--- Chapter I -- An Unexpected Intern
--- 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.
-=-=-==--=-=-=-=-=-=-=-=-=-=-=-==----
Author's Note
Hey! Please read Chapter two for the continuation and be sure to give feedback! I'd love to hear your opinion
=== Chapter II === "Date" Night
====== Chapter II ======
Jackk was pacing back and forth in his living room as he was kind of scared of such a simple thing, however he was one to overthink way too much for his own good
‘Why did i accept this..” he muttered anxiously to himself, brushing his charcoal grey mane back as he sighed “Fuckfuckfuckfuckfuck..” He added, stomping his hoof lightly as he soon heard his stopwatch chime
Ring ring ring!!
That meant it was time to head over to Winter’s place for what would be a very embarrassing night.
Heading out his front door, Jack hid his embarrassment and shyness through a content smile as he began trotting forward, it was even quieter than on his way home, most ponies were home now, either making dinner or spending time with others, any tourists were in their hotel rooms relaxing, and any ponies out were admiring the well lit streets coated in crystals
Jackk had often walked through these streets at the evening/might and so did many, it was calming to see the illuminated city and hear the calm current of the river nearby in the distance, it was also a nice place to meditate and just get away from all the hectic ponies and businesses around
“I’m so nervous..” The stallion had whispered to himself in a pitiful manner, he knew he’d probably be proven wrong eventually, but his heart was beating out his chest and he couldn’t help it
After walking through the city’s square he was almost at his destination, and he got more hesitant as he got closer, nevertheless he managed to toughen up and reach his home
Knock knock knock !
Winter jolted up from his seat as he heard the hoof knock on the door “Eep!” he squealed lightly as well
As Winter got up from his seat he brushed himself off and spritzed on some cologne, he headed to the front door and happily greeted the stallion
“Hey Boss!” he said with a warm smile and enthusiastic tone
Jackk blushed quite a bit from the term as he smiled weakly back at him “H-hey.. Uh- Winter” he soon replied with a giddish grin as he kept a bit of distance from the door
“Are you ready for dinner?” Winter soon added as he stared at him with a small blush, keeping a playful grin in his direction
“Reaaady as I’ll ever be” he replied with a awkward smile as he rubbed his other hoof with his own
Winter grabbed a light blue silk scarf and soon headed out the door, closing it behind him as he looked back at Jackk with a warmer smile and nodded his head in the direction they were headed so Jackk could lead the way
“After you!” Winter said enthusiastically, and shortly after the grey stallion had done so, trotting forward and onto his way to a more lowkey middle class restaurant for them to eat at. He wasn’t much of a fan of fancier things anyway
“So uh.. Why did ya decide to work at the library?” Jackk said as the stallion averted eye contact towards the other, not even caring if he looked shy
“Oh well, i needed something to do while doing all my school work for college!” Winter replied, staring up at the larger stallion with his dorky grin
“Oh? What are you studying for hmm?” Jack asked in return as he tried starting up a conversation, after all, no guarantees he’d talk much in public.
“Well i really like cooking so i decided to do some studies on it” Winter gestured “I started cooking when i was a filly!” He soon added
“Really? That’s nice, i’d love to try some of your food sometime” Jack replied with a cheeky grin as they walked down the empty streets of Canterlot
“What about you? What do you wanna do in life?” Winter said.
“I like magic.. And the science behind it, and spells are cool too” Jackk said while scratching the back of his head
“That’s really cool!” Winter replied loudly
That caused Jackk to blush quite a bit from the compliment as he smiled dorkishly as well now, his hoofsteps were also starting to pick up which he did when he got nervous
“Thanks” he replied after a few minutes of awkward silence
“No problem bud!” Winter said with a happy glee as he nodded his head
After awhile of walking and chit chatting the couple had made their way towards the restaurant and went inside, the place was well lit with candles and a few strands of small lantern bulbs, Jackk had made his way up to the reservation desk and cleared his throat as he was about to die from embarrassment by saying
“Reservation for two, sir” Even though the two weren’t actually a couple he still felt awkward in applying that
“You got it!” the waiter said with a small grin as he winked at the two, which of course made the grey stallion’s heart drop to his stomach
“Th-Thank you, sir” Jackk soon said to him as he trotted along, grabbing a menu as well
“Thanks!” Winter also said as he soon followed behind the other
The restaurant had more of a diner feel rather than a elegant restaurant that the inner city had, Of course the gentlecolt Jackk was, he pulled out a chair for Winter to place his flank on as he soon seated himself across from him, such a gesture made Winter blush a light tint of pink
“Thanks for agreeing to come J, after all you didn’t have to” WInter said as he looked around the eating establishment
“It’s no big deal.. I don’t go out often anyway” The unicorn said in a soft chuckle as he looked around as well, trying to ignore the fellow ponies in the restaurant as he didn’t wanna get too nervous
“Still, i appreciate it Boss!” Winter chirped out as he smiled warmly at the grey pony who was being shy and sorta closed off from the other
Jackk picked up the menu that was on the table, eyeing through it to see if anything peaked his attention, and a few entrees did as well a desert displayed on the menu
“Lemme know when you’re ready to order” Jackk said to Winter as he kept his muzzle engulfed in the menu to avoid noticing the other ponies
“I think I already am” Winter quickly replied back as he set his menu down “Are you?” he added
“Uhh yeah, i think so,” Jackk set the menu down and took a sip of water before shouting… somewhat “Waiter!” His voice was still calm and didn’t have a lot of umpf to it, though he waved his hoof and a waiter did soon trot over
The small male Pegasus with a silky green coat and a soft charcoal grey mane had flipped his note pad and gotten his pen before asking “What can i get for you two tonight?”
