Be sure to check out the previous installments of DAC first!
It was the first day of Gareth White's fourth month at Darkholme Academy.
On his first day, he had been given an enema for the first time, taken a butt plug up his ass for the first time, and had his cock and balls tortured for the first time. During his first week, he constantly struggled with the feeling of his training harness: the two-and-an-half inch wide plug up his ass fifteen hours per day and the chastity tube, which, although allowing him to have an erection, prevented him from doing anything with it.
But since that painful and uncomfortable first week, Gareth had come to slowly but surely enjoy some of the things about Darkholme. The feeling of ultimate fullness experienced via the double mineral oil enemas that must be held in the ass for the duration of Anal Retention 120 - a class he attended twice a week; the smell and taste of Mistress Carver's gaping, wet anus - granted, he only got to experience that after failing an easy pop quiz on proper slave etiquette, and it was accompanied by a fast, stinging urethral sounding; and the feeling of being able to cum every second Saturday - provided he make sure all of his seed ended up in his mouth, were things he had come to cherish.
The class he struggled the most with was Mistress Aitken's Intermediate Predicament Bondage. Not only were their tasks painful (as most tasks were), but they were also incredibly lengthy and required a great deal of endurance to complete.
And today would be no different.
The classroom in which IPB was held was one of the few in Darkholme that didn't actually contain desks. Mistress Aitken had explained that IPB was a practical subject, and as such, the students would need as much room as they could use in order for the whole class to participate simultaneously in the often humiliating - but always painful - challenges.
Gareth and nineteen of his fellow students walked into the room, all sporting their training harnesses. Gareth himself had moved up to a size three plug (three inches wide) only a couple of days previous, so he was feeling especially uncomfortable.
Twenty chairs were set up in a four by five grid in the middle of the room. Leg straps were attached to the front chair legs, and wrist straps were attached to the arm rests. A nasty-looking contraption sat underneath the seat, but Gareth didn't have time to give it a thorough up-and-down before Mistress Aitken spoke.
"Good afternoon, students."
"Good afternoon, Mistress Aitken," said everybody.
Like most of the staff, Mistress Aitken was wearing tight latex pants, (very) high heels, and a corset. She was one of the younger staff members - Gareth guessed about twenty-seven or twenty-eight, and she looked it. It wasn't uncommon for students to gain erections in her classes - even through the intense pain, her red lips, flowing blonde hair and curvy ass were enough to get anybody going. And her punishments for erections were the worst - she had once kicked Gareth in the genitals for simply being at half-mast and followed that up by ripping out his training plug and giving him a rapid fist fuck which lasted for five minutes. Gareth couldn't feel his ass for hours afterwards.
As with many of her classes, Mistress Aitken began by unlocking each student's training harness. Sighs of relief filled the air as the hot leather fell off their bodies and their cocks touched the cool air. The butt plugs, however, were still firmly in place, and were not to be taken out until Mistress Aitken gave the word.
After she had unlocked the last harness, she said, "Off with them."
Looks of concentration - and pain - filled each student's face as they pulled with their hands and pushed with their ass. Gareth, having not had much time to get used to the size three, struggled with the black beast. Students were not permitted to bend over whilst taking out their plugs - the task had to be completed whilst maintaining a good posture - so Gareth had to pull and push with all his strength just to budge the thing.
Gareth struggled not to wince as the three-inch plug parted his anus painfully. It fell out with a slurp, leaving a trail of ass juice and lube in his crack. Gareth could feel his ass gaping wide open.
He brought the plug to his mouth and started licking it. It was expected of students to clean their plugs whenever they were removed - Mistress Aitken didn't even have to tell them to do it anymore. Gareth slathered the whole thing in saliva, making it even wetter than it had been, before dragging his tongue across the whole thing and then sucking off the wide tip, tasting his own ass juices. It came off his puckered lips with a pop.
