Be sure to check out the previous installment of DHC first!
"Asses up!" she called as the dormitory's ceiling lights blinked on. In the two rows of fifteen single beds on either side of the room, the students of dormitory B3 began to stir.
It was Iris Belle's first day on the job. After graduating from Darkholme's sister college the previous year with stellar grades (especially in Pain Threshold Expansion 320 and Advanced Anal Retention), she was approached by Headmistress Ives and offered an assistant position here, which she accepted gratefully. She fully understood the "Submission is Pleasure" motto, and wanted nothing more than to instill that knowledge among others. In particular, those of the opposite gender.
Headmistress Ives was standing behind Iris - she was to be her supervisor during the first day. She was dressed in an uncharacteristic business jacket and long pants - Iris guessed it was to demonstrate that it was not her, but Iris, that would be in control today. Iris herself was wearing a full latex bodysuit, which extended to the top of her neck. In her gloved right hand she held a riding crop. In her left was a small bag filled with various devices, whose uses the students in the room were clearly aware of - they were all up now, on all fours, bare asses pointed toward the middle of the room.
"Any student whose ass is not presentable must be punished," whispered Miss Ives. "If all of them are acceptable, pick somebody to punish anyway. Be creative. And if any of them get hard during your inspection, deal with them thoroughly."
Iris nodded, making sure to keep her eyes forward, and her back straight, in order to symbolize her dominance over the naked students. She picked the right side of the room, and began to walk down the line of beds. Headmistress Ives remained at the door. Better think of some interesting punishments fast, thought Iris.
Next to each of the beds was a small table, upon which sat one item: the student's personalized chastity and training harness. She noted the varying size of the butt plugs that sat inside them - most looked to be between one-and-a-half and two-and-a-half inches wide, but she did spot one or two that must have been at least three. Iris herself, unlike most senior students, had managed to reach the size five plug before graduating - a four-inch beast which always made sure her ass was ready for even the harshest of punishments. She had passed the Final Exam - a test which turns most students into whimpering, quivering messes - without batting an eyelid.
All of the asses so far were clean shaven and, well, clean. So, not wanting to disappoint Miss Ives, whose unrelenting gaze Iris was completely aware of, she stopped at a random bed.
She reached out and grabbed the student's right ass cheek, making sure to dig her nails in hard. The student, who looked to be in his late teens, exhaled sharply but said nothing.
"Name?" asked Iris sharply.
"Brian. Brian Yarnell."
"Mister Yarnell, are you aware that your ass has not been properly shaven?"
Even though his ass was smooth, the student knew better than to question the judgement of a staff member.
"Yes, mistress. Sorry, mistress," he said, hastily.
"I'm afraid an apology won't make things better," said Iris, and reached into her bag of goodies.
She fiddled around for something good, eventually ending up with a six-inch dildo with a tapered bottom which then flared out into a wide base, much like a standard butt plug. The base itself, however, was much larger, and contained a panel with some buttons.
Iris took some lubricant from the bag and greased the thing up loudly, making sure the student could hear what he had coming.
Then she pointed the rubber cock at his ass and pushed. Get ready, she instructed silently.
"Ugh," he said, when the head popped in. Iris kept the pressure on, however.
"Uuuuuuuuuugh," he moaned, as the rest slid in with a greasy sound. His ass visibly tightened around the tapered bottom, fixing the dildo in place.
Iris bent down, and started to press some of the buttons on the base. "What does it feel like? Speak up now, so everybody can hear."
Humiliated, the student's face turned red. "It feels like, uh..."
Without warning, Iris gave his ass a sharp, stinging whack with the riding crop. He yelped.
"It-it feels like there's a big greasy cock in my ass, mistress."
"Does it feel good?" queried Iris.
"Yes, mistress." The student hung his head.
"Good. Now I'm going to make it feel even better" she said, and pressed another button.
The student moaned again, longer and louder, shuddering as he did it. Although Iris couldn't see it, she knew the dildo was currently inflating inside his anal cavity. A quiet hiss emanated from his ring, confirming what she already knew.
"It will inflate to nine inches in length, three inches in width," she said, loud enough for everybody in the room to hear. "Then it will deflate back to normal size. Then it will inflate again, and so forth, until I see fit to remove it."
The student let out a gasp of relief as the cock inside him shrunk.
Iris nudged his balls with the riding crop. "Miss Ives? Could I have your assistance with this one?"
"Certainly," she said, and approached the student, who was now groaning again as the rubber dildo-plug inflated once more.
"If the student's cock begins to grow hard, please let me know. Can't have him enjoying this punishment, can we?"
"Absolutely not," said the headmistress, who then turned to face the rest of the students. "And that goes for all of you!" she yelled. "If Mistress Belle here catches any of you with an erect cock, you will be in a worse place than Mister Yarnell here!"
"Yes, Mistress," came a chorus of male voices.
Iris gave Brian's balls a quick slap with the crop. "The plug will be removed once my inspection has finished." He whimpered in response.
The new assistant continued her rounds, this time pausing at each student, intimidating them, making them fear that they might be next in line for punishment. She crossed over to the opposite side of the room and walked back along the other row of exposed butt-holes.
She stopped behind one of them. No pause - this was a full on halt.
The student's cock was twitching. His face pointed towards the wall - no doubt a look of intense concentration covered his face. She watched as his cock slowly, but surely, increased in size and hardness.
Silently, she brought down the crop in a blindingly fast arc, smacking the student's balls.
