Student-Principal Confidential

by Rally-Flag

Rating: mature
Tags: Sex, Main 7 (EqG), Principal Celestia, Human, Vice-Principal Luna, Original Character, Romance, Equestria Girls
Length: 17061

Principal Celestia has spent too long focussing on her career. Does she have room for someone else in her life?

Rally Flag is a senior student at Canterlot High School, who has lived with the Apple Family for the past few years after the loss of his parents. One day he helps out his high school principal with some yard work, developing something of a crush on her. Society says that they could never be together, but he isn't so willing to give up on that possibility.

Cover art by LDR: http://ldraptor.tumblr.com/post/116747172302/shaded-sketch-commission-for-bosssnikrot

Published 2016-09-05 21:10:01 UTC
Last updated 2023-10-30 08:11:50 UTC

Boys Will Be Boys

The afternoon sun shone high in the sky over Canterlot, bathing its denizens in an end of summer heat that was offset nicely by a cool gentle breeze. All through the town people were going about their daily business, families making final preparations before the school year began while teenagers made the most of their last two weeks of freedom. Over at Sweet Apple Acres the Apple family was holding their yearly reunion, cousins and aunts and uncles catching up with each other and enjoying the festivities. It was for this reason that Applejack had politely asked the final member of their household to spend the day out of the house, her long time friend Rally Flag.

Rally Flag was a fairly average guy, slightly taller that most other boys his age with green skin and blue hair. His eyes were the same shade of blue that his hair was, a little piercing at times and distant at others. He wore a long sleeved shirt and jeans, the mostly white shirt offset by its black sleeves and the picture of a military style banner on the front. His final defining feature was the scar that ran along his left cheek, a memento of the car crash that had claimed the lives of his parents when he was fourteen and the reason he had lived with Applejack and her family for almost four years.

For his part Rally didn’t mind spending the day away from Sweet Apple Acres while the reunion took place, never having been close to the extended members of her family. His eighteenth birthday had been a week prior, and birthdays always made him reflect on just about everything. Riding the streets on his bmx bike he thought about all the gifts his friends had given him, still feeling guilty that he could never afford to buy them gifts too. Briefly he wondered how Rainbow Dash was doing, his freshman year friend having gone camping with her father for the week. Finally he thought about his parents, grateful as always that at least in the last few moments he had seen them alive they had accepted he was more interested in pursuing sports as a career than running the family business.

A spluttering motor broke through his musing, the teenager having been riding his bike mostly on autopilot up until that point. Eyes focussing again, he sought out the noise only to find an older woman standing over a lawn mower. Her multicoloured hair was tied back in a ponytail, the soft colours complimenting her pale complexion nicely. She was wearing a black Slayer t-shirt and purple shorts, a pair of thongs on her feet the only thing protecting them from the ground as she scowled at the uncooperative machine in front of her.

“Principal Celestia?” He asked, coasting his bike until he was close enough to be able to speak normally. Her purple eyes flicked up to acknowledge him, an exasperated smile appearing on her face as she recognised the student.

“Hello, Rally.” She greeted him, grateful for the distraction. Mowing the lawn was one of her least favourite household tasks, and the student’s arrival could starve off her frustration for a little while. “Have you been enjoying your summer break?”

“Yeah, it’s been alright.” He said, feeling his face heat up a little. His eyes seemed to not be looking at any one thing for too long, switching from her single storey house back to her face. The lawn mower. Her shirt. The row of hedges by the driveway. Her shorts. “Uh, want some help with that?” He asked, blinking to try and keep his eyes on hers. The question had just fallen out of his mouth, Rally unsure why he had asked it. There wasn’t much time left of summer break, surely he didn’t want to spend any of it mowing a lawn?

“If it’s not too much trouble.” Celestia said, watching patiently as he dismounted his bike and took off his helmet. Kneeling next to the mower Rally located the cord and gave it a swift yank, the engine spluttering once more. A second yank saw it roaring to life, the teenager grinning in satisfaction as he stood up and grabbed the handle. He could feel it vibrating in his hands, starting to push the mower before she could say anything. “Rally, you don’t have to mow the lawn as well!” She piped up, starting after him.

“It’s alright, I don’t mind.” He said over the sound of the engine. Returning his attention to the task at hand he kept pushing the mower along, the principal now standing in the one spot in amazement. She hadn’t asked him to do it, or offered him any kind of payment. He had just done it. Shrugging, Celestia picked up the hedge trimmers that she had left by the front door and got started on the row of shrubs that ran alongside the driveway. For a time they simply worked on the lawn, the sound of the mower dominating the area as could only be expected. Every so often Rally found himself stealing glances at Celestia, his blue eyes drawn to her attire, the casual clothing showing off her modest figure in a way that her usual suit could never achieve.

Why was he staring at her so much?

“Think that’s it.” Rally said finally, stopping the engine and surveying the lawn. It hadn’t exactly been long to begin with but now it was much neater, the grass barely high enough to reach all the way up Celestia’s thongs. Likewise she had also finished trimming the shrubs, leaves and tiny branches littering the ground around them. The principal smiled as she examined his work, grateful for his help.

“You did a wonderful job, Rally.” She said, watching him beam at her praise. “I wonder, could I get you to empty the catcher into our green bin in the backyard?”

“Sure thing.” He replied, pushing the mower around to the back of the house. Finding the bin, he opened it and removed the catcher from the mower. Grass clippings fell into the bin in a torrent, a few stray blades missing and falling onto the ground. Rally wiped his brow and glanced out into the street, noticing that a couple of other houses also had their green bins out the front ready to be picked up. “Bin night?” Rally asked as he brought the green bin out to the front yard, Celestia starting as he once more did something without being asked.

“Oh! Yes!” She said, rushing over to grab one side of the bin and help him with the load. Together they brought the bin over to the curb, setting it down and opening it ready to receive the trimmings. Student and principal gathered up the leaves and branches, carrying them over to the bin to finish the clean up. Once that was done they stood back and admired their work, Rally wiping his brow from having mowed the lawn in a long sleeved shirt. “Would you like to come inside for a drink?” Celestia asked, the blue haired student nodding in acceptance and following her inside.

Dusty pink walls greeted him in the entry hall, Rally noting a door to his right that he guessed led to the garage. On his left was the living room, a comfortable looking couch sitting in front of a sizable television with a Wii U hooked up to it to his surprise. She led him through there to the dining table, a modest round table from which the diners would have a clear view of the television or the outdoor pool. Gesturing for him to have a seat at the table, Rally picked a chair that faced the kitchen as Celestia opened a low cupboard to retrieve a pair of glasses. Inadvertently his eyes came to rest on her rear as she bent over to get the glasses, Rally feeling his face heat up in embarrassment at just how well she filled out her shorts. He looked away as she filled them with water from a purifier, almost ashamed for staring at her butt at all.

“I truly appreciate your help today, Rally.” Celestia said as she approached, placing a tall glass of water in front of him. Finally able to look back at her, he nodded thanks as he picked up the cool glass and took a few welcome sips. While he was doing so the principal rummaged through her purse that had been on the table, finding a twenty dollar note and offering it to him. “Here’s a little something for your efforts.” She could see his eyes light up at the offer, though he looked a little troubled as well.

“You sure?” He asked. “It’s no trouble at all!”

“You didn’t have to help me.” She countered, smiling as he took the money and stuffed it into his pocket. “Actually, how would you like to make it a regular thing? If you would like to swap numbers I’m sure Luna and I would greatly appreciate your help.” Rally thought about it for a moment, draining the last of his drink.

“Okay.” He agreed, smiling at the prospect.

***

Try as he might, Rally couldn’t help but think about Celestia over the intervening time between then and school resuming. While it made sense if she called him to ask for help with some housework, he also found himself thinking about the principal at other times that had nothing to do with her. Shortly after the first day of mowing the lawn he had been invited to join Rainbow Dash and Pinkie Pie at the movies, the teenager confused as to why he had wondered what Celestia’s opinion of the movie would have been. Harvesting apples with Big Macintosh a few days later he didn’t know why he was curious about her favourite food. It wasn’t until the night before the school year was due to start that he figured it out.

Dinner that night had been a normal affair for the Apple family, all gathered around the table enjoying Granny Smith’s delicious spiced chicken drumsticks, mashed potatoes and fresh mixed vegetables. Rally had been unusually quiet, half eating the food and half just pushing it around on the plate while the rest of the family had talked about the days events. Excusing himself, he went back to his room in the loft of the barn and found his sketch book, one of the few things he could use to switch off the swirling thoughts in his head. Sitting at his desk and switching the music play list on his computer to random, he started to sketch randomly whatever came to his mind. Only once he saw Celestia’s face smiling back at him from the formerly blank page of his sketch book did the reason for his recent dwelling on her make itself clear, replaced by a gnawing unease at his crush on the principal.

Why? What was it about her that made him fall for an older woman? On the surface he wasn’t arguing that he found her attractive, in a regal and poised kind of way as well as filling out her shorts nicely. They had talked on occasion at school and Rally knew that she was intelligent and caring. She had even come to visit him in the hospital after the accident to offer to take him in, though Granny Smith had already done so. But what had made him think of her as more than just a good hearted person? Why did he start to feel butterflies in his stomach as he thought about her, why did he wonder if there could possibly be a future for them together?

