The Quest For Fluttershy's Cherry

by Clopmama

Rating: mature
Tags: Other, Romance, Fluttershy, Sex, Human, My Little Pony: Friendship is Magic
Length: 1765

One man's quest to do Fluttershy.

One man's quest to do Fluttershy.

Published 2012-07-20 21:44:03 UTC
Last updated 2012-07-27 11:02:21 UTC

Chapter 1

It is a truth universally acknowledged that any man must want to do Fluttershy. To drive his rock-hard penis into her time and time again at an increasingly frantic rhythm, her shivering and squirming and making cute sounds below him, while he pounds on relentlessly and fills her up whole.

This simple truth also was subject to much secrecy; because of course, everyone knew it besides Fluttershy, and everyone went to great lengths to hide this self-evident fact from her pristine and by-nature innocent mind. Some of her friends, first of all Rarity, tried to gery gently prepare her for this fact, mentally, before Fluttershy would find out the hard way, which by some miracle hadn't happened yet. She would try to talk to Fluttershy in a roundabout way, for example, hadn't Fluttershy thought about any colts recently? She hadn't. She hadn't? But then what the had she been thinking about? Her animals, which are so sweet and cute and last week Angel Bunny had taken her on a picknick and generally after a while Rarity just gave up, one eyelid fluttering in a somewhat deranged way, short of yelling outright at Fluttershy that there was a whole throng of men acutely interested in having her and pounding her relentlessly.

Anyway, at least, that's what I had heard before I came here, not through a magical portal - come on! - but by means of a newly established transatlantic connection, plane going from NYC to Equestria, Canterlot Airport, in about 11 hours. I have to confess that the exact and sole motive behind this visit was not of a cultural nature or even, Celestia bless, to further the understanding among our nations; in fact, my goals were much less lofty. Indeed, all I wanted, the singular purpose of my trip, was to find and do Fluttershy. Once in Ponyville, I knew my opportunity to finally have Fluttershy was well within reach. Yes, I would have her, and have her good, until she wouldn't be able to walk straight on all four hooves the next day and like it, too.

At Canterlot, I took the Friendship Express bullet train to Ponyville, a refleshingly uncomplicated direct connection that took approximately four hours from station to station and conveniently served up hot and remarkably sugary beverages at your seat (at least in first class, which I had the privilege of enjoying). I leaned back, taking in the scenery rushing past outside, a smile on my lips, and thought about all the delicious opportunities I was surely going to have giving it good to Fluttershy. Yep, that was totally going to happen, I could feel it. In my loins.

Are you still reading, by the way? It is common wisdom that people just skip these, say, introductory parts in a clopfic. They are there merely to provide extremely superfluous and impractical leadup and to give the story an at least remote air of legitimacy and writerly aspiration, no matter how thin. I can't blame you if you skip this, hell, I always skip this just to get to the part where there's sweet me-on-Fluttershy sex, that is, to reiterate, my penis balls-deep in her delicious ponyvag...

But first things first. There's more exposition before you get to the good part. So anyway, I was sitting there on that train with dirty thoughts of Fluttershy on my mind, when the conductor came. She was pretty in the sense that female conductor mares can be pretty, with that uptight and almost archaic uniform composed of square shapes and a dark navy blue that suited her just perfectly, and the slight squeak she made as she asked me for my ticket. No doubt there weren't often human travellers on this route, and the thought of seeing one must have been new to her. I was surely the first human she had encountered. Her first time. As it would be Fluttershy's.

I cordially and warmly smiled and said that unfortunately I didn't have any funds because I hadn't yet had the opportunity to change my hard US dollars into slightly less hard Equestrian bits but that that was no problem, because I did have other, even harder bits. I winked at this point and I'm pretty sure she didn't find it cheesy or a turn-off or anything but rather maybe exotic and playful or even cute in the way ponies tend to find inapproriate things someone says who is not from the same ethnic or familial circle cute, or a child, maybe. I knew that normally, she would have had to kick me off the trian and alert authorities and a surcharge or at the very least sternly tell me off, but she did nothing of the sort. She only giggled when I told her that she was prety in the special conductor way, with her uniform and everything. I told her how much I liked mares who wore a uniform.

