The Dark Apprentice

“Hey Pinkie Pie!” Twilight called out as she entered Sugar Cube Corner. “I’m here for Spike!”

Spike came out of the kitchen wearing a lampshade on his head and holding a half-eaten cupcake. “Oh hey Twi,” he said. “Listen, do I have to come home right now? Because we were going to try something cool with pop rocks.”

“Spike?” Twilight asked. “Why are you wearing a lampshade on your head?”

“Duh!” Pinkie Pie called out from the top of the stairs. “Because he’s a lamp, silly.” She slid down the bannister.

Twilight looked from Pinkie Pie to Spike. “I see. Pinkie Pie has to get tired of you at some point, Spike.”

“No way, Twilight!” Pinkie Pie said. “He’s a hoot! Show her that thing you do with your tongue, Spike!”

“Oh, believe me,” Twilight said. “I’ve seen it.”

Spike threw himself to the floor at her feet, clasping his claws together. “Can’t I stay for just a little longer, Twilight? Please?”

You have friends? Then seek their counsel. An idea began to form in Twilight’s mind. “Let me talk to Pinkie Pie about it,” she said. “Upstairs. In her room. Where nopony can hear us.”

“Okay!” Pinkie Pie shouted. “Wait here, Spike!”

“Uh,” Spike said, eying them. “Okay?”

Pinkie Pie shot up the stairs, and Twilight followed her. When they were in her room, Twilight made sure the door was locked, then soundproofed the area with magic. She also tamper-proofed her soundproofing spell for good measure. “Okay, Pinkie Pie, I need to talk to you about something.”

Pinkie Pie nodded, smiling. “Uh-huh.”

“Look, it’s...” Twilight didn’t know if it was an okay thing to talk about with your friends or not. Was there a specific protocol she had to observe? “It’s...”

Pinkie Pie slowly leaned forward. “Uh-huh?”

“It’s about, I mean, I don’t think I can say it...”

“Say it!” Pinkie Pie shouted. “Say it say it say it I want to know!”

Twilight flinched. “It’s about.... se-eh-ex,” she said. drawing the last word out into a mutilated whisper. She flattened her ears against her skull and cringed, waiting for the fallout.

Pinkie Pie nodded. “Uh-huh?”

Twilight was noticing a distinct lack of fallout. A veritable absence of fallout as well as anything fallout-related. “Wait, that’s it?” she asked. “That’s not weird?”

Pinkie Pie scoffed. “Ptcha, Twilight. Why would it be weird? We’re friends.”

“I don’t know,” Twilight said as her face began to burn. “I just thought that it wasn’t really something ponies talked about. I don’t want to be nosy.”

Pinkie Pie cocked her head, smile never leaving her face. “You’ve never talked to anypony about sex before?”

“Well, no!” Twilight said. “I mean, when I was little my mother explained everything and gave me a book....” Twilight stopped and stared at the floor for several moments. “Yeah,” she said at last. “Pretty much never.”

“So you’ve never... you know?” Pinkie Pie wagged her eyebrows.

“No,” Twilight said. “Never. Being Celestia’s pupil attracted some attention from the stallions, but I always turned them down.” Twilight sighed. “I was never even curious.”

“But you’re curious now?” Pinkie asked.

“I could lose my virginity tonight,” Twilight whispered. She remembered that she wasn’t allowed to mention Luna to anyone. “I mean, I don’t want to grow old and die never having been with anypony, but I don’t know if now is the time.”

“So don’t,” Pinkie said. “You don’t have to do anything you don’t want to.”

Twilight frowned. “That’s the thing,” she said. “The more I think about this, the more I realize that I’ll always have doubts. It’s always going to be scary, isn’t it? And if I’m standing here, arguing in favor of it, then I have to want it at least a little, right?”

Pinkie Pie wrinkled her brow. “I suppose,” she said. “So who’s the pony?”

“Nopony you know,” Twilight said. “But they’re trustworthy. And...”

