Twilight's Harem

by KnightMysterio

Wonder Blunder

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Princess Twilight's Harem
Chapter 5: Wonder Blunder
by Jonathan “KnightMysterio” Spires

All characters not my own copyrighted to Hasbro and used for non-profit amusement reasons. Story contains NSFW content and should not be read by minors. In short, sex both implied and otherwise is taking place here. The initial part of the story takes place four days after chapter 4.

/\/\/\/\/\/\/\/\/\/\/\/\/\
Ponyville...
Morning...
/\/\/\/\/\/\/\/\/\/\/\/\/\

Rainbow Dash stared at the letter she had received from Scootaloo. She found herself at a complete and total loss for words, unable to fully wrap her mind around what her number one fan and little sister/daughter figure was telling her. Oh, it wasn't that what she was explaining was complicated. In fact, it was a rather sweet letter otherwise. It was just that last paragraph...

“By the way, me and the girls have decided to be Spike's harem when we grow up. Sorry for not writing sooner, we just needed to work out the logistics and stuff. Diamond Tiara and Silver Spoon are in it too. Doesn't that totally suck? And yes, we know what being in a harem means. Diamond Tiara explained it. Should have figured the jerk knew pervy adult stuff too.”

Rainbow Dash shook her head, grumbling. “Spike now,” she muttered. “SPIKE has a harem now, and my almost-little-sister is in it.” She scowled. “Twilight, you and me is gonna have to have a little TALK about that assistant of yours...”

She flew out of her house and headed straight for the library, stopping just long enough to grab a couple donuts for breakfast. As she reached the library, she saw Applejack and Rarity heading towards it as well, both of them carting letters which the chromatic pegasus could easily guess the contents of.

Rarity and Applejack nodded to Rainbow Dash as she flew up to the group. “Well. It seems we all need to have a talk about Spike with Twi,'" Applejack said.

“Oh indeed,” Rarity said. “Part of me is pleased with the fact that our little Spikey-Wikey is starting to grow up, but there's the whole 'sister in his harem' thing I need to have words with him about.”

“He just better keep his mitts offa Scoots,” Rainbow Dash said darkly. “Even after she gets old enough...”

“I share your sentiment Rainbow Dash,” Rarity said, quirking an eyebrow. “But let's chat with Twilight about this first.”

As they reached the library, however, something surprising happened. Discord stepped out, a thoroughly amused expression on his face. He noticed the approaching mares and grinned wickedly.

“Before you say anything, everything that's going on in there is Twilight's doing. I had no hand in it whatsoever, although it has encouraged me to hang around town for the next few weeks,” he said.

Great, Rainbow Dash thought internally. That's all we need, Discord hanging around.

“You need it more than most, Rainbow Dash,” Discord said, answering her thoughts. Rainbow Dash scowled, and thought something else. Discord snickered. “Same to you. But I meant what I said. Things are about to get very silly for you, Dashie.”

“Well, that can't be good...” Applejack muttered. “What's goin' on this time?”

“Spoilers,” Discord tutted. “You have to find out for yourself. Now if you'll excuse me, I promised Fluttershy I'd help her create a concert for her birds, and I have to pick up the tuba still.”

He vanished with a snap of his fingers, leaving three mares staring at the spot where he was with a look of utter bafflement. After a few moments of trying and failing to wrap their heads around the image of one of Fluttershy's tiny birds playing a tuba, they shook their heads and decided to just continue on their original task.

A maid opened the door, the pegasus clad in a form-fitting black dress and white apron. The maid's mane was bound up in a cute bun, the maid's tail line with bows. The maid blinked, gasping.

“Oh!” the maid said in a soft, breathy voice. “Miss Rarity, Miss Applejack, Miss Rainbow Dash! Welcome to the library. Can I help you with anything?”

Rarity frowned. “Er... Yes. Is the Princess in? We need to have a few words with her about letters we received from our sisters.” When did Twilight hire a maid? And why does she look familiar?

The maid nodded. “Relating to Spike, yes?” the maid asked. “Mistress is already trying to deal with it.”

Applejack nodded, staring at the maid in confusion. “Um... Yeah. Seems Spike's got hisself a harem and... err... ah'm sorry, but do ah know you from anywhere?”

The maid blushed, a sheepish look crossing the pegasus's face. “...You do actually. But I look different now since I've joined the Mistress,” the maid said in a soft, breathy tone.

Rainbow Dash rolled her eyes. “Great. Twilight's got another slave,” she muttered, staring at the maid. “...I swear I know you from somewhere.”

“I'm honestly surprised that YOU haven't recognized me yet,” the maid said in a manly voice. “Guess my new look really changed things.”

Rainbow Dash's jaw dropped in sudden recognition. “Wha... ju... kaham....” she stammered.

Applejack and Rarity traded worried looks. “Dash? What is it? Who is she?” Applejack said.

“S-SOARIN!?” Rainbow Dash almost shrieked.

“Oh mah...” Applejack said, her eyes widening.

