Cheerilaid
-by Drace Domino
“This goes against everything I’ve ever stood for!” Twilight Sparkle lamented, though still kept herself balanced with one hand while the other reached down to begin pulling her panties aside. As she wobbled back and forth to kick them down to her ankles, she looked to where she was keeping herself steady, and a wistful look crossed her features. Books, beautiful books! Idly she pawed her fingers across the spines, and murmured in a tiny voice. “I’m sorry, books! I promise I’ll come back and ready all of you some day!”
“You’re being so horribly dramatic, darling.” Rarity rolled her eyes, as if she had never been accused of the same. Once Twilight’s panties were on the floor of the library Rarity slid behind her, moving her arms up and around her friend in a tight, fond embrace from behind. “After all the things we’ve done together over the past few months, this is a hurdle for you?”
Being a pregnant teenager putting out for her friends on school grounds was one thing, but doing it in the library? It made sense that for Twilight Sparkle, it was perhaps a bridge too far, but she was going along with it anyway. As she spun in Rarity’s arms the fashionista had to step back just a bit to make way for Twilight’s pregnant belly, stretching out her shirt and showing off a noticeable bulge. With her pussy bare underneath her knee-high pleated skirt, Twilight slipped her arms up and over her beautiful friend’s shoulders, murmuring softly as she shrugged.
“Can we try to be quiet, at least?” Twilight offered, and nibbled nervously at her bottom lip. “If Ms. Cheerilee found us, I don’t think I could ever look her in the eyes again!”
“Don’t worry, darling, we’ll be as quiet as the golden undertones in my upcoming summer ensemble.” Rarity cooed, and drifted closer to press her mouth against Twilight’s on. She waited mid-kiss to add as a tiny afterthought, whispering while their tongues first contacted. “That is to say, enchantingly subtle, dear.”
It wasn’t subtle enough. There were few things that could grab a librarian’s attention quite like the sight of a pregnant teenage girl heading with a friend to the very back section with the most dense and boring books - to say nothing of the fact that Twilight Sparkle was hardly a master of deception. She was twitchy, nervous, and had the look of a sketchy shoplifter from the second she and Rarity stepped into the library, and any teacher could’ve spotted them and known they were up to something. And Ms. Cheerilee, with a grunt and a sigh, had no choice but to put down the stack of returned books she was sorting and follow after them.
It was a task the older woman didn’t exactly relish. When she became the school librarian, she had done so half in part because it seemed like a relaxing way to build on her career. Who even used libraries these days anyway, except for the most bookish and nerdy students that always showed the place proper respect? Unfortunately for Ms. Cheerilee, she hadn’t thought about an entire different subset of students that would be visiting her domain on a nearly weekly basis - the hornballs.
The sweet older woman had lost count of the number of times she had to pull a pair of students out by their ears because they were trying to fool around in the back of the library. Teenage hormones raged heavy and hot, and they naturally assumed that CHS’ kindest teacher was also its most naive. Cheerilee was sure that plenty of students managed to get away with fucking right under her nose, but when she managed to catch some of them the punishment was usually swift.
Rainbow Dash had been banned from the library for months.
Sure enough, as Cheerilee crept through the aisles of the library, peeking in between gaps in the books, she soon discovered Twilight and Rarity engaging in exactly what the older woman expected. That sweet young Twilight Sparkle was crouching down, her hands underneath her pregnant tummy to keep it balanced as she slowly and greedily sucked on Rarity’s ivory cock. From the tip to the base she was slurping upon it with long, wet strokes, and since her hands were busy holding her belly she couldn’t wipe away the long strings of spit that slathered from her lips before they fell to her pretty dress shirt or the pleats of her skirt. Rarity was quiet contently leaning against the books - which was an infraction all its own - savoring the blowjob and rocking her hips from side to side in order to ensure that her cock managed to bounce to every wall of Twilight’s throat.
“Darling, you’re doing spectacularly.” Rarity giggled, and stroked her fingers through Twilight’s hair. She held her cock at the base and gently pulled it from her friend’s lips, only so she could lightly give her a few slaps back and forth with it, only making Twilight all the more of a mess. “I daresay that this sort of deep library research suits you! And you look absolutely ‘sexy librarian chic’ right now!”