Now, dear reader, at this point I must confess that there had been at least some intent and design behind this whole business with the conductormare, since I had calculated that before I could bask in the glory that must have been Fluttershy's ponyvag (or ponybackdoor, mmh...), I would surely have to relearn at least some technical knowledge. By which I mean -- for all the sexual act's naturalness and immediacy due to its very animalic nature, the fact remained that I had never shagged a pony (understood here the cartoon kind, though certainly also no other kind) before, and that kind of lack of familiarity with the basics of pony anatomy could be cumbersome and an obstacle to rutting Fluttershy basically senseless by expertly and repeatedly aiming my rock-hard cock at her well-lubricated hole (or holes), thus making my mark, and then jackhammering her until she would wince for mercy with that cute squeaky voice of hers. In other words, I would have to practice with a lesser (to me) mare first, to ensure no lingering, remaining awkwardness in my sure-to-be orgastic/orgasmic encounter with that sweet yellow pegasus.

Of course, maybe I was getting ahead of myself here and thinking too far, worrying about things needlessly, since after all Fluttershy herself was highly unlikely to have any experience on that front -- and here be it with human or pony. Therefore any ensuing awkwardness she would almost certainly book on her account, relieving me of that responsibility, and basically have nothing to measure my performance against, which meant that I had a good hand either way (in both senses of the word). But I was an overperformer on that front, and besides, I ultimately wanted to pick up as many mares as at all possible along the way (and why not!), until I could get to my true objective, after which, I was sure, I would never again have anything measure up to it.

But anyway. Without boring my readers with the details of that encounter, which I will save doing for the climactic me-on-yellow-pegasus coupling, I did have an encounter with this filly, during which I may or may not have deposited a moderate to large amount of semen in her reproductive part, if only so as to prime the pump.

To be continued…

Chapter 2

Anyway, long story short. By the time we arrived in Ponyville, I was sweaty all over, the conductormare lay on the ground covered in numerous kinds of bodily fluids but smiling blissfully, and I had saved myself the cost of one train ride. It was safe to say that so far, I was happy with how my little trip to Equestria was going.

I stepped out of the train, paying little heed to my happily trembling equine sexual partner, and breathed in the fresh and wholesome air of Ponyville. An economy whose principal products were apples did have the advantage of clean air with a pleasantly rural smell that reminded me of freshly cut grass and ponyvag. Indeed, I noticed suddenly, my eyes swelling in their sockets like saucers, all the ponies running around here were completely naked! Just as I had expected. They weren't as uptight down here in lovely Ponyville as back up in hoity-toity Canterlot. I could almost feel a string of saliva running from my mouth. This was just too good to be true. Delicious... ponyvag... everywhere!

I innocently asked the first mare I ran across in front of the station for directions. "Excuse me, M'am---err--"

"Cheerilee." The brightly purple pony looked at me questioningly. I placed her in her mid-twenties. Her bright three-flower cutie mark was so outrageously innocent and happy that I felt my penis spring to life immediately.

"Miss Cheerilee, I am looking for, you know, Fluttershy. Would you happen to know where I can find her?"

"Fluttershy?" She looked at me in surprise. "She's not very often seen around town, she usually tends to the animals at her hut near the Everfree Forest. What would you want from her, anyway? It's rare to see humans around these parts."

"Do you prefer a pleasant lie or the honest truth?"

She skewed her face in reflection. "The honest truth," she concluded.

"Well, I'm afraid to say that I came to have wild, unbridled (or possibly bridled) sex with her."

"Oh."

"Yeah."

"You know, I can't approve of that. Especially as a responsible schoolteacher."

"I understand. I feel horrible."

"There are some who find pony-human sexual relations repugnant."

"Ah, there's some, there's others..." And internally, I thought that I could care less of what anyone or anypony thought once I would feel Fluttershy's satiny pussy walls clench around my rock hard cock until she begged for release, which I totally wouldn't give to her immediately because I wanted to savour rutting her until the very last moment where...

"I guess you're right," she said. She looked at me with a very weird expression, not repulsed at all, but on the contrary, curiously, almost morbidly so. "S-say--"

"Yes?"

"H-have you done it?"

"Done what?"

"Well--" Her face turned a scarlet red, which was barely noticeable against her lilac coat. "You know, with a pony..."

"Oh! That. Yeah, I've done it," I said casually. Like just five minutes ago, on the train, I added inwardly, and then, not without pride: "My semen is still fresh in that mare."

"What?" She recoiled.

"Oh, was I out loud? Damn... I was definitely out loud, right?"

"Yes. Follow me to the schoolhouse. It's closed right now."

And then we fucked.

I just keep getting better at this, don't I?