Eight Awesome Angles: a Windows Eight OS Story

by Hand-Made

Rating: mature
Tags: Slice of Life, My Little Pony: Friendship is Magic, Alternate Universe, Human, Other, Original Character, Sex
Length: 1985

Congratulations! You're the proud owner of a new operating system pony. It's the latest and greatest system yet to be released in Equestria. Too bad she's perpetually trying to get into your pants.

Congratulations! You're the proud owner of a new operating system pony. It's the latest and greatest system yet to be released in Equestria. Too bad she's perpetually trying to get into your pants.

A one-shot clop about horny filly Winnie and you, her owner, trying to alleviate heat.exe from her active programs list.

I wrote the character of Windows Eight, a.k.a. Winnie, for the now defunct browser pone threads. There are a few browser pony-esque stories floating around fimfiction. Check them out for some decent laughs and artificial intelligence clop.

Comments welcome and appreciated as always. Enjoy!

Published 2014-03-04 17:30:05 UTC
Last updated 2014-03-04 17:30:05 UTC

I/O

A pair of technicolor eyes spin rapidly in multiple directions, processing your requests efficiently and without delay.

"Hmmmph! I'm so bored! When are you going to take advantage of my awesome tablet game programs and put away these silly spreadsheets?" Windows 8, your new operating system, whines as you complete a series of important charts about hardwood densities.
In the light of multicolored tabs, ever her impatient expression looked only all the more adorable.

"Now Eight, you're supposed to be as efficient and sophisticated as your predecessor; patience is a virtue. I need to finish these charts for next week's cabinetry class to give the students." you tease the young operating system softly with a chuckle while closing out of your work for the day with a simple wave of your hand.

"Pssh, I'm way better than big sister!" she blows a raspberry into the air. "...and I thought I told you that my name is Winnie!" she states with a wink, giving off a light neigh and a giggle.

You cannot help but roll your eyes at the pun. Shame she seems dead serious about the name though.

"Careful, Eight. Flirting will get you into trouble..."

"Oh I'm programmed for anything; surely a tough OS like me can handle anything~"

Winnie climbs onto the bedspread you were laying on, shaking her tiny rump blatantly towards your face. You rub your eyes in mild frustration.

"Will nopony save me from this turbulently horny filly?" you groan; Eight was certainly trouble.

The other ponies warned you about getting an OS that only cost forty bits...but nooo, you had to be on the cutting edge of Microsoft's latest OS and tablet tech. Your reward for your devotion? Possession of one of the strangest, most obnoxious little tablets this side of Equestria. There's no way they all can be like this...

"Alright, alright, we can take a break and play a touch screen game." you sigh in resignation and bring up some tiles as Winnie looks up at you expectantly.

"Want to try out a round of Grumpy Griffins? We can only play a few rounds though, I need to finis-mmpphh?!" you're cut off as Winnie shoves her sky-blue lips against yours, closing her eyes and the tiles around her shut with a signature "click".

Caught off-guard, you cannot help but feel a small, flat tongue hungrily seeking yours as moments later the filly pulls back and leaps onto your stomach. What is even more shocking is the thin strand of saliva that she has somehow produced, linking your lips moments longer before succumbing to gravity.

"Hey..." Windows Eight pants, "today I heard about oak, red pine, yellow pine, and even maple...but there's only one wood I'm interested in." she grinds herself roughly against your crotch; you cannot help but be bewildered by not only her increasingly annoying puns but also her increasingly mare-ish behavior.

You also can't help but to immediately start growing inside of your trousers; it has been far too long since you have taken care of business. Taking a second to shake yourself from the mental situation, you quickly raise your hand and flick the tip of her tiny unicorn horn.

"Ah!" she cries out as the assault on your lower half is halted.

"Start Task Manager." you stoically command. You're going to find out what's making your OS behave so lewdly and, whether virus or hacker, somehow put a stop to the madness. Her horn glows a silvereye-gray as she rubs it with a hoof.

"Let's see...Processes...Memory...hmmm? What's this?" your eyes go wide as Winnie looks up at you, a look of perturbation melting into slight nervousness. "Eight...would you care to explain to me how the task HEAT.exe found its way to the top if your service list?"
"It's Winnie! ...a-and I'm a big filly with n-needs too, ya know!" she scrunches up her nose in a blush, a slight waver in her voice from shameless arousal. "I f-found it on the internet and thought it'd be a fun game for my coltfriend and I to play..."

"Eigh-...Winnie, you're my OS, not my marefriend. Besides, you really couldn't handle this anyway. You don't know what you're getting into." you sigh.

"That's not fair! Other fillies do it with their coltfriends, why not us?!" she implores with a voice crack.

Looks like the foal's not having any of it; you upgraded specifically to avoid this garbage. You knew Windows Seven probably had some negative influence on her little sister, but nothing like this. Hearing of this problem before, you only heard one way to stop it...but if it was the only way to get your productivity back and halt this filly from stealing kisses at night, then consequences be damned.

" Winnie."

Her pouting stops imediately.

"Yeeessss?" she blinks with a 'click'. You know that hormonal tone of voice, laden with bubbling lust; you lay back on the bed.
"If you really went through all the trouble to set this up, then I suppose you've earned your 'prize'." you flatly state, letting your own arousal seep into your growing manhood. You've thought about getting some mareish relief before, but not with an OS pony...and certainly not with a in-estrus filly. Winnie squees with delight, and wasting no time, magics your pants off. Her smile of eager confidence soon wavers however as your member is finally unveiled; it towers thickly over her face and horn.

