At last, the very next day and after much anxious searching, Rarity finds him...
Flash Sentry sits alone on the bleachers beside the Canterlot High School football field after last period.
But he isn't alone for long.
"There you are, Mr. Sentry," Rarity says, walking up while hugging her bag to her chest.
He looks up, his perpetual slump of gloom ultimately disturbed. His eyes widen, and it looks for a moment as if he's going to dash away. But the generous purpose that has bought Rarity there—seemingly—anchors him in place. Besides, he's too gentlemanly of a young man to ditch a lady twice. Rarity has bet on this, and although she evidently wins—the defeated look on his face as he slumps again only breaks her heart all the more.
"Rarity, I'm sorry," he exhales, eyes clenching shut. Lines along his face betray a lack of sleep, and he runs a nervous hand through his hair. "I ran out on you without saying a word. That was... super rude of me." He gulps. "Especially after you... you were so kind to—"
"There will be a time for apologies," Rarity says. She squats down next to the larger teenager, and yet her petite size somehow dwarfs his feeble posture. "As for now, I simply wish to know that you are alright." She clenched her teeth. "Fleeing the Boutique in melodramatic fashion is one thing, but ignoring my texts? And Sunset's as well?" A stern breath, but she then softens noticeably. "What if something truly terrible had happened to you? How would your friends be able to aid you in time?"
He doesn't say anything. He doesn't even move. Rarity's hunt has come to an anticlimactic end, and it wounds her.
"Mr. Sentry... Flash..." She bites her lip. "Has something truly terrible happened to you?"
He only fidgets, eyes stuck to the lower seats of the bleachers below them.
"If..." Rarity's voice lilts in noticeable worry, distress. She holds a shaky hand over her chest. "If I-I said or did something to trigger an awful memory in you—"
"You didn't do anything—" he mutters.
"I most certainly did! I... I crossed a boundary. One that I wasn't entirely certain existed, but nevertheless... here we are." She takes a breath, calmly placing her bag beside herself before scooting closer to him. "Flash..." She rests a hand on his shoulder. "...it pains me to think I've done something to hurt a dear friend of mine. Won't you please tell me what's amiss?"
His eyes darted halfway towards her.
"Yes—believe it or not—you are a close friend. I value your strength and sincerity. And—above all—your loyalty." She smiles sweetly. "I think about it every night and day, and still I cannot fathom what we girls did to deserve such a chivalrous soul as you to bless us on a regular basis. Now—please—let us take care of you. Tell me what is wrong so that we may right it!"
He opens his mouth... lingers... then says nothing.
With a brief huff, the fashionista folds her arms. "You know, if Rainbow were here, she'd have punched you several times by now."
"You're free to do the same, Rarity," he mutters.
"No." She shakes her head. "That is not my style. Besides, I hurt you enough as it is."
He groans, grasping his head in two hands. "You didn't hurt me—"
"I most certainly did! I pressed too hard without thinking! Why else would you have run out of the Boutique?"
He wrings his hands together, growing more uneasy.
She sees it. She speaks—gently. "It's when I offered to make you a dress, isn't it?"
He tenses up.
A soft smile. "My darling Flash, do you truly... honestly believe that you're the first and only man to step into my Boutique, secretly desiring the exquisite feeling of being enmeshed in something beautiful?"
His eyes look towards her, only for him to pretend that they didn't.
She sees that too. "It is true. I assure you. In fact, at least ten percent of my clients who order dresses aren't female," Rarity declares. She crosses her legs daintily and leans back, breathing more assuredly. "It's gotten to the point that I've felt compelled to... draw the truth out of my male window-shoppers, rather than just let their suppressed potential to inquire fester and stew into despondent oblivion." She clears her throat. "I... thought that I had gotten good at reading the body language of such a situation, and I saw it in you when we were talking about those designs I had made. The look in your face. The twinkle in your eye. It's none too different from the female clients who see their finished commission for the first time. And... and th-that's a tender-hearted joy that I absolutely hate to squander. But..." Her voice shakes with brief but genuine emotion. "...what I despise even more, Flash, is doing anything to hurt my friends or make them feel uncomfortable." She swallows delicately, then declares: "My offer still stands. That shall never change. But I must know—is there anything I can do to rectify what's been done? How can I help you to know that... that it's alright. It's perfectly fine to desire to dress beautifully."
He rubs his hands together, slowly rocking back and forth where he sits. Rarity's presence has transformed him from a slumped pile of sighs and into a jittery pantomime of passing a kidney stone. Nevertheless, the fashionista waits in silence, drawing the truth out of him with persistent, patient stillness. At long last, it springs forth.
"I... I don't talk about it much..." Flash practically whimpers, still avoiding her gaze. "By that I mean frickin' not at all." He gulps hard. "It... it's nothing but a stupid, weird complex."
