The Headmaster's Office Ch. 05

In the three weeks that had passed since her punishment first started, Reena was barely any closer to finishing than when she began. She stared down at the half-finished piece of paper in front of her, her fingers trembling as she held onto the pen.

On the Proper User of Titles And Addresses: While present on academy grounds, students are required to obey all instructions issued to them by the faculty members of the school. This rule applies regardless of whether the semester is in session. Upon being a command, students will greet faculty members with the proper form of address and in the appropriate present position, including but not limited to...

Another mind-numbing passage from the student handbook that she was supposed to copy all the way through from front to back. In the span of nearly a month though, she had barely managed to get even a quarter of the way through. Only a hundred pages so far out of the four hundred that existed, and that didn't even include the prefix or the index. Add those on, and it was closer to five hundred in total.

Reena groaned as she spotted yet another error. The word "And" was supposed to be lowercase when used in a title, and she had written it the other way around. Letting out a sigh, she reached for a fresh piece of paper and started over again at the top of the page. This was the third time she had messed up so far, and she only had herself to blame. If she wasn't careful, then the end of her punishment would only get further and further away.

From across the room, the headmaster glanced over the top of his desk with a concerned look in his eyes.

"Is everything alright?" he asked.

"Y... yes sir," mumbled Reena.

"Are you sure? Should I turn it down or...?" asked the headmaster.

And there was the question that she had been dreading all day. A cold wave of panic washed over her as Reena froze in place. She hadn't even made any noise! There was no way the headmaster could have known just how close she was to a climax from by looking at her.

Tightening her grip on the pen, she tried to avoid his gaze. She could ill afford another infraction, especially not when she was already halfway through the hour-long period that she was supposed to stay.

"Oh no, I'm perfectly fine sir," she blurted out, "There's... there's no way something like this would ever make me cum sir."

"Are you sure?" asked the headmaster, "You know what happens if you do right?"

Her hands trembled, and Reena struggled to focus on the words in front of her as they blurred.

"Y... yes sir," she said, "I promise I'll hold it in sir."

A moment of silence passed as the room grew quiet again, and she shrunk down underneath the intensity of his stare. The fact that her nipples were standing straight up from her chest didn't help at all with the color running across her face. Stiffening as they swelled against the air, the two points felt especially sensitive as they rose up from the center of her B-cup breasts.

After a moment of trepidation however, the headmaster finally seemed to relent.

"Well, if you insist," he said, "Just let me know if it becomes too much for you, and I'll be more than happy to start the timer over again at a lower frequency again."

He looked back down to his desk, and Reena let out a sigh of relief as his gaze shifted away from her naked chest. The comfort didn't last long however, as the dildo she was sitting on continued to buzz in her rear.

A soft hum, almost like that of a whisper filled the room as it vibrated deep inside her bottom, dragging her slowly up towards the peak. Then, just when she thought that this time was finally going to be it, the stimulation cut off for the umpteenth time, and she felt the walls of her tunnel clench down in frustration and despair. A feeling of emptiness raced through her as her legs snapped together, and her toes curled inward in a desperate attempt at relief.

"Mmmnnhhh..."

Biting back a moan, Rena whimpered quietly under her breath. That must have been the fifth or sixth time she had been edged today, and she winced as her hips jerked forward in the punishment chair. Closing her eyes, she forced herself to ignore the throbbing between her legs. Now was not the time to be caught up in her desires like this, not while she still had to focus on the current task at hand.

No matter how much she tried to resist though, every time it happened, the results were the same. A soft buildup of vibrations to bring her right to the brink, followed immediately by the painful frustration of not being able to finish as she was once again denied. And the worst part of it all was that it was done without any stimulation to her tunnel or her clit. Only the endless movements of the dildo as she sat there with its full length buried up her rear.

"Pleasepleasepleaseplease..."

