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The Trials and Tribulations of Tolliker

by Tolliker

Chapter 2: S1E2: Much Ado About Rimming

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Season I Episode 2: Much Ado About Rimming

—|—

The upholstery was a pleasant color, a light cream that gleamed when the morning sunlight shone through the windows of the truck. It smelled of apples and sweat with a hint of stallion, and wrinkled quite delicately wherever Umber shoved his face into it.

"Bi…Big…oh Celestia," he cried. Big Macintosh, whose muzzle was crammed rather solidly between his flanks, smiled, not that Umber would have seen. Big Mac knew he was like this at most stallion events, and had heard he was in private from gossip, but liked to think that he was loudest with him.

The smaller stallion's breath became erratic; he was close. Macintosh closed his eyes and pressed in deeper, as experience had taught him. Umber pushed harder into the passenger's seat of the truck, muffling his ever-louder moans, and Big Mac felt him shudder as the hint of stallion wafting about the cabin became much more.

Macintosh's snout withdrew from Umber as the smaller stallion collapsed in contentment, sprawled over the seats. Smiling again, the larger stallion moved to lie down next to him, nuzzling his mane as he enjoyed the afterglow.

Umber looked up at him, panting slightly. "By Luna, you're fantastic."

Smiling sheepishly, Mac shrugged. "Just repayin' a favor."

"May be," said Umber, "but I don't know if I can compete with that. You're, like, the best at it in all of—"

"Big Macintosh, you get out here right now!"

The stallions jumped up rather awkwardly, Umber dropping right back down again to try covering himself as best he could. Macintosh peered through a window of the truck to see a particularly miffed Applejack glaring back up at him.

"I know you two are in there," she continued, "there ain't no reason to hide. 'Tain't anythin' I haven't seen before at those 'visits' you boys have in the barn. Now, get down here!"

Reluctantly, Big Macintosh toggled the door of the truck, and it swung open to reveal the two. Umber dropped out first, leaning down to try and cover up. Big Mac followed, slamming the door closed and circling round to block Applejack's view of the other colt, scowling at her.

"Now then," she started, "what were you two thinkin'? Doing it in a truck, out where anypony can see ya?" She directed her attention at Umber, who was desperately hiding behind Macintosh. "Not t' mention hear ya."

Macintosh scowled at her. "It's not like anypony's out today, and we're a might far from town. Everypony's got their apple orders fer this week."

"Everypony but Tolliker, you mean."

Umber's head popped out from behind Big Macintosh. "But he's out of town for the next week. He's getting fabric from Trottingham."

"That might be," said Applejack, "but he had to stop by the farm to get some supplies before he left, they don't have Apple family apples over there. Ya'll are lucky he didn't hear ya; I dunno if we coulda convinced him ya'll were 'redecoratin'' the inside of a truck."

She sighed, and her face softened. "I'm sorry. I don't disapprove or anythin', it's just…be more careful next time, sugarcubes. And try to be a little quieter," she added, eyeing Umber, "ain't no reason for them t' hear ya all the way in Canterlot.
"Now," she continued, "if ya'll two are a might done here, it's time for breakfast. Apple Bloom finally figured out how to make a decent apple pancake, and I ain't lettin' her big brother miss out on it. You can come too, Umby, I know how much ya like apples."

So the three ponies began to trot up towards the homestead, following the trail of a different, but still delicious, scent.

—|—

The streets of Ponyville weren't bustling, but they weren't abandoned either. Crème Brûlée, Caramel, and Toffee pitched their wares from the stall outside their forge. Haute Cuisine worked at the café, serving Bon Bon and Lyra a plate of alfalfa scones, while Pokey Pierce and Ace browsed the menu at another table, holding hooves. The Cakes walked towards another end of town, on a catering errand, while Pinkie ran through the streets playing tag with the twins.

All in all, it was an average day for the town, and Umber took it in as he walked towards his house. He passed by Ponet, painting a scene of Canterlot as seen from the central plaza of Ponyville, while Lily and Roseluck arranged a batch of daffodils and irises. Yes, perfectly normal.

