It's actually something you'll enjoy a lot.
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I'd like to have a word with you...

It's actually something you'll enjoy a lot.

It's actually something you'll enjoy a lot.

You didn't know why you agreed to this, she asked you point blank about it, and the only thing that the two of you could get in real trouble about it was the simple fact that she was an authority figure and you her student. You remembered how when you were on your merry way to lunch, it was a few weeks ago, after a long morning of dealing with your teachers. When you were stopped by an other student. The student wore a navy blue button up and slacks, with a midnight violet sweater vest over it, he said he was a personal assistant to Vice principal Luna and had a message for you from her.

"Really? What does she want with me?" You asked as you dug your hands in your pockets nervously.

"I don't know, all I know is that she wants you to have lunch with her." He said and went back to his own business. You couldn't help but be worried that the principal had found out about the pepper gum you gave Ms. Harshwhinny, oh she really should learn to stop being so uptight and take a joke. Or maybe the spiking of coach Iron Will's protein shake with estrogen pills. (he had serious man boob chaffing after that one) Or hell maybe she found out about...that peep hole you drilled for Soarin into the showers in the girl's locker room. You drilled it for him, but if he squealed in order to save his own sorry ass he is so dead. You think to yourself.

"Ahhh Mr. Anon, a pleasure to see you." A soft but intimidating voice says snapping you from your thoughts. You look up to see her, Vice Principal Luna. She wears her long button up blazer with the moon emblem in the white collar, and her short violet skirt. She has long fishnets on her long shapely legs, and black heels on her feet. You wonder if she's allowed to dress like that to school, sure her skirt isn't that short, and her blazer covers her up to the elbows, leaving only her arms bare, but those net stockings. You wonder if they go all the way up her legs, maybe to some...tight black waist garters that ride along her butt just so...

"Mr. Anon? Are you okay?" The vice principal asks as she takes a seat at her desk, you can't help but shake your head snapped from your fantasy. You always had something of a fetish for older women, but the Vice Principal? She was kind and not too bad a looker, not by any means. It's just, you never thought you'd be fantasizing about what she had under that blazer and skirt. She just didn't seem to be you're type at first, but now...you couldn't help but feel flustered realizing you had been thinking about her.

"I'm fine Ms. Luna, I just...I don't understand why I am here, and I'm not playing stupid if I'm in trouble." Your words make the vice principal giggle, Vice Principal Luna, an older woman with a passion for keeping the school running as smoothly as possible, and who demanded respect from all who were under her metaphorical wings, giggled.

"You know how I take the performances of each of my students very seriously don't you?" She says as she picks up a photo of her and her sister, they stand outside the school some time ago, she smiles at it before putting it back. "The faces I see passing through this place, are young minds my sister and I think of as...well You may not know it but the students like yourselves are like...our children. In a manner of speaking." She adds quickly to make the statement seem less...awkward.

"I'm sure you do Ms. Luna, and I appreciate the sentiment, but it's not like I churn out F's year, so really I have to ask why your treating me like I am?" You ask her even thought you know she means well, what's a (surrogate) mother to do?

"Mr. Anon, you're a very bright member of the Canterlot High family, and you are more or less passing on the average, but that's exactly what I wanted to talk with you about, you see...I think if you apply yourself, and are are a bit more diligent in your studies, you could get on the credit roll or maybe even..." You only catch bits and pieces of what she says, you don't mean to not listen, it's just.

"Gee, I'm sorry I'm not on the same wavelength as your sister's favorite, the transfer case from Crystal Prep, what was her name? Twilight? Luna doesn't seem angry at your comment, but she does give you a look.

"Mr. Anon, its not like that at all, I'm not saying you need to be comparing yourself to anyone else, your perfect just the way you are, and you ARE a good student, I only ask that you try and be a GREAT student." She says before placing a hand on your shoulder and using her free one to mae ypu look into her eyes. She always was the more compassionate and loving of the principal sisters. She was more the cool older sister to the students while her actual sister was more a strict but caring mother.

"Your so beautiful." You mouth silently or you think it's silently until you see that she looks taken aback by what you just said. She blushes hard and then giggles again. she cranes her neck a bit and you swear you see that her shirt collar...isn't attached to her shirt. Like, its a collar that she'd fasten around her neck like the kind you put on your cat with a little bell.

"What...did you just say...Mr. Anon?"The illusion fades almost as soon as she showed you, and you gulp before trying you best to save yourself.

