Tuesday, September 16, 2025

Emily's Turn - A "Little Schoolgirl" Story

 “I can’t believe she checked me!” Emily said in righteous indignation as her lunch tray clattered onto the cafeteria table. Her delicate lips pressed tightly together in a furious frown. She flipped her long blonde hair back over her shoulder as she sat down across from the other two girls, both of whom had sympathetic looks. Ashley nodded as she unpacked her own lunch. 

“You never break the rules,” she said knowingly. “It had to just be a random check. You know. Ever since Jenni has been stuck with that harridan in ISS, they’ve been doing way more.”

The other girl, Cindy, snorted. She was short and curvaceous, almost bordering on plump. “Jenni’s isn’t ‘stuck’,” Cindy declared. “She is in ISS because she likes having her filthy little cunny beaten to a pulp.” 

Ashley looked surprised at Cindy’s comment but Emily didn’t reply. It was more than a rumor that Jenni was a nympho humiliation pain slut. Emily couldn’t figure out how she hadn’t been expelled, considering the number of school rule violations the girl had committed. But maybe Ms. Fontaine was keeping her enrolled because, as much as Jenni was a masochist, Ms. Fontaine was an even worse sadist. They complimented each other. And deep down, Emily wondered about ISS. Was it really as bad as everyone said?

Cindy gave Emily a sympathetic smile. “But I admit, Ms. Fontaine checking you seems like a waste of any opportunity. Considering how often it happens, doing a panty check on you seems a little pointless. There had to be another girl disobeying the school uniform rules.”

“Like you?” Emily teased.

Cindy’s eyes widened. “Me? No way. I’m wearing all the required underclothes. I wouldn’t dare.”

Both Emily and Ashley nodded and all three started to eat. It took only a minute, but then Ashley looked up. “Well, at least you know it will be a while before she checks you again.”

Emily glanced at the other girl. “What do you mean?”

Ashley shrugged. “Well, Ms. Fontaine never checks the same girl twice. She cycles through them. So unless you do something specific to attract her attention, you know she isn’t going to drag you up to the front and check you again for at least a week.”

Emily leaned back, chewing thoughtfully. But it was Cindy who leaned forward. “Really?” She asked, but before Ashley could answer, shook her head. “I’m also curious as to why you’ve even been keeping track. Were you planning on going commando the day after you get checked next?”

Emily blinked, shocked at Cindy’s accusation.

Ashley laughed. “Hardly. And I wasn’t keeping track of it for any nefarious purpose, but I’ve noticed. If that’s what you mean.”

Cindy grinned. “So you were thinking about it.” She teased Ashley. “That is quite daring.”

Ashley’s face turned bright pink. “I’m not a slut, like that girl, Jenni.” Ashley shook her head. “She gets off on breaking the rules.”

But Emily pursed her lips thoughtfully. “Still, it would be nice to pull one over on Ms. Fontaine. Could you imagine her finding out later that her students were all tricking her like that?”

Cindy blinked. “Like what?”

Emily rolled her eyes. “What you just suggested.”

“Going commando?” Cindy asked, just a little aghast.

Emily nodded. “The day after they’re checked, they’re the one breaking the rule. And Fontaine never suspects.” She gestured with her fork. “It would be the ultimate insult once she finds out. It will be so embarrassing, she’ll never do a uniform check again.”

Cindy gave Emily a skeptical look. “What about the other classes?” She asked. “Ms. Fontaine isn’t the only teacher who does uniform checks. Practically everyone does.”

Emily took another bite of her food and grinned. “We’re talking just for this one class. A quick trip to the bathroom to remove your bra and panties before class, and then going back afterward to put them on.”

Ashley’s eyes widened. “Wait. Bra too? Are you insane? She’ll notice!” 

“Not if we are wearing our school cardigans. It’s almost cold enough,” Emily said after a moment. “That will keep her from seeing…” she blushed. “I can’t believe I’m saying this. Pasties?”

Ashley barked out a laugh. “Duct tape,” she said with a grin. White duct tape. I saw it at the hardware store with my dad.” 

Cindy looked back and forth between the two girls. “Are you both insane?”

Emily leaned back. “To teach that bitch a lesson? Wouldn’t it be grand?” Then she gave Ashley a very direct look. “You said it. She never checks a girl twice. Are you in?”

Ashley bit her lip, but then nodded. “I guess so,” she said uneasily. “And only for Fontaine’s class. I’m not risking a trip to In School Suspension.”

Cindy frowned. “Emily, it’s still a risk. A big one. If Ms. Fontaine finds out…” 

“How would she find out?” Emily asked. “Unless someone told her?” She shook her head and her eyes locked in on Cindy. “And you? Will you do it the day after you get panty checked?”