“Just hurry up, Rarity…” Twilight murmured, and licked the other girl’s cock from her balls all the way up to her tip. “I really want to finish before Ms. Cheerilee finds us…”
Well, at least they were aware. Ms. Cheerilee rolled her eyes at that, and continued to watch from the sidelines through the gaps in the books. In truth...this wasn’t the first time she had lingered upon catching a pair of students. One of the things that annoyed the otherwise sweet older woman was just how much catching these little brats worked her up - and the simple fact that it seemed like everyone at CHS was getting laid except for her. It was one thing if the students wanted to fuck each other’s brains out in the janitor closet or in their cars in the parking lot, but doing it where they could rub it in? That was just rude.
And if they were going to be rude, Ms. Cheerilee was going to watch. The woman’s throat tightened, and as she gazed from side to side the folds of her soft pink hair bounced around, finally settling once she was sure that nobody was watching. From there, she gently let a hand slink down the front waistband of her skirt, guiding the fingers to slip underneath her own panties to a pussy that was already wet. There was something about spying on the students while they fucked that drove her absolutely wild, and the few minutes she gazed upon each pair was what she considered her payment for having to deal with them.
It was because of these brats that she spent more time tossing and turning than she did sleeping at night, and she deserved something for all of her frustration. Watching Twilight Sparkle suck Rarity’s cock down to the hilt while she pleasured herself would serve as fine compensation. With one hand resting at the top edge of the books and her breathing low and quiet, Ms. Cheerilee’s eyes narrowed and she gently hooked two fingers within. Wet, tight, warm...in her more lonely hours, she lamented the fact that nobody seemed to want her lonely librarian pussy. But for now, it was nothing more than a source of thrilling delight that quivered through her the deeper she touched herself.
Her eyes were open wide, transfixed upon the sight of Rarity and Twilight Sparkle while they continued to play. After the blowjob Rarity pulled Twilight Sparkle up to her feet, and forced the girl to press her palms to the bookcase opposite of Ms. Cheerilee, presenting her purple rump with a flip of her skirt. Ms. Cheerilee was already burning with excitement, and when Rarity lined her dick up not to Twilight’s soaked pussy but her tiny pucker of an ass, the older woman nearly moaned loud enough to alert them. They were pounding each other’s asses now, too?! These fucking students!
Twilight’s face showed a few signs of strain as Rarity pushed forward, easing her impressively large cock into that little hole, and with Twilight’s own dense spit to keep her cock slippery and wet, started to assfuck her with profound delight. Twilight Sparkle was biting at the edge of her shirt to stop from crying out, and every time Rarity thrust into her from behind Twilight’s belly and breasts swung back and forth. A bred, shameless teenage slut - that was what Twilight Sparkle had become. She was proof to Ms. Cheerilee that even the good, studious girls that respected the library could still to the pain in the ass horndogs making her job miserable.
Ms. Cheerilee drew close in her climax, nearly pushing herself there against her deep pink folds until a presence arrived she hadn’t expected. She was left with a spinning head and a racing heart as she felt a powerful figure press from behind her, one hand closing over her mouth to stop her from alerting the girls, and the other clenching around her wrist where it dipped underneath her skirt. With a muffled whimper Ms. Cheerilee flinched - her entire body tightening and convulsing in fear, and when she tilted her head to look behind her a familiar, dominant voice spoke in a teasing, toying whisper.
“Don’t spook them, now.” Principal Celestia purred, and gestured to where the girls were still going at it. “How will you finish if they run off and leave?”
As a sign of trust, Principal Celestia soon let her hand leave Ms. Cheerilee’s mouth - if she wanted to pull away and alert the girls that their fun was over, it was her choice. Instead, the pink-haired librarian swallowed nervously, and looked torn between watching as Twilight Sparkle was publicly assfucked and gazing at the woman still holding her wrist and stopping her from fingering herself. When she finally spoke it was with a voice as quiet as she could manage, and with it, she immediately proved to the principal of Canterlot High that the last thing she wanted to do was to scare the girls off and end the show.
