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1. It started normally... kind of (SigmasonicX)

Captain Twilight Sparkle of the Sundowner Fleet sighed, stretched her arms up, then disembarked her airship as her crewmates tied it to the dock. A gust blew her long purple hair back, and with a white-gloved hand, she adjusted her wide-brimmed captain’s hat, then looked ahead.

Among the warring pirate factions of the Equestrian skies, there was one place of true neutrality, and it was the dirtiest, most corrupt place known to man: Klugetown. Feared by all honest citizens as the place to go if you want your clothes taken straight off your back before you reach the town’s border, it is nonetheless the safest place for a buccaneer to relax, find a crew, and plan their next adventure.

Unfortunately for Twilight, none of those were the reason why she was there.

She walked to a building that stood out from the rest, if only from the effort put into keeping the outside clean—certainly not an easy task in that dusty town. Clear windows showed the inside of what at first resembled a pub, but featured what could only be called a cozy and family-friendly atmosphere. Not that the customers reflected this, with their eyepatches, daggers, and pistols, but there was only so much one could do there.

The store was called Carousel Coffee, as depicted by a colorful logo above the door. In the Equestrian mainland, coffee was rare and exotic, so the idea of opening a shop just to serve it was close to incomprehensible. However, in Klugetown, coffee, sugar, cinnamon, and all kinds of other expensive commodities flowed freely. While simple proximity to the places they were produced certainly influenced this, no shop here got all of their wares legitimately.

Twilight took a breath. There was still some time before her appointment, but waiting out here wouldn’t delay it more. The bell rang as she opened the door, and several seedy figures looked up at her from their sweetened coffee drinks and scones.

“Hello, and welcome to Carousel Coffee!”

Sticking out from the crowd was the woman behind the counter. Twilight knew she was straight, but she couldn’t help but note her gorgeous curly purple hair and striking blue eyes. She never failed to note those ever since her first visit to the cafe, and her subsequent visits that she completely coincidentally timed to be during her shifts.

The woman put her hands together. “Oh my, if it isn’t Captain Twilight Sparkle, my dearest customer.”

Twilight smiled at the compliment as she walked to the counter and sat at a stool. “Hi Rarity!” she said more eagerly than she intended. “The usual, please.”

Rarity leaned on the counter. “A medium latte again? Darling, I would have expected a dangerous pirate to be more daring.” She motioned her head to her right. “Take that customer.”

A pirate with wild pink hair banged on the counter, startling the other cashier, a woman with short blue hair—a Miss Coco Pommel, as Twilight recalled. The pirate screamed, “I want a frappuccino with jelly beans of every flavor, whipped cream, caramel, and cotton candy, and I better be able to float a chocolate chip cookie on top, because I got those, sister!”

Coco nodded with wide eyes and gritted teeth and got to work.

Twilight shook her head and slid some copper coins. “I think I’ll pass. Plus, I expect to be here for longer than usual.”

Rarity took the coins and quickly got to work. “Oh? Did you have a stressful voyage? A chance encounter with the famous fashionable masked pirate hunter Radiance, perhaps? And now you feel the need to talk to the cutest girl you know for some comfort.”

The pirate captain blushed. “Well, I, you know, the voyage was kind of rough, but, I mean, it wasn’t that bad, I didn’t need to, for that, to talk about that to you, and, well, it’s something else.”

Rarity seemed unperturbed by whatever just poured from Twilight’s mouth and gave an easy smirk that Twilight would have found sexy if she wasn’t straight. “And what might that something else be?”

Unfortunately for Twilight, her mouth hadn’t stopped spewing. “I’m meeting my mom here!” She covered her mouth, but relaxed upon realizing that would have been obvious to Rarity once her mom arrived anyway.

Having finished steaming the milk, Rarity moved on to preparing the espresso. “Oh my, how interesting! Captain Twilight Sparkle’s mother. Though I sense some unease from you about this. I suppose it is true that all pirates have mommy issues.”

Twilight blushed again, though this time in offense. “What, no, that’s not true. My mom is actually quite supportive of me being a pirate, in fact. The issue is more that…” She hugged her arms. “... My mom has been bothering me for a while about getting a boyfriend, and I just know she’ll bring it up today.”

