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Tropes pertaining to Chengar Qordath's fanfic The Life and Times of a Winning Pony and related works.

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Ponyville

    Cloud Kicker 
The story's main protagonist. When young, she was enrolled at the West Hoof military academy in order to enter the Guard like the rest of her family, but stress from the lifestyle and the high expectations of her family caused her to snap and run away during the graduation ceremony.
  • Action Girl: She has her moments — she did, after all, spend a good portion of her youth training to go into the military. The most notable moment is during the Battle of Canterlot, where she takes charge of the Kicker clans and scattered guardsponies to organize a resistance against the changelings.
  • Badly Battered Babysitter: She winds up becoming one after somehow ending up in charge of Dinky, Alula, and the Cutie Mark Crusaders at the same time.
  • Black Sheep: She feels like one to her family for dropping out military school and not carrying on the family tradition of going into the Guard.
  • Blood from the Mouth: Played seriously when she gets her ribs broken.
  • I Banged Your Mom: She uses this to force a stalemate in parental sex squick while talking with Sparkler, as she did in fact sleep — repeatedly — with her adopted mother, 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 I’m not gonna mess it up just for one night of meaningless sex.
  • Ladykiller in Love: In regards to Derpy. She was downright shocked when she found herself turning down two offers for three-ways.
  • Military Brat: Her parents — and pretty much all of her family — are in the Guard, and she received military and martial training even before enrolling at West Hoof. Naturally, this had a major impact on her lifestyle and worldview.
  • Reconstruction: To an extent, she is a reconstruction of the "Charlie", from Two and a Half Men, character type. She's actually relatively nice, 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.
  • The Tease: Teasing Blossomforth is practically Cloud Kicker's hobby.
  • 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.
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    Fluttershy 
  • Affectionate Nickname: Cloud Kicker calls her "Eepysqueak", as that was what she thought her name was when they first started talking when they met in Flight Camp. In the present, 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.
  • My God, What Have I Done?: In chapter 9 of Life and Times, She went to Rainbow Dash for sex advice regarding her relationship with Cloud Kicker, which resulted in RD and Cloud nearly killing each other. Fluttershy broke down crying while muttering this, blaming herself for what happened.

    Blossomforth 
  • Beware the Nice Ones: Blossomforth is usually a pretty nice pony, but she can very fearsome when properly riled.
  • But Liquor Is Quicker: Blossomforth makes a very clumsy attempt to seduce Cloud Kicker after she gets drunk.
  • Can't Hold Her Liquor: Blossomforth is apparently a lightweight. She also can't keep her mouth shut.
  • Character Development: Blossomforth slowly develops a thicker skin in response to Cloud Kicker's teasing. By the time of The New Life, she's to the point where she's joining in with her.
  • Deadpan Snarker: When she's not being embarrassed by Cloud Kicker.
  • I Think You Broke Him: Cloud Kicker has a tendency to break Blossomforth when she's teasing her throughout most of Life and Times.
  • Straight Man: She often takes this role to Cloud Kicker.
  • Uptight Loves Wild: The straight-laced, easily flustered Blossomforth ended up in a relationship with the sexually uninhibited Cloud Kicker.
  • 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.
  • "The Reason You Suck" Speech: In Chapter 6 of Life and Times, Blossomforth starts out by calling Cloud Kicker out on her tendency to be a bit self-centered and inconsiderate, but before long it morphs into something nastier, and then things get worse.

    Rainbow Dash 
  • Asexuality:. According to Cloud Kicker, Rainbow's relationship with Pinkie is the first romance she's ever had, and in chapter 9, it is revealed that there may be a physical reason for Dash's lack of sexual activity. It's also 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.
  • Cluster F-Bomb: She drops one at the beginning of chapter 16 of Life and Times, immediately followed by a Shout-Out to the page quote for this trope.
  • 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 of Life and Times.
  • Has Two Mommies: She's the biological daughter of two mares (G3 Rainbow Dash and G1 Surprise) something possible in-universe through very powerful magic and/or The Power of Love.
  • I'm Cold... So Cold...: She went into shock from blood loss after almost getting disemboweled with a vicious kick during the incident in Flight School.
  • 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.
  • Oblivious to Love: Played incredibly straight in The Incredibly Dense Mind of Rainbow Dash.
  • 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.

    Derpy 

    Sparkler 
  • Broken Pedestal: Seeing Derpy physically lash out in anger is enough to severely shake Sparkler's faith in her, as it brought back painful memories of her physically abusive foster father.
  • I Banged Your Mom: Cloud Kicker uses this to force a stalemate in parental sex squick while talking with her, as she did in fact sleep — repeatedly — with her adopted mom.
  • Related in the Adaptation: Whereas in the show, she's merely a background pony without any real development, here she turns out to be the daughter of Twilight Velvet due to a revenge-affair against her husband for an affair of his own (one that produced Vinyl Scratch). Twilight and Shining spent their lives believing her to have died as a foal, when in reality, she had simply been given up for adoption.
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    Dinky Hooves 
  • Children Are Innocent: Dinky is so cute and innocent that her appearances border on Tastes Like Diabetes.
  • Has Two Mommies: There's an in-universe rumor that this is the case, due to the fact that's it's possible in the fic's verse for two mares to conceive through The Power of Love or some very expensive magic, combined with the fact that Cloud and Derpy hung together an awful lot, and that they did have sex before Dinky was born. This is false: a one-night stand between two pegasi wasn’t likely to include either of the required factors, and at any rate Dinky's canonical sire turned out to be Shining Armor.