One last burst of agonizing pleasure to keep her right on the edge, and Reena let out a silent prayer of thanks as the dildo finally ceased. Instead of a blessing however, the break was more of a curse instead. While long enough for her to cool back down, it was also just short enough to ensure that when the vibrations started up again, she would wind up hitting the next one even quicker than the last. The first couple of times it happened, it was mostly fine, but over the course of an entire hour, it would get harder and harder to think of anything except how much she wanted a release. A release that she would never get so long as her work was incomplete.

One... two... three... four... five...

Deep breaths now, and counting out loud inside her head, Reena lowered the pen back against the page. If she was quick about it, she could probably get at least a few paragraphs copied over before the next round of vibrations started up all over again. Repeat the process a few more times, and she might even be able to complete another chapter, bringing her one step closer to the end.

"Are you sure you're alright?" asked the headmaster.

Staring down at the miniscule text in front of her, Reena tried to hide her tears as they flowed down her face. At the current rate she was going at, the semester would end long before she would be able to get even three-quarters of the way through to the end.

"Y... yes sir," she sniffed.

"You know, if you're not feeling well, then maybe we should stop for today," said the headmaster.

"But what about...?" she asked.

"You can pick up from where you left off tomorrow," said the headmaster softly, "As long as you're still committed, then you're welcome to keep coming back for as long as it takes."

Of course, there would be consequences for stopping early, but between the endless vibrations of the dildo and the soul-sucking dullness of the task, there really wasn't much more that she could take. Every second that she sat there felt like torture as she tried to push past the frustration between her legs, and already she could feel the wetness of her own arousal clinging to her as it seeped out onto the seat. She felt sore all over, and the feeling of emptiness wasn't helped at all by the fullness in her rear.

In the lazy sunlight of the room, with the passage of time frozen in between, it was only with the slightest moment of hesitation that Reena dared to nod her head. She had to pick now, before the situation got any worse and she accidentally came.

"Thank you, sir," she whispered.

She would have to make up for the time she forfeited at a later date, but by now, she was past caring what her future self would think.

&&&&&&

As always, saying yes was the easy part. Actually following through, however, was another matter entirely. Reena winced as she stood up, and the dildo she was sitting on slowly slid out of her rear. With the tip being just a little wider than the shaft, she felt it pushing against the insides of her rectum as it scraped past. Then, it was finally out of her, and she let out a sigh of relief.

"Present," said the headmaster.

Placing her arms on top of her head, she turned around to face him with her breasts thrust up into the air, and tracing his hand over the stiffness of her nipples, the headmaster lingered over the tiny nubs for what seemed like an eternity as she held her breath.

"How close were you really?" he asked.

Reena grit her teeth, wondering whether it would be worth it to lie.

"Eighty percent," she mumbled.

"Only eighty?" said the headmaster.

His hand moved downward to press against the hood of her clit, and she winced as he brushed over the sensitive bump at the top of her slit. A spark of pleasure shot through her, and it took her almost everything she had to stop her hips from jerking forward in response.

"Maybe ninety," she gasped, "It's... it's hard to tell..."

Another touch, and she whimpered as she tried to hold herself still. She couldn't afford to show weakness now, not when she was already this close to the edge. A few more seconds, and she really might not be able to hold it in anymore. If that happened, all the work she had done would have been for nothing, and she would have to start all over from zero again.

Tap, tap, tap...

"Please sir!" cried Reena, "Ninety-five!"

Tracing his finger one last time over the folds of her lips, the headmaster moved down at the last second to rub against the outer rim of her entrance, and Reena grit her teeth in frustration as she was denied once more. Still keeping her hands together on top of her head, she breathed hard as she tried to ignore the ache between her legs. She could feel her clit straining upward as it throbbed underneath the tight confines of its sheath.

"A little close there, don't you think?" said the headmaster.

"I'm sorry sir," mumbled Reena.

"And only after a half hour in the chair," said the headmaster.

"Please sir, I'll do better next time," promised Reena.

For what it was worth, it felt more like an eternity instead. The headmaster reached out to pat her bottom, and his fingers dipped in between the curve of her cheeks to press against her anus as well.

"Of course," he said simply with a smile.

