1 - 20 of 29 Works in Castiel/Dean Winchester Flirting

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  1. Tags
    Summary

    Castiel has been leaving a rose for the beautiful lounge singer for almost 4 months now. How has Dean not noticed? Well, its Valentine's Day, and Cas ends up getting exactly what he needed.

    Language:
    English
    Words:
    4,244
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    46
    Bookmarks:
    6
    Hits:
    955
  2. Tags
    Summary

    Ever wondered what would happen if Canon Dean met Destiel? Wonder no more...

    When Dean and Cas hit Otherworld with a bang, it begins a descent into crazy town.

    Oh yeah, this is going to be a mind fuck of the epic kind...
    This universe is like theirs but so not.
    They're pretty sure Jack has been kidnapped. His 'Baby', well he can't talk about that, it's just too horrible. Old friends are back, new enemies are made. Emotional fuckery is dumped by the ton, how is Dean supposed to deal with this shit? What is worse...Cas is keeping a secret. A long-held secret. Dean was raised from hell, but what happened down there and why is it so important? The revelation could destroy everything.

    It's funny, it's sad' it's emotionally traumatic, there is angst and fluff and declarations of love and discovery and AU and Canon and smut ...everything really.

    Check tags for warnings.

    Language:
    English
    Words:
    36,838
    Chapters:
    12/12
    Comments:
    69
    Kudos:
    123
    Bookmarks:
    44
    Hits:
    2246
  3. Tags
    Summary

    Castiel és Dean szomszédok. Nem találkoznak sűrűn, míg egy nap Cas a rengeteg narancs szín alsóneműit teregeti ki, Dean pedig ennek a szemtanúja lesz, és flörtölni kezd a szexis szomszéddal "ezerrel". :) ❤️

    Series
    Language:
    Magyar
    Words:
    610
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    18
    Hits:
    72
  4. Tags
    Summary

    Seemingly 'straight' and unknowingly bisexual Dean finally gets the courage to go to the local Pride parade and is nervous out of his mind. Until he meets the beautiful Castiel who is of course openly gay and proud of it.

    Language:
    English
    Words:
    1,802
    Chapters:
    1/1
    Comments:
    19
    Kudos:
    92
    Bookmarks:
    3
    Hits:
    1518
  5. Tags
    Summary

    Cas and Meg are getting ready for a Netflix and Chill night in their shared off-campus townhouse and things go slightly askew when the Pizza Man shows up.

    Language:
    English
    Words:
    947
    Chapters:
    1/1
    Comments:
    13
    Kudos:
    22
    Bookmarks:
    1
    Hits:
    223
  6. Tags
    Summary

    If global warming was a person then it might just happen to be Castiel.

    Oneshot/drabble

    Language:
    English
    Words:
    102
    Chapters:
    1/1
    Kudos:
    7
    Bookmarks:
    1
    Hits:
    169
  7. Tags
    Summary

    4/20 is a magical day for the Winchesters. It's a holiday that is held near and dear to their hearts, and their wallets, as business always does well. But to Dean, this day becomes even more special as he takes a chance and helps out the lost, but well-meaning Cas - who doesn't know the first thing about weed.

    By helping him, though, will Dean find an even greater high?

    Language:
    English
    Words:
    7,702
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    20
    Bookmarks:
    1
    Hits:
    291
  8. Tags
    Summary

    Dean just wants Cas to do something stupid.

    Oneshot/drabble

    Language:
    English
    Words:
    147
    Chapters:
    1/1
    Kudos:
    25
    Bookmarks:
    2
    Hits:
    333
  9. 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:
    1,485
    Chapters:
    1/?
    Comments:
    6
    Kudos:
    16
    Bookmarks:
    4
    Hits:
    171
  10. Tags
    Summary

    Dean's in his last year of college. The last semester, actually. The long classes, the assignments, it's all beginning to take its toll, so when he gets a day off from work, he decides to go home after school, do his homework, and kick back to catch up on the latest season of Doctor Sexy M.D. that he's been missing. He plans to just kick back, alone in his room and marathon the entire season. His parents are still at work and he has the entire house to himself, so imagine his surprise when someone knocks at his bedroom door, interrupting a very dramatic scene.

    In walks a man so gorgeous it instantly takes away any anger he'd had a moment ago at being interrupted. The question is, who is this guy?

    Hi, I'm Castiel, I guess I'm your cleaning lady.

    Dean didn't even know his parents had hired anyone to clean their house but staring into those blue eyes and seeing that killer smile aimed in his direction, he really couldn't be all that upset over the interruption.

    Series
    Language:
    English
    Words:
    3,670
    Chapters:
    1/1
    Comments:
    11
    Kudos:
    218
    Bookmarks:
    14
    Hits:
    1466
  11. Tags
    Summary

    “You know,” the shopkeeper murmurs, so close that Dean can see the different shades of blue in his eyes, “magic comes at a price.”

    Dean grins again. “I’m sure I can think of somethin’ to repay you.”

    Dean meets a witch. He doesn't believe. Then he does.

    Language:
    English
    Words:
    11,398
    Chapters:
    1/1
    Comments:
    41
    Kudos:
    249
    Bookmarks:
    66
    Hits:
    2347
  12. Tags
    Summary

    When Charlie talked him into joining the prom committee, Dean was not happy about it. He’s not even interested in going to prom, let alone planning it. But a meeting at committee chairman Anna Novak's house changes all that. When Dean meets her smoking hot dad, a punk gothic god covered in the most alluring tattoos, it alters his entire perspective. Now he’s hanging out with Anna all the time and finding every excuse to flirt with her gorgeous dad.

