THE NEXT DAY

"Well, let's get the ball rolling," Dempson said. Overlord said to wait until today to make the escape. "Something about a 'Nightmare Night' festival in Canterlot. They must need extra guards there to make sure it doesn't get rowdy or something," he thought. Taking the large pin that some sort of mutated pegasus-pin cushion hybrid gave him, he tried to recall, unsuccessfully, his lessons about lock-picking he got from his friend.
"Damnit! How do I get out of this cell now?!" he mentally berated himself. Dempson stood and, noticing a crack of mortar in the wall, chipped away at it with the needle. After several intense minutes worrying about the few guards coming and seeing what he was doing, he chipped enough of the plaster away to take out the bricks, forming a hole that was just barely large enough to crawl through. Dempson slipped through the hole and ran, hoping he could evade capture long enough for Overlord to break out.

Dempson ran up the wooden steps of the dungeon, taking two at a time, before emerging from underground in some sort of statue garden, right next to a stone, mish-mashed creature that posed as if he was singing.
"Whoever sculpted that thing must have been drunk," Dempson thought to himself. "Wait, do they even have alco-" bbbllllAAAAAAAARRRRrrrmmmm
Dempson was cut off in his mental rambling by the sound of a horn, almost like an...
"Alarm! They know I've escaped!" Dempson shouted in his mind "Hell in a Haybale, I'm running on limited time here. Gotta make this count!"

Dempson looked up from his sprinting to see a swarm of pegasi and...
"Celestia. All according to plan." Dempson ducked, weaved, and dodged throughout the garden, fleeing his pursuers and the magical blasts of the Solar Princess.
"Catch me if you can, Sun-Butt!" He shouted, seeing the Alicorn grow more and more frustrated, before letting loose a torrent of pure light energy.

Deep below ground, there was a click...
creeeeeaaak...

Dempson ran into a maze made of plants, now running from dozens of Earth Ponies, Unicorns, Pegasi, and one pissed off Princess. He heard a tune play, a song that had assisted thieves, rogues, and assassins flee from their crimes. A song, forever immortalized in the natural magic of Equestria's singing...

Dempson ran through the tunnels of foliage, guards chasing after him. Going through another tunnel, he looked to his left, seeing a grey Earth Pony with blue and red hair, blue headphones, and a gravestone mark chase a yellow pegasus with a green and yellow mane, holding a toaster made of... "Is that wood?!"

He took another turn, this time ending up between the Earth Pony and Unicorn guards. Looking between them as they glared at him, he ran down a straight path in the middle, the chase resuming.

Taking one last corner, he looked back, seeing that he finally lost the guards tailing him. Turning, he took a step forwards...
Only for his foot to fall on nothing, and he, too, fell down the cliff, landing in every thorn bush and rock pile on the way down.

Looking up from the Dempson-Sized crater, he briefly wondered how he wasn't dead. "I'll file it in the 'Questions of Insanity' folder. I have more pressing matters to be concerned with." Dempson looked around, finding himself in an extremely large hole, bordering on excessive how deep it was. He looked to one of the cliffwalls, riddled with ledges and holes. He walked up to it and, placing his feet at hands on it, started to climb...

Before he was shot with a stasis spell and trapped on the wall. He levitated upwards, finding himself surrounded, pegasi hovering where he came from, unicorns, earth ponies, and an angry princess with a glowing horn where he wanted to be.

"I have had it up to the tip of my horn with you, 'Puppeteer.' Now, let's get you back to your cell, before I become truly annoyed," Celestia snarled, before teleporting herself and her captive just outside the gates of the dungeon, expecting to hear the same insults and threats hurled at her like every other time she came here. But, as Celestia prepped a deafening spell to mute the voices, she looked around to see that all the cell doors holding the mutations were open, the cells empty.

"What did you do?!" Celestia shouted, her eyes seething with rage. "They were trapped here for a reason, creature!

"Yeah, so no one would know what you've done," Dempson said, before being thrown face first into a cell, the door slamming shut and freezing over. Dempson looked around before sighing. At least he had done his part, now it's time for Overlord to come through on his promise.

As Dempson waited, an inky black sludge drifted across the floor, coming to a halt in front of him. The sludge slowly took the form of a thin, skeletal man with yellow orbs where their eyes would be. The sludge pointed at Dempson, before beckoning him with a single bony, whispy finger.

"I'm going to assumed that you're the Shadow Walker that Overlord sent?" Dempson asked, already assuming the answer. The Walker nodded, before beckoning again. "Want me to follow you?" A nod. "Alright," Dempson stated simply, running a probability check in his mind about how likely this was a trap. "If this is a trap, and I go, I may wind up in agony or worse. Trap, don't go, I stay here and rot peacefully in my cell, throwing away the one chance at freedom," Dempson contemplated, before settling on an answer. "Option B it is," He said, before following the Walker into a dark corner of the cell.

"Now, what is thi-wagh!" Dempson was cut off by a feeling of cold, numbness, then blacking out...

"...grugh..." Was Dempson's ever so sophisticated introduction, as he was roughly deposited on the floor of what seems to be a cavern. He blearily looked around, his eyes coming to a rest on the bleeding, hulking set of armor towering over him.

"Hello," The Overlord said, helping Dempson up. "As you can see, I kept my part of the bargain."

"Gruh," Dempson mumbled again, feeling seeping back into his body as the numbness of shadows faded away. "What is this place?"

"This is a cavern not far from the Everfree Castle." Overlord said, gazing out over the landscape

"Ah," Dempson deadpanned, "And where exactly is this cavern?"

"In the Everfree Forest. Hence, the castle being called the Everfree Castle. Kind of obvious, but right now I am to happy to be annoyed."

"Ah, good." Dempson smiled for the first time in weeks. He glanced out of the cave, before rolling numbers in his head and coming to a conclusion. "Well, it seems like it's about twelve o' clock at night. I'm gonna get some shut-eye," he said, mumbling the last part through a yawn.

" Very well. I will have Sunshine wake you up in the morning. Just, wake up when she tells you to, or you may have to deal with ice. Lots of ice."

Dempson paled at a tumbling thought. "Gotcha," he said, before shambling into the cavern for a place to sleep.

Author's Note

Third chapter. Now things finally get interesting.
Rate, comment, and all that crap. I'm gonna keep going even if you hate it, so yeah.