Derpy Colada

by NotProud

Rating: mature
Tags: My Little Pony: Friendship is Magic, Dark, Dinky Hooves, Other, Sex, Tragedy, Derpy Hooves
Length: 4420

Forbidden desires, unspoken knowledge, an innocent filly, and Derpy Hooves...

Derpy's a mare of little brain,
Who doesn't know wrong from right.
Won't you be surprised whom she takes home today
To sleep in her bed tonight?

Published 2012-10-14 02:00:01 UTC
Last updated 2012-10-14 02:00:01 UTC

Chapter 1

Derpy Colada
By NotProud

My Little Pony: Friendship Is Magic and all non-original characters are owned by Hasbro and Lauren Faust. No copyright infringement is intended. If you paid money to read this, please report whomever you paid to the law enforcement of your country!

She had her eye on this one for some time, but in every way until now she had been obstructed. Close observation was necessary, but not too close, not to raise suspicion. That happened once before, and it was hard to talk her way out of it. But months of dedicated attentiveness had finally paid off: the cracks in the protective net have appeared.

“But Blisswing, how are we supposed to get around? Or do you forget that your wife and child don’t have wings?”

“Surfer, sweetie, I know, but momma doesn’t have long! We have to go see her!”

“I still don’t know how you expect us to do that!”

“I... I could carry you!”

A snort of disbelief. “Both of us. Really? What was your wingpower during the torrnado? 4? 4.5?”

“Look, I’ll find a way, but we can’t argue about this for very long! Don’t tell me you don’t want me to see my mother before she dies!”

“I’m sorry, Bliss. If worst comes to worst, we can always stay behind and you can go.”

“Stay behind! That’s an idea!”

“What?”

“What if Piña stays behind? We could find a foalsitter! She shouldn’t have to face death at her age anyway.”

“Well, I suppose... But where will we find a foalsitter?”

“Ahem.”

Their eyes turned toward her, curious and properly aligned.

“Hello, nice ponies!” she announced in a cheery voice. Cheerfulness would keep them off guard. “My name is Derpy Hooves and I could not help but overhearing your conversation just now! I would be very pleased and honored to offer my services as a foalsitter while you visit your ailing mother!”

The parents blinked as her words sank in. The father spoke first.

“Oh... Uh, Derpy was it? Do you have any credentials?”

“Uh-huh! I have a daughter of my very own, my little Dinky, who I raise all by myself!”

The expressions of confusion turned quickly into appreciation. They’d been won over already, they just didn’t know it yet.

“But, we wouldn’t want to impose, Miss Hooves. I mean, parenting singly can be pretty taxing, I’m sure...”

“Oh, not at all, it would be a pleasure! Dinky isn’t much trouble, and she loves having friends over to play with!”

They looked at one another. “Well, what do you think, Bliss?”

“Sounds good to me, Surfer! Looks like Miss Hooves here is just the answer we were looking for!”

She grinned wide as the mother shook her hoof. “Miss Hooves, would you kindly meet us after school tomorrow? We’ll have all of Piña’s things packed and ready to go home with you!”

“I’d be delighted to! I’ll see you both then!”

The next day after school, just as promised, Derpy stood across the street from the school, waiting for the parents of Piña Colada, and the little filly herself. Her coat was a soft pink, her mane a shade of darker pink and with a white stripe. Derpy smiled as her parents led her over to her.

“Hello, Miss Derpy!” cried Surfer. “I cannot thank you enough for offering to do this for us.”

“It’s nothing!” Derpy exclaimed cheerfully. “No problem at all!”

“But where’s your daughter?” asked Blisswing, looking around confused.

Derpy looked sad. “My poor little Dinky had to stay home from school today. She wasn’t feeling well.”

“Oh dear!” Surfer and Blisswing looked at each other. “Piña won’t get sick, will she?”

“Don’t worry about that!” said Derpy. “It was just a tummyache. Dinky will be right as rain by tomorrow and then she and Piña can play together! Won’t that be fun?” She looked at the filly as she asked the question.

