The Darkholme Academy Chronicles: Orientation

Introduction:
Gareth stood in front of the tall black gate. A duffel bag full of clothes and toiletries was clenched in his left hand. Behind him, the taxi pulled away, back in the direction of the small airport at which he had arrived only an hour ago.
A woman in a knee-high black skirt and black business jacket was striding towards the path that connected the gate to the expansive, black and red building that was Darkholme Academy.
Gareth pulled out a small booklet from a pocket in his bag. A Guide to Darkholme, it said on the cover. Underneath that was a grainy photo of the very same building that stood in front of him – only it didn’t seem half as big – and the tall black fence that ran the perimeter of the grounds seemed to have been photoshopped out. In the corner was the academy’s logo: a curled up mouse, around which were the words “Freedom in Discipline.” Made sense, seeing as the school was – as the booklet advertised – the “number one reformatory school for young men struggling with authority.”
Gareth was a couple of years out of high school (a place he barely graduated from) and was jobless and living out of his parents house. Most days he would spend masturbating to hardcore pornography while his parents were at work – he loved watching big-breasted pornstars taking big cocks and toys up their assholes – so it was much to his dismay when they saw it fit to send him to Darkholme, so that he may learn some valuable life lessons. He just saw it as more school.
“Good morning,” said the woman, who had reached the gate and was now unlocking the large padlock, which up until now, Gareth hadn’t noticed.
“Morning,” he replied.
She swung open the gate and extended her right hand. Gareth took it. She was much taller than him – a whole foot, maybe.
“Headmistress Ives,” she said.
“Gareth.”
She beckoned for him to step through, and he did. The headmistress quickly locked the gate behind him, and started back towards the building. Gareth followed.
The grounds were rife with activity. Groups of young men, who all looked to be around Gareth’s age, were performing fitness activities on and around the running tracks which surrounded the main building. A huddle of runners in plain grey gear came by on the track. As each one passed, they offered a small nod to the headmistress, and said, “Good morning, Miss Ives.”
She smiled at each one, but said nothing. Gareth noticed that some of the boys held looks of intense concentration on their faces, as if they were performing mental calculus during their run. Weird, he thought. How long do they make us run for? The close encounter also gave Gareth a better look at the uniform – the shorts were a bit too short for the weather – any weather, in fact.
“Mister White, I take it you’ve come to be acquainted as much as possible with our facilities and academic background?” asked Miss Ives, abruptly.
“Uh, yeah,” said Gareth, brandishing the guide book.
“Oh, that.” Miss Ives gave a short laugh. “That’s just marketing. Here,” she produced another, similar looking booklet from her jacket, “this one’s a bit more detailed.” Gareth hoped she was right: the original booklet contained a lot of writing, but didn’t say much other than how great the school was. Marketing, indeed.
The front cover of the “real” booklet showed a similar picture, except the fence was fully visible. The logo, too, was different. Instead of a mouse, it showed a rat, and the phrase that surrounded it was “Pleasure in Submission.” Gareth stifled a laugh. How does this woman not get how kinky that sounds? He pretended to flick through it.
They reached the front doors: two recently painted black monoliths. Headmistress Ives pulled one of them open for Gareth and ushered him inside. A large lobby greeted him – a desk sat on his immediate left, manned by a young blonde woman. A staircase sat in the middle of the room, leading to the second floor landing from which extended a variety of corridors. Two more large doors stood on either side of the staircase, and another stood on the opposite side of the room to the desk, and on it were the words “Headmistress’s Office” in thick, black letters.
Headmistress Ives closed the door, and stepped in front of Gareth. “Nurse Verne will be arriving presently. After the medical, you will be shown to your first class. You will be joining registration group C7. You will share classes and activities with all students from that group.”
Gareth didn’t really listen to the last part. “Um…what did you mean by ‘medical’?”
Headmistress Ives smirked. “Did you read the guidebook I gave you? Or did you just flick through it?”
“I, uh-”
“I think you better skim it a little before Nurse Verne arrives. I’ll be in my office.” With that, she left.
