Canterlot Burglar
Chapter 33: Shadow Loses Her Virginity
Previous Chapter Next Chapter“It’s okay...you can do this. It’s just in and out. Nopony’ll even know you’re there…”
Shadow frowned. That little would-be pep talk that she’d given herself just then had only really served to depress her.
I mean, it’s not like I’m small or anything, right? I’m a pretty good size for my age. Hell, some ponies might say I’m too big, but what do they know? She thought to herself. It wasn’t her fault for being naturally larger than other ponies where it mattered. She’d just been born that way. If everypony was going to get vindictive or uppity about it then that was their problem, not hers.
Matters of size aside, Shadow was hesitant. She’d never done this sort of thing before. It was such a Sky thing to do. The young filly considered this her last bastion of childhood innocence, and didn’t want to ruin it just yet.
“Come on Shadow, you’re fourteen. It was only a matter of time before you’d have to do this. Besides, you’re tough enough to handle it, right? Who knows, you might even like it!” She muttered to herself. She smiled brightly for a moment before her face fell once again. The words just sounded too hollow.
What am I saying? I can’t do this, especially not with ponies watching! I’m just not ready! Shadow did a nervous little dance on the spot, glancing around. Besides, what if Sky sees me and sees what a bloody amateur I am? What do I do then? I’ve never done this before! Heck, I never wanted to do it! I’m just not that kind of pony! What if he laughs at me? I mean, he seems pretty...new to this as well. He doesn’t exactly look like the kind of pony who gets to do this stuff much...but he’ll have expectations himself, right? Oh, Luna help me...
Shadow considered taking a step back, but she was too far gone now. After all the times that Sky had done it, she couldn’t deny that she wasn’t the teeniest bit curious. So many questions ran through her mind. What did it feel like? How embarrassing was it going to be? What would happen if somepony saw her doing it? Shadow put her hooves on her fuzzy little stomach. She felt ill just thinking about what would happen if Rat or somepony else caught her doing such a shameful thing.
It’s okay, though. Just because you’re not that kind of pony doesn’t mean you can’t just...you know...try it once. Nopony will judge you for just experimenting a bit, right?
She caught herself hyperventilating. Of course they would. If she got caught doing this kind of thing, especially with another pony, then she could kiss her reputation goodbye. This was the sort of thing that her damn sister was known for, and look how she turned out! Shadow didn’t want that for herself, not one bit.
The filly slapped herself across the face to try and come back to the land of the living, blinking a couple of times and trying to focus. The enormous weight of what she was about to do bore down upon her like an ocean liner with a brick on the accelerator.
But if I do this, there’s no turning back. Not ever.
Shadow bit her lip, shivering. She wasn’t going to admit it if anypony asked, but she hadn’t been this frightened since the Elements Job. It was too big a step for a pony as young as she was. She didn’t feel ready yet. Still, Sky clearly wasn’t going to judge her for it, so there was that.
I’ve got to do it. It’s gotten her out of trouble enough times, right?
She closed her eyes, breathing deeply, before finally taking the plunge. Shadow took it in her hooves, looking down at it with something approaching absolute terror. She’d certainly seen a lot of them before, thanks in no small part to her sister, but holding one in her hooves was a different matter entirely.
She closed her eyes, cringing as she slipped it in. It was too late to turn back.
In that moment, Shadow took a step into marehood that she knew she’d never be able to take back. She wasn’t comfortable with it, but a small part of her mind knew that someday she’d have had to do this anyway, no matter how she felt about it.
Yet with the horrific act came a strange sensation of euphoria. Beyond the obvious initial discomfort that she’d been expecting, it really wasn’t so bad. She could kind of see what Sky found so appealing about this kind of thing, even though Shadow was resolved to not make this a habit. It felt good, but not that good. Most of her enjoyment wasn’t from the act itself, but from the feeling of relief that ran through her once-cold veins, relief that it wasn’t as bad as she’d always told herself it would be. Still, it wasn’t brilliant, either.
