A Lovely, Yet Frightful, Night

by Michael Hudson

Rating: teen
Tags: Original Character, My Little Pony: Friendship is Magic, Romance, Fluttershy
Length: 3773

A nervous stallion goes all in by asking the shy mare he likes. He only hopes the assassin's costume he gave her helps him make this Nightmare Night something spectacular.

A nervous stallion goes all in by asking the shy mare he likes. He only hopes the assassin's costume he gave her helps him make this Nightmare Night something spectacular.

Thank you to those who proofread, Magello, RK_Striker, and Cyberbolt.

Published 2014-11-01 04:00:08 UTC
Last updated 2014-11-01 04:00:08 UTC

For my lovely

Fluttershy finally finished slipping on the overcoat, and now pulled the hood over her head. She looked in the mirror and only could barely see her mouth slightly open as she stared at the beautiful white and steel outfit she had adorned. Complete with buttons and strap to hold everything in place, she could see how an assassin might wear this.

She tried to strike a pose with one of the bracer covered hooves shooting forward and imagined a blade jutting out of it. She gave herself a small chuckle as she put it back down. Jumbled was right. Pretending to be one might be some fun.

She swallowed hard at that thought. Jumbled had been mysterious about where the odd items that he sold came from before, but she had to admit that the price made her fear just how special the clothes might be. “One date with me, in that costume, on Nightmare Night. Then it’s all yours.”

She smiled to herself though as she grabbed a piece of chocolate from the literal box of chocolate he had given her at the same time. Jumbled had said that this was the best way for him to even attempt to get a date with her, and she couldn’t help but say yes to the sweet little gesture.

She breathed deeply as she went down the stairs to put on some tea. It was about a half hour before he would be here, and she was already feeling very nervous about the date. It’s not like this is my first time going out with someone, but Jumbled has always been friendly, regardless of how distant he can be at times.

She brushed her fears to the side as the scent of jasmine filled the air. Promptly five minutes before he was supposed to arrive though, a loud knock came from her door before a muffled voice could be heard saying, “Sorry I’m early.”

Fluttershy took one last sip of her tea before moving to the front door. She opened it slightly and a red stallion waved back to her. He was in a blood red shirt tonight instead of his normal white polo and hopefully had contacts in instead of his glasses. His orange and turquoise mane looked like he woke up and simply patted it down around his horn as it did everyday. Overall, Jumbled looked his normal excited self as he smiled in the doorway and Fluttershy wouldn’t have it any other way.

Jumbled for his part lost his breath as she opened the door the rest of the way. She knocked the hood out of the way and gave him a slight smile with an equally small blush. Even with the concealing features of the cloak, her slender figure and beautiful face still stunned him as they always had. Jumbled felt himself pale and thought, Well there goes my hope that the outfit might help my confidence.

Fluttershy blushed slightly as she asked, “So, did you have a plan for tonight?”

“Ah, of course, yes. Um... do you need to do any last minute things though?” Jumbled glanced nervously around the cottage but only saw the tea cup as a hint to what may be needed to be done.

“No, not really. However, would you like to come in and finish a cup of tea with me? I’ll admit that I am still a bit nervous about tonight.”

Jumbled’s eye twitched as he walked in. “You nervous? What about me? I thought this was good idea but I have to somehow convince you Nightmare Night can be fun, make sure we both have a good time, spend probably a fortune on damages when something goes wrong, and still make sure this succeeds as a date with the prettiest mare in Ponyville!” Jumbled’s shoulders slumped but then he grinned at her. “Then again, you have to deal with all of the insanity.”

Fluttershy turned her head away and gave a slight chuckle. “Maybe some tea would be good then? Help us both calm down.”

Jumbled bit into his cheek and nodded. “I was really hoping I could be smoother when I came over. Sorry.”

Fluttershy set out a cup and shook her head. “I– I like this. It feels more natural than you trying to be smooth, besides,” she said as her volume dropped with her confidence, “I don’t think we need to both be pretending to be something we’re not tonight.” She retracted her hoof when Jumbled gave her it a small squeeze.

“I think you doubt yourself too much. Besides, we’ll be together, so you have nothing to worry about.” He shotgunned his tea and then gagged at the bitter taste. He weakly stated, “Come on then, let us begin our adventure.”

Fluttershy chuckled and finished her drink before pushing the hood back up and following him. The two trotted down the dirt path from her cottage to Ponyville proper with jumbled almost on a constant ramble as he tried desperately to find something to talk about. Fluttershy decided to stop him when he asked, “Nice weather we’re having, right?”

“Maybe we could simply walk in peace?”

