Flightschool Reunion

by slep

Rating: mature
Tags: Anon, My Little Pony: Friendship is Magic, Second Person, Fetish, Rainbow Dash, Comedy, Fluttershy, Sex, Twilight Sparkle, Profanity, Slice of Life, Human, Romance
Length: 9402

Unlike so often when Fluttershy shows up knocking on your door, today she's seeming... Skittish? Nervous? Not trying to get in your pants for once? Well. This is new. What's the catch?

Being no stranger to Fluttershy's daily antics & attempts at love, Anon must've suspected today's encounter to be much of the same.

Not so.

To a man of lesser wisdom, this might be cause for celebration: Was the pegasus finally turning a new leaf? Don't be ridiculous, of course not. Shy's always wanting something, and much to Anon's (spoken) regret, she tends to get it one way or another.

Today, it's her favorite human as her Plus One to this year's Cloudsdale Flightschool Reunion.

Time flies, but does Anon?

It's certainly been awhile! Much of that time was spent writing elsewhere I'm sure you'll never guess where, but recently I figured why not turn some of these more worthy works to prose, maybe spiff them up a bit, and give them to a wider audience? So, that's the plan!

Published 2024-01-28 22:30:01 UTC
Last updated 2024-01-28 22:30:01 UTC

Too Cool For School

“This sounds like bullshit.”

Fluttershy squirmed in frustration.

”I-it’s not bullstuff! I’m being serious!”

You might’ve preferred a fetish guess to this bullshit. The premise was so stupid, you would’ve figured it to be an outright trick, if you didn’t already know Fluttershy to be a terrible liar.

”It’d just be for one night, and then we could go back to our normal, hidden-from-the-world, loving relationshi–”

You lean up against the door, glaring– but not because of the much-too overbearing sun on this beautiful Equestrian morning.

“Shush. We don’t have a loving relationship. I tolerate your constant shenanigans so that I don’t go mad from isolation, and you get an outlet for all your sexual deviance so that you don’t end up in a jail cell or mental ward.”

Fluttershy scrunches her snout.

”T-that is… a very misguided view of our bond, Anon.”

She leans from side to side bouncing on her hooves, the usual cocktail of embarrassment and self-loathing shame digging tendrils into her confidence. There came something else with her current disposition, though. Something strange.
Usually Flutters is more comfortable with you than any of your other mutual friends, especially when alone.
It takes some level of self-assurance to openly grope someone, knowing full well the action won’t be appreciated nor reciprocated.

Maybe assurance isn’t the right word…

Regardless, you never liked seeing her so vulnerable.

”I-it’d just be for one night…”

She reiterated herself, voice on the precipice of total defeat.

...

“Will there be drinks?”

Flutters’ head popped up slightly.

”Oh– um… probably?”

And that’s how you got roped into attending Fluttershy’s Flightschool Reunion.

The conversation had shifted from your porch to your living room, as it often did when Fluttershy visited. She always seemed to think this was a sign of progress being made on her part. You always chose not to think any further upon that train of logic. Your single loveseat had become basically one of her possessions that happened to be in your home, Fluttershy seemingly being the only living thing to ever occupy it for your daily prolonged interaction. The cushy sofa adjacent to it, however, was very much your territory; and you lay upon it currently like the glorious resting lion that you are.

Such a stud.

”C-can we discuss something else other than our date for pillowtalk today? I-I mean, you already said yes to coming, so I, um, just think harping on it more might be a bit repetitive…”

You hate how she refers to your neighborly invitations for platonic conversation inside your living room as ‘pillowtalk.’

“No, I need more info than just ‘flightschool reunion.’ First off, I imagine this shit is gonna be in Cloudsdale? How do you expect me to get up there exactly?”

Fluttershy sipped her tea. Well, technically it was yours, but she was always using your things anyways, and you hate tea.
You only buy it out of routine at this point. For Fluttershy.

”That won’t be an issue: Twilight has a spell for cloudwalking, you see. We’d just need to take Cherryberry’s balloon up to the clouds really.”

She coughed, blowing harshly on the steaming teacup.

”B-bah! … Or maybe I could carry you up myself.”

You scoff, lazily tossing up one of your throw-pillows.

“Please. You’re like, a third of my weight. We’ll take the balloon.”

Fluttershy makes an angry face. A cute, smushable, angry-little-kitten face. You’d never tell her that though.

”I-I’ll have you know I can throw around Harry when he wants a massage, mister!” She lowers her eyelids and does some brief display with her wings ” and I can mare-handle a big grump like yourself too: Firm enough to make you obey, but gentle enough to make you feel safe– you’d be moaning like a colt, and shamefully begging for more, your pride in total shambles! But a mare like me, oh no no, momma wouldn’t let you hurt like that for long–”

“Tut-tut! You’re getting sidetracked, and I don’t want you leaking on the couch again. That smell doesn’t fuckin’ fade I swear.”

The damned mare smiles.

”I’m glad you’re always able to smell me even when I’m not here, sweetie~”

You toss the pillow up again.

“Shtappit, you’re trying to derail the conversation and it’s not gonna work.”

Fluttershy pouts.

“Now, when is this reunion happening? I might need Rarity to make some adjustments on my fancier shit– haven’t worn them in ages and I’m not about to look like a clown if I can help it.”

”Oh– um, tonight.”

Fuckin’–

“... And you waited until today to ask me out– invite me?”

Finding her tea to be much more interesting than eye contact now, Fluttershy pauses.

”... W-well, I was just going to not attend at first, but… Oooh! You know how Rainbowdash can get when she wants to go and do something, and some of her fondest fillyhood memories come from when we were in Flightschool together! She won’t let me just not go!”

You sigh. Sometimes, you really wish Fluttershy would redirect some of the hopeless-confidence she has toward you at some of the other facets of her life. It’s mind-boggling to think that the same mare who will willingly show up to your door with a bike pump in one hoof and a butt plug in the other and be serious also can’t say no to her friend’s bullshit. With a grunt, you kick yourself up from the couch and move to your bedroom, Fluttershy following behind.

