The Mystery Of Simian Island

by Violet Runner

Rating: everyone
Tags: Comedy, King Sombra, Other, Adventure, Pipsqueak, Crossover, Zecora, Alternate Universe, Princess Luna, My Little Pony: Friendship is Magic
Length: 4604

Pipsqueak wakes up on an island and decides to become a Pirate.

After washing up on the shores of Brawl Island Pipsqueak Driftwood decides to follow his dreams to become a swashbuckling pirate. Little dose he know that his humble pursuit will take him on an adventure to the mysterious shores of Simian Island in order to save his new marefriend, Governor Luna, after she's foalnapped by the evil ghost pirate Sombra.

All characters are age appropriate there will be no foalcon.

Published 2013-09-03 16:20:02 UTC
Last updated 2015-12-03 20:35:04 UTC

Chapter 1: The Three Trials

A white earth pony with brown patches, wearing a pair of pants washed up on a beach. Dizzy he struggled to remember where he was and how he got there. Despite his best efforts he couldn't seem to remember how he got there, but one thing in his mind was certain he had a dream and is going to see it through.

Spotting a light on the side of a small mountain he decided to see what it was and if he could find someone who could help him. He walked up a small path leading up the mountain. When he got to the top he saw a gray pegasus mare sitting by a fire.

“Hello! My name’s Pipsqueak Driftwood and I want to be a pirate.” He said walking up to her.

“Yikes! Don’t sneak up on me like that.” She said turning to look at him.

“Er… I’m over this way miss.” Pip said see the mare facing the wrong way.

“Ah.” She said turning the right way this time, allowing Pipsqueak to see that she was cross-eyed. “Well then, Threepwood-“

“DRIFTWOOD.” He corrected. “Pipsqueak DRIFTWOOD.”

“I see.” The cross-eyed mare said making her eyes cross the other way. “So, you want to be a pirate, eh? You look more like a flooring inspector.” She dead panned. “But if you’re serious about pirating go talk to the pirate leaders. You’ll find them in the GRIME BAR.”

“Gosh. Thanks! I’ll do that. Bye now. I’m off to seek my fortune.” The white earth pony said happily.

“Good luck.” The Gray mare said before he started to walk away.

“Um…” He said turning around again. “Where did you say those pirate leaders were?”

“The GRIME-BAR.” She said clearly.

“Right. Thanks.” He said before heading back down the path.

As he walked back down the path he noticed a sign post with two signs on it. One was pointing towards the top of the mountain and said Look Out. The other was pointing to another path and said Town. Turning down the path he eventually found himself at the entrance to a small port town with a sign that said welcome to the Town of Ponyville here on Brawl Island. A few feet away he could see a small building. As it was the only one with any lights on in the area he decided to check it out.

“The GRIME BAR!” He said reading the sign above the door to the building. “This must be the place.”
He was about to open the door and walk in when he noticed there was a small poster on the wall next to the door. “Huh? What’s this? Re-elect Governor Luna. When there’s only one candidate, there’s only one choice.” He read before shrugging it off and walking it to the Bar.

As he walked into the bar he was a little surprised at what he saw. The bar was filled with many drunken sailor ponies and griffins many of which were passed out, there was even one purple mare with a grape and strawberry cutie mark swinging around on the chandelier that was made from an old anchor. Before he could take two steps a small dog with a bone in its mouth ran up to him and started growling at him.

“Ruff.” Pip said looking down at the dog.

“Ruff, a-roof arf! Woof woof arf woof warroof, Brawl Island! A-roof wuf: Sombra! Grrrrrrr.” The dog barked back at him.

“Wuf, Sombra?” He asked the small dog.

“Worf woof woof ruff ruff wor-roof wuf? Ruff arf-arf, bow-ruff Governor Luna! A-OOOOOOOO! A-OOOOO! (Ruff ruff ruff) Bow-roo wuf rowwf- Arrooof- Sombra! Grrrrrrr! Arf, oof-oof, Brawl Island! *Sniff sniff*” The dog explained before running away.

“I have no idea what he just said.” He said to himself as he continued walking through the bar.
As Pipsqueak walked through the bar he noticed a griffin that was wearing a big button that said: Ask me about Equestria Girls. Curious he walked up to him.

