Best Me If You Still Can

by KillerChainsaw

Rating: mature
Tags: My Little Pony: Friendship is Magic, Romance, Porn, Sex, Scootaloo, Diamond Tiara, Slice of Life
Length: 3788

Scootaloo and Diamond Tiara once again try to 'best' each other, however this time there's a certain 'perk' for the one who comes out 'on top'.

This story is a sequel to another story of mine called 'Besting A Pegasus', please read that story before reading this one. Also there is a scene included from another one of my stories, it's called 'A Surprisingly Pleasurable Hypnotism', and you can choose to read it if you want to, but you don't need to read it in order to understand what will be happening in this story just so you know.

After 'besting' each other multiple times teenagers Scootaloo and Diamond Tiara have eventually started to date in secret, both of them wanting to have as much time alone as they can without any of their friends finding out about their relationship. And so one afternoon while Scootaloo is going to meet up with her marefriend, she stumbles across a very surprising sight, which in turn gives her quite the interesting idea to share with her secret lover.

(Contains teenage Scootaloo and Diamond Tiara 'besting' each other with the winner particularly benefiting from it this time :raritywink:)

Written for:

superfun

Published 2020-10-16 16:10:01 UTC
Last updated 2020-10-16 16:10:01 UTC

If You Succeed Your Reward Will Be...

As late afternoon was beginning to slowly settle in Scootaloo was happily gliding through the sky, a content smile resting on her lips, while a cool breeze flowed through her magenta mane, as she breathed in the refreshing air. The orange pegasus currently making her way over to Diamond Tiara's place, since the two of them had agreed that they would meet up later on today, it being easy to see that Scootaloo was glad to be going to spend some time alone with her marefriend, although it hadn't been long at all since they were last together she still wanted to be with the other young mare as much as she could.

The two teens having only been dating for a little while now, and suffice to say they were quite clearly in the 'Honeymoon' faze still, where they always wanted to be with each other, and it wouldn't take long for their time alone together to often become quite 'intimate'. The young mare already imagining what could end up happening between her and her adorable marefriend once she would arrive at the earth pony's house, having been told earlier that day that they would have the place all to themselves for hours, which caused Scootaloo to get excited by just thinking about such a window of opportunity being wide open for them both.

The smiling pegasus glancing down to the ground below as she was just about to pass over her mentor/elder sister figure's cloud home, expecting to see the cyan mare returning home from her work like normal, however what she actually saw causing her to do a quick double take, her eyes going wide as she took in the surprising sight she was seeing at the moment. Trying to make sense of the scene that was currently playing out just below Rainbow Dash's house, but that shocked expression of her's not staying for long it seemed as instead it soon gave her quite the interesting idea, one that resulted in her lips forming into a smirk before she simply just picked up speed, and took off to make a quick detour before heading off for her marefriend's home hoping to get to her desired destination as quickly as she could.

....

Diamond Tiara not expecting to see her marefriend show up at her door earlier than she had originally said she was going to before, but not complaining in the least as it was clear to see that she was more than delighted to spend some time alone with the pegasus, since although she wasn't going to admit it she had actually been missing Scootaloo quite a considerable amount when they were apart. Welcoming in the orange mare and leading the way up to her bedroom, it not being all that long before they were both laying on the earth pony's bed, kissing passionately and wrapped in each other's warm embrace.

There lips soon parting however as Diamond Tiara was now resting her head on Scootaloo's chest, nuzzling into her soft fur and sighing contently, breathing in her marefriend's scent while the pegasus just gazed to her with a smile, currently stroking the other young mare's mane gently.

"So was there some sort of reason why you got here much earlier than what we had planned on?" The earth pony asked, raising her eyebrow to Scootaloo as she just shrugged her shoulders in response, causing Diamond Tiara to seem more suspicious of what the orange mare's true intentions were when she arrived at her place just a few moments ago.

"Do I need a special sort of reason for wanting to see the pony that I love a little sooner than what we agreed on?"

"Well you're lucky that my parents left for their 'very important business meeting' just before you showed up, otherwise I doubt it would've been easy to explain to them what you were doing here, without revealing our relationship to them both," rolling her eyes Diamond Tiara could easily tell that the smirking mare laying beside her wasn't telling her the whole truth right now, but guessing it was likely the best she was going to get with the pegasus at this moment in time.

