1 - 20 of 230 Works in Flirty Dean Winchester

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  1. Tags
    Summary

    The boys and Charlie go to an old school diner and Dean hits on the waitress, which doesn’t go the way he expects...

    Series
    Language:
    English
    Words:
    571
    Chapters:
    1/1
    Hits:
    16
  2. Tags
    Summary

    Ever since the Winchester Brothers died. Secrets about the monsters got out with hard proof to the mass media. Cyberlife rose not long after due to the public's fear towards those that lurk in the darkness.

    Androids are now among the public but many humans especially human hunters are skeptical about these humanoid machines. Especially since these two particular prototype androids WH100 and WH200 aka Sam and Dean have taken over the big hunts in Detroit.

    These two codependent androids can detect any non-human person almost instantly and can destroy any non-human being that is highly likely to be a threat to humans, even the ones who were once humans.

    However, over time about the uprising, the boys are starting to have doubts. Sam is starting to have doubts that all monsters deserve to die while Dean is thinking if he should break free from humans’ control.

    Will they side with Connor? Join Kara and Alice's journey? or Join Markus?

    Their choices are up to you the reader!

    Language:
    English
    Words:
    1,196
    Chapters:
    5/?
    Comments:
    3
    Kudos:
    4
    Bookmarks:
    1
    Hits:
    64
  3. Tags
    Summary

    Cas, a 3rd-year biology student, is an introverted and very anxious guy. Full of insecurities, he doesn't need to add one more thing to worry about in his life (and certainly not his potential "asexuality"). However, one day, he meets Dean at a poker night his roommate Balthazar is hosting.

    Dean is Cas’ exact opposite : easy-going, confident, funny… and also, very flirty. They keep bumping into each other around the campus and, somehow, every time Cas is with Dean, all of his worries seem to go away…

    However, when Cas learns about Dean’s reputation as “the master of one-night stands”, he is certain that they are DEFINITELY ABSOLUTELY not compatible. Or, are they?

    Language:
    English
    Words:
    57,219
    Chapters:
    11/11
    Collections:
    1
    Comments:
    10
    Kudos:
    53
    Bookmarks:
    14
    Hits:
    942
  4. Tags
    Summary

    You're a hunter on a case with the Winchesters, but your relationship with Dean is much more complicated than the case you're solving.

    Language:
    English
    Words:
    2,794
    Chapters:
    3/3
    Kudos:
    20
    Bookmarks:
    2
    Hits:
    452
  5. Tags
    Summary

    Castiel was raised by a Yakuza family. But he decided to sacrifice himself and go to jail to protect his little brother making him promise he would abandon the criminal life.
    But his little brother didn't keep his promise. That's why the special agent Dean Winchester will try to convince Castiel to help the police to catch his brother, by getting inside one of the most dangerous prisons as an undercover agent.

    THERE'S NO RAPE/NON CON IN THIS FIC.

    Language:
    English
    Words:
    2,688
    Chapters:
    1/1
    Collections:
    1
    Kudos:
    26
    Bookmarks:
    4
    Hits:
    305
  6. 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:
    40,410
    Chapters:
    9/?
    Comments:
    20
    Kudos:
    35
    Bookmarks:
    5
    Hits:
    1209
  7. Tags
    Summary

    Dean and his younger brother Sam, both rent boys, were invited to stay over at the Novak mansion with the intentions of being paid to service the sons bearing the Novak name.

    Of course, Sam enraptured the attention of one Gabriel Novak and Dean was left to choose from the Novak bunch. But then Dean meets the youngest of the Novak family, Castiel, and for the first time, Dean finally understands what it is to want.

    Beneath that shy facade that Castiel hides behind, Dean knows that there’s a possessive, dominating, and beautiful monster waiting to claim his victim. That victim was clearly Dean.

    Language:
    English
    Words:
    6,808
    Chapters:
    1/?
    Comments:
    7
    Kudos:
    30
    Bookmarks:
    10
    Hits:
    302
  8. Tags
    Summary

    Summary: Dean tries to stump you, the self-proclaimed champion of anti-pickup lines, with the cheesiest, cringeworthy lines he can think of.

    Language:
    English
    Words:
    2,574
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    27
    Bookmarks:
    3
    Hits:
    247
  9. Tags
    Summary

    Returning from a hunt, TFW 2.0 find Crowley in the War room wearing Betty White. Then they morph into the other Golden Girls. Except Cas, he's the Naked Chef.

    Series
    Language:
    English
    Words:
    4,813
    Chapters:
    1/1
    Collections:
    1
    Comments:
    22
    Kudos:
    8
    Bookmarks:
    2
    Hits:
    86
  10. Tags
    Summary

    The title is self explanatory

    Language:
    English
    Words:
    528
    Chapters:
    1/1
    Kudos:
    79
    Bookmarks:
    3
    Hits:
    787
  11. Tags
    Summary

    The angel of the Lord sighed. “Jealousy is an ugly emotion.”
    Dean smiled, holding back a snicker. Cas looked at him with a frown. “You think this is funny.”
    “A little bit, but not because it’s stupid,” Dean explained. “It’s not stupid. I think it’s funny because it’s really cute.”