"Nothing Vice Principal Luna." No matter how safe and secure you can feel when you're with her, you had a feeling them she didn't feel the same. Sure she loved her students, but like she said, it was in a sisterly way, or strictly platonic kind of love. After all, she was the Vice Principal, and you a Canterlot High student. It was wrong, it was amoral, but to you...it was what you desired, but did she feel that way about you?

"Now you'll remember and consider what I've been talking about?" She says,you can't help but notice she rolls her tongue on her lips to where you can practically see the saliva pooling on the tips of her lips moistening them just so, as you swear you can spot a glimpse of a black bit of material sticking out of her her desk before she slams the drawer to her desk closed.

"How I can be very successful if I just work a bit harder in class?" You tell her. She smiles and nods but you know she knows, there's no point in beating around the bush or playing games. Her exterior shows that the student/Vice Principal roles they have to play is fading, and the real reason you both really want to be here makes itself known.

"Yes, you're a good student, you can be a great one, but...that's not what I've asked you in here for." She makes sure the door is well locked, and the dismissal bell is just about to ring, she places a soft kiss on your cheek as that sharp ring echos and the others scuttle by, shadows of a world that you want only to leave you both alone. At long last, the halls go dead silent. The Vice Principal's kissing you, on the cheek sure but you already feel like you're desires are starting to be realized.

"How long?" She says peeking from out of her office blinds to watch the last bus pull away from the school, you tell her you don't understand. As she checks and double checks untill she's sure the student body is gone. "How long have you felt the way you do about me my student?" She says neither angry or touched, just interested.

"Since I've been here, these girls...are just girls...I want to love a woman." You tell her bluntly wondering how long she'll go along for the little game. You try playing to her ego by making her seem like she's the only one for you, and she is. You like the other girls at school, they are very nice to you and almost all of them are so sweet, especially the perky ones like Pinkie, or the kind ones like Fluttershy and Rarity, but she trumps them all soley because she's the kindest, most beautiful one of them all.

"People wouldn't understand us." She says with her back to you as she unbuttons her shirt making you raise a brow a bit. You didn't think she'd be so...quick to point out the flaws, but you wonder if she's only trying to see if you are clever enough to find a way around them.

"People wont have to know." You retort twirling a lock of your emo like cowlick of black hair, you aren't a goth or emo by any true means, the hair, the Anarchy A black tee and ratty ripped jeans aside, but you do like a few of their trends. Plus you still have planty of friends at school. She turns to you revealing a skin tight black latex corset under her blazer and button up, and her shirt collar does indeed fasten around her neck like a pet's collar.

"I doubt you're old enough to even know half the games I like to play." She says licking her lips again before letting out a soft moan, that coupled with her attire, are enough to get the snake in your jeans awake. Games? The school Vice Principal had a kinky side? Then again a job like a School authority figure, could use a stress reliever or two.

"I'm old enough, I know my way around a few things, I know the rules when it comes to the collars and cuffs, leather and lace scene Vice Principal Luna." You say reaching out and touching her collar, your finger strokes the moon emblem making her squeak softly but not in protest. She knows your serious about it all, and her armor of the tough, decision making, hard worker is starting to crack.

"I don't wont you to be a boyfriend to me, I'm not a desperate spinster who wants a husband and children before it's too late, and this wouldn't mean I'd be cutting you slack or looking the other way when you slip up. I still have a job to do, and an image to uphold, and...you are still my student you know" You tell her you don't care, that these will be two separate worlds that will have their time and place. Before getting behind her and wrapping your arms around her waist and taking a long drawn out whiff of her hair. It smells like her office, lavender and lilac. The life of the student and Vice Principal will be kept as far apart from lives of the two forbidden lovers that is so sinfully delightful to you both.

"Why fight what we know we both want even with the risk? The fact that it's a forbidden romance, doesn't that excite you Ms. Luna?" You ask as your hands caress her soft midnight blue skin she shivers at how cold they are at first but then purrs softly as they warm up.

"Answer me one thing?" You ask her as you slowly kiss the back of her neck and nibble on her ear, making her melt in your arms as they embrace the sleek vinyl latex of her corset. You wonder just what else she has to play with and who will use it on whom.

"Yes my student?" She says her mouth hanging open as her tongue lolls out in pleasure, making you wonder if she's getting aroused and pleased from just being touched and kissed. You notice she's been turing all the pictures in her office around, as if she didn't want her sister to see this, which put a funny image in your head of a photo Celestia looking un-approvingly at her through one of the photos.