“Welcome back to school, senior class.” Cheerilee’s voice rang out over the general murmuring of the students, their talk dying down as the teacher set up to begin their lesson. For his part Rally hadn’t been paying attention in the slightest, already with his notebook out and sketching things in pen. As Cheerilee started writing things on the whiteboard the pages of his notebook slowly filled up with pictures of Celestia, one hand propping his head up while a faraway expression settled on his face. Just two weeks ago all he had wanted was the planned out days of the school year, and now that it was here he wanted to be at Celestia’s house with her, doing work or even just hanging out with her and getting to know her better.

“Rally Flag?” He didn’t even hear Cheerilee’s voice as she called out his name, too engrossed in the current sketch to pay attention. All around him his classmates were turning to glance at him, the teacher already having noticed that he hadn’t been paying attention and deciding to use it as an example. Sighing, Cheerilee started over to where he sat to snap him back to the present. “Honestly, I know it’s the first day of school but the least you can do is-oh!” Drawing close enough to see the latest addition to his book, her face grew bright red at the sight that greeted her. “Young man! That is hardly appropriate to be drawing in your school notebook!” Snatching the notebook from underneath him, the first Rally even knew she was there was his pen being dragged along the page, leaving a sharp black line on his sketch.

“Miss Cheerilee!” He yelped, looking up at the teacher ashen faced.

“Principal's office. Right now!” She hissed, blushing furiously in both anger and embarrassment at what he had been drawing. “The rest of you, read up to chapter three of your textbooks until I get back.” The entire class was silent as she marched Rally out of the classroom, the green skinned student looking thoroughly ashamed of his actions.

“Can’t we talk about this?” He pleaded once they were out of the classroom, though a stony glare from the teacher made him fall silent. They walked through the quiet hallways, his blue eyes switching between his notebook and her face. It was almost maddening in the silence, wild ideas of snatching his book and bolting running through his mind. The idea became more and more insistent as they drew closer to the principal's office, Rally nearing the verge of panic. “Aww, c’mon Miss Cheerilee! I promise I’ll pay attention in class!” Rally said, his voice rising in pitch a little as he made a last bid for mercy.

“I’m sorry, but this is out of my hands.” Cheerilee said firmly, knocking on the door of the office. He gulped nervously, indecision between snatching his book and just accepting his punishment leaving him paralysed.

“Come in.” Celestia’s voice rang out, Cheerilee opening the door and ushering him inside. The last time Rally had been in there was when he was fifteen, a year after the accident when the principal had wanted to check up on him. It hadn’t changed in the slightest, a bookshelf in the back corner and a whiteboard with the day’s tasks written on it. The right hand wall had a yearly planner on it, while filing cabinets framed the door. Celestia’s purple eyes flicked up from her paperwork to regard them as they entered, the teacher pointing to the chair in front of her desk imperiously. “How may I help you?” The principal asked evenly, watching the subdued student sink into the chair.

“My apologies for having to bring a student to you barely half an hour into the first day of the school year, Celestia.” Cheerilee said, the principal glancing at Rally again. It was uncharacteristic of him to have to be brought to her office, and judging by how pointedly he was staring at his knees he wasn’t happy about the situation. “Just have a look through this. I have to get back to my class.” Handing over the notebook the teacher left the office, closing the door behind her. To Rally, the click of the latch might as well have been that of a stockade, guillotine poised overhead.

“Principal Celestia, it’s really nothing!” He said, his voice rising in pitch once again. “I was just drawing some pictures, that’s all!” Her eyes met his, closely gauging his behaviour. It was very different from the hard worker she had seen the past two weeks, or the withdrawn orphan of the past four years. Now he seemed panicky and closed off, like he wanted to be anywhere but here.

“Be that as it may, you should be paying attention in class.” She said sternly, opening the notebook. Rally could only sink further into the chair as she paused in surprise, unprepared for the sight that greeted her. “Rally, these are pictures of me.” She said, her voice trailing away slightly in wonder. The entire first page was dedicated to facial expressions, ranging from neutral to mirth and even an adorable pout. Curiously flicking to the next page she saw that the drawings had become more ambitious, full body sketches of her in various kinds of clothing. Her casual wear was the first thing she noticed, almost looking out of place among other such pieces as a Greek goddess dress and a playboy bunnysuit. “Why would you be…” She started, the rest of the sentence vanishing as she flicked the page once more to reveal the last piece he had been working on. Her jaw dropped at the nude sketch of her he had drawn, a blush spreading across her pale features.

“I’m really sorry!” He moaned, burying his face in his hands in shame. Her eyes flicked up to stare at the subdued teenager, taking in just how ashamed he was of his actions. Being principal of a high school meant that she had seen many similar problems arise in her time there but to be the focus of it was unfamiliar territory, leaving her with little idea how to best resolve the situation.

“Rally…” She said, pausing to rearrange the words in her mind. Her face felt incredibly hot, the principal clearing her throat to force herself to focus. “Listen, I’m flattered that you would think of me like that but I’m afraid that I just don’t feel the same way about you.” His posture, slumped in his seat with his eyes on the ground and face hidden from her view suggested to her that while the news wasn’t unexpected it was still hurtful for him to hear. Getting up, Celestia walked around to rest a comforting hand on his shoulder. “I’m not going to punish you for this.” She said gently, gesturing for him to stand up. “But I need you to promise to try and move past this, alright?” Standing, she noticed that while he was close to just half a head shorter than her his current demeanour made him seem so much smaller.

“Principal Celestia…” He muttered, his face burning. He understood that she didn’t share his feelings and that she was trying to help by letting him down gently. He wanted to just accept her words and leave the office, to try and forget his dumb crush and move on with his life.

His heart wasn’t willing to give up so easily.

Without warning Rally stepped closer to Celestia, their bodies scant inches apart. She squeaked in surprise as his hands came up to rest on her neck, getting a brief glimpse of his eyes filled with resolve in stark contrast  to her own very wide eyes. She had no chance to do anything as he pulled her face down to meet his, pulled their lips together into an electrifying kiss. Celestia was paralysed, the teenager’s mouth surprisingly soft and his kiss filled with genuine passion if clumsy. After a few seconds which seemed to span hours they broke apart, panting as their faces glowed bright red. She regarded him with shock, briefly concerned if he was going to do more.

“I-I’m sorry!” Rally stammered, snatching his notebook off her desk and bolting out of the office, leaving Celestia standing there bewildered. He ran until he reached his locker, stopping at it to bring his forehead to rest against the cool metal, panic having been replaced with a mild loathing of his actions.

***

“You’ve been quiet all day. Is something wrong?”

Celestia looked up from her dinner, startled out of blankly pushing her macaroni and cheese around the plate. After the first day back of the school year neither her nor her sister Luna had felt like cooking a proper meal that night, so they had bought a cheap and easy meal on the way back from school. The principal had been uncharacteristically silent the entire time, though Luna had said nothing until just then. She looked at Luna for a couple of seconds, then sighed and looked back at her meal.

“No, it’s…” She began, before taking a deep breath. “Well, I don’t know. It’s a long story.”

“I have all night.” The vice principal said gently.

“A student was sent to my office today.” She continued, running a hand through her pale hair. Her sister merely listened, not wanting to interrupt. “He had been drawing in class. Drawing pictures of me. One of those pictures was… explicit.” Luna raised her eyebrows, but took a mouthful of food instead of speaking. “He seemed quite sorry for having done it, and I was quite willing to just let him down gently and just give him a warning… although he grabbed me and kissed me.” The vice principal’s splade clattered to her plate, staring at her sister with wide eyes.

“Are you alright?” She gasped, immediately fearing the worst.

“Yes, I’m fine.” Celestia said, facing Luna to show her sincerity. “After it ended, he panicked and ran out of the office.” She took a quick mouthful of food and washed it down with a sip of wine, wanting to settle herself as the feelings of shock crept back into her mind. “I think what has me the most humbled is that, well… I think I enjoyed it.”

“Are you sure it doesn’t have anything to do with a lack of any action?” Luna asked, getting a look that was a mix of incredulity and venomous from her sister. “Come on, Tia.” She added, rolling her eyes at the display. “I know for a fact that you haven’t had any since I graduated college.”

“That doesn’t make it any more tactful, Luna.” She retorted. “Not all of us got to enjoy being single in Europe for a few years.” The blue haired woman inclined her head to concede the point, knowing that things had been rough for both of them. Shortly after graduating Luna had broken up with her boyfriend due to his belittling her wanting to be a teacher, the persistence he displayed causing her to leave the country to get away from him. Celestia’s own boyfriend of seven years had been completely unsympathetic towards her feelings, causing the older sister to break up as well. But where Luna had continued to balance her work and personal lives well, Celestia had thrown herself into her career.

“Anyway…” Luna said, more to spare both of them an awkward silence. “What do you plan to do?”

“I don’t know.” She admitted. “I should just try and forget it and move on, but somehow I don’t think it will be that easy.”

“Perhaps things will be clearer in the morning.” The vice principal said, turning back to her dinner. “After all, you don’t want to let a confused thought process make you do something you’ll regret.” Celestia nodded in acceptance, the sisters falling silent and turning their attention back to the television.

***

Tuesday had passed like any other school day, but for Rally he had felt incredibly guilty about what he had done the day before. The entire school day had been spent doing his best to avoid any place where he thought Principal Celestia might be, unwilling to confront her. His friends hadn’t failed to notice that he was more on edge, though Applejack had been the only one to say anything about it. None of them were speaking to each other for reasons that Rally didn’t know, nor were they interested in sharing those reasons. All in all it left him with no one he felt comfortable talking to.

