Better you than me, dearest. 

Laila's next step after re-summoning Jay is indeed packing up her things, or more accurately, haphazardly scurrying around the cramped attic bedroom above her teacher's workshop and gathering up her small number of personal possessions. Gather coins and biscuits into robe pockets, check; strap knife to leg, check; shove notes and inkwell-case and half a block of cheese into embroidered satchel, check; don dramatic swooshy hooded travel-cloak, check; pick up painstakingly carved staff, check. Ta-da, a wizard prepared for travel. 

Probably. 

You look very regal, Jay says loyally, regarding her from his perch on the recently-cleared desk. Where are we going, again? 

Well, first, the guard post, the Captain said he had a couple other people who wanted in, but after that -  

She scribbles a note and pins it with a bit of clay to the bookshelf:

On a quest, paid the rent through Solstice, send if you need anything -- L 

- after that, we're getting on a boat. 

A boat! Gosh! What! So exciting!!! 

Laila loves her ridiculous tiny thrill-seeking fae creature very much. 

It's a short walk down the road from the market district to the guard captain's post, where she promised to show up around sunrise. Along the way, she fidgets with the straps of her satchel and her staff, trying to make them sit nicely and not shift too much when she moves her shoulders. Can't have your outfit falling apart while you're trying to look like a professional. 

"Good morning!" she greets the door guard sunnily, earning a vague, slightly sleepy wave in return as she glided by, and then stops dead in her tracks. 

Excuse me, is that - 

"Light be upon you," says the demon. 

She rather towers over the watchmaster, with broad shoulders, heavy-looking horns, and wings that, even politely folded, nearly brush the ceiling. However, she is smiling in a very sincerely friendly fashion, and has a bright golden sun-disc emblazoned on the front of her tabard. It clashes bizarrely with her faintly scaled red skin and short, acid-purple hair. 

Next to the big demon there is also a smaller one, almost offensively orange, wearing handcuffs with a chain stretching some distance and fastened to her belt. Unlike his compatriot (or perhaps jailer), he has cloven-hooved goat's legs, and is just about Laila's size, aside from the tall, spiralling horns. The distinctly less friendly way he is smiling makes it very hard to ignore the fact that he has fangs that could probably tear a small animal cleanly in half.

??????? pit fiend ?????????????

" ... and ... to ... you?" hazards Laila, blinking rapidly. 

"Delmirev Serra, sword of Lathander, at your service," with a polite incline of the head. "I am told there is a woman who may need to be rescued from pirates?" 

Jay has obviously never met a pit fiend in person, but this woman sure does look like the pictures in that one book. He flutters anxiously on Laila's shoulder. 

Laila has several questions, but the first one that comes out of her mouth, somehow, is, "Wait, isn't Delmirev the northern dragonkin clan?" 

" ... yes?" 

“She thinks she’s a dragon,” stage-whispers the prisoner.

Serra shoots him a glare only slightly less poisonous than her hair. “My parents were proud children of the clan Delmirev and so am I,” she insists, crossing her arms.

Okay! Great! Definitely not in any way questioning that!

"It's lovely to meet you, Serra. My name is Laila and I am a student of the arcane. This is my familiar, Jay. I don't know much more than you about the situation, maybe the watchmaster could enlighten us?" 

The watchmaster can totally do that! He is definitely not in any way freaked out about how he asked the church of Lathander for a paladin and they sent him demons. Nope. Totally fine over here. 

He explains at length that, a ways off the coast, there is an island containing a fairly well-fortified pirate town. This has historically been largely ignored by their local leadership - it's far enough away that most of their attacks are focused on other neighboring polities, and merchant ships mostly just sigh and price the risk of pirate attacks into the cost of sailing through the area. It was been rumored that the pirates have a young dragon working with them, and unfortunately, the rumors were confirmed at the same time as the situation abruptly became much more urgent: the mayor's daughter, always something of a free spirit, had apparently encountered the dragon and some of its minions, tried to seduce the dragon, and been kidnapped. Naturally, they now suddenly had funding to rally together a fleet, but scouts had reported that a direct frontal assault would be fairly unwise, because of the surprisingly well-manned signal towers. 

His clever idea, therefore, was to send a small strike team in first to disable the night watch on one side of the island, and then mount a surprise attack. 

"That kinda sounds more like an organized ... town ... than like a bunch of pirates," objects Laila. "How sure are we that they aren't mostly innocent?" 

"Kidnappers and attackers of merchant ships are not innocent." 

"Yeah, but that's just the people that leave the town, I mean, I'm not saying I think it's entirely ethical to live in a town economically based on piracy but the people who live there are probably mostly basically civilians." 

"Surely our honorable fleets would not harm civilians." 

"I really hope not!" 

Pointed look at the watchmaster. 

"Of course not," he assures them. "Enemy combatants only, and our primary goal is distraction and rescue."