Charlie Bradbury was not one to take no for an answer, she'd been the only girlfriend he'd ever had, however short lived. It creeped them both out so much, they decided to run the opposite direction. She started dating girls, and he dated guys, and they'd never really thought too much about it. She'd been one of his best friends since, and would always be. So when she called, he answered. When she said you're coming to pick out rings with me, he said yes ma'am. Thus leading to Dean "the straightest gay man alive" Winchester shopping for jewelry. While his partner, and his brother, both more suited for the job, were lucky enough to stay back at the house. It was going to be a long day!
Sam and Castiel were left to entertain themselves, which always led to hijinx. Growing up in a home full of "essence of Gabe" as Castiel liked to call it, was more than enough to rub off on him. Sam just had always enjoyed messing with his brother, he didn't need a reason but they'd had plenty over the years. So here they were after over two decades of pranking together trying to come up with something new. They were at a loss for quite some time, but it was nice to reminisce on all the things they'd done over the years.
From the smallest things like putting a whooppie cushion in his seat, to the bigger schemes like hiding his car at Uncle Bobby's and then Sam saying that Dean had left it at Cas' and Cas saying that he hadn't drove it there, he'd left it at home. It went on for three trips back and forth between the houses before Dean started to believe it was stolen, so they told him where it was before someone got hurt, it was his absolute favorite possession.
"Oh my god, do you remember all those Dean Traps you used to set?" Sam asked, it was unnecessary because of course Castiel remembered.
"Hey I'll have you know Sam Winchester, those actually worked .. so in the words of my boyfriend, "Bite Me"
"Oh god, there were so many though, like the one with the Cars! Now THAT was hilarious!"
Castiel smiled unable to keep his happiness from showing, it was one of his more insane ideas.
-? Years Earlier-
A very young Dean Winchester had a fascination with classic cars, so of course a very young and somewhat clueless Castiel, started building model cars. He'd only pick Dean's favorite makes and models, ensuring what he assumed would be Dean's eternal gratefulness. However, as per usual that's not exactly how things went down. When Castiel had finished making his third and final car, his face beamed with pride. He gathered the first one with him and bounced all the way over to the Winchester home, which was as much his, as theirs by that point.
He rushed into Sam's room and hid the small car behind a box in the closet and waited. Cas and Sam were best friends, and Castiel had been crushing on Dean since the moment they met which was when they were five. Here he was, nearly seven years old and he still didn't have the courage to really talk to the other boy. He would always say "Hello Dean." but that was about as much as he could manage in one meeting. So he opted to be discretionary with his gifts, which was probably the worst part of the plan.
Once he knew Dean would be asleep he snuck quietly to the room next door, his hands shaking the entire time. He left a much smaller version of Dean's favorite Dodge Charger on his nightstand before creeping out slowly and running over to Sam's room in hopes of easing his anxiety.
The next morning Dean woke up and the first thing he'd seen was the General Lee out of the corner of his eye. He was suspicious at first but hey, it was a cool car who's gonna look that kind of gift horse in the mouth. It wasn't until he'd thanked Sam for it and was met with a genuine look of confusion that he suspected more was going on.
The next night Dean stayed up all night hoping to get a glimpse of what was happening but there was nothing, so he slept in a little late the next morning.. when he woke up there was another car on his table. This time it wasn't the famous Dodge Charger but it was an equally impressive sky blue Chevelle. He was starting to be a little creeped out that someone or something was coming in his room while he was sleeping. So he did the only thing a boy like Dean could do, he made a phone call.
"Hello."
"Hey Uncle Bobby, I gotsa question."
"How can I help ya boy?"
"You ever heard of a car fairy?"
"A what now? The gruff older man asked clearly confused.
"You know like a tooth fairy only instead of losin teeth and bringin money it just brings you little cars?
Bobby outright laughed in his ear, like not just a little chuckle a full on laugh.
"No Son, can't say I've ever heard of anything like that..what's it takin' stead of teeth?" He asked, Dean wasn't sure why he asked, it was clear that his uncle idn't believe in whatever it was./p
"Not sure, haven't noticed anything missin just yet but I'm sure it's takin' somethin'."
"Well you get more details on this thing and we will try to figure it out."
"K bye."
"Now Dean, I know your momma is raisin' you better than that."
"Sorry, Thanks Unlce Bobby! Talk to you soon, bye."
That night he just went to bed, what was the use in stayin up if the thing was just gonna come when he was asleep. So he made some new adjustments to his room and fell asleep with a smirk on his face, whatever was coming that night he was prepared.
Castiel came really close to bribing Sam with candy to take it for him, but then he'd have to tell his friend he was the one leaving the cars. In spite of Sam Winchester's loyal and protective personality, he was certainly unable to keep anything from his big brother. Castiel had learned that lesson early on in their friendship, the hard way.
So against his better judgment he went to put the third and final car in the room of the eldest Winchester. He got to the door and twisted the knob but his knees were shaking he knew if he went any further he'd be discovered, so he left it by the door and went back to bed. Once safe in the interior of Sam's room he smiled, it was finally over. He had just wanted to do something nice for Dean, so he knew that good things happen to people who are nice, and cool, and perhaps his cuteness had something to do with it too, but Cas wasn't going to admit to that anytime soon.
