1 - 20 of 161 Works in Dean Winchester Has Self-Esteem Issues

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  1. Tags
    Summary

    AU where Dean and Castiel are paramedics and the perfect work partners and they finally stop dancing around their feelings for each other. Only problem now is, Dean won't come out of the closet and Castiel is in a questionable relationship with some douchebag lawyer who doesn't exactly want to let him go. Dean and Cas' sexual and working relationship heats up as the rest of their lives start to break down. Their job is saving the lives of strangers, but can they save themselves and each other? Or will it all come crashing down?

    Language:
    English
    Words:
    43,538
    Chapters:
    9/?
    Comments:
    56
    Kudos:
    82
    Bookmarks:
    34
    Hits:
    1814
  2. Tags
    Summary

    Dean Winchester isn't the most popular boy in his school. In fact, you couldn't get lower on the totem pole than him. But he's come to accept it, even if it means dealing with people like Gordon every time he tiptoes out of the status quo. Making first impressions is hard given that he's known most of his classmates since the beginning. But besides Charlie, he doesn't have anyone in his corner.

    Except for Castiel, the school's quarterback who transferred to their school last year. But he'd never go for someone like Dean...

    (This fic is based around the totally adorable Dean characterization in 14x04)

    Series
    Language:
    English
    Words:
    3,840
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    110
    Bookmarks:
    7
    Hits:
    708
  3. Tags
    Summary

    Dean and Sam's points of views on their relationships and lives throughout the years. John Winchester is more harmful than good, especially to Dean. Sam struggles with the guilt of what his brother's given up for him over the years. Dean suffers from abuse, low esteem. TRIGGER WARNING for eating disorders/abuse. Pre-series. UPDATED: Periodic point of views from John and Bobby as well. John is a real SOB.

    Language:
    English
    Words:
    151,016
    Chapters:
    62/?
    Comments:
    406
    Kudos:
    944
    Bookmarks:
    91
    Hits:
    21716
  4. Tags
    Summary

    Dean has some self-esteem issues, especially considering he's put on a few stubborn pounds lately. Castiel knows, and he's tired of waiting for Dean to learn that he is perfect just the way he is.

    Kissing, touching, and reassuring praises ensue.

    Series
    Language:
    English
    Words:
    1,542
    Chapters:
    1/1
    Kudos:
    22
    Hits:
    321
  5. Tags
    Summary

    It's just a little question. Easy, right? Not when you're as emotionally constipated as Dean Winchester. But he loves Cas, and wants to be with him for the rest of his life, so it's an obvious choice. Just... will he survive the asking?

     

    And how the hell is asking a guy to marry you more difficult than hunting literal monsters?

    Series
    Language:
    English
    Words:
    1,147
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    88
    Bookmarks:
    4
    Hits:
    669
  6. Tags
    Summary

    Dean should have known better. After five years of being in a relationship with Cas and Jimmy Novak, he usually knew when the twins were up to something. But somehow he’d missed it this time around, and now he has to deal with the consequences, which include being interrupted during blowjobs by the whispering twins. Dean is sure that they are keeping something from him, but he can’t for the life of him figure out what that ‘something’ is.

    Language:
    English
    Words:
    1,511
    Chapters:
    1/1
    Collections:
    1
    Comments:
    2
    Kudos:
    28
    Hits:
    342
  7. Tags
    Summary

    Cas and Dean are US Marshals investigating a series of occult murders along the US/Mexico border. Reality is not what it seems...

    Series
    Language:
    English
    Words:
    20,946
    Chapters:
    9/?
    Comments:
    4
    Kudos:
    10
    Hits:
    171
  8. Tags
    Summary

    They were hunting a witch and she cursed Dean. He - an alpha!- got switched with an omega in heat. Things go downhill from there.
    Or do they?

    Language:
    English
    Words:
    10,746
    Chapters:
    4/4
    Comments:
    6
    Kudos:
    92
    Bookmarks:
    12
    Hits:
    2579
  9. Tags
    Summary

    Dean is more okay with being a werewolf than anybody expected. Probably because he towers over Sam, and loves it.

    But he is also far more cuddly as a wolf, and more receptive when Cas tells him how worthy he is, and how loved.

    Language:
    English
    Words:
    1,116
    Chapters:
    1/1
    Collections:
    1
    Comments:
    6
    Kudos:
    114
    Bookmarks:
    4
    Hits:
    911
  10. Tags
    Summary

    It's the weekend after homecoming. Dean, Anna, and Charlie discuss midterm grades. Dean gets annoyed with Anna bragging about her scores, so Dean makes sure to improve his intelligence. Cas knows something's up with Dean and tries to confront Dean, and as usual, Dean pushes him off and gets mad, and this is their first real fight as a couple

    Series
    Language:
    English
    Words:
    1,814
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    24
    Bookmarks:
    1
    Hits:
    519
  11. Tags
    Summary

    Dean is a mechanic, working and living at the Novak mansion where he doesn't like anything about the upper class snobbish family, especially Castiel. The boy is stuck-up and Dean has better things to worry about than why Castiel got under his skin so quickly.

