Midnight in the Garden of Principals and Fembois

by shortskirtsandexplosions

Rating: mature
Tags: Romance, Equestria Girls, Sex, Flash Sentry, Principal Celestia, Slice of Life
Length: 3618

Late at night, after an evening of fun with Flash Sentry, Principal Celestia reflects on how lucky she is to have a femboi princess to call her own.

Late at night, after an evening of fun with Flash Sentry, Principal Celestia reflects on how lucky she is to have a femboi princess to call her own.

Tags: [F/M] Gentle Femdom / Pet Play / Age Difference / Sissy Cross Dressing / Flagrant Femboi Idolizing
-Flash Sentry is age Eighteen because of-fucking-course and I also don't like steel bars.

Cover Art by Pia-Sama

Published 2019-01-19 05:40:03 UTC
Last updated 2019-01-19 05:40:03 UTC

Letting Sleeping Dolls Lie

Her house echoed briefly with running faucet water. There was a flicker of light—there and gone again. The hushed hallways fell into shadow once more. Soon, Celestia's softly-padding footsteps scuffled the carpeted stretch from the bathroom back to her bedroom. The woman walked mostly-naked, wearing nothing but a lace violet thong and an unbuttoned ice-blue nightie. Her hair cascaded in irregular strands, tickling her shoulders and the furthest fringes of her ample bosom.

She teetered for the last stretch before her bedroom, thrown off balance by an all-encompassing yawn that made her seem twenty years more diminutive, if only for a silly second. She stretched her arms up towards the doorframe as the gesture culminated... and then she stopped suddenly with a slight quiver to her areolas.

Celestia gazed lengthily into her bedroom. She wasn't looking at the jasmine-scented candles that had burned halfway down their jars with smoldering wicks. She wasn't staring at the distant television which had been set to low volume, currently flickering through a three-decade old marathon of nearly-forgotten gameshows. She wasn't even glancing at the ottoman situated oddly in the center of the room, its quilted surface dotted with abandoned beads, dildos, a rider's crop, and three half-empty jars of personal lubricant.

No, Celestia was looking at her bed—a queen-sized spectacle of tangled silk sheets and shiny blue satin—and more specifically the lithe young form that lay chest-first in the middle of it, his precious face buried deep within a plushy plateau of pillows... his bare shoulders and supple back slowly rising and falling in cherubesque slumber.

This was not a strange sight to the voluptuous principal. In fact—for all its pleasures and perils—it was something she had gotten used to seeing in the middle of the night over the past three months: an entire school semester filled with joy, naughtiness, and a daunting game of ultimate risk-taking. Oh, the young man was legal, alright. She had that going for her: eighteen delicious years of tender, virile sincerity that simply melted at her commanding touch. The whole world as Celestia knew it—of course—would nevertheless collapse if their "affair" was ever discovered... much less the multiple kinky ways that they had explored said relationship in and out of the scholastic work place. Seeing her young lover anywhere, including in her room, gave Celestia's heart a startled flutter—one that she had grown quite addicted to in its adrenaline rush, even if she had long learned to dismiss it.

But now—for a strange and breathly reason—she allowed the sight of him to absorb itself into her mind, and heart... where the flutter persisted without ceasing. That flutter turned into a flushed warmth that spread rosily through her exposed bosom, circulating into a pair of awoken nipples that hardened in sequence with her painterly smile.

Flash Sentry lay sleeping in her bed; he was a part of her bed. In more whimsical ways than Celestia could count, this living treasure had become a part of her home—a priceless portion of what she had come to identify as her own. And though she didn't actually possess him (they had certainly role-played at length that she did), she had enough memories—both precious and perverted—to frame around the sight of him then and there and realize just...

Just how lucky of a "mistress" she was.

Celestia raised a hand to her smiling face, chewing and suckling on a delicate knuckle as she took a time to stand there and bask in the sliver of warmth lying halfway beneath those loose silk covers, like a messily unwrapped present. Sneaking Flash Sentry into her home was always like enjoying Christmas every weekend. She had certainly had her fill of her "toy" hours ago—back when the candles were considerably taller, more fragrant, and dancing from the melodic sounds of both the boi's agony and ecstasy. Through the whole chorus, the song had belonged to Celestia, and her heart still rang with it—chiming even more so at just the mere sight of him.

So—feeling purely decadent—Celestia crossed the distance so that the sight would be ever more closer. She slid herself into bed beside him, descending onto her spot like a silent cloud. The mattress was still warm from where she had woken up just a few minutes ago for a midnight visit to the restroom. She remembered falling asleep at the culmination of their activities with Flash cradled in her arms. At some point in the middle of the night, tossing and turning must have separated the two. Celestia felt immeasurably guilty for that, and she washed those sins away with the sight of him—just... lying there in a full recline, with an arm propped against her smiling chin as her eyes traveled all over the lengths of the young man.