The receptionist was typing furiously on a keyboard, but other than that, the place was silent. Gareth opened the guidebook and started to read the introduction. It said:
“Welcome to the Darkholme Academy, where you will learn, over time, to become a productive and subservient member of society. Through our discipline-based curriculum and authoritarian teaching methods, we will transform you into a submissive individual, fit for reintegration into your home life. These methods, in particular, may initially seem strange, though we are sure that you will come to appreciate them for the positive effects they will undoubtedly have on your outlook and attitude.”
He was about to flick to the next page when a mature woman in a light blue nurse’s outfit came through one of the doors next to the stairs.
“Gareth White?” she asked, looking at him. She was red-headed, plump, and spoke with a slight English accent.
“Yeah, that’s me,” he replied.
“Right this way.”
Gareth followed her through a maze of doors and corridors he was sure he would never remember. I better be getting a map of this place, he thought. I could get lost for days.
“Just through here, please.” Nurse Verne opened a door, leading into a small white room, which looked like pretty much every other school nurse’s office he had ever been to. Gareth entered, and Nurse Verne shut the door behind him.
“Now,” she said. “Did you go through the guide book?”What is so important about this guidebook? thought Gareth. “I, uh, didn’t quite get through all of it.”
“Oh, that’s unfortunate,” she said. “Don’t worry, everything is standard procedure. Could you please take of your clothes for me, Gareth?”
Gareth wasn’t sure whether he heard her correctly. “You want me to what?”
Nurse Verne approached him and placed her hand on his wrist. “You are to take off your clothes,” she said sternly, before lightening her voice. “Standard procedure,” she repeated and sat down at her desk.
Gareth shuffled uncomfortably for a moment, and then placed his duffel bag on the floor. Nurse Verne spun in her chair to face him, recognizing his trepidation. “Gareth,” she said. “If you won’t take off your clothes, I’ll have to take them off for you.” She unbuttoned the top of her outfit, and allowed her fingertips to graze the top of her large breasts.
Gareth felt himself become hard. He had a bit of a thing for matures – many times he’d cum over videos of mature women getting a pounding, or even getting it on with each other.
He stripped off, displaying his half-mast six-inch cock to the nurse.
“There,” she said, standing up. “That wasn’t so hard, was it?” Her eyes flitted to his cock for a moment.
“No, I guess not.”
She went into the cupboard and took out a large red rectangle of rubber. It looked like a hot water bottle. She took it to the sink and began to fill it up with water. “We have to get you prepared for integration into the Academy’s health schedule. Pop up onto the table for me, will you? Face down, please.”
Gareth did so without hesitation. His cock lay pointed upwards, and he stroked it on the table’s soft top, making sure that Nurse Verne couldn’t see him while he did it.
“The schedule requires that you are cleaned out completely,” said Nurse Verne, turning. The red bag was full to the brim, and she hooked it somewhere up behind Gareth. “For that, I am required to give you a thorough enema.”
“A what?” Gareth was very familiar with that – he loved his kinky Japanese porn too.
A hand shot up between Gareth’s legs, gripping onto his vulnerable testicles. Gareth winced, and Nurse Verne released her grip slightly, and started to massage with her thumb. Gareth moaned.
“There we are,” she cooed. “You like that, don’t you?”
“Mmmm,” said Gareth in reply.
“Good.”
Gareth felt another hand move up above the other, towards his anus. The fingers were wet – greasy, even, and they stroked all around his virgin hole, covering it in the substance. The other hand kept going on his balls.
The fingers withdrew for a moment, before being replaced by something else – something rubber, about the size of a thumb. Gareth knew exactly what was going to happen – his cock was fully erect between his stomach and the table. Who knew this would turn me on?
He felt the rubber tip being pushed onto his ass. Naturally, his muscles tightened up, but, with the help of Nurse Verne’s generous lubricant application, his anus couldn’t keep the intruder out for long, and it slipped into him, all the way. The tip was long, and a bump at its base prevented it from coming out without a pull – or a push from Gareth. He heard a click, and warm water started rushing into his anal cavity.
“Uuuuuuuugh,” he moaned, involuntarily.
