How To Best A Pegasus

by KillerChainsaw

Rating: mature
Tags: Diamond Tiara, Slice of Life, My Little Pony: Friendship is Magic, Romance, Scootaloo, Sex
Length: 4972

When certain secrets are in serious danger of being leaked, desperate times, call for desperate measures.

Being a growing female pre-teen is hard for Diamond Tiara , and it's even harder when she has to keep a certain secret hidden from everyone else.

However after going back to find something in the classroom one day, Scootaloo stumbles upon this little secret of her's, and decides to use it to her advantage. After many pleads the pegasus agrees to keep quiet about what she saw under one simple condition...
...can the earth pony 'best' her?

(Contains: Pre-teen Diamond Tiara and Scootaloo, 'besting' each other in the classroom :raritywink: )

Published 2017-02-07 16:50:01 UTC
Last updated 2017-02-07 16:50:01 UTC

Maybe A Little Difficult, But Not Impossible

After what seemed like a particularly long and tiring day for most of the young pre-teen students of the school in Ponyville, the bell had finally rang and their teacher had dimissed them, as they were all more than happy to set off back to their homes on this hot summer's day.

"Phew, finally got out of there, am not sure why, but I just couldn't concentrate today," Apple Bloom sighed as she and Sweetie Belle stood outside of the school house, while all their other classmates came running out of the the small school, as most of them headed off for their homes.

"You're not alone there, I don't think anypony could work while being cooped up in this heat," Sweetie Belle agreed not understanding how their teacher could expect them to work while being in such heat in the middle of summer.

"At least we've only got a little while longer here, right?" Apple Bloom smiled, lightening the mood a little.

"Yeah I guess, after our last few tests are finished, school will be all over and done with for us," Sweetie Belle, smiled back, knowing that even though their days of school had been quite difficult lately, it would all be over soon, and none of them will have to worry about school or tests ever again.

"Hey guys, do you know where my cap that Rainbow Dash gave to me is?" Scootaloo asked as she came running up to her two friends, seeming to be in quite the panicked state, and she frantically turned her head in all directions, wanting desperately to find her missing item.

"Ya mean the one ya were carrying around everywhere with you today?" Apple Bloom asked with a slight smirk, as she thought about how the orange pegasus had been holding onto that cap like it was some sort of saftey blanket for her, even though she may have been a little old for such things now.

"Didn't Miss Cheerilee take it away from you, when you refused to take it off eariler on?" Sweetie Belle asked.

"You're right, thanks Sweetie Belle, I'm going to ask if she still has it," Scootaloo excitedly began to ran off back to catch their teacher before she started heading home herself.

"Do you want us to wait for you here?" Sweetie Belle called to the pegasus.

"No, you two go on ahead, I need to meet up with Rainbow Dash afterwards anyway," Scootaloo answered as she waved to the other two poines, and picked up her speed, while Sweetie Belle and Apple Bloom just shrugged their shoulders, and started to walk back to their homes together.

Meanwhile Scootaloo had luckily been able to just catch their teacher, before she had started to leave for her home, running up to the mare, Scootaloo skidded to a halt once she was close, as she stood with an innocent smile.

"Miss Cheerilee, can I ask you something?" Scootaloo asked, as she was able to catch the older mare's attention and stop her in her tracks for a moment.

"Oh of course, what can I help you with Scootaloo?" Cheerilee asked kindly to her student, smiling politly to the pegasus.

"Can I have my cap back now please?"

"Ah yes, I said you could have it back after class didn't I? I think I left it behind my desk, it should still be there," the mare thought out loud, as she turned to go and head back into the now empty school house, before Scootaloo stopped her.

"It's okay I'll go get it," Scootaloo quickly stated, wanting to hurry and grab the cap, before she had to run off and meet up with Rainbow Dash.

"Okay, but don't let me catch you wearing it again, after all I've already told you to not wear it in school," Cheerilee warned as she gave the pegasus a slight stern stare, to let her know that she wouldn't think twice about confiscating that cap again, if Scootaloo decided to disobey her a second time.

