Rainbow Dash and Gilda have had a bet going, and Dash knows just the pony to collect with.
Long ago, Dash and Gilda had a bet. This is the story of how that bet came about, and then lengths to which Dash will (not?) go to beat her old friend. There will be silliness, and shipping is guaranteed.
A word or two of explanation: This fic is a collaborative effort between the author and her lady, AveryStrange. The first chapter was written jointly, and then we split and took the story in very different directions! Choose your own adventure.
“Lydia eyed the heaving creamy mounds of fur and flesh before her, and reached with trembling claws for the laces of Charlotte’s bodice, quivering with anticipation and need.”
Dash paused to work her tongue around her lips, her whole mouth having gone very dry. Across the tiny cabin she and Gilda shared for the summer, the griffon lay on her bed, eyes trained on her pegasus friend. Dash’s hooves shook as she held the pilfered novel before her, afraid the camp counselor would notice its absence from her bunk at any moment, and burst in on them, demanding its return. They were just getting to the good stuff, too.
“Ceasing her fumbling, Lydia raised her eyes to Charlotte’s, stunned by the depth of feeling in the limpid blue pools. Capturing her mouth in a gentle kiss, Lydia fluttered her eyelids, relaxing into the heat of Charlotte’s body against her, and raising her claws again to the cursed laces. She knew where her talons were needed, and was determined to get there.”
“I think she’s gonna touch her tits!” hissed Gilda, talons pointing to her own, still flat, chest. Dash jumped a little where she sat, eyes immediately going to the door of their cabin.
“Shut up!” Her voice was hoarse. “Somepony will hear. Besides, why would she need to undo Charlotte’s bodice to get at her boobs?”
“Uh... duh?” Gilda could only point once more at her chest. Rainbow blinked obliviously.
“That’s your chest, dummy. Boobs are way farther down.” Rainbow started to gesture, but apparently thought better of it.
“What are you, stupid? Have you ever even seen a boob?” Gilda’s eyes narrowed. “I bet you haven’t.”
“What? Of course I have!” Dash retorted, cheeks flushing. “I’ve, I’ve even touched them! They’re like...” her eyes darted around the room, “sandbags.”
“God, Dash, you’re so stupid. Even I know that boobs feel like water balloons!” shouted Gilda, forgetting that they were attempting to be stealthy.
“Oh yeah?” Dash retorted, getting louder as well, “I bet you just made that up! I’ve touched way more boobs than you!”
“Nuh-uh!”
“Yeah-huh!”
“Just what is going on in here?!” The door to their cabin burst open, clattering against the wall. Through it stepped an irate pegasus pony several years Dash’s and Gilda’s senior. Her eyes darted back and forth between the two ponies, focusing in on the novel still held in Rainbow’s hooves. The counselor’s eyes narrowed, then widened in shock. Dash and Gilda had only a split second to trade a fearful glance before counselor’s senses returned to her.
“MY BOOK!”
“Oh, ah yes, this is a book. Is it your book? I had no idea!” Gilda widened her eyes, feigning innocence.
“We thought it was... educational! Yeah!” Dash chimed in. The counselor only seemed to get angrier, storming up to them. She held out a hoof, saying nothing but trying to bore a hole in the filly with her gaze. Rainbow handed the book over, which the counselor tucked quickly under one wing.
“Lights out. Now.” With that, the counselor turned around and stormed for the door. Gilda’s eyes went to the window on the far wall, noting the still bright sky.
“But-”
“Now!” The counselor slammed the door behind her. Gilda and Dash traded another glance, but quickly got about preparing for bed. In a matter of minutes they had the lights out and were settling into their respective bunks.
Moments passed in silence as Rainbow Dash eyed the setting sun, mentally reviewing what exactly Lydia had been doing with Charlotte’s bodice. As long as no one was going to know, she had to admit that although the text had been startling, inspirational even, she’d never been so far herself.
In fact, had she but known, Gilda’s thoughts were running in much the same channels, though with a pause or two to marvel at Dash’s seeming ignorance of basic anatomy.
