"Anon...." a voice echoes around you, causing your eyes to open only to find yourself floating in a seemingly endless void of darkness.
"Who's there?" you ask while looking around to find nothing.
"Anon...." the voice calls again. "There is something I would like to show you. It's something that I'm sure my favorite student would love to see."
"Student?" you think recognizing who that voice belongs to. "Principal Celestia?" You ask before you find yourself in of Celestia's office. Daylight pours in through the open window behind her desk as you sit in front of it. Surprisingly, you're the only person in the room. But that doesn't last long as you hear the sound of the door leading into the small office opening. You turn around to find Principal Celestia leaning against the doorway wearing a tight purple bikini.
"Hello there, Anon," she says in a seductive tone as she stares at you with bedroom eyes. "Do you like my outfit?"
"Y-yes," you stutter in response. "I love it!" This makes her smile before giving her lips a lick. You watch as she steps into the room before closing and locking the door behind her. Once done, she turns around and makes her way over toward you, giving her hips a playful swing as you watch her ass jiggle with each step. When she gets close, she lays a hand on your shoulder before circling around you, giving your eyes plenty to look at.
"Like what you see?" she asks as she stops in front of you before she turns around and bends forward toward her desk, presenting her rather stunning yet also covered derriere to you.
"O-of course!" you reply. "W-why wouldn't I?" Celestia just giggles a bit after hearing what you said.
"Well then...." she softly says. "Why don't you give my beautiful rear a squeeze," your eyes widen after she says that. You then slowly reach out with your hand and gently grab onto her soft cheek before giving it a squeeze. Celestia moans while you reach out with your other hand and do the same thing to her other cheek. "Oh yes..." she groans. "Squeeze my ass like I know you've been wanting to for so long."
As she continues to moan, you begin hearing another sound. It sounds like another voice, but you can't really tell as your focus is on Celestia and her soft cheeks. After a few more seconds pass, she turns around and straddles herself on your lap before gently sitting down on it.
"Anon..." a new voice echoes as Celestia reaches behind her back. Shortly after, the straps holding the fabric come undone, but the top doesn't come off.
"Are you ready for this?" Celestia asks before winking as her hands grip the edge of her top.
"Anon." The voice says again, this time a bit louder. "Anon. Wake up!"
"Come on, Anon. Wake up," Sunset Shimmer says as she pushes on your shoulder. You groan in response before your eyes slowly open to find yourself sitting in the cafeteria at an empty table. You raise your head up to look toward her. Sunset just smiles as she looks down at you. "Morning sleepyhead," she says before sitting down beside you.
"Hey, Sunset," you reply before rubbing your eyes. "How long was I asleep for?"
"About 15 minutes. Just enough time for you to almost miss the majority of lunch. I know you have a free period after this, but I figured you wouldn't want to spend it sleeping here."
"I suppose so," you say while stretching out your arms. "I was just having a nice dream."
"Well judging from the little sounds you were making in your sleep, I take it you were having that dream again?"
You give a small sigh after she says that.
"Yeah," you reply. "It’s been occurring more and more lately. I don't know why."
"Maybe it's your mind telling you to just go for it and talk to Principal Celestia about how you feel."
"Yeah," you say in a sarcastic tone. ”Hey Principal Celestia, I’ve been fucking you in my dreams for the past month. Wanna make it a reality? Yeah, that’d go over well.”
"Hey," Sunset says as she puts her hand on your shoulder. "As long as you don’t say that, I think she might be open to it.."
"Oh yeah?" you ask before turning to look at her with a raised eyebrow. "How so?"
"Just... trust me on this," she replies.
“But even if I was brave enough to do it. How do I tell her?” you ask before turning your head to look at the woman of your dreams. Principal Celestia is sitting by herself, happily enjoying her lunch. As you stare for a few more seconds, your eyes just can’t seem to look away from her well-endowed breasts.
“I’m sure you’ll find a way,” Sunset replies before getting up. You do the same and start making your way toward the dishwashing room, which will make you walk by Celestia’s table. As you approach, she looks up to you and smiles, making you feel warm inside.
“Hello Anon,” she says as you walk up beside her.
“Hey there, Principal Celes-” Your own sentence gets cut off as you feel Sunset bump you from behind. This unexpected feeling causes you to temporarily lose your balance. “No! No! No! No!” you cry out in thought as you stumble forward, losing control of your tray and what remained on it. The contents go airborne for a moment before they find a new home on Principal Celestia’s lap.
The sight of this makes both of your eyes shoot wide open as Celestia looks between you and her now ruined attire.
“Anon, what are you doing?!” you hear Sunset yell from behind you. Glancing back, you see that Sunset has a frightened look on her face. “Not a food fight!”
“What?!” you immediately reply before turning around to face your friend. “Why would I--”
“Anon! No! Not a food fight!” she calls out, putting an extra emphasis on the last two words.