Cindy sighed. “Well… I suppose.”

Emily grinned. “Good. Then tomorrow, we start!” 


 *** 


The next day, right before class, Emily snagged Ashley’s arm. The hallway was almost empty and Ashley found herself pulled into a niche between the rows of lockers. Emily smiled with mischievous eyes. “Here,” she said, thrusting a small, folded bundle of cloth into Ashley’s hands. The blonde looked down in surprise. 

“Wait. Seriously?” She said in astonishment. “I thought you were joking!” 

Emily shook her head. “Nope. Doing it.” 

“For real?” Ashley said in an almost panicked voice.

“Want to check me?” Emily asked with a grin. She grabbed Ashley’s wrist and started to pull her friend’s hand to her skirt. “I don’t mind your finger inside me.”

Ashley was too shocked to resist and a second later she felt the soft and very wet petals of Emily’s bare slit against her fingers. For a second, she almost pulled her hand back, but she found herself rubbing Emily’s flower, dipping in deeper as Emily let out a soft groan.

“Oh,” Emily gasped, jerking back. Her eyes flashed with pleasure. “That makes this even more worthwhile.” 

Ashley lifted her hand. Her finger was coated with moisture and for a second, she didn’t know what to do. Emily’s eyes met hers and Ashley brought her hand up to her mouth and sucked the goo off. Emily’s eyebrow went up.

“After school today,” Emily said with a grin. Ashley nodded wordlessly. 

“Alright.” She said softly. Emily’s underwear was still bundled tightly in her other hand and she tucked it away into her bag. “Good luck.”

“I’m going to want those back,” Emily said, pointing.

Ashley blew her a kiss. “Dream on,” she said in a teasing voice.

The two girls entered the classroom, one in violation of the school rules, both desperately wet. Cindy was already sitting at her desk near the back of the room and she gave the two girls a little wave as they came in. She didn’t seem to be aware of what was going on, undoubtedly forgetting the conversation over yesterday’s lunch. Emily moved to her seat and slid into the desk, careful to keep her knees tightly together. Her blue cardigan did a decent job of keeping the erect points of her nipples hidden. Ms. Fontaine wasn’t in the classroom yet and Ashley, who was seated close to the front of the room, in the second row, gave Emily a cheerful smile. Emily’s eyes narrowed and she nodded. 

Then the teacher walked in. 

Ms. Fontaine was inordinately beautiful, with long and lustrous blonde hair, a pretty face, and what could be argued to be one of the best asses in the school. Her penchant for tight dresses with collars that dipped down, almost, but not quite low enough to violate the faculty’s dress code, kept the boys’ attention. Even her discipline was rather lackluster, with most punishments off-loaded to after-school detention, to let one of the other teachers take care of the more corporal aspects of discipline. But if anything, Ms. Fontaine was prideful. She tolerated no disrespect. It was one of the reasons that Emily’s daring caper was so risky. If caught, she wouldn’t just be sent to after school detention for a punishment. She’d most certainly be sent to spend a day with Jenni in ISS.

Ms. Fontaine came into the classroom with a beaming smile and she glanced across the rows of assembled students with a calm and pleasant demeanor. She set a notebook down on her desk and then stepped out in front of the class. Emily licked her lips. Here it came. Every start of class she would check a different girl, and if Ashley was right, there wasn’t a chance in hell that Fontaine would select Emily. Not two days in a row. 

Ms. Fontaine crossed her arms. “We will start with uniform compliance,” Ms. Fontaine said, just like she always did. Emily was acutely familiar with the process. One of the female students would be asked to come to the front of the classroom, stand with her arms behind her back, hands clasping her elbows. Ms. Fontaine would order the poor girl to arch her back, thus pushing her breasts forward, and the teacher’s penetrating gaze would linger on the student’s bosom, checking for the required bra, visible through the shirt. Then the girl would be asked to spread her legs. Some girls preferred to lift their skirts and display their panties. Others opted for Ms. Fontaine’s fingers to quickly check them. Emily preferred the latter, which is what had happened the day before, Ms. Fontaine’s delicate touch stroking the cotton covered folds of Emily’s sex. 

Emily shifted her weight and when Ms. Fontaine looked at her, she felt her insides squirm. The teacher smiled and for a second, Emily felt a sudden rush of fear. Then Ms. Fontaine’s eyes continued down the row. Emily took a deep breath, unaware she’d been holding it in, and then sighed in relief. Which is when Ms. Fontaine’s eyes flickered back to her.

“Emily,” Fontaine said firmly. “Come to the front of the room.”

A ripple of astonishment went through the class as Emily’s mouth dropped open. “What?”