Twilight remembered waking up, safely nestled against the curve of Luna’s body. She remembered Luna’s breath brushing warmly past her ear. Physical contact with other ponies was almost completely alien to her, but being beside Luna for those brief moments had felt good. In more than just the way snuggling a teddy bear did.

“I’m attracted to them,” Twilight said. She immediately regretted how clinical the words sounded.

“So, yes?” Pinkie Pie said.

Twilight looked up. “Pinkie Pie,” she said. “What was it like for you?”

Pinkie Pie grinned. “I was young,” she said. “Really young.” A bubbly laugh escaped her lips as she stared at nothing in particular. “But it was my birthday.” Pinkie Pie giggled. “We were so terrible. But it was fun.”

“Fun?” Twilight asked.

“Yep!” Pinkie Pie said. “Tons of fun! It’s a whole new kind of fun, Twilight.”

“Huh.”

“I could show you,” Pinkie Pie said.

“W-what?” Twilight said. She did not just offer to sleep with me.

“We could have sex,” Pinkie said.

She just offered to sleep with me.

“Not now, obviously,” Pinkie Pie continued. “We’d have to get rid of Spike. But if you want to sleep with somepony, you should start with somepony you know, right? I’d be making you happy. It would be just like throwing you a party or baking you a cake.”

“I—” Twilight faltered with the words. “I’m sorry, Pinkie Pie. You’re my friend and all, but it would be... strange.”

Pinkie Pie snorted. “Only if you made it strange. You’ve gotta figure these things out sometime, Twi. What about just a kiss?”

Pinkie Pie was coming on to her. Pinkie Pie. Twilight felt her muscles tense, and a voice in her head started screaming at her to run away. “I don’t know, Pinkie Pie...’

“You need to relax,” Pinkie said. “It’s okay if you say no, Twilight.”

You would do well to relax, Luna had said. “Wait,” Twilight said. Pinkie Pie cocked her head to the other side. “It would be like an experiment,” Twilight said. “You’d be adding to my data set to help me reach a conclusion. And it would just be between friends.”

“Huh?”

Twilight’s heart raced. “Kiss me, Pinkie Pie.”

Twilight expected Pinkie Pie to say something in response. She thought that Pinkie Pie would slowly lean forward and let their lips barely touch. She figured she’d see it coming.

Instead Twilight found her Pinkie Pie lips on her own almost instantly. Pinkie’s eyes were shut, and her mane tickled the edges of Twilight’s face. But her lips! Twilight had once read that the lips were one of the most sensitive parts of the pony body, and now she didn’t doubt it. She could feel every millimetre of Pinkie Pie’s lips pressing against hers, wet with saliva. It wasn’t a tiny peck, either, Pinkie Pie worked her mouth against Twilight’s vigorously.

It felt good. Twilight didn’t have any experience she could compare it to: getting a massage? A hug? That steamy dream she’d had when she was younger involving Cadance?

“Silly filly,” Pinkie Pie muttered against Twilight mouth. Pinkie brought her forelegs up to wrap around Twilight’s neck and pull her closer. “You have to kiss me back...”

Twilight did. Or she tried, at least. The movements of her lips felt clumsy and inexperienced, but she thought she at least managed to passably emulate Pinkie Pie’s.

That was, at least, until she felt Pinkie’s tongue slide forward to press against her teeth. The rough texture was alien to Twilight, but not unwelcome. Without thought, Twilight opened her mouth wider so as to allow Pinkie Pie to continue her quest.

Tongues touched, and a high pitched groan escaped Twilight’s lips. Kissing. Kissing! This was why everypony had been so keen on mashing their faces together all the time. It felt good, really good. She let a foreleg wrap around Pinkie Pie’s neck. Had she really only wanted a peck on the lips just seconds ago? Now she didn’t want to stop. The rational part of her mind tried to cut in and remind her of something. That was nice. Twilight was busy kissing Pinkie Pie.

