Author's Note

Art by Combos & Doodles

Nietzsche alive, this picture is so friggin' magical.

@_@

Remember how I didn't give this story a "pr0n" tag?

Well, it's still pr0n to me (dammit!), and this chapter is no exception. Consider this a... softcore entry into the glories of literary Cross Dressing Smut. If you're like me and you get happy tingles in your chest vacuole over paragraphs describing someone putting on a sundress or accessorizing to match a clutch purse... then that's the kind of kinkiness you're in for with this fic.

At least until Dickfall, anyways.
-SS&E

It's Bring Your Sissy to Work Day!

An animated Princess Rapunzel raised her two-dimensional hand, levitating a bright yellow lantern across the sparkly background of Flash Sentry's laptop screen. Elaborate golden font appeared, trailing with flowers and flanked by cartoon frying pans:

You're the light of our life, Princess!

Beneath this was a separate text box, where appeared the words:

Hope you're doing better, Flash! Don't let Sunset snuggle all the fun outta ya! XOXOXOXO! Rarity, Applejack, Rainbow Dash, Pinkie Pie, Twilight Sparkle, and Fluttershy!

Flash Sentry nibbled on the last of his buttered toast. He gulped, then took a steady sip of orange juice. All the while, his eyes remained pensively glued to the e-mail that had been sent to him overnight.

“...just gotta drop by Cadenza Corp,” Sunset Shimmer could be heard saying. In the kitchen behind Flash, she was standing before the sink, washing dishes in the early morning light. “I pay them regular visits, and I've been... uhhhh... a little be delayed this week. Heheh... I-I don't mean to imply anything by saying that. But... I gotta make a stop at their labs, is the long and short of it.”

Flash blinked. His eyes drank in the super girly, glittery e-mail once more. Then—with his mouse cursor—he backtracked to the main inbox of his e-mail account.

Everything had been checked “read.” There was still no message from Mother, Father, or Magnolia.

He bit his lip.

“I'd say that it'll be a quick visit, but—truth is—they're always finding ways to steal my time for as long as they can. Heh...” Sunset placed plate after plate in the dish drainer as the faucet ran. “Sometimes I think they all have a crush on me. But the actual truth is that they really really rely on my knowledge in Equestrian magic over there. Twilight can only help the Corporation so much, and our mutual friend from the Princess' court only comes to make house calls with the girls at the manor.” She switched the faucet off and dried her hands with a dish towel. “Hell, if she did visit the lab instead, I'd be out of a job.”

Flash clicked on the refresh button.

The inbox reloaded. Still there were no new messages aside from what Sunset's friends sent.

The boi sighed. Leaning back from his crumb-covered plate, the young twenty-two-year-old murmured: “Sunny...?” He pointed at the latest Disney-themed e-mail header. “...do the girls think that I'm dying or something—?”

“I know!” Sunset leaned over him, towering with a bright and bushy-tailed grin. “Why don't you come with me!”

“... … ...” He blinked. “Come with you where?”

She rolled her eyes and ruffled his silky blue hair. “To Cadenza Corp, silly!”

He fussed, shaking his head so he could see past his bangs once more. “Uhhhh...” He brushed his locks smooth and watched as Sunset reached over to take his plate and utensils. “...Cadenza what now?”

“The laboratory belonging to the people I work for.”

“I... thought you had a career as a superheroine.”

“I do. Assisting at Cadenza Corp is... uhhhh... part-time.” Sunset marched back to the sink and washed Flash's plates. “And believe you me: it's a small price to pay for all of the rich things my friends and I are paid.”

“You're... funded?” Flash squinted. “The Elements of Harmony, I mean?”

“Why—of course we are, sweetie!” Sunset winked over at him. “Secretly, granted. But what did you think? We were all mooching off of Twilight's parents?”

“I-I didn't know that Twilight Sparkle was rich—”

“Aaaaaaaand with the Elements of Harmony being out of order for nearly a friggin' month...” Sunset clenched and unclenched her jaw, sighing. “Let's just say I'm not about to shirk my responsibilities when duty calls.”

“And duty calls... today?”

“I've been putting it off. But I really... really need to show up and take a look at the projects they're working on. Give them some advice. Magical advice.”

