1 - 20 of 64 Bookmarks by Themostchalant
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Cas steps further into the motel room, sees the pipe and the baggy on the floor, and says, "So, how do you do it?"
Dean chokes on his pie.
Sam doesn't help him. "You… you want to smoke weed with us?"
"Sure," Cas says levelly, sitting down on the floor and frowning at their supplies in concentration. "Though, I will confess that I've never done this before."
"Yeah, no, Cas, that's-- that's fine," Sam stutters. "Uh, Dean hasn't really, either."
*
Or, a oneshot where Dean's never really smoked before, and Sam thinks 4/20 is a good day to introduce him. They get Cas in on the fun, too.- Language:
- English
- Words:
- 4,315
- Chapters:
- 1/1
- Collections:
- 1
- Comments:
- 9
- Kudos:
- 70
- Bookmarks:
- 6
- Hits:
- 545
Bookmarked by Themostchalant
27 Apr 2026
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Your period hits you like a bus, and you're worried you're going to ruin Dean's day of rock 'n' roll and pie by being exhausted and crabby. But Dean isn't going to let his Sweetheart suffer when he can lend a helping hand (or other body part)!
This contains period sex, in case I haven't made that abundantly clear. No Red Wings, but it is mentioned.
- Language:
- English
- Words:
- 1,627
- Chapters:
- 1/1
- Collections:
- 1
- Comments:
- 18
- Kudos:
- 74
- Bookmarks:
- 9
- Hits:
- 1,113
Bookmarked by Themostchalant
08 Apr 2026
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You and Sam come up with a plan to complete a hunt, which Dean heavily disapproves of. What will happen when you ask Dean for some advice and help for the hunt? What will it be?
Bookmarked by Themostchalant
03 Apr 2026
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You’re a hunter running with the Winchesters who happens to be a virgin. You so don’t want that become a thing, so, of course, it becomes a thing.
- Language:
- English
- Words:
- 29,935
- Chapters:
- 17/17
- Comments:
- 319
- Kudos:
- 1,426
- Bookmarks:
- 139
- Hits:
- 33,400
Bookmarked by Themostchalant
13 Mar 2026
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In the spring of 1944, the 104th Medical Battalion of the United States Army is disbanded, and its men reassigned to various infantry companies in preparation for their invasion of occupied France. For First Lieutenant Novak, this is less than helpful, as he has so far met his platoon’s designated medic a grand total of twice, and has both times found Sergeant Winchester to be the optimum combination of reckless, arrogant, and downright insufferable so as to make cohesive platoon function near impossible. When the time comes to move out, however, Castiel has to reconcile himself to the fact that men are going to go down and trust that Dean Winchester may well be the only person who can put them back together again. WW2 ETO infantry AU.
Series
- Part 1 of Ninety One Whiskey
- Language:
- English
- Words:
- 401,183
- Chapters:
- 20/20
- Collections:
- 15
- Comments:
- 2,942
- Kudos:
- 14,382
- Bookmarks:
- 4,930
- Hits:
- 634,974
Bookmarked by Themostchalant
24 Feb 2026
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Dean's refusing any help to get over his sex curse, no matter how many women you find for him. If only he'd just tell you why.
Series
- Part 38 of Dean Winchester I Will Love You
Bookmarked by Themostchalant
22 Feb 2026
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Dean Winchester is your friend and hunting partner but can it stay that way with the way you've both been feeling about each other.
Bookmarked by Themostchalant
05 Jan 2026
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You've been a hunter for a long time and had known the Winchester brothers in passing before. You heard they stopped hunting, or died, or something, about a year ago when suddenly a dirt-and-blood covered Dean Winchester interrupts your friendly bonding session in the forrest and sends shocks straight to your core.
Bookmarked by Themostchalant
30 Dec 2025
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Sam and you have admitted your feelings for each other, but one evening takes you a step further…
Sam's POV: retelling and continuation of “You’re bossy. And short.” and “No hair of the dog”.
This accidentally got smutty.Series
- Part 3 of Bossy & Short
Bookmarked by Themostchalant
28 Dec 2025
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When you go to visit your parents for a few weeks you’re met with a blast from the past, your best friends big brother is your parents pool guy. A brother that you used to have the biggest crush on when you were younger, what’s the worst that can happen when you watch him work?
Bookmarked by Themostchalant
24 Dec 2025
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Y/N was currently fighting two very strong demons, sexual frustration and boredom. It had been over a month since she had a good lay and about two weeks since she and the Winchester brother's went on a hunt.