Jumbled glanced down. “Sorry. I don’t really like the quiet I guess. Adds to the nervous energy I have. If it bothers you though...”

Fluttershy looked away with him and the silence grew between them. She could feel her own worries and fears growing as her mind drifted to the pranks that were probably planned for scaredy mares like her. She found her breath starting to become shallow when Jumbled bumped into her. “Eep!”

Jumbled smirked at her and slightly bumped her again. Fluttershy blushed bright red. “Sorry. I thought you might have been something else.”

“I know. Why do you think I bothered you?” Jumbled gave her a small smile before turning his head away. “It’s a shame that the running of the leaves already happened. I think the orange leaves would look nice, even in the dark of the night.”

Fluttershy nodded slightly as her wings finally started to relax. She could see it in her mind now, the glorious hues bathed in moonlight with every pony out to celebrate them. That would be wonderful. She glanced back at Jumbled and saw him smirking at her.

“A little distraction can go a long way.” His voice lost its slightly mocking tone as his eyes looked away from her. “Now if only my mind didn’t need more than a little distraction.”

Fluttershy opened her mouth, but Jumbled took off as he yelled, “I smell caramel apples!”

She smiled to herself. Jumbled had always been a little pudgy, but something told her that his hunger wasn’t the only reason he had commented. She bit into her lip as she thought, I do hope he’s okay though. I should probably just leave it though seeing as it seemed to actually make him upset and he wants the night to be happy.

She was still pondering the problem when a brown bat flew up and bopped her on the muzzle. “Agh!”

Jumbled came around the corner and pulled the caramel apple with licorice bat wings back. He looked at the panicked mare and promptly smacked himself. “I swear I didn’t mean to scare you like that. I... just stopped thinking for a moment.”

Fluttershy became quiet as her breathing returned to normal. She glanced down and then weakly asked, “Can I have one of those?”

Jumbled glanced at the apples and nodded. He slowly moved the apple to her and watched as it swayed up and down.

He gasped as he realized how he might be able to recover from the terrible joke. “Do you want to bob for apples?”

Fluttershy glanced down at his untouched sweet. “Don’t you want to eat first?”

Jumbled glanced down and chuckled nervously. “I mean afterwards. Give us something to do instead of simply trying to keep talking like this.”

Fluttershy gave him a smile that made his legs weak. “I like talking to you though.”

She’s just telling you that. He slammed a mental door on the rogue thought and merely mumbled, “Thank you.”

The two sat in another awkward silence before they dumped their apple cores and moved along. They now were with the other crowds and Ponyville looked exceptional. Lights were strung from every house and illuminated the streets in a wondrous multi-colored glow. Ponies were prancing around in a myriad of costumes and generally enjoying themselves in the cool night air. Fluttershy swallowed hard as she saw Big Mac had painted himself green and was roaring and chasing little kids. Don’t worry about it. He would know better than to scare you. Besides, ponies usually target their friends, not people they can barely see.

Jumbled tapped her with his hind hoof. “Come on slow poke. We have a shady looking friend of yours to see.”

Fluttershy bit into her lip in concern before she saw Applejack and almost bursted out laughing. She was in the same exact outfit as one of the Flim Flam brothers and even had a big fluffy mustache under her muzzle. She turned to them. “Gonna try your hands at apple bobbing Jumbled?”

“Seeing as I suck at bucking them, I say why not? Any open buckets for the two of us?”

Applejack leaned over to look at the white figure behind him and bit into her cheek. It took her a few moments but the way the stranger started to rub the ground gave her shy friend away. “Fluttershy, is that–”

“Shh. We’re trying to keep her identity a secret so that no pony pranks her.”

Applejack pursed her lips. “Alright. Go on ahead, but let me talk to Fluttershy first.” She waited for Jumbled to trot away before turning to Fluttershy. “What are you doing out tonight?”

She swallowed hard. “Jumbled asked for me to go on a date with him tonight. He even gave me this nice outfit to help me blend in with the crowd.”

Applejack bit back on commenting on how the white did the exact opposite. She instead warned, “Don’t let him do anything just because you’re scared, alright? I know Jumbled’s decent, but nopony really knows what he’s like, and I don’t want him trying to use your fears against you.”

Fluttershy glanced at the nervous stallion who was trying to act like he wasn’t watching them. He couldn’t stop fidgeting and glancing back though and he walked to the other side of the open barrel when their eyes made contact. Fluttershy turned back to her friend. “I don’t think I have anything to worry about. Not from him.”

Jumbled tried to calm himself with a deep breath as Fluttershy came over. He gestured to a small pink trail behind her. “Don’t want that giving you away now.”