Rarity quirked an eyebrow. “Heavens. A Wonderbolt? When did Twilight acquire one of you?”

Soarin blushed. “Us, actually. She got two of us. And it wasn't so much Mistress Twilight acquiring us as Lady Derpy acquiring us FOR Mistress Twilight.”

“Mragaglhpha...” Rainbow Dash stammered, still in shock. Rarity and Applejack traded confused looks.

“It's better if I just show you,” Soarin said in that disturbingly gentle womanly voice. He motioned for the three mares to come in, calling out into the library.

“Miss Spitfire? Mistress Derpy?” he called out.

“WHAT?!” Rainbow Dash shrieked, several glass items in the room cracking, Rarity, Applejack, and Soarin flinching from the sound.

A disturbed mewling came from a nearby room, and Cheerilee poked her head out from behind a door. She mewled happily upon seeing the three mares at the door and trotted up to nuzzle them.

“Nyapplejack! Nyarity! Rainya Dash! Is good to see you!” she mewled.

The others just grinned nervously, letting the kittyfied schoolteacher (who now had whiskers drawn on her muzzle and a sack over her tail that made it look like a cat's tail), nuzzle up against them. They had found out about Cheerilee's personality shift the day after it had happened, and were still trying to adjust to it.

Soarin called out again, and there was a sound of books falling from an upstairs room. After a few moments more, Spitfire came out, leading a slightly dazed Derpy.

“Sorry about that,” Derpy said. “We were adjusting books upstairs when I accidentally knocked over a shelf onto my head.” She shook her head, trying to clear it. “Stupid goofy eyes... I just don't know what went wrong.”

“You really need to get that checked someday,” Spitfire said, not noticing Rainbow Dash at first.

“Well, if I save up my pay...” Derpy said, she and Spitfire gliding down to join the others. She looked at Rarity's smirk and blushed. “And no, I wasn't speaking in euphemism. We really were readjusting some books upstairs.”

Rarity giggled. Applejack just rolled her eyes. Rainbow Dash just stared, her jaw dropped.

Spitfire shook her head, chuckling, and turned towards the others. She started to question Soarin, the maid-stallion standing a respectful distance from the group and looking downward, when she noticed Rainbow Dash staring at her.

“Eep!” she squeaked, startled. She coughed nervously, and said, “I... ah... I suppose some explanations are in order...”

Applejack nodded. “Ah think ah can speak for Dash here when ah say we're all wondering how you'n Soarin here got them slave rings around your Cutie Marks.”

“Some explanation of Soarin's behavior would be appreciated as well,” Rarity said, keeping silent her desire to comment on Soarin's outfit.

“Bahalama...” Rainbow Dash stammered, seemingly unable to form coherent words.

Spitfire's eyebrow twitched in frustration. “Mouth shut and stand at attention, soldier!” she snapped. Rainbow Dash eeped and immediately stood stock straight, saluting. Rarity and Applejack giggled despite the absurdity of the situation.

Derpy chuckled. “Maybe I should be the one to explain things,” she said, petting Cheerilee when the kitty pony came over to cuddle her. The whole thing started a couple days ago when Twilight got a rather desperate, panicked-sounding letter from Spike...”

“Lemme guess,” Applejack said, holding up Apple Bloom's letter, “somethin' about the Cutie Mark Crusaders and those two bullies deciding they was Spike's harem?”

Derpy nodded, sighing. “Yep, that's it,” she said.

Cheerilee giggled. “Well, maybe Spike can keep Diamond Nyara and Silver Spoon in line better than I can.”

“This isn't funny in the slightest,” Rarity snapped.

“Depends on where you're looking at it from, Nyarity,” Cheerilee teased, her tail flitting about playfully.

“Anyway,” Derpy said, getting the subject back to her story, “Mistress Twilight immediately set out to try and correct this mess. She left me in charge of the library and the others...”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Two days ago...
/\/\/\/\/\/\/\/\/\/\/\/\/\

“Derpy, I need to try and fix this mess,” Twilight said, hastily packing some books into a bag. “I'm gonna go to the camp and try and talk the girls out of it, and if that doesn't work then I'm going to try and talk to the parents of Babs, Diamond, and Silver, to see if I can get out of this without a lawsuit.” She sighed, shaking her head. “I'm HOPING I won't have to talk Rarity, Applejack, Rainbow Dash, and Scootaloo's caretakers at the orphanage out of a lawsuit, but I'm not gonna take any chances.”

Derpy frowned. “Is there anything I can do?” she asked.

Twilight nodded. “Just take care of the library and the rest of the harem for me. I've already showed you how to manage the checkout system, and the library's closed this weekend, so you should be fine. Also, I need you to run to the Cloudsdale Alchemic Concern for me and buy some supplies for an experiment I'm doing for Princess Celestia.” Her horn glowed, a bag of gems and a checklist levitating over to Derpy.

“Sky crystals,” Twilight said. “Use them to pay for the supplies I need. They're extremely expensive, but so long as you don't lose a single one of the gems we should be fine.”