“Aye.” The Griffin greeted when he noticed Pip.

“Aye, yourself.” Pipsqueak said happily.

“Aye.” The griffin said taking a sip of his drink.

“Nice hat.” He said looking at the griffin’s hat, which had the name Grip on it.

“Aye.” Grip said.

“So, tell me about Equestria Girls.” Pip said looking at his button.

“You mean the latest animated masterpiece from Hasbro! Why it’s an extraordinary movie with an awesome story stunning 2D and 3D animation, memorable songs. Not to mention all the references and nods to the Brony Fandom. Starring the voices of great stars such as Tara Strong, Ashleigh Ball, Andrea Libman and Tabitha St. Germain. Blu-ray now in stores. Beat the Rush! Go out and Buy Equestria Girls today!” The Griffin said excitedly.

“Geeze, what an obvious sales pitch.” The want-to-be pirate said looking at the half slobber griffin.

“Sorry, I just get carried away on some topics.” Grip said apologetically.

“Nice talking to you.” He said backing up a bit.

“Aye.” The griffin said as Pip walked away.

Pip noticed three mares sitting at a table at the back of the bar away from everypony else. One was a White Unicorn with a two tone pink and purple mane. The second was a Yellow Earth Pony with a red mane with a bow in it. And the third was an Orange Pegasus with a purple mane.

“What da ya want, colt? The Yellow Earth Pony asked with a southern accent.

“I want to be a Pirate.” Pipsqueak exclaimed.

“So what?” The Orange Pegasus said flatly.

“Why bother us?” The Earth Pony asked.

“Hey, don’t forget we’re short on help because of this whole Sombra thing.” The White Unicorn reminded her friends.

“So?” The Pegasus asked looking at the Unicorn.

“So, no pirates means no bits, and no bits means no cider. We’re getting dangerously low on cider…”

“Hmm.” The Orange mare said looking pip up and down. “Do you have any special skills?”

“I can hold my breath for 10 minutes.” He said proudly.

“Well…” She said sceptically. “All right, but you don’t become a pirate just by asking.”

“Ya’ll have ta go through…” The Yellow mare began.

“The Three Trials!” The three said in Unison.

“Er… What three trials are those?” Pip asked.

“There are three trials every pirate must past.” The Earth Pony mare said.

“You must master the sword by besting the sword master of Brawl Island. You should get somepony to train you before you do that.” The Pegasus explained.

“Tha art of thievery. For this, we want ya to get a small item for us: The Idol of Many Hooves. It’s in a glass case in the Governor’s mansion just outside of town.” The Yellow mare explained.

“And the quest.” The White Unicorn said taking a drink of cider.

“The what?” The yellow Earth Pony asked.

“Treasure hunting, you dodo.” The Unicorn mare explained.

“Oh, right. There’s supposed ta be a treasure buried some were on tha island.” The red manned mare said. “You must prove yaself in each of these three areas: swordplay, thievery and, Er, treasure huntery. Then return with proof that you’ve done it.” The southern mare repeated.

“And then you must drink cider with us.” The Pegasus finished off.

“Cider!” The three mares shouted together.

“What’s in Cider anyway?” Pip asked.

“Cider is a secret mixture which contains one or more of tha following ingredients.” The red manned earth pony said.

(For the love of [insert deity or other religious figure name here] do NOT mix and/or consume the following concoction. Seriously YOU WILL DIE IF YOU DO!)

“Kerosene.”

“Propylene glycol.”

“Artificial sweeteners.”

“Sulphuric acid.”

“Apples.”

“Acidtone.”

“Red dye #2.”

“Grim.”

“Axle grease.”

“Battery acid.”

“And/or Jalapeño peppers.” The Earth pony mare finished. “As you can probably imagine, it’s one of the most caustic, volatile substances known to ponyind.”

"This stuff eats right through these mugs and the cook is losing a fortune replacing them. Ha ha.” The Orange mare laughed lifting up her empty glass to show that it had a hole in it.

“Well. I better get started on those trials.” The White Earth Pony said before leaving the bar.

