Chapter One
The Principal’s Principles
-by Drace Domino
Friday nights were usually boring for Principal Celestia. Not by choice, of course, but by circumstance - the poor woman invested so much of her time and energy into taking care of the students at Canterlot High that she never really had time to build a network of friends outside of school. There was no group of like-minded women she could connect with over a round of drinks while they talked about the men they were seeing, no couples that were ever trying to hook her up with a date of her own, and even her own sister was usually busy with her book club! For as much as Principal Celestia seemed like the cool head of CHS, for as much as the students looked up to her and admired what she did for them, once Friday came around it was usually the segway into a long, boring weekend.
And as such, she usually didn’t fight it when the other teachers asked her for help on Friday nights. While Ms. Cheerilee was out on a date, it was Celestia that was picking up the slack for the younger woman - hunched over the desk in her office and tackling a few more bits of paperwork that she was asked to handle. It wasn’t really that she minded helping out so much, but would it really have killed Cheerilee to see if her newest date had a friend for them to double up?! Such was the life of the principal of CHS - selfless, put upon, and honestly...frustrated.
“Well, another week down,” Celestia murmured to herself as she finished up the final bit of paperwork for Ms. Cheerilee, sliding it to the edge of her desk for the younger woman to pick up on Monday. “Another week down and...another weekend ahead of me.”
The mere thought of such a thing was enough to put a heavy weight on her, and she grunted while fishing her phone free of her pocket. Just like every week, she’d sent out a few feelers to some of her peers in the hopes of arranging something to do - maybe a new traditional of going out to a fancy restaurant and treating themselves after a long week’s worth of work, or perhaps she could wrangle some of the singles to hit the club with her on Saturday night! Unfortunately, as she scrolled through her messages Celestia’s heart steadily sank, and her frustration grew all heavier.
Luna. Harshwhinny. Cadance. Even Cinch, whom Celestia had texted out of sheer desperation, left her message on “read.” No replies. No counteroffers to do things next week. It’d seem like once again, Principal Celestia was a cool woman at school and a total loser afterwards. With a heavy sigh and a grunt from the back of her throat, Celestia tucked her phone back into her pocket and murmured to herself in irritation.
“Maybe I should see if one of the students want to hang out,” she grumbled, before absently chuckling and shaking her head. “Because that’s not a recipe for disaster.”
Celestia left her office that night much in the same way she did every Friday - with a nagging dream that next week it’d be different. Maybe she’d finally convince her little sister to skip her book club and go dancing with her, or perhaps she and Harshwhinny could go to one of the bars in town and see if they could scan for handsome, younger men. Hell, at this rate, she’d take that miserable old bat Cinch out on a date, just to say she did something other than graded papers and went home to stuff her face with ice cream and masturbate in the shower. As the responsible woman tucked her hands into her pockets and milled about through the halls of CHS, her heart sank heavier and harder than usual. She did this same song and dance every week, and yet...it never got any easier. There was no toughening up a lonely heart.
From there, she went about all of her usual responsibilities - making sure every door to the school was locked, ensuring the alarm system was turned on, and double checking that Pinkie Pie hadn’t left any of the ovens in the Home Ec room on. Which she did, of course, but at least she left a tray of cupcakes on the counter, complete with a tiny note from the sweet girl to the miserable, lonely old woman that prowled the halls late at night.
“Thank you for being the super best principal EVER!!!” Celestia read the note in a fairly deadpan voice, but admittedly...it did make her smile. As she casually tucked the note into her pocket and scooped up the six pack of brightly-decorated cupcakes, Celestia gazed at the treats with a half-lidded look and a tiny smile, murmuring half to the snacks and half to herself. “You and a bottle of scotch will make for a good enough dinner, I guess.”
It was minutes later that Celestia had piled into her car - the only one left in the parking lot at that late an hour. The sky was dark and the evening was well under way for most of the city, leaving Celestia with little more to do that night than get home without feeling too bad for herself. With the tray of cupcakes on the car seat - one of them having already been consumed - the woman gave a labored sigh as she turned the ignition and started to drive, firmly suspecting that the most eventful and exciting moments of her day were already behind her.
She’d be wrong, but not without more than just a few bad decisions along the way.