Derpy gaped. Sky crystals, magically charged gems that formed only in clouds, were the absolute rarest and most valuable gems in existence, formed by a process that took years and involved heavy amounts of chaos magic. For Twilight to have even just the six in the pouch was an incredible thing. The pegasus looked inside, seeing the softly glowing, sky-blue crystals, watching the cloudlike formations inside them float about.

“You can count on me, Mistress,” Derpy said, saluting.

Twilight smiled and kissed her on the cheek. “Hopefully this won't take too long,” she said. “Goodbye, Derpy. And thank you again.”

Derpy nodded, blushing a little, Twilight vanishing in a pop. The former mailmare grabbed some bags to hold the supplies on Twilight's checklist and took to the skies, heading for Cloudsdale. Humming to herself, pleased that she was being trusted with such a big mission, she didn't notice as the bag of sky crystals slowly slipped out of her grasp, Derpy having carried them in her hooves instead of her mouth.

When she did notice, it was already too late. The bag slipped out of her grasp, Derpy yelping as it went plummeting down through the clouds.

“Nononononononono!!!” Derpy shrieked, breaking through clouds as she powerdove after the sack as it got farther and farther away. She cursed herself, knowing she just cost her mistress a fortune, that she'd messed up yet AGAIN...

Only for both Derpy and the sack to crash face first into a rather solid cloud.

“I just don't know what went wrong...” Derpy moaned dazedly, pushing herself upright. She felt her hoof touching something and lifted it up, realizing it was the gem sack. “Hahah! Success! No Derpy the Failmare today, folks!”

She put the sack into her mouth, and then paused, feeling something round and lumpy underneath her. “What the...” she reached down into the cloud and scooped up some of what was underneath her. Her eyes straightened themselves out in shock when she saw the sky crystals she was holding.

/\/\/\/\/\/\/\/\/\/\/\/\/\
Golden Oaks Library...
Now...
/\/\/\/\/\/\/\/\/\/\/\/\/\

“You found an ENTIRE CLOUD OF SKY CRYSTALS!?” Rainbow Dash almost shrieked.

Derpy giggled, nodding. “Finally my luck's having a turnaround,” she said.

Rarity shook her head, amazed. “How... how many did you find?”

Derpy gestured absently to Soarin, the maid pegasus nodding demurely and heading into another room. There was a brief sound of a safe tumbler turning, and soon after Soarin came out with three bags filled with five gems each, setting one each in front of Rarity, Applejack, and Rainbow Dash.

“Enough to share, even after Mistress Twilight made a big donation to the city,” Derpy said simply, smiling.

“...I think I just came,” Rarity said, biting her lip and grinning.

“...Ah could buy TEN WHOLE HOUSES with this!!” Applejack shouted, shocked.

Rainbow Dash stared at Derpy, and then quickly zipped downstairs, coming up with a device from Twilight's lab. She activated it, a green magical light washing over Derpy, Soarin, Spitfire, and Cheerilee.

Nothing happened.

“Good theory, cadet, and good execution,” Spitfire said, Rainbow Dash blushing at the praise, “but there's no changelings here.” She shook her head, chuckling. “Things are weird enough, thanks. Now let Mistress Derpy finish her story.”

“Thank you,” the walleyed pegasus said.

Rainbow Dash just grumbled, flying over to Rarity and Applejack, the former giggling despite herself as Cheerilee cuddled up to the pegasus.

Derpy smiled. “Anyway...”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Cloudsdale...
Two days ago...
/\/\/\/\/\/\/\/\/\/\/\/\/\

Derpy smiled, whistling to herself. She had gotten all the alchemy materials first, including some extra, leaving her with plenty of sky crystals to play around with. She had some time before she needed to get back, so she decided to just glide around the majestic cloud city, taking in the sights.

She giggled happily. She had only been here a few times, having lived on the ground most of her life, but she was always fascinated by the ancestral city of the pegasi. And to her delight, she only crashed into things by accident three times! A personal best! This was definitely her day.

The moment the thought passed through her head, a nearby casino caught her eye. She hesitated, mulling the decision over as she studied the neon lightning that lit up the gaudy sign. The Skyway Robbery, the casino was called. Derpy giggled. She had never been into a casino before...

“Well, why not? I'm sure I'm pushing my luck, but I can actually afford it this time,” she said. She glided up to the door, skidding to a halt just outside the door.

The bouncer at the door took one look at her eyes and said, “Sorry. I don't think this place is for you.”

Derpy glared at him. “Excuse me?”

The bouncer, a lavender and orange pegasus stallion, sneered and said, “We don't got 'special' games for 'special' ponies. Why don't you go back to your nursing home, lady?”

Derpy sighed. But she was long used to ponies thinking she was retarded just because of her eyes. “So I guess I won't be spending my sky crystals here, then?” she said, holding up one of her bags of sky crystals.

