1 - 20 of 114 Works in Awkward Dean Winchester

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  1. Tags
    Summary

    Dean Winchester was your average bartender, save for the fact that he’s an orphan with a seriously bad penchant of falling in love with the worst men possible. Time after time, broken heart after broken heart, normal people would give up on ever finding their soulmate. But not Dean; he still holds onto hope that he will meet the man of his dreams. And the Adonis with the blue eyes could be him, even if he wears such a creepy trench coat. He should have known his heart would lead him to nothing but trouble…

    Cas - or Eros, as he’s better known - drags Dean into a world he never knew existed but has lived alongside his own for longer than he ever realized. He meets the refugees of Olympus, cast out after the Fates banished them, and learns not only about the lives of the homeless Olympians but also his own heritage. They keep telling Dean he has the power to save them all, but all his life he never had the power to control anything. His heart is even more powerful than his will, still pining after the man who uprooted his comfortable ignorance. Then again… could it be Dean Winchester’s heart that is the key to saving them all?

    Mini-Bang for the Destiel Harlequin Challenge 2019

    Language:
    English
    Words:
    30,516
    Chapters:
    5/5
    Collections:
    1
    Comments:
    5
    Kudos:
    54
    Bookmarks:
    9
    Hits:
    648
  2. Tags
    Summary

    In which Dean believes the beautiful man waving is waving at him.
    ~~~
    The man gave a weak laugh that could have easily passed as cough and deepened his gaze into the floor, which Cas did not like considering he had such beautiful green eyes and having them pointed at the floor prevented Cas from admiring them.
    “So, uhh… I havn’t seen this movie yet” the man started, slowly lifting his gaze at Cas like a hurt puppy.

    “So then why did you go on a rant about it?” Cas furrowed his brows squinting at Dean.

    Language:
    English
    Words:
    4,479
    Chapters:
    3/3
    Comments:
    5
    Kudos:
    86
    Bookmarks:
    2
    Hits:
    871
  3. Tags
    Summary

    It's Valentine's Day and Cas is tired of Dean

    Series
    Language:
    English
    Words:
    519
    Chapters:
    1/1
    Kudos:
    12
    Hits:
    240
  4. Tags
    Language:
    English
    Words:
    937
    Chapters:
    1/?
    Comments:
    2
    Kudos:
    12
    Hits:
    175
  5. Tags
    Summary

    Dean needs more coffee before he can insert his brain to mouth filters in the morning.

    Language:
    English
    Words:
    666
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    64
    Bookmarks:
    2
    Hits:
    554
  6. Tags
    Summary

    Dean Winchester gets a new neighbor. A new cute neighbor.

    His last relationship blew up in his face, so he's thrown himself into starting a business- Winchester Luxury Auto. Because he's been so busy, he hasn't really had time for fun.

    In fact, he's been so busy with work that he doesn't sleep very well. And it seems neither does the new neighbor. Dean accidentally catches Castiel up late one night, and he just can't seem to stop looking.

    Until Charlie finally does something about it.

    Language:
    English
    Words:
    8,983
    Chapters:
    1/1
    Comments:
    12
    Kudos:
    284
    Bookmarks:
    38
    Hits:
    2222
  7. Tags
    Summary

    With Christmas just around the corner, Dean has to do some serious grocery shopping - enough to feed an army. Literally. And a few extra guests. He takes Jack and Cas with him to the grocery store. But will they be bringing home only food? Or is there more to find? The smallest of things can be the most thoughtful presents, given the right meaning and intention.

    Language:
    English
    Words:
    2,893
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    87
    Bookmarks:
    11
    Hits:
    571
  8. Tags
    Summary

    Dean has been distant and Castiel anxious over a spur of the moment kiss nearly a month ago. With Christmas at hand, Cas decides to bring a little cheer into the bunker with the hopes that this might break the tension between him and Dean.

    Language:
    English
    Words:
    2,138
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    73
    Bookmarks:
    5
    Hits:
    571
  9. Tags
    Summary

    A few days ago, the undies you thought would warm your body so well turned out to be vibrating panties. Gah! For the love of Thor! How mortifying. But Dean’s got a plan to make it all better…
    .
    Sequel to The Wonders of Modern Technology.

    Language:
    English
    Words:
    7,080
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    68
    Bookmarks:
    11
    Hits:
    1411
  10. Tags
    Summary

    Cas lives alone, and with the holidays arriving, he sets about filling his home with Christmas cheer, even if he's the only one that will be celebrating it. He's lonely, with no family, no real friends, and when he thinks about how he's going to be spending another Christmas alone, he whimsily makes a wish, asking Santa to bring him someone that he can fall in love with, and that will love him back. It's funny how sometimes, even the wildest of wishes can come true.