***
Celestia only intended to make one stop on her way home that night, to grab the bottle of scotch that would complete her dinner for the evening. She managed to carry out that plan easily enough but it was on the final stretch of her trip that she was unexpectedly derailed, and in a fashion that led to her night taking a turn for the better. With the bottle of booze sitting on the passenger’s side beside the leftover cupcakes, Principal Celestia’s car suddenly came to a halt - tires screeching and car jostling as the educator slammed on the brakes, her eyes wide at what she was witnessing in the suburbs.
It wasn’t all that uncommon to see some of the college kids having a party on a Friday night - especially during the fall, when their parents tended to take last-minute vacations before the winter months started. Sure enough, one of the houses a few streets away from Celestia’s was in the middle of such chaos right now - music blasting, a line of cars parked along nearly every inch of the street, and more than a handful of college students having a good time out in the lawn. Usually, it was nothing that Celestia would care about beyond being at least a little jealous that they were having a better night than her, but that evening...that evening she just had to take action, because she recognized one of the faces in the crowd.
Flash Sentry.
The young man was stumbling around the lawn in a clearly inebriated state, with a line of college kids watching him and laughing. It was a scene Celestia could remember clearly from the old days of college - a bunch of cool older students got a high school senior drunk, chuckling as he got completely wasted and set himself up for a bad evening filled with poor decisions. Throughout the years as a principal she’d had to break up more than a few of these incidents, and when she saw one of her own students as the victim, something inside of the older woman sparked. With her eyes flashing with an irate fury and a twist of her fingers setting the car to idle, she swung the door open and started a ferocious march towards the lawn - eyes narrow, mouth a thin, angry line, and her fists tightly clenched.
Thankfully, the sight of an approaching authority figure was enough to send most of the college students scattering, fleeing into the house to continue the party in peace. The only person that seemed unaffected by her presence was Flash Sentry himself, and as Celestia got within a few feet of the boy, she could tell just how far gone he was. A haze of beer surrounded him and he was only barely able to stay on two feet, tripping and stumbling with each wobbly step. When he laid eyes on the approaching woman his voice suddenly filled the air - innocently jovial, complete with slurred speech and a wide swing of his arms.
“PRISSIPAL CLEEEESTIA!” Flash beamed, his eyes shining - if a bit glazed. He was dressed in his typical CHS football jersey and a pair of baggy blue jeans, the latter of which were stained with grass across the knees from more than a few tumbles in the lawn. He was even holding a tall can of beer in one palm, which he didn’t even register the loss of when Celestia snagged it from his grasp and threw it to the grass below. “DNT KNOW YOUUUUU PARTIED!”
“I don’t,” Celestia responded shortly, curtly, and grabbed the boy by the wrist while moving a hand behind his back. She started to usher him towards the car with a slow growl setting at the back of her throat, fighting back the urge to storm the house party like any proper vengeful teacher would. “And neither do you. I’m taking you home.”
“MMMKAY, I think ‘m reaaaady,” Flash practically purred, a clear sign of just how drunk the boy was, seeing as how he didn’t fear any reprisal from his parents. As he walked with Celestia he swung an arm around her shoulders and hung on her like an old coat, forcing the older woman to take a long, deep scent of just how blasted he was. “S’fun party though, right? Y’see me dance? You make out with anyone?”
Celestia grunted underneath the boy’s weight - and the weight of his words. As she hobbled her way towards the car with Flash Sentry in tow, the older woman chose not to answer him - he was clearly so addled that it wouldn’t make much of a difference. It was all too obvious that the boy had been drinking heavily throughout the entire night, and even if she did let him stay at the party, he wouldn’t remember anything by the time the morning came. Left to his own devices and the bad intentions of the college students, Flash would only get himself in trouble...and that was before she even considered the possibility of the boy driving home. With the heart of a responsible educator and a loyal principal, Celestia shuffled her way to the car with Flash as her burden, only barely listening to him while he spoke.
“Ssss’okay, Celessssstia,” Flash slurred, and sounded a little somber by the time they reached the car. Celestia was still fumbling with opening the passenger’s side door as she balanced Flash against her as the boy kept ranting. “I struck out, too.”