The bouncer snorted. “Yeah right, like you actually have a bag of...” he trailed off, staring at the softly glowing gems. He giggled nervously, holding the door open for her. “Come right in, ma'am. Please, enjoy yourself at the Skyway Robbery.”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Golden Oaks Library...
Now...
/\/\/\/\/\/\/\/\/\/\/\/\/\

“You DID report him to the manager, didn't you?” Rainbow Dash said.

“Of course I did,” Derpy said. “I did that first thing.”

Rainbow Dash huffed, nodding. “Good. I may not like you all that much, but you're a good pony and a good mom. You don't deserve to be treated like that for something you can't help.”

Derpy blushed, grinning, and continued her story.

/\/\/\/\/\/\/\/\/\/\/\/\/\
Skyway Robbery...
Two days ago...
/\/\/\/\/\/\/\/\/\/\/\/\/\

Derpy looked around the casino, grinning widely. The center of the casino was a wide tower, the different floors having no rails to make it easy for pegasi to fly from place to place. Games, bright lights, the smell of alcohol and good food, and the sound of laughter surrounded the walleyed pegasus.

She eventually decided on a place and flew up to it, spying a set of couches and a big monitor showing a racetrack and various racer stats. What caught her eye immediately afterwards were the twelve pegasi gathered around the couches, laughing and having a good time.

She recognized them immediately, of course. Anyone who was around Rainbow Dash for more than a day knew who all of the Wonderbolts were.

Placing a sky crystal on the bar (making the bartender's jaw drop in the process), she told him to use it to pay for the next few rounds of drinks for the Wonderbolts and whatever they were eating. The bartender nodded, eagerly flitting off. Derpy flew over to the couches and sat down, calmly sipping her own drink, a tomato juice. When the next round of drinks came (nothing alcoholic, as the 'Bolts were all professionals) and they found out Derpy paid for them, several of the Wonderbolts began to talk with her.

“I remember you from Tornado Day in Ponyville,” Spitfire said. “You had a good top speed. Little clumsy on your flight path, though.”

Derpy just smiled, appreciating the honesty. “Thanks. I've always had trouble flying straight. These damn eyes,” she muttered.

“They're a pretty color, I know that much,” said Soarin, chuckling when Derpy blushed. “Thanks for payin' for our drinks and food.”

Derpy smiled. “You've all done so much for Equestria. Plus, I kinda want to make Rainbow Dash jealous, say I got to hang out with the Wonderbolts.”

Several of the Wonderbolts, familiar with Rainbow Dash, just chuckled. “Hey, Dasher's alright,” said Fleetfoot, tossing some popcorn into her mouth. “Great flier, responsible leader... She just needs to dial down the fangirlism a bit.”

“Tru dat,” said Skybird, sipping his drink.

Spitfire laughed. “Hey, lay off. She's more than proven herself, she's just got to get her teamwork up to par before we make her part of us officially,” she said.

/\/\/\/\/\/\/\/\/\/\/\/\/\
Golden Oaks Library...
Now...
/\/\/\/\/\/\/\/\/\/\/\/\/\

Rainbow Dash squeed happily. It was disturbing. “Did you really say that?” she said, her eyes sparkling.

Spitfire rolled her eyes. “Yes, and I meant it. But that's not the point of the story,” she said calmly.

Rainbow Dash coughed, forcing herself to calm down. “Right, sorry.”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Skyway Robbery...
Two days ago...
/\/\/\/\/\/\/\/\/\/\/\/\/\

“Hey, thanks for paying for our munchies, by the way,” Soarin said.

Derpy nodded. “Thanks. I had a bit of a windfall recently, figured I'd indulge myself for once,” she said, holding up one of her bags of sky crystals showing it to them. The Wonderbolts all stared, shocked.

“Holy...! Where did you find this?! HOW did you find this?” Surprise said, the white and yellow pegasus amazed.

Derpy giggled, closing up the bag. “Sheer dumb luck,” she said. “I was running some errands for Princess Twilight and accidentally dropped the six that she had before... I literally crashed right into the cloud.”

“Wow...” Spitfire said softly. “Wait, for the Princess?”

Derpy nodded. She hesitated a moment, and said, “You've heard about the recent stunt the nobles pulled on her, right?”

There was a brief moment of hesitation as they all tried to recall. Spitfire was the first to remember. “Oh yeah, I've heard of that. Something about some old BS law that says that princesses have to have a harem...” Her eyes widened when she saw Derpy blushing. “Wait... You mean YOU...”

“I'm one of Princess Twilight's harem girls,” Derpy said, smiling

“Lucky lucky,” teased one of the Wonderbolts. “I know some guys who'd give their wings to share a night with a Princess.”

Derpy shrugged. “I kinda had to...” she said.

“Had to? How do you mean?” Surprise asked.

“Prince Blueblood decided he didn't like me,” Derpy said, scowling.

As one, the Wonderbolts cringed. They'd all heard of the decidedly unpleasant prince and didn't need further explanation than that.

The conversation became much more pleasant afterward, Derpy casually chatting with the Wonderbolts. All the while, though, Soarin had a thoughtful look on his face.

“Hey, Miss Derpy? You ever gamble?” he asked.