“You heard me young lady. I said come to the front of the room. I will be checking your uniform today.”

Emily blinked. “But.. but you checked me yesterday!” Emily protested, her eyes widening in alarm. 

Ms. Fontaine grinned. “I’m fully aware of that. But you look like the kind of girl who likes to get away with things. Come up here now!” She snapped her fingers and pointed at the floor next to her. 

Emily almost panicked. She glanced at Ashley, but her friend was looking away. Ashley hadn’t been wrong about Fontaine always picking someone else. Why had Ms. Fontaine suddenly changed her selection process? Emily slowly rose from the desk, her mind frantically churning through possibilities, looking for a way to avoid what was coming. For a second she considered running for it, charging through the door and belting down the hall. But that wouldn’t just earn her a spanking. She’d end up in ISS for sure and everyone knew about the horrible things that happened in there!

She took a breath, only to realize she was shuddering, the fear inside her now rippling with energy. She gulped, moving up to the teacher, who’s eyes glittered. Ms. Fontaine smiled and gestured for Emily to face the class. Emily licked her lips as she brought her arms backward, clasping her own elbows as she thrust her breasts forward. The cardigan she wore opened at the front and her bodice became immediately visible. Thankfully the room was warm. Maybe Ms. Fontaine wouldn’t notice?

“Hold yourself just like that,” Ms. Fontaine said simply. She reached around the desk, opened the drawer, and pulled out a small canister of compressed air, the kind used for cleaning debris out of keyboards. She gave it a quick shake and then held it up. “Now, if you’re wearing a bra, like you were yesterday, this shouldn’t be any problem. Will it?”

Emily stiffened, sucking in a breath, but then the cold air hissed out of the small can, striking her left breast. The cold air seemed to blast straight through the thin cotton of the school uniform blouse and Emily felt herself tightening as the cold lashed at her nipple. A moment later Ms. Fontaine moved the can and directed it at Emily’s other breast. It didn’t take long for Emily’s body to betray her. The cold was bitter and two distinct, perfect bumps pressed outward against the material.

“My my my,” Fontaine cooed. “It seems that you thought you could pull a fast one on me,” she chided. Fontaine reached up and to Emily’s shock, stroked the hard, sensitive tip right through the material. Emily let out a soft groan, only to gasp as Ms. Fontaine flicked her finger against the same spot. “Such a naughty little girl,” Fontaine continued. “Well, it looks like someone will be getting punished today. Of course, the big question everyone is now wondering, is it just going to be those firm, round breasts of yours that get the punishment, or is some other part of you going to be placed on display and spanked properly?”

The boys in the class all seemed to be leaning forward, eyes bright with excitement and Emily flushed crimson. She knew what was coming next and she closed her eyes, not wanting to see the salivating stares of her classmates. “Now hold still while I check you,” Ms. Fontaine announced. Emily felt the waft of air as the front of her skirt was lifted, and not just a little. She yelped as Ms. Fontaine completely exposed her, even before putting her hand down between Emily’s legs. The entire class gasped, except for Ashley and Cindy, both of whom flinched slightly. Then Ms. Fontaine, despite being able to plainly see Emily’s violation, slid her finger down through Emily’s sex, the slick wetness actually enabling the teacher to thrust her digit deep into Emily’s pussy. 

“My goodness,” Ms. Fontaine whispered. “How daring of you.” Emily gasped and felt herself ripen instantly, her pussy practically gushing with juice as Ms. Fontaine fingered her. A moment later Emily’s hips were pumping lewdly as the English Lit teacher curled her finger, caressing the inside of Emily’s sex. Then Ms. Fontaine moved behind the girl and with her other hand, cupped Emily’s breast, pinching her nipple beneath the shirt material lightly.

“I suspected you might try something like this,” whispered Ms. Fontaine into Emily’s ear, her fingers still swirling inside Emily’s sex and pinching her nipple. “I’ve always thought you might be a naughty little slut. Of course you like having my hand up your skirt. I can’t believe you’re this wet! But I’m going to take care of that in a moment. I don’t usually punish students, but I’m going to make an exception in your case. Does the thought of punishment turn you on?” 

Emily groaned, trembling as Ms. Fontaine continued to torment her. Suddenly, the teacher let her go, pulling her hand out from under Emily’s skirt and stepping away.. 

“Not wearing a bra,” Ms. Fontaine declared, holding up her glistening forefinger. “Is violation number one. Not wearing panties,” she added, holding up a second finger, is violation number two.” A third finger popped up. “And your audaciousness to think you could possibly trick me, is violation three.” She put her hands on her hips with a glare. “I know I’m not known for punishing students, but this was a bridge too far, young lady. And I am about to correct you.” 

