Windy Whistles Upgrades to Gilf

by Crimson Prose

Rating: mature
Tags: Rainbow Dash, Comedy, Wonderbolts, Sex, Slice of Life, My Little Pony: Friendship is Magic, Soarin, Thunderlane, Other
Length: 2803

Rainbow's parents are proud, but impatient for a grandfoal. Windy decides to help Rainbow out by testing the Wonderbolt stallions on her behalf and choses one. Grandfoal making ensues.

Bow Hothoof and Windy Whistles are very proud of their daughter Rainbow Dash, but are impatient for a grandfoal. Windy decides to take matters into her own hooves by testing the goods on her daughter's behalf in the Wonderbolts locker room. Grandfoal-making ensues.
An alt version of this story has been made where Rainbow doesn't consent. Go there at your own risk, I guess.

Thanks to Stardoost for proofing!

Inspired by the cover Image by Shinodage. The full explicit version can be found by searching for "artist:shinodage,windy whistles" on derpibooru. The tumblr where this was posted is user name shinonsfw.

Contents: anal, blow job, embarrassing parents, gangbang, impregnation, incest, licking penetration, locker room, milf->gilf, orgy, public sex, triple penetration, photos, straight sex, vaginal, virgin holes

Published 2017-10-11 20:20:07 UTC
Last updated 2017-10-11 20:20:07 UTC

Rainbow Dash: #1 Gangbang Slut!

It’d been a tiring show, as it always was, but it’d gone well. Rainbow was as impressive as always, and she’d even convinced her parents to not bring fireworks. That was good; Rainbow was sure Spitfire wouldn’t tolerate any more Wonderbolts getting set on fire mid-show.

That didn’t keep them from following her back to the locker rooms after the show. Most of the Wonderbolts’ parents drew the line well before watching them strip out of their sweaty uniform and shower, but not Rainbow’s.

“You were just wonderful today, Dashie,” Windy Whistles said for the fifth time as Rainbow unzipped her uniform.

“Sure were!” Bow Hothoof added. “And might I say, the hottest mare in the show! When are they gonna make our Dashie captain?”

“Thanks, but they don’t choose the captain with a pose-off, guys,” Rainbow chuckled as she peeled off her uniform. She blushed at her dad saying such a thing, but was used to it.

“Speaking of how toned and alluring our daughter is,” Windy nudged Rainbow with a wing. “When are we getting a grandfoal or three to cheer on?”

“And which Wonderbolt will have the honor of being the father?” Bow added.

“How do you know it’ll be a Wonderbolt?” asked Rainbow, grumbling as she tossed her uniform in with the other dirty ones for washing.

“Oh, come on, Dashie, we know you well enough to know it will be,” Windy giggled.

“Who else would be worthy of a go at the greatest Wonderbolt to ever live?” asked Bow.

“A go?” Rainbow couldn’t believe even he put it like that. “I’m gonna go shower.” This was in danger of getting even worse than usual; it was time for a retreat.

“Do you want us to come with you?” Windy asked excitedly.

“I’ll soap you up good, sweetheart!” Bow claimed.

Oh yeah, definitely worse than usual. Could they at least wait until other Bolts weren’t around to do this?

“I can soap myself up fine, Dad,” Rainbow said between gritted teeth, ignoring the snickers from elsewhere in the locker room. “If you’re so desperate to get a grandfoal, why don’t you interview the Wonderbolts while I’m in the showers. Alone.”

“Sure thing, Dashie!” Windy sounded overjoyed.

“Oh, for Celestia’s fiery giant plot, I was joking!” Rainbow groaned and shook her head. “Do whatever you want.”

Dash headed into the shower, sighing. She was the first in the showers today since most Wonderbolts liked to talk about how awesome they were for a bit first. Rainbow usually did too, and would continue to yammer on about it in the shower. But since her parents were being especially weird today, she wanted to get done as fast as she could.

Half-way through showering, it seemed odd that none of the other Wonderbolts had wandered into the showers too. Rainbow hoped that her folks weren’t pestering them too much. She was rinsed and almost done by the time another entered.

“That’s some mom ya got, Crash,” Fleetfoot chuckled as she took the shower spot next to Rainbow.

