1 - 20 of 311 Works in Dean Winchester Has Self-Esteem Issues

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  1. Tags
    Summary

    Dean dies. Jack brings him back and gives Sam and Dean a chance at having a real, happy life in a world where they can still save the world sometimes. But when Sam sees him alive and immediately accidentally kisses him, Dean finds himself having to deal with feelings he's shoved down for most of his life.

    Set in Season 6 of Buffy, but more wincest-focused.

    Language:
    English
    Words:
    75,974
    Chapters:
    31/33
    Comments:
    153
    Kudos:
    81
    Bookmarks:
    21
    Hits:
    2290
  2. Tags
    Summary

    One day, Cas arrives home from work to find his husband, Dean, in bed with another man, enraged he kicks him out and files for divorce, he gets even angrier when Dean doesn’t fight him.
    Meanwhile, Dean is devastated, he committed a grave mistake and lost everything. It doesn’t matter that it hurts to breath, it doesn’t matter that he didn’t consent, it doesn’t matter that he said no. Everyone says he is a cheater, so he must be
    Dean goes on a spiral after that day, will anyone find out the truth? Will they save him on time?

    Language:
    English
    Words:
    6,101
    Chapters:
    3/3
    Comments:
    55
    Kudos:
    97
    Bookmarks:
    10
    Hits:
    1644
  3. Tags
    Summary

    Dean is finally where he belongs... on his knees before Castiel.

    Language:
    English
    Words:
    30,142
    Chapters:
    23/?
    Comments:
    85
    Kudos:
    233
    Bookmarks:
    46
    Hits:
    7360
  4. Tags
    Summary

    When Dean attempted to sell his soul to save Sam, the deal did not go through. With his brother dead and Azazel having slipped through the woodwork, Dean must learn to cope with it all. As an Omega, this is a difficult task, one he was certainly well equipped to handle. But when a hunt in Austin, Texas, causes him to cross paths with an Alpha Texas Ranger that looks identical to his brother, the Omega is stumped on what to do. Why did this Alpha look like his brother? And why did he have to be such a pain in the ass? All good questions, given some of Dean's past experiences with Alpha's.

    With an unwanted Alpha tagging along, will Dean still be able to fulfill his duties as a hunter? Or will their subgender's and temperaments cause more harm than good? Only time will tell...

    (My first omegaverse fic; bear with me on this. Sorry if its a bit cringy in some parts.)

    Series
    Language:
    English
    Words:
    13,293
    Chapters:
    3/?
    Comments:
    4
    Kudos:
    14
    Bookmarks:
    1
    Hits:
    186
  5. Tags
    Summary

    It’s sort of hilarious that Dean ever thought that he could not have this. That he was ever dumb enough to think that he could pass this up, with the option out there in the universe.

    (In which they continue to work on that domestic-bliss thing).

    Series
    Language:
    English
    Words:
    79,518
    Chapters:
    16/?
    Comments:
    146
    Kudos:
    253
    Bookmarks:
    30
    Hits:
    6936
  6. Tags
    Summary

    "Hmmm." Cas' hand left Dean's cock to trace his ribs. "You could use some meat on your bones, it's true. Guess I'll just have to keep cooking for you."

    Dean squirmed self-consciously. He would rather go back to having sex and not talking about his body.

    Suptober Day 13: Morning After

    Series
    Language:
    English
    Words:
    802
    Chapters:
    1/1
    Collections:
    1
    Comments:
    10
    Kudos:
    84
    Bookmarks:
    3
    Hits:
    551
  7. Tags
    Summary

    Dean thinks about the things he’s been avoiding, late at night, face buried in Castiel’s lake-ruined trench coat.

    Language:
    English
    Words:
    834
    Chapters:
    1/1
    Kudos:
    8
    Bookmarks:
    1
    Hits:
    75
  8. Tags
    Summary

    When Cas tells Dean he loves him, Dean demands a list of reasons why.

    Language:
    English
    Words:
    1,401
    Chapters:
    1/1
    Collections:
    2
    Comments:
    6
    Kudos:
    44
    Bookmarks:
    1
    Hits:
    268
  9. Tags
    Summary

    Dean Winchesters attempts suicide on a dirty motel bathtub, ending brain dead on a hospital. A trickster promises John and Sam that he will save him for “free”, as long as they both get through watching a series of Dean´s memories, good and bad. The twist is that they will feel everything Dean did at the time and they can stop it at any time, but then Dean will die. They both accept thinking it cant be that bad. Spoiler: it is worse.

    Language:
    English
    Words:
    68,634
    Chapters:
    29/?
    Comments:
    621
    Kudos:
    1212
    Bookmarks:
    177
    Hits:
    39692
  10. Tags
    Summary

    Dean is struggling in the early stages of alcoholism. Basically, he is drinking for all the wrong reasons and is ignoring every instinct he has telling him to pull it together. He’s alone. Why not drink ‘til he dies?

    whumptober 2022 | no.8
    “stomach pain”

    Series
    Language:
    English
    Words:
    1,047
    Chapters:
    1/1
    Collections:
    1
    Comments:
    4
    Kudos:
    10
    Bookmarks:
    2
    Hits:
    317
  11. Tags
    Summary

    A brief look at the end of 15x18 if the Empty had only taken Billie in the dungeon

    Series
    Language:
    English
    Words:
    873
    Chapters:
    1/1
    Collections:
    1
    Kudos:
    22
    Hits:
    315
  12. Tags
    Summary

    Dean thinks he's an irredeemable bad boy, but Cas knows better.