However, eyes had been watching him the whole day without him knowing. Where she could, Celestia had been observing him and trying to get an idea of who he was and what it might have been that had caused him to develop a crush on her. He didn’t seem to have many friends, and the ones he did have didn’t seem to get along with each other. Apart from them he didn’t seem to talk much to anyone else so her initial assessment was a quiet person. Things were different on the baseball field, and during try outs for the school team Rally had been full of confidence and energy. Looking over his permanent record it became clear to her that sporting was where his strengths lay, his grades in everything but gym and health leaving him with a C+ average.

Thinking back to the time she had spend with him over the last couple of weeks, she knew that he was a hard worker and a honest person. She also thought about how he had been for most of his time at Canterlot High School, having lost his parents when he was fourteen. On the surface he seemed unchanged, but looking over his yearbook photos it was apparent that the smile never reached his eyes. The more she looked at the photos, the more she wanted to comfort him, hold him close and let him know that someone could care about him.

But could she care about him the way that he felt about her?

When Rally woke up Wednesday morning he was feeling slightly better about what had happened. Truthfully he still felt pretty bad, but after his baseball try out and not having run into Principal Celestia he was cautiously optimistic that she might be willing to forget the whole sordid scandal. Much like every school morning he got up to his alarm, picking up his clothes and taking them with him to the house. He was certainly grateful that the wet part of the year had already passed, the morning sun warm on his skin as he walked from the barn to the house. As he entered the living room he saw that Applejack had already showered and dressed, guessing that Apple Bloom was using the bathroom since she was the only one that was missing. Rally let himself smile, glad for the normalcy.

He was feeling quite peaceful on the ride to school, taking a leisurely pace on his bike as he thought about nothing in particular, mind free to wander. As always he chained his bike up next to the soccer field, just in case the team decided on an impromptu game after school. Expecting Rainbow Dash to be waiting next to his locker to talk about the other upcoming try outs, he entered the school and made his way there to find his assumption was correct. “Hey Dash.” He said as he approached, the rainbow haired girl turning at his greeting.

“Rally Flag, please report to the principal’s office.” Celestia’s voice rang out from the pa system, the words puncturing his good mood like a bullet through a beach ball. The blue haired teenager’s face fell, his shoulders slumping in a defeat he was sure was catastrophic. Why was she calling him to account now? Why not yesterday? Rainbow Dash noticed his shift in mood, the blue skinned girl clapping a hand on his shoulder in support.

“It’s probably nothing, Rally.” She reassured him, giving him a bright smile and completely ignorant of Monday’s events. “I’ll catch ya later.” Walking off and depriving him of a reason to put off going to her office for even a couple of minutes, he had no choice but to start walking. He grew increasingly anxious with each step, various scenarios running through his head and getting more and more dire. Was she going to give him detention? Suspend him? Expel him? Have him arrested for sexual harassment? Before the scenarios could become truly ludicrous he found himself standing at her office door, the teenager swallowing nervously before knocking.

“Come in.” Her voice sang out, his hand almost shaking as he opened the door and stepped inside. Celestia looked over from where she was standing at the year planner hung on one wall, indicating that he sit down in the chair in front of her desk. Her expression was unreadable as she continued to mark specific dates on the year planner, only adding to his mounting guilt as he sank into the chair.

“You, uh, wanted to see me Principal Celestia?” He asked nervously.

“What is it that you see in me?” The question was the absolute last thing that he had expected to hear from her. Anger, unhappiness, some kind of threat of punishment was what he had been expecting and what he had tried to mentally prepare for. The flat toned question about his personal feelings had caught him completely off guard, making him feel like slime. She seemed to notice his discomfort, leaving the calendar to sit opposite him and fix her purple eyes straight onto his blue eyes. “You obviously think more of me than just my physical appearance, or you wouldn’t have reacted the way you did on Monday. So tell me, what do you see in me?” Her eyes bored into his like a drill, almost threatening to rip the answer straight out of his brain if it came to it.

“I-I don’t know!” He said, his voice rising in panic. Celestia’s gaze didn’t waver, silently demanding better than that. At any moment he felt like he would be strapped to the chair, electrodes placed on his head and legs before the switch was thrown. “Everything!” He yelped, his heart threatening to burst through his ribcage. “Just, you’re so nice, and pretty, and smart…” Rally trailed off as he noticed that she remained as inscrutable as ever. It was humiliating for the teenager, having to explain to her how he felt about her when he knew that she didn’t feel the same way. Wordlessly she nodded, getting up again and walking around the desk.

“Rally, if you’re going to be honest then I should be too.” She said, moving around to stand behind him. “It has been some time since I’ve… well, been with someone.” He didn’t turn around, but the sound of the lock being pushed in on her office door caught his attention through her odd admission. “If you promise to keep this between us…” She continued, resting a hand on his shoulder momentarily before shifting it under his arm to coax him up. The touch sent sparks coursing through him, making his mind go numb and his body do whatever she willed. “Maybe we can work something out…” Her face filled his vision, the unreadable expression replaced by a lustful smile and hungry eyes as she leaned closer.

For Rally, it was as if the universe exploded.

Celestia’s soft lips pressed against his own, his eyes going wide as electric shocks coursed through his body at the touch. It was much different to the first kiss, her experience making itself clear to him as she took the lead. For what felt like an eternity to Rally he was paralysed, wanting nothing more than to surrender himself to her every whim, to give in and be her devoted love slave. Eventually she pulled back, leaving the teenager in a stupor at what had just happened. She smiled warmly at him, a friendly chuckle escaping her as she took in just how stunned her kiss had left him. “Come now Rally,” She said coyly, batting her eyelashes at him. “Surely you must understand that this is a tremendous risk for me, so don’t leave me with nothing to show for it.”

“Guh?” Was all he could manage, his eyes finally managing to focus again. The first thing they managed to find was her purple eyes, noticing the sincerity of her words reflected in them and her inviting smile. Finally his brain got back into gear, the student blinking twice before his mouth twisted into an idiotic grin, his face heating up at everything that had just happened and everything that could happen. Noticing for the first time that Celestia was sitting on the side of her desk, beckoning to him with one finger and a suggestive wink. He moved towards her, eager to taste her wonderful lips again just as the bell for first period rang. “Awww man, no fair.” He grumbled, annoyed that now he finally had a girl’s interest something was keeping them apart so soon.

“I’ll write you a note.” She breathed, grabbing him by the front of his long sleeved t-shirt and pulling him the rest of the way. Convinced by her argument Rally went willingly, enjoying the warmth and softness of her body and the intoxicating scent of her perfume as she pulled him into another kiss. This time he tried to follow her lead, doing his best to kiss her back without disappointing her. Her hands snaked their way up to hold his head gently, one hand running through his hair and the other coming to rest on his cheek. His own found their way onto her hips, caressing her through her pants lightly. “We don’t have too much time though.” Celestia whispered, Rally taking the opportunity to move from her velvety lips to her smooth neck, planting kisses on her pale skin and causing her to shiver in delight. Emboldened, she let one hand fall between them, cupping at her prize that she had felt shortly after the second kiss.

“Principal Celestia!” Rally half yelped in shock, his eyes going wide as she took hold of his hardening shaft through his jeans.

“We’ve already passed the point of no return.” She purred, fondling him through the coarse denim. “I do hope that what I’m feeling now is accurate.” The older woman added, her other hand snaking down so that she could easily undo his belt buckle. Rally gulped nervously as she did so, struck dumb once again. He had fantasised about this, about how eager she would be and all of the perverted things that would follow, but now that it was actually happening he was painfully aware at just how inexperienced he was. “Oh my!” Celestia gasped as she swiftly yanked down his now undone jeans and boxers, exposing his semi-hard erection to her hungry eyes. “You’re quite a big boy, aren’t you?” Her soft hands wrapped themselves around his half-hard cock, not the biggest she had ever seen but the biggest she had been able to enjoy.

“You really think so?” He panted, becoming fully hard in her skilful hands in mere seconds. Not having seen another man’s equipment outside of porn videos online the teenager couldn’t really compare himself to anyone else, but to hear it from a woman with experience gave the compliment real weight. Nodding, Celestia began to slowly explore his length with both hands, her lips returning to his for more kisses. He felt her tongue poking out to lick at his lips, the teenager opening his mouth slightly to allow her entrance. Their tongues danced briefly in his mouth, one of her hands finding one of his and guiding it around so that it rested just above her own pants. Her intention clear, Rally undid the button and zip on her purple pants, loosing them sufficiently for him to slide one hand into the front of her panties, coming into contact with her damp sex for the very first time.

“Mhm, just like that.” She whispered to him before returning to the kiss, glad to feel his fingers touch her so intimately. Almost uncertainly he slid one finger a short way into her passage, the principal letting out a slight moan at the feeling of his digit stroking against her insides. For the longest time she had been the only one to pleasure herself, and to have a student doing such things to her in her office was getting her incredibly excited. “Rally, I want you right now!” Celestia hissed, moving him back so that she could stand up. He watched her, mesmerised as she turned around and slid her pants and panties down with a delicate slowness. Finally able to see her bare ass and pussy as she bent over her desk, the only thing that stopped him in his tracks was a sudden self doubt.

“I, uh… I’ve never done this before.” He stammered, face burning in embarrassment as he admitted to her that he was a virgin. Here she was, and experienced, beautiful and confident woman who was willing to have sex with him and he was only being stopped by the thought that all he could do was disappoint her. Celestia looked back at him over her shoulder, batting her eyelashes and wiggling her butt.