Fontaine pointed at one of the boys seated at the front of the class. “Jimmy, Please go next door and if Mr. Cooper’s punishment chair isn’t in use, bring it into our classroom.” She frowned. “I guess I’m going to need to request one.” She looked over at Emily, who was still standing in the front of the class, a horrified and hopeless expression on her face. “Well? Strip girl. You know the drill. Or do you need help?”

Emily shook her head. Slowly she brought her hands up to her chin and her fingers found the first button of her blouse. One by one, she unfastened her shirt, exposing creamy white skin until the entire front was open. Emily closed her eyes, not wanting to see the salivating looks of her fellow students as she pulled the loose shirt tails out of her skirt. Every boy in the class, and even many of the girls, stared in fascination, and undoubtedly lust, as Emily finally bared her breasts, exposing the raised, pink tips. The shirt fell down off her shoulders and Ms. Fontaine grabbed it before it could fall to the floor. 

“The skirt now, you slut.” 

Emily felt another spasm ripple through her and she couldn’t tell if it was from the utter humiliation of being stripped in front of the class, or from the pure arousal shooting through her. Maybe it was both? Was this feeling why Jenni seemed to like it so much? She unclipped the waistband of the skirt, feeling it loosen from around her waist. With an endearing hip wiggle, she shifted left and right and the blue plaid material fell down around her ankles. 

Just at that moment, the door opened and the young man sent for the punishment chair pushed the plastic and metal frame seat into the classroom. It was obnoxiously wide, and Emily’s mouth fell open as she realized how she was to be restrained. The chair itself was canted backward slightly, undoubtedly to expose her sex more thoroughly. But there were telescoping metal bars sticking outward from the sides of the chair, each capped at the end with a Velcro style manacle dangling from a metal clip. The worst aspect of the chair though was the molded anal plug in the center. It was disturbingly thick and Emily felt her bottom pucker at the thought of having to sit on the pointed phallus. Ms. Fontaine produced a bottle of oil from her desk drawer and quickly lubricated the spade shaped plug.

“Now have a seat,” she ordered.

Emily, her arms crossed in humiliation across her chest, turned and faced her class. Ashley’s expression was a mixture of sympathetic horror and lust, the girl clearly having mixed feelings about her friend’s nudity and coming punishment. Cindy, sitting in the back, had closed her eyes and was looking away. But everyone else seemed enraptured, watching as Emily moved slowly into position, gripping the arm rests of the punishment chair. 

She sank downward, bracing herself for the frightening touch of the plug. She wasn’t technically an anal virgin, but she’d never had to endure this kind of thing at school. She almost jerked back up when she felt it against her buttock, just an inch to the left of her bottom. She adjusted her descent until the tapered tip was pressed up against her opening. Her calves strained to keep her up, but both the knowledge that she had no option, plus her tiring muscles, kept her moving and the first inch of the anal plug slid into her rear. Emily gasped, then groaned. She halted her descent, her body resisting the intrusion. She pulled back up, altered the penetration angle, and pushed down again. A bit more went into her bottom, the accompanying ache strong. She started to lift herself up again, only to feel the strong, firm hands of Ms. Fontaine on her shoulders.

Pushing downward.

The anal plug popped into Emily’s bottom firmly and the girl yelped, startled as she was left with no recourse. It didn’t hurt per se, but it was an uncomfortable thick firmness in her ass that she wasn’t accustomed to. Instinctively she jerked her hips forward, but the plug held her in place. Ms. Fontaine’ hands maintained the downward pressure as she wriggled, until finally Emily groaned, accepting both the penetration and her position.

“That’s a good girl,” Fontaine cooed. “Now give me your hand.” The teacher reached down, running her fingers over Emily’s forearm to her wrist. Fontaine pulled, forcing Emily to move her other hand to cover her bosom. Fontaine stretched Emily’s arm outward along the bar and two simple leather straps with buckles secured the errant limb to the frame. Emily realized she was panting in near panic as Fontaine pulled the other hand away from her chest. The leather straps held Emily in place and she realized that even had she wanted to pull herself free of the plug, she would be unable to do so. Not the way her arms were bound.

“Now, your legs,” Ms. Fontaine said, coming around the chair. She looked down at Emily, who was already quivering in trepidation, her knees tightly together. “Spread your legs or I will have two of the boys do it.” Emily’s mouth gaped open as she stared up at the teacher. Trembling, she slowly opened her legs. Emily licked her lips from her seat on the second row, staring at the dark pink and very wet petals of Emily’s now visible sex.

