guffaw. A hand tapped Jake on the shoulder and he jumped, then realized it was Sam tapping him. Sam had stepped back and had slipped the dress off over his head and dropped it on the floor. He pointed that Jake should do the same, and then started yanking of the shoes and knee socks. Jake stepped back and hurriedly pulled his own dress over his head, then struggled with the shoes. Pip was continuing to stalk his prey, and all eyes were focused on him and the pudgy, unlucky Tommy.

"Drop 'em," Pip ordered. "Prove it to us. Show us your pathetic little stub is limp, and maybe we'll believe you. Maybe."


The fat boy looked down, then up again. "Please," he whined. "Please, you gotta believe me. I never...please!" He looked from one boy to the other. Sam and Jake were down to their girlish panties now. Jake looked at them, considering. Then he slipped them off. Being naked would be embarrassing, but nothing compared to being caught in girls' underwear. Sam nodded and slipped off his own, his small penis dangling as he leaned over and picked up the pile of clothes, then slipped back into the darker corner of the room and dropped them in the hamper. He sidled back up to Jake and they moved back up to look over the shoulders of the back row of boys.

"Boys, help Tommy-boy drop his drawers," he drawled. The two henchmen were on either side of Tommy in an instant, one grabbing his hands and pulling them over his head, the other grapping handfuls of boxer and yanking down. In an instant, they fat boy's bare pubes were exposed, and his infantile genitals. The crowd of boys shifted and crowded in, staring at his crotch. Jake stood on tip toes himself, caught up in the drama.

Tommy's small penis, normally almost hidden in the fat of his crotch, projected like a little prong, curving up slightly, the mushroom head swollen and redder than the thin shaft. His balls were pulled tight and hidden, his scrotum a wrinkled patch under the projecting organ that pulsing slightly, prophesying doom.

"Look, he's got a boner!" a boy shouted excitedly. "Now he's going to get it!" The other boys were silent, some looking on with eager glee, others with concern, or even pity. Tommy squirmed belatedly, as if trying to hide his shame, but he was far too late. His stiff member arched accusingly as he moved, too short to really bob up and down as he wiggled.

"Take him to the glass room. I'll report to Sister Grace and get the self-abuse paddle," Pip said. A struggling, protesting Tommy was dragged toward the punishment area. Pip pushed through the crowd pausing as he spotted Jake and Sam, standing naked in the back of the crowd. "Welcome back, boys," he said with malice dripping from his voice. "Did you have a nice time playing with the girls at your little pajama party? Did each other's hair, I see." He shoved on out. A few of the other boys now noticed Sam and Jake. There some comments about their hair, and their nudity, and the pathetic state of their small, limp genitals, but it didn't last—Tommy, twisting and flailing as he was dragged to the glass room, was too loud not to attract most of the attention in the room.

"Nooooo!" he was wailing. "It's not fair! I didn't play with it! I don't do that any more! Really! Don't paddle me! Please!"


Jake, with some effort and taking quite a bit of hair with it, tugged the rubber bands out of his own hair, then began working on the hair of Sam.

"Ow!" Sam complained.

"Sorry," Jake muttered. "They're hard to get out." He continued to work at the stupid pig tails, and Sam flinched and bit his lip. The rubber band tore loose, taking a good deal of red hair with it. The door on the glass room shut, slightly muffling Tommy's continued protests. Jake finished pulling out the rubber band from the second tuft of Sam's hair and looked for a place to put the hair-filled rubber bands. He finally slipped to the hamper and tossed them in.

"Let's find some underwear so we won't be so out of place," Sam whispered. Jake nodded and they tried to slip quietly to their bunks.

"Hey, look! The new kids are all nakey!" a medium-sized boy chortled. Heads turned to look. Another kid wolf-whistled.

"Hey, squirts! Did you forget your clothes while you playing with the girls?" an older boy taunted. "Wish I could play naked games with the girls."

Sam and Jake lowered their heads and pushed toward their bunks. Slinging open the top of his locker, Jake pawed through his stuff, looking for his spare underpants. There was pair of jeans, a ratty, too-small shirt, some socks, but not underpants. A glance at Sam showed him similarly dismayed. Jake shrugged and pulled out his jeans, lifting one leg and starting to slide it in. Pip breezed through the door just then, carrying what looked like a slightly oversized ping-pong with no padding, just a bare, polished wooden surface. He frowned at the boys as he went by. "You know the rules, runts," he said. "Only night clothes at night. That's undies or pjs, nothing else.

