1 - 20 of 609 Bookmarked Items in Top Castiel/Bottom Dean Winchester

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  1. *

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    Summary

    Dean Winchester is on his own for the first time at 23 after Sam leaves for school. Feeling more alone than he ever has before, Dean finds himself drawn to his window where he can see into the apartment of a hot/weird guy. Each glimpse he gets causes him to like the guy a little bit more, and after forming a strange, one-sided connection with him, he can hardly believe his luck when the hot/weird guy turns out to be the owner of the coffee shop he just started frequenting. Now, if only he could crack the cool and collected shell the hot/weird guy uses in public to reveal the geeky side he’s so used to seeing through the window, everything would be perfect…

    Language:
    English
    Words:
    68,465
    Chapters:
    10/10
    Collections:
    1
    Comments:
    491
    Kudos:
    788
    Bookmarks:
    153
    Hits:
    5743
  2. 32

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    Castiel and Anna Novak roll into town on Castiel's motorcycle. They're polar opposites; Cas wears a leather jacket over his many tattoos, Anna wears a flower crown to compliment her dresses. The moment Dean Winchester sees the brother and sister pair in their high school parking lot, he is instantly curious. Dean wants to pursue a relationship but will Castiel's past experiences keep them apart or can they overcome the blinding anger, desperation, and fear?

    Language:
    English
    Words:
    35,104
    Chapters:
    16/16
    Comments:
    68
    Kudos:
    215
    Bookmarks:
    32
    Hits:
    4203
  3. 24

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    Surfing the internet, Cas discovers a little thing called Kinktober and decides to convince Dean to play along. Who is Dean to say no to anything Cas wants? Unless of course, Cas wants to talk about these things in front of Sam. Because, no, that would not be cool.

    Check the chapter titles and beginning notes of each chapter for the kinks contained within that particular chapter and any applicable warnings. Tags will be updated as I go since this is not entirely written yet and I'm not 100% where the boys will want to take this. If you think I've missed a tag, please please please please tell me so I can fix it.

    Language:
    English
    Words:
    57,371
    Chapters:
    14/32
    Comments:
    34
    Kudos:
    135
    Bookmarks:
    24
    Hits:
    4254
  4. 80

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    From a prompt. Sam finds links for gay porn and a search for huge cocks in his browser history and the boys figure out that it was Castiel who was watching it. Dean, convinced it will attract Cas, starts wearing his boxers around the bunker to give Cas an eyeful of his goods. Cas catches on to what Dean’s trying to do and flips the script a bit, surprising Dean. Smut ensues. Not AU, but also not really from any specific time in canon aside from sometime after they move into the bunker and Cas has gotten his grace back.

    Language:
    English
    Words:
    8,412
    Chapters:
    1/1
    Comments:
    94
    Kudos:
    543
    Bookmarks:
    80
    Hits:
    5972
  5. *

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    Dean and Lisa have been living together for a year. Dean works as a mechanic and studies architecture at night, while Lisa works full time as a real estate broker but dreams of becoming a yoga instructor.

    When they win a trip to Las Vegas they hope, with some luck, they can change their financial situation and live the life they have always dreamed about. Instead, they meet a powerful billionaire, Castiel Novak, who makes them an offer – one million dollars for one night with Dean.

    Language:
    English
    Words:
    61,648
    Chapters:
    22/22
    Collections:
    1
    Comments:
    190
    Kudos:
    455
    Bookmarks:
    126
    Hits:
    6110
  6. *

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    Dean grew up thinking -- knowing -- he'd be an alpha.

    Until he failed to present. As a beta, he has no mating cycle, no noticeable pheromones, none of the physical markers that are so important in a world of alphas and omegas. He's out of place. How is he supposed to navigate his relationships and find love when he doesn't fit into the neatly-defined boxes he's used to?

    By the time he meets his new roommate, Castiel, he's more or less given up on finding a mate. He wears his secondary gender like a chip on his shoulder. But you never know what the future holds, who will come into your life, and how they might change it forever.....
     

    Queer themes, finding identity, reconciling the past, and a whole lot of smut.

