I'm probably just going to add on to this one Paste instead of chaptering it out like I did with the Timberwolf Study - there's no storyline here, just little drabbles as I think them up. (Also there's not going to be any incest so don't get your hopes up)
Parts will be marked with Seasons to give an idea of at what point of canon (and character development) the characters are set in, and ages. Pre-Show stuff will be marked Season 0.

Part 1: Season 0 (Fluttershy - Age 12, Gale/Anon - Age 8)
>Your mane is pink, your demeanor is quiet, and your loudest scream registered at 10 decibels, (You) must be Fluttershy!
>Throwing yourself (read: daintily resting upon) your couch, you can't stop the gentle snort that passes for extreme frustration to escape out your snout
>It happened
>Again
>The local Hayburger chain completely ignored that you asked for no pickles on your order
>You're not sure if it's just a Cloudsdale thing or if the chain's pickles are all just uniformly that unpleasant level of sour
>But there they were, three sickly green slices of defiance on top of your hay patty
>Staring up at you, daring you to do something about it
>And like clockwork you just started whining
>You wanted so badly to get out of the booth but you were already trembling from anxiety
>Just before you could feel your vision get hazy with tears a hoof reached over across to rest on your foreleg
>And you looked up to see that smile
>Sympathetic, gentle
>Never judging or pitying
>And in a way the tender nature of it burned
>Your littlest brother, Gale Incognito
>Though lately he was insisting on going by "Anon"
>You had asked him once why
>He said something along the lines of the only nickname he could think of for 'Gale' was 'Gay', and that he was just going to go with something he was already familiar with
>You've never heard anyone call him Anon before he brought it up
>Regardless
>Your babiest of brothers took your tray from you and took it back to the counter
>Explained forthright that you didn't want pickles
>No stuttering, no raising his voice to complain
>Just the easiest clarification in the world
>He made it look so easy!
>And when he got back to your booth he even waited for your corrected food to come back before he even started on his just so you didn't have to just sit there and watch him eat
>But what really rankled you was when the food finally came back
>And the server complimented him on being such a good, doting older brother
>And he just gave that gentle laugh and corrected her
>He didn't mean anything malicious by it
>You aren't so sure about the server though
>Not to be pedantic but Anon is half your height...
>But you swear you saw the server side-eye you pityingly as she went back to the kitchen
>You wish you were as brave as your little baby brother...

>Your coat is green, your mane is black, and you are full of hay tendies
>Surely, you must be Gale "Anon" Incognito
>And man, you're pretty sure Hayburger had to have accidentally ordered like twice as many pickles or something this year from their supplier
>They're always adding them even when they're not asked


Not so confident in this next bit, but that last exchange has been on my mind all day

Part 2: Season 0: (Zephyr Breeze - Age 11, Gale/Anon - Age 8)
>You're lanky as hell, and you have the finest marebun in Cloudsdale - that's right, you gotta be Zephyr Breeze, future malewife to Rainbow Dash
>And right now you're putting the finishing touches on your little bro's style
>Gale - or Anon, as he's going by lately has always been a pretty chill pony
>And that even extends to his mane, it doesn't resist the comb, it follows your hooves directions
>Nothing bothers it, much like the colt it's attached to
>His green eyes are shut, but you can tell by the swivel of his ears that he's listening to your every word
>It's a skill you haven't mastered, personally, you do love talking about yourself
"I gotta admit I was kinda annoyed at you always wanting me to style your mane Anon, but maybe there's something to this - Rainbow Dash could totally use the Zeph Effect on her scraggly mane, y'feel me?"
>Anon opens one of his eyes at that, staring at you with a look that manages to both be totally placid yet look directly into your soul at the same time
>You're not sure where he picked that up, no one in the family can manage that kind of balance
>"What is it you like about her so much anyway, Zephyr?"
>Right to the point, Anon rarely beat around the bush
"Well, y'know..."
>You fidget as you start to put away your combs
"She rules, y'know? She's always winning races, and she doesn't hesitate to speak her mind, and..."
>Anon hums, considering
>"But what about her really strikes you as someone you want to be with? Can you imagine actually sitting at home, having a conversation with her about things you like?"
>The thought of that dries up your throat a bit
>What do you and Rainbow have in common, really?
>You're both Pegasi, you both care for Fluttershy and Gale, you... like apples?
>While you enjoy a private little panic attack, Anon takes a few steps away towards the window
>"You know what I think?"
>A breeze blows through the sculpted hole in the cloud wall of your bedroom, partially ruining your work as it dramatically makes its' way through your little brother's dark mane
>"I think, more than obsessing over trying to make people like you, you should try to live a life that makes you happy before anything else. What do you like to do, big brother?"
>A lightning bolt jolts down your spine as twin flashes of light go off in your bedroom
>Just like that, your little brother's cutie mark appeared
>A bold, black question mark standing amidst a stiff breeze
>"Well, would you look at that."
>A similar mark sits on your frame, though your gale buffets a lazy feather