“I try not to,” Derpy said. “My luck usually works against me.”

Spitfire glared at him suspiciously. Soarin smiled, a calm, easygoing smile. “Well, we've been placing bets off and on as the races have been going on. Why not get in on it? There's a new race coming up, you might win some more pocket money.”

Derpy frowned, looking at her ten bags of sky crystals, tied up against the larger bags of alchemic supplies she had with her. “I don't know, Soarin...”

“C'mon! It'll be fun,” he insisted. “Here, they're talking about it right now.” He gestured to the monitor, which had begun showing profiles of the racers.

“I suppose it couldn't hurt,” Derpy said after a long moment. “Who are you betting on?”

Soarin gestured up to a lean-looking pegasus with a cyan and orange coloring. “Quicksnap,” he said. “He's the odds on favorite.”

Derpy stared at the skinny pegasus for a long moment, watching as he did exercises to limber up and then looked over the other contestants. Her eyes settled on a slightly chubby black and red stallion and she nodded. “Okay, I'll take that bet. All my remaining sky crystals on Coltic Thunder to win.”

Soarin grinned wickedly. Spitfire blinked. “Woah, wait a minute,” she said.

Soarin chuckled. “It's cool, it's cool. I won't take all her money,” he said. “Just a bag or two.”

Spitfire scowled. “Aren't you forgetting something? You need to MATCH her bet for it to be legal! How in Tartarus are gonna match SEVERAL BAGS of sky crystals?!”

Soarin blinked. “Good point,” he said, calling over an employee. “Hey, what would I have to give to match a bet of... how many sky crystals do you have?”

Derpy did a quick count. “Seventy-two,” she said.

Soarin giggled compulsively. The employee nearly choked, the words 'big spender' flashing in her head. “Sir...” the casino employee said, “To match a bet of that magnitude you'd have to bet yourself and at LEAST one other pony at minimum.”

Soarin blinked. “What do you mean?”

“You'd have to wager yourself and another's freedom. You lose, you and the other pony you bet belong to the winner forever. That is the ONLY thing capable of matching that many sky crystals in value.”

Derpy blinked. “Wait, I thought sex slavery was the only legal kind of slavery left, and it only had to last a year,” she said.

“Legal loophole,” Spitfire said, sipping her apple juice. “Princess Celestia's been trying to close it for years, but the nobles have been fighting her all the way. Still, it's never really come up in ages because nopony's been dumb enough to...”

“I'll take it. I bet me and Spitfire against Derpy's gems,” Soarin said, nodding, several of his teammates spitting out their drinks in surprise. “Write it down, make it official.”

“WHOA!” Spitfire said, alarmed. “Wait a moment! You can't just...”

Soarin grinned. “Spitfire, just look at Quicksnap! He's lean, he's agile, he's quick... it's a sure thing! We can't lose!”

Spitfire looked up at the lean pegasus. He did seem to have a lot of speed on him... And Soarin was rarely wrong about such things. Still...

“I don't know, Soarin... If we lose...” Spitfire said softly.

Soarin smiled. “Trust me,” he said. “I know what I'm doing.”

Spitfire stared at her longtime friend and flying partner for a long moment... and sighed. “Okay. Fine, I agree. Make the bet.”

The employee shook her head, pulling out a notepad and writing down the bet. Derpy said nothing, she just stared at the monitor, watching the race intently as it started. Spitfire and Soarin sat nearby, Spitfire biting her lip nervously, Soarin watching in amusement.

Sure enough, Quicksnap took an early lead, and seemed to be dominating the race, Coltic Thunder several lengths behind. But as the race reached its final lap, Soarin's face slowly began to fall.

/\/\/\/\/\/\/\/\/\/\/\/\/\
Golden Oaks Library...
Now...
/\/\/\/\/\/\/\/\/\/\/\/\/\

Rainbow Dash facehoofed. “Lemme guess. Coltic Thunder put on a burst of speed near the end while Quicksnap started to tire and slow down,” she said.

“Yes,” Spitfire almost snarled, Soarin whimpering.

“It was a sure thing!” he wailed in his real voice.

Derpy and Spitfire glared at him. “I don't recall either of us giving you permission to speak in your normal voice,” Spitfire said.

“Sorry...” Soarin said in his womanly voice, shying away from the two of them. Applejack grimaced, not sure how she felt about this.

Rarity shook her head. “Wait, I don't understand. How did Coltic Thunder win?”

“Remember when Twi got fourth place in the Running of the Leaves, and second place year after?” Applejack said. “She held back, keepin' up with the pack but not goin' all out. When she got near the finish line, she put on a big boost o' speed and jumped ahead of everypony.”

Rainbow Dash nodded. “Plus, Quicksnap, from the sound of things, was much leaner than he should have been. Pegasi can tap into fat reserves for a boost of speed, so I never let myself get too skinny.”

Derpy nodded. “And Quicksnap was exercising way too much before the race,” she said. “Whenever I went out to make a far away delivery I always made sure to be well-rested so I wouldn't get tired along the way.”