“Mmm,” said Nurse Verne, and fondled one of Gareth’s buttocks. “Most of the new ones enjoy that.”
Gareth was breathing deeply. He couldn’t help but feel himself being filled up – it was a weird sensation, and it spread throughout his insides. A gurgling noise came from somewhere inside him.
“Once you’ve taken the whole bag, and I’m satisfied that you’ve been thoroughly…hm, ‘irrigated,’ I will allow you to expel the water and whatever else is in there.” She motioned to a door at the back of the room, indicating that that was where the toilet was.
Gareth moaned in reply. He was acutely aware of how full he was now feeling, and how urgently his bowels wanted to expel their rapidly expanding contents. It was like nothing he had ever felt before: like a massive dump just waiting to go, but getting bigger and bigger all the time. He had to squeeze his ass hard so as not to accidentally shit the tube – and everything else – out.
The water continued flowing for a few minutes, Gareth moaning intermittently. Nurse Verne simply stood and watched.
When the flow stopped, Gareth picked his head up and looked at the bag. It was definitely empty; so was the clear tube that ran from it into his asshole.
“Good boy,” said Nurse Verne. “I don’t think I’ve seen a new student take the whole bag that fast.
“Can I go, now? To the toilet?” Gareth’s voice was shaking. His cock was still fully engorged.
Nurse Verne laughed. “No, of course not.” She approached the table. “Tighten,” she commanded, and Gareth complied, knowing exactly what she meant. The tip was extracted, taking with it a few drops of water, but Gareth managed to successfully hold everything else inside.
Then she made him go into several different positions on the table. On his side, on his back, on his other side, on all fours (that one felt particularly embarrassing), then on his side again, and so forth.
“Have to make sure you’re getting a thorough clean-out,” she said, aiding him into what would be the last position. “How do you feel?”
“Full,” said Gareth.
“Well, that’s how you’re supposed to feel. You can go now,” she said, motioning to the door again.
Gareth clambered off the table and waddled, hunched over, through the doorway. He felt the full weight of his ass’s contents as they sloshed from side to side as he moved.
He entered a room almost the same size as the office – a toilet sat in the corner, next to a sink, and across from a shower. For any unfortunate messes, thought Gareth. There wasn’t a lock on the door.
Gareth plonked himself onto the toilet and let loose. A loud, long and wet fart exploded from his ass, and it was followed by a torrent of shitty water.
“Uuuuuuuuuuuuuuugh,” he moaned loudly, barely over the sound of the water hitting the bottom of the bowl. The rapid expulsion felt great – his cock was just as stiff as ever.
When the first rush of water ceased, a knock came at the door. “I forgot to mention.” It was Nurse Verne. “Feel free to use the facilities at your discretion. You’re to be in there for half an hour in order to make sure that you’re completely flushed out.”
“Uh, okay,” said Gareth, before another explosion of water shot out from his now tender anus. Thirty minutes? he thought. Perfect.
He grabbed his cock with his right hand and started jerking. He clenched his ass tightly, stemming the flow – he figured the combined feeling of water rushing from his ass and cum blasting from his cock would be exhilarating.
As he jerked, Gareth fantasized giving anal to Nurse Verne. He imagined leaning her over the table in the office, ploughing her with long, deep strokes until she came, just from the sensation in her ass. However, he couldn’t help but derive pleasure from the feeling in his own asshole – that intense fullness, waiting to burst forth.
His cock pulsed, preparing to shoot his load – his breathing intensified, but Gareth dared not moan – he didn’t want Nurse Verne to know what he was doing. He edged closer to orgasm, and closer, and his ass started to spasm as a new feeling spread inside it – a warm, tingly feeling – and he was just seconds from exploding from both his dick and ass.
Then the door burst open. It was Headmistress Ives.
“Ah!” exclaimed Gareth, letting go of his cock – and ass. The water streamed out, along with another wet fart, and he felt his face go crimson.
“So,” said the Headmistress. She was no longer wearing her jacket. Instead she wore a tight leather corset, which lifted her breasts, displaying them high up on her torso. “Is there a reason that you feel comfortable using our facilities for masturbation?”