“Uh-huh!” Piña exclaimed, smiling brightly.

“Now, Piña,” said Surfer, “do you have all your things packed?”

“Yes mommy, right here in my saddlebags!”

“You behave and listen to what Miss Derpy tells you, okay?”

“I will, daddy! I promise!”

Piña’s mother and father gave her kisses on the forehead as Cheerilee came out of the school house and over to them.

“What’s going on here?” she asked, looking from the parents to the foal to Derpy.

“Oh, Miss Cheerilee! Surfer and I are about to go visit my mother in Cloudsdale on short notice. Luckily, Miss Derpy here offered to foal sit for us. Isn’t she great?”

A wave of nausea seemed to pass over Cheerilee’s expression, and she swayed on her hooves a bit. She mumbled something under her breath, then said, “Um, foalsitting? I see. You know, Derpy isn’t exactly the best choice for that...”

Derpy frowned. “Miss Cheerilee...”

“I mean,” Cheerilee continued, “you two have only just recently moved to Ponyville. There’s a lot you don’t know yet about...”

“Miss Cheerilee...!”

Cheerile gritted her teeth, staring right at Derpy while she spoke, saying each word clearly. “You don’t know what she’s like.”

“Now hold on, Miss Cheerilee,” said Surfer, concerned. “Just because Derpy has a... a condition doesn’t mean she’s unfit to foalsit!”

“That’s right,” added Blisswing. “She’s got a daughter of her own!”

“And furthermore, I’m shocked that a teacher such as yourself would even think about judging another pony the way you just did! If anything, I’d say you owe Derpy an apology.”

“It’s all right,” Derpy said, a hint of sadness in her voice. “I’m used to it. No apologies needed.”

“And none offered,” grunted Cheerilee. “I see you two won’t reconsider, but don’t say I didn’t warn you.” She gave Derpy a glare, then turned and trotted back into the school.

Blisswing and Surfer looked at each other, at a loss for words.

“My goodness, what a scene!”

“Don’t worry about it,” Derpy said, lightening the mood. “You two should get going. Your little Piña is safe with me!”

“All right. Again, Miss Derpy, we can’t thank you enough.”

Blisswing took hold of his wife under her arms and, with a great deal of strain, lifted into the sky.

“Bye-bye, Piña! Stay safe!”

“I will, mommy! Say hi to gramma for me!”

Derpy and Piña waited and watching as Blisswing hauled his wife slowly toward the north. Then when they were out of sight and the little filly was tired of waving to them, they turned and moved off down the road.

“So are we going to your house now, Miss Derpy?”

Derpy chuckled. “Not quite yet. We have to make one stop first.”

The Flighty Pegasus was dark inside and smelled dusty and faintly like smoke. Piña squinted against the glaring lights in the darkness and looked up at Derpy.

“Um, I’ve never been to a place like this, Miss Derpy,” she whispered.

“It’s okay. We won’t be here long. Go find a table somewhere out of the way and I’ll join you shortly.”

“O-okay...”

She watched Piña trot off, drawing glares from the patrons. Most of them were stallions, and all of them were rough, burly looking sorts, wearing leather jackets and smoking cigars. At least one pony drew in a sharp breath when they saw the filly and then Derpy standing by the door. Derpy paid them no attention and went to the bar instead. She ordered her drinks, then joined Piña at the table.

“If you don’t mind me asking, Miss Derpy,” Piña began, “why are we here?”

Derpy smiled. “It’s a favorite place of mine to come when I meet a new friend. Also, there’s a special reason, all for you.”

“For me?” The slight fear in the filly’s face vanished, replaced by eager curiosity.

Derpy nodded. “Do you know where your name comes from?”

“Of course!” cried Piña. “It means pineapples and coconuts! I really like pineapples!”

Derpy smiled. “You’re a very smart filly. But there’s another meaning to it as well...”

“One tall porter, one piña colada,” said the waiter, suddenly appeared at their table. He set the fruitier drink in front of the filly, and her eyes widened. The concoction was white with little yellow chunks of pineapple, frozen, with lots of fruit slices and an umbrella at the top.

