Contains vague references to Fluttershy's early sexual experiences that some (including the author) might find disturbing. Also contains references to incest. Why can't I write nice things?

Also before anyone @s mea bout it, Fluttershy's cottage has always been an animal shelter and I don't know what the point of Fluttershy Leans In was supposed to be.

The Queequeg's cafe down by the train station gleamed with homogenized corporate perfection, from the dark polished floors to the plasticized gleam of the pre-packaged pastries, to the cheerful efficiency of the uniformed employees. Fluttershy hated it here.

“We could have gone to Sugarcube,” said Fluttershy to Applejack as they waited in the long line to order. She felt exposed here. Too much open space, too many unfamiliar ponies. She liked Sugarcube, where one of her few friends worked and where she knew everypony, at least well enough to know that none of them was going to grope or attack her. She wished she still had her decorative planter disguise, but Applejack had insisted she leave ‘them crotch-smelling begonias’ by the door.

“No, we can’t. Too many ponies we know go there. Nopony comes to this Queequeg's but tourists and ponies waiting for a train. And what we gotta talk about here is family shame.”

“Oh! Family shame?” said Fluttershy, wings fluffing out with interest.

“What can I get started for you?” said the chubby little unicorn barista, smiling a professional smile.

“I’ll have a trenta apple macchiato with an extra shot of espresso,” said Applejack.

“Great, and for you?” said the Barista.

“Um… Coffee?” said Fluttershy, who had been too busy worrying to take time to look at the menu.

“Light roast or dark?”

Fluttershy’s eyes widened until the whites showed all around. She was not ready to make such a momentous decision on such short notice. “Guh?”

“Um… Light roast or dark?” repeated the barista, looking concerned.

“Light?” said Fluttershy, hesitant, trembling. Dark sounded scary.

“Tall, grande, or venti?

Fluttershy crouched down until only her ears poked up over the edge of the counter.“I… I don’t know what any of that means.”

“Oh, for Harmony’s sake. Just give her a tall dark roast, light with cream, with a hazelnut shot and a salted caramel drizzle, okay? C’mon, Shy. Let’s get you comfortable.” Applejack guided her to a back corner booth where she could see the door, then went to wait for the drinks.

Fluttershy gazed around the Queequeg's sullenly. Applejack had meant well in picking this seat, but there was no easy access to exits from here. She supposed she could throw Applejack at any dangers that appeared, be they monsters or overly friendly strangers. As soon as she came back. She hunched down in the plastic-coated seat like a newly cutie marked filly out with her mom, wings hanging limply at her sides. Her forelock slid out of her bun and fell over her left eye. She let it stay there.

Why was she here? Why was this any of Applejack’s business? This place was making her uncomfortable, and she’d been out long enough that she was starting to get separation anxiety from her animals. Were they all okay? Yes, Angel had promised he and his cousins would keep an eye on things, and yes, they did run her animal shelter like a prison camp while she was out, but that itself could be a problem. Like that time they’d organized a firing squad to punish the capybaras for messing in the cottage. She’d arrived just in time to stop the execution, and Angel had promised never to do that or anything remotely like it ever again. But the capybaras had picked up a smoking habit from their last cigarettes and they left their butts everywhere.

Applejack plopped Fluttershy’s drink down in front of her and sat across from her in the booth. Fluttershy sniffed cautiously at her drink, checking for tell-tale signs of poisoning. Applejack was apparently a horrible bitch who interfered with her friends’ sexual autonomy, but she wouldn’t poison her. The same couldn’t be said for those shady baristas. “So what’s the problem? Why am I here? What’s wrong with Macintosh. Is he gay?”

Applejack sighed and slumped in her seat. “No? Yes? He don’t seem particular. Our Macintosh, he’s a bit of a swordspony.”

“Swordspony?” said Fluttershy, brows knitting with confusion. She’d never seen Macintosh near anything more deadly than a firewood ax.

“It’s fancy talk for ‘he sleeps around a lot,” said Applejack, looking sadly at her coffee, "And I wish I didn't need to know the term."

Fluttershy’s face brightened. “Oh! I get it! The sword is his penis!” Informed of this exciting news Fluttershy tried very hard to keep a goofy smirk off her face and her wings folded modestly at her sides. “Anyway, um, you don’t say. That’s… um… terrible.” If Macintosh was that easy, she could shift her plans from ‘getting to know him’ to ‘persuading him to let her be his personal training dummy’.

Applejack looked around to make sure nopony was eavesdropping. “First there was Caramel. I done told him it’s not appropriate to hammer the hired help but he didn’t listen and I had to let poor Caramel go. Then there was that whole disaster with Miss Cheerilee. That was pretty normal, except he cheated on that poor mare constantly. Then there was that baker pony, whatever her name was.”

“Pinkie?”

“Gol darn it Fluttershy I know what Pinkie’s name is!” Applejack narrowed her eyes. “Though now that you mention it I’ve seen the two of them slipping out of Berry’s bar together a time or two.”

Fluttershy mock-gasped. “But Pinkie’s your cousin!”

Applejack took a sip of her drink to steady her nerves. “Oh, he ain’t shy about cousins. Him and Braeburn are all over each other every family reunion. And something happened between Marble and him, but neither one of them’s talking.”

Fluttershy decided the coffee wasn’t poisoned if Applejack hadn’t dropped dead. She pushed her mane out of her face and leaned in to scoop the salted caramel off the top. The hot ropes of gooey, salty-sweet goodness warmed her belly and made her think of Macintosh squirting in her mouth. Which made her feel sad that the fantasy wasn’t real, mad at Applejack for getting in the way of that fantasy, and so horny she felt a puddle forming in the plasticized fabric under her butt. “So why is any of that a problem?” she said, her voice half-muffled by caramel.