"Yes. Of course Miss Cheerliee," Scootlaoo nervously nodded with a smile, being sure to do as her teacher said this time, as she was sure that there would be no doubt her cap would be taken away for longer, if it would happen to get confiscated again.

"Good," Cheerliee replied to Scootaloo with a smile, nodding to her, before she waved a goodbye, and started to head to her home again. Scootaloo waving to her, with a nervous smile still all the while.

She waited til her teacher had left, and by now all of her classmates had vanished from the school as well, leaving Scootaloo as the only one there right now. The pegasus sighed heavily, as she smiled and turned to go back into the school house, walking up the steps, and slowly opening the door. Slipping into the classroom, and walking behind the teacher's desk, as she searched for her missing treasure.

Her eyes lighting up as she smiled happily, seeing the old cap that Rainbow Dash had lent to her, picking it up and hugging it close to her chest, more than glad that she had been able to get it back, after all she was a little afraid of what the cyan pegasus just might say to her if she had lost something that she had given and trusted her with.

Scootaloo sighed with relief, as she held the cap close to her, certain that she wasn't going to let go of it again, until she was able to return it to Rainbow Dash. Deciding to just quickly head out of the school now, Scootaloo turned towards the slightly ajar door, thinking that she could probably catch up with Apple Bloom and Sweetie Belle if she was fast enough.

However as she went to leave for the door, something stopped her in her tracks. Standing still, her ears twitched to the sound of an odd voice that was awfully quiet, but still noticeable. With a confused expression Scootaloo looked around the room, turning and walking towrds where she could hear the quiet voice coming from every now and again, stopping as she came to the last row of seats in the classroom, and could hear the slight voice louder now, as it almost sounded familar to her.

Looking past the rows of chairs in the classroom, Scootaloo was speechless, her cap dropping to the classroom floor, as her lavender eyes fell upon a certain light pink earth pony tucked away in the corner of the classroom, her breathing coming out in heavy pants, her eyes shut tightly, her fur coat looking damp with sweat, her mane in an untidy manner, and her hoof resting inbetween her legs, as it moved in a fast motion, while small moans were escaping her lips.

Since the earth pony hadn't seemed to notice the pegasus standing there just yet, Scootaloo slowly swallowed, as she walked up to the other pony, and wondered just how long it would be before the panting pony would realise she was being watched right now. Seeming to still be lost in pleauring herself, Scootaloo blushed a little, before she called out to the earth pony in a whispered tone.

"Diamonds?"

The pegasus questioned, calling the earth pony by the nick-name she had given her, and had started calling her by not too long ago, as she moved closer to her again, and stood with her eyes still wide from seeing such a sight, as one of her friends touching herself in the empty classroom.

Hearing a familar voice whispering out the nick-name that a certain pegasus had started calling her by as a way to tease and get on her nerves, Diamond Tiara opened her eyes slowly, before they widened, and she automatically sat up straight, moving both of her front legs, so that they were covering her soaked sex, while she tried to slow her heavy breathing down.

"S-S-Scootaloo? W-what are you doing here?!?" the earth pony asked in a raised voice, her face turning to a deep crimson colour, as she bit her bottom lip a little.

"Couldn't I ask you the same question?" Scootaloo asked back as she sat down in front of the other pony, still blushing slightly as she glanced to the earth pony's covered crotch.

Diamond Tiara turned her head away from the pegasus, as she avoided looking at her, slightly squrming against the wall, she was obviously still very much aroused at this point.

"I didn't know you were into these kind of things,"

"W-what kind of things, what are you even talking about? I-I wasn't doing anything!" Diamond Tiara stated in a rushed voice, as she tried to think of some kind of excuse, but none were coming to her at the moment, as her mind was already blank from how close she was to making herself climax a few seconds ago.

"Really?" Scootaloo moved closer to Diamond Tiara again, as she slowly reached out her hoof, and pressed it against the earth pony's front legs, causing her to tremble and let out a small moan, as she could feel the back of her front legs rubbing aganist her soaked folds,

"Then why are you acting like a pony who has just been pleasuring herself? You're already drenched right, just how close were you before I interrupted you?" Scootaloo now smirked as she thought she could tease the earth pony with this a little.

