MilfSamWinchester
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Summary
He meets Dean at a cafe when he's a month away from turning 16.
Bookmarked by MilfSamWinchester
09 Sep 2026
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Season 15 Sam finds an AC/DC band t-shirt in a closet in the bunker that used to belong to a 14 year old Dean, he puts it on and models it for Dean. He loves what he sees and a fun chase through the bunker ensues with Dean feeling possessive and toppy when he catches Sam.
Series
- Language:
- English
- Words:
- 2,115
- Chapters:
- 1/1
- Collections:
- 1
- Comments:
- 4
- Kudos:
- 222
- Bookmarks:
- 61
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Bookmarked by MilfSamWinchester
09 Sep 2026
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Prompt: And if you're open for prompts again, how about a first time after Stanford. Dean and Sam are in a fight about why Sam left and Dean found out, he was the reason, bc Sam was always in love with him and he interrupted the argument with a fierce kiss. Bottom Sam, Bonus for coming untouched. That would be great!!! Thank you! <3
Series
- Part 112 of Kink/Request Fics
Bookmarked by MilfSamWinchester
04 Sep 2026
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Summary
“Like, what does that even mean?” Sam complained, staring at the empty crossword. “I thought it was ‘starter,’ but that’s only seven letters. Position for beginners…”
“It’s ‘missionary,’” Dean blurted, the answer tumbling out before he could stop himself.
His eyebrows pulled together. “What does that mean?”
…
“I can show you,” Dean finally said, selfish and disgusting, the words coming out quieter than he'd intended. “But we have to move to the bed.”
Bookmarked by MilfSamWinchester
29 Aug 2026
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Summary
This is Dean's official stance on the song "Carry On Wayward Son" by Kansas. And this is Sam's reaction to it.
Series
- Part 33 of The Chicago Verse
Bookmarked by MilfSamWinchester
26 Aug 2026