Chapter Text
August
Blue eyes stared down in glee at the young man walking near the construction site, watching all the amazing stuff he could use to kill him—out of context, he understood that sounded bad. He wasn’t a serial killer or anything; it was just his career. His career in question? Well, Castiel was a Reaper. You know, those skeletons with the scythe? That was him. Except he wasn’t a skeleton, wore robes…or had a scythe. The whole thing was a rude stereotype. He looked just like everyone else. He wore a full Techwear outfit, with a red hood that he kept up most of the time and black boots. He was an angel of death…in training. He still hadn’t gotten his wings.
All potential reapers had to perform a solo reaping, which meant they had one target they had to kill off. The baby reaper passed all his schooling; now it was for the real deal. This was why he was casually following this man walking lazily in a tan trenchcoat and suit next to this active construction site. The man looked like he was made of money, not a speck of dirt on his lavish clothes. Honestly, Castiel thought that maybe he must have been a model or an actor. He was rather handsome—Focus.
His target? Dean Winchester. There was nothing more than a picture of him and a magical pinpoint of his exact location on his reaper watch that someone at the academy shoved into his hand before he left. This was going to be the easiest reaping ever! He was going to get his wings on the first day! The reaper in training took a seat on a support beam to watch the show.
Castiel’s eyes moved to a steel beam held on a crane that rested nearby overhead as he waved his hand. Making the wind blow a bit harder, the beam started to teeter slightly. The crane operator didn’t seem to notice, just waiting for the go-ahead to move it into place. Just as Dean walked under the crane’s bolt holding the beam snapped, falling from the crane towards the unsuspecting man. Castiel smirked, watching it fall, but…something happened that made his blood go cold.
Dean tilted his head…glanced up at him with amusement, a smirk sliding on his face.
Humans…can’t see reapers unless they allow it, and he was for SURE not allowing it.
How…?
No way?
He couldn’t see him…right?
Then…Dean just stood there in the direct path. He kept his eyes on Castiel as the beam slammed to the ground, causing dirt to fill the air. The reaper in training held his breath, trying to look through the thick dust; however, when it cleared…Dean cockily stood next to the fallen beam. Missing death by a near centimeter, people screamed in horror, but Dean didn’t seem phased. He didn’t break eye contact. He didn’t even get dirt on him; he was unscathed in every way possible.
Son of a bitch—
“You need to try harder than that!” The target called up to Castiel playfully, who gawked in horror.
No…he couldn’t see him! There was no way!
The reaper glanced around the beam of the unfinished building he was standing on as though hoping to find the person Dean was talking to.
“I was talking to you, little bird,” The human called up lazily, turning to face him as Castiel did the same. This man was talking to him like he was ordering a burger. The reaper slowly pointed to himself. “See any other flightless bird around here?”
Castiel awkwardly waved down at him in disbelief, tensing as Dean playfully awkwardly waved at him back.
“...You can see me?” The reaper called down as Dean shrugged like it wasn’t a big deal. Meanwhile, Castiel was losing his fucking mind. Castiel stood. “...What the shit.” The reaper waved his arms in disbelief and scoffed before putting one on his hip.
“They didn’t tell you much this time around, huh?” The human asked, blinking up at him. “Always a gamble what they send you down here with.”
“This time…?” Castiel choked. “...Do you deal with reapers often?”
“More often than not,” Dean stated CASUALLY. Like this was normal. “I see you about every year with a new game plan to reap my soul.” The reaper stared, dumbfounded. “...I assume it’s going well?”
“...Uh…” Castiel spoke as Dean noticed a crowd starting to form. His watch beeped, gaining his attention, glanced at his watch before deciding to leave.
“...Well, good talking to you.” The human saluted, walking away. “I have an appointment.”
“Hey, wait-!” The reaper choked as Dean continued his journey around the building, but stopped when he almost slammed into the reaper who stood in front of him. “How can you see me?!”
“I forget, you baby reapers are like chickens. You can’t fly, but you can glide faster than the speed of light as long as it's a downward angle.” Dean chuckled as he moved around him. “You’re unlucky.”
“What?” Castiel followed after him.
“Why you got stuck with me,” The human explained simply with a fucking smirk on his face. “You’re just very unlucky.”
