1 - 20 of 63 Works in Heartbroken Dean Winchester

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  1. Tags
    Summary

    What is it that makes Dean call his little brother a woman and make references to his underwear? An argument with Sam, who has enough of this sexualized teasing, brings the truth to light: A story of loneliness.

    Language:
    English
    Words:
    2,954
    Chapters:
    3/4
    Kudos:
    9
    Bookmarks:
    2
    Hits:
    322
  2. Tags
    Summary

    Whumptober 2023.
    Each Day A Different Challenge.
    Thank You For Reading.

    Series
    Language:
    English
    Words:
    436
    Chapters:
    1/1
    Kudos:
    7
    Hits:
    123
  3. Tags
    Summary

    When Dean realizes he has feelings for his longtime best friend, Cas, he struggles to accept it, along with his newfound sexuality. Asking Charlie for advice results in an explosive argument that threatens the very foundation of his friendship with her.

    Dean copes with his ever-growing emotional turmoil through music and songwriting and finds success in expressing himself in a way he was never able to with words. He finally decides to express his feelings to Cas, but he hesitates every time he tries.

    He is shattered when he sees Cas in the arms of another, and he has to come to terms that his hesitation may have ruined his chance at finding the happiness he truly believes he doesn't deserve.

    But fate may have other plans.

    Language:
    English
    Words:
    75,249
    Chapters:
    19/?
    Comments:
    55
    Kudos:
    104
    Bookmarks:
    24
    Hits:
    3,999
  4. Tags
    Summary

    Cas has been in love with his roommate Dean for years, but he knows he doesn't have a chance. Nothing demonstrates this fact more clearly than the way Dean is constantly trying to set him up with people.

    It hurts like hell, having the man he wants trying to match him up with anyone else.

    In a moment of extreme frustration, Cas tells Dean he already has a date planned for that weekend, and then his best friend Meg convinces him to keep the ruse going.

    Dean's reaction is not what he expects.

    Series
    Language:
    English
    Words:
    4,862
    Chapters:
    1/1
    Comments:
    52
    Kudos:
    474
    Bookmarks:
    64
    Hits:
    4,416
  5. Tags
    Summary

    Cas hadn’t noticed how broken Dean looked until Dean’s eyes met his. His face hardened though immediately and his entire body went rigid as his red-rimmed eyes widened. Within a second Dean’s gun was in his hand and had it pointed directly on Cas.

    “Woah, woah! Dean! Wait a minute-“ Sam yelled as he put his arm out and stepped into the like of fire.

    “No, Sam! Fuck that!” Dean roared angrily, “Who the hell are you?” He yelled taking a step forward still pointing his gun firmly at him.

    “I am Castiel. I believe that I-“

    “Bullshit.”

    Basically the day after Castiel dies at the hands of Lucifer on the day that Jack was born, a past version of Castiel from 2012 gets mysteriously dropped down at his own hunters funeral.

    Language:
    English
    Words:
    20,231
    Chapters:
    4/4
    Comments:
    13
    Kudos:
    210
    Bookmarks:
    36
    Hits:
    2,532
  6. Tags
    Summary

    'after “you don’t have to say it, i heard your prayer” cas should’ve kissed dean HARD. & dean would pull back eyes big & say “cas, cas i lo-” & cas would cover dean’s mouth. say “dean. don’t say it. please.” so dean wouldn’t. & they’re together physically for the rest of s15 & dean doesn’t know what’s going on, thinks maybe cas just wants him like this & doesn’t love him back & he’s too nice to reject dean for loving him out loud so he doesn’t want dean to say it at all. but then the dungeon. cas’s deal. & he finally says it out loud but its too late'

    OR

    the devastating deancas fic i need to get out of my system-
    --------------------------------------
    !!!All credits for the idea to @C0WBOYLIKEME on twt!!!

    Language:
    English
    Words:
    5,541
    Chapters:
    4/4
    Comments:
    4
    Kudos:
    47
    Bookmarks:
    6
    Hits:
    719
  7. Tags
    Summary

    Prompt: "We had a really bad break-up three hundred years ago, but neither of us realized the other was immortal until we met today while shopping for groceries." AU

    Series
    Language:
    English
    Words:
    16,789
    Chapters:
    6/6
    Comments:
    12
    Kudos:
    82
    Bookmarks:
    22
    Hits:
    2,594
  8. Tags
    Summary

    In a world where everyone's born with their hearts outside their chests and a special black box, Dean learns early on that he's never known the kind of fairy tale love that most people know.

    Maybe all he's ever known is heartbreak.

    Language:
    English
    Words:
    6,550
    Chapters:
    1/1
    Comments:
    12
    Kudos:
    85
    Bookmarks:
    15
    Hits:
    799
  9. Tags
    Summary

    The story is set in the aftermath of the Michael–Lucifer showdown from Season 5. While falling into the pit, however, Michael latched part of his grace onto Dean, while Lucifer turned Castiel into a demon. Harrowed with the problem of being a demon, Castiel went MIA, locked up by Crowley as a prisoner and bait for other angels, leaving behind a heartbroken angel Dean. But when an emergency comes up, and Dean is summoned for help by Castiel— things begin to fall in place. Can Dean and Castiel go back to how they were before the Swan Song? Or will their fates be unchangeable?

    "Cas, I want to go back to how we were. You an angel, me a human. There's got to be some way, right?"