"But we don't have..."Sam said. Pip cut him off.

"Nothing else. If you lose your undies, you sleep raw. Now if you'll excuse me, I have to blister an Onanist's fat behind. Make sure you watch, so you'll know what to expect when I catch you two at it. 'Cause I will catch you at it." He moved on to the glass room. Feeling conspicuous, Jake and Sam sat on Jake's bed. Around the room, boys sat one beds or stood along walls, all eyes fixed on the glass wall and the struggling fat boy inside it, now stretched across the desk, which had been moved so his fat butt faced the watching boys. His tightly puckered, almost red asshole peeked shyly from between huge buns. Pip entered the room and took up a position standing by the boy's side. He raised the paddle. Tommy had stopped struggling and was looking fearfully back over his shoulder, his eyes fixed on the slab of wood that was soon to kiss his backside again and again. Pip raised his voice loud enough to be heard clearly in their room and in the squirt dorm that looked into the adjoining side of the room. The curtains to the girls' dorms remained closed, so clearly "Onanism," whatever that was, wasn't as serious trying to look at naked girls in the shower.

Or so Jake reasoned at first. But the next few minutes changed his mind. Pip proceeded to paddle Tommy's fat butt with enthusiasm, each blow making a sharp smacking noise as the paddle impacted it. Tommy cried out from the first blow, and was soon sobbing loudly and shamelessly as Pip continued methodically beating his butt, spreading the spanks around the huge surface area. The curved globes were soon a blushing pink, then mottled red, then a glowing, angry red. Lines of blisters blossomed up and down both sides of the deep butt crack, then began appearing in the lower centers of the expansive buns themselves, multiplying until masses of them were clustered on the sit spots and higher, an oval of angry red welts on each side of the now wailing boy's butt. The paddling seemed to go on forever, and while some boys smirked that superior smirk boys show when someone else is getting it, most seemed disturbed by the beating Tommy was getting.

After an eternity, Pip finally landed three final, extra-hard blows, and then stopped. Tommy had stopped struggling long before, so even though Pip's henchmen released him, he continued to lie limply over the desk, sobbing loudly. A boy sitting on the bunk two down from Jake and Sam spoke up. "A hundred," he said. "He got a hundred, 'cause it was his third time." He looked at Jake and Sam. "You get 50 the first time," he said. "The first time you get caught. You get 50. Then 75 the second time, and 100 the third. He better not get caught again. He gets 200 if he gets caught again. Beloved Virgin, that's got to hurt."

Tommy finally showed some movement. He had reached back with a shaking left hand and gingerly placed it on his butt, feeling around the most blistered area and wincing. His right hand shakily moved to his other bun and cupped it as well. He flinched with the contact to his blistered surface, but his hands remained cupped on his butt, gently massaging as he cried. Pip smirked at the watching boys and tossed the paddle jauntily in the air. Trying to catch it, he missed entirely and it went clattering to the floor. Disgusted, he left it there. "Get that," he told one henchman. "And you, get him to his bunk." He stalked out, headed directly to his bunk area and thankfully not passing near the still naked Sam and Jake. In the glass room, Tommy was forced to his feet, and turned to face the boys as he was half-dragged out the door, still clutching his butt. His face was a puffy mass of tears and dripping snot, and he was still wailing loudly, his voice getting louder as he entered the dorm again. His penis, Jake couldn't help but notice, wasn't hard any more—it had disappeared into the fat of his bald pubes, a barely visible button over a wrinkled, bald scrotum. He was deposited face down in his bunk, where he quickly grabbed a pillow with one hand and buried his face in it, while his other continued to cup and massage his blistered, red butt.

"They'll put him in a box tomorrow," the boy across from them commented. "He won't touch it for sure for at least two weeks."

"A box?" Sam said, puzzled.

