Chapter 4
by RetrospectiveInsomnia
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Chapter 4
Sasha Blair was the third girl to enter, and the fifth girl to undress. Somehow though, despite having gotten away with just a mere handful or so of taps and not much else, she found herself standing first in line as they were led over to the stations at the back of the office. Blinking, she followed along. What foul luck. Like an entire game full of bad hands. All the same though, the rules were still the rules, and so she said nothing as she continued to walk forward clad only in her panties minus a bra. She had forgotten to put one on in the morning rush.
“Over here,” said the head nurse, “This one.”
She stopped, and Sasha blinked as the woman waved her forward from behind her mask. A bit like a conductor, and the entire class turned to stare as she **** herself to move along. Better an awful plan executed today than a perfect one never, after all. Or so the saying went.
The assistant standing next to the examination table smiled at her, and she **** herself to sit down. Nurse Foley, her nametag read, complete with a ‘Nice to meet you’ scrawled across the top.
“Hello,” she beamed, “Do you want to start with your name?
“Sasha Blair,” said Sasha awkwardly.
“And your class?” she said.
“I’m eighteen-…,” said Sasha, “Er, I mean, I’m in Mr. Johnson’s class.”
“Oh, just like my little sister then!” said the nurse, “Makes sense, since you look about the same.”
Her teeth flashed out, and it was hard not to shrink back a little under the intensity of her gaze. Especially since she only seemed to be about a decade or so older, and the feeling wasn’t made any better as the woman reached over to snap a pair of gloves onto her hands. Like two little safety pins of cleanliness, and she waved for her to lie down on her back.
“Now, Sasha,” she said, “This will only take a moment so if you can keep your hands by your sides for me, that would just be perfect. Any questions before we begin?”
“Should I have any?” said Sasha.
“Do you want to?” teased the nurse, “No points against you if you choose the right to remain silent.”
Sasha blinked at the phrase. That was a joke, right? It sounded like one. There was a pair of handles built into the frame, and she took hold of them without further instruction. Then, with the smoothness of the parchment paper pressed up against her shoulders, the nurse was standing directly over her a moment later as she placed her hands against her stomach.
Press, press, press, her fingers went. Like the soft bristles of a brush tracing a gentle pattern up her skin, and it was hard not to flinch as the soft touch of the latex finally reached her chest. Or rather her lack of a chest, since all that happened in place of the massage she had been expecting was the ticklish dance of something tracing around her nipples until they were standing up stiff.
Doing her best to ignore it, Sasha looked up at the ceiling as she bit down on her lips.
Press, press, press…
The stimulation continued on for what seemed like another couple of minutes before the nurse took a short break to write down the results of the exam. There was the sound of a pen scratching against a clipboard, and she moved her attention back over to where she was lying across the bench. This time to the place where her crotch lay between her legs.
“Any discomfort or swelling?” she asked.
Presumably they were still talking about her breasts.
“No,” said Sasha.
“And what about over here?” she said.
It was hard to concentrate with the way her fingers kept moving over her skin. Especially as the woman drew aside the fabric of her panties to examine her slit. There was the soft touch of air blowing across her folds as she reached over to peel back her hood, and then moving both of her legs to the side so that her knees were pressed up against her chest, she placed her hands on either end of her labia to spread them apart so that her hymen could be seen.
The shame of her embarrassment rose up across her face, and Sasha blushed as she felt the opening of her tunnel let out a twitch. And then a second one a moment later as the fingers returned again to circle her now exposed clit.
“Relax,” said the nurse, “I don’t bite.”
Press, press, press…
“Unless you want me to that is,” she said with a rather mischievous grin.
There was another look that hinted at something that was most definitely not appropriate, especially in a conversation between two girls of which one was currently naked, and Sasha felt herself curl up even more as a blush rose across her face. Gradually, she could feel the tip of her ears turning red. Oh god, the shame. As if she would ever sink so low to do something like that. Even if it had been almost an entire year now since she had last managed to save up enough points.