    "There is no way such a thing could happen, Dean, until God himself willed it. And God, as we know, couldn't care less. We can't change this."

    "But there could be someone, right? There has to be someone with some kind of information on this situation? Maybe a witch or an angel expert, someone?"

    Language:
    English
    Words:
    14,905
    Chapters:
    6/6
    Collections:
    1
    Comments:
    12
    Kudos:
    81
    Bookmarks:
    19
    Hits:
    1,472
  10. Tags
    Summary

    Dean misses Sam, but Sam's toying with them both.

    Language:
    English
    Words:
    2,714
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    52
    Bookmarks:
    5
    Hits:
    581
  11. Tags
    Summary

    It's been a year since Cas was taken by the Empty. Another Christmas Dean spends alone, aching for Cas to be back. With Last Christmas playing on the radio, Dean is left replaying their last memory together on repeat, wishing he could go back and tell Cas how he feels. But he can't. All he can do is sit in the Impala and read Cas a special poem and hope his Angel can hear him. One he's read a thousand times over the last year. A Christmas present to Cas, confessing what Dean should've said all along.

    I love you, I meant it.

    Language:
    English
    Words:
    914
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    93
    Bookmarks:
    6
    Hits:
    544
  12. Tags
    Summary

    Dean's POV for the dreaded phone call and its aftermath.

    After Cas calls him a murderer, Dean drives to Bobby's. Pressed for details, he tells the devastating story. Plagued by dreams, he chooses to continue hunting only to find himself in Cas's path.

    Series
    Language:
    English
    Words:
    3,385
    Chapters:
    1/1
    Comments:
    5
    Kudos:
    60
    Bookmarks:
    2
    Hits:
    663
  13. Tags
    Summary

    Dean Winchester left the hunting lifestyle behind after a mistake was made, resulting in the person he was closest to in the world getting hurt. He moved far away and decided to try out a new life as a college student. Two years later, he had moved on, found love, and was beginning to get used to this new way of life. But even Dean knows the past always comes back to bite you--sometimes, literally.

    Series
    Language:
    English
    Words:
    8,455
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    8
    Hits:
    402
  14. Tags
    Summary

    Dean is captured by a djinn. He experiences the most happiness he had in a long time.

    Series
    Language:
    English
    Words:
    3,764
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    63
    Bookmarks:
    4
    Hits:
    970
  15. Tags
    Summary

    Loving Dean wasn't summer.

    Language:
    English
    Words:
    6,308
    Chapters:
    1/1
    Comments:
    15
    Kudos:
    73
    Bookmarks:
    18
    Hits:
    991
  16. Tags
    Summary

    Sam Winchester is fine. Perfectly fine! Why wouldn’t he be? Just-just don’t ask his family
    I suck at summarizing stories, just trust me, tragedy death and destruction ensue!

    Series
    Language:
    English
    Words:
    1,051
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    30
    Bookmarks:
    3
    Hits:
    1,069
  17. Tags
    Summary

    Lucifer will be a father and Castiel knows he has to prevent that. But that means he has to leave Dean and look after Kelly and Jack. He hates breaking his promise, but there is no other way. Dean doesn't want his Daddy to leave, but he stays quiet.

    Series
    Language:
    English
    Words:
    6,814
    Chapters:
    1/1
    Comments:
    17
    Kudos:
    245
    Bookmarks:
    20
    Hits:
    4,318
  18. Tags
    Summary

    Balthazar from the past goes to Dean and casts the spell that serves not only as a time travel spell, but also as an alternate dimension spell, taking him back to the events of "The French Mistake". He sees Misha and vows to keep him safe.

    Language:
    English
    Words:
    5,834
    Chapters:
    5/5
    Comments:
    6
    Kudos:
    56
    Bookmarks:
    5
    Hits:
    1,402
  19. Tags
    Summary

    “My whole life I’ve seen you jumping from one person to another and now-”
    “You won’t get it,” Dean mumbles, Charlie’s hand covering his in a soothing gesture, her thumb stroking his knuckles.
    “Then make me, Dean!” Sam burst out like Dean had expected him to, “You can have anyone you like! So why are you so stuck over one person?”
    “Because I-” he chokes on his words, taking an unsteady breath before he is ready to speak, “Because even if I can have anyone, they are not him.

    Language:
    English
    Words:
    6,898
    Chapters:
    6/6
    Comments:
    7
    Kudos:
    83
    Bookmarks:
    7
    Hits:
    1,511
  20. Tags
    Summary

    He was the loser in high school.

    He was the geek with glasses that roamed the high school hallways, always completed his assignments on time and aced his exams.

    He was the one that never got asked out to prom.

    He never had a boyfriend anyway. He never had much friends- just a friend, Charlie Bradbury. Third wheeling to prom it was.

    Then, something life altering happened on prom night, the soul bond of two wolves. One popular alpha and one worthless omega.

    The handsome shocked alpha said, “It just isn’t right, I’m sorry.”

    And he left him, with an aching and broken heart.

    10 years later, when the handsome alpha comes rolling back into town, he wonders if the strong wolf remembers him?

    Maybe, maybe not?

    Castiel knew he couldn’t face the alpha, Dean Winchester. He wouldn’t be able to handle another round of heartbreak, not again.

    Then, Sam and Gabe plan an engagement party….

    Language:
    English
    Words:
    5,356
    Chapters:
    5/?
    Comments:
    78
    Kudos:
    283
    Bookmarks:
    35
    Hits:
    5,975

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