“What are you trying to-”
“Food fight!” another student’s voice calls out, cutting your question off, before you soon find a half-eaten hamburger flying through the air. Watching helplessly, you see the food land in the hair of Rarity. Not surprisingly, she begins to scream before Applejack and Rainbow Dash start throwing their food in retaliation. Unfortunately, their aim isn’t as good when throwing food as they would be throwing balls so multiple students get caught in the crossfire.
Soon enough, the entire cafeteria erupts into a chaotic scene of food and garbage being flung through the air as you and Sunset duck for cover underneath the table that you were by.
“What the hell, Sunset?” you ask while looking at her. “Why would you do that?”
“Trust me, Anon,” she says while looking at the excitement as a slice of cake gets splattered across Pinkie Pie’s face, who just licks it off with her unusually long tongue before giggling. “You’ll thank me for this later.” But before you could question her again, you hear the sounds of the cafeteria doors bursting open.
“Enough!” Vice Principal Luna’s voice calls out from the other side of the room. As soon as she says that, the entire room falls silent. A couple of seconds later, both you and Sunset emerge from under the table and take a look at the mess only to find an irate Luna standing by the doors. “I want to know right now who is responsible for this!”
“It was Anon, Vice Principal Luna,” Sunset replies, making you dart your head in her direction before looking to see that Luna’s eyes are now locked onto you. “He was the one who started it by dumping his food on Principal Celestia’s lap.”
“What?” You protest. “B-But I-”
“Anon…” Luna growls as she walks over to you. “I have half a mind to sus-”
“Luna. Stop," Principal Celestia says before getting up from her table, cutting off whatever Luna was going to say. "I’ll handle this,”
“Allow me, sister,” Luna replies before glaring at you, making you tremble a bit under her gaze.
“No. I will deal with Anon,” she says. “I was in here when this whole situation began. Therefore I will be the one who will deal with him.”
Vice Principal Luna sighs. “Very well then. I guess I’ll stay here and see that this mess is cleaned up while you and him have a talk in your office.”
“That will be fine.” Celestia says before you feel her hand on your shoulder. Looking up, you find her looking down at you with a stern expression. “My office. Now.”
You sigh before nodding. But before you start walking, you glance over at Sunset, who just winks at you for some reason. This unexpected action makes you raise your eyebrow at her before watching her walk away toward her friends.
“Thanks a lot, Sunset,” you think before you begin to follow Principal Celestia out of the cafeteria.
“Anon. Words can’t describe how disappointed I am in you right now,” Celestia says as the two of you pass a group of students. She isn’t making any effort in concealing this from the others. But then again, she really can’t with the giant stains on the crotch of her pants and the bottom of her coat. “Why would you do something like this?”
“Principal Celestia. It wasn’t my faul-”
“I don’t want to hear it right now, Anon,” she harshly replies, cutting off your attempt to defend yourself. Sensing that any form of defense will only worsen the situation, you choose to keep your mouth shut until the two of you reach her office. Not wanting to go down without a fight, you decide to try defending yourself once more.
“It wasn’t my fault, Principal Celestia,” you say while she opens the door leading in. "I didn't start the food fight. I'd never do anything like that!"
“Oh?” she asks. “Well then. Why don’t we go inside where we can talk in private.”
You sigh for a moment before nodding your head in response. She walks inside before stepping aside and allowing you to enter before closing the door behind you.
“So. If you are not to blame for starting this food fight. Then who is?” she asks as you take a seat in front of her desk.
“S-Sunset,” you reply. “She bumped into me from behind on purpose. And then she blamed me for starting it.”
“Why would Sunset Shimmer do something like this after all of the things she’s done for this school?” she asks while walking by you before sitting down in her chair behind the desk.
“I don’t know,” you reply. “Maybe she’s.....”
“In the past, maybe she would've done something like this," she says. "But what reason would she have to start this kind of trouble? From my point of view, I think you’re the one obviously responsible here.."
“But I swear!” you protest. “I’m innocent!”
“Unfortunately Anon, I’m not seeing any evidence that will sway me from what I saw,” she says. “I’m very disappointed in you right now. You were one of my most well-behaved students. What caused you to do something like this is unknown to me.”
You just sit there in silence. The woman of your dreams is pissed off at you and no matter what you say, nothing will convince her that you weren’t the one responsible for starting the food fight.
“Now because of this, I have no choice but to wear my backup attire for the rest of the day.” You wait for her to continue her lecture, but an unexpected silence fills the room. Glancing upward, you see Principal Celestia looking at you as though some idea had formed in her mind.
“Why is she looking at me like that?” you think before she clears her throat.
