Femboi and Chill

by shortskirtsandexplosions

Girlfriends and Chill

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Author's Note

Art by Twilite-sparkle-plz

This is an ongoing fanfic concept. My first "non-oneshot" of the early 2019 Sissy Skirts Bridge-Burning Tour(TM). While it's not a daily, expect it to look and feel like one. It's simply a series of gratuitous vignettes starring the Humane 7 of EqG and my femboi OC Cherish Lynne. Cherish has been a very special part of my heartfelt imagination for quite some time now, and now he/she/they are getting their chance to shine, one cuddly chapter after another.

I have several "harem fics" like this planned, but they're all long and involved and take forever to manifest from thought-onto-word-processor. With this concept, I'm just jumping into it. This is purely me enjoying myself (when has that been new), and I hope others get to enjoy themselves while reading it too.

I'm grateful to the artists who--over time--have been gracious enough to bring "Cherish" to life. Now it's my turn to attempt the same.


This story will not be heavy on sexual stuff. At least not at first. It's rated M because--for me, at least--it's super dense sissy/crossdress pr0n. With lots of squirmy pink goodness.

Maybe later, I'll have slightly "moister" things happen. And when I do, I'll be sure to tag the chapters accordingly.

Until then, expect predominantly cuddly/fluffy/teasing bits. That's the bread and butter of this fic.

Tee-hee... "butt-er"


Girlfriends and Chill

“Oh Cherissssssssssh!” Rarity's voice echoes harmoniously across her penthouse apartment. “Cherish Lyyyyyyyyyyyyne!

“C-coming!” you stammer, pouring the last of the buttery popcorn into a large ceramic bowl. You slap the microwave door shut, temporarily deposit the empty bag onto the kitchen counter and... hop down from the footstool you were using to reach it all. Reaching two trembling wrists up, you grasp the bowl with heroic hands and carry the hot salted bounty towards your destination.

The lights dim as you enter Rarity's living room—which has become a veritable No-Man's-Land strewn all over with sleeping bags, pillows, blankets, gossip magazines, brushes, make-up kits, and lots and lots and lots of bare feet. Seven beautiful young women are settling down before a wide screen television for a night of cinematic fun-times, and your toes are being added to the mix, cautiously girl-stepping through the mine field of estrogenical detritus to arrive at the center of the “audience.” It's a wonder that Rarity would allow her own home to get this bomb-crater'd with chaos, but—for her friends—she makes exceptions.

And you're among them—you with your dangerously petite stature, limping about in one of Fluttershy's old high school bedshirts: a frilly yellow and pink thing that reaches down your slender legs to just below your knees. Beneath the article, you feel tender and naked—wearing nothing else but lilac-colored nylon panties. But that's okay. Here—among these college friends you've made these past few months—you feel safe. Safe from regret... safe from embarrassment... safe from judging...

“Finally!” Rarity stretches out on a red sofa, having the whole piece of furniture to herself. After all, she's the host. “Couldn't carry on without you, darling—”

“Enough talk!” Pinkie Pie squawks, and her pink hands reach across your vision of Rarity to ensnare you. “Let's get snuggling with the snackies!”

“Gaaah!” you yelp, eliciting a giggle from the rest of the women as you collapse in Pinkie's arms, nearly dropping the entire bowl of popcorn to the unblemished carpet.

...well... not so much “safe” from cuddles.

“Heeheee!” Pinkie Pie hugs you from behind. You've collapsed in her lap, surrounded by tangled bedsheets and overlapping pillows. A stuffed alligator brushes across your exposed thigh as you fumble to sit upright with her ample bosom pressing against the back of your neck. “I've got the pretty pretty princess popcorn dispenserrrrrrr!” She ruffles your pixie short blonde hair before reaching a hand into the bowl to scarf up some puffy kernels. “Nomfff! Hmmmmmm-mmmm! Sluttery-buttery!” She grabs another palmful and reaches it around, almost cramming it into your tender face. “Wanna have a bite, Chi-Chi?”

“N-no thanks!” your voice cracks. There's a chill in the room. You blush, realizing that the hand-me-down nightshirt you're wearing is riding up. You try tugging it down to cover the exposed sliver of pink panty-lace peeking through, but it's no use. You hear more giggles, so you resort to pulling a blanket over yours and Pinkie's lower limbs. That does the job. “I... uh... I'll wait until the rest of you girls have had your share first!”