    Series
    Language:
    English
    Words:
    16,292
    Chapters:
    1/1
    Comments:
    23
    Kudos:
    240
    Bookmarks:
    28
    Hits:
    1969
  11. Tags
    Summary

    Post 14x04

    Dean's riding the high of his adventure in Salem, and decides to invest in something he's always wanted, but was too shameful to buy. However, now that he did, the fear resurfaced, and he's not sure if it was a good idea. Will Dean decide to experience the pleasure, or let the pain overwhelm him before he even begins.

    Series
    Language:
    English
    Words:
    3,429
    Chapters:
    1/1
    Comments:
    5
    Kudos:
    113
    Bookmarks:
    10
    Hits:
    1097
  12. 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:
    8
    Kudos:
    270
    Bookmarks:
    18
    Hits:
    2328
  13. Tags
    Summary

    Again, they're having a late night talk.
    Again, they're talking about human love.
    Again, Cas is trying to understand.
    For the first time, he's confessing.

    Or: Dean recaps some stuff he's gone through b̶̶e̶̶c̶̶a̶̶u̶̶s̶̶e̶̶ ̶̶o̶̶f̶ with Cas while they are having one of the infamous half-drunk late night conversations, resulting in a lot of awkwardness (plus an awkward first kiss, and a small sequel/extra part/bonus chapter/thing).

    Language:
    English
    Words:
    5,830
    Chapters:
    2/2
    Comments:
    6
    Kudos:
    54
    Bookmarks:
    5
    Hits:
    605
  14. Tags
    Summary

    Three Months.

    Yep, its been three months since Dean saw the man. Well, technically, he sees him everyday. He stands right below the abandoned building, and feeds the stray cats. Dean's bakery faces the building, and he can't help but swoon over the mystery man.
    Finally, he decided to walk across the street and take his chance. But things might not go as planned, but that isn't a bad thing, is it?

    Language:
    English
    Words:
    2,325
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    78
    Bookmarks:
    3
    Hits:
    849
  15. Tags
    Summary

    He briefly wondered if he could get away with saying that he had fallen, and Cas’ lips happened to be in the way, and the brief slip of tongue had just been the oral equivalent of reaching out a hand to steady himself. Dean Winchester could sell sex to a prostitute, but he thought this one might be beyond even him.

    Series
    Language:
    English
    Words:
    314
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    50
    Bookmarks:
    1
    Hits:
    381
  16. Tags
    Summary

    Dean has been side glancing at Castiel Novak for months, pretty much since the semester started. Charlie his BFF has harassed him to ask the guy out but Dean, he's not sure. He wants him but Cas is just... perfect and Dean so isn't.

    The Christmas party is tonight and she's demanding he makes a move. He has no idea how to approach the guy. Thankfully fate is a bitch, and she might just intervene.

    Language:
    English
    Words:
    2,986
    Chapters:
    2/2
    Comments:
    19
    Kudos:
    238
    Bookmarks:
    31
    Hits:
    2267
  17. Tags
    Summary

    At 18, Dean is beginning to realize he may not be as straight as he thought. Home alone, he is finally able to experiment and well...he just can't seem to stop.

    Series
    Language:
    English
    Words:
    37,472
    Chapters:
    11/11
    Collections:
    1
    Comments:
    89
    Kudos:
    615
    Bookmarks:
    93
    Hits:
    23906
  18. Tags
    Summary

    Dean ends up with a Rabbits Foot in his possession, will it mean good or bad luck for him and Cas?

    Language:
    English
    Words:
    895
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    30
    Bookmarks:
    1
    Hits:
    233
  19. Tags
    Summary

    “That’s not yours.”
    Castiel blearily glanced up at the words, still rubbing sleep from his eyes as he stumbled into the kitchen. He blinked and shook his head in an attempt to clear away the cobwebs. “Huh?”
    “That shirt,” Dean elaborated, a mug of coffee paused in its journey to his mouth as he looked at Castiel expectantly. “I’ve never seen you wear it before. Actually…” The mug was set down as Dean’s eyebrows scrunched together. “Dude, is that mine?” he asked incredulously.
    ______
    Basically pure fluff with Dean and Cas being awkward bumbling idiots.

    Language:
    English
    Words:
    1,134
    Chapters:
    1/1
    Comments:
    21
    Kudos:
    218
    Bookmarks:
    16
    Hits:
    1529
  20. Tags
    Summary

    Cas is trying to find a lubricant that he can enjoy. Awkward conversations, humor, and slippery fun ensues.

    Language:
    English
    Words:
    2,060
    Chapters:
    1/1
    Comments:
    9
    Kudos:
    32
    Bookmarks:
    3
    Hits:
    830

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