It was an opportunity, Gregory had been told, which most of Canterlot would die to have. Yet here he was, trying to not look ungrateful as Luna dragged him from store to store and encouraged him to dress in all manner of outfits.

“No,” Gregory said from behind the curtain in the dressing room.

“How can you say no if you haven’t even tried them on?” Luna demanded from the hall, ignoring the many ponies poking their heads out to steal a glimpse of the queen and prince.

“Like this. NO!” Gregory retorted.

“Come now. It’s the latest fashion from celebrity seamstress Rarity,” Luna encouraged as she levitated the clothes hanger holding the pair of lacey black panties. “All the up-and-coming celebrities are wearing a pair.”

“Perhaps it’s the color,” Blueblood suggested, trying not to imagine what Gregory would look like in some of the more suggestive articles he’d seen. “Perhaps navy blue would be better? With your coat, it should blend into your fur to the point of being nearly invisible. That way you achieve the allure of keeping your stallionhood hidden without being too obvious about it.”

“Uh uh.”

“But…” Blueblood pleaded.

“Never gonna happen.”

Luna had one last idea. “Not even under a pair of dress slacks?”

“No!” he said finitely.

Luna and Blueblood gave simultaneous sighs of defeat before meeting one another’s eyes. Both had put up a valiant effort to dress the stallion in lacey underwear, but his stubbornness proved to be an insurmountable foe. The royals shared a nod of quiet respect, similar to that of fellow warriors on the field of battle, before departing for garments that would more likely meet the picky stallion’s tastes.

The royals had been at this for over an hour and the crowd outside the store showed no signs of breaking up any time soon. While the guards they brought managed to keep most ponies away with little more than a mean look, the pair still had their shopping interrupted by brave ponies running up and asking for autographs and the like. They’d picked out a store in the more common area of Canterlot to avoid being harassed by nobles and so far it seemed to have worked.

“I still say he’d make a remarkable first impression in one of these.” Luna held up the latest of Gregory’s rejects. It was a pair of stallion’s trousers, but with a hole cut out in the groin area for the sheath and balls to poke through. “It’s both classy and functional for when you meet that sweet young filly for the first time.”

“I’m afraid you and I have different interpretations of what qualifies as class.” Blueblood shook his head. “That sort of thing screams to the world that he’s just a cheap whorse looking for some quick fun.”

“Cheap?” Luna was aghast. “We would never suggest that dear Gregory is cheap! But what’s so wrong about announcing his status as an expensive stud?” She emphasized.

Blueblood stared up at the alicorn in disbelief. “Was that really how they used to do things in your day?”

“But of course.” Luna said in equal disbelief. “None of this pitter pattering around with innuendo and subversion. When a mare liked a stallion, she’d present her plot for mounting. And when a human pony served as stud or brood mare for the crown, they wore it as an invisible badge of honor; and sometimes not so invisible.”

Blueblood just shook his head. “I find that hard to believe. According to him, the majority of human cultures have been almost entirely monogamous for several thousand years. On top of everything else they go through, I simply don’t see the human ponies of the past so casually casting off their cultural norms.”

“For a former human, he holds some rather misguided beliefs regarding his people’s history,” Luna said as she examined another line of slacks. “For the longest time humans were the more primitive of our cultures in numerous ways. We remember a time when human ponies looked upon a cobbled road as if it were equal in wonderment to pony magic. They did not have the same monogamous taboos drilled into them, and thus were more willing to accept the nature of pony herds.”

“You don’t say.” Blueblood was intrigued. He’d always been enthralled by stories Celestia had told him of humans coming to Equestria. Despite their seemingly primitive nature, early human ponies showed remarkable levels of ingenuity and cleverness. Many of Equestria’s technological and social developments could be traced back to human ponies and their descendants, which was exactly what made them so coveted and why he needed to be presented as an asset of the crown as soon as possible.

Blueblood glanced over his shoulder at the changing room. Beneath that unassuming nature lies the potential for one of Equestria’s next greats, he thought. Despite his timidity, the unassuming Gregory held a tremendous amount of power, or rather, any pony that held him held his power.

