Drunken Fluttershy
"You take her home before she ruins any more of my bar!"
The swinging door just misses your backside as you drag Fluttershy out, narrowly avoiding a flung glass from the bartender. If he really cared that much about operation costs, you'd think he'd be more careful with his serving devices.
"Come on, Fluttershy, you've had way too much to drink."
"No, I didn't, I... um, I only had... this many." Fluttershy holds up her hooves for a moment, and you roll your eyes. She looks at them after a few seconds, puzzled.
"Wait... didn't I have more hands than this? Can I borrow yours?"
Without bothering to reply, you hoist Fluttershy up from her staggering position near the ground and drag her forward. Every step she takes, you feel her lurching in an off-kilter direction, like her legs are trying to lead her to five places at once. You've never known her to be a drinker... but the sight at the bar tonight was a scene to be seen, starting from a sip or two to full on drunken blubbering and downing pint-glass after pint-glass. The fact that she showed up to the bar by herself was warning enough.
"Why doesn't anypony like me?" she started, the hints of drunken depression already lingering at the edges of her voice.
"Everyone likes you, Fluttershy," you counter.
"No, I mean, like me like me."
The conversation degenerated from there, until your unceremonious exit prompt from the bartender.
"I'm nice to everyone... I'm polite, and I don't get in anyone's way... why doesn't anyone want me to be their marefriend?" Fluttershy slurs drunkenly as you struggle to cart her home.
"Can we not talk about this, Fluttershy? You know I think you're a lovely girl. I'm sure it's just a matter of time before you find the right colt to sweep you off your hooves-woah!"
Fluttershy's feet give out as your sentence ends, and as you struggle to keep her upright, you realize how heavy even a tiny pony can be when they're full of drunken dead-weight. Fluttershy's fall drags you down with her, and the two of you eat a faceful of dirt as the ground comes up to meet you. You cough with the force of the impact, but manage to collect yourself relatively quickly. Fluttershy, for her part, doesn't seem to notice she's fallen - she's staring at nothing in particular with a distant glint in her eyes. She doesn't seem to notice she's pressing down on top of you either.
"Fluttershy... could you get up, please-"
The wind is knocked out of you when Fluttershy readjusts herself, moving further up your abdomen and pressing her hooves into your stomach. As you groan and struggle to recover your breath, you hiss a sharp intake of air when you find her eyes locked onto your own from only an inch away. You can smell the beer on her breath.
"Do you think I'm pretty?"
Oh boy.
"Yes, I think you're gorgeous, now can we please-"
Tongue. Lips. And the taste of beer. Your mouth parts before you can will it closed, and Fluttershy presses her face forward, locking lips with you and trailing her tongue over your own. You feel the intake of an entire evening's worth of drinking layering over your taste buds. It's almost enough to make you pull back - but Fluttershy's warm body on your chest and her hushed moaning into your mouth manages to keep you in place.
A strand of beer flavoured saliva links your mouths as Fluttershy pulls away.
"Um," you stammer in a very Fluttershy like manner.
Fluttershy doesn't waste a second. She throws herself forward, pinning you to the ground and diving hungrily onto your mouth, panting and grinding against you like a mare possessed. You're vaguely in disbelief of what's happening, but the feeling of a depraved pegasus pressing herself against you, accompanied by her frantic tongue movements and saliva-filled kissing, means you can't really compose the forethought to push her off. In fact, you feel yourself growing hard almost instantly, your erection pressing through your jeans right into Fluttershy's stomach.
After what feels like minutes of making out, Fluttershy pulls her face off yours again, but she moves her hooves to pin your arms to the ground.
You can feel her hot breathe on your face. The smell makes you cringe a bit, but the sensation is countered as she begins grinding her hips into your crotch. You move up to meet her touch involuntarily.
"I can be a good girlfriend... you believe me, don't you?"
Words fail you for a moment. You simply nod, unable to turn away from her look of desperate seduction. She shows her approval of your answer by giving an extra hard press of her body into your dick. You barely manage to stifle a groan.
"Please, let me... I want to show you..."
Before you can surmise what she might mean by such a statement, you feel teeth on your zipper. As drunk as she is, Fluttershy moves with a purpose, unbuckling your pants and dragging them down in record time. Even in the height of passion deepest in your memory, you can't remember getting undressed faster - or having anyone so eager to get you naked so fast.
Fluttershy tilts her head curiously at the sight of your tented boxers. The way she looks at the head of your cock straining against the soft material is almost like a filly seeing the world for the first time, so full of amazement. It's a look innocent enough to remind you that for all her sudden lust, Fluttershy is still by and large a very naive girl. Despite all urging of your cock inches away from her face, you manage to prop yourself up on your elbows and look down at the bemused pegasus ogling your piece.
"Fluttershy, look, you don't have to-"
Drunkeness apparently bringing out Fluttershy's penchant for interrupting, you catch sight of a determined gleam and a staunch expression before you feel her lips wrapped around the head of your cock. She traces them over the underside of your shaft through the front opening of your boxers. As you let out a groan into the night, it occurs to you momentarily that you're in an alley not far away from Ponyville proper. Anyone could by and see you with Fluttershy's mouth swallowing your-
"Jesus!" Thought stops as you feel the head of your cock pressing into something. Moisture envelops every inch of your rod, and you look down from your propped up position to find Fluttershy with her throat bulging from swallowing the entire length of your dick. For her first time, you can't believe what you're seeing.