Biting down on her lips, she looked away. As it was, the worst she had ever done was to hold hands with a boy, and that had been all the way back before her parents had decided to send her here. Past that, the closest she had gotten to the pleasures of a relationship was when Mr. Johnson had called her up in front of the entire school at the end of the year reward ceremony, and in that brief moment of time that he had spent congratulating her on a job well done, it had taken less than sixty seconds for the vibrator he was holding to push her over the edge before he finally pulled it away.
For a single second, she hoped for bliss. Like every other girl who had gone before her though, if that was the expectation then she was sorely disappointed. Instead, there was a brief moment of agonizing regret where the walls of her tunnel quivered on the edge of something that might have been relief, and then after another couple of weak contractions that offered not even the slightest hint of release, she was back in her seat again with her panties soaked through and her fingers clenched together into a fist. And a deeply frustrated thought that maybe she would have been better off if she had decided to skip out on the entire thing.
Ruined orgasms were always like that though, she had to remind herself afterwards, awful all around and in no way satisfying. And at least she got a choice unlike most of the other girls in their class. Several of whom were seated right next to her, and all of which had to suffer through the entire hour-long ceremony with their legs pressed together and a punishment plug buzzing away in their rears.
The rest of the week was only made a little bit better by the fact that she was actually able to fall asleep. Not so much for the inhabitants in the other half of the dormitory she shared, whose gifts of academic failure kept them awake long into the dead of night as they sobbed against the emptiness that lingered underneath the sheets.
“Sasha, dear?” said a voice.
Back in the present, she blinked as her thoughts were interrupted by the sound of her name. The nurse was looking over at her again, and she tried to remember the current topic of their conversation. Something about biting? Then she realized that the woman had her fingers curled past the waistband of her panties, and was in the process of dragging them down her legs.
“Your underwear, please,” she said, as if it was obvious what she meant. Which it sort of was, seeing as the entire reason she was here was for the exam. Sheepishly, Sasha relented, lifting up her hips so that the material could make it past, and then with her body laid flat, her legs were moved to the side again so that her crotch could be seen.
This time, there was no pretense made about hiding her shame. The cold touch of the air brushed over her lips and with her knees pressed up against her chest, it was as if every last inch of her most intimate places were on display. Including both at her privates and her anus, and against the heat of the arousal making its way past her slit, it was almost like she was standing naked in front of the entire world with all her secrets laid bare.
The nurse reached out her hand to touch her again, and dimly she realized that she was starting to get wet.
“Eager now, are we?” she said.
“I…,” said Sasha, “I’m not…”
“Or maybe you really did want that kiss,” the nurse teased her again, her fingers dancing just beyond the delicate nub of her clit, “Though on which one of your mouths is anyone’s guess…”
If there was ever a sign from heaven, then this might have just been it. Or maybe the woman was actually a demon from hell, a succubus of the night who preyed on the unfortunate souls who got in her way, and she was now staring down the end of a gun barrel at the last remaining seconds of her life. Sasha couldn’t decide. Especially not as the touch dragged closer and closer towards in between her legs, and as another trickle of arousal leaked out past the opening of her entrance she could practically feel the heat rising up across her face again. If only she weren’t so weak.
Press, press, press…
They were back to the same game from before, and she whined against the stimulation as her head tilted back. Her entire body was now on fire now, her back arching up in vain, and the pressure building up inside her felt like a bomb just waiting to detonate. Only that she didn’t have permission, even as the fingers came back for a second touch and then a third with each one giving her just enough to leave her wanting, and by the time the nurse stopped again, her brain had all but melted under the weight of the heat.
If this went on any longer, she thought, then she was definitely going to break.
“Please…” gasped Sasha.
“Please what?” said the nurse, smiling again sweetly.
“I…,” she said, “Down there!”