"S-shut up,"

Diamond Tiara said in a low tone, trying to slow her breathing down again, as she cursed herself for letting Scootaloo catch her like this, knowing that she wouldn't hear the end of this now, as even though the two were friends, the pegsus had an annoying tendency to tease and really push her buttons.

"So is this why you always ask Miss Cheerliee if you can stay behind and 'study', just how long have you been doing this for?"

"...not long,"

"Imagine what the other poines in our class would say if they saw you like this," Scootaloo thought out loud, only speaking hypothetically really as she chuckled at the thought slightly.

"P-please don't tell them Scootaloo, nopony can know, please I'll...I'll do anything,"

Diamond Tiara pleaded as she hated the fact that the pegasus had found out her secret, but now she was scared for the chance of her telling their classmates about it, if that happened it would all be over for her, her secret would be no more.

Scootaloo was going to agree to keep this as a secret at first, opening her lips to assure the earth pony that she wouldn't go and tell anyone else about what she had seen, but after she saw how much the normally high class acting pony was now pleading to her, desperately not wanting to let her little secret get leaked, the pegasus got an idea and smirked again.

"Hmmm, you'll do anything?" Scootaloo questioned with a raised eyebrow to the earth pony.

"If it will make you keep quiet about this then, yes," Diamond Tiara nodded, wondering just what the pegasus would want her to do, in order for what she saw today to be kept as a secret, and hoping that it wouldn't be too embarrassing for her.

"Okay I'll keep my lips sealed about this, if you can 'best' me," Scootaloo smiled as she thought she could use this situation to her advantage, after all she could see that the earth pony was still awfully aroused, and seeing her masterbating by herself, had actually turned the pegasus on a little.

"Best you? What do you mean?" Diamond Tiara asked as she was both confused and scared for just what Scootaloo was planning here.

"Well if you can make me cum before you do, then I'll act like I didn't see anything and keep quiet, however if you end up cumming before me, then I might just tell the rest of our class about your secret," Scootaloo explained as she leaned into the earth pony, waiting for her to answer.

Diamond Tiara didn't know how to reply as she definitely didn't want her secret getting out, but she also was unsure if she should really let herself be ropped into this as she thought that perhaps the pegasus was just teasing her again, and wouldn't actually go through with this little 'game' of her's.

"S-Scootaloo we can't do something like that,"

"Why not? You seem to really need it right now, and you said you would do anything right? Or do you want me to tell everypony in class about your little secret?" Scootaloo whsipered into the earth pony's ear her voice dripping with desire and lust, as she caused Diamond Tiara to shiver and blush deeply.

Diamond Tiara felt like her mind and body were at war with each other, she knew agreeing to this wasn't a good idea, but at the same time she couldn't risk her secret being found out, plus she could still feel her core begging for more attention, as she had denied herself the release that she had been and still was craving for.

"So Diamonds, what will it be?" Scootaloo asked as she slowly licked the earth pony's ear, and caused her to tremble all over, while a small moan escaped her lips.

With a heavy, defeated sigh, the earth pony eventually gave in.

....

Scootaloo now lay on the classroom floor, with Diamond Tiara laying on top of her, their lips locking in a heated kiss, as slight moans could be heard from both of them, their tongues twisting and turning in a passionate way. Both of them feeling out of breath as Diamond Tiara forced her tongue further down the pegasus's throat, before their lips parted, and Scootaloo panted heavily, her body trembling while she was still giving out small moans.

"You're quite weak to kisses huh?" Diamond Tiara thought out loud, as she watched the pegasus recover from the deep kiss, gaining a slight shrug from Scootaloo as she just smiled back up to the earth pony, the two leaning in for another kiss.