Luckily a late night argument with Dean after another of her failed hook ups leads to fixing one of her problems.
Bookmarked by Themostchalant
24 Dec 2025
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Request: Can you write a smut story with dean in it I was hoping a friends to lovers sort of thing
Bookmarked by Themostchalant
01 Dec 2025
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~Dean Winchester has got quite a mouth on him, and he knows just what do to drive you insane...~
Bookmarked by Themostchalant
01 Dec 2025
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You're not cursed. You don't feel anything wrong. If anything, you feel better, because there's a weight lifted off your tongue that lets you say whatever you want.
And most of what you want is Dean.
Series
- Part 15 of Dean Winchester I Will Love You
Bookmarked by Themostchalant
30 Nov 2025
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You’re just drunk.
Sam turns the words over in his head like a prayer, clinging to them when you keep trying to shove past his limits. He’d thought he knew how the night would go: you and Dean working your way through half the bar, Sam nursing a couple of beers, steady as always. And in the end, he’d be the one to slide in the driver's seat of the Impala, headlights carving through the dark road, while you and Dean dissolved into each other in the back seat. Your giggles would be drowned out by the scrape of Dean’s mouth, and his hands would be too curious, too certain. Sam would keep his eyes on the road, ignoring the slow twist in his stomach.
--
Or rather, Dean goes too far one night, and the best way you know how to get back at him is to get under his brother.((NO WINCEST, SEASON 2!SAM))
Bookmarked by Themostchalant
30 Nov 2025
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Birthdays: Winchester Sandwich Style by Sam_Is_My_Safe_Word for DandelionDreaming
Fandoms: Supernatural (TV 2005)
19 Aug 2022
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Summary
You came out here to write. A little hideaway from the world. It was going nicely. Then a '67 Impala brought you some neighbours for a weekend.
Flirting ensues, both of them trying to catch your attention. They 100% have it!
A generator mishap leaves you offering them a warm place to spend the night.
Drinks, life stories and a stolen towel lead you to the only rational thing to do when you've got the Winchester brothers on your sofa propositioning you.
You hang on for the ride of your life.AN: No wincest.
Series
- Part 2 of The Birthday Trilogy
Bookmarked by Themostchalant
29 Nov 2025
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Wayward and Wanting - Wanderlust with the Winchesters by Reedemer46
Fandoms: Supernatural
20 Apr 2025
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Summary
Series of one shot adventures featuring the Brothers Winchester and likely others. Mainly reader driven stories. I don't own any of these characters. If you have a particular request, let me know. I'll do my best to accomodate.
Bookmarked by Themostchalant
10 Nov 2025
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Sorry's Smutober Spectacular 2025 by sorryitsmyfirstdayonearth
Fandom Supernatural (TV 2005)
30 Oct 2025
Summary
1. Bodily fluids - Dean - Oct 2
2. Cockwarming - Sam - Oct 4
3. Gender swap - Dean - Oct 5
4. Fuck or die - Sam & Dean - Oct 7
5. Blindfold - Sam - Oct 9
6. Threesome - Meg & Ruby - Oct 11
7. Phone sex - Sam - Oct 12
8. Making out - Sam & Dean - Oct 14
9. Erectile dysfunction - Sam - Oct 16
10. Overstimulation - Sam & Dean - Oct 18
11. Sexting - Dean - Oct 19
12. Semi-public sex - Sam - Oct 21
13. Strapped - Dean - Oct 23
14. Bratting - John - Oct 25
15. CNC - Dean - Oct 26
16. Masturbation - Sam - Oct 28
17. Humiliation - Dean - Oct 29
18. Biting - Sam - Oct 30- Words:
- 40,576
- Works:
- 18
- Bookmarks:
- 13
Bookmarked by Themostchalant
08 Nov 2025
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Summary
Leave it to the universe to put you on a collision course with none other than Dean Winchester right after a break up. Then again... he might have just the right medicine.
Prompt: Rebound Sex
Series
- Part 6 of Avery's Kinktober 2025
Bookmarked by Themostchalant
13 Oct 2025
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Can This Feeling Haunt You Too? by godmadeaterribleerror
Fandoms: Supernatural (TV 2005)
26 Aug 2025
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Summary
When you and Dean are hit with a love spell that doesn't work, you have to confront some feelings.
Series
- Part 30 of Dean Winchester I Will Love You
Bookmarked by Themostchalant
05 Oct 2025