A/N: Hey guys! This story comes from an AMAZING prompt by from RosexShaffer on the Glee AU meme. It's mainly Brittana, but all the characters will be in here, so there will be some side Klaine, Tike, Samcedes, and Finchel/Faberry. Quick disclaimer: this takes place in the 1700s, but most of my information about the time period comes from Pirates of the Caribbean. Some of the things the characters say or do may not be true to the time period. I've done my best to keep it accurate while still making it enjoyable to read and trying to stay true to the characters' voices (this will be especially true in their language! I am certain that pirates didn't talk this way, but the Glee kids do, so I want them to be in character, know what I mean?) Anyway, I just had to get that out of the way-thanks for reading!

This story is rated T (for now) but there could be some potentially triggering material since abuse is a major theme (for the most part, it won't actually be happening, but it will be talked about and the aftermath will be described). But I promise, this will NOT be all darkness and angst. It's mostly romance/humor/adventure so enjoy.

Chapter 1: A New Purchase

"Ship on the horizon!"

Santana jolted at the sound of Tina's voice, waking up from her light nap. For a second, she looked around the room trying to figure out where she was. The captain's cabin. Right. Which meant that she was the captain. Which meant that Tina's call was meant for her. Shit. Santana swung her legs over the edge of her bed and stuffed her feet into her boots just as her door flew open.

"Did you hear?" Blaine asked breathlessly, poking his head through the door.

"Of course I heard," Santana said, lacing her boots and reaching for her spyglass.

"Oh," Blaine said apologetically. "Sorry. This first mate thing is kinda new, I'm not sure how much I should actually be doing."

"Just...tell me things I don't already know," Santana replied, flattening her messy hair with her fingers. Blaine watched her curiously.

"Were you sleeping?" he accused.

"No," Santana replied hastily. "I was working."

"On what?"

"Stuff," Santana said shortly. "Schuester left a great big mess, you know that? That man had no plans."

Blaine nodded. It was true—and part of why they had mutinied him in the first place, less than three days ago. Santana and Blaine had been his first and second mates, respectively, and they had since moved up in the ranks. As the new captain of the McKinley, Santana was determined to triple their income and increase their luxury expenditures. Pirates had a reputation for being lazy and unorganized, but Santana and the rest of her crew were actually putting in a lot of work.

"The ship is about an hour away," Blaine told Santana as they left her cabin and walked across the deck. "That gives us enough time to get away, don't you think?"

"Of course," Santana replied. The McKinley was the fastest ship in the Caribbean, everyone knew that. Navy ships and other pirates were never too much of a threat as long as they didn't let their guard down. In all the two years that Santana had been aboard the ship, they'd run into trouble only once. Which, to Schuester's credit, was a pretty damn good record.

They reached the bow and Santana pulled out her spyglass. She located the ship that Tina had spotted, drifting on the horizon with its bow pointed straight towards her. The sails were gray and the wood looked battered and old. This was definitely not the Royal Navy.

"What is it?" Blaine asked finally. "I can't see, the sun's too bright."

"Unmarked sails," Santana replied, folding the spyglass and slipping it back into her pocket. "It's right on our path and it looks like we're on theirs." She looked at Blaine stonily, trying to mask her apprehension. This was her first major decision as captain. Her first big test. "Should we divert?" she asked, trying to sound as collected as possible.

"I don't know," Blaine said. "We're low on supplies, particularly food. We might want to chance a trade."

"They could be pirates, too," Santana pointed out.

"All the better," Blaine said. "We've got the gold. Why risk going to port? Besides, it could be days before we get there."

"Maybe..." Santana said. She didn't want to admit to Blaine that she was scared. What would everyone say if they knew? Santana was well respected on the McKinley—she was good at looting and fighting, and she was never afraid to put people in their place. But when it came to matters of diplomacy, her courage often failed her. It was hard to out-negotiate ruthless captains, especially when so many of them were men twice her size.

"We're low on rum," Blaine said, interrupting her. "I think we'll be out in a day or two."

Santana grimaced. If there was one thing she and her crew couldn't do without, it was rum. "We'll sail towards them and signal to trade," she said. "But tell the crew to keep an eye out. I don't want any of those unknowns coming on our deck."