“I’m sorry to hear that,” Celestia rolled her eyes with no true enthusiasm behind her words, just as she finally managed to get the door open. At one point she leaned forward to push the cupcakes and scotch to the backseat of the car, only to then turn back to Flash to assist him into the open seat. “Maybe you’ll have better luck with girls your own ag-mmmph!”
The drunk boy was on her in an instant, moving so fast that Celestia didn’t have an opportunity to respond or stop him. One second she was about to spin him into the passenger side seat and the next she herself was being forced into it, weighed down by the body of the drunk boy collapsing against her in a full-hungry embrace. Flash’s drunken state pushed him into a rather bold moment of bravery, forcing his mouth flush against that of an older woman’s, his hands moving forward to not just grasp his principal but grope her. It happened so fast that Celestia was utterly helpless to stop it as she was forced on her rump in the seat, eyes going wide and her entire body flinching as she was unexpectedly assaulted.
It was overwhelming. The scent of Flash’s hard-partying figure filled Celestia’s senses as the boy pressed his mouth hungrily to her own, lips parting and his tongue breaking past the older woman’s lips to steal a lewd, wholly inappropriate kiss between them. His tongue swept greedily back and forth and fully informed Celestia of just how damn much he’d drank over the past few hours, offering her a flavor of beer and even harder liquors that still clung to his lips. In the same moment he groped at her hungrily, one hand lunging forward to squeeze at the older woman’s breast, fondling her through the fabric of her shirt and bra in the clumsy style of an inexperienced teen. His other hand was even more bold, lowering down to help itself to a tight, snug handful of his principal’s rump. As he kissed and groped Flash essentially collapsed atop Celestia and in that moment the older woman could feel a clear impact of something pressing against her - the heavy bulge at the boy’s jeans which he shamelessly grinded against her, rolling forward with a single, heavy, heaving thrust.
Celestia broke free of his unexpected assault before too long, but it still left its mark. She grabbed his shoulders and forcibly shoved him away, even as her legs stretched out so she could kick over to the driver’s side. For the moment she kept her cool and stayed calm - frowning with lips glistening with excess beer and a teen’s spit, her shirt snagged and a few buttons popped by how hungrily he kept his grasp around her breast. When she finally managed to kick into the driver’s side, Celestia gave an angry grunt and yanked Flash all the way in - hissing from the back of her throat in a barely-restrained fury from the boy’s brash, drunken actions.
“Flash, I’m absolutely telling your parents about this!” She swore, though in the moment her primary concern was getting the drunk boy in his seat. Even after yanking him down like a rag doll, Celestia had to pull his legs inside before stretching far over his body, reaching for the handle of the open door. With one palm slapping down another half-assed attempt to grope at one of her hanging breasts, Celestia snagged her fingers around the handle and swiftly slammed it closed. A split second later she pressed the button to activate the child lock, and shortly thereafter she was reaching for the seatbelt, moving it across Flash’s chest and lap while she kept glaring at him. “I’m so disappointed in you! I don’t think I’ve ever been this angry with a student! How dare you try to kiss me!”
She’d realize, once she was back in her seat and trying to collect herself, that her words had only managed to fall on deaf ears. Flash Sentry - post drunken grope and finally sitting back in a comfortable seat - had fallen into a deep, drunken sleep. Celestia simply stewed, settled into her own spot, and cast an irate glare at the boy before staring down at the steering wheel. She was angry beyond measure - her blood boiling at not only how forward Flash had been, but the irresponsible college students that let him get this drunk to begin with. What if she had been a girl from CHS? What if she was a student that wasn’t able to defend themselves?! Celestia swallowed heavily - her spit laced with the flavor of Flash’s alcohol-infused own, and she took a long, deep breath of the smell of sweat, booze, and bad decisions in the car.
She was mad at him, yes, but more mad at herself. That was the first kiss she’d had in years.