The following morning Dean was very disappointed to wake to an empty net, more disappointed to wake up without a car at his bedside. He laid in bed just a little longer that day thinking maybe he shouldn't have been trying to trap whatever it had been, it was clearly smarter than him, and now there would be no more cool cars. That's what he thought, until he opened his door and found one with his foot. He looked at it in awe..and he knew, he just knew it would be the last one, because it couldn't have gotten any better. It was a 1967 black Chevy Impala and the best car in the whole world.
John, Mary, Sam, and Cas were all sitting at the breakfast table when he got downstairs with it.
"Okay, it was one of you.. I just want to know who to thank." Dean said smiling staring at the small car.
Castiel nearly choked on his biscuit and Sam patted him on the back as Mary stepped in.
"Maybe it was the car fairy."
Sam laughed but everyone else was stoic faced and intrigued.
"Uncle Bobby said there ain't no such thing, and then he laughed at me."
Mary smiled and patted Dean on the shoulder.
"Well Bobby is a smart man Dean, but even he doesn't know everything!"
-Present-
That was the last discussion about the cars, but Dean had kept the small Impala all these years and Cas still catches him looking at it and smiling sometimes.
"You do realize he still doesn't know you made those for him" Sam said with one of his most genuine smiles.
"It would do you well to remember to keep your mouth shut about it as well!" Castiel teased.
"Which one of the traps was it that finally worked? I can't remember"
Castiel blushed, even after all these years with Dean and he still blushed when he thought back to the first time they had kissed./p
- 23 years earlier-
It had been seven whole years he'd been in love with Dean Winchester, and he'd done nothing to let him know, so Sam decided it was about time to do something, they'd began setting traps for Dean six months earlier but all Sam's ideas were too good, because Dean could smell a trap a mile away. If something seemed too good to be true he knew better than to fall for it. Sam was out of ideas at that point, so Cas tried to think of something. He'd tried mistletoe at Christmas, and Dean laughed and patted him on the shoulder, and nudging him toward Sam in a rather suggestive way. That was by far the worst attempt, so he decided simple..he'd go with simple..so he asked for Gabriel's help and pretty soon they were ready to go.
He was at the playground next to the Winchester house, he'd made sure that Sam would have Dean bring him at exactly 5 o'clock. All Sam had to do was make his eyes real big and look sad, Dean called them puppy dog eyes, Cas didn't understand why, Sam was very much still a regular boy when he made the face, but it worked, so he didn't question it further.
Once at the playground he placed the warm circle on the table and wrapped a string around it, he kneeled behind the picnic table and waited for his friend. When Sam got there he looked around but didn't see Castiel anywhere, but he saw a pie and knew his friend wouldn't be far off.
He sent Dean after a bottle of water from the vending machine and hid behind Cas who was, as he'd figured right next to the pie.
"Cas! This isn't going to work, Dean's too smart...hmm..." But before he could finish whispering, his brother walked up to the table and inspected it.
Dean looked down and the pie was already cut into slices. Who leaves pie unattended? Obviously someone who didn't deserve it. His hand reached into the silver pan and jerked a piece out. As he chewed he realized it was one of the best pies he'd ever had, maybe even better than his mom's.
Castiel stared awestruck, Dean Winchester was eating his pie, and he obviously liked it, he was happy and smiling and there wasn't anything more beautiful. Castiel was sure of this, if nothing else in his life, that he knew for a fact.
"Pull it, Cas! ...well now you missed him." Sam whispered.
Sam walked off and Cas eventually moved up to the seat of the picnic table but he was still in awe. That was until about 5 minutes later when Dean came over and just kissed him, right on the mouth.
"What, why, ..wha..." Castiel said as his face continued to get even more rosy.
"Thanks Cas, I love pie! "
-Present-
"I know what I'm going to do Sam, I'm going to trap him! "
Sam just rolled his eyes and smiled at his very romantic best friend, he knew they weren't going to be playing any pranks today. So he followed Cas into the kitchen and talked to him as he baked. Sam would have offered to help but they both knew they were better off if he didn't.
When Dean came home to the smell of freshly baked Apple Pie, he knew he'd made the right decision. He smiled as he took his jacket off at the door and walked into the kitchen. Cas's hair was showing behind the table with a string wrapped around the pie pan. He couldn't help but chuckle, instead of stealing a piece of pie like he would have normally, he walked around and lowered himself to his knees and pulled his boyfriend in for a smiling kiss.
When Castiel laughed and stood up he reached his hand down to Dean to offer help but was rejected. Instead Dean reached into pants pocket and brought one knee up and opened the small black box in his hand. Castiel instantly looked shocked and began to tear up.
"Cas, I love you. You're the only person I've ever considered spending my life with and I'd be honored if you'd have me."
Castiel went from teared up and in shock to full fledged crying in under a minute as Dean took the ring and slipped it on his finger. It was gorgeous, a silver band with etchings and a small green stone in the center, it would have been perfect no mater what, because it was Dean, and he would always say yes to Dean.
"YES! YES! YES!"