For Lyra, life is pretty swell. She has the best fillyfriend anyone could ask for in Bon Bon and she doesn’t need to worry about work or any complicated drama. Overall, she can live her life at her own tempo.

If only things stayed that simple.

Side story to The Life and Times of a Winning Pony and the rest of the Winningverse and approved by Chengar Qordath and Comma Kazie.

Three hundred years before the banishment of Nightmare Moon, the world was a very different place—and some ponies lived very different lives. A pegasus who serves the gryphons of Eaglesburg is fed up with the way he and his fellow ponies are treated. But escape from the cruel gryphon overlords seems impossible, and he has little hope.

Then his grandfather tells him of a legend—a young country ruled by kind pony princesses, where pegasi, unicorns and earth ponies can live peacefully. The pegasus and his earth pony friend, along with a small unicorn filly who is in immediate danger from her gryphon masters, make a daring escape. They head north toward their only hope for freedom—the land of Equestria.

On one of her regular hunts for gemstones, Rarity discovers a treasure trove beyond her wildest dreams... and the lavender-scaled dragon who collected it. Despite a rocky first meeting, Rarity and Greenfire soon find themselves drawn to each other more and more. But the question remains: How did a young dragon end up in the Everfree Forest all alone?

An alternate universe story that puts our favorite purple dragon and his beloved fashionista into a slightly different situation. Art used with permission from the wonderful ArtisteFish!

Now with a TV Tropes page! Thanks go out to Poptard and whoever else might feel like editing it.

Fan Works
Climbing the Cliff by Pia-chan (from chapter 5)
Such a Pleasant Chat by Fukaï
Some Form of Tea by Pia-chan (from chapter 4)
Promo Animation by CMagic (mild chapter 6 spoilers)

New! Part 3: After Twilight notices Applejack becoming increasingly obsessed with the game, she tasks Pinkie Pie (of all ponies) to keep an eye on her. The two head out into Ponyville in search of adventure and the perfect game.

Part 1: Twilight has finally convinced Applejack to join her other friends in Spike's weekly D&D game. However, will she be able to figure out the rules before they all drive Spike crazy?

Part 2: Applebloom, Scootaloo, and Sweetie Belle have stumbled across Twilight's D&D books, and convinced her to take up the dice once more. But will anypony meet their high standards to be their Dungeon Master? More importantly, what will happen when you-know-who finds out?

Tinder Lightheart, a compassionate colt nearing adulthood, operates an orphanage previously run by his parents, with help from his brother Warden and his sister Airy. Together, the Lightheart siblings raise young orphans and see them off to new homes, giving them a chance to experience what true love and a family feels like. One filly, Felicity Gardens, has been in the orphanage for far too long, and while Tinder's fears for her grow, an unseen entity looms ever closer that threatens to rip apart everything he has worked to achieve. A story of turmoil and misfortune, An Instance of Happiness follows Tinder Lightheart and his family as they learn what a true family is, and discover it through their hardships, complicated further by the meddling mischievousness of Felicity.

This story is a sequel to The Flight of the Alicorn

Rarity was certain her troubles with magical gemstones had ended, but an unexpected royal visit soon convinces her otherwise. In order to save an ailing Princess, stop an ancient menace, and avert a disaster that threatens the survival of a lost tribe of ponies, Rarity, Blueblood, and a brave group of friends will travel to strange and foreign lands, and into the fathomless depths beneath tormented seas. In her quest to uncover the secrets of the Abyssal Forge, Rarity will have to use all her charm, wit, and skill—and rely on allies old and new—as the unlikeliest of ponies once again attempts to save the world in style.

Part Two of Three
The Adamant Triskelion - Book One: The Flight of the Alicorn
The Adamant Triskelion - Book Two: The Abyssal Forge
The Adamant Triskelion - Book Three: ???

Beautiful cover art by Lucky Dreams.

If you came to hear a story, I’m sorry to disappoint. I suspect this’ll just end up as one big confession, really. When you’re the first Teutscher to set hoof into Equestria, I suppose that’s to be expected. And when you’re the universe’s favorite chew toy, doubly so. Still, with enough wit, some Prussian ingenuity, a droll sense of humor, and wanton murder, I might just survive this. Then again, when you’re going up against an unending list of things like government conspiracies, that guardian angel who keeps telling you to kill ponies, psycho Equestrian girls with allophilia, a lunatic princess, the legions of the Inferno, the Equestrian culture itself, swashbuckling sword fights, and laissez-faire economists, you begin to realize why there’s a big “if” in the middle of your life.

Your thoughts/critiques/deathreats are welcome in the comments. Spoilers are also encouraged. If you don’t have anything to complain about, do please tell me what you liked so I know what worked.

Now on TV Tropes. Posted on the Equestria Daily 5/28/13. Now in ePub format for your convenience.

For almost a thousand years, the immortal Nightmare Moon has reigned over Equestria as Empress. To the average pony, Nightmare Moon is an overarching enigma whose rule is absolute and whose wrath is terrible. But to Twilight Sparkle, who as an orphan has never known her parents, the Empress is something else entirely. When the young unicorn is brought under the royal wing as an apprentice, she learns a great deal more about the supposed tyrant than she ever knew. But as Twilight is introduced to life with her new mentor, she is thrust into a world of political intrigue, conspiracies and secrets. Secrets that were never meant to be revealed. As allies and enemies plot against the very peace of the nation, will Twilight fall prey to the perils of her new position? Or will she prosper and find in Nightmare Moon the mother she never had?

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My eternal gratitude to my editor, LordOfTheWrongs, without whom Night's Favoured Child would not be the story it is today.

Now with added TVtropes!

Twilight's in some pretty deep trouble. It's bad enough that she put on a lot of weight, really let her mane go, and seems to have picked up a bad habit of chewing on anything. No, that really doesn't compare with the claws that have replaced her hooves, the fact that she can stand up to about 25 meters tall, breathes fire, and had an involuntary species reassignment spell cast on her.

Mostly thanks to Trixie, looking for means to prove herself the more powerful of the two, they've both found their ponyhood lacking due to a transformation into dragons by the Bag of Tirek. Worse yet, Trixie has fallen to his corrupting influence, and become his new lieutenant in the world, preparing to release him from his adamantium tomb.

Now, it is up to Twilight and her friends, and anypony else they can drag kicking and screaming into the fight to catch Trixie and save her from her from the taint that has corrupted her, and that threatens to corrupt the world. A tall order, to be sure; but when the odds becomes so great, the fight needs to go big, lest ponykind go extinct.

Twilight's ascension to the throne was supposed to be a joyous occasion, but as the months have passed and the shadows of the world grown a little darker, the lessons of her mentors and the weight of her responsibility has done nothing but made her more uncertain about her ability to rule.

Now, on the day of a grand gathering of nations, an attempt on the life of one princess and the abduction of the other brings with it an old foe and the weight of the world. With the fate of empires resting on her shoulders, Twilight must undertake a grand journey into the heart of madness and the untold history of Equestria to save her princesses and the world entire...

But save them from what?

Featured on Equestria Daily 10/12/13
I am humbled once again to be assisted by the brilliant RainbowDri in bring this story to fruition. I couldn't have asked for a more insightful assistant or all-around excellent guy.
Coverart supplied by the extremely talented dreampaw (Power leads to corruption). I can't thank her enough.