1 - 20 of 211 Works in Insecure Dean Winchester

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  1. Tags
    Summary

    Dean Winchester has a lot going for him: he's beloved by his students, he's finished writing his first book, and he's living comfortably in New York City. The only problem is... he's single. That wouldn't bother him much if his family wouldn't be visiting for the holidays. With cuffing season over, Dean has to face his family alone... or will he?

    Castiel DiAngelo is a simple detective who hasn't really celebrated Christmas in over 9 years, holidays and family being a sore spot for him. But after taking Dean up on an offer, he finds that you can't really avoid the holidays.

    Will these two be able to pull off a seminal holiday trope? Or will certain developments get in the way...

    Language:
    English
    Words:
    72,338
    Chapters:
    15/15
    Comments:
    62
    Kudos:
    266
    Bookmarks:
    50
    Hits:
    3968
  2. Tags
    Summary

    Dean didn't have a soulmate. He'd just come to accept that.
    Usually, on your 18th birthday, the body swap took place. But that had never happened to him. And now at age 31, he'd given up on the whole thing. He'd never really thought he was worthy of a soulmate anyway.
    In his life, people came and went, nothing was ever permanent.

     

    title from Never too late by Three Days Grace

    Language:
    English
    Words:
    4,773
    Chapters:
    2/2
    Comments:
    7
    Kudos:
    80
    Bookmarks:
    7
    Hits:
    944
  3. Tags
    Summary

    Gabriel's careless gift becomes the promise of a lifetime.

    Language:
    English
    Words:
    9,051
    Chapters:
    2/2
    Collections:
    1
    Comments:
    18
    Kudos:
    124
    Bookmarks:
    12
    Hits:
    525
  4. Tags
    Summary

    Whenever shit hit the fan with either of them, they ran to each other. It was safe there. No one could touch them there. They’d go off to their own little sphere where nothing could go wrong. It was safe there, and that’s how it worked.

    Language:
    English
    Words:
    1,982
    Chapters:
    1/1
    Comments:
    20
    Kudos:
    65
    Bookmarks:
    4
    Hits:
    538
  5. Tags
    Summary

    Dean always knew he'd be an Alpha.
    Except, he isn't.

    Or
    The A/B/O Destiel one where it's more Dean angst and hate on John Winchester than actual Destiel.

    Language:
    English
    Words:
    6,667
    Chapters:
    4/?
    Comments:
    11
    Kudos:
    90
    Bookmarks:
    13
    Hits:
    1358
  6. Tags
    Summary

    In the middle of planning his wedding with Dean, Castiel reflects on the other only relationship that ever came close to theirs.

    Language:
    English
    Words:
    1,086
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    32
    Bookmarks:
    1
  7. Tags
    Summary

    Sometimes, the biggest of changes start with the smol-est of creatures, especially if those changes are long-time coming.

    Language:
    English
    Words:
    7,194
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    92
    Bookmarks:
    7
    Hits:
    638
  8. Tags
    Summary

    After Michael leaves, Dean is a shell of who he used to be, Cas fights to pick up his broken pieces and put him back together again. Will they make it or will they break even more?

    Language:
    English
    Words:
    2,417
    Chapters:
    1/?
    Comments:
    1
    Kudos:
    16
    Bookmarks:
    2
    Hits:
    413
  9. Tags
    Summary

    Now that the Winchesters are living in the bunker, they have their own rooms and while this sounds ideal, Dean finds that having his own room is causing a lot of sleepless nights. Ignoring the issue only makes it worse, so finally he bites the bullet and secretly sleeps on Sam’s floor.

    Turns out it’s not so secret and the brothers must navigate through new sleeping arrangements and unspoken feelings.

    Language:
    English
    Words:
    11,154
    Chapters:
    1/1
    Comments:
    17
    Kudos:
    180
    Bookmarks:
    23
    Hits:
    1725
  10. Tags
    Summary

    Dean has home and school issues and Mr. Novak is here to help.

    Dean is only 16-17 here and in 10th grade while Cas is 25 so if you don't like underage don't read.

    COPIED FROM WATTPAD THIS IS MY STORY

    Language:
    English
    Words:
    33,198
    Chapters:
    22/22
    Comments:
    31
    Kudos:
    102
    Bookmarks:
    17
    Hits:
    3384
  11. Tags
    Summary

    “Any luck?”

    In lieu of response, Cas throws back the rest of his Moscato. His burp is way too guttural, even for someone with as raspy a voice as him. It actually hurts his throat and a small amount of bile swims to the surface. “Augh—I… I’m good.”

    “And we’re done with the alcohol,” Dean declares, plucking the wine glass in one swift move.

    Language:
    English
    Words:
    1,557
    Chapters:
    1/1
    Comments:
    15
    Kudos:
    99
    Bookmarks:
    5
    Hits:
    685
  12. Tags
    Summary

    Cas was the perfect man. He was nice, tallented, gorgeous, easy to talk to, and Dean had fallen hard and fast for the man.

