1 - 20 of 110 Works in Comfortably Bisexual Dean Winchester

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  1. Tags
    Summary

    John Winchester has moved his sons every few weeks for the past thirteen years since his wife, Mary, died in a house fire. Finally, his oldest son, got sick of it and put his foot down. He and Sam were going to finish high school in one spot. Surprisingly, John agreed. Now, Dean and Sam were staying with family friend Bobby Singer in Sioux Falls, staying put for the first time in their short lives. Dean decides he's starting over, and he's going to be better. His actions will have real consequences, here, and he doesn't want Bobby to have to deal with the kind of student he's been in the past. Unfortunately, he ends up in the principal's office the second day of school. Fortunately, the punishment he gets is to be tutored by the mysterious Castiel.

    Language:
    English
    Words:
    5,889
    Chapters:
    3/?
    Comments:
    2
    Kudos:
    11
    Bookmarks:
    1
    Hits:
    61
  2. Tags
    Summary

    The Devil is gone, and Dean adjusts to life with a nephilim baby and two Castiels hanging around.

    Series
    Language:
    English
    Words:
    3,927
    Chapters:
    1/?
    Kudos:
    4
    Hits:
    50
  3. Tags
    Summary

    One day a rift opens up between the main universe and the Apocalypse universe, and Dean, Sam, and Cas travel to the universe where humans and monsters are being systematically eliminated by angels of the Lord.

    Dean meets the Castiel that fell from Heaven without Dean there to catch him, and Dean's own Castiel stoically attempts to come to terms with an alternative version of himself that clings to Dean in a way he always wanted but never thought he could have.

    Or,

    12x23 was ooc garbage, and it would have been so easy to have written the episode in a way that honored the characters and canon and made a whole lot more goddamn sense.

    Series
    Language:
    English
    Words:
    11,654
    Chapters:
    3/3
    Comments:
    2
    Kudos:
    31
    Bookmarks:
    1
    Hits:
    450
  4. Tags
    Summary

    Castiel just wants to get home and hang out with his cat, but an empty gas tank and a dead phone battery have other ideas. Good thing Rocky's Bar is within walking distance... Now all he has to do is work up the nerve to go inside.

    Singles Night at Rocky’s is a good time. Or, usually it’s a good time. Any other time but tonight, it would be a good time. It’s just, Dean’s tired and grumpy and right now -- still figuring things out after Bela -- not in the mood for what Charlie's roped him into. But then a weird guy walks into the bar and, well...

    Turns out one guy trying to figure himself out and one guy trying to figure out the world actually make a pretty good team. Funny how that happens.

    Language:
    English
    Words:
    16,858
    Chapters:
    4/?
    Comments:
    17
    Kudos:
    63
    Bookmarks:
    11
    Hits:
    666
  5. Tags
    Summary

    Their relationship wasn't exactly forged by fire, but perhaps Dean's lengthy period of pining was just his waiting on fate. Because like very few others around them, protectiveness is a dominate trait.

    Language:
    English
    Words:
    1,446
    Chapters:
    1/27
    Collections:
    1
    Kudos:
    6
    Bookmarks:
    3
    Hits:
    73
  6. Tags
    Summary

    Although the story takes place in the Fallout universe, you don't have to know the games.

    Castiel Novak was born before the Great War. He got into Vault 111 by mistake. Coincidentally, that’s the Vault designed to observe the effects of long-term cryogenic suspended animation on unsuspecting test subjects. Suddenly, Castiel wakes up, finding the other cryo-capsules empty. Confused, he leaves the vault and sees himself standing in front of a whole different world.

    Dean Winchester was born a long time after the Great War. He was raised in a hopeless world and learned how to deal with raiders, mirelurks and deathclaws at an early age. He lives in the small village called Sanctuary. He just thinks that maybe, life is getting a little less bad after the past events but then a confused, helpless, and odd-looking guy crashes into his life.

    Language:
    English
    Words:
    92,746
    Chapters:
    51/51
    Comments:
    21
    Kudos:
    90
    Bookmarks:
    25
    Hits:
    3472
  7. Tags
    Summary

    Dean is going to community college to appease his parents. He signs up for and Anatomy class and is partnered with Castiel.

    This is just a cutesy little story based on actual events in the author's life...well the first couple chapters, at least.

    Series
    Language:
    English
    Words:
    11,750
    Chapters:
    4/?
    Comments:
    6
    Kudos:
    7
    Hits:
    177
  8. Tags
    Summary

    "Dean Winchester was 18 and one day when he took his little brother and ran. "

    Language:
    English
    Words:
    5,065
    Chapters:
    2/?
    Comments:
    1
    Kudos:
    43
    Bookmarks:
    5
    Hits:
    502
  9. Tags
    Summary

    [podfic version]
    Dean Winchester is not a cat guy.
    But one softhearted Sasquatch brother and a mad dash to the pet store later, Dean somehow finds himself the sole caregiver for an abandoned baby kitten. It's a good thing that quirky pet store girl gave him the Twitter handle for her cat rescue buddy, CJ. Dean doesn't know about the kitten, but he sure as hell could use some rescuing right about now.

    Castiel Novak is not a baker.
    But one interfering best friend and some dismal Yelp reviews for his brother's coffee shop later, Castiel somehow finds himself standing in front of a cook top in his very first baking class, his non-existent baking aspirations literally going up in smoke around him. It's a good thing his gorgeous, green-eyed classmate is there to rescue him...