    Language:
    English
    Words:
    65,726
    Chapters:
    21/21
    Comments:
    892
    Kudos:
    895
    Bookmarks:
    172
    Hits:
    9473
  7. *

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    Dean Winchester was raised to become one of the best witch hunters the world has ever known, and his life's mission has always been to gank the witch who killed his parents when he was a boy. He's been hunting witches his entire life, and the one thing he knows for damn sure is that all witches are evil.

    Castiel Novak is a witch who was raised by two of the worst witches in history, but as far back as he can remember, he's only ever felt disgust and horror over the evil things his brothers do. After tragedy strikes close to home, he has to decide once and for all what kind of witch - and man - he truly wants to be.

    When Dean, his brother Sam, and Castiel all come face-to-face for the first time, they'll each be forced into making choices that not only have the power to alter their lives, but the lives of those they love most as well.

    "It is our choices that show what we truly are, far more than our abilities.” - Albus Dumbledore

    Language:
    English
    Words:
    132,636
    Chapters:
    16/16
    Comments:
    605
    Kudos:
    413
    Bookmarks:
    104
    Hits:
    4119
  8. *

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    A simple case turns Dean upside down as he attempts to deal with the effects of a particularly strange love spell.

    Series
    Language:
    English
    Words:
    28,226
    Chapters:
    5/5
    Collections:
    1
    Comments:
    323
    Kudos:
    1497
    Bookmarks:
    350
    Hits:
    16532
  9. 50

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    Opening his own clinic, Doctor Castiel Novak is doing his best to get his business and brand out and established in his new community. What he doesn’t expect is to come face to face with his high school crush and first lover, Dean Winchester at a local LGBTQ community health event. He’s even more shocked when he learns that Dean is the popular bisexual porn star Dean Smith, who in between shoots volunteers at the local community college LGBTQ organization.

    Though Castiel tries to brush their chance encounter off as nothing more than a sheer coincidence, suddenly Dean is everywhere. Dean makes it clear that he wants to see more of Castiel, but Castiel isn’t sure what to do about these conflicted feelings for Dean he’s had ever since he and Dean last saw each other years ago. Add in a brother and best friend/employee who seem determined to meddle in his love-life and Castiel is beginning to think the universe might just be pushing him and Dean Winchester back together.

    Language:
    English
    Words:
    53,799
    Chapters:
    10/10
    Collections:
    1
    Comments:
    45
    Kudos:
    215
    Bookmarks:
    50
    Hits:
    2139
  10. 7

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    Summary

    Dean has a huge daddy kink and Castiel has a huge thing for being in charge and dominate. Castiel has had trouble in the past finding a good bottom boy to take all he has to offer and satisfy him. Dean has had trouble finding a man to be his daddy and be patient enough to love him while fulfilling his needs. When the two meet, the end result is a perfect night neither of them will ever forget.

    Series
    Language:
    English
    Words:
    778
    Chapters:
    1/1
    Comments:
    13
    Kudos:
    83
    Bookmarks:
    7
    Hits:
    2617
  11. 23

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    Ten years ago today he had met Castiel in that barn, nothing had ever been the same. When he had told Castiel this, he had initially tilted his head and furrowed his brow – before Dean could question the expression, Sam had joked that time to angels is probably as inconsequential as bicycles to fish – but Castiel had abruptly grinned, stating that he would find something to do to celebrate his decade of knowing the brothers.

    Language:
    English
    Words:
    9,668
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    167
    Bookmarks:
    23
    Hits:
    1489
  12. 4

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    Cas is reluctant to the entrust his beloved car to a stranger but his first meeting with the owner of Winchester Vintage Automobiles convinces him to let go and Dean Winchester’s expertise is only one of the merits of signing up for his Lincoln’s restoration.
    Dean, on the other hand, already has enough going on with a family conflict and finding out that his new favorite client isn’t as straight as he'd assumed causes even more turmoil. Eventually, Dean has to face some truths about himself and Cas is happy to help.

    Language:
    English
    Words:
    5,912
    Chapters:
    2/11
    Comments:
    1
    Kudos:
    10
    Bookmarks:
    4
    Hits:
    198
  13. 15

    Words:
    10,730
    Works:
    4
    Bookmarks:
    15
  14. 48

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    Summary

    Angels develop knots when they have sex with their true mate.