“Anon,” she says. “If it was my sister in this position and not me, she wouldn’t hesitate at giving you a suspension.” This statement makes you gulp as the memory of what Vice Principal Luna probably was going to say. “But,” she continues. “Fortunately for you, I believe that detention will suffice.”
“D-Detention?” you stutter as she pulls out a small piece of paper.
“But... In the event that you decide to skip out on it,” she says. “I will have no choice but to issue a suspension.” Once she finishes saying that, she hands you the paper. It turns out to be a detention slip saying that you will report to back to her office after school for it. “Do I make myself clear?” she asks, making you look back up at her.
“Crystal clear,” you reply in a depressed tone. “I’ll be here.”
“Good,” she says. “Now please leave so I can change my clothes.”
“Yes ma’am,” you say before turning around and walking toward the door. Once back out in the hall, you close the door behind you. “Well…” you think as you start walking down the hallway. “Guess I can just kiss my chances of being with her goodbye.”
As you continue to walk, a question begins repeating itself over and over again in your mind.
“Out of all the beautiful girls at this school, why did I have to become attracted to Principal Celestia of all people?” you ask yourself in thought as you walk by the lunchroom to find some students still hard at work cleaning up the mess that you were blamed for causing. Not wanting to cause anymore trouble though, you quickly make yourself scarce and soon find yourself in the main lobby.
But as you walk outside into the front courtyard, your mind goes back to the day that your attraction toward Principal Celestia really took off.
A cold wind blew through the air on a beautiful fall afternoon as you and several other students were helping out at a car wash fundraiser. The reason behind it was to help raise money for the repairs to the school after the Fall Formal. Many students had shown up to participate, the majority of them volunteering their time. All except for Sunset Shimmer, Snips, and Snails who were forced to participate as part of their punishment. As the tasks were given out, you were given the responsibility of hosing down each car after they've been scrubbed.
As you sat and waited for the first car to be ready for you to do your part, you were able to watch Principal Celestia and Sunset Shimmer working on Big Mac's truck. Celestia had decided to wear a plain white t-shirt and some small jean shorts. Whenever it became time for her to bend down to get her sponge in the soapy water, you couldn't help but notice her red underwear underneath show each time.
While she scrubbed away, her white shirt was growing wetter as time passed due to being pressed against the wet metal. It wasn't long before you started to see through the fabric to find a matching red bra underneath.
"Keep it together, Anon," you thought before reaching above your eyes and pulling down your sunglasses so you could stare without making it obvious to everyone around. "Last thing you need right now is to be out in public with a bulge in your pants." Despite some of your classmates wearing swimsuit tops where their upper bodies were being shown off, your eyes continued to stay focused on Celestia. There was just something about her being like this that you found more attractive.
"Anon!" Celestia called out as she turned around and started waving at you. "This one's ready to be hosed down!" With the way she was facing, it was impossible for you not to see her bra underneath her wet top. This was making your struggles with keeping your stiffening member under control even more difficult. And now, you had to go up to where she was standing.
"Alright!" you called back before getting up from your chair. You then bent down and picked up the hose before you started to make your way over there. As you walked, your eyes were looking in other directions while your mind was trying to think of anything that would help keep your situation down below in check. However, your actions caused you to not be aware of what's going on around you as you bumped into Sunset and her bucket of soapy water.
"Gah!" Sunset called out as the two of you fell to the ground. But when you landed, the hand holding the nozzle clenched out of reflex, resulting in a torrent of water being sprayed in whatever direction it was pointed at. It only lasted for a few seconds before you let go of the trigger, but the damage had already been done. Looking up, you found that it had completely drenched Principal Celestia.
"Oh my God!" you said before quickly helping Sunset back to her feet. "I'm so sorry, Sunset! I didn't mean to bump into you."
"Why don't you watch where you're going!" she replied in a harsh tone before she quickly grabbed her bucket and stormed off. Once that was done, you heard Celestia clear her throat, making you look in her direction. She was now standing directly in front of you with her white shirt now soaked so badly, her red bra could be seen very clearly underneath.
"I'm sorry, Principal Celestia," you said as she wiped her face dry.
"What exactly happened, Anon?"
"Shit!" you said internally as your eyes darted from left to right repeatedly. "Quick! Think of something!"
"Anon?"
"I uh..." you said. "I was distracted by a bee."
"A bee, huh?" she asked before raising an eyebrow.
"Y-yeah," you replied. "I'm sorry. I didn't mean to spray you." But to your surprise, Celestia just gave you a gentle smile.
"No worries, Anon," she said before pointing to her shirt. But whether intentionally or not, her finger was pointing directly at her now completely visible bra. "I was already wet from scrubbing. So no harm done."
"Oh. Uh... okay," you said before quickly rushing off to do your task.
