Chapter One
The Fluttershy Diaries
-by Drace Domino
There were times when Fluttershy’s desire to help her friends conflicted with her tendency to hide from anything that made her the slightest bit nervous, and this was certainly one of those instances. As she stood side-by-side with Twilight Sparkle on the empty sidewalk, the two women looked at the store in front of them with a contrasting level of enthusiasm. For Twilight, that moment was nothing but raw excitement. The books sitting in the window, the rows of shelves deeper in the store, and even the rack of bookmarks just past the door was enough to make her eyes light up. She rocked back and forth on her heels and even cautioned a few looks back in Fluttershy’s direction, hoping to stoke the same level of enthusiasm in her otherwise timid friend. Unfortunately for her, all of the casual glances in the world couldn’t push confidence into Fluttershy, who was focused entirely on the name of the store hanging overhead.
“The Tartarus Archive - Musings of Mystical Erotica.” The girl said it out loud with a slight wobble to her voice, and she even took a half-step back as if trying to hide behind Twilight. Dressed as she was in her usual long green skirt and a soft pink blouse, it was easy to assume that she was the last person that would step foot in such a store, and she seemed eager to reinforce that opinion. She finally managed to squeeze a whimper from the back of her throat as she looked through the window, spotting a stern-faced cashier that was already giving the pair a lazy look. “Oh, gosh, Twilight, I don’t think we should be going inside there. I mean…that looks a little…uhm…naughty, isn’t it?”
“Fluttershy, that’s the point!” Twilight smiled, and took the time to regard her friend with a kind, considerate look. Fluttershy always took just a little extra work, but it was worth it for a loyal, sweet friend. “Tartarus Archive is the only place in town that has the books I’m looking for. I can’t order them online, what if Shining Armor or my parents were to find them?”
“But…but…” Fluttershy squeaked, and let her voice drop to an even lower whisper than it already sat at. “Have you considered maybe reading…nicer books?”
“I have. They just don’t do anything for me anymore.” Twilight Sparkle simply shrugged, and lifted a hand to adjust her glasses, speaking in a matter-of-fact fashion. “It’d be irresponsible for me to learn about sex by going out and doing it, so by my estimations the best way to curate that knowledge is by consuming erotic literature! It combines my love of books, my love of learning, and what I’m increasingly starting to believe is my love of multi-partner sexual situations where a solo woman is the center of attention!”
Fluttershy just blinked.
“Twilight? Are you sure you should be telling me this much about y--”
“Gangbangs, they’re colloquially called.” Twilight lifted a finger pointedly, far too focused on the learning aspect to pay attention to any social cues. “Granted, there’s a lot of different types of them, and reading a variety of stories is the only way I’ll be able to discern what type I want to participate in one day. Whether or not I’ll allow all three of oral, vaginal, and anal penetration, if I’ll permit them to quote unquote ‘bukkake’ me or not, if I’ll require them to use protect--”
“Okay, okay, I’ll go in with you already!” Fluttershy blurted out, her cheeks already blushing vibrantly while she looked around frantically from side to side. The city streets were empty, but that didn’t matter - she could always find the headspace to imagine there were people lurking nearby listening. “J-Just please stop talking about it before somebody hears us! I don’t want anyone to think we’re…we’re dirty!”
“Thanks, Fluttershy.” Twilight Sparkle just beamed, and slowly reached down to take her friend’s hand. She pressed their palms tightly together and allowed their fingers to interlock, taking a firm grip that she had no intention of letting go anytime soon. Her other hand pushed to the door as they began to enter, and she gave Fluttershy one last vote of support before they stepped inside. “You’re a really good friend. That’s why I knew I could trust you to come with me.”
If Twilight Sparkle only knew the power of holding Fluttershy’s hand, she could’ve skipped trying to convince her at all. From the very second her purple fingers moved to lock against Fluttershy’s own yellow ones, the timid girl instantly felt more relaxed. More at ease. She effectively melted into the touch as she stared down at the spot where their hands were linked, focusing on it even as they moved through the store. She barely even noticed when they stepped inside or when Twilight Sparkle offered a pleasant greeting to the cashier, simply floating along beside her friend like a pink-haired balloon happy to be touched.
