--- Chapter I --

It was a fairly sunny day in the city of Canterlot clouds forming and parting throughout the day, as the busy square was filled with chatty ponies and tourists a small grey and blue unicorn was in the mix of it all heading to work

His simple name was Jackk

The grey stallion trotted through the packed cobblestone roads as he headed to the castle library for work, as usual he stopped for a cup of apple cider and a small apple pie for breakfast and as he waved and nod at any ponies making eye contact he continued subtly rushing

Jackk Skies was the assistant manager of the castle library he actually just got promoted about a week ago, he had been working off and on as roomkeeping and librarian but he has always worked at the castle since he was a young stallion, he seemed to admire their work and loved the atmosphere of the town and castle as a whole

Once getting to the castle gates, Jackk headed into the castle, of course showing Identification to the guards that were on duty, as he slowly trotted up the corridors of the castle he soon reached the arched doors of the library, once using his magic to trot right on in he was quickly greeted by his boss Sunburst, who was interning at the time for the owner of the library.

“Hey J!” Sunburst shouted from one of the book isles as he had a warm smile on his face, brushing his mane back and setting some books down

“Hello, Sun.” the grey stallion replied with as he had a sort of content smile, a bit frazzled from the walk here

Nevertheless he set his bag down on the other side of the library’s desk, as well clocking in for the day

“How has your morning been?” Sunburst soon said as he narrowed his eyes towards Jackk

“Fine i suppose, my parents were visiting for the weekend which was nice..” Jackk replied, his voice was quiet and shy compared to some of the ponies here

“Oh how nice” the nerdy pony said “We got another intern from Manehattan” Sunburst added as well

“Whats their name?” Jackk replied, his ears perked up as he narrowed his hazel eyes towards the orange pony

“Winterfall Storm” Sunburst quipped

Said pony came trotted out from the halls, he was a short all white stallion with incredibly deep blue eyes, Jackk had narrowed his eyes towards him but his eyes also quickly parted as a small blush started to form on his cheeks

“Hey all!” he chirped as he trotted over towards the desk, making the grey stallion start to blush a bit more, he wasn’t a very expressive pony but he sure was into stallions, perhaps he hid that side of him as a professional thing perhaps he just wanted to stay in the closet, no one really knew why and there were only maybe three friends of his that knew he was mega gay

Nevertheless as Winter did approach the other stallion scooted away to allow him free space
Such a gesture made Winter a bit weary he got in his way

“Excuse me.. Sorry.” Winter said quietly towards Jackk as he went and grabbed a cart from the back to collect some books. Jackk’s blush had faded for the most part after

“No.. uh. No worries” He said, on the outside he was content but on the inside he was absolutely dying of embarrassment for himself i mean yeah, Sunburst was cute, but he wasn’t really his type, and besides saying two words to the other he didn't have much interaction with him whatsoever

Yet something sparked inside him just looking into his baby blue eyes

After having a moment of sheer embarrassment and overthinking Sunburst did burst his bubble by shouting quietly;

“Hey! J! Can you go shred some old damaged books in the back?”

Jackk did jolt up a bit from the sudden tone but quickly stumbled forward trotting to the back room for the book shredder “Yes sir!” he said as he done so

Sunburst merely scoffed as he smiled softly “What a dork” he muttered to himself as he seen him leave

The stallion headed into the room, seeing Winter collecting a few books and placing them on a book cart “Oh hey” Winter said to Jackk with a soft smile

“H-Hey..” Jackk replied with as that familiar blush crept back to him with full force

Jackk was also shy to begin with, back in Friendship school he never interacted with many ponies nor did he ever go to parties in college, he was always just this way, but he also did know how to interact with other and didn’t necessarily need help with that, he has a few friends and quite a few acquaintances so he wasn’t just some emo stallion that hated everyone

Still it was hard in the aspect of romantic relationships, he didn’t understand flirting, hints, heck even if you straight up went to the stallion and kissed him he’d still be confused

He never had a relationship like that though

With that he stood tall and eyed around the room for the shredder, “I heard you're my boss Jackk” Winter said with a smile as he finished placing his books around

“Indeed I am Winter” he said in return, keeping a soft and content grin on his face

“Are you okay?” Winter asked sweetly

“What do you mean?” Jackk replied

“You just seem off.. You don't make any eye contact to me and you stay quiet..”

Jackk seemed to get a bit more shy and embarrassed by that reply, his blush deepened further, so much so he in fact could notice it

“I’m just.. Not talkative is all” He soon replied after gulping nervously as well, keeping his eyes stared towards the ground

“Oh, well that’s understandable” Winter happily replied as he smiled a bit warmer “What if we went to dinner? As co workers of course but ya know, a bonding experience”

And with just that sentence, his heart felt like it exploded, into a million fucking pieces just like that

“U-Uhh..” Jackk was absolutely speechless from what his newfound co worker just said, as he eyes narrowed all over the place in embarrassment and as his blush poked up to his ears Winter quickly said;

“It's okay if you don’t wanna..” He started to frown a bit as he ears folded back as well, a small quiver to his lips at times

He felt as if he crossed a line or made the other feel super awkward (which he sorta did) and he didn’t like that

“Sorry..” he soon added as he got up and started pushing the cart forwards and heading out

“Wait!” Jackk lightly yelped out as WInter jolted up from his position and narrowed his eyes towards the grey stallion “I-I uhh.. I will do that” He soon added as he looked over at Winter with a shy look

Winter seemed excited, he nearly couldn’t contain his grin as he blushed deep “Really?!.. Er i mean- Are you sure?” Winter said enthusiastically

“Yes Winter, around 7 o’ Clock got it?” Jackk replied with a semi stern tone

“Yes boss! Got it!” WInter happily replied back as he smiled brightly and headed out to go do his workly duties

And with that, it seemed they might start being friends, little did Jackk know, Winter found him quite attractive as well and was actually flirting with him (badly) when asking.

Overall the work day was quite boring and slow, with only a few ponies returning some books and some browsing the selection of them, Jackk had anxiously waited for the work day to be over so he could have a nice dinner with his new co worker and perhaps friend
Yet it still felt awkward, he didn’t know how to feel about some random, hella cute stallion to just ask him on what was practically a date… in his eyes anyway

Nevertheless he still was up for it and even a little excited as he typed in his daily notes for the day, getting ready to clock out for work, Winter had already done so about thirty minutes ago so he knew he’d probably have to walk to his place

“J! Hey! Were those books taken care of?” Sunburst suddenly chimed as he looked quite tired himself, occasionally pushing his glasses up his snout

“Yes Sumburst, got it” Jackk soon replied with as he finished writing his notes. Setting his work book aside as he quickly clocked out and grabbed his bag

“See ya tomorrow lad” Sunburst said with a soft smile as he waved him off

“See ya Sunny!” Jackk quickly replied with a bright smile back as he waved towards him as well quickly heading off and out of the castle as he awaited what might be a long and embarrassing night for him

As he walked back down the much less crowded roads of Canterlot he was constantly thinking to himself

“What if this is a bad idea..” he whispered to himself “what if he just wants to be friends and that’s it, why am I thinking this’ll be.. More?” he added with an even quieter tone at the end, the grey stallion let his mane flow down over his face as he pondered his thoughts, over and over again, he worried, a lot, it was just in his nature

And as cool as he tried acting, he really was just an incredibly shy and vulnerable stallion.

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Author's Note

Hey! Please read Chapter two for the continuation and be sure to give feedback! I'd love to hear your opinion