Fluttershy's First

Prologue

Hearths' Warming Eve was drawing ever-closer by the hour and, rather than grey, Celestia's shortest day churned its golden hue to an unmasked ocean of stars set deep within an inked swell of rolling blue.

After several straight days of light snowfall, Cloudsdale suddenly called for a cloudless night to betake Canterlot, and relying on their number one weather pegasus in all of Equestria, Rainbow Dash's plan for a snug, warm day under the covers had to be cancelled, and not without a few choice words from beneath the blankets as she received a surprise visit from the Cloudsdale weather coordinator at her stoop. With her usual attitude Rainbow Dash was slow to start, but with the midday sun beaming down upon her castle in the clouds far above the cloudline, she reasoned it was a lost cause to try falling back asleep. And as she was quick to remember what day it was, her heart flew as fast as she did.

Tonight wasn't just Hearths' Warming Eve. A month before the celebration, Rainbow Dash was the last of her friends to reach her 18th birthday, and with Fluttershy the only one in the group still to have lost her virginity, Rainbow Dash, Twilight, Applejack, Pinkie Pie and Rarity had planned for months on taking Fluttershy to a mature mares' and colts' club where she could finally meet a stallion. The group was always apt to helping each other in these sort of situations. It was mostly Twilight the one who received the majority of the advice needless to say, with Rainbow Dash already having lost her virginity to Applejack a while back; Rarity reaching her marelyhood with a fashionable colt at the Canterlot wedding afterparty, leaving Spike in shambles with a bottle of Sherry in a ditch a mile off, nearly dead of alcohol poisoning even after he barely managed to survive the frigid winter air. Twilight herself matured significantly after talking him out of suicide 3 times in the year to follow. More than once she was left in tears waiting up all night listening to Spike's tiny broken heart as he lay motionless, the stark white sheets of the hospital bed following his shallow breaths rise and fall as he still held on to whatever he had left in his life, and she holding on to his tiny claw, forcing herself to think of something other than the thoughts that forced their way in. Pinkie Pie's first came to no surprise to the others. Considering her bit excessive friendliness, especially to strangers, she was quick to take up other ways in making her newfound friends happy.

Applejack's story was a rather interesting one. With her extended family spread to nearly every corner of Equestria, she was rather hesitant in picking herself a stallion, or even another mare for that matter, due to her fear of incest. Wandering outside the old gates of Sweet Apple and growing up under the life of Ponyville and even Canterlot, the social norms of her friends and others she met made the idea rather taboo, bittering in her heart the small glimmer of intimacy she held in for Big Macintosh that never came to be; and regardless, she herself wasn't the one to take a particular interest in the thought of living a homely life. Her heart sought freedom, and the day she came to realize the sonic rainboom she witnessed from her windowsill was caused by none other than Rainbow Dash, Applejack's simple hidden, long-time crush on the Cyan pegasus swelled within her until she could no longer hold it in. Most of the mares' stories were met with smiles and even jokes from her friends as they each shared them one-by-one over the years. Most of them.

It was much of a shock to the others when they discovered Twilight had gone all the way, even reaching any sort of intimacy with another would've been news. After her endurement of Spike's own shattered love-life, the others held off pushing her to find a one special somepony. The Mane were careful to be sensitive to Twilight's growing insecurities and she was often spared any jokes relating to her being single. When the group often visited the library with flowers or other gifts to hopefully cheer the unicorn up, Twilight regarded them with longing looks and a smile that hid something deeper. The day Twilight told her friends that she had lost her virginity, the group was out at lunch and Twilight didn't even look up to meet the eyes of her friends, but let them sit in silence for a few moments in disbelief. It was a secret she held in for nearly a year, and something she buried deeper inside her after Spike's passing. But the day came when Twilight revealed to the others that she had in fact, slept with Princess Celestia. It was a sex pact, one of the more intensive trials Celestia called for on Twilight's quest to becoming an alicorn, and ultimately an heir to the throne.

Tests... There were always tests.

Sleeping with the Princess. Becoming so close to her mentor to keep herself from ever going back after having gone so far. To have to slay her own number one assistant, who just weeks before had been fast asleep in her arms; yet in his heart he grew distant and in his pain festered, until it turned him into the monster that all dragons inevitably become, and this time he would never be brought back, Celestia calling upon Twilight to commit the unthinkable. It was nothing more than a test. Just a test.

Fluttershy on the other hoof was a different story entirely. Whatever commentary the friends spared on Twilight they returned with unrelenting force on the innocent pegasus. For months Rarity, Applejack, Pinkie and Rainbow Dash debated whether or not Fluttershy was more embarrassed when they had told her they arranged a late-night date with her and Big Macintosh or with the Cutie Mark Crusaders. The former resulting in her spending 3 weeks locked in her cottage, and after the latter she moved in with Angel's parents. Even after the groups' most sincere efforts to find Fluttershy her one special somepony, she would only respond with an excuse that she wasn't good enough, or that it would never work out, or a squeak. But after months of planning, a special opportunity presented itself on the most celebrated of all nights. Vinyl Scratch and Octavia were to be hosting an all night lock-in dance party in the royal Canterlot Palace ballroom. Over 3,000 ponies, 12 straight hours of heart thundering music, and no exit until the break of dawn. If this wasn't the night Fluttershy was to lose her virginity, the others mutually agreed they would officially deem Fluttershy to be a tree.

