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#i have never written saileen before and like ive said in the past dialogue is NOT my forte so im sorry in advance if this bad
chocolatecakecas · 3 years
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Yeah, Should Have Seen That Coming: Saileen Bachelor Party Ficlet
Congrats to the soon to be Mrs. and Mr. Leahy💚💍!!!
Sam had the brilliant idea to have their bachelorette/bachelor parties on the same night. Two separate parties, at least a week before the wedding to avoid any last minute mishaps (learning from the mistakes of Dean and Cas' party last month). They had thought of everything, Sam even remembered to invite Adam this time. They were each going to have a perfect party with no unforseen issues, because they both deserved a night of fun.
Dean was granted the privilege of being Eileen's best man maid of honor, so he shut down his bar that night, and threw her an absolute rager. He even dragged the stripper pole back out at Eileen's request (though Dean thinks it was a shame Cas wasn't going to be there to use it) and set up a mechanical bull. So of course Cas was chosen to be Sam's best man, and for his party, Sam just wanted a normal, quiet night. Just board games, beer and burgers at the bunker (Crowley was pissed he got stuck at Sam's instead of Eileen's, but Garth was thrilled about the prospect of playing Monopoly). So that's exactly what Cas planned to give him. He makes sure he's got Sam's favorite beer, burgers from the place that makes his favorite vegan burgers, he's taken care of everything. And all Sam has to do is grab the board games from one of the storage rooms.
What could possibly go wrong?
Well, considering Sam and Cas are involved? 
Everything.
(read the rest under the cut)
They ended up on a hunt before the party even began. Sam had accidentally bumped into a shelf in the storage room, knocking over a cursed object, and then picked it up without thinking("Sam why did y- "It just looked like a piece of wood!" "It's not, its cursed it's called t-" "Well that doesn't help me now, Cas!"). And so it turned out, they unleashed an ancient curse that if they didn't break by midnight, the world would be "shroud in 5 billion years of darkness". But Sam won't let anyone call Eileen or Dean ("I just don't want to ruin her party!" "Sam the world could en-" "Yeah, but that happens all the time. How often do you get to have a bachelorette party?")
So it was up to Sam, Cas, Jack, Crowley, Garth, and Adam (Kevin was already halfway up the steps and on his way to Dean's bar before Sam even finished explaining what happened).
And a lot can go wrong over a few hours, especially if the threat of the end of world is looming over you.
In the past three hours, they managed to successfully tear apart the entire archives looking for lore, had Jack fly them to three different states to wake up three experts on the subject, fought and killed one of Crowley's old nemesis who had an ingredient they needed for a spell, were briefly transported to a different dimension, twice (Jack was able to get them home, but they had to go back because Garth forgot his phone). Then of course they summoned the wrong ancient god, then had to figure out how to kill them, before they eventually summoned the right one needed to break the curse.
At that point, after some encouragement (yelling) from everyone, Sam finally gave in and tried to facetime and text Eileen, finally allowing Cas to call Dean too.
But neither of them answered because Eileen was currently in the middle of an intense drinking contest between Rowena, Mary and Kevin (who arrived 2 hours ago and mentioned nothing about the curse), while Dean (totally sober mind you) learned he was amazing on the stripper pole, as Charlie, Kaia and Claire cheered him on, and Jo along with some of Eileen's hunter friends were trying out the mechanical bull.
So they were on their own, and quickly running out of time.
But unfortunately for them, the three hours of chaos was a complete waste, since they discovered a bit too late that lore was wrong. Because the weapon that was supposed to kill the God was clearly not working since it seemed to be chasing them around just fine, with a giant stake in it's neck. So they hurriedly decided splitting up would be the best course of action, and they scattered in all directions as they ran into the woods(where they had landed when Jack zapped them back) trying to confuse the God. 
Which had been a complete mistake ("It can clone itself!" "Yes, thank you Sam, I hadn't noticed").
And currently, Crowley and Garth were both knocked out by some of the God's clones, and Jack was nowhere to be seen, leaving just Sam and Cas to fight with what they had (2 guns, an angel blade, and half a flask of holy water, so nothing)
Now there was only five minutes until midnight and the God had them surrounded, as it threw their useless guns and blades halfway across the forrest.
And only one thought rang through Sam's mind.
"Eileen is gonna kill me if the world ends before the wedding"
"Well if you hadn't touched th-"Cas started
"Thanks Cas, you really know how to make a guy feel better" Sam yelled back, swiflty cutting him off.