“What does that mean?” The reaper had to slightly jog to keep pace.
“What’s your name?” Dean spoke as Castiel sucked in air.
“Does it matter?” The reaper in training asked.
“We are about to spend a lot of time with each other; we should get names out of the way.” The human beamed. “Besides, if you want an answer to your question-”
“-Castiel.” Castiel choked quickly as Dean chuckled.
“Good boy.” Dean cooed. Castiel’s ears flushed at the praise.
“Now answer the question.” The reaper in training hissed, and Dean stopped instantly, making Castiel ram into him. The reaper pulled back in surprise. The human eyed him lazily.
“You, my little baby chick, have just got stuck reaping the soul of the one man who can’t die.” Dean wiggled his eyebrows at the proclamation as Castiel sucked in the air at the words. “Good enough answer?” The lucky man turned to leave. The reaper in training hesitated only a moment before jogging after him.
“That’s impossible,” Castiel choked. “You would have to be-”
“Incredibly lucky to cheat death over and over again?” Dean hummed his answer as Castiel slowly nodded. “Lucky for me, unlucky for you. I am.” The reaper in training clenched his teeth in disbelief, glaring at Dean. “Don’t believe me?” The lucky man mocked, offended. “Want me to prove it?”
Dean didn’t wait for an answer as he simply glanced over his shoulder to see a bus coming up on the road beside them. Dean smirked softly, staring at Castiel, slowly backing up into the street. He didn’t break eye contact with Castiel standing in the bus’s path, rather unbothered by the idea. There was no way the bus had time to come to a stop on its own.
If this idiot wanted to do the hard work of killing himself for Castiel. He’d take it.
However, a loud popping noise made the reaper in training break his eye contact with Dean to watch the bus come to a perfect stop in front of him, once again a centimeter away from hitting him. The bus was smoking, the engine having locked up before reaching Dean. The driver, panting with worry, poked his head out the window, checking on Dean. The lucky man waved him off but didn’t bother speaking with him as he continued on his way.
“...How?” Castiel choked in disbelief following him.
“I gambled against Fortuna and won,” Dean explained lazily. “I could ask for anything, so I asked for her luck.”
“The Goddess?!” The reaper in training was flabbergasted. “How did you win?!”
“I had too much to lose.” The lucky man shrugged. “Well, I won fair and square. So now I’m so lucky I escape everything: death, age, illness. I’m too lucky for all of that. So…every year they send the reaper to come try their luck. They always fail and go back. I haven’t seen one succeed yet.”
“How many times?” Castiel asked. He knew every reaper that had failed to reap their first within the allotted time, one year, had lost their ability to be a reaper. They would have returned to their afterlives with no chance to try again. No. He worked so hard that he couldn’t let that happen to him. The benefits of a reaper outweighed anything else. Not only can you freely enjoy the human world, but you also get to see the dead again…The reaper in training’s eyes fluttered at that thought. There…was someone he wanted to see. So he couldn’t give up. Dean’s voice jarred him from his thoughts.
“Gods. Who knows?” The lucky man winced. “More than one hundred at this point.” Castiel stared in disbelief, his heart pounding in his ear.
“Dean, how… old … are you?” The reaper asked softly as Dean smirked at that.
“...Now that’s also an excellent question.” The lucky man pointed at him. “Don’t remember.”
“Holy shit,” Castiel mumbled in horror. “...I’m never going to get my wings.”
“Sorry.” Dean playfully pouted and drew a tear down his cheek. “Told you, you’re unlucky… I’m very lucky, though. You’re pretty cute.” The baby reaper stopped as Dean continued, a blush filling his cheeks.
“I’ll reap you and get my wings, Dean Winchester! You hear me!” Castiel yelled stubbornly as the lucky man lazily waved him off. Castiel pouted, trying to figure out another way. Glancing at the watch that read the ever-lowering timer.
Castiel’s Deadline to kill Dean Winchester start date: August 1, 2024.
