Twilight's Smarty Pants

by ThePhantomAssassin

Rating: mature
Tags: Sex, Twilight Sparkle, My Little Pony: Friendship is Magic, Other, Romance, Comedy
Length: 4724

Late one night while working on a mass-disenchantment spell, Twilight discovers that her doll Smarty Pants isn't a doll, but in fact a pony.

Late one night while working on a mass-disenchantment spell, Twilight discovers that her doll Smarty Pants isn't a doll, but in fact a pony. A smart one at that, and he wore pants.. Back in his day, stress relief didn't involve a trip to the spa. It usually involved a hotel room and a couple drinks.

Though a Library will work just as well, with or without drinks.

Published 2012-12-25 03:50:01 UTC
Last updated 2012-12-25 03:50:01 UTC

Chapter 1 of One (If you're lucky)

Twilight’s Smarty Pants
By ThePhantomAssassin

This is narrated by the same guy who did ‘The Hitchhiker's Guide to The Galaxy’ so when a somepony isn’t talking think his voice. Smarty Pants will be played by Doctor Emmett Brown from Back to The Future. If you don’t know who that is you are sad and you should feel sad.

Edited and Pre-Read by: J0HNS0N

Chapter 1 (Heaven help you all if there is more)

Twilight, wasn’t lonely by any terms you could place on her. She had plenty of friends all of whom she keeps in close contact with. One thing our overly studious unicorn doesn’t have in all those friends however, is a male friend. Or more to the point a coltfriend, or even just a friend with benefits.

She knew Big Macintosh, but she didn’t know him. Everything she knew about the stallion was what Applejack has told her. Not straight from the… Uh…. Horse’s mouth. There was Spike, he was guy, but he was like a little brother to her. Maybe even a son. That would be weird… There were a few guards she knew up at the castle, but they were married, or in a few cases, gay.

That was every male she knew. Discounting her actual brother Shining Armor. So what was a mare like her to do when it came to comforting herself? Clop? Sure, why not. How long does it last before that doesn’t cut it anymore? Before it doesn’t fully tend to the garden? Before it doesn’t scratch her itch? You get the idea.

She needed an actual stallion to scratch her itch. Tend to the garden. I’m repeating myself. Sure, she could use magic, but that would be like putting a band-aid on a bullet wound. It might stop the bleeding, but it doesn’t solve the fact that there’s a lead slug in your ass. Assuming that’s where you were shot. What kind of psycho would shoot someone in the ass…?

Nevermind… I don’t think any of us needs to know. Anyway, that’s the setting, that’s her dilemma, onto the story yes?

[Horizontal Rule thing.]

Twilight was studying in her room, at her desk. Her Smarty Pants doll, which she had to re-acquire from a workhorse who shall remain nameless, was sitting in the back corner of the desk watching her work like a creepy ass stalker. Well, as it turns out, that’s not far from the truth. Inside the doll was a sentient pony that has been trapped in the doll that Twilight’s dad found at a garage sale.

What happened to him that put him in that form? Well, he tells Twilight in a little bit, so you suck out for a while.

Twilight was working to create a new spell that would dispel many spells and enchantments at once, instead of one at a time. That way one could theoretically save time removing the enchantments on multiple items you wanted to re-enchant instead of dispelling the old enchantment one by one wasting time. We all know how Twilight likes her efficiency.

She was going use a pulse of magic to dispel the enchantments on many items at once. I should also mention that Spike is conveniently away at a sleepover with the Cutie Mark Crusaders at the Clubhouse. Twilight had run the calculations a few times to make sure everything was ready. She had several items that were enchanted to test if the spell really worked. All with little ol’ Smarty Pants in his little blue polka dotted pants watching.

“Okay!” Twilight said. “Here we go, final check list check. Calculations checked? Check. Formula for the spell? Check. Items for enchantment testing to see if they’ve been disenchanted? Check. Alright, times up, let’s do this.” Twilight’s horn glowed her magenta magical color as she prepared the spell. The magic around her horn bobbed and weaved like the oceans the spell weaved itself around her horn so it would do as it is instructed.

