Wincest

VICE by awabubbles (PDF)(WIP) ~ Dean Winchester is an undercover cop in the sex trafficking unit of the Chicago PD. He suffers from the loss of his former position in narcotics, a bullet injury that causes him to limp, and the sudden divorce of his wife Lisa who'se kicked him out of the house and kept their son, Ben. Dean meets Sam during one of his stings, an underage prostitute who loudly proclaims his sexuality and a penchant for older men. They become slowly fascinated with each other, developing a strange and twisted relationship, while Dean struggles to regain what he's lost, and Sam looks for any way out of his life on the street.

Fathers and Heroes by BenLMoore (PDF) ~ I considered putting this in 'Epic' because it is but it's more wincest so here we go. Sam Winchester, an unassuming accountant with a deranged boyfriend meets a green-eyed high school quarterback at a party for his estranged father and soon discovers that the kid doesn’t know the words "appropriate" or "legal.” For better or worse, the bond between them is irresistible. Dean is streetwise and cocky, and there's no way this ends well for Sam.

Going Down by HazelDomain (wincest) (PDF) ~ Dean Smith is a high-level sub. He tries not to spread the news around, but it gets pretty hard sometimes.... like around the super-hot dom Dean keeps meeting in the elevator.

Run So Far (That I Am Standing Still) by DickBaggins (PDF) ~ (wincestiel) Sam Winchester's been in love with his big brother Dean for as long as he can remember, and he's never told anyone but Dr. Cas Novak. From their first session together, Cas finds himself fully entrenched in Sam's sad story with a fervor that's not entirely professional. Under his overly intimate and fairly unorthodox methods, even Dean notices the change in his usually gloomy brother and decides maybe therapy's not so bad.

Retail Therapy by All_the_damned_vampires (part1 - part 2 - part 3) ~ RPF (Jensen/Jared paring) ~ This story could go under Dragons but honestly it's not that bad. Starting from a masquerade prompt and spinning out of control in both length and content, this trilogy tells the story of Jared, just your average joe, kidnapped by enamored sociopath Jensen. This story is so good I'm going to include a real rec from my friend AzrielRose :

"It’s 2:45 am, my alarm’s gonna go off in 3 hours, and I’m still reading that fic I rec’d, Retail Therapy because IT IS SO FUCKING GOOD!!! It has kidnapping and human trafficking (you’re like of course you’re reading that), so how is it sooooooo different? There are all these characters and they are bad, bad people but so fucking likable, down to the worst villain! And they’re all terrible in unique ways, how the fuck is this author doing this???? And then there’s Jared at the center, this naturally submissive tragic cinnamon roll who somehow manages to be sassy, who manages to call them on their uniquely fucked up shit (not always, mind you, but he keeps coming around), you expect him to doormat his way through but he gets his licks, and then there’s the way people get attached to him because of that natural submissiveness. The sex scenes are so hot, Jensen is the rapiest motherfucker, but he’s suppressing it, he wants Jared as his submissive little slave first, and then there’s all this extremely tense hitman/mafia drama, like actual plot and things, and every person has an agenda and manipulates Jared for like 700 different reasons.

I fucking cannot. I should’ve been asleep hours ago goddamn it. This thing is a goddamn masterpiece. There’s spanking in it, too (aside from other kinds of impact play). Wanna know who fucking does it? Jeffrey Dean Goddamn Morgan, but he prefers to be called DADDY. "

Emancipation by wayardseraph (wincest) (PDF) ~ The law doesn't look kindly on slaves who kill their masters, even abusive assholes like Dean's. After putting up with the abuse for years, Dean snapped. No regrets. Now he's in prison awaiting trial and fighting off guys after his pretty ass.

It Was On Sale HazelDomain (wincest) (PDF) ~ Dean's been hunting solo ever since his dad died, and he knows damn well he's running on borrowed time. The simple solution was to buy a slave, someone who could watch his back and help with the heavy lifting. The man he finds is young, healthy, obedient, and inexplicably cheap. And that's just the beginning. Dean figured he'd deal with the catch when he found it.

