Fun With Derpy

by Rainbow Chaser

A little help?...

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Author's Note

I might make one more chapter or an epilogue for this story. It's hard trying to write stuff on the fly. But I hope you guys enjoy it.


A little help?...

As the sun sets, you keep going over the scenario in your head over and over again. Tonight, after eyeing after her, and after that little show she gave you today, you were going to ask Derpy to be your mare friend. After talking with some of the stallions about who they'd been with, who they want to be with, and so on... You remember that conversation perfectly... You and a bunch of stallions in a bar sipping back cider, swapping stories. A few of em you'd recognized purely by reputation.

"Well ah'd have to say, my best lay, was mah sister's best friend fluttershy.... However if ah were to pick any mare in Ponyville, it would be that miss cheerilee from the schoolhouse. She can teach me a lesson any day...." As you look up you see who was talking. A large and rather muscular stallion: the farmer from Sweet Apple Acres. A few of the other stallions chuckled, yourself included. "Well golly Big Mac! Ah thought you always said AJ-" Just then the larger pony hoofed the other one, a smaller pony with a blonde coat and orange mane wearing a cowboy hat and vest. No doubt another Apple farmer.

"Braeburn ah told you once and ah'll tell ya again! Nothing happened between me an AJ. That was a rumor made up by Rainbow Dash as a crude prank." The red stallion replied. "Well sorry cuz... Ah didn't mean nothin by it." The younger one responded. As you sip your cider another stallion pipes up.

"I'll tell you who my best lay was. It used to be spitfire, but recently I started seeing one of the reserve members from the academy, Rainbow Dash. By celestia that mare will make you feel good a million times over in ten seconds flat!" Exclaimed the stallion. "Right is that because y'all can only last so long Soarin?" The older stallion said chuckling. You couldn't help but almost spit out your cider laughing at this response. Also looking over in surprise to see that it was very much indeed the same Soarin from the wonderbolts. "No it's not like that! Anyways... I guess if I were to pick any other mare out there, I'd probably pick princess Twilight. Wouldn't mind really teaching her how to use those wings." He said with a smirk. Just then the older stallion from before, Big Mac looked over and sees you looking in his direction.

"What about you city boy? Y'all got a story to share?" You realize he's talking to you and after a few moments you trot over to their table, and sit down. "Well I guess the best lay I've ever had was my girlfriend back in Manehattan before we broke up. She was real sweet but always too wrapped up in her dress making and costume designing. We only had sex once." As you tell your story you remember how you both felt, she was a virgin and so were you. You chuckle thinking about how hard it was to line yourself up the first time and wound up missing and cumming all over her. She was really pissed because you messed up her favorite skirt. "I guess if I were to pick any mare here in Ponyville, I'd probably go with that cute mailmare.... Derpy." The others stare at you in confusion.

"Out of all the mares in Ponyville let alone equestria. You'd choose Derpy Hooves? What's the point? She's not as hot as rarity or twilight, and don't even get me started on the eyes..." Soarin said. You think for a moment, then smile. "Yes... Yes I would choose her. There's something about her that makes me happy... I think I'm in love with her..." The others laughed at this response which leaves you a bit red in the face. But you take a deep breath. "I can't explain my feelings. They're just there." You respond. Then Big Mac takes a good look at you. "Well have ya told her yet?" You start to blush. "N-no I haven't..."

So now here you are, you have made a decision. With a bouquet of daisies in hoof, you make your way to Derpy's house. But as you reach her front door, you start to get nervous. What if she says no?... What if this is all a joke to her like some kind of game?... No. You've put it off for far too long. It's time to saddle up and grow a set. You take a deep breath and knock on the door. After a few minutes a voice is heard from inside.

"Come in!" You open the door and your jaw drops. There, right in front of you in the middle of the living room, is Derpy, all tied up, Rump in the air presented to you. "Oh anon! I've been expecting you! Please come in and close the door." She stares at you with a cute but lustful gaze knowing exactly what you want, and seeing just what she wants as your cock springs fourth to full hardness the closer you get to her.

"Derpy did.... Did you do all this for me?...." You say as you get close, eyeing the prize she has presented to you. You get a closer look and you can already feel yourself dripping pre as you get a good whiff of her wet pussy which, to your surprise smells just like blueberries. Well blueberry muffins to be exact. You get another whiff and she giggles, feeling your hot breath on her folds.

"Well... Don't just stand there, have a taste." She says with a voice that sounds bubbly and sexy at the same time. You happily oblige, and start licking her mare hood and plothole with delight. The taste of her juices, much like her scent, reminds you of blueberry muffins, and it only makes you want more. As you continue to lick, she lets out cute little squeaks and moans, and next thing you know you're caught off guard as you feel a sudden warmth envelope your shaft as she starts sucking on your cock. This sends you into a frenzy which causes you to bury your muzzle in her pussy as far as you can and lap up more of her feminine juices.

Feeling yourself come close, you pull away after a moment to compose yourself. By this time, she's become untied and is now on all fours, raising her ass in the air wiggling it at you. "Little help?..." She says staring back at you. You immediately mount her and line yourself up. "Ready?" You ask so as not to surprise her. "Mhhn! Just put it in me! Mount me! Fuck me! Fuck me until I can't walk!"

Hearing this, you immediately thrust into her leaving yourself completely hilted for a moment. Her wings immediately go stiff and her tongue hangs out of her mouth, her face twisted up in an expression of euphoric pleasure. You hold it a bit longer savoring the warmth and wetness of her pussy wrapped around your cock. After a few minutes of this, you start thrusting in and out of her, squeezing her flanks as she starts to moan. After all of your fantasies, all of your clopping sessions dreaming about this.... It's finally happening. It's real. Here you are, fucking the mare of your dreams and this is a dream come true.

After ten minutes, she pulls away and puts you on your back. "Sorry anon... But after hours, all deliveries must be made in the rear...." As she says this she straddles you and positions your cock right against her plothole. When she's done teasing you feel yourself enter her, feeling tighter than before, but still just as pleasurable. She looks right at you as she rides your cock, those beautiful, cute crossed eyes locked with yours, and she bends down to kiss you for a good five minutes before pulling away.

"I've been waiting for this all day. I couldn't stop thinking about you... Haah... And your big cock... I even came back to see you again when I saw you in your living room." When she said this you completely lost it. You thrust hard into her unloading your seed right into her anal passage. As you do this she screams out and squirts her feminine juices all over, moaning loudly in an orgasmic high.

Once you both come down from your orgasms, she gets up, your softening member sliding out of her with an audible pop, as your seed spills out of her in a steady stream. "Were you really thinking about me today?" She asks as she starts to clean your cock. "Hnnh.... Y-yeah.... And the day before that, and the day before th-that..." You say in between moans. At this point, you don't care if she knows. You decide to make your move. "D-Derpy.... I... I've fallen in love with you.... Ever since the first day I met you." She looks up at you with sparkling eyes. "R-really?...." You nod.

"Yes really.... Ever since I moved to Ponyville I've admired you from a far... I've always dreamed about this... Often. And now I finally have my chance.... Derpy Hooves, I am madly in love with you and I want you to be my mare friend." You say proudly. At this she looks at you and tears come to her eyes. "N-no pony has ever wanted me to be their mare friend... They've always looked at me like I was messed up in the head..." When she says this you feel real bad for her. "I don't think that... I think you're the most wonderful mare I've ever met." She kisses you for another five minutes then pulls away. "Yes... I'd love to be your mare friend."

You lay your head back smiling in delight as she cuddles up to you cutely, slowly falling asleep. And as your eyes start to drift off, you realize you can finally say, you have finally lived your fantasy...

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