“I see...” Flash nodded. As he looked aside, his mind wandered to last night... when he had awoken in Sunset's bed. He had heard far more than the amazon had likely expected. Unless—of course—her telepathic abilities had made up for it, in which case there was nothing to fuss over.

Or was there...?

“I think you should come with me!” Sunset said. Just like the morning before, she was all sunshine and rainbows. Practically high. Perhaps... in afterglow. “It'd be a learning experience! Besides...” She turned around and leaned back against the kitchen counter. From the scale of things, she almost looked like she was a petite teenager again, standing in shorts and a t-shirt and rocking back and forth on the tips of her toes. That smile ever tender and friendly. Loving. “...it could do you good to get out of the house.”

“We got out of the house yesterday, Sunset.”

“I know. But it was rainy and gloomy and all you had to talk to was me.”

Flash genuinely puppy-eyed at that. “What's... so bad about talking to just you?”

“Awwwwww... honey...” She reached over and squeezed his shoulder. “Think about all the days, weeks, months you've spent cooped-up in the apartments your parents gifted you.”

Flash shuddered. “Must I...?”

“Point is, I wanna draw us away from that! Let's get some sunshine into your life! Brightness! Positivity!”

“You've got duties to attend to, Sunset. But so do I.” He looked back at his laptop. “I've still got to get on board with...” He paled slightly, remembering once again that there was absolutely no response from his family. “With... with... with...”

“All in good time.” She leaned over like a bosomy right angle and hugged the seated boi from behind. “Come on! Let's live in the moment! See some new places! Well... new for you...”

Flash squirmed where he sat. His eyes trailed to the wrist of the woman embracing him from behind. A beaded bracelet settled to a stop in the morning glow. Somehow—even with the sun's godrays pelting it at full force—the silver looked tarnished. Faded. Flash almost swore he could see through the thing.

“We're just... gonna dip in and out so you can help with your benefactors?” Flash said.

“Shouldn't take too terribly long. Maybe we can do some shopping on the way back.”

“I...” Flash bit his lip, looking aside. “...I dunno.”

“Heehee!” Sunset patted his head and scampered off. “Come on! It'll be fun!”

He started sliding out of his chair, adjusting the lengths of the Princess Peach bedshirt. “Lemme just get back into my hoodie and—”

“Nuh uh! You're not bummin' around in that drab getup for a second day in a row!”

“C-Could I just wash it really quick before we go?”

“There's no time! But don't you worry, Flash! I've got something that you can wear!”

Flash blinked hard. “... … ...you do?”

“Flaaaaaaaaaash!” Sunset Shimmer leaned against the doorframe to her bedroom. She wore a black leather jacket with orange and yellow accents. A red t-shirt and dark black jeans completed the look. The amazon tapped her shoes impatiently against the edge of the wall. “Come on out already! We can't keep Cadenza Corp waiting!”

Silence.

She narrowed her eyes, leaning her head closer to the doorframe. “Flaaaaaash??? What's taking so long???”

A squeaky voice echoed from within. “What's the deal with these pockets??? I can't fit anything in them!”

“Never mind the pockets!” Sunset smiled, arms folded. “How's everything else fit?”

“It... they... uh... they fit just fine... I guess...?”

“Then what's the big deal? Come on out, silly!”

“I dunno... something feels off. C-can't I just go and put on my normal sweatclothes?”

“Nope! No can do!” Sunset shook her head. “I threw those into the wash about five minutes ago.”

“Five m-minutes ago?!?! You didn't tell me that!”

“They were still moist and smelly from all the rain yesterday!” Sunset leaned towards the door, eyes narrowing. “You're telling me that you wish to wear stinky, smelly, damp clothes?”

“... … ….okay, you've got a point.”

“Heheheh...”

“But I really really really wish that you had told me before—“

“I had it all taken care of, Flash! It so happened I've some hand-me-downs that could fit you! Now come on out!” Sunset exclaimed. “I want to see how they look!”

There was a smattering of silence on the other side. Then, the door to Sunset shimmer's bedroom opened with a click.

Curious and excited, Sunset Shimmer took a step back from the door and craned her neck to see.