And Pinkie Pie was busy kissing Twilight. Their tongues snaked around one another as her hooves dug their way into Twilight’s mane. We’re making out, Twilight thought as Pinkie Pie pulled them to the floor. I’m making out with Pinkie Pie. They didn’t speak, other than Twilight’s occasional moan. Twilight was fine with that; she liked hearing the wet smacking of their lips and tongues running over one another.

It was perhaps ten minutes before the heard a knock at the door. Pinkie Pie pulled away, and the first sensation Twilight registered was that her mouth was empty. Cold.

“Spike!” she whispered. Her eyes shot open and she threw herself to her hooves. “We forgot about Spike! She wiped a bit of her—or was it Pinkie Pie’s—drool from the corner of her mouth. Then she undid her sound spell.

“Come on in!” Pinkie Pie called to the door. She climbed to her hooves and smirked as she bumped her flank against Twilight’s. Twilight blushed furiously. Had all of that actually just happened? Yes, she realized. Yes it had.

Spike swung the door open. “You guys have been in here a while,” he said. “Did you figure it out?”

“Huh?” Twilight said. “Figure what out?”

Spike gave her a confused look. “If Pinkie Pie can keep me,” he said. “That’s what you were talking about, wasn’t it?”

“Yeah,” Twilight said. “Yeah, it was. Pinkie Pie can keep you for another day.” She grinned like an idiot. “Pinkie Pie can do whatever she wants...”

* * *

“As in, sex,” Twilight said. “Your first time, specifically.”

Twilight and Rarity were the only two ponies in the carousel boutique. The curtains were drawn; pulled shut by Twilight. It seemed appropriate, given the subject matter. The result was that Rarity’s kitchen was dim as Rarity prepared them each a cup of tea. Twilight waited at one side of her tiny table.

“What?” Rarity said. She dropped a teacup to the floor, but Twilight caught it with her mind before it could meet an untimely fate.

“Really, Twilight. That’s not something you just come right out and ask a lady! Since when were you so... so forward?”

Since my first kiss! Twilight’s sang in her head. “I’m sorry, Rarity,” she said. “I just thought that it was something friends could talk about.”

Rarity ducked into the seat across from Twilight’s and began to nurse her tea. “We most certainly can, Twilight.” Her voice dropped to a whisper. “But you have to whisper conspiratorially and lean in, like this.” Twilight did as she was told. Having friends was pretty strange sometimes.

“My first time was absolutely dreadful, darling. He was a highborn lout from Manehattan; I was an airy little teenager dreaming of a knight in shining armor. He wanted sex; I wanted a fairytale. It all came down to the fact that he was dishonest and I was gullible. He left the morning after. I was just another notch in his horn.”

Twilight gasped. “That’s terrible!”

Rarity shrugged. “I was devastated. It didn’t meet my expectations, but then, nothing would have, looking back. The first time is terrible for everypony, in some way. It was over a year before I tried again, and this time I made sure he was a gentlecolt.” Rarity sighed. “Yes, he was a very nice fellow. Terrible at sex, though. Very unfortunate, that.”

“So you don’t even care?” Twilight said. “That you were used your first time?”

Rarity chuckled. “Twilight, it was my first time. It’s always dreadfully embarrassing and horribly awkward. I mean, what did I expect? I got it over with and learned a valuable lesson about stallions in the process.”

“Huh,” Twilight said. “Thanks, Rarity. You’ve given me a lot to think about.”

“What about you, darling?” Rarity asked. “I hear the students in Canterlot can get quite... kinky?” Rarity tittered. “Surely you have some nasty stories to share.”

“Hmm?” Twilight said as she stood. “My first time? Call me crazy, but I’m thinking it might be tonight.”

Twilight’s teleport took her away just as Rarity’s teacup shattered against the floor.

* * *

Applejack heaved the bale of hay up into the rafters, a sheen of sweat glistening on her brow. “Don’t know why you’re asking,” she said in her characteristic drawl. “But I don’t see any reason not to tell ya. I lost it to my coltfriend. He’d sneak out at night and knock on my window.”