For all her attempts to communicate though, the only thing she got in response was another soft touch along the inside of her thighs. Biting down on the inside of her cheeks, she squirmed as the fingers returned to linger just out of range. There was another tap as they moved closer, tracing a thin boundary around the crease of her legs, and she gasped as the feeling slowly dialed in. Just when she thought that this time was finally going to be it though, she sobbed as the nurse withdrew her hand less than a millimeter away.
“Naughty girl,” she said, “This is supposed to be a medical exam, not a brothel.”
“But I can’t!” said Sasha, “Oh please, you don’t understand. They only let us do it once a year and even if you can get enough points for it, they still make sure it’s ruined. And then because they don’t allow you to have anything inside of you when it happens it just feels so hollow and empty, and then you have to wear a plug for an entire week afterwards since you can’t sit still in class and…”
Her voice trailed off, and the fact that they were already well beyond that point by now was not lost on the irony of the situation. Nor was the fact that she was practically begging to be masturbated now, and all of a sudden she realized that she had no idea if anyone else was even looking. Which was not good at all unless she rather liked the prospect of being locked up in chastity again with the key thrown away, and so it was only through a **** measure of panic that she was able to stop herself in time. Like, even if there was someone standing close by, surely there was no way they could actually hear, was there?
With her heart pounding in her chest, Sasha pushed herself up from the table to look around. To her relief, however, aside from the other two dozen or so stations scattered about the room, there was nobody there. Over by the window, Mr. Johnson stood facing away from her as he looked outside. Besides him was the head nurse, her clipboard still held in her hand, and the two leaned in together as they talked in a small voice.
“Now, are you going to behave?” said her own nurse, “Or do I have to go and get the straps?”
“Not the cane?” said Sasha weakly. That had been way too close for her to believe.
“I can get that too if you want,” said the nurse, giving her a new and interesting look, “Though I’m afraid you’ll have to get started on your vegetables first before we bring out the cake. Not that it looks like you’ve taken any carrots down here before, even tiny little baby ones…”
She smiled at the joke, and Sasha felt herself curl up even more inside her head. Past that though, her expression grew a little more serious as she shifted her focus over to actually making it through the rest of the exam. Which just had to include another half dozen rounds of slowly being edged again with nothing but her nipples and her clit, and by the time they were ready to move on the entire world was once again swimming in a healthy shade of pink. And blue, and red, and every other color of the rainbow as Sasha struggled to set her thoughts straight, and so she could hardly be blamed when the nurse had to help her turn back around so she could lift her bottom into the air.
The cold glare of the lights shone down on them both, and crouching down on all fours with her head pressed against the surface, she shivered as she felt the familiar touch of lubrication slide down between her cheeks. A finger quickly followed to help spread it against her rear, and a short press from there was all that was needed for the tip to slide in. Slowly at first as it stretched apart the tightness of her ring, and then with much more intent as the nurse pushed her arm all the way forward until her bottom was flush with her hand.
Following that was a brief moment of awkwardness as she moved her finger around as if looking for something specific, and then the entire weight of the world seemed to jump up all at once as she started to massage the delicate place where her g-spot was through the thin layer of flesh in between.
“Oohhh!” gasped Sasha.
And then a second louder cry a moment later as the nurse placed her thumb over her clit.
“Hush now,” she said, “Bear with it. Just another couple more minutes now, and then we’ll be finished.”
There was no way that was true, but it was impossible to think as the fingers moved again inside of her with a gentle stroking motion as if rocking her to sleep. And against the feeling, it was all she could do not to curl up and faint. Or do anything at all besides lie there and take it as she was once again **** to the very edge of the abyss.
Sasha sobbed as she lay there panting. The darkness peered up at her, threatening to tip her in, and she clenched her fists together until her nails dug into the palm of her hand. Even if she was somehow able to make it past the finishing line at the end the nurse would simply pull her hand away again, and then whatever pitiful excuse of an orgasm that still remained would be completely ruined leaving her worse off than when they had started. Like water out of a broken vase, and she desperately clung to whatever remnants of self-control that she had left.