Maybe it’ll feel better if I get a bigger one next time… Shadow mused.
She still felt concerned that she was a little too young for this sort of thing, but Sky had always told her that there’s no right or wrong age for it, no matter what anypony said.
When she’d finally decided that she was done, Shadow frowned, doubtful about the choice she’d made. Perhaps a bigger one would have been better, but it was too late now. She’d already put it in her saddlebag and left.
Yes, at the young age of fourteen, Shadow had gone and bought a bouquet, and she’d done it all by herself. Best of all, nopony had seen her do it.
...What?
* * *
“So the courier’s picking up the letter for Silver Tongue at ten tomorrow, under the rollercoaster at Celestialand.” Sky nodded, examining the documents she’d stolen from Tommygun. “Huh, they’ve even got a photo of the guy. Maybe the Marefia were interested in Silver Tongue’s little scheme, too.”
“That makes sense. If a weapons contractor company starts acting weird, I guess the mob would want to get in on whatever they’re up to.” Rat chuckled. “So what’s the plan?”
“The plan is that we show up under the rollercoaster as well and make sure that the courier hands the letter off to us...then we shut him up.” Sky grinned cheekily, eyes flashing in the moonlight. “After that, we leg it back to Canterlot and work out what to do from there.”
“Yeah, about that.” Rat scratched the back of his head. “Look, I’ve been thinking...and I might’ve had a talk with Fox, too...and we...I don’t suppose you’d mind having us tag along, would you?”
Sky frowned. “That’s kinda...out of the blue. Mind if I ask why?”
“Well…” Rat smiled sheepishly. “It’s kinda...for Fox’s benefit, plus you’ve gotten me in trouble with Tommygun now, so I figure that we’d best vanish until the heat dies down. Besides, I showed you around my city, and it might be pretty cool to see yours, too.”
Sky pursed her lips, nodding slowly. “Well...I guess that sounds okay, yeah. Besides, watching Fox and Shadow together’s far too cute. I could stand to see a little more of that.” She giggled quietly, looking around in case Shadow was watching. When she was satisfied that she wasn’t about to be accosted by a pouty little filly, she turned back to Rat conspiratorially. “Okay, come on. Place your bets. Do you reckon they fancy each other?”
“Oh, I’m gonna say…” Rat glanced around, looking for his own younger sibling for a moment. “...yeah, definitely. I haven’t seen Fox this fucked up since he got hit by that carriage a few years back.”
“Damn…” Sky cringed. “Yeah, sorry about that. Shadow’s got a mean swing, especially if somepony looks like they’re hitting on her. Still...she looks pretty fucked-up herself. If I didn’t know any better, I’d say that they both blew off a hell of a lot of steam while we were settling our differences.”
“Well hey, you’re not wrong.” Rat smiled. “It’s like what they say about ponies pushing you down in the schoolyard when you were little.”
“What, if a colt knocks your ass down, it means he likes you?” Sky giggled. “I worked out that that one was bullshit when I pushed my crush down the stairs. I...well...I thought he’d kinda take it to mean that I really liked him.”
Rat laughed, shuffling closer and putting a foreleg around her. “Oh, that’s adorable! Damn, you must’ve been a cute filly.”
“Yeah, well you were probably still a stupid chump back then, too.” Sky stuck her tongue out, putting her good wing around him. “Still...you’re a cute stupid chump.”
Rat and Sky sat there in contemplative silence for a while, before he finally cleared his throat. “Um...thanks for changing me back into a stallion again.”
“Yeah, well you were a butt-ugly mare.” Sky chuckled. “And hey, thanks for helping me get this shit with the super-stallions sorted out. I guess you really put your head on the block for me, huh?”
“Eh, what are friends for?” Rat shrugged.