“Thank you,” said Derpy, and took a sip of her beer. Then, when the waiter didn’t move, she said, “Thank you,” again, with more force.

“You wouldn’t be foalsittin’ again, Derpy, now would ya?” the waiter asked, an edge to his voice.

“It’s none of your business,” Derpy huffed, and the waiter, shaking his head, moved away.

Piña was still staring at the frozen drink when Derpy broke her concentration.

“Now then, Piña, this is a very special drink that has the same name as you. And it’s made with pineapples and coconuts and all kinds of other yummy things. I thought you might want to try one.”

Piña looked at her, eyes wide with wonder. “You mean this is all for me?”

Derpy nodded. “Uh-huh. Try it, you’ll like it!”

Piña grasped the straw in her lips, pursing them, and took a huge sip.

“Mmm, it’s yummy! Although... It tastes kind of funny.”

Derpy chuckled softly. “Don’t worry about that. You’ll get used to the taste soon enough. Just focus on the yummy parts. And don’t drink too fast, you don’t want to freeze your brain!”

Piña nodded and began taking small sips while Derpy nursed her own drink. After a time, she became aware of the eyes of the other patrons on her. She scowled into her glass for a few minutes, the filly not noticing, until finally she stood, slowly, and leaned over to Piña.

“Just a moment, sweetie, Derpy has to say something to these ponies.”

With that, she whirled and faced the room.

“What?” she cried. “What are you all staring at? You think that Derpy’s stupid, huh, ‘cuz of her eyes, is that it? That she can’t have a good time with a friend without mean ponies whispering about her behind her back! Well, you can all just shove off, all right? Derpy is tired of your looking and talking and everything else!

“Who wants a piece of me? Huh?” She glared at each pony in the room, and one by one they averted their gaze.

“That’s what I thought.”

She sat back down at the table. Piña had drunk more than half of her drink by this point and eaten most of the fruit pieces.

“Are you all right, sweetie?” Derpy asked calmly. “That didn’t scare you, did it?”

“No, Miss Derpy,” Piña said, appearing unphased. “But my head feels kinda swimmy.”

Derpy tutted. “You haven’t gotten a brain freeze after all, have you?”

Somepony next to the table cleared their throat. Derpy turned a two-way glare to the waiter from before.

“Excuse me,” he said, his voice low, “but I’m going to have to ask you both to finish your drinks and leave.”

Derpy snorted, but said nothing, instead taking a long pull off her beer and slamming it on the table, just in front of the waiter’s nose, so that he got some of the tip of it. Piña happily sucked down the rest of her drink, and wobbled a bit as she got out of the booth. As Derpy shoved the waiter aside to leave as well, he grabbed her by the elbow and hissed in her ear.

“Dammit, Derpy, you don’t have to do this. Leave her alone!”

Derpy sneered. “Who’s gonna stop me? You?”

The waiter appeared to think for a moment. Then he released her and turned his head away, shamed. Derpy and Piña trotted to the exit without a backward glance.

“Miss Derpy?” Piña asked, her voice wavering. “Why did you yell at those ponies?”

“Sometimes,” Derpy said after a long pause, “mean ponies think that I’m stupid because of the way my eyes look. And sometimes I get frustrated and yell at them. Sometimes yelling is the only way to talk to ponies like them. I’m sorry you had to see that. But don’t worry. I know you don’t think that about me, right?”

“Right!” Piña chirped, then nearly toppled over. Her steps were very unsteady and Derpy chuckled, lifting the filly onto her back.

“Come on,” she said, “let’s get you home.”

As they walked through the streets of Ponyville, shutters and blinds closing. Doors swung shut. Welcome mats were removed. It didn’t matter to Derpy, though. She lived on the edge of town, at the end of a lonely road with no neighbors nearby. It was nice and quiet, just her and Dinky, just the way she liked it.

She walked up to the little brick house with the thatched roof, pulled out her key, and opened the door.