“Don’t worry, I’m not grading you.” She said, winking back to help lighten the mood. It worked, Rally letting out a short laugh as he felt some of his nervousness melting away. Now he felt ready to do it, one hand coming to rest on her hip and the other one holding his cock steady. He stepped closer in behind the principal, rubbing the tip of his shaft along her wet slit a couple of times before pressing into her warm passage for the first time, letting out a groan of pleasure as his penis was enveloped by the slick heat of her pussy.

“Nnnh, Principal Celestia!” He sighed aloud, listening to the rainbow haired woman moan in delight as she was filled by his rigid length. To him the moment was perfect, being able to share such an intimate moment with the woman he harboured feelings for was something he never wanted to end. He felt Celestia start to rock back against him, eager for the real action to truly begin, pressing him a bit further inside her before moving away again. Her movements triggered an instinctive response from Rally, the green skinned teenager bringing his free hand to rest on her other hip before he started to thrust slowly into her welcoming body, the friction of their movements sending ripples of pleasure through both of them.

“Yes, just like that!” Celestia gasped, the principal looking back over her shoulder to watch him as he lost his virginity to her. The teenager’s face seemed to have a slack look to it, almost as though he were unsure of what he was supposed to be feeling at that time. When he caught her gaze a smile found its way onto his face, that simple expression causing what tension was still in between them to bleed away and washing Celestia’s doubts about whether she should be doing this away. It didn’t matter whether or not it was right in society’s point of view, just that it felt right to her. “It feels so good, Rally!” She moaned, her arms folding under her head so that she was at a right angle, her knees buckling slightly at his continued thrusts.

“This is amazing!” He groaned, scarcely able to believe he could be so lucky. It wasn’t as though he didn’t think the girls his age were attractive, able to find something in each of his friends that he could like and even nasty girls like Trixie and Sunset Shimmer. But ever since he had first seen Celestia doing yard work that day it was like no one could ever compare to her. Now that he was allowed to have her, watch her beneath him cry out his name as he gave her this incredible pleasure, he never wanted to let her go. With that thought in mind he suddenly stopped, taking enough of a step back so that his shaft slid out of her pussy. She blinked, confused as to why he had stopped.

“Uh? W-what… don’t stop now…” She panted, reaching back with one hand to try and pull him closer by his shirt. The smile was still on his face, Rally grabbing her hand softly and urging her to stand up again. Confused, she followed his lead, both of them stepping out of their pants as the student brought his principal around to sit on the side of her desk.

“I wanna see you.” He said, putting his hands on her waist and urging her to move back a bit. Understanding his intent, she moved back on her desk far enough to allow him to climb up as well, lying back as he positioned himself to thrust his cock back inside her inviting passage. She let out a moan as he penetrated her once more, her hands coming to rest on his shoulders while her legs arched up to wrap around his waist. As he reached her deepest point with his tip they stared into each other’s eyes, blue meeting purple as an indescribable feeling filled both of them. It wasn’t as complex as love nor as base as lust, but to Rally and Celestia it felt like they had both found a piece that had been missing in their lives.

Soon enough Rally was pumping into Celestia with renewed vigour, the mere ability to be able to look at her beautiful face filling him with a desire to make sure that she was fully satisfied. He wanted nothing more than to please her, to do whatever it took to make her happy and want to be with him as well. Her hands moved from his shoulders, one resting on the back of his neck and the other finding its way into his hair, the blue strands falling between her fingers as she brought him down to kiss him again. He went willingly, their lips meeting for several lustful kisses before he buried his face into her silky neck and pale hair. “Nnngh! Oh man, don’t think I can hold on any longer!” Rally grunted into her neck, still thrusting rabidly into her.

“Do it!” She moaned into his ear, her body rocking back against his thrusts instinctively, feeling his tip go as deep as possible inside her. “Cum inside me, Rally!” It was all the encouragement he needed, the teenager thrusting his hips a few more times before going rigid in her grasp. One final groan escaped him as he hit his climax, the tip of his cock stroking her deepest point before he came, shooting his warm seed deep into her body. The last thrust combined with the feeling of being filled by him was enough to trigger Celestia’s own orgasm, her inner walls tightening around his shaft along with her arms and legs as utter pleasure coursed through her body. Gripped tightly by her pussy he felt himself milked of the last of his cum, burying his face back into her neck as they shared their orgasms with one another.

After a moment Celestia felt her death grip on Rally start to relax, letting her legs rest beside him while her arms moved down to hold him in a tender cuddle. He was lying on her, out of energy and panting heavily into her hair with the wonderful smell of her perfume mixed in with their sex making the teenager feel incredibly happy. Finally he managed to lift his head up to look at her properly, noticing that the principal had a dreamy smile on her face as she regarded him closely. What made her happiest was that Rally had a genuine smile, one that caused his eyes to light up as well unlike every other smile he had over the past few years. “Thank you, Principal Celestia.” He breathed, leaning down to softly rub his nose against hers.

“I should be the one thanking you.” She murmured gently when he pulled back slightly, one hand coming up to rest on his cheek and run her thumb along the scar that adorned it. It felt a little rough, though he didn’t react to the touch any more than to gaze lovingly down at her. A minute passed as they allowed their breathing to slow down and bodies to cool, the last of their pleasure fading away as Celestia smiled ruefully. “You better get to class.” She said, disappointment in his imminent departure clear in her voice. Reluctantly he got off her, his shaft now soft as he pulled out of her and stood up to find his discarded clothing. Pulling his jeans and boxers on Rally couldn’t help but stare at her pussy as she bent over the desk to write out the note which would explain his being late to class, watching with interest as a trail of cum started to find its way down her inner thigh. His gaze was interrupted as he noticed her writing a second note before she handed him both pieces of paper, a coy smile giving him no clue as to what it was.

“You’re giving me detention?” He asked incredulously.

“I never punished you for drawing inappropriate pictures in class.” She replied as she pulled out a tissue to wipe away some of the excess seed before putting her panties back on. Rally was about to protest before Celestia gave him a sly wink, leaving him with little doubt as to her intentions. “Report to my office after school, Rally Flag.” He grinned at her and nodded his reply before leaving her office the happiest he had been in a long time.

Detention

“Rally Flag, you have some nerve showing up to my class forty minutes late!”

Rally paused half way through the classroom door, his gaze drawn immediately to Ms Harshwhinny and her clearly unhappy glare. The eyes of every student in the room were also on him as he closed the door, from Applejack’s concern and Rainbow Dash’s curiosity to Trixie’s mocking grin and Sunset Shimmer’s outright scorn. For his part he was too happy to really take notice, barely able to keep an idiotic grin off his face as he approached the teacher while offering the slip of paper Celestia had given him.

“Sorry Ms Harshwhinny.” He said as she took the slip. “Principal Celestia asked me to help her with something.” The teacher scanned the piece of paper for a couple of seconds before her eyes flicked back to him, clearly not happy about it but accepting his excuse nonetheless.

“I wish she would have waited to do this after school hours. Students need to take their classes in their entirety.” Harshwhinny grumbled, though it was clear to him that she really just wanted to get back to teaching. “There’s only one seat left, so take it and try to catch up.” Looking over the class Rally noticed that the last vacant seat was about half way down the rows and next to the window, Pinkie Pie on the other side. As he made his way to his newly assigned desk he couldn’t help but notice the poofy haired girl grinning widely at him, the look almost concerning though he shoved it to the back of his mind in an effort to actually focus on the lesson.

With just fifteen minutes left of the class Rally found it difficult to do that. His thoughts would drift back to Celestia, her satisfied smile as he lay on top of her, both of them spent from their sex. A dreamy smile settled on the blue haired teenager’s face, one hand propping his head up while the other put pen to paper, writing something about the lesson subconsciously. Barely five minutes of that had passed before he had given up on the lesson, already planning to ask Fluttershy for a recap before returning to daydreaming about the principal. The ringing of the school bell shook him back to his senses, most of the class already gathering up their books to head to the next lesson. He stood up, about to close his own book as Pinkie Pie collided with him in a tight hug.

“Uh, Pinkie?” He asked, more confused than anything else about the surprise hug. Out of the corner of his eye he noticed Fluttershy huffing quietly at the display, probably relating to the feud his friends were having that none of them were interested in talking to him about.

“You’re happy!” She said gleefully, not letting him go for a second. His face was practically buried in her hair, an almost overwhelming scent of her strawberry shampoo filling his nose. Pinkie pulled back just enough to beam up at him, clearly not concerned with the somewhat shocked look Rally had on his face right that second. “That was a real smile you had! Not like all those other smiles you get when you want to be happy but you can’t quite manage to be, but an actual really truly happy smile!” He blinked at her explanation before it occurred to him that he had in fact been smiling ever since leaving Celestia’s office earlier. She had a point though, Rally realising that he hadn’t been forcing himself to smile as he had for the past few years. It had just come naturally.

“Guess I haven’t been this happy in a while.” He admitted, the two of them leaving the classroom to find their lockers in the crowded hallway. Dimly he realised that this probably meant that he would be hanging out with her for the day, her presence all but guaranteeing that Fluttershy and Rarity wouldn’t talk to him. He might still get to talk with Applejack or Rainbow Dash, depending on which one talked to him first. Given that Dash had wanted to talk earlier he was reasonably sure it would be her.

