Care to Buy a Lady a Drink?

by MisterEdd

Rating: mature
Tags: Human, Anon, Original Character, My Little Pony: Friendship is Magic, Second Person, Alternate Universe, Comedy, Rarity, Porn, Sex, Profanity, Slice of Life
Length: 4660

While at the bar one night, you learn first-hand how "lady-like" Rarity gets when she's hammered

You're Anonymous, aka Anon, a human that wound up in Equestria after a spell gone wrong, courtesy of Twilight Sparkle. Unable to replicate the results, Twilight explained that there was no way to send you back home so it looks as though you're stuck in a world of happy dancing talking ponies. But hey, they have alcohol, so it's not all bad. One night, you visit Ponyville's only bar and find that one of your friends Rarity is there as well and she looks awful. You decide to cheer her up and buy her a drink...

A few rounds later, you decide to do the chivalrous thing and walk a very inebriated and musically-inclined Rarity home. Once there, you help her settle down and hope to get some shut-eye. Little do you suspect, your night is about to take a most unexpected but pleasant turn...

Contains: Drunk Rarity, Anon, a buttload of booze, serious discussions, human-on-pony action, cuddling and moments of d'aww!

Cover art from Derpibooru

Whoo-hoo, Featured!

Edited by Snowliaison

Published 2020-04-25 02:10:01 UTC
Last updated 2020-04-25 02:10:01 UTC

Wine Not?

Stepping through the double doors of The Water Trough, you took a deep breath and sighed, the smell of cheap liquor, cigarette smoke, vomit and stale peanuts filtering through your nostrils. R&B music echoed through the jukebox in the corner as you strode across the room, the other occupants going about their normal business, not even glancing in your direction. After your time spent in the small town, in the bar especially, ponies just got used to you. Climbing atop a special seat built to accommodate your height and weight, you rapped your knuckles on the counter to wait for Top Shelf to take your order. As you were a regular, you and the barkeep were on a first name basis.

Your name is Anonymous, or "Anon" for short and you had the supreme honor of being Equestria's first and only human in existence. You'd just come home from work and barely shut the door when a crazy light enveloped you and had you hurtling through time and space, definitely not screaming at the top of your lungs like a nine-year-old girl. You tumbled across a hard surface and when you'd gotten your bearings, you'd discovered that you were in a crystal castle of some kind and furthermore, a collection of wide-eyed technicolor ponies were gawking at you. You did not freak out and started swinging a nearby hat rack at them (despite only one of them actually wearing a hat) while not hysterically screaming for them to avoid any rectal probing. Eventually, after calming you down (which consisted of the purple one tying you up in magical bonds while the soft-voiced yellow one stroked your head), the lead pony named Twilight Sparkle explained that she was performing a spell to yank an object through separate universes but accidentally grabbed you.

Twilight was nice enough to give you a room while she and the other princesses figured out a way to send you back home. After weeks of trial and error, however, they came up empty-handed...or empty-hoofed and explained that you were essentially stuck here. Maintaining your composure, you simply walked to the nearest bar (since it was a small town, they only had one) and drank yourself silly. You totally did not curl up into a ball and start crying, bemoaning the fact that you'd never see your parents or your cat Chairman Meow again. Nope, you handled it like a total boss and Fluttershy did not have to be called in to take you back to the castle, snuggling with you until you fell asleep.

Nobody's buying this, huh?

Anyway, you eventually got over the pang of never being back home but it was only through the combined efforts of time, introspection and the support of your amazing new friends. And booze. Lots and lots of booze. Seriously, how weren't you dead from alcohol poisoning by now?

A red-brown unicorn came into view, a light purple aura telekinetically wiping a glass with a cloth. Shit, magic was cool! Top Shelf was easily the best bartender you'd ever met, being witty and friendly but not afraid to let you know if you were being a dick. He had this mustache and mane style that made you think of a 70's porn star, you know with the fluffy hair and thick Jesse Ventura-type mustache like in Predator. Honestly, why did Jesse have to ditch it? He looks like an angry potato without it!

"Hey Anon," Top Shelf grunted. "Back to try and kill your liver?"

