Anton and Jeremy were nowhere to be seen for the next few days, and when they finally showed their faces, there were bruises and bite marks on both their necks, collarbones, and probably on other parts of their bodies too.
For Henry, nothing changed. He was used, bred, and tenderly taken care of once he’d performed his duties. But for all the fun he had, today was both terrifying and exciting.
Tonight, the wheel might turn in his favor, or doom him to another month of agonizing chastity. He wasn’t sure he could take it any longer, not that he would’ve had a choice. But if he did pick the short straw again, pulling out of the game and finding another place to stay was an idea he was considering.
He wrapped his blanket around his thick legs, ground his locked dick into his mattress, hoping to feel the slightest sense of relief. As he intensified his thrusts, he sucked on two of his fingers and tentatively massaged his entrance.
He must’ve looked pathetic, desperate.
The painful awareness that came with his situation had changed him. Denying that he enjoyed what was happening to him would’ve been pointless, yet two fingers stretching his hole weren’t enough, and he needed some warmth encasing his dick. The cold chastity cage kept him from the pleasures he most craved, and it drove him madder now than it did a month ago.
The sentence had been worthwhile, a true teaching moment, but he had been taught enough.
He groaned as he felt precum spilling on his pristine sheets. Then he pushed harder against his prostate, hammering it until it was so sensitive he began to sweat and twist as if he was being tortured.
Groggy, with his hole dripping with spit, he checked his alarm clock and sighed.
It was time to go to class, and he hadn’t even cum.
His morning was all about listening to boring lectures and subjects he only half cared about. They would determine his future, whether he’d become a successful chiropractor or a college dropout with forgotten dreams. In this instant, none of it had weight. His brain was in his dick, and his thoughts swam in his balls.
He put his forehead down on his table, shut his eyes, and clenched his fists under the table.
“What’s wrong, dude?” A nerdy guy named Jackson asked.
He was cute, slim, and stringy with brown eyes and a mullet. Not his usual type, but there was something about him that made Henry want to bend him over and fuck him.
“Just a headache,” he lied.
“I got something for that,” Jackson offered. “I get them often.”
“You should get them checked out then.”
“I did. Good news is I’m not dying. But my eyesight doesn’t help.”
Henry nodded, shifting on his seat as precum soaked in the fabric of his underwear. Ever since becoming a chastity boy, he’d become a faucet.
“Laser surgery might help.”
Jackson laughed. “That’ll wait until after I pay for my student loans.”
They stopped talking when the professor shot them a dirty look, and once the class was done, Henry considered slipping his number to the surprisingly confident nerdy boy. But he figured it’d be wiser to wait until tomorrow. If he got locked again, there would be no point.
So he waved his unexpected crush goodbye and braced for the rest of the day.
When dawn came, Henry hurried back home with featherlight legs. Football practice had been brutal, and it showed in the few bruises blooming on his skin and the swelling in his right wrist.
Oakfield House was rather dark, and when he locked the door as he stepped into the hall, all he could hear was voices coming from the dungeon in the basement.
Dutifully, Henry stripped and made his way down.
Everyone was dressed but him. The boys had picked their smart clothes, white shirts with black slacks and black leather shoes.
As usual, Anton and Jeremy were next to each other. Charles had his arms crossed over his furry chest, and Jordan stood in the center.
“Naked already. You’ve been well-trained. I wonder who you should thank for that.”
Henry bowed his head and knelt. “You all, sirs.”
“Such a good boy,” Charles whispered.
Henry blushed, a reaction he was sure he’d never outgrow.
“Tonight might be your last night locked,” Jordan announced. “Or it might be the beginning of another month in chastity.”
Shivers coursed through Henry’s body, and he pinched his lips to prevent any sort of begging. He wouldn’t give any of them the satisfaction.
Not before knowing his fate at least.
That’s when Henry noticed a bench he hadn’t seen before. It was long, knee-high, made of dark wood, but its strangest feature was the seven dildos screwed on it. They went from small to enormous.
Blood left his face.
“I guess you know what’s next,” Jordan smiled. “You have to fuck yourself on each and every one of them before we play the game.”
“But…” Henry stared at the biggest rubber cock. At least 10 inches and thick. “I don’t know if I’ll be able to…”
“It’ll be a long night of punishment if you can’t,” Jordan cut him off. “We got a few hours before midnight. If you make it through before then, we play the game faster. If you don’t, you’ll get your hole stretched longer. Your choice, boy.”
His brothers nodded; only Charles had a semblance of pity in his eyes, and Henry was grateful for that.
He took a deep breath. “Where’s the lube?”
“That’s the spirit,” Jeremy said, kissing Anton’s cheek before hushing something in his ear.
Anton’s shoulders dropped, but the instant throb in his pants showed he was more excited than sad.
Henry coated the first dildo, or rather, butt plug, and easily lowered himself on it. Meanwhile, his tormentors got to business as well. They kissed, they groped each other, they tore off their well-ironed clothes. Henry even noticed buttons bouncing to the floor.
His asshole got accustomed to the first toy in less than a minute, so Henry got to the second. It demanded more effort, but when it entered him, Henry let out a soft moan. He was facing his companions, and neither of them seemed to pay attention to him. Though he knew this wasn’t true.
Stolen glances were enough to push him further.
The third toy was a snug fit, and the rings of his hole fought it. It wasn’t longer than the second one, but it was wider.
He bit his lip, stared down at his locked manhood, and imagined himself getting fully hard.
Soon, he hoped.
The fourth one was longer and wider. Hesitantly, Henry slid off his previous fuck toy after coating the one that followed with a healthy amount of lube. When he crouched over it, the stretch caused him to wince. His hole couldn’t take it, not without some effort. It was at least 7 inches, and thicker than any of the guys’ dicks.