When it was ready, she let it go. A magenta shockwave, pulse, magical wave thingy burst from Twilight’s horn. Disenchanting every item in the room. Including the doll, although nothing happened to it at first. Twilight’s spell ran its course and she went around and checked the items to see if it worked. And it did. “Yes! It worked! I can’t wait to tell the princess!” As she documented the results from the test, the doll on the desk started glowing. She of course noticed as soon as it started.

No I’m bullshitting you. She didn’t notice until it was over powering the full moon that was shining in through the window. It also out did the candles.

“What the deuce is that light?” Twilight asked the empty room as she looked up at the doll. She lifted her hoof up to shield her eyes from the light ~~of creation~~ of the doll returning to its original form. The expanding doll fell off of corner of her desk into the ill-placed trash can that is about to explode like a really fat guy who hasn’t eaten in a few days that happened to teleport into an all you can eat buffet.

Twilight wasn’t doing anything besides watching this incredibly bizarre scene unfold before her. The doll was emitting a faint noise. If one strained their ears, they might call it screaming. Which it is, but we find that out in a minute. The doll has filled up the bottom of the poor trash can, and said trash can was bulging outwards. Had we been able to hear the inanimate object speak, he would’ve said this.

“What is this? Twilight’s doll? (We are assuming he can hear.) Why would she throw this out? Why is it glowing? (We are also assuming it can see. Somehow…) It’s expanding? I’m already quite full thank you. Please stop. Stop. Stop. Please! It’s starting to hurt! No! No more please! Aaaa!!” The trash can exploded outwards. The remnants of its container making a tragically small mess from the loss of what was a very nice guy. He was Steve. I bet you didn’t even care to ask his name till I told you huh? You should feel bad....

As the doll expanded into a fully fledged pony size, the screaming could be clearly heard. When he finally stopped expanding, he stopped glowing. He kept screaming though. Probably quite the painful experience. Can you imagine the stiffness that comes from being an inanimate object for one-hundred and ninety eight years? Not to mention the pain of expanding in general. Anyway! He stopped glowing and proceeded to keep screaming as he rolled around on the floor steam rising from his new body. Well, newly reacquired body.

Twilight’s thought’s on this matter was a simple sentence. “What the hell did I do this time?” Sooner or later more rational thought re established itself as the dominant thought in her brain as she processed the fact that ‘Hey! That stallion in front of me was my doll and he seems to be in a large amount of pain! I should do something!’

So she did. Or tried to anyway. “Ohmygosh! Here let me help!” Twilight walked over and knelt by his flailing and rolling form to cast a healing spell. His body rolled right into her horn. His hooves jumped to the stabbing sensation of his side as he started screaming with renewed vigor. “I’m so sorry! Hold still I’ll to help!” He rolled away from her after she jabbed him with her horn, so as Twilight got back up to go over to help, he rolled into her legs, and knocked her right on top of him.

“Goddess damn it! You aren’t helping! Go stand over there for a minute!” He shouted. Twilight sheepishly stood up and walked away from his writhing form. He stopped screaming, but was now hunched over in pain. Twilight cast a spell to take the edge off the pain. From where she was standing, not trying to jam her horn into his chest cavity. Why didn’t she do this before you are probably asking? Hell if I know. Ask Twilight not me. I’m just writing this.

Smarty Pants fell over to his side and just panted heavily. I’m sure you are probably also wondering why nopony else heard his screaming yes? Well Twilight’s neighbors complained about the noise she sometimes made in the middle of the night during her research and experiments, she so put an enchantment on the entire library to prevent sound from passing out of it. But wait! Why didn’t it get dispelled? Well the dispel spell didn’t encompass the entire tree that is the library. Convenient because sooner or later Twilight’s going to be the one screaming isn’t it? Albeit for a different reason.

“Who are you?” Twilight asked.