Fluttershy liked holding hands. Maybe more than anything else in the whole world. It made her feel safe, it made her feel loved, and it made her feel…other things that she had never really been able to properly sort out. But either way, Twilight Sparkle could’ve marched her from one end of town to the other and she wouldn’t have said a word of complaint so long as the nerdy young woman kept their hands linked and their palms pressed together. The tactile sensation of her friend’s touch was all Fluttershy needed.
“Hmm…I’ve read this one. Read this one. Borrowed this one from Octavia…” Twilight Sparkle’s words finally drew Fluttershy out of her blissful stupor, and when she looked up the young woman saw that they were standing in front of a tall bookshelf filled with tawdry, filthy stories. Some of them opted for a subtle presentation with titles like “A Kiss from Twelve” while others were far more crass, sporting names such as “Spitroasted Schoolgirl Whores.” Twilight Sparkle appraised them all with the same level of scrutiny, with a shopping basket looped around her free hand that was already carrying a few titles. “Ohh! This one takes place in a movie theater! Have you ever thought about having sex in a movie theater, Fluttershy?”
“What?!” Fluttershy’s squeak filled the mostly-empty store, followed by a frantic bit of blubbering. “N-No! I mean, why would I--how would you even without a bed, and, and, and--” She suddenly dropped her voice to a low, scandalous whisper. “What about the other people trying to watch the movie?”
Twilight’s nose scrunched up briefly, before she tossed the book into her shopping basket with a smile.
“Well, if it’s a boring movie, I guess they could join in, too!” She finally answered. “The more the merrier, right? Gosh, I think gangbangs are neat.”
Fluttershy simply whimpered, and let herself focus on the touch of Twilight’s hand against her own. It didn’t matter if her friend was actively pursuing countless titles to fantasize about a dozen men running a train on her. It didn’t even matter that if anyone they knew spotted the two of them in a naughty place like the Tartarus Archive that rumors would swirl about them at school. So long as she had that sweet contact with her friend - and it was even better when Twilight Sparkle idly brushed her thumb back and forth against Fluttershy’s fingers. That was the good stuff.
That sweet bit of kindness kept Fluttershy complacent the whole time Twilight shopped, filling her basket up with books she was almost certainly going to treat as how-to manuals for the day she was able to fulfill her naughty fantasy. When they stood in front of the cashier, Fluttershy did her very best to shrink away from the stranger’s line of sight - hiding herself behind a desk-mounted bookmark rack and trying to shrink away. Still she could hear the conversation between Twilight and the older girl, each moment filling Fluttershy with more and more tension.
“Wow, it must be great to work here with all of these amazing books.” Twilight gushed in her usual nerdy state, and Fluttershy could see her lean forward and squint, actively reading a nametag. “Chrysalis. That’s a pretty name. Have you read every book here?”
“Can’t say I have.” Came the slow, lazy reply, as the cashier stretched out to take Twilight’s books, slowly tallying them at the register. As she worked, Fluttershy dared to peek around the bookmarks at her, staring with wide eyes as a unique-looking girl that was intriguing and frightening in equal measure. Chrysalis was slender and tall, with jet black skin and long, untamed green hair - the former of which carried a few hints of silver thanks to piercings in her nose, lip, and ears, and the latter which sported a single butterfly barrette clinging to the side of her head. She was pretty, in a dangerous way, and as she kept ringing up Twilight’s purchases, couldn’t help but make a playful comment. “Sensing a trend with these titles. You’re a real slutty piece of work, aren’t you?”
“Me? Oh, gosh no! Not yet, at least. But maybe one day!” Twilight beamed, adjusting her glasses and happily letting any possible insult vault far over her head. “Do you think these will give me proper insights to when and if I do decide to conduct myself with this sort of behavior?”
“Uh…sure.” Chrysalis’ response was flat and deadpan as she let her eyes glaze over the last title in her hand. “You’ll be ‘A Cheerleader Cumdump Part 4’ before you know it.”
