1 - 20 of 246 Works in Dean Winchester's First Time With a Man
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When fate entwines a dragon's fiery heart with his mortal enemy's burning passion, sparks fly.
Unbeknownst to them, their forbidden love is mirrored by a deeper truth.
As their love grows stronger, the secrets of their past threaten to tear them apart. They must confront the ultimate question: can love burn brighter than the flames of war? -
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It’s been about two months since Cas first made with the laying on of hands, and god, Dean just can’t get enough.
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- Part 2 of An Idiom A Day...
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Jack, Sam and Dean check into a haunted hotel for a case, intriguing the receptionist. Jack shares a romantic moment with the receptionist when he rescues her, but as Sam helps him prepare for the hookup, he realizes Sam is the one he really wants.
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The Winchesters go on what they think is a routine vampire case while Castiel is off to find a lead on God's location. Meanwhile, Dean is coming to terms with not only his feelings for Cas but how to deal with them when the angel finally returns.
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Summer before junior year of high school Castiel decides to share some secrets with his best friend.
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The one where Dean is more than glad to help out.
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Life can change in a moment, from a single decision, a choice... As Dean knows all too well. For a single night, he tasted freedom and it was incredible. He'll never forget that taste, or that man, carrying the memories with him at every moment even if he isn't brave enough to make a new choice.
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We're taking a trip, folks, so buckle in as we watch Dean strut his stuff and get the world drooling at his feet.
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Dean has one of those nights where the universe hands Sam all the smiles and leaves him the tab. Tipsy and sour, he finds Cas in the bunker library, polite, patient, and asking if there’s anything he can do to make it better. Dean takes him at the wrong/right angle. A lesson turns into discovery; a slow line finally breaks. Dean shows, Cas learns fast, and a frustrated night becomes something that feels suspiciously like home.
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Dean Winchester never thought he'd find himself in a bar in L.A. flirting with a firefighter named Buck — let alone wanting more than just a one-time hookup. But when Dean asks for round two, rougher and more intense than ever before, Buck’s more than willing to give him exactly what he needs. First times aren’t always gentle... but sometimes, that’s what makes them unforgettable.
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All Dean Winchester knows is repression. At no time in his life has he ever felt safe to explore his attraction to other men. He has all but convinced himself that it doesn't exist--that heterosexuality is the only option. But try to deny it as he might, Castiel's presence in the bunker is a mounting reminder that he will never be the man his father wanted him to be. He doesn't know how much longer he can keep the charade...or even if he wants to anymore.
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Sam built a new life at Stanford, new friends, a girlfriend, a future. But Dean never really left him, not from his memory, not from the shadows. When they finally come face to face again, what’s unspoken between them refuses to stay buried.
Series
- Part 3 of Wincest Stories
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Dean makes a promise to not let Cas die a virgin. After his plan at the brothel fails he decides to put his plan B into reality, whick ends in him taking Castiel's virginity in the impala. Kind of missing scene from season 5 episode 3. Or how it could become a canon.
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Benny and Castiel learn that their son Dean and daughter Emmy are much closer than the average siblings. And these kids like to play games. Always protective of his young sister, teenage Dean is eager to play Prince to her Princess, even more so when their dads catch them and join the fun.
Heed the tags, there's a whole smorgasbord of deceased pigeons in here.
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After the poor psychic girl's case (Magda, her name was Magda), Sam's premonitions are back. Dean needs to get to the bottom of it, naturally. And if a few more things come to light in the meantime, they'll deal with everything the way it deserves. Alternate season 12 with a soulmate twist.
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In Heaven, Dean Winchester and Castiel were supposed to finally find peace — but something unsettles them. There is silence where there should be relief, and Jack realizes: not everyone rests as they should. In an attempt to fix it, he tries to bring them back to Earth, to 2025. But something goes wrong. The spell shatters, and the two wake up in 2002.
There, Dean is twenty-three and drifting aimlessly through Palo Alto, watching his brother from a distance. As he observes Sam’s freedom, he feels the urge to try something like it — even if just for one night. He ends up getting sucked off by some guy in the Impala. He just didn’t expect to be seen.
Castiel, a socially awkward barista with scared blue eyes, witnesses the moment. Worse: he’s the acquaintance Dean had promised to rent a spare room in his apartment to. Now, the two are stuck living together, carrying secrets they don’t even know they have — while Jack, somewhere between Heaven and Earth, tries to find a way to fix everything.
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After finally communicating, single dads and neighbours Cas and Dean are finally in a committed relationship. Now the pair are beginning to explore each other's bodies and their burgeoning sexual relationship.
Told in a series of loosely connected oneshots focused on exploring Cas and Dean as they explore each other and their interests, each chapter will be focused on a different sex act or kink.
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Cas’ roommate, Dean, finds himself questioning his sexuality after various incidents involving him and Cas making out. To help him figure things out, Cas suggests they spend the summer at his family’s estate with his siblings, Anna and Michael, who won’t say no to helping Dean out in crisis. Cas’ motif here is obviously of selfish reasons, hoping that Dean figures out what he’s looking for is actually him. The only question is, will Cas be ready once Dean gives him the chance?
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Getting stood up by his best friend wasn’t exactly on Dean’s agenda tonight but here he is.
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The one where Cas saw an opportunity and grabbed it by the balls (literally).
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Castiel runs away from the religious cult in which he was raised. He ends up in a small town in central Arkansas, broke, alone, and hurting. When he meets Dean, however, things seem to be looking up.
Dean wishes he could run away from his current life...well, mostly, he wants to run away from his father. He hires the new-to-town Jimmy to work in his family's diner. The longer they spend time together, the more profound their bond grows.
Can the men overcome their pasts and presents with help from each other?
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Dean was drunk, that's what got him into this whole mess. No, that's a lie, he was lonely.
His brother left, his father shortly after, and he needed somebody, so he followed Sam to Stanford from a distance. Just to make sure the kid was ok, of course. On the south side of the university, Dean found an abandoned courtyard that he could just relax in, close enough to keep an eye on his dorky little brother, but somewhere where Sam wouldn't see him. But what really caught his eye about the courtyard was the statue, a beautiful angel with messy hair and eyes turning down at the corner, and Dean thought that if there was no one else around to talk to, then he might as well talk to this statue.
He didn't know the statue was watching him back.
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Or: Dean accidentally does something emotionally healthy and falls in love with an angel along the way
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It was supposed to be a one time thing, Castiel was content to know that he got to see his crush's dick and then he'd never see Dean again, but that first time led to so much more.