Pinkie's Worst Date

by r0bosaur

Rating: mature
Tags: Fluttershy, Pinkie Pie, Sex, Alternate Universe, Human, My Little Pony: Friendship is Magic, Dark, Comedy
Length: 4311

Pinkie Pie is seduced by Fluttershy... whether she likes it or not.

Pinkie Pie recounts her one and only sexual encounter with the demure, pure-hearted, lovable Fluttershy to her friend, Rainbow Dash. It's... not what Dash was expecting.

Cover art by LittlePirate and edited by me.

WARNING: This story is kinda fucked up. Don't read it if you're offended by rape!

Published 2013-05-15 20:00:02 UTC
Last updated 2013-05-15 20:00:02 UTC

Pinkie's Worst Date

NOTE: This story starts after chapter ten (The Party: Part Two) of my previous story; She Said “I Love You.” It’s not required reading, but it may help you to understand this story. Plus, it’s not half bad if I do say so myself.

Rainbow Dash was reclining at the outdoor café. The sun was shining, the birds were singing, her coffee was strong, and Pinkie Pie was late. Dash had prepared for this, as Pinkie wasn’t the most punctual girl on the planet, but it was somewhat annoying all the same. Dash was dressed lightly for the summer day, wearing light shorts and a tank top, but the sun was still near-sweltering. She pulled her retro 90’s shades over her eyes and tried to relax while waiting for her friend to arrive.

Suddenly, Pinkie was upon her. She sat down heavily in the chair opposite of Dash, which startled her to attention. Pinkie had the ability to be both loud and flamboyant while completely stealthy. It was an ability that Dash would like to study if she were a more scientifically-minded girl.

“Hey Dashie! Sorry I’m late! I was up like suuuuuper late last night and I totally forgot we were gonna hang out so I slept in until Mrs. Cake woke me up! Were you waiting long?”

“Not at all,” it was a lie, but she didn’t want to hurt Pinkie’s feelings. “I practically just got here.” Dash could tell that Pinkie had just gotten out of bed and threw on the first things she could find. She was wearing heavy black boots, blue knee-length socks, a frilly pink skirt, and a lemon-yellow hoodie zipped up to her neck. Dash had the feeling that there was nothing under the hoodie.

The waitress came by to take their orders. Dash got a refill on her coffee while Pinkie ordered some extravagant cake concoction. Pinkie watched the waitress' shapely ass as she made her way past the nearby tables and into the café. She leaned across the table towards Dash. “O.M.G! Did you see her butt Dashie? I just wanna grab it and give it a squeeze!”

“Yeah, real nice.” Truthfully, Dash hadn’t even noticed. She used to have wandering eyes (and slightly wandering hands) up until about half a year ago, when she started dating Applejack. Since then she’d been making a conscious effort to keep her eyes (and hands) to herself. Or, preferably, to Applejack.

“Daaaaaash… you weren’t even looking.” Pinkie had a pout on her face. “Remember when we would go around town, picking up chicks and dudes to bang?”

“I remember the chicks, but the dudes were all yours.”

Pinkie leaned back and let out a wistful sigh. “Those were the days.”

“Geeze Pinkie, you sound like an old man.”

“Well maybe I feel like an old man! I mean, you’re all steady an’ junk with AJ, Big Mac is with Cheerilee, Twilight won’t fool around with me anymore… it’s like I’m the only one without someone! It totally sucks!” She thumped her head onto the table in depression.

“Well… I guess we’re all growing up or something. It’s bound to happen sooner or later, I guess.” Dash sipped her coffee, waiting for Pinkie to break herself out of her funk. “Maybe you need to try being in a serious relationship for once in your life.”

Pinkie sat up. “Look at who you’re talking to, Dashie! I can barely focus on one conversation at a time! I can’t do… relationships." She shuddered slightly at the utterance of the 'R' word. "And who would wanna take a chance on dating me anyways?”

“Well…” Dash racked her brain for an answer. “I mean, everyone loves you Pinkie! It can’t be that hard. Rarity may be out of your league… and totally straight as far as I know… but maybe Fluttershy? Didn’t you mess around with her once?”

