1 - 20 of 28 Bookmarks by MilfSamWinchester
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Dean cares for Sam's wounds while he's asleep. As he himself drifts off, he awakens to something pressing and grinding against his thigh.
“Sammy… What’re you dreaming about hm?”
Contains dominant Dean, being pushy and kind of a dick in the beginning, he softens up near the end, and has a sweet remorse for his actions.
*CONTAINS SLIGHT NON-CON IN THE BEGINNING! (turns consensual later)Bookmarked by MilfSamWinchester
14 Sep 2026
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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:
- 223
- Bookmarks:
- 61
- Hits:
- 3,085
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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“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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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
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Midnight is bed time and the boys go through their routines, this time with a new addition thanks to Sam and his phone.
Series
- Part 35 of The Chicago Verse
Bookmarked by MilfSamWinchester
26 Aug 2026
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Sam arrives home one evening to find Dean dancing in the kitchen. He hopes to catch Dean in the act. What happens is so much better.
Series
- Part 36 of The Chicago Verse
Bookmarked by MilfSamWinchester
26 Aug 2026
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Sam is in the cage, Lucifer finds a new way to break him.
Lucifer takes the form of Dean to tempt Sam into giving in to his true feelings for his brother.
Bookmarked by MilfSamWinchester
24 Aug 2026
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Dean fucks Sam like the world is about to take him away. Hard, deep, relentless. He holds him through every broken sound, every tremor, every moment Sam’s mind starts to slip.
Whispers of 'I’m here' and 'I’ve got you' while he drives him past the edge and keeps him there.Just one night. Just them. Just Dean refusing to let go.
Bookmarked by MilfSamWinchester
24 Aug 2026
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Wandering through a flea market, Sam finds one item worth asking Dean for.
Series
- Part 90 of The Chicago Verse
Bookmarked by MilfSamWinchester
22 Aug 2026
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Sam and Dean exchange Christmas gifts to each other, as well as celebrate their first Christmas together in their new home.
Also a new member to the family.Series
- Part 16 of Starting Over
Bookmarked by MilfSamWinchester
21 Aug 2026
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Secret Santa for twitter Holiday gift exchange - Wincest gifset
Wincest Au in which Dean gets Sam a puppy for Christmas and Sam has to show Dean how happy he made him ;)
Bookmarked by MilfSamWinchester
21 Aug 2026
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Sam and Dean are a day away from the two year anniversary of when they started dating and four month anniversary of their engagement, which falls on the same day. Like always, they like to keep it simple and plan to spend the day cuddling in bed.
Sam, however, doesn't expect Dean to ask a question he never thought he'd hear, especially at such an ironic time.
Bookmarked by MilfSamWinchester
20 Aug 2026
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Sam and Dean are teachers at Arizona high and they have a secret.
Bookmarked by MilfSamWinchester
20 Aug 2026
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It looked like any other normal semester but things went to hell with the pandemic, now Sam has to teach using a laptop and hope his students don´t find a lot about his private life and his husband. It all goes well until one day their dog makes a surprising visit to his homemade classroom, interrupting the class.
Bookmarked by MilfSamWinchester
20 Aug 2026
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Bookmarked by MilfSamWinchester
20 Aug 2026
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Sam plans a romantic date. It's not likely to go well, he thinks.
Dean decides to prove him wrong.
Bookmarked by MilfSamWinchester
19 Aug 2026
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His eyes wandered down to Sammy’s hand, and that was the chick flick of all chick flicks: imagining the curve of a small silver band gracing his little brother’s paw, the ultimate symbol of Sammy belonging to Dean, and Dean belonging to Sammy.
He was Dean Winchester, of course he jerked off, ring on his finger, Sammy on his mind.
Or: that one fic where Dean accidentally proposes to Sam.
Series
- Part 1 of retired hunter fluffery
- Language:
- English
- Words:
- 2,188
- Chapters:
- 2/2
- Collections:
- 1
- Comments:
- 16
- Kudos:
- 97
- Bookmarks:
- 9
- Hits:
- 1,144
Bookmarked by MilfSamWinchester
19 Aug 2026
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Being retired and wearing matching rings is no reason for Dean to not panic about the really important questions. Such as if Sammy would rather enjoy blue or pink bubbles.
It was all Sammy’s fault. Sammy had decided to buy silver rings and pink was the perfect addition to silver. Everybody should have the opportunity to bathe in pinkish bubbles at least once, especially Sammy. Sammy deserved everything.
Series
- Part 3 of retired hunter fluffery
- Language:
- English
- Words:
- 2,538
- Chapters:
- 1/1
- Collections:
- 1
- Comments:
- 6
- Kudos:
- 41
- Bookmarks:
- 2
- Hits:
- 409
Bookmarked by MilfSamWinchester
19 Aug 2026