    Language:
    English
    Words:
    2,807
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    112
    Bookmarks:
    13
    Hits:
    769
  12. Tags
    Summary

    You convince Dean and Sam to stop at a bowling alley.

    Language:
    English
    Words:
    1,677
    Chapters:
    1/1
    Collections:
    1
    Kudos:
    13
    Bookmarks:
    1
    Hits:
    182
  13. Tags
    Summary

    You convince Dean and Sam to stop at a bowling alley for a couple games.

    Language:
    English
    Words:
    1,677
    Chapters:
    1/1
    Kudos:
    6
    Hits:
    85
  14. Tags
    Summary

    Castiel’s newest case leads him to interrogate Dean Winchester, who thus far has always weaseled his way out of actually getting convicted. Well, Castiel is here to change that. And no amount of shameless flirting will convince him otherwise. Then again, this time Dean might actually be... innocent?

    Language:
    English
    Words:
    5,991
    Chapters:
    1/1
    Collections:
    1
    Comments:
    3
    Kudos:
    109
    Bookmarks:
    15
    Hits:
    1197
  15. Tags
    Summary

    Have you ever had dirty thoughts about Jensen Ackles and/or Dean Winchester?

    Of course you fucking have. And, to make shameless use of an SPN Family hashtag, #YouAreNotAlone.

    This fic is basically intended to be an Ackleholics Anonymous community: a safe space for all of our confessions. The idea is that each confession will inspire a one-shot (all to be posted as unrelated chapters), so that we can collectively indulge in all these filthy fantasies. Any and all confessions are welcome, whether sweet and fluffy, or just plain filthy smutty. Scenes can range from softcore and vanilla, to sinfully kinky and fucked up.

    So if you've ever had a dirty thought about this drop-dead gorgeous sex god... come on in and join the club ;)

    Language:
    English
    Words:
    93,917
    Chapters:
    43/?
    Collections:
    1
    Comments:
    1441
    Kudos:
    561
    Bookmarks:
    98
    Hits:
    51912
  16. Tags
    Summary

    Supernatural AU: Dean is the son of a wealthy businessman on a trip to New York City to ‘learn the family business’. Dean’s not really sure that’s what he wants—he’d much rather party until the sun comes up. That all changes when he meets a man who throws his world into a tailspin—Castiel, the hotel bellboy who underneath that enticing red coat is so much more than he seems. Now Dean's got his work cut out for him--he's got to somehow prove to Cas that he's more than what the tabloids say about him.

    Language:
    English
    Words:
    220,188
    Chapters:
    23/40
    Comments:
    78
    Kudos:
    101
    Bookmarks:
    23
    Hits:
    4245
  17. Tags
    Summary

    Dean Winchester has had a week from hell. Dean is a man of simple needs. So after a long week there are only a handful of things he wants. None of which will happen if he can't get home first.

    Language:
    English
    Words:
    7,996
    Chapters:
    1/1
    Collections:
    1
    Comments:
    2
    Kudos:
    46
    Bookmarks:
    4
    Hits:
    541
  18. Tags
    Summary

    Castiel is a realtor, and Dean is the client he is trying to help find his dream home. Dean is constantly flirting with him, leaving him flustered because he would really like to flirt back, but he needs to keep professional.

    Over the course of several months, Castiel gets to know Dean as he takes him to each house, learning what he likes and dislikes.

    Language:
    English
    Words:
    694
    Chapters:
    1/1
    Comments:
    25
    Kudos:
    334
    Bookmarks:
    18
    Hits:
    1174
  19. Tags
    Summary

    Summer of ‘07 saw Cas packing up his life and going away from Lawrence.

    Summer of ‘19 saw Cas packing up his and his daughter’s life and shifting back to Lawrence.

    Different times, completely different lives, but there was one person in his heart both times: the insufferable Dean Winchester.

    Language:
    English
    Words:
    91,352
    Chapters:
    25/?
    Comments:
    78
    Kudos:
    141
    Bookmarks:
    39
    Hits:
    5810
  20. Tags
    Summary

    “Dean, hands to yourself please.”

    The man in question straightens up in his chair, turns his flirty smile from the man two seats from him and onto officer Novak. “Sorry, Cas.”

    “Cas?” Hannah asks.

    “We get some regulars. They come to know a few of the officers, the patrol officers, especially.” Novak explains, the look on his face, almost slightly bored, slips a little. “As you know, I’m usually the one monitoring the Strip.”

     

    Police!Officer Cas is being filmed at work (A-la: Jail Las Vegas) for a reality TV show. Meanwhile Dean is a sex worker, not only familiar with the Strip’s booking process, but with a certain blue-eyed officer.

    Language:
    English
    Words:
    134,901
    Chapters:
    22/22
    Comments:
    897
    Kudos:
    1044
    Bookmarks:
    206
    Hits:
    20120

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