1 - 20 of 50 Works in Dean Winchester/Sam Winchester First Time Having Sex

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  1. Tags
    Summary

    Sam tried hard to get air into his lungs, but the weight on his back was solid and unmoving. He could vaguely hear voices talking as he tried to focus on what they were saying and not the pounding in his head.

    “You tried to fuck over the wrong person, Dean, and now you're gonna pay the price for the money you lost me.”

    Sam blinked again, trying to catch sight of the room. He looked up from the tiled floor to see Dean struggling against some brute who had a knife to his throat and an arm wrapped around his chest.

    “I was gonna let you earn it back yourself, but I think I’ll get my message across a lot clearer if baby brother here clears your debt.”

    Language:
    English
    Words:
    8,761
    Chapters:
    3/3
    Collections:
    1
    Comments:
    16
    Kudos:
    100
    Bookmarks:
    13
    Hits:
    2043
  2. Tags
    Summary

    The enormous guy leans in to say, “How’s one hundred for your boy?” nodding meaningfully in Dean’s direction.

    A hundred dollars? For a blowjob? Sam’s too impressed to be angry, or offended, or disgusted.

    In fact, he’s downright intrigued. Could he…?

    Fuck. Of course he could. Dean wouldn’t stand a chance. And it’s not like they don’t always need money; motel rooms and bar tabs and silver bullets aren’t exactly free.

    Sam flashes a soulless smile (hah) and says, “He’s a biter.”

    Language:
    English
    Words:
    11,758
    Chapters:
    1/1
    Collections:
    1
    Comments:
    52
    Kudos:
    189
    Bookmarks:
    44
    Hits:
    5516
  3. Tags
    Summary

    Dean takes Sam to see fireworks for the fourth.

    Language:
    English
    Words:
    780
    Chapters:
    1/1
    Kudos:
    149
    Bookmarks:
    3
    Hits:
    990
  4. Tags
    Summary

    When Sam falls unwell after a hunt dealing with a witch and needs to have an appendectomy, all Dean thinks they need to worry about is Sam taking it easy for six weeks. But that isn't all they have to worry about.

    Series
    Language:
    English
    Words:
    3,107
    Chapters:
    1/1
    Comments:
    5
    Kudos:
    201
    Bookmarks:
    10
    Hits:
    2483
  5. Tags
    Summary

    When Dean hears Sam pleasuring himself at night, he invites Sam into his bed.

    Language:
    English
    Words:
    569
    Chapters:
    1/1
    Kudos:
    184
    Bookmarks:
    18
    Hits:
    1245
  6. Tags
    Summary

    Sam drunkenly confesses his feelings and desires for his brother Dean after he comes home from a one night stand.

    Language:
    English
    Words:
    2,441
    Chapters:
    1/1
    Kudos:
    75
    Bookmarks:
    11
    Hits:
    1537
  7. Tags
    Summary

    En una noche de caza, Dean deja solo a Sam.
    Pero Sam va a enseñarle que a él NADIE lo deja.

    Language:
    Español
    Words:
    1,452
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    10
    Hits:
    133
  8. Tags
    Summary

    House Campbell is looking to help secure the future of its pack by securing an alliance with House Winchester, a house from another pack.

    Dean Campbell heads to House Winchester's annual masquerade ball to show a willingness for his house to form a stronger alliance. That he might also find a mate there is just an added bonus.

    Series
    Language:
    English
    Words:
    2,518
    Chapters:
    1/1
    Comments:
    9
    Kudos:
    134
    Bookmarks:
    13
    Hits:
    2060
  9. Tags
    Summary

    Castiel gave his favorite pets a new Eden to live in, to worship their new God, and they haven't seen another human being since. One spring, something gets into Dean--something that feels like melting, like opening, like trembling.

    Written for the fabulous all_the_damned_vampires for the 2019 Spring Fling event, for the prompts of Wincestiel and slavery. Beta'd by the wonderful sweetheartdean and interstitial, with Enochian from the amazing monicawoe!

    While we're at it, for SPN Kink Bingo, this can fill the handjob square!

    Series
    Language:
    English
    Words:
    4,757
    Chapters:
    1/1
    Collections:
    2
    Comments:
    25
    Kudos:
    56
    Bookmarks:
    2
    Hits:
    1062
  10. Tags
    Summary

    WARNING MATURE AUDIENCES ONLY

    THIS IS WINCEST

    Smut, Porn/what Plot
    Top!Dean, Bottom!Sam
    No Drama or Angst,
    Instead of sleeping I wrote this.

    WORDS: 3975 ~ Work is Complete.

    Not Season specific. Sometime after S10 while brothers are established in the bunker.

    A/N: What's different about this fic is you will read their minds as you read this fic. Their thoughts are written between asterix and written in italics. (Example: *That's just great!*) Things spoken out loud to each other are in quotes as usual. I hope this isn't too confusing.

    SUMMARY: The brothers return home after a hunt. Sam has an injury and goes to Dean for wound care with his shirt off. Things somehow turn toward sex. We get to hear their innermost thoughts as well as their dialogue with each other.