“She probably would have rejected me even if this whole food fight thing never happened,” you think as you lean up against the Wondercolt statue. “But after today, I probably have a better chance of winning the lottery than being with her,” you continue thinking before looking down at your watch and find that your free period is a few minutes away from being over. After a long sigh, you start walking back toward the school. “These next couple of hours are just gonna drag on.”
“Alright, class,” Ms. Cheerilee says just as the final bell rings. “Remember to look over Chapters 10 & 11 so you’ll be prepared for the test on Monday.” But the only response that she gets is a few groans, which just makes her roll her eyes. As you walk out into the hallway, you turn and start walking toward her office.
“Lets just get this over with,” you think as you round a corner before coming to a stop in front of her door. As you put your hand on the doorknob, you sigh for a few seconds before turning the knob and pushing the door open. Once inside however, you see the room is empty. Principal Celestia is nowhere to be seen.
“Weird,” you think before taking a seat in front of her desk. “Is she gonna be here? Or am I to be trusted to stay here by myself?” Your questions are soon answered as the sound of the door behind you opening makes you turn your head and find something you never thought you’d see.
Standing in the doorway is none other than Principal Celestia who is carrying a load of papers and folders in her arms. But as you look closer, you see that she’s wearing a red tank top similar in style to Fluttershy’s. Looking down, you find that she’s wearing a pair of tight blue shorts that leave so much of her beautiful snow white thighs exposed for all to see.
“Well,” She says as her eyes look toward you. “I’m glad to see that you’re a man of your word, Anon.” After saying that, she begins walking over toward you. “Sorry for not being here when you arrived. I had to get these papers from Ms. Harshwhinny.”
“Is anyone else gonna be coming?”
“Nope,” she replies. “It’s just you and me.”
“I see,” you say as she walks by your seat. But as she passes, the stack of papers and folders slip out of her grip and fall to the floor.
“Whoops,” she says before chuckling softly. “Guess that’s what I get for trying to take everything on one trip.” Immediately after saying that, she bends down to start picking up the papers. But little does she realize that by doing this, her ass is now on full display for your eyes to enjoy.
“Those shorts ain’t leaving much to the imagination,” you think while staring at her ass for a few seconds before looking away to try and not make it obvious that you’re checking out your Principal’s ass. After a couple of minutes, Celestia straightens herself up before looking back at you for a moment.
“So….” she says as she starts walking around her desk. “Got any plans for the weekend, Anon?”
“Well I was kinda hoping to go hang with my friends tomorrow,” you reply. “Why?”
“Just asking,” she responds. “Trying to make a conversation since it looks like you didn’t bring anything to do while you’re here.”
“I got all of my homework done in class,” you say. “It wasn’t much.”
“I see,” she says as she sits down. After saying that, she tilts her head down and starts writing on the papers she brought with her. With the conversation over for the moment, you turn your head just as Sunset Shimmer passes by with her friends.
“You’ll thank me for this later,” her voice echoes in your mind as you watch her walk by.
“Not entirely sure why I’d thank you for this, Sunset,” you think after she disappears from your view. “If you did all this for nothing, you’re definitely gonna hear about it on Monday.”
“Have you been sleeping well, Anon?” Celestia asks, making you turn to look back at her.
“Huh? Oh. I’ve... had some days of good sleep. Some days of bad sleep. It’s different each night.”
“I see,” she replies. “Have any interesting dreams?”
“Uh…. nothing out of the ordinary,” you reply before thinking back to your dreams of her. “Just things that I like to dream about, I guess.”
“Care to share?” she asks while standing up and walking around her desk before sitting down on it. She then crosses her legs before leaning forward slightly. “We do have quite a lot of time to spend in here. It would be kinda boring to have to sit through it in silence.”
“Well….” you reply. “I’ve uh…”
“Yes?” she asks before raising an eyebrow.
“Been… having dreams about a woman.” You soon feel your forehead become sweaty as the air around you starts feeling hotter.
“I see,” she replies. “Do you have a crush on this woman?” Your eyes just look away toward the window. “Come on. You can tell me. I promise not to tell anyone.”
“This is it!” you say internally. “This is your chance to finally tell her!” After saying that in your mind, Celestia uncrosses her legs and leaves them spread slightly open. You clear your throat before looking back toward her. “Um… maybe.”
As you look at her, your eyes slowly drift down from her face to her well-endowed breasts that heavily protrude out from her body. The fact that you’ve never seen her with another man amazes you since she has a gorgeous figure. Soon, your eyes stop when her crotch comes into view. From this angle, you have a clear view at her inner thighs.
You won’t lie when you say that Celestia’s waist is bigger than what would be considered normal. But the way that her body has formed around her beautiful derriere and thighs give her even more of an irresistible body.
“Don’t you know it’s impolite to stare, Anon?” she asks, breaking your self-induced trance.
“Shit!” you think as your cheeks burn with embarrassment. “She caught me!”