Scootaloo just brushing off her marefriend's lecturing words, showing that she wasn't really paying much attention to what she was going on about at the moment, as she instead just nodded her head before she began to lightly kiss the earth pony's cheek, trailing down to her neck slowly while causing Diamond Tiara to just sigh again. However this time it was a much more heavy sigh, knowing that although the pegasus had grown just like she had, but unlike her she could often still be very childish and sometimes irritating whenever she acted like she wasn't really listening like this.

"Hey...you know something you haven't done in a while?" Changing the subject just like the earth pony knew she would, Scootaloo obviously dodging the other young mare's question, while simply just waiting for her's to be answered instead.

"What?"

"You haven't bested me in quite a while now, I wonder if you can still do it," the pegasus just smirking to her marefriend who had responded to her in a very reluctant tone, only for her expression to look more taken aback now, as she knew that the orange mare was trying to challenge her at the moment, causing her to already easily tell where this conversation was going.

"Of course I can still do it, I've bested you plenty of times since we started going out,"

"But what if this time we make it a little more...'interesting'?" Scootaloo causing Diamond Tiara to raise her eyebrow once again, hoping that she wouldn't regret asking her smirking marefriend to go into more detail, while it was clear to see that the orange pegasus had probably been eagerly awaiting to talk about this since the minute she arrived not too long ago.

"What do you mean?"

"Well before I came here, I saw something that gave me the perfect idea for us to try out..." the orange mare pausing and moving to now get off the bed as she walked over to where she had left the saddle bag that she had brought over with her, reaching inside of it and pulling out a lilac coloured dog collar and lead to match, which she had bought just before coming to Diamond Tiara's house. The earth pony's eyes widening when she saw what Scootaloo was holding, causing her to blush deeply, turning away a moment later while her marefriend just continued on.

"If you can best me then you can take me for a little walk using this, but if it turns out that you actually can't best me, then I get to walk you instead. Sounds fair right?" She finished as she held out the dog collar and lead for the other mare to see clearly, while Diamond Tiara just looked to her marefriend, unsure of what exactly she should say, this situation definitely not one she could have thought she was going to be in when Scootaloo came round to her's today.

'A dog collar and lead? Just where did this so-called 'perfect idea' of her's come from?' Thinking to herself with a slight sigh Diamond Tiara seemed like she was debating whether she should really agree to this 'idea' of Scootaloo's, or just refuse, 'Honestly I wouldn't mind getting to see her looking all embarrassed while getting walked around town by me, but...if I end not being able to best her then...No I can easily best her, I've done it before, plus since we've been dating I've learnt what all her weak points are, so I should be able to pull this off with no trouble at all,' after going through it all inside her mind she didn't see why this could not end up going in her favour, and so agreed to her marefriend's idea with a nod, turning back to look to the orange mare with more of a confident smile now.

"Sounds fair to me I guess, although I'm pretty sure I'll be the one taking you for a walk by the end of all this," trying to sound smug Diamond Tiara was sure she could step up to the challenge and come out on top, while it was obvious that Scootaloo believed that she would be the one to easily 'best' the other young mare, as she simply just shrugged her shoulders before putting the dog collar and lead down on to the bedroom floor, making her way back over to lay on the bed again a moment later.

"We'll just see about that, Diamonds," the pegasus calling the earth pony by the nickname that only she ever addressed her as, smirking back to her marefriend once again, before she was back to laying beside Diamond Tiara and kissing her lips passionately, while she linked her forelegs around Scootaloo's neck and soon let herself be pinned down to the bed by the orange mare.

Diamond Tiara wanting to get the advantage on her marefriend as quickly as she could, knowing that she would have to act fast if she didn't want to give Scootaloo a chance to make her melt with sensual kisses, or causing her to become weak from attacking her most sensitive areas. The earth pony looking like she knew exactly what she needed to do in order to have more of a fighting chance, going for the neck first as although it wasn't a weak point for the orange pegasus, Diamond Tiara was certain that it would still turn her on, and hopefully distract her a little.

Luckily for her Scootaloo seemed to give in a bit, simply just leaning her head back to give her marefriend more of an easy access, as she was currently showering the orange mare's neck with light kisses and small bites every so often, causing Scootaloo to moan slightly while she smirked and let herself melt into this moment. Letting Diamond Tiara think that she was getting the better of her for now, when in reality the smirking pegasus was just waiting for the right moment to strike back at her lover.

Allowing Diamond Tiara to flip them over and now be the one pinning her down onto the bed, while the earth pony soon moved on to start licking, kissing and sucking on the underside of Scootaloo's wings, knowing that she would definitely get more of a reaction out of her lover since that was one weak point that never seemed to fail her. She being right as the orange mare widened her eyes when feeling her wings being attacked, her body starting to squirm and tremble, but just biting down on her bottom lip, holding back her moans and focusing on not letting herself fall victim to her cunning marefriend so easily.

