1 - 20 of 132 Bookmarked Items in Businessperson Dean Winchester
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After 15 years, a wedding in Vegas 12 years ago, and half a dozen impulsive decisions (including a matching tattoo they still see daily), Dean and Castiel are getting a divorce.
It's been six months since they've separated, and Dean is still in denial, back in his childhood bedroom at Bobby and Ellen's. On the other side of town, Cas is playing the dangerous games of how-many-shifts-in-the-ED-can-I-pick-up-before-collapsing and will-my-liver-survive-to-see-another-day.
Then Dean gets called in the middle of the night by Sioux Falls General Hospital, telling him his husband’s life is hanging by a thread after getting hit by a car on his way back home.
A coma, serious injuries and several surgeries later, Cas is back home with mandatory presence required to help him with reeducation and monitoring his progress. And against all odds, Dean is the one staying around to help.
Dean and Cas’ respective worlds get thrown for another ride, shifting perspectives again.
What if things between them were salvageable? What if everything wasn’t the way they thought it was in the first place? Is it worth trying to glue the pieces back together?
An exercise in healing and second chances.
- Language:
- English
- Words:
- 81,674
- Chapters:
- 9/9
- Collections:
- 5
- Comments:
- 708
- Kudos:
- 1,817
- Bookmarks:
- 589
- Hits:
- 37,336
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Castiel always notices the same guy in designer suits come into the Walmart where he works as a cashier, but he only comes in after midnight. Dean leaves his phone behind one night, Castiel sees the nude pictures he has because he is one nosy boy. That's where it begins.
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Castiel’s job is hard. Not only is he running a big corporation, but now he has to find a thief in their midst. So, to unwind, he turns to his old way of relaxation, a good old-fashioned scene. Little does he know that the Dom he met online is actually his newest employee.
Dean Smith is a giver. He just likes taking care of people, helping in any way he can. So when he enters the Safe and Bound house to find that his new sub is no other than his new boss, he does everything in his power to get the man to relax.
Together, they fight corporate greed and build something…profound.
- Language:
- English
- Words:
- 17,683
- Chapters:
- 5/5
- Collections:
- 1
- Comments:
- 84
- Kudos:
- 104
- Bookmarks:
- 25
- Hits:
- 1,225
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Stars and Broken Gravel - A Year of Pack WA-D.Winchester-003274b by WeirdLittleHeart
Fandoms: Supernatural (TV 2005)
01 Oct 2025
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A modern Alpha/Beta/Omega story about a year in the life of a Pack. Specifically, a year in the life of Washington State Pack WA-D.Winchester-003274b. It is centered around the love story of the Pack leader, Omega Dean Winchester, meeting his True Mate, Alpha Castiel Novak. Throughout the year, Pack members work, play, interact with each other, and interact with the world. They experience the inevitable ups and downs that a year of interacting with the world can bring. Relationships are forged and grown. Past traumas and family dramas surface. Moves are made. Crimes are solved.
As Dean and Castiel’s relationship develops, they deal with everything that happens to or around them by leaning on each other and taking comfort in a strong, supportive Pack built on love.
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Castiel doesn’t have a lot of luck when it comes to romance. He downloads Tinder on a whim and soon finds out it’s not any easier in the virtual world. He’s about to give up completely when a miracle happens: someone keeps talking to him even after Cas explicitly says he doesn’t want to date. As days go by and Cas and the man continue to chat, Cas begins to question his own rules.
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Dean’s life is simple: work, gym, weekend, rinse, repeat. He’s not really an expert, but he doesn’t have any qualms about chatting people up as he works out. At least not until he tries to offer well-meant advice to a blue-eyed hottie in shorts and gets shot down – turns out the guy is a real jerk. Unfortunately, that’s only the beginning of their new spiteful relationship.
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What Cas and Dean don’t realise is that they have two things in common: they both go to the same local gym and they both have a very good friend on Tinder.- Language:
- English
- Words:
- 17,598
- Chapters:
- 5/5
- Collections:
- 2
- Comments:
- 112
- Kudos:
- 959
- Bookmarks:
- 174
- Hits:
- 8,204
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After telling his family he’s gay, Castiel winds up homeless. With the help of his best friend, Cas finds himself a home and a new family. He also finds himself in love with his best friend. A love that endures no matter the circumstances of their lives, even in the wake of Dean’s rejection.
