A Walk on the Wildside

by JackStarhopper

Rating: mature
Tags: Anon, My Little Pony: Friendship is Magic, Second Person, Fetish, Romance, Fluttershy, Porn, Sex, Profanity, Slice of Life, Human, Twilight Sparkle
Length: 4334

You’re smitten with Fluttershy. Does she feel that way about you?

You are Anonymous. You’ve been living with Fluttershy since you inexplicably landed in Equestria, the magical land of ponies. You’re incredibly shy to say it, but you’ve been in love with your housemate ever since you heard her singing in the woods. Is it possible that this feeling goes both ways?

Cover Art by Darknisfan1995

Published 2021-10-12 23:00:00 UTC
Last updated 2023-07-08 16:39:22 UTC

De-Fluttering a Pegasus

Author's Note

I’m probably a little late to hop on this bandwagon, and the fat is dying down, but here’s my first Clopfic. Nothing special; just, Anon (Aka, you) accidentally walks in on his mare friend Fluttershy, while she’s pleasuring herself, and you can probably guess where it leads?

De-Fluttering a Pegasus

After a long day of work, you come to the cottage on the Outskirts of Ponyville where you’ve been staying for the past eleven months, two weeks, and three days. You go inside, looking for the mare you’ve been living with.

“Fluttershy, I’m home! You here?”

No pony answers and you assume your Mare-Friend’s not home. Feeling up for a little catnap, you carry yourself upstairs, and accidentally walk in on your housemate, who is apparently in the middle of a private moment; rubbing her hoof in circles along what appears to be her slit, causing you both gasp in surprise. It has been almost a year since you started dating the yellow Pegasus. Well, you’re not entirely sure if “dating” is really the correct word; With her it was really more like, sharing a bunch of lovely nature walks.

You still remember the first day you met her very clearly; You were doing research out in the woods when you had just been inexplicably dropped in a strange land with only the clothes and equipment you had on your back, and you had no idea where the hell you were. You were walking through the forest, when you heard something that made your heart soar. You heard a singing voice that could have easily come from a Disney Princess. You turn in the voice’s direction to see… Her. She was the first pony you had laid eyes on, and she took your breath away. Her light rose mane flowed so beautifully in the summery air. She stopped what she was doing momentarily and turned to see you there before letting out a gasp.

“Um… Hello?”

Never the worst thing to start with.

“Oh! Hey! I didn’t see you there. Actually, I’ve never even seen you out here before!”

“You’re right! I’m really not from around here at all.”

“You okay with my singing?”

“Actually, you have a lovely voice! Forgive my prying, but are you actually a…”

You pause to look at her for a moment more.

“A flying horse?”

She let’s out an adorable giggle.

“Very smart of you! I’m indeed a Pegasus pony.”

You ask her where you are, and she tells you that you’ve come to Equestria, the magical land of ponies. She also told that you were in the woods just outside of Ponyville.

“Well, thanks!”

“You have anywhere to go?”

“Well, If I’m being honest, I really don’t.”

“How would you like to stay at my cottage? It’s not far away.”

You agree and you follow her home. It’s small, but comfortable. Around her cottage was lots of cute little animals.

“I live in that cottage with all my little Animal friends.”

“Get outta here! I love animals too! So you’re like Ponyville’s creature sitter miss… Pony? I think we were so caught up in the moment earlier that we completely failed introduce ourselves.”

“Well, I’m Fluttershy! What’s your name?”

“Oh! Okay! My name’s Anonymous, but you can call me Anon.”

That night, she fixed you a pretty good meal; a House Salad, and some chamomile tea. Seems that she was just a simple pony with simple dreams, although she was rather curious about you. You explain to her that you’re a human, and that you’re from another world.

“Thanks for letting me stay at your place!”

“It’s nothing really Anon! We don’t get a lot of guests in this house. I’m a little shy around others.”

You notice a little white rabbit enter the cottage through the a little Doggie door. The little bunny comes up to you and checks you out.

“Hey there little fellow! Who’s this little guy?”

“Anonymous, meet my friend Angel Bunny! Angel Bunny, Anonymous.”

Over the next day, you spend your time exploring the rural town that is your new home. The place is small but comfortable, and its inhabitants seem to care for one another more than themselves. You soon start working a number of Odd jobs in town, from Sweet Apple Acres errands to Sugarcube Corner delivery. Just a few daily tasks to bring home some bacon. Not that ponies eat bacon; you’re pretty sure they live solely on a vegetarian diet, but whatever. Getting these odd jobs was surprisingly easy, as you are endowed with something no pony has; Hands.