“...w...what are you doing here, Principal Celestia…?” Perhaps not the best question she could have asked. Why she was holding her wrist would be a good one, or perhaps why she was pressed desperately close against her from behind. Failing that, she could have inquired about the massive erection that was pushing against Celestia’s slacks and squarely against Ms. Cheerilee’s round, warm rump. All of them would’ve been fine things to ask of the other woman, yet...this was all rather new to the librarian whose pussy had gone practically ignored since she got her degree a few years ago.
“Same as you.” Principal Celestia smirked, and gave a slow lick of her lips as she squeezed a little tighter. She wasn’t even looking at Ms. Cheerilee anymore - her eyes drawn through the gaps to watch Twilight bouncing back and forth, taking Rarity’s ivory cock all the way to the depths of her ass. By that point she had folded one forearm to the bookcase while her other arm lowered, holding her belly which had finally been exposed. With the shirt pulled up, that bred pregnant, purple tummy was on full display - and Celestia rolled her hips harder against Ms. Cheerilee’s rump as she beheld her. The top educator’s voice was still dominant and teasing, though still kept at a sweet whisper, even going so far as to rest her lips at the edge of Ms. Cheerilee’s ear. “Don’t let me stop you. Show me what you were doing, you spying little slut.”
The words took Ms. Cheerilee understandably by surprise, and Principal Celestia wasn’t in a patient mood. As the other woman took her time in responding, Celestia’s hand unwrapped from her wrist and flattened across it, sliding straight down her skirt to mirror the woman’s position. She glided her fingers across Cheerilee’s own, cradling them and even pushing overtop her digits within the warm, wet confines of her slit. As Cheerilee made a scrunched face as she was penetrated by two more fingers, Celestia simply offered a hungry laugh at the edge of her ear, and whispered with a rising heat in her voice that wouldn’t be resisted.
“...someone’s soaked.” She purred, and rocked her hips forward once more with a slow push, grinding against Cheerilee all the harder. The bulge at the front of her pants was wedged so close against her that Cheerilee’s skirt had folded around the edges, and her plump, inviting rump was cradling it. With her dominant tone continuing, Celestia pushed those two fingers just a bit deeper, and with them took Cheerilee’s own - forcing her to stretch even tighter than before. When the librarian practically called out in strained shock and pleasure, Celestia merely guided her head towards the teenagers only a few blocked feet away, clicking softly as her whisper went on. “Quiet now. Wouldn’t want the students to know you’re a dirty, horny cunt that watches them fuck.”
Ms. Cheerilee swallowed her cry, though it was replaced with heavy breathing that continued to resonate within her. How could Principal Celestia be doing this? Why was she allowing it? Were the rumors about the school’s top educator true?! Either way, Cheerilee stood with her feet just a little wider apart as she struggled to make room for the four fingers penetrating her, and she could feel her glisten rolling down her own digits, no doubt coating Celestia’s as well. Her eyes were trained upon the teenagers still having their fun - on Rarity’s pure white cock plunging deep into Twilight’s ass, on Twilight’s pregnant tummy swinging like a pendulum. Celestia absolutely delighted in her stunned state, and her free hand slid in between them, her hands moving to the edge of her belt as she continued to speak.
“Look at that pregnant little tramp…” Celestia cooed, her voice still so low it went unheard by the girls. She paused long enough to give Cheerilee’s throat a tiny lick, and it was enough to distract her from the fact that the belt finally came open. Celestia’s cock was soon pulled free and resting against Cheerilee’s rump against the fabric of her flowered skirt, and the poor librarian was left utterly oblivious, stunned as she was by everything that was happening and everything said to her. “Bet you’re jealous of her. Sucking dick, taking it in the ass, all with a little bun in the oven. How many times have you stood back here fingering your pussy, pretending you were one of the girls that sneak over here to get fucked?”