"A cock box," the boy said. "You had to have seen 'em—there's a squirt in the dorm that shares the showers with us who's wearing one right now. Must pull his pud all the time, because he's had one before, too, and he got 75 from Sister Mary Catherine in the glass room a few weeks ago. Blistered his butt but good. They're made of some new stuff that's hard and black—Bakelite, they call it, I think. You'll see him get fitted tomorrow—they have to find one with a hole in it the size of his boy stuff. You know, the parts that stick out. Tight enough to stay on, but not so tight it cuts the blood off. If it cut the blood off, his cock and balls would fall off." He looked delighted at the prospect. Tommy's sobbing was diminishing to muffled cries and hiccups.

"Lights out in 5," Sister Grace suddenly called from the doorway. "Everyone in their bunks, please." Jake sighed and climbed naked between his sheets, and Sam crawled into his own bunk. Around them, boys slipped into bed, some grumbling, some quiet. It felt strange, the sensation of his cock against the sheet. But he didn't get hard—his cock ached from overuse and seemed uninterested in any kind of stimulation, thank the Virgin Mary. Or whoever was in charge of wieners up there, Jake mentally amended, then felt shame for thinking like that. Tommy continued whimpering into his pillow, making no move to get under the sheet. The boy who'd been talking to Sam and Jake moved to Tommy's bunk and put a hand on the back of his neck.

"Come on," the boy urged. "Quiet down. If you're still crying when they shut off the lights and it bugs him, he'll give you more, you know that." Tommy shook him off angrily and turned his head the other way on the pillow, but he muffled his sobs. With a free hand he struggled to pull the sheet over his body while still cradling his butt with the other hand. The blisters, up close, looked a bright, disturbing red. The other boy looked one more time at Tommy's bright red, blistered butt, and then shrugged and went to his own bunk. Sister Grace spoke from the door once the room quieted.

"I'm very disappointed that one of you has succumbed again to that disgusting act," she said. "God will not admit an Onanist to the kingdom of Heaven, you know. I'm going to require that all of you sleep with your hands outside the sheets tonight, and continue that practice until I feel I can trust you all again." Groaning, the boys all withdrew their arms from inside their sheets. Jake and Sam slid their own hands outside the sheets. Sister Grace scanned the room and nodded approvingly.

"You'll see," she said. "It fills you with such holiness to resist your foul, base urges. You boys are all my shining lights of God, you know. I see the goodness in all of you." She frowned as her eyes crossed Tommy, still comforting his smarting, blistered, red ass, only partly covered by the sheet as he lay on his stomach. But she let it pass—the boy was entitled, after all-he'd just received a memorable spanking, even if it was fully deserved. His third time, no less! Why hadn't he learned the first two? Why did boys find that disgusting touching of themselves so hard to resist? She never touched herself—never had, never would. She almost shuddered at the prospect, then flipped off the lights and let the door shut behind her.

Shower time the next morning was another shock. The naked boys gathered around the clusters of nozzles, as usual, Jake and Sam sharing with the two boys from the dorm as usual. Tommy had groaned loudly when prodded from his bunk by one of Pip's minions, and walked stiffly to the bathroom naked with the other boys, his butt now black and blue with tinges of green and his blisters still prominent. He didn't touch himself front or back, Jake noted as they took their turns peeing, but shook himself off by bouncing on his midsection with his knees and wincing. Sister Grace paused before turning the large shower valve. "As we discussed last night," she announced loudly, "and in light of the incidents of late of lust that seem to be stalking the boys in this orphanage, we've decided to take steps to reduce this soul-endangering outbreak. Sister Mary Catherine argued for cold water alone, but I convinced her and the others to temper it somewhat. Still, this will be a bit of a shock, I'm afraid."

What felt like icy-cold water shot out of the nozzles. It stung the skin, and in moments all the boys were shaking, the younger ones squealing, the older ones grumbling loudly. "Hurry up with the soap and shampoo, boys," Sister Grace called over the complaints. "The faster you wash, the faster I can turn it off." Shaking with the cold, the boys hunched over but got to work, soaping quickly, shampooing, and squealing as they ducked under the ice-like streams. The air actually felt warm when the stinging spray was shut off and the boys stood, dripping waiting for their towels. Several younger boys behind them were glaring at Jake and Sam as towels were given to the boys in line, with the big boys getting theirs first, as usual.