"Let me be the judge of that, darling."
"Rarity..." He grumbles, frowning at nobody but himself. "It's not every woman's job to entertain the stupid, gross fetishes of a dude—"
"Flash, look at me."
Biting his lip, he slowly does so. His eyes are round and vulnerable—something she has half-suspected.
She keeps her sympathetic breaths straight. "You are my friend. And I wish to help you. You say that you've never talked about it before. Well, let me change that," she says. "Let me help you get it out into the open. So you will be free."
Flash Sentry gazes at her, this time unflinching. The shakes stop, and soon he's exhaling the truth like a deflating balloon, slow and quiet and tender in his tone.
"All my life... for as long as I can remember... I've been in love with girly... feminine things..."
Rarity simply nods.
"And I-I don't just mean girls... as in women. The opposite sex." He gulps, smiling for the first time since she arrives, but it's a plastic gesture. "Although you're all pr-pretty great too..." The smile fades, and he's wringing his hands again. "But... mmmm... stuff that's attached to girls. Like... things that society says should be attached to girls. And not boys. Dresses. Makeup. Accessorizing..."
"Indeed..."
"But—uh... not just the superficial stuff, but..." He sighs slowly—but lightly. His eyes travel up to the sky, twinkling slightly as he speaks: "The stereotypical emotions assigned to girls. Sensitivity... compassion... selflessness and steadfastness. I mean—sure—it's not indicative of all girls—"
"But girlishness," Rarity clarifies.
He swallows. "Right." He swallows again. "I... I don't particularly know where it all began." He glances at her again. "Playing house with girls in preschool? A sleepover my older sister was having that I happened to participate in—like—when I was super, super young?" He shrugs. "Whatever it is, it's a super positive memory. Like... something that has forever impacted me on a... nearly spiritual level."
Rarity smiles. "Well, that's certainly relieving to hear."
"And... and for years—even long before puberty—I just... just..." Flash fought the bumps in the road to confess it out loud: "...fantasized nonstop about playing dolls... but... for real. The big leagues. In real life. Dressing up like... mmmm... those beauties in princess movies. It's so simple and yet so complicated all the same. But—whenever I see someone or something pretty—I want to be that." His features deflate, and he's hugging himself at this point, gazing into some far off indefinable pinprick of purpose. "I want to feel soft... to be soft. To be encompassed in the essence of gentleness. To smell good. To talk with a honey'd voice and be precious and be rare and be cherished... be cherished just for who I am and how I could be packaged and... a-and knowing that it's not laziness and it's not opulence but... but some sincere extension of prettiness that I could somehow... just somehow possibly own."
She looks at him. She says nothing. She waits.
And, soon enough, Flash Sentry delivers: "Sunset Shimmer? Twilight Sparkle?" A shrug. "They were amazing experiences... well..." A brief eye-roll that summons the tiniest of chortles from his listener. "...for better or for worse... and while I enjoyed their company and I... still admire them in a certain capacity..." He rubs the back of his head, shuddering. "I... I-I think what I desired the most from them wasn't so much their femininity... but being close to their femininity... so that... so that I-I could feel what it was like to possess something close to it... not them, of course—but something that belonged to them... th-that could belong to me too. I... I just wanted to understand more. But I can never seem to understand... no matter how close I get. And... and even today..."
He looks at Rarity.
"I adore you... I adore each and every one of you girls. You're... you're just so amazing and spectacular and..." He lingers, then smiles tenderly, his voice taking a slight lilt. "...and so beautiful. And so strong. And so confident. Sometimes I worried over myself... because one day I would wake up and... and I-I would be in love with Fluttershy. But then that afternoon I would think I was in love with Applejack. And the next day you and the next day Pinkie Pie and the next afternoon Rainbow Dash and..."
A brief bout of silence, as Flash winces—as if having traipsed too far into this new undiscovered country. But Rarity's silent stalwart gaze gives him lease to finish:
"I wondered how I could possibly be in love with so many girls all the time. And then... it occurred to me... that maybe I was in love with all of you... and yet none of you. Thinking too hard on the matter—and, God forbid, confessing it would..." He grimaced, having crossed that very same threshhold. "...it would ruin something so wonderfully precious... so wonderfully precious as being your friend... being around all of you so often, every school day and every afternoon and every weekend... listening to you all talk... seeing you all do great and kind and magical things for those around you... smelling your perfume and complimenting your outfits and admiring the graceful ways you carried yourselves about and then... then... feeling this awful gnawing feeling whenever you all went off to enjoy a slumber party or some other deeply personal activity and knowing that... th-that I couldn't join you. All because..." He clenches his teeth. "...all because there's so much stupidity in the way... stupidity that just... just complicates everything."
