1 - 20 of 278 Bookmarks by pointlessTheo
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Dean Winchester was going to die.
When he didn't present at sixteen as expected, Dean was illegally recorded as an Alpha. He has known for a long time that he wasn't one, but to stay and protect his young brothers, Dean accepted the lie and hid his true nature until it couldn't be hidden anymore and his first heat came.
None of it mattered after Dean was framed and sent to prison.
An Alpha prison.
Shot full of suppressants that would give him at most a month until his true nature was revealed, Dean was thrown into a dangerous world where if even one Alpha discovered the truth, Dean's life would be forfeit.
Fate has a funny way of working though, in even the filthiest, most dangerous of places.
- Language:
- English
- Words:
- 92,023
- Chapters:
- 32/32
- Comments:
- 1,656
- Kudos:
- 1,545
- Bookmarks:
- 263
- Hits:
- 39,349
Bookmarked by pointlessTheo
25 May 2026
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Summary
Castiel liked quiet. He liked predictable. You could probably call him boring and not be wrong, but Cas didn't care. He was happy that way.
Until one day, his street got torn up as a construction crew moved in, loud and persistent and, as far as Cas was concerned, specifically sent to ruin his life. Especially one construction worker who seemed to take that job personally.
Dean had to be boring. He had to be quiet, predictable, and boring. Because those were the pillars of stability.
With a bipolar diagnosis and the baggage of everything he blew up on the road to getting it, he knew better than to take the little things for granted.Then, a regular job on a regular street brought C. Novak into his life. C. Novak, who was rude, infuriating, and, unfortunately, smoking hot.
Cas and Dean both had to learn to make room for things that mattered, even if they weren't little joys. Even if they could be disruptive. And annoying. And they had to learn to navigate the room that was made for them.
Somehow, between the arguments and minor freak-outs, they both had to learn how to make space for something bigger than routine.
Series
- Part 1 of Good Days and all the rest
Bookmarked by pointlessTheo
22 May 2026
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Summary
Ten months ago, Castiel’s life changed for the worse. Now, he’s an agoraphobe with PTSD, OCD, and a few other acronyms and diagnoses to go with those. His siblings are worried that he’s wasting away without real human interaction.
As the anniversary of Castiel’s accident draws closer, his brother and sister hatch a plan that will—hopefully—bring a little spark back into Castiel’s life.
Bookmarked by pointlessTheo
12 May 2026
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Summary
Don’t panic.
Don’t beg.
Don’t give them anything to use against you.It’s been Dean’s mantra for the past five years, and somehow, against all odds, he’s managed to survive. Survived being betrayed. Survived being sold. Survived being beaten and used and thrown out like yesterday’s trash — and, miraculously, he’s managed to do it all with his spirit still intact.
But now he has a new owner. One who is powerful yet principled, careful where others were careless. A man who should be like all the rest and somehow isn’t.
Dean doesn’t know what’s more dangerous: a system he understands, or a man who refuses to follow it — but when Castiel looks at him like he might actually be worth something, Dean's not sure the answer matters anymore.
A story about survival, second chances, and what it means to be seen.
- Language:
- English
- Words:
- 48,874
- Chapters:
- 16/16
- Collections:
- 1
- Comments:
- 109
- Kudos:
- 346
- Bookmarks:
- 62
- Hits:
- 4,931
Bookmarked by pointlessTheo
12 May 2026
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When Dean suddenly catches a whiff of the best scent ever he becomes convinced he has found his Mate.
Or,
The one where Dean’s inner Omega might possibly be the biggest dumbass in history.
Bookmarked by pointlessTheo
30 Apr 2026
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Summary
Dean Winchester presented Omega, turning his entire world upside down. Now, he has a curfew, omega classes, and faces the possibility of losing his dream to go to Engineering School. He rebels against his restrictions, mourning the life he had as an un-presented 16 years old. Unfortunately, he realizes how much he had once he loses it all.
Claimed, kidnapped, bound for life to a man twenty years his senior - how can Dean keep on living?
Edit: mind the tags! It's not as graphic as some DDNE fics but it *is* graphic and it has elements of sadism.