He glanced back up to see the God (who's name Sam had already forgotten) inching closer, holding them in place as they were readying themselves to smite them.
Sam took one last look at Cas and the reality of the situation finally set in. This was it.
All Sam wanted was one normal night, but now the world's ending again and he doesn't even know the name of the God ending it.
They were screwed. Now he'll never see Eileen again and they'll nev-
Suddenly a wooden stake was shoved through the back of the God's neck with a crunch, sending them crumbling to the ground. It burst into black flames, disappearing.
And standing above them in a, 6 inch heels, covered in glow stick bracelets, and a bride sash, was a very tipsy Eileen.
She and Dean helped pull them to their feet, and Sam could cry at the sight of her (and he did).
As soon as he was standing, Sam frantically began rambling and signing trying to explain and apologize all in one breath. But Eileen simply took hold of his hands, stopping him in his tracks.
"You were supposed to use sheep's blood, idiot" Eileen signed with a smirk.
Then she grabbed by the shoulders, yanking him down into a deep kiss.
"Wait how did-where did yo-"Sam started as he broke away. He quickly takes in his surroundings spotting Claire and Kaia helping Garth to his feet, Rowena trying to wake Crowley, and Charlie and Jo who are probably trying to convince Adam not to leave. He finds Dean, Cas and Jack off to the side huddled close together, while Dean probably tells his husband how much of a dumbass he is.
"Jack flew to the bar, and we read through your's and Cas' texts. We were able to piece it together from there, and apparently you guys can't read. Maybe leave the hunting to the pros?" Eileen teased, swaying slightly (okay maybe she was a little more than tipsy). Sam tightly wrapped his arms around her, keeping her steady, as a smile grew on his face.
"I don't deserve you" Sam sighs, cupping her cheek.
"Yeah, you don't" Eileen shrugged with a smirk growing on her lips.
"She's right, you really don't" Dean's voice cuts through as he, Cas and Jack make their way over. Cas punches him in the arm with a fond smile.
"Well, that certainly didn't go as I had planned" Cas huffed.
"Yeah, understatement of the year buddy. But when does it ever?" Sam laughs, feeling a bit of relief.
Then Sam has another brilliant idea, smiling as he turns back to Eileen.
"So my party....was ruined by an ancient God. Mind if we crash your's?"
And an hour later, Cas (much to Dean's delight) is now spinning around on the pole while Dean, Charlie and Jo cheers him on. Crowley, Rowena, Garth and Jack (with a shirley temple of course) are seated at the bar, talking about god knows what. Claire, Kaia, Kevin and surprisingly Adam have just returned from the parking lot, giggling a bit too much. And Sam is now seven shots in, messily making out with Eileen in one of the booths. Eventually they pull away, just sitting in a drunken daze as they stare at each other.
God he can't believe she's gonna marry him. He really is the luckiest man in the world.
And before Sam can relay this sentiment, Eileen downs her glass, signs "watch this", and runs to take a turn on the stripper pole to the thrumming bass.
With a laugh he surveys the bar, watching his family drink and laugh without a care in the world. He spots Eileen and Dean by the pole in the center of the room, heads thrown back in laughter, as Cas and Jack cheers them on. So Sam quickly slides out of the booth and makes his way over, plopping down inbetween Jack and Cas, watching his fiancé and brother dance to the beat like idiots. Heart swelling at the sight of his family.
And yeah maybe this isn't the night they had planned, but it was certainly a night they'd never forget.
(Especially since Cas had shirts made that said, "I survived Sam Winchester's bachelor party")
Tag list:
(Please let me know if you would like to be added or removed!!!💛)
@wormstacheangel @smiledean @shelikestv @chaoticdean @midnightwings-deancas @jellydeans @sunshine-jack @archervale @wikiangela @organicpurplepants @writtendevastation @tkdwolf2012 @doemons-blog
@rolling-stoned-girl @skylerkernaghan @shadowywerewolfqueen @the-cookie-navy @thelahatiel @thefantasyfiend @castielle-deanna @aestheticflyer26 @multi-fandom-imagine @x-mypeopleskillsarerusty-x @wellofwoes @becky-srs
@multi-fandom-dark-lord @perfectkoaladream @castiel-for-lunch @it--hurts--to--become @bowtiesandneckerchiefs @dakiaty @feraldean @teamfreebees @keshetcas @hrh-princess-bea @martymar1963 @midnight-sparks-studio @slipper007 @rainbowsam @winchester-novak
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