You grinned, "'Try' is the key word. Bastard is hard to kill, you know?"

"That I get. My grandfather had a bottle of beer with every meal until the day he died."

"What'd he die of?"

"Crushed by a fallen piano," he answered without a hint of humor in his voice.

"Oh. Well hey, at least he knows how to play B-flat."

The stallion narrowed his eyes at you and you were afraid he was going to introduce his hind hoof to your anus when he burst out into laughter. "Oh sweet Celestia, that's a good one! I'm going to have to remember that one! Ha-ha-ha, 'B-flat!'"

You broke into nervous chuckling while subtly checking your pants for shit. "Glad you think so, Top."

"Whew! So, what can I get for you?"

"I'll take a double whisky on the rocks."

Top Shelf nodded and went to work preparing your drink. Normally you would share a drink and a good yarn with a mare named Berryshine, who became a good friend and drinking buddy. Unfortunately, she was busy that day so you decided to fly solo. Either way was fine for you and you were glad that Berryshine had something else to do besides drink. She was an even worse alcoholic than you were!

You heard a sigh beside you and you nearly fell over when you saw who'd taken a seat. It was Rarity, fashion designer and Miss Prim-And-Proper herself, in a dump like this. Hey, it was a dump but it was your dump! It'd be like Anna Wintour visiting a bar in Chicago and ordering a margarita. Some things just don't mix.

"Rarity?"

The mare turned and gave you a lazy smile. "Hello Anonymous. I bet you're surprised to see me here."

"'Surprised' is an understatement," you retorted as Top Shelf set your drink down in front of you. "What in the name of Princess Celestia's giant keister are you doing here?"

"Barkeep? I'll have a glass of your best wine."

"Coming up, miss."

Rarity then sighed and placed her chin on her hooves. "I'm feeling rather down and I know how often you come in here so I thought I'd come check it out for myself."

A glass full of red wine was deposited in front of her.

"Here you go, miss."

"Thank you," Rarity muttered and took a sip. "That's surprisingly not bad."

"So why are you here?" You were legitimately curious. "You're a classy, elegant lady. This is the last place that I'd expect you to be."

Rarity smiled at this, a real smile. "I suppose I wanted a change of pace. Misery loves company after all."

And Annie Wilkes loves Misery, You thought to yourself. Ponies still didn't get half the jokes and references you made so you often told them to yourself. "What happened?"

Taking another sip of wine, Rarity stared into her glass. "I guess I'm just doubting myself."

You scooted closer. "In what way? I wouldn't imagine somepony like you having room for doubt."

There was that smile again. Man, she had a great smile. And a nice rump too. Yeah, you weren't ashamed to admit that you'd wonder what it'd be like a fuck a pony. An Equestrian pony, not an Earth one. It only made sense, seeing as how you were the only human here and all there was were ponies. You'd become aware of the shape of their curves, the crescents that lay beneath their swaying tails and their perky little udders. One of these days, you were totally going to stick your wick in one.

"I certainly hide it well, don't I?" Rarity tittered wryly. "I mean, the confidence, the poise, the voice." She then frowned. "It's just not enough. I'm not enough."

You emptied your drink. "What are you talking about? You're a goddamn national hero! You're one of the richest ponies in Equestria and a fashion icon! Everypony loves you!"

You could see your praise was having somewhat of an effect but she still looked dejected. "Do they? Or do they love what I represent?" She swirled her wine around and sipped it. "They love Rarity the Hero, Rarity the Fashionista, Rarity the Face of Cosmare and Neighbelline. But do they love Rarity the Mare?"

The wheels in your head turned. "You think that everypony only cares about your wealth and fame."

Rarity nodded solemnly and downed her glass. "Barkeep, another. And leave the bottle."

"You've got it, miss," Top Shelf replied, refilling Rarity's glass and setting the bottle in front of her.

"Thank you." No longer satisfied with dainty little sips, she took to gulping the wine down. She nodded and turned towards you. "You've hit the proverbial nail on the head, Darling."

You were flabbergasted. "What about your friends? Your family? They love you."