“Can't believe I forgot all that...” Spitfire muttered. “Stupid Soarin...”

Rarity nodded. “All right, that makes sense.”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Skyway Robbery...
Two days ago...
/\/\/\/\/\/\/\/\/\/\/\/\/\

“COLTIC THUNDER WINS! OUT OF NOWHERE, COLTIC THUNDER PULLS AHEAD AND COMES IN FIRST PLACE!” shouted the announcer.

The Wonderbolts table was dead silent. Soarin's jaw had dropped almost to the floor, his expression hilarious to those who passed by. As was Spitfire's expression of sheer, fuming rage that she directed at Soarin. The other Wonderbolts turned to Derpy, staring at her as she got out a couple sky crystals, giving them both to the stunned bookie that had written down the bet.

“For your trouble,” she said. “One for the casino, and one for you to keep.”

The bookie just nodded numbly. Derpy grinned. “Can you get me a couple ropes? Something to use as leashes, I mean.”

The bookie nodded again. “There's... there's some rope in the back...” she said, gliding off to get them.

Derpy popped her neck. “Soarin was right, that was fun!” she said, chuckling. She turned to Fleetfoot and said, “Do you have a schedule of Wonderbolts events I could have? Mistress Twilight will want to make sure that they don't miss a show.”

Fleetfoot blinked. “Wait, you... she's gonna let them still fly with us?” she said.

Derpy frowned. “Well, why wouldn't she? This is Twilight Sparkle we're talking about here. Multi-time world hero. She's not about to deny someone their livelihood, now is she?”

“True...” Surprise said. “She did help us get those new fireproof suits...”

The other Wonderbolts started to relax. “We'll mail you the schedule for our training sessions and shows,” Fleetfoot said.

Derpy grinned. “Thank you!”

Skybird cackled. “Don't play with them too roughly, we need our captain in top flying shape!” he said.

“But... but it was a sure thing...” Soarin said softly.

“You BLITHERING IDIOT!” Spitfire snarled. “You bet our FREEDOM on a RACE!!! I don't know who's dumber! You for making the bet or me for going along with it!!”

Derpy just shook her head at them. The bookie came back with the ropes, Derpy getting her to help them tie them around the necks of the two Wonderbolts she had just won. She said her goodbyes to the other Wonderbolts, picking up her bags, and led her two new toys out, Soarin muttering 'It was a sure thing' over and over while Spitfire came up with increasingly creative ways of berating Soarin.

They didn't even notice, Soarin still muttering the same five words over and over again and Spitfire still snarling at him. They didn't notice the trip back, Derpy whistling to herself, didn't notice Twilight appearing in a flash.

“Oh! Derpy!” the alicorn said, smiling. “I'm very glad to see you.”

“Good afternoon, Mistress. How'd it go with the Crusaders and the two bullies?”

Twilight groaned softly. “That bunch can be remarkably stubborn when they set their minds on something,” she growled. “I need to talk to their families now... Why do you have Spitfire and Soarin on leashes?”

Both Wonderbolts flinched, startled, noticing Twilight for the first time. Derpy giggled. “I brought home some presents,” she said, tugging Spitfire and Soarin forward. “I've had a VERY good day.”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Golden Oaks Library...
Now...
/\/\/\/\/\/\/\/\/\/\/\/\/\

“...And that's pretty much it,” Derpy said, Spitfire sighing and looking down at the ring around her Cutie Mark.

Rainbow Dash's jaw was drooping open again, the pegasus still in shock over what happened to her idol. Rarity looked from Soarin, acting meek and demure, to Spitfire, who just seemed depressed by the whole ordeal.

“...You seem to be taking this rather well,” Rarity said.

Spitfire shrugged. “As Derpy said back then, it's Twilight. Mistress helped me with some paperwork I had to do, having it shipped here, and the sex wasn't that bad. Soarin and I go back to Cloudsdale in a couple days for a training session at the Academy.”

Rainbow Dash nodded. She knew about that too. Applejack frowned, and asked, “That still don't explain why Soarin's actin' like a girl.”

Derpy gestured to a pile of papers on the nearby desk with notes scribbled on them. “Mistress is experimenting with fetishes. She saw how mad Spitfire was at Soarin and decided that an experiment in sissification was in order.”

Soarin blushed. “I... I'm actually kinda enjoying myself... And this dress makes me feel pretty...” he said softly.

Rainbow Dash made a strangled mewling noise. So distracted by this was she that she didn't even notice that Cheerilee had been playing with her colorful tail for the past ten minutes.

It was at that moment moment that Twilight Sparkle chose to appear again, an irritated look on her face and a bag held by her magikinesis. She turned, noticing her friends, and said, “PLEASE tell me you're here to yell at me.”

“E-Excuse me?” Rarity said, baffled.