There wasn't much else to say after that as he walked over to his desk. Taking out a second dildo from the drawer, a flesh colored one this time around, he attached it by the suction cup to the floor.

"Five minutes," he said, "And then you're free to go. You can start whenever you please."

That meant now, and getting down on her knees, Reena shuffled forward to take the toy in her mouth. The taste of the rubber hit her, and she gagged as it pushed against the back of her throat. It felt humiliating to degrade herself like this, but unless she wanted to risk an infraction, then there was no choice for her except to continue.

Slowly, Reena drew her head back until only the tip of the dildo was pressing against her lips before sliding back down again until the entire thing was buried inside the warm confines of her mouth. Repeating the movement, she slowly licked upward along the entire length of the shaft with her tongue.

"Mmnnnnn..."

Five minutes, that was all that she needed to do. She repeated the mantra to herself over and over again. What was five minutes of humiliation compared to an entire hour of being edged with her rear? But kneeling down on the ground like this with her bottom stuck up into the air, she couldn't help but blush again at the wetness slowly leaking out of her slit. Every second that passed made the shame feel even worse, and she tried not to think about what she looked like with the full length of her privates exposed for the entire world to see.

The headmaster looked over from behind his desk, and it took her a few moments of panic to remind himself that he probably didn't care. He must have seen at least a hundred other girls bend over in front of him in this exact position before.

"Having fun?" he asked.

"Mmhnn...," said Reena.

"You know, you could always request a lower setting the next time around," said the headmaster, "Of course, you'd have to compensate for it with a longer session in the chair, but it should be easier for you to focus with the vibrations turned down."

He reached out to press a finger against her anus again, and Reena moaned as she sank her mouth down on the dildo once more.

"Mmhnn...," she said.

It was a kind offer, but it seemed almost redundant as she licked upward along the length of the toy. If she couldn't stand even thirty minutes of being edged, what good would increasing the total amount of time do for her then? Even with the vibrations turned down, the frustration of being denied felt so much worse than everything else.

Her clit throbbed again underneath her hood, and she tried to ignore the frustration of the denial as it screamed out. Her entire body felt like it was on fire, and a small part of her wished that she would be allowed to ride the dildo instead. Unless she wanted to risk losing her virginity however, there was little chance of that.

"Four minutes left," said the headmaster.

Still four? There was no way only a single minute had passed in all that time, and already her jaw was starting to feel sore. Reena shivered again as she felt her hips rise further up into the air. The constant texture of the phallus against the inside of her mouth wasn't helping, and she felt her concentration starting to waver again as a fresh trickle of wetness leaked out from between her legs. Every time she leaned forward now, she could feel her labia parting to reveal the thin membrane of her hymen inside her virgin tunnel.

"Three minutes," said the headmaster.

He opened a drawer, and hammered into her through a multitude of experiences before, Reena braced herself for the sudden touch of lubrication between her cheeks. A vibrating plug, a string of beads, or perhaps even a fig of ginger, she closed her eyes as she prepared herself for the worst. A moment later however, when nothing happened, the headmaster laughed as he looked down at her with his finger still pressed up against her hole.

"Were you expecting for me to put something inside?" he asked.

"Mmhnn...," said Reena.

A smile stretched across his face, and he laughed as he rubbed his finger against the outer edge of her ring.

"Don't worry," he said, "I won't put anything inside unless you really want me to. Of course, I can't say the same about your other bits down here though..."

With her hips raised up at just the right height, it was more than easy enough for him to reach down to rub along the length of her lips, and in the midst of her lust filled brain, Reena could almost see him smiling as he peeled back the hood of her clit. Sparks of pleasure shot through her as he brushed lightly around the circumference of her bean, and she whimpered as he denied her the satisfaction of anything more than a light touch across her skin. Already swollen and stiff from her earlier ordeal in the chair, she could feel her clit straining upward even more as it throbbed against the air.

The worst was yet to come however, and as the headmaster reached into the drawer again to take something out. Tensing up, she heard the unmistakable sound of a jar being opened, and then a cotton swab as it was coated with a generous amount of capsaicin oil.

