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I asked for a little bit of clarification, because this is a fairly broad topic, and I can talk about Team Free Will in canon or their individual relationships and how it works, or Wincestiel in fic, which is a whole different beast, or my own personal beliefs about Wincestiel, within canon and fic, or I could just link to the Wincestiel big bang I just posted and call it a day. But I think I will try to address some of the other things first, because I have a lot to say about Wincestiel and it's confusing and convoluted sometimes.
Canon - Team Free Will
For a long time, Team Free Will was a V-shaped relationship, centered on Dean. I think Sam probably wanted to be closer to Cas, but Cas was not interested in befriending the boy with the demon blood. That has always made me a little bit sad, but it was reasonable for Cas's characterization, and I never turn down Sam angst. Sam angst is my favorite.
Cas's growth as a character has been fascinating, especially as it relates to the Winchesters. Loving Dean comes naturally to him; Dean is the Righteous Man, Dean is the one that will save humanity, fulfill the angels' plan. And then, when Cas starts to doubt, Dean is the one that teaches him about rebellion and thinking for yourself and all the good (and bad) things about being human. And all of it - because of Sam. Everything Dean does is for Sam, and I think, finally, at the end of it all (by which I mean the end of S5), Cas understands and wishes, perhaps, he might have gotten to know Sam a little better.
The next few seasons wander, a bit. Cas deceiving the Winchesters really puts a wrench in things relationship-wise. The look on Dean's face when he finds out Cas betrayed them, oh man. OUCH. Cas shifts Sam's crazy onto himself, still unable to actually get to know Sam any better. And he does it for Dean, again, because it's Dean's disappointment that gets to him, not Sam's plight, though I think he feels for Sam when he sees him.
So really, what I'm saying here, is that Dean is the glue that holds a lot of the SPN family together, but especially Team Free Will. Sam and Cas take a long time to figure out what they are to each other. I think Sam probably trusts Cas mostly because Dean does. He can see that Cas helps them and all that, but it's Dean's unshakeable faith that Sam trusts, not Cas himself. (And oh, how he would like a little of that for himself, yes? Yes.)
Season eight we're back to Dean and Cas, together in Purgatory, and then the Cas and Naomi storyline, and the tablets and the trials. This is a turning point for Sam and Cas, I think. When Cas sees what Sam is willing to do to save the world (or just make it a better place) - again - I think something changes in the way he views Sam, something fundamental. Which is why in season nine, we actually get to see Sam and Cas interacting, having actual conversations, hugging. Sam and Cas have forged their own relationship, and, interestingly, it was mostly absent Dean. Dean was pissed at Cas and Sam was pissed at Dean, so that left Sam and Cas to work together while Dean went off and did stupid things like hang out with Crowley and get the Mark of Cain.
They're all battered and broken now, but I think there's a balance between them. I feel like they work together, have a system of checks and balances so none of them goes too far off the rails. We'll see when we get to the back half of season ten, but they've been doing a really good job of balancing the three of them so far.
So that's canon - more a Team Free Will thing than a Wincestiel thing, because of course the three of them as a romantic relationship will never happen onscreen.
Subtext - Sam/Dean/Cas
As Destiel shippers will attest, there is a ton of canon Dean/Castiel smoldering. There's tons of looks and moments and for me personally, every time Cas beats the shit out of Dean, I drool buckets. It's the reason 8.17 is my second fave episode (right after the 200th musical ep).
And as Wincest shippers will attest, there really is a lot of Sam and Dean standing too close together, and they are way closer than normal brothers. I can do incest, but I have to work at it for myself, though I can read other peoples' takes on a breezier acceptance of it.
There are some delightful Sam/Cas moments in the later seasons – the hug where Sam has to tell Cas to hug back, the hug where Cas keeps holding on to Sam even after it's over, some of the looks like when Cas tells Dean that Sam's damaged in ways even he can't heal.