In truth, there weren't many "lengths" to be had. Of all of the partners Celestia had enjoyed—and also regretted—Flash Sentry was by far the most petite of the bunch. This was due to more than the mere fact that he was at least half her age. In his last year of high school—it would seem—the eighteen-year-old's growth took an indefinite holiday. It was one of the first things Celestia had keenly noticed about him—aside from his sparkling blue eyes, silk-soft hair, and divinely spankable derrier.

When the first push came to the first shove and the two found themselves rapidly making out in the break room after the final bell one day, Celestia discovered that she could effortlessly hoist Flash up onto the coffee counter and press him hard against the faculty bulletin board—a mutually-relished feat that led to no small amount of ravenous fondling. As that breathless fling flung itself into a full-fledged affair, Celestia chanced upon other stunts she could pull—with Flash as the starry-eyed trapeze artist of her dominant ministrations.

But it wasn't until the collar came into play—and all of the other frilly things associated with it—that Celestia truly realized that they had both stumbled upon a match made in heaven. With all of her previous partners, Celestia had desired more than to be "on top." She had wanted—even demanded—full control. Unwaveringly. With blushing cheeks, a nod, and a pair of knees that knew when and where to bend. Unsurprisingly, most of her past flings weren't entirely copacetic with this deep need burning within the bosom of the palpitating principal. Celestia wanted more than just a partner that mirrored her passions. She wanted a doll... something that she could cherish, embellish, and—yes, on occasion—even be playfully cruel with. The problem was finding someone who wouldn't have a problem with this... who would somehow be so insanely aligned with her unquenchable kinks that it wouldn't be interpreted as one-sided... which it was.

Celestia wasn't willing to settle for less than what her heart desired, which is likely why she went through so many failed Mr-Right-Nows while on the grand search for Mr. Forever. For years, Celestia fumbled, growing further and further from realizing the idol in her dreams. She rationalized that it was for the best; rarely did any of her partners ever measure up—or measure down to the tender template that she was looking for... someone whom she could equally benchpress, snuggle, or both. A few catered to Celestia's requests, but they were too imperfectly large and oafish for the job. She was a poor woman looking for a purse dog while drowning in a sea of Great Danes.

But then Flash Sentry happened—and he happened again. And again and again and again—until Celestia realized that a horribly bad career decision was also simultaneously the lover... the pet... the doll that she he always wanted. For—against all the astronomical odds working to ruin their combined destiny—Flash had long fantasized about becoming that very same plaything, and Celestia was his magical opportunity to serve, please, and exalt someone with far greater power, majesty, and feminity than himself.

And it was a feminity that Principal Celestia shared. Gladly. Obsessively, with surreptitious trips to the local boutique. With late night visits to every custom-made-and-ordered dress shop online. With lavish layers of pink and frills that neither of them dreamt could exist until they realized they could exist fashionably—and felicitously—on his supple person while he giggled and quivered in his mistress' arms.

He was more than her pet. He was her princess, and—Lord knows—Principal Celestia spoiled him rotten... so long as he worshiped her rotten. And even still, despite the increasingly opulent lengths they took their erotic role play, Flash never once talked back to her or overstepped his bounds or showed any certifiable degree of arrogant dissent. He knew where the limits of his role lie. It was more than the collar that they had ritualistically adorned him with. Flash understood that Celestia was giving him something far too precious to give up: himself—or at least the adorable anomaly that he was allowed to be when he was with her.

At first, Celestia feared that this role they had adopted for him was the sole carrot on a stick that was keeping him around. But then came the nights—and those soft satin moments after "playtime"—when he would cling to her and his muscles would still be spasming and his legs would curl up along her thighs and by his breaths, his whimpers, his cries... she knew... Celestia knew that he belonged to her and couldn't bear to end up anywhere else. And she loved him for that.

She loved him... so much so that it nearly brought her to tears... just as it was making her eyes water right now. Right now, as she observed him... absorbed him—lying there in bed, light as a feather and yet pliable as clay, inhaling and exhaling the scent of her that clung to everything soft and silky and warm in that domain. The bed was an extension of her—a soft and motherly embrace—and it caressed him at the same time her misty eyes did.

A tiny hum purred from Celestia's lips. She raised a finger—pretending at first to brush her girlish cowlicks straight. Eventually, even this facade ended, and that same hand stealthily slithered over until it crossed the posterior of the boi. With a shameless flick of the wrist, she unpeeled a length of the silk sheets, smiling at what she could once again admire.

