Chapter 1
Spy Glass sniffled softly. Today was probably the worst day of his life so far. Not only was he in big trouble, it wasn't even his fault this time! Now he was stuck hiding under a slide in the cool dirt of the playground while Ms. Cherilee looked for him. When she had cornered him after class he had taken his first opportunity to run. She had been so nice about it, but Spy Glass knew that if he gave in now, he'd be stuck. Every year the school play would come and she'd look to him to play the lead!
It had all started with that stupid play. The play was just a bit of pony history, and Spy Glass had happily chosen the part of some background pony with no lines; a part that happened to be about a minute long... and mostly behind some scenery. Spy Glass had picked the sea captain because the part was accompanied by narration, which meant he didn't have to talk at all.
Unfortunately, Spy Glasses's anonymity was not to last. When the lights came up on the nautical history of Equestria Spy Glass manned his tiny cardboard ship fiercely, glad of the obscuring bed-sheet sails and squeaky, lisping voice that told his story for him. The 'ooh'ing and 'ahh'ing that suddenly interrupted the narration was not welcome. The realization that the audience’s attention was directly focused on Spy Glass himself was far less welcome. It had certainly been a dramatic way to get one's cutie mark.
But the cutie mark itself was the problem! Spy Glass looked mournfully at his flank, where the twin masks of the theatre gazed back at him- one smiling and the other mimicking his own frown. A cutie mark was supposed to represent your destiny, and what it was that you were best at. And Cherilee had been delighted that one of her students had blossomed into a stage pony. Even the other foals now looked to him to do the speaking parts presentations!
“Hey? You under there Spy Glass?”
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Cherilee frowned in worry. Spy Glass had been missing for over half an hour, and she was starting to get concerned. After a thorough search of the school courtyard she had begun the long trot toward Ponyville proper, where Spy Glass lived. Cherilee hoped to find the little pony with his parents. Perhaps they could help her understand what had so gotten into the little foal. She hadn’t even gotten to ask him about the play before he had bolted from the school house in a panic.
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The top of an orange and purple head lowered into view from the slide, and Scootaloo’s worried frown followed close behind. “I found him guys!”
“Yeah! We saw you take off and were hoping you were ok!” Sweetie Belle piped as she scampered around to peer into the hiding place.
Spy Glass dried his eyes with a fetlock. “I’m ok guys. I’m just trying to avoid Ms. Cherilee. She wants me to act in the play!”
“Act in the play? Why would you be running away from that?” Applebloom asked from atop the slide, where she was holding Scootaloo’s back hooves.
“I just don’t like being in front of ponies. And ever since I’ve got this darn cutie mark everyone expects me to be an actor and stuff. And I don’t want to!”
Scootaloo’s tail swatted Applebloom’s nose, prompting a cacophonous sneezing fit. “Ooof,” Scootaloo grunted as she landed snout-first in the dirt.
“You mean your cutie mark isn’t what you want to do!?” Concern was growing on Sweetie Belle’s face as she helped Scootaloo to her hooves.
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Cherilee paused in front of the cottage. She’d rarely been to this side of Ponyville (it wasn’t the side with Sugar Cube Corner!), and she wanted to be sure she burst into the correct house with her concerns. Reassured by the hoof-painted ‘Glass Residence’ on the mailbox, she knocked on the front door. Cherilee’s face fell when she saw the concerned look on Mrs. Glass’s face. “Spy Glass isn’t here, is he?”
“No! Did he not leave school with the rest of the students?” Mrs. Glass ushered Ms. Cherilee in and gestured to a cushion with a hoof.
“I held him after to ask him about the upcoming play, but before I could utter more than a sentence he bolted for the door and I haven’t been able to find him since!
“Ah, the play. Oh dear.”
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“Maybe it just means something else! Like you enjoy being happy… and sad?” Scootaloo frowned, her wings buzzing distractedly, “Nah, that doesn’t make sense.”
“What exactly were you doing when it showed up?” Applebloom asked, “Were you doing anything not actor-ish?”
“I was just being the ship’s captain like I was supposed to! I was imagining sailing across the sea to new places, and fighting off giant eels, and maybe even pirates!
"Pirates huh?"
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~Some Time Later~
Spy Glass peered at the horizon through the eye slits in his mask. His hooves gripped the great wheel of his vessel firmly, steering her through the choppy waves, tacking back and forth across the brightly-lit surface. Beneath the mask, Spy Glass grinned ferociously. This was what he was meant to do.
Her Majesties’ Ship, the Jester, slit the swells pursued its quarry. A single, black-sailed changeling vessel had been spotted, and the HMS Jester had been called upon to overtake and capture the enemy vessel before it could plunder the coastal cities of Equestria.
The captain of the Jester, Spy Glass himself, was now famous enough that even the sight of his garish red and green sails could send a changeling vessel into a hasty retreat. If they were unlucky enough to be overtaken and boarded, the visage of the captain wearing his black and gold mask often inspired spontaneous surrenders. Its leering rictus and frown juxtaposition had already overseen many a surrender, and many less peaceful maneuvers as well.
Spy Glass signaled for the deck-hooves to prepare the grappling hooks. They were nearly within boarding range, and the black vessel’s doom was at hand. It would not escape from Celestia's shining glare, nor her righteous right hoof.
“Yes. This is my destiny. It just took a little looking to find.”
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In 'The Pasture' elderly ponies home, Cherilee smiled at the newspaper in her hooves. The front page headline read, ‘Another daring rescue at the hands of Captain Glass!’
Cherilee set the paper down and leaned back in her rocking chair.
“I can’t help but take a little credit for that one. I did cast him in the part myself!”