So, there are nice canon moments for all the pairs that could lead to a little something more. There are even a few that could work as subtexty for the three of them, maybe, though nothing comes to mind off the top of my head. I don't think it takes too much – obviously, actually, since one of my requirements for a 'ship is for me to believe just a small tweak in canon could lead to it. Usually this means that the pair/group has amazing chemistry which, considering the Destiel and Wincest shippers out there, I have to say, yeah, they do. Swinging those two juggernauts around and making it into a threesome? Yeah, that's pretty much my default setting.
Fanon - Wincestiel
I find that there are a lot of tropes in Wincest and Destiel that don't make their way into Wincestiel too easily. Apparently it's harder to negotiate a threesome first time than a pair.
The thing I see most is a pairing that invites the third in. I've seen this both as Destiel and Wincest, but I can't actually remember an instance of Sam/Cas inviting Dean in. I think that's because a) Sam/Cas is the rarest pairing out of Team Free Will and b) there is another trope that happens where Sam and Cas get together first.
That trope is that both Sam and Cas are in love with Dean and they make do with each other. It's not really my favorite trope, as I love Sam and Cas and hate to see them "settling" for each other.
I don’t mind stories that go from two to three, but honestly, I prefer it when the three of them sort of circle around each other and figure it out. There's a hilarious fic somewhere where Dean and Cas vie for Sam's affections, which is kind of the opposite of normal (where everyone wants Dean) that I enjoyed a lot.
I haven't yet seen this one, but I'm sure it exists. The one that I really really want is where Cas is involved with both Dean and Sam and then it turns into Wincestiel. Actually, I have read that, and I loved it. I will take more of it though, because I love that dynamic.
Recs
My very very favorite Wincestiel stories.
The Bright Waters Meet by
The_Bookeeper, 1875 words, teen and its sequel:
stop and remember me, 788 words, teen. My bookmark notes: Oh god, the Sam angst is going to make me diiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiie. The Enochian just really, really makes this. ETA: There is a sequel that is even MORE lovely and angsty and breaks me heart in two. GORGEOUS. More notes: these are short but they pack a MASSIVE punch. Easily my favorite of all my Supernatural recs, no lie.
Safest Place to Hide by
bree_black, 30k words, explicit. My bookmark notes: Perfectly believable Wincest and asexual Cas. Beautiful coming together and healing of Sam's soul after hell.
Into the Light of the Dark Black Night by
BewareTheIdes15, 23k words, explicit. My bookmark notes: Fantastic description, lovely Dean POV, angsty as hell and scorching sex. Brilliant.
Take This Trick and Spin It by
cautionzombies, 13.5k, explicit. My bookmark notes: Perfect and gorgeous; more about their devotion than anything and wonderful Cas POV.
Ripening by
Vera, 4200 words, explicit. My bookmark notes: True, equal Wincestiel with gorgeous slow sex and a great understanding/explanation of the dynamic between them.
Greed by
HigherMagic, 9500 words, explicit. My bookmark notes: AMTDI but with witches; sneaky Castiel, guilty Dean (oh, the angst is delicious), confused but well-meaning Sam. Lovely and everything I could want with this trope.
Under Every Sky by
Vera, 24k words, explicit. My bookmark notes: The one where there's another Sam and Dean in a post-apocalyptic world, and our Cas ends up there. A lovely, rich world, bittersweet and gorgeous, a delightful read. (BITTERSWEET ENDING! Just keep that in mind. It's so beautiful, though!)
AND! I'm super late on this post, partially because life happened, but also partially because I posted a Wincestiel big bang a while back, thinking there wasn't going to be any art. Found out
wifihunters was having a tough time IRL but was still working on the art and now it's live and holy crap IT IS AMAZING.