"Sure thing," Blaine said. He left, and Santana watched him go, feeling nervous. She hurried to the other side of the deck and went up the stairs to the quarter deck, where Artie was standing at the helm. He gripped the spokes of the wheel tightly as he balanced expertly on his peg legs. How he managed to walk around with two wooden legs, Santana would never know. All she knew was that he'd lost them both in a shark attack when he was just a boy. That must have been some shark, she thought.

"Peg Legs," she said. "I want you to steer us straight for that ship over there. I'm going to signal a trade."

"You got it," Artie replied.

"But...be on guard. Just in case I change my mind."

Artie nodded. "Yes Captain."

"Captain, huh? That's new."

Santana turned to see Quinn walking across the deck, a satisfied smile on her face. Quinn had been the most passionate supporter of Schuester's mutiny, and every time she saw Santana, she seemed to be reminded of their success. "I still haven't quite gotten used to it," Santana admitted.

"Captain Santana Lopez," Quinn said thoughtfully. "It does have a nice ring to it."

"Better than Second Mate Quinn Fabray?"

Quinn grinned. "You serious?"

"Completely serious," Santana confirmed. In general, the McKinley wasn't big on hierarchy and everyone shared most of the work. But she'd known in the back of her mind that it would be her job to replace Blaine once he became first mate, and she'd been thinking long and hard about it. Quinn was Santana's oldest and closest friend, and she was smart. "Besides me and Blaine, you've been here the longest," Santana said. "I know I can trust you."

"Sweet," Quinn said, looking as though she wanted to hug Santana. To Santana's relief, though, she restrained herself. Public displays of affection weren't really their thing. "Thank you so much," Quinn said instead.

"Don't thank me yet," Santana said. "You've got a job right away. We're going to trade with this ship."

Quinn looked out on the horizon at the strange ship, which had moved closer since Santana had last looked. She nodded. "Let's do it," she said.

For the better part of the next hour, Santana paced back and forth across the deck, waiting as the two ships drew closer and closer together. She looked at its ominous tattered sails and scanned the side of the ship for a name. Unable to find one, she turned to Blaine and gave him additional orders. "Get the entire crew on the deck," she said, hoping to alleviate some of her unease. "They can do work or talk amongst themselves or whatever, but I want them to be watching for anything suspicious. Only you, me, and Quinn will go aboard."

"Got it," Blaine said, turning to the rest of the crew to pass on the orders. Santana walked towards the rigging to where Puck was standing.

"I'm putting you in charge while the three of us go over there," Santana said. "If they're aggressive, don't hesitate to open fire."

"So it's official, then?" Puck asked. "Quinn's the second mate?"

"I'm sorry," Santana said sincerely. She knew that, at least among the boys, Puck was the obvious choice. He had been responsible for more than half their loot under Schuester. "I've known Quinn a long time. It seemed right."

Puck shrugged. "It's okay," he said. "I trust your decisions. It's just that, some of the others might not."

"What are you talking about?" Santana asked.

"Nothing really," Puck said. "Just talk around the bunks. It's not important."

Santana narrowed her eyes. "Puck..." she began. If people were already questioning her judgment, she wanted to know right away. Mostly so she could decide whether to change her behavior or tell them to shut the fuck up.

"Don't worry, I'll let you know if there's a big problem," Puck said. "Just...don't do anything too extreme. Remember, you're still new." He punched her playfully on the arm. "You ready for this trade, sis?"

Santana laughed. "I sure am, bro," she replied, feeling comforted at the reference to their old inside joke. When Puck had first tried to join the crew of the McKinely, Schuester had thought Puck seemed untrustworthy. But Santana had felt that a strong, badass guy was exactly what they needed, so she told Schue that Puck was her long lost brother. It had been a huge risk, since the two had never met before, but Puck had turned out to be a great asset. And he and Santana had become fast friends.

Santana left Puck and headed towards the bow so that she could signal their friendly intentions. As the other ship got closer, she watched the crewmen assemble on their deck. They were all male, large, and oafish, and Santana knew that the price of a bad trade could be their lives. Figures, she thought, that they would encounter some scary weirdos right after she became captain. She stood firmly as Artie spun the wheel so that the ships were positioned side by side. "Anchor!" Santana called out. Mercedes and Quinn picked up the anchor and dropped it into the water. Santana looked up to confirm that Tina was still in the crow's nest, keeping an eye on things. She pretty much always was, so Santana was not surprised to see her now, crouched down so that she was mostly hidden from the other crew. When Santana caught her eye, Tina gave her a thumbs up. So far, so good.

