The Life and Times of a Winning Pony (also available at FF.Net) is a My Little Pony: Friendship Is Magic fanfic by Chengar Qordath. The story tracks the life and times of Cloud Kicker, a fun-loving Ethical Slut with a tendency to have lots of random sexual encounters and end up in wild misadventures. The story weaves reasonably well into actual episode screentime, and also is unique in pointing out some of the cronyism inherent in Equestrian societySide-stories and recursive fanfiction for this fic have been written by numerous authors, and these are collectively referred to as the "Winning Verse". They range from the comic tale of Pinkie Pie's attempts to make a romantically dense Rainbow Dash realize her affections, to the more serious story of Derpy Hooves running off to Ponyville after being kicked out from her family for an unplanned pregnancy. This fanon universe also splits off into a second alternate universe, usually referred to as the Dead-Derpy-Verse, where Derpy dies, leaving behind two daughters and Rainbow Dash as the god-mother. The side stories are collected here. The stories in the alternate universe are collected here.
Action Girl: Cloud Kicker has some moments of this, thanks to her military training.
Asexuality: Rainbow Dash. According to Cloud Kicker, Rainbow's relationship with Pinkie is the first romance she's ever had.
In chapter 9, it is revealed that there may be a physical reason for Dash's lack of sexual activity.
To be fair, it's not clear whether it has to do with the physical damage, or an aquired fear of anyone messing around down there.
It's made blatantly clear through Dash's narration in The Incredibly [Adjective] [Noun] of Rainbow Dash stories that she's a complete dunce when it comes to anything related to physical intimacy. Early in the latter, she's reasonably sure Cloud Kicker's reference to "pie" is an innuendo, but can't be arsed to make sure, or even care.
Badly Battered Babysitter: Cloud Kicker winds up becoming one after somehow ending up in charge of Dinky, Alula, and the Cutie Mark Crusaders.
Breakout Character: The author wrote a previous fan fiction, The Incredibly Dense Mind of Rainbow Dash. Word of God: 'Somehow, Cloud Kicker and Blossomforth really managed to steal the show in terms of what I enjoyed writing. To heck with RainbowPie, Cloud Kicker/Blossomforth is my new OTP. In fact, I will e-mail cupcakes to the first person who writes a good Cloud Kicker/Blossomforth story. Pinkie Promise.' Note that RainbowPie was the actual primary ship being built in the fic.
Broken Pedestal: Seeing Derpy physically lash out in anger is enough to severely shake Sparkler's faith in her.
Cat Fight: Blossomforth and Assertive!Fluttershy get into a particularly nasty one.
The fight between Rainbow Dash and Cloud Kicker is technically a Cat Fight but you would not tell from seeing it. It ends with a concussion, broken face bones, a broken leg, broken ribs, a dislocated wing, an eye injury, a collapsed lung and is finally decided by a Groin Attack so vicious it causes serious internal injury and near fatal bleeding
Catch Phrase: Cloud Kicker almost always refers to sex as "banging."
OOC Is Serious Business: When she doesn't. Non-dramatic, by the way; "And then we made love" is the sweetest sentence in the entire fic.
Cerebus Retcon: Rainbow Dash' crashing is usually treated as a Running Gag. It's not so amusing anymore when it's revealed to be happening due to an eye injury, that could possibly blind her.
The Clan: The Kicker family is big and almost all of them are in the military.
Conflict Ball: Everyone gets hit with shades of this in chapter 16, from Rainbow Dash growing incredibly violent and Blossomforth uncharacteristically trying to pick a fight with Derpy, with bug insults coming from both sides. However, it appears something else is at work here.
In later chapters, there's a growing tendency for characters to get into arguments, along with the trend for those involved to end on bad terms.
Cool Big Sis: Cloud Kicker tries to be one to her little sister, Alula.