    Suptober prompt: Pillow Talk
    Flufftober prompt: “You've told your parents?”
    Fictober prompt: “Nobody warned you about me?”
    Inktober prompt: Scurry

    Series
    Language:
    English
    Words:
    1,006
    Chapters:
    1/1
    Collections:
    2
    Comments:
    16
    Kudos:
    80
    Bookmarks:
    3
    Hits:
    406
  13. Tags
    Summary

    Dean has a small crisis of faith at a fall festival.

    Suptober prompt: Maze/Maize
    Flufftober prompt: Wearing Each Other's Clothes
    Fictober prompt: “I chose you.”
    Inktober prompt: Gargoyle

    Series
    Language:
    English
    Words:
    875
    Chapters:
    1/1
    Collections:
    2
    Comments:
    10
    Kudos:
    60
    Bookmarks:
    1
    Hits:
    330
  14. Tags
    Summary

    Castiel loses his virginity to his first love, Dean Winchester. Dean joins the army and leaves a heartbroken Cas behind. Cas writes letters for two years, but never gets a response.

    Six years since he last saw him, Dean is coming home. Castiel is terrified to see the man who broke his heart, but he refuses to hide from him. Maybe he shouldn't have worried at all...

    “Nice to meet you.” He leaned forward and gave Jo a quick one armed hug.

    “And this is her best friend, Castiel.” He was sweating as Dean’s eyes roved over him. God he hoped he wouldn’t bring up the letters. Castiel stared in open mouth shock at what he said next.

    “Hi, nice to meet you. I’m Dean Winchester.”

    Language:
    English
    Words:
    30,591
    Chapters:
    13/13
    Comments:
    12
    Kudos:
    190
    Bookmarks:
    24
    Hits:
    3423
  15. Tags
    Summary

    Sam had seen more things than he would tell, that he would let anyone know.
    Dean could understand things Sam wouldn't say, but his mind wasn't right.
    John let his mind wander and his hand and it just so happened that it was Sam who was close.

    Series
    Language:
    English
    Words:
    4,266
    Chapters:
    7/26
    Comments:
    4
    Kudos:
    34
    Bookmarks:
    8
    Hits:
    1669
  16. Tags
    Summary

    A hunt goes on longer than expected in the heat of summer. Are Dean and Castiel friends with benefits? In a secret relationship? Who's to say. All Dean knows is that he's drunk in the back of the car and he cried like a baby coming home from the bar.

    Language:
    English
    Words:
    5,040
    Chapters:
    1/1
    Collections:
    1
    Comments:
    20
    Kudos:
    77
    Bookmarks:
    21
    Hits:
    492
  17. Tags
    Summary

    While sorting through a storage room in the Bunker, Dean breaks something and is suddenly fifteen with no memories of his adult life. I’m sure it will all work out great.

    Language:
    English
    Words:
    21,512
    Chapters:
    7/?
    Comments:
    80
    Kudos:
    411
    Bookmarks:
    82
    Hits:
    6898
  18. Tags
    Summary

    Dean’s thinking of ending things.

    With Cas, that is.

    This isn’t like the book. It’s not a horror story, unless you know how easily a person can become a house haunted. Unless you know how, eventually, it becomes almost easy to choke down even the sharpest words. Unless you know how it feels for every escape attempt to fail. Unless you know a secret can be as heavy as dread and just as dark.

    That’s in the past, or maybe the point is that it never will be, not for Dean. He still answers his father’s calls and keeps an extra fridge in his unfinished basement, after all.

    Language:
    English
    Words:
    4,381
    Chapters:
    1/1
    Comments:
    29
    Kudos:
    258
    Bookmarks:
    42
    Hits:
    1071
  19. Tags
    Summary

    When Castiel shows up out of nowhere with another angel telling Dean that he has to torture the man that tortured him, of course his immediate answer was no. How could they expect him to stand in the same room with the Demon that made him wear his own insides? But in the end, he does it. But only because Castiel promises that no harm with come to Dean.

    OR

    Castiel convinces Dean to torture answers out of Alastair, promising that it's safe for Dean. But just like always in the Winchester's life, something goes wrong.

    Series
    Language:
    English
    Words:
    4,206
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    48
    Bookmarks:
    8
    Hits:
    690
  20. Tags
    Summary

    — Сейчас я собираюсь поцеловать тебя.

    Кас делает паузу, давая Дину шанс отступить, но Дин просто облизывает губы и ждёт.

    Кас пытается вспомнить, каково это было в первый раз, когда он поцеловал мужчину. Всеохватывающе, мир сошёл со своей оси, ощущение щетины под пальцами было так интенсивно, и он испытал то чувство, которое никогда не испытывал с женщинами, как бы сильно их не любил.

    Series
    Language:
    Русский
    Words:
    126,428
    Chapters:
    79/79
    Kudos:
    12
    Bookmarks:
    1
    Hits:
    413

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