Twilight scratched furiously at the nape of her neck. Being in Applejack’s barn with all the hay in the air around her always made her itchy.

“Anyway,” Applejack said. “He came out one night and told me he was ready. So we snuck out here and I gave myself away right in that corner over there. Course then it was later in the season and there was more hay to lie on. We made like bunnies for near on four hours before gran came in round morning. Almost gave her a heart attack.”

Twilight was taken aback. “Four hours?” she asked.

Applejack nodded. “You unicorns have got your horn-play and them pegasi have their tingly little wings. Earth ponies have got stamina. And I’ve got more earth pony in me than any other stallion or mare in Ponyville.” She puffed out her chest. “You want to tumble with Applejack, you train for four to six weeks, load up on carbs, and bring plenty of water.”

“Huh,” Twilight said. “So how was it?”

Applejack frowned. “It was sex,” she said. “For four hours.” She turned away to heave another bale into the loft. “Was great.”

* * *

“I bet it in a race,” Dash said as they strode along the road leading out of Ponyville. Dash had finished her weather work in a small amount of time, as always, and it was a cloudless, sunny day. Twilight had caught her heading to Sugarcube Corner to relax.

“You what?” Twilight said.

“My virginity,” Dash said. “I bet it in a race with this colt, Blackblitz. If I lost, he’d get to screw me under the bleachers during our third period spare.”

Twilight took this in silence as they walked. Betting it in a race? That sounded so... well, it sounded exactly like the kind of thing Rainbow Dash might do, actually. “So you lost?” She asked after a time.

Dash sighed. “I tried. Really, I did.”

“But he was faster than you?” Twilight asked.

Dash scoffed. “No!” she said. “I meant I tried to lose, Twilight. I’d had my eye on Blackblitz for months. But in the end I just couldn’t do it. I had to win.”

“Wait,” Twilight said. “So you didn’t have sex with him?”

Dash waved a hoof. “No, we still had sex. The race was really just his way of letting me know he was interested. He was still up for it when we were finished.”

“So if you bet your virginity,” Twilight said. “What did he bet?”

“Oh, that,” Dash said. “If I won he had to get his friends to stop harassing Fluttershy. He did, and we were kind of a thing for awhile because he was boning me anyway, so they all knew she was off-limits.”

“Wow, Rainbow Dash. That was very good of you.”

“Yeah,” Dash said. “I’m pretty awesome.”

“So what was it like?” Twilight asked.

“The race? It was around the regular track, but we cooked up a thunderstorm and made it so that the windshear—”

“Not the race, Dash. The sex.”

Dash waved a hoof again. “Oh, the sex. Let’s just say he misunderstood what I meant when I said I liked it fast. He’d cringe for two months afterwards when I called him Blitz. Why are you asking all this stuff, anyway?”

“Well,” Twilight said. “I’m doing a study, sort of. Collecting data for an experiment I might perform, so to speak.”

Dash arched an eyebrow. “You’re getting laid tonight?”

Twilight gave a little pout. “That obvious, huh? I’m asking everyone.”

“Oh,” Dash said. “Well then ask Pinkie Pie. She’ll have sex with anyone.”

“Rainbow Dash!”

“What?” Dash said. “It’s not bad thing, she’s just being Pinkie Pie, is all. One time I walked in on her and Pokey at one of her parties and she said, “‘There’s always room for one more!’ and I was like ‘well in that case—’”

Twilight felt her face burn as she blushed furiously. “Rainbow Dash!”

Dash seemed to catch herself and gave a light laugh that sounded a little too forced. “Too much?”

“Too much.”

“Well don’t ask Fluttershy,” Dash said.

“Why not?” Twilight asked. Fluttershy was the only friend remaining for a complete data set.

“Virgin,” Dash said matter-of-factly. “And being Fluttershy, she’s... well, you know, shy, about it.”

“Right then,” Twilight said, wheeling on the road to face the direction of the library. “Data set is complete. Time for the next item on the checklist!” Twilight waited for Dash to ask what it was.