"Very efficient, boys," complimented Mistress Aitken. "Now, line up in front of the room. Face the wall. Bend over."
The students did so immediately, displaying their loose, plug-gaped assholes to their mistress. Gareth was in the middle somewhere.
"Today," she said, making her way to the start of the line, "you will be tested on your ability to make decisions."
She was moving up the line, pausing at each student.
"Up until now your tests have been tests of skill and endurance forced upon you by me."
As she neared Gareth, his asshole winked.
"Today you will have to test yourselves, to choose to put yourselves through pain, in order to pass."
Gareth heard her stop behind him, and then felt a small tube being pushed into his ass. It barely touched the sides of his anus. Then a cold substance started to fill him - it was thick, and Gareth came to the conclusion that it was lubricant. It filled up his whole ass to the point where he believed it would overflow and start pouring out over his balls. Gareth bent down further to ensure that gravity would keep the goo up inside him.
She stopped and pulled out the tube, and moved on to the next student.
When she was done, she commanded them all to take a seat.
As Gareth walked to a chair on the right edge of the room, he figured out what was going to happen. A large hole had been carved out in the middle of each of the seats. Underneath was a large black dildo - about two inches wide and eight inches long - attached to a rod, which was attached to a metal box. Also coming from inside the box were three chains, attached to a parachute ball stretcher, which was laying on the ground. I guess I'm not going to enjoy this class, thought Gareth. He sat with his asshole clenched tight so as to not lose any valuable lube.
When everybody was seated, Mistress Aitken moved around the room and fastened everybody to their chairs by the ankle and wrist straps. She also attached the top of the parachute to their balls, but left the chains loose. When that was finished, she produced a small remote control, and said, "I'm going to move the dildo up slowly. Position your anus over it when you can feel it."
Gareth felt a nudge at the top of his crack and moved up the seat to allow the dildo to enter him. Understanding fully what was going to happen, he pushed some lube out of his ass and onto the big knob. His hole gave way immediately, and the head popped up into him. The dildo then stopped.
"Has everybody been penetrated?" asked Mistress Aitken.
"Good." She pressed another button, and the dildo lowered itself out of Gareth's ass.
Then she pressed another button, and the chains attached to Gareth's balls started receding into the box. A whirring noise accompanied the movement. Just when Gareth felt his scrotum begin to stretch downwards, the chain stopped.
"On the end of each of your armrests is a button. Feel for them, but do not press them."
Gareth flapped his constrained hands over the armrests, locating the buttons.
"Found them? Good. As I mentioned earlier, today will be about decisions. Will you make the right choice, even if it means pain? Torture? The game I've created today will answer those questions for you."
Gareth didn't like the sound of that. His ass twitched in anxiety - the dildo had felt good, at least.
"The button on the right, when pressed, will make the dildo start to fuck you. Every subsequent press will increase its speed. The left button will lower the speed, but won't ever stop the device - only I have the power to do that. Your ass will be fucked for fifteen minutes. Once the time is up, everybody will be free to leave - everybody except the student who reached the lowest maximum speed. They will be punished for failing to make the right decision. Do you understand?"
"Good. Now start your devices," said Mistress Aitken. "And make as much noise as you like. You'll need to."
Gareth pressed the button at his right hand immediately, and immediately, the dildo began to creep back up towards his ass. It pushed against his wet hole for a moment before forcing itself back up inside. Gareth pushed back on the two-inch wide invader, knowing that if he didn't lather the whole thing in as much lubricant as possible, he would miss out on the only part of this that was at least semi-enjoyable.
Gareth moaned quietly as the dildo moved deeper inside him. It stopped only once it was all the way in, its artificial balls pressed right up against Gareth's skin. Its tip nudged against him, and his cock twitched in response.
Then the cock started its slow journey downwards. Its thickness made it feel as if it were dragging his insides out with it. When the head popped out of his anus, Gareth kept pushing, and farted out a dollop of lube onto its head before the return journey began.