“What’s she doing?” deadpanned Rainbow.

“Right now?” smirked Fleetfoot. “Getting Soarin’s big blue dick up the posterior.”

“Oh, stop it,” Rainbow groaned. “Please tell me that was a bad joke.”

“Go take a look,” laughed Fleetfoot. “Haven’t seen anything like this since Stormy Flare staggered into the showers drunk off her plot.”

Rainbow hoped that Fleetfoot was pulling her tail. She pushed through the crowd of her comrades in one corner of the locker room to see, and found that Fleetfoot was not. Dash blushed harder than Applejack getting caught eating strawberries.

There, mere hooves from Rainbow’s locker, was her mother, face down ass up on the floor. Soarin had mounted her, the older mare’s plot firmly in his grasp as he drilled his shaft home into her tight tail pucker. He clenched his teeth, grunting as he packed Windy’s tight behind full.

Rainbow watched Soarin’s sack swing and smack Windy’s drooling slit with each thrust, her honey drooling down her hind legs. As Soarin continued pile-driving her rear, his thick spunk overflowed, oozing strands into a puddle on the floor between Windy’s hind hooves. More oozed forward all over Windy’s signature yellow vest. Given the amount all over the floor and drooling down her legs, Rainbow doubted that Soarin was the first to unload there while she was showering.

Rainbow first thought was that her dad would be peeved, but no. Her father stood a few steps away watching. He sat on his haunches, stroking his own throbbing member with both front hooves. He barely slowed down as he waved at Rainbow.

“Hey Dashie!” Bow said. “Looks like your mom found a real winner, right?”

“What’s going on here?!” Rainbow Dash demanded, hyperventilating from embarrassment.

“Hey Dash.” Thunderlane brushed a wing against Rainbow as he edged up to her right side. “Are you ready to join your mom over there?”

Rainbow could feel Thunderlane’s eyes, and a dozen others, on her. She glanced to her left, finding Silver Zoom eyeing her the same way. They both hung free of their sheaths, understandable given the blatant act of milf-ing in front of them. From the looks of it, they’d already had a go at Windy too. That was some rapid-fire sluttery.

“H-ahh,” Windy looked back at Dash, rolling her hips against Soarin with practiced movements even as his own hips stopped. “Of course she is!” Windy spoke on Rainbow’s behalf. “My Dashie can take all three of you at once!”

“Oh really?” asked Thunderlane, taking the statement at face value.

“Is that so?” asked Silver Zoom.

“Mom!!” Rainbow exclaimed, blushing enough to match the red in her mane.

On one hoof, Rainbow appreciated getting attention from stallions, or mares, especially Wonderbolts. Despite Rainbow’s ego however, she was inwardly reluctant when it came to sex. She wanted to be with a Wonderbolt, but had never rose above considering them heroes, which kept her from making a serious move.

And of course, admitting she was still a virgin wasn’t easy. Not even Fluttershy was a virgin, for crying out loud, yet somehow Dash was. It’d be humiliating for her first stallion to realize that, and she was certain he would.

Her parents, on the other hoof, definitely didn’t realize.

“I think it’s time our little Dashie had a turn,” said Windy. “I’m sure her foal factory is just dripping with anticipation!” She wasn’t wrong.

Soarin pulled free from Windy with a lewd slurp and was seconds from stuffing it into the hole that Rainbow came from when Windy waggled her hips away. She hooked one of her hind hooves around Soarin’s and sent him sprawling onto his back on the floor, a dreamy expression on his face. Windy turned, pushing him flat onto his back with one hoof and waving for Rainbow to approach with the other.

“Ow,” Soarin grunted as he flipped, breathing heavily and looking between Windy and Rainbow.

“That’s enough milf for you, Mister Wonder-Dick,” Windy giggled. “Time for you to bake a hot new milf, and to upgrade me to gilf! Come on over, Dashie. I know a well-fucked mare like you knows the drill.”

“Careful not to break anything, Clipper,” chuckled Spitfire, near the front of the crowd, watching with amusement. “Again.”

“Mom, just…” Rainbow sighed, pushing her hind legs together. Even having just stepped out of the showers, the wetness was obvious to anypony that looked, and many were. She wanted to tuck her tail to hide it, but she couldn’t get it to tuck; her body was rebelling.