“So you really never touched a boob, huh?” Gilda asked, breaking the silence. Dash stiffened slightly, trying to come up with some kind of clever retort.
“It’s not like you have either!” She replied, making sure to keep her voice low. It was light enough that she could still see Gilda from across the room, and she could see the griffon about to respond.
“Your own don’t count.” Dash preempted. “Not that you have any.”
“Hey!” Gilda rolled over to glare at Rainbow. “And it’s not like you ponies have any either! Like, what’s up with that?”
“Uhh, Gilda, I’m telling you... look, nevermind. I feel bad for your first girlfriend. When you finally get one, I mean.”
“Whatcha mean, finally?” Gilda hissed. “I’m gonna get one way before you! You boobless dunce.”
“BOOBLESS DUNCE!” Yelled Dash, before a look from Gilda quieted her. “I’ll have you know that ponies have lovely breasts, thank you very much, Miss Speciesist.”
“Ponies might, but you certainly don’t,” quipped Gilda, looking her friend up and down. “And I don’t care what you think, I’ll be touching a boob way before you do!”
“No way,” hissed Rainbow, sensing a challenge, “I bet you I will touch a boob way before you.”
“Oh, it is SO on,” replied Gilda, heedless of the racket they were making.
“LADIES!” Yelled the voice of their counselor. Reluctantly, Rainbow Dash rolled over, pointedly ignoring Gilda, and mentally vowing to get the best of her in the Battle of the Boobies.
“It’s a bet then.” Gilda hissed, after several minutes. “First one to touch a- no, first one go all the all the way wins.”
“All the way?” Dash asked, her curiosity getting the better of her. She turned over to see Gilda nod.
“Like the bigger kids talk about. Like.. Lydia and Charlotte were doing.”
“But we never found out what...” Dash swallowed, her throat suddenly dry.
“Oh, come on Dash, don’t tell me you don’t know!” Gilda hissed, looking at Dash in amusement.
“What! Gilda, of course I know what big girls do together, duh!” Dash puffed out her chest, trying to look experienced and worldly. “I’ll take your bet, and you know I’ll win!”
Dash was flying high. It was cool even on this summer day, and Dash wore a broad smile over her face. She had just gotten a rare letter from one of her oldest friends, Gilda letting her know she’d be in the area in a couple of weeks. While even Dash found the griffon abrasive at times, there was no denying all the experiences they had shared each summer. It had been a couple years now since camp, and almost as long since the two had met up, so Dash was more than enthusiastic.
Her mind turned over the many adventures they had that summer. Races and dares, pranks and bets. Like the time they had beaten the entire boys camp handily in a race, or the time they had dumped an entire bottle of hot sauce in the mess hall’s dinner, or the time Dash had snuck into the counselor’s bunk, stolen a book she kept under her bed, and... oh, horseapples. Dash’s mood (and altitude, as her wings briefly locked up) significantly dropped at a sudden memory..
It had been something of a silly bet, between two girls who barely even understood their own sexuality, but it had been a bet made nonetheless. What if Gilda was coming to announce her victory? What if she asked why Dash had never collected on the bet? What if Dash had to admit she had never even....
It was embarrassing, beyond embarrassing to Dash she had still never dated. Things had just always gotten in the way. For a while she had figured Fluttershy could have been the one, given how attached the older filly had been to Dash when they were growing up. But somehow it had just never quite happened, the merest hint of romance sending Fluttershy into a flustered state that could last for days. Very quickly after it had been made, Rainbow had forgotten about the bet entirely, and hadn’t put any conscious effort into dating for years.
It wasn’t like Dash didn’t have any options. Ponyville was chocked full of single mares, and the brash pegasus knew she had more than a couple admirers among them. The question simply was, who could she get with on short notice? She needed somepony who knew her, liked her, and wouldn’t be too-much of a hold out. Somepony she didn’t have to overtly woo too hard; Dash didn’t want to be a creep about it. After all, she couldn’t waste time with the whole ‘courting’ thing, especially given she barely knew how that worked to begin with. That struck out most candidates... but made Dash wonder. Would any of her friends...?