At long last, the little fae of a boi stepped out. Without the full quintuple-x pyjama top—or the extra bulky hoodie—Flash looked considerably smaller and more delicate than he already was. The twenty-two-year-old was dressed in a short-sleeved green blouse with blue denim jeans. It was simple, conservative, and plain—yet the slimness of the outfit (and especially the jeans) showed off his effeminate, slightly curvaceous figure. A brown belt with tiny silver rhinestones completed the look. He stood in the light of the hallway, toeing the carpet with a sheepish look.

“Awwwwwwwwwwwww...!” Sunset cupped her hands by her smiling cheeks. “Oh sweet Celestia... you look even more adorable than I ever imagined in that!”

“I... guess...?” Flash squirmed visibly.

“Does it feel comfortable?” Sunset leaned in. “Be honest.”

“It... fits almost perfectly.”

Sunset's eyes narrowed. “Then why are you squirming?”

“I dunno.” Flash flexed his arms, glancing at both his peripherals. “The sleeves are... sorta puffy.”

“Are you telling me you hate 'puffy'?”

“... … ...”

“Still...” Sunset leaned back, scratching her chin. “I feel like something's missing...”

“Sunset...” Flash sighed. “Do I really gotta go out wearing this—?”

“Oh! Of course! I know!” The amazon practically pounced on the ground in front of the boi.

“Gaaah!” Flash flinched, nearly falling over.

A kneeling amazon steadied him. “Don't. Move.” She reached her giantess hands in, fiddling around Flash's left ankle. Then his right. Within seconds, she had swiftly rolled up the legs of the jeans by a few inches until they were just below his knees. This evidently accomplished something, and she stood up with a bright grin. “There! Now, turn around.”

“Sunset—“

“Turn. Around.”

Gulping, the boi did a slow, skirt-less twirl.

“Heeeeeeeeehehehe!” Sunset let loose a girlish giggle of delight, clapping her hands. “I knew it! Wow... that's on point! I gotta say... I never thought it'd look so good on you, but I guess you're just so adorable you make anything sparkle, Flash!”

“If... uh...” He rubbed his feet against an exposed ankle. “...you say so.” His eyes narrowed at the rolled-up legs. “Is... that really necessary?”

“Oh hush. You've got kissably beautiful skin, Flash. Let the air have some fun, won'tcha?”

“Uhhhh...”

“And don't worry. I've got some sandals for you to try on.”

“Sandals?” He winced noticeably. “But... isn't it autumn out?”

“Unless it's the dead ass sleet of winter, there's no excuse to not wear sandals,” the amazon said.

“But you're not—”

“It's either that or ugly-ass oversized brown boots.”

“... … ...” Flash blinked. “Sandals it is.”

“Follow me into the living room!” Sunset exclaimed, walking with a smile and a skip to her huge step. “Don't wanna keep Cadenza Corp waiting any longer!”

“I... I'm sorry—”

“Don't be! Just come along!”

Flash stepped after her. He blinked, feeling the a/c of the household breezing past his exposed ankles and arms. Even he had to admit—wearing those large, girly pyjama tops around the house helped him feel snug and comfy. But something about this outfit and its absolute zero restrictions made him feel... lighter. And free-er. Even the normal sweatclothes that he wore out in the open before he reunited with Sunset always made him feel a tiny percentage like the Michelob Man. He had an affinity for needlessly thick, obscuring, and drab wardrobes.

In hindsight—Flash realized—he typically wore those bulky, thick clothes as a means of combating the lithe, girlish figure that fate had long bestowed him. When he didn't, a good number of people looked at him. Stared, even. Most of them men his age and older. He'd be lying if he said that a very hidden part of him didn't enjoy that... to some degree. But, practically-speaking, it was just awkward and distracting. And he had a life to live—a life of drifting from apartment to apartment while doing tiny things to appease the demands of his family.

And—with each passing day—it truly felt as if that dull, drab life was coming to an end. It may have felt weird in a lot of ways, but the things Sunset insisted on Flash indulging in felt like a breath of fresh air. It was only right now that it felt like she was being more... insistent on the challenges/changes. Flash couldn't help but remember a foggy conversation he had enjoyed with the telepath the night before. What if... what if he was being dragged towards the point of no return—?

“Here ya go!” Flash nearly ran into a pair of brown-and-green sandals being dangled in his face.

“!!!” He hopped back with a start, but nervously took the pair in his girlish hands. There was a tiny, crimson cluster of apples in the centerpieces where the toe-straps met. “It... uh... kinda seems juvenile?”