12 Months left, starting now.
___________________________________________________________________________________
September
(Castiel’s Deadline to kill Dean Winchester - 11 Months remaining)
Dean lazily stood texting on the corner of the street, drinking at a cafe, every single day for a month, and Castiel had failed. The baby reaper sat leaning on a nearby emergency fire escape, watching as he hoped the meat in his breakfast sandwich that he ordered would kill him due to the improper handling. He blinked lazily as the server brought it to Dean, who grabbed the sandwich. The reaper in training sat up happily. This was the closest he got to killing Dean all month! He watched Dean open his mouth to take a bite from his sandwich…when a seagull snatched it from his hand, taking off with it before the bite. The lucky man blinked lazily, watching it go as Castiel groaned loudly, which made Dean glance up at him.
“...Botulism?” Dean called, unimpressed as Castiel rolled his eyes. In the blink of an eye, he appeared in the chair in front of Dean. “Lazy on your part.”
“It would have worked if a Seagull hadn’t stolen your lunch.” The reaper scoffed, throwing his hand in the air. “...Very unlucky by the way,” The human smirked softly but said nothing as the worker returned.
“Sir, I’m so sorry. I noticed a seagull stole your lunch.” The waiter spoke before placing a sandwich and a piece of cake in front of him. “For the inconvenience, on the house.”
“Thank you.” Dean smiled kindly at him as Castiel looked pissed, crossing his arms. So maybe Dean was lucky. “Some sweets for my sweetheart?” The lucky man slid him over the small piece of cake. The baby reaper eyed it disinterestedly. “Come on, try it, you might like it.”
“I’ve had strawberry shortcake before,” Castiel commented as Dean smirked at that answer, almost amused. “I was human once.”
“...What does it taste like then?” Dean questioned. The reaper eyed him quietly for a moment, taking in the strawberry shortcake in front of him.
“Like strawberries and shortcakes,” Castiel stated, waving him off.
“Is it sweet or sour?” The lucky man asked, making Castiel ponder the question. When he thought about it…he didn’t know…why couldn’t he recall why? He assumed maybe it had been too long since he had had it.
“I don’t remember,” The reaper in training mumbled as Dean ushered him to eat. Stubbornly, Castiel grabbed a fork and took a bite, trying to look annoyed…but it was so good…and so sweet. Castiel lit up slightly as he chewed.
“Good?” The lucky man asked while drinking his coffee.
“No.” The baby reaper lied as he continued to eat the cake like a starving man. Dean eyed him affectionately, watching him enjoy the cake. Castiel got a bit of frosting on the top of his lips as he finished eating, quite content with the delicious snack. Dean stood, grabbed his stuff, and slid the breakfast sandwich to Castiel. “Running off so soon?”
“You’ll like that. It has a bit of a kick.” The human stated, sliding on his coat. The cold wind picked up, making Castiel fidget.
“...You disappear sometimes,” The reaper curiously inquired with a shiver as Dean eyed him. “...Around this time, almost daily. No matter what I do, I can never find you.”
“Lucky like that,” Dean spoke as he gave his non-answer before instinctively placing a scarf to lightly dangle from Castiel’s neck. He paused slightly when he realized he had done it, sighing affectionately and shaking his head at himself. “...This is New York. It’s Cold. Start dressing more appropriately. You might not die, but you do feel things.” Castiel glanced down at the scarf around his neck when he felt Dean sliding his hands down it.
“...I’m not going to say Thank you,” Castiel grumbled, stubbornly crossing his arms and turning away despite enjoying the warmth. The lucky man smiled softly at him, gripping both ends of the scarf.
“Never expected you to,” Dean hummed before adding. “Oh, and Cas?” The baby reaper glanced up at him.
Dean pulled Castiel closer with the scarf, brushing their lips together in a kiss. The reaper in training’s eyes widened as Dean kissed the sweet frosting away. Castiel could taste the frosting stolen by Dean’s lips as he pulled back only slightly before pressing another tender, quick peck to his lips. When Dean’s lips left him, pulling away, his eyes followed Dean while even his ears flushed pink. Castiel couldn’t help touching his lips, watching him go.
“You had a little something on your face, no need to thank me.” The lucky man waved, not even glancing at him.
Castiel sat there, dumbfounded as he slowly glanced at his sandwich. He picked it up, eating it in silence before the realization hit him.
That bastard kissed him.
“YOU SON OF A BITCH! I’ll REAP YOU ONE DAY, WINCHESTER!” The reaper stood yelling after him as Dean snickered to himself before he turned the corner, leaving his sight. “JUST YOU WAIT!”