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Roll With It, Baby

Summary:

August 1987. Indianapolis, Indiana.

The Pan-American Games are back again, and professional roller skaters Castiel Milton and Dean Winchester are supposed to be teammates--and friends. Over their six years on the US team, they’ve done their best to get along, but with Cas as a roller figure skater and Dean as a roller hockey player, they sometimes miss the mark.

But something’s different this year, at their second Pan-American Games. Maybe it’s the sultry end-of-summer heat over the main stadium at the Indianapolis Motor Speedway. Maybe it’s the competition. Maybe it’s Rick Astley's recent hit single "Never Gonna Give You Up."

Whatever it is, the next two weeks are going to change things…potentially forever.

Notes:

UPDATE: This has FANART now! made by lovemuppet here (haybibiboi on Tumblr)! it's linked below!

https://haybibiboi.tumblr.com/post/629569287437287424/fan-art-for-one-more-offbeat-anthem-s-fic-roll

SECOND UPDATE: One of my pals, lucifer_sings_in_soprano, wrote a one-shot sequel, if you wanted more of the boys skating! It's SO CUTE! Read it here: https://archiveofourown.org/works/26570473

THIRD UPDATE: lovemuppet wrote a one-shot/timestamp, too! the deancas rollerskating extended universe is getting out of hand and I LOVE it. read it here: https://archiveofourown.org/works/26582623

This sprang to being in a fit of listening to 80s music and thinking about roller skating (I skate—not professionally, but I can dance and have done a 5k on my skates). It’s a bit ridiculous, definitely niche, and something no one asked for—but it’s also, I hope, a ton of fun. The 1980s is my favorite decade in history, and I enjoyed a chance to dress our boys like fools and have a good time. The research for this was also really fun—it’s not 100% historically accurate, but I tried my best!

Thanks to elephino_forthehalibut for beta-ing for me, and a plethora of pals over at the profound bond discord server for giving me great ideas in terms of chapter titles, song usage, and also just letting me talk nonstop about this work. if you're 18+, join us! we're good fun! https://discord.gg/profoundbond

Content warning: listed as teen for swearing and mentions of sex. Includes mild references to abusive parents, homophobia, the foster care system, the AIDS crisis, and one usage of the f-slur.

Also! If you liked this/want some vibes, I made a playlist of all the songs used/mentioned in this fic, to help you vibe. Here it is! https://open.spotify.com/playlist/1nGekBDQ2ek0SLj1c5gwTq?si=vo9XfIA2RYG6u7bUMAv-yA

Chapter 1: I Like the Way You Roll

Chapter Text

August 5, 1987 (two days before the games)

Dean

Dean rolled out of bed with a thunk at the sound of his alarm clock radio blaring Livin’ on a Prayer.

We gotta hold on, to what we got! It doesn’t make a difference if we make it or not! We got each other, and that’s a lot, for love——

“Oh, fuck off,” Dean muttered, smashing the button on top to turn it off. He could smell bacon cooking in the kitchen—probably his brother, Sam, who was apartment sitting for him during the Pan-American Games…which were in two days.

“Double fuck,” Dean swore, stamping into the kitchen, “Hey, Sammy.”

“Someone’s in a crummy mood this morning,” his younger brother commented, sweeping his hair out of his eyes (if only he would let Dean give him a haircut).

“Gonna be late to practice."

“What’s Coach gonna do?”

Dean poured himself a cup of coffee, “He’ll live. I’m the best forward the roller hockey team’s got—and we’re gonna need it, if we want to medal.”

“You’re also modest.”

Dean took a gulp of his coffee, “And?”

“And nothing.” 

“Hm.” Dean snagged some bacon and toast from the stove and headed back to his room to get dressed.

Fifteen minutes later, he swung his car (a 1967 Chevy Impala that everyone on the team persisted in making fun of) into the Albuquerque Sportsplex lot. He knew that the loud engine of the Impala would immediate alert everyone to his presence, but screw that noise. He was only ten minutes late. Who would mind?

“You’re ten minutes late.”

“Good morning to you too, Milton. Do you always sleep with a stick up your ass?” Dean asked. Cas just rolled his eyes and stalked away, roller-skates in his hand.

Castiel Milton (or, as everyone on the team called him, Cas) was the most infuriatingly attractive person Dean had ever met—in terms of him being both infuriating and attractive. Cas was a stickler for following the rules, was an absolute beast at roller figure skating (he had dominated the long program event at the 1983 games), and he had perpetually tousled black hair, vibrant blue eyes that nearly had their own gravitational pull, and…

Dean stopped his mental description of Cas there. He was about to have to get into his practice uniform, and there were some things he didn’t need showing.

“Someone’s late,” Steven Coleman, one of the roller hockey goalies said, striding past Dean, “Don’t let Coach see you.”