Fluttershy glanced back and brought a hoof around to tuck it into the robes. “Thank you.”

“No problem. Um... you don’t have to tell me, but what were you and Applejack talking about?”

Fluttershy glanced back and then gave him a wide grin he could barely see. “Nothing. Just catching up.”

Catching up about me and how I don’t deserve her I bet. Jumbled stuck a hoof into the water and let the chill chase the doubt away. “F–f–feels great.”

Fluttershy gave him a small smile. I guess we’re both pretty bad about hiding what’s on our mind. She stuck her own hoof in and splashed a little bit of water at him. Jumbled raised on his hind legs to slam down on the barrel, but then saw Fluttershy curl up to avoid the water. “Um, maybe we should just try biting them out instead of splashing them out.

Fluttershy nodded and they both took in a large breath of air before dunking their faces in. She desperately sought an apple, trying to get into the game. She opened her eyes slightly and saw red directly in front of her. She lunged forward and bit down with all her might.

“Ow!” Both of them came out of the water as Jumbled yanked his head up. They looked at each other and Fluttershy gave out in a panicked yelp, “Oh my gosh! Are you–”

“One moment.” Jumbled brought the outstretched hoof that meant silence and licked it, He then held it up as if checking the weather before chomping down. “Ng. Okay then, I think I can say with absolute certainty that I taste terrible and that I’m sorry you had to experience that.”

She stepped back while giggling and Jumbled gave her a large grin before slamming his head back into the water. Fluttershy stepped out of the splash zone and watched as Jumbled Thought stayed underwater. And waited. She started to move closer when finally Jumbled finally emerged and gasped for air. He swiped at the air in front of him as he frowned. “I was really hoping to get you an apple that time.”

She stepped closer with a soft smile on her face. “That’s okay. Besides, I already had one tonight. Why don’t we go somewhere else since neither of us seem to be doing great at this?”

Jumbled brushed his wet mane out of his face and blushed as he looked at the soaked head of Fluttershy. It really just makes her look even cuter. “Um, yeah. That would probably be for the best. Somewhere we can dry off perhaps?”

She glanced around and swallowed hard at the surrounding ponies. “Rarity’s should have plenty of towels, and it would be a good place to take a break from the crowds.”

“Sounds like a plan!” He put a hoof to his mouth as the two slowly trotted off towards the boutique. I feel like I’m missing something. Think brain, think! He let out a sigh as nothing came to him. Jumbled glanced over to his side and pushed the worry away, calling this part a win.

They ducked through the carnival going on in Ponyville, attempting to blend in with the crowd. This included listening to different pitches for “scary” souvenirs and gorging themselves on kettle corn so as to make sure none of the food vendors would bother them too much. Jumbled just barely got Fluttershy to agree to watching him play a few games. However, he wasn’t ever good at carnival games and only by slamming the strength tester with his head instead of the hammer did he win her a stuffed chimera and earned a bruise in return. In his opinion, worth it.

However, as they neared the boutique, Jumbled finally put together what it was he had been forgetting about when he heard, “And the pony to get the biggest reaction wins.”

Rarity glanced out amongst the crowd and saw an unfamiliar red stallion in an even more garish blood red pushing a white robed mare away from the boutique. She bent over to the microphone and stated in her lovely voice, “Why don’t the lovely couple in the back come back and participate in the Scare Off?”

Jumbled felt the force stopping him from guiding Fluttershy lessen as the news dawned on his companion. However, she was not fast enough to stop the crowd of excited ponies from coming over and try to convince them to join in on the yearly competition. A stray hoof of encouragement to Fluttershy’s head instead of back and the hood came down. There was a pause as everyone realized that the mare that would decide the winner was in their midst.

Ponies surged forward, trying their best to show off their scariest maneuver. Caramel gave his best “Woo” while covered in a white sheet while Snips tried waving his cardboard scissor hands in her face. Even Rainbow got a little too excited, releasing a clap of thunder just over Fluttershy.

However, before she could scream, the air was knocked out of her by a sudden hug by Jumbled. He promptly tossed her in the air and she was suspended there with his magic before being pulled along as he trotted away. About half the crowd surged forward as the other half stayed behind, including Rainbow who was now getting yelled at by Rarity for her crass behavior.

Jumbled charged forward, his hooves thundering on the ground. He knew normally he would tire out quickly. However, this time he had two things pushing him to sprint and never stop. There was the panicked Fluttershy who was forcing him to break out in a sweat to keep up with him, and the second was the knowledge that he didn’t have far to go.