There was no denying that Blueblood found such power attractive, but more than that he simply liked Gregory. Having no knowledge of Equestria, Gregory had no compulsion to grovel before the princes, princesses, or queens as so many others. He wasn’t a yes mare, always agreeing with the pony in highest authority even when they went out of their way to sound stupid. He wasn’t a gold digger, being very frugal in nature. And he wasn’t a brownnoser, despite Blueblood’s fantasies. Gregory, once he got over his bashfulness, was not afraid to speak his mind. He was honest in his interactions and held a bottomless well of interesting stories from the human world, which he took much delight in sharing. No matter the circumstance, Blueblood never failed to find Gregory’s presence an absolute delight.

“And then we return from a thousand years of banishment to learn that humans have surpassed ponies in ways never imagined,” Luna continued. “Coal for train engines, airships that fly faster than ponies, and I still don’t fully grasp this internet he speaks of, but it sounds amazing.”

“Yes,” Blueblood said dreamily. “He is.”

“What?”

“What?”

“What did you just say?”

“Nothing.”

Luna narrowed her eyes accusingly down on the stallion. “You know I have seen your dreams, little prince,” she flashed a toothy grin. “There is nothing you can hide.”

“Y-you look in on those kinds of dreams?” Blueblood asked as his cheeks reddened.

“Glance would be a better word, as I do not make a habit on needlessly intruding on such private fantasies. However, an instant in the dream realm can last a remarkably long time.” She glanced around conspiratorially and leaned in closer and whispered, “As does your perception of Gregory’s endurance.”

Blueblood’s tongue caught in his throat.

“But you’re not too far off,” she teased. “Legends of human pony stamina are not as exaggerated as most seem to believe.”

Blueblood licked his lips as his imagination ran wild.

“If anything, tales of their exploits do not do them justice.” Luna grinned before falling over with laughter. At his confusion, she pointed between the prince’s legs where the desired result had been achieved. Thankfully Blueblood had managed to hide his shame behind a marnnequin stand before Gregory emerged with his latest outfit.

It was a simple black vest with a white undershirt and black dress slacks. The outfit seemed a little generic, nothing to make him stand out, but it also seemed suitable for him. However, Gregory being a simple wall flower was not a destiny his royal care givers were willing to tolerate. The look Luna gave Blueblood said as much, that Gregory must be made to mingle with the ponies who would have a vested interest in his future.

***

After buying a single outfit, now carried in Luna’s magic, the prince, queen, and stud-to-be walked leisurely down the streets of Canterlot towards their next destination, chatting amicably as guards followed in tow.

“Let me get this straight,” Luna continued. “The game is that you give any prompt you can think of-”

“Yes.” Blueblood nodded, glad that Luna understood his explanation.

“-no matter how obscure, simple, or silly-”

“Right again.”

“-and Gregory is able to turn it into a story?”

“More like I’m retelling from when I grew up,” Gregory corrected.

Luna frowned in thought as her head swiveled about. A boast such as this needed to be tested. “So, if I were to give you the prompt of,” she spotted an appliance store, “toaster oven?”

“I’d tell the tale of The Brave Little Toaster,” Gregory answered proudly. “It’s about a group of appliances that venture across the wilderness in order to find the master they fear has forgotten them.”

Luna blinked in surprise. “To be clear, this is set in a world where the forces of nature run wild with no one to tend to them?”

“That’s right.”

“It sounds like a tale most harrowing.” Luna grinned excitedly.

“It really gets ya in the feels in places.”

“Feels?” Luna asked.

“Human slang for feelings,” Blueblood answered, proud of his knowledge. “I think it’s quite cute.”

“Yeah, but it’s also got a lot of visual stuff I’m not sure I can do justice to,” Gregory said apologetically.

“Nonsense.” Blueblood waved his hoof. “Your narrative abilities have proven quite vivid thus far. I’d dare say you’d give the orators of old a run for their money.”

“Speaking of money,” Luna interjected. “Have you been giving any thought to acquiring a job?”