“Yeah...friends…” Sky chuckled weakly. “Wow...I haven’t had a friend in...like...forever.”
“We don’t get them much in our line of work, huh?” Rat nodded. “It’s so hard to make friends when you don’t know who to trust, who’s gonna throw you under a carriage…”
“Exactly!” Sky beamed. “See, you get it! I can’t even count the ponies who’ve made friends with me and led me into a trap just because I’m a walking lottery ticket.”
“The job’s fun, but it comes at one hell of a price, huh?” Rat nuzzled her cheek. “Speaking of stuff that costs an arm and a leg, I don’t suppose you wanna talk about…?”
“I know.” Sky yanked her bad wing up, letting it settle uselessly on the picnic table they were sat at. “Let me guess, you want to talk about my fashion accessory?”
“Yeah, I mean…” Rat frowned, trying to find a way to be tactful about this. “It was bleeding like fuck earlier and you didn’t exactly seem to care. I don’t care where you’re from. That shit ain’t normal, sweetheart.”
“It’s okay, Rat.” Sky beamed, tucking it back in by her side. “Trust me, it’s been like this for ages now. I’m used to it. Besides, when this shit’s over, I’ve got a little money set aside to get it fixed!”
“Don’t suppose you wanna go into how it happened?” Rat ventured, putting his hooves together and shuffling closer.
“Eeeh, it’s how every burglar gets hurt. You get cocky, you make a few mistakes, accidents happen. Every job’s a lesson, right?” Sky shrugged. “I stopped paying attention and I got in trouble for it. Guess I had it coming.”
Rat nodded quietly, fully aware that Sky wasn’t telling him everything. “Well hey, you seem to be getting on alright without it, huh?” He patted her on the back again. “Anyway, you probably wanna change those bandages. They’re pretty much bled through. Last thing you need is an infection because you can’t take care of your damn self.”
“Yeah, you’ve got me there.” Sky sighed. “Fine, I’ll go freshen up if it’ll get you off of my fucking back.”
As she got up and slung her saddlebags over her back, Rat gave her a smack on the flank. “Don’t make me wait too long, sweetheart. I’ve still gotta punish you for nearly getting us all killed.”
Sky rounded on him, kissing him on the cheek and winking. “You’ve got it.” She whispered, before trotting off to the public toilets to get herself cleaned off.
Rat waited in silence for a while, before rolling his eyes and casting his little weight reduction spell again. As he followed her at a distance, his hoof-falls fell completely silent. He was unnoticeable, a ghost.
Sky trotted into the little mares’ room, closing the door behind her. Rat approached the door himself, aware that he hadn’t done anything like this since high school. Still, in high school he was driven by something other than pure curiosity. What little he’d read of Sky’s diary earlier that day had left him wondering exactly what had happened to her.
Frowning, Rat held his breath as he opened the door a crack, peering inside.
Sky tugged at her bandages, gently and quietly unwrapping the sodden bloodstained rags as carefully as she could. The only noise was her heavy breathing, along with the occasional squeaky whimper of pain. Her legs shook underneath her as she pulled the last of the them off, dropping them to the floor in a messy heap.
“Fuck…” She breathed, placing both of her forehooves on the sink. Her shoulders rose and fell with her desperate panting as she looked herself in the mirror. Anypony who was watching her could be fooled into thinking that she was about to give birth, though she was far too thin for that.
With a laboured groan, Sky closed her eyes and extended her bad wing.
Rat stuffed a hoof in his mouth to stop himself from gasping. He’d thought it was broken, certainly, but this was something else entirely. It was practically mangled. Eight huge puncture wounds, so big that some of her bone structure was visible through the torn bloodstained feathers. How Sky was still alive with that thing, Rat couldn’t possibly imagine. Each wound looked like it had necrotised slightly, and all of them were dribbling a little trickle of blood onto the floor. The little white pony waited until she’d extended it all the way before finally opening her eyes again.
