Hello there.

Chapter mildly updated 6/13/2020.

“This is a foolish endeavor, Twilight Sparkle, and far too reckless,” was Luna’s blunt remark as she stood before the six bearers of the Elements of Harmony. The bridge that led to the screaming faced portal in the lake was just behind her as she continued, “I am shocked that you six all decided to go on this mission. If it wasn’t for my sister informing me of your reckless decision, I wouldn’t be here to try and persuade you to abandon this foolhardy quest. Do you realize your importance and value to Equestria as a whole? Do you not understand what may happen if one of you is lost? Should even one of you fall, our greatest defense against evil is useless.”

“I know it’s reckless, and I know how important we are to Equestria, but we need to do this, Princess! You didn’t see the look in Trixie’s eyes, she seemed like she genuinely wanted me dead, and would gladly do it herself. Whatever she’s planning, it must be bad and we need to stop it!” Twilight replied. She sighed softly, knowing that the Princess only had the best intentions for them, “But, I can promise that we will proceed with the utmost caution when we go through the portal.”

Luna grimaced but knew that she could not truly stop Twilight and her friends from entering the portal. To do so would be to take away their freedom to go and do what they feel is right, if this is what they feel needs to be done then she will allow them. Even if she thinks it foolhardy. “Then shall I take it you will not abandon this undertaking of yours?” Luna tried once more.

Twilight nodded, “Yes, Princess.” Twilight knew that this is what they needed to do, something big is brewing and she and her friends need to stop it. Whatever it may be.

The Princess of the night sighed and bowed her head in defeat, but stood aside to allow the six mares to cross the bridge. She smiled as she watched them proceed, but she was determined to relay them one last warning, “Safe journeys, my friends, and beware of the machinations of the mad god. I know all too well the price one will pay for such a mistake should you let your guard down around him.”

With that last warning given, the six mares began their journey across the bridge.

Twilight felt nervous as she and her friends slowly traversed the stone bridge. Sure, she spent the last few hours doing some last-minute researching and studying anything about Oblivion she might have missed, but she still felt like she was getting cold hooves. Soon she and her friends will be on a completely different plane of existence, that was a fair distance from the home she has grown accustomed to in Ponyville.

“You alright there, sugar-cube?” Applejack asked, giving a concerned glance over at the purple unicorn as she trotted a little more quickly to walk next to her.

“I’m fine,” Twilight replied. “I’m just nervous about actually entering the portal. I mean it’s one thing to travel around Equestria or to go up to the Crystal Empire, but another plane of existence is a whole other level. Oblivion is such a vast expanse, and we haven’t even scratched the surface of its mysteries.”

“Shoot, Twi. Ah getcha, I’m worried too. Ah don’t even understand much about anything about this whole other ‘planes of existence’ thing. Don’t know much about this Sheo-whatchamacallhim, or Oblivion, but ah do know that somepony’s gotta do somethin’. And ah think that those ponies should be us, we just gotta stick together.”

Twilight smiled as the group neared the portal, “Thanks, AJ.”

“Anytime!”

“Oh, how adorable!” said a voice that came out of nowhere. “Six little brave ponies ready to venture out into the unknown! Solve puzzles to unlock doors! Slay the mighty beast! Explore a whole new realm! Unlock the mysteries of the universe! Or die trying and failing, at any rate, no skin off my bones really. Just yours.”

Rainbow rubbed her ear, “So is this that all-powerful god everypony keeps on talking about?”

“Ah, what a wonderful question my dear! Yes, this is Sheogorath, Prince of Madness, yadda yadda yadda. I thought it was rather obvious, perhaps I didn’t make this portal clear enough as to who owns it? I know you mortals are rather slow on the uptake, but do try and keep up will you?” Rainbow scowled at the portal but the mad god continued on, “Anyhoo, do come on in, do come on in! Lovely weather here on the Shivering Isles, why I haven’t made it rain cats and dogs for at least a fortnight! Oh ho ho, the blood. Was. Everywhere!”

The voice of Sheogorath cut off as Fluttershy gasped at the implication and left the six ponies to stand in front of the glowing portal. After briefly consoling the butter-colored pegasus the six friends looked at each other and nodded before jumping into the portal.

The first thing the six mares saw upon exiting the other side of the portal was a small stone brick room with a stone table standing over a round rug and a stone chair on each of its sides. A metronome was ticking away on the table and the only source of light came from a few small candles sitting in a candle stand next to the table. Finally, there was a simple wooden door leading to someplace else on the other side of the room.

The second thing they noticed was a unicorn pony that looked like he was somewhere between his middle-aged years and his older years. He was sitting on the other side of the table, sporting a snappy black suit jacket and a red shirt under it. He didn’t seem to notice the mares as he focused his attention on the scroll floating in front of him.

There were a few tense seconds of silence between the two parties before it was broken by the elder pony’s detached sounding voice, “Well, don’t just stand there staring at me stupidly. Whoever is in charge should take a seat, the others can just stand around.” He waved a dismissive hoof near the end of his sentence.

He motioned at the other empty seat with a gesture, not taking his eyes off the scroll.

Twilight’s friends gave her encouraging shoves and grins, so with a small smile, she took the seat in front of the strange pony before them. Once she was seated the elder unicorn stopped his writing and rolled the scroll up before making it disappear in a flash of light. He turned his rather bored-looking gaze upon Twilight, “So, mortal, what may I do for you. Are you here about the door or anything else for that matter?”

Twilight cleared her throat, “Uh, a little of both really. I-uh, we want to know why there is a portal to here in our Realm. We are also trying to stop somepony who we believe to have some evil plan.”