“I always got ‘peaked-in-highschool’ vibes from Rainbow, but clearly that isn’t the case. Why the fuck does she care about the reunion if she’s already in the Wonderbolts? Surely they have cooler shit going on, no?”

You find some of your more presentable clothes and move to try them on. In the past, you wouldn’t dream of doing such things like taking off your shirt in front of Fluttershy, but time has taught you that she’s (more or less) not gonna try anything too crazy. Though, her oogling probably doesn’t bode well for your bed, considering that’s where she is sitting now.

”Ohhh~... I– um, ahem. L-like I said, Rainbow just has a soft spot in her heart for things like this. She wants to remember those days when she was a no-name flyer, just another young pegasus eager to prove herself. It gives her the motivation to continue on her path, a-and I want to be there for my friend.”
”... Even if I…”

She sputters off, mumbling under her breath.

You button up the white dress shirt, peering back at Flutters with a glance. “Even if you what? Are terrified of crowds? Flutters, you don’t need to torture yourself just to support your friend. It’s not like she can’t go on her own. You and I are just gonna be wall flowers latched onto the punch table anyway. Rainbow ain’t gonna hang out with us.”

Fluttershy flops over onto her back, weakly rolling about in your covers. Gettin’ her fuckin’ Fluttershy scent all over your shit like usual.

”I know… b-but it’s just so hard to say no to her when she gets like this! Plus, she was always at my side when we were younger, always defending me from…” She picks up your pillow and stuffs it over top her face, muffling herself.

You roll your eyes.

“Defending you from the breeze up there I’m sure. Look, if we’re gonna go, then there isn’t any point in moping about it. The choice’s been made. We’ll go, get drunk for free, you pretend to get sick, and we’ll bounce early yeah? Everyone wins.”

She’s at your side in a flash, hugging you from behind. ”Oh Anon, that’s a wonderful idea! Y-you know I’m not much of a drinker– Rainbow won’t question it!”

“Oof! Yeah yeah… I’m not overdressing for this am I? I don’t know how reunions work.” You pry off her hooves and try to remember how a tie works. Fluttershy takes notice of your struggling.

”Here hubby, let me help.”

Before you can chastise her for calling you that, Flutters is already at your neck. Her skill takes you aback slightly: In seconds your tie is presentable and tidy. It looks a bit odd though. You give it a few curious tugs, nearly choking yourself in the process.

“Ack! Flutters, you sure this is a proper knot?”

”Oh of course! I have plenty of practice with that one. It’s a sort-of modified Arbor knot.”

You shoot her an accusing look.

“... Why?”

She smiles genuinely.

”Well, you’re my muse. You inspire me to learn all sorts of new...”

You tune her out as you finish readying yourself. For better or worse, at least you know now that Shy is more than proficient in tying the sort of knots that tighten the more you pull on them. Concerning.

”... And, oh, you know– I could show you some of the other knots I’ve been studying too, i-if you’re interested of course. I think the Handcuff knot in particular is especially interesting.”

You shake your head, making your way to the door.

“Sounds like asking for trouble, so I’ll take a raincheck on that. Come on now, Rainbow is only ever punctual for the shit she wants to do, and we both know how pissed she’ll be if we’re late. Still gotta swing by Twilight’s for that cloudspell too…”

Fluttershy watches you mumble off and walk out, watching with half-lidded eyes.

”Mmh, some other time, then.”

”So, you finally decided to take up Fluttershy on a date, huh?”

Besides still occasionally pestering you for sweet human knowledge, another of Twilight’s favorite pastimes when it comes to you is teasing.

She only does it out of genuine concern though, and will thankfully not push the issue when it becomes obviously grating on you. It’s more than can be said for most other ponies in town.

“I think of it more as helping out a friend.”

Fluttershy puts up a wing, whispering in Twilight’s ear “i-it’s a date.”

A book is levitated down from it’s shelf and Twilight clops her hooves together. ”Well I’m happy that you two are finally getting out of the house either way, regardless of the ‘why.’ Plus, I have an excuse to pour over Endless Horizon’s ‘Pegasi Studies’ again! She made much more than the cloudwalking spell, you know. I won’t bore you with the details now, but if you ever feel the desire to, oh, I don’t know, bottle up some storm clouds in your house for when you need some ‘electric decor,’ you know who to ask!” Her words topping off with a gigglesnort.

“No thanks. Honestly, I’m only subjecting myself to this cloudspell out of necessity. Magic's too fucky for me to be trusting of some bottled lightning.”

Twilight lightly scoffs, flipping through the book. ”So be it~ but it wouldn’t be so scary to you if you actually tried learning about it, yaknow.” Finding the page, her horn sparks to life, and the process is over as quickly as it began. You hear a low ‘poof!’ yet you feel no different.

”See? Nothing ‘fucky’ about it, Anon. All it takes is some competency in what you’re doing.”

Fluttershy winces at the repeated use of that word.

Twilight teleports to your side, lifting one of your legs at the calf, inspecting something that you can’t see. Apparently happy with her observation, she poofs back to her desk in the middle of the library. ”Now, you’re looking very spiffy mister– but I expect you need to get ready for the date too, Fluttershy?”

You roll your eyes, much to Twilight’s enjoyment.

”Oh, I wasn’t exactly planning on wearing anything…”

She says that, but the gears are obviously turning in the yellow mare’s head now.

”... B-but maybe I should, huh? I mean, it is a reunion after all…”

She looks you up and down.

”And Anon is looking so handsome too… Oooh, you’re right Twilight!”

With that, Fluttershy's head is butting up against your rear, slowly pushing you to the door.

”C’mon Anon, we need to get to the cottage! I need you to decide which dress I should wear!”

Twilight calls out “knock ‘em dead, filly!” as the two of you depart, giggling to herself before turning back to her book.

You're thankful that this detour didn’t lead you to Rarity’s at least. God knows the two of you would never get out of there in time for the reunion.

”H-how’s this one? Do you think my rump looks particularly, um… smashing?”

Fluttershy is steadily making her way through her entire wardrobe, displaying herself to you each time. ’Displaying’ in this case often being quite literal, particularly when the dress has a high-cut skirt. In turn, you sit with your legs crossed atop the pegasi's poofy comforter, a loose fist struggling to support your chin as you try to avoid direct eye contact with Shy's rump.