“Awwwwww...” A warm, velvety voice. You smell the vanilla perfume before you even see her, and soon you're feeling Fluttershy's tender lips feather-brushing the side of your cheek with a sisterly kiss. “That's so sweet of you, Cherish.”

“Yeah yeah—whatever!” a voice cracks, and the “smallest” of the women reaches her blue hand in, snatching a huge wad of popcorn. “All the more for us!” Rainbow Dash settles beside you and Pinkie, munching away. “Mrmmmfff... Mrmmmff—shdard da vilmm awruddy!”

“We're getting to it!” Sunset Shimmer growls from across the room. A slight, womany sigh. “Twilight... sweetie... what's wrong? Can't get past the menus?”

“I'm trying to figure out if we should have subtitles on or not!” the bookish lady responds, adjusting her glasses. “I was trying to take a vote, but then Cherish came back with the popcorn and everyone got distracted.”

“I don't think it's that important, Twi—”

“Of course it is! Democracy is always important! There's eight of us here and the tie-breaker goes to Spike.”

“Spike's back at your place.”

“Yeah, but I have his cell phone number.”

“Pffft! You gave your dog a cell phone?

“Well, he's got a Youtube channel so why not?”

“Hee hee hee hee!”

Through all of this, Applejack's voice cranes in through your distant peripheral vision. “Gosh dang it, Pinkie! Please tell me you ain't gonna hog 'em throughout the entire movie!”

You blink. You open your mouth to say something—

“Uh uh!” Pinkie Pie manages between popcorn scarfs. “Cherish got to sit with you all throughout Wreck-It Ralph last week!”

“But this week we're watchin' one of them scary horror flicks!” Applejack's green eyes glisten in the dim light from the plasma screen. “What if he's frightened? The poor angel deserves some strong arms to make him feel safe-like—”

“Pllbllbllbbb!” Pinkie raspberries across room. Your nostrils fill with the scent of popcorn butter and cotton candy. “Nuts to you! Here—with me—he can feel safe and well-fed!”

“Uhm...” Fluttershy's cheeks turn pink from across the pillow'd sea. “...I could certainly use some strong arms around me, Applejack.”

“Tch...” The farm girl blows out the side of her freckles, pouting with crossed arms. “T'ain't the same.”

“Maybe... uh...” You nervously smile, imprisoned between Pinkie's possessive arms and the popcorn bowl. “...maybe we c-could switch at intermission?”

“Girls!” Rarity's voice sharply pierces the moment. “Stop fighting! Honestly! This is undignified of young ladies such as ourselves! The movie's two hours long, from what I hear. We'll all get plenty of time with our favorite little princess.” Then, after a punctuating sigh, she smiles slyly into the shadows of her lavish apartment. “Besides... this is my home. Once the final credits roll, he's all mine.”

“Look, who cares who gets passed the frilly basketball boi!” Rainbow Dash's voice drones, eyes rolling. She glares across the room. “Sunset! Twilight! Why the heck hasn't the movie started yet?!”

“Like I said—I'm waiting on you girls to stop bickering so we can cast a vote on—”

“Screw subtitles! They cramp my style!”

“But—democracy—Rainbow—”

“Screw it! I'm declaring a dictatorship!” SWOOOSH! In a magical blur, Rainbow Dash now stands behind Twilight, bending over to grab the blu-ray remote. “Yoink!”

“Hey—!” Twilight stammers, causing Sunset to giggle.

SWOOOOOSH! Rainbow sits back down next to you and Pinkie. “Finally! She clicks a button, and the opening title crawl begins. “Let's get the chainsaws and guts rolling!”

“Boy howdy!” Applejack scoots up towards the television.

“Weee-eeee-eeeee!” Pinkie hugs you tighter, resting her grinning chin on your rounded shoulder. “Are you ready to get freaked-out, Chi-Chi? Huh?! Huh?! Huh?!?”

“I... uh...” You can't stop trembling. The half-empty bowl of popcorn rattles in your weak-wristed grasp. A dainty clearing of the throat, and you smile wanly into the blood red title screen flickering before you and the girls. “I'm ecstatic!”

“Awwwwww...” Pinkie nuzzles the nape of your neck, solacing you with her warm breath and melodic voice. “Don't you get all squirmy-squirmy! Auntie Pinkie Pie's here! Everything's going to be okie-dokie-lokie!”

“I know...” You breathe in. You breathe out. “...what's to be sc-scared of?”

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