“Argh...fucking thing…” She grunted, turning side-on so that she could run her wing under the tap. The water washed most of the blood away, though Sky was shaking more wildly than ever, squeezing her eyes shut and whimpering. She was in a great deal of pain. By the looks of it, giving birth would be preferable to this.
Sky worked hard to clean herself off, doing her best to ignore the stinging sensation. She whimpered louder as the cold water hit her damaged nerve endings, a few tears running down her cheeks out of pure reflex. In time, however, she managed to clean out each and every one of the wounds, folding her wing in again and pulling some bandages out of her saddlebag.
“You’re...you’re the worst burglar ever…” She said, her voice only a little louder than a whisper.
“How’d you know I was there?” Rat asked quietly, pulling the door open and leaning against the doorway.
Sky glanced up at him for a moment in surprise before cracking a little smile. “You’re as subtle as Celestia’s ass after too much cake.” She extended and retracted both of her wings experimentally. “Ha...happy now?”
“Yeah, that kinda satisfied my curiosity.” Rat looked away from her bad wing in disgust. “That doesn’t look like it was an accident, sweetheart.”
“Yeah, well if we can get my name cleared, it won’t be a problem for much longer.” Sky shrugged, pulling a roll of bandages out of her saddlebag. She held onto the end, tossing the roll over to Rat. “Here, cop this.”
Rat caught the roll of bandages in his mouth as Sky began to wind them around her wing.
“Besides, it’s okay! This thing only hurts if I push it too hard, plus it got me off of work for a couple of weeks while I recovered. Gotta love holidays, huh?” She carried on, reeling him in a little more with every moment.
“ ‘m...no’ ‘n ‘rouble, ‘m I?” Rat mumbled through the bandages.
“Trouble, you? Nah, you’re all right, sweetie. Just...you know...keep your muzzle out of this shit in future, okay? You look pretty ill after seeing that.” Sky giggled, winding layer upon layer around her wing until the wounds were completely unnoticeable. Finally, she yanked the roll out of Rat’s mouth, drawing him close and giving him a peck on the lips. “Nopony should have to see that, should they?”
“Asking a burglar to keep out of your business?” He chuckled quietly, not pulling away. “How many times has that worked for you, huh?”
“Well, I can always distract you, instead.” Sky whispered quietly, putting a hoof on his cheek and fluttering her eyelashes. “You know, give you somewhere else to stick your muzzle, hmm?”
“Sky...you know I’m gonna find out sooner or later, right?” Rat smirked, putting his forehooves on her shoulders and giving them a squeeze.
“Then let’s make it later.” She smiled softly, cocking her head. “Right now, I’d settle for just having a little fun.”
Rat rolled his eyes, giving her a soft kiss. “Fine, but then we’re gonna have a talk, all right?”
“Deal.” Sky giggled, grabbing his cloak and pulling him into a cubicle.
I guess I’m just gonna have to wear you out until you forget to ask about it again, then… Sky thought to herself, crossing her wings behind her back.
* * *
Two young ponies in hooded cloaks trotted through Central Park towards a drop point. There was no specific drop point, you understand, just wherever the two happened to meet. Each had a plan, a message and a present for the other.
The two of them finally met by a large fountain. This part of the park felt a world away from any of the hustle and bustle of the city, and the water glowed a bright blue in the relative darkness. This was a magical little place, a sanctuary of quiet and peace at the centre of this monstrous metropolis. However, while the two ponies could certainly appreciate the aesthetics, they each had a very important task to do.
Shadow was the first to draw back her hood, her face illuminated by the blue light.
“That’s you, isn’t it?” She said as grumpily as possible.
“Yeah.” Fox nodded, pulling his own hood back. “Yeah, it’s me. I came to sort something out with you, I guess.”
“Yeah, well, me too.” Shadow nodded, clambering onto the edge of the fountain and looking down into the illuminated coin-filled depths.