Chapter 2: The FlimFlam Circuse

Deep beneath Simian Island, the ghost pirate Sombra's ship lay anchored in a river of magma. The ghostly figure of a Black and Red Unicorn stood in his cabin looking out the window as a skeletal Earth Pony entered.

"Captain Sombra...sir...I..." The Earth Pony began but was interrupted.

"Ah... There's nothin' like the hot winds of tartarus blowin' in your face." Sombra said not turning around.

"No sir... Nothing like it... hahahaha" He laughed nervously. "Ah... Sir... I..." The Earth Pony said trying to get back to why he was there.

"It's days like this that make you glad to be dead." The ghostly Unicorn continued turning to face the Earth Pony.

"Oh yes sir...glad to be dead..." The skeletal Earth Pony repeated nervously.

"Ye are glad to be dead, RIGHT?" Sombra asked glaring at the skeletal Earth Pony.

"Oh yes sir. I-I feel so lucky that you happened to capture my ship, then murdered me and everypony on board... Hahaha... yes sir...lucky." The Earth Pony said with a sigh.

"Glad to here it." The Ghost Unicorn said with a smirk. "Now what was it you disturbed me for?"

"Ah...yes sir...well, you see, we might have a problem on Brawl Island."

"PROBLEM?!?" Sombra asked angrily. "What possible problem could there be!? I've got those sissy pirates so scared of the sea they're afraid to take a bath!" He said marching up to the skeletal pony causing him to back up a bit.

"Well... There seems to be a new pirate in town." The skeletal pony said cowering a bit. "Actually, he's a pirate wannabe. Young, inexperienced, probably nothing to worry 'bout. Don't know know why I bothered you with it. Hahaha." He chuckled nervously again, looking away from the ghostly Unicorn. "I'll have him taken care of myself." The Earth Pony said turning to leave but was stopped by Sombra.

"Wait! I'll Handle this personally. My plans are to important to be messed up by an amateur." Sombra said turning back to the window.

"Yes sir." The skeletal Earth Pony said before leaving.

Pipsqueak stood outside the GRIME BAR think about which of the three trials he was going to do first when he saw a cooking pot sitting on top of some garbage bins. It was a descent size just big enough to fit over his head as a make shift helmet.

"Look at this pot, somepony through out a whole cooking pot and it's in great shape. Sure it has a few dents but it looks usable." Pip said to himself looking it over. " You know what? I know I have a bunch of stuff to do but I'm taking this, I'm taking this pot." He said picking it up and putting it on his head after thinking about where to put it.

Looking around he noticed some lights coming from a clearing close to the sign that pointed to town and the lookout. as he started to walk towards the lights he noticed a new sign on the post that said "Clearing" and pointed towards the lights. after questioning how he didn't notice that sign before he continued towards the lights. As he entered the clearing he noticed a big tent and went inside to find two Faded-Yellow Unicorns arguing.

"I would get in the cannon, but the gunpowder makes me sneeze." The Unicorn with the mustache said.

"Well, I can't do it, I sprained my hoof setting it up." The one with out the mustache said rubbing his hoof.

"I hardly think that compares to my chronic allergy. You get in the cannon."

"You don't have any allergies you faker. YOU get in the cannon."

"No. YOU get in the cannon."

"No. YOU get in the cannon."

"Slacker!"

"Loafer!"

"Ruffian!"

"Fop!"

"Weasel!"

"...Ahem..." Pipsqueak said getting there attention.

"Say there, son, how would you like a chance." The Unicorn with the mustache began. putting his hoof around pips shoulder.

"A once in a life time chance." The one with out a mustache added.

"To perform an amazing feat!

"A death-defying Feat!"

"Well, not so death-defying, really."

"A dangerous feat."

"No, not dangerous at all!"

"An easy feat!"

"But exciting!"

"With the Amazing!"

"World Famous!"

"Flim-Flam Bothers!"

"That's us. My brother Flim." The Unicorn with a mustache said introducing his brother.

"And my brother Flam." Flim said doing the same. "Sound good?"

"Good." Flam repeated.

"It's very simple, really."

"See that cannon over there?" The brother with a mustache asked, to which pip nodded. "All you have to do-"

"Is get in the cannon-" The one with out a mustache continued.

