Cheers For Best Headmistress
Author's Note
Apologies for the wait. Here's the story for the Princess of Infidelity contest and trust me when I say this... I... cannot believe I actually made something like this, I'm just... speechless. Anyways, as always, thanks for your patience and support, stay tuned and keep bronying on.
Cheers For Best Headmistress
Crystal Prep Academy. One of the most prestigous schools in Canterlot City where the richest and smartest of teens enroll into in order to secure their futures when they graduate. Just like their parents before them... at least that's how it used to be until Abacus Cinch was fired. The Board of Education didn't take too kindly to the former head mistress blackmailing one of her top students into helping her school win the Friendship Games all for the sake of keeping the school's reputation.
Luckily, Crystal Prep is now under new management and has been going quite smoothly ever since Cadence was promoted from Dean to Headmistress. Since then, tensions have gotten lower... with time, that is and more and more gifted students were given a chance to enroll into this school.
Of course, being one of the youngest headmistresses can take a toll on Cadence. Luckily, she has Shining to help her relax when the day is done. But sometimes, even he can be too tired to help out and would come home passing out on the couch after a hard day's work. Oh, speaking of which, because of Cadence's promotion to Headmistress, her salary was raised and she and Shining have been saving up some extra money and put it all into their brand new house, which they've now been living in for a few months now.
And having plenty of time to settle down after the move, it was almost time for another important event for the couple to get ready for; Cadence's birthday. Needless to say, she and Shining sent out invitations for her birthday party to her families, especially her in-laws and a few friends.
Of course, there was one special guest she invited. And boy would her family be surprised. Soon, the day finally arrived for Cadence's birthday. Almost everyone was present and accounted for and the entire house was set up for everyone to have a huge blast. There were big speakers set up in the living room by the TV so the music could be heard at full blast. A large selection of food was placed on the kitchen counters and a whole table of snacks set up in the middle of the living room.
There was even different kinds of drinks. Canned and bottled soda, beers, juice boxes and water bottles, all set up for anyone thirsty. At the beginning, everyone was enjoying the party, talking amongst themselves, sharing their stories with how life's been treating them.
And now, as the party progresses, there's a knock on the door. "Oop. I'll get it." Cadence calls out, then puts her drink down on the coffee table. She goes over to the door and answers it. Behind the door, she gasps in delight to see a familiar face. A young man who has dark grey skin, crimson red eyes and pitch black messy, shaggy hair, wearing a thin, black hoodie, blue t-shirt underneath and brown pants.
"Hey, Principal Cadence! Happy Birthday!" he says.
"Shadow Force! Thank you, but you don't have to call me "principal." We're not in school right now, so just call me Cadence and please, come on in." Cadence says, letting him in.
"Sweet. Thanks Cadence," Shadow replies, pumping his fist, walking in.
Cadence closes the door and watches Shadow mingle with the others. Shadow Force has been one of her best students over at Crystal Prep Academy. He's not like the other students who try to act all prestigious and top-notch... or "uptight" as they put it. No, Shadow is more of a laid-back and carefree guy. Despite this, he actually still finds time to study hard and get good grades. It still comes as a surprise knowing he's Sombra's son, the man who used to be Cadence's teacher.
When it comes to parties, Shadow knows how to liven up the tempo. He puts in the extra effort to bring out the party animal in everyone around him.
It's that kind of energy in a young man that just made her so... envious of him. Ah, she can still remember the days of when she was a passionate, young teenager. Back when she was a cheerleader, she was practically the most popular girl in the entire school. It was no surprise she had a few boyfriends during her time, but nothing serious until she stuck with Shining. What she wouldn't give just to at least feel younger.
"Hey, Cadence! Whatcha starin' into space for, come on! Get your boogie on!" Shadow calls out while dancing to the rhythm of the music beats.
The young headmistress snaps out of her thoughts and joins the others in a big dance. The lively beat in the living room was really got everyone busting a move or two. But the biggest stars were actually the birthday girl and surprisingly... her special guest, Shadow. Little did he know, Cadence was checking him out while she was shaking those milkshakes of hers. And every moment she takes to glance at this young, energetic, spry, lively young man, she couldn't help but feel turned on.
