Twilight cleared her throat. “In any case, back to backgrounds. The basic idea is that it gives a little snapshot of what your character was doing before they became an adventurer. Spike, you mentioned you were going for Acolyte?”

“Yup.”

“So that background would describe how that upbringing affected his character.”

Rarity nodded as she looked through the list of backgrounds. She hovered over some longer than others before eventually making her choice. "It seems that the most logical fit for me would be the Outlander. That's rather the idea of a Barbarian, isn't it?"

"Historically, that's true," agreed Twilight, "but of course you can pick any background you'd like."

"In any case, that's what I'll stick to. Let's keep things simple to start with, shall we?"

Twilight nodded. "Speaking of keeping things simple, and Ponies who rarely do - Pinkie, you look like you've come to a decision."

Pinkie was in fact bouncing in her seat, like a foal who had guessed the answer to the teacher's question. "Yup! I'm gonna be a sailor."

"A sailor, huh?" muttered Twilight as she jotted the choice down. She looked back to Pinkie and spoke up. "That's not what I would have imagined, but I can see how it works."

"I'm a different girl in every port!" beamed Pinkie.

Rarity smirked wryly. "I'm not quite sure that's how it goes, darling."

"How what goes?" asked Spike. Rainbow Dash and Applejack giggled, while Twilight turned slightly red.

"I, uh", prevaricated Twilight, "I'll tell you when you're older."

"Oh, OK." said Spike innocently, "Like that time I found a store that sells hoof-cuffs?"

The giggling from the peanut gallery intensified, and even Rarity and Fluttershy could not resist joining in. "Yes, Spike", said Twilight as she turned approximately the shade of Big Macintosh on a hot day, "exactly like that." She adjusted a few sheets of notes theatrically. "On to the next of our stalwart heroes. Fluttershy, how's your backstory coming along?"

"Oh, I'm quite proud of this, actually. I'd like to have the artisan as my background. See, I used to be a, uh, candlestick-maker but then one day I got bored of it and I went off to have an adventure."

"Sounds like an interesting character. Do you have a name?"

"I'm working on it. You can just deal with the others until I come up with one though, I wouldn't want to hold anypony up."

Rainbow Dash sat up a little straighter in her chair. "Hey, Twilight, you mentioned Monks were, like, those guys in secret hidden temples, right?"

"A lot of them, yes."

"So I'll take hermit. That's what that is, isn't it?" Rainbow was fairly confident she had the word right, having seen it in a number of pulpy adventure novels. It seemed to mean either shut-in or weirdo, and she liked her odds.

"Yes, hermits are people who live off away from the rest of society. Back when I was more of an introvert, I used to think of my library in Canterlot as my hermitage."

"Well ya had Spike, didn't ya?" asked Applejack as she gestured to the dragon in question. "Not quite a hermit."

"No, that's true. In fact, Spike here is probably the main reason I wasn't even more of a shut-in than I was when you met me."

Spike made a gentle gesture with his hand as if to brush off the praise. Twilight didn't have the heart to tell him it was the sort of thing that only really worked for a girl. "Aw shucks, you'll make me blush."

"Any time, my number one acolyte. Applejack, you're the last one without a background. I imagine your character didn't spring fully formed from the head of Faust?"

Applejack chuckled. "Well she might tell you that, even if she didn't. She's a charlatan." Applejack pronounced the word as if she were talking about a man named Charlie.

Rarity could not help but correct her. "It's pronounced with a softer ch. More like a sh, really."

"Well how come it ain't spelled with a sh, then?"

"It's from Prench, originally." Rarity struggled not to preen too obviously, though any mention of Prance made it a struggle.

Applejack shrugged. Prench folks did things funny, and that was explanation enough in her mind. "Fair enough. I figure it means a Flim Flam kinda Pony."

"That's about right. If I recall correctly, there are some details about that background that we'll have to work out in private, but for now I think we're all set. Now it's onto our gear! Fluttershy, you've already chosen a lance, but the fighter starts the game with enough weaponry to start her own war."

Fluttershy nodded. "I'd like the light crossbow and a warhammer. Oh, and the explorer's pack."

"I'll tell ya what, Twilight, I'm real glad those premade backpacks are all there. I'd hate to have to try and pick all that stuff out one by one."

