Charles led the boys into a large room lined with dungeon equipment. The boys were neither alarmed or impressed, the Academy used the same equipment plus several devices not evident here.
"Kneel"
The boys obeyed and knelt in the same order as before. The floor in this room was cold concrete though the room itself felt warmer than the hallway. A faint cloud of steam crawled from under a glass opaque door.
"After I get you prepped and ready to go to work, you're allowed fifteen minutes in the steam room."
Charles slapped Lyn''s head "You first. "
Charles tugged the chain connecting the two nipple clamps and led the grimacing young man to a whipping table. "Mount up, bitch, your little butt cheeks need to be bright pink for tonight's festivities "
Lyn was bound onto the table, wrists and legs restrained by thick leather straps. A chin rest had been added to the device so Lyn's face was in position to align with Charles's groin.
Once restrained, Charles tested the straps for tightness, satisfied the boy was helpless. Unable to make the smallest movements. Perfect!! Charles patted the slightly raised bejeweled butt.
"Such a small butt. Perfect for your master's well endowed poker pals. All big dicked and always horny. They'll love burying their fat cocks in this little hole"
Charles twisted the buttplug, moving it slightly in and out of the clenching cheeks.
"I guess you like that. They'll love you clamping that pink rosebud on their hard cocks "
Moving to the front of the table, Charles held his dick in his hand and rubbed the head against Lyn's lips. The boy was trying for eye contact but as soon as that dick was heaved deep into the small boys throat, all Lyn could see was Charles's stomach. Charles was trying to make the boy gag on his hard dick but no matter how deep he shoved into the throat he was unsuccessful. A fast fucking followed, ramming Lyn's throat repeatedly.
"Nice start, now for the main event"
Charles circled around to the boys bottom and having picked up an oversized ping pong paddle he rubbed it's sand-paper-like surface over the upraised buttcheeks.
Charles may have thought he was frightening the boy on the table, but Lyn loved it. He loved being unable to resist any torment meant for him. The thought of being spanked just made his dick ache against the metal chastity device. Inside he was secretly smiling, awaiting the sting, he was wishing he was being fucked at the same time.
He savored the lingering taste of Charles's dick, the smell of his crotch. He thought: the only thing that could make this better is two big cocks slamming my mouth and ass as my buttcheeks were paddled. Maybe something to come later?
The four kneeling boys watched as Charles raised the paddle far over his head, and with what appeared to be all his strength, spanked Lyn's small butt. The sound reverberated making it seem to go on forever. Charles changed cheeks and repeated the spanking which now resembled a beating. The small white buttcheeks we're taking on a ever darkening red color. No pink cheeks. Blistering looking red cheeks. Lyn hardly uttered a sound but his face was a grimace of pain, tears pouring and dropping to the floor.
"That's right bitch, keep clenching that pink hole of yours. I'm beginning to enjoy the fuck out of this" Lyn's asshole had been clenching after each spank.
The paddling went on for a half hour. Charles periodically shoved his hardened member deep into Lyn's throat, wiping the boys tears with the head of his saliva coated dick.
"Ok. I'm done. Just need to tidy up a bit"
Charles pushed a tennis ball sized gag into Lyn's mouth then after, attached a metal ball stretcher and hung a half full gallon of water from it.
"I'll keep filling that for you, bitch"
With a satisfied grin Charles surveyed the kneeling boys. After slapping each head he pulled Roger to his feet's by his ear.
"You're special 'Pimples', we're gonna open you up so you'll have a gaping pussy for whoever wants to use the strap-ons. Now turn around and bend over that padded stool. Touch the floor and spread your legs. I've a new speculum I've been dying to try out."
Roger obeyed and and was strapped to the stool, his butt plug glimmered in the light. Charles unexpectedly twists the plug and gingerly pulls it from its anal home. After a brief smiling inspection it is inserted into Roger's mouth.
"Keep it warm, bitch"
Charles fingered Roger's slightly loose-looking asshole, then inserted a two prong metal device with a screw tightener to spread the prongs apart, thus potentially turning Roger's asshole into a loose, gaping pussy. The prongs were touching each other when inserted but slowly spread apart as the screw was tightened. Charles slowly turned the screw to watch the prongs open to create a two inch gaping hole, he then poked a finger into Roger's now gaping asshole, then withdrew and put the finger in his mouth.