Of course, she's not the only one stealing a few glances. Shadow would sneak a few peeks at Cadence when she's not looking, admiring how sexy she looks when she's dancing. 'Damn... if she were younger or if I was older, I'd wanna make her my gal.' he thought.
The music keeps going and Cadence really starts to shake her groove thang. Her friends and family whistle and encourage this birthday girl to keep it up. Of course, the more she does shaking her sexy ass to the music, she's turning on more than just her boyfriend. Shadow steals a few glances at Cadence's hot, cloth-covered ass while enjoying the party to the fullest. Even Cadence is checking out her special guest's ass, licking her lips in secret, getting more excited by the minute.
Eventually, the song ends and everyone applauds her. She applauds back and then the music on Shining's iphone, which is attached to the speakers, plays another lively song.
While the song plays, some of the people keep dancing while others talk amongst themselves, enjoying the snacks and drinks, typical things you do at a party. Cadence decides to step into the kitchen and treat herself to a nice cold bottle of apple cider. Shadow also steps into the kitchen to get a drink.
"Hey, you got some hot moves there, Cadence," Shadow whispers.
"You didn't do so bad yourself, Shadow," Cadence whispers back, giggling. "So, how are is my special guest liking the party so far, is it to your liking?"
"You kidding? This party's off the charts!" he says with a thumbs up.
"Well, that's good to hear," she winks before heading back to the party with her bottle of cider. Shadow can't help himself but admire his principal. The way she always cares for others, be they her family, or her students, she's the best thing that's ever happened. Shadow sighs happily before sipping his soda.
"Cool party, huh?" Shining says, coming over and getting some punch.
"You bet. The only thing that could make this party even better is a little bit of karaoke. I love singing in front of an audience and uniting people through music," Shadow replies, getting Shining to chuckle a little.
"Hmm... that's not a bad idea," Shining says, then pats Shadow on the back. "Hey, everyone!"
Getting everyone's attention, Cadence goes and stops the music. "What's on your mind, dear? Is there something you want to tell us?" the birthday babe asks.
"Actually, our little friend here has a suggestion," Shining says, nudging Shadow forward.
"Guys, this party is great and all, but what do you all say to a little bit of... KARAOKE? Nothing gets a party going better than a little bit of karaoke! What do you guys say?" he asks.
"Hey, now there's an idea!" Twilight Velvet agrees.
"Sure, but I'm not sure I can sing. I'm... sorely lacking in that department," Night Light says. He chuckles nervously since he's never been good at singing.
"I don't mind some karaoke," Twilight Sparkle adds.
"Sounds like we're gonna have a real blast tonight. And... since you were the one who suggested it, why don't you start us off, Shadow?" Cadence offers.
"Maybe... but I think you should go first. It is your birthday after all," Shadow replies.
"Ooh, chivalrous. Well, if you insist, then I don't mind starting things off," Cadence says. The others in the house all cheer as Cadence turns on the TV and puts it on the YouTube app. There, she selects a song of her choosing before everyone watches as she wows the crowd.
After her song finishes, her friends and family cheer and clap at the stunning performance she gave and she bows for the praise and goes to join her friends. "Now then... I believe it's your turn, Mr. Karaoke, so how about you show us what you got, Shadow Force," she encourages with a wink.
"Alright, but get ready for a blast from the past!" Shadow replies. He then steps up and selects his song and the moment the others hear this theme... they instantly knew... he's not messing around.
The young man takes off like a professional singer. The energy he gives off livens the mood in the entire house, getting everyone to clap with the beat.
Some of the people whistle and cheer as he keeps singing his heart out. Shadow even busts a few moves, as if his body has bonded with the music. Cadence, while watching him strut his stuff and singing so well, can't help but feel so turned on by this lively youth.
Moments later after he finishes his song, everyone cheers for him, clapping away. "YEAH!!! Who else wants a chance to blow the roof off this place?" he asks.
"Ooh! Let me!" Velvet says, stepping up while Shadow steps down. He then sits down and has a few chips while Cadence chugs down the rest of her apple cider.
"Hey, babe, I'm gonna use the restroom, I'll be right back," Shining says. He then plants a kiss on his girlfriend's cheek before leaving.
With her boyfriend occupied, Cadence turns to Shadow and then walks up to him, then gets behind his seat and leans down to his ear. "Shadow, would you mind heading upstairs to my room? I need your help with something and Shining isn't available at the moment." she asks sweetly.