“Flutters, I’ve told you every dress so far has looked great. I can’t tell if this is just an excuse to look pretty and show off in front of me, or an attempt at stalling.” At that, Fluttershy turns her head back, still presenting her rear to you.

”P-pretty?”

You pinch the bridge of your nose. “I’m leaning more towards ‘stalling’ as time goes on.”

“C’mon girl, seriously. Rainbow is probably trying to track us down right now. If you still really don’t want to go, I’ll just tell her so and she can be pissed with me instead–”

Flutters stomps a hoof.

”N-no! It’s not like that!”

That takes you aback.

”I-I want to go out with you and have a nice, m-maybe even romantic night! I want to dress nice and show you around Cloudsdale! I want to show Rainbow that I’m not scared anymore!”

... Now probably isn’t the best time for you to correct some of the wording she used there: Angry outbursts are a pretty alien thing to witness from Flutters. Instead, you keep your voice calm, but curious.

“What are you scared of? Was highschoo– er… Flightschool a bad experience?”

Fluttershy whimpers, her tail returning to its usual spot clamped down low between her legs. Seems you hit a nerve.
Not a few moments later, the mare can't help but gallop up into your lap without a care for the dress.

”Oh Anon, it was awful! I-I wasn’t a strong flyer, and that alone was enough to get bullied. Worse than that though, I-I was lanky and tall for my age– pair that with me being such a doormat... a-and they walked all over me!”

Her words give you no time to remark your displeasure at the breach in personal space, but that's hardly even your own focus right now. A few tears slip onto your pants, and it dawns on you just how much you hate what you’re seeing. You’ve seen Fluttershy from afar when she wasn’t around you once or twice, and you’d been told some things by her friends, but it was never very easy to actually believe. ’Fluttershy was a mare too afraid to speak out against being overcharged dramatically for a single cherry?’ Yeah right. This is the same mare who routinely broke into your house to sniff your laundry basket, and had the confidence to say “hello” after being caught?

Their words had to have been dramatic hyperbole at the very least, you’d always thought. But seeing her in this state…

... You’d much rather wake up to her trying to sneak into your bed.

Some strange feeling tears at you inside, and while you offer her a few reassuring mane pets– your mind is elsewhere, and you quickly pick her up and move for the door.

“We’re finding Rainbow.”

Fluttershy settles into the bridal carry quite easily.

”B-but,”

“Hush. We’re finding Rainbow, and we’re gonna have a good night out.”

That shuts her up quick. She only offers a quite “Eep!” in response, a blush warming her cheeks.

Even if just for a night, you’d play into it.

You just didn’t want to see her like that ever again.

A bolt of rainbow streaks rapidly towards you, and a voice follows with it.

”Took you long enough! I’ve been looking everywhere for- Anon?”

Apparently she’d honed in on the yellow-and-pink without really noticing she was being carried.

“Hiya.”

Any real anger Rainbow might’ve been feeling is forgotten fast. ”You- you got Anon to say yes to tonight, Fluttershy?”

She nods meekly, looking up at you with a big forced smile. Rainbow pumps a hoof in the air.

”Heha! Nice goin’ girl! I knew you had him in the bag!”

Just ignore it, Anon.

Rainbow’s glee quickly gives way to concern. ”But uh, yaknow he can’t get up to Cloudsdale on his own, right? Uh,” she sizes you up “I’m not too sure we’d be able to carry him all the way up there. N-no offense!”

You feign a scoff. “Hmph. But yeah, I wouldn’t be comfortable getting carried up higher than Canterlot Mountain by hooves alone anyway. Flutters and I are going by hot air balloon. You’re welcome to tag along too if you’d like.”

Rainbow blinks, and her excitement returns in a flash. ”Oh yeah! That’s a way better idea! It’ll be like that time the rest of the girls came up to watch me at the Young Flyer’s Competition! I take it you’ve already stopped by Twilight’s and got zapped with the cloudwalking spell?”

You rock on your heels and give a smile. “So she said. Personally not looking forward to that first step onto the clouds, but we’ll cross that bridge when we get there.”

Rainbow slaps a hoof onto your shoulder. ”It’ll be fine! Celestia knows Twilight wouldn’t have left you leave the library if she didn’t think the spell had worked. And as for joining you two… I think I’ll fly up there on my own, maybe bust some stray clouds that might be in your guy’s way, yaknow?”

She flashes Fluttershy a wink.

”Yep, you two just get nice and acquainted with one another on the ride up. The reunion should be in full swing by the time you reach Cloudsdale anyhow. Just don’t take too long, or there won’t be any punch left!”

Rainbow slams a hoof against her chest, looking cocky. ”Well, don’t let me keep ya waitin’, the sun is already gettin’ ready to set. See you there!”

With that, she’s gone– a few clouds already punched to nothing in her ascent.

Cherry Berry’s blimp is within sight, so you continue on. You take note of the town starting to close up for the night around you. Ponies in the marketplace meander to lock up their wares, eyes lingering just in case of a last minute sale. Perfect for you and Flutters, considering Cherry is still sitting atop some crates by her balloon, idly reading a newspaper with candles melted atop the wooden boxes to hold them steady. You call out to her from the distance, her grumpy persona briefly cut through by the prospect of some late bits.

All the while, you take note of Fluttershy.

Surely carrying a grown mare like this, especially one whom the whole town gossiped about in terms of a potential relationship, was going to spark another wave of rumors about the two of you. More important than that though: She hadn’t said one word to Rainbowdash– or anything at all since leaving the cottage.

You squeeze her with your hand– immediately regretting it as she moans.

Maybe you should’ve just said something.

“Gah! H-hey, you haven’t said anything since we left. C’mon now, if we’re gonna have a good night, you gotta get in the mood.”

Fluttershy smiles, her nerves leaving her for just a moment.

”K-keep squeezing my cutiemark, big boy, and I’ll be in the mood for sure~”

You deadpan.

“Ha-ha.”