Instead Dash took off in the direction of Sugarcube Corner. “Have fun!” Dash called back.

Twilight reviewed item two of her mental checklist. Oh, she’d be having fun, alright.

* * *

Twilight got back to the library with six hours to spare before Nightfall. She spent four of them studying up on the library’s woefully inadequate selection of books on everything sex. Mostly stallion-on-mare, but plenty of techniques that could be adapted or re-imagined.

It didn’t help her come to any sort of decision. Luna was certainly a beautiful mare, yes, and she was trustworthy and interesting and was most definitely a skilled partner, if she was to be believed. How many ponies had dreamed of taking the Princess of the Night to bed since her return?

But Twilight was Twilight the Virgin. It was all she had ever been. When stallions and mares had approached her in Canterlot, eager to take a piece of Celestia’s prized pupil, Twilight had turned them down on the premise that she didn’t need intimacy to be the mare she wanted to be. That hadn’t changed. And if she slept with Luna, she’d never, ever be Twilight the Virgin again. She’d be giving up the starry-eyed preteen who mastered magic under the tutelage of Celestia, filing her away as another part of her life.

Frustrated, Twilight cast away her books and climbed into bed. I’m being ridiculous. The past is the past and I’m not giving up my childhood by accepting a perfectly natural part of adulthood.

And there was the matter of Luna. Luna, who had held Twilight close throughout the night. Who had demanded Twilight give the matter her full attention before coming to a decision. The Princess of the Night was beautiful, but what made her beautiful? Surely aesthetics were something that could be quantified.

The way her mane flowed around her head, exotic, cool, and filled with twinkling stars. The way a lock of the ethereal hair curled just above her brow, tucked neatly underneath her tiara. The sheer force in the princess’s gaze. The graceful curve of her belly into a powerful chest, the slant of her ears, the taught shape of her skin over her hindquarters, the way she looked so right when set against the night sky, the way her voice made Twilight listen with every fibre in her body...

Would Luna remove her tiara as she lay Twilight down? Would she take off her regalia, piece by piece, and let Twilight run her hooves across her bare body? Would she lean in, breath against Twilight’s mouth, and kiss her? Would she keep kissing her, working her way down Twilight’s body until...

Twilight didn’t need to call on what she’d read out of books to know what to do next. Under her purple covers, she slid a foreleg down past her waist and gingerly stroked it against her marehood.

She shuddered as a wave of pleasure coursed through her body as the aching need she’d brought on with her fantasies was somewhat abated. Twilight gave a little whimper and threw her head back, where it pomfed against the pillow. Her horn flashed once, and every blind in the library was drawn closed as the latch on the door turned.

Twilight thought back to kissing Pinkie Pie, the other mare’s tongue playfully tangling with her own and they used their hooves to pull each other close. But now Pinkie Pie went further, picking Twilight up and throwing her onto the bed before pouncing. They’d roll around, laughing and screaming in ecstasy as Pinkie Pie let Twilight explore. No boundaries.

Twilight jammed her eyes shut. Her mouth broke into a silly smile and she cried out, wrapping her hind legs around the hoof she was using to pleasure herself. She rolled onto her belly and bit into her pillow, tasting cotton.

But she wanted to taste Applejack. The mare said she’d made love for hours. How messy it must have been, when they were finished! Twilight would have leaned in licked the sweat off of Applejack’s powerful body, the cum off her freckles, and then they’d share a sticky kiss...

“Mmmph!” Her hoof and her bedsheets were getting soaked. Was this wrong, wanting to sleep with her friends? She was just fantasizing, but...

But Twilight wanted somepony there with her, at that instant. She knew she was abandoning reason. Her head felt fuzzy, and she couldn’t wipe the smile off her face, but her nethers felt so good. They burned, and the rest of her body was catching fire too.

Rarity would make her tea and they’d tell each other silly stories. Then they’d go up to Rarity’s enormous, soft bed and they’d lie down and Rarity would say this is how us ladies treat one another, darling. And it would be soft and gentle and slow but not any less sex, and they’d suck each other’s horns like only unicorns could...