“No miss, I, um-”
“You are not here to jerk off. Nurse Verne has kindly performed her job, and all she has requested of you is compliance.”
“I’m sorry, headmistress.”
Headmistress Ives lifted her left hand. A small, cage-like device hung from her pinky. “I don’t think you are, Mister White.” She knelt down in front of him, and clicked open a ring at the bottom of the cage. She looked into Gareth’s eyes. “Continue,” she said.
“Huh?”
“Continue.”
“Okay, okay,” said Gareth, and tried to relax his bowels. He couldn’t help but look at the device, however. The cage was just over the length of his erect cock. Small spikes penetrated the space inwards, and a three-inch metal rod extended downwards from inside the top of the cage.
She gripped his rapidly shrinking cock, holding it upright. Gareth couldn’t help deriving pleasure from her grasp – his cock immediately stopped shrinking. Then, she put the cage over his member, pushing it down until the rounded end of the rod touched the tip.
Then she pushed some more.
“Hnnnnnnnn!” Gareth gripped the sides of the toilet bowl as the rod was forced into his urethra, expanding the inside of his cock. “What- what are you doing,” he managed, through gritted teeth.
Headmistress Ives remained silent as she pushed the last inch into Gareth’s dick. Then, she grabbed his balls with a thumb and forefinger and clicked the metal ring back together around the base of both his cock and scrotum. She produced a small padlock, and fastened it to the ring, locking it in place.
Gareth’s cock was now trapped in the infernal device – the combination of the spikes and the rod sent all kinds of pain up and down its length. Gareth squirmed on the toilet, whilst squirts of water continued to shoot out from his ass.
Headmistress Ives stood up. “Nurse Verne informs me that you have just over twenty minutes left. Perhaps now you’ll learn that this proud Academy is not a place for such activities as that.” She gestured up towards the ceiling, where Gareth could see a black dome – a camera. Then she turned towards the doorway. “Nurse Verne, I’ll return when the remaining twenty minutes are up. I’d like to finish the medical myself, to ensure that no more hijinks occur.”
“I will see you soon, Mister White,” and she left the room, closing the door behind her.
The last twenty minutes passed slowly. Try as he might, Gareth couldn’t get free of the cage and the constant pain that came with being trapped inside it. Nor could he get off the toilet and into a more comfortable position, given the randomness of his anal expulsions.
He had to wait it out.
At some point, he figured his ass to be completely empty. A couple of big pushes came with only small, high-pitched farts and the feeling that he was going to shit his whole ass, so he cleaned himself off and lay down on the cold, tiled floor, and waited for something to happen.
And something did happen, when, at the end of the twenty minutes (or so Gareth presumed), a command came.
“Time is up,” came Headmistress Ives. “Clean up, and come back.”
He took the opportunity to pause and take a couple of deep breaths, preparing himself for whatever else she might have in store for him.
On the table was a black, leather harness. Gareth’s heart sunk.
Headmistress Ives, who had been sitting on the one chair, stood up. “I hope you learned your lesson, Mister White.”
“Yes…I have, Miss Ives.”
“Good.” She motioned for Gareth to approach the table.
The harness consisted of three parts: the leather itself, which, when fitted together, looked to be connected by straps held in place by lockable metal parts. Gareth realized that, just like the cock cage, this would be padlocked indefinitely. Attached to an open metal ring on the front was a plastic tube with a hole at its top. The tube itself curved upwards, resembling an erect penis. The third thing was what gripped Gareth’s attention most. It was a black, rubber, two-and-a-half-inch butt plug.
“Standard uniform for all students of Darkholme Academy. Nurse Verne informed me that she felt your to be ass suited for the size two plug.”
“Size two?” Gareth asked.
She looked at him quizzically. “We go up to size five. Would you like me to request a larger one?”
“No, no.”
“Fine.” She seemed disappointed.
Ives approached Gareth, then unlocked the cock cage. She clicked it open, removing the spikes from his skin and freeing his now purple balls, then pulled it slowly from his urethra.
“Uuuugh,” moaned Gareth, as the metal slid out of him. His cock flopped down once the thing had been taken out.