Undeterred by the current speed, Gareth pressed the button on the right armrest, intending to get used to the steadily increasing speed as fast as possible.
He gasped as he realized what was happening, as did some of the other students. Not only did the dildo increase in speed to what would equate to a slow fuck, the chains receded further into the box, stretching his balls even further.
"Oh, did I forget to mention that?" laughed Mistress Aitken.
It was clear that the faster the dildo went, the more strain would be placed on their balls. Still, a stretch did not necessarily mean pain - Gareth guessed that it would be a couple more presses before his testicles were really in trouble. So, with that in mind, and the dildo now thoroughly lubed up, he pressed the button twice, in quick succession.
Gareth's balls were yanked down about half-a-centimeter, and the speed of the dildo increased sharply. Now it only took about a second for the entire eight-inches to fill his ass. It was ploughing him nicely now, and his balls were only just starting to feel pain. Better savor this, thought Gareth. I probably won't get another chance to enjoy it.
Gareth closed his eyes and moaned quietly, feigning displeasure. The room was filled with the sound of the whirring motors, but he shut them out, choosing instead to focus on the sound of the dildo pounding his slippery, wet hole. It filled him up, then came all the way out, then punched back into him again. Each time it did his ass became a little looser, and Gareth's moans became a little louder.
Slurp, slurp, slurp, slurp, slurp, slurp, went his anus, as that pleasuring warmth crept through his anal cavity.
Gareth pressed the button in order to wake himself from the dream. Better stop before I get hard, he thought.
Again, his balls were stretched, and again, the dildo increased in speed. The pain in his balls remained bearable, as was the speed of the fucking, so he pressed the button again, and again.
"Ugh!," he shouted, as his scrotum stopped stretching and his balls squashed up against the inside of the parachute. Pain shot through him, and he slammed his fingers onto the left button, relieving himself of the pain.
Take it slow, take it slow, Gareth reminded himself. He sat still for a moment, eyes closed, giving his scrotum a moment to get used to the increased tension. His sloppy pounding continued all the while.
He repeated the process for the next three presses. He would hit the button, then wait for his balls to get used to the tension, take a moment to enjoy the big cock as it rammed his unbelievably loosened asshole, and then press the button again.
Some time later, the dildo was all-out raping Gareth's ass. He couldn't tell whether it was going in or out, simply because it was going to fast. His anus didn't even have a chance to tighten up during the nanosecond of time during which it was all the way out of him.
His balls mus have been purple - they certainly felt as if they were. Never before had they been stretched so far - not even in Mistress Butler's Enduring CBT 210 class.
He was moaning openly now, as were most of the class. The whirring of the motors was all that could be heard as they worked overtime to pound the student's assholes at unforgivable speeds.
Gareth couldn't bear to bring himself to push the button again. He no longer felt a stretching pain, but an intense, dull one, coming from his testicles themselves - and it wasn't going away.
The students surrounding him seemed much the same - the speeds of their dildos were similarly blinding - he couldn't tell whether they were going faster or slower. One student was writhing in his chair, groaning in pain. He smashed the button on his left a few times, and let out a loud sigh as his balls were given a reprieve - but not for long, as he hit the right button several times and resumed writhing and groaning.
Gareth would have forced himself into the same state if it weren't for the whistle.
"That's time!" shouted Mistress Aitken, and pressed a button on the remote. Gareth's balls were given back to him, and the dildo slowed to a halt, then withdrew slowly from his ass. The smell of twenty gaping assholes filled the air.
Mistress Aitken did another lap of the room, this time pausing at each chair to make a note on a small notepad and to undo each students bonds. Please don't let it be me, prayed Gareth.
Their Mistress, now having completed the lap, stood at the front of the room. "To the nineteen of you who passed, well done. You may reinsert your training plugs and leave. Mistress Belle is waiting outside to lock you all back up. And to you," she turned to Gareth, and looked him straight in the eye. "You made the wrong decision."