Even for such an experienced weather-mitigater as herself, Rainbow Dash had to admit her mid-afternoon toil was a rather exhausting ordeal, due to the excessive amount of cloud buildup of the past few days that had to be cleared in a matter of hours. But the result of the weatherpony's dedicated labor left Canterlot in celestial beauty, with the frosted-over shingles of the royal city rooftops and the silvered blacks of the rivers left glistening beneath the dust of stars beginning to emerge overhead, and the welcoming warmth of firelight deep within nooks and crannies of windows to compliment. Though she regretted missing out on a good afternoon's rest due to her plans that would surely take up her entire night, Rainbow Dash made a mental note to set her internal clock on snooze for the next few days.

But as she remained in the air looking down across Equestria, not a cloud in sight, she scanned the terrain nearly a mile below, scoping out her target of interest. First she eyed the outskirts of Ponyville, running adjacent to the rolling mountains of the western wilderness until her gaze landed flush to the Everfree, set afire by the somber sun cradled by the horizon infinitely beyond. In the safer regions of the Forest a grouping of oaks separated themselves from the dense elms and pines, creating a home that consisted of colonies of small woodland animals, nuts, berries, other assorted fruits for food, fruit groves, larger woodland animals, half of a woodland, Angel's parents and, as of recent, Fluttershy.

The plan being simple enough, Twilight, Rarity, Applejack, Pinkie Pie and Rainbow Dash were to begin their expedition at the doorstep of Mr and Mrs Angel. Unbeknownst to Fluttershy, her idea of a calm outing with her friends for the Hearths' Warming Eve celebration in Canterlot was going to be nothing calm, an understatement of an outing and sure as hell close to her friends.

Having to begin without her, the group agreed they would meet back up with Rainbow Dash somewhere along the several hour trip from Ponyville to Canterlot.

Rainbow Dash eyed the blotches of treetops hills beyond.

No... Too late. They've got to be way farther ahead than that.

She brought her focus a few miles closer, to the sharp outline of Ponyville rooftops silhouetted against the dense terrain. The last of the shutters closed; smoke trickled out of nearly all of the chimneys in feathery trails. It was too quiet, too lonesome. The pony residents there had long ago brought their celebrations to the indoors. And left no sign of her friends.

She scratched a hoof on the side of her head before running it through her mane. The road leading eastward out of Ponyville trailed off in the layer of white that blanketed the landscape, and the growing darkness swallowed up her sight before she could make out any of the familiar landmarks.

Her heart beat ever so slightly faster as she looked back up to the mountains and the last glimmer of crimson sunlight that oozed over the peaks.

I lost my friends. Even if I got to the party, that's still over 3,000 ponies I'm gunna have to go through to find them.

She closed her eyes and slid a hoof across her face as she let out a moan of annoyance that drifted out lazily as it froze in the air. Her wing beats were the only other sound to break the silence in a repetitive thrumming, leaving her to debate how she was going to begin the night until the deep holler of a train whistle gently cracked the frozen air across the valley.

-Wait!

A spark flashed in her eyes as Rainbow Dash spun toward the Canterlot side of the mountain range. Settled amongst the scattered peaks rested a plume of smoke following the thread of train tracks from the royal city to the valley below. And sure enough a yellow light led the way as a train emerged from one of the dozens of tunnels winding deep within the ivory rock.

She remembered only one train ran that night, a one-way trip from the railway station not far from Ponyville to the top peak of Canterlot Mountain. A smile rocketed across Rainbow Dash's face as her friends were no doubt on their way to the top.

Her heart raced, and a tiny burn found itself welcome in her lower stomach in her rekindled excitement. She tucked her wings, dipped her nose and dove headlong into the expanse of winter tundra that exploded out miles before her. The last crimson of the sun fell below the horizon, and with one final yell Rainbow Dash billowed the sky to ribbons behind her on her course to the train below.

"I'm comin' Fluttershy!"

* * *

Outside the Palace archway, the line of mares and stallions dressed in their most flashy attire that would impress even Photo Finish herself, snaked for hundreds of feet across the courtyard down along the lower mezzanines. Only a dozen ponies or so were ahead in line of Twilight, Applejack, Rarity, Pinkie Pie, Fluttershy and Rainbow Dash as they each shivered and laughed away at the night ahead of them. All of course except for Fluttershy who was scampering in place like a little filly waiting to open her gifts for Hearths' Warming Morning. Except she wasn't smiling, but rather biting her lower lip and making tiny squeaking noises in the back of her throat.

"Aw c'mon you guys, when do I get to take this stupid thing off anyways?" Fluttershy was growing more than anxious as the pounding bass that flooded its way through the stone pillars and nearing entrance thundered within her rib cage and settled in her stomach. It didn't much help either that her friends had blindfolded her and would refuse to let her take it off.