As the weeks turned to months, you found yourself more and more with Fluttershy on your mind. She really had a soft spot for animals just like you. That time you went with her to the Grand Galloping Gala in Canterlot, you two spent lots of the night in botanical gardens at the castle. There, you watched all the exotic animals that lived there. Occasionally, one or two of them would check you two out, and your date would talk to them. She’s also showed you a lot of her favorite spots in the forest, which you too have taken a liking to. You also came to Equestria with a travel guitar that you called Annabelle. You played it for her every night after dinner. She loves to sing the songs you’ve taught her. Her favorites from your world included the Beatles, Lifehouse, and Bob Seger. Likewise, you enjoy writing chords for the pieces that she’s taught you. Eventually, to participate in her pony-pet play dates, you decided to adopt a creature from her animal sanctuary. You eventually decided on a little Sugar Glider, which you named Zeppelin. You’ve also come to be pretty good friends with all of hers. All the time though, your thoughts always drift towards Fluttershy. She’s super cute, and with a nice plump ass, and a big set of Teats that look almost human, say for being located just above her nether region. You often have dirty fantasies involving her, which feels so wrong, just because she’s not even your species. Her friend, Twilight Sparkle also told you about the time she accidentally turned Fluttershy into a vampire, which really gets you turned on to her. Maybe she likes you too? You don’t really know, but every day that went by, the question was always on the front of your mind; could she really be the one for you?

Now that you’ve seen her masturbating, it seems that you’ve got some explaining to do. You sit on her couch next to Angel Bunny and Zeppelin, waiting on your mare-friend. She soon sheepishly trots down the stairs, sorta hiding her face in her mane parting. Despite this, you can see that she’s got an adorable blush on her face that almost makes her look closer to Pinkie Pie than herself.

“Umm… Anon?”

“Yeah Fluttershy. I didn’t mean to barge in on you. I don’t know what came over me. I should have knocked.”

“It’s okay.”

You get up and are about to go feed the Chickens and collect eggs when Fluttershy puts a hoof to your shoulder.

“Yes Fluttershy?”

“Hey Anon, could I tell you something…personal?”

“Absolutely!”

You follow the pink and yellow Pegasus up to her bedroom, and you take a seat on her bed. Fluttershy sits next to you, fidgeting with her hooves and blushing even hotter than before, making her look like an overripe tomato.

“Anon… I’m a…*”
But all you heard at the end of that sentence was her mumbling as she sometimes does when she’s nervous.
“I’m sorry could you repeat that?”

“I’m a virgin!” That time, she kinda squeals the words.
“Gee Flutters, so am I. But why are you telling me that?”

She looks shyly into your eyes.

“I’ve sort of always…”

You put a hand to her red hot cheek when she pauses.

“Fluttershy. You can tell me what you want to say. I won’t judge you. I promise.”

“The thing is…”

She pauses once again out nervousness.

“I’ve had a crush on you since that day we met out in the forest around my cottage.”

You continue looking into her lovely cyan eyes.

“You have?”

“Yes! When you saw me masturbating earlier, I was thinking of you. The way you lift the chicken feed, water the flowers, and clean the cottage with your shirt off. Something about it just drives me wild. I know you’re probably feeling super uncomfortable right now, and if you don’t want to be friends anymore, I’d understand.”

She closes her eyes and turns her head down, now more embarrassed than you’ve ever seen her.

So she genuinely thinks you’re attractive? Actually, come to think of it, a lot of times on the nature walks you shared, she did seem rather flirtatious, but it’d never get too lewd with her. Usually, it’d be an innocent act of simply brushing her long tail against your crotch or bending over to pick something up, but nothing more than that. Now, you realize that she was purposely presenting herself to you. Seems that your wish has come true. You run your fingers through her light pink mane, and look again into her eyes.

“If I’m telling the truth, your crush on me goes both ways. I think you’re really beautiful in an Au naturale kind of way. You’ve got a lovely mane, a cute booty, and the most beautiful Singing voice I’ve ever heard. That day we met, and I heard you singing in the woods, It absolutely made my heart soar!”

Still blushing red-hot, she gives you the most adorable smile ever, and it isn’t long before she brings her lips to yours. For the moment, they’re soft, quick kisses, nothing too sexy, just sweet; You’re just trying to accommodate her shyness. But before long, it turns up to super sultry. She brings a hoof to the back of your neck, and you’re now tying tongues. The dance of tongues lasts for what seems like an eternity. Time seems to stand still.