Twilight Sparkle simply preened at the idea, and even blushed quite a bit, her hand tightening within Fluttershy’s own. It was a good thing, too, since when the cashier finally stretched up to look over the bookmarks and spot the pink-haired girl hiding from her, it would’ve been enough to make Fluttershy flee if Twilight wasn’t holding her in place.
“Who’s your jittery little friend?” Came the natural question, as Chrysalis let her emerald green gaze narrow on Fluttershy. “Doesn’t say much. She your bottom?”
“B-Bottom? I…I don’t understa--”
“Oh, she’s my friend! One of my best friends!” Twilight smiled brightly, and stepped closer to Fluttershy, as if sensing her friend’s flight response about to activate. “Actually, she was super sweet in coming with me today, so I’d like to buy her something. She’s not really into all of the naughty stuff, though, so…do you have any suggestions?”
Fluttershy simply froze in place while the two women talked about her like she wasn’t there, deciding on her fate that evening. Twilight Sparkle’s heart was certainly in the right place, but in the moment, all the pink-haired girl wanted to do was get the heck out of the store and hide under her covers back home, so she could parse this harrowing experience. Chrysalis let the question linger in the air for a long moment before finally reaching underneath the counter and pulling something up - a solid black book with a green ribbon bookmark dangling from it, complete with a butterfly logo on the front.
“Here’s a blank journal, since it seems like she doesn’t have much to say.” Chrysalis offered a thin smile, and gently dropped it on top of Twilight’s stack of dirty gangbang books. “You’re the only customer I’ve had all day, so…free of charge.”
“Wow, really? That’s so nice of you!” Twilight beamed, and went back to finishing the transaction. Fluttershy nervously stood at her friend’s side the whole time, and even managed to squeak out the faintest bit of a “thank you” in the direction of the mysterious cashier, but as the two girls finished shopping and made their way towards the door, she couldn’t help but feel uneasy.
Uneasy…but still comforted by Twilight’s touch. There wasn’t much a good handholding couldn’t fix.
***
Fluttershy didn’t think of the journal again until late that night, after her evening shower and the slow, delicate crawl into bed. Dressed in loose-fitting pajamas with an adorable bunny print and surrounded on all sides by stuffed animals, the young woman finally sat at the head of her bed with her back against the wall, rump supported by a small pile of pillows. It was there, for the first time since receiving the journal that she allowed her fingers to pass over it, murmuring softly to herself in her typical downtrodden, self-doubting way.
“Oh Fluttershy, you’re so silly sometimes.” She murmured, her lower lip sticking out in the form of a tiny pout. “All Twilight wanted to do was share something she liked with you, and you could barely even force a peep out.”
It wasn’t for lack of wanting to, it truly wasn’t. Though Twilight’s interests certainly veered more…exciting than Fluttershy was used to, there was a genuine desire within her to bond with her friend. She liked Twilight. She liked feeling safe alongside Twilight. And even though the academic, intensely nerdy girl sometimes let her mind trail off in directions that Fluttershy couldn’t follow, that didn’t mean the pink-haired sweetheart couldn’t at least try! For the moment, she sat on those tiny regrets while staring at the butterfly embossed on the front of the journal, tracing it with her thumb in a slow, idle motion to ease her into a more relaxed state. It was odd - holding the thing made her feel a little bit better. But then…it was a gift from Twilight, after all, and a kind gift from one friend to another always had the effect of lifting one’s spirits.
“I guess I should write down some thoughts in it.” She murmured, finally opening the front cover as she reached out with her free hand, scooping a pen off the nightstand. Before her there were lineless pages begging for her thoughts - endless potential that only she would see. She trusted her parents and her friends to never peek at something so private, and so Fluttershy knew this was a place for her to write down her filthiest thoughts. Her most scandalous fantasies. Her most nagging, intense daydreams that kept her frustrated throughout the long days at school. Finally she pressed her pen to the paper, and started to write. “I wish Twilight would hold my hand more often.”
Afterwards, she scrunched up her nose and gave a tiny huff, reading the words back in her mind.