Pinkie was bolt upright in her chair. “No way! Noooooooo way! Fluttershy is… out of the question!”

“What’s wrong with Fluttershy? She’s so sweet and charming and demure…”

“Have you ever had sex with her?”

“Well… no…”

“Then you have no idea.”

“Okay so… fill me in.”

Pinkie glanced around nervously. “Let’s go back to your place first.”

Pinkie rarely cared who overheard her talking, even when she was talking about a sexual experience in great detail, so her caution was more worrying than her frightened expression.

They made their way to Rainbow’s house in silence. Once inside, they sat down at the kitchen table and Dash simply waited for Pinkie to start explaining. “Dashie…" Pinkie was fidgeting in her seat. "Did I ever tell you what Fluttershy is like in bed?”

Dash once again racked her brain for the answer. “I… seem to recall you mentioning it being a bit rough?”

“That’s not even half of it… Okay, so it all started about a year ago…”

In fact it was ten months and twenty-three days ago. Pinkie was walking home from Sweet Apple Acres, having visited Big Mac and his big cock, when she stumbled across Fluttershy in a meadow. She was crying, with her assorted animal friends trying to comfort her.

Pinkie ran over and threw herself over her friend. “Flutters! What’s wrong sweetie?”

Fluttershy rolled onto her back to look into Pinkie’s blue eyes. Her own teal colored eyes were bloodshot from her tears. “Oh, P-p-p-p-Pinkie! It’s s-s-s-s-so awful! Wh-wh-what do I dooooooooo?” She broke into sobs once again.

“Let’s go back to you cottage and make you some hot cocoa, okay? Then you can tell me all about it when you feel like it.” Fluttershy nodded at the suggestion, and the girls made their way to her cottage. They sat in the kitchen, and after a copious amount of hot chocolate, Fluttershy was ready to speak about her ordeal.

“I… I have a c-c-crush on Thunderlane.” She went red at the words.

“Aaaaw, you would be a cute couple… I think?” Pinkie sipped her cocoa eagerly.

“But…he’s dating Flitter… and when she found out… oh Pinkie, she said such mean things to me… it’s just awful!” She broke out into sobs once more, and fresh tears cascaded down her face and dripped into her white turtleneck sweater. She focused on her lap and her pink hair cascaded over her face, completely covering her features.

“Oooooh sweetie!” Pinkie hurried around the table to embrace her friend. “It’s okay sweetie! Flitter is a total bitch to everyone… Thunderlane is gonna break up with her sooner or later! Then you won’t have to listen to that stupid meanie butt ever again!”

Fluttershy buried her face into Pinkie’s chest and sobbed softly. They remained like this for a few minutes. “Oh Pinkie…” Fluttershy’s words were somewhat muffled by Pinkie’s boobs. “Why can’t everyone be as sweet as you?”

“Because when I was born I got two scoops of sugar instead of one!”

Fluttershy giggled as she removed her face from Pinkie’s chest, wiping her eyes on her sleeve. “Oh my! I’ve ruined your shirt!” Pinkie’s t-shirt was stained with Fluttershy’s tears.

“Oh it’s alright! It’ll come out in the wash.”

“Please, let me wash it for you! It’s the least I could do!”

Pinkie’s protests were cut off before they could be voiced, as Fluttershy yanked the damp shirt over her head with a single motion. Fluttershy hurried away with the pilfered garment towards her laundry room. Pinkie was left standing in the kitchen, clad only in a pair of Daisy Dukes and a pink bra. Fluttershy didn’t like it when people wore shoes in her house, so she was barefoot as well.

Fluttershy hurried back into the kitchen, her eyes ringed in red but otherwise bright as they usually were. “It shouldn’t take too long to wash. Do you want something to eat?”