Gareth's stomach was doing backflips. Mistress Aitken said nothing to him as the students left. Once they had gone, she moved silently to the cupboard at the back of the room, and Gareth could hear her drag out something large. Then she approached him, and locked him back into the chair.
"It's a shame, really. If you had just pushed the button twice more, you would be free. But, I suppose learning is difficult for some." She brought up her heel and kicked the chair over. Gareth toppled back onto a large mat. "Tilt your head back."
Gareth did what he was told. Upside down, he could still recognize the fucking machine in front of him. This one was smaller - the dildo maybe six inches in length. Mistress Aitken brought out a head strap and fastened his head back.
"We're going to play a similar game," said Mistress Aitken. "I'm going to start the machines at an intensity of my choosing. You must push the button four times. You may not leave until you have done so. Do you understand?"
"Yes, mistress" replied Gareth.
"Open your mouth."
Gareth did as he was told, and Mistress Aitken slid the fucking machine closer to his head. She then plugged the new fucking machine into the chair, and pressed a button on the remote.
Everything started at once, but slowly. Gareth's balls inched away from him slightly. The eight-inch dildo slid into his ass slowly. And the new dildo found its way over Gareth's tongue and down his throat. It went all the way down, until its balls nudged his nose. Gareth tried his hardest not to gag before it withdrew, just as slowly, taking with it a strand of saliva, which then draped itself on Gareth's face.
"In order to stop you from cheating, I've set this up so that you must endure each setting for ten seconds before pressing the button again," she paused. "You may begin," she said, and pressed a button.
Everything started at full-blast. His balls were immediately stretched out nearly as far as they were during the first test, and the cock started ramming his ass with earnest, as did the new one in his throat.
Gareth tried to blot out everything in his mind and focus on the ten seconds. Ten, he counted. Nine, eight, seven, six-
He gagged, spluttered, and send a glob of spit rolling down his face and over his right eye.
Four, three, two, one-
He pushed the button. He figured that the device's current state is what it had reached during the first task. His ass felt like it was about to fall out, and his balls felt like they were being crushed between the parachute and his own scrotum. Again, he gagged, and snot exploded from his nose. Tears ran from his only good eye.
He pressed again, and writhed in pain. The dildo started slamming his throat as spit flowed freely from his spluttering mouth.
Gareth screamed silently as he felt his whole body being pulled down the chair by his balls. He was gagging freely, and now wore a mask of spit and snot.
Gareth's ass finally gave way. It started farting out globules of lubricant around the blur that was the dildo. His anus now hung totally loose around the speeding shaft. The pain in his testicles went all the way up into his stomach - it was like somebody had kicked him there a hundred times. He could hardly breathe between the throat-dildo's rapid strokes.
And then it was over.
Mistress Aitken bent down and wiped the slime off Gareth's face with a cloth. She said nothing as she lifted the chair up and released her prisoner. She beckoned for Gareth to stand up, and he did.
"Bend over," she said, and he did.
Gareth's legs were shaking as he took the opportunity to survey his wrecked testicles. They were purple.
He felt fingers tracing the inside of his gaping ring. A cool, thick substance was being spread around.
"This will make you asshole tighten up. Quite rapidly, I might add."
"Thank you, mistress," said Gareth.
"I have a class in one hour. You are to thoroughly clean every dildo that was used during today's class."
"Yes, mistress," said Gareth. He was partly relieved. The taste of twenty assholes is nowhere near as bad as what I just went through.
"Start now," she said, and Gareth did as he was told.
He bent down on all fours underneath a random chair and tool the wet dildo into his mouth. It tasted of ass and lube, and he sucked on it greedily.
Gareth could feel his anus start to tighten up, and he couldn't help but smile. Both his ass and cock twitched at the thought of his three inch training plug, which would be forcing its way past his tight ring and filling up his anal cavity very, very soon.