"That's something I dislike about 5th edition, personally." Said Spike, "I always feel like half the fun of O&O is putting your character together just right. But we've got a big enough group that I'll just go with the default gear this time."

The rest of the group chose their starting gear, some ponies taking longer than others. Eventually, even Rarity was satisfied that she had her character just so, and Twilight felt ready to begin the game proper.

She cleared her throat from behind her Ogre Queen Screen. "I'm going to stick with a winning tradition and start us all off in an inn. We'll get to what you do inside in a moment, but for now why are all of you spending the evening at The Leaping Wizard? It's not exactly the fanciest place in the world - not horrible, but not the kind of place you'd bring your parents either."

Pinkie made an amused noise. "I'd like to hear the story behind that name. Oh! Speaking of stories, maybe that's why I'm there. Does the inn have a bard or a skald or anypony like that?"

"It does now", said Twilight, scratching out some of her notes and hastily writing in replacements.

"As for me", mused Rarity, "I imagine that a barbarian isn't welcome in some of the finer establishments. Ragna's here because this is the nicest place she can get a room."

Fluttershy took her turn to speak up. "A barbarian coming to town sounds awfully scary. I'm there to keep an eye on Rarity and make sure she doesn't raise any trouble." Rarity leered at Fluttershy and raised her forelegs up ready to pounce. The rest of the table giggled.

"Excellent!" Beamed Twilight. "Lastly, what are a monk and a cleric doing at the Leaping Wizard?"

"We're arguing about philosophy." Deadpanned Spike. Rainbow sniggered.

Twilight rolled her eyes. "Well, it's as good a reason as any. OK, so you're all in the tavern one evening, when…"

+++

The gentle, insistent rain drummed against the windows of the Leaping Wizard, as it had all night. All of the inn's regulars were seated at their accustomed spots, along with a few newcomers and outsiders taking shelter from the weather. Farmers swapped jokes and anecdotes each had heard a dozen times before over their pints, while a storyteller regaled all who would listen with the tale of how prince Haygen was kidnapped by Griffons.

A Changeling sat listening, idly turning one of her hooves into a paw and back. A hulking barbarian towered over the bar, while a knight tried and failed not to look like she was spying on the outsider. Another foreigner was sitting with a priest in one corner of the room, the conversation veering between religion and beer.

On the other side of the tavern, a slick-looking Pegasus sat down at a table with a Griffon wearing a dark hood. The Pegasus' pale blue coat and claret mane contrasted with what little was visible of the Griffon himself. "Howdy, Lars. How's business?"

Lars the Griffon looked up from his drink, though he kept a talon wrapped around it protectively. "It's been better, Wandering Eye. Seems all the low-hanging fruit around here's already been picked."

Wandering Eye shrugged languidly. "Heights never bothered me none." She shook her wings meaningfully. "If there ain't no easy jobs, that must mean you know about somethin' dangerous you're too chicken to go and do yourself."

"Don't bring race into this, it's crass. But you're right. As a matter of fact, I know about a potential big score. You're probably not going to fancy it any more than I do, but you might as well know all the same. Have you ever heard of Castle Innskar?"

Wandering Eye paused for a second. The thunder rolled, sounding as if it were right above the tavern. "Reckon I have. Didn't think anypony lived there these days."

"No pony, no.", agreed Lars, "The castle's latest inhabitant is a horse of a different colour."

"What's that you said about crass?"

Lars shrugged underneath his voluminous cloak. "I'm sorry, I couldn't resist. Word has it that the new master of Castle Innskar is a Vampire. I know it sounds a little far-fetched, but I've heard this from people I trust implicitly."

"Who do you trust, anyhow?" asked Wandering Eye as she raised one eyebrow.

"People who are bad at lying."

Wandering Eye laughed into her drink, and spent the next few seconds trying not to choke on it.

Lars thumped her on the back. "Even if you are going to go for it, I wouldn't recommend trying something like that alone." he said meaningfully.