    Language:
    English
    Words:
    51
    Chapters:
    13/13
    Collections:
    1
    Comments:
    146
    Kudos:
    68
    Bookmarks:
    12
    Hits:
    1512
  10. Tags
    Summary

    This thing Dean has going on with Crowley, it's really not a big deal. Yeah, he's hiding it from his friends and family, but he hardly has to tell them about everyone he ever sleeps with. After all, it’s only straightforward, morally dubious fun. It’s just sex.

    Which is why Crowley giving him the sweater comes as something of a surprise.

    Series
    Language:
    English
    Words:
    10,378
    Chapters:
    1/1
    Comments:
    55
    Kudos:
    500
    Bookmarks:
    71
    Hits:
    2132
  11. Tags
    Summary

    This is so stupid. Dean’s driving only just over the speed limit, stopping crisply at every stop sign, and slowing down when the traffic lights turn yellow instead of speeding up and trying to make it through. He never drives this carefully. He doesn’t drive this carefully when they have bodies in the trunk.

    Apparently, having a couple grams of weed on him turns him into a goody-two-shoes.

    Language:
    English
    Words:
    3,423
    Chapters:
    1/1
    Collections:
    1
    Comments:
    17
    Kudos:
    83
    Bookmarks:
    15
    Hits:
    434
  12. Tags
    Summary

    Dean sneaks into his boyfriend's bedroom in the middle of the night to whisk him away for some classic Winchester romance.

    Language:
    English
    Words:
    4,464
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    53
    Bookmarks:
    2
    Hits:
    656
  13. Tags
    Summary

    Castiel is a painter in France who lacks inspiration. His brother Gabriel manages to convince him for a night out of drinks. There he meets a beautiful man named Dean who suddenly sparks his inspiration after a “one night stand”. Him and Dean both agree to hook up again and so begins their sexual friendship. But of course, they catch feelings for each other.

    That doesn’t mean they were on the same page...

    Language:
    English
    Words:
    60,067
    Chapters:
    43/43
    Comments:
    10
    Kudos:
    41
    Bookmarks:
    8
    Hits:
    1520
  14. Tags
    Summary

    Castiel and Dean have finally expressed their feelings for one another and are becoming comfortable with the title of relationship between them. However, there is one thing that is making Castiel uneasy and it’s up to Dean to reassure the angel that their love is so much more powerful than sex.

    Language:
    English
    Words:
    2,940
    Chapters:
    1/1
    Comments:
    11
    Kudos:
    86
    Bookmarks:
    8
    Hits:
    670
  15. Tags
    Summary

    Cas wasn’t at school that morning, which was the first red flag in Dean’s mind.

    The second red flag, which made the first red flag look pale in comparison, was that Gabriel was standing next to Baby after school, leaning on her hood, his hands tucked in his pockets, face grim.

    ~
    alternatively, the one where Chuck makes good on a threat to send Cas away to a catholic boarding school, John drives his children away for the last time, and Dean, Gabriel, Sam, and Cas find their way out of a place that had never really been home.

    (COMPLETE, UPDATES REGULARLY)

    Language:
    English
    Words:
    18,934
    Chapters:
    7/7
    Comments:
    15
    Kudos:
    87
    Bookmarks:
    18
    Hits:
    1106
  16. Tags
    Summary

    This is the last installment for the series. Thank you for reading! :D <3 <3 <3

    Series
    Language:
    English
    Words:
    754
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    29
    Bookmarks:
    1
    Hits:
    202
  17. Tags
    Summary

    Sam has been thriving at university every now and then he would come home to visit Dean, stay the night at his place and watch him as he works on cars, sometimes he brings his friend over to meet Dean and stay for the few days he's there. That friend being none other than Castiel Novak, the handsome, hot as fuck, psych student. Every visit Dean stops himself from jumping the man, shoving his tongue down his throat and fucking him without mercy against the wall. Seeing the man alone is hard enough, painfully, literally hard.

    One visit, one night, when Sam has to go out, purposely leaving the two alone in the house together Dean decides he can't hold back anymore.

    Language:
    English
    Words:
    3,732
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    223
    Bookmarks:
    14
    Hits:
    3329
  18. Tags
    Summary

    Dean chooses to stay at Sonny's, on the condition that Sonny gets Sam away from John.

    When the court papers are served, John downs two bottles of whiskey, and puts a bullet in his son's head.

    Six years later, after Dean has finally started to live again, something that looks like Dean's dead brother walks out of the grave.

    Language:
    English
    Words:
    2,585
    Chapters:
    1/1
    Comments:
    16
    Kudos:
    153
    Bookmarks:
    28
    Hits:
    791
  19. Tags
    Summary

    What it says on the tin. Season 5 episode3: Free to be you and me.
    Dean won't let Cas die a virgin, Cas won't settle for less than his best friend. Good for him.

    Language:
    English
    Words:
    666
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    51
    Bookmarks:
    1
    Hits:
    601
  20. Tags
    Summary

    After fourteen years of driving across the country, Dean has finally decided to hang up his keys, settle down, and take over the Singer Auto Shop. Only one more week of driving stands between him and the next chapter of his life.

    One problem—Cas doesn’t know yet.

    For seven years now, Dean and Cas have been hooking up in the rare times their routes cross each other… and Cas secretly wishes their no-strings-attached arrangement could turn into something more.

    While Cas tries to find the words to tell Dean what he really wants, Dean wonders how Cas will fit into his life after he quits driving. Nowhere better to figure it all out than on the open road.

    (Inspired by the song "Drive Me, Crazy" by Orville Peck)

    Language:
    English
    Words:
    36,487
    Chapters:
    8/8
    Collections:
    1
    Comments:
    174
    Kudos:
    536
    Bookmarks:
    137
    Hits:
    4688

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