“Ooh! Ooh! This calls for a party!” Pinkie added, almost seeming to not notice him speak at all though he knew that she heard and remembered practically everything when it came to friends. He rolled his eyes good naturedly, amazed that someone could be happier for his being happy than he was. “I know, we’ll have it after school today! That way Maud and Limestone and Marble can all join in! We’ll have plenty of games and cake and it’ll be a ton of fun!”

“How about an invite for me too then?” Rally and Pinkie glanced over their shoulders to see Rainbow Dash just behind them, looking at him oddly. Rainbow Dash was almost a head shorter than he was in contrast to the half a head Pinkie was, but he knew it would be crazy to judge the best athlete in the school on her height. He had always respected her abilities ever since freshman year, growing into a friendly rivalry when she realised that he was skilled enough to snatch a win from her every so often. It left them as firm friends and had introduced him to most of the others, the only exception being Applejack who he had known since kindergarten. “So what was so good that changed your mood from this morning, Rally?” She asked, one eyebrow raised slightly as they found his locker.

“Uh, Principal Celestia gave me some great news while I was helping her.” He said, opening his locker so that he didn’t have to look at her while answering. “Kinda personal though, don’t really wanna talk about it just yet.” He added, realising that leaving the question open could lead to more awkward questions. He had promised not to tell anyone, and while he was sure he could trust his friends it was more important to keep things under wraps for now. As he searched for the book for next period the picture of his family caught his eye, Rally pausing as he wondered just what his parents would have thought. His mother Glacia, her snow white skin and exquisite dress with her blue hair held up in an elegant style. His father Zephyr, slate grey skin and slicked back black hair with an expensive looking black suit on. Himself, thirteen years old without scars and looking awkward in his own suit. The only one missing was his older sister Olivia, the girl having eloped with a French transfer student a year before that picture was taken when she was eighteen.

Not that he missed his sister. She hadn’t replied to any of his emails after the accident when he had needed someone to talk to, leaving him nothing but bitter towards her. He might not have been officially adopted by the Apples, but he considered them more his family than Olivia.

“Eh, okay.” Rainbow Dash said as he retrieved his book for next period, closing the locker before the trio headed for their next stop. “Soccer tryouts are on tomorrow, so make sure you get enough sleep tonight. I want all the best players on the team again this year.” He gave her a relaxed smile as they stopped at her locker, though she was too preoccupied with the lock to really notice it.

“Yeah, yeah.” He said flippantly while she swapped books. Out of the corner of his eye a swish of rainbow hair caught his attention, his gaze drawn to Principal Celestia as she made her way down the hallway. For a brief moment her purple eyes met his blue eyes, the older woman giving him a quick wink and getting a happy grin in return. The moment passed, Pinkie Pie having noticed his grin which caused one of her own to appear.

“There’s that smile again!” She declared, Rally unable to help but chuckle at the observation as they set off for her locker. After all, he felt like he was on top of the world.

***

Celestia sighed, tapping the form that she still needed to fill out with the end of her pen. Ordinarily she would have had all of the work for the day done at least half an hour before the end of the day, but this had turned out to be far from a typical school day. It had been something of a battle with her conscience the previous night, the debate on what to do with regards to Rally Flag raging in her mind until she finally fell asleep. Eventually she had realised that she was sick of focussing on her career, sick of just sitting with her drink while Luna, Cheerilee and Harshwhinny found people to spend their nights with when they went out. She had wanted something to make her heart beat that little bit faster, to give her that wild feeling she remembered from her teenage years. Rally Flag, a student at her school, had certainly given her that opportunity.

That morning she had woken up with her decision firm in her mind. Sitting next to Luna at breakfast she had wondered if her sister had noticed any change in her demeanour, if she had noticed her nervous energy as she mentally prepared herself for what she was going to do. By the time he entered her office she was struggling to keep herself from jumping the teenager once the door was shut. Now, she was convinced that the morning had only been a sample of what he had to offer and Celestia was determined to have it all for herself.

After what she considered far too long the final bell of the day rang, her heart pounding against her ribcage as she waited for the arrival of her new interest. It didn't feel right to call him a boyfriend just yet, as they wouldn't be able to do all the things a couple could do together. As she waited for him she considered her office, wondering if she needed to do anything in preparation for his 'detention.' Glancing behind her she looked at the whiteboard with the remnants of her to do list, a single item that related to the paperwork strewn on her desk. Coming to a decision she got up and erased it, reasoning that she wouldn't forget the last task of the day when she was nearly finished it anyway. No sooner had she wiped it off the board did a knock on her door grab her attention, her heart quickening a little as she turned to face it.

"Come in." She called out, a small surge of excitement going through her as she watched Rally open the door and step inside. Celestia smiled suggestively as he closed the door behind him, watching him like a predator might eye off its latest meal. "Rally." She said, watching as he deposited his backpack next to her desk only to stand there awkwardly, unsure of what he should be doing. Deciding to save him the trouble she circled around the desk to join him, the teenager seeming more at ease when she leaned down to kiss him, the prompt enough for him to follow. Their lips met for a few seconds, brushing against each other and sparking the start of lustful feelings. When she drew back he tried to follow, finding something plastic held up to block his lips from kissing her. Curious, he looked at the object to see that she was holding up a whiteboard marker with a coy smile. "Ah ah ah, you're here for detention." She chided him, unfazed as his face fell.

"Really?" He said, his disappointed tone making it clear that he had been hoping for a repeat of the morning's events.

"Fifty lines, 'I will concentrate in class.'" Celestia instructed, Rally sighing audibly but taking the marker nonetheless and heading for the whiteboard. Satisfied that he wasn't arguing, she watched as he uncapped the marker and wrote the first line of his punishment. As he started on the second line she wrapped her arms around his midsection, resting her head on his shoulder so that her cheek brushed against his. "I don't want you to think this means I didn't enjoy this morning." She murmured gently into his ear, one hand tracing her fingertips along the middle of his chest through his shirt. He smiled at her admission, the happy feelings returning at the combination of her praise and her touch. "I have no regrets." She continued, planting a kiss on his cheek.

"I really liked it too." He replied, his free hand coming up to rest on hers as it trailed up and down his torso. At his touch her other hand came up to slap him on the wrist, causing him to jump slightly. "What was that for?" He asked, almost sounding hurt.

"You're supposed to be writing lines." She chided him, which only lead to a confused look from the teenager. She greeted him with a kiss, the  told him to write lines, then started to make moves on him only to chastise him when he responded in kind. What the hell did she want from him? "I can see this isn't making sense to you, so think about what you're writing." Still confused, he read the line over and tried to make sense of it in context. "Basically, you are going to concentrate on writing lines. If you lose focus..." She continued, he hand making its way around to run a finger between his butt cheeks. "Well, I won't be the one getting penetrated." Rally's eyes grew wide at her declaration, now fixed firmly on the whiteboard. He had no objections to gay people but he certainly wasn't interested in her putting anything in his ass.

Gulping, Rally once again raised the marker and started on writing lines. Deciding it would help his cause to focus on just one thing, keeping his hand steady enough to write properly seemed like the most logical choice. He could feel her hands returning to his torso, this time her fingers slipping under his t-shirt to trace light circles around his belly button. It was difficult to ignore her and write lines at the same time, but he was managing to get them done in a reasonably legible manner. Once the fifth line was finished Celestia started to up the ante, her hands making their way to his belt buckle and undoing it. Rally could still feel her gaze watching him intently for any sign of his concentration wavering, the blue haired student keeping his eyes stonily on the whiteboard as she pulled his jeans and boxers down with one fluid motion to expose him to her office.

"I especially enjoyed this." She purred into his ear, one hand wrapping itself around his faintly stirring cock. Her touch quickly finished what her teasing had started, his shaft growing fully erect in a few seconds. Rally could feel muscles in his face tightening in protest as he forced himself to keep his eyes on the whiteboard, his hand starting to tremble slightly as he made to start on the sixth line. The principal's hand made slow, deliberate strokes along his length, her lips kissing at his bare neck and letting her breath ghost on his skin. He shivered faintly at the combined intimate feeling of her kisses on his neck and the more direct pleasure of her hand stroking his cock, wanting nothing more than to bend her over her desk and have his way with her. However the penalty for not focussing was still in place and he was equally determined not to let her win.

Rally suppressed a grunt as Celestia found a rhythm, her hand maintaining an even pace as her kisses ceased to allow her better observation. The speed of his writing had definitely increased, sacrificing some neatness for the chance to finish quicker and spare himself the torment. Smirking, her other hand found its way down to cup his balls gently, massaging them with care. His hand froze at the new sensation, the blue haired student mentally ordering himself to keep writing even as he yearned to look down and see what she was doing. Blinking hard, his attention locked itself back onto his goal of writing out the fifty lines as quickly as possible. Eleven lines were on the board now, Rally not caring that they weren't perfectly straight as he started on the twelfth, feeling reasonably confident that he could finish without incident.

Keeping a close eye on him, Celestia could sense an emerging feeling of confidence coming from the teenager as he reached the fifteenth line. It wouldn't do to let him get too confident, the principal moving around so that she was standing just to his right side, partially in his field of vision. To his credit Rally kept his blue eyes firmly on the writing, ignoring her almost completely even though his writing was still affected somewhat. Her devious smile was still there, fuelled by the thought of how difficult things were about to get for him. Rally could see her in his peripheral vision as she got onto her knees, the principal licking her lips hungrily as she came face to face with his cock. Now on his sixteenth line Rally had to suppress another groan as he felt her wet lips give the tip of his penis a gentle kiss, his writing hand freezing once more.