“Don’t worry,” she says before softly giggling. “I’m not mad.”
“Y-You’re not?”
“Anon. I’m just gonna cut to the chase,” she says. “I know about your dreams of me. I know you’ve been attracted to me for quite some time.”
“H-How did you-” Your sentence gets cut off as Celestia places her hand in front of your mouth and motions with her other hand to be quiet. Not knowing what else to do, you slowly nod your head until she takes her hand away.
“Enough talk,” she says. “If you truly feel this attracted to me, then why aren’t you showing it by grabbing my breasts?” Your eyes widen before looking directly at her rack. The signal couldn’t be anymore obvious to you. Nodding slightly, your hands slowly reach out and gently grab both of her breasts. Celestia softly moans as you squeeze them. Her breasts feel like two massive water balloons in your grasp.
As you do this, Celestia motions for you to get up. You quickly obey while still doing what she wants you to do. Suddenly, her arms wrap around you and pull you close, pinning your arms between your body and hers. You tilt your head up and see her look down at you with bedroom eyes before she leans forward and firmly plants her lips against yours.
Your eyes shoot open at this unexpected move before they slowly close as you succumb to your feelings. Celestia gives a muffled moan while her tongue forced its way into your mouth. Your own tongue is no match for this unexpected, yet welcome intruder as it pins yours down, mixing your saliva with hers.
With her arms keeping yours in between the two of you, your hands continue squeezing her breasts as best they can. Her nipples can be felt in your palms as they are undoubtedly hard from what you’re doing. Celestia’s muffled groans aren’t doing you any favors as far as your stiffening member is concerned because it is as hard as stone right now.
One of her arms moves around from behind her back before you feel her hand grab at your shaft through your jeans, causing you to softly groan. As she squeezes, she gives an approving moan before you feel her hand move up and skillfully undo your pants button. Once done, it falls to the carpet, leaving your boxers and unmistakable bulge exposed for her eyes to see.
Celestia breaks the kiss a few seconds later and steps back, leaving only a thin strand of saliva keeping your lips connected. It doesn’t stay for long as she playfully licks her lips while her eyes drift downward toward your crotch. She gives you a playful smile before the hand that undid your pants reaches into your boxers and takes hold of the prize within.
The feeling of her fingers wrapping around your shaft makes you groan while she starts to gently move her hand up and down. Along with doing this, her other hand moves down to the edge of her top before you watch her pull it up, exposing more of her beautiful body to you. The hand in your boxers unfortunately withdraws so she can get it off more easily before she flings it across the room.
Your jaw drops slightly as you stare at her beauty. Her purple bra looks fantastic on her body, even though it seems to be having trouble with keeping her breasts contained within. As she stands less than a foot away with her hands on her hips, you realize that she’s even more beautiful than you ever dreamed of. Celestia notices your facial expression and giggles softly before reaching up behind her back and unhooking her bra straps.
The two purple straps fall down her arms until the only things keeping it on her body are her hands as they cup and squeeze her breasts. Your eyes plead with her to let the fabric fall to the floor.
“Are you ready for this?” she asks in a seductive tone while staring at you with lidded eyes. You eagerly nod your head in response as your eyes widen with excitement. Celestia chuckles softly after seeing this before her hands move away from her body, allowing the bra to fall.
Once it reaches the floor, you look back up to the unfiltered beauty of Principal Celestia standing in front of you while completely topless. Her erect nipples protrude from her breasts, giving you the clear sign of her arousal. She then sits down on her desk, spreads her legs apart and motions for you with her finger to come to her.
Doing as she wants, you come and stand between her legs. Your eyes continue gazing at her nipples as one of her hands comes up and cups her left breast. She jiggles it a few times before pointing it toward you, giving clear instructions for what she wants done next.
Wasting little time, you bend down enough to where her nipple is on the same level as your mouth. You then lean in close enough to give it a kiss before opening your mouth and encompassing her nipple with your lips. Celestia gives a soft moan as your tongue begins lapping at it while you begin to suck on it as well.
While doing this, you feel her hands make their way down your back until her fingers curl around the edge of your shirt. Sensing that she wants it off, you move back and allow her to pull the shirt off of your body. Once off, her eyes examine you as you stand in front of her. She smiles at you, giving you the impression that she likes what she sees.
“Very nice,” she says before sliding a hand down your chest until it stops on your bulge. After saying that, she stands up and unbuttons her shorts before moving her hands away. Despite being unbuttoned, the shorts stay where they are. She then starts wiggling her hips from side to side, making gravity start to pull the shorts down until they fall to her ankles, revealing a purple thong for your eyes to see.
Looking closer, you find the area between her legs is drenched. The darkened color compared to the color of the strap around her body gives you a clear indication that she is enjoying every second of this.