***
The car came to a stop a few minutes later, but it wasn’t anywhere near Flash’s house. Celestia found herself driving along the outskirts of the suburbs before coming to a stop along a seldom-travelled road, pulling to the side and past a few bushes to keep the vehicle obscured. It all happened before the woman really knew just what she was doing, and even while she drove she found herself justifying her destination in a variety of ways - if she dropped Flash off at his house in his current condition, obviously his parents would be furious! If she delayed things, then maybe he’d have a chance to sober up and escape some well-earned severe punishments! She was indeed telling herself that the diversion from her destination was for Flash’s benefit, but in reality...she just needed a few minutes to think. Once she parked, Celestia turned the headlights off and shut down the ignition, leaving the car quiet and dark while the woman pressed her palms to the sides of her head and drew in a few deep, steadying breaths.
While Flash was literally asleep in the seat beside her, the principal of Canterlot High was tormented with certain thoughts she couldn’t push away. Flash had been so bold when he tackled her into the seat, groping and kissing and grinding her as if he had been invited to do so. The way his hands felt against her breasts, the taste of his beer-soaked lips, the sheer girth that he rubbed against her in those fleeting few seconds...all of those sensations had made Celestia squirm the entire drive to that point, and now? Now, she was sitting on impulses and thoughts that she never would have suspected herself capable of before. Amidst her deep breathing and her trembling, Celestia gazed over to the boy beside her, buckled up and secure but still thoroughly asleep. When she finally spoke her voice was quiet, exploratory, and she even stretched out a hand to poke at the young man’s arm.
“Flash…? Flash, are you...awake?” After a few nudges, Celestia lifted the same hand and waved it in front of Flash’s face. When she didn’t receive a response, it was more clear than ever the boy was out cold, the result of his first drunken night of teenage excess. The poor thing had chugged himself into a stupor, and Celestia had seen enough drunk students in her day to know he’d most likely be out until morning. And that thought in particular made the older woman tremble, both with the frustration over what Flash had done, and the guilt she was experiencing over certain...temptations. Her eyes finally drifted down along Flash’s body, gazing to where his jeans were still fiercely tented by something underneath. The benefit of youth - hard as a rock and thrillingly stiff, even while the boy himself was unconscious. Celestia, almost by pure instinct, started to reach out towards his bulge, only to stop herself halfway through with a forced, strained laugh.
“H...Haaaa, what...what am I thinking?!” She shrugged, doing everything she could to stop herself from reaching out again. “I can’t! I mean, it’s clear that he wanted me to, but...but even if he was awake, I...I just couldn’t!”
It was a poor sign that she sat there for a solid two minutes telling herself the same sort of platitudes, only to still fail to convince herself in any meaningful way. While the car sat dark and quiet, Celestia was afforded all the time she needed to talk herself out of this madness, and still she stumbled - just as her hand stretched forward again and again, only to peel back at the last second. Whether it was a noise from out in the woods beyond the car or Flash’s body suddenly shifting, or Celestia’s guilt spiking she always seemed to stop short of her destination, and each time she failed to reach his bulge a part of her grew more and more determined. In the end, Principal Celestia effectively talked herself into the exact opposite of what she should do, and after enough false starts she finally closed the distance between them, pressing her hand against Flash’s bulge through those thick, tight jeans.
“Mmmnnnggg…” A whimper escaped the back of the sleeping boy’s throat, letting the older woman know that despite his slumber, he could still feel. He even shifted a little in place, but the seatbelt was thankfully tight enough to keep him in position. With her eyes splitting their attention back and forth between Flash’s face and his lap, Celestia rolled her fingers in a slow pawing gesture, marvelling at the girth that was pressing against Flash’s pants.
“...wow…” She whispered to herself, and gave a nervous, quiet swallow as she groped her student. Perhaps it was just how long it had been for the older woman, but even without seeing it, she was sure Flash was hung like nobody she’d ever been with. The boy was a surprising stud, sporting an enormous length below his jeans that he’d been keeping secret all this time. Celestia couldn’t help but chuckle to herself as her hand kept rolling back and forth - massaging, groping, fondling. “Bet you’d split someone like Twilight in two, wouldn’t you, big guy?”
All she received in response was the faint murmuring of an unconscious student - and a surge of guilt as her debauchery pushed her forward. Celestia went from groping to even more depraved action quite quickly, her other hand soon stretching forward so she could maneuver her fingers at Flash’s jeans. While keeping her eyes laser focused on the boy’s face and tracking him for any signs that he might wake up, she slowly unbuttoned his pants before pinching the top of his zipper, sloooooowly beginning to yank it down as quietly as possible. As she proceeded, the older woman’s breath was steady and silent, her heart racing faster than she could ever recall and her voice carried out in a hushed, delicate whisper.