Fluttershy was right out, obviously. Rainbow wasn’t sure Fluttershy would date anypony, and as close as the two of them were, she just couldn’t see it happening. Applejack, on the other hand, Dash lingered on for several moments, before dismissing given the farmer’s traditionalist attitude towards most things. The idea of coming on to Twilight left a bad taste in Dash’s mouth; the unicorn was just too naive, it felt slimy to use her. Rarity was still busy trying to convince the world she was straight (Dash was privy to a lot of gossip from Fluttershy, so knew better) so that struck out another option. The only one left in Dash’s mind was... was... it was genius!
Dash fluttered down to Sugarcube Corner and let herself in. It wasn’t yet lunchtime, meaning that the normally popular eatery was still rather quiet. Neither Mr. or Mrs. Cake were around when she entered, but Rainbow could hear noise from the kitchen. She was familiar enough with the Cakes that she hopped over the counter and poked her head into the back. Luckily for her, it was Pinkie Pie whipping up a batch of cupcakes, no doubt for the incoming lunch rush. Dash paused a moment, taking in the quiet song Pinkie sung herself as she worked. They way Pinkie danced around, her smile, her love of life was just so apparent in her work. Rainbow decided that if she was going to do this, she was going to do this right.
“Oh, hey Dashie!” Pinkie noticed Dash staring, but offered her a friendly smile. “Sorry I can’t play right now! The Cakes had to do an emergency delivery and left me in charge!”
“Hi Pinkie.” Dash had never really taken notice of Pinkie Pie’s nickname for her, but now it made her wonder. “That’s okay, I was just wondering if...” all of the sudden she felt her confidence drain away, “...um, y’know, if you weren’t busy later...” she mumbled.
“Oh, I can totally play then!” Pinkie replied. She took a moment to suck on the batter spoon like it was a lollipop. “Me mudd mve mks!”
“Um, no, like, we hang out all the time,” Dash rubbed one foreleg with the other, “so I was thinking we could do something different this time? Maybe, like... dinner?” Wow, she really did feel like a dweeb right now. Pinkie was just so focused on her, it was intense. Rainbow had never noticed the pink party pony’s eyes before. They positively shone, especially now.
“Dinner? Dashie, are you asking me on a da~ate?” Pinkie sing-songed. Dash nodded, looking a little red. The exuberant pony bounded straight over the counter in an instant, grabbing a hold of Rainbow’s face.
“Oooh, of course I’ll go!” Pinkie tittered. Dash briefly thought Pinkie was going to kiss her there and then, but to her disappointment Pinkie let go of her.
“I’m so excited! We can go sledding together and go on balloon rides and to the county fair and share cotton candy and-” Pinkie gave a rare pause to breathe and Dash capitalized on it.
“Uhh, how about we just start with dinner?” She asked. “I’m pretty sure it’s too... summer... to go sledding anyway.” She filed away the county fair idea in case a second date was in order. After all, even if she did manage to win Gilda’s bet (possibly today, at this rate), no reason for them to stop dating. After all, this was beginning to look like a better and better idea.
“Okie dokie lokie!” Pinkie replied. “I need to finish all this baking anyway! Besides, where are we going to find a ukelele on such short notice?”
“O-kay... so, yeah. I can come over after you finish work?” She asked, receiving an exuberant nod from her friend.
“Wow,” Dash added under her breath, “this is easier than I thought.”
“Oh Dashie, were you worried?” Pinkie caught Dash’s words, and shot a smile in the surprised pegasus’s direction. “I like you, silly.”
Rainbow had never felt her cheeks redden quite as much as they did in that moment. She just nodded, her mouth too dry and awkward to risk speech on. Pinkie just got right back to work like nothing had happened. Dash looked around, and seeing no real reason to linger, let herself out. Okay, so she definitely wasn’t suave. But a dinner date was easy, right? You eat dinner, you walk home together, you... okay, Dash was stuck on that. But Pinkie definitely had some ideas of her own. Pinkie Pie was so confident, so energetic... so playful, and adorable, and... Dash walked face first into the door out of Sugarcube corner. Instead of little stars, little Pinkie Pies bounced around her head as she fell back. Embarrassed, she quickly opened the door and exited, mind turning to their date tonight.