“No thanks Flutters, I’m totally full!” Pinkie slapped her tummy to emphasize the point. The slap sent a jiggle through her torso and into her breasts, which quivered to the force of her slap. Fluttershy’s eyes were drawn to Pinkie’s half-bared body. Pinkie may be called fat by crueler people, but Fluttershy saw her as a full-figured woman. She was hourglass shaped, with thick thighs and a round ass, large breasts (even bigger than Fluttershy’s own, which were large in their own right), and a soft midsection. She was perfectly cuddleable, reminiscent of a sexy teddy bear. If such a thing existed.

Fluttershy drew close to the other girl. “Oh Pinkie, you’ve let yourself go a bit.” She took the excuse to touch Pinkie and pinched her belly.

Pinkie giggled and slapped away Fluttershy’s hand playfully. “I can’t help it! I work at a bakery! Everything there tastes soooo goooooooood!”

“I didn’t mean to sound rude! I think you look… amazing…” She pinched Pinkie’s belly again. “You’re so soft Pinkie.” Pinkie continued to giggle, but didn’t slap away Fluttershy’s hands. “And your… your…” Her hands made their way up Pinkie’s stomach and groped at her breasts. “They’re so big!”

Pinkie went flush and giggled once again. “You’ve got big sweater puppies yourself, missy!”

“Oh noooo… not like yours… mine are too big for my body, they look so out of place. Yours are so pretty!” She leaned in and kissed Pinkie’s breasts.

Pinkie giggled at the attention. “What are you doing Flutters? Stop messing with my boobies!”

Fluttershy looked up at Pinkie, gazing deeply into her eyes. She stood on her tiptoes slightly and kissed her. They held the kiss for only a moment until Pinkie broke it.

“Fluttershy…” she glanced around nervously. “W-what are you doing?”

“You’re so beautiful Pinkie. And you’re always so nice to me…”

“W-well of course… I mean… you’re my friend… I never thought of you…”

“Sexually?” Fluttershy was stepping forward, forcing Pinkie ever backwards. “But you fuck everyone else.” Fluttershy’s sudden cursing startled Pinkie. “You never thought of playing with my tits? Never thought of eating my pussy?” The look in Fluttershy’s eyes was hard to describe. It was a mix of lust and anger. “Is my body not good enough for you? Do you think I’m too pure for you?”

Pinkie was starting to be scared of Fluttershy at this point. “W-w-well I-”

“I masturbate three times a day, at least! I own ten vibrators! I pound my cunt and ass every day! I love getting fucked as much as the next girl! What makes you want my cunt less? Am I not dirty enough for you? Is it because I don’t dress like a slut?”

“F-Fluttershy… I-” Suddenly, Pinkie was bowled over and landed roughly on her back. She glanced around until she realized that she was on Fluttershy’s bed.

Fluttershy climbed into the bed, straddling Pinkie’s hips with her own. She raised her skirt to her stomach, revealing her dripping wet pussy, matted with bright pink hair. “Is this cunt not good enough for you? Or do I need a cock before you’ll think about fucking me? Is that it?" Pinkie could feel Fluttershy's warm juices dripping onto her stomach. "Are you too much of a cum dumpster to eat my cunt?” Fluttershy was shouting now.

“Fluttershy… you’re scaring me…” Tears were welling up in Pinkie’s eyes.

“So why don’t you call Big Macintosh? Or is he too tired from shooting his cum into your shitter?” Pinkie gasped, and Fluttershy smiled cruelly. “Yes, I know Big Mac fucked your slut ass this morning. You’re his usual cum-dump, aren’t you? He’ll use you until Cheerilee opens her legs for him, then he’ll throw you aside like the cum-soaked rag you are!”

“It’s not like that! He-“ her protests were cut off by a hard slap to the face.

“Did I say you could speak to me, you whore?” The look in Fluttershy’s eyes had become manic, mingled with pure ecstasy. “Maybe I should put your mouth to better use.” She raised her hips and brought them over Pinkie’s face. Her pussy was only an inch or so from the other girl’s face. “Eat me out, slut.”

Pinkie shut her mouth tight and looked away. Fluttershy slapped her hard until Pinkie looked up at her. Flutterhsy took the opportunity to bring her hips down hard into Pinkie’s face. “Now, eat my cunt!”