'She's still so weak on the underside of her wings...maybe this really will be easier than I thought,' Diamond Tiara thought as she looked down to her panting marefriend, seeing that she already had a glazed over gaze in her purple eyes, as she continued to squirm and moan in response to all of her lover's advances, unknown to her that Scootaloo was just 'playing it up' as best as she could. The pegasus definitely getting stirred up from all this, but also being glad that the underside of her wings weren't the weakest area on her body, however guessing that it wouldn't be long before the earth pony would attack those places as well, so she would have to cut the act and turn the tables back on her soon enough.

Continuing to let her marefriend think she had her beat for a little while longer, laying back on the bed and waiting until she felt Diamond Tiara's tongue starting to travel towards her waist area. Once she did Scootaloo acted fast, pulling herself up to flip them over again so that she was now on top of the other young mare, smirking when she saw her surprised expression, showing that she clearly wasn't expecting what had just happened.

"Sorry Diamonds, but I'm afraid I'm not going to make this that easy for you this time," lowering her tone into more of a seductive one the orange mare didn't even give her taken aback lover a chance to respond and compose herself, instead she simply just positioned her hind leg so that it was overlapping Diamond Tiara's, causing their aroused sexes to kiss and begin rubbing against each other, while the pegasus held her lover close and was already slowly grinding into her.

"S-Scootaloo...that's not...fair...AHH!"

Crying out in sudden pleasure Diamond Tiara bit down on her bottom lip hard, tying desperately to hold back her moans as she felt like cursing herself for falling for her sly marefriend's play, staring to pant heavily and notice her mind going blank, her body reacting to Scootaloo's movements and her hips beginning to thrust against the orange mare in return.

"I never said we would be playing, 'fair',"

Whispering that last word into the earth pony's ear, causing her to shiver all over and moan louder when she felt Scootaloo increasing her pace, thrusting roughly against her, while she rested her chin on her marefriend's shoulder and tightly held her front hooves around Scootaloo's neck. Not being able to help but just react to the pegasus's advances, Diamond Tiara knew she had to do something in order to stop her body from giving into her lover, as she could already feel heavy pressure building up from inside her lower abdomen, singling that if she didn't do something soon this would be all over for her in only a matter of minutes.

Having to think fast she tried to keep herself focused as best as she could, while also thinking of ways she just might be able to turn things around and have everything working in her favour once again. Not getting many ideas at the moment it seemed she soon bit down on her marefriend's shoulder hard, it wasn't enough to break the skin and draw blood, but she was still able to leave a red mark there, hoping that it would be enough to catch Scootaloo off guard if only a little. However her plan not working out very well, as although the bite did cause the pegasus to wince a bit in pain, it didn't make her pause or even really slow down for that matter, instead she just returned the favour on her shoulder.

Seeing as how her first method didn't work out all that well, Diamond Tiara figured that trying to beat Scootaloo at her own game might just give her a better chance at turning the tables on her marefriend, increasing her own rhythm and thrusting roughly against the orange mare, however she soon realised that this was a mistake on her part. Scootaloo simply just smirking as she took this as a challenge that she was more than pleased to raise to, thrusting harder into the earth pony as she caused their swollen clits to brush over each other every so often, both of them trembling as a result of this.

It not being long before Scootaloo was overwhelming the other young mare, and Diamond Tiara finding it considerately difficult to try to match her rhythm each time her lover increased her pace, it becoming harder and harder for the earth pony to hold back, feeling her mind quickly going blank and the pressure now building up so much that she knew it wouldn't take much for her to be thrown over the edge.

'I can't...I can't keep going like this...it's too much...it all feels too good,' she knew she was close and would be reaching her limit anytime soon, biting her bottom lip seeming like the only thing she could do at the moment to try and hold out for just a little longer, however Scootaloo clearly seeing that her marefriend was just barely hanging on at this point, and so knew exactly what to do in order to push her beyond the threshold.

Pressing her lips to the other young mare's in a passionate, deep kiss, while also doubling her efforts at the same time, this seeming to be all it took for Diamond Tiara to be caught off guard and not being able to hold back any longer. Feeling her breath hitch inside her throat as Scootaloo proceeded to suck roughly on her tongue, while still thrusting hard against her overflowing slit, causing the earth pony to widen her eyes before shutting them tight, her loud cries of release being muffled by their kiss and after a simple minute more an intense climax began to ripple throughout her entire body.