Scootaloo let herself relax as she didn't mind the earth pony getting the upper-hoof on her, after all her being the more domiant one wasn't part of the deal, as long as Diamond Tiara could make her cum before she herself came, then her secret was safe, and the pegasus didn't really seem to care what the other pony did to her at this point, as their deep kiss continued and they're moans matched one another in volume.

While focusing on the pegasus's weak point, and kissing her deeply, Diamond Tiara let her hooves wander freely to wherever they felt comfortable, running down the other pony's body, and following along the feathers that spread out to her small wings, going slow as she softly caressed her fur.

As her hooves traveled down to the uderside of the pegasus's wings, and the earth pony got a little bit more firm with her touches, Scootaloo suddenly shivered all over and let her voice get a little louder, biting down on Diamond Tiara's bottom lip, before their kiss was broken and she panted heavily again, while Diamond Tiara seemed a little surprised by Scootaloo's reaction just now.

Diamond Tiara gazed down to the pegasus, as she slowly stroked the underside of Scootaloo's wings with both hooves, taking note to the fact that when she stroked the left one, there was much more of a reaction from the other pony. Watching the pegasus's reactions to her touches closely, Diamond Tiara slowly stopped stroking her right wing, and instead just focused on stroking her left one, as she would slowly travel her hoof down to the underside of the wing every now and again, running her hoof along each and every feather ever so softly.

Scootaloo lay moaning, as her body would shiver and shake with every slight stroke, biting her bottom as she struggled to keep her voice quiet, while she continued to squirm underneath the earth pony, blushing deeply as every little touch sent shockwaves through her body.

"You're left wing is awfully senitive it seems, especially on the underside,"

Diamond Tiara commented as if she was talking to herself more than Scootaloo right now, leaning down as she watched the pegasus shake and squirm in reponse to every little thing she did to her left wing, licking her feathers lightly, while listening and actually starting to like hearing every small moan that would leave the other pony's lips.

"I wonder what other parts of your body are weak," the earth pony let herself smile for a moment, actually feeling like she had the control here, as she ran one hoof down the rest of Scootaloo's body, searching for more of her weak spots, while she was still lightly stroking and licking the underside of her left wing.

Scootaloo felt like fighting back, but simply just let Diamond Tiara still do whatever she wanted, after all she seemed to be so into this right now, she didn't look like she was going to just stop at any time soon, and to be honest at this moment in time since the earth pony was going after her senitive spots, there wasn't a lot she could do.

As her hoof traveled further down, and then would move to run back up the pegasus's body, Diamond Tiara noticed something each time that she would pass over Scootaloo's stomach, she's didn't shake or shiver anymore, and her moans were now much quieter it would seem, as everytime her stomach was stroked she would relax, and seem to completely submit to the earth pony laying on top of her, causing her mind to slowly go blank, and her heart to beat just a little faster.

Diamond Tiara slowly caressed Scootaloo's lower abdomen, her hoof traveling up to run over her stomach every so often, watching as her slight touches caused the pegasus to melt underneath her, smiling more as she was actually starting to enjoy this, 'She's cute,' the earth pony thought to herself, as she gazed down to Scootaloo's blushing face, and was lost in her cute reponses, never relising how senitive a pegasus like her could be.

"You know if you want to make me cum, this isn't the way to go, the least you're doing is simply stirring me up," Scootaloo stated with a slight smirk, seeming to be still able to speak without pausing anywhere, even though it was clear to see that she was very much turned on right now, and was just asking for more attention from the other pony.

"What do you want me to do then?" Diamond Tiara asked as she stopped for a moment, and sighed, blushing as she didn't feel like she could look the pegasus in the eye for more than a second anymore.

"Well could you get off me for a minute?" Scootaloo asked as she smiled up to the earth pony. Doing as she was told after a short pause Diamond Tiara stepped off of Scootlaoo and instead just sat down beside her, while the pegasus sat back up on the classroom floor and moved closer to her again, leaning into her as the two kissed, both of them blushing a little.