Celestia steps out of her shorts and comes up in front of you before wrapping her arms around your body once again. They pull you close to hers, forcing her breasts to be pinned against you. But this time, your arms are able to wrap around her body as well.
“Go ahead,” she coos into your ear. “I know you’ve been wanting to.”
Your eyes widen as your fingers drift down toward her ass until they reach the fabric of the thong before stopping. This is the moment you’ve dreamt of for months. Slowly, your hands dip under the fabric and glide across her pillow soft cheeks. Celestia groans before she leans down and starts nibbling on your ear.
The bulge in your boxers gets harder as you squeeze her ass, earning a soft moan from her as your fingers move back up and curl around the edge of her thong before pulling it down.
After the purple fabric drops to the carpet, she steps out of it before bending down and picking it up. Once done, she stands straight up again before putting her hands on her hips, proudly displaying her body for you.
“Lose the boxers,” she says before pointing at the one thing of clothing keeping your member from her eyes. After looking between your boxers and her body multiple times, your hands grip the edge of them before you pull them down. Celestia gives you another approving moan as you step out of your boxers. She then steps back and sits down on her desk before spreading her legs once again.
“Come here, big boy,” she says while motioning with her finger for you to come to her. “Come and make your Principal cum.”
“A-Alright,” you stutter before stepping between her legs, getting down onto your knees and leaning close to where she can prop her legs on your shoulders. The air around you fills with her scent as your face moves close to her pussy. “I’ve been dreaming about this moment for so long,”
As soon as it does, Celestia’s soft thighs gently press against the sides of your head, signalling to you that there’s no going back. Not that you wouldn’t want to anyways. The taste of her juices may be a bittersweet one, but it is something that you eagerly want more of.
You soon feel her hands running through your hair again as your tongue begins moving up and down along the folds of her pussy before it brushes against her clit. This makes her hands grab a chunk of your hair and tug slightly, which causes some discomfort for you. But the pain is worth hearing her moans of joy as they grow louder in volume as she inches closer to the edge of her orgasm.
“Oh Anon,” she groans. “You’re so talented.” If her thighs would allow you, you would’ve replied. But instead, you keep stimulating her clit with your tongue before sliding it down toward her entrance. Once there, you push it inside as far as you can go. Celestia’s thighs add a bit more pressure, but the softness of them keeps it from being uncomfortable for you.
Soon, you feel her lean back on her desk before hearing one of her drawers open.
“What is she doing?” you think as you hear something rattling around inside the wooden desk before you see her sit back up with a purple colored dildo in one hand and a bottle of lubricant in the other. You look on as she sets the dildo down before pouring some lube into her hand.
“I want you to do something else while you eat me out,” she says as she starts rubbing her oiled hand up and down the plastic shaft like you wish she was doing to yours. Once she’s done, she holds it out for you. “I want you to slide this inside my ass.” After saying that, her legs spread apart enough to where you can pull your head slightly back.
“Okay,” you reply before taking the plastic toy from her grasp. Looking at it for a moment, you find that it seems to be the same size as your own shaft.
“But before you do that. I need to do something else.” After saying that, you watch her pour some more lube into her hand. She clenches the lubed up hand into a fist before rubbing more onto her index finger.
“Is she really gonna do what I think she’s gonna do?” you ask yourself in thought before your question is soon answered. Celestia’s slick hand comes down between her legs and positions itself in front of her hole. Your eyes widen as she gently slides her index finger inside all the way up to her knuckle. Her moans make your shaft ache from being so hard as you watch what she does.
“Okay,” she says after doing it a couple more times. “I’m ready for it.” Once you hear that, your eyes look back and forth between her asshole and the toy.
“Well….” you think. “I’m sure she’s probably had this up there many times before if she’s been keeping it in her desk.” Your hand then proceeds to aim the tip of the plastic object directly at her asshole before pushing it up against it. Adding a little bit more force, the tip slowly enters within.
“Yes,” she groans before leaning backward slightly. “Keep going until I tell you to stop.”
“Alright,” you reply while continuing to push the toy further inside. Once the toy is almost completely within, you see her hand come up and signal for you to stop. You just nod before taking your spot back between her legs.
After getting into position, you feel her hand on the back of your head before she pushes your face back into her crotch. Taking the hint of what she wants, you start licking her moist pussy again while pulling the dildo out of her hole until only the tip remained in her before pushing it once more.
“Oh yes!” she cries out while you watch her hands clench tightly around the edge of the desk. Your tongue eagerly continues its task of running through her folds, tasting her juices. While doing this, your eyes look up and see that Celestia is massaging her breasts, adding to the amount of pleasure that she’s receiving.
Her breathing grows quicker as you keep pushing and pulling the dildo in and out of her asshole while focusing your tongue's actions on just her clit.