"I know but, and I'm ashamed of even saying this, but they're not enough." Rarity ran a hoof around the rim of her glass. "I want a relationship. You know, coltfriend, marriage, foals? And yet, so far, all of the stallions I've met are shallow, inconsiderate, sex-crazed ego-maniacs!" Noticing your expression, she cleared her throat and touched up her mane. "My apologies."

"There's no need to apologize, Rarity. I'd be pissed if I were in your horseshoes," you admitted and then thanked Top Shelf when he refilled your glass. "Actually, I sympathize."

One perfect eyebrow went up. "You do?"

You nodded and stared straight ahead. "I'm in a world where I'm the only one of my kind and excluding Ponyville, the citizens of said world go out of their way to avoid me, at best seeing me as a freak and at worst, something that needs to crawl into a hole and die."

Something touched your left hand and you saw it was a hoof, prompting you to look at Rarity. There was such sadness behind those blue orbs as well as guilt. "I'm so sorry, Anon. I've only been thinking about what I've been going through and I ignored how you must feel."

You laid your other hand atop her hoof, gently stroking the toe and walls with your thumb. "It's okay, really. You've had a lot on your mind so there's no need to beat yourself up."

Rarity shook her head. "It's not okay. You're my friend and I should've taken your feelings into consideration."

"Well as your friend, I forgive you." You grinned and she did the same. "Tell you what: why don't us two, lonely souls just sit here and drink? It's on me."

"Anon, I couldn't possibly-..."

"It's fine, really. I've got plenty of bits and besides, I know you're the Element of Generosity but just once, can't you let someone else do something nice for you just for the hell of it?"

Contemplating your words, Rarity nodded. "Since you put it so elegantly, why not?"

"Hey Top Shelf?"

The bartender slid across the floor and faced you. "What can I do you for?"

"We're going to have some more wine and whiskey. A lot more."

~*~

Rarity leaned against you for support as you both stumbled your way back to Carousal Boutique, red-faced and stinking of booze but high in mirth. Although you'd drunken quite a lot that night, you were only slightly buzzed, having long since built up a tolerance to spirits thanks to your time spent at The Water Trough. Your companion, however, was obviously not accustomed to imbibing large amounts of alcohol, having gotten tipsy from only drinking half the bottle. The mare was currently latched onto your arm with a foreleg while her unoccupied hoof clasped the wine bottle. A glass of wine floated above her head, surrounded in her signature light blue magic aura.

As it turns out, Drunk Rarity was a fan of singing.

"In Docklin's fair city, where the mares are so *hic!* pretty...!"

She always had a lovely singing voice, but it was currently hampered by her intoxicated state, coming out screechy and slightly off-key, interrupted here and there with giggles or hiccups.

"...I first laid eyes on...he-he-he...sweet Molly Malope!"

You were soon at the door of the boutique and after missing the lock a couple of times, you managed to unlock the door and usher Rarity inside, who was mercifully done with her caterwauling. Slamming the door with your foot, you flipped the light switch and blinked a couple of times at the change in visuals. You hung your coat up-only for it to fall down-and jumped ten feet in the air when something shattered. Rarity had dropped both the wine glass and bottle, watching disheartened as the red liquid seeped across the floor. She stared up at you, tears in her eyes and gesturing towards the mess with both forelegs.

"Why? It's such a waste! This is the worst thing ever!"

You shook your head and dragged yourself to the kitchen, inadvertently knocking over a chair and a few knick-knacks. A few paper towels fixed the spilled wine issue and you stood back to appraise your quick thinking. You turned and couldn't help but snicker as Rarity thumped one forehoof then the other on the first step of the stairs. She wobbled unsteadily, making it up to the third step before collapsing on the stairs. You did not let out a high-pitched giggle at the sight.

"Anooooon! Help me," she whimpered with a pouting lip. "The stairs are being rude!"

Oh, those eyes. You couldn't help but be pulled towards them. Gently lifting the mare up bridal-style, you slowly stomped up the stairs, being careful to not lose your footing. Turning the corner, you bumped your shoulder into the wall beside the door, corrected yourself and grabbed a hold of the knob as if holding on for dear life. With a twist, you shoved the door open.