“You kinda seem juvenile!” Sunset Shimmer said, sticking out a tongue and chuckling. “Come on! We don't want to be late!”

“Uhhhh...” Flash slid one sandal on, and then the other. He wasn't expecting the wedges in the heels to be quite as thick, and he teetered a bit upon first standing. “Guhhhh—“ He breathed out the side of his clenched teeth. “I was... s-sorta hoping to bring my phone...?”

“Yes yes yes.” Sunset turned towards the sofa, rummaging through a pile of things. “And you have other important things that you usually carry around with you.”

“But...” Flash fidgeted, plucking uselessly at the sides of his jeans. “...these pockets couldn't even fit postcards. How am I going to—?”

“How else?” Sunset Shimmer turned back around, brandishing a soft felt burgundy object. “Ta-daaaa!”

The boi blinked, frozen in place upon seeing the object. “... … ...Sunset, that's a purse.”

“You're a purse!”

He sighed hard. “Sunset—”

“Here!” She practically tossed it at him. “I already put your stuff in it!”

“Mmmf!” He caught it to his tender chest, his eyes darting to peer down the half-open lid of the bag. He could already see his phone, hand sanitizer, wallet, the pocket-knife that he never used...

“I took the liberty of adding a few things,” Sunset said, grabbing her own purse.

Flash squinted. “... … ...Tic-Tacs?”

“Heehee... can't go anywhere without a packet of those!”

“Sunset...?” He bit his bottom lip, hugging the article awkwardly to his green blouse while looking up at her. “What's wrong with my messenger bag?”

“Well, for one, you insist on calling it a 'messenger bag.'”

“... … ...huh?”

“Seriously, Flash. You've carried that thing around for how long? Since graduating CHS? You're already used to bag-life. Why not upgrade?”

“How's this an upgrade?”

“Uh...” Sunset leaned over to glare at him. “Because it's small. Light. Accessible. And not a stupidly dull, drab, big, oversized, brown 'messenger bag.'”

“But... b-but...” He rubbed one exposed cankle with another, glancing nervously out the door. “...what if people see me out in public with it—?”

“Then bonus!” Sunset grinned, stretching her arms out. “Add that to the high score!”

“Sunset...”

“Oh, excuse me, princess.” Sunset snorted back a laugh while smirking wickedly down at the boi. “But just who was rambling sleepy-drunkily about the pure joy of carrying a purse out in public last night?” She waggled an eyebrow. “Among other things?”

Flash's heart jumped... then sank... then jumped again.

She had him there.

All things considered—knowing even a fraction of the full conversation he had had with Sunset the evening previous—she was going to have him in a lot of places. This was a losing battle from the start. He might as well accept defeat with dignity.

Flash took a deep breath, steadied himself, and slid his wrist through the handstraps of the purse. “Alright...” His voice was adorably scratchy, despite his proud and tall stance. “...let's get this over with.”

“Oh no no no no no no sweetie.” Sunset shook a finger. “You're gonna break your fragile little wrist if you do that all day. A purse that size? You gotta hook the larger strap cross-body... over your far shoulder. I promise it's waaaaaay comfier. Like this!” She pulled the strap of her own purse over her head so that it crossed over her ample torso. At last, the bag itself rested effortlessly against her hip, with easy-access for her hands. Nevertheless, the amazon struck an adorable pose. “Ta-daaaa! See?”

“...alright... erm...” Flash nevertheless struggled with the stupidly easy motion. At long last, he had the burgundy bag resting against his hip with the strap crossing over from his shoulder. He resembled a daughter mimicking her mom. “Uhm... ta-da...?”

“Heehee! Right on! Now turn around again.”

“But—“

“Turn arounddddd...”

Sighing, Flash slowly did so, his arms lazily outstretched like a tired ballet dancer. The bag lifted a bit until he came to a stop. “There. Are you happy—?”

Flash! Sunset finished snapping a photo with her cell phone. She swiped right, grinning. “Perfect!”

“Sunset!!!” Flash's voice cracked, and his cheeks matched the color of the purse. He clasped both hands together, shivering and pigeon-toe'd. “What are you doing?! Delete that! Delete that!”

“Why should IIIIIII?” she cooed, plinking away at the screen of her mobile device.

