Student-Principal Confidential

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.