His chest tightened when he looked at the last stage of his trial. Ten inches, as thick as a wrist.
Fuck.
He looked up and saw Charles staring at him. He and Jordan were naked, stroking each other’s gorgeous cocks. On the other side of the room, Anton was religiously sucking Jeremy’s pink dick, hands behind his back so he wouldn’t feel the urge to pleasure himself while performing the act. As Henry admired them, a steady hand landed on his right shoulder.
“I’ll help you,” Charles told him before forcing him down.
“Please, please, Charles.”
“Don’t talk. Do as you’re told,” he said, his voice commanding but gentle.
Henry gripped the bench and let Charles guide him. Jordan had sat in one of the leather chairs scattered around the room, and lazily wanked off. He spat on his dick from time to time, but never stopped looking at Henry.
Being exposed was part of being a slave boy, and Henry knew he had developed an unhealthy need to be watched. His cock tried to get hard, but it was only squeezed tighter.
He cried out.
“I know, babe.” Charles gave him one last push, and Henry cried again. “See, it wasn’t so bad.”
It wasn’t.
“I wanna stroke my cock, Charles. I want it so fucking bad,” Henry whined.
“The faster you get to the big dildo, the sooner you’ll know what happens next. Okay?”
Charles’s circumcised cock was as hard as it could be, and Henry was close enough to reach for it. So he did; he gobbled it up and buried his nose into Charles’s thick bush.
“Shit!” Charles yelped. “Fuck, easy!”
Henry kept sucking, and fucked himself slowly on the dildo to ensure he was open enough for the fifth.
He brought Charles to the edge, servicing him even if his eyes were blurry and his jaw hurt. Then, Charles pulled out and kissed Henry as a reward.
“Get to the bigger dildo, now.”
Henry obeyed.
His hole was ready, oozing with thick lube. As he tried to get onto the fifth dildo without even pouring lube on it, Charles stopped him and shook his head. Carefully, he ensured all 8 inches were slick enough for Henry to fuck himself without getting hurt.
It did help, but as Henry’s butt hit the wood, his voice caught in his throat.
“Only two left,” he heard Jordan say. “You can do it! And guess what, you got three hours before midnight.”
Henry had been at it longer than he had thought. His joints hurt, his asshole was on fire, and his cock leaked so much that some cum was pouring out too.
The fifth dildo opened him up to the point he thought he might rip. The hurt wasn’t unbearable, but bouncing on it proved terribly uncomfortable. But endurance demanded strength, so Henry let himself go and pushed out his hole to ease the friction. It burned, it hurt, but slowly it turned into pleasure. His shrunken dick began to grow again, and Charles placed a hand on his lower back and massaged him.
After a few minutes and without a single word, Charles ushered Henry to the sixth dildo.
9 inches.
Longer, but not thicker.
He had already prepared it, and all Henry had to do was sink on it.
He did it in a single, sharp thrust.
The pain shot up in his stomach, and Henry lurched over. Tears pooled in his eyes, and the moans of Anton and Jeremy fucking faded in the background. Charles’s worried voice anchored him, but he had a hard time making out what he was saying.
“Stupid boy!”
He heard.
Henry chuckled. “It didn’t tear, don’t worry.”
“It better not. It’s no good damaging yourself,” Charles said, kissing the top of Henry’s head. “I should spank you bloody for doing that.”
“Wouldn’t that hurt me more?”
“Only for your own good.”
Henry smiled again, still dizzy and ready to tackle the biggest dildo.
“Let’s get to the end of it,” he said confidently.
“Fuck no! Let this one do its work first,” Charles replied.
“I can do it. I want this damn cage off!” Henry said, feeling the huge 9-incher pop out of his hole.
Charles nearly emptied the bottle of lube on the last dildo. In that moment, all the guys gathered around Henry to see how well he’d do, or whether he’d fail. He had done well up to this point, and he knew he’d blow them away.
He positioned himself, exhausted and shaking.
His muscles ached, his asshole throbbed, and his cock… He didn’t even want to think about it anymore. The slightest brush on his balls overloaded him with arousal. Once free, he’d cum in less than a second. For now, all he did was spread his asscheeks and swallow the tip of the 10-inch rubber cock with his overly sensitive hole. The first few inches were easy, but as the tapered end widened, Henry found it especially hard to keep going.
The end was thicker than a soda can. When he reached halfway, he lingered there for a while.
“Can’t do it?” Jeremy taunted him.
“I can! Just let me breathe for fuck’s sake.”
Jeremy slapped the back of his head. “What’s that, slave?”
“Sorry, master Jeremy,” Henry answered with spite in his voice.
“You better not draw the short straw next, or I’ll be sure to punish the fuck out of you.”
“Leave him alone, Jer!” Charles spat.
“Defending your boyfriend now?”
“What if I am?”
“Fuck,” Henry groaned, splitting himself open as he pushed all his weight down.
One inch.
Fuck.
One more inch.
SHIT!
That’s eight inches, he counted. Only two more.
The pain prevented him from breathing properly. Sweat produced a thin sheen over his skin, and his damp hair flopped into his eyes.
As his hole was torn open, he stared deep into Charles’s brown eyes for comfort, and then he felt Jordan’s hand on his nape.
“I’m so proud of you right now,” he said. “You’ve come such a long way.”
Henry nodded and grinned.
The praise was all he needed to take all ten inches.
He let out a long, ragged breath and let his head drop.
He had done it!
His hole was on the brink of ripping, but all he could think about was that it might be the end of his tribulation.
“I…” He swallowed hard. “Let’s fucking end this. Let’s play. Let’s see who’s getting locked next month.”
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