Yanderpy: Chapter One

Today, you're on your way through the market. There are ponies by and behind stalls, ponies milling about, ponies just about everywhere.

Some familiar faces smile and wave. A particular orange-maned mare spots you from afar, and gives you a toothy grin.

You do like this particular pony.

You feel a slight tugging at the corners of your lips, parting them slightly so that a sliver of white shows. Carrot Top wiggles her brow playfully, gesturing for you to come on over to her stall. You, of course, are all too happy to oblige

“Hey, Anon,” the carrot farmer calls out. As you approach, you notice something behind her – it looks to you like a grey butt and a blonde tail wiggling around in the air, although you can't tell for sure since... well, it's a grey butt with a blonde tail sticking out of a box. You must put that aside for the moment, however, as there are more important things to attend to.

“Hey, Carrot,” you greet her in turn. There is momentary eye contact – and then Carrot Top quickly distracts herself with rearranging her carrots.

“So, Mister Anonymous...” she says, her head hidden from view as she ducks behind the counter. A few beats later and she reappears wearing a pretty hat. It's made out of straw, with a few flowers embedded on the outside. It suits her nicely. “What are you up to today?”

You prepare one of your world-famous subtle lines by Anon. “Just coming by the market to pick up some food when I saw your...” Your eyes begin to focus on what's behind her, causing you to pause mid-sentence. You, however, miraculously manage to pick off where you left off. “...pretty...”

It's hard to be smooth when there's a bubble-emblazoned butt still squirming around in the air just within your field of vision. Carrot Top picks up on your unfocused eyes, following them until she finally notices her friend.

“Oh! Uhm...” She blushes, looking back and forth between the two of you undecidedly, before quickly trotting up to the other mare.

“Derpy, what are you – Are you okay?”

Bubble Butt seems to have gotten herself stuck halfway inside a crate. She attempts to free herself by pushing on the side of the box with her hind legs, but if the past few minutes are anything to go by, the effort is futile.

“Uh, do you need help?” you ask, already making your way to the back of the stall.

“I-it's fine,” Carrot Top says, shaking her head. “This happens a lot, it's no big deal, really.”

“I'm okay!” a muffled voice calls out from within. “I think I might just need a little bit of help, though. Just a little!”

“Alright. Uh...”

As she really is just an ass sticking out of a crate, the dilemma of where to put your hands while pulling a pony out of a box has made its presence known. There's nowhere you can really grab that won't be uncomfortable for either party involved, except...

“Here. Just hold still, little pony.”

The two legs cease their struggling. You grab one in each hand, and, quite easily, lift blondie out of the box.

“Whew.” She wipes the sweat from her forehead, still hanging by her hind legs. In an admittedly boyish voice, she says, “I just don't know what went wrong.”

You set the grey pony down. She smiles up at you in this funny way. Funny because, well... she seems to have a lazy eye. No, not seems – she actually has a really bad lazy eye. Like, one that causes you to expect some kind of mental condition from her.

You really shouldn't judge. One side of her face looks intelligent, at least.

Carrot Top is quick to make introductions. She stands between the two of you, holding out a hoof that gestures to each of you in turn.

“Ditzy, this is Anonymous. Anon, Ditzy.”

As Ditzy holds out her hoof, you find it rather hard not to stare at just how badly skewed her right eye is. Nevertheless, you take her outstretched hoof.

“Nice to meet you, Ditzy,” you say, pointedly keeping your smile at a polite size.

“You can just call me Derpy!” she chirps. “Most of my friends do.”

You wonder why.

The next day, you're up bright and early.

Why? Because mornings are great, of course! They're the start of a mysterious, exciting new day!

Knock knock!

Speaking of which, you wonder who’s at the door. You set down your piece of toast and make your way to the door, coffee mug still in hand.

“Special delivery package for Mister Anon – ”

The mare you now recognize as Derpy gasps as she realizes who stands before her. You, ever the calm, collected guy, just lean against the door frame and take a sip from your mug.