”Shouldn’t be more than twenty minutes up to Cloudsdale. Get lovey-dovey or whatever, I don’t care, I’m not here.” Cherry sends another plume of fire up into the balloon, before reclining back with her paper again.

Flutters gives you a hopeful grin, putting a hoof atop your hand as you look out over the steadily growing Equestrian landscape.

”H-her words, not mine, Anon.”

You roll your eyes, holding your tongue even when she presses her head against your shoulder. If feeding into her desires will calm her nerves, then it’s worth it. The sun lazily slips below the horizon, casting out it’s final hours of calm warmth, allowing the slow chill of night to take hold.

This isn’t to imply the remaining light is weak, though. Brilliant hues, ranging wide from orange, to red, into deep indigo all streak the sky and make for a truly beautiful display. You’d heard some ponies make small talk about how the twilight each day had been restored to a past beauty not seen since before Luna’s banishment, long before any of them were alive.
Something about how Luna’s return and reconciliation with her sister is reflected in the sky, when their respective realms touch, and one allows control over the other. You found yourself in this world a few years after her return, so while you couldn’t make comparison, certainly no one could argue that the setting of the sun wasn’t truly a sight to behold.
The colors just poured out from that yellow sun, and eventually came to make contact with the beginnings of Luna’s night.
They entwined themselves with such literal force that one might mistake it for something akin to a physical object, like a breathing oil-canvas painting moving across the firmament of the heavens.

As if the light was so strong -so thick- that you might just be able to touch it, were you close enough.

”Anon?”

Fluttershy rubs her head against your arm.

“Yeah?”

”... Have you ever been in an air-balloon before?”

You keep staring across the expanse, noting to yourself how vibrant the verdant pastures of Sweet Apple Acres remain, even as the light begins to pull from the land. “No. I’ve never been this high up while still being out in the open, more or less.”

”What do you mean?”

You focus on the treeline of the Everfree Forest, and catch a realization that, even from up here, you cannot see an endpoint to it. Just a sea of treetops, steadily growing much larger the closer you look to the horizon, stretching far beyond.

“... I’ll explain it some other time. It’s really not important.”

Fluttershy huffs, a grumpy little scrunch accentuating her snout.

”I-I’ll hold you to it, mister.”

A brief lull of quiet overtakes you both.

”... I… I really like it when we just… can talk.”

You cast her a questioning look.

“We can always do that, Shy.”

Fluttershy takes a moment to collect her thoughts, pressing up closer against you.

”I-I know, but… but sometimes we just get so caught up in our routines, o-or we’re focused on the girl’s and their antics, or…”

”... I-I just like when you and I are each other’s focus.”

You can’t help the smile that breaks out across your face.

Fluttershy’s usual antics and the annoyance you usually equate them with seem far away from your mind now. It honestly feels a bit odd, though, you’re not quite catching onto that at the moment. Just as you’ve forgotten about Fluttershy’s hoof that was once atop your hand, and how it has seamlessly wiggled itself to be wrapped up in your palm.

“Well, I guess it’s pretty easy to start going on auto-pilot after a while around here.”

The balloon is getting into higher altitudes now, and a wild breeze sends a chill through the basket. It catches you off guard, and apparently it does the same for Flutters. She shivers, and quickly worms her way against your chest, your arm falling in line and wrapping around her as the two of you lean against the side of the basket overlooking the world. Clever girl…

Cherry puffs another burst of fire into the balloon.

Cloudsdale isn’t so far off now.

”Anon?”

”Be honest.”

Uh oh.

Fluttershy keeps her gaze toward Cloudsdale, the cloud city seeming to still be well-awake with lights and movement even as the sun sets.

”Do you think you could ever actually fall for me?”

The question freezes you in place. Suddenly, it seems like even the wind has stopped it’s gentle whirling to listen for your response. In the calm, you realize that Cherry Berry had long since stopped turning pages in her newspaper too. Something told you she had found another way to pass the time.

You chance a glance down at Fluttershy, and see only the pink of her mane, flowing gently with the ascent of the balloon through the air. Was she keeping herself braced for the response?

... Would telling her no actually give her closure?

Would telling her no bring everything to an end?

The antics, the headaches…

The daily visits?

The refreshingly genuine talks on the couch?

The light in her eyes and the smile she’d give when she first saw you each morning?

...

“... Do you…”

Fluttershy chances a glance up at you, but only for a glimpse of a second, snapping her head back down to the nearing Cloudsdale.

“Do you remember when you first started trying to… trying to ‘court’ me?”

Fluttershy stays quiet, silently goading you to continue.

“Those first few days, I tried being nice. I thought it was some crush out of curiosity, or exotic factor, and that it’d pass when you saw I wasn’t biting.”

Unconsciously, you pull her a bit closer to you.

“Those first few weeks, though… I started getting annoyed. I thought ‘how couldn’t she see that I wasn’t interested? How wasn’t I making myself clear enough?”

“Those first few months, then… I realized just the kind of mare I was dealing with. It was one I didn’t know existed, both from where I come from and here in Equestria.”

“You have this drive, Shy. When I started putting my foot down with you, you met me with equal force. You don’t quit, even with odds that seem entirely against your favor.”

Something grips you, and you find your chin resting gently atop Shy's head, partially obscuring your face in her mane.

... The fuck? What are you doing!?

You catch yourself and pull back.

“... N-now, ah, think about where we are now. Nearly a year since I came to this world, and any animosity I might’ve held against you is gone. Truth be told, I’m not quite sure when it happened, but… I mean, five months ago? Inviting you into my house after your daily guess? Especially if it was one that was way off the mark, or just outright absurd? I never would’ve done that.”

Regardless of what the body language might speak, your chin sinks back down atop Shy all the same. Something about it feels right, despite some parts of your mind firing obscenities at you.

“... What I’m getting at is: I’m perceptive enough to see that you’ve broken down my walls quite a bit, and I’m not stubborn enough to be unable to admit it. So…”

“Yes. I think I could fall for you. I’d be a fool to try and convince myself otherwise.”

Quiet reigns.

So much so that you could swear to hear that tear drop that splashes against your hand.

Oh, look at that, it’s found its way around Fluttershy’s hoof again.

That’s funny.