Pinkie was too afraid of the repercussions to ignore the demand, and set to work. Fluttershy’s juices poured into Pinkie’s mouth and down her throat. The excess dribbled down her chin and streaked her cheeks. Fluttershy ground her hips into Pinkie’s face to the motion of the girl’s tongue. “Do you like my dirty cunt, whore? Do you like how it tastes? I didn’t wash myself this morning because I knew you would be eating me out today. Does it taste like my piss?”

Pinkie couldn’t respond. She barely had enough air to breathe, and Fluttershy’s hips were grinding into her so hard that she could do little more than move her tongue around inside of Fluttershy’s pussy. In truth, Pinkie couldn’t stand the taste or smell of Fluttershy. She was clearly telling the truth about washing, and the smell of her dirty pussy had permeated her pubic hair, which was buried in Pinkie’s nose. Pinkie Pie was gagging as she tongued Fluttershy’s vagina and gasped for air.

Fluttershy’s hands grasped Pinkie’s head, pulling her in closer. “Do it harder, whore! I’m about to cum all over your face!” She pulled Pinkie by her hair, digging her into her cunt. She bucked her hips into Pinkie’s face hard enough to give her bruises that wouldn’t go away for a few days, and screamed as she came. “YES! EAT IT YOU WHORE! EAT MY DIRTY CUT! FUCKING EAT ME!”

As her orgasm took over, she roughly threw Pinkie’s head down onto the bed, and fell over backwards, knocking the air from Pinkie’s lungs. She trapped Pinkie under her body weight. “That was half decent, you pathetic slut. Did you like the taste? I wonder how long you’ll have the smell of my cunt in your hair?”

Pinkie sobbed softly. “Fluttershy… I wanna go home… please…”

“Oh no… we’re only getting started.” She stood up on the bed and peeled off her clothes. Her breasts were slightly smaller than Pinkie’s, but were perkier. She was also thinner in both the waist and thighs, but still had well-shaped hips. Pinkie would have found the sight erotic if she wasn’t so terrified of Fluttershy right now. She threw the clothes at Pinkie, who was still on her back. “Now strip.” Pinkie made no movement to comply. Fluttershy kicked her in the ribs. “I TOLD YOU TO STRIP YOU PIECE OF SHIT!”

Sobbing, Pinkie removed her clothes, revealing her thick body. Fluttershy got on her knees, between Pinkie’s legs. She made to push her legs open, but Pinkie held them shut. After Fluttershy slapped her once more, she opened her legs for the girl. Pinkie’s vagina was cleanly shaven, and unlike Fluttershy, completely dry at the moment. This didn’t stop Fluttershy from roughly shoving two fingers inside as deeply as she could. “You’re so dry Pinkie… that won’t do at all. How am I going to fuck you with a dry cunt?” She withdrew her fingers. “Don’t fucking move.” She got off the bed and walked to the open closet nearby.

Pinkie considered running, but was too scared to move. Too scared of what Fluttershy might do to her if she tried. After a minute of rummaging around, Fluttershy returned to her wearing a black strap-on and carrying a bottle of lubricant. She leaned in close to Pinkie and whispered into her ear. “Tell me where you want me to fuck you.”

Pinkie merely sobbed in response. Fluttershy spoke again, more angrily than before. “Tell me where you want me to shove my big black cock. Do you want it in your whore cunt, or your whore ass? Tell me or I'll shove it down your throat and make you black out. Then I'll pick a hole."

Pinkie choked back a sob to respond, barely above a whisper. “M-m-m-my… v-v-v-vagina…”

“Your what? You don’t have a vagina, you worthless whore. Tell me where you want it.”

“M… m-my… my whore c-c-cunt…”

“Say it properly. Tell me what you want me to do to your whore cunt.” She was rubbing lube onto the strap-on as she was whispering.

“F-f-fuck my… my whore cunt with your b-big black c-c-cock.”