Lot 607 by Jay Tryfanstone (tryfanstone) (wincest) (PDF) (Part 2) ~ want one of the boys being sold at a sex slave auction and the other to be a wealthy, no-nonsense buyer. No one is allowed to test drive the slave all the way but the auctioneers use...instruments and display him for the buyers.

Prime by meus_venator (wincest) (PDF) (Part 2) ~ In a cruel and capricious society where slavery is the norm, first born children or Primes become masters, all younger siblings become slaves or Secs at the age of sixteen. Second born son, Sam Winchester, has evaded his fate and helped others do the same while attending college and living as a Ghost, but his luck has just run out.

Kill The Lights by silver9mm (wincest) (PDF) (MOBI) ~ With Ruby's help Sam finally rescues Dean from 'hell' but it may be too late to save him. Dean has changed in ways that Sam was not prepared for. MCD it's not pretty. But it is amazingly well written.

50 by hellhoundsprey (wincest) (WIP as of 9/15/2018) (PDF) ~ Mr. Smith and Mr. Wesson fall in love. This is a highly abusive relationship and it's so so well written. Mind the tags. Here is a coda inspired by 50: This is

My Brother's Key Keeper by NinNinNin (wincest) (WIP) (PDF) ~ Dean gets hit with a curse that make him hard and leaking cum constantly. Sam's brilliant solution? Put Dean in a cock and sound cage. Or. The one when Sam fulfill his dirtiest fantasies about his brother.

Move Over by Vera (Vera_DragonMuse) (PDF) ~ so this is not exactly wincest but I wasn't sure where else to put it. It's a smutty one shot with Castiel/Gabriel/Dean/Sam. Sex in a foursome is surprisingly complicated, but Dean manages.

Save a Horse, Ride a Hunter by CluckU, Mumble_Bee (PDF) ~ The enormous guy leans in to say, “How’s one hundred for your boy?” nodding meaningfully in Dean’s direction. A hundred dollars? For a blowjob? Sam’s too impressed to be angry, or offended, or disgusted. In fact, he’s downright intrigued. Could he…? Fuck. Of course he could. Dean wouldn’t stand a chance. And it’s not like they don’t always need money; motel rooms and bar tabs and silver bullets aren’t exactly free. Sam flashes a soulless smile (hah) and says, “He’s a biter.”

Pretty Now by natashawitch (PDF) Summary: Driven to sell himself once more on the streets of Chicago, Dean finds a client who keeps him. My Comment: This was a really good story. I don't normally read dean/Sam but I was looking for older dark fic and came across this and thought I'd give it a try. I thought it was ironic that Sam was much better off with his foster family and while, yes, it was child sexual slavery, Dean was for all intense and purposes better off with his kidnapper. If John had not been such a huge abusive jackass Dean probably could have recovered more quickly. I also loved that he had a trust set up that he told Sam about and Sam was able to use that to get them away from John. You really did a great job making Sam the hero. Author Response: Thank you so much for leaving your comments on my story which is from quite a while ago now. I'm very pleased you enjoyed it so much and as a bone fide SamGirl I'm very happy you enjoyed young hero Sam in my dark fic. My Response: Honestly, it's difficult to find fic where Sam is portrayed in a positive light. Sadly I understand that my issue stems more from my wanting to read destiel rather than wincest. But I love Sam and I'd love to find more stories where he's a strong supportive brother. I don't even mind if he is in a semi-romantic relationship with Dean (because who wouldn't want to hit that?) but even those seem to have Sam as a darker character. I have found some really good wincestiel; but I find that I really respond very strongly to Cas/dean stories the most. But yes I am reading Tread Softly now and I'm savoring it. Thank you for sharing your stories. <3