"Mm. Strawberry. We learned from the Academy to have the flavored water available for your douche. Would love to eat that sweet tasting hole."-
Roger had struggled against the deep seated prongs as they spread his asshole wide. He had accommodated speculums at the Academy and during other part time postings, but he intuited that Charles wanted to make them as uncomfortable as possible as soon as he could. So Roger played the virgin and reacted accordingly.
Charles took a sharpie and drew arrows pointing to the boys hole, covering the few pink pimples.
"Who's next?"
Putting a finger in each nostril of another boys nose, Charles led him to a sling and motioned him to sit in it. Thus seated, Charles bound his wrists and ankles to the sling with chains which were locked into place. The boy, Paul, watched as Charles picked up a metal plug and headed back to the sling.
"This will replace the blue jewel stuck in your butt. But this one has a feature I hope you'll like. First it will feel warm, then, if I choose, it'll feel like the inside of your sweet little asshole was hit by lightning. The initial feeling is quite pleasant, sensual even, your prostate will vibrate a bit with the warmth, feels nice. I'll give you a taste of the whole range of intensity and let you settle on the one you like best. But once you choose I'm taping a vibrator to your balls to see if we can coax a no-touch stream of cum for your master. The combination of the gentle heat and the vibrator have, in the past accomplished the deed nicely. Your master will then elect one of your brother bitches to clean up your gooey mess , lucky whore. You all should look on this exercise as a real compliment. Your master enjoys dishing out punishment much more than praise. So you should take the kudos when you're offered it. "
Charles removed the jewel plug and this too was placed in the mouth of the boy whose butthole had hosted it. He then gently replaced that plug with one made of dull metal which left a dark appendage sticking out of Paul's butt. A remote was laid on Paul's stomach. "We'll use that to find your desired intensity "
Charles then taped a rather large headed vibrator to Paul's groin, set snuggly between the boys scrotum and chastity- encaged dick.
"All righty then"
Picking up the remote Charles turned the dial to the highest setting. Paul's body went into a tight spasm which arched his back dramatically off the sling. A deep panicked groan rose from the boy, hands tightly gripping the chain restraints. Charles then reduced the electro intensity slowly until Paul's body was again resting in the sling.
Paul was no stranger to this kind of pain, he had volunteered for it when the Academy filmed their live stream.
"Oops". Chuckling, Charles again set the remote on Paul's stomach.
"You!!" Charles was pointing at Gene, who rose and stood waiting for instructions.
"Well bitch, I'm getting bored. Get into the cage against the wall, put on the collar, lock yourself to the cage, and leave the key in the padlock. There's about four dildos attached to the floor, different thicknesses and lengths. Put your butt plug in your mouth and starting with the smallest fuck yourself until you've used them all to end up pumping your ass up and down the longest, thickest one. Make sure you're sitting on the floor with that fat dildo all the way up your ass when the master comes in here."
Quickly obeying, Gene was soon collared, locked to the cage and sliding his asshole onto the first dildo. The green jeweled plug in his mouth.
Looking at Buster, hands on his hips, Charles seemed to be deciding what to do with the "three-holer".
Pointing at Buster "position three"
Buster was on hands and knees with his butt thrust up as high as he could, like earlier in the day for his Master. Charles, with no caution whatsoever tore the butt plug from Busters ass. The sudden assault made Buster yell in pain and attempted to reach a hand around to his damaged asshole.
"Well, well . At last someone broke the silence. But move your hand again without permission and you'll find it permanently taped to your back ". Charles walked around and stuffed the buttplug in the boy's mouth. "Get it nice and wet, bitch"
Circling to Buster's backside, he lined up his hard dick with the injured asshole and ruthlessly shoved it in. Then began the rough fucking, pulling completely out of the asshole he shoved it into the slit just below. This back and forth went on until his breathing became heavy and the strokes harder and faster.
Pulling free, with dick in hand, stroking it, he stood before Buster.
Understanding what he was expecting to do, Buster rose and his tongue pushed the buttplug into view. Charles grabbed the plug and slammed his dick down into Buster's throat, as hard and deep as he could manage. The gagging began immediately as did the fervent mouth fucking, until Charles grabbed Buster mouth, setting his dick head just inside, as it furiously spurted white cum onto Busters tongue.
"Keep it there. Don't swallow. I have somewhere else for it to go. "
Charles squeezed the remaining cum onto the boys tongue. Looking at it he had to smile at what a puddle it made. "Nice load, if I do say so myself"
Charles, dick in hand, walked around the room and assessed the progress of the four. Stopping behind Lyn. The boy was trembling despite being unable to move. His face and bald head streamed with sweat. The gallon jug of water had begun jerkily swaying side to side. The strain on the boys scrotum was obviously torturous.