“Dinky!” she called softly in the darkness. On her back, the filly stirred. “She must be asleep.”

“Nngh, where are we?” Piña mumbled.

“Home,” Derpy said simply. “Come on. Let’s go into the bedroom so we don’t disturb Dinky.”

“I don’t feel so good,” Piña moaned. There was a hurking noise and Derpy trotted quickly to the bathroom, carrying her. She set the filly on the tile and let her empty her stomach into the toilet.

“Aww, you poor thing,” Derpy cooed. “Had too much to drink your first time.”

When she was done, Derpy wiped the filly’s mouth with a warm washcloth and then led her into the bedroom, locking the door behind her, and helped her onto the bed. It was a simple bed, with no posts or endboards, and a very plain sheet. It matched the simple surroundings of the bedroom. The saddlebags were left on the floor.

Derpy curled her legs around the filly, holding her gently, letting her body heat warm the foal.

“There, do you feel better now?”

“Uh-huh.”

“That’s good. Just rest for a bit, I’ll be right here if you need anything.”

The filly’s breathing soon became level, and Derpy found herself wondering if the anticipation wasn’t better than the actual event. The warmth of the filly in her embrace, the soft, supple body, the unaware innocence: it was making her squirm. She did her best to hold still, though, and let the filly rest a bit. But she could not deny the urge that was rising inside of her.

After ten minutes had passed, she finally gave in. One hoof stroked down the filly’s side, caressing and gentle, and after a few strokes, Piña stirred.

“Mm? Miss Derpy?”

“Right here, sweetie.”

“Okay.”

She kept up the stroking, caressing mane and body alike. She planted a soft kiss on the top of the filly’s head.

“Has anypony ever told you that you’re a beautiful little filly?” she murmured.

“R-really? No, nopony has. Thank you, Miss Derpy!”

The filly rolled over, all smiles, and Derpy smiled back. “Do you like me, Piña?”

“Yes, Miss Derpy! I think you’re a very nice pony, and it’s sad that other ponies are mean to you for no reason.”

Derpy hesitated slightly. “I know of a very nice... very special way you can show me how much you like me, Piña,” she said.

“What’s that, Miss Derpy?”

Derpy’s smile got wider as she paused, savoring the anticipation. “Give me a kiss.”

The filly didn’t even blink. “Okay!” she exclaimed, and gave Derpy a kiss on the cheek.

“No, no, sweetie,” Derpy laughed, “I meant a real kiss. On the lips.”

Piña’s cheeks suddenly flushed, and she looked to the side. “Uh... Are you sure? I don’t even kiss mommy or daddy on the lips.”

“Well, I’m not your mommy, so it’s okay,” Derpy said, placing a hoof gently on the filly’s shoulder.

Piña took a deep breath. “Um, okay... If you say so, Miss Derpy.” She closed her eyes, puckered her lips, and moved forward. Derpy met her halfway, pressing her lips to the filly’s, holding her tightly to herself and kissing her passionately, sliding her tongue into the girl’s mouth. When the filly began to squirm, Derpy released her and grinned.

“Did you like that?” Derpy whispered.

“Um... It was... nice...”

“I know lots of nice games, Piña,” she continued. “Would you like to see some nice ways to feel really good?”

Piña seemed unsure for a moment, then nodded without saying anything. “What kind of nice games do you want to play, Miss Derpy?”

Derpy smiled and said, “I’m going to teach you the difference between colts and fillies.”

“Oh!” Piña perked up. “I know that!”

Derpy blinked. “You do?”

“Uh-huh! I saw once when my daddy was peeing...” She giggled. “Boys have a thing between their hind legs, right? And girls don’t have anything.”

Derpy made a tut-tut noise with her tongue. “Now, now, that’s not true! Girls do have something! How else do you pee?”

“Oh.”

“Here,” Derpy said, shifting onto her hooves, “take a look at mine.”

She turned around, crouching and lifting her tail so the filly could see her sex.

“It’s like a big hole!” she exclaimed.