    Twilight Sparkle 
  • Bread, Eggs, Breaded Eggs: When she's startled out of an eavesdropping spell in Princess Twilight's Profoundly Peripheral Protector, she awkwardly tries to claim she was distracted due to thinking about "magic and friendship, and the magic of friendship".
  • Posthumous Sibling: Believed her youngest sister Amethyst Star to be dead from a young age. Turns out, she was really given up for adoption and goes by the name Sparkler now.
  • Related in the Adaptation: To Vinyl Scratch, her half-sister on her father's side. Also, to Sparkler, half-sister on her mother's side.
  • Super OCD: Much like in the show, she's obsessively devoted to tidiness and schedules and loves little as much as extensive periods of time spent sorting out and organizing large amounts of stuff. In Journey of the Lesser Lights, she eagerly jumps on the chance to organize over a millennium's worth of junk, clutter and mementoes stashed by Luna and Celestia in the basements of Canterlot Castle, and ends up spending over two weeks quite literally camped in there alongside Storm Kicker having the time of her life sorting through the disorder.

    Storm Kicker 
  • Bodyguard Crush: Implied, but ultimately subverted. While she is devoted to Twilight, the moment Twilight brings up the possibility of courting her own bodyguard in the Freeport Venture crossover, "Princess Twilight and the Disastrously Daunting Dinner Delegates", she politely refuses.
  • Bodyguarding a Badass: After becoming the head of Twilight's guard. This is actually the core of one of Twilight's objections to having dedicated guards — as alicorns, the Princesses can go one-on-one against threats that would trample straight over even competent and well-prepared guards.
    Twilight: If anything, I would have to protect them during a crisis.
  • Hunter of Monsters: She started her career serving in the Long Patrol, an order of guardponies that patrol Equestria's wildernesses to hunt dangerous monsters. This is a large part of why she was assigned to protect Twilight, due to Ponyville's closeness to the Everfree and its monsters.

    Twinkleshine 
One of the members of Twilight's guard, and also one of her old friends from Canterlot. She's also become romantically involved with Cloud Kicker's father following his wife's death.
  • Likes Older Men: As Twilight points out in The New Life of a Winning Pony, she's consistently shown romantic interest in older stallions: she had a serious crush on a teacher while in school, and eventually becomes involved with Tornado Kicker, who's a good couple decades older than her.
  • May–December Romance: With Tornado Kicker. They are genuinely in love with each other and theirs is by all appearances a healthy relationship, although he's old enough to be her father — literally: Twinkleshine is young enough to have been in the same classes as Tornado's eldest daughter while in military school.
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The Kicker clan

    Nimbus Gust 
Cloud Kicker's strict and demanding mother.
  • Freudian Excuse: Her extremely strict parenting style is due in large part to her own experiences growing up: she was born in a household that provided little guidance or order for her life, and only obtained these when she joined the Guard. She also spent a good part of her youth drinking, partying and sleeping around, something that hurt her academic performance. As a result, when she became a mother herself, she tried to give cloud the stability she never had growing up and based herself on the only source of structure she knew, and later doubled down when she thought that Cloud was repeating her mistakes. That said, it's acknowledged in the story that this does not make up for the fact that she was not, in the end, a good mother.
  • Hard-Drinking Party Girl: In stark contrast to her adult behavior she spent most nights of her West Hoof days drinking and engaging in a long series of one-night stands. Wind Kicker, her roommate back then, noted that she always came back to their room "smelling of alcohol, sex or both". She eventually gave of the one-night-stands when she started dating Tornado and the alcohol when she got pregnant. Part of the reason for her strictness with her daughter was that she thought Cloud was beginning to repeat her mistakes.

    Tornado Kicker 
Cloud Kicker's father, and the leader of the Kicker clan.
  • May–December Romance: After Nimbus dies, he eventually pairs up with Twinkleshine, who is young enough to have been in the same classes as Tornado's eldest daughter while in military school.
  • Parent with New Paramour: He begins dating again a couple years after Nimbus' death, forming a relationship with Twinkleshine, a unicorn guardsmare. Cloud is rather uncomfortable with this, as — besides the general uncomfortable feeling of her dad being with someone besides her mother — Twinkleshine is young enough that she and Cloud were in the same classes in West Hoof.
  • The Patriarch: His role as the head of the Kicker clan.

    Alula 

    Wind Kicker 
Cloud Kicker's aunt, and Tornado Kicker's younger sister. She works a professional psychiatrist for the Guard.
  • The Shrink: She's a psychologist by profession, and this seeps into her private life — she's always more than willing to psychoanalyze her family members if she thinks it could help them with their issues.

