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Fanfic: The Life And Times Of A Winning Pony

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 society

Side-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.
  • Affectionate Nickname: Cloud Kicker calls Fluttershy "Eepysqueak" as that was what she thought her name was when they first started talking.
    • In the present, but before they make up, it's become a bit of a Berserk Button for Fluttershy (as much of one as it can get with Fluttershy) as it reminds her of the Flight Camp incident, which she still blames herself for.
  • 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 acquired 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 doesn't 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.
  • Blood from the Mouth: Played seriously when Cloud Kicker gets her ribs broken.
  • 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.
  • Bully Hunter: Cloud Kicker does not like bullies.
  • Can't Hold Her Liquor: Blossomforth is apparently a lightweight.
  • Cat Fight: Blossomforth and Assertive!Fluttershy get into a particularly nasty one.
    • The fight between Rainbow Dash and Cloud Kicker from their flight camp days is a brutal aversion. The sum total of the resulting injuries included a concussion, broken face bones, a broken leg, broken ribs, a dislocated wing, an eye injury, a collapsed lung, and a Groin Attack so vicious that it ended the fight and caused 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.
  • Cerebus Syndrome: While Life and Times started as a bit naughty romantic comedy, it gets more and more drama-driven by time, with some serious character backstories, a complicated Love Triangle, and the closer its story arc gets to The Canterlot Wedding.
  • Cluster F-Bomb: Dropped by Rainbow Dash at the beginning of chapter 16, immediately followed by a Shout-Out to the page quote for this trope.
  • Combat Pragmatist: Cloud Kicker has been through military school. She uses a pegasi version of krav maga.
  • Character Development: Blossomforth has slowly been developing a thicker skin in response to Cloud Kicker's teasing.
  • Childhood Friends: Cloud Kicker, Derpy Hooves, Rainbow Dash, and Fluttershy are all old friends from Flight School.
  • Childhood Friend Romance: Cloud Kicker and Derpy Hooves.
  • Children Are Innocent: Dinky is so cute and innocent that her appearances border on Tastes Like Diabetes.
  • 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.
  • Deadpan Snarker: Blossomforth, when she's not being embarrassed by Cloud Kicker.
  • Dented Iron: It seems a life of constant crashing head-first into things is finally taking its toll on Rainbow Dash. She has a breakdown in chapter 10.
  • Did They or Didn't They?: It's left unclear if Cloud Kicker actually banged Princess Luna or if it was just a drunken sex dream.
  • 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 
  • Evil Matriarch: Nimbus Gust comes across this way.
  • Expy: Cloud Kicker takes several cues from Charlie Sheen, including using tweaked versions of some of his more infamous quotes as chapter titles.
  • 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."
  • Godzilla Threshold: Anything that justifies taking Shadow's armor out of the vault.
  • Good Bad Girl: Cloud Kicker.
  • Groin Attack: When it is delivered by a horse, it matters not if you are male or female
    • Played for Drama, since Cloud's desperation kick on Rainbow Dash resulted in Rainbow being unable to have kids. Ever.
  • Grumpy Bear: Blossomforth can be rather grouchy times.
  • Growling Gut: Pretty much every time eating is mentioned.
  • Happy Ending Massage: Rarity inadvertently sets one up for Cloud Kicker.
  • 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.
  • Hidden Depths: Cloud Kicker insists that she has them. To be fair, she actually does.
  • 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.
  • I Don't Want to Ruin Our Friendship: Presumably the reason one of Cloud Kicker's rules is that friends are off-limits for relationships.
    • It's also why Cloud won't sleep with any of Rainbow Dash's friends.
    Cloud Kicker: The boss might be friends with some real hotties, but banging one of them would get real messy real fast. The boss and I have a good thing going, and Iím not gonna mess it up just for one night of meaningless sex.
  • If You Ever Do Anything to Hurt Her...: "You feather things up with Derpy and I'll kill you."
  • 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.
  • In Vino Veritas / But Liquor Is Quicker: Blossomforth makes a very clumsy attempt to seduce Cloud Kicker after she gets drunk.
  • I Think You Broke Him: Cloud Kicker has a tendency to break Blossomforth when she's teasing her.
  • It's All About Me: Cloud Kicker can be a little self-centered at times.
  • Ladykiller in Love: Cloud Kicker in regards to Derpy. She was downright shocked when she found herself turning down two offers for three-ways.
  • Lethal Harmless Powers:Light refraction spells can be used to create pretty light shows, focus light for long range observation... or cut enemies into smoking chunks with laser beams.
  • Like an Old Married Couple: Cloud Kicker and Blossomforth.
    • Said word-for-word by Nurse Redheart.
  • 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. 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.
  • My Brother Is Off Limits: Applejack tries to run Cloud Kicker off the farm when she catches her talking to Big Mac.
  • 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.
  • No-Holds-Barred Beatdown: Cloud Kicker unleashes one in Chapter 5.
  • 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."
  • Not So Stoic: Derpy usually displays almost saint-like calm and composure. Then Blossomforth tries to take Cloudkicker from her.
  • 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.
  • Odd Friendship: Cloud Kicker and Blossomforth have one.
  • One Steve Limit: Cloud admits at one point that name duplication has been an issue in her clan, since there are only so many names one can combine with "Kicker" that still sound good.
    • The Lunar Rebellion also feature Nimbus Kicker as a character, while Cloud Kicker's mother is named Nimbus Gust.
  • Orphanage of Fear: Where Sparkler, Derpy's adopted child, came from.
  • 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...
  • Poor Communication Kills: Almost literally back in flight school.
  • Recursive Fan-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.
  • Red Oni, Blue Oni: Cloud Kicker is red, Blossomforth is blue.
  • 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.
  • Shout-Out: Perhaps unsurprisingly given one of the author's other works there are one or two references to The Dresden Files.
  • 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.
    • As are the chapter titles.
  • Threat Backfire: In Chapter 16:
    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.
    Rainbow Dash: Over my dead body!
  • Tranquil Fury: Cloud Kicker's reaction when Derpy is insulted.
  • Tsundere: Blossomforth is very much so for Cloud Kicker.
  • Twin Threesome Fantasy: When Rarity arranges an apology, Rarity arranges an apology. Well, accidentally.
  • Unusual Euphemism: Cloud Kicker certainly enjoys Derpy's muffins.
  • Uptight Loves Wild: Part of what drew Blossomforth to Cloud Kicker.
  • Unresolved Sexual Tension: Rarity and Applejack. Also possibly Cloud Kicker and Blossomforth.
  • 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.
  • We Used to Be Friends: Cloud Kicker and Fluttershy.
  • 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.
  • Wham Line: In-universe, Derpy saying "I love you too" when CK tells her she turned down not one, but two threesomes.
  • 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.
  • Will They or Won't They?: Cloud Kicker and Blossomforth.
    • Applejack and Rarity, too. They did.
  • 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:

  • And Then What?: Used by Celestia to deliver an intellectual beatdown on Apple Tree in The Lunar Rebellion, illustrating that his positions - while valid concerns - are also immensely complex problems without the easy solutions he advocates.
  • 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.
  • Mythology Gag: Rainbow Dash's parents are the G3 Rainbow Dash and Surprise, a G1 pony that was the inspiration for Pinkie Pie.
  • Nightmare Fetishist: Midnight Sparkle in The Lunar Rebellion. Her reaction to a unicorn lieutenant who made the mistake of trying to pick a fight with Shadow Kicker was to excitedly ask him if he's going to die.
  • Not Quite The Right Thing: One of the first moves of the Ephorate in The Lunar Rebellion is to assist the Earth Pony populist movement in overthrowing the upper class elite and forgiving the debt of working farmers, which Celestia had previously refused to do. Shortly thereafter, we see exactly why she thought it was a bad idea: unable to collect on the money owed to them, the banks of Manehattan almost immediately go bankrupt. The new Earth Pony government, meanwhile, proves to be as uneducated, stubborn, and shortsighted as they are idealistic, and have absolutely no idea how to handle the situation.
  • Principles Zealot: Fair Deal, full stop.
    Fair Deal: Neigh, I say. I am not backing up, not one step, ever.
  • 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:

  • 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.

Letters From A Disgruntled Friendship StudentFanWorks/My Little Pony: Friendship Is MagicLife In Manehattan

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