1 - 20 of 248 Works in Flirty Dean Winchester

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  1. Tags
    Summary

    (A/B/O; O!Cas find that A!Dean keeps flirting with people and decides it’s time to mark his territory)

    Series
    Language:
    English
    Words:
    2,207
    Chapters:
    1/1
    Kudos:
    42
    Bookmarks:
    1
    Hits:
    833
  2. Tags
    Summary

    The Bachelor is back on April 30th!

    Dean Winchester is on a ground-breaking journey to find the love of his life. With 16 amazing women and men ready to steal Dean's heart, anything is possible.

    Dean: "I'm a Chef from Kansas and I'm ready to fall in love and find my person. I want to get married; to settle down and create a life full of love and adventure. I truly believe my future husband or wife is here."

    "How could you not fall for Dean? He's the whole package." "Dean has everything you could ever want in a husband. He's funny, he's hot, and he can cook." "I could see myself marrying Dean."

    Romance is on the horizon for Dean: "I could see myself falling for so many of these amazing people." "What would life be like if we got married?" "I can't picture my life without you."

    But with romance comes drama. And lots of tears. "I'll do whatever it takes to get my time with Dean." "You back-stabbing, two faced bitch." "Go on, tell Dean what you told the cameras yesterday you lying asshole." "What Dean doesn't know won't hurt him."

    But will Dean find his forever person? "I'm so in love with you." "I want to put this ring on your finger so badly." "You're it for me."

    Language:
    English
    Words:
    15,877
    Chapters:
    1/11
    Comments:
    48
    Kudos:
    82
    Bookmarks:
    18
    Hits:
    919
  3. Tags
    Summary

    Sam and Dean take things a lot further in preparation for what Sam thinks Jack wants.

    Let’s be honest, it’s porn with a smattering of plot. And if you’re into it you’re somewhat as bad as me! ;)

    Series
    Language:
    English
    Words:
    17,309
    Chapters:
    4/4
    Comments:
    2
    Kudos:
    24
    Bookmarks:
    5
    Hits:
    1388
  4. Tags
    Summary

    Heya folks! We have a cross over for ya here, story focuses on Harry and Dale, yet Dean & the boys play a major role.

    _¤_
    "Hey Cas, have you seen Sam?" Came an easy Midwestern accent, but when they finally turned bright green eyes to Cooper, a moment of realization came over them. "Shit, man!" The other male said a bright laugh and smile on his face as he pulled back his arm, "Sorry, 'bout that, you look like my buddy Castiel."

    "Castiel? Like the Angel?" Cooper asked his dark brows pulling upwards, "Excuse me, but I don't think we have met but with this being such a small town and myself not here for long I don't think we have had a chance." Dale gave the other male a bright smile and offered a hand, "Deputy Dale Cooper. "

    Language:
    English
    Words:
    2,830
    Chapters:
    3/7
    Comments:
    4
    Kudos:
    6
    Bookmarks:
    2
    Hits:
    132
  5. Tags
    Summary

    A Valentine's Day SPN100 challenge and DEW fic that has been sitting on my computer for two months. Wow: Heart and DEW theme: Valentine's Day. Valentine's Day is one of Dean's favorite days, but there's one day that tops it, as Dean's date learns the hard way. Actual drabble 100 words on the dot.

    Series
    Language:
    English
    Words:
    100
    Chapters:
    1/1
    Collections:
    1
    Kudos:
    4
    Hits:
    26
  6. Tags
    Summary

    Castiel needs to borrow someone's jeans, Dean is happy to be of service.

    Series
    Language:
    English
    Words:
    1,760
    Chapters:
    1/1
    Comments:
    10
    Kudos:
    82
    Bookmarks:
    3
    Hits:
    588
  7. Tags
    Summary

    It's been freaking six months. yes, full Six months and still when Castiel comes out from the office, Dean freaking Winchester will sit outside of the office, in the huge guest area with something new, something different kind of gift in his hand.

    Dean was asking for Out on a Date. A one date.

    Dean was in love with Cas, but Cas had some trust issues.

    So will they make it out?😍

    Language:
    English
    Words:
    55,984
    Chapters:
    12/?
    Comments:
    22
    Kudos:
    68
    Bookmarks:
    10
    Hits:
    3181
  8. Tags
    Summary

    (Season 13) Castiel is back from The Empty eager to raise his infant son. Dean isn't thrilled about raising a baby but he's determined not to make the same mistakes with Cas that he did before he died.

    Language:
    English
    Words:
    19,756
    Chapters:
    14/14
    Comments:
    14
    Kudos:
    145
    Bookmarks:
    6
    Hits:
    2646
  9. Tags
    Summary

    Sam Singer is a lonely kid at highschool. He's got his best friend, Cas, but he's resigned himself to being single and ignored by the guys in his small town. That is until Dean Winchester arrives from out of town. Sam knows that Dean could have anyone he wants, but that doesn't stop a part of him longing for the mysterious handsome stranger. Will a relationship ever blossom between them? Can it, when Sam's walls are so heavily guarded?

    Language:
    English
    Words:
    12,049
    Chapters:
    10/?
    Comments:
    28
    Kudos:
    68
    Bookmarks:
    10
    Hits:
    1193
  10. Tags
    Summary

    "I think it is all a matter of love: the more you love a memory, the stronger and stranger it is." - Vladimir Nabokov

    Castiel knows Dean will never fall in love with him, no matter how long he pines for him. But when a witch curses Dean to lose his memory and Cas is called in to help, Dean starts flirting with him. Cas tries to focus on the case, he really does, but he’s caught up in the whirlwind of feelings Dean is stirring up. When he steps into a diner to pick up a bacon cheeseburger, milkshake, and a slice of pie for Dean, he gets taken by the Loughlins instead, leaving Dean alone in the cold.