“Really, Fluttershy? That’s all the dirtier you can get?” She asked of herself, and took the time for a long, deep breath. That night in her room, the atmosphere was perfect for fantasizing. Still warm and fresh-scented from the shower, she sat in a space lit only by the nearby desk lamp, giving her sanctuary a feel of quaint peacefulness. The only noises outside were those of the birds settling into their nests and the bugs going about their evening activities, both of which were sounds that had only ever brought Fluttershy comfort. As she sat with her legs folded and the journal in her lap, she finally let her eyes open once more, speaking in a softer - and more thoughtful - tone. “Twilight Sparkle was having a lot of fun with her fantasies even though they weren’t about her. Maybe…maybe I can do the same?”
The mere act of starting to fantasize was an exciting prospect for her. Fluttershy wasn’t exactly like the rest of the girls in her friend group - something she had been keenly aware of for some time now. While Pinkie Pie, Rarity, Applejack, Rainbow Dash, and Sunset Shimmer were all happy to change with the other girls during gym class, Fluttershy had always slinked into the background, hoping none of them ever noticed. It didn’t matter that she knew they’d love her no matter what, and it didn’t even matter that she felt entirely safe around her best friends.
She didn’t feel strange because she had a penis. She felt strange because the thing was so gosh darned big.
As she sat there trying to fantasize, Fluttershy idly slinked a free hand down the front of her pajamas, and slowly pulled it out. The inches upon inches of pale yellow flesh were an impressive, girthy sight even when she was flaccid - big enough to stuff her panties to the point of overflow even when she wasn’t excited. Even now as she sat with it in her hand, the thing was starting to perk up and spring to life, no doubt assisted by the leftover excitement that had nagged at her during the shopping trip with Twilight. It was almost painful to keep herself in check while Twilight was going on and on about how exciting group sex would be, and now…now those memories were flooding right back into Fluttershy’s mind, all while she tried to come up with a fantasy of her own.
“Let’s see…I think that the most beautiful girls at school are…hmm…” She tapped her lower lip with her pen, all while her free hand gave a slow, tentative stroke to her unit. It responded with a faint twitch, creeping ever-closer to a fully aroused, sturdy state. “Oh, I know! Principal Celestia and Vice-Principal Luna! Ohh, they’re so pretty! And nice! And I bet they wouldn’t think too kindly of me having dirty thoughts about the--”
She suddenly scrunched up her nose, gripped her unit with a firm hold, and bonked herself on the forehead with the end of her pen.
“No, Fluttershy! It’s okay for you to fantasize! You don’t have to feel bad about it!” With that reassured reminder, she took her pen down to the journal once more, finally starting to write. “I think it would be really…uh…sexy…if Principal Celestia and Vice-Principal Luna wore really short skirts to class! And what if Principal Celestia wore her hair in a cute ponytail, too?”
She wrote the words exactly as she said them, in the form of rambling thoughts about what she’d find sexy in her own timid, tender way. There was a slight wobble to her normally tidy handwriting, though, a result of her other hand slowly working up and down a shaft that was growing increasingly more stiff within her palm. Excitement tended to creep over Fluttershy slowly thanks to her mild nature, but once it started it was difficult for her to push away, and before long her hand was sweeping back and forth without conscious thought. That girthy yellow cock twitched within her open palm and caused her fingers to give it a firm squeeze at the base, drawing a long but sweet moan from the very back of her throat. At the same time a blush cascaded over her cheeks, and she whispered to herself in a delicate, almost reverent tone.
“Oh…oh my, that’s…that’s certainly an exciting thought.” She marveled at what she’d already written - outlining a world where principals wore short skirts and where Twilight Sparkle was eager to hold her hand. Still, in that moment of delicate privacy Fluttershy allowed herself to be greedy, just as she started to unfold her legs from under her to shift onto her knees. “I…I wonder what else I could think of if I put my mind to it…”
As it turned out, she could imagine quite a bit that she couldn’t quite put words to just yet. Flashes of flesh and pleasure, scenarios that blinked in her mind that were inspired either by rumors she heard at school, or odd fantasies that picked up from casual gossip amongst her friends. Even Twilight’s dirty little dream about getting gangbanged popped into Fluttershy’s mind, in particular how fun it would be to watch such a thing take place in person, but that notion like so many others failed to make it onto the paper. In fact, Fluttershy so quickly lost control of herself that the only dreams that would get scribbled down that night were the ones that were already there - mostly-innocent musings about her principals and her best friend, that were still enough to force her into a state of bliss.