“Howdy, Derpy. Didn't know you were my mailmare.”
“I- I didn't know, either,” she admits, rubbing the back of her head sheepishly. “And you'd think I would have recognized you, since you're – you're – ”

You decide to answer for her. “Kind of hard to miss?”

“Y-Yeah.” The head rubbing continues, except with the added extra of a blush. “No offense.”

“Don't worry about it.” You smile, taking your own hand and mussing up Derpy's mane. She looks up at you in wonder, and her blush deepens.

“Anyway,” you start, eying the package by your doormat, “what's this?”

The blondie seems to be snapping out of a trance. “Oh! Um, this!” She picks up the package with one hoof, holding it out to you. “It's for you!”

You chuckle as you take the box. “Yeah, I can see that. Do I need to sign something, or...?”

Her ears perk up, and she starts looking for something. “Oh, yeah! Let me just... Grr, where did I put that clipboard?”

She looks through her saddlebags, then lifts up one of her hooves to check underneath her, before taking glances back from whence she came and yelling, “Shoot! I think I dropped it somewhere! Uh...” She prances nervously on her hooves for a moment, before bolting off in another direction. “Be right back!”

You watch with morbid fascination as she flies headfirst into a tree trunk, and then after dizzily walking in circles for a minute finally shoots off into the sky again. Numerous postcards are left behind in her wake, and you can only shake your head before taking your package inside, along with the clipboard left on top of it.

The next few days, for the most part, go by pretty uneventfully. You haven't seen much of Carrot, but Derpy shows up knocking at your door every morning to deliver your mail.

One morning, you decide to ask how Carrot is doing. As you learned the first day you met the bubble mare, Carrot Top and Derpy are roommates.

“Carrot?” Derpy asks, tilting her head in question. “Why do you want to know about Carrot?”

Oblivious to this, you just sip your coffee and present your reason quite plainly. “Well, I just haven't really seen much of her lately... I was gonna ask if she was doing anything this weekend.”

Upon hearing this, Derpy suddenly looks hurt. Her ears flatten out against the sides of her head, and her eyes turn downcast. “So all that time... we spent together... It meant nothing to you?”

“What?”

The mailmare sullenly turns away, dragging along her bag with her as letters fall to the ground like dead leaves. You're left standing in your door, thoroughly and utterly confused. Guilt tinges the edges of your mind, as well.

Why did she respond that way? Did you say something wrong...?

Tissues... check.

Hoof moisturizer... check.

Open magazine full of Equestrian beauties... check.

You've never actually gotten it on with a pony before.

It took you awhile to even consider becoming attracted to them. Interspecies erotica, more commonly known as bestiality or zoophilia where you were from, was considered one of the most taboo acts to possibly commit.

Now, you're in a land where this same act is not only accepted, but quite common. This, along with the fact that your balls have nearly become smurf-blue over the past two years, convinced you to let go of your previous mindset, and explore what the animal-like denizens of Equestria – and beyond – had to offer.

Being the softy that you are, you'd like your first doggy-style in this world to be with somepony special. This, and this alone – not because you don't have game, or anything like that – is the sole reason why you've yet to get yourself a taste of that sweet pony vag. Still, you've whacked it off to ponies many times before, and have once again made it part of your daily ritual.

You feel your pants becoming tight as you browse through the many pages of the magazine. You imagine yourself pounding away at a particular mare's supple tush, grabbing hold of each cutiemark and... Oh yeah, you're ready. You undo the button and begin to unzip your pants, ready to unleash the beast from its cage and –

Kock knock knock!

You groan, zipping your jeans back up and buttoning them again before slipping all your fapping supplies back under the bed.

“Coming!” you call with a hint of frustration as you waddle to the front door.

You unlatch and open it, revealing the little gray pony that had run off earlier this morning. You're not used to seeing her without her mailmare uniform on – it's kind of cute to see her dressed like that, really.