He looked up. It was perfect weather, Central Weather Control hadn't declared any storms for the day. Pushing back the hems of his sweater, Umber's wings stretched and began to beat, lifting him up into the air, above a lone, fluffy cloud. He landed, and pulled out a small sketchbook he always had, hidden in a concealed pocket within his top (courtesy of Rarity's sewing expertise).

He looked around. Canterlot Mountain rose in the distance, elegant and regal as always, but Umber had already drawn that countless times. He wasn't planning to sketch anything that stretched before him; he simply needed the quiet and the peace. Dragging a pencil across the paper, he began placing lines, long elegant curves that seemed to gently wave in an invisible breeze. Her mane had been beautiful to Umber, the first time he'd seen her, but it was to all her subjects, as it should be. More strokes materialized, coalescing into a form of delicate posture but divine power: Princess Celestia of Equestria.

For Nightmare Night, Umber had spent three months on his costume, almost as much time as Twilight Sparkle, and it had been perfect. Much like Twilight, though, nopony had initially realized who he'd been, so he'd made it into a game. Whoever correctly identified his costume got a free portrait sketch. Of course, he hadn't expected Her Highness Princess Luna to arrive, and she had guessed immediately. He'd sketched her of course, it wasn't his best from all the trembling he did due to the rather intimidating presence of Her Highness, but she had declared it a "PORTAIT WORTHY OF A PLACE IN OUR ROYAL GALLERY," which he'd taken as a sign of approval. She'd taken it with her, and the next he'd heard of it was when he received a letter in the mail, from Princess Celestia herself, asking for a counterpart to be installed in the Royal Solar Artistry Gallery, along with a sum of three thousand bits.

Umber hadn't felt as lightheaded since that time Brolly had convinced him to join the "Hundred Mile High Club."

Here he was, though, sitting on a cloud, drawing an image of the monarch and goddess of Equestria. He'd forgotten his paints, but all he planned to do today was preliminary sketching. He'd decided to redo Luna's portrait and send the two in together, but they'd need time and inspiration to complete in any worthwhile way. So he sat, basking in the light of the sun as he honored its steward.

He sighed, and looked up at the clear blue sky. It was a peaceful day.

BAM!

Umber felt his pencil fly out of his mouth and into a nearby grass patch, and he fell for a few meters before extending his wings to halt himself. The sketch of Celestia began to float to the ground as slow as a leaf, giving him plenty of time to catch it and place it in his concealed pocket. His pencil, however, was another matter.

He heard an embarrassed sounding giggle from above, and looked up to see a slightly bashful Rainbow Dash.

"Uh…sorry?" she said.

Ah, so she had flown into him. Not surprising, she'd slammed into the side of the Apple barn during a stallion event only two weeks ago.

Here," she said, "you lost that, right?" She flew nimbly down towards the grass and nabbed the pencil in her mouth. Umber descended towards her, looking grateful if slightly irritated. "Thank you," he said, quietly thanking fate that the picture was undamaged. He could replace a pencil. "What were you doing?"

"Oh, just practicing for the Annual Aerial Athlete Alliance Race. Gotta prove I'm the best in Equestria again. You alright?"

He nodded in affirmative, before continuing, "But, I thought everypony knew you were the best in Equestria. What's left to prove?"

She smiled confidently. "Well, that is true, but I still have to go to competitions. It's not like everyone will believe I'm number one unless I prove it. Besides, it's fun."

"Uh huh." Umber looked down, thoughtfully, before asking another question. "So, in order to be the best at anything, you have to win a contest?"

"Basically."

"And this applies to everything?"

"Yep. Why, you got an idea for one?"

Umber smiled, blushing slightly.

"Maybe."