The ship lowered their plank and Mike and Sam caught it, resting it on the side of the McKinley and securing it with ropes. Santana once again scanned the side of the vessel for a name. Finally she saw it, in faded letters. The Titan. "Good evening," one of the men on the other side called out. "Feel free to come aboard our ship."

Santana looked over at Blaine, who nodded, and walked nervously towards the plank. Mike and Sam helped her up, and Blaine and Quinn followed closely behind her. When she got to the other side, she chanced a glance behind her and was pleased to see that her crew was following her orders. They were all on deck, cleaning and making repairs, but Santana knew that they were watching out of the corners of their eyes to make sure everything was going according to plan. Once Blaine and Quinn had arrived on the deck as well, the man who had first spoken asked, "Which one of you is the captain?"

"I am," Santana said, stepping forward. She noticed the man's eyes widen slightly in surprise, and the corners of his mouth twitched. Santana had to restrain herself from rolling her eyes. Why was it such a big surprise whenever a captain turned out to be a girl? With a steely expression, she held out a hand. "I'm Santana Lopez, captain of the McKinley."

"And I'm Captain Dave Karofsky," the man replied, reaching forward to shake her hand, though the amused look never left his face. "Captain of the Titan."

"Are you pirate?" Blaine asked. Santana turned around and glared at him, angry that he was speaking when she was supposed to be the one in charge. Didn't he know that made her look weak? Karofsky laughed, and his men began to chuckle along with him.

"We prefer the term 'Gentlemen of Fortune'," he said. "And what's it to you? I don't see any white sails on your ship." He squinted towards their ship, and Santana followed his gaze, glad that one of her more forward-thinking crewmates had thought to take down their Jolly Roger. If the Titan wouldn't admit to piracy, neither would they.

"Look, we'll mind our own business if you mind yours," Santana said. "This is a trade. We're not doing anything political."

"Agreed," he said. "Now what are you looking for?"

"Food," Santana said. "We need meat and rum. And bread, if you have any."

"Oh, yeah, we've got tons of that," Karofsky said. "We got fresh meat from port a few days ago, and we have a lot of salted meat as well."

Santana's mouth began to water at the thought of having fresh food. "Do you have any fruit?"

"Sure, tons of it." He smirked at the longing expression on her face. "Why don't you come below deck and take a look at what we have?"

He turned around and Santana, Blaine, and Quinn followed him. "Aw yeah, fresh meat," Quinn sang quietly. "I'm so excited..."

"Quinn, don't embarrass yourself," Santana said, though she felt excited as well. But that didn't mean she had to behave like a child. "We don't want them to think we're amateurs."

"If we look too eager, they'll rack up the price," Blaine added. "It's basic negotiation training."

"Well, thank you very much, Mr. Basic Negotiator," Santana said. "Your advice was both necessary and solicited."

Blaine rolled his eyes and they turned to descend the ladder into the hull. Santana was surprised to see that there were even more people below deck. They were mopping and dusting just like her own crew members were doing at that very moment, but there was something a little off-putting about them. They looked nothing like the crew of the Titan that had greeted them on the deck. Their arms and legs were thin and skeletal, and their hair was matted and dirty. One of them made eye contact with Santana as she passed, and she shuddered at the scared look in his shrunken eyes.

Quinn came up right behind her. "Santana," she said quietly into Santana's ear. "I think this is a slaver."

Santana turned to Quinn with wide eyes. A slaver? They had never been in contact with a ship like that before. Everyone on the McKinley had pretty much agreed that there was something abhorrent about selling humans like they were goods. But a trade was a trade, and Santana was in no place to be picky. "What are we gonna do about it?"

"I don't know. Nothing I guess," Quinn whispered as Karofsky led them to yet another ladder. They descended to the next level and found themselves in a huge room with barrels and boxes stacked to the ceiling.

"Here's our magnificent cargo hold," Karofsky announced. "Take a look around, find what you like."

Santana forgot all about the slaves as she looked around the hold at the boxes of food and goods. She had never seen such an accumulation on one ship before. These guys were really cleaning up. Beside her, Blaine and Quinn were similarly dumbstruck. "What should we take?" Quinn whispered. "There's just so much of it."

"Everything we can carry," Blaine said, and Santana had to agree. They needed rum and meat, obviously, but the thought of getting some fruit and vegetables was so tempting.