The pen dropped from Fluttershy’s hand as she braced her palm against the wall, nearly doubling over while her other palm continued to pump her length. Kneeling with her pajama bottoms tented against the mattress and her slender frame heaving from desperate, hungry breath, Fluttershy filled the room with the sound of flesh on flesh and her own tender, sweet whimpers. From time to time she even glanced down at the book to reread the mild wishes she’d already written down, and each time her hand pumped a little faster. Just how short would Celestia and Luna’s skirts be? Would Celestia wear her ponytail on the side, or at the back? Would Twilight hold her hand while she was having sex with a bunch of strange boys? There was simply so much to fill her mind with naughty pleasure!
Naturally, it all proved to be too much for a girl that even under the best of circumstances had what could only be called delicate tolerance to stimuli. The joy of pleasuring herself while engaging in fantasy pushed her wickedly close to the brink, something that she simply didn’t experience all that often. Too many times Fluttershy tried to hide her enormous member away even when it was rock hard in the middle of the night, leading to sleepless nights followed by sticky mornings after midnight ejaculations. But this? This was a case of her taking matters into her own hands, and it felt wonderful.
She squeaked and gasped multiple times before the big moment came, and with one final stroke pumped her unit all the way down to the base. She was left so overwhelmed that her other hand had to reach down and join the first - sharing a space that was easily big enough for them both to hold an entire fistful of cock as the mammoth flailed. Her tip spasmed amidst a series of involuntary muscular reactions and with a shockwave of pleasure the first load of cum finally emerged, shooting so far and so fast that Fluttershy didn’t even realize it reached all the way to the floor at the foot of the bed until she’d notice the stain in the morning. From there, rope after rope of cum launched from her tip against the sheets below her, painting damp ropes against the fabric that were warm to the touch and carrying a faintly earthy, sweet smell. Not even her precious new journal was spared a dose of Fluttershy cum, with a splatter of white plastering the scribbles she’d already written down.
It was nothing short of overwhelming for a girl like her. Intense in a way that Fluttershy simply wasn't programmed to process. By the end of it, her forehead was lined with sweat and she was left wheezing, desperately trying to catch her breath while her member still spasmed within both fiercely clenching hands. There was the brief, glowing aftermath of post-release bliss that filled her…followed, unfortunately, by a rush of timid shame.
“Oh, no no no, such a mess!” Fluttershy whimpered, and tucked herself back into her pajama bottoms - albeit after the third try. She quickly slammed the journal shut with cum trapped between the pages and slung it off to the side, reaching out for a tissue box on the nightstand in the hopes of sopping up the spunk. “Fluttershy, you…you dirty thing! You can’t think naughty stuff like this!”
For the sweetest young woman at Canterlot High School, it was a night filled with one staggering, wild peak followed by a long drudge through the same insecurities she always struggled with. She’d be going to bed that night still feeling dirty about what she’d done, laying there in a sticky mess with her flaccid member still leaking cream against her pajamas. Not even throwing her arms around her biggest, fluffiest stuffed animal and burying her face into his chest helped push aside the discomfort, but at least before too long she fell asleep.
And in the morning, she’d wake up to a whole new world. Stuck within it like cum trapped between pages of a journal.
***
The next morning, Fluttershy did everything in her power to avoid looking at the journal sitting on the floor. She idly kicked it underneath her bed when she got up in the morning, and with most of the shame of last night’s indecency pushed aside, pushed herself up to her feet to get ready for school. The act of showering felt particularly cleansing that morning even if the girthy weight between her legs didn’t want to behave, always forcing itself to stand upright in the morning as if it deserved even more attention than it already got. The chill of the shower - kept purposefully cold - was thankfully enough to keep it at bay long enough for her to tuck it into the tightest panties she could manage. A flowing skirt and a cute white blouse later, and she was on her way to school, feeling…exhausted, but not significantly more so than usual.
Days were difficult for Fluttershy. If she didn’t have her friends to make her feel safe, she simply didn’t know what she’d do.