“I am Smarty Pants.” He replied standing shakily onto his hooves. “I am a master of alteration and transformation spells. Permanent spells. The fools up in Celestia’s damned school doesn’t believe that’s possible, but I plan of proving them wrong!” It is at this point he got a better look around and noticed. “This isn’t my laboratory… Where are we?”

“My library. In the town of Ponyville.”

“Ponyville? Impossible. Ponyville hasn’t even been formally recognized as even a settlement, much less a town. It’s nothing more than a bunch of fools in tents trying to grow an apple farm to sustain themselves. There’s no way to grow Apple trees fast enough to sustain them. I ask again, and no lies or I will turn you into doll with the spell I’ve created that will thrust me to the top of Canterlot’s scholars.”

“What’s the date?”

“What do you mean? It’s July 16th 879. What kind of librarian doesn’t know the date? I weep for the ponies of this town.” Twilight started pacing saying ‘Oh no’ over and over and over and over and over and over again. “What’s your problem?”

Twilight sighed and looked Smarty Pants dead in the eyes. When she noticed “You have a red eye and a blue eye.”

“Yes, I know. Going to make fun of me? No pony will miss a librarian who can’t keep the date…” He threatened. Quite the guy isn’t he? Rude bastard.

“No, no I just didn’t notice until now. What is the last thing you remember?”

“What an odd question. I will humor you. Last thing I remember before waking up here was preparing to cast my masterpiece of a spell which was going to turn a lab rat into a doll until the enchantment was dispelled. When the fool next door blew something up with his alchemy again. What kind of mare names her foal Edward anyway? There was a blinding light, a searing pain all over my body, and then I was here. Why?”

“Because the date isn’t July 16th 879. It’s November 14th, 1002. You’ve been in the form of a doll for hundreds of years.”

“Preposterous. That would mean that the Mare in the Moon would’ve returned and brought about night time eternal. And you are much too relaxed to have existed in eternal night for two years.”

“Nightmare Moon. She tried, but my friends and I became the bearers of the Elements of Harmony and defeated her purging her hate and spite transforming her back into Princess Luna. Princess Celestia’s little sister. I’m the bearer of the sixth element. The Element of Magic.” She said this all with a straight face while she looked Smarty Pants in the off colored eyes.

“My goddess… You aren’t lying, are you…?”

“I’m afraid not…”

Much to Twilight’s surprise, he started laughing. “Excellent! That means it worked! My spell worked like I thought it would! Take that you old hopefully dead bastards! I was right!” He spent the next few minutes using fancy words relevant to magic and many words too large and complicated for me to spend time looking for them to make the story better. Twilight understood all of it though, and that’s all that really matters.

“Oh wow. That’s ingenious.”

“Wait, you understood that?”

“All of it.”

“Who are you, really?”

“My name is Twilight Sparkle, I am widely accepted as the most powerful unicorn in Equestria behind only the Princesses. I am also the personal student to Princess Celestia herself.”

“Really? So you are incredibly smart, and good looking? Quite the fine mare indeed.” Twilight blushed at that.

“So you don’t care that I’m really close to the princess? Most stallions only see me for my connection to her…”

"Why should it matter? I’m not sure how things work now but back in my day, ponies who went after other ponies did it for two reasons. Sex, and love.”

Twilight blushed heavily at his casual speech about a touchy subject as sex. “How can you talk so easily about such a thing?”

“Are ponies nowadays really such prudes? Seesh. Back in my day it was good stress relief. Only the ones who did it solely for pleasure were looked down upon as time wasters and a weight upon society’s shoulders. Ponies with high stress job were often found at bars looking for a little stress relief.”

Twilight being the oh so curious mare wanted to know more. One thing she liked in particular was the fact that sex didn’t seem to be a big deal for Smarty Pants. Which was good since Twilight was quite stressed as it were.

“Something the matter Twilight?”

“Hmm?” Twilight was lost in thought thinking about the possible situations she could find herself in. Naughty pony. “No, not really. Just thinking.”