—|—

It was a momentous undertaking. Umber had called all the stallions of Ponyville into an emergency meeting to plan the event. Doctor Whooves was tasked to help Derpy and the rest of the Equestrian Mail Service deliver the invitations to every stallion in Equestria. The Night Guards were added as a supplement to secretly get the message to the colts of Trottingham, avoiding Tolliker's attentions. They reasoned that only about half of the male population would be interested anyway, Big Macintosh's skills were more legendary than was previously thought.

Then of course, was the selection of the judges. Representing Canterlot was the elegant and sophisticated Fancypants, who would be judging contestants' style (with blessing from Fleur, of course). From Cloudsdale would be Fire Streak, aerial extraordinaire and member of the most elite flyers in Equestria, the Wonderbolts, who would measure skill. Finally, last but most certainly not least, was every stallion's favorite colt, Umber, of Ponyville, and resident expert on passion.

It was certainly going to be an interesting competition.

—|—

Fluttershy sat above the streets and houses, looking out at the scene that stretched throughout Ponyville. Mayor Mare had been ecstatic at the influx of visitors, bringing in thousands of bits as they camped out in their long, winding line. The crowd had made Fluttershy nervous, though, so she had flown to the most secluded space at the moment: the Library balcony.

Twilight was inside, conducting some sort of scientific experiment that had to do with her studies. Pinkie was off helping the various restaurants of Ponyville feed the visitors, and Applejack was filling orders that flooded her nonstop. That left Rarity and Rainbow, both of whom Fluttershy hadn't seen today.

She sighed, and looked out at the lines of stallions. Some of them were very appealing, she had to say, especially a flame colored Pegasus with piercing turquoise eyes. She was too shy to introduce herself to them, though, and Angel wasn't anywhere near her, so she'd just have to sit here and imagine. They'd all come to see Umber anyways.

She sighed again.

"Enjoying the show, are we darling?"

Gasping in fright, Fluttershy whipped around to see Rarity eying her, a big smirk on her face.
"Well, I…um…I—"

"It's fine, darling," said Rarity, interrupting her, "they are quite fine specimens, aren't they? I'd go out to meet them, but I really just stopped by to get a book on suit making. With this many stallions in town, I can't afford not to dabble in colt's-wear, and I'm a tad rusty at it."

"Oh. Do you need any help sewing?"

"No, darling, I'm fine."

The door behind them opened, and Twilight came out onto the balcony, her mane slightly singed at the edges. "Uh, Rarity," she began, "you might not want to go in there for a while. I don't think that smell will come off anypony that touches it without industrial strength cleaners."

"Alright, darling. I guess I can stay a while…enjoy the view."

The three fillies gazed out upon the line and watched as it moved slightly, another stallion entering Umber's house at the far end of town.

"Why are all these ponies out here anyways? Is there some sort of party at Umby's or something?"

Rarity gave her a cynical glance. "Darling, why else would there be a long line of stallions at Umber's house?"

"You don't mean that they all came just for him?" she asked with a hint of disbelief. "Is he that popular?"

"You really do need to get out more, Twilight," said Rarity, "and as for your question, you'd be rather surprised. I've heard Umber's reputation has gotten him solicitation from as far out as the Griffin Countries. He even has a regular visitor from there."

"Wow," was all Twilight had to say.

And so the three resumed their appreciation of the vista, enjoying the peace and quiet (and abundance of fine stallion), at least until Rainbow Dash dropped in unceremoniously, crashing into Twilight and Rarity and knocking them into a pile in the corner of the balcony.

"Hey girlsh!" she cried, seemingly a little tipsy, "you've got to try this shtuff. I found it in the Apple barn."

Fluttershy gasped. "Oh no, Rainbow, you didn't! Applejack said she's been aging that cider for years now."

"Of course not, silly," she slurred, "I just got the cheapy stuff. Now, you, me, gonna go catch us some stallion tail."

"But…but…you know I'm not a one night pony!"

Rainbow rolled her eyes. "Then ask him on a date. Duh. You can be so dumb sometimes, Flutters, but I love ya anyways. Come on, that's it." Rainbow got the dubiously willing pegasus up in the air and soon they were gone, flying erratically down towards a group of stallions.