Rarity gasped as she pressed the coffee. “How scandalous! You’re telling me that the Dread Pirate Sparkle doesn’t already have a special someone?”

Twilight frowned. “Well, I mean, I’ve been busy. Attacking royal caravans, evading the pirate hunter, all that. Not much room for romance.”

Rarity looked into her eyes. “But Captain Sugar Belle has a special someone. Heavens, even Mudbriar of all captains has a girlfriend.”

“Well, it’s different for me.” Twilight sighed. “Look, I’ll be talking about all this with my mom anyway, so I’d rather not…”

Rarity nodded. “My apologies. It’s completely up to you to determine when you’re ready for romance.”

“Yeah.” Twilight said. “If only there was some way to get her off my back. Like, I don’t know, you pretending to be my girlfriend.”

Rarity blinked.

Twilight realized what she just suggested and quickly added, “I’m kidding! Just a joke! Besides, it wouldn’t work, because I’m straight.” The overly precise part of her mind chose now of all times to act up, and she added, “As far as I know.”

The barista hummed as she poured steamed milk over the prepared espresso and presented the cup to Twilight. “Well, pretending shouldn’t be an issue, since I’m straight too.” She winked. “As far as you know.”

Her face turning red, the pirate captain accepted the drink.

Rarity served another customer as Twilight sipped her latte in peace. Or as much peace was allowed in a pirate town, as a fight over cards broke out and quickly died down behind her, and her pink-haired seat neighbor loudly nommed through a drink that would have surely killed anyone else.

As the fated time approached, Rarity leaned over and tapped the pink-haired pirate’s shoulder. “Pinkie, time for a shift change.”

The woman, Pinkie, saluted and said, “Okie dokie!” She swallowed the rest of her calorie bomb, and with uncanny speed, she leapt into a side room, then came out in Carousel Coffee uniform.

“You’re leaving?” Twilight asked Rarity. “I was hoping you’d still be here when my mom came.”

Rarity smiled as she walked toward the side room. “Alas, I have better things to do with my time than keep serving coffee. But don’t worry, I think you talking to your mother will be more pleasant than you expect.”

The other barista, Coco, went into the room too. She soon came out in a pirate’s clothing, holding a large knife between her teeth. A new barista, a lovely but fragile-looking girl with long pink hair, took her place. Twilight ordered another latte from Pinkie, and noted that Rarity still hadn’t left the side room.

The door rang and Twilight turned to see a woman with purple and white hair and civilian clothes waving at her. “Twily! It’s so good to see you!”

Twilight smiled. “Hi Mom!”

Her mother, Twilight Velvet sat down next to her, unheeding of the pirates around her sizing up her robbability. They hugged, and Velvet said, “How has the pirating world been treating you?”

Before Twilight could respond, her mother said, “Oh, but first, I should probably lead with the fact that I found the perfect man for you!”

Twilight forced a smile. So she went there already. “Oh. Interesting.” She leaned over to look behind her. “Is that him there?”

Velvet hummed in confusion, then looked back at the bruised and beaten man she was holding in a telekinetic grasp. “Oh, him. Nah, this is just someone who tried to mug me. I forgot he was there.” She released her magic and he fell to the ground in a heap. The other pirates turned away and whistled, pretending the thought of mugging her never crossed their minds. “The man I’m talking about is waiting just outside, actually. Do you want me to bring him in?”

Twilight frowned. “Mom, I didn’t ask you to do this!”

Velvet waved her hand. “Oh, but just give him a chance, Twily.”

The pirate captain gritted her teeth. Couldn’t someone save her from all this?

“Sorry I’m late, dearest.”

Rarity stood at the side door, having changed into a gorgeous red dress and adjusted her makeup. Twilight thought she looked great just as a barista, but she was absolutely dazzling now, and her mouth hung open.

She approached Twilight Velvet and extended her hand. “You must be Twilight’s mother. It’s a pleasure to meet you. I’m Rarity.” She gave a sly smile. “Twilight’s girlfriend.”