You'd only ever been in Rarity's bedroom once, having to help her search for a missing earring the day of an important press conference for the opening of a store in Las Pegasus. A quick jab to the light switch with your elbow caused the room to be illuminated, revealing the big canopied bed and purple curtains. You carefully deposited Rarity on the bed, ensuring that her head was on the pillow. You sunk to your knees beside the bed and sighed, thinking back on what a weird but ultimately fun night you had. You heard the mattress squeak beside you.

"Oh Anon?" You turned and your jaw dropped. Rarity was laying on her side with one foreleg propping her head up, the other rubbing her stomach in little circles. "You're not thinking of leaving, are you?"

"I...I was hoping you'd let me spend the night. The couch sounds pretty nice."

She giggled sultrily and gave you a half-lidded stare. "How gallant of you. But as you can see, there's plenty of room for both of us." You could feel your boner rising. "Wouldn't you like that...Darling?" You'd heard Rarity use that word so often but never in that context. She was horny and wanted your dick.

Awesome!

However, the more responsible part of your brain woke up just in the nick of time. You managed to pull yourself to your feet. "R-Rarity, listen, you're had too much to drink and you're not thinking straight-..."

"Oh sweet Anon, I am thinking straight," Rarity interjected, undressing you with her eyes. "Don't blame the wine. I've wanted you for so long that it hurts." Her tone went from seductive to desperate. "I've thought about having you inside me." Her hoof traveled southward, your eyes tracking its movement as it came to rest on her most holy of holies. Using the toe, she forced her lower lips open, revealing her engorged and wet vulva. "Don't you want me too?"

You swallowed hard. "Fuck yes. But you're drunk...and I don't want to take advantage of you."

The hoof moved up and down, eliciting a moan from the unicorn. "It's not taking advantage if we both want it," she murmured, her slit now winking at you, serving as a silent beacon calling for your dick. Speaking of your dick, it had become so erect from Rarity's lewd little display that it was starting to hurt.

You knelt beside the bed and placed a hand on her cheek. "I want this. I want you." Indigo eyes shimmered in the light and you could swear you saw tears. Slowly, you leaned forward until your lips met. Apart from the fuzz surrounding her lips and the slight pronouncement of her muzzle, it was no different than kissing a human woman. Maybe it was the forbidden nature of the act or the needy whimpers of the mare beneath you as you locked lips but right now, you'd never wanted anyone as badly as you wanted her.

You started out gentle, knowing that it was how she'd want to be treated but you were surprised when she shoved her mouth firmly against yours, her lips smacking and suckling, demonstrating her apparently long-held desire for you. You quickly reciprocated, your hand caressing her cheek as you pressed harder down onto her mouth. Your tongue slipped in between her teeth and hers was there to meet it. They lapped at one another, no pattern, no rhythm, only lust. She tasted like wine, a nutmeg-infused sweet and tangy concoction that helped to send more blood downward.

You both pulled away, heaving in the air you'd lost in your kiss. As you looked at one another, something seemed to click in both of your alcohol-addled brains. You scratched one of her ears, an action that earned you an appreciative purr.

"I don't want this to just be a one-night stand."

"G-good. Me neither, Anon."

"I really like you," you admitted.

Rarity smiled. "I really like you too. You're so sweet and you treat me and my friends right."

Uncertainty creeped into the back of your head. "So you don't...you don't mind that I'm not a pony?"

She giggled but you could tell there was some doubt there as well. "Not at all. I'll admit that I once saw you as well, you. Over time, I found myself intrigued by your appearance. Does it matter that I'm not a human?"

You lightly kissed her lips. "No. You're beautiful the way you are."

She blushed at this. "And you're very handsome yourself. Anon, it's...well, been a long time since I've been...intimate with anypony."

"How long is a 'long time'?"

"A few months?"

You raised an eyebrow.

"A few years."

Sitting down on the bed, you pulled her into your arms. "It doesn't matter. You and me, that's what matters."