"Mmm..." She murmured, just loud enough for him to hear and pique his interest. His face was stonily on the whiteboard, though his eyes had widened a little at her latest attentions. Celestia kept watching his face for any sign of his attention wavering even as she poked her tongue out to rest on the base of his shaft, running it slowly along the rigid length right up to the very tip. The warm, wet feeling along his cock was probably one of the most intense things he had ever felt save actually having sex with her that morning, but as he felt the head of his cock become enveloped by her heated mouth he realised that things were about to get so much harder. His first blowjob, the first time he had ever had this done by the woman he admired so much and he wasn't even allowed to look! It was so unfair!

Now on his twentieth line, Rally had to contend with the swirling mess of thoughts going on in his head. On the one hand he was amazingly happy that a woman as incredible as Principal Celestia was willing to be with him and do all these great things with him. But on the other he was feeling pretty angry that he basically wasn't allowed to enjoy it right now, that he was forced to try and ignore her talented mouth and tongue and instead write lines. Finally there was the sinking realisation that if he gave in and did lose their impromptu competition, he would simply surrender himself to the punishment no matter how much he didn't want to. He liked her too much not to do so.

The combination of physical pleasure and psychological torture continued for what Rally swore was an hour at least, though he had continued to write out messy lines in a reasonably consistent manner. He was unwilling to risk even the quickest glance down, unsure of just how much the principal could see from her current position. Temptation to do so fought a constant battle, arguing that when more of his shaft was in her mouth she couldn't possibly be able to see his face and he could afford a quick peek. Reason countered that if he did look he might not be able to look away and thus would definitely be caught, and reassured him that it would all be worth it in the end if he just hung on. All he had to do was keep writing...

"Just five more lines..." Rally managed to gasp out, knowing that his writing had gone from passable to a barely legible squiggle during the ordeal. He was leaning against the whiteboard, sure that at least some of the writing had been smudged or erased by his sleeve. Now he was on the brink of release, Celestia having used every second of that time to drive him wild with pleasure. At his statement however, Celestia stopped touching him completely. Suddenly aware of the cool air caressing his shaft and seeing her get up and walk away in his peripheral vision, he could barely muffle a scream of frustration. Rally wanted to put her back on her knees and make her finish what she had started, but he had already come so far and he wasn't about to give up now. Scrawling out the last remaining lines in a manner that could only loosely be considered words, Rally turned around with a scowl and fully ready to demand that she finish the job only to find her on her knees behind him, smiling up in approval.

“Very good, Rally.” She said, her hand coming up to hold the base of his cock. “I thought you might like to see the finish.” Blinking, his glare disappeared almost immediately as he watched her wrap her luscious lips around him once again, the pleasure that had started to face returning in force to compliment the visual gratification of the principal sucking on his cock. Now he could really enjoy himself, surrendering completely to her as she set a quick pace to finish him off and relieve him of the earlier torture. Moaning, Rally rested one hand on her head as she brought him straight back to the brink, finally taking just his tip on her outstretched tongue and rapidly jerking him off. He felt his climax hit, their eyes meeting for a brief instant as he came, Rally feeling immensely relieved as he shot his seed into her mouth and all over her tongue, the sight making him incredibly horny even as he enjoyed his orgasm. “Tasty...” She purred, closing her mouth and deliberately swallowing his cum.

“Principal Celestia...” He panted, watching as she got back to her feet only to plant her lips on his in a lustful kiss.

“I’m glad you enjoyed it.” She said, just inches away from his face. “But now I’m all hot and bothered, and I still have paperwork to do.” She simpered, holding his hands and guiding him over to her desk. “You put your pants back on and hop under there while I clean this board quickly, and then help me out.” He nodded almost dumbly, more than happy to do what she wanted. Safely tucked in under her desk he watched her legs as she wiped off all of the lines he had written, until finally she rested her hands on the top of her purple pants, sliding them down along with the frilly panties to expose herself to the office. His eyes were firmly fixed on her pussy, licking his lips in anticipation as she sat down in her chair and rolled it in, her legs on either side of him making the space a tight fit.

Rally felt her hand reach under the desk to rest on his head, guiding him to his destination with only slightly less encouragement than the sight of her slit so close to his face already filled him with. He brought his arms up to rest on her spread legs, his hands coming to rest on her ass and stretching his neck far enough to bring his mouth into contact with her crotch. The smell of her arousal filled his nose and only made him want her more, but as he extended his tongue to lick along her slit for the first time he found it was nothing compared to the taste. Warm and sweet on his tongue, he lapped at her in an effort to get more of her wonderful flavour, the principal moaning softly above her desk as she felt the teenager eating her out. Much like his kissing he lacked skill but made up for it with enthusiasm, allowing her to keep focus enough to fill out the last of her paperwork.

“Tia?” Student and principal froze at Luna’s voice and the accompanying knock on the office door, realising for the first time that day just how insecure her office was for their current activities. “Are you busy?” Tapping his head quickly to get him to stop, Celestia righted herself in her chair and hoped that her sister didn’t need much.

“No, come in.” She called back, keeping control of her voice easily enough as Luna opened the door. Celestia watched as she closed it behind her and sat down, offering her a pleasant smile even as she cursed her sister inwardly for her awful timing. “What can I do for you?” She asked, eager to cut to the chase.

“I just wanted to let you know that I’ve been talking with the technicians and it appears that the upgrades to the computer lab won’t be finished until at least Tuesday next week.” The principal made a face at this unwelcome news, while hidden under her desk Rally grinned evilly at an idea that had crept into his mind.

“That’s unfortunate, but I suppose it can’t be he-elped.” She responded, her speech wavering for a second as Rally returned to his previous task of licking her pussy. Outwardly she maintained her composure, though her thighs tightened around his head in an effort to get him to stop. With his face pressed right up against her slit, it was a doomed attempt. “Did they say anything else?” Celestia asked, hoping that her sister didn’t notice her breaths becoming a bit shorter.

“No, they have everything they need to do the task.” Luna said, her eyebrows furrowing slightly at the faintly odd look on the principal’s face. She was smiling but it looked as though it was fixed, a faint blush starting to spread on her pale cheeks. Underneath the desk Rally started to tease at her clit, his hands squeezing her backside while his tongue flicked over the sensitive nub of flesh, causing Celestia to shift in her seat at the pleasure now spreading through her. “Are you feeling alright, Tia?” She asked, her face filled with concern.

“Ah, I’m fine Luna.” She replied, gesturing to the forms still on her desk. “I’ve just been sitting for a while and still have some paperwork left to do before I can stretch my legs.”

“Alright then.” The vice principal said, getting up to leave. “I’ve finished my work for the day, so I’m going to go and do the shopping. Did you need me to get anything that wasn’t on the list?”

“N-no!” Celestia said, a sudden surge of pleasure causing her voice to rise slightly. She couldn’t believe how close she was to her orgasm, unsure of if it was the fact that it was a student eating her out secretly in front of her sister or just how pent up she was that was speeding up the process. All she knew was that she wanted Luna out of the office.  “I’ll see you at home.” The vice principal nodded, exiting the office and closing the door behind her. Once it was closed the barely maintained neutral look shattered, anger being the dominant emotion due to the ordeal he had just put her through. “Rally are you ins-aaah!” Her protest was cut short at the sudden arrival of her orgasm, her inner walls tightening around the student’s tongue while her thighs gripped his head tightly. She collapsed forward onto her desk, stuffing her hand into her mouth to try and muffle the rest of her moans.

Slowly, Rally felt the pressure her thighs had on his head ease up as Celestia’s body went slack in her afterglow, finally able to bring his head back to admire his handiwork. The sheen of her juices wasn’t just on her pussy but also partially on the chair below. Now that he was further away he could also feel that his chin was wet too, licking along his lips only to find her sweet taste lingering on there. Easing himself out from under her desk, Rally stayed on his knees long enough for Celestia to meet his gaze, though her own was withering. “Not a good idea?” He said, a touch of worry in his voice as he realised that he may have made a grave error.

“You need to use better judgement in the future, Rally.” She panted, the student nodding his acceptance. After a moment her gaze softened again, satisfied that he had learned his lesson. Celestia beckoned him closer, giving him a passionate kiss and happy that she had made the right choice with him.

Extra Jobs

Rally stared at the ceiling of his room, lying on his bed with his arms folded behind his head and one knee propped up in the air. The fan above was on a low setting, balancing the temperature nicely as he thought about everything that had happened between him and Celestia earlier that day. His computer was still on, a video on YouTube about Team Fortress 2 playing in one tab and MyStable open on another, neither of which he was paying any attention to. Today had been the best day he had had in a long time, not just because he had lost his virginity to a beautiful woman but also feeling like someone cared about him again. He knew that his friends all cared about him, that the Apple family cared about him, but today felt like an emotional dam had come down and for the first time he was actually able to realise it.

Tapping his foot on the white sheets restlessly, he wondered why despite all of that he wasn’t smiling right that moment. He did feel happy, but at that moment he also felt lonely. While he had been at school Celestia had felt accessible, but now that he was at home it felt like she was out of his reach. He raised his hand above his face, letting the black sleeve fall down his forearm a short way to reveal his watch. 8:34pm. Dinner was always dead on 6pm with the Apple family so there was little chance of him being disturbed, Rally glancing at his night stand where his phone sat. Maybe he could call her? Rolling onto his side he grabbed the phone and unlocked the screen, pausing right after he remembered that Luna shared the house with Celestia. A phone call might be overheard and would lead to awkward questions. He let his hand and the phone fall to the bed before remembering that he could text her. Hastily he typed out a message and sent it.