- Language:
- English
- Words:
- 194,048
- Chapters:
- 78/78
- Comments:
- 1,452
- Kudos:
- 2,328
- Bookmarks:
- 261
- Hits:
- 95,749
Bookmarked by pointlessTheo
26 Apr 2026
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Summary
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.
- Language:
- English
- Words:
- 231,675
- Chapters:
- 48/48
- Comments:
- 3,469
- Kudos:
- 1,185
- Bookmarks:
- 218
- Hits:
- 41,622
Bookmarked by pointlessTheo
18 Apr 2026
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Right Kind of Trouble by AmberXBoone, corrupt_touch (AmberXBoone)
Fandoms: Supernatural (TV 2005)
08 Mar 2026
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Summary
Castiel Novak has been all over the world, managing pop stars and indie rock bands and 1980s hair metal comebacks. But the rockstar life has caused his personal life to fall apart and he finds himself newly divorced without anyone waiting for him at home. So, one Saturday night, he finally takes up the Management Company's invitation to see one of their biggest acts, Angel Sigils, fronted by Dean Winchester, often described as a reckless bad boy by more than one music magazine.
And Dean is mesmerizing and everything that Castiel needs for a night. Until he's woken up in Dean's bed by a call naming him Angel Sigils' new manager.
Bookmarked by pointlessTheo
09 Mar 2026
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Summary
Dean has a good life. Sure, his daughter’s dead, and he has a permanent limp because of a stupid drunken decision a year and a half after Emma’s death. But now he's a world-famous author, fifteen years sober, and has wonderful friends and family by his side. Though… his house seems a bit too empty. There is a reason he spends most of his time at Sam and Eileen’s place.
But, after the CEO of the biggest tech company in the world comes to one of Dean’s book signings for his daughter, Dean can't stop thinking of the CEO's bright blue eyes. Except that Dean isn’t looking for a relationship. Yes, he’s comfortably bisexual, but that’s beside the point. Dean has had too many failed relationships and has too much baggage. So, why does Castiel keep emailing him? And why does Dean keep emailing him back?
Series
- Part 1 of Written Between Us
- Language:
- English
- Words:
- 178,168
- Chapters:
- 43/43
- Comments:
- 296
- Kudos:
- 459
- Bookmarks:
- 115
- Hits:
- 14,086
Bookmarked by pointlessTheo
27 Nov 2025
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Summary
Castiel spent decades living in shame about his omega status. Now divorced and nearly fifty, he’s finally living openly when one reckless night with a younger alpha, Dean, leaves him staring at a pregnancy test.
Castiel must confront the reality of what that night meant, and what comes next.
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Or: Old!Cas gets pregnant after a one night stand with Young!Dean.- Language:
- English
- Words:
- 59,004
- Chapters:
- 10/10
- Comments:
- 611
- Kudos:
- 1,311
- Bookmarks:
- 257
- Hits:
- 23,856
Bookmarked by pointlessTheo
24 Nov 2025
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Summary
The mildest of scandals could destroy the reputation of an omega in a very short time. Dean learns it personally when rumors about him and his friend Benny start circulating in his community. The best option to correct the situation is to arrange a marriage for Dean as soon as possible. Castiel has recently inherited the title and fortune as Lord Novak after the death of his father. With his new role in society, his mother strongly believes Castiel needs a mate.
Having both Dean and Castiel agree to the union and arranging the mating is the easy part. They have mutual attraction and their values seem to be well-matched. However, it turns out navigating a relationship is difficult when neither party is sure whether the other has been forced into it.
Lack of communication, fear of rejection, and jealousy surely aren't going to make the situation any easier.
- Language:
- English
- Words:
- 30,260
- Chapters:
- 6/6
- Collections:
- 1
- Comments:
- 41
- Kudos:
- 304
- Bookmarks:
- 77
- Hits:
- 4,814
Bookmarked by pointlessTheo
19 Nov 2025
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Summary
Dean Winchester is nothing special. He’s the kind of guy who spends his days and nights working multiple shitty jobs in Nowhere, Kansas. For him, the supernatural isn’t extraordinary either — it's just another part of everyday existence, like taxes and Madge Carrigan’s homophobia. All except angels, that is — they're rare and powerful and dangerous as fuck.