His last statement has a breath of finality to it, which is what triggers Rarity into finally responding.
"That all sounds so very sweet, Flash," she states. "Especially coming from someone like you. You mean a lot to us... and it's awful to think you've felt left-out. Alienated, even."
"Yeah, well.." Flash rubs the back of his neck again. "Don't stress it. That's all my fault, not yours."
"It's not a question of 'faults,' darling." She gently clasps her hands together and leans forward, eyes gently coaxing something within his own gaze. "Flash, have you ever taken the time to consider whether or not you may in fact—"
"I'm not trans," he almost grunts.
She blinks, reeling slightly. "I am by no means a psychiatrist, dear. It was simply an inquiry—"
"Sorry... sorry." Flash facepalms, sighing hard. "That... that came across badly. I-I don't mean to imply that there'd be anything wrong with me being trans or genderfluid or whatever. But... but it's not any of that."
"Are you certain?"
He slides his hand slowly down, revealing a bitter smirk. "Is anyone certain?"
Rarity chuckles breathlessly. "I... could not pretend to account, personally."
"Me neither. Cuz I'm not trans. And I've got nothing on those who really are," Flash says. "I just think that actual trans people have a lot of challenging crud to go through and... and what I am simply isn't comparable, and I don't want to insult anyone by grouping myself with those who struggle with stuff I can't even comprehend."
"I don't truly think it's that incomprehensible to someone like you, Flash—"
"I'm just a natural-born dude and I recognize that," he carries on. "That's me; I'm certain of that. And... and it's that personal distinction that... th-that makes my obsession with definitively 'un-dude' stuff—like dresses and makeup and slumber parties—all the more... enrapturing." He sighs. "...biggest and boldest word I could think of."
She giggles lightly. "And quite a good word it is, indeed. So..." She crosses the other leg over and rests where she sits. "You identify as male."
"Yes ma'am."
"And... you're a male-identifying and male-coded soul who loves the idea of cross-dressing."
He fidgets noticeably. "... ... ...you make it sound so innocent."
She gives a light shrug. "I don't see why it can't be."
Two lazy eyes glare in her direction. "Have you seen the websites that crossdressers frequent on the Internet?"
"Is there a reason I should have?"
"Do you know who Jamie Farr is?"
"I'm afraid the name escapes me at this moment, darling."
"Doesn't matter. I was just trying to come up with a metaphoric archetype."
"An archetype of what?"
"Basically..." Flash gestures with two shaking hands. "...the only people I ever seem to have anything in common with are predominantly super furry basement neckbeards who share the cringiest of photos across niche Internet message boards. And—lemme tell you, Rarity..." He breaks through his nervous veneer with an even bitterer chuckle. "...that much hair and pink lace does not belong in the same digital room."
She tries her best not to grimace. "Your hyperbole... is certainly making its way into my mind."
"Reality sucks," Flash grumbles. "When the day comes that I'll finally gain the courage to act out my most sincere of personal fantasies, I'll be two hundred and twenty pounds and pot-bellied as all get out. Heh... try putting a ballgown on Shrek after rolling through a bathtub of Rogaine." He runs a hand over his face, sighing heavily. "I'll be the Drag Queen of Cringe. It's only fate."
"Flash..." Rarity rolls her eyes before tossing him a snide smile. "I do believe you have frolicked from whole-hearted confession into mental meltdown."
"Well..." He hugs himself, slouching away from her. "...what did you expect?"
"To be honest, a lot worse than what you're telling me now."
"What can be worse?" He mutters, clenching his eyes shut. "I'm helplessly imprisoned by my own obsession."
"Humor me for a moment, darling." Rarity folds her hands together, cocking her head towards him. "If you were—this very second—granted a visit from your Faerie Godmother..."
His eyes instantly fly open at that; she tries not to giggle.
"...and with a wave of her wand you were gifted the absolute most beautiful shimmering ballgown in the land..."
His lips pressed together. "...with puffy shoulders?"
"Yes!" She finally chuckles. "And a tiara to boot." Her eyes narrowed. "Imagine—this very moment—you were so lacily clad, with an invitation to the ball... to be with all the other pretty maidens whom you've admired from afar all your life..." She leans forward, resting her chin in her hands. "What would be the first thing that you would do?"
"Like... what do you mean?"
"As I said—humor me."
He's silent for a while, contemplating. Then, closing his eyes, Flash shudders to say: "I... I think I would cry..."
She listens.
"I would just... cry and cry... until the makeup ran down my face. And..." He gulps. "...then I would clean my face up... reapply the makeup... and just... cry some more..." A sniffle. "...and then I would lie down in a soft, plush bed somewhere in that very same gorgeous dress and... fall asleep thinking of each and every one of you... and h-how I could somehow thank you all for the greatest magical gift ever come morning."