“...m...more than...I can remember…” Cheerilee finally managed to speak, and the trembling squeak in her voice would’ve been enough to alert the girls were it not for the sound of flesh slapping on flesh that filled their own proximity. Rarity and Twilight were understandably distracted, whether it was with the grip of a wonderfully tight purple ass around their cock or the feeling of that ivory rod plunged deep into a glorious little pucker. It was only by the grace of their horny teenage lust that they didn’t hear Cheerilee speak, and the librarian’s words were practically sobbed past trembling, lonely lips as Celestia helped to finger herself. “...they...they sneak here to do it so much…”
“I’ve seen the written complaints.” Principal Celestia merely smirked, and continued to move while keeping Cheerilee distracted with those fingers. She kept guiding the woman’s touch deeper into herself, coaxing her with fingers riding fingers, just as her other hand slowly began to lift Cheerilee’s skirt. Another lick to the librarian’s throat made her quiver, and Celestia pursed her lips to blow a gentle breath across her flesh before whispering again. “Why do you think I never did anything about it? I wouldn’t want to deprive you of the closest thing you get to someone fucking you…”
Celestia’s words were harsh and rude and violating, and yet...Cheerilee couldn’t possibly deny them. The fact that she was still standing there on trembling knees while her employer coaxed fingers within her was testament to that - it had been literal years since Ms. Cheerilee had anything close to sex, and the recent boom in student lust had at least given her something to fantasize about. She always reported it because she was a good teacher, but she had always taken the time to pleasure herself because she was a lonely, desperate, horny woman that had been aching for that sort of attention.
And now, without even realizing that it was coming, Cheerilee had it. She was left disappointed for a few fleeting seconds as Celestia started to pull her fingers away, and with them Cheerilee’s own cradled against her. But soon the librarian realized just what her situation was - that her skirt was lifted above her rump, that her panties were pulled aside, and that Celestia’s cock was pressed to the entrance. Cheerilee was too slow to whisper a single word of refusal before Celestia pushed herself inside, crowning her fingers at the edge of Cheerilee’s hood to keep her stretched for the moment.
Moving fast, Celestia closed her palm around Cheerilee’s mouth as she penetrated her, knowing full well that the woman’s first dick in half a decade would no doubt make her fill the whole library with her moans. Her other hand remained lingering close to Cheerilee’s pussy, fingers kneading against her hood and keeping her twitching and teased. The ease of her pearl pink cock pushing into Cheerilee was smooth and delightful, and though she didn’t go fast for that first moment she did go deep. Very, very deep. Inch upon inch of her cock slipped into Cheerilee’s pussy until she was all the way to the hilt, and while the other woman was left handling the girth of her impressive member she bucked her hips forward once more for good pleasure. It made Cheerilee brace her hands all the harder to the books in front of her, and she went cross-eyed briefly as Celestia fucked her deeper than any toy she had ever used even in her most daring, lonely nights.
“That’s a good whore.” Celestia purred, and when her hand left Cheerilee’s mouth it only travelled so far as her chin. She held it firm and forced her gaze ahead, letting her watch where Rarity was pulling her dick from Twilight’s ass and lining it up against her slippery, soaked teenage pussy. Both Cheerilee and Twilight were in the very same position - hands to the bookcase, rump stuck forward, barely standing on trembling knees. The only difference was that Rarity seemed playful and loving to her friend no matter how hard she was fucking her, Celestia seemed more intent on reminding Cheerilee what a depraved slut she was...a complaint she could not object to. “You’re not as tight as Twilight, but...you’ll do.”
Her words were less a confession that she had gleefully fucked a student, and more of a boast that Ms. Cheerilee wouldn’t be the last whore she wrapped around her dick. Celestia’s smile was broad as she tightened her grip against Cheerilee’s hair and started to fuck forward with an increasingly rapid pace, ensuring that she thrusted down to the hilt with every movement. She was still careful to the point that she didn’t make enough noise for Twilight and Rarity to hear, and was endlessly more concerned that Cheerilee herself would be unable to hold back from crying out. The only safeguard against that outcome was the librarian’s knowledge that if she did, she’d no longer be able to get fucked - something she had desperately yearned for over years of long, frustrated loneliness.