“A little.” Gregory shrugged. “I’m not exactly what you’d call skilled labor.”

“There’s no need to feel rushed, of course,” Blueblood insisted. “The crown is more than willing to support you for as long as it takes to get on your hooves. That said, I understand the palace mail room is a bit understaffed at the moment. Perhaps you can find something there to occupy your time until you know what you want?”

Gregory chuckled. “Where I’m from you have to take this really elaborate test to get a job at the post office.”

“The benefits are quite coveted, but this’ll only be a part time position for you,” Blueblood informed, leaving unsaid what Gregory’s real job would be. “Think of it as training in pony interactions for your real duties.”

Gregory grimaced, knowing full well what Blueblood was referring to. However, before he could once more express his apprehension with such a task, a pink earth mare materialized out of hammer space.

“Hiiiiii Luna!” She greeted with the volume of an air horn.

“Pinkie Pie,” Luna greeted right back and pulled the mare into a hug.

“And hello to you too, Blue.” She waved from the confines of Luna’s grip.

“Charmed.” Blueblood nodded back. “What brings your pinkness here this fine day?”

“My pinkness is here to help my sister Maud move into her new apartment,” Pinkie said, bouncing out of the hug and continuing to bounce in front of her royal friend. Despite the debacle at the Gala many years ago, Twilight had insisted that the prince wasn’t such a bad guy. Rarity still held a small grudge, but the others were willing to at least be polite, save for Pinkie who was just too Pinkie. “She’s trying to get a job at Canterlot University as a teacher in geology. We kinda got separated on the way, so now I’m waiting for her to find me.”

Gregory bobbed his head in time with Pinkie’s bouncing, trying to see if there was a windup lever somewhere.

“Maud Pie is moving to Canterlot?” Luna asked. “Whatever for?”

Pinkie stopped bouncing and pressed her cheek against Luna’s, whispering conspiratorially. “It’s a secret.”

Blueblood caught Gregory’s look of confusion and smile sympathetically. “Pinkie Pie. Friend of the crown, hero of Equestria, former Element of Laughter, and current member of the Council of Friendship.”

Gregory tilted his head. “Would you be insulted if I said half those things sounded like they were made up, like for some sort of marketing plan for little girls?”

“Not at all,” Blueblood said graciously. “Would you be afraid if I said those were some of the least interesting aspects of this mare?”

Gregory glanced between the prince and the pink mare. “Somewhat.”

“Oh. Ohohohohohohoh!” Pinkie exclaimed as she ran up to Gregory. “Who’s this? A new friend?” She gave a sideways glance at Luna, accompanied by a shit-eating-grin and suggestively waggling eyebrows. “Or his he your new colt toy?”

“Gregory is no such thing,” Blueblood sighed in exacerbation. He was not in the mood to deal with the pink mare’s pinkness today. However, he quickly recovered as he recalled the mare’s other abilities. “However he is in the market to make some new friends,” he added suggestively.

It was brief, but Luna’s smile widened ever so slightly as she gave her nephew a nod. This, she thought, is how the maneuverings of the court should be handled.

“Friends!?” Pinkie exclaimed from about four feet in the air. “That’s my specialty. I just love-love-love making new friends.”

Before he knew it, Gregory’s hoof had been seized by the sentient glob of cotton candy and was in the process of being shaken right off. He tried to pull away, but she seemed utterly oblivious to his plight.

“Hi Gregory. My name’s Pinkamina Diane Pie, but most ponies call me Pinkie,” she said as she finally released the stallion’s sore hoof. “Can ya guess why?”

It took Gregory a moment to realize he’d been asked a question and he rubbed his foreleg. “Um, because you’re… pink?”

“Got it in one,” Pinkie congratulated. “You must be really smart.”

Gregory frowned, unable to determine if she was being genuine or condescending.

“By the way, why are you wearing pants?” Pinkie casually asked as she leaned to the side for a better view of the stallion’s rump. “Not trying to hide something, I hope. Hiding stuff from your friends is never a good idea.”

