Milkmanpie
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Summary
Dean's sixteen when he meets John's well-to-do boss, Castiel Novak, and he's quick to develop a crush during a time where he's only begun to discover his preferences. He dates the beautiful Lisa and practically raises his younger brother Sam, because it's what John expects. But Castiel appears to see Dean in a way no one else does, and despite him knowing there's no way anything can happen between them, he relishes in the idea that Castiel cares at all for his well-being.
Between mounting pressures from a teenage Sam that no longer wants a caretaker, John's nudging for Dean to follow a career path he doesn't want, and a mysterious check for the exact amount of one semester at the school Dean had been eyeing, Dean finds himself reconnecting with Castiel.
And Castiel has a very interesting proposition for him.
Series
- Part 1 of Sweet Boy
- Language:
- English
- Words:
- 195,727
- Chapters:
- 21/21
- Collections:
- 5
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- 1,215
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Bookmarked by Milkmanpie
21 Jul 2025
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It was an accident. He slipped. That doesn't mean he isn't going to take advantage of the opportunity that presents itself.
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Post Lawsuit, Buck accidentally cuts his arm. He decides that maybe not getting help is best for everyone.---
TW for suicidal idealization and injury that turns into a suicide attempt.- Language:
- English
- Words:
- 36,091
- Chapters:
- 14/14
- Collections:
- 5
- Comments:
- 559
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- 10,894
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- 2,365
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- 285,797
Bookmarked by Milkmanpie
25 Mar 2025
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All Dean wants is a little privacy. Cas doesn't understand.
- Language:
- English
- Words:
- 94,118
- Chapters:
- 18/18
- Collections:
- 10
- Comments:
- 4,559
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- 23,297
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- 5,865
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- 570,766
Bookmarked by Milkmanpie
06 Jan 2025
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Summary
Newly single Dean Winchester is looking for a way to help pay the bills after his ex, Lisa, leaves him high and dry - taking half of the furniture along with half of the rent money when he finds out she's been cheating on him with another man. Castiel Novak is making a big move from Illinois to Kansas for a new job working nights as a L&D nurse at Kansas Memorial Hospital alongside his MD brother, Gabriel, and is having trouble finding a place to stay that's affordable on his nurse's salary. What happens when Gabriel and Dean's bff Charlie conspire to get the two men to share rent - and the bed - without ever meeting or knowing who the other one really is?
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The one where Dean thinks his new roommate Cas(sie) is a chick and Cas is just as confused by who he's sharing a bed with.
- Language:
- English
- Words:
- 61,864
- Chapters:
- 1/1
- Collections:
- 1
- Comments:
- 101
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- 525
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- 157
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Bookmarked by Milkmanpie
31 Dec 2024
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Summary
In which Dean is forced to deal with his trauma and come to a reckoning with himself. Also, Cas is there.
See notes for more specific Content Warnings.
*** *** ***
"No one hates you as much as you do," Crowley told him once. That's Dean's whole M.O. right there. His two fundamental truths are that it is his job to save everyone, and that no matter how many people he saves it will never change the fact that he is 90% crap.
Dean knows who he is. Yeah, he's done some good for the world, okay, he gets that. But deep down? The person he is inside is still worthless. Dean will never be good enough, never be any kind of role model. He's never going to shake that, so if that's what this whole seven trials angelic bullshit is about, then he and Cas might as well hold hands and drive off the cliff now.