“I want her plot,” Thunderlane said, sliding a hoof back to rub behind Rainbow. It slid across her slit and circled her tight ponut, using the lubrication from one hole for the other.

“Buck you,” Silver Zoom said, pushing Thunderlane’s hoof aside and tracing around Rainbow’s slit with his own. “You’re a reserve. I get first choice, and I call Crash’s ass.”

Thunderlane grunted, “Fine, I’ll just take that muzzle that she’s always bossing me around with.”

Normally putting a hoof there would result in Rainbow putting a hoof upside both their heads. Instead, she froze, her brain and bits arguing over her next move.

“Come on, sweetheart, no need to be shy,” Bow said, giving Rainbow a push toward Soarin from behind, then licking his hoof clean. “Oh honey, you should get a taste of our daughter’s love honey, it is just the best.”

“Oh, I will,” Windy smirked. “By licking it off our new son-in-law when she’s done.”

Windy caught Rainbow as she was pushed by Bow and pushed her downward onto Soarin, who was still on his back. Soarin stared, wings spread, with an ‘I can’t believe this’ expression. Rainbow straddled Soarin with her steaming wet slit pressed against his already well-used shaft. Luckily it wasn’t too well-used to take a dive in Rainbow Gash, as he was still rock hard.

No sooner was Rainbow straddling Soarin than Silver mounted, his own meat pulsing against her behind as he wormed it to her tail hole. When she tried to speak, Rainbow was smacked in the face with Thunderlane’s stiff meat, thick and as red as her shamed face.

“That’s it, gather round colts,” Windy smirked, sitting on her haunches next to them. She leaned in, kissing first Thunderlane and then Silver. She slid a hoof between her own thighs, gathering her own love honey and spreading it onto Silver’s shaft, lubing him for her daughter’s plot.

Rainbow argued the whole thing out in her head. What sense she had left told her that going from virgin to impregnated on a whim wasn’t a bright idea, even if she liked Soarin. On the other hoof, her ego was at stake now, and if she chickened out after getting this far, it’d look uncool to all her Wonderbolt friends.

Soarin took Windy’s assurance that Rainbow could take it at face value, so he wasn’t gentle with her virgin hole. He lifted her plot, lodged his firm tip between her lips, and yanked her down as he rammed upward. He was larger than any of her toys had prepared her for, and Rainbow stretched wider and deeper than ever before.

Rainbow bit her tongue in an effort not to scream, but that problem was solved when Thunderlane pried her muzzle open and shoved himself into her maw. He wasn’t much smaller than Soarin, and didn’t hold back either. Rainbow gagged, the shape of his shaft visible through her neck as he rammed her throat, not stopping until his fleshy orbs bounced on her chin.

Dash’s throat treated Thunderlane to the convulsions of her attempted squeals as Silver pushed home into her rear. The lubrication Windy provided him didn’t do much with him plowing a virgin plot. Rainbow shivered as the thick meat invaded her in a way she’d never intended.

All three stallions thrust roughly, and Rainbow’s brain lit up with something more intense than she ever thought possible. It should have hurt like Tartarus, but the drunkenness of her lust turned it into the purest bliss she’d ever felt.

She tried to regain her senses enough to appear that she knew what she was doing. Attempts to roll her hips in time with the first-class banging resulted in her flailing between all the sweaty stallions. None of them minded.

“Damn, Crash,” Spitfire commented. “You make me seem decent by comparison. It’s a pity your name didn’t lend itself to a filthier call sign like mine does.”

“And what’s your call sign, fire crotch?” Bow turned his attention briefly away from his daughter’s gangbang.

“Swallowfire,” Spitfire narrowed her eyes at him. “You want to know why?”

“I have a guess!” Bow grinned.

“Hey, Miss Crash’s Mom,” Spitfire called over to Windy. “Is it okay if I blow your husband?”

“Sure thing, sweetie!” Windy nodded at Spitfire, most of her attention on Rainbow at the moment.

“How about that,” grinned Spitfire. “You’re the only one to say yes to that question… other than my own mom.”