For too long she had been considered cute, but not fuckable enough to be worth pursuing, and her own insular tendencies kept her away from the clubs and bars that would’ve given her the lay she so achingly needed. It was all for Principal Celestia’s benefit, though, as the top educator of CHS was free to enjoy yet another soaked cunt that was gloriously grateful for the opportunity to be used. When Cheerilee peeled her eyes away from the girls in the distance it was just so she could gaze behind her towards Celestia’s face, and be reminded of the level of domination she was under, and of how desperately she wanted the other woman to use her like a depraved, hungry little whore. It was the first time that Cheerilee had finally known the sort of fun that her students got to indulge in all the time, and there was a part of her that didn’t want it to ever end.
“Maybe I’ll stop by here more often, slut.” Principal Celestia finally hissed, leaning forward to once more press her tits against the other woman’s shoulders, moving her mouth to the edge of Cheerilee’s ear. As the two watched the teenagers beyond the bookcase fuck and near their own finish line, Celestia’s breath was hot and heavy on the Cheerilee’s face, cascading across her with power and presence. “Next time I check in, I expect you to come right back here and wait for me. And if you’re lucky and I’m not busy with a tighter piece, I’ll let you suck my cock.”
There was a soft pause in her voice, just as she pushed forward one more time in particularly deep fashion, so hard that Cheerilee’s fingers nearly yanked the books from the shelf. When Celestia spoke again it wasn’t just proof of her dominance over Cheerilee and the others of the school, it was a promise - a promise that the school librarian’s peeping tendencies were about to get more difficult to indulge in, while at the same time more rewarding.
“And even if I’m not here to fuck you, you’ll get to watch me while I make one of those slut students of ours my bitch.” Another short thrust, enough to slap her balls against Cheerilee’s hood. “Wouldn’t you like that?”
Ms. Cheerilee had been on the bottom of this encounter ever since the beginning, and there was no stopping that anytime soon. With her eyes darting from Celestia to the two girls in the distance, she found herself tracing the figure of Twilight Sparkle - of her plump, pregnant, exposed belly, of the look of delight on her slutty face, and of the sight of Rarity’s cock lodged deep in her pussy unloading a torrent of cream. The two girls were clearly spasmed in climax, and they were making a mess of it. Twilight’s juice was dripping to the carpet below and as Rarity shuddered and pulled her cock free, a large glob of white fell from her hole to the floor below. A wet, creamy mess that only seemed to build as Twilight swivelled to her feet, dripping load after load of cum as she struggled in her pregnant state to get her panties back on.
“We...we should really clean all this mess up.” Twilight murmured, looking at the intense, rich creampie that now sat in a puddle on the floor. “If Ms. Cheerilee sees the mess, she-”
“Goodness, darling, we don’t have time!” Rarity called out, just as she snaked a hand around Twilight’s wrist and began to pull her away. “We’re almost late for class!”
That was all Twilight needed. While Cheerilee was still bent over and threaded with cock mere feet away, the two girls started to pad away, grabbing their things and heading towards the front of the library once more. As they nearly fell out of range of the two older women, Twilight could be heard to offer one last thought - one that made Cheerilee’s pussy tighten around that massive, pearl pink cock stuffed inside of her.
“I wonder why Principal Celestia didn’t join us like she said she would?” She murmured, respectfully. “I hope she’s not working too hard…”
Principal Celestia merely beamed at that, grabbed her cock around the base, and yanked it free of Cheerilee’s pussy with a pop. Now that the two women were in some semblance of privacy, she could speak louder and more clearly, and as she did so she tightened her grasp around the base of Cheerilee’s head by means of her hair. She forced the slutty librarian to look back at her, and spoke in a bold tone that suggested the most depraved moment of Cheerilee’s day had yet to come.
“I’d say I’m working plenty hard.” She observed, quirking a brow. “More so than you. You haven’t even kept the library clean.”
***
Less than a minute later, the two women had changed aisles in the library, and now Cheerilee was braced on her hands and knees staring down at the creamy mess that had been left for her to clean. A heaping, fallen creampie of Rarity’s making was still sitting there in all its glory, and as Principal Celestia knelt behind the librarian, she pushed the tip of her cock to Cheerilee’s pussy once more, preparing to lunge into her again. The principal’s smile was dominant and fierce as she started to nudge her hips forward, and with her hand once more locking around Cheerilee’s hair, stated to push her closer to the puddle on the ground.