“But... that...” He whimpered. “Who are you sending it to?”

“Nobody for you to be worried about.”

“B-but that's st-still somebody!”

She slid her phone back into her purse and winked down at the boi. “Flash, sweetie, even if I sent it to the worst dictators on this planet... the most it would do is brighten their day with how utterly adorable you are.”

He stood in her shadow, gnawing on his lip. “I... uh...” He absent-mindedly fiddled with the taut strap of the purse. “I... I... I...”

“Oh goddess. One of these days, I'm gonna eat you up. I swear.” She walked over, squeezed his shoulder, then turned him towards the front door. “Let's bounce. Maybe the autumn air will cool you down. Heheheheh...”

Flash squirmed in the passenger's seat, resting the purse in his lap. He raised a finger and poked at the poofy shoulders of the green blouse.

“I swear... there's something familiar about this outfit...”

“So, ever since the geodes were found in Camp Everfree,” Sunset Shimmer was speaking as she drove the car down a narrow country road flanked by forest. “There've been other manifestations of Equestrian Magic... distilled into physical constructs. Twilight and I together built a device that could root them out.” She winked aside. “In truth, it was mostly her genius design. I just helped her figure out a formula by which it could detect magical signatures.”

“I mean... it's obvious that it's been worn before,” Flash muttered, glancing down at the rolled-up legs of the jeans. Even that looked familiar. “But by whom...?”

“As the Elements of Harmony, we need to protect the citizens of this world from all magical threats. This includes Equestrian magic that may appear inert... but still holds a chance of manipulating the environment or people around it.” Sunset cruised the vehicle around a hilly bend in the road. “But sometimes we find... nodes full of constructs that are simply energy batteries for magical leylines. These we donate to Cadenza Corp's Industry Division... so that they can experiment on making new and safe ways of mounting non-lethal defense. Y'know... in case the Elements of Harmony lose their abilities for good? Someone good and virtuous could take our place in a non-threatening way!”

“...but I haven't seen this purse before...”

“Also, there's an effort to harness the power of the Equestrian constructs into new forms of boundless energy so that we can power microscopic machines to aid in the battle against cancer—but I've already hinted at that the other day...”

“...because if I did, I would have remembered it.”

“Flash!” Sunset's face scrunched. “Are you even listening to me?”

“Huh?” Flash looked up at her. “Something something magical horse batteries?”

She chortled. “Dang it, Flash—this is serious stuff! Slowly, bit by bit, the Elements of Harmony and Cadenza Corp are saving the world! I'm trying to tell you—it's a supremely wonderful thing!”

“Right. I believe you, Sunny.” Flash nodded. “And... you're getting paid for it?”

“Heh...” She smirked. “The girls and I are being supported for it.”

“Like... the house you live in. They built it for you—even made the furnishing and stuff for how super tall you all are.”

“Very good, Flash.” Sunset nodded. “They did the same for the rest of the girls. Plus... there's the manor...”

Flash squinted. “The manor?”

“Oh yeah. Didn't I mention that? Anyways, that's where Twilight and the rest have been hanging out as of late.”

“... … ...” Flash looked out at the trees and shrubbery passing by the forested road. “You girls... also have a manor...?”

“Look. It served a different purpose before we moved in. But... yeah.” Sunset cleared her throat. “I try not to brag about it.”

“There's a lot you must try not to brag about,” Flash murmured. “I keep finding out, bit by bit.”

“Yes, well... I'm mostly focused on making sure you come out of your situation A-okay,” Sunset said, briefly reaching a hand over to squeeze his shoulder through the puffy blouse sleeve. “Maybe you can forgive me for making the revelations... uhm... only when they need to be made.”

“So long as you're not hiding a massive shotgun under your clothes or something,” Flash muttered.

“Hahahahaha...” Sunset laughed nervously. “Haaaaaa ha ha ha ha ha...”

“...?” Flash looked over.

“Ha ha ha ha ha ha...” Sunset sweated a bit. Her hands gripped tighter to the wheel. “Heheheheheh... heh heh... hoooooooooo boy...”

Flash was silent. Even as Sunset continued chuckling, unabated. His eyes glanced to the silver beads of her bracelet, then back to her. “So... we're just in and out for you to check on their experiments?”

