HEADCANON: How he spoils you

Time for another HC! This one comes as a Patreon request from @spnbabe67 ❤️

Request: Which one of the big 5 do you think would spoil you the most? And, what do you think each of their ways of spoiling/indulging in you would be?

᯽ With Dean Winchester, Beau Arlen, Soldier Boy (Ben), Mark Meachum & Russell Shaw ᯽

Tags & Warnings: (18+) | Some smutty musings, mostly with SB of course lol

᯽ Mark Meachum

Pratt Fall

Pairing: CEO!Dean Winchester x Assistant!Reader

Summary: Behind every powerful man is a resourceful woman. He doesn’t realize how much he relies on you, until he realizes how much he wants you.

AN: This was originally requested as a birthday fic for a lovely Patreon member, @redhoodieone! It's my first attempt at an office AU with Dean, but I know it's a popular trope for a reason lol. Hope you guys enjoy this little snack of office smut ❤️‍🔥

Posted on Patreon: Feb. 7, 2026 | Word Count: 1.7K

Tags & Warnings: 18+ | Office politics, power imbalance (but not really), hint of angst, but mostly smut (v. fingering, oral – female receiving)

Series Masterlist ➤ Dean Winchester Masterlist

“Dean, you’re driving me crazy!” you snap. “Just read the speech as written. Sam and I worked on it for two weeks. It’s perfect.”

“Yeah, but it doesn’t even sound like me,” he grumbles. “What the hell does ‘solidarity’ mean?”

You utter a sigh as you follow him into his office, shutting the door behind you with your ass. Your hands are full—with a large binder of purchase orders that still need to be approved by the very man who can’t seem to take anything seriously.

THE ASSISTANT || Series Masterlist

Pairing: CEO!Dean Winchester x Assistant!Reader

Summary: Behind every powerful man is a resourceful woman. He doesn’t realize how much he relies on you, until he realizes how much he wants you.

AN: Thanks to the resounding feedback on Pratt Fall, here's a mini series for CEO!Dean and his Executive Assistant. 😉❤️

Series Tags & Warnings: 18+ | Office politics, power imbalance (but not really), single mom!reader, deadbeat dad, angst, drama, mutual pining, smut (v. fingering, oral, p-in-v, office smut, etc.) | inspired by Two Weeks’ Notice (2002)

Chapters:

Listed in written order instead of chronological order -

➤ Pratt Fall

➤ Mutual Engagement

➤ Nothing by Halves

Series complete!

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Mutual Engagement

Pairing: CEO!Dean Winchester x Assistant!Reader

Summary: Let’s take it back to Day 1. Here's how you got the job at HunterCorp as Dean Winchester’s Executive Assistant, how you kept it, and the day your professionalism with him finally broke.

AN: Ready for more Boss Man Dean? insert Chandler Bing gif (Friends fans will know lol) This of course is in the same world as Pratt Fall, but it spans the year building up to that moment.

Posted on Patreon: June 19, 2026 | Word Count: 9.6K

Tags & Warnings: 18+ | Single mother!reader, ft. a deadbeat dad, mutual pining, Dean’s dirty thoughts, office shenanigans and smut (v. fingering, penetrative sex – yes, on the desk)

Series Masterlist ➤ Dean Winchester Masterlist

“No,” Sam says, snatching the resume out of his brother’s hand.

“Aw, come on,” Dean says. He swivels in his leather chair but doesn’t bother getting out of it.

Sam levees him with an exasperated look. “This girl spelled ‘assistant’ with three Cs and a Y.”

“She’s funny,” Dean shrugs, once again taking a look at the applicant’s profile on his computer. In his opinion, her pouty lips and dewy young face speak for themselves. “And smokin’ fucking hot.”

“She’s illiterate,” Sam deadpans. He sorts through the resumes he printed off and hands his brother three strong candidates that he picked himself.

Back in Black

Pairing: Dean Winchester x Reader

Summary: When Dean comes back from Hell, you quickly realize that his subconscious remembers more than his waking mouth admits.

AN: Requested by Ashley Klann on Patreon! I’ve written a “back from Hell” piece before with an Omegaverse twist, called Make it Right. But here’s a more canon-rooted drabble. 💜

Request: After Dean comes back from hell, he has nightmares and a breakdown. The reader is there to comfort him and just holds him, and he ends up letting all pent-up feelings out.

