Classroom Stories - Cover

Classroom Stories

Copyright© 2023 by RetrospectiveInsomnia

Chapter 4

Erotica Sex Story: Chapter 4 - 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, and the students just can’t keep their heads clear of lustful thoughts as they sleep. With months of denial in between, they have little option but to keep themselves chaste as they wait for their long-anticipated release.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   ft   Coercion   NonConsensual   Heterosexual   Fiction   School   BDSM   DomSub   MaleDom   Humiliation   Light Bond   Rough   Sadistic   Spanking   Anal Sex   First   Masturbation   Sex Toys   Voyeurism   Small Breasts   Teacher/Student  

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 forced 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 forced 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 desperate 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.

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