“Hahaha—oh! Uh... yeah! Totally!” Sunset gulped hard, wiping the sweat dry. She looked beautiful and composed yet again. “Cadenza's got their best people working on it, but they still don't fully understand how to harness and control magic. So Twilight and I stop in every once in a while to brush them up and do a little overview.” She blinked. “I've already been over this, haven't I?”

“Yes you have.” Flash nodded. “You seem distracted, Sunset,” he droned. The boi remembered the amazon pacing outside the bedroom door the previous night, looking frazzled and anxious. “Is everything okay?”

“Why wouldn't I be?” Sunset craned her neck. “Ah! Look! We're coming up on the entrance gate.”

Flash watched as the car veered off onto a side-road. A large pink-and-gold sign read “CADENZA CORP INDUSTRIAL FACILITY” in bright, reflective font. Up ahead, Flash could make out a security gate.

“It won't take long for us to pass through,” Sunset said. “They all know me here. We're practically family.”

“But... uhm...” Flash squirmed in the passenger seat. “What will they think of me? Won't they be concerned that you're bringing a stranger along?”

“Naaaaaaaah.” Sunset smirked, reaching for her purse. After fishing around, she produced a magnetic card. “Hell, they'll probably think you're my baby sister.”

“Sunsetttttttt...”

“Heehee! Face it, Flash. You're too adorable to be threatening.”

The shift in the vehicle's path caused Flash's image to be reflected slightly in the car's inner windshield above. He had the first opportunity to see over half of his body in that getup.

“Why... is it so familiar...?” the boi whispered.

“Probably because you've got a dollop of country town flare in ya, Flash.” Sunset rolled down the window and greeted the security guard at the gate. “Hiya, Frank! How's the kids?”

Flash looked down at his sandals. His eyes centered on the plastic apples clustered at the toe-straps.

“Growing inches every day! Who's the pretty one, Miss Shimmer?”

“This is Flash. 'Pretty' is the word! Like a sister to me. Say 'hi,' Flash!”

But the boi was too busy paling and grimacing. “Oh my God...” He hugged the purse to his chest. “These are Apple Bloom's clothes!”

“Whelp! Gotta drop on in!” Sunset waved as the gate lifted. “See ya, Frank!”

“Give my love to the boss lady!”

“Sunset...!” Flash squeaked, gawking at her as he hugged the purse tighter. “Why am I wearing Apple Bloom's clothes?”

“Because they fit you,” she calmly hummed, aiming towards a parking space.

“But... but...” Flash bit his lip. “It's weird... isn't it? She had these on when she was a middle schooler.”

“No she didn't.”

“... … ...she didn't?”

“Heehee... you're puny, Flash. But not that puny.” Sunset settled the car into a stop and shifted it into park. “Those are hand-me-downs from when Apple Bloom was in her Junior Year. Turns out she had a massive growth spurt.”

“She d-did?”

“Yeah. You probably weren't paying much attention cuz you were too busy being you. Also you graduated. But you should see Applejack's 'baby sister' now!” Sunset put on a wry smirk, wagging her eyebrows. “She's about 6'1” and drop-dead gorgeous. No joke—she's in the supermodel business. For a while there, Applejack was scared that she had 'inherited' a bit of her Amazonian magic nonsense... but... nope! Just a really, really ripe apple.”

“Huh...”

“So yeah. I'm pretty sure Apple Bloom only wore that outfit you're wearing once. She was too busy becoming a human skyscraper. At least... that's what Twilight said that Rarity said that Applejack told her when she gave Rarity who gave me the clothes yesterday morning. The girls all made a bet on whose outfit would fit the best. Rainbow still thinks Scootaloo's will look good on you. Rarity's still banking on Sweetie Belle—but she ended up the shortest of the three little scamps. Heheh... even now that they're a second year into college.”

“Wait...” Flash's eyes narrowed. “...just how many outfits are you trying to throw on me—?”

“We're heeeere!” Sunset popped the car door open and stepped her massive self out. “Just on time, too! Who'd a thunk it? Heehee! Come, Apple Flash!”

“Ennnnngh...” Flash girl-stepped out of the car and pensively followed the amazon towards the main buildings, clutching the strap of his purse the entire way.

The autumn air nipped at him playfully, exacerbating his soft goosebumps.