“That’s better.” She tore Pinkie’s legs apart once more and roughly shoved the dildo inside of her. Pinkie held back a gasp as the dildo entered her as deeply as Fluttershy could force it. It was at least ten inches long, and very thick. Fluttershy started fucking her roughly, not giving her any time to acclimate to the intrusion. The powerful thrusts were forcing her higher and higher up the bed, until the headboard was connecting with Pinkie’s skull. The force of the thrusts was great enough to knock the air out of her lungs. Soon enough, she was seeing stars and her vagina was going numb.

A sudden slap brought Pinkie to attention. Fluttershy had stopped thrusting and was looking at her with complete anger in her eyes. “I said; how many times did you make Big Mac cum today?”

Pinkie choked back a sob before answering. “Th-three.”

“And where did he cum? What part of the cum dumpster did he use today?”

“M-m-my mouth. And t-t-twice in my... my b-butt.”

“That was just this morning, right? Let’s see how he treated your ass, shall we?” Fluttershy roughly grabbed Pinkie by the waist, lifted her off the bed and threw her down once more, this time on her stomach. “Lift up your ass, whore.”

Pinkie didn’t comply, and soon felt a sharp pain across her bottom and heard a loud smack. Before she could process it, she felt another. The pain seared through her body, like hot lightning. She looked behind herself to see Fluttershy holding a riding crop high above her head and smiling. “Do you want another? Do you like being treated like the worthless piece of shit you are?”

Pinkie raised her hips, resting on her knees. She hoped this was enough to avoid another whipping. She felt Fluttershy dig a finger into her pussy and move it around roughly. “I gotta get nice and lubed up for this," her whisper was full of cruelty and lust.

Fluttershy coated her finger with the lube inside of Pinkie, and withdrew her digit when it was slick enough. She poked it into Pinkie’s tight anus, which opened somewhat to accommodate the intrusion. “Looks like you’re used to getting fucked in the ass, aren’t you? Is that all your good for? Do the boys prefer fucking you in the shitter? Do they think your cunt is too used up?” Pinkie’s sobs gave her the motivation to push deeper. Soon she had two fingers inside the girl’s anus.

Pinkie felt Fluttershy’s fingers spread her anus open as widely as she could. She was afraid Fluttershy would open it too widely, she could almost feel her anus tearing apart. She heard Fluttershy’s cruel laugh coming from behind her. “I KNEW IT! His cum is still inside! You didn’t shit it out? You dirty whore!” Pinkie could feel whatever semen still remained inside of her bowels start to drip down her legs, and began crying once more.

Suddenly, Fluttershy withdrew her fingers and roughly picked up Pinkie, forcing her to stand on the bed. Fluttershy came in close and forced Pinkie’s mouth open. She shoved the fingers she had just used on Pinkie’s anus into the girl’s mouth until she gagged.

“What’s the matter? Don’t like the taste of your own shit? I thought it would just taste like cum at this point, since you get fucked more often than you shit.” She withdrew her fingers. “Now then… I want you to push out all the cum that’s in your whore ass. Right now!”

“F-f-f-Fluttershy… please…” Pinkie’s sobs were cut off by a punch to her stomach, and a hand roughly grabbing her around the throat.

“You don’t get to talk. Now squat down and SHIT!”

Pinkie complied, frightened by the prospect of a sudden increase of pressure on her trachea. She squatted over the bed, and Fluttershy pulled a pillow under her rear. Pinkie stayed like that for a minute, too embarrassed to do what Fluttershy wanted. Suddenly, the grip around her throat tightened and Fluttershy whispered in her ear. “If you don’t do what I tell you, I’m going to choke you to death.” There was no anger in her voice, just a cold promise.

Pinkie held back another sob, and pushed. Soon she could feel the semen dripping out from inside of her. “That’s a good whore… push harder.” Pinkie complied, pushing out more semen onto the pillow. Soon enough, there was a small white puddle coating the pink pillowcase. Pinkie pushed out the last of it, and sighed slightly when it was over.

“Push harder.”

“B-b-but that’s all of it!”

Fluttershy responded by simply cutting off Pinkie’s air. Pinkie pushed while her vision started going dark. After a moment, Fluttershy released her grip and Pinkie gasped for sweet air.