“Hey Flutters. How would you like to take a walk on the wildside?” You eventually break away from the kiss to say in an erotic growl. She immediately responds in a shrill, yet unbelievably sultry voice,

“I’d love to Anon.”

The previous sultry kisses were now joined by long-Drawn out embraces, as you and Futtershy explore one another! Her wings hugging you, as her primary feathers are feeling your back like extra-long digits. Meanwhile, you’re using both of your hands likewise, right feeling her from her wings down to her juicy voluptuous ass. Your left hand feeling its way down the front of her body, from her teets down her lady parts. You begin by softly massaging her slit, not yet Penetrating. You hear her pant softly as you rub. The next stroke goes inside, and you move your fingers in circular strokes along her opening. Eventually, you find her magic spot, causing your mare-friend to go rigid with her wings shot to full extension and her eyes roll up in her head from the pleasure you give. Meanwhile, your cock is also starting to come to life. You continue abusing that G-Spot until she lets out a loud cry of bliss, as she clenches onto your finger. She coats your fingers in her fluids. After about a minute or so of mind-numbing ecstasy, you hear her squeal out, “ANON! PLEASE STOP TEASING ME FOR JUST A MOMENT!!!”

You stop fingering her as she lightly pants.

“Oh my god! Did I do something wrong? Was I too rough? I’m so sorry I…”

She puts her hoof to your mouth.

“No! That was just perfect… but I think it’s my turn to tease you some.”

She points a hoof to your belt, likely asking you to undo it for her. You do so, and she drops your khakis before she starts teasing you. She starts with long, painfully slow licks along your throbbing manhood, before she kisses and licks the tip, and eventually takes your entire shaft, threatening to send you into a fever pitch. You’re hardly the biggest guy around downstairs, but the size difference between you two makes your cock look rather huge. You’d think that given her meek demeanor, she wouldn’t even go anywhere near this, but alas, here you are, receiving oral pleasure from the shyest mare in Equestria. As she’s giving you amazing head, you lick your fingers to taste the fluids she left behind. The taste of her mare Juice is as sweet as she is. For about a minute more, she deepthroats your cock like you wouldn’t believe. She probably would have made your cock explode from this alone, but before long, she lets your dick out of her muzzle with a plop, and looks up to you with smoldering Bedroom eyes.

“ I’d really like to have you in me! If… If you wouldn’t mind?”

“Yeah! I think we’ve had enough foreplay! Let’s fuck!”

“Oh Anonymous!”

You never dreamed in a million years that you’d be getting laid, and most certainly not with a pony. Turns out that this was nothing short of pure, unadulterated bliss. You start with soft-slow thrusts into her opening, trying not to be too rough, and even so, she’s panting as though running a marathon and she grips extremely tight. Grasping her by the flanks, your hips soon connect with hers. Her panting increases in volume until she starts giving you moans of a lust-Driven slut. The sound of sex fills her bedroom, and the chorus of love builds to crescendo, echoing throughout the cottage. Good thing Fluttershy lives on the very edge of town, because she’s a bit of a screamer. She’s now having trouble forming coherent thoughts. She moans, squeals, pants, whines, the whole nine yards.

“Oh Sweet Celestia Anon! This is amazing!”

She rasps out over the pleasured ecstasy. You flip her on her back before you go missionary on her. And gradually start thrusting harder and faster. Her legs wrap around your hips as you thrust.

“You… *grunt* enjoying yourself…*grunt* Fluttershy?”

“Anon! You know I’m… OH GOSH!!!”

She lets out a long powerful cry as she orgasms. Her walls clench on your cock like a vise, as she gyrates and squirms like crazy from the shear force of her orgasm, and she leaks a small gush of her fragrant juices. You’re not far behind her. The fluid she just leaked lubricates your cock enough to thrust harder and faster than before. It isn’t long before you find your own climax and release load upon load of your seed deep into her.

The cries and moans fade, and soon, you’re lying in bed with your pale gold date, spent from the longest, hardest orgasm either of you have ever experienced. After a lifetime of being the town shut-in, the element of kindness has finally been deflowered. You’ve finally lost your own virginity as well, and neither of you have any fucks left to give. After what feels like an eternity of post-coital snuggling, Fluttershy breaks the silence, softly singing the ending of Night Moves, and eventually you join her. After you two finish singing the song, she lets out a happy moan and turns toward you.