"Sure, okay." he shrugs, not knowing her plan. He gets up and sets his snacks and drink aside, then heads up the stairs with Cadence, with no one paying attention.
Cadence happily shows him where her room is and then once there, Shadow opens the door, entering the master bedroom and admires the decor. It has a king-size bed on the left-hand side of the room with two layers of blankets, four pillows at the head of the bed, two on the left and right. On the far right is a door that's wide-open leading into a big walk-in closet. Right in the back of room, in the center area is a big dresser with a large mirror with 8 drawers.
The bed has two nightstands, one on each side and on the right hand side, mounted on the wall, is a flatscreen TV, no doubt for late night TV shows before bed.
"Hmm... it sure is nice and roomy. You must be one lucky girl, Cadence," Shadow says, looking around, not knowing that Cadence is slowly closing the door. The thirsty, hot principal had loads of plans for this lively young specimen, licking her lips in anticipation.
"Thanks, Shadow. Now could you sit on the edge of the bed?" she asks.
"Sure, but... how is this gonna allow me to help you?" he questions, confused.
"You'll see. And sit facing the exit, please," she instructs.
Shadow looks at her with more confusion before shrugging it off. He walks over to the bed and sits himself down while Cadence heads off to the closet. She gives a faint giggle as she closes the closet door behind her, then turns on the light. Shadow sits there patiently waiting. His feet dangle over the floorboards, he hums the tune of the song he sang earlier to ease his boredom.
Minutes later, he hears the closet door open along with Cadence's faint footsteps. "Okay, Shadow, you can go ahead and look now." she says.
The young Sombra spawn looks behind him and nearly feels his heart leaping out of his chest from seeing his principal all decked out in a Shadowbolt cheerleader outfit. Her outfit looks like it's barely able to fit her, particularly around her massive HH-cup boobs and her fantastic ass. Shadow can clearly see part of her lower breasts showing from under her shirt. Her miniskirt's a little... too small and does nothing to show off her turquoise-striped panties and soft, smooth thighs.
Her cheerleader outfit is an indigo color, just like the normal school uniforms, with gold trims. She has her hair tied in a cute ponytail, making her look younger. "So, you like what you see?" she asks.
Shadow's mouth opens up, but no words come out. His eyes dialate and his whole body heats up and on for the icing on the cake... the beast from within is now poking through the confinements of his clothes, begging to be let loose and ravage her sacred dungeons. Cadence has him right where she wants him... Of course, Shadow slowly forms a smile on his face. A very... smug one at that.
"Hot damn, Cadence. I'm surprised you'd show this to me of all people. I gotta admit, seeing you in that outfit makes me wanna take you and make you mine right here and now," Shadow admits.
"Well then... what are you waiting for, an invitation?" Cadence asks, posing all sexy. Shadow can't believe what he's hearing right now. Is she ACTUALLY giving him the green light to get laid with her? This has all got to be a dream, a very wet, but very vivid dream.
"Well... before I even THINK about fulfilling my wet dreams, I gotta know... why me? Usually this is the kind of thing you would show Shining Armor." Shadow points out.
"True, but there's something very unique about you, Shadow. While you do have good grades like your classmates, you seem to give off a more... more... exuberant vibe. You're outgoing, free-spirited, you even brought the party to life with your positive energy. You might not be as zani as Pinkie, but you do make everyone feel good and that kind of attitude is what I like most about you." Cadence explains.
"Awww, you're making me blush." Shadow says, playing it humble. "Then again, I try to make myself different from my old man, even if he doesn't approve of my... "reprehensible childishness." Shadow quotes before blowing a raspberry as a sign of rebellion towards his father.
"True, but let's not talk about Sombra. Right now... today is about you... and me. So... what do you say I bring your little wet dreams to life... sound good?" Cadence advances towards Shadow, adding some extra sway to her hips, her boobs jiggling with the tight confinements of her cheerleader shirt. She eventually presses herself bosom against Shadow's chest, then guides one of his hands under her shirt to grope her soft, squishy, pillow-y bosom, causing him to gasp in shudder from pure excitement.
That's it. Now Shadow's completely under her spell. He lifts her top off, freeing her two big girls from their tight clothing prison, jiggling so beautifully. Shadow gets his shirt off and lunges at Cadence, mashing their chests together as well as their lips, too.