"And we shoot you out of it." Flam finished.

"Quite safe, actually." Flim said reassuringly. "So what do you say?"

"How Much will you pay me?" Pipsqueak asked not fully trusting the two.

"How about 478 "Bits?" Flam said.

"Ok, sounds good!" The White Earth Pony said surprised at the large sum of money.

"Great! I see you already have a helmet so let's do the trick." Flim said looking at the pot on pips head as they walked over to the cannon. "Now just get in the cannon and well take care of the rest."

Doing as he was told Pipsqueak got in the cannon and after a few seconds was shot across the tent and smacked into a one of the beams holding up the tent, losing the pot before falling to the ground just missing a soft pile of hay.

"It worked!" Flam said astonished.

"Oh I'm so relieved." Flim said before noticing pipsqueak lying on the ground. "Hey Kid?"

"You in there?" Flam asked looking at him.

"I'm Spike, are you my mommy?" Pip asked still dizzy from the impact.

"He's alright." The mustached Unicorn said happily.

"Hooray! We are spared another embarrassing and financially depleting lawsuit." Flim said helping him up.

"Here's your Bits for helping us out." Flam said handing pip a bag of Bits and pushing him, out of the tent as he started to come to his seances.

Chapter 3: Maps, Voodoo and Bald Ponies

Pipsqueak shook his head clear as he walked back into town. As he walked past the GRIME Bar two ponies walked out.

"So ya apparently this guy has a map to the lost treasure of Brawl Island and is willing to sell it to any one who knows the code." one of the ponies said.

"Oh? And what is this code?" the other one asked.

"First he asks you if you have a cousin name Sven. Then you say 'My cousin Sven sends his regards'." The other pony said as they walked away.

"Hmm if I buy that map and find that treasure then I can complete the treasure hunting Trial." Pip said to himself before walking into the main part of town.

As he entered the main part of town a Griffin wearing a trench coat walked up to him.

"Excuse me, but do you have a cousin named Sven?" The Griffin asked.

"My cousin Sven sends his regards." Pip said recognizing the code he just herd about.

"Shhhhh! Pipe down, will ya?" He said looking around. "That ugly sheriff might be around here. Now then... let's talk business." The Griffin said opening up his trench coat to reveal a bunch maps sticking out of different pockets. "You want to by a map to the Legendary Lost Treasure of Brawl Island? Only one in existence." He said unrolling one of the maps. "Only 100 bits."

"I'll take it!" The Pinto Earth Pony said pulling out the Bits he got from the Flimflam brothers and handing him the correct amount.

"There you go. You've made a wise decision." The griffin said handing him the map. "Now get lost." The griffin said leaning against a nearby wall.

Pip couldn't help feel like he had been ripped off. Shrugging it off he continued his walk through the town when he noticed a strange looking building with an open sign on it. walking inside he saw many strange things scattered about the room. Among them one thing seemed to stand out.

"A rubber chicken with a pulley in the middle..." He said looking at it. "What possible use could that have? Oh well It might be fun for a few laughs." He said picking it up and putting it in his pants.

"What can I do to help you?" A voice asked from be hind him. Turning around he saw a zebra sitting in front of a bubbling green cauldron.

"Well...uh..." Pip began but was interrupted.

"Wait... I feel something and it's not what I ate." She said putting a hoof to her head. "The spirits tell me you name would be...Guybrush Threepwood. No, no Pipsqueak Driftwood!"

"Wow! That was amazing. Do you know any other tricks?" Pipsqueak said amazed.

"A trick it was not. To gain insight from the spirits I was taught." The Zebra explained. "I sense your guilt of stealing my chicken grows. Take it it's yours." She said with a smirk.

"Why don't you want it?" The Earth Pony asked nervously. "Is it jinxed with an ancient Voodoo curse?"

"No, the pulley squeaks from not being oiled for weeks." She said with a shrug. "That is all I can tell you now. come back later and i shall tell more to thou." The Zebra said before disappearing in a cloud of smoke.

"Wow!" Pip said before leaving.

Pipsqueak continued his walk through town when he suddenly heard someone call to him from a near by ally.