“Yes!” she cries out while her hands grab your hair once again. “Yes, Anon! I’m gonna cum! I’m-” Her own sentence gets cut off as she cries out in orgasmic bliss. Both of her hands suddenly grab the back of your head and push your face deep into her crotch as you taste her cum.
Once her orgasm dies down, her grip on your head loosens and allows you to move away from her crotch before you sit in the chair in front of her.
“Did you.... like that, Principal Celestia?” you ask while breathing heavily.
“Please,” she says. “Just call me Celestia. You’ve earned that privilege after giving me such a wonderful orgasm.” After saying that, she gets off of the desk and approaches you before getting down on her knees. “Now it’s time for me to return the favor.”
“Yes!” you say internally as you spread your legs wide, allowing her to get between them to have unlimited access to the prize that she wants. Your cock stands proud and fully erect while under her gaze. Celestia licks her lips for a bit while looking at your shaft before her hand cups your balls, giving them a light squeeze.
“I hope my skills in this aren’t as rusty as I think they are,” she says before leaning forward and giving the tip of your shaft a soft kiss. After that, she opens her mouth and licks the tip before going down to the base of the shaft and licking up the entire length. You moan in approval as she does it again while continuing to massage your balls. “You like that?” she asks in her seductive tone.
“L-Like it?” you reply. “I-I love it!”
Celestia just giggles after hearing that. “Trust me, Anon. I’m just getting warmed up.” After saying that, she takes only the tip of your shaft into her mouth before closing her lips around it. You immediately feel her tongue lap at it relentlessly before feeling more of your member enter her mouth.
“Oh yes.” you groan while she keeps going down until your entire length is inside. She then hums a little, making her throat vibrate around your tip. You gulp a bit as she pulls her head up before quickly going back down. The process repeats itself over and over again as her head bobs up and down, leaving a thick coat of saliva on your cock.
As she continues deep throating your shaft, you start to feel pressure build from your impending orgasm.
“C-Celestia,” you say, gaining her attention. “D-Do you want me to cum in your mouth?”
Celestia simply takes your shaft out of her mouth. “Depends,” she replies. “Do you want to cum inside my mouth? Or….” Her eyes dart down a few times, signalling to you exactly what she means.
“But I don’t have a condom,” you think as Celestia just stands up and walks over to her desk. “Why would she want me to cum inside her?” She then clears everything off of it before turning around and laying down across it on her back. “Maybe she’s on the pill or something.”
“And now for the final touch,” she says while grabbing the plastic dildo once more. “I’ve been wanting this to happen for a long time.” As she says that, she grabs the bottle of lube and gives the toy a fresh coat. Once done, she starts rubbing it all over the toy with her hand just as she did before. However, this time she doesn’t give the toy to you and positions it in front of her asshole before sliding it in until it’s almost completely within.
“Double penetration?” you ask in thought. “Who would’ve thought that my Principal was this kinky.”
“Alright, Anon. I’m ready,” she says before spreading her legs wide as you approach her with your still erect shaft. Once you’re in between her legs again, you lean forward and rest your hands on her soft thighs before she scoots up enough to where you won’t have any difficulties with what you’re about to do.
Looking down, you notice that she’s leaving one hand down by the end of the toy, making sure it stays deep inside her asshole. She then uses her other hand to spread the folds of her pussy to where you can clearly see the entrance to her pussy.
You move your waist up until your tip makes contact. Not wanting to look like you’re hesitating, you gently slide your shaft in, making her groan with pleasure as you penetrate her body. She slowly moves her hand that was keeping her folds spread away as it isn’t needed anymore. The warmth you’re feeling as your cock goes in her completely makes you feel good as you slowly pull out before going in a bit faster and harder.
“Oh Anon….” she groans while cupping her breast. You look on as she tilts her head forward enough to where she can suck on her own nipple. For a minute or so, she simply sucks on it while you continue thrusting into her. Each thrust inward makes her groan more and more.
Soon, you feel her hand that was keeping the toy in her asshole start pulling and pushing on the toy to match your movements. Whenever your cock would slide in, she’d pull the toy out as best she could before shoving it back in when you were pulling back.
“Fuck me hard!” she says, obviously enjoying having both of her holes fucked at the same time. “I want this so much!” Doing as she wants, your thrusts are given extra force, making her breasts jiggle each time your body collides with hers. But by doing this, the pressure of your imminent orgasm starts building up once more.
“Celestia!” you cry out. “I’m about to cum!”
“Do it, Anon!” she replies. “I want to feel filled for the first time in years! Blow your seed into me!”
You grunt a bit as you try holding back for as long as possible, relishing this opportunity. Even though she said that this wouldn’t be the only time, who knows when the next chance will come.
But alas, all good things must come to an end. With one final thrust inward, your cum shoots out as though it was being fired out of a cannon, sending spurt after spurt of your seed deep inside her. Celestia groans in delight as she feels her womb being filled with your load.