    Castiel Novak swore off romantic relationships when his mate died a decade ago. Now he writes novels, throws lavish Halloween parties, and drinks with his fuck-buddy, Meg. When he meets Anna’s stunning friend, Dean, all his determination to keep emotions out of the equation goes flying out the window. Now it’s all he can do to keep his hands to himself in the face of relentless temptation.

    Will Dean ever get to see how far down Mr. Novak’s tattoos go? Will Castiel get over his hang-ups and let Dean in? Or will they both go their separate ways without ever knowing if their explosive chemistry could be more than just a tryst behind the pool shed? Featuring sexist classmates, a champion robot named Leia, growly alphas, and a prom theme from Hell (er… Hogwarts).

    Language:
    English
    Words:
    35,253
    Chapters:
    1/1
    Collections:
    1
    Comments:
    76
    Kudos:
    565
    Bookmarks:
    108
    Hits:
    5830
  13. Tags
    Summary

    After what was supposed to be a normal hunt, Sam and Dean Winchester are killed. Crowley and Castiel bring them back to life, but with a problem. Mary, Cas, and Crowley now must learn how to deal with Sam being soulless and Dean being a demon until they can fix it. When an unfortunate confrontation between Sam and Dean occurs, Dean is severely damaged and Gabriel is forced to come to the rescue. Can Dean control his demonic instincts? Is he even really what he thinks he is?

    Language:
    English
    Words:
    27,025
    Chapters:
    11/?
    Comments:
    20
    Kudos:
    87
    Bookmarks:
    11
    Hits:
    1590
  14. Tags
    Summary

    "Charlie, I've died and gone to Heaven."
    "Impossible when you're already an angel, Cas."
    "Well I'm about to lose my halo to that Hunka Hunka bowlegged sin that just strutted through the doors."

    Series
    Language:
    English
    Words:
    660
    Chapters:
    1/1
    Comments:
    11
    Kudos:
    60
    Bookmarks:
    2
    Hits:
    817
  15. Tags
    Summary

    "What are you doing?" She repeats, lowly.

    "Playing the part." He whispers back, then louder. "Pumpkin."

    "How about you chill with the pet names, handmaiden." She pinches his side.

    Dean ends up squirming away from her sharp nails. "Ow, that hurt, schmoop-sie poo."

    "I'll kill you." She says, not bothering to lower her voice.

     

    After seeing his friend sad over her breakup, Dean offers to pretend to be Charlie's boyfriend to get back at her ex-girlfriend, Anna. Too bad the guy Anna brought with her is the most gorgeous man Dean's ever seen.

    Language:
    English
    Words:
    4,423
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    107
    Bookmarks:
    11
    Hits:
    1249
  16. Tags
    Summary

    "Wait, did you think I was a phone sex operator when I answered the phone?"

    ”No... no!” Castiel scoffs. “Okay, maybe for a split second. Your voice is..."

    "Sexy?"

    Castiel nearly falls off the bed at the sound of that word coming from that mouth.

    Series
    Language:
    English
    Words:
    1,252
    Chapters:
    1/1
    Comments:
    5
    Kudos:
    105
    Bookmarks:
    6
    Hits:
    1273
  17. Tags
    Summary

    “Don’t leave me out here all by myself, Cass. We can just stay where you can stand up. Didn’t mean to push you too much….Come on. Please? I was having fun.” Dean pouted like he knew the effect he had. He quirked one eyebrow and bit the side of his lip. Castiel squinted his eyes and tore his gaze away from Dean’s, eyeing the beach like it was his salvation. Dean waded closer and smiled. “You definitely are more of a bird than a fish though. Still a pretty bird though, even a half drowned one.” As soon as the words slipped out of Dean’s mouth, his eyes widened and his face bloomed with a pink blush. Castiel’s eyes widened as well and he let out a ragged breath, staring at Dean’s grip on his wrist. “I meant…I...” Dean mumbled.

    “You make a handsome fish….” Castiel grinned softly as he looked down at the water. He wouldn’t look up in case his words weren’t well accepted. Dean still had a grip on his wrist under the water and he kept bracing for Dean’s usual response, which was to pull away.

    Language:
    English
    Words:
    4,253
    Chapters:
    1/1
    Comments:
    24
    Kudos:
    132
    Bookmarks:
    18
    Hits:
    1262
  18. Tags
    Summary

    The boy’s eyes flicker to Zach, who’s moseying down the hallway and handing out high-fives like money. When he doesn’t say anything, Cas rambles on, “Don’t worry, it happens a lot—I mean, if you are worrying. You're definitely cuter than most people I've been pushed into." ABORT! ABORT! ABORT! "Sorry, I don't know why I—"

    "This happens a lot?"

    Cas’s eyes widen. If that voice can’t cut through the toughest stains, nothing advertised on television will. “No—I mean... yeah, it does, but—”

    “Kay, cool, thanks,” the boy says, moving past Cas in a determined stride.

    Language:
    English
    Words:
    2,095
    Chapters:
    1/1
    Comments:
    11
    Kudos:
    277
    Bookmarks:
    24
    Hits:
    2197
  19. Tags
    Summary

    Written for the wonderful leviathncas on Tumblr, who provided me with the following prompt:
    "It could be worse."

    Dean's day was going so well...

    Series
    Language:
    English
    Words:
    1,203
    Chapters:
    1/1
    Comments:
    9
    Kudos:
    68
    Bookmarks:
    3
    Hits:
    698
  20. Tags
    Summary

    One morning, when Castiel is running late for work, he catches the eyes of a certain green eyed mechanic, whilst he is waiting for the next train to central Bronx

    Language:
    English
    Words:
    956
    Chapters:
    1/1
    Kudos:
    28
    Hits:
    643

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