"Who said anything about being alone?" asked a newcomer. An Earth Pony with a dark grey coat and a brown mane stood over the table. She was dressed in strange, foreign clothes, covered in all manner of sigils and signs. Next to her stood a Zebra, dressed more recognisably as a wandering priest of Rojobrasa, Alicorn of Life. The familiar sign of the interlocking wheels stood out in gold against his white robes. "Sorry to interrupt, but I heard you talking about something that sounded real interesting. Dikembe and me want in." She turned to her erstwhile conversation parter. "You do want in, right?"

The Zebra nodded, his expression stern. "You've got that right. Vampires and their kind are an insult to Rojobrasa."

The foreign pony nodded proudly. "Well there you have it. You have a Vampire problem, and we're willing to help - for a share of the proceeds, of course."

Wandering Eye looked at the pair of them skeptically. "What kind of monk goes out lookin' to make a profit?"

"The kind who wants to eat." She stuck out a hoof, and Wandering Eye shook it dubiously. "Name's Thunder. Pleased to meetcha."

Wandering Eye looked from one of them back to the other, and she found it harder to tell who she thought was the bigger fool. "And you really want to go huntin' for Vampires with folk you just met?"

"Well I sure do!" announced a new voice, full of bubbly cheer. The Changeling had wandered over, and inserted herself in between Thunder and Dikembe. "That sounds like a blast! I'm Buzzer. I'm a Changeling - you could probably already tell that - and I-"

Wandering Eye slammed a hoof down on the table. "Hold it right there, missy!"

"Buzzer."

"Sure. But hold it right there anyway. How'd y'all overhear us? We was bein' quiet, or at least I thought we was."

Buzzer giggled. "Oh, I just gave myself dog ears, and then I could hear you just fine."

"What kind of dog?" Asked Dikembe.

Suddenly, each of them was struck with an irresistible feeling that they were getting off-topic, and that they ought to return to the matter at hoof. Lars cleared his throat slightly awkwardly. "Are there any others in this tavern who want to interrupt my conversation?" he asked as he rolled his eyes.

The barbarian lurched up from the bar and loomed over him. Next to her, the knight abandoned all pretence of staying hidden and wandered over to join the group. Thunder looked the two over appraisingly, pondering whether or not she could beat them in a fair fight. She rather fancied her chances. The group of six fell into a hubbub of chatter and idle musing, with Dikembe and Ragna's voices clearest in the noise.

"Very well!", declared Lars, his voice cutting through all others, "It appears you have yourselves an adventuring party. Now, which of you knows how to get to Castle Innskar?"

The thunder rolled again, louder than before. Eventually, the knight spoke up. "Um, I don't think any of us do."

Lars chuckled. "I thought as much. Well, I'd be happy to give you a map…for the low, low price of 20% of your loot."

"20%!" choked out Dikembe, "Why, you no-good, dirty rotten…" The nameless knight had to hold him back.

Wandering Eye held up a hoof for peace. "Now hold on a second, we can be reasonable about this. Lars, we've done business before, right?"

"Sure, lots of times."

"And have you ever asked for a slice of the pie that big?"

Lars scratched one talon under his beak. "There was that time at the pyramid of Nephren-ka…"

"And was you takin' a fifth of the booty despite bein' one of seven?"

Lars' talons scraped along the tabletop. "Alright - fine! I was being greedy! You can't blame a guy for trying, can you?"

"I guess I can't."

Thunder groaned. "OK, look, are you two going to sit there and talk about old times all night? Some of us have adventures we want to be on. Lars, why don't you just take a 10% cut and be happy with it?"

Lars sighed. "Very well. That will have to do." He reached into his cloak and pulled out a rolled-up map. He slid it across the table to the waiting party. "This will show you the way to Castle Innskar. I look forward to meeting with you again - if all of you make it back!" With that, he stood and strode out of the Leaping Wizard, pulling his black hood up as he stepped out into the stormy night.

"That was neat", said Buzzer as the rest of the party looked over the map. "So now what?"

Once again, the six of them suddenly felt strongly that they were tired, and ought to go to bed to begin their adventure bright and early the next morning. They paid the innkeeper with only a bare minimum of arguing over prices, and went off to their separate rooms. They would wake refreshed, and ready to begin their perilous quest.

Author's Notes:

And so the quest begins! From now on, the story will be divided between the "real world" of the cast and the world of their game. Hopefully the game section was easy enough to follow.