"Then let's get started." Her horn glowed and your shirt burst open, scattering buttons all over the room. Before you could protest, Rarity's lips crashed against your own, her hooves sliding over your now exposed chest. Alright, fuck the shirt. Your fingers trailed her chest, moving down her stomach and udders before coming to rest on her marehood and without a second thought, you dove right in.

Rarity's head snapped back, a low moan escaping her lips. You grasped at the nub, pinching and teasing it before using your index and middle fingers to spread her lips, earning you a moaning huff. She was putty in your hands. You curled your fingers inside them, moving them in a clockwise motion. You grinned as Rarity slammed her head back onto the pillow and you traveled upward. Now, if only you could find that magic spot...

"Uh, uh, Anon!"

...Found it.

Relentlessly, you focused your attack on that one spot. Rarity's eyes clenched shut at the over-stimulation, her chest heaving as she fought to steady her breathing. Before you could go any further, the front of your pants were surrounded by a blue aura before being burst open, snapping your zipper and yanking the button right off. You noticed a look of pure lust on Rarity's panting face. She lifted her head up and stared you down.

"Enough...games. I...want...your...cock!"

Your hands quickly seized your Li'l Anon and pulled it out of the slit in your underwear, allowing it to stand proudly for Rarity to see. Wait, what if she didn't like it? The shape was all wrong and despite the fact that you were more than half the size of a regular pony, you knew that stallions packed bigger dicks. Doubt was a terrible and intrusive foe that crumpled the will of even the most powerful of men. Even through your semi-drunken haze, you felt ashamed of your freakish anatomy.

However, this all changed when you saw Rarity eyeing your Johnson the same way Twilight does a new book. Rolling onto her side, Rarity rose to her hooves and slowly approached your erection, her nostrils flaring at some scent you couldn't detect. She pressed her face fight against your dick, inhaling your scent and even moaning in the process. Her tongue darted out and gave your shaft a long, hard lick, flicking at the head to catch some pre-cum that'd gathered there. Her eyes were practically pinpricks at this moment.

"A-Anon?" She managed, her chest shuddering as she took a breath. "Fuck me."

Damn, talk about a motivator!

Seizing the mare by her luscious hips, you spun around so that you were laying down and she was seated on your stomach. It was a nice change to see the diminutive mare looming over you, her eyes glazed over with raw carnality. Walking backwards, she raised her butt above your cock, a thin layer of mare cum drizzling over it. Slowly, she lowered herself so that the head prodded her lips, drawing a hiss out of both of you. Even if it was just the entrance, she was internally hotter than any girl you'd slept with before and you were looking forward to exploring her depths.

Rarity's lips grabbed at your head every time it entered, massaging it and giving it a sneak peak at how the rest of her would feel. You were eager and rearing to go but this was nice too, a nice little appetizer before the main course. This was new but the pleasure you were getting from it garnered no complaints from you. You watched as Rarity levitated your necktie off of you and poked her head through the loop, letting it fall around her neck. She then winked at you and you blushed, excited at the prospect of owning something that'd been in contact with Rarity.

Then, without warning, she slammed her butt down, taking your entire length inside of her.

"JesustapdancingChristonawaterbed!"

Spots danced across your eyes, your member encased by the smooth, soft insides of Rarity's love canal. She was hot before but now she was boiling! It was a wonder that you didn't nut immediately considering your dual situation of no sex and the snugness of easily the best pussy you'd ever been inside of. You noticed Rarity had gone completely still, her mouth flapping open and closed but nothing was coming out. You were about to ask her if she was okay when-

"Ahhhhhuuuuuuahhh!

You felt her clench herself around you, her body lightly shuddering atop you. A flood of mare cum seeped down your hips and thighs. Damn, it really had been a long time for her!

"Rarity...did you just cum?"

Floating down from her high, the mare peered down at you shamefully, her hooves reaching up to touch her burning cheeks. "I...um....yes. I'm so sorry!"

You rubbed her hips. "Shhh, hey it's okay. It was actually kind of hot to think that I made you cum so easily."

She sniffled, "R-really?"

"Really."