"Is this love?" You whisper in her ear as you slide your hand under her midnight purple skirt, just as you fantasized, she has on lacy black. The best the Victoria's Secret in Time's Square had to offer, and a black lace garter hooked to her black fishnets. Your hand feels soft fabric as you rub the dripping wet fabric of the vice principal's underwear. You never go past the fabric, nor do you rub her too strongly. Her arousal fills the office room up and makes you want to shove that length of your erection in her, but you resist your lower brain's demands to crack through the last of her armor. Which shatters as your finger presses against the nub of her clitoris, she know's you've won, she doesn't care.

"Do you want it to be?" She says as her senses are overloaded by your attentions as you release her. She moans and sits in her chair, her eyes gazing aimlessly as she breathes heavily and kicks her heels off. Then her stockings come off and her garter, and finally her soaking wet Victoria's Secrets. "Oh my..I..need to...give me a moment." She says as she does her best to maintain her composure. "Keep these...come back next week, and I'll have my answer for you then." She says getting her other clothes back on.

"What about mine?" You hesitate before you take the undergarments from her desk and take a soft restrained sniff of the arousal on her panties. The scent of a woman makes countless fantasies and fetishes run through your mind. "I want to love you in my own special way."

"Then next week...no sooner no later, after the last bell. If you're not here then, don't even dare ask me about it again. I'm a woman that likes to keep to a timely schedule." She dismisses you at long last and when you got home that night, you jerked off so many times with her panties and stockings in your free hand against your nose that night, it took a whole bottle of snuggle and soap and a box of baking soda just to get the crusty smell of dried semen out of your bedding and pajamas.

Now it was a week later and you stood outside her office door again, you decided to try spicing things up if she wants to take things further. For once in your life you're glad the stores are trying to wring what little Holiday money they can out of the lesser holidays by having Valentine's candy on sale almost literally the day after Christmas. there's a long rose in cellophane in your hand and a box of Godiva Decadent delight in a heart box in another, only the best...for her. In addition you went to Chinatown yesterday and had to ask around until you found it, but you found an herbalist who was wiling to sell you (only because you only LOOKED young) after a flash of your I.D and as best an explanation you could without flat out saying, "I hope to fuck my Vice principal," a powder made of dried seahorse, gecko tail, and crushed turtle shell. A supposed "Ancient Chinese" secret to having a four hour erection without the risk of dying of a major heart attack when you climaxed. You took it at lunchtime, and was very thankful that your only class after that was art till dismissal.

The whole time you sat there with your raging boner poking the confines of the leopard print underwear you thought you'd surprise her with...if she says yes. You dat through art class usibg its time to work on whatever projects you and your fellow students vpuld work on. You found yourself drawing sketch after sketch of her. The art teacher Ms. Clay, walked up to your stack of sketches of Luna and chuckled.

"You know, Anon, Pablo Picasso went through several periods in his artistic life. The blue period when he battled depression, the rose period when had his beloved wife, tell me are you going through your Luna period?" She asks gigling, you ignored her and waited for the last bell to ring. Now your hand knocks softly on her office door.

"Who's there?" She asks, clearly in case it's her sister or the janitor who made a fine inventor in Ms. Finish's play last month.

"Me..." is all you say as you feel the tightness in your pants grow uncomfortably tight in anticipation.

"Enter." She says with a purr, She sits on top of her desk in an outfit similar to last time, only now she's added a leash to her collar, a ball gag dangles from her neck with it, she has spiked cuffs around her wrists and thin chains hang down from her ceiling, little more than wallet chains but she has them none the less. Her left hand holds a rolled up black bull whip and her right a bottle of hard liquor, no wine for this occasion. It's Fireball Cinnamon Whisky, the stuff that burns your throat, boils your stomach and is not for the faint of heart. A plate of oysters on the half-shell sits on a bed of ice on a silver plate, she takes one and slowly moans as she licks the meat from the shell and swallows it loudly mhhhhhing in pleasure as she does.

"Oh Anon, is that rose for me? She asks as you hand it to her and she seductively holds it against her skin. You nod and hold the Godiva Dark Decedents to her. "Oh and chocolates too, how sweet." She helps herself to a dark chocolate honey bee dream. She mhhhs seductivly as she savors it. Through she dosen't have her sister's famous sweet tooth, which makes her lick her lips in delight everytime she enjoys a good cake with her morning tea. Luna appreciates a treat as much as the next gal.

"So...we're doing this?" you ask her as you notice she's added black and blue striped gloves and stockings to her outfit, her panties have a midnight blue heart on the crotch, and her collar is now as spiky as her bracelets.