>Your flank's recently tattoo'd, you got a nice forest green coat, and your half-hour of getting your mane teased has been wasted by you standing too close to an open window - that's gotta be Gale "Anon" Incognito in the pilot's chair
>And you completely forgot that your big brother's cutie mark didn't actually have anything to do with manestyling, despite that being his future profession
>Part of you wonders how he got it originally, but you're plenty happy to have been a part of it this time around
>Hopefully he'll take your words to heart
>God knows you have no idea what you're going to spend your life doing in Horse World
>Mom and Dad would probably appreciate only having to deal with one NEET crashing on the cloud couch

Part 3: Brief Season 7 Interlude ( Fluttershy - Age 22, Gale/Anon - Age 18)
>Another lovely day has graced Ponyville
>And with it a chance for a picnic with some of your best friends
>Today was a lovely little get-together with just Rainbow Dash and Applejack
>Rarity unfortunately had a large order she was nearing the deadline on, Pinkie Pie was foalsitting, and Twilight was running an experiment with Starlight
>Say, with all those names listed, logically that must mean (You) are Fluttershy! Well spotted.
>As you enjoy a rose salad a bit of news you received earlier jolts to the forefront of your mind
"Oh, Rainbow. I received a letter earlier today, I thought you'd like to know that my brother is going to be passing through town soon."
>Rainbow pauses mid-drink to pull a face that has nothing to do with the lemonade she was enjoying
>"Eesh, thanks for the heads up Flutters, I'll skip town for a few days."
>You tittered
>Even if Zephyr had gotten a bit less transfixed on Rainbow enough to approach other mares, he still had a soft-spot for her she wasn't thrilled with
"Oh, no, it's not Zephyr. It's Anon! I haven't seen him in a bit, with all his traveling, you know."
>Rainbow's expression shifts quickly from reluctance to an easy smile
>She and Anon didn't interact much - being several years younger than her and yourself made her not very interested in hanging out with your babiest of brothers
>But they definitely got along better than she did with Zephyr
>"Oh, cool! I'll stick around, then."
>You both share a smile before Applejack clears their throat to enter the conversation
>You and Rainbow both stare over at her, who's hitting you with that raised brow of hers
>"So does that about do it for the Shy family, then?"
>At your puzzled expression, she clarifies
>"Ah mean, is that the rest of yer kin, Fluttershy?"
"Oh! Yes, Anon - Gale Incognito, Anon is just his nickname - is my youngest brother, mother and father were done after three... why do you sound annoyed, Applejack?"
>"Well it's jes'... it's kinda odd t'me how some of us are holding family members in reserve."
"What do you mean?"
>"I mean, Twilight never even talked about her brother until she got that wedding invitation, when Pinkie told her Cutie Mark story she didn't even mention Maud -- and I swear I heard her bring up a previously unmentioned brother awhile back -- and I've known you for years and I never even knew you had a brother, much less two!"
>Come to think of it that did kind of keep happening, didn't it?
"Well... I can't speak for Twilight or Pinkie, but Zephyr and Anon just never really came up in conversation."
>Rainbow Dash piped up at that. "Yeah, They're way different than Fluttershy - they don't really have anything to do with animals and all that."
>Applejack huffed. "Ah'm just sayin', when ah introduced y'all to the family, ah didn't make Big Mac hide in the shed just to blindside y'all with him later!"
>You managed to repress a shudder
>When Applejack introduced you her family, it was in the midst of another Family Reunion
>It took hours to get through all the Crisps and Deliciouses and the Dessert Names
>You sometimes still have nightmares of the fit Angel threw when you got back several hours later and gave him dinner late
>That's in the past though
>If Anon does really swing by Ponyville you do hope the girls like him
>Zephyr certainly made an... impression, but Anon always had a way with strangers that even as social as meeting the girls and becoming an Element forced you to become, you still don't think you could do things as fluidly as he does
>Hopefully he's been treating himself well