"Your fault," a smaller boy muttered. "You had to get caught trying to see some pussy."

"What was that, young man?" Sister Grace said, handing him a towel from the pile.

"I was just telling the new kids to be careful, because today is Challenge Day," he said innocently.

"Yes, you should all be careful," Sister Grace mused. "I'm not fully convinced that Challenge Day is such a good idea. But Sister Mary Catherine insists upon it, and Mother Superior has given it her blessing. And Mother Superior is guided by God." She handed Jake and Sam each towels, and they dried off, dropping the towel in the hamper and walking naked back into the dorm. They followed Tommy out, walking haltingly and wincing, his sore, blistered butt scabbed over roughly on the sit spots and clearly hurting. Once at their bunks, Jake and Sam were faced with the fact that they still had no underwear to put on. Jake shrugged and pulled his own pants on without underwear, and Sam followed suit. It felt funny for a minute to be wearing pants without underwear, and Jake grew half hard instantly, but after a time he adjusted and his penis returned to normal. He almost reached to the front of his pants to adjust himself but immediately thought better of it as he caught a glimpse of Tommy gingerly rubbing his still sore butt and standing by his bunk looking disconsolate, his small genitals cold-shrunken and barely visible. Onanism had something to do with touching your wiener, and Jake sure didn't want to risk the punishment this boy had gotten.

They were barely dressed when Sister Mary Catherine glided between the bunks and stopped by the still-naked Tommy's bunk, setting several brown-black objects on the cot beside the unfortunate boy. Jake eyed them with interest—there was a small, oblong black box, and several of what looked like large rubber grommets. The grommets had the same outside diameter but were of differing thicknesses, from about an inch across to almost 2 inches. Sister Mary Catherine pointed to the bunk. "Stand there, boy," she said in a no-nonsense voice. "Hands behind your head and keep them there." Despite the fact that standing on his bunk would expose Tommy's humiliation to the entire bunk house, the fat boy immediately crawled slowly onto his bunk, his blistered butt clearly hurting, and stood up, wincing as his large butt muscles flexed in the process. He faced Sister Mary Catherine, resisting the powerful urge to cover his genitals from her obviously disapproving gaze and instead drawing his hands up in the proscribed position. His position put his genitals just below her gaze, and she frowned down at the shrunken, barely visible penis head and the drawn-up balls, looking like a tightly-wrinkled patch of skin with no visible contents.

"Stop hunching over," Mary Catherine barked. "Stand up straight, shoulders back and straight." Tommy straightened his back. "Bring that enormous fundament of yours in, boy! Stand proudly and accept your just punishment!" Jake and Sam weren't sure what a "fundament" was, but Tommy must have known, because he tightened his enormous butt with a wince, bringing it in and thrusting his bald genital region toward the nun. His genitals were no more prominent than before—he almost looked as modestly endowed in front as a girl. His face displayed fear, although of what Jake and Sam weren't yet sure.

"Hrrrmph," Sister Mary Catherine muttered. "It's always the most modestly endowed who are the most lascivious. That makes my job so much more difficult." She turned to Jake, who, having then next bunk, was standing the closest, finishing the buttoning of his rather ragged shirt. "Sister Grace has gone to the administration building already, I believe," she said serenely. "Poorly endowed little boys like this one require a small insert diameter, and thus a small hand. I can handle the bigger boys, but not ones with worms as small as this one. Your own physical immaturity will be to an advantage, I believe. You will apply the insert I select once I have examined him and verified his small size. It will also do you good to apply the grommet—you should know just what awaits you firsthand if you continue down the path you're following." She pointed at the collection of grommets on the bed. Jake, mystified, looked at the assortment of 4 differently-sized rubber circlets.

"If my experience is any guide, the inside diameter will be the one we want," Mary Catherine continued. "Pick that one up and hand it to me. I will show you how it is to be applied." Jake picked up the grommet with the smallest internal diameter. Sam looked at it, then looked up a Tommy, standing nervously on his bunk. Tommy was white as a sheet now, and trembling. HE apparently knew what was coming, and feared it. Mary Catherine turned to Sam. "Make a fist, young man," she ordered. "And hold it out in front of you."