The other pony hummed, “I see, I’m afraid I can not begin to fathom my Lord’s reasons for putting the portal there in the first place, but if he wills it then it shall be so. It is no danger to your realm or any of its denizens if that is your concern. It is but a simple invitation. As for your other reason, I assume you are referring to the three who came through your portal before you? Best of luck in that regard I suppose, it’s none of my business really.”

“But, how can he will the portal there? I thought he was blocked from doing anything in our realm?” Twilight asked, genuinely curious.

The older stallion shrugged, “He can not enter your realm in full physical and magical power certainly, but he can still affect your realm in more ways than one. So long as it is but a portal to his realm and he does not try and go through himself, there is naught the spell the Elements of Harmony created that prevents him from entering your realm can do. If the spell prevented any contact with the planes of Oblivion, then conjuration as a school of magic would nearly be completely useless, yes?”

“So, who are you?” Twilight eventually asked as she accepted his answer. She perked up as if she forgot something. “Oh! My name is Twilight and these are my friends, Rarity, Applejack, Fluttershy, Rainbow Dash, and Pinkie Pie,” Twilight pointed a hoof at each mare as she called their name.

“My name is Jeeves, chamberlain to Lord Sheogorath. Charmed, I’m sure,” Jeeves replied. “Is there anything else you require, or shall we finish this up? I do have many important duties I must attend to.”

Twilight seemed to think it over before replying, “I do have two more questions… Earlier you called us mortals, are you not a pony like us? And, where does the door behind you lead?”

“I called you six mortals because that is what you are, and what I am not. I am not a pony, despite my deceiving appearances, I am a Daedra,” Jeeves flatly said, as if the topic was the most mundane of things to speak about. “As for your second question, that brings me to what we need to discuss. The door behind me leads to the Shivering Isles, the portal behind you leads you back to your realm. You must make a decision here to press on, or turn back. You will not be punished if you choose to leave now, your choice is your own. If you do continue through the door then all you must then do is pass through the Gates of Madness, if you’re successful then you might just find what you seek.”

Twilight didn’t need to think it over, “We’ll go through the door, we’ve come this far and won’t stop now.” Twilight’s other friends all gave their own confirmation.

Jeeves smiled a tiny bit, “Enthusiastic, I see. I pray you to keep that, it may serve you well.” Jeeves got up from his seat and said, “One last thing. When you reach the Gates of Madness, do mind Mr. Fluffles, he gets agitated when he hasn’t had his favorite meal and the troublemakers have been annoying him lately.”

Twilight quirked an eyebrow but nodded and watched as Jeeves opened the door, a bright shining light came from the open doorway and he didn’t hesitate to step through it. As the door closed behind him, shutting the light off, Twilight stood from her seat and looked at her friends, “Are you girls ready?”

The five mares nodded and before they all started to walk up to the door, the room around them disintegrated. The six mares stared in wonder as the walls themselves turned into beautiful butterflies and fireflies that spun around them before spiraling up into the air to disappear.

“Oh my, how pretty,” Fluttershy said as she watched the display, momentarily forgetting about the situation.

“Come on girls, we should hurry if we want to catch up with Trixie,” Twilight said as she looked out at the brightly lit, walled off, rather simple looking landscape. Large roots jutted out of the ground here and there, and even the trees looked twisted and strange. The purple mare could see a gatehouse further into the Shivering Isles from her spot at the top of the high pathway they found themselves on, and beyond that, she could vaguely see another landscape that looked to be split into a bright forest and a dark and grim looking twisted marsh.

The six bearers of the Elements of Harmony began their walk down the large hill, passing broken pillars of some old construct. Twilight winced in pain as the mares walked under a large root arching over the pathway.

"Are you alright, Twilight?" Rarity asked, noticing Twilight stopped walking to rub the base of her horn. The others stopped what they were doing to look at Twilight in concern.

"I-I'm fine, I just have this weird pressure on my horn. Do you feel something similar?" Twilight looked at her friend questioningly, wondering if the other unicorn could feel the same mild pain she did.

Rarity stared up at her horn cross-eyed for a second before closing her eyes to concentrate. After a minute she shook her head, "I'm afraid not, dear. Anypony else feel strange?"

A chorus of denial came from the other four.

Twilight put her hoof back down, "I'll just have to deal with it, for now, we'll figure it out when we get someplace safe. I think I saw a village by the lake when we were further up."

"Want me to check it out?" Rainbow asked, flapping her wings enough to give her some hover over her friends.

"Alright, but only keep a lookout from the air. We don't need you getting caught off-guard by any nasty surprises," Twilight agreed.

"Che! Don't sweat it, Twilight. I got this!" Rainbow flapped her wings harder and shot upwards through a gap in the large roots covering the pathway. A few seconds ticked by and Rainbow came tumbling back down, only barely able to save herself from a nasty collision with the ground. She dropped back to her hooves, panting with exertion.

"Well, dang, Rainbow. Ah reckon ya need ta work on your stamina a bit there. Yer already plum tuckered out," Applejack said, letting Rainbow lean on her for support.

"I-It's not that," Rainbow replied, pausing to catch her breath. "Once I got higher than a couple of meters I suddenly needed to use a lot more strength to keep myself flying. It only got harder the higher I went," she gasped for breath as Fluttershy rubbed her back, "Heck, doing a Rainboom is easier than flying higher than the roots of these creepy trees."

"What do you suppose this means?" Fluttershy asked to no one in particular.

Twilight bit her lip as she rubbed the base of her horn, "I have a hunch, but I'll need to think it over a little more. We can rest here a bit to let Rainbow recover."

"Sounds like a plan..." Rainbow muttered as she collapsed onto her haunches and groaned.