This story is a sequel to The Life and Times of a Winning Pony

In the time since she became Derpy's daughter, Sparkler Doo has come to trust and love her mother more than words can express. Three years of tender, loving care and patience brought Sparkler out of her shell, showing a scared little filly that she was loved—and safe.

All it took was one fateful lapse in judgement to bring that crashing down. Now, with her faith in her mother shaken to its core, Sparkler has to take a step back and try to pick up the pieces.

Assuming she wants to.

This story takes place in tandem with the events of Chapter 19 of The Life and Times of a Winning Pony

Blossomforth is fresh out of college and ready to take on the world. Sure, moving to Ponyville to get a job on the weather team is going to be a bit of an adjustment, but it's nothing she can't handle. Besides, Rainbow Dash seems like a fine boss. Everything is looking good for our favorite watermelon-maned pegasus.

Then she meets a pony named Cloud Kicker.

Part of the Winningverse

Cloud Kicker might just have the wildest life of any pony in Equestria. Marvel at the insanity that is her life, and laugh at the suffering of her poor beleaguered best friend, Blossomforth. And maybe, just maybe, there's more to her than just the lovable sex maniac everypony thinks she is.

This is a semi-sequel to "The Incredibly Dense Mind of Rainbow Dash." Not really a proper sequel, since it's focused on Cloud Kicker and Blossomforth instead of Rainbow and Pinkie, but it's in the same continuity. So I guess that makes it a follow-up-side-quel story. Or something. You don't need to have read "The Incredibly Dense Mind of Rainbow Dash" to read or enjoy this, but you ought to read it anyway, just because.

TvTropes Page

The central story of the Winningverse.

We got a tag for Cloud Kicker, but Blossomforth still deserves one too.

Cloud Kicker might just have the wildest life of any pony in Equestria. That may just be why Princess Luna wants Twilight Sparkle to study the insanity that is Cloud Kicker's life for a sociology report. Unfortunately for Twilight Sparkle, she is going to have to survive the circle of jealous friends, paramours, enemies, crazy co-workers and disappointed family members that surround this crazy pony. Will Twilight Sparkle be able to complete this assignment before it spins out of control, or will she be reduced to a neurotic mess?

A Winningverse Story.

Things couldn't possibly get any worse for Rainbow Dash. Her job is falling apart, she's convinced that she's made her friends hate her, and even her dream of some day joining the Wonderbolts is in peril. While things are looking pretty bleak for Ponyville's coolest pegasus, her best friend and kinda-sorta fillyfriend Pinkie Pie is determined to whatever it takes to help her, and she's not going to quit until she can put a smile back on Rainbow Dash's face.

This is a side-story of "The Life and Times of a Winning Pony" which occurs after the events of Chapter Ten of that story.

Cheerilee loves teaching. Despite all the trials and tribulations it presents, it's worth it in the end when her students learn something new. Not even a letter from the Ministry of Education reminding her about the impending teacher evaluations can sway her. But tack on her new relationship, the constant 'help' of the Cutie Mark Crusaders, and some strange behavior from Dinky and Sparkler, and her life is about to become a lot more complicated.

This story is set in parallel with The Life and Times of a Winning Pony and The Study of a Winning Pony with the approval of Chengar Qordath, Comma-Kazie and Ponibius.

Cover art used with permission, source is here

Twilight Sparkle. A name known to everypony in all of Equestria. She's saved Equestria multiple times now, and with her and her friends being the Elements of Harmony, as well as being Princess Celestia's "Most Faithful Student", she enjoys a great life.
But what was before that? Follow her on her journey through foalhood, and her times as Celestia's Student.

This is my first fic, so constructive criticism is appreciated very much.
A huge thank you to WhatTheMoo and Knight Of Cerebus for proofreading this fic.
And a huge thank you to TwinTailsInc for allowing me to use his artwork