Cadence's lips are soft and warm. Cadence feels how warm Shadow's lips are. This young man is eager to make her his and just thinking about it is making her wet. He grabs her ass and kneads her ass cheeks like balls of dough, then spanks her, making her moan and gasp in the kiss. She separates her lips from this spunky young man for a moment to gaze into his shiny red eyes.
"Wow... you're something else, Cadence." Shadow praises. 'Never thought I'd be living one of my wet dreams like this, this is too cool!' he thinks to himself.
"And I've got plenty more surprises for you. Here, have a seat," she playfully shoves him onto her bed and undoes his pants and pulls them down, along with his underwear. She now has a full view of his hardened, rock hard manhood as it stands tall and proud. From her perspective, he has to be at least... 14 to 16 inches long... and approximately 2 inches wide. "Shadow Force... how do you fit this monster of yours inside these tight pants, it must be so unbearable for you!" she says in surprise.
"I could ask you how you fit those big, beautiful girls in that tight little clothing fabric you wear to keep them consealed, it's gotta be painful," Shadow rebutts.
"Touche," she winks. "Luckily, I know of a way to calm this monster down. Just sit there and watch your principal work her magic on you." Cadence surprises Shadow as she gets up close and grabs her two pillow-y girls, and opens them up before closing them onto Shadow's dick. She begins to tittyfuck her young party guest while flicking her tongue against the tip of his hard shaft.
Shadow groans from her soft, squishy mounds hugging his manhood. And her warm, wet tongue flicking against the tip of his cock... it's unlike anything he's experienced in a dream.
This... is the real deal. And by god, he's loving every waking moment of it. Cadence looks up at her special guest, giggling at his twitching smile. She gives him some extra pleasure, taking in the entire top half of his throbbing, beefy monster dick. Her soft, warm lips wrapping around his cock and her tongue swirling around the base while she sucks on him hungrily... She's practically an animal.
'Fuck, man! She's really good at this!' Shadow says in thought. Just then, he thinks about something and forms a sneaky grin on his face. 'Maybe it's time I show her what I'M capable of.'
Soon, he puts his plan into action and stops Cadences before bringing her up to him eye-to eye, "Whoa, Shadow... where'd you find all this strength?" she asks, clearly turned on. She doesn't break eye contact from him, probably knowing what's about to happen.
"Easy. I'm about make you feel so good and make you all mine," Shadow boldly claims. He pulls her in for one big, deep, passionate, sloppy, wet kiss on the lips before laying her down on the bed.
"Ooh, someone's getting rough. I LOVE it when you get rough," Cadence says seductively. Shadow cannot believe how much of a bimbo his own principal has become. HIS bimbo. And just thinking about it thrills him to no end, so he over her and wraps his cock in between her huge bosom again. He squishes the two beautiful mounds together on his cock and thrusts his hips back and forth. Cadence watches as his gigantic behemoth cock plays peek-a-boo with her and booping her nose a few times.
She opens her mouth, sticking her tongue out, flicking it against his tip a few times. Then he thrusts deeper, getting his upper half of his cock into her mouth. She sucks him as hungrily as she did before, only now, he's the dominant species.
Cadence moans and slurps on his raging hard-on, desperately trying to get him to cum. All the while, she can feel her own pussy growing wetter with every thought of wanting him to take her. She doesn't wanna admit it, but Shining NEVER did her this rough before ever since they got married. She can hear him breathing like a wild animal as he was pumping his dick through her boobs and into her mouth.
And just as he's about to cum... he stops and pulls his cock away. "Don't think I'm done with you yet, because the fun has barely begun... for you," Shadow says, getting up in her face.
"Sounds hot. What are you gonna do to me?" she asks, fluttering her eyes at him. Shadow responds by getting down to face her crotch area. There, he can clearly see her soaking, wet panties and pulls them off, revealing the hidden treasure under those damp under-garmets. "Are you gonna stick it in, baby?" she asks in a seductive manner, about to spread 'em open wide with her two fingers. But Shadow stops her, chuckling as he looks up, grinning at his horny principal.