"Fresh meat for one night," Santana decided. "And some fruit and vegetables for tomorrow. Then everything else has to be in preserves."

"How about fresh meat for two nights?" Quinn asked. But Blaine shook his head.

"They've already had it for a while. We don't want to poison ourselves. It's summer, anyway, it won't keep very long."

"Fine," Quinn said with a sigh.

Santana turned to Karofsky, feeling happier and more confident than before. "Let's talk prices," she said.

Fifteen minutes later, the four of them had formed an assembly line to lift their purchases out of the hold. Santana took the boxes from Quinn and handed them up to Blaine, who was standing in the middle of the ladder with his leg wrapped around the wood to brace himself. He lifted the boxes to Karofsky, who pulled them up from the top with inhuman strength. When all the goods had been assembled on the second level, Santana and Quinn climbed up. "Alright," Karofsky said. "Let's take these to the next ladder."

He grabbed the largest barrel and Blaine, clearly wanting to prove his strength as well, picked up two of the remaining boxes. Santana rolled her eyes and grabbed a crate of apples—no need to overextend herself. They walked through the corridor, once again passing by several skeletal slave-workers. Santana averted her eyes as she walked, even though she felt guilty. Wasn't giving the Titan their money only encouraging them to buy more slaves? She decided not to think about it. They needed food, this was a matter of life and death, really.

As she neared the ladder, the door to one of the heads opened suddenly, and someone collided hard with Santana. "Shit!" Santana exclaimed as the crate fell from her hands and several apples cascaded to the floor. She immediately dropped to her knees to rescue her purchases. There was no way she was giving up fresh apples, they were her favorite fruit. The clumsy intruder bent down to help, and as they reached for the same apple, Santana's fingers brushed against a soft hand. She looked up and found herself staring into a girl's deep blue eyes.

"Sorry," the girl whispered, looking terrified. Santana wanted to reassure her that it was okay, but the girl's appearance shocked her so much that she could not find the words.

"Brittany!" Karofsky roared. He reached down and seized a handful of her long blonde hair, pulling her roughly to her feet. Brittany's eyes screwed up in pain but she didn't make a sound. "You idiot! Don't you ever watch where you're going?" He looked down at Santana. "Get up, she'll clean this for you."

Santana looked up at Quinn and Blaine. Both of them were staring back at her with wide eyes. "It's no trouble," Santana said to Karofsky. "I'll do it myself." Blaine shook his head vigorously at her, but she ignored him and began to put the fallen apples back in the crate.

"No, really, don't," Karofsky said. "She needs to learn to pay attention, she's always doing stuff like this." Santana looked up at the girl called Brittany and saw that her eyes had filled with tears. Karofsky looked at her, too. "Well?" he demanded. "Are you going to pick up those apples or just stand there?"

"There's no need," Santana said coldly. She may not have raised an objection to the rest of the slaves, but hell if she was going to let this poor girl be abused right in front of her eyes. She picked up the last apples and got to her feet. "Shall we continue?"

Karofsky looked at Santana angrily, and for a moment, she feared that she had gone too far. Beside her, Quinn gulped. Then Karofsky turned unexpectedly to Brittany and slapped her hard across the face. Brittany stumbled back, covering herself with both hands. Santana could see that she was biting her lip to keep from crying out. "Alright," Karofsky said, sounding slightly out of breath. "Let's get this stuff on deck."

Blaine and Quinn were dead silent as they turned back to their goods. Santana's heart was racing. What was going on? She couldn't help but stare at Brittany as she handed the boxes up to Blaine, her heart aching as she saw that the girl's shoulders had started to shake. She was probably crying, but her eyes were still hidden behind her hands. "Azimio!" Karofsky called out from above them. "Get the guys to take these boxes across to the McKinley!" They finished passing everything up, and Karofsky stuck his head down into the hull. "You get up here too, Brittany, you might as well make yourself useful."

Santana watched as Brittany removed her hands from her face, revealing her red eyes and an ugly welt forming on her cheek. She pushed past Quinn and Santana and began to ascend the ladder. Santana noticed for the first time that she was wearing a dress, which was torn in many places and caked with dirt. It looked as though she had worn nothing else for a very, very long time. Once she had reached the top, Santana and Quinn began to climb up after her. "We need to get the fuck out of here," Quinn muttered. Santana nodded in agreement.