“You dirty cunt!” Fluttershy slapped Pinkie across the face with all her might, knocking the girl off the bed. “DID I SAY YOU COULD DO THAT?” She hopped off the bed and grabbed Pinkie by her hair, pulling her up into a kneeling position. “LOOK AT WHAT YOU DID!” Pinkie looked to find the pillow, covered in Big Mac’s semen, with Pinkie’s own feces sitting on top.

“I NEVER TOLD YOU TO USE MY BED AS A TOILET!” She threw Pinkie towards the mess, which she landed in face-down. Before she could stand up, Fluttershy was pushing her down once more. “I’ll show you what happens when you disobey me!” She spread apart Pinkie’s ass with one hand, and guided the dildo inside of her anus with the other. She shoved it in as deeply as it would go, and Pinkie screamed in pain.

Fluttershy fucked her mercilessly, driving Pinkie’s face deeper into the mixed puddle of semen and feces. The pain was excruciating, and Pinkie was positive that her anus would be bleeding before this was over. She was pulled back roughly by her scalp, and felt Fluttershy’s strong fingers wrap once more around her throat. She squeezed down on Pinkie’s throat as she pounded her anus as hard as she could. Pinkie couldn’t breathe and couldn’t move. The pain was fading as her vision blurred and went dark.

Pinkie awoke on her back, in Fluttershy’s shower. The water was running cold and her skin was pruning. She wasn’t sure how long she had been unconscious for. As she turned off the water, she heard Fluttershy from the next room, humming to herself. Pinkie froze on the spot.

“Pinkie Pie?” Fluttershy was calling out sweetly from the next room. “Are you up? Your shirt is all dry. I put your clothes on the counter. Pinkie glanced around until she found her clothes. She dried hurriedly and dressed. She slowly left the bathroom, trying to move as silently as possible, hoping to escape before Fluttershy could find her. She turned the corner to find herself back in Fluttershy’s bedroom, with its owner sitting on the edge of the bed, once again dressed.

The bed was neatly made, the sheets were tucked in and there was no mess on the pillow. Fluttershy herself was perfectly put together, without so much as a single pink hair out of place. She smiled brightly and got up as Pinkie came in. She advanced on Pinkie, who was frozen on the spot, terror welling up inside of her.

Fluttershy embraced Pinkie in a loving hug and gave her a gentle kiss on the lips. “Oh Pinkie, I had so much fun today. I had no idea you felt that way about me.” Fluttershy’s voice was back to normal; she was sweet and quiet, with no hint of cruelty or lust.

Pinkie was dumbfounded. “I-I-I-“

Fluttershy put a finger to her lips. “Ssssh… you don’t have to say anything.I love you too, Pinkie Pie.” Fluttershy kissed her once more. “I hope you’ll come visit me again soon. Do you want to get dinner tomorrow?”

Pinkie leaned back in her chair at Dash’s house. “And that’s it. I’ve been avoiding her since then.”

Dash picked her jaw up off the floor and tried to find an appropriate response. "What. The. Fuck?"

"I know, right?"

“And she… she was… totally normal after? Like it was no big deal that she nearly choked you to death?”

“Yeah! It’s like she thought that was a totally normal way to have sex! I couldn’t sit for two days, and I had bruises around my neck for a week!”

“That’s… that’s fucked up.”

“I know, right! And she’s been sexting me ever since! Look,” she dug her phone out of her pocket and flipped to a text. “here’s one: ‘come over right now and eat my smelly cunt. I haven’t washed it in a week.’ Here’s another: ‘I’m gonna pound your shit-hole so hard I’m gonna make your guts fall out.’ Who the hell writes this?”

Silence fell over the girls like a wet blanket, and they sat awkwardly for a few minutes. Neither of them could think of anything to say. Eventually Pinkie excused herself, and headed home. Halfway to Sugarcube Corner, her phone buzzed in her pocket. She dug it out to see another text from Fluttershy. She opened it to see that it contained a picture of a naked Fluttershy brandishing a hatchet. The text read “come over right now or I’m going to kill you <3”

Pinkie knew she wasn’t lying. She was too scared to refuse.