“I need a normal reaction to the girls deciding they want to be Spike's harem,” Twilight said. “I just finished talking with the parents of Diamond Tiara, Silver Spoon, and Babs Seed, along with Scootaloo's caretakers, and they all were just weird about this.”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Sunny Smiles Orphanage...
Earlier...
/\/\/\/\/\/\/\/\/\/\/\/\/\

“Oh, Scootaloo's always getting into situations like this,” said the pegasus nurse. “But so long as Spike doesn't do anything ungentlemanly towards her until she turns eighteen, then it should be all right.”

“Oh yes indeed,” said the unicorn. “Spike is SUCH a nice dragon. Always helpful and friendly.”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Rich Estates...
Earlier...
/\/\/\/\/\/\/\/\/\/\/\/\/\

Filthy Rich just sighed. “I've just about given up trying to get my daughter to stop being a bully, especially towards the Crusaders. She just keeps ignoring my advice to her.”

“Indeed,” Topsy Turvy said. “If Spike can keep our lovely Diamond from being mean to everypony else, then I say more power to him.”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Silver Estates...
Earlier...
/\/\/\/\/\/\/\/\/\/\/\/\/\

“Ohohohohoho!” tittered Silver's mother, Silver Shield. “Our little Spoony is such a social climber!”

“Ohohohohoho!” tittered Silver's father, Silver Hammer. “Indeed! Attaching herself to a Princess's aide this early!”

“Ohohohohoho!”

“Ohohohohoho!”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Babs Seed's Manehattan Home...
Earlier...
/\/\/\/\/\/\/\/\/\/\/\/\/\

“Is the dragon fuckin' her now?” asked Babs's mother.

“No, of course not,” Twilight said, huffing.

“Is he plannin' on fuckin' her anytime before she turns eighteen?” asked Babs's father.

“OF COURSE NOT!” Twilight shouted.

Babs parents looked at each other and said, “Then we don't see the problem.”

/\/\/\/\/\/\/\/\/\/\/\/\/\
Golden Oaks Library...
Now...
/\/\/\/\/\/\/\/\/\/\/\/\/\

Rarity's eye began twitching, Applejack and Rainbow Dash staring at Twilight with their jaws dropped, Derpy, Spitfire, and Soarin having similar expressions on their faces. Cheerilee just mewled, having dealt with Diamond's, Silvers', and Scootaloo's families before now. She knew that would be their reactions.

“...Everypony in this town is nuts,” Rainbow Dash said after a long moment.

“Ah'm startin' to think so,” Applejack said, shaking her head.

“I've been saying that from the beginning,” Twilight muttered under her breath.

Rarity, finally, huffed. “You know what? I'm done. I quit. I'm through fighting this nonsense,” she said, picking up her bag of gems.

“Rarity...” Applejack said softly.

“So long as he doesn't lay his grubby mitts on our sisters and/or sister figures before they're adults, then I say fine,” Rarity said, shaking her head.

“I'm so sorry about all this,” Twilight said.

Rarity giggled. “It's fine, darling. I'm not mad at you or Spikey-wikey,” she said. “I just... er...” She noticed Twilight's bag that she had appeared with, taking special note of the long, cylindrical box in it, one that bore the label of a shop in Canterlot she was familiar with. “....Spent the day in Canterlot, did we?”

Rainbow Dash and Applejack turned to the alicorn, confused. Twilight blushed, levitating the package out of the bag. “Yeah... I needed a break after that fiasco with the families, and I remembered you telling me about this place, and I figured it might have what I need to help Spitfire with something.”

Spitfire blushed brightly.

Applejack sighed. “Ah know ah'm gonna regret asking, but... okay, what'd she need help with?”

Twilight just looked at her pointedly. “I... ah... I'd never had anal before and... ah... I couldn't fit your brother's penis up my ass...” Spitfire said, her blush deepening. Applejack gagged.

Rainbow Dash squeaked, blushing, while Rarity and Applejack's eyes widened, naughty thoughts flowing through both mares' minds.

Twilight levitated out a long, thick dildo, holding it aloft like a sword. Rarity gaped. “Is... is that as big as Big Macintosh?” she asked, breathless.

“Little smaller, actually. It was the biggest size they had,” Twilight said casually, looking over the manual that came with the dildo.

“S-Smaller?” Rarity stammered, visions of Mac dancing through her head. And, to Applejack's dismay, her own head as well.

“Oh merciful skies...” Spitfire said, gulping nervously.

“This works out for me, as we can use it as a training device,” Twilight said. “After all, you seemed to greatly enjoy it when Mr. Cake and Soarin took you up the rear, now didn't you?”

“That's... true...” Spitfire said, grinning weakly.

Twilight looked thoughtful for a moment. “I'm gonna test this out on her,” she said. “If you wanna stay, that's fine, but things may get squishy in here rather quick.”

Rarity shook her head. “Oh dear... This may be unladylike of me, but I have to see this...” she said.

Applejack just muttered something incoherently, trying to dispel the incestuous thoughts that were flowing through her head.

Rainbow Dash squirmed uncomfortably, not wanting to be the one who left first. She REALLY didn't want to see this, but didn't want to lose face by retreating before the others.

Twilight shrugged. “Okay then...” she said. “Spitfire, lean forward and raise your tail.”