“Wider,” insisted Fontaine. “All the way until your knees are against the frame.” Emily did as ordered, closing her eyes again so she didn’t have to see the hungry stares of her fellow students, or Ashley’s hungry eyes. She spread herself open, chest heaving, her bottom clenched tightly around the plug, and she felt Ms. Fontaine wrapping another leather belt around her thigh. 

“Hmmm, shoes and socks on? Or off?” Ms. Fontaine asked loudly, seemingly to the class.

It was Ashley who responded. “Shoes and socks off,” she said with confidence. “She’s got really cute toes!” 

There was a flurry of laughter and Emily opened her eyes to look at Ashley in surprise. Ms. Fontaine smiled and nodded. “A worthy recommendation. And you can come up, Ashley, and remove them.” 

Ashley’s eyebrows went up and her cheeks turned bright red. Slowly, she stood up and moved in front of Emily. The two girls looked at each other as Ms. Fontaine stepped out of sight, going to her desk. Then Ashley knelt down and began pulling off Emily’s shoes and socks. It didn’t take her that long, but Emily saw the way Ashley kept looking at Emily’s exposed slit. She even licked her lips! Another rush of arousal shot through Emily as Ashley finished, her soft fingers caressing the bottoms of Emily’s feet with a quick touch.

“Thank you,” Ms. Fontaine said quickly, shooing the girl away. “Now we will begin the sensitization process before corporal punishment. And I have just the right thing.” 

In her hands she held a plastic bag filled with over two dozen colorful clothespins. She plucked one out and held it up as she bent down over Emily’s body. “These will undoubtedly hurt,” Fontaine added, pinching the first peg open and attaching it directly on Emily’s left nipple. Emily grimaced as a sharp, tingling pain shot through her breast. “But I do believe that’s the point.”

“Owwww,” Emily whimpered. “That hurts!” 

Ms. Fontaine grinned, pulling a second clamp out of her bag. “It’s supposed to. Now, just let me put one on your other nipple.” Ms. Fontaine set the second clothespins in place, sticking straight out from Emily’s bosom, both pink nubs now firmly pinched between the plastic maws of the colored clothespins. Emily mewled, wincing as her nipples began throbbing. 

“Now, let’s get your clit,” Ms. Fontaine added. A third clothespin appeared in her fingers and Emily stiffened in alarm as the teacher bent down. She used both hands, one to spread Emily’s petals, exposing the tiny nub at the apex of Emily’s sex, the other positioning the clamp. Emily let out a screech as the clothespin closed, a sharp agony shooting up through her loins, making her bottom tighten down uncomfortably on the plug in her ass. She shuddered, pulling on the straps holding her in place as the various pains seemed to flow through her.

Then came more. Ms. Fontaine began pulling more clothespins out of her bag and bits of soft breast to either side of Emily’s nipples were quickly subjected to similar torment. Her chest heaved as she wriggled on the chair, unable to truly move or free herself. Shards of pain shot up through her breasts. Then the teacher moved down to Emily’s pussy and began adding more clothespins, running them down each side of Emily’s labia. 

Emily whimpered, wincing as her body was forced to cope with the throbbing pain of the various clothespins, but as Ms. Fontaine went back to her desk to put away the bag, Emily began to feel bits of her body going numb. The pain lessened to a throbbing ache, though Emily wasn’t any less absorbed with the predicament of her situation. A sudden gasp of the students in front of her drew her attention away from herself, back to the teacher. Ms. Fontaine had appeared to the side, holding a ridiculously large vibrator with an extraneous arm. 

“Because I want to be generous,” Ms. Fontaine said simply. “I’m going to provide you a distraction from the pain you are feeling.” She squatted down in front of Emily, but by her thigh so as not to block anyone’s view of Emily’s slick slit. “This vibrator is not here for your pleasure, but to make it possible to tolerate the punishment. Do you understand? You are not to cum.” And with that admonishment, Ms. Fontaine slid the entire thing straight into Emily’s spread open slit.

Emily squealed as her pussy tightened involuntarily around the thick, massive phallus. She felt the arm against her folds, pressing tightly against her clothespin clamped clit. Ms. Fontaine hadn’t turned it on yet, but even without the vibrations, Emily felt herself locking around it, her hips jerking. Ms. Fontaine then pulled a strange hinged support arm out from under the chair, twisted the base of the vibrator to maximum, and snapped it in so that the vibrations roared into Emily’s stretched cunt. 

Emily’s hips rolled in spastic pleasure, the forced sexual stimulation overloading the young girl’s libido. In seconds she moved from the humiliation of her exposure and the pain of the clamps, to coming close to orgasm. She shuddered, teeth clenched, only to mewl in desperation.

“Um… Ms. Fontaine?” Ashley said from her seat, raising her hand. “I don’t think she can handle that much vibration.”

