#SimonsAdventChallenge
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A Woolly Hat
Written for @simons-thirst-squad’s Simon’s Advent Calendar Challenge
Prompt-Woolly Hat
SimonxReader
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It all started with a package left outside his room. Simon had a rough day, and was ready to call it a night. Although keeping track of the days, it was generally believed to be near the middle of December.
And if the weather was any indication, it was shaping up to be a cold winter. Even the hot water afforded to the citizens of the Sanctuary didn’t seem to be enough to fully warm him up. He kept his towel around his neck, using it as a makeshift scarf to keep in what little warmth the shower had given him.
So when he saw a bag hanging from the door to his room, Simon was a little confused. He glanced up and down the hallway, seeing if whoever had left the package was still around. The dark hallway was empty and quiet, only the ever present hum of machines reverberated through the building. It was after curfew after all.
Seeing no one, he grabbed the bag and entered his room. He hung his towel up and turned the gift bag over in his hands. There was no note on the outside, so he assumed it was for him and opened the bag. Inside was a pair of gloves. As he examined them, he saw that they were handmade. The knitted stitches were even and tight, but did not have the appearance of a pair made by machine. The yarn was smooth, dark blue with brown accents.
When he tried them on, they fit well, keeping his hands warm while still allowing for movement. Each stitch flexed easily, but stayed snug against his skin. He pawed through the rest of the bag, but there was no note explaining the gift or who it was from.
Simon yawned, the events of the day catching up with him. Giving the gloves one more look, he removed them and set them down on his desk. He’d worry about the mystery gift tomorrow. The comfort of his warm bed beckoned to him, and the fell asleep as soon as his head hit the pillow.
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The next few days passed without incident. Simon was thankful for the new gloves that had appeared at his door. His old pair had gotten ragged, allowing wisps of cold air to stiffen his fingers. Now his hands stayed warm and decidedly not stiff.
While walking with Negan one morning to survey the supply trucks that had returned that morning, the aforementioned boss zeroed in on the new addition to Simon’s wardrobe.
“Pretty fancy gloves you got there, Simon,” Negan said offhand.
Simon flexed his hands.
“Yeah, pretty nice,” he said simply.
“Where’d ya get them? Looks homemade.”
Simon shrugged.
“Got left at my door.”
Negan’s eyes lit up and his mouth split into a shit eating grin.
“Oh ho, does Simon have a secret admirer?”
Simon internally groaned. Negan may be king dick in charge, but he could be like a gossipping soccer mom when he wanted.
“I don’t know about that. Probably a thank you gift from someone. The people love their Saviors,” he evaded.
Negan didn’t want to let the matter drop. After all, needling people was one of his favorite past times. Negan liked to think he was a pretty fair guy, so even his second-in-command was not safe from this activity.
“Wonder if she’s cute? I know there is till some prime wife material running around,” he mused out loud.
When Simon only hmm’d in response, Negan shook his head.
“What’s the matter? Don’t want a little lady to come home to? Knitting you socks? Shit, that sounds nice. Wonder what else she could knit?” Negan trailed off as he let his mind wander.
Simon thought about Negan's words. He had a few companions since the world fell, and never more than a night. It was all stress relief, more like mutual masturbation than anything including feelings. In the beginning, the world was unstable, too unstable to pursue anything of merit. Even now, with the security of Sanctuary, the idea of having something serious with someone seemed farfetched.
Simon was broken from his thoughts when Negan’s hand came down abruptly on his shoulder.
“Or… it could be a guy,” Negan said, raising his brows exaggeratedly.
Simon’s groans were audible this time, and Negan laughed at his reaction. The mustached man cut his eyes to his leader in annoyance.
“What? No judgements here,” Negan said twirling Lucille before raising his hands in a defensive shrug.
A shout drew the pair’s attention, and Simon was thankful for the interruption. Negan gave Simon a wink.
“Enough gossiping, apparently some assholes can’t do their jobs properly. Let’s get to work.”
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A few days later, another gift was left. Simon opened the bag quickly, and found a chunky knit cowl scarf folded neatly at the bottom.
This time, there was a note. He unfolded the scrap of paper, and smiled at the words written in a delicate script.
Glad the gloves fit. Stay warm.
Simon fingered the soft yarn. This time it was a dark grey. Instead of hanging, the ends of the scarf would button under his chin. It was as if the maker made it specifically with Simon’s job in mind. A dark color and no dangling bits for a walker to grab ahold of.
Negan once had a slight mishap when a walker grabbed his scarf from behind. After that, Negan made sure his trademark red scarf was tucked securely into his jacket.
Simon scoured the note, looking for any clue as to who had written it. The handwriting, he guessed, could be seen as feminine. The message itself was written on a random scrap of paper. No hints as to the identity of the person to be found.
As he held the gift in his hand, he was surprised that a literal lightbulb didn’t appear over his head.
The Marketplace. If they were getting yarn, it would have either been a perk from scavenging or bought with points. As far as he knew, none of the Saviors had a talent for knitting, so it had to be a worker. Plan and gift in hand, he headed to the communal area of the factory.