"Oh God, Fluttershy..." your words are halfway between a plea and a warning. Fluttershy, for her part, pays no attention, simply raising her head with a look of determination still locked on her face. She reaches the apex of your erection, lapping at the tip with her lips still locked onto your member, before lowering her mouth again, bottoming out and deep-throating you with no regard for her own comfort.
The next minute is a blur. Part of you is vaguely aware that a drunken Fluttershy shamelessly sucking your dick in an alley is the least right thing imaginable - but the other part of you can't help but groan and fight the urge to cum when you feel your head pressed into the back of the inexperienced pegasus' throat. You're not sure if you believe anyone can have a natural talent for swallowing cock - but you're willing to concede Fluttershy is at the very least a prodigy in her own right.
Fluttershy seems to have forgotten about anything other than your dick. You catch the rest of her body moving every once in a while, arching slightly with what you can only guess is bipartisan arousal . For the most part, every single ounce of her attention is focused on repeatedly bottoming out and almost choking on your dick. You worry once or twice when you feel her gag slightly, but she recovers like a champ, resuming her pace without hesitation.
Eventually, the depravity of the situation, along with the unparalleled feeling of a sloppy blowjob that only inebriation can provide, drags you close to the edge. There's no doubt in your mind that you have to give Fluttershy some kind of warning. She's so distracted you're worried she might not notice you, so you tap her on the head as you speak.
"Fluttershy, I’m getting pretty close..."
She jerks her eyes up to meet your face as she feels your fingers in her hair. Her eyes are wide as she stares up at you with her throat entirely full of your cock. You feel the suddenness of the stop in her movement. Then you feel the twitch in her throat as she gags.
A second one comes after. She doesn't catch it this time.
The sensation that follows isn't one that you can place. It's wet, and warm, but so was Fluttershy's mouth. This is much more... substantial. And sticky. Your mind thinks vaguely of the gallons of beer that passed Fluttershy's lips earlier. The noise of her final gag makes you remember them more vividly.
"Mmph-" Fluttershy's eyes squeeze shut as she yanks her head back. The look on her face has warped from determination to desperation. Every ounce of her fights to hold back the night's rememberance of each drink from returning.
She's not successful.
Warm, backwashed beer sprays all over your crotch, coating your dick and your boxers in a waterfall of musky moisture, smelling a thousand times worse than anything you remember drinking in your lifetime. The part of you that wants to yell out is buried in shock, and, as an aside, concern. The look on Fluttershy's face as her stomach empties its contents is so pathetic that you almost manage to force your mind away from noticing that she's heaving fifty bits worth of hot alcohol all over your legs.
"Hurk..." Fluttershy's wail as the last of the beer leaves her stomach is the definition of pathetic. You only keep to the ground out of sheer shock, knowing full well you should pull yourself up and comfort her. She reels back from your body, landing sadly in the dirt with her feet between your legs. You can hear the sound of sniffles as she heaves the last drops of moisture onto the ground. She looks every bit the part of a pegasus who's spent the night abandoning their self-esteem.
You let a minute pass as she collects herself in the last throes of vomiting.
"Fluttershy..."
She pulls herself up so fast you can't believe it.
"No! I'm sorry, I'm so sorry, please don't hate me, I can do it, I promise I’ll make it better!"
Fluttershy's face staring up at you from inches away from your crotch is the most conflicting thing you've ever felt. For one, despite the disgusting sensation of having your dick covered in beer-puke, you're still hard, mostly from the amazing sensation of Fluttershy's overly-enthusiastic blowjob. Secondly... for some reason you can't pinpoint, Fluttershy looks amazingly more attractive than she did a minute ago. Her hair is messy and matted, specks of dirt in her pink mane... and her eyes are tearing up at the edges, streaks of moisture trickling down her cheeks. There's a smear of regurgitated beer at the corner of her mouth, and her expression is so desperate and pathetic, she looks like a drug-addict begging for bits at the Canterlot train-station.
She looks worthless.
"Hng..."
You groan wordlessly as she throws herself onto your cock again. The sensation of one warmth is immediately replaced with another, and she deep-throats your dick with gusto, swallowing your whole length every second without pause.
The feeling of closeness returns. Your balls start to clench.
"Fluttershy..." you mumble again, reaching one of your hands out and placing it on top of her disheveled mane.
"Mmhm," Fluttershy murmurs into your cock. She keeps up her pace, bobbing her head up and down and running her tongue along the underside of your shaft with every other swallow. You clench your fingers in her hair, preparing to deliver the extent of your pent-up arousal into the back of her throat.
"Urk-"
The instant you start to cum, you feel the sensation of warm backwash on your dick. Fluttershy's throwing up again, but she doesn't stop moving her head. The vomit lands on your dick as you meet it with spray after spray of cum, the two fluids mixing together in Fluttershy's mouth and cascading back over your dick as Fluttershy bobs her head up and down. You hear her sniffling and moaning at the same time, tears welling up in her eyes from the acidic bite of the beer as it returns through her throat. There's much less of it this time, but still enough to more than equal your cum for volume - you're surprised, mostly, because you don't think you've ever cum more in your life.
Eventually, your cock ceases its firing squad, and Fluttershy bobs her head one or two more times before pulling off with a 'pop', and a muffled gag. A splash of cum and puke lands in the dirt to your right, and some stains your jeans. Well, the part of them that was untainted by the first bout, anyway.
"I can be a good girlfriend..." Fluttershy mumbles to herself, curling up into a ball at your side.
Absentmindedly, you reach a hand out onto her shoulder and stroke up and down her fur. Sweat and matted dirt greet your fingers.
Well... you can't argue that she's not eager to please.