Disproportionate Retribution: Pretty much all of the cast who know about it agree that Cloudkicker was being incredibly stupid when she slept with Blossomforth behind Derpy's back. However, they also agree that Derpy punching Cloudkicker in the face in a fit of thoroughly uncharacteristic rage was going way too far.
Ethical Slut: Cloud Kicker, to the point of actually having a list of rules.
Everyone Is Gay: All of the Mane 6 are gay, and mostly every other girl is too. In fact, only one couple is heterosexual. note It's Big Macintosh/Cheerilee, and they aren't even together yet in their story.
Extreme Omnisexual: Not only does Cloud Kicker have an interest in both genders, but also claims to have been involved with just about every intelligent species in the show.
Fantastic Arousal: Wingboners (a Pegasus unfurling their wings when aroused) are present.
Foregone Conclusion: Near the end of "The Pony Who Doesn't Fit Into Their Little Box", Chrysalis gives Cloud Kicker the following offer: giving up Shadow's armor in exchange for having her and her loved ones leave Canterlot unharmed. She then leaves to go gloat about her victory of taking over Canterlot. You are invited to guess what happens next.
Gilligan Cut: Sparkler makes a Pinkie Promise that she has no romatic interest in Cloud's cousin Star Kicker. "Less than two hours later, I caught Star and Sparkler making out behind the equipment building. So much for Pinkie Promises."
Has Two Mommies: An occasional rumour in-universe surrounding Derpy's natural daughter, and a certain mare who was hanging around her at the time. While feasible in-story, it's only available 'when some very high-level and hard-to-get (not to mention expensive) unicorn magic was involved, or when the Magic of Love gets tossed into the mix. A one-night stand between two pegasi wasnít likely to include either of those factors. Not that crazy rumors have ever been deterred by a few inconvenient facts.'
Heroic BSOD / Heroic Safe Mode: In the wake of discovering her mother's mangled corpse and killing the Changeling responsible, Cloud spends the entirety of Chapter 17 in a near-catatonic, emotionless state.
Hypocritical Humor: Cloud Kicker tells Derpy off because she made Fluttershy cry, when she overheard Derpy implying that she was going to steal Cloud Kicker from her. Once she kicks Derpy out, Cloud sleeps with Fluttershy and discusses running away to get married afterwards.
I Banged Your Mom: Cloud Kicker uses this on Sparkler to force a stalemate in parental sex squick while talking with Sparkler ... adopted daughter of Derpy.
Military Academy: Cloud Kicker went to one for four years, but dropped out shortly before graduation. Specifically, She ran off in the middle of the graduation ceremony.
My God, What Have I Done?: In chapter 9, Fluttershy went to Rainbow Dash for sex advice, which resulted in RD and Cloud kicker nearly killing each other. Fluttershy breaks down crying and muttering this.
Military Brat: Both of Cloud Kicker's parents are in the Equestrian Royal Guard, as is most of her extended family.
Never My Fault: Rainbow Dash's huge ego makes it impossible to apologize to Cloud Kicker for firing her in a fit of anger. She does want Cloud Kicker to come back, but she refuses to accept the job after picking apart how Rainbow just wants to make herself not look bad in front of everypony else.
Noodle Incident: Something happened between Cloud Kicker and Fluttershy that destroyed their childhood friendship.
No longer hidden, as of Chapter 9. Fluttershy and Cloud Kicker became a couple in flight school. Then Fluttershy created a misunderstanding that started a fight between Rainbow Dash and Cloud Kicker that left both with life-threatening injuries. Then Fluttershy panicked and broke up with Cloud Kicker as she was being flown to the hospital.
Also, the Lunar Rebellion. All that's really been established about it is that it happened 900 years ago, it started in Cloudsdale, and Cloud Kicker's family was one of the few pegasus families to remain loyal to Celestia.
Though the sidestory The Lunar Rebellion is beginning to shed some light on said rebellion.
"This rope can hold a weight of a stallion the size of Big Macintosh, suspended from the ceiling."