You’re about to break out into emergency damage control, questioning the problem, when Flutters spins and grips you in a great bear hug. Taken aback, you return the hug with much less force, and wonder if you made the right choice.

”T-thank you.”

...

Yeah.

The basket pushes through the ground layer of Cloudsdale not long after that. This seems to be a relatively distant “field” you’d all landed in, a mile or two out from the actual “city limits.” You peer out over the basket’s edge with an admitted fair bit of trepidation.

... It certainly looked compact enough, but…

”So, you two want me to be here, what, five or so hours from now to pick you back up?”

You look to Fluttershy. “Ball’s in your court. When do you think we should bow out?”

The mare in question idly fiddles with her dress.

”U-umm… M-maybe three hours? N-no, four! Two!”

You give Cherry an apologetic grin.

“Three hours from now will be fine. Thanks, Cherry.”

The earthpony gives you a once-over, concern breaking through her gruff exterior. ”And you’re SURE you won’t plummet through the cloud floor the second you step out of the basket?”

You turn to the clouds, then to Flutters.

She gives you an encouraging nod.

”I-I won’t let you fall, sweetheart.”

Gah.

“Only one way to find out.”

Hoisting a leg over the side, you touch your foot to the clouds, toes first. It gives way a bit, but the deeper you press, the more it resists, until you’re pressing your full weight in that leg against the cloud.

...

You flip yourself over the basket, planting two feet firmly in the clouds. Fluttershy instinctively latches onto your shoulders, flapping her wings fiercely under her dress.

“E-easy girl! It’s good. Hoo shit…” You stomp your feet a few times. “Haha! Well ain’t that something, huh?”

Cherry Berry eyes you.

”... Very nice. See you in three hours.”

Cherry turns from your pair, lights up some candles in the basket, and opens up her paper once more. Whether truly genuine or knowing she can get away with it here, or a mix of both– Flutters capitalizes on the opportunity and hugs your barrel again.

”Oooh, sweetie! You were so brave! Welcome to Cloudsdale!”

Even you can’t help but swell with a fair bit of pride, standing atop the sky. By now, the sun had nearly fully given the night the main floor, and distant specs of light spotted the ground across the Equestrian landscape. From up here at the cloud edge, you could trace the outline of Ponyville, and follow the railroad up to a surprisingly illuminated Canterlot.

It's magnificent.

You grandstand for a few seconds more, it dawning on you that you are the first, and very well possibly the only human who will ever physically stand atop the clouds.

Feels gud.

“Ahh… Suck my dick, world.”

Fluttershy giggles.

”Hehe, w-what?”

... Maybe not the best company to say such a thing aloud.

You walk alongside Flutters through the streets of Cloudsdale. The whole city is awake tonight, it seems. Pegasi move to and fro, mingling out in the streets, increasing in density the closer you approach to the Junior Speedster’s Flightschool. Apparently, pegasi love any excuse to party. Fluttershy’s nerves had cooled quite a bit since you’d both left the cottage, but now it seemed like they were making a vengeful return.

She presses against your hip.

The chat the two of you had been having during the walk into the city had died out the second she saw the first crowd.
It didn’t help either that, for many pegasi here, this was their first time seeing you. Thankfully, some Ponyvillian pegasi could be seen scattered amongst the crowds, and they’d give the both of you happy smiles and waves. If it helped Flutters any, she wasn’t showing it.

... There’s this twinge in the back of your neck, you feel it more and more with each passing moment of seeing her like this.
This wasn’t the mare you knew.

Why was it making you so upset?

You’d like to chalk it up to simply being bothered by a friend’s obvious discomfort, but you knew that was wrong– and you don’t like where this train of thought is going. So, in an attempt at taking both of your minds off of their respective fears, you try small talk.

“You grew up here, huh?”

Fluttershy peels her eyes from the faceless crowds, her big teal eyes thankful for an escape.

”Y-yes. I don’t like it very much, though.”

“Too loud?”

Wings ruffle underneath their confines beside you.

”T-that, and… mmh…”

Fluttershy nearly stops in place, trying to find the right words. You lean up against the wall of some street corner and give her time, using the opportunity to scan the locale a bit more thoroughly.

”... T-there’s just so many of them.”

Surprisingly tall cloud formations bloom and curve overhead, oddly stagnant. Lights are obscured within them, and pillars line some of the indents in their wispy design. You realize that these great mountains of cumulus are, in fact, inhabited.

”It’s not entirely that they’re ponies… It’s just…”

These “buildings” all revolve around one huge structure, a thing seemingly combining both cloud and some form of machinery you can’t quite compare to anything you’d ever seen prior.

The Cloudsdale Weather Factory.

”... They aren’t my ponies. My type of ponies, that is.”

”Maybe it’s still an irrational fear, but I don’t think I fear strangers too much, not anymore at least. Everypony I hear mention it shrugs off their ‘diagnoses’ of me as agoraphobia, or fear of large crowds, or whatever. Simple answer, right? ‘Quick fix, Fluttershy.’ As I’ve come to try and face these things, though, the answer I’ve found instead is… a-a sort of fear of being misunderstood, o-or even an incapability to be understood entirely by ponies I meet.”

She laughs, and it carries with it a twinge of bitterness.

”Looking back on it now, and how scared I was to come here tonight, I think that confirms it, in my head at least. I-I thought when I was young ‘I’m not being loud, or rude, so there isn’t really reason to catch any scorn.’ I was wrong, obviously, but that was my mindset at the time.”

Her words sober you.

”Opening up to them didn’t work, and seemingly, neither did keeping out of their way, until it eventually just... did. Maybe they found somepony else to ridicule, I don’t know. I’ve always been of a quieter temperament, but that really sealed the deal for me: Don’t get in ponies’ way, and you won’t have to deal with their outbursts.”

You slide down the wall, sitting at her side, listening.

”I guess I internalized that quite a bit before I met Twilight and the girls, and maybe even still do. It can be real easy to shrug off some of their antics sometimes, and I think that makes me come off as apathetic, or maybe even cruel…”

”– but the girls were the closest I thought I’d ever get to being able to really, truly express myself. A-and, well, that was fine for me, I’d thought.”