“Hey, Derpy.”

“Hey, Anon. You wanna hang out? Can I come in?”

Normally, your little friend would be perfectly fine – no, welcome to come enter your humble abode. Right now, however, your balls are starting to ache, and little Anon is still very eager to come out and play.

“Uh, not right now, okay Derpy?” You force a smile so as to not seem hostile.

“Oh?” She cocks her head. “Why not?”

Bitch, when someone says 'not now,' you're not supposed to question it, you're supposed to scram.

“I'm just a little busy, Derpy...”

“With what?”

You grit your teeth, holding back your frustration. “I'm kind of tired right now, y'know? I had a long day at work and stuff. I was just sleeping when you knocked on my door...”

Bullshit.

“...and after that I need to clean up my house and stuff. Y'know, things that are really kind of boring.”

“Oh, okay. Can I wait inside then?”

Why won't she take a damn hint?!

“Listen, Derpy.” You breathe in deeply. “If you want to watch me jack off and sleep for half an hour, I invite you to come right on in.”

“Okay, I'm coming in.”

Before you know it, the pony has forced her way into your house, leaving you both flabbergasted and very annoyed at yourself for not leaving the door latched when you opened it.

You close the door and lock it, then proceed to walk back into your room where you know Derpy has gone.

“Hey, Anon, what's this?” she asks when you walk inside. She holds up a note, and you squint your eyes to read it. Upon realizing which particular note it is, they snap wide open in surprise. You immediately snatch the paper away from Derpy.

“Wow, you saved a letter from Carrot?” The pegasus shakes her head. “Better watch out, Anon. She's a real heart-breaker. A stallion-eater. Rawr.” She accentuates this by snapping her teeth together.

“I didn't save it, I just left it on my dresser,” you argue, stuffing the note into your pocket. “Why are you looking through my stuff, anyway?”

“Just trying to find those letters I made you. You did get them, right?”

You did get those letters. Every morning Derpy personally brought you, along with your normal mail, an average of three messages from herself. They were usually along the lines of, Hi Anon, hope you have a nice day! or We should really hang out sometime!, always with a childish-looking picture. The letters were cute, but you never really mentioned them to her after receiving them.

“Yeah, I got them.”

“Soooo...?” The little pony flutters her eyelashes. “Whaddya say? Wanna hang out soon?”

“I– Sure, yeah, I guess.”

“When?”

“I don't really know, let me check my–“

“What about tomorrow?”

“Yeah, yeah, I think I can tomorrow, after work.” The thought of spending hours alone with this mare gives you an queasy feeling, however. “Hey, maybe you can invite Carrot to come along?”

She just smiles. “I think Carrot's busy tomorrow.”

“Oh. Well, just ask her anyway, alright?”

“It's like I said. I think Carrot's busy tomorrow.”

The next morning goes as usual.

Derpy greets you as she delivers you your mail. You and her discuss where and when to meet up later. Derpy insists on coming over to your house after you get back from work, and starting off the day from there. You agree to this.

“Five o' clock. Okay, Derpy?”

“I thought you get off work at four?”

How did she even know...?

“Uh, yeah, but I like to relax for a bit. Daily ritual, the three 'S's, all that. You know.”

“Oh, okay. So how long do you need to relax?”

“I... Well, it takes me like, fifteen minutes to walk home. That gives me about forty-five minutes to do my thing.”

“Is half an hour enough time? I can be here at four-thirty, if you want.”

“No, I don't want. Five o' clock. Got it?”

“Sounds good. I'll be here at four-fifty.”

Realizing that you're going nowhere with this, you finally give in.

“Okay. Four-fifty.”

Her smile widens into a toothy grin. “Okay, Anon! See ya later!”

You're roused from your nap by a loud knocking.

“Anon! Anon! You in there, Anon?”