Derpy nodded. “Why don’t you take a closer look. You can kiss it if you like.”

“Umm... Miss Derpy, I’m not certain I should.” The filly fidgeted, looking down, and Derpy felt heat rise in her face. “It’s just... That’s your no-no place, isn’t it...”

“Piña.” Derpy’s tone was cold and flat. “Remember what your mommy and daddy told you.”

“Umm... What’s that?”

“They said you have to behave.” Derpy took a deep breath, saying each word clearly. “And you have to do what I say. And you listen to your mommy and daddy, right?”

Piña swallowed and nodded.

“That’s because you’re a good filly. So why don’t you listen to Derpy and give her a big kiss on her hind lips? Don’t worry about no-no places, your mommy and daddy trust me.”

“O-okay... If you’re sure...”

Derpy repositioned herself with her rear end right in front of the filly’s face. Piña leaned forward and planted her lips against Derpy’s hindquarters.

“Ooh, yes, just like that...”

Then she felt a small tongue flick out and begin exploring her insides. Derpy felt her knees begin to buckle and fought to keep herself upright. This one was a fast learner.

“Yes, yes, just like that...”

“It tastes funny,” Piña complained.

“Shhh, keep doing that, don’t stop... Yes... Nnngh! Oh, you’re such a good little filly!”

It didn’t take long for Derpy to climax all over Piña’s face. The filly gagged and drew back, sputtering.

“Miss Derpy, you peed on me!”

Derpy couldn’t help but laugh as she collapsed on the bed. “No, sweetie, that’s not pee. Don’t worry, it’s clean. Come here and let me clean it off you.”

The filly did as told, and Derpy slowly licked her own juices off of Piña’s face. The filly giggled as it tickled her.

“Am I a good kisser, Miss Derpy?” she asked.

“Yes you are! Regular kissing and special tummy kisses too! I’m so proud of you. Which is why now I want to repay the favor.”

She pushed the filly gently onto her back, and did not hesitate to begin licking between her legs. Piña squirmed and made little noises as Derpy attended her. It was so much fun, listening to their first time being touched and licked this way. They never had any idea what was in store for them.

“I-I feel so strange, Miss Derpy!”

“Hush, you’ll feel very good very soon.”

Watching a foal’s first orgasm was always a special treat. Piña squirmed and drew her forehooves up to her chest, then cried out loudly, her eyes squeezed shut.

“Didn’t that feel good?”

“I... I dunno... I feel strange... I think I peed.”

Derpy frowned, but Piña’s eyes were still closed, so she didn’t notice. “Well, I know another nice game we can play. You just wait here for a moment and catch your breath.”

Derpy hopped off the bed and trotted to her closet. Though her room was mostly bare save for a small end table with a few pictures on it, her closet was another matter. Along with a few simple dresses, her Nightmare Night costume, and coats for rainy or cold weather, there was a large collection from her past exploits. Locks of hair, hoof clippings, bits of fur all lined the upper shelf of the closet. She gazed at them proudly and thought about how soon, a little bit of pink mane would join them. Yes, the mane would do nicely. Just a small keepsake before this one went back to her parents.

Beneath the shelf was a box, that Derpy began looking through. She hummed a little song, one that tended to come to mind in these situations, as she lifted out various implements and studied them before putting them back into the box.

“Um... M-Miss Derpy?” came Piña’s soft voice. “What’s that song you humming?”

“It’s a favorite of mine,” Derpy replied without turning around. “I’ll sing it for you.

“Do you know the muffin colt...”

With a soft “aha!” she found what she was looking for. She put it on while she sang.

“The muffin colt, the muffin colt...”

She turned around so the filly could see what she had put on. It was not very long, but the black straps stood out against the gray skin on her hips. It swayed a little bit as she walked on her hind legs, using her wings for balance, and finished her song.

“Do you know the muffin colt, who lives on Derpy’s legs?”

Piña giggled. “Miss Derpy, that’s silly! It looks like you have a boy thing!”

“That’s because it is a boy thing, sweetie. Not a real one, of course, just a toy. But I’m going to put it inside you.”

