"Yeah, I'm sorry guys. I'm going to have to call it there. There's a presentation in the morning that I need to be up early for." Twilight's voice announced apologetically, backed by the sound of the click-clacking keys on a keyboard. "Great session today, though! We'll pick this back up on Wednesday."
Flash smiled and nodded at his webcam. He was sat comfortably wrapped up in two separate duvets, leaning back against a few fluffy pillows smooshed between the wall and the headboard of his bed. Only his feet and the better part of his head and upper torso poked out of the mound of fluff. A laptop sat demurely in his lap, providing the only dim light source in the cramped, somewhat messy bedroom. A pair of headphones ensconced the boi's ears, which a few feminine voices were occasionally buzzing through.
"Oh, shoot, yeah! I totally forgot about that. I'll be down there with Applejack to give you a ride, if she's awake." A voice that was unmistakably Rainbow Dash's perked up. "I think it's her day off. I'll text her later for ya."
Twilight gave the group a thumbs up, sporting a tired smile "Thank you, Dash. I appreciate it. I'm trying not to stress out over it, but it's pretty important for my final grade." There was a bit more shuffling of papers and what sounded like a swivel chair rolling away from Twilight's desk. "I'll be off now! Thanks everyone! You too, Flash and Mac! Have a good night!"
Flash opened his mouth to respond, but a sudden disconnect sound tone cut him off. He cleared his throat and tried again. "U-uh, yeah! See ya! ...Shoot, she's already gone, huh?"
"Eeyup." A slightly distant and sleepy Big Mac chuckled.
Flash and Rainbow both giggled at that, along with Sunset's quieter groggy voice joining in too. Sunset's webcam was basically pitch black, apart from a mess of fiery hair splayed out atop a pillow. From what Flash had heard, she'd been up and down all afternoon, busy with the same assignment Twilight was working on. Now, she was in the same boat as Macintosh. Drifting in and out of sleep.
The call went quiet, only interrupted occasionally by Rainbow Dash's quiet cursing and the mashing of a controller. From the sound of it, she was plugging away at a new video game or some such on another screen. Something that involved lots of shooting noises. Not particularly Flash's cup of tea, if he was honest. Still, he was thankful for any white noise at all that kept potential awkwardness at bay.
Suddenly, the sound of a new person joining the call made Flash jump. The icon of a small white cat on a purple background popped up on screen, with a webcam loading up too after a couple of seconds.
It showed Rarity, the fashionista, sitting in an office swivel chair, already dressed down to her pajamas. A matching set of silky black blouse and bottoms. Her hair was wrapped up in a towel, and she was without any of her usual makeup. She gave a dainty wave. "Good evening, darlings~!
Rainbow glanced over and whistled. "Heya, Rares! Let me guess, just got out of the shower? Lookin' good~" She winked vibrantly at the camera.
Rarity rolled her eyes. She was used to her friend's brashness by now. "I did, yes, dear. It might do you some good to do the same at some point." Rarity quipped back, sending Rainbow into a coughing/laughing fit. She smiled coquettishly and addressed the rest of the voice chat. "Regardless, how are you all tonight? I'm not interrupting your board game, am I?"
"Oh, no, Twilight had to end early because of the exam tomorrow." Flash answered earnestly before Rainbow had a chance to retort. "Sunset and Mac are too sleepy to continue, I think."
"Ah, that's fair." Rarity nodded, pulling a brush from somewhere off-screen and brandishing it. "But how about you, dear? Still bright eyed bushy tailed at this hour? Rainbow, I can understand, but I'm fairly sure it's past your bedtime." Rarity accused Flash in a motherly tone. He shyly nod-nodded. It was something she'd only started doing recently, for no discernible reason, but it made his cheeks go hot every time she did.
"U-uh, yep! I'm feelin pretty comfy. But not really tired." He wiggled a little in his lump of blankets as if to demonstrate this. As he did, the blankets covering him parted just enough to show a glimpse of his pajamas underneath. He urgently pulled them back together.