She’d only made it a few blocks past her house before she was stopped on the sidewalk - called out from across the street by a familiar and enthusiastic voice. Fluttershy’s head lifted up like a bunny popping from its burrow on a fresh spring morning, her eyes lighting up and a smile forming on her lips as she heard a tone that always brought her comfort.
“Fluttershyyyy!” It was Twilight Sparkle again - already crossing the street while she waved, moving with a happy trot to her step. She was dressed every bit as adorably nerdy as ever, complete with a pleated schoolgirl skirt despite the fact she hadn’t attended Crystal Prep in almost a year by now. It just suited her somehow. “Fluttershy, it’s so good to see you! Mind if I walk with you to school?”
“Oh, of course, Twilight!” Fluttershy smiled sweetly, her hands folded together in front of her lap while she waited. “But…you don’t usually come this way in the morning. Is anything wrong?”
“Of course not!” Came the perky response as Twilight closed the distance between them. “I just couldn’t wait to see you again!”
And without any warning - or asking any permission - Twilight Sparkle took Fluttershy by the hand and held it tight. Palm-to-palm, fingers interlocked, immediately swinging back and forth while they moved along the sidewalk. Twilight delivered that touch as naturally as one could be given, like it was simply…assumed that they always held hands. When Fluttershy looked at her with a slightly shocked look, Twilight simply offered her a sweet smile and kept trotting forward, humming adorably while she did so.
Fluttershy’s heart was in her throat and her eyes were as big as saucers, but…she didn’t say anything. She was smart enough not to ruin a good thing when she had it!
She was fortunate enough to keep Twilight’s hand secured in hers the entire trip to class, and loved every single second of it. The tactile contact of Twilight’s palm to hers, the slight brushes of their fingers over each other, even the tiny blushes that were shared between two friends - Fluttershy was completely engrossed in it, to the point that she didn’t even question just how odd it was for Twilight to push the issue to begin with. Daydreams that she might have scribbled into a journal the night before were the furthest things from her mind as they walked, and though Fluttershy didn’t exactly ask, judging by the look on Twilight’s face her purchases from the store last night left her feeling satisfied. At the very least, she wasn’t gushing on and on about gangbangs anymore - her inquisitive and curious nature had been satiated for the time being by the small mountain of fiction she’d purchased from Tartarus’ Archive.
It was probably best, Fluttershy decided, to not ask any questions.
She didn’t give the events of that morning a second thought until the two finally made their way through the front doors of CHS, still hand-in-hand and still with Fluttershy practically floating on a cloud alongside Twilight. When they entered the building and set their gaze on the hallway ahead of them, though, something caught the girl’s eyes and shook her down to her very core.
“Good morning, students!”
“Hello, everyone! Study hard today!”
The usual greetings offered by Principal Celestia and Vice-Principal Luna filled the halls, but it was how the two looked that sent shivers down Fluttershy’s spine. Each one of them was wearing not just a short skirt, but a scandalously short one. Snugly fit around their curvy hips, riding so high that it revealed where their thigh-high stockings gripped along their legs and showed just the faintest hint of panty, the two women stood in the hall waving to their students with bright, friendly smiles.
“Rainbow Dash, take that hat off!” Principal Celestia called out as she pointed towards the crowd, and then to another student further along the hall. “Diamond Tiara, I heard about that perfect score you got on last week’s test, good job!”
Fluttershy - who had been frozen in place ever since she first saw the two women in their short skirts - looked slowly up along Celestia’s body with an ever-increasing feeling of strange, aroused dread. It wasn’t just the skirts, but the principal’s hair, as well. Bouncing from side to side with every bob of her head, flowing beautifully and looking every bit as sexy as Fluttershy had anticipated, the older woman’s hair had been affixed into a tight-fitting ponytail at the base of her neck.
The skirts. The ponytail. The touch of Twilight Sparkle’s hand inside of her own. There were too many coincidences piling up on each other, and Fluttershy’s heart rapidly started to race…just as her member began to twitch within her panties.
Things were changing for the sweetest young woman at CHS, and she was going to change the whole darn school along with her.
End of Chapter One.