Ms. Fontaine looked down at Emily. “What is it that Ms. Temis is always saying? A lack of control is not my fault?” She shook her head. “Control yourself, Emily. Or you will be spending the rest of the day in ISS.” 

She turned her back on Emily and went back to her desk. 

Ashley’s eyes narrowed and she watched Emily twitch violently. “Uh… Ms. Fontaine? What about the punishment?” 

Ms. Fontaine sat down at her desk. “What about it, my dear?” 

Ashley blinked. “Isn’t Emily supposed to get a whipping, and a spanking?” She asked, clearly concerned.

“And she will,” assured Ms. Fontaine. “But near the end of class. For now, she will sit and endure both the clothespins and the vibrator. Hopefully controlling her baser instincts.” She glanced over at the now crooning girl and frowned. “Though perhaps a gag might be wise.”

To Ashley’s shock, Ms. Fontaine then started the lesson. Emily’s noises got louder, and more frequent, until after about five minutes Ms. Fontaine’s threat of a gag was realized. The rubber ball was jammed between Emily’s teeth, effectively muting her to a tolerable level. That was for the best, because a minute later Emily screamed in release, fluids squirting out from between her legs, around the vibrator, her cute little toes curling. 

Ashley looked over at the teacher, who noted Emily’s orgasm with a discerning eye, then continued on with the lecture. In the punishment chair, Emily slumped, panting hard, then began whimpering again as the incessant torment and stimulation continued. 

“Um… Ms. Fontaine?” Ashley asked again, interrupting and raising her hand.

“What is it now, Ashley?” 

“I think… I think Emily exploded!” 

Ms. Fontaine pressed the tips of her fingers together. “Indeed. I observed Emily’s lack of decorum, just as you did.”

Ashley gave Emily a concerned look, especially as it was becoming increasingly obvious that Emily was getting sensitive. “But… don’t you think you should turn off the vibrator?”

“Why would I do that?” Ms. Fontaine asked curiously. 

Ashley blinked in surprise. “Because she’s getting sensitive?”

Ms. Fontaine took a deep breath. “Ashley, are you aware of what happens to recalcitrant students in ISS?” 

Ashley gulped. “Sort of,” she admitted.

Ms. Fontaine nodded. “Then you know that In School Suspension is where students are sent when they violate the rule about orgasming during sensitization or punishment. They are subjected to non-stop stimulation to help desensitize them. And should they cum again, then they are sent back to ISS the next day.” She glanced at Emily. “I suspect it will be a week before we see Emily back in class. She appears acutely ripe to this kind of torment.” Ms. Fontaine glared at Ashley. “Now, you will please stop interrupting me.”

Over the next twenty minutes Emily suffered. Her nipples and clit throbbed horribly as her heart labored to push blood into the crushed extremities. The other clothespins on her breasts and labia ached horribly, almost as much as the thick plug buried in Emily’s bottom. But the worst part of it all was the vibrator. It confused her constantly, waves of pleasure kept streaming upward through Emily’s body, mixing with the pain and supercharging the sensation. By the time Ms. Fontaine stood up, ending her lecture with ten minutes to go before the bell, Emily was right on the edge again, struggling to keep from having another orgasm.

“I believe it’s time to remove the clothespins,” Ms. Fontaine declared. She stood and pulled a medium length flogger from her desk drawer and shook out the leather strands. Ashley’s eyes widened as Ms. Fontaine moved into place next to Emily. She ran the long leather thongs through her fingers, then pulled back, clearly aiming for Emily’s chest. 

“Here we go,” Fontaine said. With a flick of her wrist she slashed the flogger horizontally across the bound girl. It wasn’t a terribly hard blow, but the leather stands caught on several of the clothespins. Fontaine knew exactly what she was doing though and none of the plastic clamps were tugged free of Emily’s breasts. Instead, it just twisted them around a bit. 

Emily yelped into her gag. Pain shot through her chest, sharp shards of agony that seemed centered on her nipples, then surged down to her stuffed and vibrated pussy. What she didn’t expect was the way her body took the pain and did with it. Her hips thrust forward, pushing against the vibrating phallus buried in her twat, even as she wriggled, causing the extended arm of the vibrator to rub vigorously against her clamped clit. Her nipples seemed to burn and throb and when Ms. Fontaine struck a second time, once more failing to knock the clothespins free, Emily squealed in confused need. Fontaine shook out the whip and smiled. “As a reminder, you still are not permitted to cum.”

