1 - 20 of 101 Works in Dean Winchester Comes Out
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“What’s that?”
Dean turned around and frowned at his brother. “What the hell, Sammy? You’ve never seen a picnic blanket?”
“I know what it is,” Sam grumbled. “It’s just… We don’t do picnics.”
Suptober - Day 2: Picnic
Series
- Part 1 of Suptober 2025
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His amazing, beautiful Cas had just sacrificed himself for him . . . he’d done all of it for him? How is Dean worthy of this kind of loyalty? Of his otherworldly friendship? Of his . . . love?
(or dean cries after castiel is taken by The Empty in 15.18, and then cas is rescued, and then deancas have a kiss and a conversation) -
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Dean's fine, really! Except he hasn't left his room in days, stinks, and can't seem to be able to put that bottle of whisky down. Sam decides to do something about it
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Cas Novak doesn’t do feelings. He’s got a good job, a luxury loft, and a steady rotation of hookups that never stick around long enough to expect more. That’s exactly how he likes it—until he meets Dean Winchester.
Dean’s seventeen, still in high school, and way too smart for his own good. What was supposed to be a one-time thing becomes complicated when Dean refuses to be another nameless man in Cas’ bed. He’s not afraid to call Cas out, push his buttons, or dig into the emotional disaster area Cas has spent years pretending doesn’t exist.
Cas never thought he wanted this kind of connection, but when there’s a violent attack, he is faced with the reality of what Dean really means to him.
Queer as Folk rewritten and reimagined.
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Castiel has been taken by the Empty, and Dean Winchester doesn't know how to cope. The grief, guilt, anger, and anguish are too much for Dean to handle after losing his best friend, and he spends several months in a pit of despair...until Castiel comes back.
Post-Canon Fix-It! This is a canon-divergence AU, where Dean actually properly mourns for Castiel, has legitimate grief over losing his best friend, and finally looks deep enough inside himself to realize he had loved Castiel all along. Basically everything after S15E18 didn't happen. There's a REASON they titled that episode 'Despair', and Dean really gets to understand what that truly means in this story.
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After an odd case, Dean messes with a time globe that accidentally switches his life with himself from a decade into the future! As he struggles to grasp through what his potential life holds, his impending relationship with Castiel becomes blurry between the lines of friendship and something more.
Dean recognizes all of this before, his biggest issue, unfortunately, is how to deal with the past without changing his future.
This fic is inspired by an ongoing mini comic strip from colorlessjay on tumblr! Please check them out!
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Dean struggles to come to terms with his bisexuality after a hunt where he's temporarily turned into a woman. Sam does his best to help his brother the only way he knows how, lore.
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Dean stumbles out of the closet.
Season 7 episode 12
- Language:
- English
- Words:
- 174
- Chapters:
- 1/1
- Kudos:
- 28
- Hits:
- 579
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It is the holiday season, and Christmas was just around the corner. Team Freewill are taking full advantage of the rare but much-needed downtime they have been having. Much to Sam’s surprise, Dean and Cas have decided that it’s time for them to have a long overdue holiday dinner. Little does Sam know that he’s about to walk into the biggest holiday surprise he could ask for.
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“I don’t know why I’m here,” Sam finally said, his voice low and uncertain. “I’m sorry, this is a waste of your time. I shouldn’t have bothered you.”
He stood abruptly, his hand already on the doorknob when the doctor spoke again, her tone gentle but firm. “What makes you think you’re bothering me?”
Sam hesitated, staring at the door. His fingers twitched, ready to turn the knob, ready to bolt.
“Who told you that your feelings are a waste of time?” she asked, her voice soft but pointed.
“My dad,” Sam whispered as if John might be just outside the door, waiting to drag him back.
“Tell me about him.”
or at 19 years old Sam Winchester decides it’s time to heal from his past and prepare for his future by starting therapy.
Series
- Part 1 of Same Broken Bones
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Look at your life, he just wants to make it right by greenjello94
Fandoms: Supernatural (TV 2005)
14 Nov 2024
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Amara brought Mary back from the dead but after a couple months of trying to adapt, Mary asks Amara to bring back John.
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change your name, change your mind.
or, sam finds out that she and her brother are the same, but different.
Series
- Part 1 of transnatural transchesters
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After joining heaven for such a long time, Dean finally meets again with Castiel... The more they talk and spend time together, the more Dean seems to struggle with everything that happened down on earth when Cas had left him. There's also this warm feeling coming from his chest that he can't describe... Will Dean be able to sort everything out ?
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Still beautiful, still Dean Winchester by Werewolf_Origins
Fandoms: Supernatural (TV 2005)
31 Aug 2024
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“I am Dean Winchester. Daughter of Mary and John Winchester. I am Sammy's older sister. I am….a woman.”
Her tired reflection gazed back at her in awe.
She did it.
She actually did it.
Or: snapshots of Dean's journey through life as a trans woman, and how she comes to accept herself.
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Series
- Part 15 of My Pride Postings 2024
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"I'm not lying," Dean finally whispers, the silence no longer bearable. "I don't want to be with her."
And he meant it.
But the same way his dad's death still weighed on him, or his mother's death, or Bobby's, or Jo's or anyone else in the long list of people they'd lost. This loss weighed on him.
"I don't think I ever should've been with her."
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Dean comes out to Cas
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He’s Old Fashioned Like That by 221castiel
Fandoms: Supernatural (TV 2005), Supernatural
30 May 2024
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“What do you think he’ll say?”
Bobby hesitated, though Dean already knew the answer. “I don't know kid, your dad- he’s old fashioned.” That was a nice way of saying homophobic. “He thinks he knows how things are supposed to be, and- I wish I could tell you he wouldn’t care but I can’t.”
“I know.”
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After four months of dating Castiel, Dean finally tells his dad
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15 year old Dean confides in 11 year old Sam after John flips on Dean for finding him kissing a boy.
Sam might be a kid, but he knows what Dean did isn’t wrong.
This is self-indulgent and mostly fluff with a little hurt/comfort.
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What if Dean and Castiel's ending turned out differently? What if it wasn't all one-sided?
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Dean Winchester is about to lose his best friend, but it makes him realize, maybe he's losing more than that. Maybe there was something there all along that he couldn't ever see until now. How will Dean cope with this newly learned information, and how will it change him from then on?
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Dean took Sammy and ran away from their abusive dad. Dean's worked as a mechanic his entire life in order to support Sam's dream of becoming a lawyer. Then someone catches Dean doing advanced math and wants to know more about Dean's life and who he is.
Something bad happens and Dean needs help. He needs to face his fear and go to court again. He doesn't want to burden Sam, who can he call? Will Dean be able to stay sober?