Pinkie Pie grinned to herself as she rummaged around in her closet. “Oooh, this is gonna be so good!” She lifted up an entire stack of boxes that were stored in the back and carried them downstairs.

It didn’t take long for her to notice the massive stallion standing at the store front’s counter once she got down. “Heya, Troubleshoes! Can I help you out?”

“Hello there, Pinkie Pie. I’m just waiting for Mrs. Cake, she said she was working on my order.”

“Oh yeah! Mrs. Cake told me she ran out of eggs and went all the way to Sweet Apple Acres to get some fresh from their coop. Shouldn’t take longer than thirty more minutes.”

“Figures...” Troubleshoes grumbled to himself, his mood souring considerably.

Pinkie’s face suddenly lit up with inspiration. “Hey! While you wait for her, you can help me out!”

“Uh, help out with what, exactly?”

Pinkie pushed the pile of boxes towards him. “Well, I’m planning all the things that everyone can do during the December orgy! And there’s like, a LOT of time to do them!”

“Wait, you’re planning already? It’s only the first of the month...”

“I know that it’s suuuuper in advance, but think of all the fun we can have together!” Pinkie opened up one of the boxes, and the contents instantly started popping out the moment the lid was open.

Troubleshoes looked around the floor. A variety of blindfolds, gags, whips, and piles of rope had scattered about. The stallion was left speechless. He obviously knew what he was looking at, but what could he possibly say?

Pinkie was busy picking up the scattered blindfolds. “Yeah, I wanted to make it so that before it hit midnight, we’d all put these on and walk around. That way, when it came time to start screwing, we’d all have sex with the ones literally closest to us! But noooooo, Twilight said it was ‘too dangerous’,” she grumbled, crossing her hooves and pouting at her plans already being spoiled.

“That’s...probably for the best,” Troubleshoes said, wincing at what kind of disaster he’d cause if he was pent up and blindfolded.

“Well, anyway, I’ll still be bringing these to the orgy at the end. Some of us are reeeaaally kinky, so I wanna spice things up this year!”

Pinkie opened up the next box, and plastic bottles and tubes of varying shapes and colors flew out of the box and onto the floor like confetti. Looking around at the mess, Troubleshoes couldn’t believe that many bottles could fit into that single box.

Troubleshoes leaned down to examine the mess, it didn’t take much guesswork to figure out they were all different varieties of lube. Oil-based, water-based, and especially flavored ones galore.

“You liiiike?” Pinkie teased, nudging the massive stallion in the ribs.

Troubleshoes let out a sharp huff, still looking at the labels on the bottles. There were so many varieties of flavored lube. There were the classic fruit ones like apple, strawberry, and cherry, more intricate ones like cupcakes, smores, and key lime pie, but hayburgers, diet root beer, and deep-fried lollipops? Most of these he would’ve sworn never existed had he not been looking at them right now.

“That’s one of my favorites,” Pinkie noted, grabbing the cupcake bottle. “So? What do you think? I figure it’s gonna be especially useful for you!”

“Hm?” Troubleshoes turned his head to look at her. “Why’s that?”

“Well, you’re pretty much the biggest pony in all of Equestria, and you are absolutely packing a real pony pounder!” PInkie said, spreading her hooves wide. “Someone, say, a super-cute party pony, miiight be curious and see how much she could fit inside of her, right?” She wiggled her rump up in the air to demonstrate.

“I...guess so…” Troubleshoes’s cheeks started burning red, looking around to check if anyone else might be walking in to see what he was currently seeing.

“Now, it might not all fit in, but the only way to know is to try. And if you make it as slippery and slidey as possible, then it’ll be that much easier to get into her!”

An all-too familiar stir started happening between Troubleshoes’s legs. “Er, Pinkie? I think you should save this talk for another ti-”

“Plus, since they’re flavored, she could have a lot more fun licking around that thick shaft…” Drool started to drip out from the corners of her lips. “That cupcake flavor going aaaall the way down…”

Unfortunately, Troubleshoes started to visualize the scene with Pinkie. He let out a small shudder as his cock started stiffening up. “L-Let’s not get ahead of ourselves here…”

Pinkie was far too busy fantasizing to listen. “Just one loooong lick of tasty, sweet goodness from the base all the way up to kiss the head…Aw yeah, that’d be goooood...”

The mental image began intruding past all other thoughts, and the more Pinkie described her horny tangent, the clearer it got in Troubleshoes’s head. He could see himself looking down, and Pinkie was there, lapping at his slick, lubed-up shaft. “M-Maybe we should put these away for now-”

“Ooh, maybe since it’s so big, we could use different flavors,” Pinkie mused, ducking down for a peek at the goods. “I’m thinking chocolate, vanilla, and strawberry for a neapolitan kind of thing, or bananas, maple syrup and cookie dough, or maybe we could just skip the lube entirely, cause I got a loooot of chocolate syrup that I can go through-”

“Uh, y-ya know what, Pinkie? I think I’ll just wait somewhere else until Mrs. Cake returns!” Troubleshoes bolted out the door, practically tripping over his own hooves as he sprinted away.

The heavy hoofsteps snapped Pinkie out of her trance. “Whoopsie! Shouldn’t go too crazy on the first day!” she giggled to herself.

As Pinkie started to gather everything that spilled out of the boxes, Roseluck entered and saw Pinkie surrounded by bottles of lube and various BDSM toys and absolutely zero context as to why.

“...I’ll...come back later,” she said, backing up with a fully red face.

Author's Note

Day 1: Game's begun!
Steel yourself, try not to cum!