”Until I met you.”

Oh, you’re staring at her now.

”You’re an unbiased party, both by your character, and your… inherent removal from typical pony culture, if that makes any sense. You weren’t raised up here. I can come to you everyday, be…” she sighs refreshingly “b-be free, and you encourage it, whether you wanted to in the past or not… You’re not like them.”

Fluttershy gets awfully close to your face.

”... A-and I like that.”

Oh man, her breath is hot.

Especially up here, so high up and with this constant breeze–

Fluttershy pouts, pressing her head against your shoulder.

”P-plus, there’s no animals up here. Little birdies can’t land on clouds, so you only ever see them in flight. No time to talk…” She gives a quiet “hmph!”

...

There wasn’t much left between the two of you and the Junior Speedster’s Flightschool now. Though the festival stretched far out throughout the multi-layered city, it’s ground zero was focused here. Pegasi spilled out from the main doors, enjoying drinks and small flight displays amongst their many conjoining cliques. In between great stacks of lenticular clouds, pegasi cut jet streams through the city sky.

In the nearby distance, the Weather Factory pumped out strangely harmonic cracks of thunder, not dissimilar to the chiming of great bells. It was a marvel you found yourself increasingly ill-equipped to take in all at once.

You had to keep yourself grounded, though.

Fluttershy didn’t shake nearly so much anymore, seemingly finding some catharsis after she keyed you in on her introspection, but this was all obviously becoming sensory overload for her. You place a supportive hand where her wing would be.

“C’mon now. Let’s just find Rainbow and find a nice corner to bird watch in, yeah?”

Fluttershy gives you a curious glance.

”B-bird watch?”

You smile at her confusion and press through the crowd, Fluttershy muttering apologies all the way.

”Hey! You made it!”

Rainbowdash, admittedly, looked pretty stunning in her dress.

”Took ya long enough! A stallion like you always knows how to find his way to the punch, ey Anon?” She playfully punches your shoulder before pouring herself another cup. ”Isn’t Cloudsdale awesome? The whole city always comes out for the reunion, and now:”

Rainbow grabs Fluttershy by her shoulders, shaking her about.

”It’s. Finally. Our. Year! YEAH!”

As quickly as she came, she’s gone again; and with apparent little care for how her dress might fare as she takes off flying through the open amphitheater. Fluttershy gives you a mischievous look, thankfully able to find some momentary humor among all the overbearing ruckus around you.

She weakly raises her cup upward and out.

”Y-yay our year?”

You can’t help but smile, meeting her cheers.

“I’ll drink to that.”

She wastes no time in downing her drink, pouring herself another from the tapped kegs. You weren’t about to bother trying to think about how they, and most of the other shit on this densely-packed cumulonimbus, didn’t slip through the floor.
This certainly isn’t what you had in mind when you thought about a ‘flightschool reunion.’

It was obvious who viewed this celebration as more of a gala, and who viewed it as an excuse to get rowdy. Multiple bands played across many elevated stages interspersed about the arena; some playing refined classical, and others not-so-covertly instigating a riot. Fancy dresses, the kind you’d see commonplace in Canterlot, danced alongside hooves barely able to hold their multiple drinks as the crowds rocked against one another, ponies switching sides with every movement.

One thing was shared among them all though: A desire to be jovial.

Honestly, it really was nice to see, and part of you wanted nothing more than to get trashed and make a fool of yourself out there with them. Fluttershy kept you sane though, even if she didn’t know it. You’d navigated to one of the many scattered open bars not ten minutes ago, and Fluttershy was already on her fourth drink. It was hard for you to guess the alcohol percentage, what with the excess sweetness and your current lack of understanding when it came to pony alcohol in general, but it certainly had a bite to it.

And Fluttershy was a much smaller creature than you.

You figure this was her attempt to avoid a nervous breakdown, or she’d took that ‘get sick and leave early’ alibi literally. You watch her chug her recent pour, and move to get another.

“That liquor ain’t going anywhere girl, you can slow it down a tiny bit. I’m already dreading the catch-up game I’m going to have to play here.”

... Admittedly, it was pretty hot watching her take her drinks like a champ.

You’d never tell her that, though.

Fluttershy giggles, lashing her tail at you as she pours her next cup. ”Mmmh~, I like the sound of you being… b-booozed up, Nonny~”

Uh oh.

”Think you can catch up, with momma~?”

...

That annoying part of your mind is already telling you that it’s a bad idea. But she just insulted your pride. You down your drink and reach for another.

“Easy there girl. You might’ve went to flightschool, but I went to college.”

Just then, a voice from the crowd cuts through the clamor.

It pulls Fluttershy right out of her sexy-taunting mood.

”Hey! Is that, uh, Shutterfly?”

A stallion bonks his friend upside the head, spilling both of their drinks.

”No you idiot! Her name is Fluttershy!”

”Ohhhh!”

The three stallions briefly dip out of the crowd and wave.

”Heyyyy *hic* Fluttershy! Glad to see ya could make it!”

You keep an intense eye on her and them, watching both parties for any sign of issue.

... And it never comes.

Fluttershy just meekly waves at them once she could break from her stun, and they sink back into the crowd, roaring for more punch.

You ended up rolling one of the kegs away from it’s perch, near one of the more quiet corners of the reunion.
Fluttershy had been pretty shaken up from the encounter. She sits at your side, up a fair distance into some stands overlooking the reunion.

Pain in the ass to hoist a keg up rows of stadium seating, by the way.

The distant lights only illuminate her face so much- you can’t quite tell her current mood. Something tells you it’s complicated though. You pour the two of you each another drink, setting hers at her rump. Her shock had dissolved into confusion not too long ago, and she was still very obviously working through her thoughts.

“... People change, you know.”

"They might do you a great disservice, and not even realize it. Especially when they’re young.”

“What might’ve hurt you so badly that you never forgot, it slipped their minds by the next week.”

“Life can be cruel, but it usually doesn’t hold a lasting vendetta against you without reason.”

You sip your drink, and hope you’re gonna be able to shake her out of her stupor. You’re not sure what to say next, you’re so bad with this shit and–

”I think that proves it, then. W-what I was talking about earlier, that is.”