Twilight spat her pillow out of her mouth and rolled back onto her back. “Auhhh!” she screamed, clamping her free foreleg over the other. She could hear her blood pumping in her ears as she bit down on her lower lip.

She would walk in on Rainbow Dash and Pinkie Pie screwing upstairs in Sugar Cube Corner and Pinkie Pie would shout, “There’s room for one more!” And Twilight would be stuck between Dash’s lithe, muscular form and Pinkie Pie’s soft body. They’d move against her, over her, flesh against flesh, and Twilight would come, screaming.

Then it would be Pinkie’s turn, and Twilight and Dash would work together, hungrily lapping at Pinkie’s marehood, sucking at her ears and her tongue. They’d make Pinkie Pie come too, and then share a victory kiss that tasted like the mare’s pleasure. Dash would be forceful and aggressive. She’d tell Twilight what to do. And Twilight would do it, she’d do whatever Dash wanted...

Twilight’s back arched involuntarily. “Ahhh!” As she touched herself, a tightness built inside her abdomen, and her thoughts became even more fuzzy. It wouldn’t be long now...

She could have Luna tonight. And she’d learn—learn!—how to please another pony. Luna would teach her, Luna would show her. How could Twilight stay afraid of this? Her body wanted it so badly she wouldn’t have been able to tear her hoof away if she tried.

Luna would lay her down and kiss her neck and face, and they’d touch each other and become wet and wanting. She’d run her tongue over Twilight’s horn as Twilight fondled her stiff wings, she slide a hoof between Twilight’s legs and show Twilight all the things she was doing wrong right now, and all the ways she could be doing it right. What would Luna’s marehood taste like? What would Twilight’s marehood taste like to Luna? When they kissed afterward, an aggressive, wet, needing kiss, would Twilight taste herself on Luna’s lips? After Luna had lapped up the juices of Twilight’s orgasm, would Twilight be able to savor her own flavour on Luna’s tongue?

Without thinking, Twilight switched hooves from her right to her left. She brought her right hoof up to her mouth and gave it an exploratory lick.

And it turned her on even more. What was wrong with her? Was she a deviant? Twilight shuddered in ecstasy as waves of pleasure coursed through her. Would Luna be proud? She put her lips around her hoof and began to suck. She was going to come, she was about to really come...

Luna’s body against hers, moving, sliding, Twilight feeling their flesh together. Luna’s tongue in her mouth, on her ear, across her marehood. Luna’s powerful forelegs on either side of her, pinning her, almost, as they panted together. Moved together. Came together.

“Mistressssss!” Twilight screamed as the full force of her orgasm struck. “Mistress! Ah! Ah!” She panted and moaned, her words lost on her own ears as every fibre of her being burned. Waves of bliss, of pure, unbridled ecstasy shot through her, and she felt herself coming from her hooves to her ears. Her nostrils filled with the scent of her sex, and her back stuck to the bed in a pool of her own sweat, and still Twilight kept coming.

At last she pulled her hoof away from her tender marehood, then collapsed on her bed, gasping. That had been... still was...

Something that Twilight really didn’t want to go without, now that she knew it existed in the first place. And she’d be seeing Luna that night.

She’d let her head clear, Twilight decided as she lay in bed. She’d let her head clear, and see if in the two hours remaining before nightfall she’d be able to find a good reason not to sleep with Luna.

It was not a long two hours. Or a long walk through the Everfree Forest. Or a long carriage ride.

She arrived at Luna’s tower in Canterlot just as the last light of sun had given way to the dark of the night, then she stepped off the carriage with smooth surety. She turned to the bat-winged pegasi that had pulled it there. “Leave us,” she said.

They left, and Twilight turned to the Princess of the Night, who sat much as she had the evening before, with her back to Twilight and gazing at the sky. Luna spoke:

“Did you come to a decision, Twilight Sparkle?”

Twilight nodded, even though she knew that Luna couldn’t see. A faint smile graced her lips. “Do it.”