Classroom Stories Ch. 02

"My... back there," she said at last, and smiling to himself, Mr. Wilson gave her one last rub around the outer edge of her anus before sliding a small vibrator past the entrance of her slit. Then, taking hold of the thin wooden rod, he raised it high up into the air.

"If it falls out, we'll be starting all over again from the beginning," he said.

There wasn't much else to say as the punishment began. The first stroke fell down vertically between her cheeks, and Amanda cried out it cut straight across the tight surface of her skin.

Crack!

"Ohhhh!" she said.

Dancing up and down in place, she sobbed as the vibrator started to buzz away inside her, the long wire flailing about as she shook her hips. Balanced against the soft sea of pleasure making its way up into her brain, however, the sharpness of the stroke cut right through her mind as the pain dragged her back from the edge.

Crack!

"Ahhhh!" sobbed Amanda.

The next stroke was just a little off center and to the right, and she gasp as her hips continued to sway. Running his fingers over the sensitive marks left across her skin, Mr. Wilson didn't even bother to give her time to recover as he raised the cane.

Crack!

Crack!

Crack!

"Higher or it won't count," he said, and she sobbed as she did as she was told, raising her bottom even higher as she bent over to push her face towards the floor. From behind, she could only imagine the way she looked with the red stripes of her punishment running down and between the cleft of her cheeks. Positioned just an inch or so below, the vibrator continued to buzz away inside her endlessly twitching hole.

"Bzzzzzzzzttt..."

Every time she clenched down, the natural movement of her walls would draw the toy deeper inside. The moment it reached far enough to brush up against her g-spot, however, the sudden increase in tightness would only cause it to retreat the other way. Thus, with every stroke of the cane, she was left with no other choice but to endure the endless thrusting of the small, egg-shaped device as it shifted back and forth inside her love tunnel.

Crack!

Crack!

Crack!

Another stroke, and then another, as each blow caused her entire world to tilt and blank out. All while she stood there with the back of her skirt lifted upward and her panties drawn down to her feet. The vibrator moved over her g-spot again and she sobbed in despair. No matter how close she got, every time she hit the edge the cane would simply reintroduce itself as she screamed out in despair.

Crack!

"Bzzzzzzzzttt..."

Crack!

"Bzzzzzzzzttt..."

Back and forth, back and forth, Amanda wailed out loud as her entire body felt like it was being drawn out like a string. Every time she thought that this time was going to be it, the red-hot fire of her punishment only drove her back to the very beginning. Another pulse from the device inside her, and she sobbed as her clit throbbed from behind its sheath. A single touch was all she needed, but with the vibrations still stuck on the lowest setting, there was just simply no way she would be able to finish.

It wasn't until they had reached the halfway point that Mr. Wilson paused for a break, and setting the cane aside he reached out to massage the swollen welts with his hand. Running his fingers over the tender surface of her anus, he played with her there for a while before finally moving down to spread apart her lips. Pulling the vibrator halfway out, he let go of the wire and watched as it slid back in.

"How many times did you try to cum just now?" he asked.

"I... I don't know," sobbed Amanda.

Another tug from the wire, and she gasped as the toy moved to press up against her g-spot again.

"If the stimulation is too strong, perhaps you would like to switch?" asked Mr. Wilson.

With her hips still shaking from the strain of having to stay bent over, Amanda desperately shook her head. While switching the vibrator to her ass would at least remove some of the stimulation, she didn't much like the thought of having her pussy caned instead.

"Please sir, my anus!" she gasped, "I'll do anything! Punish my anus, just please don't spank my pussy again."

Mr. Wilson smiled, and letting go of her lips, he watched as her labia closed up again. Even despite the harshness of the punishment and wetness clinging to her lips, only the tiniest sliver of pink was left visible around the place where the wire stuck out. A perfectly painted picture of virtue, were it not for the way her clit jutted out underneath. Still trapped behind its hood, the sensitive little organ looked painfully swollen as it strained against the tightness of its sheath.