Piña grew white. “W-wait, inside me? What do you mean, Miss Derpy?”

With a quick flap of her wings, Derpy rose into the air and landed on the bed

“Don’t fret now, sweetie, just lie back and trust Miss Derpy.”

“B-but that looks like it will hurt!”

“Hush now, I wouldn’t hurt you! Your parents trust me, after all.”

Panic rose in the filly’s voice. “I suddenly don’t feel very good, Miss Derpy. I don’t think I wanna do this.”

“You have to do what I say, Piña,” Derpy said, her voice growing harsh in frustration. “Remember you promised to be a good filly!”

“B-but...” Trapped between her own instincts and the words of her parents, Piña began to cry.

“Now, now,” said Derpy soothingly, “I’m sorry if I yelled. Don’t cry, sweetie. This will be fun and I promise it won’t hurt. Well, it might hurt a little at first if you haven’t done this before. But it won’t last and I double promise I’ll be extra gentle.”

The filly quietened, but continued wailing softly. Just then, the door gave a clicking sound and Derpy froze.

“Mommy?”

Derpy turned slowly, strapon bobbing suspensefully above the filly. She just saw the glow vanish from her daughter’s magic that had unlocked the door. Dinky stood there, eyes slightly glaring at her.

“H-hello there, muffin! What are you doing?”

“Help!” Piña cried. “Dinky, help, I think your mommy is a bad pony maybe!”

“She is a bad pony,” said Dinky slowly, without emotion, and she took a slow step into the room. Derpy began to sweat.

“Dinky, honey, mommy is busy right now, maybe you should come back later...”

“No, mommy,” Dinky said, her voice still level and dull. “You are a very bad pony.”

Piña’s tears broke, and she smiled with what seemed like hope. “Dinky, quick, help me and we can escape!”

“No.”

The word cut through the tension in the room like a shock to the system. Dinky kept taking slow steps in, all the while glaring at her mother.

“Mommy,” she said slowly, “you are a very bad pony because you invited Piña Colada over for secret playtimes and you didn’t tell me.”

Piña’s jaw dropped open and her eyes brimmed with tears.

“Ohhh!” Derpy laughed, still sounding nervous. “Well, muffin, mommy thought you were asleep. You can have secret playtimes with us if you like.”

Dinky gave her a quick smile, then levitated herself up onto the bed, next to Piña’s head.

“Did mommy teach you how to do special tummy kisses?”

“Yes I did, Dinky.”

Dinky spread her legs, placing them around Piña’s head.

“Then kiss me there,” she commanded.

Piña began to cry, but nopony heard it. All thoughout Ponyville, windows were shuttered, doors were locked, lights were out and ponies slumbered blissfully, their pillows bunched tightly around their ears.

(A/N: If you read this far, you have my sympathy.

Let me say that I do not believe Derpy is a child molester. I am not a child molester either, nor do I plan to be. This is just the release of much darkness from my soul as many of my stories are. I could not get this one to leave me alone until I wrote it, and it very painful to write and took me to dark places I did not wish to go.

To turn this tragedy and horror tale into something positive, I will leave for you a message.

This story happened because the ponies in Ponyville knew what was going on and did nothing to stop it. Do not be like them, dear reader. If you even suspect that a person is molesting children, report your suspicions to your local authority. They will do the investigation, even if you are wrong, and keep your name from it, but it is not worth letting a child be hurt because you were afraid or unsure.

In the same way, if you think a man has touched a woman inappropriately, if you know he does this often at social gatherings or something, and he says he is lonely or has autistic, do not listen to him. Do not give him your sympathy. No mental health or loneliness can excuse the wrongness of touching, which is akin to rape. Tell this person strongly that you disagree with their behavior, and you shall not invite them to another gathering until they change it. They may whine and attempt to gain your pity, but be strong, for the protection of others is most important.

I hope this message will help with the trauma inflicted by Derpy Colada.

I Am Not A Proud Pony

It Had To Be Done)