---
“And that’s when I said, Oatmeal? You’re crazy!” Pinkie finished with a giggle. Across the table, Dash burst into laughter. Two plates of thoroughly cooled food sat almost untouched between the two ponies. Rainbow looked again at her date. They had swung a patio table on short notice, and Pinkie was lit by the orange rays of the setting sun. Without even communicating it, both of them had known to dress up slightly without overdoing it. Pinkie’s hair was a curly mess of course, but she had groomed her coat and put on a little makeup, showing a girly side Dash forgot existed in her friend. The brash pegasus in turn had pulled an old and ill-used brush through her mane and tail until they smoothed themselves out. Her bangs were even and her tail curled around in the cutest manner.
The evening had gone wonderfully. It was strange, given they had been friends for so long, but Dash had never really taken notice of all the little things before. The way Pinkie fluttered her eyelashes, how bubbly her laugh was, how cute she smiled. Rainbow couldn’t remember the last time she had this much fun, and she hadn’t even beaten anypony at anything! Instead she had just sat here and listened to Pinkie’s anecdotes and life stories, occasionally doing her best to offer something interesting in turn.
Once or twice the conversation had accidentally turned to more serious topics. Dash had feared she had blown it when she had made what she thought was a harmless comment regarding a bucket of turnips. But in the end Pinkie had seemed touch by how vehemently Rainbow apologized and swore her continued friendship to Pinkie, whatever moments she may have. Another time Pinkie had brought up her family, only to fade into a wistful stare at the horizon. Dash had brought her back with a tightly squeezed hoof and meaningful stare into the other pony’s eyes. It was clear something was going on between them, way more than Dash had expected.
Now the conversation was slowly dying down, and both ponies agreed they were done with their meals. Despite eating so little, Dash wasn’t the least bit hungry. She had other thoughts in mind. She hadn’t expected to enjoy this so much. Courting was easy, she figured, given how happy the both of them seemed with the date.
“So... how about I walk you home?” Rainbow asked, feeling more confident with herself. Pinkie gave a sly smile and battered her eyelashes.
“Okie dokie lokie.” She replied, bubbly and... seductively? Dash was pretty sure she had never heard that tone of voice from her friend before. It sounded like when Rarity was getting a stallion to do something for her. Funny how Rarity could get any stallion to do anything, yet remained so staunchly single, Dash thought with a smirk. She followed slightly behind Pinkie, drinking in the sight of her friend’s body. In short, she spent the short walk back to Sugarcube just straight up leering at Pinkie Pie’s hindquarters.
“Hey Dashie.” Pinkie looked over her shoulder as they reached the door. She clearly caught Rainbow staring at her backside, but simply grinned at the lovestruck pegasus.
“Mr. and Mrs. Cake are probably already asleep.” Pinkie stated. “Wanna go have a little fun?”
Dash’s brain exploded, her knees quivered, and her wings shot open all at once. Pinkie Pie giggled and opened the door. After a second, lust took over Dash’s vacant mind and drove her forward. Sugarcube Corner was strange to her in the dark, but she only cared about the staircase on the other side of the room. There was a light coming from the top of the stairs, along with the sound of melodious giggling. Thoughts of the future near and far swam in Rainbow’s head. She could collect on Gilda’s bet with her fillyfriend as proof. She and Pinkie could go sledding and to fairs and she’d buy Pinkie Pie a cotton candy larger than her head. And then another. They could go out on adventures, go pranking, and at the end of the day... she reached the top of the stairs.
Several minutes passed as the sun set. Few ponies were still on the street, but a few were lucky enough to be around Sugarcube Corner when it happened. From the single lit window, a blue-and-rainbow blur shot out like a bat out of hell. Dash panted as she raced far, far away, not even daring to look back. Had she, she would have seen Pinkie Pie run to the window behind her. The pink party pony’s forelegs were covered in black latex sleeves, and she looked rather like a unicorn with the strap-on wrapped around her forehead.