Despite the early hour, there were still people picking over organic pickles, new clothes, and other sundries. Simon nodded to several workers before coming to a stop in front of Shirley. She was in charge of deducting points for purchases and keeping the marketplace in some semblance of order.
Simon gave the octogenarian a winning smile as he leaned on her desk.
“Good morning sunshine.”
The older woman was living proof that the 80s were the new 60s. She had survived the initial outbreak alone in her house, shot gun in hand. When they had found her, Negan loved her no nonsense attitude when she berated them for wearing dirty boots inside her house. And now she ruled the Marketplace with an iron fist.
“Cut the baloney Simon,” she said dryly, not looking up from her ledgers.
“You wound me,” Simon said dramatically, clutching his hand to his chest.
Shirley sighed and looked at Simon, lowering her glasses to put the full force of her glare on him unhindered.
“What do you want?”
Simon produced the gloves and cowl, setting them on top of her books.
“You sell any yarn lately? Knitting supplies?”
Shirley furrowed her brows.
“Not too many people waste their points on craft supplies,” she said examining the items.
“Though these are pretty nice. They’d be good sellers.”
She looked back up at Simon who was looking at her expectantly.
“A name?”
Shirley held out her hand expectantly, raising a brow. Simon sighed.
“Aw, c’mon Shirl. We can call it a Christmas gift for your favorite Savior.”
She pursed her lips and flipped through her ledger.
“You find me a bottle of wine. Nice stuff, off the books.”
“Yes ma’am,” Simon agreed quickly.
As Shirley scanned the pages, she found the entry she was looking for and wrote down the details of the purchase.
She handed Simon the information, jerking it back when he reached for it.
“A red, preferably Cabernet. A shiraz will do if you can’t find one. Not a pussy Merlot.”
“You got it,” he said, thinking of the wine surplus that the Saviors had squirreled away.
Shirley gave him a long look before handing over the paper.
“Be nice to her. If I hear anything untoward, I will display your balls right here on my desk.”
Simon gave her a reassuring nod, while his balls seemed to climb back up into his body at her words.
“Now scat so I can get back to work.”
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You sat in one of the greenhouses, knitting needles clacking between your fingers. The woolly hat you were working on was coming together quickly. Sure, a loom would be faster, but in your opinion, not as well made.
You had spent the last bit of your surplus points on the new yarn. It was thicker and a higher quality than your previous finds. It was perfect for a toboggan for a certain Savior.
Elsie, one of the other women working in the gardens had tried to convince you to just give Simon the gifts, rather than leave them for him to find. But you couldn’t. You fucked up your first and only meaningful interaction with the mustached Savior, and still felt embarrassed months later.
A shadow fell over you, and you nearly jumped to your feet. You scrambled to gather your things.
“Sorry Marv, I didn’t realize my break was over,” you said hastily, keeping your eyes down to not draw the ire of your boss.
A hand, slimmer than Marv’s, reached down to pluck the half finished hat out of your hand.
“This gonna be for me too?” a familiar voice asked.
You looked up to see Simon studying the hat’s stitches, careful to not let your hard work unravel.
“What?” you squeaked, not mentally nor physically prepared to see the object of your affection standing next to you, let alone talking to you.
“Your name is (Y/N), right? Work in the green houses. I asked around,” he said, still looking at the hat.
You chewed your lip, running through all the possible scenarios that could take place. All seemed to point to disaster.
Simon picked up on your unease and knelt next to you.
“Didn’t mean to scare ya. Just wanted to say thank you.”
“You’re welcome,” you said softly, keeping your eyes to the ground, hoping your hair camouflaged your red face.
A warm hand cupped your chin and brought your eyes up to meet his.
“So what reason does a pretty gal like you have for giving an old man like me gifts?” he asked, giving you a smile.
“I wanted to say… thank you. You probably don’t remember, but you offered me gelato on my first day here,” you explained hesitantly, not wanting to revisit your embarrassing first meeting with him.
Simon’s eyes widened when he remembered the event.
“You ran away from me. Negan busted my balls for days after that. Said my mustache scared you off,” he said, laughing at the memory.
His laugh was infectious, and you couldn’t help but giggle softly.
“It wasn’t your mustache. I like it. You just took me off guard. I didn’t expect to draw the attention of the right hand man of Negan,” you explained through your laughter.
“You say that, but you are still laughing. I’m not sure if I believe you,” Simon said, mock pouting.
“I do, I do,” you promised.
Simon looked at you unconvinced.
“Prove it. Meet me for gelato, tonight after dinner. For real this time, no running.”
You felt your face heat up, but found yourself nodding at his request.
“Wouldn’t miss it,” you said.
Simon smiled, and stood up, offering a hand to help you up. It was then you noticed he was wearing your gloves, and the cowl you had made him.
You took his hand, and he helped you up easily. After standing, he kept a hold of your hand, giving it a soft squeeze.
“See you tonight,” he said, bringing your cold fingers up to his mouth to place a kiss on the tips.
You nodded, liking the way his mustache brushed against your skin.
“Tonight.”
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