But even as Fontaine swung once more, this time managing to knock one of the half dozen clothespins off Emily’s tits, the young girl knew that resisting the urge to orgasm was beyond her strength. There was just too much stimulation going on to hold back. The vibrations between her legs were clearly the largest of her problems, with the pulsing heat of her breasts a close second. But even her ass was puckering around the plug and her panting body trembled from the vibrator, Ms. Fontaine continued to swing the whip. More of the clothespins were ripped free, each time eliciting a sharper cry from the bound and gagged student. But it was Ashley who was the first to note that the clothespins on Emily’s nipples had resisted each blow. Each stroke twisted the two clothespins viciously. Finally Ms. Fontaine lowered the whip, twenty full strokes delivered.

“Um… Ms. Fontaine? What about the last two clothespins on Emily’s nipples?” Ashley demanded.

Ms. Fontaine rolled her eyes. “They’ll remain until I’m done,” she said curtly.  

Ashley looked confused. “But… Ms. Fontaine. That was twenty strokes!” 

Ms. Fontaine reached over Emily’s outstretched thigh and pulled the vibrator completely out of the poor girl’s trembling pussy, eliciting a mournful cry that could be heard despite the gag. 

“You misunderstand, Ashley,” Ms. Fontaine said. “They’ll remain on until I’m done with all of Emily’s punishment.” And with that, Ms. Fontaine snapped the flogger down between Emily’s legs. 

The first stroke ripped three of the seven clothespins completely off and Emily shrieked, a high-pitched warble that even the gag couldn’t really silence. Her little feet kicked wildly and then the flogger snapped back in, once more catching on the plastic pegs. It took four more strokes to free all of the clothespins but the one attached to Emily’s clit, which bounced and jiggled madly with each blow. 

Ashley watched, cringing as the flogger bit heavily into Emily’s vulnerable and exposed sex, causing the bound girl to jerk and jump, screeching into her gag. But even as Ms. Fontaine focused her attention on Emily’s pussy, Ashley realized what was happening. Her eyes widened as Emily’s hips rolled and her back arched. Ashley gulped, then began shaking her head. Ms. Fontaine passed ten, then hit fifteen, but from the way Emily was quivering, Ashley knew that her friend wasn’t going to make it.

On the nineteenth stroke Emily screamed, fluids once more streaming from her sex. This time there was nothing to impede the effluvium and cum splattered onto the floor as Emily quivered and tensed. Even Ms. Fontaine seemed a little taken aback as the bound girl exploded, her sexual tension overwhelming any pain. Then Emily’s eyes rolled up into the back of her head and she slumped forward. 

Ms. Fontaine looked alarmed and she quickly lifted Emily’s chin, checking on her well-being. After a moment, Emily began groaning and Ms. Fontaine straightened, clearly looking relieved. She went back to her desk and picked up the phone.

“I need an office aid in Room 105 for an escort to In School Suspension,” she said briefly. “Emily Williams. That’s right. Multiple Uniform Violations and cumming during both sensitization and punishment. Yes. Thank you.” Fontaine set the phone down. “Ashley, please gather up Emily’s belongings, including her shoes and socks, and put them in her bag.”

“Yes ma’am,” Ashley said, feeling awful. Emily sat there, eyes unfocused, a line of saliva dripping from her mouth down to her chest, spasms still rippling their way across her petite frame. Ashley collected Emily’s uniform, then her shoes and socks, and lastly, snuck Emily’s panties and bra into her friend’s bag, as Ms. Fontaine removed the ball gag.

Two aides showed up a moment later, both young men, and they helped Ms. Fontaine pull Emily up. She didn’t even appear to be able to stand on her own and the two boys held her between them.

“Did you want your clothespins, Ms. Fontaine?” One of the boys asked. 

Ms. Fontaine smiled. “I’ll collect them from Ms. Temis after school today. Just get her out of my classroom.” She waved her hand and the two boys carried Emily out, one taking the bag Ashley held out to him, silent.


***


Ashley waited quietly outside of In School Suspension. The last bell had rung, but it took almost a full ten minutes before the door opened. The first girl to come out was a dark haired beauty with a lush, over-ripe look. Her uniform skirt was hemmed far too short, and her shirt bulged where it tried to close over her breasts. In the gaps, Ashley could see the marks of a whip. The girl looked up in surprise and came to a halt. 

“Oh,” Ashley said. “Hi Jenni.”

“Hello,” Jenni replied, smiling softly. “I guess you’re waiting for Emily?” 

Ashley nodded.

Jenni licked her lips. “She’s coming. The first day in ISS is always hard.”

Ashley blinked. “Is she… okay?”

Jenni shrugged. “Mostly. She was physically capable of handling both the punishments, and the torment. But I’m not sure she was mentally prepared for it. And Ms. Temis can be… strict.”

“Punishments?” Ashley gasped. “What punishments? I thought ISS was just about control!” 