When they got to the deck, Santana was pleased to see that the rest of her crew had already taken most of the boxes across and were now sorting them for storage. Blaine was waiting for them by the plank. Santana automatically sought Brittany out and was surprised to see that Brittany was staring back at her. Her eyes were wet and pleading, and before Santana knew what she was doing, she was walking determinedly towards Karofsky. "How much?" she demanded, cocking her head towards Brittany.

Karofsky looked at her in surprise. "I didn't think you were interested in goods of this nature," he said. "Otherwise I would have brought out a finer selection." He smirked and Santana forced herself not to grimace.

"How much?" she repeated.

"She's not for sale," Karofsky said. "And besides, you don't want her. She's useless." He shoved Brittany's shoulder as he spoke, causing her to stumble. The members of Karofsky's crew who were watching snorted in amusement, and Brittany looked down at her feet.

"I do want her," Santana said. "And if she really is useless, you can give her to me cheap, right?"

"Not so fast," Karofsky grumbled. "She does have her uses. Why don't you let me bring out all of our products and you can take a look?"

Quinn and Blaine had joined them now, looking at Santana curiously. "What are you doing?" Blaine asked quietly. Santana ignored him.

"I want her," Santana demanded. "Tell me what it's gonna cost."

Karofsky's eyes narrowed in anger. He glanced around at the rest of his crew, who were all watching him. Then he turned back to Santana. "Fine," he spat. "I want double what you're paying for all the goods I just sold you."

"Santana..." Quinn began.

"Done," Santana said.

"What?" Blaine demanded. Santana turned on her heel and glared at him until he stepped back demurely. "I'll get the gold," he muttered, heading for the plank. Santana nodded and turned to Quinn. Quinn just shrugged, and Santana stepped towards her, out of earshot of Karofsky and Brittany.

"I had to do it," she whispered, suddenly feeling insecure about her impulsive decision.

Quinn nodded. "I know."

"She just seems so scared."

"They all do," Quinn pointed out.

"I know, but her more than anything." Santana swallowed hard. "The way he just hit her..."

"I know," Quinn said again. "I know." There were several minutes of silence as they waited for Blaine to come back. The rest of the Titan's crew resumed their duties, but Karofsky remained next to Brittany, still as a statue. Santana watched Brittany carefully, hoping for some eye contact from the girl, some sign of relief or gratitude that showed that Santana had done the right thing. But Brittany kept her eyes fixed on the deck.

It wasn't long before Blaine came back, carrying two burlap sacks in his arms. "Here you are," he said breathlessly. "This is all of it."

Karofsky stepped forward and took the two bags, weighing them in his hands. Then he nodded, satisfied. "Take her," she said, shoving Brittany forward. Brittany stumbled and steadied herself on Blaine's arm.

"Whoa. You alright?" Blaine asked. Brittany just nodded. "Come with me," he said, leading her towards the plank. Quinn followed close behind her and Santana stayed where she was, watching them. Only when Brittany made it all the way across to their own ship did the knot in Santana's stomach loosen slightly. She turned back to Karofsky.

"Thank you for the goods," she said tersely.

"You're welcome," Karofsky replied, swinging the bags of gold smugly. "It was a pleasure doing business with you. Maybe we'll meet again."

"I sure hope not," Santana replied. She turned and headed for the railing, climbing up onto the gangplank. Puck was waiting for her on the other side, and he took her hand to help her climb down.

"Well, that went pretty well for your first negotiation, didn't it?" he said brightly.

"It was fine," Santana replied. She turned around to address her crew. "Make haste!" she called out. "I want as much distance between us and that ship as possible! Let's move."

Puck raised his eyebrows. "What's wrong?" he asked.

"That guy gave me the creeps," Santana admitted. "I didn't like what was going on over there."

"Does this have something to do with that girl Blaine just brought over?" Puck asked. "Mind explaining that move?"

Santana shrugged helplessly. "I just...I don't know. Yet."

"Remember when I told you to not to do anything extreme?" Puck asked. "Well...this could be considered a little extreme."

Santana took a deep breath. "I'll just have to risk it." Puck still looked uncertain. "It's okay," Santana continued. "I'll see what's up with her and then I'll send her on her way. We'll make the money back in our next raid. In a couple of days, it'll be like she was never here."

Puck shoved his hands in his pockets and sighed. "For your sake, I hope you're right."