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.
This fanfic provides examples of
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.
Belligerent Sexual Tension: Applejack and Rarity, to the point that arguing and foreplay are virtually indistinguishable.
Beware the Nice Ones: Blossomforth is usually a pretty nice pony, but she can very fearsome when properly riled.
Black Sheep: Cloud Kicker feels like one to her family for dropping out military school and not carrying on the family tradition.
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.
Cat Fight: Blossomforth and 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."
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.
Chivalrous Pervert: Cloud Kicker sees herself as such. Actual results... vary
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.
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.
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 wasn’t likely to include either of those factors. Not that crazy rumors have ever been deterred by a few inconvenient facts.'
Rainbow Dash with her Amazingly Embarrassing Parents, and her method of conception gives a shred of credibility to the rumors stated above.
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.
Hidden Depths: Cloud Kicker insists that she has them.
Hot Mom: Derpy Hooves, at least according to Cloud Kicker.
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.
Idiosyncratic Episode Naming: Every chapter title follows the format of: "The Pony (Adapted Charlie Sheen Quote)"
I'm Cold... So Cold...: Dash goes into shock from blood loss after almost getting disemboweled with a vicious kick
Innocent Innuendo: Cloud Kicker, at a party, chats up Derpy. The conversation turns to 'eating muffins'. After being reminded of innuendo, Blossomforth figures Derpy was talking about actual baked goods. Naturally ... they spend several minutes putting together muffins. Then they clean up the leftover batter, up to when Derpy accidentally spills some. All of it lands on very lickable parts of herself, and nowhere else.
Love Triangle: Blossomforth is Cloud Kicker's best friend hoping for a Relationship Upgrade, Derpy is currently in a very loose relationship with Cloud Kicker.
Military Academy: Cloud Kicker went to one for four years, but dropped out shortly before graduation.
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.
Back in flight school, Rainbow Dash and Cloud Kicker got into a fight over a serious misunderstanding. Between the Unstoppable Rage of one and Combat Pragmatist tendencies of the other, they managed to cause each other life-threatening injuries.
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."
Oblivious to Love: Played incredibly straight by Rainbow Dash in the story's prequel. Averted by Cloud Kicker; she's well aware of Blossom's interest, but has been deliberately ignoring it in the hopes that Blossom would get over her crush.
RecursiveFan Art: The page image for one. The author actually posts any Fan Art of his works on his blog.
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.
Sex for Solace: Cloud Kicker and Blossomforth finally do the deed in the wake of Cloud's mother being found dead at the hands of a Changeling Infiltrator.
Sex Is Good: Cloud Kicker's general philosophy and how she explains her lifestyle choices.
Sexy Discretion Shot: Heavily utilized to keep the fic from entering mature territory.
Straight Man: Blossomforth often takes this role to Cloud Kicker.
Tap on the Head: Discussed - at one point Cloud Kicker finds herself in a situation where she needs to disable a pony without causing injuries and she finds her options very limited.
The First Cut Is the Deepest: Chapter 9 kinda gives us an explaintion why Cloud Kicker doesn't want to have a romantic relationship.
The Tease: Teasing Blossomforth is practically Cloud Kicker's hobby.
Theme Naming: Cloud Kicker's family engages in this.
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, I’m sure my queen will overlook such minor affairs when I present her with the corpse of one of the Element Bearers.
Vitriolic Best Buds: Cloud Kicker spends a lot of time poking fun at Blossomforth, who eventually starts giving back as good as she gets. Despite that they're still best friends.
Well Done Daughter Girl: Cloud Kicker seems torn between striving for her family's approval and insisting she doesn't care about it.
Wham Episode: Chapter 6 has Cloud Kicker pull Blossom's crush on her out into the open during a fight that seems to have torn their friendship to pieces.
And then we have Chapter 9...
At the end of Chapter 15: Cloud Kicker's mother has apparently betrayed Equestria, and she intends to kill her.
The next chapter then hits us with a double-whammy: the traitor Nimbus Gust is actually a Changeling Infiltrator... who has already killed the real Nimbus Gust and dumped her body in a cave.
What the Hay Best Friend? / "The Reason You Suck" Speech: In Chapter 6 Blossomforth starts out by calling Cloud Kicker out on her tendency to be a bit self-centered and inconsiderate, but but before long it morphs into something nastier, and then things get worse.
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.
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.
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.
And when she does, she freaks out at the idea ofdating her mom until Twilight and Pinkie calm her down.
Mythology Gag: Rainbow Dash's parents are the G3 Rainbow Dash and Surprise, a G1 pony that was the inspiration for Pinkie Pie.
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:
Children Are Innocent: Dinky, oh so much, in "From the Mouth of Fillies" and its sequel "Changes".
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.
(also available at FF.Net
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