Despite knowing how Cas feels, Dean clings to his best friend through the years. In high school and college. As roommates. Through Cas becoming a firefighter and his own journey to become a business owner. With shared time and space, Dean begins to see Cas in a new light. His attraction grows, along with his feelings.
Letting those feelings spill out one night, Dean changes the trajectory of their lives. As their relationship grows, they are confronted by Cas’s past and must relive a painful and damaging event in Dean’s life. But it is the life-changing fire, which is their greatest challenge, making them face their deepest fears and test the strength of their love.
- Language:
- English
- Words:
- 82,919
- Chapters:
- 13/13
- Collections:
- 2
- Comments:
- 68
- Kudos:
- 357
- Bookmarks:
- 170
- Hits:
- 10,087
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Bookmark Notes:
Dean n cas. Cas becomes a firefighter. He got kicked out when he was a kid. Dean doesn't know he's in love with cas for a long long time.
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When Dean’s business partner Rhonda asks him to do the modeling for their company’s marketing campaign due to the original model falling ill, Dean begrudgingly agrees. He has never done underwear modeling and hasn’t done any modeling for at least 15 years, but his face won’t be shown in the photos, and it will only be one day with the world-famous fashion photographer Castiel Novak.
Only Cas Novak turns out to be incredibly attractive. Dean just needs to keep reminding himself that he’s a professional and can act like it, even when he’s only wearing a pair of panties in front of the hottest guy he has met for a while.
- Language:
- English
- Words:
- 6,856
- Chapters:
- 1/1
- Collections:
- 1
- Comments:
- 19
- Kudos:
- 329
- Bookmarks:
- 50
- Hits:
- 2,894
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Dean Winchester, CEO, frequents the diner on the corner of Main and South for lots of reasons: pie, the jukebox that plays 80s music, and Castiel, the sweet, handsome waiter who always has time for Dean. When he sees Castiel unexpectedly on Christmas Day, he learns more about the quiet man... and receives two precious gifts that money could never buy.
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When restoring his beloved car, a gorgeous lady named Baby that he inherited from a friend, Castiel Novak finds a box in her trunk—a time capsule, put there by two young boys many years ago. Moved by its contents, Castiel brings the box back to its owners, Dean and Sammy Winchester. There’s an instant spark between Castiel and Dean—first of attraction, then of anger. They both love Baby, and both of them want her. They take their conflict to the road, each convinced of their rightness and determined to do what it takes for what they want the most. For love.
As they battle for Baby, two men discover the meaning of history, of home, and of finding what you’re truly looking for.
- Language:
- English
- Words:
- 30,781
- Chapters:
- 13/13
- Collections:
- 1
- Comments:
- 843
- Kudos:
- 774
- Bookmarks:
- 199
- Hits:
- 8,196
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Wealthy, handsome, and very single Dean Winchester wanted to be CEO of his family's wine business. But in order to be considered for the position, he signed a contract with a clause that he had to be married wholeheartedly for at least a year by the eighty-fifth anniversary of the company, which was when his grandfather would name the next CEO. Guess who put it off until the last minute? But hey, he already arranged to marry one of his employees, no problem...well, no problem until she didn't show up, anyway.
The random employee he dragged along to witness the wedding had a solution.
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Thrift shops are not for the poor, they are for the very poor and desperate. Who would want pre-owned clothes that smell like someone else, that no matter how many times you wash them, they never lose the original owner's scent? Someone who doesn’t have any other options, someone like Castiel.
However, one day, in the lead-up to Christmas, he catches the scent of an alpha (who smells exactly like apple pie) on a $3 second-hand trench coat, that makes him do stupid things.
In a world where alphas are given all the advantages of life, there aren’t many options for omegas. It is either find an alpha to support you or live a life well below the poverty line. Castiel had chosen the second option. It seemed noble at first, but after a decade on his own, life continues to wear him down.
All that changes when he meets the jacket's original owner (and promptly throws up on him), causing him to rethink his decision.