Sam almost jumped when she spoke to him but he did as he was told, holding his small fist in front of him. Sister Mary Catherine turned to Jake. "Hold out your right hand, young man," she ordered. "Put your fingers together with your thumb against the others. She showed him with her own hand, and Jake followed suit. She then took the grommet and began sliding it onto his fingers, stretching the rubber until it passed his knuckles. "Now open your fingers and thumb," she ordered. Jake strained, and was just strong enough to stretch the grommet, like a rubber band, making the hole in it wider. She nodded approvingly. "Now relax your fingers again," she said. "Don't let the insert off your fingers. Stand ready." She turned to Tommy. "Hold still," she ordered.

Every face in the dorm was riveted on Tommy's crotch. Boys with bunks behind his had finished dressing quickly and moved to the other side so they could watch the process with wide-eyed fascination. Sister Mary Catherine didn't hesitate. She grasped Tommy's bare crotch low down, where the "V" of it met his fat legs. Pressing her fingers in, she probed. Tommy shifted uncomfortably. "Hold still, I said," she snapped. "Do you want me to have the head boy slipper you?" Tommy held still. Sister Mary Catherine probed more deeply, finding, isolating, and palpitating the two small lumps buried in the boy's pubic fat and forcing them out, stretching the scrotal skin and making the boy's balls press the skin out until the wrinkled skin bulged in front of him. Gripping more tightly and working her fingers, she forced the small, almond-sized lumps to the front of the scrotum, stretching the tightly wrinkled skin. Tommy let out a little squeak and started to pull his crotch away. Sister Mary Catherine dug her fingernails into the base of the boy's scrotum. "Stop that muling, you lascivious brat," she snapped. "Hold still!" Tommy, biting his lip, froze, and she angled her fingers so the nails no longer dug into his skin. He gasped as she pulled hard on the two little lumps, making them stick out prominently and giving form to his normally flat scrotum, but he didn't pull away. She let go and studied the small sack she'd formed with her fingers, satisfied with her work. She then glared at the tiny button that was his circumcised penis. "This will not do," she stated. "We must trap all your lascivious parts at their base."

Frowning, she reached into a large pocket of her habit and withdrew a rubber glove. Tommy, looking down, stiffened, his face turning white. He looked like he was about to faint. Jake, remembering, felt his heart start pounding as she slid on the glove. He knew what had happened to both him and Sam every time a glove like that came out. Sure enough, she then probed another pocket, coming up with a small jar of Vaseline. As they, and the boys in the dorm, all watched with varying degrees of emotion, Sister Mary Catherine liberally coated her index finger in the jar, set the open jar on the bunk, then placed her free hand on the boy's stomach, well above his genital region. "Don't you dare move or tighten up," she ordered. "Or it's the slipper for you. I don't care how blistered your bottom already is." Leaning over, she expertly parted the boy's lower buttocks with her thumb and second finger, then without warning or hesitation plunged her greased finger between the two fat loaves of the boy's huge butt low down, near his legs, her finger angled upward.

Tommy stiffened and squealed, but managed, barely, not to let go of the back of his neck. Sister Mary Catherine pushed her finger deeper, then twisted it. Tommy squealed again, softer this time, his buns trembling as he fought the urge to clench, to push this intruder out of his rectum. His penis twitched, twitched again, and then like a phoenix rising from the ashes, began to accordion out of his groin. As she continued to twist her finger this way and that, the boy's penis extended more, in little pulses driven by his beating heart. Within a minute, it was curving up like a too-thick little coat hook, complete with the knob at the end. Jake, standing closest, could see a protruding vein that marred the smoothness on one side with a blue track, and the rather disgusting tangle of skin on the underside, just back of the tight pee slit that marked the lower tip. To Jake's chagrin it was as big as his—maybe he did have the smallest wiener in the dorm, he thought. Still, he was glad not to be in Tommy's place at this moment.

Sister Mary Catherine's bark startled him out of his contemplation of the sudden appearance of the unfortunate Tommy's genitals. "Now, boy!" she snapped. "Open your fingers and put them over his lascivious parts! Thumb under the sack, fingers surrounding the rest!"