Percussive Maintenance : Ever since her and CK's punch-up back in flight camp, Rainbow Dash's eye rolls back in her head every so often, and giving herself a smack is the only thing that will reset it. She nearly knocks herself insensate in chapter 10. it seems to be taking it's toll...
Reconstruction: To an extent, Cloud Kicker is a reconstruction of the "Charlie" from Two and a Half Men, character type. She's actually relatively nice, and clearly has rules she follows, and isn't exploiting people.
Changeling!Nimbus Gust: I suppose I should thank you, though. I admit, some of my plans did not develop entirely to my satisfaction, and the fact that you found my papers earlier than planned was unfortunate. However, Iím sure my queen will overlook such minor affairs when I present her with the corpse of one of the Element Bearers.
Your Cheating Heart: When they start to get serious, Derpy starts to fear this about Cloud Kicker. She did admit to loving both of them, and she had spent most of her time with either of them instead of Derpy, after all. When Derpy expresses her concern to Cloud about her lingering feelings, Fluttershy overhears and breaks down crying, thinking herself the reason for Derpy's stress. Cloud Kicker angrily kicks Derpy out and then sleeps with Fluttershy, making the whole thing a Self-Fulfilling Prophecy.
Tropes used by the "Winningverse" side stories include:
Brainwash Residue: Cheerilee is worried her feelings for Big Macintosh might be this.
Early-Installment Weirdness: The Incredibly Dense Mind of Rainbow Dash was originally written as a one-shot story without any indication of starting an all-out Shared Universe, and thus contradicts some of the later established backstories. It was afterwards rewritten to fit the current Winningverse canon, but the original version was also kept for comparison.
Exact Words: In the Lunar Rebellion, Shadow Kicker promised a Griffon Archduke that she wouldn't castrate or flay him if he revealed where the remaining pony captives were, not that she wouldn't have him hung.
Grumpy Bear: In her story, Raindrops is a typical example.
Het is Ew: Apparently. There are hardly any heterosexual couples, Applejack actively guards Big Macintosh from courting mares, and since magic can help with same-sex conception, some family trees are filled entirely with females.
Hero of Another Story: Since most of the side stories take place simultaneously and sometimes intersect, the POV characters are all this to each other.
Like Parent, Like Fillyfriend: Rainbow Dash's mother Surprise and her fillyfriend Pinkie Pie are... remarkably similar. She doesn't seem to notice.
Sink or Swim Mentor: In chapter 7 of The Lunar Rebellion, Celestia purposefully refrains from interfering in a fight between her subordinates, hoping they will learn to work it out themselves. It backfires disastrously, the argument escalating nearly to the point of violence rather than simmering down and continuing to erode their confidence in her leadership.
Unperson: Damnatio memoriae, a posthumous punishment used among pegasus clans during the era of The Lunar Rebellion. A pegasus who has particularly shamed his or her clan is completely expunged from their clan's records following their death.
Unusual Euphemism: Rarity refers to Cloud Kicker's fondness for banging as "socializing".
Tropes used by the "Dead Derpy Verse" side stories include:
Driven to Suicide: Sparkler stops eating and drinking after Derpy's funeral and throws away her food to cover it up. While it's not clear if it was an intentional suicide attempt or just a side-effect of depression, the end result is that she nearly dies before Rainbow Dash figures out what's going on.
Please Wake Up: When Dinky finds her mother's body in Changes, she thinks Derpy is just sleeping and cuddles up with her. Then she realizes she won't wake up and this trope happens.
The Plot Reaper: While not TECHNICALLY an example...this DOES solve the Cloud Kicker/Blossomforth/Derpy love triangle.
Promotion to Parent: In "Changes" Rainbow Dash finds herself no longer acting as the world's greatest baby-sitter, but a mother, and isn't quite prepared to cope with the promotion and the death of one of closest friends.