The eagle eyed seamstress raised an eyebrow at him. She let him squirm under her gaze for a few moments, before finally closing her eyes and turning away. She reached up to undo her towel, and it began unraveling, revealing perfect glossy purple locks cascading down her back and shoulders. She brought the brush to it immediately, as if tempering metal, running it through with practiced precision.
She spoke to him as she carefully brushed her hair, keeping a trained eye on him all the while. "I see you're wearing the pajamas I made you. How are they? Comfortable? Let me get a look at them."
Flash's face went very red. Embarrassed, not only for her tone, but also for having to potentially show what he was wearing to the group. Even if most of them were asleep. He took a deep breath and released his grasp on the blankets, letting them fall down around his shoulders.
Revealed was what looked like a long-sleeved bed gown. Or a nightie. It was cleverly made to resemble the classic girl's sailor-style school uniform. Though instead of the standard uniform fabric, it was made of a comfortable fleecy material, and the top also didn't separate from the skirt at the hip. Flash looked away shyly, fiddling with the sleeve cuffs.
Rainbow cursed under her breath as another muffled digital explosion went off on her end. Flash guessed she was probably losing or had just lost whatever she was playing. Her gaze briefly flicked towards the webcam, and she smiled at him. "Oh, yeah! I recognize those! You made one for Pinkie a while back, right Rarity? At the sleepover at Sunset's."
"That is correct, yes. Though she didn't wear it for very long. I don't think she's one for pajamas at all." Rarity pondered aloud, tapping a fingertip to her chin.
"Or uniforms. Or fleece. I think she prefers lighter stuff. Like satin?" Rainbow offered, and Rarity hummed. "I think she wears a lot of chiffon, like Fluttershy."
Flash blinked confusedly at the pair on the screen. He daintily raised a finger. "Uh, I didn't realize you knew so much about fashion, Rainbow?"
"Huh? Oh, yeah. You pick up on this stuff, hanging around Rarity for so long, I guess." Rainbow laughed, scratching the back of her head. "And I've been getting into it, kinda. Being more girly. Learnin' more about makeup and that stuff."
He nodded eagerly at that, his attire and her video-games both forgotten about for the moment. "Yeah? That's cool! That's basically what I'm trying to do with this." He blushed, fiddling with his silky necktie. "Like, tapping into my feminine side. It... makes me happier. Lighter. I feel more confident and less anxious when I'm dressing up. If that makes sense."
"I get like that sometimes." Rainbow admitted, her voice a tad softer than usual. Flash listened intently, holding in a breath. "I mean, like, not entirely. But I get wanting to be more feminine, for sure. Last night, I wore nail polish for the first time since I was like fourteen!" She chuckled, and Flash giggled along with her. "And I know it's harder for you. As a dude. You guys are basically taught at a young age not to explore that stuff, right?"
"Precisely." Rarity spoke up, being careful not to be too loud. "Which is why we're not judging you for wanting to express yourself around us. As a group, we're for you, dear. Even if you're not... erm..." She trailed off, delicately motioning at him.
"Not trans?" The boi answered. He felt his heart beating in his ears, drowning out the sudden silence. A red hotness spread over his face. "I... I dunno if I am. If what I feel counts as 'dysphoria' or whatever it's called. I don't know if it qualifies."
The pair remained quiet, patiently listening to Flash suddenly spilling his heart out to them.
"Like, a few nights ago, I was dreaming about things that made me happy. About what my ideal world would be like. I thought about pink dresses and white lace stockings. Fluffy petticoats. Pretty little purses with shiny metal clasps..." He smiled, genuinely, at the thought, staring off into space. Then he winced, delicately holding a hand against his chest. "But... it hurts. T-to not have that. Y'know? To not be that. I want to be girly and pretty and delicate and pink. But I don't see anything wrong with being me, too. Having both seems like it'd be way too hard."
"That sounds pretty rough, yeah." Rainbow agreed. Nervous head-scratching turned into full blown twirling locks of hair around her finger. "But I don't think there's any of us who don't work at it at all. None of us are naturally pretty like that, if that helps at all."
Flash nod-nod-nodded. He let out a long sigh, wrapping blankets tighter around himself. He rarely felt emotionally fragile like this, especially around others. There was something therapeutic about it, though.