With some effort, Tommy forced the ring of rubber to stretch again, until his fingers were far enough apart to place them around the other boy's genitals as instructed. His fingers brushed the throbbing tip of the organ as he did so, and he marveled at how hard it was, and yet, how soft the skin of the little ball sack was at the same time. He had to open his fingers wider to enclose the entire package, small though it was.

"Good, good," Mary Catherine said, withdrawing her finger from Tommy's ass. Tommy squeaked as her finger withdrew, squeezing his ass tightly. Jake remembered the burning that he'd experienced in his own rectum when in Tommy's position, and sympathized. "Let the insert slide off the tips of your fingers, then withdraw them," she ordered. Jake did so, and the rubber piece settled neatly against Tommy's groin, outlining his now prominent genitals and holding them firmly out from his body. Sister Mary Catherine wiped the glove on a cloth she pulled from her capacious habit pocket, and then probed the small package with her gloved fingers. Tommy's penis was already shrinking, but the ring kept it from disappearing.

"Is that comfortable," she asked Tommy, looking up at his white face.

"It's – it's – it's awful tight," Tommy stuttered in a small voice.

"Good," Mary Catherine said. "It should be tight and it shouldn't be comfortable. It's clearly not blocking circulation," she added. "Or you wouldn't have shrunk back to innocent proportions. I'll just make sure it's not too loose." She gripped the insert from the outside with her gloved hand and pulled on it, yanking the boy's penis and balls painfully. Tommy squeaked and stiffened again. The ring stayed tight against his groin, his balls and penis head trapped in it. She nodded her head in satisfaction and let go. "Perfect," she said. "Take one last look at your disgusting parts, boy. You won't see them again for another week." Slipping off the glove, she picked up the box parts from the bunk. The two halves fit together neatly around the boy's genitals, and she secured them with a screw that passed from one side to the other, using a screwdriver she had in her habit. God, what didn't she have in that habit, Jake thought to himself. In moments, Tommy stood there with a small brown-black box where his bare genitals had been. Jake could see the small group of holes in the bottom, apparently there for the boy's pee to drain out when he had to go. He thought back to the boy from the squirts dorm who'd been wearing a similar device. Now he understood—the box prevented touching the penis, even to pee, even to scratch. Tommy's penis was now a prisoner in a box, trapped there because Tommy had supposedly touched it. He vowed not to touch himself again, even to pee. But as he made that vow, he remembered how good it felt to touch his penis, especially when it was hard, how wonderful it felt to rub it, with that pleasuring building until shivers when through you, like God and Jesus were both kissing your organ...

The blasphemy of what he was thinking shocked him back into awareness again. His dick was hard, he could feel it against his pants, pressing the hard denim as he had no underpants to wear between them. His flushed guiltily and looked away from the box on the boy's crotch, only to realize that Sister Mary Catherine was studying his expression. As he blushed with guilt, her gaze slipped deliberately down his body, stopping at his crotch, which she studied openly.

"You'd best watch yourself, boy," she said. "You, too," she said, her gaze sweeping across Sam. She turned to look at all the raptly watching boys in the dorm, some looking at Tommy with pity, some with horror, many with eyes glinting with excitement, and quite a number, including Pip, with a superior smirk on their faces. "All of you," she added, speaking more loudly. "I have more chastity boxes coming in. And I can order as many more as I need." She turned and glided toward the door, her smooth, battle-cruiser like motion contrasting with her clearly disapproving face. She stopped at the door.

"Get dressed, you disgusting little Onanist," she snapped at Tommy, who was still standing on his bunk with his hands behind his head, looking down at the box on his crotch with undisguised horror. "The rest of you, get to breakfast now! He's already made you late, and you know how special today is."

Tommy scrambled down from the bunk, wincing as his butt ached from his spanking just hours before. He snatched up his pants and began dragging them on. Jake puzzled a minute, then realized that Pip had forbade the boy from wearing underpants, supposedly so that it would be obvious if he got hard. In moments the box disappeared, although it made a square bulge on the front of his pants. Boys were already filing out the door to the dining hall, and Jake and Sam joined them.

"What did she mean, special?" Sam asked Jake.

Jake opened his mouth to acknowledge that he didn't know.

"It's Challenge Day, stupid," one of the older boys who hang with Pip said. "You two should prepare to get your butts whopped."