Image imported from ponerpics 
Original Description:
 
Friendship Is Magic: The Next Generation begins thirty years after the birth of Princess Flurry Heart, and the story is… a bit darker and more complicated than My Little Pony: Friendship Is Magic before it. It delves into the backstory around Alicorns, where they came from, why Discord is the only Draconequus, and who is the prisoner in the deepest darkest cell of the cosmic oubliette that is Tartarus…  
(And admittedly, FIM:TNG does take some liberties with the events of MLP:FIM, mostly in regards to Equestria Girls and all episodes after and including The Cutie Re-Mark. That will become more apparent when it comes to the character bios for Sunset Shimmer, Flash Sentry, Starlight Glimmer, and others.)
 
The next character on the chopping block is Whirlwind, age 24, known to his friends as Windy, the son and only child of Rainbow Dash & Fluttershy. He is his mother Rainbow Dash’s protégé as a weatherpony in Ponyville, although he would much rather prefer the paperwork in scheduling the weather rather than be active in the skies despite his broad wings and impressively strong Pegasus magic. Not lost on his moms is the fact that his nickname is reminiscent of his mother Rainbow Dash’s mother Windy Whistles. He doesn’t particularly care; he’d much rather not deal with ponies. Well, most ponies.
 
Windy’s special talent lies in generating circular wind currents in any direction. In his work with Rainbow Dash in the skies, he usually applies this to projecting clouds along particular straight lines to clear the skies. But while he’s on the ground, he uses it more for holding small objects aloft or to offer soft landings to certain Pegasi in Ponyville. He much prefers this to the former.  
Windy’s cutie mark on its own
 
Windy was always a tall and lanky colt, much like his mother Fluttershy was when she herself was a filly. This is not at all to his liking, as he is immensely self-conscious of how tall he is, how much space he takes up. He wishes that he could be invisible and just disappear. Maybe if he realized that his hearing is a bit more sensitive than most ponies then he would realize that he acquired something else from mama Fluttershy…
 
If you thought that Fluttershy was quiet and socially withdrawn, then Windy makes her look like a real social butterfly. Windy spends practically every moment drawing up new weather plans when he’s not being pushed or dragged into active weatherpony duty or friendmaking. Despite all of the adoration from his mothers as he grew up, or perhaps because of it, he does not much like other ponies looking at him or being in the presence of other ponies. A certain family member has been rather proactive about bringing him into those sort of situations, in a sort of cruel kindness to him. It will be more helpful to him later if he can at least weaken his phobia for social settings.
 
As a colt, Windy was constantly the subject of photographs from his family, particularly from Fluttershy of all ponies. The constant physical adoration from so many other ponies may have inadvertently fostered his aversion to too much gregarious activity. And though he despises being dragged into too many social situations, and though he finds Shamrock and the others to be far too rowdy for his tastes, he is still… fond of them? He’s kinda like Nageki from Hatoful Boyfriend in that sense. Even he is surprised by how far he’d go for his friends.  
He refers to Rainbow Dash as Mom, Fluttershy as Mama, and Pinkie as Mum. (more on that last one later)
 
Whirlwind’s coat fill comes from Mrs. Shy’s glasses, and his coat outline comes from Mr. Shy’s irises. His eye color comes from Windy Whistles’s mane colors, and his freckles from Mrs. Shy’s colors. His mane color comes from Bow Hothoof’s coat color tempered slightly by Zephyr Breeze’s coat colors. His cutie mark colors come from Mr. Shy’s mane colors.
 
The rainbow streaks in his mane and tail, huh? Well, Windy and the other children of the Mane Six from Friendship Is Magic bear the mark of the Rainbow Power their mothers earned from the Tree of Harmony. The colors come from the coat colors of each of the Mane Six. Although he balks at the notion, he feels like he is quite capable of magic towards great harmony when he is close to the other three children of the Mane Six, but there is just something missing there. Do they need six to do this…?
 
Rainbow Dash & Fluttershy knew each other practically all their lives, and Fluttershy carried an infatuation for Rainbow for almost as long. It was around the episode Hurricane Fluttershy that Rainbow Dash began to reciprocate those feelings, although it wasn’t until shortly before Flutter Brutter that either of them acted on it. Not surprisingly, it was Rainbow Dash who made the first move, although she can strongly attest to how surprisingly assertive Fluttershy can be as a romantic. It might have something to do with taking some lessons from her alter. Rainbow Dash has moved her cloud home to be located over Fluttershy’s cottage, and she flies down to Fluttershy’s whenever they want to cuddle together, among other activities.  
…yeah, I forgot to mention this, didn’t I? Although Fluttershy & Rainbow Dash are married, as are Pinkie Pie & Rarity, the long-standing on-and-off infatuation that lurked between Rainbow & Pinkie just could not be stymied. An accord was reached between the two couples to allow for Rainbow & Pinkie to have romantic interludes on the side, such as the pair of them seated side-by-side at their many double-dates.
 
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Since my Duchess Skystar was uploaded here, I decided to get on with uploading the rest of the Friendship Is Magic: The Next Generation cast.