Luckily for Rainbow, she was too well-fucked to pick up the conversation, bouncing about like a rag doll. Dash grabbed hold of Thunder and Soarin to steady herself, bracing against them and rolling her hips as she caught up with the movements. It’d take more than a trio of hot stallions wrecking her virginities to knock her out.

All their bodies crashed together in a chorus of wet sticky flesh; so much for the shower. She strained to keep from collapsing entirely, limbs shivering as Soarin and Silver rammed in together. Her belly swelled on the in thrust as her pelvis strained to keep it all contained. Oh well, this wouldn’t be the worst way to crack her pelvis.

“That’s it! Go Dashie!” smiled Windy. She waved a flag with Rainbow’s cutie mark in one hoof as she caressed Thunder’s swinging sack with another and licked her daughter’s face. She savored the look of bliss on Rainbow, eyes rolled back and neck convulsing in gagging motions to milk the shaft ramming her gut.

“That’s our daughter!” Bow was every bit as enthusiastic, waving a flag with one hoof.

His other hoof gripped Spitfire’s head. He sat up, pushing her muzzle down to his crotch. Spitfire slurped his already exposed shaft, swallowing against the tip and sliding it into her throat without the slightest hint of a gag reflex. She swallowed to massage it in her throat as she bobbed her head and turned so she could watch Dash get a triple-pounder.

“Are you close to giving me a grandfoal?” Windy whispered to Soarin as she lowered her head and licked his face too.

“Nngh,” Soarin was in no shape to talk.

“Tsk, foal-making takes such a toll on most stallions,” Windy giggled. “Here, dear, let me help.”

Windy slid around behind the group, ducking her head between the two violently thrusting stallions and ran her tongue over Soarin’s ball sack. She slurped one and then the other, cleaning her daughter’s cunt honey from each before nibbling at Rainbow’s nether regions.

“Mm, so proud of you Dashie,” Windy said as she took a long lap, feeling Dash’s tightly stretched lips around Soarin’s shaft. “You two are just going to make the best grandfoal ever!”

Rainbow squealed, or at least made a valiant attempt before gagging more. Windy purred as her face got a wash of Rainbow love goo as Rainbow climaxed. Both pussy and ass twisted and convulsed around their invaders, milking them with new vigor, while the moans sent more shivers through Thunder’s shaft in her throat.

The vibrations set Thunderlane off first, and Rainbow drowned in thick seed. She couldn’t remember the last time she breathed, but didn’t care how much bluer than usual her face was. Dash might have passed out, but after blasting a few spurts into her belly, Thunderlane yanked free to give her face a bath in it. She drooled cum like a rabid whore as her face got a coat of white paint.

Silver and Soarin went off together, so tightly packed that none escaped as they expelled their hot load. Rainbow’s belly swelled until she looked pregnant already as her womb and gut flooded with thick spunk. They continued packing her full like a pair of jackhammers ramming her from behind until the impacts caused her to knock Thunderlane onto his back.

“It’s a good thing your mom warmed us up or I don’t think I’d lasted long,” panted Silver.

“That’s what moms are for!” smiled Windy.

“That is not,” Rainbow said, gagging up cum between words. “What moms are for, Mom.”

“It’s what this mom is for,” grinned Windy.

“Go Dashieeeee,” Bow did his best to cheer, though he had trouble. He grasped Spitfire’s head in both front hoofs and rammed his own load down her gulping throat. True to her nickname, she didn’t spill a drop.

“Does this mean me and Dash are getting married?” panted Soarin when he came out of his fuck-coma.

“Only if you want to live, sweetie,” Windy smiled. She was as protective of Dash as she was encouraging, it seemed.

Snap! There was a click and a camera flash as Soarin and Silver pulled free. There were a few more flashes as their excess spunk poured from both Dash’s rear entries. Windy wasted no time fulfilling her previous promise, going down on Soarin’s spent dick to taste her daughter’s wetness. Another snap got that too.

“Wow!” Scootaloo fangirled. “I just caught the moment that I became an aunt! Sorta.”

“Best aunt ever!” Bow encouraged, cock still hanging out.

“Oh my Celestia, who let her in here?” gagged Rainbow.

“Yeah, maybe we should hire security at some point,” Spitfire chuckled as she wiped her muzzle on a towel.