Fucking dammit. You know for a fact it's not four-fifty yet. You check your clock and find that she's half an hour early, clocking in at four-thirteen P.M.

“Anoooooon!”

You poke your head out of your room, and scream down the hallway, “I'm awake, alright?! Just hold on!”

She seems to be satisfied with this response, as the knocking stops. You swear under your breath, and grumpily answer the door.

“You're half an hour early,” you tell the little gray mare.

“Well, you're not just gonna leave me out here, are you?”

Maybe I will. Ever think of that?

“Ugh... I guess not.” You close the door, unlatch it, and then open it back up for her. “But next time, you're stuck outside until I say so.”

She happily prances inside. “Got it. Just trying to be early so we can have as much time together as possible!”

“Five or ten minutes is fine, but seriously, Derpy.”

She just goes straight to your room again. You sigh, feeling like you've just been intruded on, and follow her in.

She makes herself at home on your spinny chair. You plop yourself down on your bed and throw your arm across your forehead.

“So...” She swings her legs side to side as she makes full use of the chair. “Whatcha wanna do?”

“Well, I was just in the middle of sleeping when you showed up.”

“I know,” she says, again rummaging through your room for things to fiddle with. People messing with your stuff without asking tends to bother you, so you keep an eye on her.

She goes through your closet, pulling out random things, until you hear a click and see the glint of metal.

“Derpy, what are you doing with my knife?” You get up from your bed and make to take back the sharp object.

She playfully jabs the knife at you, stopping you in your advance.. “Yar! You ain't getting this back from me, matey!”

You really don't feel like putting up with this. “This is serious, Derpy. That's a weapon, and you shouldn't be playing with it. Put it down.“

“Oh, come on, Anon, loosen up. It's not like I'm actually going to stab you or something.“

“I don't care. I don't want you playing with it.”

“Ooh, look at this blade.” She pretends to admire the craftsmanship of your knife. “Very good balance. Where did you get this?”

“None of your business. Put it back where you found it, okay?”

“Can I try it out? Is there anything around here I can cut? Maybe I can carve our initials into your wall, so that you can always –”

You've had it with this shit. “Derpy, fucking put that thing down, now!”

“Okay, okay, you could've just asked nicely.” She carelessly throws the knife back in your closet without folding it back up. She then fiddles with her hooves a bit, before giving you a curious, somewhat concerned look. “Am I bothering you, Anon?”

Good lord...

“Yeah, a little bit...”

“Oh. Sorry, Anon.” her ears flatten against her head, and she wordlessly sits down in your chair, staring down at the carpet.

You watch her for a moment. You know she's just putting on a show. You know she's just trying to make you feel sorry for her. And yet...

You sigh. “I'm just a little grumpy right now. I didn't really get very much of a nap earlier.”

“So you just get really grumpy when you're tired?” This revelation seems to raise her spirits a little.

“Yeah...”

“Oh. You can go to sleep if you want, I'll just wait here until you're done.”

“Eh, no thanks.” You pull out some socks and shoes, and start putting them on. “We'll just go outside now, alright?”

“Okay!” she says, hopping off your chair. She goes and sits by your door, watching as you slide your socks on. Out of the corner of your eye, you watch her as she watches you.

Your eye twitches, and you smile politely at her. “You can wait outside, if you want. I won't be long.”

“Oh, no, I'm fine. I'll wait here with you.”

Normally, this really wouldn't bother you. In fact, a lot of the stuff she does wouldn't bother you if it were someone else doing it. Something about her just... irritates you.

Or maybe you really are just grumpy.

You shouldn't really shouldn't let little things bother you, Anon.

Note to self: try to be nicer to Derpy.

Author's Note

So, here's to hoping that the first chapter wasn't too uninteresting. Next chapter will be out soon, hopefully by tomorrow.

My proofreader asks to remain anonymous. ~~Haha. Just like in the story.~~bad joke here. Anyhow, three chapters remaining after this, I promise you won't be kept waiting for very long.