The story behind this story is that I signed up for a Wincestiel big bang last year, and the epic story I'd been working on (I had 25k words done going in – I really thought I could finish it!). But then I've realized it's roughly a 100k word story and I wasn't going to finish in time for the deadline. But it was a 10k minimum and I can pull that out in a day if I need to, so I came up with a second story and started to write. What if Cas asked the Winchesters out on a date – both of them? But then I couldn't finish that one either (though they extended the deadline by a month – I could've probably made it if they'd said something when I sent my defaulting email). And so when this Team Free Will Big Bang came up, I decided to finish that romcom idea because I loved it so much. I'm still working on the other epic story, and hoping to finish that one next year. I've got another one in the works, too, an alt!season 9 that I think will be awesome. But anyway – I finished this one, and there is freaking GORGEOUS art to go with it. :D :D :D :D
Title: The Three Body Problem
Author:
kisahawklin
Artist:
wifihunters
Art Post: Gorgeous art here
Pairing: Wincestiel
Rating: NC17
Word Count: ~36000
Warnings: None
Summary: Cas asks the Winchesters on a date. Yes, both of them.

Here is my December meme topics post, if you have something you desperately want to ask me.
Canon - Team Free Will
For a long time, Team Free Will was a V-shaped relationship, centered on Dean. I think Sam probably wanted to be closer to Cas, but Cas was not interested in befriending the boy with the demon blood. That has always made me a little bit sad, but it was reasonable for Cas's characterization, and I never turn down Sam angst. Sam angst is my favorite.
Cas's growth as a character has been fascinating, especially as it relates to the Winchesters. Loving Dean comes naturally to him; Dean is the Righteous Man, Dean is the one that will save humanity, fulfill the angels' plan. And then, when Cas starts to doubt, Dean is the one that teaches him about rebellion and thinking for yourself and all the good (and bad) things about being human. And all of it - because of Sam. Everything Dean does is for Sam, and I think, finally, at the end of it all (by which I mean the end of S5), Cas understands and wishes, perhaps, he might have gotten to know Sam a little better.
The next few seasons wander, a bit. Cas deceiving the Winchesters really puts a wrench in things relationship-wise. The look on Dean's face when he finds out Cas betrayed them, oh man. OUCH. Cas shifts Sam's crazy onto himself, still unable to actually get to know Sam any better. And he does it for Dean, again, because it's Dean's disappointment that gets to him, not Sam's plight, though I think he feels for Sam when he sees him.
So really, what I'm saying here, is that Dean is the glue that holds a lot of the SPN family together, but especially Team Free Will. Sam and Cas take a long time to figure out what they are to each other. I think Sam probably trusts Cas mostly because Dean does. He can see that Cas helps them and all that, but it's Dean's unshakeable faith that Sam trusts, not Cas himself. (And oh, how he would like a little of that for himself, yes? Yes.)
Season eight we're back to Dean and Cas, together in Purgatory, and then the Cas and Naomi storyline, and the tablets and the trials. This is a turning point for Sam and Cas, I think. When Cas sees what Sam is willing to do to save the world (or just make it a better place) - again - I think something changes in the way he views Sam, something fundamental. Which is why in season nine, we actually get to see Sam and Cas interacting, having actual conversations, hugging. Sam and Cas have forged their own relationship, and, interestingly, it was mostly absent Dean. Dean was pissed at Cas and Sam was pissed at Dean, so that left Sam and Cas to work together while Dean went off and did stupid things like hang out with Crowley and get the Mark of Cain.
They're all battered and broken now, but I think there's a balance between them. I feel like they work together, have a system of checks and balances so none of them goes too far off the rails. We'll see when we get to the back half of season ten, but they've been doing a really good job of balancing the three of them so far.
So that's canon - more a Team Free Will thing than a Wincestiel thing, because of course the three of them as a romantic relationship will never happen onscreen.
Subtext - Sam/Dean/Cas
As Destiel shippers will attest, there is a ton of canon Dean/Castiel smoldering. There's tons of looks and moments and for me personally, every time Cas beats the shit out of Dean, I drool buckets. It's the reason 8.17 is my second fave episode (right after the 200th musical ep).