“Easy...eaaaasy...God, can’t believe I’m doing this…”
Disbelief aside, the proof was soon right there in her hands. Mere minutes after Celestia parked the car, she’d managed to fish out Flash Sentry’s length from his pants. It wasn’t particularly difficult to do so - the boy’s cock was so hard and so excited that it had already found the gap in his boxers, pushing against it vigorously enough to pop free as soon as his jeans were loosened. His cream-colored shaft was exposed even before Celestia suspected, and the principal gave a pronounced gasp as it stuck straight up from his lap, announcing its arrival in glorious fashion. It was huge, more than the teacher expected despite her fondling, and she could feel every muscle in her body go tight upon witnessing it. A pathetic gasp escaped the back of Celestia’s throat and she ravenously pressed her thighs together, trying to control a certain, shameful heat that had been building ever since Flash’s stolen kiss. Before she even realized it, she’d closed her fingers around Flash’s length, squeezing and studying, gauging his reactions as she felt his heat through the inches of that stiff, glorious cock.
The woman desperately bit down on her bottom lip, her mind spinning. She wanted to strip down and ride it right then and there, but...but that was absolute madness, wasn’t it?! She’d already crossed so many boundaries, there was no way she could get away with something so foul and depraved! Refusing to let herself humor such an idea, Celestia finally spoke with a trembling voice, just as her hand started to buck back and forth across Flash’s twitching, young shaft.
“Just...just a handjob,” she promised the sleeping boy - and also herself. “It...it’ll help you sleep easier.”
More justification. More convincing herself that what she was doing was for Flash’s benefit and not her own mature, wicked hunger. Flash’s cock felt incredible within her grasp, warm and inviting and flawlessly stiff. Smooth to the touch with a glistening head already glazed in some fondle-forced precum. He was almost so thick that Celestia couldn’t close her fingers all the way around him, and as a result she soon closed both hands over his shaft to make sure he was being treated properly. For all she knew, this was the boy’s first handjob ever! It only seemed fair that it would be a good one...even if he wouldn’t remember getting it.
Back and forth, back and forth, Celestia stroked Flash Sentry’s rod, her hands moving slowly and carefully while she continued to split her attention between the boy’s cock and his face. She nibbled her lower lip while her cheeks flushed with color as she kept fondling the young man, her mind constantly spinning between thoughts of shame and guilt over what she was doing and the twisted justifications she managed to conjure. After all, Flash clearly had been interested in her! He was the one that made the first move! Besides, surely he’d never remember this! The young man barely stirred while his principal kept pumping his length, fidgeting from time to time but only in the most modest of ways. A tiny whimper here, a twitch of his chest there, and through it all his length remaining rock hard within the older woman’s grasp. Gloriously hard. There was nothing like a hung, teenage stud!
Celestia was breathing heavily by that point, but not because of the effort. Her excitement was building as she gazed down at Flash Sentry’s length, watching as her hands seemed to move without her even meaning to control them. When one palm slid across Flash’s cockhead and collected a glistening touch of precum, when the other slid deep into the boy’s boxers and cradled his sack...surely that wasn’t her doing these things! She gave a nervous gulp and even whispered to herself as she kept pumping him up and down, her wrist rocking back and forth while she felt the boy’s pulse against her warm, inviting palm.
“He’s...he’s so big, I…” The older woman’s passions were flaring, excitement burning inside of her that she could possibly hope to fight against. Her thighs squeezed together mightily as she actively squirmed in her seat, and a whimper escaped the back of her throat that soon rolled across her tongue in the form of a faint whisper - words that she knew were objectively wicked for her to say, and yet carried her forward while her head started to drop. “Maybe...maybe if I...if I just take a taste…”
With that, Celestia’s head dipped down into the lap of her student, mouth open and eyes closed as she invited his cock into her maw. She met his tip with an uncurled tongue that immediately swirled around him, slurping in a slow, satisfied circle as she practically shook with excitement. Still barely able to believe she was doing all this, Celestia kept her hands locked against Flash’s member - one holding his shaft at the base and the other fondling his balls, even as she ushered inch after inch of his stiff, young dick straight down into her mouth. Slowly she slurped and suckled, kissed and licked, even pulled back to brush it across her cheeks in affectionate fashion, and when she paused long enough to gaze up at Flash’s face she was satisfied to see that he was still asleep. It was almost a shame - the boy’d never know he got a roadside blowjob from Principal Celestia, a woman more than twice his age.