"W-wow." she coughs, her smile still shaky, "Sis-7 didn't say anything about them being so big." The light blush that graces her cheeks begins to flare into most of her face. You can't help but chuckle.
"Hey! Don't laugh!" Winnie pouts with a squeak.

"Can't help it. I told you that you wouldn't be ready for thissss..." you hiss as the head of your cock is sloppily licked and taken into her mouth. Although she cannot take you deeply, by Celestia, she certainly is trying her damnedest. Without further ceremony, she pops your member out with a slight cough.

"S-see?" she mutters, wiping her lips with a blue hoof, "I'm programmed to take on anything."

Confidence once again fills her voice as her eyes meet yours; they spin once and blink with a 'click'. You grin; this might turn out more interesting than you'd imagined.

"Well then, big filly..." you take three fingers, spitting on them gently and spreading your saliva with hers along your aching shaft. "Turn around and let's flush your processes."

Winnie smirks, turning around and presenting herself without hesitation. Her dark-blue tail is flung aside to reveal a pair of darker blue lips and a pink, winking clitoris. The small clit, winking lewdly in a rapid motion, signals a fierce need for attention. Rising to your knees, you cannot help but shake your head. You half expected her unable to have downloaded the "full package" without you even knowing, but it looks like the filly really did her homework. Winnie must really need this...

You align your crown against her entrance and are rewarded with a small squirt of juice onto your aching glans. The smell is intoxicating, like fresh lavender and a slight musk. Setting your hands on her pert butt, you tense up in preparation as you grind against her winking. Your girth is nearly wider than her entire marehood.

"Hey..." Winnie pants, lowering her head to the mattress, "I've always wanted....I just need....just....just take me!"

Nodding softly, you begin the first slow thrust into her shallow depths, taking your time as immediate tightness threatens to squeeze you back out.

"Ahhhh!" Winnie cries out before burying her face into some sheets. "T-t-too big..."

She grunts from the girthy invasion as the first few inches of shaft cram her clitoris back inside it's hood. You keep sliding in, tightening your glutes to push harder so that you might overcome her tight ridges. Your efforts are rewarded with more heavenly-scented squirts of filly juice onto your shaft as you soon hit Winnie's cervix. She might have went all out on her downloaded marehood, but she certainly didn't take into account your particular size. Guess she should have snooped harder when you were toweling off from your showers...

"Oh Winnie...you're so damn tight..." you throatily groan as she manages to begin massaging your length with her walls, doing the best she can as you split her apart.

"Oh DOS, buck me." she achingly whines, grinding her teeth against the bedspread.
So brazen.

You slide nearly all the way out, making sure your glans hit every ridge of your delicious filly before shoving yourself back in without warning. Winnie screams in agony and delight, finally feeling you, her self-proclaimed coltfiend, claiming her tender hole. Your thrusting speeds up, yet you still remain half exposed as her moist lips squirt more and more liquid onto your remaining shaft. Every stroke elects mewls of animalistic arousal as Winnie begins to wiggle her hips slightly, struggling unsuccessfully to burry you deeper into her.
"S-so bucking big...ah!" she squeals, feeling you smack her ass softly mid-thrust.

"Language, young filly..." you chide sarcastically as your hand wanders over her slight mounds, tweaking her nipples gently.
"H-how AHH-are you still g-GAH-going?" Winnie hoofs at the bed but finds little purchase, helplessly trying to lean into your quickening thrusts. Sounds of high-pitched squelching fills the room as a thicker musk starts to permeate the air. Looks like she couldn't take into account human stamina either...

"S-something's haaapAAAA!!!"

Before she's able to ask anything else, Winnie's voice cracks and her face contorts into a scrunch before blushing fiercely. You feel your manhood drenched in sickly-yellow juice as Winnie screams into the air arcing her back and locking up against the sheets as her anus puckers from the ferocity of her first real maregasm. Your mind clouds over with lust as you feel yourself swell larger inside; animal instinct drives you to attempt to cram every inch of yourself into your young lover.

Alas, only about half of your shaft is able to be buried into this tight filly as your head knots itself tightly against her synthetic womb. You grip her haunches, putting your weight against her as you moan her name into the room before the first blast of your love explodes into her cervix. Winnie cries out, nearly snorting and gasping for air as her walls contract sporadically around you, instinctively milking you for every last drop.

Thick ropes of seed quickly fill what little space Winnie has as it quickly overflows down her thighs. Dollops of rich, fertile cream pour from your head into the squealing filly as the entrance to her womb rubs your glans oh-so well. After what feels like an eternity, you finally finish emptying yourself into her, pulling yourself out with a pop as a river of cum flows out onto the already large mess on the sheets. With a grunt, Winnie collapses her sweating body against the bed. You follow suit, laying yourself against her as you both struggle to catch your breath. She runs her forehooves over her stomach while your pull her close.

"My belly feels so full..." she groans, voice raspy from the screaming. Wiggling to turn herself around in your arms, Winnie peppers your face with her lips, leaving little kisses everywhere.

"Stop! Hey!" you can't help but giggle at the shower of adorable gratitude as she eventually snuggles up against your chest. The smell of sex hangs heavily in the air.

"Hey...?"

"Yes Winnie?" she smiles as you call her by her self-chosen name.

"Do you...think we can run this program again sometime?" the filly blushes, hiding slightly behind her forehooves as her eyes spin once with a click. You can't help but grin and rub her dark-blue mane. Looks like you won't be getting your future work done on time either.

Oh well...once a Windows OS, always a Windows OS...