Seeing your nod, Rarity went from embarrassed to coquettish. "Oh, is that so?" She sat up, your dick sliding along her velvety interior and drawing a groan from the both of you. She descended, letting out a squeak. "You're going to cum in me." It wasn't a suggestion. "Mmmmm," she moaned, building up a steady rhythm. "You're going to mark me, make me your mare...ah!"

Your hands grasped her thick rump, squeezing the pliable flesh of her cheeks between your fingers. Rarity mewled at this so you squeezed a little harder, her humps increasing in speed. Just a few hours ago, you were just some strange alien in a world that didn't care about you. Now you had one of its greatest heroes, a drop-dead sexy mare that stallions would kill to be with, moaning whorishly as she bounced in your lap, riding your dick like a pogo stick. You weren't one to be smug but who's the freak now, assholes?

Up, down, up, down, Rarity went, her distinctive coif bouncing in tune with her strokes. Sweat trickled down her brow, her mouth jutting out as she sputtered out words you never in a million years would've heard her say. It was getting harder and harder to stave off your own orgasm. Don't cum, don't cum, don't cum! You repeated this mantra over and over in your head but the breathtaking mare riding you wasn't making it easy.

Okay, Betty White naked! A fat guy vomiting! Aunt Margaret in a bikini! Wait, why isn't that one working?!

The wet smacking of your hips meeting filled the room along with the stench of sex. Thankfully, Rarity's little sister Sweetie Belle wasn't staying over tonight so you could partake in this inter-species romp. Plus, it'd be a shame if you ended up traumatizing the poor filly. I mean, who would want that on the night you and Rarity first got intimate?

Gyrating her hips, Rarity stared down at you hungrily, her sweat-matted mane covering one eye. You realized that she'd been doing all of the work and that was no good. You grabbed a hold of her midsection and hefted her off of your soaking lap. She sputtered puzzlingly at you.

"A-Anon, what do you think you're-...?"

Switching to a seated position, you impaled Rarity down onto your dick, bringing out a howl of pleasure from the unicorn. You repeated the motion, creating a new cycle comprised of lifting her up and slamming her back down. Sweet Jehoshaphat, it was incredible! You thrust into her at the same time you rammed your hips together, making her scream in delight. Her tongue lolled out of her mouth, her forelegs flopping at her sides.

"Rarity, I don't think I can last much longer..."

Your confession snapped Rarity out of her reverie. "Yes, yes! Fill me with your seed! Breed me!"

"You realize that I can't actually get you-..."

"Pump me full of your cum! Ravage me!"

Who can argue with that?

Your upstrokes increased, your hips bucking wildly. No longer capable of comprehensible speech, Rarity was reduced to incoherent blubbering and wails of passion. You could feel yourself approaching the edge. With a final thrust, you grit your teeth and grunted as your cock erupted.

"Fuckfuckfuckfuck!"

Rarity convulsed as she was filled with your semen, a low shriek passing her lips. Rope after rope entered her womb and after the seventh spurt, you finally felt your balls relax. Your toes uncurled and you finally laid your head back down. Jizz seeped from Rarity's marehood and pooled around your stomach but you didn't care. You just had the biggest orgasm of your life and even better, it was with someone that you cared about.

Speaking of which, Rarity gave it a minute before weakly rising off of your now-soft dick, which plopped out of her folds as she tumbled onto the bed beside you. You wrapped both arms around her and pulled her close, setting her head on your chest. Neither one of you spoke, instead simply enjoying each other in your post-coital bliss. You gently trailed your fingertips along her coat, something that evidently you both enjoyed. She took to lazily drawing little figure-eights on your stomach.

Ten minutes had passed before a small voice spoke up.

"Anon?"

You turned, finding Rarity staring tenderly at you. "Yeah?"

Biting her lip, she searched your face for something. "Who am I to you?"

You smiled, "Rarity the Mare" and kissed her above her right eye.

This made her giggle and she hummed in delight.

"What about me?"

Rarity yawned and closed her eyes. "The best thing to ever happen to me," she murmured and before long, was fast asleep. Your heart slowed down at her words before resuming its normal pace.

"Me too, Rarity," you smiled and drifted off to sleep.