1 - 20 of 50 Works in Castiel/Dean Winchester Flirting

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  1. Tags
    Summary

    When you’re a frequent lucid dreamer, sometimes it’s hard to remember what’s real. For Cas, he knows the green eyed man is real... and he knows he’s out there somewhere.

    Language:
    English
    Words:
    2,724
    Chapters:
    1/1
    Comments:
    28
    Kudos:
    83
    Bookmarks:
    14
    Hits:
    295
  2. Tags
    Summary

    Dean and Cas are roommates, and now they’re stuck together during quarantine. Not that Cas minds, except Dean is being extra flirty, which is proving to make Cas’ crush on Dean explode more and more. Every day Dean seems to be ramping up the flirting, showering Cas with romantic gestures that just seem to go over Cas’ head. Dean makes a bold move, one that Cas can’t mistake, that finally pushes them together.

    Series
    Language:
    English
    Words:
    6,528
    Chapters:
    1/1
    Collections:
    1
    Comments:
    34
    Kudos:
    173
    Bookmarks:
    22
    Hits:
    1058
  3. Tags
    Summary

    So, so many years - oh, so many almost’s and maybe’s - and all it takes in the end is a Led Zepp song you can dance to, and they finally fall in each other’s arms.

    OR

    The One in which Dean Winchester wears hamburger pajamas and decides to teach Castiel how to dance.

    Language:
    English
    Words:
    1,127
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    93
    Bookmarks:
    6
    Hits:
    382
  4. Tags
    Summary

    For Cas, it’s just another normal day at Pages & Pies… until a handsome stranger comes in and ends up checking out more than just a book.

    Language:
    English
    Words:
    2,121
    Chapters:
    1/1
    Comments:
    12
    Kudos:
    121
    Bookmarks:
    7
    Hits:
    541
  5. Tags
    Summary

    Cas and Dean have been dating for a month, but Sam is clueless, despite the fact that they haven't been hiding that they're together. Or so they thought. After reflecting on Sam's obliviousness, Dean deviously suggests he and Cas try to be as obvious as possible to see how long it’ll take for Sam to realize. Cue Dean and Cas' escalating attempts to prove they're together, and Sam mistaking every scenario until Dean just can't take it anymore.

    Language:
    English
    Words:
    4,990
    Chapters:
    1/1
    Comments:
    40
    Kudos:
    266
    Bookmarks:
    31
    Hits:
    1538
  6. Tags
    Summary

    What happens when Sam, Dean and Castiel are stuck in the bunker for quarantine?

    Language:
    English
    Words:
    2,650
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    100
    Bookmarks:
    2
    Hits:
    821
  7. Tags
    Summary

    Sam glances at the car that landed in the bunker. “Tell me who convinced Dean to drive that.”

    “What’s wrong with Darling?” Hippie Sam demands.

    “Well, how do you get in there?”

    “I… climb inside?” Other Sam seems skeptical. "What car do you drive?”

    “Oh you’re going to love this. Dean calls her Baby.”

    ...

    “Lookin’ good Baby.” It’s Dean’s voice.

    Dean talking to his car is nothing new, but he doesn’t want to freak out hippie Sam.

    “Thank you Dean. You look lovely as well.” Says another voice.

    Sam feels the beginnings of a tension headache. Sure, Dean talks to his car… but it never freaking replies!

    “Damn Cass, if you keep lookin’ at me like that, we’re gonna have to take Baby for a little spin.”

    Sure, Cass and the Impala might have some similarities: they both have black hair (if paint and your vessle’s hair colour counts), they have a very calming effect on Dean, they wear the same outfit all the time and Dean’s both given them nicknames. But is it possible to confuse an angel with a 1967 Chevy Impala?

    Well there’s only one plausible explanation.

    Hippie Dean is flirting with Cass.

    Language:
    English
    Words:
    1,311
    Chapters:
    1/1
    Comments:
    11
    Kudos:
    106
    Bookmarks:
    11
    Hits:
    823
  8. Tags
    Summary

    Dean Winchester is a workaholic librarian employed by the largest and most magical library in the world. When he begrudgingly participates in an anonymous, penpal-style book exchange, he’s swept up by a chance encounter with a stranger. But how is he supposed to stay focused on his reading when a blue-eyed hottie in a trenchcoat is wandering around the library, just begging to be kissed?

    Language:
    English
    Words:
    28,036
    Chapters:
    6/?
    Collections:
    2
    Comments:
    308
    Kudos:
    265
    Bookmarks:
    68
    Hits:
    4664
  9. Tags
    Summary

    Dean's present for Cas goes missing and Castiel doesn't know how to cook, but is it really too late to save their Christmas?

    Language:
    English
    Words:
    2,462
    Chapters:
    1/1
    Kudos:
    33
    Bookmarks:
    4
    Hits:
    398
  10. Tags
    Summary

    When Dean decides to meet his friend from Twitter IRL as a surprise, he doesn't quite expect the guy to be so hot, or for that hot guy to flirt with him, or anything else that comes after that for that matter.

    Language:
    English
    Words:
    5,238
    Chapters:
    1/1
    Comments:
    10
    Kudos:
    95
    Bookmarks:
    15
    Hits:
    953
  11. Tags
    Summary

    “Cass said yes.” Dean chirps happily. He leans closer to Sam, “when I asked him to marry me.”

    Choking, Sam gives him an incredulous look.