"Regardless, darling, we do understand your plight, and we can try to empathize. We're here to support you, trans or not. Rainbow and I, and the rest of the girls too. Even if that support is teaching you how to apply make-up, using your preferred pronouns, or just being on here to listen. Whatever you're more comfortable with."
"Right! What she said!"
The timid boi's heart swelled. Gratitude radiated off of him in waves. "T-thank you, guys. I really, truly appreciate hearing that." He smiled wider than he had in a long while. His cheeks hurt. He felt tears springing to the corners of his eyes.
"Anytime, man." Rainbow saluted goofilly, before finally turning her attention back to her game. Rarity, for her part, kept her attention on him, cupping her cheek with the palm of her hand. A manicured nail tapped her temple.
"On a slightly different note, Flash. I have a request to make of you. I'm moving a bunch of my returned sales items away from the boutique for a few days, while I get the sales floor sorted out. My storage room is in need of cleaning, you see." Rarity explained. "I was wondering if you'd be able to hang onto them for me for safekeeping. Would you do that for me, dear?"
"Sure, yeah! Of course I can, Rarity!" Flash perked up immediately.
"Wonderful. My fullest gratitude, Flash." Rarity clapped, before writing something down on a nearby notepad. "I'll have Rainbow drop them off at your house tomorrow."
By the time Flash awoke the next day, the sun was already high in the sky. Someone was knocking on the front door, quite loudly, interrupting his slumber. His laptop still lay next to him, left open on an empty video call room. His blanket hung half off the bed, while still managing somehow to wrap itself around his legs. Birds chirped outside his bedroom window.
The sleepy boi dragged himself out of bed, much in the same way a hermit crab would vacate an ill-fitting shell. He brushed his teeth, scruffed his hair up a bit, and made his way downstairs. By the time he made it to answer the door, he was feeling pretty alright.
"Sup, sleepyhead." Rainbow grinned at Flash as he peeked around the gap in the door. "S'just me. Here to drop these off," she motioned to the two shiny black rubbish bags she was holding. "You good to pick 'em up off the doorstep or can I come in?"
Flash silently opened the door as he stepped back into the living room, tiredly rubbing an eye with the sleeve of his pj's. "Heya, Rainbow. G'mornin'," he yawned.
Rainbow Dash confidently strode in and dropped both bags on the floor, beside the dinner table. She wore a pair of shorts and a flannel shirt, knotted loosely at the bottom. She stretched, lifting her arms above her head, and something let out a satisfying pop. "Rarity says thanks again, by the way. She's been real busy lately. I guess we all have, huh?"
He awkwardly nodded, yawning again. "Yeah. Sorry, still kinda sleepy. I was up way too long last night."
The athlete laughed at that. "I can tell! You've still got your pajamas on. Lookin' cute," she winked.
Flash squeaked, blushing. He'd completely forgotten what he'd been wearing. He smiled bashfully at her, rubbing an upper arm with his hand. "T-thanks!"
"No prob'. Now, I gotta get outta here. Applejack's waiting on me. I'll see ya later, cool?" Without waiting for a response, Dash gave a quick salute and hurried back out through the door, hopping up into the back of a red pickup. It drove off promptly, leaving Flash alone once again.
Closing the door, Flash glanced over to the black bags. He noticed one of them had a tag hanging off its side, with his name written on it in an elaborate font. Curiously, he kneeled down to see what it said.
Dear Flash Sentry~
I must apologize. When I asked you last night to hold onto some things, I may have been fibbing. In truth, these clothes are a gift. From what you've told me thus far, you don't have many feminine clothes with which to wear. As a fashion designer and producer of such articles, I thought you might appreciate some.
Again, apologies for lying to you. But at the end of the day, you've never been good at receiving gifts, dear. So some subterfuge may have been necessary.
Please do take care of these, though. I worked quite hard on them. I would deeply appreciate it.
Much love,
Rarity
Intrigued, Flash ripped open the bag closest to him. Sure enough, it was piled high with girly outfits, each individually wrapped in gossamer packaging. He smiled, and his heart swelled.
Author's Note
This was purely self-indulgent, I swear 