Gregory took a step back, overwhelmed by the cotton candy’s bubbly personality and not liking the idea of her staring at his backside. “I, um…”

And just like that, Pinkie’s jitteriness promptly fell to a more manageable level. She’d identified this pony as an introvert and adjusted her friend-making strategy accordingly. “Sorry.” She traced her hoof along the concrete in embarrassment. Her mane had deflated slightly, just enough to make her look smaller and less imposing. “Didn’t mean to frighten you like that. I just kinda get carried away when I meet new ponies.” She offered her hoof apologetically.

After a moment’s hesitation, Gregory reached out and was relieved to be met with a much more gentle hoof shake.

“Better?” she asked.

“Better.” Gregory smiled.

“I’m glad.” It took all of Pinkie’s willpower not to cartwheel around in celebration. “Where are you guys heading, anyway? Mind if I join you?”

“We were just doing a little shopping for Fancy Pants’ charity function tomorrow, but what about your sister?” Blueblood asked. “I thought you were looking for her.”

“Oh silly-billy,” Pinkie said with a dismissive wave of her hoof. “I’m not looking for her. She’s looking for me.”

“And now she’s found you,” came the apathetic reply from behind Pinkie. It was an earth mare with a bluish gray frock that hid most of her body. She had gray fur, just like Gregory, but her mane was well-trimmed and had a dull violet color. Her eyeshadow was the same shade of violet and her half lidded turquoise eyes beheld the scene before her with their usual lack of discernable emotion.

“Maud!” Pinkie screamed and torpedoed into the new mare, who remarkably withstood the full force of the blow without so much as a nudge. “I missed you,” she said, clinging to Maud’s head like a face hugger. “Where were you?”

“At the apartment,” Maud answered plainly.

“Huh. The one place I didn’t check,” Pinkie admitted as she slowly descended back to the ground with the speed of a feather.

As Gregory wondered whether or not the pony shaped piece of cotton candy had some sort of grudge against the laws of physics, his attention was caught by the new mare’s eyes. They were half lidded and unfeeling, but also had a depth to them that Gregory couldn’t quite discern.

“Hello, your highnesses,” Maud said dispassionately as she bowed to the royals.

“A pleasure as always, Maud,” Luna beamed.

“I trust your parents are well?” Blueblood added.

“Still working the rock farm,” Maud answered as she faced Gregory. “And who might this be?”

“Oh. Silly me,” Pinkie giggled. “This here is Gregory. He’s my new friend and he’s going to Fancy Pants’ party tomorrow, just like you.”

“Oh?” Luna asked. “It’s been a while since a Pie has last attended a Canterlot party.”

“I organized a flash rave just two weeks ago,” Pinkie said giddily.

“The invitation was for my parents,” Maud said dully, never taking her eyes off Gregory. “But they were busy and suggested I try it out to get a taste of the Canterlot night life.”

“Splendid!” Luna cheered, noticing the way both gray ponies were staring at each other. “Thy sister Pinkie has offered to accompany us on our shopping venture. Wouldst thou be interested in doing the same?” Luna had a bad habit of slipping into her old-timey talk whenever she got excited.

“I’d like to, but we’ve still got some unpacking to do,” Maud said dispassionately, never letting her eyes stray from the gray stallion for too long.

“Oh well,” Pinkie said as she drooped her head low, only to pop back up the next second. “I guess that means we’ll just have to see you at the party tomorrow.” She beamed at Gregory.

“Y-yeah,” Gregory stuttered, never taking his eyes off Maud. “I guess I’ll, um, see you then.”

“I hope so,” Maud said evenly as she turned and departed. It was a shame the earth mare was wearing a frock because her tail, intentionally or unintentionally, was flagging ever so slightly off to the side.

Unbeknownst to Gregory, Luna and Blueblood shared a knowing smile.

Author's Notes:

Just a bunch of harmless meetings that I’m sure will have no long term impact on the story. There was a fun bit of cultural clash regarding the panties and hints are dropped for the larger meaning I was alluding to the first time around.

Also, could someone please give me some constructive feedback? I sincerely want to improve my writing and I can't do that if people don't tell me what they dislike.