    “I know right.” Dean chuckles, “It only take you almost killing a guy to realise that you’re in love.”

    “I don’t think this is a good idea.”

    Sam’s voice is choked and Dean is suddenly pissed again. “You can’t even be happy for us. After all we’ve been through; we finally found something worth living for.”

    “You’re right Dean. I’m sorry.”

    “Sammy why are you crying?”

    OR

    What if Dean didn't miss and instead of stabbing the book, he stabs Cass?

    What if his mind blocks out the trauma leading Dean to believe Cass is still alive... just invisible?

    Language:
    English
    Words:
    1,256
    Chapters:
    1/1
    Comments:
    16
    Kudos:
    134
    Bookmarks:
    12
    Hits:
    1582
  12. Tags
    Summary

    The version of Castiel from Episode:5.04 The End meets his end and finds out what the afterlife has in store for him.

    Series
    Language:
    English
    Words:
    485
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    4
    Bookmarks:
    1
    Hits:
    75
  13. Tags
    Summary

    Castiel, Dean, Sam, and Charlie work for an Multinational Intelligence Organization (H.A.V.E.N), but is everything at Haven what they signed up for? Is their more hidden from the public about Haven? Can they find out the truth that has been brewing right underneath them? In this alternative universe the Winchesters lived a normal childhood. Castiel, Charlie, and the Winchester grew up together and now work side by side keeping the world safe. Until, something happens how will the others began to start moving forward. One year later, Castiel and Dean will undercover secrets that will change everything and endure troubles none of them would have ever expected to face. While discovering feelings that have been growing since childhood and into their adult lives.

    Language:
    English
    Words:
    28,738
    Chapters:
    6/?
    Comments:
    2
    Kudos:
    9
    Bookmarks:
    2
    Hits:
    172
  14. Tags
    Summary

    An overwhelmed Castiel is dragged to a Halloween frat party by his well-intentioned friend Charlie when he decides he needs to get some fresh air.

    Language:
    English
    Words:
    2,698
    Chapters:
    1/1
    Comments:
    14
    Kudos:
    54
    Bookmarks:
    4
    Hits:
    743
  15. Tags
    Summary

    A romantic comedy about a man who must steal a painting from a New York gallery to help conceal his family's art forgery, and the burglar who helps him.

     

    This bit of fanfiction is based on the 1966 movie How to Steal a Million - starring Audrey Hepburn and Peter O'Toole.

    Language:
    English
    Words:
    27,861
    Chapters:
    6/6
    Comments:
    29
    Kudos:
    98
    Bookmarks:
    30
    Hits:
    1420
  16. Tags
    Summary

    Dean has horrible back pain after an accident and when it gets worse he seek out specialist help. Castiel is a doctor who uses acupuncture in his practice.

    Series
    Language:
    English
    Words:
    22,534
    Chapters:
    7/7
    Collections:
    3
    Comments:
    45
    Kudos:
    200
    Bookmarks:
    27
    Hits:
    3580
  17. Tags
    Summary

    Of course when Dean gets pulled over he's not wearing any pants.

    Language:
    English
    Words:
    3,405
    Chapters:
    1/1
    Comments:
    16
    Kudos:
    149
    Bookmarks:
    9
    Hits:
    948
  18. Tags
    Summary

    One guy asks two girls to go out on a double date. Girls say yes, and it turns out that the girls are actually a couple! (Prompt)

    Dean Smith and Castlel James are on business trip to Japan. They've been best friends for 5 years and Castiel thinks he's only got a few nights before he'll break from being forced to witness any more of Dean's one-night stands. He's jealous, and he's starting to feel at the end of his tether.

    Things go from bad to worse when Dean decides to rope Castiel into a double date so he can score a hook-up with a shy local. At least that's what he thinks...

    Castiel doesn't suspect that Dean's been harboring feelings of his own. When Dean learns that his supposed date wanted to take her girlfriend out on the town with the cute gay couple she met at work, panic sets in. If this girl seems to know he's in love with Castiel, is it obvious to everyone? Can they go back to pretending none of this ever happened? Especially when they're both so comfortable in their parts?

    What a double-date mix-up!

    Language:
    English
    Words:
    25,145
    Chapters:
    18/18
    Comments:
    65
    Kudos:
    183
    Bookmarks:
    18
    Hits:
    2118
  19. Tags
    Summary

    Max Banes's arrival at the Bunker (along with a semi-unexpected guest) causes a whole other level of stress that Dean isn't prepared to deal with. Thankfully, Sam and Cas know exactly what to do to bring some semblance of normalcy to his life.

    Series
    Language:
    English
    Words:
    3,224
    Chapters:
    1/1
    Kudos:
    40
    Bookmarks:
    1
    Hits:
    321
  20. Tags
    Summary

    Dean and Cas have been best friends since they were freshmen. It is now their senior year, and Dean had come out as bisexual over the summer. It took a huge weight off of his chest. Unfortunately, his father didn't accept him after he came out, and took to beating him. When Castiel discovers this during their first day back at school, he tries his best to prove that Dean isn't what his father says he is. Castiel's perseverance and his love for Dean prevails, and it brings his and Dean's relationship to a whole new level.

    Language:
    English
    Words:
    11,723
    Chapters:
    7/7
    Comments:
    16
    Kudos:
    92
    Bookmarks:
    11
    Hits:
    1841

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