Posted on Patreon: May 15, 2026

Word Count: 1.3K

Tags & Warnings: Set around mid-season 4 (when Sam was traipsing around with Ruby). Established relationship, angst, feels, hurt/comfort to the max

Dean might’ve been able to shrug off ghost sickness. He might’ve been able to look you and Sam in the eyes, with his third beer in hand, and claim he didn’t remember anything about his four months in Hell.

But what he just couldn’t do was make you believe it. Not a month ago, not last week, not tonight.

Nothing by Halves

Pairing: CEO!Dean Winchester x Assistant!Reader

Summary: Dean attends your daughter’s play—and meets your ex-boyfriend for the first time. The only real commitment Dean Winchester has ever had is to his work. Is he really a man you can rely on?

AN: We had some office spice. Ready for some fluff and family feels?

Posted on Patreon: June 26, 2026 | Word Count: 2.5K

Tags & Warnings: Single mother!reader, ft. a deadbeat dad, jealousy, fluff and feels

Series Masterlist ➤ Dean Winchester Masterlist

Dean finds a guest spot in front of the school. The old Impala rumbles to a stop there, and he climbs out, grabbing the bouquet resting in his passenger seat.

His keys jangle in his other hand as he makes his way to the front office to check in, just like you told him to in your texted instructions. The nice ladies there give him a guest badge that he slaps on his chest, over his dress shirt, and they tell him how to get to the theater.

He feels awkward and out of place walking down the halls of this school alone, but you had to take Emma over there early before the show. 

The hell am I doing here?

He has to fucking wonder.

But he promised you. He promised the kid. So he’s here.

RETURN TO ME || Series Masterlist

Pairing: Dean Winchester x Reader

Summary: Just outside the small town of Salida, Colorado, the Winchester Ranch spans from the forests and mountains of Antero to the frosty edges of Breckenridge. John Winchester isn’t about to concede his family legacy to anyone who comes to take it, but he’s sure trained his sons to protect it—with their own sets of skills.

When you return to Salida after 12 years, your reason brings you back to the ranch you couldn’t wait to leave, and to the boy you never wanted to see again. Well, Dean Winchester is a man now, and despite your best efforts, you aren’t immune to the pull of his charms, or the darker secrets of his world.

AN: Ready for some more Cowboy!Dean? 🤠❤️ Imagine Yellowstone meets Sweet Home Alabama, set in the Colorado mountains!

Supporting Cast: Sam Winchester, John Winchester, Jessica Moore (Jess), Castiel (Cas), Benny Lafitte, Brady (Weiss), Jack Kline, Kevin Tran, Dick Roman, and more character cameos as well as new OCs along the way

Series Tags & Warnings: 18+ || Modern Cowboy!AU, romance, exes to lovers, smut, angst and messy drama (reader and Dean aren't perfect), jealousy, violence and death, family secrets, and more chapter-specific tags || background Sam x Jess and other pairings

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"How far will you go? You should know, you'll be on my mind..."

℧🌹 Chapters:

Ain't so hard to recognize

Pairing: Dean Winchester x Plus-size!Reader

Summary: Our green-eyed hunter somehow never marked himself as the jealous type, but turns out, it doesn’t take much.

AN: Surprise! Here's an angsty fun one-shot requested by Jacqueline on Patreon. Time to let this drop here. Hope you enjoy! 🧡

Word Count: 3.6K

Posted on Patreon: Mar. 24, 2026

Tags & Warnings: (18+) | One-sided semi-flirting, jealousy, angst, established relationship, curvy reader, Dean's self-worth issues, love confessions, romantic smut (v. fingering, penetrative sex, cowgirl)

Now Playing: “The Rain Song” by Led Zeppelin

There’s only one good bar in Lebanon, Kansas. After six months of living here, you’ve more than confirmed it in a town of less than 200 people.

They’re frankly lucky to have one working stoplight. 

But after a long and stressful hunt finally pays off, you can usually convince Dean to take a detour on the way back to the bunker.

A few years ago, back when you first met the brothers Winchester, and before they had a bunker to go home to, Dean was always the one suggesting a few celebratory beers after the work was done. Or a motivation beer, during.

Sam was usually the one wanting to go back to the motel, either to crash, or to do some more research without the smell of cigarette smoke and sweat (or some drunken idiot puking in the corner).

Dean was the one more guy.