"Hello? Anypony in here?" He asked looking around not seeing anyone. "HELLO?!?"

"You know, bad things could happen to a pony in a dark, deserted ally like this one. And at this time of night, nopony would be around to see it." A bald, Black Unicorn stallion said seeking up behind him.

"Oh really? That's interesting. Well, see ya." Pipsqueak said nervously trying to leave.

"Now, why are you in such a hurry?" The Unicorn said blocking his path. "I'd better get your name."

"I'm Pipsqueak Driftwood, and I'm a mighty pirate." Pip said introducing himself.

"Listen Threepwood-" The unicorn began.

"Drift-wood. Pipsqueak Driftwood." He corrected.

"What ever your name is, Listen: I'm the sheriff around here. Sheriff Fester Shinetop. So take it from me. This is a bad time to be visiting Brawl Island. A very BAD time." Shinetop said looking Pipsqueak dead in the eye. "My advice to you is to find some were else to take your vacation. Some where safer." He said before walking away.

"Boy, I feel much better knowing there's an officer of the law around." Pipsqueak said sarcastically once the sheriff was out of ear shot. "*Sniff Sniff* Hey did that guy sort of smell like a rotting corps?" He said sniffing the air before walking out of the ally.

Chapter 4: Trolling

Chapter 4: Trolling

“Hmm, I have a feeling that I’m going to need a few things if I’m going to complete these trials.” Pipsqueak said as he walked out of the ally. Spotting a general store he decided to check it out.

“Ahoy there, fancy pants.” An old Gray Earth Pony greeted as he walked into the store. “I’ve got a good deal on swords today, if you are in need of one.”

“Hello.” Pip said walking up to him.

“So, what do you what?” The shop keeper asked.

“I’d like a sword, a shovel and… I think that’s it for now.” He said looking around the shop.

“Great. Here’s your sword, best 100 bits you ever spent.” The Gray Earth Pony said handing it to him as Pip gave him the bits. “And here’s your collapsible shovel, it will pay for itself, believe me. You’ll dig up 75 bits in no time. But hay, save some treasure for the rest of us, would ya.” He said with a laugh as Pip paid for it before leveeing.

“Ok let me think,” Pip said to himself as he pulled out the map he bought. “According to this map the treasure is somewhere in the woods, so I guess I should head there.” He then folded it up and put it back in his pants before making his way through town.

As he came to the docks he saw a red fish laying right in the middle of the road.

“I should really pick this up before somepony trips on it.” Pip said picking it up. Seeing it was dead and there were no garbage bins around he decided to take it with him and put in in his pants with the rest of his stuff.

Pipsqueak continued his walk until he came to the weird sign post which now had a new sign that said “Sword Training” and pointed down a previously unseen path. Shrugging followed the new path until he came to an old wooden bridge. He was about to cross it when a Troll jumped in front of him blocking his path.

“None shall pass!” The Troll shouted, startling him.

“What?” Pip asked backing up a bit.

“None shall pass.” The Troll repeated.

“Don’t mess with me Troll I’m a mighty pirate!” He said trying to sound tough.

“You’re no pirate.” The Troll said with a laugh. “Why, the town drunk could out–insult you on her back! …And probably would.”

“Oh, yeah?” Pip said as tough as he could.

“Yeah!” The Troll said unfazed. “You know, you could stand a lesson or two if that’s the best you can come up with. Anyway if you want to get across my bridge you have to pay a toll.”

“What’s the toll?” The Pinto Earth Pony asked.

“Well I’m kind of hungry right now. Why don’t you bring me something to eat and I’ll let you pass.” The Troll said scratching his chin.

“Will this do?” Pip asked pulling out the fish.

“That will do nicely.” The Troll said before taking it before moving out of the way. “Alright you may pass.”

“Thanks.” Pip said continuing on his way.

Once Pip was out of site, the Troll removed its head to reveal a women in her late thirty’s with long red hair. She quickly ate the fish hole before putting the troll mask back on and walking away.

Chapter 5: Learning the Art of the Blade

Pipsqueak walked up the path and stopped when he came across a wooden building with a sign in front of it.