"Oh, I'm sticking something in it, just not... "THE" something." he specifies. He then leans down, coming face-to-face with her wet, leaking pussy. "Mmm, down the hatch," are the words he exclaims before latching his lips onto her pussy lips, getting in some French make-out sessions with it.
Cadence's whole body jolts from Shadow's tongue suddenly intruding her womanly area. She lets out a sharp, shuddered gasp, arching back. She can hear his lips smacking and feel his tongue slurping and rubbing against her inner walls, slurping her delicious strawberry shortcake-flavored juices. She doesn't wanna attract Shining up here or risk having him hurt Shadow because of what they're doing. Then again... just the thought of running the risk of being caught is making her even wetter right now.
Shadow Force continues to savagely slurp and suck out her tasty juices, making out with her leaking vulva like a hungry predator devouring its prey. He slips his tongue out from time to time, flicking it against her winking clit, making Cadence squirm under his control.
Some of her juices squirt onto his face and he just chuckles and keeps eating her out. Whether she admits it or not, one thing she can't deny is how fantastic Shadow's bed skills are. He might even be on parr with her husband, if not better. And being only 18 years old, that's making her more wet. Her inner walls even start to get tighter around his tongue, but not tight enough to trap him inside. He pulls out before his squirming bimbo headmistress in a cheerleader outfit could even think of cumming.
"Uh-uh, you can't cum yet. So naughty," Shadow says, hovering over his headmistress. He slowly descends down onto his hot, sexy bimbo. He grabs his cock, all nice and hard and throbbing and aching to claim his grand prize right in front of him.
Shadow could've had Cadence remove her cheerleader's outfit... but let's face it, she looks WAY too hot, sexy and cute in her old cheerleader outfit. At least he has a good view of her massive boobs and her love tunnel entrance, which is begging him to take her. Without any further delay, Shadow hooks his arms around her legs, then sinks his big, phat cock into her sweet sex hole all in one go. She inhales, biting her lower lip as his cock not only fits well... but is also re-shaping her pussy.
"From this day on... I'm gonna make you mine and rock your world in ways your husband couldn't even DREAM of doing, my sweet, lovely bimbo." Shadow boldly whispers in her ear.
"Mmmm, do it, baby. Show me how good you are. Mark my pussy with your phat, manly cock," Cadence whispers back to this energetic, horny young man. Shadow plunges in for a hot, wet, sloppy kiss and starts his steady rhythm of thrusts, pounding her pussy with finesse. Cadence moans in the kiss, intertwining her tongue with her young lover. Her pussy lubes and hugs his massive thing like there's no tomorrow.
Shadow has her pinned down in a mating press and isn't planning on letting her go. His wet dream of claiming her has only just begun. He's captivated by her warm lips, soothing voice, soft skin, in fact... everything about her is perfect in his eyes.
The only problem... is who she's married to. But he plans to fix that... or maybe that's just his lust talking, his desires to keep her all to herself. If that's the case... is she on the same boat? After they have their fun, will she just... blow it off as just a one time deal? No... it's best not to think about it. At least, not right now. He's having the time of his life with his dream girl and he's making every second count.
He unhooks his arms from her under her legs and wraps them around her head and back, picking up speed in his thrusts, pounding her womanly spot a bit more rapidly.
Cadence ceases her opportunity, locking her legs around Shadow's waist. Her arms then wrap around his back and she moves her hips in sync with his. She moans more erotically, feeling their bodies merging as one in the heat of the moment. They break the kiss, now feeling their heavy breaths on each other's faces while hearing wet slaps from down below. Hearts would form in her eyes, staring into her dominant alpha male.
The pressure in his ballsack start making itself known and Cadence's pussy is lubing him up while tightening up around her phat cock. These horny sex maniacs are close to their 1st orgasm.
Cadence tightens her grip on Shadow, keeping her arms and legs wrapped around him while he thrusts out of control, pumping his dick in and out of her wet passage. Cadence moans helplessly while Shadow pants heavily and growls like a wild animal. His hips now moving all on their own. As his cock plows her even deeper, he can feel his climax getting closer. Shadow and Cadence feel like they're both in heaven.
At last, the instant release hits them hard. Shadow silences Cadence with another deep smooch as he shoots his hot, sticky seed deep into her love caverns. Cadence screams into the kiss, spraying her love honey all over his cock and balls like a garden sprinkler.