“What the fuck did I hire you for, if you can’t keep this place clean?” She asked in a seemingly innocent tone, rolling her shoulders and giving a chuckle. “Get to it, Cheerilee, or I’ll find another whore to run the library.”
Cheerilee certainly didn’t want that - especially not on the day that she felt more fulfilled and satisfied with her job than ever before. She swallowed nervously and gazed over her shoulder to the dominant, radiantly-haired older woman, and when she spoke her voice was less of a whisper and more of a tiny squeak, submissive and obedient to the highest degree.
“Y-Yes, Principal Celestia.” She agreed to the command, and shuddered in excitement. “Please...please keep fucking me while I clean up the mess…”
Ms. Cheerilee was proving herself to be a fine whore for the woman that ran CHS, from how she presented her pussy to be freely claimed to how her head bobbed forward and her tongue trailed out, eager to clean up the mess left by her fashionable student. Celestia timed things so that Cheerilee didn’t receive the reward of her cock until she had first pressed her tongue into the puddle of Rarity’s cum, and only once she slurped across it and gave a nervous swallow did she finally get to enjoy the full weight of it again. Once she had proven that she was willing to do as she was told, Celestia gave her the proper reward she had promised in full - grabbing hold of her hips and starting to fuck her, rough and hard and so powerfully from behind that it almost became hard for Cheerilee to keep her head in position. The librarian was forced to press her palms tight to the floor below as she kept dipping her tongue down, lapping up the leftover cum from two of her students’ sinful union. The taste of Rarity’s spunk flavored with Twilight’s juice was one that Cheerilee would remember for the rest of her days, for it came in the same day that she first bent over for Principal Celestia and allowed her plump, pink pussy to be used for her delight.
It went on like that for several long moments, and through it all Cheerilee did her best to clean the mess while Celestia used her as a slutty, repressed cocksleeve. When the older woman’s climax finally arrived it was more than enough to push Cheerilee over the edge as well, and both women were left hissing in pleasure as that pearl pink cock started to pump glorious loads into Cheerilee’s pussy. There was never even any whisper of pulling out - and if Cheerilee wound up looking like Twilight Sparkle, she would just be thankful for the opportunity. As the librarian spasmed in climax, trembling and twitching and violently shuddering, her pussy was pumped to the point of overload, cum dripping down from above to make a mess of her own.
“Not bad, Cheerilee.” Celestia finally observed, offered the woman’s ass a firm open-hand slap, and then pulled her cock free with a loud, wet noise. In the aftermath Cheerilee couldn’t stop cum from oozing straight out of it, dripping more and heavier down to the carpet below to mirror Twilight’s previous actions. When Ms. Cheerilee looked up at the other woman - still fully dressed but very clearly just recently used as a horny sleeve for dick, she was blushing when she finally spoke.
“Do...do you want me to clean this mess up too, Principal Celestia?”
The response was surprising, as Celestia merely shook her head and gestured to the aisle that Cheerilee had been peeking from previously.
“Fluttershy will be here in a few minutes, and she can clean it up.” She offered dominantly, letting her still-soaked cock swing back and forth while she did so. She was utterly shameless in how open and obvious she was, relying on her dominant grace and simply expecting others to do what she desired. “You can go back and watch. But don’t touch your pussy, Cheerilee. It’s mine now.”
“Y-Yes, Principal Celestia.” The librarian submissively nodded, and brought herself up to wobbly knees before rounding the corner to do as she ordered. Sure enough, it wasn’t long after that Fluttershy visited Principal Celestia, and the older woman wasted no time in ordering her to her knees to clean up the mess that was just made. The entire time, the school librarian simply lurked and watched.
She knew that CHS had a problem with lust that ran wild through the whole school, but had no idea that it went this deep or this depraved.
And finally...she was a part of it.
The End.
Author's Note
Been a while since we've had a new piece of the EBFiTS saga. Hope you enjoyed it!
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