“About what? Your studies been stressing you out lately? Hrmm” Twilight much to Smarty Pants’ delight didn’t catch the emphasis on stressing, which indicated she was in fact, stressed. Or completely clueless.

“Yeah, making that spell took a lot of work and research. Tons of calculations. Now that it’s done, I can relax and unwind. The spell worked even better than I had hoped! If you are any indication.”

Smarty Pants smiled a sly smile. “Would you like some help relaxing Twilight? I’ve been told I’m quite the masseuse.”

“Oh! That sounds wonderful!”

“Go ahead and hop up onto your bed and lay down on your belly. I’ll get started on your shoulders.” Oblivious Twilight nodded and smiled happily as she hopped onto the bed and sprawled out onto the bed on her stomach. Smarty Pants walked up onto the bed and sat down just behind Twilight’s hips as to avoid sitting directly on her.

He bent over and rubbed his hooves together as he started working on Twilight’s shoulders. “Quite tense. Have you ever had a massage before?”

Twilight gave out a throaty moan as Smarty worked his magic on her shoulders. “Mmmm… Once or twice. Not- Oh yes… Not recently however.”

“I can tell. Your muscles are tense and firm. Several knots. I haven’t even gotten to your back or flanks yet.”

“M-my flanks?”

Smarty Pants leaned further over to Twilight and whispered in her ear. “Oh yes… I’m going to leave you in a state of relaxed bliss…” He laughed as he felt her shiver beneath his hooves.

“I don’t think I’m comfortable with that…”

“Don’t worry. Think of it as me repaying a debt for you freeing me from the dolls form. You said you were stressed yes? This will help you relax. Not to mention with as much as we have in common, I have a feeling we will become fast friends. Who knows, maybe it will lead to more?”

Whether he knew it or not, the thought of possibly having a coltfriend and her own very special somepony really appealed to the young unicorn. All she’s had for long term company discounting her recent acquisition of five friends is Spike and her brother Shining Armor. Spike was like a son to her, and Shining Armor was her brother. She didn’t like the thought of turning to her brother for sexual relief (Much to the authors dismay. WINcest FTW [And PRINcest]{Within the pages of a story.}])

While Twilight was thinking this over, Smarty Pants has moved down to her lower back. “How are you feeling?”

“Better than I have in a long time… You really are quite the masseuse, you weren’t just bragging.”

“It’s simply what I’ve been told.”

“Well they weren’t exaggerating. Not in the slightest.”

Smarty Pants couldn’t help but smile at the praise he was receiving. While from Twilight’s point of view it’s been hundreds of years since he’s done anything, from his point of view, it was literally yesterday. So his skills were sharp as a lego mine that is awaiting being stepped on. Twilight was putty in his hooves, she just doesn’t know it yet.

Smarty Pants at this point has moved down to Twilight’s hips and thighs working the knots out of those areas. Paying particular attention to her cutiemark. She was moaning and squirming beneath his skilled hooves, her tail occasionally flicking about in agitation.

“Twilight?”

“Hnn… Y-yeah?”

“Perhaps you’d be interested in a little more to help you relax? I can’t help but notice how you seem to be a little excited at the moment and as it’s my fault from the looks of things, I’d like to take responsibility.”

Twilight looked up at him. The lack of an immediate response means two things. Either she was considering it, or she was so shocked by his blunt question that her mind hasn’t caught up with the spinning wheels. Her eyes were searching his for hints of deception of any kind of unpleasant thought that could even remotely be considered negative.

Finding nothing but kindness and a genuine desire to help her, she came up with an answer. “Okay. Just… Be gentle okay? I know that it’s clichéd but it’s my first time…”

“Really? Well, then after this how would you like to go out for dinner? I don’t know how things work here but when someone agrees to some stress relief even though it’s their first time, it’s customary to take them out to dinner and see if it would be possible to have some kind of relationship.