“I decided to treat you lightly, given that you’re new here,” said Ives, as she discarded the cage. “If you do that again, the punishment will be much more severe.”How could it be any more severe than that? thought Gareth. He didn’t want to find out.
Ives produced a pump-bottle filled with a clear substance. She offered it to Gareth, who took it.
“Lubricant,” she said. “To help you put on your uniform.”
Gareth thought that, like the enema, he would have the task performed for him. “You want me to…?”
“I want you to plug up your own asshole, yes,” she said sternly. Ives then leaned onto one of the counters on the edge of the room. It was clear to Gareth that he would have an audience.
He took the plug in hand, and started to pick up the harness.
“No,” said Ives. “That is not to move.”
“What? How-”
“Get up onto the table,” she said, staring at Gareth.
“Okay,” he sighed.
“Yes, miss,” said Ives.
“What?” said Gareth, before realizing what was obviously a mistake. “Oh. Yes, miss.”
He clambered up onto the table and got down on all fours. The way the harness was laying necessitated that he point his ass towards the headmistress. He imagined it was what she wanted, anyway.
Gareth pumped out some lube onto his palm, then rubbed it over his anus, before testing its tightness with a finger. He shuddered as his fingertip entered his own asshole – it was cold, but his ring twitched with pleasure.
He moved to the plug, applying a generous amount of lube all over it, even over the tapered bottom. Once it was slick and shining, he hopped up like a rabbit and dangled his ass over the tip.
He took a breath, and lowered himself.
Thanks to the lube, his ass opened up immediately, welcoming the big black invader. Gareth slid down further, moaning as he went, until he started to feel a stretch. He stopped, then pushed down a little, further expanding his tender hole.
He paused as soon as he felt pain, then raised himself all the way off the plug. He reapplied lube to both the plug and his ass, and used three fingers to coat the inside of his butt with the slippery goo. He shivered as his fingertips brushed up against the walls of his ass. Again, his cock hardened.
He sat down again, and his ass gave way to almost the whole thing.
“Ugh,” he moaned, as it entered him. Why does this feel so good? he asked himself.
This time, he only felt pain when he reached the widest part of the plug, but he knew, with a little extra push, it would pop right in. He took a breath.
“Do it,” said Ives. “Submission is pleasure.”
And he popped onto the plug. His ass tightened around the base immediately.
“Mmmmmmm,” Gareth said, his ass gifted by the full feeling that the invader brought. As with the enema, it made him feel as if he needed to void his bowels, but he didn’t care. Submission is pleasure.
Ives didn’t waste any time. She came to the table and began strapping Gareth into the harness as he kneeled down to make it easier for her. She placed his hard cock straight through the metal ring and into the tube. It was only then that Gareth realized it was a chastity device: there was no way to remove his cock unless the entire harness was unlocked and taken off.
“The device will allow your cock to become erect, as you can plainly tell. Rather than use a device that constricts the penis, however, Darkholme uses this in order for the staff to easily identify any horny students. Although you may derive pleasure from the butt plug’s presence, understand that you are not to gain an erection during classes or activities, or when in the presence of a staff member. Do you understand?”
“Yes, miss,” said Gareth.
“Good,” she said.
Gareth got off the table. The harness felt strange; like a big, warm diaper, and the butt plug made him walk bow-legged. His erection began to shrink.
“Welcome to Darkholme Academy,” said Headmistress Ives, as she led him out of the office, past his crumpled old clothes and duffel bag. Gareth suspected he wouldn’t need them anymore.
“Ah,” she said. “It seems everybody is back from physical education.”
And they were. Crowds of male students marched along the corridor, clutching notepads and books. All of them were wearing a harness, and none of them seemed phased by it, or each other’s nakedness. Gareth couldn’t help but wonder which of them wore size fives.
Ives handed him a sheet of paper. On it was a timetable, detailing Gareth’s personal schedule.
“Slave training 101.” She pointed down the corridor. “Straight down, turn left. Room zero-zero-nine,” she said, before marching back towards her office, leaving Gareth alone in the river of people. He looked at the timetable again.
“Welcome to Darkholme,” it said, in large bold letters.To be continued…

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