The crowd steadily closed in on him, their raucous call for their judge back growing ever stronger. Jumbled turned a corner and all the crowd saw as they followed was a quiet back street of Ponyville, and a manhole cover placed neatly in the street. The crowd grumbled as they trotted away to find someone else to give them the crown through an ear piercing shriek.

Jumbled finally eased his breathing as he heard the crowd shuffling away above them. He turned to Fluttershy who was only now standing up. He bit into his lower lip and then sighed. “Welcome to my little cave. You should probably go sit on the bed or something. I’ll make cookies.”

Fluttershy watched him trudge off and frowned at the words. They sounded detached, as if they were prerecorded. She stepped forward to follow him to the kitchen before pausing. She was in the sewer and had seen him take the manhole cover off and put it back on. However there was no deadly stench as one would expect and plenty of light. “Where are we?”

Jumbled sighed. “The sewer. Of course, this isn’t a main part of the sewer. Instead, it was probably used at one time as a staging area for ponies who were going to clean the tunnels. However, with magical items that can do the work for them, they abandoned this place. All speculation of course, but no matter what it gave me this nice little hidey hole.”

Fluttershy felt her jaw go slack in awe. “It must have taken you so long to clean this place up.”

He put down the cookie dough and started to numbly slice into it as he said, “Yep. Was supposed to be a stallion cave or something, but I never ended up talking to any of the others in town to see if they wanted to come over. Not that I’m surprised, I had to use you coming to my place of work to ask you out instead of the normal and smart thing by going to your house.” Jumbled waved a hoof in a circle while stating, “Yay for introversion.”

She prodded the ground as Jumbled continued to work. He probably blames himself for getting me to almost have a panic attack. Fluttershy bit into one of her hooves before glancing to the low hanging pipes. A quick glance down at the white garb she was in, and her mind was made up.

Jumbled sighed as he pulled the cookies out of the oven. He had heard some clanging, but the pipes made noise all of the time. He only hoped that she could forgive him and take the cookies as apology and not hate him. Why would she hate you? You were doing fine and Fluttershy will forgive you.

Really? You broke your word to a mare far out of your league, how could you possibly deserve– His thoughts were abruptly cut off as something slammed down upon him. His vision was blurred as he glanced up into an intriguing combination of bright red and yellow. A sweet voice broke through the confusion as a worried, “Are you okay?” came to his ears.

He blinked a couple times as the blur slowly faded and found deep azure eyes staring at him. He was stunned for another moment before chuckling. “Was I just assassinated?”

Fluttershy let out a deep sigh. “I.. I thought it might cheer you up.”

Jumbled’s face darkened. “I was supposed to be the one making sure you were happy, not the other way around.”

Fluttershy bit into her lip. “I am happy though.”

“Don’t patronize me.” He immediately regretted it as Fluttershy shut her eyes and glanced away. “No, I know you weren’t, its just that I know I screwed up and I couldn’t afford to do that, not tonight.”

Fluttershy climbed off, finally getting the two out of the rather embarrassing position the jump from the pipes had caused. “I know everything you did was to make me happy, and that meant a lot to me. I know that you hold my best interest in heart, right?”

Jumbled bit into his cheek before slowly nodding. “I promise, I didn’t mean to scare you. I didn’t plan to show you any of this either so I didn’t come off as just some some crazy loser. I just once wanted to prove I could be normal and at least decent if not a little cool. That way I may have just had a chance.”

Fluttershy put a tender hoof onto Jumbled’s own. “I said it at the beginning. I don’t like it when you pretend. It’s better when yourself, and I want to see more of that. Can you keep showing me that, and possibly more?”

Jumbled smirked as he rubbed her hoof back. ‘The rabbit hole goes down pretty deep, and I know it will make you run. Are you sure?”

Fluttershy stomped her hoof down. “Of course… well, yes, I hope.”

Jumbled couldn’t help but beam at her. “Can this idiot of a stallion first know whether or not he may get graced with a second date then?”

Fluttershy leaned in close, her cheeks slowly becoming red. Jumbled’s breath caught as they’re muzzles were merely inches from each other. He took a large swallow as she started to stammer and pushed her head back. “Thank you, and I promise, no more trying to pretend I’m something I’m not. I promise, from now on to be unadulterated Jumbled Thought.”

The two curled up on the bed found in the cave, and talked late into the night, a bond swiftly forming as the two let their fears, worries, and themselves be seen by one who wanted nothing more than just that.

Author's Note

For my beloved Assassinshy, in hopes that looking to this fic will help rid her of any fears you may have for my feelings, just as you have shattered mine.