"What did I say?"
"S-sorry mistress I couldn't help it, I-I-I-"
"Shut up!" she yelled, and he went silent. Iris noticed that the student had a size three plug in his harness, and came up with an idea immediately.
"Miss Ives, I'm sorry to trouble you again, but could you fetch me a size four plug from Nurse Verne's office?"
"Certainly," she replied. "This one isn't much enjoying himself." She gestured to Brian, who was writhing as the plug inflated for the tenth time - his cock was completely limp. "I'll be back momentarily," and she strode out of the dormitory.
"Better get you prepared for your upgrade," snarled Iris. God, this feels so good, she thought. No wonder my teachers didn't skimp out on the punishment!
Attached to each corner of the bed was a single brace - two for the wrists, and two for the ankles. Iris bound the student, who was still whimpering from the blow to his now very tender balls - now he could only move his ass backwards and forwards. Out of her bag she produced a large cock ring, designed to be fitted around both the scrotum and the base of the cock. Attached to it was a long string.
Iris clicked the ring on and gave it a tug.
"Do not move," she commanded, drawing the student's cock and balls up behind his legs. Then she let go.
"Do you know how large a size four plug is?" she asked.
"Three-and-a-half inches in width, six inches in insertable length. Seven inches total length," recited the student.
"Correct," said Iris, and, without warning, shoved the first three fingers of her lubed-up hand up the student's ass.
"Uuuugh," he moaned, and instinctively moved away.
Not so fast, thought Iris, and with her other hand, yanked the string attacked to the cock ring, pulling the student right back onto her stiff digits. And she kept him there, slowly increasing the tension on the string.
She introduced a fourth finger to his butt-hole, and then a thumb, and all the time thrusting in and out of the steadily loosening ass. Once he got past the joint of her thumb, she pulled his genitals down, forcing him into a kneeling position, and rested her elbow on the bed, fist pointed skyward.
He had nowhere to go but down - and down he went. Iris could feel his ring expanding around her fingers as he sunk.
He stopped dead once he reached her knuckles, panting, fighting against the taut string. It was clear his ass wasn't quite ready for the rapid expansion.
But Iris didn't care.
She gave the string an even bigger yank - the ring slid down the student's cock and scrotum, then stopped once his balls had nowhere to go, bunched up against the end of his dick. And she yanked again.
He slammed down with all his weight onto Iris's awaiting hand, as she kept the pressure up on the string. The student moaned and writhed, trying as hard as he could to fight through the pain(s).
Just as Iris thought he might not be able to do it, he came down with slurp onto her wrist. Iris gasped - she couldn't help but feel a little turned on. Both his anus and anal cavity gripped her hand like a wet glove.
The student was panting as sweat dripped from his brow. Judging by how tightly his ass was gripping Iris's wrist, she figured he was still in pain. With her free hand, she removed the ankle braces and then the cock ring, allowing his now purple balls to breathe.
But it wasn't over yet. I have to show them that being new does not make me any less harsh than Ives.
Iris made a fist with her right hand, then sharply pulled it from the student's ass. It made a wet popping sound upon exit, and ass juices dribbled out of the gaping hole. She grabbed the student's right arm and wrenched it behind his back.
"Your ass will need to be ready for when mistress Ives returns with your new plug. So," she lathered his hand with lube, then shoved it into his own, ready ass. "Better keep it loose."
The student groaned, and shoved his face into his pillow. His hand wasn't going anywhere.
She checked the remainder of the silent students. All of their asses passed.
Once more, she approached Brian. The hissing noise was still going, but he had stopped moaning.
"What have you learned?" asked Iris.
"I am to keep my ass thoroughly prepared for inspection each morning. If I do not do this to a satisfactory level I will be punished," he recited.
"That's right," said Iris, then pressed the 'STOP' button on the base of the plug. It didn't deflate, but simply remained at whatever size it was currently at. Iris aimed to find out exactly what that size was.
She grabbed the base and wrenched it out of his ass.
It was almost at full size, and his anus stretched away from his body as it was pulled out with a long, wet slurp. The head popped out, and Brian's hole started to wink involuntarily. He shuddered in relief.
"What do you say?" asked Iris, and stroked his balls with the crop once more.
"Th-thank you, mistress."
Hmm, thought Iris. Miss Ives still hasn't returned. I should probably come up with one last punishment, so she can see just how much of an excellent mistress I am.
A smirk came across her face. "Brian, you did so well there. I think a reward is in order."
Headmistress Ives marched back along the corridor towards the B3 dormitory. Nestled in her cupped hands was a size four butt plug.
As she approached the doors, she began to hear loud moans coming from within the room. I wonder what she's come up with, she thought, and smiled.
As she entered, her eyes were drawn to three people. The first was the student who was receiving the new butt plug. He was on all fours, bucking back and forth on his bed. Behind him was Miss Belle, who was on her knees, also on the bed. She was rapidly thrusting the half-inflated dildo plug in and out of his asshole. Her hair had come undone, and her fringe was splayed out across her sweating face - she was really getting into it.
The third person was Brian Yarnell, whom she had been tasked with watching earlier. He was on the floor, on his knees, face buried in Miss Belle's ass.
"Yeah! How do you like it!?" yelled Miss Belle as she ploughed the student's ass with the massive dildo. She turned, then shouted at the other one, "Yeah, uh, shove your tongue up my dirty hole! Lick it clean!"