Rainbow Dash shook a bit more of the cold off and giggled through her smile that would never leave her face, "No you can't take it off! We already told you Fluttershy, it's a high end restaurant, only top of the top ponies get in. We wouldn't want you to go telling everypony about Rarity's super special hangout would we?! The crowds back at Ponyville would never let you sleep!" She spoke matter-of-factly and had to stifle another laugh.

"Well, I guess I wouldn't want all that attention..." Fluttershy seemed to calm down some after taking in the rainbow mare's words, "But why aren't you blindfolded? And who are all these other ponies around us? And why do we have to wait outside in the cold for so long?"

"My darling, the others are blindfolded!" Rarity gave a wink toward Applejack who promptly shoved a hoof in a puzzled looking pink mare's face. She stroked a hoof down Fluttershy's cheek, "And this music you hear is all part of the entertainment! Why, the others you hear around us all have reservations at the same diner, and this being Hearths' Warming Eve and all, there is a dreadfully long wait."

"AHEM! NEXT!"

"Ooooooh that's us!" Rarity turned and nearly had a heart attack as she exchanged bounces between legs.

"Oh gosh, is that our waiter?" Fluttershy tried to look worryingly in the general vicinity of Rainbow Dash or any of the others.

"Well uhhh," Applejack tried to cover while Rarity paid the minotaur bouncer, who had a distinctly similar look to that of Iron Will, pumping out his chest and trying his best to occupy the front archway entrance which was roped off with posh red ropes and stood guard by goats in neckties, "he's... He's our uh-"

"Yeah!" Rainbow Dash pushed the farmer-tanned pony aside, "He's our waiter, big guy, looks pretty scary, best not to talk to him."

"Well he doesn't sound very nice." Fluttershy whimpered, leaving Rainbow Dash to cover with more excuses until Rarity was finished.

"Sixty bits?!" Rarity gave a look of disgust as she was taken aback by the minotaur's demand. After years of practicing with appearances, she deftly regained her composure in a matter of milliseconds. It was time for a more alluring tactic. She closed her eyes, cleared her throat, and stared the grizzled minotaur right in the buckle, "Surely such a strong and handsome man such as yourself who clearly knows a thing or two about grooming, couldn't possibly charge a pretty little thing like me sixty bits just to take her girls out on a lovely evening!" Her eyes glimmered over as she stared up through Iron Will's massively forested chest of hair while neon green, purple and blue lights flashed across his face from the palace windows beside him, waiting for any sign of change as she batted her eyelashes sensually.

He leaned over, arching an arm over his head and pointing a finger down upon the ivory unicorn to show his authority, "YOU MUST PAY IRON WILL WHAT YOU OWE IRON WILL. IF YOU DON'T PAY, YOU MUST GO AWAY!"

Rarity gave up, her eyebrows furrowing in annoyance. She pulled Iron Will down more until his face came deathly close to hers. He sniffed at the minty perfume that wafted off Rarity's fur like evergreen and butterflies, making his eyes water. She stared past him, refusing to make eye contact, "If you let us in for free, I'll give you thirty minutes to do whatever you want to me." Her words weren't harsh, they weren't bitter, it was just an assault of utterly blunt syllables.

His eyes grew wide and Iron Will snorted and stood up authoritatively, looking around. "WELL UH, AHEM, RIGHT THIS WAY!" He stepped aside, bowing partly as a uniformed goat lifted a ruby-red rope for the six mares to enter. "ENJOY THE PARTY!"

"Wait, did he just say party- ?" Fluttershy didn't even have a chance to breathe before Rainbow Dash sprung into action, the Cyan pegasus shoving into Fluttershy's butt, pushing her toward the entrance.

"What? Pffffff," came Rainbow Dash's muffled sputter from beneath a poof of plush pink tail, "that's just uppity pony talk for fine dining experience."

"Rainbow Dash wait! How do you even know where we're going?" Fluttershy tried to retreat, but she couldn't get a hoofhold as she slipped across the slick stone flooring.

"Hey don't worry about it, c'mon! We're being seated!" Rainbow Dash took the upper hoof and forced the creamy banana mare forward under the archway, Rarity and Applejack following suit.

Pinkie Pie, trotting ahead, turned to see if the purple unicorn was coming. For most of the night Twilight had remained silent and as she stood now, staring up into the high towers of Canterlot, her mind seemed elsewhere, as it had been for unnervingly long now. It was hard for the pink pony to come to understand she could no longer cheer her best friend up; for there was nothing to fill the irreparable hole left in her unicorned friend. Pinkie brought Twilight's gaze down with a stroke of her hoof across her chin until their eyes met. Twilight saw her, but looked through; there was a shell that wound its way around her heart. Twilight was still there, but was growing more distant as time was beginning to wear her out. But for a moment she found her way back, and smiled easily at the mare that held her cheek, "You comin' Twilight?" It wasn't in her cheerful pitch that she used for most everypony, but Pinkie Pie spoke in a much softer, considerate tone. Twilight smiled a little more and followed the pink mare into the heavy glow of lights.