She can’t, not right now, not with everyone else watching. If nothing else, she was absolutely sure of that. Famous last words though, for someone with so little conviction.
Rub, rub, rub…
Press, press, press…
A second finger joined the first, spreading her cheeks apart even more to push against her ring, and she gasped as they slid past the frictionless rim of her anus. Like a mechanical piston with the endless thrusting of the movement working deeper and deeper into her rear, and she could already feel her g-sport starting to swell up within. Her clit as well, standing straight up at the top of her slit, and after just another touch, another stroke, another pinch of her nipples as they rubbed against the bench, she cried out in ecstasy as every muscle in her core tensed up in preparation for her climax. Close, she was so close now. Just a little more, and then…
But of course, that was not to be. At the very last moment when she could feel her body starting to give in, there was the awful weight of emptiness inside her again as the nurse pulled her hand away, and all of a sudden like a bucket of cold water dumped over her head, everything stopped all at once.
“No!” she cried, “I was so close!”
Desperately, she tried to reach down with her hands, but the nurse was already there as she held them out of the way. Her fingers tightened down against her wrists, keeping them secure even as she thrust her hips out against the emptiness of the air, and if there had been so much as a single extra flick against her labia, then that was all she needed to bring herself over the edge. Too bad there wasn’t though, and against the endless burn of frustration rising up deep inside, there was nothing she could do but sob as she felt the tears leak down her face. Both from above and below, the fluids of her arousal pouring out like a river against the inside of her thighs, and she watched as a single strand of stickiness stretched out to soak into the parchment paper placed between her legs.
One… two… three…
The nurse leaned forward to whisper into her ear, and the count reached the latter half of the double digits by the time she was finally able to remember how to breathe. Then the grip on her arms relaxed, and she sniffed as the woman reached out with a tissue to dab away at her face. And then her other place down below as she tried not to wince. Following that though was still one last step to complete, and so bending over again with another sigh of despair, she resigned herself to her fate as she pushed her bottom back up into the air.
The heat rose up inside her again, and she felt another drop of lubrication flowing down between her cheeks. This time though, instead of the soft touch of fingers there was the blunted end of a device that she knew all too well by its shape as it slowly pushed past her ring. So too did every other girl in her class.
Sasha groaned. Bit by bit she felt it spreading her apart and as the widest point made it past, she gasped as the muscles of her anus gripped down against the base. There was a mirror set out besides her, and after taking another moment to recover, she turned her head to see.
“Pretty, isn’t it?” said the nurse.
It was, if you didn’t count the feelings that it came with. Buried between the soft curves of her rear was the tapered end of a training plug, the size measuring out at just the right length for a girl her age, and she blinked as she shifted her hips. In response, a soft hint of frustration echoed out from within with the fullness of the device coming entirely from the wrong place, and she bit down as she felt her clit let out another twitch.
Fortunately for now, however, that was all there was for the exam. Pulling herself back together, she spread her legs one last time for a quick application of numbing cream. The brush dipped back into the jar a second time to make sure that everything was covered, and she sniffed as she brought her hands up to her face.
“Oh, don’t cry now,” said the nurse, “It’ll ruin your complexion.”
“But it hurts, and I can’t even feel anything,” sobbed Sasha.
“You’ll be able to at the end of the semester though, won’t you?” she said.
“But the points…,” said Sasha.
She blinked away the haziness of the tears, and the nurse reached over for a tissue to wipe them away.
“How many do you have right now?” she said.
“Sixty-one,” said Sasha.
“And how many do you need?” she asked gently.
“Seventy-five for a ruin,” said Sasha, “Ninety if I want to do it with a vibrator instead of just a finger on my… down there.”
One hundred points bought her a full orgasm instead, but there were less than a dozen applicants each year who were able to qualify for that. Which really said something about the level of dedication needed since there were well over a thousand students that lived at the academy. It wasn’t good for her to focus on such things though. Especially as the nurse finally put everything away.