“Because I don’t want you getting hurt, Fluttershy! You’re kind of a… well. I don’t wanna be mean. But you’re kind of a shut-in. You don’t know how the world works. And Macintosh is a very worldly pony.”

Fluttershy lapped up another mouthful of coffee. it was good, but she missed the caramel. “That’s not a very nice thing to say.”

Applejack took off her hat and rubbed the top of her head. “I’m not trying to hurt your feelings, Shy, I’m just trying to protect you.”

Fluttershy batted her eyelashes. “Because I’m so sweet and widdle and innocent?”

“Um…”

“I was pretty young the first time I let Rainbow Dash use me. I didn’t understand what she was doing, but I let her do it because I loved her. Pretty soon I got to love what she was doing to me, too. It would have been perfect, except of course this was Rainbow Dash and she didn’t want to be ‘tied down’.” Fluttershy hooked her hooves in the air when she got to the scare quotes. “So she used to pass me around to her friends. Which was a lot of fun.”

Applejack’s mouth slipped open.

“But then, of course, because this is Rainbow Dash, and because she didn’t want to be ‘tied down’,” she made the scare quote hooves again, “She dumped me as soon as things started getting serious between us. As if I wouldn’t let her sleep around! So I moved to Ponyville to open my animal shelter and a few months later who comes crawling back down to the ground with her tail between her legs? That’s right. Rainbow Dash.” Shy wiggled her hips against the booth seat, spreading mare goo across it. “Guess she can’t stay away from this.”

“Fluttershy, that’s horrifying!”

Fluttershy blinked, legitimately confused. “Why? It was all consensual and amongst my peers.But Rainbow isn’t getting any more of the Flutterbutt until she apologizes for breaking my heart. After that I’ been mostly flying solo. I Or I was until Rainbow introduced me to your group. I’m always welcome in Pinkie’s bed. I’m a little vanilla for Rarity, but she and Twilight have taught me a lot of things. You know all those nasty rumors about Canterlot Unicorns? Turns out they’re true. Like, I was scared to try pee stuff, but Rarity broke me in gently and now I can’t get enough.”

“I’m just going to expunge that last sentence from my memory. You never said that, okay?”

Fluttershy shrugged. “I don’t care if you judge me for liking pee.”

“Judge you for what? I don’t remember you saying nothing about pee. But… wait, that’s all of our group but me!”

“Yep.”

“Dangit, I don’t know how I feel about that. If they’re with you, that means they’re probably all crosswise amongst each other, too. That’s fine, it’s none of my business, but…”

Fluttershy slid a hoof halfway across the table. “Do you feel left out? If you’re curious, we can cuddle and see what happens.”

Applejack sputtered. “No! No, I…” She covered her face with her hat and started to hyperventilate into it.

“Deep breaths,” advised Fluttershy. “Don’t try to fight the panic. Just let it wash over you.”

A minute or two of controlled breathing later, Applejack peeked over her hat. “I misjudged you, Fluttershy. And not in a good way. I’m tryin’ not to judge you now.”

Fluttershy shrugged. “I’m not ashamed. I like sex. It makes me happy, and it’s a way to get close to other ponies without having to talk to them much.” As she spoke, a wicked little idea wormed its way into her mind. She pushed her mane out of her face. “Oh! Just had an idea!”

Applejack leaned back and looked at Fluttershy sidelong. “I don’t know if I wanna hear this.”

“If you’re uncomfortable with Macintosh exploring his sexuality… well. I don’t want to sound like I’m bragging?” She wiggled her hips in her seat suggestively. “But nopony’s ever said no to another taste of this once they’ve had a sample. If Macintosh and I were to become involved, I’d be able to keep an eye on him for you. Keep him out of trouble.”

Applejack narrowed her eyes. “Out of trouble?”

Fluttershy blushed. “Well, I’d do my best.”

Applejack took a sip of her coffee. Then another. Fluttershy could tell she was thinking and didn’t interrupt her. “I’m scared for him. I’m afraid he’s gonna get some disease, or get somepony pregnant and it’s gonna be a huge shame for the whole family.”

Fluttershy bit her lower lip. Oh hey Applejack did I mention I want to have foals? I love caring for small creatures and also getting knocked up is hot, and I hear some mares get incredibly horny when they’re pregnant. I’m not getting any younger and I’m just looking for the right stallion before I ask Twilight to take off the birth control spells. Maybe not a good time to bring that up. “You know,” she said, “I do go to Twilight for checkups and birth control spells pretty regularly. I could take him with me.”

“Twilight ain’t a doctor.”

“Not a doctor of medicine, sure. But she’s a horny little magic pony,” said Fluttershy, looking down to hide her smirk. “And that’s just as good, right?”

Applejack puffed air out through her nostrils. “ If you start sleeping with him, is it just gonna be you, or is gonna be you and all your friends?”

“Um, I wasn’t planning on doing a lot of sleeping with Mac.”

“Fluttershy! Try and take this seriously!”

Fluttershy reached forward and put both hooves on Applejack’s. She looked her in the eye. “Not everyone can stay with one pony for their whole lives, Applejack. I’m not promising you to make him an honest stallion for you. I’m promising to help him safely be himself.”

Applejack held Fluttershy’s gaze. Fluttershy’s instinct was to look away demurely, but she fought it—the staredown felt like Applejack testing her. Like if she looked away she was weak? Or not worthy of Macintosh? Or something silly like that? Fluttershy didn’t see things that way, but she stared back without blinking.

Long seconds passed. Her eyes were getting dry. Was Applejack done yet? She felt herself aging, her biological clock ticking inexorably. She was tired of being around other ponies, and she needed to get back to the animal shelter.

“All right,” Applejack said at last. “I ain’t sure about this, but this is what we’re gonna do.”