"Sit Mr. Anon, sit and eat with me." She says helping herself to more chocolates. You oblige her taking a seat and grabbing an oyster off a plate. "Shot?" She asks as she lowers her eyes to you. You notice that the bottle has a good bit of liquor gone already, you only feel pissed she couldn't wait for you.

"I don't see any glasses Ms. Luna." You say as she pours a few streams of booze onto her latex top it slides down the material to her navel which the top doesn't cover.

"Come now Mr. Anon, I thought you said you knew how to play?" She says giving her whip a little crack, teasing but still noticeable in the low light of her office candle light.

"Just testing you," you say as you lean down sticking your tongue out and licking the slick rubbery latex top. The fiery alcohol is like acid but you hold out for her. She moans and purrs like a kitten as you slurp and kiss the fabric off her top, her large breasts sway side to side as you bury your face in the valley of her cleavage. you finish your drink and take another oyster as does she, only you bring your oyster to her mouth and her to yours, as you take turns feeding each other. The process is repeated until the oysters are all consumed. she swipes the platter away getting ice and shells all over her clean floor.

"Oh my...I've been a bad girl" She says as you unzip your jeans, her eyes lighting up as the rock hard bulge behind the leopard print underwear as she unzips her corset, freeing those massive mounds of her perky breasts and protruding hard nipples. She clips the thin chains to her bracelets, turns on her side and gives her own nipples a hard squeeze and a lick. "I need to be punished." She says handing you her whip and turning on her side. You take it but you're not sure how to approach the task she's given you.

"Have you know?" You say as you're now completely naked save your own socks, your four hour miracle dust holding up nicely.

"Yes," she says with a hiss as she gags herself and gives her panties a wiggle tempting you. You unfurl the whip and smack it across her back as light as possible, behind her gag she scoffs and say something that sounds vaguely like "harder!" You comply and smack her plump rear harder than before, making her moan into the gag as a wet patch appears in her crotch, her chains rattle softly. You whip her again and again, red streaks form on her bare skin. You never guessed it, but apparently being the younger of the two sisters seems to have given her a bit of a submissive side. you notice the candles and an idea comes to mind, but you don't know if she'll be into it.

"Ms. Luna?" You ask her as she struggles to breath in her bliss, she turns her head to you making a soft "Hmmm?" behind the gag. You pick up one of her lavender scented purple candles and let a few drops hit the wood of her oak desk, she arches an eyebrow before moaning loudly and nodding as she shakes her rear again pleading with her eyes, begging with her body for you to do it. You let a few drops of fat hot wax hit her skin with soft sizzles. she screams and moans in a mix of pleasure and pain, as you paint her back and ass cheeks with wax. Streams of it pooling and running down her back and sides in patterns like the swirls on a lollipop. To your surprise, she turns on her back and gives her breasts a massage. "Are you sure?" You ask her, because though you enjoy playing with her, the last thing you'd ever want to do to this beautiful woman is hurt her, emotionally or physically. She may be the one who likes a little pinch and squeal with her partners, but you're not a sadist.

"Yes...I want it." She says removing her gag. You shrug and let a drop hit her hard nipple with a fizzle. She screams and gasps for breath, you're so glad she scheduled this for after classes, the noise would have had half the school on the door trying to break in if the place wasn't empty. "Ohhh FUCK! Anon please...more! paint my boobs with wax, make me scream! I think I'm gonna cum from the pleasure alone!'' She screeches a guttural yell as you drizzle more wax on her nipples, breasts and cleavage. Her navel makes her knees buckle as she screams like a banshee until her voice just peters out completely and she collapses into a puddle of lust driven bliss on her desk. The vice principal of Canterlot High has deteriorated into a chained up, gagged, and lust driven slut in front of you.

"So are we finished here?" You ask her as you don't mean it. You want to ravage her now that the foreplay is done with and you only hope she wants it too.

""Like hell we're done you handsome stud...don't you want the main course?" She asks releasing herself and kicking her panties off her ankle making them land on your head. She giggles getting on her hands and knees, apparently Vice Principal Luna enjoys doggy. She raises her rear in the air her face laying on the wood of her large desk, you wonder just how many other students she's had back here, surely you're not her first? You don't care. You get behind her whip in hand as you crack it against her hip, making her moan and shudder as your hands grab her ass and around her waist as you get into position on your knees to shove your penis into her hole...another idea come to mind.