Hey, did you enjoy today as much as I did?

Getting up and sitting in his desk chair, Rally set the phone down in front of his keyboard as he waited for Celestia to reply. On the screen was the video, several YouTubers having teamed up to play a round of Mann vs Machine with some very questionable tactics. He switched the tab over to MyStable, checking some of the notifications that had started to pile up. Pinkie had liked some things he had posted, Rarity had invited him and Applejack to her upcoming birthday dinner, Trixie had left an obnoxious comment on an old picture of his. He frowned, unable to remember why he had even added her on there but not bothered enough to remove her. After about ten minutes of aimless browsing his phone played the message tone, his eyes lighting up as he saw it was from Celestia.

Yes, very much. We will have to do it again soon. ;)

Her confirmation left him with a big smile on his face, glad to know that he had been good enough for the principal. The fact that she had suggested that they do it again was very encouraging, Rally almost quivering with excitement as he sent a reply.

Anytime you want <3

He didn’t have to wait long for the next reply, Rally guessing that she hadn’t been with her phone when he had sent the first message.

Can you come over on Saturday morning? I need to do some yard work but we can play once that’s finished.

Sure thing. Looking forward to it!

Feeling pretty good about where things were going Rally put his phone back down and turned the screen off, his confidence back and leaving him wanting to play some video games. Closing the web browser and opening up the game client, he paused just before opening the game when he heard his phone go off again. Curious, he found another message from Celestia waiting for him. His jaw dropped at the sight that greeted him, the principal having sent him a picture of herself. She was lying on her bed, the sheets strewn messily around her and a pillow propping her head up. Celestia was giving the camera a suggestive pout, her free hand holding one finger up to her lips but what really got his interest was the lack of any clothing above her hips. Her breasts were completely exposed, looking very soft and inviting and leaving him wanting nothing more than to touch and kiss them.

Rally got back out of his chair, heading for the bed with his phone in one hand and the other fiddling with his belt buckle.

***

Saturday could not come fast enough for Rally. There were still two more days between then and him, but fortunately he had things to keep him occupied until then. Thursday saw the soccer team try outs during final period, Rally’s improved mood getting him playing his absolute best and only narrowly being outperformed by Rainbow Dash. To celebrate they had gone out to a movie and pizza after school with the rest of the team. Due to his detention on Wednesday Pinkie Pie had rescheduled the party to Friday after school so Rally had plenty to enjoy, even if her father kept a close eye on him the entire time. He had almost wondered if he would have enough energy for Celestia after those two days, but getting an early night on Friday was easy enough and he felt refreshed and energised when he woke up on Saturday morning.

“Ah, Rally. Right on time.” Celestia said as she opened the door on Saturday morning, the teenager greeting her with a bright smile. She was wearing the same clothes she had worn when he had first done yard work for her, the black t-shirt and purple shorts he remembered so well giving him a great view of her figure. Beckoning for him to follow her around the side of the house, Celestia gave him a quick wink as he followed her with his bike. “Luna went home with someone last night, so we should have the house to ourselves for the morning.” She murmured, his smile growing at her implication. “We’ll just take care of this yard work first, alright?”

“Sure.” He said, leaning his bike against the wall before joining her at the shed. “Want me to do the mowing?”

“Please.” She replied, allowing him to take the lawn mower out so that she could grab the hedge trimmers. Silently they both headed back to the front yard, Rally stopping a the gate to prepare the mower while Celestia moved to the shrubs along the driveway. As the mower roared to life she started clipping at the bushes, glancing over her shoulder to see him starting along the fence. A faint blush spread along her face as she imagined what he would look like without his shirt, sweat glistening on his bare chest as he did all that work. She bit her lower lip, sorely tempted to just call off the work and get him into her bed right then but resisted the urge, knowing that the work had to be done or Luna might suspect something when she got home.

Contenting herself with thoughts of what was to come she turned back to the bushes and started work on them, going a bit faster than she normally would in anticipation. Likewise Rally was going as fast as he could while still trying to do a decent job, not wanting to disappoint Celestia in any way. The minutes passed by, both student and principal mostly caught up in their own thoughts as they did the best job they could in as short a time as possible. Soon enough the lawn was finished, the catcher emptied into the bin followed by the clippings off the shrubs to leave the front lawn looking very neat and tidy. Rally checked his watch, noting that it had barely been half an hour of work but the result was worth the time.

“Anything else to do?” Rally asked, wiping his brow on his sleeve. It had been quite warm, leaving the teenager sweating a little.

“No, that’s all we needed to do.” She replied, shooting him an impressed smile. They both knew why he had really come over that morning, but the fact that he was checking to see if anything more was there showed a good work ethics. “How about we have a glass of water?” She suggested, the teenager nodding in response and following her back around the side of the house. Depositing the mower and trimmers back into the shed principal and student headed around the backyard pool into the kitchen, Rally taking a seat at the table while Celestia fetched two glasses and filled them with water from the purifier. Gratefully he accepted one of them, downing the entire glass quickly and enjoying its coolness in his mouth. “So, I was thinking that since we’re both all hot and sweaty, how about we have a shower?” Celestia purred once she had finished her glass, fixing him with an amorous gaze.

“Sounds great.” He said, reaching over to hold her spare hand. He ran his thumb along her smooth skin, smiling happily at the simple gesture. The fact that he could just hold her hand like that, even though he couldn’t do it in public, made him feel a warmth he hadn’t felt in a long time. They were silent for a minute, gazing at each other with their thoughts their own.

“I suppose it’s hard to get in the shower if we just sit here.” She said, causing both of them to laugh. Spurred on by the thought, Rally stood up while keeping hold of her hand, letting Celestia lead him down the hallway towards the bathroom. When she opened the door he was surprised at just how roomy it was. Directly across from the door was a double basin, the side closer to the wall home to Celestia’s bathroom apparel while the other belonged to Luna. The floor was smooth black tiles with a single step up into the biggest shower he had ever seen on the right hand wall. He could see two shower heads in there, once again each side home to the belongings of one sister. “The glass on the doors turns opaque when either shower is in use.” Celestia explained, gently encouraging him into the bathroom. “Sometimes we sleep in, so we shower together.” She added, a deliberate purr in her voice. “It’s so nice to help clean each other, rubbing our hands all over each other’s wet, soapy bodies...” She smirked at his expression as his imagination took off, a faint blush and grin appearing at the thought of Celestia and Luna fondling each other.

“Not gonna lie, I want in on that.” He said, turning back to her as her foot clicked the door shut. They stepped in close, their arms wrapping around one another in a close embrace as their lips followed suit, student and principal sharing a passionate kiss. Celestia’s hand snaked up to his neck, his own coming down to tenderly squeeze her firm backside and hold her close, the principal able to feel his growing desire. It only made her want him more, her hands trailing down his neck and back, running along the fabric until they reached the bottom of his t-shirt and started to lift it up. Rally’s eyes went wide mid-kiss as he realised what she was doing, his hands coming up instinctively to grab his shirt and hold it down as the kiss broke. She stared at him in confusion as he took a step back, looking down and blushing in embarrassment. “No one...” He mumbled, still not able to look at her directly. “No one’s seen me without my shirt on since... since...”

“The accident.” She finished, getting a small nod in response. His face was burning, the student clearly not having realised until that moment he would be going without it in the shower with the promise of sex distracting him. Gently, Celestia took his hands in her own and simply held them, her thumbs rubbing along his green skin in an effort to calm him. His knuckles were white due to the grip he had on his shirt, but she could feel it beginning to relax soon enough. After a minute he finally released the fabric, looking up at her where she could see that while he still had worry in his eyes, he also wanted to trust her, to let her in. Her fingers slowly slid up under his shirt, the bottom of it coming up as she hooked her thumbs onto the fabric. Standing as close as she was to him Celestia couldn’t see anything yet, Rally raising his arms and allowing her to take it off completely. “Oh, Rally.” She whispered as she got her first look at his bare chest, her eyes drawn to the scar that ran from just under his left collar bone all the way down to his navel, realising for the first time just how close he had come to death that day.

Rally couldn’t stop her from giving him a hug. He closed his eyes and let himself be held, the warmth and closeness of her body keeping him from feeling as self conscious as he had been initially. To his knowledge the only person who had seen it apart from himself was the nurse who had removed the stitches, and now his shoulders slumped in her embrace as he thought that she wouldn’t want to be with him now that she had seen it. She felt the movement, bringing her head back to give him an affectionate look. Lifting his head up Celestia gave him a tender kiss, her fingers curled under his chin while the other hand ran up the back of his neck and into his hair, the fine strands falling between her fingers softly.

“Principal Celestia...” He breathed, blinking when he saw the odd smile she was giving him.

“Rally, when it’s just us you don’t have to use my title.” She gently admonished him, the teenager blushing as he realised how silly it sounded. “Just call me Celestia.”