“Wait, Dashie, come back!” She called out. “It’s okay! We can only use the mini dildo cannon this time! Come baaaaaaaaack!” Seeing Dash instead disappear into the difference, she placed her hoof against her chin and frowned.
“Hmph. Guess it’s time to go back to Rarity.” She said, closing the window. In the distance, Rainbow Dash had reached her home. Let Gilda come, bet or not. If that was sex, Dash was quite happy being a boobless dunce until the day she died.
Rainbow Dash twitched in her sleep, dreaming of speeding through the air with Gilda, as they had at camp two summers prior. A particularly violent twitch started her into wakefulness, and she scrubbed at her face with a hoof, fighting off the fog of sleep. Swiping at her eyes once more, she thought back to the still unfinished business with her friend: their bet. It hung over her, unspoken of in their letters. The only thing stronger than Dash’s embarrassment at failing to get so much as a kiss was her determination to win. The ‘boobless dunce’ comment still stung, but she rather liked her chances against someone who didn’t even know where boobs were.
Glancing out the window, head still muzzy, Dash realized it must be rather later than she’d thought, since the sun was already well on the way to its zenith. As she listened she heard Pinkie Pie squealing about her latest project. Rainbow wondered idly what her friend could possibly want with a guitarra de golpe.
A sudden shout of “Cutie Mark Crusaders Mariachi Band, YAY!” cleared that one up.
Pinkie bounced into view, shepherding three smaller foals, who held guitars, guittarones, and a fiddle. A quick scan identified the Apple Bloom, Scootaloo, and Sweetie Belle.
Collecting her thoughts, Dash was dismayed at what she found. The bet was still heavy on her mind, along with a depressing truth. She was as ignorant of the ways of dating as Sweetie Belle or Apple Bloom and dammit she wouldn't put it past Scootaloo to have one upped her in the lady department. Forgot embarrassing, this was mortifying. She was Rainbow Dash and someone as thrilling as her in the air shouldn't be so stupidly fumbling in more delicate matters. She wanted to be the Casanova of the skies, not a boobless dunce. Not that she was stupid or something. She could have had any number of mares, but Rainbow Dash wanted the best. She deserved the best, and the best just wasn’t putting out. Oh no, the best would rather make a freaking mariachi band with some actual boobless dunces.
She'd had her eye on Pinkie Pie and Dash was positive that she was no prudish virgin, and had some sweet moves. (Or so she heard. Pinkie Pie was a shameless pony, and she usually got what she wanted. And according to Cloudchaser, who just loved to share the latest news with her coworkers, what she wanted turned out to be half of Ponyville.) Dash wasn't about to pick up second tier techniques. She carefully curated her competent facade and she wasn't about to accept a crack in it. Not that Dash knew what a facade was, because really, words like that were best left to Rarity.
And if there was more to her attraction to Pinkie Pie, she wasn't about to look too closely at that, let alone ask her friend on something like a date. Who was she, Fluttershy??
Shrugging, Dash bounded down outside and winged her way towards the Pony Mariachi. Pinkie Pie picked up her head, ears pricking up at her friend’s approach.
"Hey! DASHIE, want to join us and play?!?" she squealed. "Ai ai ai, Mariachi!"
Okay, so Pinkie could be a bit of dork, Dash supposed, but she had a very endearing way about her, with enthusiasm for traditional Mexican music shining in her face, chest rising gently as she inhaled to plead with Dash to humor her, withers sloping gently into the curve of her back up to where it rounded over her full and gorgeous flanks...
"DASH! Equestria to Dash, come in Dashie!" Hollered Pinkie Pie.
Rainbow Dash started and hovered slightly, shocked from her pleasant reverie by Pinkie's yell and the vigorous waving of what must be an extremely sturdy violin.
“Umm, yeah, hey!” said Dash, pulling herself together and trying to act like she hadn’t been checking out her friend. “I was just... really, um, focused! On how I could help with the... music, you know, the mariachi music.”
Pinkie Pie, oblivious to Dash’s discomfort, extended a hoof, presenting Dash with the violin. It shook slightly as the pink filly vibrated with with excitement. Carefully, Dash took the instrument, and Pinkie Pie immediately bounded off, returning almost instantly with two giant, garish sombreros, seemingly produced from thin air. Sometimes it was best not to think too hard about how Pinkie Pie did things. She bounced where physics feared to tread.
