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. She was eighteen years old now. How on earth did such a thing happen?

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 to 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.”

That was more than enough to get her to shut her mouth, and clenching her teeth together, Mary forced herself to decide.

“Thank you for punishing me with a plug, sir,” she said.

With that out of the way, the headmaster smiled as he got up to walk around the edge of his desk. Running his hands up the inside of her thighs, he used his fingers to feel in between the sensitive folds of her lips. Desperately, Mary prayed that she was still dry. Even if she wasn’t the one who started it, she could still end up with another infraction if she went past the limits of her permitted arousal.

For the next few minutes, she held herself as still as possible while the headmaster teased her around the hidden entrance of her virgin tunnel. Then, satisfied at her abstinence, he moved further upward to press against the puckered entrance of her backdoor. There was the cold touch of lubrication, and then the sensation of something entering her as he pushed the tip of his finger ever so slightly inside.

“Ahh…,” said Mary.

It was hard to stop herself as her voice flowed out. Spreading her cheeks apart even further, she forced her bottom up even higher as she tried to escape the intrusion.

“Sir, please, not so sudden,” gasped Mary.

“Hold still now,” said the headmaster. “You wouldn’t want me to put it in the wrong hole now, would you?”

Judging from the way her insides were starting to clench, it was doubtful whether her body felt the same way. There was no way she could ask for such a thing, however, without also giving up her virginity as well. And with her purity being a requirement for her continued enrollment at the school, her parents would be more than disappointed with her if she did.

“Ohhh…,” said Mary.

It seemed like an eternity went by as she lay across the desk, and she breathed out a sigh of relief as the headmaster finally drew his finger back out. It didn’t last long, however, as he reached for the plug next.

“Ready?” he asked.

With the only other option being fifty strokes with the paddle, and then ten more upon both her holes, it wasn’t exactly as if she could say no.

“Yes sir,” said Mary, “Thank you, sir.”

It was then that the real punishment began. Still keeping her cheeks spread apart with her hands, she took a deep breath as the headmaster reached down to press the plug against her backdoor. The tip of the toy slid inside, and aided by the lubrication, the rest of it followed soon after as well. She felt her body stretching around the widest point near the base, and then she gasped as the muscles of her ring squeezed down.

The plug was now inside her, but it wasn’t over just yet. As the headmaster pressed a button, the entire device started to vibrate. Biting down on her lips again, Mary struggled to keep herself still. Between her legs, she could feel the walls of her tunnel clenching down. With nothing to hold on to, however, it didn’t feel satisfying at all. A minute passed, and then another as the headmaster reached down to run his finger in between the soft contours of her folds, teasing her ever so slightly without letting her spend.

“Hold it in now,” he said.

Mary tried, she really tried. With the fullness of the plug still stuffed up her rear however, she couldn’t help but be dragged higher and higher up the mountain and towards the edge. Especially when the headmaster reached down to peel away the hood of her clit. Her nipples were harder than steel now as they pressed against the surface of the table, and she could hear the beat of her pulse pounding in her head. When the headmaster brought his finger back down to circle the entrance of her tunnel again, it took her everything she had to stop her hips from thrusting back against his hand.

“Please sir, I can’t,” she begged.

But the headmaster simply shook his head.

“Ten minutes, hold it in,” he said, “For every minute you don’t, it’ll be a week in chastity.”

There was no stronger motivator than that, and Mary clenched her teeth together as she did her best to endure. Nothing worse than being locked in a chastity belt, and even the red-hot touch of the cane was much more preferred. Or in this case, a vibrating plug stuffed up her rear as she bent naked over the edge of a desk.

The next ten minutes that passed did so with a slowness that made her wish she had never ended up where she was now. Desperately, she did everything she could to stop herself from going over the edge. Biting down on her lips, digging her fingernails into her hands, it all seemed futile against the constant stimulation between her legs. Still, she held on with a grim determination that only ten weeks of chastity denial could bring about.

It was only when the headmaster finally reached for her clit again that she finally broke.