”Ponies who can… be that way, regardless of their justification…”

”I just don’t like that.”

”I don’t want to be around ponies who can be so mean, and simultaneously mean nothing by it. Words just thrown out, not with the intention of actual malice, but with no intention behind them at all.”

Fluttershy takes a long sip of her drink after her words.

“There’s nothing wrong with that, girl.”

You in turn sip yours.

“But that alone shouldn’t sour you to distrust anyone else who could come into your life, because not everyone you meet is gonna be that way.”

Fluttershy sighs, taking another gulp. To your surprise, a smile has found its way onto her face. She flicks her tail against you again, leaning into you.

”... But it hasn’t soured me.”

“Oh?”

”I’m still here giving you a chance every day, aren’t I?”

You sip your drink, leaning back into her.

“Psh. You wanting me to fuck you doesn’t equate to your avoidance in making new friends.”

”Anon!”

Fluttershy bats at your shoulder with a hoof.

”I don’t want to you-... w-well, ok, I do, but that’s not what I meant. I mean… you’ve said some pretty mean stuff to me over the months.”

Damn it… The feeling of guilt! You’re surprised how hard it hits.

”But, I’ve, um, definitely earned some of those, um h-harsher remarks at times.”

“Uh huh. Like that time when-”

Fluttershy tips your cup back into your lips, silencing you.

”S-specifics aren’t important right now.”

”W-what is important is that, through it all, you never stopped… listening to me. H-heck, even, tolerating me. I-I’d come to accept that the ‘real’ me as just intolerable, something not to be shown, or else I’d just be ridiculed again- but you showed me that wasn’t the case. Even if it wasn’t your intent... A-and now look at us!”

”You said it yourself earlier: Doing the things we do together now? You never would have done it -I could only dream of it- Neither of us ever thought it’d happen.”

... Admittedly, you had been legitimately hanging out with Fluttershy more and more.

Hell, after saying no to her daily fetish guess, you basically just stepped aside and let her in to chat these days.

Yeah, actually– the fuck is up with that?

The fuck is up with you?

When did that start happening!?

And why was it so enjoyable!?

This is fucking Fluttershy we’re talking about here!

Where’d all that grumpy asshole energy from this morning go?

Hearing her build upon your thoughts from earlier alongside the personal insight she gave you back on the street really drives the point home for you: You might’ve let your guard down a bit more than the ‘yeah, I could totally see me falling for you’ comment implied.

And where does that leave you now?

Well, with a buzzed Fluttershy nuzzling your side, apparently.

”M-my point is… your words never stung like theirs did.”

Fluttershy giggles.

”T-there was no bite to your bark.”

Hmph.

”I’d show you me, you’d show me you, and then we’d go inside and talk about life, or each other, o-or just whatever.”
Fluttershy leans you back, taking care not to spill your drink, before flopping her upper body across your chest; forehooves tucked together and staring up at you with a heartwarming smile.

”I-I’ve never really had that with anypony else. Besides you.”

”That’s why I like you so much.”

...

“... Was that ‘I show you me, you show me you’ talk a double entendre?”

Fluttershy’s smile turns devilish, and she moves her rump in between your legs, fully laying atop you.

”We could make it one.”

You blow some of her mane into her face.

“Or, you could get off of me and we could get back to drinking. It’s a pretty good view up here-” you gesture with your drink out across the wide expanse before you “-not that you’re looking.”

Flutters lets the loose strands obscure her face, probably thinking it gives her some extra sex appeal.

She bites her lip. ”I think my view is already pretty good.”

You huff.

“At least let me lean up a bit– these stands might be made of fuckin' cloud, but it certainly doesn’t feel like it.”

Feeling that the current closeness between your privates is victory enough at the moment, Fluttershy does relent, turning her rump in your lap and allowing you proper seating again. You’d not admit it to her, but the warmth she provided was very nice. It wasn’t going through your head at the time, but dress clothes are usually quite thin, and it only gets colder the higher you go up in Cloudsdale.

Damn pegasi probably don’t even notice it.

This particular pegasus does notice your shiver, though.

”Aww, poor baby…”

Fluttershy wiggles her entire body up against you, taking special consideration with her rear. Her wings ruffle and slowly begin to rise at the feeling of your member rising to attention.

“Hey now, I’m not fuckin’ cold. Quit it or you can’t sit in my lap.”

Gotta reign her in early, or else she’ll never calm down. Pegasi seemed to be easily the most ‘instinctual’ of the three pony races, and Fluttershy was no exception. You’d never seen her drunk prior to this either. Earlier you thought that maybe it’d mellow her out some; get her mind away from her more lewd mannerisms.

You’re starting to see more and more that it’s not the case.

She gently presses the back of her head up into your chest, giggling.

”S-sorry, it’s been awhile since I’ve actually got to feel it. So easy to lose myself sometimes…”

She mumbles off, sipping her alcohol with two hooves on her cup now.

”Mmmh… but you’re really not cold, Anon?”

It’s gonna be much harder to lie to Fluttershy from here on out, after hearing everything she’s told you tonight.

“... I am, but between the alcohol and you, it’s not bad.”

“I just can’t have you squirming on my dick while we’re out in public.”

Fluttershy coos, tail swishing the best it can.

”It’s fine while we’re in private, then?”

You down the rest of your drink.

The back-and-forth between the two of you continues for a little while longer, before Rainbow makes an appearance again.

”Hey you two– oh! Um…”

Rainbow zips over to Fluttershy, trying to whisper in her ear. ”Shit, am I cock-blocking right now? Should I go?”

She’s not very covert.

Fluttershy giggles, whispering back. ”Oh, don’t worry Rainbow. I already got him~”

Rainbow’s eyes light up, all pretense gone now.

She openly pumps a hoof into the air and cheers. ”Aww yeah! I knew you had it in ya girl!”

You roll your eyes as you sip your drink. “We didn’t actually do anything, for the record.”

Rainbow blows a raspberry.

”Ho’ yeah Anon, I’m sure. I bet you’re still inside Flutters and it’s just covered by her dress.” Rainbow winks at Flutters, giggling.