Which is why it's a monumental inconvenience when a devastatingly handsome and mysterious angel walks into the bar where Dean works. Suddenly, Dean's life is a bizarre interspecies romance novel — all stolen glances, intense conversations, casual murder, and a dizzying, fast-track fall into love. In fact, Castiel is everything Dean never knew he wanted, right down to the scary, otherworldly perfection.
All is not what it seems, however, as when Dean finally gets a peek behind the heavenly curtain, he discovers Cas has a secret that's not merely a lie, but a stunning, earth-shaking betrayal that threatens to destroy everything Dean just started to believe in.
- Language:
- English
- Words:
- 72,423
- Chapters:
- 13/13
- Comments:
- 733
- Kudos:
- 714
- Bookmarks:
- 207
- Hits:
- 16,084
Bookmarked by pointlessTheo
19 Nov 2025
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Summary
John Winchester had finally done it: he found Azazel, the man most responsible for killing his wife and burning down his home.
He killed him. He burned down the warehouse they were in to bury the evidence.
Unfortunately, the warehouse belonged to the Houston branch of the Russian Mafia.
After dealing with John Winchester, Castiel's men find his omega son hiding in the bathroom. They bring Dean with them and, when Castiel joins them by chance, invite him to play Fuck, Marry, Kill to decide his fate.
Castiel choses marry.
- Language:
- English
- Words:
- 52,369
- Chapters:
- 30/30
- Collections:
- 1
- Comments:
- 862
- Kudos:
- 1,139
- Bookmarks:
- 231
- Hits:
- 23,268
Bookmarked by pointlessTheo
16 Nov 2025
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Summary
Dean Winchester and Castiel Novak used to be inseparable. Not just high school best friends, but the kind of soul-deep, ride-or-die connection fueled through their mutual love for music that felt like it could outlast anything. Near the end of their senior year, though, something happened that irrevocably broke them apart.
Ten years later, Dean owns a cozy little record store in downtown Lawrence, Kansas, has a dog he'd die for, and hasn't seen or heard from Cas since graduation. He’s made peace with the silence. Or so he thinks, until a familiar figure moves into the long-vacant house across the street.
Castiel Novak has spent the last ten years flying standby and building a life he can live with. It's not glamorous, but it's stable: quiet nights, early flights, and a cat who doesn’t ask too many questions. When he moves back to his hometown to be closer to family, he’s not expecting the past to be waiting for him at the end of the driveway.
Especially not in the shape of Dean Winchester.
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Titled after lyrics from "Suzie Chapstick" by Green Day (x)
- Language:
- English
- Words:
- 50,890
- Chapters:
- 9/9
- Collections:
- 2
- Comments:
- 180
- Kudos:
- 657
- Bookmarks:
- 104
- Hits:
- 6,039
Bookmarked by pointlessTheo
23 Oct 2025
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Summary
After breaking up with his long-term boyfriend—and the Dominant who once held every part of him—Dean is restless, raw, and lonelier than he’ll admit. Meg steps in with a solution: her best friend Castiel, a quiet man she swears is exactly Dean’s type. Dean doesn’t do blind dates, but Meg is relentless, and Cas seems harmless enough in theory.
In practice? Not even close. Castiel radiates command, the kind of presence that makes Dean’s pulse stumble. His voice leaves no room for argument, his gaze cuts straight through Dean’s defenses, and his restraint carries the promise of punishment waiting just beneath the surface. Dean thought he was finished with Doms. Castiel intends to remind him exactly what it feels like to kneel.- Language:
- English
- Words:
- 79,035
- Chapters:
- 10/10
- Comments:
- 238
- Kudos:
- 560
- Bookmarks:
- 122
- Hits:
- 14,273
Bookmarked by pointlessTheo
16 Oct 2025
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Summary
Dean Winchester has spent decades hunting the vampires who destroyed his family. Armed with half-memories and a perfect plan, he sets his sights on a charming bloodsucker in a quiet New York town. One drink, one date, and Castiel Novak will be dead. That’s the plan.
But Castiel isn’t what he expected. Stoic, disciplined, and impossibly old, Castiel hasn’t tasted human blood in centuries—until Dean. One bite shatters the past. Memory magic falters, and suddenly, Castiel finds himself drawn into a mystery that blurs the line between vengeance and something dangerously close to desire.