"Mmhnn...," she cried, but the headmaster ignored her.

"Just a little something to think about later on in class," he said, "Plus, it'll help you keep your hands away from yourself unless you want to risk having your fingers burnt as well."

Snapping on a pair of latex gloves, he reached down to press the end of the swab against the opening of her tunnel, and desperately shaking her head from side to side, Reena did everything she could to escape. No matter how hard she tried however, the movements were futile as the headmaster held her down. Keeping her spread open with one hand, he slowly inserted one end, and she cried out as the substance oozed out into the depths of her hole.

"Mmmnnnn!"

The moment the oil touched her, it was as if her body was filled with nothing but the harsh grating of rusty sound. Liquid fire, and then pain. It was the only way to describe how awful it felt. Halfway gagged though with the dildo still in her mouth, there was no way for her to scream unless she wanted to choke herself. Swallowing hard, Reena desperately stared at the floor in front of her and doubled her movements as if it would help. Behind her, she could hear the headmaster as he coated a second swab with oil before dabbing it around her clit as well.

"One minute," he said, "Stay strong now."

Sixty seconds, that was all that was left on the timer. But having been kept on the edge for so long, her entire body was beyond sensitive now, which made her feel all the more vulnerable as the oil went to work. Reena whimpered as the heat spread through her, amplified further by the frustration bottled up inside.

The headmaster reached out to insert a finger back into her bottom, and the suffering only intensified as he began to slowly thrust them in and out. Doing her best to hold herself up, Reena gasped as the dildo slid out of her mouth.

"Sir, please...," gasped Reena.

"Have you decided to go back to the chair?" asked the headmaster.

"Sir, please! I'm going to cum," cried Reena.

Teetering on the edge of the most wonderful orgasm in the world, it was as if her head was filled with nothing but noise as she struggled against the last inch of the abyss. Every time she peaked, the headmaster would stop, and she cried out loud as both her holes clenched down. The more she tried to move, however, the more the oil ended up being spread around. She was so close now, just a little more and...

"No you won't," the headmaster said softly, "I won't let you degrade yourself. Maybe a ruined release at the end of your punishment, but for now, you'll need to hold it in until the end like a good girl."

An eternity of frustration as the words stabbed through her, and Reena closed her eyes in submission as tears of desperation flowed down her face. The headmaster was right. She couldn't afford to cum, not when she was already a quarter of the way through. Sobbing, she opened her mouth to swallow the dildo again as she counted down in her head. Watching her from behind, the headmaster put his finger back into her bottom once more.

Edge, lick, edge, lick...

The cycle seemed to go on and on until all five of her senses had abandoned her and left. The only thing she could feel now was the endless burning of her privates as she was edged. That, and the tension of her muscles as the frustration coiled up inside. With nothing to focus on except the blank white surface of the wall in front of her, it wasn't long before her imagination started to run wild.

It was impossible, it was absolutely impossible, but looking up from where she knelt, she could almost imagine a stranger standing in front of her, his member in her mouth where the dildo would have been. Smiling, he reached down with a blindfold, and her vision went dark as he wrapped it around her head. A hand pressed down against the back of her neck, and she gagged as something stiff pushed its way past her lips.

Slowly, the stranger started to move, and then there was no time to think, only to draw in whatever air she could get as she tried to make him spend. The faster he finished, the faster she could breathe again, and a single wrong move on her part was enough for her to pass out. Desperately, Reena moved the tip of her tongue up to service the head.

Edge, lick, edge, lick, edge lick...

Please, hurry up, she begged.

Lick, lick, lick...

A long time seemed to pass as the stranger used her, and it was only when she was at the limits of her consciousness that he finally relented. Grunting hard as he pushed one last time into the back of her throat, his member swelled up as it pulsed in her mouth, and she felt the bitter taste of something salty spurt out. It coated the surface of her tongue, and she gagged at the disgusting texture slid down her throat.