“Please sir, not there! I’m going to cum,” cried Mary.

Desperately, she tried to move herself out of his reach, but there was no escaping it as the headmaster reached out to press against the sensitive organ at the top of her lips. Squeezing her eyes shut, she tried her best to hold herself still. By then, however, it was already too late. The walls of her tunnel spasmed once, twice, three times, and then her endurance failed.

Mary cried out as every muscle in her body tensed up in preparation for the most wonderful climax she had ever felt. Just before she could go over, however, the headmaster withdrew his hand.

“No!” she cried.

The only orgasms that were permitted at the St. Margaret’s Academy for Wayward Girls were those that were given out for good behavior, and bent over the edge of the desk like this with her bottom thrust up into the air, there was no way that she was going to be allowed one now. Out came the leather crop from its drawer as the headmaster raised it high into the air. There was a swish as it fell, and she cried out as it landed squarely against the tender flesh of her virgin hole.

Smack!

Smack!

Smack!

Dancing up and down in place, Mary cried out at the thrashing between her legs. She had been so close. Only a few more strokes and she would have been able to go over the edge. With the pain of the impacts landing against her privates, however, there was no way she could finish now. Laying face down, she sobbed as her orgasm was cruelly beaten into submission, even as her hips thrust backwards in frustration against the empty air. Thrust back inside, the long-awaited pleasure was left with nowhere else to go except to swirl endlessly around.

Smack!

Smack!

Smack!

Smack!

Smack!

Smack!

It was only after another half-dozen strokes that the headmaster finally lowered his hand, and she cried out softly as he reached out to massage the soreness of her flesh. In her haste to escape, a few of the blows had wandered off course, drifting up and across to where the fullness of the plug filled her backdoor. Those were the ones that hurt the most, and the sudden shock of the crop as it forced the toy further inside had had almost caused her to scream out loud.

“Is it over?” she sobbed.

“Ten minutes and thirteen seconds,” said the headmaster, “I suppose that’s enough for today.”

Sniffling, Mary wiped away her tears as she lay across the desk. Reaching out for her clothes, she made to take the plug out, but the headmaster stopped her.

“No, keep it in,” he said, “You can drop by tomorrow though to have it removed before the start of school.”

As if acknowledging what he just said, the plug turned on again, and she jumped as it vibrated softly against her backdoor. A few seconds later, however, she let out a sigh of relief as the power cut out.

“It’ll be a good reminder for you to wake up early as well,” said the headmaster.

He smiled as she reached for her panties to slide them back around her waist. With the plug set to stimulate her at random intervals every few minutes now, she would have to be careful to ensure her thoughts stayed pure until it came out. That was easier said than done though with the heat of her arousal still swirling about.

Her nipples stood up rock hard from the center of her chest as the headmaster drew the covering of her hood back over her clit. Staring straight ahead at the wall opposite to her, Mary tried to keep her voice down. It felt frustrating to have the tiny nub forced back into the confines of its sheath, but at least it wouldn’t rub against the inside of her panties as she walked down the hall.

There was a chime from the clocktower down the hall, and the headmaster glanced over at his watch.

“Fifteen minutes before class starts,” he said, “You better hurry or you’ll be late again.”

“Yes sir,” mumbled Mary.

Grabbing the rest of her clothes, she hurried to get dressed and made for the door. The plug shifted inside her as she moved, and she clenched her teeth together as the walls of her tunnel squeezed down. The denial felt almost painful as stimulation blew fresh air over the embers of her pent-up arousal.

Looking back over her shoulder, she saw the headmaster waving at her one last time with a smile on his face. Then the door closed, and she had other things to worry about. Like how she was supposed to make it through the day without giving out. Already she could feel herself growing wet again, and there was little doubt her panties would be soaked through by the time lunch came around. The soft vibrations of the plug as it turned on again didn’t help.

Adjusting the toy inside her, Mary slowly set off towards the lecture halls. Her legs ached from where she had bent over the desk, and she had a long day ahead of her still.