“Sweet Celestia, that was amazing Anon!”

“I had fun too Fluttershy.”

“You feel like going to the Smoky mountains with me and Twilight for a research trip next month?”

“Oh yeah Flutters! It’s a date!”

You then go in for another passionate kiss.

Well played Anon; You and Fluttershy are now officially an item. You now have the world to look forward to.

To Be Continued...

The Call of the Wild

As Celestia’s first light hits your sleepy, tired eyes, you yawn and stretch as you get up, extra careful not to disturb your sleeping lover, softly snoring in bed beside you. You then step out of bed and go down stairs to fix some breakfast; fried eggs, pancakes with maple syrup, and some cider from Sweet Apple Acres, along with some Sourdough toast and zap apple Jam.

You climb the stairs to the bedroom, and awaken your darling girlfriend with a soft kiss on the lips. Her eyelids slowly part as she yawns, revealing to you her beautiful, cyan eyes.

“Good morning love!”, she says in her adorably shrill Voice.

“Good morning Fluttershy! You snore like a purring cat.”

She then pulls you in for a few more kisses. When the kiss breaks, and with a little blush on her face, she gives you a sweet smile.

“Last Night was just so magical Anon.”

“I feel like a new man myself Flutters. Come on! I’ve made us some breakfast.”

With that she follows you down to the kitchen.

Over the next two weeks, you and Fluttershy continue to flirt like lovers do. You give each other kisses, and I Love You’s throughout the day. Your evening music jammings were often concluded by some passionate kissing. You’d also shower together. You didn’t have sex every single night though. After all, you would soon be going to the Smoky Mountains, and would be for the most part, all alone, able to go at it like a couple of wild animals. There would still be the daily teasing though, and occasionally hot sex, but life isn't a porno, so you tried to hold it back some until your big trip. You don’t want to get too wild and over do it before then.

Now, after a few weeks of preparation, it was the day. You carried your research equipment, and Fluttershy’s luggage down to Twilight’s balloon mooring. After that, you went back to her cottage to escort your girlfriend down.

“So, Ladies! You ready to roll?” You ask Twilight and Fluttershy, as you’re about to take off. You all give the signal that you’re good for takeoff. With that, Twilight magically unties the ropes anchoring down her balloon, and you’re off.

After a couple of hours in the sky, you reach your destination. you land atop the Eastern side of the Smoky Mountains. You were staying at the home of the McColts. Fluttershy and Twilight told you about the time they had been summoned to the Smoky Mountains to resolve a many-years-long feud between them, and their neighbors, the Hooffields. Since then, it seemed that the two clans had made up big time. Once a week, the Hooffields would bring a wagon full of fresh produce over to their side of the mountain. In return, the McColts would inspect their neighbors’ property and do repairs if necessary.

About an hour or so after sunset, you find a little note on Fluttershy’s bed; “go to the south wall and follow the fireflies.” This is obviously your girlfriend leading you to a private setting for make outs. With Big Daddy McColt’s directions, you go to where the note tells you to go. After you look around, you find some fireflies hovering in a line leading off into the forest. You follow the airborne fireflies for what you’d have to guess was about a quarter mile or so. The fireflies lead you to a small meadow where you find your girlfriend waiting for you.

She's sitting on a soft bed of grass in a sexy pose. She turns to you and gives you a flirtatious bedroom-eyed smile. “Hey you! Whatcha doing?”. You return her flirtatious assault, "Ah, nothing! Just out observing the forest at night!" With that, you sit down on grass beside your girlfriend as a thousand or so of fireflies blink and light up the surrounding bushes. "You know why Fireflies glow in the night, don't you?" Fluttershy asks you, her voice a tad bit more sultry than usual. You look at her and respond. "Indeed I do. It's their visual mating call. A female in season flashes on the ground while a male flashes on the wing, searching for her light." She then turns to you, her eyes heavy-lidded, her gaze full of hunger and lust. “You're absolutely right my love!” Looks like the fireflies aren't the only things feeling frisky tonight. Fluttershy starts kissing your face sensually, stroking the back of your head with her primary feathers.