    There was only one problem...

    His best friend was a total bitch.

    Series
    Language:
    English
    Words:
    22,014
    Chapters:
    3/3
    Comments:
    18
    Kudos:
    58
    Bookmarks:
    10
    Hits:
    1099
  13. Tags
    Summary

    Dean is a ladies' man and he's currently dating the infamous Rhonda. Castiel is the new guy in school, all sassy and gorgeous. Sam and Jess have the perfect relationship. Will everything remain the same after Cas and Dean meet?

    I want to tell you. Cas is 17 for a few chapters. But Dean it's just 18. That's why the underage. But there's no Anal involved in the underage sex
     

    Based on this. Fun - The gambler We heard it and it ticked us.

    THIS IS NOT ABANDONED - 50% OF THE FIC IS ALREADY WRITTEN. - WE'VE BEEN HAVING SOME BETA PROBLEMS LATELY BUT WE HOPE THEY WILL BE SOLVED SOON. LOVE U ALL. PLEASE, KEEP TELLING US WHAT YOU THINK ABOUT THIS.
    Update: 03/08/2017 STILL NOT ABANDONED. WE ARE FINISHING OUR LAST BIG BANG. THIS TIME A SABRIEL. YOU CAN READ IT IN 10 DAYS. SO PLEASE REMEMBER. WE DO NOT FORGET YOU.
    Update 04/25/2017. We are back on a regular posting. We will be posting every other week. Thanks for the patience.
    Update 01/27/2018: We are not abandoning this. We have just too much on our hands. I'm so sorry this is taking too long.

    Language:
    English
    Words:
    88,874
    Chapters:
    15/20
    Comments:
    22
    Kudos:
    69
    Bookmarks:
    18
    Hits:
    2288
  14. Tags
    Summary

    He’s got his career and his family; he’s a happy man. All he wants now is to fall in love with his soulmate. The person who will complete his life in every way. If Dean were a praying man, he’d ask for Novak to be his.

    Language:
    English
    Words:
    5,216
    Chapters:
    1/1
    Comments:
    11
    Kudos:
    91
    Bookmarks:
    7
    Hits:
    483
  15. Tags
    Summary

    Nervous that Cas hasn’t wanted to fuck Dean yet because he thinks it’ll be too tight, Dean endeavors to remedy that.

    Or,

    The one where Dean must have read something wrong while he was ordering his new butt plug.

    Series
    Language:
    English
    Words:
    6,434
    Chapters:
    1/1
    Comments:
    42
    Kudos:
    342
    Bookmarks:
    38
    Hits:
    3496
  16. Tags
    Summary

    A long ride home after another hunt leads somehow to a strange conversation between Castiel and the Winchesters. How does Cas look without his vessel? Will Sam and Dean ever be able to see his wings?

    Dean is more and more aware of his feelings for his best friend and Angel but can you really fall for someone without even knowing their looks?
    Can it possibly get any more awkward?
    Probably not, but then it starts to get hurtful ...

    Series
    Language:
    English
    Words:
    3,153
    Chapters:
    1/?
    Kudos:
    6
    Hits:
    227
  17. Tags
    Summary

    Dean's subconscious fights Michael with all he has, leading to a series of barely coherent hallucinations and Dean kicking Michael out. When it's finally only Dean again, he's not fully there. Castiel tries to rebuild him one more time, but when the pieces aren't all there, how will he and Dean fit?

    Series
    Language:
    English
    Words:
    37,519
    Chapters:
    8/8
    Comments:
    92
    Kudos:
    156
    Bookmarks:
    32
    Hits:
    2485
  18. 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:
    110
    Bookmarks:
    26
    Hits:
    1680
  19. Tags
    Summary

    The drawback to having an insatiable passion for art and self-expression is the death of a muse. Slapped on his left upper bicep is a giant, glowing red handprint. Just below that is a name that wraps around his entire muscle in sloppy cursive, but still clearly reads—“Castiel.”

    Language:
    English
    Words:
    1,470
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    38
    Bookmarks:
    2
    Hits:
    512
  20. Tags
    Summary

    Dean sucks at relationships. He’s beating himself up in Benny’s bar, because his insecurities resulted in a fight with his beautiful, perfect omega, when he gets a text: “I know it’s not a good timing, but my heat came up, could you stop by?” He’s staring at the text, being sure there’s certainly something he missed, because this is something they don’t do. After eight months of relationship their sexual life is practically nonexistent. Another text follows: “I’d need you to fix the washing machine, I guess I’m gonna need it.” Well, that’s it.

    Or: When Dean is too horny and Cas so virgin it’s not humanly possible.

    Language:
    English
    Words:
    5,224
    Chapters:
    1/1
    Comments:
    20
    Kudos:
    370
    Bookmarks:
    33
    Hits:
    3686

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