Though from one scholar to another I don’t think that will be a problem once we get to know one another.” Twilight was shocked to say the least. If her open mouth and wide eyes said anything. Here he was, this strange stallion old enough to be her father’s father in terms of age about to rut her because Celestia damn it does she need it, and now he’s asking if she’d like to start dating for a while! And you know what? She liked the idea.

“That’s sounds lovely Smarty Pants! A little backwards from my point of view, but I’m used to strange happenings around here.”

“What do you mean?”

Twilight could only laugh. “I’ll tell you at dinner. For now, I do believe you have some work to do…” Towards the end of that sentence, Twilight lidded her eyes and tried to sound sexy, and seductive. For the most part, she succeeded.

“Very well. Roll over onto your back if you please.” Twilight hesitated, but after a short while she complied. Smarty Pants backed up a bit and gave her room to roll over. When she did, he crawled on top of her and brought his face to hers.

He looked into her eyes as if asking for permission to kiss her. A point made clear as he started bringing his face closer to hers. Twilight closed her eyes and leaned her head up granting him his permission. Then he connected his lips to hers.

Nothing fancy at first; just a simple kiss. From Twilight’s point of view, it was electric. It was her first kiss with somepony she felt she could safely call her coltfriend. She felt his lips pressed against hers and every nerve in her lips were telling her two things. First, they were softer than she expected, and the second was that it felt great.

There was more to come however, oh so much more…

Smarty Pants lifted up and smiled warmly at Twilight’s expression. He bent down and kissed at her neck, sucking gently and licking at her in a show of affection. Much to his chagrin he was finding himself quite enamored with how he was making her squirm beneath him. She really was cute when you stopped to admire her...

After a minute of teasing her neck he started heading down south to her moist marehood.There was a saying though, it’s not the destination, but the journey. On the way, he needed to make a stop. Along the way to the promised land, he stopped by the mammary mountains that are Twilight’s breasts.

He took one of her nipple into his mouth and started sucking on it gently while biting down on it enough for her to feel his teeth. He wrapped his forelegs around her hips to prevent her from moving around too much.

Twilight’s mind couldn’t process what was happening. It infact gave up shortly after Smarty Pants kissed her. So there’s no way it could process the lightning bolts of pleasure surging up her spine as he licked and lapped at her tits. Or the longing sensation between her thighs she couldn’t hope to deal with on her own at this point.

When Smarty Pants was done there, he moved further down to the crown jewel. He brushed his teeth against her aroused clit which caused Twilight to let out a high pitched little squeak as her body tensed up with a sudden orgasm.

Smarty Pants felt his chin get hit by her bodies sudden ejection of liquid from her cunt. “Twilight. Let me know next time you are cumming. I was looking forward to getting a taste...” He said with a husky tone

Twilight was panting for breath, gasped out an answer regardless. “S-sorry... Didn’t e-expect that... So good...”

Smarty Pants only smirked up at her from between her parted thighs. Only for a second. He lowered his muzzle back down and licked right up the center of her snatch. Twilight let out a deep throaty moan as he passed from top to bottom and back to the top again.

Without warning, while Smarty Pants was over the entrance to her cunt’s cave her thrust his tongue in and started swirling it about. Twilight arched her back and squirmed as she tried to cope with the awesome amounts of pleasure she was receiving. Smarty Pants was actually having a tough time holding her still.

He pulled his tongue out and started running it around her slit like a race track. When he got the the top of her pussy he flicked her clit for added stimulation.

“C-Celestia damn it! Smarty Pants! Give it to me!” Twilight begged, desperate to have something fill up the void within her.

Smarty Pants got up from between her legs and crawled on top of her panting form. Sweat matting both of their coats. He looked into her eyes. “Are you sure about this? There will be no going back.”

“I’m sure. Quick like a band-aid please...” She asked as she looked up at him. Her ears folded back against her head.

He leaned down and rested the side of his head against hers in a comforting gesture. “Don’t worry. It won’t hurt for long. Maybe a minute. I’ll be here for you. Okay?”