“G...God, so good…” Celestia murmured to herself as she returned to her work, sucking on Flash’s cock amidst a state of full blown euphoria. The long months, even years, that the older woman had gone without affection had finally pushed her to the breaking point, and she was celebrating her newfound madness with a heaping mouthful of flavor. Each time she pressed her head forward she took half of Flash’s cock or more into her mouth, even trying to deepthroat him a few times with mixed levels of success. The boy had a real monster hiding between his legs, and a cock this big would require some practice to gulp down. More time than she had that night, unfortunately. Instead, Celestia had to satisfy herself by slathering Flash’s cock in her spit before sealing her lips around the midpoint of his dick, just before closing her fist around his member at the same point. With her lips and the top ridge of her fist forming a seal against each other, she suddenly started to bounce up and down.
Shrlp, shrlp, shrlp! Wet, sloppy noises filled the car, which by that point was rocking up and down thanks to the momentum of the older woman. Flash - still blissfully unaware of anything more than a particularly good dream - slept through the entire thing, his head resting back and a line of drool escaping the corner of his lips. Throughout the entire event he didn’t so much as stir while Celestia sucked him down hungrily, greedily, ravenously, up until the point his slumbering body finally hit a point of pleasure that couldn’t be resisted anymore.
It was a true nocturnal emission if Flash had ever had one - encouraged by the wet, greedy mouth of his principal in the passenger side of her car. With nothing more than a tiny jerk of his body, Flash’s tip started to release a sudden torrent of cum, and Celestia was completely caught off guard by it. The first jet of spunk that fired into her mouth was enough to nearly make her choke, and she ended up coughing and gagging as it clung to her throat. In the seconds that followed - seconds during which her fist kept jerking him off through pure momentum - Flash’s dick continued to spasm, launching jet after jet of cum straight at Principal Celestia’s face, plastering her with thick ropes of white spunk that she had worked so hard to earn. By the time Celestia managed to swallow down the first shot Flash was already finished, leaving Celestia’s still-gripping hand coated in excess seed and the older woman’s face and hair streaked with lines of white. She was almost afraid to look up for fear that Flash might have woken up, but when her eyes finally lifted she breathed a sigh of relief - he was still leaning back, still dozing, still drunk beyond his years.
“Fuck, that was...that was intense, Flash,” Principal Celestia soon whispered, mostly to herself as she slowly sat up. With her face still plastered in cum, she gazed at the rear view mirror - blushing almost instantly when she saw the mess that was made. With no tissues on hand, the mature, responsible teacher did the mature, responsible thing - press a finger against the spunk that clung to her face and slowly slid it towards her mouth, her lips parting and her tongue stretching outward. Each taste of cum across her tongue made her shiver all the more, excitement building and bubbling, by that point long having bested any concept of shame that could possibly claim her. She ended up cleaning herself of Flash’s cum through a series of greedy swallows, and by the very end was dragging her tongue across the hand she used to jerk him off, cleaning the last few drops from the crook between her thumb and forefinger. Only then, in the heat of the car filled with a musty, scented air, did Celestia whisper once more. “I...I should get you home, shouldn’t I?”
At that point, she couldn’t wait to drop him off at his house, just because that meant it was all the quicker she could get home and stuff a hand down her pants. With nothing else planned that evening other than a bit of depraved shower masturbation, Celestia soon turned with the expectation of tucking Flash Sentry back into his jeans. When she reached over, however, she paused.
Flash was still drunk. Still asleep. And still...hard.
Very, very, very hard.
The woman bit her lips together as she gazed down at the young man’s enormous length, jutting upright from his lap and still wearing her spit along every inch. And at that point, a thought popped into the principal’s mind - one she wasn’t proud of, but was still more than willing to give herself over to.
What...what else could she get away with that night with her inebriated student?
The End.