'I couldn't do it...I'm cumming...' this thought being the last to run through her mind before it went completely blank, all her muscles tensing up as she trembled all over, feeling Scootaloo still thrusting against her, causing her to ride out her breathtaking orgasm. It not being long until all the pleasure got too much for even the pegasus, resulting in her climaxing soon after her marefriend had.

The two eventually parting and collapsing beside each other on the bed, both of them panting heavily as they tried to get their breathing back to normal, Diamond Tiara feeling slight tears of bliss escape from her eyelids and slowly run down her cheeks, while her heart pounded inside her chest and she was still squirming slightly from reaching her limit only a few seconds ago. Scootaloo being able to miraculously recover quite quickly, even though she came straight after the other young mare, she now sighed deeply and came to rest her chin on her marefriend's chest, smiling to her while she waited for the still panting earth pony to come down from her high.

"So Diamonds...what do you say we go for that walk, once we've freshened up a bit, hmm?" The orange mare smirking with a raised eyebrow to her exhausted marefriend, causing her to soon just roll her eyes and nod her head reluctantly in reply, having finally recovered now it seemed, figuring that it was better not to get herself worked up again since she was already tired from being well and truly 'bested' by Scootaloo. Instead she simply just cupped the pegasus's cheek in her hoof and sighed when she felt the other's lips brush against her forehead lightly, accepting that she had lost at this point and knowing that she would have to prepare herself for what was to come next.

....

An hour later Diamond Tiara was being walked around the local park in Ponyville by her marefriend, who seemed all too happy with herself, tugging on the lilac lead that she was holding onto with her wing, singling for the earth pony to keep following along behind her. The matching dog collar luckily fitting her well enough and wasn't too tight around her neck, however it was obvious that she was still feeling a lot of discomfort at the moment, blushing deeply when the odd stallion or mare would stare at her as they walked past, causing her to only be thankful that there weren't many other ponies in the park at this time of the day.

'I never should have agreed to that stupid 'idea' of her's, this is so embarrassing,' trying to just keep her gaze on the grass below her right now, the earth pony continued to stay silent and act as nonchalant as she could in this uncomfortable situation she was currently in, figuring that if she would just get this walk over and done with quickly then she wouldn't have to think about it ever again. However her hiding her face behind her mane, causing Scootaloo to frown when she looked back to her marefriend, as she soon halted and caused the other young mare to do the same.

"Aww come on Diamonds, cheer up. This isn't so bad, there aren't that many ponies around here and look the lead and collar even match your mane. So maybe all the ponies that are staring at you could see it as a nice...'accessory'," speaking in a bit of a nervous tone Scootaloo could already tell that her marefriend was definitely planning of a way to get her back for all this, while Diamond Tiara just glared back to the pegasus in response.

"The minute we see any of our friends, you are taking this off me, got it?" Giving Scootaloo a warning stare and causing her to just nod back to her with a nervous smile, both of them calling themselves lucky that they hadn't seen any of their friends just yet, and hopefully they wouldn't happen to run into anyone else they knew well while they were still on this 'little walk' together.

"Where did you even get this idea from anyway?" Asking after sighing heavily, Diamond Tiara thought she might as well ask the question that had been at the back of her mind since the other young mare had told her about this 'idea' of her's earlier, it being clear that she was currently trying to distract herself from being nervous about the occasional stares and weird looks she was still getting every so often from the other ponies in the park.

"I saw Rainbow Dash and Rarity doing this while I was making my way over to yours eariler, only Rarity was just wearing a collar when Dash was walking her around below her house," the pegasus simply answering in a unfazed tone, as she began walking once again, however being stopped when her marefriend hadn't moved and was instead just standing still, looking back to Scootaloo with a shocked and clearly confused expression.

"Wait...you saw Rainbow Dash and Rarity doing this?" She questioned in a lowered tone so that any other pony walking past wouldn't hear her, while Scootaloo just nodded to her in reply, not really seeing it being all that much of a big deal as she started to go into more detail of what exactly she saw eariler. The two young mares soon continuing their short stroll through the park together, neither of them really realising just how much of a big secret they had stumbled upon that afternoon.

Author's Note

This is the last instalment in this series of Scootaloo x Diamond Tiara one-shots just so you know, and honestly I've loved writing each one of them. :pinkiehappy:

Hope you all enjoyed and thank you for reading. :twilightsmile:

KillerChainsaw ;)