“Oh Anon….” she groans as you slowly pull your cock out of her. Once out, you notice a bit of your cum leak out of her pussy and onto her her fingers that are still keeping the toy inside. She then moves her hand and sits up, keeping the plastic shaft in her, before you watch as she licks her fingers. Her tongue wraps around each finger, getting all of your excess cum off. Once she finishes, she turns and gives you a warm smile. “Thank you so much, Anon.”
“For what?” you ask.
“For giving me an experience that I’ll never forget,” she replies before reaching out and opening a drawer in her desk. You look on as she pulls out a little box of pills. She then reaches down and picks up a water bottle before putting one of the pills into her mouth. Once she finishes that, she guzzles down at least half the water in the bottle along with the pill. “There,” she says before putting the bottle down. “Can’t risk getting pregnant. Especially with a student. Even though you’re old enough as far as the law is concerned.”
“So that’s why you weren’t worried about me cumming in you,” you reply before chuckling softly. “That would definitely be a really awkward talk with my parents.” This makes her giggle before standing up and wrapping her arms around your body. You do the same and pull her body close to yours as the two of you stay in a hug for at least a minute or so. “Speaking of parents. I’m sure they’re probably wondering where I am.”
“Just tell them that you were given an opportunity for some… extra credit,” she replies before placing her lips on yours.
“So what exactly are we?” you ask after she breaks the kiss. “I mean. I have no problems with us being an official couple and all. Even if it’ll just be our little secret.”
“Hmm….” she replies. “That does sound tempting. Maybe we can start out as friends with benefits and see where things go. But that of course doesn't mean I'll be fudging your grades or anything if you do poorly in a class. Can't have any suspicions of me playing favorites.”
“Of course,” you reply. “I wasn't expecting any special treatment anyways.” As soon as you finish that sentence though, another thought comes to mind. "By the way. How did you find out about my dreams about you?"
“Sunset told me about them roughly a week ago," she replies. "Granted I was a little surprised by what she said. But when I remembered how you acted at the fundraiser a few months back, it all started to make sense." She then places her hand under your chin before giving you a kiss on the cheek. "There is something else that I wanted to do as well,” she says after standing straight up once more. "But if you don't want to or can't, it's perfectly fine."
“What is it?”
“Maybe on Monday, we could meet up at Sugarcube Corner for some coffee and cake. I’ll get there before you do and we can pretend like we just so happened to bump into each other.”
“Sure!” you enthusiastically reply. “I have nothing else planned for that day anyway."
"Wonderful."
"And when are we gonna have one of these moments again?”
“Hmm…” she says. “How about sometime next week? I have a couple of meetings with the School Board that I’ll definitely need some stress relief afterward.”
“You got it,” you reply. “Want my number so you can text me?”
“I was just about to ask you the same question.” After saying that, she reaches into her desk and pulls out a sticky note before writing down her phone number on it. Once she’s done, she hands it to you. “And I have one other thing for you,” she says before picking up her thong and holding it out for you. “Think of it as a token of my appreciation for what you’ve given me.”
“T-Thank you!” you happily reply before taking the thong from her hand.
“You’re quite welcome,” she replies before bending over to pick up the rest of her clothes. But as she does this, you notice that her dildo is still deep inside her asshole. An idea quickly rushes into your mind after seeing this.
“Hey uhh.. Celestia?”
“Yes sweetie?”
“Before you put your pants back on. Is it alright if I uh… spank you?” Upon hearing that, Celestia just smiles before turning and presenting her beautiful ass to you. Taking full advantage to make the last part of your dream a reality, your right hand slowly raises up before quickly coming down hard onto her left cheek.
SMACK!
Celestia lets out a sudden gasp while she looks back to find a pink imprint left on her white cheek. She straightens up slightly before both of you watch the toy slowly slide out of her asshole until it drops to the floor. Celestia softly moans before looking back at you with lidded eyes and a smirk.
“I can tell that we’re both going to enjoy this relationship very much,” she says before grabbing you in her arms and firmly planting her lips onto yours. Your eyes shoot open at the suddenness, but close soon after before you wrap your arms around her body.
“Yes we are, Celestia,” you think as her tongue enters your mouth. “Yes we are.”
Author's Note
What's up everypony? I'm truly sorry for the long time between this one and the last one. I never would've guessed it was this tough to make a cougar story. That being said, I hope you enjoyed reading this new addition to the series. If you did, please leave a like and fave. It is really appreciated. 
Also, I want to send out a special thank you to Holy and Damien Darkside for being my proofreaders for this project. Both of them offered me great advice and taught me new methods of writing. So thank you very much, you guys. 
The next story in this series will feature Adagio Dazzle.
Full steam ahead, my fellow bronies and pegasisters.
- Harms Way