Dean rolled his eyes.

This day could not end any sooner.

**************************************************

August 6, 1987 (one day before the games)

Castiel

“Nothing short of—Gabe, give me duffel back!”

“Or what, Cassie?”

“Or I’ll kill you.” Cas narrowed his eyes, his eyebrows slanting inwards, “Seriously, I can’t be late. The shuttles to the airport are leaving at nine am sharp.”

“Oh,” his older brother teased, “And if you’re late, Dean Winchester will never you let you hear the end of it?”

Cas elected to ignore Gabe, “Please give it back.”

“Fine. But check to make sure you got everything. I don’t want any panicked phone calls from Indianapolis while I’m trying to relax without you for two weeks.”

Cas rummaged through his suitcase and duffel, “Skates…backup skates….fix kit…extra bolts…practice clothes….short program costume….long program costume…..regular clothes…”

“Underwear?” Gabe asked.

“Duh.”

Gabe slapped Cas on the back, “You’re gonna do great, buddy. You took bronze in 1983, and you’ve grown so much since then.”

“Yeah….” Cas sighed, “I just hope the injury doesn’t act up.”

“Cas, that was three years ago.”

“And?”

“And I want you to stop worrying about it. Now, let’s get in the car, I thought you didn’t want to be late.”

Later, at the Sportsplex, as Gabe’s truck sped away, a voice behind Cas said, “Nice pimpmobile, Milton.”

“It’s a Lincoln Continental, not a ‘pimpmobile.’”

“Even better, air-quotes. I know what kind of car it is—but I also know that only losers drive one.” Dean was smirking at him.

“Nice of you to show up on time,” Cas replied, “Finally learned how to actually wake up to your alarm?”

“Ha.” 

Cas had never quite gotten a handle on Dean. Even though they were both now, after six years, considered veterans on the team (the only one who had been around longer was Jo Harvelle, one of their inline speed skaters), Dean had always seemed brash to him, like the anthesis of someone who would dedicate their life to roller skating. He was all leather jackets, dirty flannels, blaring rock music from the speakers of his insufferably loud Impala that he persisted in calling Baby….

At least he wasn’t a figure skater like Cas. If Dean was in one of those sparkly get-ups, paired with his ocean of freckles and his (indescribable) green eyes…it would have been too much. The hockey uniform was enough on its own.

And it wasn’t like they were enemies. 

Right?

“Okay,” Coach Lafitte said, coming in front of them, “For those of you who were at the last games, you already know how this works. For the newbies, welcome to the party. I expect the US roller skating team to be on their best behavior. No shenanigans. No sleeping with people on the other teams.”

“Can we sleep with people on this team?” Dean muttered, and Cas elbowed him to shut him up, earning another smirk.

“You all need to make sure you show up to things on time, I’m not your mother, I won’t babysit you. And take care of yourselves. We don’t want any injuries, okay?”

There was a chorus of nods, and then they were all piling into the shuttles. Cas ended up wedged into the window on the back row next to Dean, who was fiddling with his walkman.

“Seriously?” Cas grumbled, “It’s less than thirty minutes to the airport.”

“Well, forgive me, but my head’s not full of air, so I actually need things to occupy my time.”

“Or maybe I haven’t been hit over the head with a hockey stick, and so my brain still works.”

“Cool it, lovebirds,” the aforementioned Jo said, her curly blond ponytail whacking the seat as she turned around, “We haven’t even left Albuquerque. If this is what I have to deal with for the next two weeks…”

“Fair’s fair,” Dean shot back, “I know you’ll be griping about missing your fiancé the whole games, the least we can do is liven it up.”

Cas watched them banter for a few minutes before staring out the window. Despite the way that Jo and Dean’s abrasiveness could sometimes be off-putting, they were his closest friends. Something about being weirdos who were really good at roller-skating, good enough to make a national team, and then surviving for six years on it (or seven, in Jo’s case), was bonding. Even if they all did different events.

And even if, three years ago, Cas had barely been able to roller skate again. If he listened, he could still hear the sickening crack of his ankle as he fell.

“Hey, Feathers,” Dean said, prodding him, “Who’s watching your apartment while you’re gone?”

Cas rolled his eyes at Dean’s nickname (Dean loved to mock him for being named after an “unheard of stupid angel”—Seriously, an Angel of Thursday? What the hell is that?), “My brother Gabe. Well, we live together.”

“I remember Gabe. He’s a—“

“Bartender at a nightclub.” Cas sighed, slumping down, “And he’s not even that good at it. He’s just good at picking up chicks.”

“I’d probably be better friends with him than you, honestly.”

“Well,” Cas grumbled, “You’re stuck with me.”

Two weeks of mostly non-stop Dean Winchester.

Yeah, this was gonna be the death of him.