"Ms. Luna? do you...have any toys? That could give attention to your...other hole?" You ask not even checking if she'd be okay with having her anus stuffed but you seem to have hit a G-spot with your request. She opens her desk drawer taking out a tube of KY passion and a large, wide dildo. It's a bright red one with a slightly thicker tip, not very anatomically accurate, but she doesn't seem to care. She gets the toy nice and slick with the KY almost the whole bottle spread down the toy's shaft. When she hands it to you, you notice its a good ten maybe foot long toy, not something to favorably compare to you're slightly above average real one, but the knowledge of where she wants it shoved more than makes up for it.

You rub the bulbous head against her dark and tight anal ring, it reluctantly tries in vain to stay clamped shut as you stretch her open with the tip. She moans and screeches in another mix of pained ecstasy from her pleasure. You're still a little gentlemanly and give her neck a few soft kisses to get her to relax and enjoy it. before your free hand rubs her pussy lovingly. Attention there makes her anal muscles relax and the toy slides in easier. your hand feels a knob on the base of the toy when in finally gets that deep, you turn on the toy's vibration to its only setting, maximum.

"Ahhhh...oooooh Yes student, just like that." She says melting in pleasure as she only sees stars as the toy buzzes away inside her asshole. She's moaning and shuddering as the toy hums away inside her, leaving only her soaking wet and noticeably aroused vagina to be filled. You resume your prior position as you press the tip against her slit, you give her one last lash with the whip as you stuff your hard penis into her, you can feel the toy inside her just under the membrane that separates her holes from each other, you feel a bit bad, like you're splitting her in two, but the glazed look in her eyes coupled with her loud and pleased moans tell you you're only giving her exactly what she wants. You thrust hard and passionately into her pussy as the toy's vibes can be felt through her on your own cock. You thrust again and again, hilting yourself with each thrust and gripping her hard as you do.

"I love you!" You cry out as you feel the orgasm building closer and closer, it's like you've got gallons of cum backed up and you need to release it.

"And I you my prince." She says before putting a hand to her lips in an opps pose. So what? some girlhood fantasy of her prince charming, what do you care? Oh you have no idea. None of it matter as you give one last powerful thrust into her and pump her filled to the brim with your jism. The both of shrieking as you climax at the same time and you finally pull out of her, both of you spent and too overcome by orgasmic bliss to do much but pass out. You get a good last view of Vice Principal Luna, dhe moans loudly lost in her bliss, as a rubber cock vibrates in jer toght asshole and her dripping wet lips leak gallons of salty, sticky semen in the nice and messy creampie you made in her.

"Good you're finally awake." Vice Principal Luna says nonchalantly as you wake up on her desk, she dressed you in your sleep, how she didn't wake you you don't know. The evidence that anything lewd had ever occurred here is gone. She's in her usual clothes again and smiling warmly, instead of a bottle of Fireball she hands you a can of Arizona Iced tea, you thank her and pop the tab sipping it as casually as possible. Give the woman credit, she knows how to be efficient.

"So...now what?" You ask her as you each drink the iced tea as she only smiles warmly at you. You are amazed at how quick her sweet and somewhat mysterious and intricate personality as the caring big sister to you, shy younger sister to her actual sister came back so abruptly. It matters not now, you and her have done things, and have a bond that can never broken between each other now.

"Need a lift home Anon?" She asks placing a hand on your face and gazing lovingly at you. You would like that very much given how late it's getting.

"I'd like that." You tell her as you kiss her, its a warm and tender kiss that is vastly different than what you did before. You moan softly into the kiss and stroke her hair tenderly before licking her cheek playfully. "I love you Ms. Luna...In my own special way."

"As do I Anon as do I." She retorts as she kisses you again, it seems to last for ages and you want only to kiss her soft warm lips forever. You and her agree to express the affection you both feel in a very special way, the other's call you an apple polisher and ass kisser, oh they have no idea. Sometimes it's a fresh cup of coffee on her desk in the mornings and sometimes to you it's a special lunch in her office, nothing like the last time as it's too risky for you to get frisky during class hours, but you're more then content to split some Thai or Sushi take out in her office, because there's so much more to your love than chains, whips, and hot candle wax, and you both wouldn't have the love for each other any other way.

"Ms. Luna?" You say to her as she feeds her face with a few strands of soy sauce soaked noodles.

"Hmmm?" She asks as she slurps her thai food down. She's so cute when she eats like that, it reminds you for all her image and prowess as the school second in command, she's only human.

"Nothing...it's not important." She smiles and helps her self to more noodles as you get back to your curry beef with rice. You can see in her eyes that she knows what you meant to say, and you both can hardly wait for the last bell.