After about 15 spurts, he pulls his cock out of her used pussy and his lips away from her soft, warm, loving, kissable lips, panting heavily. The only thing that connects the two sex-driven lovebirds is the single thin strand of saliva on the tip of their tongues. "Happy Birthday, Cadence," he whispers to her. Just then, both of them go stiff for a split second when they hear knocking on Cadence's door.
"Cadence, babe? Where are you? You in here?" Shining's voice calls out.
"Shit! Quick, hide in the closet," she whispers. Shadow quickly jumps off the bed, grabs his clothes and runs off into the closet while Cadence hides the stains on her bed using the thick blankets and then heads into the closet just in time for Shining to poke his head in.
"Honey? You in here?" Shining asks.
"Y-Yeah babe, sorry if I worried you. Something I can do for you?" Cadence replies, poking her head out from her walk-in closet door. Shining doesn't know that inside her dark walk-in closet, Shadow is currently standing directly behind Cadence and his raging hard-on has been revived by the sensation of having it rub against her huge, jiggly ass.
"Yeah, everyone's wondering why you're taking so long up here," Shining says.
"Well... I was... hoping to put on something more comfortable for my birthday, that's all. But you know how it is... having a variety of outfits to choose from," Cadence says. Just then, she feels something enter her pussy and she arches back, which Shining notices.
"Is something wrong, baby? You look... distraught," Shining asks.
"No! No, I'm fine. Just... lost in thought. Really DEEP thought," Cadence assures with a nervous chuckle while she looks behind her, seeing Shadow has once again started fucking her doggy style. Now it's gonna take a miracle for her to convince her husband to leave or risk exposing her secret affair with a student. She does her best to not let the pleasure take over.
"Well, when you do find the right outfit, come back down. Everyone's waiting for cake. We can celebrate your birthday without a delicious cake," Shining says.
"I'll keep that in mind. Thanks, honey," Cadence replies. Soon, Shining leaves the room, closing the door and Cadence is pulled into her walk-in closet and had her light turned on by Shadow. "Shadow... you have got some nerve sneaking another fuck sesssio-- AH!" she's stopped by Shadow plunging his cock deeper into her pussy and is pulled in by her young lover. His hands grope and fondle her big ta-tas, making her moan.
"Apologies. But I can't help it when you're looking so damn sexy," Shadow replies. Cadence tries to protest, but with Shadow pumping his manhood into her tunnel again, she can't get a word in.
Or, to be more precise... he won't let her protest. And with one BIG thrust into her womb, she's fallen back into his mercy once again. Shadow pours in double the effort of pleasuring this married headmistress, making good on his promise to make sure SHE belongs to him. His cock is turning her insides into mush and his hands are fondling and groping her beautiful breasts.
Her pussy tightens around his cock once more. 'Oh, what's the point, this is too good!' she says in thought, letting this rambunctious party animal mark her as his girl.
Cadence's mind is going blank. He's becoming more rough with his cock while feeling her all throughout her body, making her weak in the knees. Her body would jolt from time to time. Her pussy rapidly taking the brand new shape of his massive meat piston. She's very surprised even, how can someone who's barely beginning his adult life have this much energy left after one love-making session?
Now she's really jealous of him. Or better yet... this could be exciting for her. The risks he's willing to take, the lines he's willing to cross, the lengths he's willing to go through just to satisfy her... to ravage her... to show her a good time... no matter where they'll be.
And with that thought, Shadow grunts again, plunging balls deep into her chambers and erupting his massive volcano, making Cadence moan, but he covers her mouth with his hand. His massive load was bigger than the last time, slightly bloating this horny, bimbofied birthday girl. She twitches and jolts, feeling each spurt fill her to the brim before she cums once again and goes limp. Shadow doesn't let her go and hugs her against him, kissing her soft cheek tenderly before he pulls out of her.
"Happy birthday indeed," she says, turning to her young lover with a sex-drunken smile. They share one last kiss, staying this way for a while.
Cadence has to face facts... no one's ever made her felt that good before in her life. Sure, she and Shining have fucked like rabbits before, but it's always him that tires out quickly. But Shadow Force... well... this was his 2nd orgasm and yet he's not even half tired. Perhaps this won't be so bad for Cadence when she needs a break from the hardships of running a school. After all, Shining doesn't have to know... right? Right?