“Okay... Celestia.” He said, grinning at this simple change. Giving him that option made him feel that she regarded him with a healthy amount of respect, that he was more than a student or a booty call. Satisfied that he knew that she treated him as an equal, Celestia brought her lips down to kiss at his neck, eager to return to their activities. He could feel the hard basin behind him, content to let her do what she wanted. Her lips and her breath against his neck sent shivers through him, his eyes closing and a raspy breath escaping him. Emboldened, she gently placed a single finger on the middle of his chest. She felt him tense up at the contact, the older woman feeling his breaths become short and his heartbeat quicken as she let the rest of her hand join it.

If he wanted her to stop, she would. But it was important for him to learn that he could trust her, that he could let her in.

“Rally...” She murmured, rubbing her hand along his torso. The teenager didn’t exactly have defined muscles but his chest felt firm, strong and fit. It was to be expected from one of the school’s top athletes, but just feeling it under her hand was getting her excited. She eased her hand across until her fingertips came into contact with the scar. Rally held his breath, unsure of what he was worried about. He knew it wouldn’t hurt. He knew it wouldn’t spontaneously open up. Above all, he knew that he could trust her. Slowly he released the breath he had been holding as her fingers made their way down the length of the scar. It was rough, the principal not having felt anything quite like it before.

Celestia’s free hand cupped his chin, lifting his face up so that she could kiss him again. Her soft lips felt wonderful, the kiss helping him to relax. Once again her lips moved to his neck but this time his hands came up to rest on her hips, sliding just under her shirt to rest on the smooth skin of her waist. Rally started to lift her shirt up, the principal stopping her kisses long enough to let him lift the black t-shirt up and off her. The bra was next, the teenager fiddling clumsily with it for a few seconds before it came undone. Celestia watched with amusement as he took her bra off, his eyes fixed on the prize that awaited him. Having only seen her breasts in a picture it was something of a treat to see them in person for the very first time.

“Whoa...” He said, struck dumb momentarily at the sight. While her breasts weren’t huge they were a nice size, the blue haired teenager reaching up almost hesitantly to cup the soft mounds as an idiotic grin spread on his face. He gave them a few gentle squeezes, catching her nipples with his thumbs and teasing them until they were hard. His tongue came out to lick his lips unconsciously, leaning in without thinking to take one of her nipples in his mouth and suck on it. Celestia let out an encouraging moan, her hand sliding into his hair once more to further encourage him. Having him suck on her breasts and grope them was making the older woman feel very close to him, a smile finding its way onto her face in between moans.

“How about we get into the shower now?” She suggested, the teenager nodding in agreement. They broke apart, walking towards the shower while undoing their pants on the way. Celestia started the water running, Rally marvelling as he watched the shower glass turn opaque almost immediately as she said it would do. “Put your clothes in a small pile there.” She said, Rally following her instruction by folding them up and putting them on top of his shoes. In contrast Celestia threw her clothes on top of his messily, her intent clear as he saw that they hid his nicely. Her panties were the last thing to join the pile, the green skinned teenager blinking as he realised that meant the principal was full naked. He couldn’t help but smile at the thought that they were fully naked together for the first time.

“I really like you, Celestia.” He said, moving to her side and loosely embracing her. She smiled gently back at him, one hand coming to rest on his lower back and holding him close. A poke on her leg alerted her to his excitement, the principal’s smile becoming more amorous as her free hand found its way to his rock hard shaft.

“I like you too, Rally.” She murmured back, her hand stroking his shaft. The touch emboldened him, one hand moving from her hip to tease at her soft folds with his fingers. A quiet moan was his reward, the teenager continuing to slowly rub at her pussy until he could feel it starting to get wet. The softly hissing water was starting to radiate warmth onto their skin, though it was nothing compared to her heat around his fingers. “I want you now.” She said, those words enough to get them both into the stream of heated water. They turned to face each other, stepping close to share a passionate kiss as the water streamed over them both. Rally instinctively rocked his hips, his hard cock thrusting between her thighs and only serving to make both of them incredibly horny. She reached down to guide his tip up, feeling it press into her entrance before sliding inside her welcoming body.

“Heh, being shorter isn’t all bad.” He laughed, Celestia joining him in a quick laugh as they both stood upright in the shower, his cock inside her comfortably as they embraced. Gently he bent his knees, the movement allowing him to pull out of her before straightening back up, smoothly thrusting into her. It had only been a few days but Celestia could barely believe how much she had missed having Rally inside her, being filled by his cock and the pleasure it gave her. He kissed at her collar as he started with a slow pace, managing to keep that position going for a bit over a minute before his knees started to get uncomfortable through the repetition, pausing for a second. “Sorry, can’t keep that up.” He apologised, the rainbow haired woman nodding in acceptance.

“Put me up against the wall.” She whispered, following his steps until she felt her back up against the cool tiles. One of his hands found its way onto her thigh, lifting her leg up as her own hands draped themselves over his neck. Rally soon after lifted her other leg up to join the first, using his body to pin her to the wall securely. She turned the shower head with one hand so that the water cascaded onto them again, leaving them slick and warm as the student began thrusting into her once more. “Oooh, this feels so good!” Celestia moaned into his ear, her skin tingling as he returned to kissing her collar again. Her ragged breath in his ear only made him want her more, his kisses on her neck becoming almost rabid. Not for the first time she was glad that he was such a fit partner to have.

“You’re amazing!” He breathed, his hands sliding down to hold her ass and squeeze it firmly. It felt soft in his grip, the teenager starting to thrust a bit harder in his excitement. Celestia moaned louder and her arms held him tighter as she felt his tip reach further inside her pussy, stroking on the sensitive nerves and flooding her senses. All she could focus on was his cock sliding in and out of her, it was all she wanted to focus on.

“Oh, Rally!” Celestia moaned, feeling the pleasure coursing through her start to really build up. She could scarcely believe how quickly it had happened, feeling her orgasm nearing all too soon. A few more thrusts from the teenager was all it took, the principal’s arms and legs gripping him close as her pussy tightened around his cock. One final cry of pleasure escaped her, Celestia feeling truly satisfied by the sex. After a few seconds she realised that something was missing, her purple eyes looking into his blue eyes in surprise. “You didn’t cum?” She asked, the student shaking his head. He had significantly slowed down his thrusts now, his shaft easing into her and gently stroking along the highly sensitive nerves. “Do you mind if I finish you off a different way?” She panted.

“Okay.” He agreed, letting her put her feet back on the floor and pulling out of her. Rally had actually been quite close himself, but her orgasm had made him want to not overdo it in case it made things worse somehow. Focussing on her, he watched as the principal got onto her knees and quickly took his length into her mouth, wasting no time in sucking him off. Her mouth felt incredible around him, accompanied with the sight of the water cascading through her rainbow hair made for a sight he never wanted to forget. She could taste her own arousal on him, sucking on his cock with all the experience she had to please him as best as she could. “Ahhh, Celestia! I’m gonna cum!” He moaned, the principal taking as much of him into her mouth as she could while one hand gently massaged his balls.

“Tia, I’m coming in.” Luna’s voice caused both of them to freeze even as Rally came, filling Celestia’s mouth with his cum. Her surprise was muffled by his cock in her mouth while the teenager stuffed one hand into his mouth to stifle a groan of his own. The principal quickly swallowed as the bathroom door opened and her sister walked in, the vice principal yawning as she approached the mirror. Luna looked somewhat dishevelled, her blue hair messy and the grey t-shirt and jeans she wore looking as though they had been in a pile for most of the night.

“She can’t see through the glass.” Celestia hissed quietly in his ear, the running water preventing her sister from overhearing. Rally’s blue eyes were wide, the fear evident to her though he stayed perfectly quiet. “Good morning Luna.” She addressed her sister, trying to sound bright and chipper. “How was your night?”

“Very enjoyable.” She replied, a broad smile appearing on her face as she stretched against the basin. “Sky High was certainly quite the gentleman you saw when we met him... and he certainly knows how to treat a woman.” The smile turned devilish, the meaning of the words clear.

“I’m glad you enjoyed yourself.” The rainbow haired woman said, able to relate to Luna’s elation for the first time in years.

“You really should have at least considered his friend though, Tia.” She added, another yawn escaping the blue skinned woman. “You don’t want to be alone the rest of your life, do you?” Rally blinked, taken by surprise at the revelation that someone else may have been trying to get involved with Celestia. The thought punctured the last of his happy feelings that Luna’s arrival had missed, his face falling at the idea that she could do better than a high school student.

“Luna, I assure you that I’m quite happy at this point in time.” Celestia said, having noticed his shift in mood. A reassuring smile was all it took to reignite the happy feeling again, Rally letting her take his hand in hers comfortingly. Out of the corner of her eye she noticed Luna moving again, her top being peeled off to reveal her lacy black bra. “Uh, you look tired. Maybe you should get some sleep?” She suggested, trying to get ahead of the vice principal’s intent to join her in the shower. She paused, hands having slid her jeans half way down her rear to reveal a matching v-string as she considered Celestia’s words.

“Good idea.” She said, yawning again even as she let her jeans fall to the bathroom floor. “I just might fall asleep in the hot water.” Leaving her clothes on the tiles she exited the bathroom, student and principal both exhaling a breath they didn’t know they had been holding. Celestia glanced over to see Rally lowering himself to the floor, joining him in a side hug as the water continued to fall onto them.

“Didn’t think you were serious about you two showering together.” He said, still a bit dumbstruck that he had almost seen the vice principal naked in the same room as the principal. She began to chuckle quietly, Rally joining in soon enough as the tension faded away.

Reunion

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Moving On

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It's A Date

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Newsworthy

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