- Language:
- English
- Words:
- 19,955
- Chapters:
- 3/3
- Collections:
- 2
- Comments:
- 163
- Kudos:
- 948
- Bookmarks:
- 184
- Hits:
- 7,823
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Their Christmas Miracle by blackhorsedances for Avonlady
Fandoms: Supernatural (TV 2005)
05 Jan 2025
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When Dean Winchester got out of the Army and went to work for Bobby Singer as a mechanic/tow truck driver, he never thought he'd meet the love of his life. Castiel Novak is gorgeous, smart, funny, and he *bakes* pies and bread. They've got a farm with chickens and ducks, and because he works from home, Cas wants a cow.
Then disaster, in the form of Cas' employers, strikes. Cas has to go back to the office, or lose his job. Dean scrambles to help, but has he helped *too much*?
When Cas disappears, Dean is afraid that he's finally driven away the love of his life. It's gonna take a true Christmas Miracle to save this situation. Fortunately, a Miracle may just be at hand.
Series
- Part 1 of Simple Gifts
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Dean receives a picture of his boyfriend Castiel in his favourite pair of panties when he's at work. Since his boy is being bad, Dean has to teach him a lesson, right?
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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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As the youngest son to the king of a small European country, Castiel had rarely felt free to be himself. After a breakup and his ex-boyfriend outing him to the public, Cas flees to America to seek some peace and quiet from the press. In his new town, he manages to escape from his bodyguards for an afternoon and meets an attractive stranger. The man, Dean, gives him a taste of what it could be like to date as just another regular person.
And that’s just the first of the strange turns his life is about to take.
- Language:
- English
- Words:
- 20,226
- Chapters:
- 5/5
- Collections:
- 1
- Comments:
- 15
- Kudos:
- 142
- Bookmarks:
- 30
- Hits:
- 1,948
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Dean Winchester lived a contented life in Erzla Cove, Rhode Island, running the family store. He had good friends, the best little brother, and a niece that he adored. The only thing missing was someone to share it with.
Castiel Novak had been through much over the years: the loss of his father, the incarceration of his brother, and subsequent guardianship of his nephew Jack, to name a few. Another loss that had affected him profoundly was that of his childhood best friend, Dean Winchester: The one who got away.
But now Castiel was hoping to change that.
Spending summers with his father in Erzla Cove as a teenager had been the only time Castiel felt truly at home, and he wanted that for Jack. Taking his late father's advice, Castiel packed up their life and moved to the small coastal town that held much of his heart, hoping to reconnect with old friends and have a second chance at love.- Language:
- English
- Words:
- 21,505
- Chapters:
- 9/9
- Collections:
- 1
- Comments:
- 95
- Kudos:
- 280
- Bookmarks:
- 71
- Hits:
- 3,270
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A Dean/Cas 1950s AU. Dean reads an elopement proposal in the town's local newspaper, written by some old soul in love with their best friend. He's mid-way through expressing to his brother how beautiful he finds it when Dean realises the proposal is for him.
- Language:
- English
- Words:
- 18,987
- Chapters:
- 1/1
- Collections:
- 5
- Comments:
- 255
- Kudos:
- 3,565
- Bookmarks:
- 701
- Hits:
- 39,134
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Dean Smith loves his fancy skyline office and his prestigeous job at Sandover but there's one thing he craves more than power and money. It's a certain tech support guy named Sam. And he has just called the young man into his office to offer him a deal that he can't refuse. Literally.
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While staying at a hotel for a work conference, Dean opens what he thinks is the closet door but turns out to be an adjoining room that has been accidentally left unlocked. He is greeted by the most attractive man he has ever seen in nothing but a towel. The man, Cas, seems incredibly amused, while Dean has zero chill about the situation. After the embarrassing encounter, Dean discovers Cas is the moderator of a panel he is speaking on.
- Language:
- English
- Words:
- 23,400
- Chapters:
- 11/11
- Collections:
- 2
- Comments:
- 162
- Kudos:
- 518
- Bookmarks:
- 97
- Hits:
- 7,003
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Bookmark Notes:
Soft, so very soft boys. No misunderstandings, no angst
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Dean has an important interview and his day starts out at rock bottom and only gets worse. But then it gets better.
This is probably more of a 'verse, fyi..