The two unicorns finally untangled themselves and got back on their hooves. "I say," said Rarity, "Rainbow Dash has never been able to hold her liquor. I'm sorry you had to see her that wa—what, what is it darling?"

Twilight was staring down at an entrance to Ponyville, looking a little panicky, and raised a hoof to point at a lone pony carrying a load of what looked like long rolls of fabric.

Rarity sighed.

"Well fuck."

—|—

Fancypants had to say, he had quite enjoyed himself. It was not quite as good as a night with Fleur, of course, but still enjoyable, and he was quite looking forward to some action with a "Big Macintosh" that the Ponyville judge, Umber was his name, kept going on about. He sounded divine.

That was not to be, though. Just as the large Apple stallion strode through the doors, two mares nearly knocked him out of the way, repeatedly shouting "PRISTINE!"

The chaos that ensued was nothing that he could quite imagine. Umber had cursed somepony not following schedules, and the stallions native to the town began to herd everypony into hiding places. As Fancy was being pushed towards a nearby bedroom, he overheard an argument between Umber and Macintosh.

"But you can't drop out, we have to prove you're the best. We can have somepony else watch Tolliker."

Mac smiled wearily. "You know as well as I do that nopony's as good at it as me. I don't need some big fancy title to be able to make ponies feel good."

"But—"

"Nope. You go on. I'll get Tolliker to the Apple farm. He's here 'bout the contest, I'm sure of it. I'll distract him, he'll be none the wiser." He nuzzled the smaller stallion's mane.

Umber sighed. "Fine. But when you're done, meet me here. We'll have a, uh, unofficial post judging. I'm sure our guests," he gestured towards Fancypants and Fire Streak, "will appreciate it if you give us a taste of your talents."

"I'll be glad to."

And with that, he was off, and after the chaos settled, the contest resumed.

—|—

The night shone with the light from the billions of stars that shone in the sky, and the great white surface of the recently featureless moon. The moonlight cast the truck in a pale glow that offset its bright red paint, and gently illuminated the two ponies as they worked.

"So, I just unscrew this bolt, and replace it?" asked Tolliker, who was sitting near a wheel of the truck.

"Eeyup." said Big Macintosh.

The unicorn's horn lit up, and a few parts exchanged themselves within his telekinetic grip. He heard a light click and rose. "Am I done?"

"Eeyup."

Tollie turned towards him, a big grin plastered on his face. "So, how'd I do?"

"Ya did great. I'd say maybe even," he pulled a light blue ribbon from his yoke, "first place great."

Mouth dropping open in surprise, Tolliker wrapped his forehooves around Macintosh's neck. "Oh, tahnk you thank you thank you thank you! I've got to go, but I won't forget this. I'll get you a new cowpony hat. Or maybe a fedora. Or a dress hat. Or an ushan—"

"That's fine, Tollie. You jus' go on home now."

The hatter smiled again. "Oh, okay. Still, thank you again!" He picked up his bag of fabric, which was nearby, and began to trot all the way back to his shop.

Macintosh watched his form fall over the horizon, before beginning his own trek back into town.

—|—

Umber was asleep on the couch, his sweater thrown over onto a nearby table.

"Umby, you awake?"

The artist turned a little, and sat up upon seeing his visitor, cracking his neck. "Hey, Big Mac. How was it?"

"Fine. He didn't 'spect a thing."

Umber smiled. "You always did know how to get rid of him best."

They sat in silence for a moment, before Big Mac continued. "So, how was the contest?"

"Oh, some pony from Fillydelphia won, I dunno. " He turned to look at Mac. "He was nothing compared to you, though."

The bigger stallion let his chin rest on Umber's head, and stayed silent.

"No, he was nothing compared to you."

—|—

Next week's episode shall be entitled "Handkerchiefs, a Reference Guide."

Next Chapter: S1E3: Handkerchiefs, A Reference Guide Estimated time remaining: 22 Minutes
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The Trials and Tribulations of Tolliker

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