    ~~~~~
    Wincest Canon-divergent meaning the story line was completely altered from SPN canon facts on purpose. SPN Characters are not mine.

    Language:
    English
    Words:
    3,975
    Chapters:
    1/1
    Comments:
    23
    Kudos:
    79
    Bookmarks:
    6
    Hits:
    2021
  11. Tags
    Summary

    Two chaotic months in 1991. A critical turning point in 1995. One day in a motel room in 2001. At Palo Alto in 2003. A troubling voicemail received in 2009.

    Sam has made an important decision, and wants to discuss these memories with Dean. Maybe he’s just buying some time, because once he's done this, it can't be undone.

    “So… what? Therapy session?” Dean leaned his head against the headboard and turned from side to side as if his neck was stiff. “I suppose you’ve earned one of those.”

    We both have.

    “Uh, yeah,” Sam confirmed apologetically. “But… therapy for me, I guess. And maybe for you, too, I don’t know. But just the two of us. So if you could hold off on making fun of me just for today, that would help.”

    “Hmm.” After a moment, Dean solemnly shook his head, but he was trying not to smile. “Yeah. I can’t promise that.”

    Language:
    English
    Words:
    35,756
    Chapters:
    8/?
    Comments:
    76
    Kudos:
    144
    Bookmarks:
    29
    Hits:
    1945
  12. Tags
    Summary

    There were plans for the resulting Winchester-Campbell union.
    Two vessels born that were to cleanse and usher in peace; they would bring the world to its knees as God's Will was carried out.

    There weren't even footnotes for the son of the Winchester-Milligan union.

    Language:
    English
    Words:
    29,544
    Chapters:
    11/11
    Comments:
    3
    Kudos:
    26
    Bookmarks:
    3
  13. Tags
    Summary

    Dean loves Sam, not just his alpha. Problem is, he never told his mate or his brother about his feelings. Time to set the record straight with a stern chat and a spanking or two - in front of Sam and Cas.

    Language:
    English
    Words:
    2,421
    Chapters:
    1/1
    Collections:
    1
    Comments:
    24
    Kudos:
    113
    Bookmarks:
    10
    Hits:
    3264
  14. Tags
    Summary

    Sam almost drowns while on a hunt and it pushes Dean's feelings for his brother to the forefront of his thoughts.

    Series
    Language:
    English
    Words:
    2,645
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    148
    Bookmarks:
    4
    Hits:
    2207
  15. Tags
    Summary

    On a hunt, Dean is put under a Fuck-or-die curse. He only has two people with him, and time is running out.
    What choice will Dean make? And how will the decision change the future for the both of them?

    Language:
    English
    Words:
    6,647
    Chapters:
    4/4
    Comments:
    16
    Kudos:
    326
    Bookmarks:
    25
    Hits:
    4091
  16. Tags
    Summary

    Sure, Sam hadn't advertised it as a "trip to Donna's sex cabin", but how was Dean supposed to know his brother wanted to actually go hiking in Minnesota in December?

    Language:
    English
    Words:
    3,621
    Chapters:
    1/1
    Collections:
    1
    Comments:
    50
    Kudos:
    229
    Bookmarks:
    24
    Hits:
    1185
  17. Tags
    Summary

    This Christmas is just going to be the two of them, and Sam's looking forward to it. He's got the perfect gift for Dean and they're going to be spending some quality time together. It'll be a million times better than one of their motel Christmases... right?

    Series
    Language:
    English
    Words:
    3,557
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    240
    Bookmarks:
    16
    Hits:
    2382
  18. Tags
    Summary

    WARNING MATURE AUDIENCES ONLY

    THIS IS WINCEST

    Smut, Angst, Drama, Action, Porn with a Plot, First Time Sex Together, Top!Dean, Bottom!Sam

    Right at 5,700+ words total - broken up into 5 chapters

    Summary: (S12/S13, but not really time line specific.) The brothers solve a case in a small town in Oklahoma. They're happy. It's a win! They plan on having a good time, when tragedy strikes. Sam gets disheartened because every time they rise, something knocks them back down. "It's Always Something!"

    Wincest Canon-divergent meaning the story line was completely altered from SPN canon facts on purpose. SPN Characters are not mine.

    Language:
    English
    Words:
    5,735
    Chapters:
    5/5
    Comments:
    4
    Kudos:
    118
    Bookmarks:
    4
    Hits:
    1270
  19. Tags
    Summary

    Sam and Dean are headed to South America to help a laid-up hunter rescue his missing daughter. But as they fumble through the Colombian rainforest, they find far more than they'd ever thought to even look for.

    Language:
    English
    Words:
    6,080
    Chapters:
    3/3
    Collections:
    1
    Comments:
    18
    Kudos:
    95
    Bookmarks:
    5
    Hits:
    720
  20. Tags
    Summary

    From the wayback machine on LJ - Y'all remember the infamous "wincest sounds" recording? Many fics were inspired by it, probably most of them better than this one. But someone asked me to give it a try, so I did. In 2012. Here it is.

    Language:
    English
    Words:
    603
    Chapters:
    1/1
    Comments:
    8
    Kudos:
    106
    Bookmarks:
    5
    Hits:
    994

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