Jackk looked at Winter before nudging his head in the direction of the waiter, implying him to order first
“Oh- I’ll have the carrot salad and hayburger!” Winter said, and as the waiter looked at Jackk the grey stallion cleared his throat
“I’ll have what he’s having” He soon said, it was actually a coincidence as he did want both those items, The waiter wrote down their orders and soon trotted off to the kitchen
“Was that actually what ya wanted?” The white pony asked
“Indeed, actually it was” Jackk agreed with as he nodded, crossing his hind legs as he stared out the window
“So uh- Tell me about yourself” Winter said as he leaned onto the table a bit, taking interest into the other stallion
Jackk bit his lower lip as he pondered his thoughts, he didn’t have a very happy life and he didn’t wanna make this dinner sad especially
“I- uh- I didn’t have a good life so far” he simply said, looking away even further from the other
The reply made winter frown immensely so, he didn’t like hearing such things mainly cause he had a tender heart, and cared about many
“Well, I’m here to listen, if you wanna share of course.. No pressure” the small fluff ball replied with, he had a bright smile on his face in hopes that the other would feel welcomed
“Well let’s see,” Jackk started, trying to find a way to start off his story “My mom and dad divorced when I was a small filly and things were rough then,” Jackk explained, as a small frown started to form on his face “I also am- uh- Gay, and a lot of the school ponies either didn’t understand or just picked on me” he added
Winter began to frown as well, again, he doesn’t like ponies going through rough patches, “Well.. Just know i think its okay to be Gay, and no pony should say otherwise, everyone in Equestria should love and be loved” Winter said with a small smile on his face
The sentence caused Jackk to blush immensely as he chuckled nervously at the gesture
“Besides..” Winter reached his hoof out to comfort the other stallion “I’m kinda gay myself” he added with a giggle
Before Jackk could say or do anything the waiter soon brought their food to the table, and after setting down the silverware and napkins they trotted off
“Thanks!” Both stallions said at the same time as Jackk began to blush deeper from the action
Winter was the first one to dig in, grabbing his fork and quickly beginning to eat his salad, humming in delight as he hinted it was good
“What kind of stallions ya like?” Winter joked, of course the comment made Jackk blush even deeper as he gave off an annoyed look, trying to hide it by eating his burger
Winter scoffed though soon assuring; “i was joking” still, the quip made Jackk really flustered and he couldn’t help it either
The area between them laid silent in sheer awkwardness for each other, Winter was first to finish his food but Jackk was not even half way done
“You ok?” Winter asked with a concerned look to his face
“Sorta..” Jackk replied
“Did i do something?” the white pony asked as he frowned
“No.. just.. I hate looking back on life” Jackk added back, sighing deeply as he picked up the pace on his food
“Well just know that’s all in the past, we can only look forward and i see big things your way J” WInter replied with, gently touching the others hoof with his own
“I.. I know..” The grey stallion seemed to be a little more happier by the younger stallion’s words
“Whatcha say we spend this summer as friends? Just hang out occasionally during and after work!” Winter suggested
Jackk had to think about the offer, on one hoof it would grow his social abilities for the better, on the other he was already nervous enough as is
“U-Uhh.. Sure” He soon agreed, narrowing his eyes onto the other as a warm smile started to form
“Great! I can’t wait” Winter replied happily as he held the other’s hoof lightly in his own
“Ready to go?” Jackk asked
“Whenever you are” Winter said back
“Check please!” Jackk shouted once more as he let go of Winter’s hoof to gather his plate, once the check was placed on the table he signed it and got up shortly after
“Come on then” He said with a somewhat happy tone this time, and as Winter got up he soon trotted towards the exit
As Jackk walked out he tipped the waiter at the reservation desk a dozen bits or so, holding out the door for Winter the two would walk the same path down back to the white fluff ball’s place
The two walked down the even brighter streets (since Luna’s moon was out and brighter than ever) and as they did, Jackk seemed to be getting closer to the other, actually walking at a leisurely pace closer by his side
“I had a nice time..” Jackk said with a goofy smile as he nudged the stallion next to him
“Really? I’m glad ya did” Winter replied as they looked over the town’s illuminated glory, basking in its beauty
There wasn’t many words for the two as they walked, after all much was said between the two today, at least, more than what Jackk would say in one day, and that was saying a lot, considering he usually spent work alone without talking to any pony besides a few ‘Hello’s and ‘Goodbye’s from Patrons and a few quips back and forth at his boss
He was actually surprised he had such a time today, and part of him was excited to go home and ponder over it, and another part secretly wishes it to happen again
As the two walked down the cobblestone roads they soon reached Winter’s place, Winter walked up the pathway but Jackk didn’t
“Oh.. right”
Winter trotted back down the pathway to give Jackk a big hug “See ya tomorrow Boss” he said with a flushed smile
“See ya Winter, Goodnight” Jackk replied, and as he was just about to turn around Winter gave him a quick kiss on the cheek
And sweet Celestia did that embarrass him
Nevertheless though he went with it and smiled back, soon turning around and trotting back down Winter yelled “Bye!”
“Bye!” Jackk replied as they both waved at each other before parting ways
And as the larger stallion walked home, he rubbed his cheek occasionally while doing his usual overthinking tangent
“Oh Celestia, He’s adorable” He said to himself with an awkward chuckle
And as he soon reached home, and as they both relaxed and soon let Luna take their dreams off
He couldn’t wait, until the next day
Author's Note
Thanks SOOOO Much for reading! again please leave feedback and i hope this didn't leave ya on a cliffhanger 