Fox hopped up next to her, fidgeting slightly.
“Ever been drowned, conehead?” Shadow asked casually.
“No?”
“If you don’t wanna find out what it’s like, take that fucking hoof off of my back right now.” Shadow growled.
Fox did as he was told, whimpering. “I’m sorry, Shadow. I’m just a bit messed up right now, that’s all.”
“Yeah, I bet.” Shadow sighed. “Okay Fox, I’ll level with you. I got you something, and I think you ought to see it.”
“Well, okay. Um...I actually got something for you as well...you know...during the chase.” Fox shuffled uncomfortably. “Er...that’s where I disappeared off to for a little while…”
“Oh?” Shadow blinked, before shaking her head. “Um, well, okay then I guess. I mean, we’re all safe, right?”
“Right.” Fox nodded. “So...do you wanna show me what you got first, or…?”
“Um...yeah, sure!” Shadow smiled a little. “Unless you wanna show me what you got first instead.”
“Well, we can...we can do it together, if you’d like!” Fox offered.
Shadow glared at him, grabbing him by the mane and slowly pushing his head down towards the water.
“No! I didn’t mean it that way! I mean, show each other what we got!” Fox yelped.
“Oh, right…” Shadow let him go, flapping her wings irritably. “Well...uh…yeah…so...at the same time, right?”
“Right!”
Shadow bit her lip. She hadn’t really had much of a plan besides “throw the flowers at him and run for it” anyway, and if they did it this way, she’d be able to run off with whatever he gave her as well! This was actually sounding like a pretty solid idea to the young mare, and she flashed Fox a friendly smile.
“Sure!” She said slyly. “On three, okay?”
“Okay.” Fox nodded.
The two ponies reached into their saddlebags, maintaining eye contact as they faced off like two outlaws in the Wild West.
“One…”
Shadow grasped the flowers, gritting her teeth as if she was about to commit murder.
“Two…”
Fox looked equally tense, his ears splaying back. He kept his gaze locked with hers, however. Shadow could feel her cheeks growing warm again.
“Three!”
The two ponies drew at the same time. Shadow lobbed the bouquet into Fox’s face.
“HA! THAT’S FOR YOU, SWEETIE PIE...I mean...ASSHOLE! See ya!” She giggled, snatching Fox’s present out of his hoof and galloping off before he could properly react. The little colt was left there with a bunch of pretty orange flowers shoved over his muzzle, giving only the tiniest of tiny little squees.
Shadow spread her wings, taking off and launching herself into the air. She didn’t stop until she was absolutely certain that she’d gotten away, satisfied that Fox was too confused to offer any kind of pursuit. She circled the park a couple of times before coming in to land atop a promising tree that hid her from observation down below.
That was too easy. He was so fucked in the head to start with, and I bet that “sweetie pie” line completely messed him up! Shadow giggled, fluttering her wings excitedly. It had gone completely to plan, just as Sky had said it would.
I guess I misjudged her. She really was telling the truth after all! Shadow mused, laying back on a branch and looking up at the stars.
“Now, let’s see what I got from Fox.” Grinned Shadow, pulling out his present to her with a cheeky little giggle.
Her face fell and her ears flicked back when she saw that Fox had gotten her.
It was a bunch of very nice roses. There was a tiny little card hanging off of it. Shadow cringed at it, flicking it open as if she expected it to explode.
Dear Shadow,
I saw these and I thought of you! They’re all thorny and they hurt when you touch them, but they’re pretty and nice if you can get past that! I know that you’re like that, too, even if you don’t want to admit it. Have a nice day!
Shadow regarded the card with abject terror, especially considering how many words appear to have been scribbled out at the foot of the card before he finally settled on “Regards, Fox.” She didn’t even want to know what he’d written there before.
The filly lay back on the branch, resting the bunch of roses on her chest. What the hell were you even supposed to say in a situation like this?
“Fuck.”
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