1 - 20 of 36 Works in Secretary Castiel (Supernatural)
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Castiel Novak, a single woman in her late twenties, discovers a job application to be the secretary of up and coming business woman, Deanna Winchester. Eager to support herself and impress her estranged family, she takes the job as the close confidant to one of the most powerful people in 2000’s Wall Street.
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Infinite Cakes Great Big Bang 2025 - You Don't Have To Be That Cute by BENKA79 - Illustrations by BENKA79, tallula03
Fandoms: Supernatural (TV 2005)
23 May 2025
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- Part 64 of Books and Fanfics Illustrations - 2020-now
- Part 37 of Supernatural Fanarts - 2013-now
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Castiel lands his dream job: he is now the secretary of the famous and successful CEO Dean Winchester. If only his boss weren't the devil incarnate, Castiel might be able to enjoy his good fortune. But the scales tip in his favor when he discovers that the cold and tyrannical CEO Winchester is the impromptu sexy exotic dancer at a club. How will this change his relationship with his boss at work and in everyday life? Will Castiel be able to resist his boss's charms?
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Always be a first rate version of yourself and not a second rate version of someone else. by CaremKefo
Fandoms: Supernatural
08 Dec 2022
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When Dean finds Castiel standing on the wrong side of the bridge railing in the pouring rain, he takes him home. He finds himself caring for the man as a replacement for his younger brother, but when Cas gradually reveals what led him to contemplate suicide Dean realises that they can't ignore his past, and takes steps to help Cas heal and move on. As Dean becomes more aware of how our pasts can affect us, and as his old trauma resurfaces, he – albeit reluctantly - starts to open up to Cas about his own past. What starts out as a friendship born of loneliness and desperation grows into something more as they are drawn closer to each other over time, and slowly help each other to mend.
(The tags probably make this sound more depressing than it's going to be.)
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Castiel is a confident, efficient secretary for the Human Resources department of a corporation where Sam Winchester works in the legal department. Castiel likes to make everyone in his office feel welcome and comfortable, and to ease their day where he can. Sam thinks they have a connection, and he hopes he can use it as a way of getting closer.
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- Part 11 of Kidnap an Angel
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A team of hunters that had taken a case a couple of towns over had just begun their way back to Lebanon when their car broke down near the highway.
Dean had taken the truck to go help them out.
Jack was at a school event.
That left Castiel and Emma alone at home.
Well exept for the dog.
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- Part 2 of Post-Series by Juli
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Taking place in the It’s a Terrible Life universe (kinda), Castiel is Dean’s executive assistant who cares a little too much. It only gets worse after they share a passionate evening after hours in the office, which has Dean spiralling and Cas trying to make sure his boss doesn’t drop dead in the office. Once he figures out Dean has an eating disorder, Castiel tries his best to help him through.
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"I dare you to give Winchester a lap-dance. Bet you'll chicken out in a second flat."
"And if I don't?" Castiel asked, as he stood up, although out of balance, not that anybody cared.
"500$. And I'll clear your raise." Mick snapped a five-hundred-dollar bill down on the table between them.
And that's how it started.
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Dean once again is jealous. The thing is, he is not supposed to.
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Castiel Novak is the secretary to Mayor Dean Winchester. He also has a hopeless crush on him but is certain the other man will never give him the time of day. His best friend Meg wants to help him get the mayor’s attention. Her methods are a bit unorthodox, but they work.
Dean Winchester is a lot of things. Some of those things he can share with the public – passionate, supportive, resilient. Other things he keeps to himself – polyamorous, bisexual, dominant. Then his secretary ends up in the paper with someone else, and Dean’s possessive side rears its ugly head.
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Castiel starts a job as the personal assistant to CEO Dean Winchester.
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Castiel is Dean Smith's new secretary and they hate each other but Castiel is his boss' nephew so he has to suck it up. Until now.
A.K.A where Castiel is cheeky asf and Dean hates him with everything he has.
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Just a collection of bottom Dean. One-Shots, each chapter is its own individual story. All Destiel, may include other characters with them.
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Destiel Office AU by Destiel_is_the_bestiel for Maybelene
Fandoms: Supernatural, destiel - Fandom
06 Nov 2018
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The prompt is: CEO Dean wanted his secretaryCastiel's attention, but no matter what he did, the guy didn't show any interest in him at all. The thing is Cas did notice what Dean wanted from him, he just tried to play hard to get in order to make sure that Dean really wanted him for a good, solid relationship and not just for one night stands. In short, Cas made Dean feel jealous by talking, touching the other guys at work but him for a whole month xD. I hope a smut scene can be included in this too if you're up for it and I really love bottomCas :P.
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- Part 6 of Destiel One shots
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A collection of Destiel one shots for Kinktober.
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Castiel is Dean Smith's secretary but he wants to be so much more.
Day 19 Prompt: It's a terrible life verse (ep 4x17)
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- Part 19 of Promptober 2018 Drabbles
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Dean and Castiel have been in love for three years. It's obvious to everyone - even themselves. But what if getting together ruins their friendship? What if they're too different? What if everything changes? There's only one way to find out, but neither one of them is brave enough to make the first move.
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- Part 32 of Destiel One-Shots
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Dean Winchester wakes up from a car accident. Besides a concussion, he feels fine. He quickly notices that who he is now, was not who he was before the accident. Instead of cold and uncaring, he is happy, and caring towards others, especially his secretary, Castiel Novak. However, Castiel is battling demons of his own, and may just need Dean to help him overcome this battle.
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Dean and Castiel meet by chance when Dean has to take Sam's dog to the vet.
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Gabriel is the head of a temp agency… sort of. After nearly a year of work, the last secretary for the law firm Winchester and Sons decided to run off with someone from the mail rooms. Normally that wouldn't be a problem, but Dean, the man requiring said secretary, has very specific requirements for the job. Gabriel really wants Dean to grow up and stop bothering him. Because he has better things to do. Like play video games. And Castiel just wants a relaxing summer away from his students, and people in general.