“Fuck it,” Rainbow Dash moaned as her nerve broke, bolting away in a streak of color. All my friends are pervs!!

“Rainya Dash a prude?” Cheerilee said. “Nyever would have thought it.”

Twilight just shook her head. “She'll be fine,” she said. “Spitfire?”

Spitfire gulped and nodded, dropping to her front knees and raising her tail. Slowly, Derpy guiding the massive tool, Twilight began to push the dildo into the pegasi's ass, pouring a clear lubricant on it as she inserted it.

“Aanh!!” Spitfire yelped. The tight pucker was spread wide by the dildo, Twilight taking careful note of the Wonderbolt Captain's reactions. The other mares and mare-like stallion in the room just watched, fascinated, as Spitfire squirmed underneath the slow insertion of the tool.

Oh Celestia it's stretching me so tight why does it feel so good?! Spitfire thought randomly, feeling herself get very wet from the sensation of her ass being filled so tightly. She winced a little, feeling her limits reached, but Twilight kept slowly pushing the dildo into her, gently caressing her flanks and keeping the lube pouring in. Spitfire shuddered, gasping softly as the dildo was worked in up to the hilt. She felt a pair of plastic balls pressing up against her ass, realizing that Twilight had fit it all into her.

“Ngh...” Spitfire grunted.

Twilight nodded. “How are you feeling?”

Spitfire managed to giggle. “Well, some ponies have told me I have a stick up my plot. I guess I do now,” she said.

Twilight smiled. “Seriously, though. How are you feeling?”

“Fully packed,” Spitfire said. “It's... tight, a little past what I can take normally. But I'm not hurting as bad as I was when Big Macintosh mounted me.”

Applejack blushed, having a sudden image of her brother humping Spitfire intensely, an image that quickly changed from Spitfire to her underneath her brother, feeling his massive member pounding into her...

“Ah... ah gotta go,” Applejack said, her voice husky. What the hay's the matter with me?!

Rarity frowned. “Will you be all right, dear?” the fashion designer asked.

“As soon as ah can stop thinking about my big brother as a sex object,” Applejack muttered, slamming the door behind her.

Spitfire chuckled weakly, laying down on the floor. “So... so now what? Leave it in until I'm... ah... looser?”

Twilight grinned wickedly. “No. Now we turn it on!”

“Turn it on?!” Spitfire said. Before anypony could react, Twilight reached down and flicked on a switch in the back of the dildo. A soft, electronic buzzing came from the device, Spitfire jerking as if shocked.

And indeed, the sudden surge of pleasure from the now steadily vibrating dildo within her ass was like electricity, the pegasus's mind shutting down from the decidedly pleasant tingling. She flopped over, shuddering in delight.

“My ass... anh...” she moaned. “So good...”

Twilight giggled, scribbling down some more notes. Rarity fanned herself a little, blushing. “Dear me. You're getting the hang of all this quite quickly,” she said.

Twilight chuckled. “When have you known me NOT to apply myself vigorously to any new project?” she said.

Derpy giggled. “'Vigorous' seems to be a very appropriate word for this whole situation,” she quipped.

Rarity rolled her eyes. “Well, I'll leave you to your playthings,” she said, picking up her gems. “We're still on for tea tomorrow, yes?”

Twilight nodded, nuzzling her. “Yes. Thank you,” she said.

Rarity grinned. “Just remember what I said about Spike. See you then, dear,” she said, stopping to pet Cheerilee, the kitty pony mewling happily. She stepped outside the library, blinking when she saw a crowd gathering near the center of town. She followed the them, coming upon a giant stage where Opal, Owloyisius, Angel, Tank, and Winona were all playing jazz music, each playing a different instrument, Gummy also on the stage with them, singing a rather upbeat song.

Also, they were all turned into bipedal versions of themselves, clad in stylish outfits. Discord was conducting the impromptu orchestra, an amused Pinkie Pie and Fluttershy sitting in the front row.

She came up to them, frowning.

“Now, before you say anything, Rarity,” Fluttershy said, “this was all the pets' idea. They wanted to be in a band. Discord just suggested jazz music.”

Discord cautiously glanced over his shoulder, watching Rarity.

The pure white pegasus stared at the stage for a moment, seeing her Opal enjoying herself greatly as she wailed away on her saxophone. She then chuckled, shaking her head.

“Sure, why not?” she said.

Discord grinned. “That's right, m'dear! Embrace the chaos!” He gestured absently with his tail, creating a plush couch for Rarity sit on. “Play it, Gummy!”

The alligator obliged.

“When I was a little gator

I dreamed I'd get the chance

To blow my horn in Ponyleans

And make the ponies dance!

I practiced playin' night and day

To make this trumpet sing!

All the cats in the bayou know

I can blow this thing!

Well I was born

I was born to blow this horn!

When I was born that early morn'

My momma said blow your horn!

I'm a star!

They all come from near and far!

Late at night to the early morn

I'mma gonna blow this horn!”

TO BE CONTINUED...

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