For Pinkie Pie, life is pretty good—she's the pinkest, perkiest, most partiest pony in all of Ponyville!

Okay, so things could be better. Her friends aren't having the happiest time right now, especially her beloved Dashie, who she hasn't seen in a while. Upon reuniting, an innocent conversation quickly turns into a sour argument, prompting Pinkie to ask herself all sorts of questions. Who's in the wrong? What should she do? Why are all the bad things happening right now?

And, most importantly, can she patch things up with Dashie before it's too late?

A side story to The Life of Times of a Winning Pony, chapters 18 to 21.

Losing your virginity is a big milestone for anypony. Especially when you finally hook up with the pony of your dreams in the process. There was just one problem for Blossomforth: when she woke up the next morning, the other side of the bed was empty. Cloud Kicker wasn't there.

Sure, Blossomforth understands why Cloud Kicker wasn't there for her. Cloud's been going through a rough time lately, and maybe their hookup wasn't timed very well. However, knowing that doesn't make Cloud's absence hurt less, nor does it make Blossomforth any less lonely. Perhaps this is a sign that she needs to put some serious thought into where her relationship with Cloud is going, before things get too far out of hoof.

Part of the Winningverse. Takes place concurrently with Chapter 18 of The Life and Times of a Winning Pony.

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

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

Raindrops clocks in and out every day for her job--ONE job, with set-in-stone expectations. Unfortunately for her, one of those expectations involves dealing with her coworkers. That's a trick in and of itself, and Cloud Kicker is far from an average coworker. With the worst storm in her career blowing in from the Everfree Forest, she has to face down unending rain, hail, lightning, and worst of all: Cloud Kicker's nymphomania. The question now is what will give first: her body, or her sanity?

A story in the Winning Ponyverse.

Rarity is alone on Hearts and Hooves Day, and she's not happy about it. A friendly afternoon in the park with Applejack promises to turn their friendship to something more – or at least it would, if either of them would simply talk to the other about it.

Between her awkward sort-of romance with Applejack, her desire to help Fluttershy find a special somepony of her very own, family, friends, and the general day-to-day chaos that is life in Ponyville, this fashionista's got her hooves full.

Side story to The Life and Times of a Winning Pony and the rest of the Winningverse. My thanks to Chengar Qordath and Comma-Kazie for their support and pre-reading assistance.

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.

So I'm awesome. Yeah, if you know me, you know that. I have Pinkie Pie for a fillyfriend, pulled off Tornado Day by the skin of my teeth, and got complimented by Spitfire from the Wonderbolts. Also, did I mention I saved her life once? Thing is, though, I don't think awesome is genetic. I mean, I love my parents and all, but ... at a distance. So naturally, they came by to visit.

A sequel to The Incredibly Dense Mind of Rainbow Dash, The Incredibly Troubled Mind of Rainbow Dash, and Chapters 1-12 of The Life and Times of a Winning Pony.

After a misunderstanding leads to a vicious fight at Flight Camp that leaves them both in the hospital, Cloud Kicker wanted absolutely nothing to do with Rainbow Dash. However, Rainbow refuses to let a single incident destroy their friendship, and has been writing Cloud Kicker letters ever since that horrible day. For more than two years Cloud Kicker has been throwing the letter into the trash unopened, but what will happen when she finally reads one? Can their friendship possibly be salvaged?

Side-story to "The Life and Times of a Winning Pony"

Blossomforth wants to comfort her friend Cloud Kicker in the aftermath of Derpy's death. However, helping Cloud Kicker move on from death of a friend and lover is a difficult thing, and before she can help her friend Blossomforth must first confront her own feelings for Cloud Kicker and the reason she never got along with Derpy Hooves. Not to mention dealing with all the regrets that inevitably come from lost opportunities.

Follows from the events of Saying Goodbye and connected to Comma Kazie's "From The Mouths of Fillies" and "Changes." References some of the events of "The Life and Times of a Winning Pony" but the two stories are not in continuity with each other.