    In a time and place where the classes don't associate with each other and rich boys only marry rich girls, Dean and Castiel find themselves learning a lot about the importance of character, friendship and love over wealth and status.

    "A coward is incapable of exhibiting love, it is the prerogative of the brave." Mahatma Gandhi

    Language:
    English
    Words:
    32,556
    Chapters:
    1/1
    Comments:
    8
    Kudos:
    47
    Bookmarks:
    13
    Hits:
    1048
  12. Tags
    Summary

    Dean is extremely stressed out with his midterms coming up and so Dr. Novak helps him study and gives him lots of encouragement and lets Dean know he is smart enough. When Dean gets the results of his exams, Cas is there for him when not all the grades were as good as Dean hoped. Cas helps Dean get through it.

    Series
    Language:
    English
    Words:
    2,385
    Chapters:
    1/1
    Kudos:
    34
    Hits:
    580
  13. Tags
    Summary

    “I’m going to kiss you now.”

    Cas pauses, giving Dean a chance to back out, but Dean just licks his lips and waits.

    Cas’s mouth is up against Dean’s for a couple seconds before Dean responds, and then it’s Cas that’s being kissed senseless, because kissing is definitely not something Dean does tentatively. Dean reaches up to cup Cas’s jaw in his hand, tilting his head for a better angle, mouth plush, tasting like whiskey.

    Cas tries to remember what it was like the first time he kissed a man. All-encompassing, the world jerking off its axis, the feel of stubble under his fingers intense in a way it never really is with women, as much as he loves them.

    Language:
    English
    Words:
    138,635
    Chapters:
    79/79
    Collections:
    1
    Comments:
    2443
    Kudos:
    1338
    Bookmarks:
    330
  14. Tags
    Summary

    In a world where a simple Omega is more than what he seems, watch as he encounters his lost history and reclaims his kingdom.
    All with the help of his mate after all... Or maybe not. :-)

    Series
    Language:
    English
    Words:
    8,123
    Chapters:
    8/20
    Comments:
    19
    Kudos:
    34
    Bookmarks:
    5
    Hits:
    1115
  15. Tags
    Summary

    Castiel Novak and Dean Winchester, Have been dating for 5 years, Two of which have been rough, particularly on Dean.

    Language:
    English
    Words:
    2,428
    Chapters:
    1/1
    Comments:
    8
    Kudos:
    41
    Bookmarks:
    1
    Hits:
    461
  16. Tags
    Summary

    Ten times Dean tried to kill himself.
    And the one time Sam stopped him.

    Series
    Language:
    English
    Words:
    8,802
    Chapters:
    1/1
    Comments:
    33
    Kudos:
    107
    Bookmarks:
    25
    Hits:
    1645
  17. Tags
    Summary

    The one where uninspired chef Dean Winchester has a one night stand with the male (!) food critic who described the flavour of his garlic bread as 'closeted' and accidentally ends up dating him to try and prove that he's a kick ass chef, thank you very much.

    (He may have a point about the 'closeted' thing).

    Series
    Language:
    English
    Words:
    109,418
    Chapters:
    21/21
    Collections:
    1
    Comments:
    1425
    Kudos:
    1023
    Bookmarks:
    221
    Hits:
    12815
  18. Tags
    Summary

    AU Season 12 Episode 3 The Foundry

    Mary's a bit more interested in Sam and Dean's past, Dean cares too much, and things quickly spiral out of control. But hey, Sam and Dean have each other to lean on when things get rough.

    Language:
    English
    Words:
    7,190
    Chapters:
    1/1
    Comments:
    17
    Kudos:
    146
    Bookmarks:
    25
    Hits:
    1701
  19. Tags
    Summary

    Dean likes Cas. Dean loses a bet to Charlie. His punishment? Use the shittiest pick-up line in existence to ask Cas out. Good thing he likes crappy rom coms so much because his life just became one.

    Language:
    English
    Words:
    3,228
    Chapters:
    1/1
    Comments:
    24
    Kudos:
    199
    Bookmarks:
    14
    Hits:
    1538
  20. Tags
    Summary

    Dean Winchester has been going to Camp Chitaqua every summer for most of his life, first as a camper, and for the last three years, as a counsellor. He’s disappointed when his co-counsellor Benny has to cancel after an accident, but his replacement turns out to be anything but a disappointment. Castiel Novak is smart, strong, bendy, super hot, and for some reason really into Dean. Dean’s summer romances have never ended particularly well, but Cas seems determined to be more than just another camp crush.

    Language:
    English
    Words:
    17,378
    Chapters:
    4/4
    Collections:
    1
    Comments:
    64
    Kudos:
    328
    Bookmarks:
    48
    Hits:
    2662

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