"Bulk Biceps' Big Body Pirate Gym! Now offering sword fighting lessons." The pinto earth pony read before walking up to the door and knocking.

"What do you want, wimpy little spineless maggot?" An extremely buff white pegasus with tiny wings asked answering the door.

"Could you train me to be better than the Sword Master?" Pipsqueak asked.

"Better than the Sword Master? You? Hahahahahahahaha!" Bulk Biceps laughed. "You could never be HALF the sword fighter Gilda is. Even with hours of hard work and sweatin' blood." The buff pegasus explained. "I remember fighting side-by-side with Gilda at Port Royal. The local constabulary had us cornered! It looked like we were done for, but then she said- But I digress." He said before getting into a long story. "You just don't have what it takes."

"I do so have what it takes!" The earth pony said trying to be tough.

"You do not!" Bulk stated a bit angrily.

"I do so!"

"You do not!"

"I do so!"

"I like your spirit." Bulk Biceps said giving in. "I'll do what I can. Of course, it'll cost you. 30 Bits should do it."

"Ok." Pipsqueak said handing over the Bits.

"Alright, now let's see your sword." The pegasus said taking the Bits.

"Ok, cheek it out." He said pulling it out.

"Yes, this is a nice one. Let's get to it" Bulk Biceps said leading him inside. "Ok you maggot." He said getting down to business. "Why don't you whip that sword out and let's see what you can do with it." The buff pony said as Pipsqueak put the handle in his mouth and stated waving it around. "Boy! You fight like a dairy farmer! I usually don't waste my time with vermin like yourself. But seeing as this Sombra thing has put a cramp on business, I've got no choice. I need the money." He explained as Pipsqueak continued to wave his sword. "I can see this is going to take some special measures. Just want you to know, I don't do this with everyone. It's only because I feel that special student mentor bits bonding that I'm going to these lengths. I'm going to put you up against, THE MACHINE!" Bulk Biceps said as he left the room

"Machine? Is this going to hurt?" The pinto earth pony asked as Bulk Biceps returned with a strange monkey operated contraption. "Yikes!" He said getting a good look at it.

"Come at me." The buff pony instructed. "Don't be afraid, you won't hurt me." He said as the training began. "Watch your foot work! Use your forte against the foible. Distance, distance! Advance, Thrust, Recover, Parry, Riposte!"

"You're starting to get the hang of it." Bulk Biceps said a few hours later.

"Not bad. You've got good form." He said even more hours later. "Now I'm gonna let you in on the true secret of sword fighting. Sword fighting is kinda like making love. It's not always what you do, but what you say. Any fool pirate can swing a sharp piece of metal around and hope to cut something. But the pros, they know just when to cut their opponent with an insult, one that catches them off guard. You see, kid, your wit's got to be twice as sharp as your sword.” Bulk explained. "Let's try a couple of insults out, shall we?" He asked to which Pipsqueak nodded. "Ok. Imagine this: We're fighting up a storm, just like Gilda and I were doing at Port Royal. There's a sudden break in the fighting and I say to you, 'You fight like a dairy farmer!'. You respond with?"

"I am rubber, you are glue." Pipsqueak said giving his best comeback.

"I can see we've got a lot of work to do here." Bulk Biceps sighed. "You should have responded with something like 'How appropriate. You fight like a cow.'. You see, it's razer-sharp wit like that that wins fights." He explained. "Let's try another. Imagine this: You're trapped up against a wall, my sword just slashed two cuts into your face. I say 'Soon you'll be wearing my sword like a shish-kabob!'. You respond with?"

"So's you're mother." The earth pony said still not getting the hang of it.

"I can see we're in deep trouble here." The white pegasus said face hoofing. "A correct response to 'Soon you'll be wearing my sword like a shish-kabob!' would have been something like 'First you'd better stop waving it like a feather-duster!'. See, razer-sharp. Now I suggest you go out there and learn some insults." Bulk Biceps said ending the lesson and kick Pipsqueak out.

"I can't help but feel like I've been ripped off. I'm sure if this was a fanfiction people would feel the same way after waiting almost two years for a new chapter." Pip said as the door closed behind him before walking back down the path.

Author's Note

It's Alive!