Flash wasn't entirely naked; he rarely ever was in his mistress' presence. Like a true doll, there was always one or two layers of playful lace left covering his naughty bits. Celestia preferred it this way: like a present forever being unwrapped. He wore sadistically tight fuchsia briefs—with baby pink lace making a floral dance across his currently unseen crotch. The rear hugged his cheeks with nylon ferocity—except for a tiny heart-shaped spot that exposed his holiest of holies. It was a goofy little sissy "window" through which a massive ten inch strap-on had waged war over five howling minutes earlier that night. In the faint light from the t.v., Celestia could swear that the young man's ass was still red from the orgasmic ordeal.

Celestia licked her lips, lifting the bedsheets a little further. Her eyes traveled down Flash's milky-smooth legs, to where twin pink anklette socks clung to his lower calves, halo'd with playful lace. Usually, she preferred keeping his toes exposed, because she adored seeing/feeling the little things curling up whenever she drove him to the stars. But this was a new "ensemble" she had prepared for Flash—whatever was left of it after she had stripped the rest in a ravenous state before. All in all, Flash looked like a survivor who had run out from the world's kinkiest ballet caught on fire, and Celestia couldn't be prouder for it.

Lifting the sheet had exposed Flash to the stale air of the room, and a layer of goosebumps rippled to live across his otherwise immaculate backside. He made a trilling sound in his sleep while his legs shifted, clearly disturbed. So—like an owner with her cat—Celestia saw fit to disturb him even further.

With a devilish smile, she leaned in and breathed hotly across his neck. She knew that the faint musk of wine lingered on her breath, coupled with the jasmine perfume clinging to her bosom to match the scented candles.

Sure enough, something subconscious within the sub responded to his mistress. After a stifled whimper, Flash pivoted his nubile body on its right side. His eyes were still shut, and in the turn of his unconscious head, Celestia could see the bubble-gum-pink collar adorning his neck. It was fringed with white lace and layered on the inside with a cushy surface—ensuring that the article would never once hurt her pet. Embroidered across the front (now the side), was the word Princess in the most girlish font imaginable. An even space away from that, and Celestia knew her own name had been monogrammed into the faux leather surface—a testament to anyone lucky enough to enjoy Flash from behind that someone else had laid claim to his sacred nethers first.

In speaking of which, Celestia's eyes soon traveled down. In shifting to his side, Flash had exposed her most cherished part to the older woman—caged as it was in a crotch of embroidered pink lace. As in all things, Flash was not very-well endowed. This wasn't something that the two of them typically chose to put to the test. Celestia had long taught Flash a myriad intricate other ways to please her, and for the majority of their playtime she had gotten her enjoyment out of making him squirm and exalt her name in between a chain of subservient tasks. But it still didn't change the fact that—at the end of the day—Celestia absolutely adored the bulge... Flash's little pronounced venus mound. The princess' precocious clitty.

And at that particular moment, there was a stirring to it. Limp, yet still courageous. Celestia half-wished Flash could wake up so she could tell him how proud she felt right then. Yet—she could make the moment prouder.

She leaned in, and with a pent-up breath, she kissed him hotly on the neck, then playfully up his forehead so she could make a rest stop in his bangs. Her nose dug lazily in those locks, relishing in the vanilla scent of the condition he made him use every night he spent over at her place... a perfect complement to the lavender body wash that she had applied to his chest and limbs as well. More than anything, she wanted her doll to smell lovely—like a dessert tray she could return to nibble on every hour on the hour.

And nibble she did, trailing her lips to his ear and then into the nape of his neck. There, she savored the scent of the boi, still sprinkled with a dash of sweat from the precious bacchanalia they had enjoyed earlier. Most of that escapade was spent with his gasping face pressed firmly between her straddling thighs, so a coy Celestia knowingly smiled at who the taint of musk actually belonged to.

"Mmmmm... having sweet dreams, my pet?" she cooed drunkenly into the air between his eyelids and her bosom. Celestia had crawled over, practically looming over him now. A nipple brushed and scraped past his nose. His sleeping face scrunched as if with an incoming sneeze, and she giggled like the teenaged schoolgirls she taught every year. "I think I'm having a dream right now..." She ran a feather-light hand down his hairless chest, around his navel three times, and down towards his waist where a lacy hem resided. "...could stand to be a touch naughtier. Hmmm?" She batted her eyelids to no one. "Wakey-wakey?"

Flash didn't respond, and yet he did. The breath... the scent of mistress being so close—coupled with her warmth and deep voice—had an apparent effect on him. Or—much rather—the littler him. Celestia watched with glimmering eyes as that tiny bulge became a hair less tiny. She pounced on the moment—in the softest way possible. The woman calmly traced her index finger from Flash's taint all the way up along front of his panties, enjoying the tickle of the floral embroidery as the crotch grew warmer... moister. At last—with expert touch—she applied a smidgen of pressure where she knew her finger was tickling the precipice of his silk-covered glans. A tiny squeak escaped from the boi's lips, and a damp circle formed under Celestia's index finger. Then—just above that—a clear droplet of precum milked through the pink lace, dancing like a tear and threatening to fall to the bed.

