deansimp01
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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
- Comments:
- 1,215
- Kudos:
- 3,345
- Bookmarks:
- 1,104
- Hits:
- 127,562
Bookmarked by deansimp01
16 Dec 2025
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Single dad and mall cop, Dean Winchester, can’t wait for Christmas to be over.
Not that he doesn’t love seeing his little girl enjoy the holiday season, but malls always go all out when it comes to this shit—music, lights, commercials, fucking cookie samples, the whole nine.
Dean can usually grin and bear it for Emma’s sake, but for some reason, he can’t shake it this year. Maybe it’s the looming stress of making ends meet and keeping Emma's world steady. Or maybe it’s the fact that this year's mall Santa keeps looking at him weird.
Bookmarked by deansimp01
14 Dec 2025
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Castiel never expected to see Dean again after all this time, but he can't say he's mad about it when Dean looks this beautiful under a haze of neon lights. No words he's written about Dean over the years could compare. Something about Dean just seems different now, and Cas can't help but want to close the distance, to learn more about the enigma of Dean Winchester.
But Castiel has changed as well, his words and appearance gaining edge and confidence, and the walls he's built to protect his soft underbelly have grown tall.
Dean's been falling in love with the emo queer kid for as long as he can remember, and he regrets losing touch with him for years after being profoundly bonded, so now he's working to try and get him back. If only it were that simple. Does Cas want to know the person Dean is now?
Can they let each other in one more time to try?
- Language:
- English
- Words:
- 35,019
- Chapters:
- 6/6
- Collections:
- 1
- Comments:
- 25
- Kudos:
- 106
- Bookmarks:
- 49
- Hits:
- 2,379
Bookmarked by deansimp01
20 Nov 2025
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Dean's been having a rough go of it lately: On top of struggling to process failing at a job he'd thought he was destined for, his apartment building unexpectedly changes their pet-friendly rules, so he's forced to start looking for a new home for himself and his dog, Miracle. At every place he visits, he runs into the same applicant—the handsome, blue-eyed Castiel and his dog, Leroy—and finds himself falling for him more and more with each tour. Suddenly, finding a new place to live and navigating his mental health aren't the only things on Dean's mind.
- Language:
- English
- Words:
- 26,874
- Chapters:
- 8/8
- Collections:
- 1
- Comments:
- 80
- Kudos:
- 252
- Bookmarks:
- 61
- Hits:
- 3,356
Bookmarked by deansimp01
14 Nov 2025
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Raise the Black by emmbrancsxx0, valleydean (emmbrancsxx0)
Fandoms: Supernatural (TV 2005)
01 Oct 2022
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Nassau, 1717. Captain Dean Winchester of the Impala is a born and raised pirate, committed to disrupting commerce and civility on a global scale. After a battle at sea with the Royal Navy, Dean discovers a stowaway on his ship: Castiel Novak, an officer from Carolina with a secret. As their relationship grows, so does England’s determination to end piracy in the New World. This is the story of how men can become legends and how love can ignite a revolution.
- Language:
- English
- Words:
- 246,531
- Chapters:
- 16/16
- Collections:
- 3
- Comments:
- 983
- Kudos:
- 1,150
- Bookmarks:
- 526
- Hits:
- 41,959
Bookmarked by deansimp01
10 Nov 2025