Chapter 2

Mornings started early at the St. Margaret’s Academy for Wayward Girls, and an hour before the first light of the sun had even broken across the sky, the dormitories were already abuzz with activity. To any visitors who happened to be walking by, it would have been a most industrious sight to see. Hundreds of girls from all over the country, doing their best to rise early and prepare themselves for school. How incredulous, how inspiring. How incredibly proper and charming. Of course, that was only if they were unfamiliar with the inner workings of the academy.

For the girls themselves, the reason was far less grandiose. Nobody, not even the most disobedient of the delinquents, wanted to be marked late for their morning inspection of the day.

Quick showers were taken, beds hurriedly made, and in between the chiming of the old clock tower at 7:00 am sharp and the first of the morning rays, it was time to begin. Standing in a line and ordered by grade, each girl would raise the front of their skirts in turn as the Sister in charge walked past to check for any signs of nightly sin. A quick swipe with two fingers along the seam of their panties, and a pink slip was handed out to the worst offenders. Then, it was off to the breakfast table for a quick bite before classes could begin.

The ritual was of such importance that save for illness, no girl was exempt from attending. For Mary Ellens however, standing in the headmaster’s office with a sheepish look on her face, that was exactly what had happened. Shuffling her feet around, she handed the headmaster the slip of paper she was holding. Yellow, not pink, thank god for that, but it made little difference all the same. Instead of being caught with her hands between her legs, she had somehow managed to oversleep, and had missed the inspection in its entirety.

From his usual place behind his desk, the headmaster looked across at her with a bemused expression on his face.

“So let me get this straight,” he said.

He stopped briefly, as if even he couldn’t quite believe what he was saying.

“You claim that you were unable to wake up in time because you spent the entire night in a closet instead of your bed,” he said.

“No sir,” mumbled Mary, “Not the entire night. Just half of it.”

“And how did you end up there in the first place?” asked the headmaster.

“I locked myself inside, sir,” said Mary.

“By accident?” he asked.

Mary looked away, in the silence that followed, the headmaster almost seemed to be at a loss for what to say. Then, to her surprise, he started to laugh, and she felt shame rush up into her face. She was here to be punished, not to be laughed at for her mistakes!

Still, even she had to admit that it was the dumbest excuse she had ever used. Or even heard, for the matter. Looking up from where she stood, she did her best to look sorry for herself. The last thing she needed now was to make the situation even more absurd.

“Well then,” said the headmaster after some time.

The sound of laughter slowly died down, and he dabbed at the corner of his eyes with a handkerchief.

“I suppose you’re here to make penance for your mistake then?” he said.

“Yes sir,” said Mary.

The headmaster was still smiling, but she felt her heartbeat slowly start to increase in her chest. While not as bad as a pink slip, a yellow slip still warranted a punishment, and she wasn’t looking forward to sitting down with a sore bottom for the rest of the day. Especially considering that most of the chairs at the school were made of oak. With nothing except the thin material of her skirt to protect her rear, just trying to pay attention in class would be a lesson in futility.

For now though, whether her punishment would end up as a spanking seemed to still be up in the air. There was more than just one way for her to repent after all, and leaning back in his chair, the headmaster folded his hands across his chest. Hopefully, he was feeling a little more lenient today.

“Alright, I do want to know one last thing though,” he said, “How on earth did you manage to get out?”

For obvious reasons, most of the doors at the academy could only be unlocked with the proper key. The fact that many of the students came from wealthy families probably had something to do with it.

“I unscrewed the doorknob, sir,” said Mary.

“Unscrewed?” said the headmaster.

His eyes widened as he leaned forward, and she blushed in turn.

“I knew I wouldn’t be able to pick the lock, but by chance I found a screwdriver inside and so I just thought that-...,” said Mary.