When an enemy from the past threatens Dean’s life, long-buried truths begin to surface. If they want to survive, Dean and Castiel will have to face the shadows they thought they left behind—and decide if love is worth the risk of becoming the very thing they fear.
Bookmarked by pointlessTheo
09 Oct 2025
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Summary
Castiel Novak’s dream of the perfect family and the perfect life went to shit the day his wife was killed in an automobile accident. He is left to raise his 8 year old daughter, Claire, on his own. He struggles with balancing being a father to his daughter and running the company (military weaponry) he started with his wife, Amelia, on his own. When he starts receiving threats on his life from his competition, he hires a bodyguard to protect Claire. He just hadn’t planned on falling in love in the process.
Dean Winchester didn’t know where his life was headed when he left the Army. He struggles with finding employment when the only job experience he has is being Special Ops and having too many kills to count. When his surrogate father, Bobby, tells him that the CEO of the largest supplier of military weaponry is looking for a bodyguard for his 8 year old daughter, Dean figures he has nothing to lose and accepts. He just hadn’t planned on getting emotionally attached to the girl and falling in love with her father.
When Castiel is away on a business trip and Dean is shot and Claire is kidnapped, both men make it their business to get her back by any means necessary, even if they have to murder the world to do it.- Language:
- English
- Words:
- 35,857
- Chapters:
- 11/11
- Collections:
- 1
- Comments:
- 34
- Kudos:
- 109
- Bookmarks:
- 42
- Hits:
- 2,139
Bookmarked by pointlessTheo
07 Oct 2025
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Summary
Kinda How to Train Your Dragon meets Monsters University. If, you know, there was more Gay Stuff.
Welcome to Prospero College! A safe haven for Monsters to further their education!
Dean's a thoroughly reluctant undercover hunter, tasked with bringing back info or bodies, whichever comes first. Should be easy, right?
A story about our actions, our nature, and the distance between the two.
Dean knows what he is.
A Dragon.
He has a Dragon across the hall from him, possibly one of the last fucking ones in existence. And he just pissed it off so badly he doubts it’ll even look at him again.
His dad was going to kill him.
- Language:
- English
- Words:
- 203,290
- Chapters:
- 57/57
- Collections:
- 6
- Comments:
- 2,368
- Kudos:
- 982
- Bookmarks:
- 310
- Hits:
- 31,771
Bookmarked by pointlessTheo
05 Oct 2025
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Summary
He thought he had control…. He was so, so wrong.
Castiel Novak didn’t need a relationship. He had Halo, a decadent club where he quenches any raw desire he chooses. He takes pleasure and he gives it - no strings attached. So when Dean Winchester comes in asking for someone cold, emotionless and filthy…well, no man quite gives or takes pleasure the way Castiel does.
Only Dean is different. Vulnerable. And carrying some deep sadness that breaks past Castiel’s carefully constructed walls and inexplicably makes him care.
Now craving controls him. Ice giving way to red hot need.
But Dean has no idea about Castiel’s other life. That he is a father. That his secrets run deep. His two worlds are about to collide with the force of a supernova.
Once Dean knows the truth of who Castiel is, will he be able to accept all of him?
Bookmarked by pointlessTheo
02 Oct 2025
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Summary
Castiel and his husband, Crowley enlist the help of rare omega to conceive and carry a child for them. Castiel is hesitant — their relationship is already on the rocks — but unwilling to disappoint his husband yet again, he agrees to spend a weekend with the omega.
It’s just sex, right? What could go wrong?
Enter Dean.
He’s confident and charming, and everything Castiel is not.
In a lakeside cabin, away from society and outside distractions, Dean quickly breaks down Castiel’s carefully constructed walls, stirring up emotions he wasn’t prepared for.
What starts as an unconventional arrangement, soon turns into something more, forcing Castiel to choose between his heart and the life he has always know.
- Language:
- English
- Words:
- 86,994
- Chapters:
- 24/24
- Collections:
- 1
- Comments:
- 557
- Kudos:
- 530
- Bookmarks:
- 113
- Hits:
- 15,209
Bookmarked by pointlessTheo
01 Oct 2025