    This would have been very good information to have ahead of time.

    Language:
    English
    Words:
    1,964
    Chapters:
    1/1
    Collections:
    1
    Comments:
    22
    Kudos:
    404
    Bookmarks:
    48
    Hits:
    8684
  15. 29

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    Dean is the king of hell, and the whole "nobody dares mess with me" thing can get pretty boring. Even punishing isn't fun anymore. But one certain angel prisoner might make things a little more interesting.

    Language:
    English
    Words:
    2,686
    Chapters:
    1/1
    Comments:
    20
    Kudos:
    241
    Bookmarks:
    29
    Hits:
    3886
  16. 54

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    Dean Winchester, part-time custodian at Sandover Industries, is an omega who listens to smutty audiobooks during his shifts. Unfortunately for him, the books are good—too good. The scent of his arousal is palpable, and the company vice president, Castiel Novak, has taken notice.

    Language:
    English
    Words:
    6,691
    Chapters:
    1/1
    Comments:
    25
    Kudos:
    417
    Bookmarks:
    54
    Hits:
    3305
  17. *

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    Dean watches as his father walks out on he and his brother for the last time. He's desperate. Sam is about to turn 18, graduate, and go off to Stanford. Dean's life has only been about protecting his brother and watching over his grief-stricken father. So when John leaves and Sam inches closer to moving to California, Dean finds himself not needed. When a chance encounter with a man named Castiel gives him the opportunity to feel needed again, Dean jumps at it. But he doesn't know what he's gotten himself into.

    Language:
    English
    Words:
    101,260
    Chapters:
    55/55
    Comments:
    227
    Kudos:
    663
    Bookmarks:
    143
    Hits:
    14897
  18. 17

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    Summary

    “Dude, don’t look now, but there’s another guy wearing the same costume as you!” Charlie daintily sipped her drink while Dean nearly spat out his beer.

    What starts with a similar costume rapidly turns into the most amazing one-night stand Dean's ever had. Cas is funny, gorgeous, mysterious and really knows how to use his... wings. Among other things.
    Dean made Cas promise to stay the night and watch the sunrise with him, but he finds himself hoping that Cas will stay a lot longer than that.

    Language:
    English
    Words:
    6,953
    Chapters:
    1/1
    Collections:
    1
    Comments:
    38
    Kudos:
    139
    Bookmarks:
    17
    Hits:
    946
  19. 25

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    Summary

    When Castiel’s grace was stolen, his life was in upheaval and he was fighting for survival. Yes, there was a tidbit of information that hardly seemed relevant at the time, but when Cas finally meets up with the Winchesters (after a Reaper attacked him with an angel blade, no less) this curious fact becomes pivotal.

    Angels don’t have secondary genders, and when Cas fell, he assumed he’d take Jimmy’s beta status. Except, now that he’s the only one in the vessel—now that it’s one-hundred percent Castiel—he has presented alpha.

    Faced with Dean and overwhelmed by his alpha senses, this new biology and seeing the hunter as an omega for what feels like the first time, Castiel is faced with a realization. Dean knows it right away, too. They’re true mates, there’s no denying it, and it could be a wondrous thing to come out of Cas’ mortality.

    Series
    Language:
    English
    Words:
    3,122
    Chapters:
    1/1
    Collections:
    1
    Comments:
    13
    Kudos:
    209
    Bookmarks:
    25
  20. *

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    Summary

    Dean's in love with Cas. Cas is in love with Dean. That much is obvious to everyone who sees them. But instead of acting on it, these two idiots seem bound and determined to score gold medals in the pining olympics. The staring, the longing, the unresolved sexual tension that's strong enough to combust and engulf the planet…is there anything that can push them out of their safe, cowardly positions? Leaving them to their own devices hasn't worked so maybe it's time to pull out the big guns.

    Language:
    English
    Words:
    41,169
    Chapters:
    8/8
    Collections:
    3
    Comments:
    238
    Kudos:
    1281
    Bookmarks:
    312
    Hits:
    19376

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