In spite of her best intentions, the hole she had dug underneath herself only seemed to grow deeper as it dragged her down. Before she could get a chance to recover however, she was cut off again as the headmaster laughed again. Clasping her hand over her mouth, she tried to preserve what little sanity there was left. The situation was getting more and more ridiculous by the minute, and she only had herself to blame. Whatever her punishment was going to be, it was not going to end well.

“That is the first time I’ve ever heard such an excuse,” said the headmaster.

“I’m sorry sir,” said Mary.

“I’m sure you are,” he said.

But a moment later, his smile seemed to fade, and the room grew quieter.

“But I assume that unless you have something else to say, then the academy is now in possession of a broken door?” he asked.

“I-...,” said Mary.

She hadn’t thought about it that way before, and now she looked down towards the floor in shame. Stuck there in the darkness though, what else was she going to do? Someone was definitely going to have to come around later to fix what she had done. It had taken her an entire half hour of fumbling about to take the handle off, and putting it back together was something well outside her expertise. Not to mention the unknown number of screws she had no doubt lost as well. With the school having been built so far out from the nearest town, she didn’t even want to think of how much it would cost to drive someone out.

“I really am sorry, sir,” she said again.

The headmaster looked across at her as if trying to decide, and a long while seemed to pass before he finally made up his mind.

“Well, I suppose if it’s just a door, then I can overlook your behavior just this once,” he finally said.

“Thank you, sir!” said Mary.

“However, structural damages aside,” the headmaster continued, “There’s still the issue of your absence this morning. The academy has a rather strict policy on such behavior you know.”

In this case the headmaster was correct. And as much as she wanted to believe otherwise, the rules were more than clear on the consequences of missing an inspection, and she had been naïve to think elsewise. Perhaps the headmaster could write off a broken door, but letting her go on such a serious charge was most likely something even he couldn’t excuse. Whatever hopes she had of escaping without punishment disappeared as she looked back down towards the floor.

There was no need for the headmaster to say anything else after that as she slowly reached up to undo the buttons of her uniform. Like every other girl at the academy, she had been punished more than enough times by now that she knew the steps by heart. Setting her school blazer to the side, she stripped free of her skirt. Then, with trembling hands, she lowered her panties down to her knees.

“Over the desk now,” said the headmaster.

Forcing herself to move, Mary did as she was told. Leaning forward over the smooth grain of the surface, she made herself comfortable the best she could before reaching back behind herself to spread open her cheeks.

“Please sir,” she said, “Can I at least pick?”

“Pick?” asked the headmaster.

Pick, of course, whether she was to have her anus or her clit disciplined today. And bent over the edge of the desk like this with the tight entrance of her ring spread apart between her fingers, it was quite clear which one she preferred.

“Oh no, not like that,” said the headmaster.

“But sir-...,” said Mary.

“What I mean is that your punishment will be quite different from the usual spanking today,” he said again, “You may still keep yourself spread open however, if you think it’ll make things easier for you.”

There was a pause as she tried to understand, and the headmaster reached into the drawer of his desk to take something out. Instead of the leather crop or the cane as she had expected, he held up a small device in the palm of his hand.

“This,” said the headmaster, “Is an anal plug.”

The toy was small for its size, though given where it was likely to end up, it was still quite larger than she would have preferred. At a little over three inches long and just under an inch or so wide, the sides flared out to form a tapered base, and she swallowed on a dry throat. Compared to a spanking, this almost seemed worse.

“Is that-...?” she asked.

“Of course,” said the headmaster, “Since you seem to have trouble waking up today, I figured I’d give you something to keep you awake.”

In a strange sort of way, the logic made sense. It was hard to argue against the facts. With something like that shoved up her rear, she would have more than enough reason to stay awake for the rest of the day. Actually being able to focus on her classes, however, was an entirely different matter.

“Is there no other way?” asked Mary.

“Not unless you want to take fifty with the paddle,” said the headmaster.

Well, fifty didn’t sound so bad...

“And ten more on your holes,” said the headmaster again, “Both of them, I’m afraid.”