"You know, I truly hate it when you boys enjoy this shit too much."
Pulling the jug downward, Lyn uttered a muffled cry. He begun sobbing miserably.
"I'm going fill your water jug, then we'll play a fun game"
Waving Buster over to where Charles stood, he pointed at the boys butt.
"Spit my load into the hole between those red cheeks, and you better hold that cum inside your ass, boy."
Charles popped the buttplug out of Lyn's ass as brutally as he had Buster's. This evinced another tortured groan muffled by the huge gag in the boy's mouth.
Charles grabbed the back of Buster's head and forced it against the pink framed hole.
"Spit it in, shove it deep with your tongue."
Lyn was indeed in severe pain, but felt no panic. His ball sack screamed with the weight it had to support and the thought of more made it worse. . He wished his dick was free to stroke, that's something that always made the pain more bearable. Lyn wasn't a pain slave but the right amount of pain delivered in right way made his orgasms explosive and long lasting.
Charles rolled another padded stool to the pair, "Lay on this table with your chin on the chin rest. Spread your legs wide" Charles stuffed a pillow under Busters butt to raise it up, then strapped him to the table so he could make no movement. Draping a cord over the boys head he inserted a 3" dildo gag into his mouth. This gag also had a 7" dildo pointing away from the boy's mouth.
"Start fucking that pink hole and shove it all the way in. Fast and furious "three-holer", yeah you'll gag but we love that sound."
Casting a wide satisfied smile around the the assembled boys, all busy getting ready for a long messy night.
"Mission accomplished "
A second pass by Roger convinced Charles to twist the screw and widen the gaping hole another half inch.
Checking on Paul, Charles decided the boy was enjoying this treatment far too much. Lifting the remote he cranked the dial up two notches and watched Paul react by trying to yell through the buttplug still in his mouth.
"That's better. Let's get some juice flowing bitch. Your master expects you to show him how obedient you are. I'd hate to see you punished for not cumming. I mean really? Gay sex boy can't shoot his wad?"
A look at Lyn and "three-hole" made him think about what more should be done. Three-hole's asshole was just too appealing.
Charles outfitted a auto-fucking machine with a two headed dildo. Both dildos were 8"x7". Thinking for only a moment that this might dampen master Wintermen's plans for the evening, he decidedly wheeled the machine to align with "three-hole"'s hungry looking fuck holes. Pushing the machine so the heads of both dildos just entered the holes, he switched on the motor.
It worked perfectly. The dildos made Buster gasp through her gag, then the gagging began in earnest. A stream of white goo drooled from his mouth.
"Now we're batting a thousand "
Charles turned and left the room. Each boy was locked into his predicament and couldn't leave, most couldn't move at all. The only loose end was the boy in the cage and the master will want to finish up with him personally.
Charles's dick had hardened again and began the familiar throbbing. Holding his member lovingly, softly stroking its length Charles knew what he must do. He needed his fuckboy. The personal cum dump who lived each day for Charles to dump as much of his cum into and onto him as possible. Charles wanted to cover his boys body in cum and lick it all off.
The two frequently showered together and drank each others piss. Charles found the thought of this so hot he was afraid he might shoot his load before he got to the waiting boy.
~~~~~~~~~
Wiley had fallen asleep with his head on the pew in front of him. The dreams hadn't yet begun but even dozing he knew he could be vulnerable. A hand laid on his shoulder and Wiley sprung to his feet and backed up, horror on his face, falling against the wooden pew. He fell backwards hard on his butt, hands were covering his face. He began weeping. "No. Please. Please. No more. Please. "
A white-bearded man was standing in the aisle, older, bald, with no malice on his face.
"Son, you were groaning. I think you fell asleep. "
The man's face had peace written all over it. Slowly the horror began to ebb from Wiley. He had awakened so abruptly he still didn't understand what was happening. The cramping muscles eased, slowly he became aware of where he was.
"I'm sorry.... I'm... pastor, but...."
"I'm called Father William, son. And you look like you haven't slept or eaten in a month", with a jovial chuckle Father William sat on Wiley's pew.
"Your soaking wet, you must be burning up. I think I should call the paramedics " Father William rose and pulled a cellphone from a pocket in his robe
"No, please. Don't do that. I....I...I have to get to ......" eyes rolling upward, Wiley fell to his knees, then forward to helplessly end up face first on the wooden floor. A pool of Wiley's urine began spreading from his pants.
"Oh, dear......"murmured the priest.