    Typhoon Season 
Cloud Kicker's uncle, and Wind Kicker's romantic partner. He's also the High Shadowvar of the Cult of Shadow.
  • High Priest: As the High Shadowvar, he's the leader of Shadow Kicker's posthumous religion.

    Star Kicker 
Wind Kicker's and Typhoon Season's youngest daughter and Cloud Kicker's cousin, Star is one of the few unicorns in the pegasus-majority Kickers. She eventually becomes part of Princess Luna's Night Guard.
  • Tracking Spell: Her special talent is tracking and location magic, and she specializes in creating small gems enchanted with tracking spells. She also has the rather impolite habit of planting these gems on the clothing and persons of everybody she meets or talks to, for the purposes of being able to track them should the need arise. This does come in handy on some occasions, such as in The Incredibly Thrilling Investigation of Storm Kicker, when Lyra goes missing and Star is able to use a gem she previously planted on her as a focus for casting a tracking spell.

Other Canterlot residents

    Princess Celestia 
  • Troll: She certainly does like her practical jokes. As an example, in Cadance's Lovely Misadventure, when Cadance asks her what kind of things she looks for in partners, she gives a description (tall, mare, pink coat, multicolored mane, alicorn) that matches Cadance herself, entirely for the pleasure of seeing her flustered and embarassed.

    Princess Cadence 
  • Oblivious to Love: Somewhat ironically for the Princess of Love, it takes Cadance surprising amount of time to realize Shining was in love with her. In Cadance's Lovely Misadventure, she managed to completely miss every sign Shining sent her way. When he said he was interested in someone in the nobility, and that he was a close friend to, she decided that meant one of his other male friends, since it never occurred to her he could possibly be talking about her.

    Shining Armor 
  • Big Brother Instinct: Despite only knowing Sparkler was his sister for all of a few weeks, he still falls into this when Sparkler reveals she's dating Star Kicker.
  • Mistaken for Gay: In Cadance's Lovely Misadventure, when Cadance was trying to set him up with a date and Shining was trying to say (in a rather roundabout way) he was in love with her, he tried to specify that his ideal date would be in the nobility, and also a close friend. Cadance, knowing that all his other friends were stallions and not realizing he was talking about her, concluded he was into guys. Afterwards, Shining was too mortified to correct the misunderstanding, although Cadance caught on on her own later on.
  • Oblivious to Love: It took him a surprisingly long time to realize that Cadence liked him that way, and didn't catch on until Musette said to his face in so many words that Cadence was interested in him.
  • Posthumous Sibling: Believed his youngest sister Amethyst Star to be dead from a young age. Turns out, she was really given up for adoption and goes by the name Sparkler now.
  • Related in the Adaptation: To Vinyl Scratch, his half-sister on her father's side. Also, to Sparkler, half-sister on his mother's side.

    Musette 
  • Blue and Orange Morality: Like all fey, she has a rather... odd... way of looking at the world, mostly centered around obligations, contracts and exchanges, where fulfilling agreements supersedes everything else. For instance, she made a contract with Vinyl Scratch after Vinyl idly said she'd "die" to be as good a singer as a famous performer, with Musette interpreting the contract to mean that she'd make Vinyl that good at the cost of her life — it's not her fault Vinyl didn't choose good terms! Of note is that Musette has come to genuinely like Vinyl and truly doesn't want to kill her — but she made a deal, and she simply can't conceive of not honoring their "agreement".
  • Cannot Tell a Lie: As a fey, she cannot say anything she knows to be untrue, and she cannot go back on her word. She can, however, doge questions, misdirect and lie by omission. This is how Shining Armor figures out what she is: he asks her directly if she is a muse. Her refusal to answer yes or no and constant attempts to redirect the conversation give him his answer.
  • The Fair Folk: She's a muse, a kind of fey that feeds off of the psychic energy associated with artistic creation and that as such lives by inspiring mortals to create artworks. Like all other fey, she Cannot Tell a Lie, is hurt by Cold Iron, and has a decidedly alien view of morality.
  • Really 700 Years Old: Visually, she looks to be in the same age range as Shining Armor and his friends. In reality, as an immortal fey creature, she's much older than that — it's not stated exactly how old, but she's implied to be in the same age range as Princess Celestia.

Others

    Queen Chrysalis 
  • Evil Gloating: Already a canon character trait for her, this is brought to new levels in Life and Times when she goes through the trouble of being in two places at once (by taking control of a random drone) so as to have the pleasure to gloat over two foes at once.
  • Hive Queen: She's this to the Changeling race, most of which consists of Hive Drones under her control. Better justified than with other examples of this trope, since she isn't a crucial node whose destruction (and thus existence) damages the whole swarm. Rather, she's essentially the conscious portion of the Hive Mind itself, and destroying her simply means she'll have to make herself a new body.
  • Resurrective Immortality: By virtue of being the consciousness of the changeling Hive Mind, she can simply spawn a new physical body for herself if her old one is destroyed. She’ll exist as long as the changeling race does.
  • Villain Override: She can possess any Changeling in her swarm, even shapeshifting to make them look like herself, something she does when she has to be in more than one place at the same time — for instance, trying to get Cloud Kicker and her group to surrender while at the same time gloating over a defeated Celestia.

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