Jenni smiled. “I heard that she exploded twice. Once during sensitization, and once during punishment. So Ms. Temis punished her for those. Worse, she came again when Ms. Temis was using the sap on her pussy. So that earned her even more.” Jenni shook her head. “And she’ll be in ISS tomorrow too. With me.” Jenni blushed and looked down. Just then, the door opened again and Emily emerged.

She looked exhausted, defeated even, but her eyes found Ashley and a strange look crossed the girl’s face. “Ashley,” she whispered.

“Are you okay?” Demanded Ashely. “I am so sorry!” 

Emily looked downward. “I have to report to ISS tomorrow.”

Ashley gulped. “I know. Jenni told me.” 

Emily took a deep breath. “Ms. Temis tortured me, trying to make me cum.”

Ashley bit her lip. “Well, at least you won’t get punished again, right?”

Jenni let out a tiny laugh and both Ashley and Emily looked over at the brunette. “Do you find that funny?” Ashley demanded.

Jenni turned back toward them. “Yes,” she said quietly. “Because we always cum. Ms. Temis is very good at finding a way to punish us.” The brunette’s eyes locked on the blonde. “And because it was really, really obvious,” she added, pursing her lips.

“What was?” Ashley asked.

“Emily liked it,” Jenni finished. 

Ashley’s face clouded. “How dare you?” She hissed. “Emily would never, ever, in a million years, be a perverted little cumslut like…” her words trailed off as she caught sight of Emily’s face. Guilt. And… arousal. Ashley blinked. “Emily?”

Emily gave Ashley an embarrassed look, then turned back to Jenni. “So, I shouldn’t wear panties tomorrow. Right?”

Jenni smiled. “Or a bra. That will start things off the way you want.” She gave Emily a wicked look. “From the way you reacted when Ms. Temis used the leather sap on your clit, I know you like that. You can also show up late.”

“Emily! You can’t seriously be considering this?” Demanded Ashley. Emily cringed but looked at her friend. 

“You don’t understand,” Emily whispered. “It was so intense! I’ve never had orgasms like that before! Even in Ms. Fontaine’s class.” Her cheeks were now bright red. “Being exposed like that, tied open, and then the whip…” She closed her eyes and Ashley was appalled to see Emily reach down and lift the front of her skirt. She wasn’t wearing panties and Emily began rubbing herself. “It felt so good!” 

Jenni’s eyes widened in alarm and she surged forward, grabbing Emily’s hand, pulling her fingers away. “Not here! Later!” She hissed, just as the door to ISS opened.

Ms. Temis emerged and looked down at the three girls in suspicion. “And what do you think you are doing here?” She demanded.

Jenni spoke up first. “Nothing, Ms. Temis. Just talking. We’re heading out right now.” She held Emily’s hand tightly, all to keep the teacher from noticing the wetness on Emily’s fingers. She pulled Emily along down the hall and Ashley squeaked, then hurried after them. Ms. Temis didn’t say anything and they turned the corner.

“You can come to my house,” Jenni said to Emily. “I will take care of you,” she added. “At least some of your needs.”

Ashley’s jaw dropped. “But… she was supposed to go to my house!” 

Jenni paused. “Were you going to satisfy her?” 

Ashley blinked. “Um.. yes?”

“Then you can come to my house too,” Jenni said with a grin. 

Emily looked up, hopeful. “Come with us?” 

Ashley gulped, then nodded. “It was really that amazing?” She asked after they took a few steps.

Emily nodded. “I can’t even describe it. Not really.” She looked at her friend. “It was worth it. Not wearing panties, or a bra. I had no idea.”

Ashley took a deep breath. “Then… tomorrow, it's my turn. Commando.” She looked at Jenni and Emily. “And I guess I’ll probably end up in ISS too.”

Emily grinned. “You won’t regret it,” she said earnestly. “It hurts, but it feels so good!”

Ashley nodded. “There’s just one more thing,” she said unhappily. “Someone will need to tell Ms. Fontaine that I’m not going to wear panties, or a bra. All to trick her.” 

Emily blinked. “Then we need to let Cindy know?” 

Ashley looked a little stricken and she shook her head. “I think.. I think you should tell her. It would be… right.” The guilty expression on Ashley’s face was unmistakable. 

Emily’s jaw dropped. 

“How deliciously naughty,” Jenni declared. “I have a leather paddle at my house. We can tie her legs apart, Emily, and give her a little taste of what’s coming.”

Emily took a deep breath and nodded. “Or what’s cumming.”

Jenni grinned. “Exactly.” 


If you enjoyed this story, check out Michael Alexander’s “Discipline for Jenni: Semester 1”, available on Amazon!