Part 4: Season 0 (Gale/Anon - Age 10)
>Your mane is perfectly swirled, your moustache is combed, you must be...
>Yeah, it's okay. Most folks don't know your first name, either
>They just call (You) "Mr. Shy" to try and sound respectful about it
>That's not going to get you down today, though
>It's Career Day!
>Taking your foal to the Weather Factory was always a joy
>Fluttershy was interested in the process but you could tell that the world of weather assembly wasn't for her
>Zephyr, well... he mainly just complained the whole time about how the safety helmet mussed up his mane
>But you got a good feeling about Gale - or Anon
>Your youngest has always been very interested in the Weather process
>Even if he initially had some odd ideas that sounded more at home in the Everfree Forest down on the ground to you
>He always listened to your explainations with such polite attention
>And that was just with you droning on!
>Now you'll have the actual equipment to show him!
>Nothing can ruin this day for you
>A broad smile (for a Shy family member at any rate) blossoms across your face as you greet your son (along with a few more of his classmates who also have family at the Factory) before guiding them all to the initial starting point of the tour
>And it's there that something dedicated to souring the occasion rears its' ugly head
>All three of them, in fact
>You're not sure how you didn't realize, given that their kids are damn near exactly spitting images of their fathers
>But the trio of rude stallions will be joining you on your tour today
>Poi, Kettlebell, and Tally
>Honestly you weren't even sure what they did around the factory
>Beyond give you a hard time whenever they saw you
>And like clockwork, the second Poi brushes his mane out of his eyes and spots you with the kids
>"Well well, about time"
>It took you no less than four minutes to wrangle the kids, but sure
>"Hoops, my boy- Dumb-Bell, Score, always great to see you kids. And is that Gale? Heard good things about you, colt."
>You start to swell with some pride at that, trust your little Anon to get along with nearly everyone
>"Say, how about we ditch Mr. Shy here and just run this tour with just us? We know this place like the back of our hooves, better than him, easy."
>And that pride dies down real quick, because of course they can't say one nice thing without putting somepony else down
>If they know the factory bettter than you it's because they spend their time lollygagging instead of doing their jobs
>Your boy Gale perks up an eyebrow at that, however
>Without more than a second to consider he responds,
>"No thanks. You can split the party if you want, but there's nopony I'd rather learn about the Weather Factory from than my old man. He's the best."
>Pride is back on
>The ruffians are displeased but they're not about to start arguing with a colt
>And being able to have a whole day of one-on-one with your son, showing him all the processes and how the machinery in the Factory works is just the best shift you've had all year
>You love your boy


>You got on the cutest little hard hat, your brain is full of weather facts, and your dad is pretty cool - it must be Gale "Anon" Incognito at the helm
>And that was really fucking weird man
>That stallion propositioning you to go hang out with his cronies and kids
>Right in front of your dad and everything
>You were surprised he didn't pull some candy and wave it around
>Those kids are kind of pricks and you're not at all a fan of how they treat your big sister
>But hopefully they aren't getting molested at home or something
>Either way, the weather in this world is fucking nuts
>You weren't sure if your dad was dumbing down the process or something to make it understandable to your presumably tiny baby horse mind
>But it really does work like he described
>Maybe you'll join him in the factory when you're older