21 - 40 of 2,568 Works in Sub Dean Winchester
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Kinktober Day 28: S&M
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Dean and Castiel start to form a relationship. Baggage, return of ex's, and a concerned dominant with a emotionally guarded submissive. Dean has walls but even he doesn't understand how to deal with them. Castiel is a patient and understanding person, he will wait, believing Dean was worth it. Dean however didn't believe he was.
Series
- Part 2 of Till a Want turns to Need
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When Dean goes with Cas on a shopping trip, his dom seems to be more interested in anything but Dean. Despite Dean's bratty efforts to get his attention, Castiel refuses to rise to the bait.
That doesn't mean he wasn't counting the infractions.
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Dean Winchester has a panty kink. Reader has a Dean Winchester kink. Both believing they're alone in the bunker leads to some interesting ways to test the boundaries of friendship.
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Kinktober Day 26 & 27: Lingerie & Hair Pulling
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She’s not ashamed to admit it, that Dean’s first thought when Cas threw her against the wall was God, it’s so hot when she’s rough with me.
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The Costume by castiels_golden_chariot (cleverunseenviper)
Fandoms: Supernatural (TV 2005)
05 Nov 2025
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He extends his hands to explore the garment, the fabric scratchy under his palms. “I want to act on the thoughts, too.” Dean’s fingers stroke down towards the hem, where the buttons close it, his eyes searching Castiel’s for approval.
Series
- Part 21 of Suptober 2025
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Getting kidnapped wasn't exactly high on Dean Winchesters agenda for the day but now that it had happened, he figured there was not much he could do about it.
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Crying Over Spilled Chlorine (Day 30, Prompt 31) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
31 Oct 2025
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The hotel they're staying at has a hot tub, one that's closed to the public after hours. Cas gets an idea, but it doesn't go to plan.
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You meet Dean Winchester at a bar, and he takes you back to his motel, where you show him who's truly in charge.
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One time after a messy and bloody hunt where Cas had to heal Dean from deadly injures he got doing a reckless action, Castiel reprimands him and calls him an idiot. It ends with Dean fantasizing about Cas fucking him while calling him a whore and he accidentally prays to Cas and the angel comes to do exactly what Dean fantasized about. Porn and A LOT of dirty talk!
Kinktober Day 30 & Day 18 – Degradation, dom/sub
Series
- Part 9 of Kinktober 2025
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Kneel and Receive, Gladly (Day 29, Prompt 30) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
30 Oct 2025
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They might as well just exchange rings at this point (they don't, but they should).
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“I ain't nothin' but a nasty dog” - Kinktober Day 29 (Omorashi) by cosmic_caden
Fandoms: Supernatural (TV 2005)
30 Oct 2025
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Dean agreed to try Sam’s strange fetish. And now his bladder as about to burst even as the two brothers were on their way to interview a key witness. Will Dean make it or will he have an accident?
Series
- Part 31 of Kinktober 2025
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From The Cradle to The Crib (Day 28, Prompt 29) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
29 Oct 2025
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Cas and Dean revisit a kink, but add a new element.
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Dean and you are training when he has an unexpected reaction to you pinning him down. You take it in stride - and Dean gets more than he bargained for.
Series
- Part 17 of Sorry's Smutober Spectacular 2025
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Just Like a Bitch in Heat (Day 27, Prompt 27) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
28 Oct 2025
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They try their hands at another scenario, one that's a bit wild.
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Castiel has been a good pet, so he gets a reward while Dean gets to watch.
- Language:
- English
- Words:
- 6,520
- Chapters:
- 1/1
- Kudos:
- 13
- Hits:
- 492
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This is part of a series called "Weird Together," so it's clearly filled with super normal stuff.
Dean being Cas' adorable pet human, Cas tasting tears for the genetic material they contain, Dean crawling across a meadow, under stars his boyfriend made, for a crumb of dick.
Nothing weird here!
(There are, in fact, many weird things here.)
- This can be read by itself.
Series
- Part 10 of Weird Together
- Part 10 of PeachyHalloween's Kinktober 2025
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Dean enters a Haunted House. If he survives the full time he leaves with half a million dollars. Dean will do anything for that money. Including suffering extreme verbal and physical humiliation. Well his dick doesn’t seem to be suffering.
Series
- Part 1 of Halloween