    Dean doesn’t remember the beautiful man with the bright blue eyes, but he’s warm and smells like Heaven, and his voice is deep like gravel road under tires. When the pretty man says, “I’m Cas. I’m your best friend,” Dean’s inclined to believe him, but there’s something else there: a fluttering in his chest, a gravitational pull.

    “Are we dating?” No, but I wish we were.

    Language:
    English
    Words:
    15,261
    Chapters:
    1/1
    Collections:
    5
    Comments:
    56
    Kudos:
    937
    Bookmarks:
    170
    Hits:
    6444
  11. Tags
    Summary

    With just a year to live, Dean meets Lou Smith. A young retired hunter with a bakery and farmhouse that might as well be a fortress. The way she smiles makes his heart skip a beat, and the closer he comes to the end, the more he's drawn in by her presence, regardless of the secrets she keeps. As Dean faces down hell hounds, Lou offers him not only comfort but possibly a way to stay out of hell.
    Part 1 of 3
    Tons of side stories!

    Series
    Language:
    English
    Words:
    51,711
    Chapters:
    16/16
    Comments:
    94
    Kudos:
    66
    Bookmarks:
    18
    Hits:
    1908
  12. Tags
    Summary

    Dean's just trying to bake a strawberry shortcake. It should be a simple enough task. Except Cas suddenly appearing by his side mentioning strawberries are known aphrodisiacs is a one-way ticket to completely derail Dean's plans. Let alone seeing Cas pick up the strawberries that Dean just so happened to drop as soon as Cas mentioned the word aphrodisiac. Something about seeing Cas' fingers wrapped around strawberries is enough to have Dean swooning. Maybe it was time to test that theory of aphrodisiacs strawberries with a kiss or two.

    Series
    Language:
    English
    Words:
    1,122
    Chapters:
    1/1
    Collections:
    2
    Comments:
    8
    Kudos:
    191
    Bookmarks:
    17
    Hits:
    1305
  13. Tags
    Summary

    Dean should not have started to play flirt with Cas to tease him, because he really was not prepared for what happened next. Especially since the flirting wasn't just teasing on Dean's end. He should probably learn how to think before speaking...

    Suptober, Day 6: Cemetery Boys

    Series
    Language:
    English
    Words:
    1,737
    Chapters:
    1/1
    Collections:
    1
    Comments:
    7
    Kudos:
    146
    Bookmarks:
    10
    Hits:
    974
  14. Tags
    Summary

    Dean, Sam, and Cass go to sunny Florida to investigate a series of disappearances on a beach. But when Dean goes missing while on the job Cass and Sam have to solve the case and find him.

    Language:
    English
    Words:
    2,523
    Chapters:
    3/?
    Kudos:
    5
    Bookmarks:
    1
    Hits:
    224
  15. Tags
    Summary

    Castiel typically dreads fire safety day... that is, unless there is a green-eyed fireman to make it worthwhile.

    Series
    Language:
    English
    Words:
    1,705
    Chapters:
    1/1
    Comments:
    18
    Kudos:
    172
    Bookmarks:
    10
    Hits:
    1032
  16. Tags
    Summary

    A brief moment between Dean and Cas- neither of them know what they're doing, but that's not the point, is it?

    Language:
    English
    Words:
    879
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    45
    Bookmarks:
    5
    Hits:
    241
  17. Tags
    Summary

    “Deana, you are awake,” John grumbles, sipping a whiskey bottle.

    “Just -- just stay out of Sammy’s room,” She holds out her hand to him, and he takes it, walking closer and lacing their fingers together. “Come into my room, Dad.”

    “Daddy,” John emphasizes, leaning closer to Deana.

    Series
    Language:
    English
    Words:
    7,018
    Chapters:
    4/4
    Comments:
    2
    Kudos:
    45
    Bookmarks:
    4
    Hits:
    3899
  18. Tags
    Summary

    This had simply never happened. Dean always checked the entire house, sometimes twice, laying sigils and protection spells and lines of salt as he went, and today was no exception. Sure, the place might have been a little strange, but it was foreclosed upon like a decade ago. So absolutely why can Dean hear someone walking around on the second floor of this abandoned house? An unchecked closet? The wind split a salt line? Some sort of undiscovered thing that was immune to all traps?   

    tldr; The empty house Dean's trying to crash in isn't as empty as he thought it would be. Enter Castiel.

    Language:
    English
    Words:
    8,178
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    111
    Bookmarks:
    6
    Hits:
    870
  19. Tags
    Summary

    Mick has to explain to Cas that he was flirting. Cas has some realizations about the things Dean has said to him.

    Language:
    English
    Words:
    371
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    76
    Bookmarks:
    2
    Hits:
    791
  20. Tags
    Summary

    Eileen and Sam are reunited, and Cas opens up to Dean while helping him face his fears. Between the grocery store, the shower, and the Dean Cave, they find joy and comfort in each other.

    The four go on a beach trip and bring Jack's vision to life. Dean figures out how he can help people even if he's no longer actively hunting.

    Cas temporarily gets called to help restructure Heaven, and comes back to earth with insights. He convinces Dean to make an appointment, and Dean gets Cas to do it too - on the condition that Dean eats healthier.

    Series
    Language:
    English
    Words:
    13,688
    Chapters:
    4/7
    Kudos:
    9
    Bookmarks:
    1
    Hits:
    335

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