As their lips parted Diamond Tiara sighed as she turned her head a little and avoided looking to Scootaloo, her blush growing deeper as she could still taste the pegasus on her lips, 'This is strange, I don't mind her kissing me, in fact...I think I'm actually starting to...enjoy it,' the earth pony thought to herself as she thought she was only doing this so her secret woudn't be leaked, but it was clear to see that there was a little more to this than she first thought.

Scootaloo rested a hoof over Diamond Tiara's, getting her attention, as the earth pony looked back to her, and shivered a little when the pegasus whispered into her ear,

"Just copy what I do okay?" Scootaloo whispered in a low tone, giving a light lick to the earth pony's ear, as Diamond Tiara just nodded while trembling slightly.

Scootaloo slowly moved her hoof to rest just below the earth pony's abdomen, looking back to Diamond Tiara as she gestured for her to do the same to her. Following through and copying the pegasus, Diamond Tiara lifted her hoof and rested it just below Scootaloo's abdomen, causing her to melt a little at the feel of her sensitive stomach being stroked lightly.

"Good, now slowly move your hoof down," Scootaloo instructed as she slowly moved her hoof down to rest over the earth pony's soaked sex, making her tremble slightly, before she copied the pegasus and did the same to her, causing Scootaloo to tremble and let out a small moan in reponse.

'She's really wet...almost as much as I am,' Diamond Tiara nervously thought to herself as they both started off slow, stroking each other's slits, while their heavy breathing matched, and they would increase their speed if one of them advanced at any point.

Diamond Tiara knew she had to not climax before Scootaloo in order for her secret to stay hidden from the rest of the class, but right now she was finding it a little hard to keep up with the pegasus, she was already more far gone from pleasuring herself, and plus getting excited while she had been stirring up Scootaloo had only made it worse. Now her body was happily basking in all the attention it was getting, her core feeling about ready to brust, as her climax was quickly building and apporaching her, wondering if she would even be able to hold out at this point.

Meanwhile Scootaloo could easily tell just how close the earth pony was, she not only was overflowing down there right now, but also her hips would roll into the pegasus's touch, it being no control of her own, as both of the two young pre-teens increased their speeds and advanced after one another, their moans matching each other as they both basked in what seemed like endless pleaure, neither wanting to end it.

Scootaloo hadn't planned on going this far, really she had planned on stopping a lot sooner, but it was already too late. She didn't expect to enjoy doing something like this with a friend, much less with a pony who used to bully and tease her not too long ago, but that is exactly what was happening right now, and to be honest, she wasn't too sure how to feel about it all.

Diamond Tiara was fighting to hold back as best as she could, panting between low moans, while she was going a little slower than the pegasus, but was keeping a good rhythm at least. The earth pony had no idea how much different doing this with another pony could feel, it felt so much better than just doing it by herself, and she couldn't believe how much she was actually enjoying it, as her moans grew louder, and she could tell she wouldn't be able to keep holding herself back for much longer.

As things continued to become more heated between them, it wasn't long before Scootaloo was just on the verge of losing herself as well, her climax quickly building up while her heart was racing wildly in her chest, blushing deeply as she slowed down a little and allowed for the other pony to overwhelm her, not minding that she was letting her get the upper-hoof again.

Seeing that Scootaloo was starting to slow down a little, Diamond Tiara immediatly took this as an opening for her to be able to maybe just get this and 'best' the pegasus, before she herself would be able to hold out no longer. Doubling her efforts and focusing on giving the pegasus's swollen clit, as much attention as her drenched slit was getting at the moment, working her way up to making Scootaloo close to being thrown over the edge.

"Ahh...D-Diamond...ahhh..."

Moaning out the earth pony's name, Scootaloo could feel her breath slowly leaving her, buckling her hips, and thrusting against the other pony's touch, as soon her back arched and she could feel her pleasure reaching its peak. Letting out a long, and loud moan of release, Scootaloo could hold back no longer, panting heavily while she rode out the breath-taking orgasm rippling through her entire body.

Having the pegasus stop as she came, Diamond Tiara carried on through, until Scootaloo started to recover from reaching her limit, the earth pony feeling glad and relived that she had been able to win their little bet, while she gazed to the panting pony, and blushed at seeing her exhausted expression.