"Well... I did suggest that there was a Faerie Godmother involved, but..." Rarity chortles again. "That's quite flattering nonetheless."
"Mmmm..." Flash nods, his closed eyes lining with moisture.
Rarity reaches over, touching his shoulder. "Flash..."
He opens his eyes, tearfully meeting her gaze.
"This beauty that you aspire to possess..." She reaches up and strokes his chin... then his cheek, collecting the tears as they form on the young man's yearning expression. "...it is not quite as elusive as you think. And—believe it or not—putting on a dress or makeup or tiara will not give you the satisfaction of achieving beauty that you think it will."
He shudders at that.
"Shhh-shhh... listen to me, darling." She strokes his cheek again. "Such catharsis must come from another place. This is true with each and every one of my clients when they put on my outfits for the first time. It's not the dress in and of itself that completes them. They themselves are the masterpiece. My artistry is simply a means—a vessel—of carrying their inner beauty to the surface. When they stand before a dressing mirror, it is something from within that is reflected back. Grace and confidence requires a certain degree of strength, conviction, and—most of all—transparency. Your so-called Jim Furrs of the Internet probably know this secret..."
Flash smiles ever so slightly, humored. He shudders as another tear leaks.
She brushes it dry with a nimble finger. "...which is likely why they effortlessly relish in sharing pictures of themselves. That insufferable 'cringe' you speak of is a frail, gossamer barrier once you've learned to embrace the fearlessness that comes with looking inward."
His lips quiver. "What... if I-I don't like what I see when I look?"
"Oh, but I think you will, darling." Rarity nods. "Especially if it's anything close to what my friends and I see." She lowers her hand to rub and squeeze his shoulder. "You are so... so very beautiful, Flash Sentry."
He hiccups on a sob, staring down at the bleachers.
She gently—but assertively—lifts his gaze again. "In all that you say and do. In your gentle restraint... in your quiet, loyal patience with the whole gaggle of us. How you love and cherish everything... but respect everything... knowing the scope of life's tender emotions and how to carefully keep the spectrum in check, even when you don't think you actually understand it. Why—if I had all the resources in the world to make a dress befitting what resonates inside of you, the gown's brilliance would blot out the sun."
He makes a sweet sound at that which forges the river—like a giggle.
She's also smiling. "And... and I know that it's hard, Flash," she coos. "From every friend and client and fear that I've ever encountered." A gulp. "It take an awful lot of courage getting to a place where you'll discover yourself. Embracing him—or her—is even harder... but also liberating. And—more than anything—I want to help you get to that place of peace and joy, for there are few acquaintances I know in this life who deserve it more."
"What..." He sniffles, staring at her. "...what if 'my place' in life is never getting to a place?"
"Mmmmm... designing a ball gown for chaos incarnate?" She winks. "Sounds like a most smashing challenge."
He laughs. He breathes. He tries to wipe his face dry with two cumbersome hoodie sleeves.
Rarity reaches into her bag and produces a delicate lace handkerchief. She hands it to him.
Flash pauses. He reaches for it... lingers slightly... then finally clasps the fabric. As she leans in for a gentle side-hug, he dabs his face dry and finds the strength to breathe straight.
"I... I don't know what I'd do if you hadn't shown up just now..."
"Ruined your handsome posterior sitting on these bleachers forever. That's what!"
He chuckles. "Even now, Rarity? You're flirty?"
"I can't help but flirt with the world, darling," she says, squeezing his shoulder again as he relaxes. "Sometimes—allure is the best way to bring an oyster out of its shell."
"Heh... yeah... I-I guess..."
"Even if there's some fumbling along the way." She nudges him. "But I stand by what I said yesterday in the Boutique."
"Hmmm?"
"My offer, Mr. Sentry..." Her mouth lingers open, and she repeats—more softly: "Miss Sentry."
She has his full attention now. Locked eyes and a thumping heartbeat.
"I would and will gladly design something beautiful for you—if you so desire." A wink. "The first one is free. The second time will cost you more than carrying heavy sewing machines, you strong thing you."
"I'll... uh..." Flash swallows. "I'll think about it."
"I hope that you do," Rarity sweetly says. "Because—and I do not mean this in mere jest—I truly, absolutely believe that you would look fabulous in a sea-blue ballgown, darling." She tilts her head to the side, sizing him up in her mind's eye. "Mmmmmm... with a lace seafoam trim and matching sleeves. Yes... most fabulous indeed."
"Mmm..." He nods stupidly into the distance. "...Flashbulous, even"
She blinks. Hard. A tiny, dainty snort, and she playfully hugs him, shaking all over with their combined laughter. "Are we seriously going to end this whole blessed thing on a Dad joke???"
And maybe we do.