... This is a bit of a compromising pose.

Briefly, you contemplate shoving her off of you.

Briefly.

Maybe Anon from a few months ago would’ve, but… You’ll let Rainbow think what she wants. Speaking of, she takes a seat beside you and Flutters, pouring herself another cup.

”Way to nab a keg, that’s good thinkin’!”

The three of you stare out across the crowd, the party still going strong.

”So Flutters, did you see any old friends? I had a great time catching up with some of the fillies who stayed in Cloudsdale. Heh, you remember Fair Winds?”

Fluttershy nuzzles against you. ”Oh… not really. But it’s okay.”

”Well, I’m glad you decided to come anyway. You too Anon! Never thought I’d see you up here of all places, let alone with Flutters.”

Rainbow punches your shoulder, but gets up in your ear after. In a rare moment of genuine tenderness, she whispers in your ear.

”I’m glad I did though.”

Seems Rainbow's a better wingmare than you'd thought. Damn mares– they're all plotting against you!

Not knowing what to say, you raise your cup out in front of you.

“... Well, cheers then. To pleasant surprises.”

The two mares raise their cups to yours.

Rainbow looks out over the crowd, her voice falling in line to something a bit more measured.

”... You know, if you two wanna get out of here, I don’t mind. I’m just glad you showed up at all. Wouldn’t have been a true reunion without the whole class coming, right?”

You nudge Flutters’ side and feel her head nod against you.

“Yeah, our ride back home is probably gonna be waiting on us soon.”

Rainbow’s ears fold back ever so slightly, her smile persisting with a touch of something forced.

“... But we still got some time to try and polish off this keg until then, right?”

You catch Rainbowdash’s eyes sparkling as that true smile returns in full.

”Aw yeah! Now that’s more like it!”

A rogue breeze makes you hug Fluttershy with a bit more ‘umph’ than before, and she hums in delight. Something tells you she won’t mind sticking around just a bit longer.

Cherry Berry idly bats around some of the cloudfloor with her hoof as she notices your stumbling approach.

”About time, you two. I’ve been waitin’ here for nearly ten minutes.”

Fluttershy mumbles out an apology. After you noticed her trot devolve increasingly into wobbles, you made an executive decision to carry her. Not much point in trying to justify yourself anymore tonight: Your head was swimming and you’d already betrayed your usual self with how much you’ve clung to Flutters.

Tonight was just a special occasion between two friends in a complicated, evolving relationship.

That’s all.

“Gah, that’s no trouble Cherry…”

You hoist you and your cargo over the edge into the basket, finding some relief fading in at the return of sturdy ground beneath you.

”Well, I wasn’t about to leave you to slip through the city when that spell wore off, so I guess I’m just glad you’re still sober enough to walk.”

You smile dumbly, finding a nice corner to sit in.

“Nothin’ sober about me at the moment, Cher.”

Cherry’s smile betrays her gruff tone as the balloon begins its descent back to earth.

”Don’t call me that.”

Fluttershy worms her way out of your grip, laying upright against you. ”Y-you just stay put down there, mister~ mmh…”

“Not goin’ anywhere…”

Maybe you all overdid it a bit.

You certainly didn’t kill the keg, but Goddamn if the three of you didn’t try.

Rainbow said her goodbyes after you and Flutters decided to call it quits, disappearing back into the crowd. It was nice to hang out, you decide. You’re happy you did this.

Soon enough, Fluttershy is quietly snoozing atop your chest. You contemplate joining her in sleep until the balloon touches back down, but this surrounding quiet and cool breeze is too good to not enjoy in the moment. Cherry eyes you from across the basket.

”Yaknow, all of Ponyville’s got bets on whether or not you’re gonna get with her.”

You twirl some strands of Fluttershy’s mane.

“Oh? And what’s your bet placed on?”

Cherry laughs.

”Hometeam.”

”Us mares gotta stick together, you know. Besides, after what I’ve seen tonight, I’m more sure of it than ever.”

You feel Fluttershy’s hot breath against your chin.

”Why are you still puttin’ up a fight anyway? I heard some rumors that she used to be pretty, um, forward… but the two of you seem inseparable these days. Why not just make it official?”

“Cause it’s not official.”

You stare up at the sky, partially obscured by the balloon overhead.

“... I got my reasons.”

Cherry just shrugs, idly piloting the balloon back to Ponyville. You can still hear the distant festivities from Cloudsdale even now.

You wonder if it really is just a matter of time.

Fluttershy hiccups in her sleep, a faint blush still written across her cheeks. You’re gonna have to carry her home.
... Or just let her crash on your couch. Though you know she’ll end up crawling into bed with you by morning, ready to try breaking down your walls and winning your heart again like always.

Maybe it’s the alcohol, but you can’t help smiling.

... Fuckin’ Fluttershy.

Author's Note

Hello again! I gotta say– I thought the process of converting greentext into prose would be way easier than this.

But! Really wasn't much trouble all the same, so I'm just whining. I never stopped writing, and I would like to actually give Marianna's Silence another go sooner rather than later, but I've since fallen into the trap of starting up stories for a bunch of ideas– and grinding my process to a halt as I lose focus on which one to target next.

Part of my plan with bringing some of my greentext stories over here is to hopefully reinvigorate me back into writing more consistently (or at least, have enough of a single story to actually qualify as a product). There's a few more stories I'd like to bring over here, so I'll be working on that most diligently for the next week or two. I'm sure I'll have a more clearer goal of where I want to take things next from there, so we'll see!

As for Flightschool Reunion here: I wrote the original for the /fr/ general nearly three years ago ~~real big fan of Fluttershy here, if it wasn't obvious,~~ and this one's still gotta be my favorite personal writing to date. I practically grew up with that general (certainly not a good thing lol but what can you do), but it was and still is my main inspiration even if I was never very good at writing for it. This might seem considerably more 'softcore' compared to other stories from the same 'genre,' but that's just how I like it. I don't think I handle this sort of slice of life low-stakes writing all that well, but it's the sort of setup I love to read personally.

Anyway, I'll cut my rambling here at least. Thanks so much for reading! As always, critique and criticism adored.