The switch was next, however, and setting the cane aside, Mr. Wilson knelt down behind her to face her rear. Placing his thumb and forefinger just beyond the edges of her ring, he slowly pulled them apart until her anus was stretched tight. Then, holding the thin willow switch just above, he gave her a quick stroke directly across its entire length.

Smack!

"Aaaiieee!" cried Amanda.

She tried to clench down against the pain, but with the fingers still stretching her apart, her muscles almost seemed as if they were stuck in place. Again, the switch came down to land against her anus, and she sobbed as the impact seemed to echo throughout the whole of her rear.

Smack!

Smack!

Smack!

Smack!

Smack!

They had to be getting close to the end, and Amanda let out a silent prayer to anyone who happened to be listening. Bent over as she was though, it was hard to be certain of how many there were left. Every second that she had to stand there felt like an eternity of torture, as Mr. Wilson continued to spread her apart with his hands. With her cheeks pulled to the side, there was nothing to protect her as the switch came back for another stroke.

Smack!

Only three more now...

Smack!

Two more...

Smack!

One more...

Smack!

As the final blow fell across the stretched-out ring of her anus, Amanda howled as the rod cut painfully into her flesh. The vibrator pulsed one last time against her g-spot, and as the sound of her heartbeat filled her ears, something inside her seemed to break at last.

"Oh!" she gasped, "Oh... oh... oh..."

She was cumming, she was cumming, she was finally going to cum, and the entire world seemed to fade away as the tension in her muscles rose up like a hurricane. Trembling like a leaf, her hips shook up and down as her clit strained against the air. Any moment now, and then... and then...

Except that no matter how long the feeling continued, her orgasm still remained elusive as ever and out of reach. There was what felt like the ghost of a contraction, and then propelled by the sudden tightness inside her body, the vibrator finally slipped out of her just as she hit the peak. Absent of that final millisecond of stimulation, there was nothing to carry her over as the movement of her walls were met by nothing but empty air.

"I'm cumming! I'm cumming!" she sobbed, but it was no use. No matter how many times she cried out, the climax never came. Desperately, she tried to move her hands down between her legs but Mr. Wilson only shook his head as he held them out of the way. By the time he let go a minute later, it was already too late. With her body already starting to cool back down, Amanda sobbed as she was left with nothing but the aching emptiness that still lingered within.

"There's a good girl," said Mr. Wilson, "You'll get another chance to try again next semester, so just be patient and hold it in until then."

Cleaning her up between her legs, he slowly pushed a medium sized dildo into her bottom before drawing her panties back up around her waist. Then, smoothing the fabric of her skirt down over the bulging base, he waved for her to go back to her desk. Slowly, Amanda winced as she sat back down in her chair. Until class was over, she would simply have to do her best to ignore the feeling of being filled back there.

"Now, since it looks like we've run out of volunteers...," said Mr. Wilson.

Up on the wall, the clock struck a quarter to nine, barely thirty minutes since the class had first begun. Looking about the room, he carefully selected his next victim. A timid-looking girl with lightly colored hair, there was just the briefest moment of hesitation as she looked up from her desk. Then, like a prisoner standing before the gallows, she slowly lifted her skirt up as walked over towards the front of the class.

With nearly an hour and a half left before the period was due to end, that left plenty of time for another few chapters at least. As the girl reluctantly slid her panties down to expose the delicate shape of her slit, Mr. Wilson couldn't help but smile again. Already, his fingers were making their way down towards her clit, and it would be quite a while before she would be able to go back to her seat. Of course, that didn't make her exempt from having to keep herself under control every time she hit the edge. It was the only way she would be able to earn the points she needed an orgasm after all, and he would have to be beyond cruel to deny her the only chance she had at relief.

As the girl slowly began to read from her textbook, the rest of the class blushed as they looked away from the scene. Keeping their legs pressed together underneath their desks, they desperately waited in silence for the bell to ring. Until it did, however, they had little choice but to sit there with their panties growing wetter and wetter as they counted down the days they had left until their next sanctioned release.