She relaxed a bit, much to his relief and nodded. He magically removed his pants, lifting both legs to completely removing his pants. He erection was exposed now, and Twilight could get a good look at it. It was above the average size for stallions of Twilight’s era. Relatively thick as well. All in all, it was a big dick. All for her...

He put the tip of his member against Twilight’s marehood. Smarty Pants leaned down and kissed Twilight. He tilted his head a little to make better connection. The kiss never went beyond a simple kiss. There wasn’t any tongue or anything like that. It was a passionate kiss meant to help ease Twilight’s nerves.

He pushed the tip inside, felt Twilight moan into his mouth. He took a deep breath prompting Twilight to do the same. Then he pushed. With a swift motion he shoved his way deep into her waiting cunt tearing through a minor resistance half way in.

Twilight clenched her eyes shut as she let out a few muffled sobs from clenched teeth. A few tears squeezed by her eyelids. Smarty Pants nuzzled the side of Twilight’s head while he whispered, “It’s okay... I’m here... You’ll be fine... You’re doing fine...” as he tried to comfort the hurting mare.

After a little while she began to relax as her body adjusted. “Okay...” She said. “I’m okay now. Just... Move slow at first, okay? Please?”

“Alright. I will. You’re being very brave Twilight. This is where it gets good however, so brace yourself. Intense pleasure you are not accustomed to is coming.” Smarty Pants to to help to mood with a little humor and for the most part it worked.

“Yeah okay bud.” She said laughing a little. “Just take it easy. Still stings a bit.”

Smarty Pants looked down at Twilight with a fond smile upon his lips. “Don’t worry. I will.” He started pulling out and let out a throaty moan as Twilight’s pussy clenched down upon his retreating member.

Twilight gasped as nerves never before stimulated were subjected to over stimulation creating a feeling she was indeed not accustomed to. Her entire body went stiff and her back arched as he plunged back into her. “Dear goddess’!”

“Yeah. I have that effect on mares.” Smarty Pants said. He was promptly rewarded with a slug to the shoulder. He laughed as Twilight screwed her eyes closed as he pulled back and pumped into her in a quick movement. Seeing as how Twilight wasn’t crying out in pain, but instead in pleasure, he continued pumping his hips back and forth back and forth back and forth back and forth. Like a swing set.

It wasn’t to last long however. Between the crazy electric shocks Twilight’s spine is sending to her brain and the fact that Smarty Pants has been crazy aroused since the beginning of this whole sexy ordeal they were both rapidly approaching climax.

“H-hey Twilight.”

“Y-yes?”

“I’m getting. Hng... Kinda close to cumming here... Your b-body your call. In o-or out?”

“W-well. Based from w-what I’ve read. And- Ah! And other v-various-”

“Twilight!”

“In! Definitely in!”

Smarty Pants leaned down and kissed Twilight passionately on the lips not hesitating to shove his tongue into her mouth in a heated battle for oral dominance. Which he won. Twilight simply didn’t have the experience to beat him at his level. She’d need to grind some more to catch up. And he’d be more than willing to help. Guess he isn’t so rude when you got to know him. Or screwed him. Whatever cums first.

The kiss, as it turned out, was the straw that broke the proverbial camel's back. Don’t want to break any actual camel's back after all. He gave a few more desperate thrusts before he came. It was glorious. His cock fired deep into her waiting cunt causing Twilight to cum at the same time.

Twilight’s pussy walls flexed and pulsated milking his member for all it’s worth as they both ascended to the heavens is mid-coitus bliss.

What cums up, must cum down however, and soon Smarty Pants found himself spooning Twilight from behind as his dick retreated into its sheath. His forelegs wrapped around Twilight’s body, her head just beneath his. “You know something Twilight? I know this is going to work out now. No doubt about it.”

“You were always my favorite toy when I was younger. Always were ‘my’ Smarty Pants.”

Author's Note

My friends showed me a YouTube video (Linked below) and the top comment on said weird ass video was “Twilight x Smarty Pants?” well being the clop writer I am, they laughingly suggested I write a story about it. Jokes on them, cause here it is.