Celestia scooped it up with expert grace. Her nostrils flared, and the woman was already licking her lips... but she resisted that heavenly temptation. Instead, with a righteous grin on her face, she pressed the finger to Flash's own lips. Instinctively, her pet suckled on the mistress' digit, and in so doing he tasted a precious dollop of himself. There was something evidently familiar about it all, and his face went flush red—starting with the ears and spreading to a tiny smile that graced the bedroom air between them.

"Sweet heavens..." Celestia at last released through a euphoric sigh. There was no subtly this time as she leaned over to kiss her plaything straight on the lips, nibbling a bit to share a sliver of that same taste that she just gifted him with. A taste she knew very well—one thing she could indeed own. "...I love my little princess so very much." She smooched his cheek. "Do you hear that?" She smooched his other cheek. "Mistress loves you, my pet." She caressed his cheek, hair, neck. Soon she was cradling his head as he felt him stirring all over from the inside out, coming to the surface of the sultry moment as she waited for his pearl-blue eyes to flutter open. "How about it, sweetie? Up for some midnight fun? Hmmm?"

There was a melodic squeak that issued from the boi's throat as Flash Sentry yawned. His mouth opened wide, then closed shut. At long last—much to his lover's delight—he curved his spine, stretched his limbs, spread his thighs apart and—

The cacophonous sound of what horrifically resembled a deep bass trumpet ripped unceremoniously across the bed, causing a layer of the silk sheets to lift and fall back down to Flash's posterior.

Three whole seconds of this nightmare ensued. Moments after, Celestia was still left numb and blinking.

Flash squinted his eyes up at her with a dumb smile. Two heartbeats later, his senses registered who he was looking at and where he was lying. "I... did you... did I...?" A slow grimace crossed his face. He sniffed the air, and that grimace increased tenfold. "Oh no! Ah jeez!" He shot up with a whimper, clawing at his face and ears in some deep wordless agony beyond embarrassment. "Principal Celestia! Mistress! I-I-I'm so sorry! I forgot where I was!"

She was already snorting. "Darling—"

"I... I-I was sleeping so soundly and... and... ah jeez... I forgot where I was!" Flash hyperventilated, grasping at the sheets as his face paled and paled. "Oh mistress! Please forgive me! I'm so sorry!"

"Sweetie—" Celestia reached for him.

"That was so disgusting! I-I promise it'll never happen again! I'm so horrible! Will you ever—"

"My pet!" Celestia grasped his shoulders with a little shake. She leaned in close, eye to eye. "Flash," she murmured, slurring beneath character. "It's alright. It's only natural. I'm not mad."

Flash stared at her, lips quivering. His voice reached a feminine octave that the woman could never... ever hate. "You're not mad?"

"No?" She said, then giggled. "A little amused... but no." She shook her head. "Not mad." She reached out and stroked his chin. "'Kay?"

He sat in her arms, panting and sweating as if he had just jumped out of a plane. Thankfully, she had caught him, and his breaths started to calm. "I... uh..." He sniffled, rubbing at the first of a few tears that had belatedly escaped his panicked eyes. "Okay. Just... still... I'm sorry..."

"Heehee... you know what it means?" She hugged him close, leaning back and hoisting his lower legs so they could rest over her shapely thighs. "Mmmmmmmm..." She nuzzled him close, cradling the petite young man in her grasp. "...you're starting to get comfortable staying over here."

Flash blinked towards the ceiling, strung halfway between confused and concerned. Nevertheless, he eased into her arms, relishing in her scent and warmth—shivering slightly. "Is this like... a year two thing?"

"Little early for that." Celestia drew a blanket over them both as she rubbed his arms and snuggled him close. "Buttttttt... I wouldn't be opposed to you bringing your toothbrush over next time." She bumped noses with his, playfully. "...maybe once you're in college?"

"I... could stay here during college..." Flash murmured.

"Why not?" She kissed his cheek, then reached in to straighten his collar. "Assuming you don't get tired of our little games."

"N-no! Not at all, Celes—er... Mistress."

"Sure beats living in a dorm."

"Mmmmm..." He rested his face against her bosom, smiling at her warmth. Her softness. "I'll say." He gulped, then cast puppy dog eyes up at her. "Do you still want to have fun with your princess after... after...?"

"Heehee..." She gave him another kiss. "Of course I do." A breath. "Just... might want to turn the sheets over first."

"Yeah..." He stared off at the rest of the room. The scented candles were dying, but still doing their job, praise heavens. "... ... ...I've got the weirdest boner right now."

And Celestia laughed and held Flash even closer, cherishing him.

Author's Note