Gingerly, Rainbow Dash positioned the violin. Hoofing the strings in what she hoped was a suggestive manner, she leered at Pinkie Pie and said, “I’d be happy to play your violin” and followed with a roguish wink for good measure.
“Okie dokie lokie!!” squealed Pinkie, briefly wondering if there was something wrong with Dash’s face.
Pinkie was distracted from Dash’s apparent new tic by Sweetie Belle faceplanting through the guitar she was holding.
“Silly filly,” pouted Pinkie, “that isn’t how you play the guitar at all!”
“Oh baby, I’ll put a little filly in your guitar...” mumbled Dash, trying to sound deep and sensual.
“Dashie, I’ve already got a little filly in my guitar! Would you like a cough drop? You don’t sound so good.” Pinkie Pie reached up into her sombrero a pulled out a little golden lozenge.
“Oh, Pinkie, how did you know, I’m really great at sucking on... things” said Dash, with what she hoped was a meaningful pause.
“That’s good! Then your throat will get better right away!” Pinkie beamed at her friend, who appeared to be practically choking on a perfectly good cough drop.
Rainbow Dash wheezed and blushed, then stammered “here, um, can’t actually play violin, gottagobye” before speeding off in the direction of Cloudsdale.
Below her, Angel scowled and vowed Rabbit Revenge on the one who spits cough drops from the sky.
Rainbow Dash swooped and soared, gradually working her face out of a look that would have made a filly weep in terror. As she neared Cloudsdale, she spied a trio of colts and veered to change course. She wasn’t in the mood for Dumb-Bell’s “Rainbow Crash” routine. She’d just go home. Gilda was gonna win the bet. At least she had groupies to look forward to, if she ever flew with the Wonderbolts.
Head drooping, Rainbow Dash winged her way towards home, wondering if maybe Twilight had a book that could help her. She was desperate enough to actually read.
“Oh HI, droopy drawers!” Squealed Pinkie, opening the door just as Dash raised her hand to the knob. Startled, Dash lifted her head.
“Uh, hey, Pinkie. Umm, how did you get up here?” She fumbled.
“I’m Pinkie Pie, wheeeeee!” was the only reply.
“So, Dashie,” continued Pinkie Pie, “I know you were so sad because you couldn’t play the violin, so I brought you something to cheer you right up!” Again, she reached into the sombrero, this time pulling out a pair of maracas. “You can shake them! Everyone can play the maracas!”
Screwing up her face and her courage for one last try, Dash purred “Oh, honey, I will shake your maracas all night long”
“But your hooves would get tired!” said Pinkie. “You keep saying the oddest things? Are you sick? Are you hiding something? What would you be hiding?! Maybe you don’t like mariachi? Maybe you don’t like me? Is that why you keep making that weird face? Well, I’m on to you Rainbow Dash, you’re not putting one over on Pinkie Pie!”
Dash inadvertently stepped back from the advancing pink whirlwind, and hovered in front of her door.
“Uh, actually, you see, Pinkie... what I mean, is, well, you know...” Dash felt herself turning crimson “what I actually mean, you know, by maracas... isn’t maracas. Because when I say that I mean that I wanna...” she trailed off, then quietly added “wanna touch you.”
“OH!” Gasped Pinkie Pie “That’s what you meant!? I’ve been hoping you’d say something for almost ever! But why would you call them maracas?”
“Oh, err, well, I thought you... I...” Dash stuttered, trying to hide her inexperience.
“You are so CUTE!” squealed Pinkie Pie, leaning over to nuzzle and nibble at Dash’s withers.
Rainbow Dash turned and gazed into her friends eyes as Pinkie’s lips hovered over her coat, searching for a sign, for permission, and liking what she found.
A whole new kind of magic was made between Pinkie and her Dashie that night, and although she won her bet, Dash realized that some things are more important than winning. Not that it stopped her from lording it over Gilda like the arrogant prat pony she was, at least until Dash got shanked by Angel.