You continue kissing your girlfriend for a solid minute, before you stick a finger into her honeypot. Not too deep, just enough to make her moan softly and quiver all her of flight feathers. Meanwhile, you can feel your dick beginning to stand at attention.“oh! You’re the worst tease there is Anon!”, she whines. “I know! I kinda have a knack for that.” She continues cooing and squirming with joy and as you continue to run your fingers inside her slit, not quite deep enough to stimulate her clitoris, and not so shallow that she gets bored. Her squirming and moaning becomes more desperate as you continue to tease “ANONYMOUS! PLEASE STOP TEASING ME ALREADY!” She finally squeals out. You obey. “Oh Fluttershy! And it was so much fun to watch you squirm!” She looks you in the eyes with a look that’s almost predatory, at least for her; the meek filly that she still has a reputation for being. “Looks to me like you’re ready for some real fun.” She purrs while pointing to the bulge in your pants with her hoof.

You undo your belt and zipper and she pulls down your pants and begins to lick you, making sure to get her spit all over your throbbing member and paying extra attention to your head. Now you’re the one starting to squirm as she begins to slowly kiss the tip before she takes half your length. Eventually, you can’t take it anymore and so you grab her mane and push her onto your cock. She gets the hint and starts to take more and more of you into her maw. You love getting Blowjobs from your girlfriend. The sensation of shoving your cock down her throat is nothing short of fucking amazing. Fluttershy doesn’t even have a gag reflex, or if she does, she’s really good at controlling it. Your mind always goes blank when she takes your entire length, bobbing out at your ball sack, while the down of her wings gently caresses and plays with your testicles.

The pleasure of her giving you head is short-lived though, as suddenly, a familiar voice causes Fluttershy to pull off your dick, gasping in panic; "Ooh! Sounds pretty wild out here!" You both sputter like crazy as you try to cover yourself before you turn to face the eve's dropper. “And not just because we’re out in the woods!”

“FOR CELESTIA'S SAKE TWILIGHT! CAN'T YOU SEE WE'RE HAVING A PRIVATE MOMENT?” Fluttershy yells at Twilight! “Not so fast Fluttershy! It’s pretty hot already, but there’s nothing wrong with her being here.”, You respond to your girlfriend’s protests.

“Thanks Anon!” Twilight answers. “I read up about an ancient law that allows stallions to have more than one mare friend.” Fluttershy looks at you. “You, you wanna?”, she asks. You look the two mares for a minute. “I’m up for an opening relationship if you are Flutters?”

After a minute or so with a pondering look on her face, Fluttershy gives you both a look of approval. "Well, what are you waiting for Twilight? Come here and join the party baby!" With that, The Princess of friendship trots over to you and starts kissing your face alongside Fluttershy. You engage in a three-way tongue wrestling match with the two mares for several minutes, each mare taking their turn choking you with their tongue. Before long however, Fluttershy gently pushes you onto your back and impales herself on your cock. Slowly, she begins to ride you. She controls the pace as she slides up and down on your shaft. As Fluttershy is giving you the most amazing cowgirl action of your life, Twilight is straddling your face as you give her quivering mound of love pudding the best action you can give. Spreading her lips with your fingers, you lick Twilight’s honeypot deeply and passionately. The sweetness spurs you on almost as much as the Action Fluttershy is giving you with her slit. You sorta figured that Twilight was out of your league ever since you arrived in Equestria, and yet here you are; eating out the Princess of Friendship while your other girlfriend is riding your cock like her own personal breeding stud. Before long, the usual late night chorus of cicadas and crickets was joined by the slutty moans of two lust-driven mares. The outdoor orgy goes on for what feels like a good half hour. Eventually, you let out a long, deep moan into Twilight’s snatch as you finally give in to the pleasure and empty your self into Fluttershy. The two mares on you find their own release as well. As you’re being soaked in Fluttershy’s love nectar, your mouth is filling with the sweet taste of Twilight’s.

You lie on the grass with your two girlfriends in your post orgasmic bliss. You have no idea how you managed to orgasm as much as you have tonight, but in the haze of it all
you’ve realized something; not only were you the one to pop Fluttershy’s cherry, but now, you’ve successfully landed Twilight Sparkle, the Princess of Friendship, hook, line, and sinker. For several minutes, you lay on the grass panting heavily with the two pleasured mares in your arms. Eventually you break the silence.
“How was that Twilight?”
Twilight Turns to you, “that was so magical!”

“Wasn’t it though?” Fluttershy adds.

“Oh yeah! My loves!”

With that, Twilight and Fluttershy nuzzle into your side, both letting out Happy moans.

It certainly has been one hell of a night.

Author's Note

I know it’s been over a year that I’ve kept you waiting, but I hope this chapter was worth the wait.