“Then you just need another fourteen more to go,” she said as if it was as simple as that. She reached out to brush the hair out of her face.
“But there’s only a week or so left,” said Sasha.
“And so are you going to let something like that get in your way?” said the nurse.
She smiled at her, and Sasha blinked. Fourteen was a lot, especially when she was just as likely to have them taken away for arriving to class late. Still though, it wasn’t an impossible task to complete, and so wiping away her tears one last time she looked back down between her legs.
The smoothness of her vulva stared back at her, the softness of her labia parted ever so slightly to reveal the pinkness of her lips, and standing straight up at the top of her folds was the miniature nub of her clit. Slowly, it throbbed in time with her pulse as it peered out from its sheath, and despite how much she wanted to reach out and touch it, the sharpness of the edge was made just a little more bearable by the thick layer of cream. At least she had made it all the way through without earning herself another punishment.
Pressing her legs back together again, she winced as she shifted her weight off the plug in her rear.
“That’s the spirit,” said the nurse, “Now let’s get you dressed again before we send you back off to class.”
Reaching out her hand, she helped her down from the table before drawing her panties back around her waist. The softness of the material pressed up against her crotch, and there was a brief moment of panic as it brushed against her slit. The feeling passed almost as quickly as it arrived though, replaced all too soon with the familiar burn of a dull and frustrated ache, and she stopped by the front desk of the lobby to put the rest of her uniform back on again.
Fourteen points across an entire week, she thought again as she went. Her nipples poked up from her shirt as she made her way back out into the hall, and placing one foot in front of the other she did her best to ignore the plug in her rear. At least it didn’t come with a vibrator built in, or if it did, the nurse hadn’t bothered to turn it on yet. Which was just about the best thing she could ask for right now, since with her panties completely soaked through, there wasn’t much of a chance that she would be able to pass a standard uniform inspection if it came down to it.
The door of her homeroom classroom was two turns down and to the right. Looking around as she stepped inside, she was greeted with the wonderful sound of silence. Apparently, she was the first one back. Good for her then, since that meant there was nobody to bother her about the disheveled state of her dress.
Her desk was in the front row and she sat down to open her textbook to the current page. The two round bumps of her seat pressed up against her, the first one wedging itself between the delicate folds of her labia while the second one **** the plug even deeper into her rear, and taking out a blank sheet of paper from her notebook, she did her best to ignore them as she started to read.
In 1880, Thomas Edison invented the lightbulb after discovering electricity. In the process, he failed over a thousand times before he finally succeeded. If she ever wanted more than just another painful and frustrating ruin with her skirt lifted upward in front of the entire school though, then she was going to have to try a lot harder than that.
Slowly, the clock ticked onward, and sitting there against the silence with nothing to distract her, she tried not to notice the growing presence of arousal between her legs.
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Classroom Stories
Chapter 1
A collection of stories about the St. Margaret’s Academy for Wayward Girls, an all-girls boarding school where chastity belts are common, masturbation is forbidden, but the students just can’t keep their hands away from themselves at night while they sleep. To combat this, every day before class, the girls are required to line up for a morning inspection with their skirts lifted up above their waists. Standing perfectly still with months of denial bottled up inside, they must do everything they can to stop themselves from getting wet as their teacher checks them between their legs. Over a thousand such girls attend the academy at various grades, and between the spankings dealt out every day and the plugs they have to wear in their bottoms as punishment, they have little option but to keep themselves chaste as they wait for their long-anticipated release.
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- denial, virgin, toys, plug, anal plug, fingering, discipline, teasing, chastity belt, edging, orgasm denial, humiliation, female orgasm denial, shame, masturbation, anal, public humiliation, spanking, punishment, nudity, buttplug, school, embarrassment, sexual frustration, teenagers, overstimulation, domination, figging
Updated on Oct 11, 2024
by RetrospectiveInsomnia
Created on Jun 8, 2023
by RetrospectiveInsomnia
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