And as Wincest shippers will attest, there really is a lot of Sam and Dean standing too close together, and they are way closer than normal brothers. I can do incest, but I have to work at it for myself, though I can read other peoples' takes on a breezier acceptance of it.
There are some delightful Sam/Cas moments in the later seasons – the hug where Sam has to tell Cas to hug back, the hug where Cas keeps holding on to Sam even after it's over, some of the looks like when Cas tells Dean that Sam's damaged in ways even he can't heal.
So, there are nice canon moments for all the pairs that could lead to a little something more. There are even a few that could work as subtexty for the three of them, maybe, though nothing comes to mind off the top of my head. I don't think it takes too much – obviously, actually, since one of my requirements for a 'ship is for me to believe just a small tweak in canon could lead to it. Usually this means that the pair/group has amazing chemistry which, considering the Destiel and Wincest shippers out there, I have to say, yeah, they do. Swinging those two juggernauts around and making it into a threesome? Yeah, that's pretty much my default setting.
Fanon - Wincestiel
I find that there are a lot of tropes in Wincest and Destiel that don't make their way into Wincestiel too easily. Apparently it's harder to negotiate a threesome first time than a pair.
The thing I see most is a pairing that invites the third in. I've seen this both as Destiel and Wincest, but I can't actually remember an instance of Sam/Cas inviting Dean in. I think that's because a) Sam/Cas is the rarest pairing out of Team Free Will and b) there is another trope that happens where Sam and Cas get together first.
That trope is that both Sam and Cas are in love with Dean and they make do with each other. It's not really my favorite trope, as I love Sam and Cas and hate to see them "settling" for each other.
I don’t mind stories that go from two to three, but honestly, I prefer it when the three of them sort of circle around each other and figure it out. There's a hilarious fic somewhere where Dean and Cas vie for Sam's affections, which is kind of the opposite of normal (where everyone wants Dean) that I enjoyed a lot.
I haven't yet seen this one, but I'm sure it exists. The one that I really really want is where Cas is involved with both Dean and Sam and then it turns into Wincestiel. Actually, I have read that, and I loved it. I will take more of it though, because I love that dynamic.
Recs
My very very favorite Wincestiel stories.
The Bright Waters Meet by
stop and remember me, 788 words, teen. My bookmark notes: Oh god, the Sam angst is going to make me diiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiie. The Enochian just really, really makes this. ETA: There is a sequel that is even MORE lovely and angsty and breaks me heart in two. GORGEOUS. More notes: these are short but they pack a MASSIVE punch. Easily my favorite of all my Supernatural recs, no lie.
Safest Place to Hide by
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Into the Light of the Dark Black Night by
Take This Trick and Spin It by
Ripening by
Greed by
Under Every Sky by
AND! I'm super late on this post, partially because life happened, but also partially because I posted a Wincestiel big bang a while back, thinking there wasn't going to be any art. Found out
The story behind this story is that I signed up for a Wincestiel big bang last year, and the epic story I'd been working on (I had 25k words done going in – I really thought I could finish it!). But then I've realized it's roughly a 100k word story and I wasn't going to finish in time for the deadline. But it was a 10k minimum and I can pull that out in a day if I need to, so I came up with a second story and started to write. What if Cas asked the Winchesters out on a date – both of them? But then I couldn't finish that one either (though they extended the deadline by a month – I could've probably made it if they'd said something when I sent my defaulting email). And so when this Team Free Will Big Bang came up, I decided to finish that romcom idea because I loved it so much. I'm still working on the other epic story, and hoping to finish that one next year. I've got another one in the works, too, an alt!season 9 that I think will be awesome. But anyway – I finished this one, and there is freaking GORGEOUS art to go with it. :D :D :D :D
Title: The Three Body Problem
Author:
Artist:
Art Post: Gorgeous art here
Pairing: Wincestiel
Rating: NC17
Word Count: ~36000
Warnings: None
Summary: Cas asks the Winchesters on a date. Yes, both of them.

Here is my December meme topics post, if you have something you desperately want to ask me.