"G-good job..." Scootaloo paused as she slowly recovered from her climax, and tried to get her breathing back to normal, shivering slightly when she felt Diamond Tiara move her now soaked hoof away from between her legs, the pegasus smiling as she was going to make sure that this wasn't over just yet,

"Here's your reward for holding up your end of the deal," she whispered, before picking up her fast rhythm again and causing the earth pony to moan and tremble all over, rolling her hips into the pegasus's touches, while there was no chance of her holding back for long now.

"Ahhh...Scootaloo....Ahhh...I can't...Scoot-

Diamond Tiara's moans were cut off as Scootaloo kissed her deeply, the earth pony lost in a world of pleasure, as she could feel slight tears welling up in her eyes, moaning through the heated kiss, while the pegasus continued to make her go crazy, bringing her closer and closer to her limit with every single stroke.

It wasn't long before the trembling earth pony could take no more, her hips buckling, and her back arching , while her loud moans of release were muffled by Scootaloo's lips, the pegasus not letting up at all as Diamond Tiara rode out her instense orgasm, and felt her mind go completely blank, feeling like she was going to collapse, before she caught herself, and began to slowly come down from her high, panting heavily as their kiss ended, and she sat recovering in her afterglow.

"Scootaloo..."

Diamond Tiara whispered out as she sighed heavily, her breathing still heavy, while she gazed to the pegasus through watery, glazed over eyes, Scootaloo just looking back to her with a smile, as she pecked her lips lightly, and could hear a small moan escape the earth pony's throat.

"So...will you keep my secret hidden from everypony else now?" the earth pony asked as she still trembled a little, while Scootaloo wrapped a hoof around her back, and held her close.

"Of course, you did hold up your side of the deal after all, so I won't tell a single soul," Scootaloo stated with a wink, as she smiled to the earth pony, causing her to blush slightly, while she avoided looking back to the pegasus, and swallowed slowly.

Sighing out of relief Diamond Tiara felt like she could relax now that she knew her secret was no longer in danger, and all should be fine, 'That felt...so amazing...I've never felt anything like that before,' she thought to herself, feeling a sense of sweet bliss wash over her whole body, as she let herself smile slightly while being in the pegasus's embrace, certain to not let Scootaloo know how she really felt about what had just happened between them.

"Although I am wondering why you were pleasuring yourself in here anyway, what's wrong with just doing it in your room or something?" Scootaloo asked as she now moved to lean against the wall, feeling quite tired, while she still held the earth pony in her warm embrace, running a hoof through her long lylic and white mane.

"To be honest I'm not sure what it is, whether it's some weird fetish I have, or something else , I just know it's the only way I can get these damn desires that I have to leave me alone," Diamond Tiara explained as she seemed a little annoyed for a minute, before she sighed again and relaxed against Scootaloo.

"So masterbating in the classroom after everypony else is gone, is the only way you can satisfy yourself? That really is a weird fetish," Scootaloo teased as she smirked to Diamond Tiara, and got a stern glare in return.

"What about you?"

"Huh, me? What do you mean Diamonds?"

"How did you know about all this, have you done these kind of things before or something? And quit calling me by that stupid nick-name already," Diamond Tiara raised her voice at that last part a little, but feeling kind of glad that doing this had changed pretty much nothing between the two, the pegasus would still tease her to no end, and call her by that annoying nick-name she had given her it would seem.

"Well you see..." Scootaloo paused, as she just leaned in and kissed the earth pony, causing Diamond Tiara to widened her eyes a little, before she melted into the kiss, and moaned slightly, their lips parting a minute later.

"...I may have some secrets of my own," the pegasus smiled with a wink, causing Diamond Tiara to blush slightly again, as the two rested their forheads against each other, before Scootaloo brought the earth pony into another deep, sweet kiss, both of them moaning in a pleasant way, while they embraced one another and their kiss grew more passionate.

Author's Note

I really do love this ship. :heart:

Thank you ever so much for reading :twilightsmile:

KillerChainsaw ;)