Dean is an aro apl a-hole

You have not disappointed me so far.

You know what's at the top of my mind today? Sadomasochism. So I'm going to ask about that here. Let me know your thoughts about sadomasochism in wincest.

And please note, the question is not "in wincest, who do you think is the sadist and who is the masochist?" because that's not the only way these things go. You're also welcome to think that neither of them are into it at all. That's a valid answer that isn't a cop-out or a non-answer, but a legitimate interpretation of the characters. Maybe only one is one of those things. Maybe you think they're both sadists or both masochists. Maybe one or both are switches. Or, of course, you can think that they're a traditional sadist/masochist pair. My point is, I don't want you to think this is a binary question or you have to give traditional/binary answers. Creativity is encouraged.

-@schizosamwincester

Had a busy week but I finally have the brainpower for this hell yeah >:3

They’re both sadomasochists (and switches) to me. They’ve both been shown to enjoy the hunt a bit too much in various situations, and they both try to atone through pain at a few points, and both of those can easily cross the line to sexual (especially for our freaks lol)

Sam’s masochism is about feeling alive and present and needed so badly it hurts (as well as the classic needing-to-atone pain, I think he’d thrive in a dynamic with punishments, literally beat into his brain and body how to mess up and move on from it without guilt) meanwhile his sadism is about being able to take and be selfish and cruel and that part of him not only being accepted but wanted and loved

Dean’s sadomasochism is generally very entwined to me. Like it is for both of them but especially Dean. He’s shown to be intense but soft in canon sex scenes, but especially with Sam he likes being able to push and get shoved right back and they are Definitely grabbing and holding each other so hard it hurts and bruises. Not to mention the fighting as foreplay (and for dominance) lmao. Like their usual post-hunt adrenaline-fueled sex often leaves them both with a few more injuries than they finished the hunt with (and gashes more open than they were too, those boys are taking every excuse to finger those things)

Dean’s dominant flavor sadism comes from enjoying the pain and control over another in that way, which is both traumatizing and healing after Hell. Takes a while for him to hurt Sam after that, even when he’s begging for it and/or visibly enjoying it.

Dean’s subby masochism that everyone focuses on takes a while to come out. It’s like pulling teeth for Sam to get that part of him even acknowledged, let alone indulged. I just love Dean taking the “big brother, protect Sammy” stuff and building his entire sense of being on it and it making it really hard for him to give up control and indulge in the more traditional submissive side of this stuff, aside from “letting” Sam win and fuck him in their fight-and-fuck sessions lmao

You know what's at the top of my mind today? Sadomasochism. So I'm going to ask about that here. Let me know your thoughts about sadomasochism in wincest.

And please note, the question is not "in wincest, who do you think is the sadist and who is the masochist?" because that's not the only way these things go. You're also welcome to think that neither of them are into it at all. That's a valid answer that isn't a cop-out or a non-answer, but a legitimate interpretation of the characters. Maybe only one is one of those things. Maybe you think they're both sadists or both masochists. Maybe one or both are switches. Or, of course, you can think that they're a traditional sadist/masochist pair. My point is, I don't want you to think this is a binary question or you have to give traditional/binary answers. Creativity is encouraged.

-@schizosamwincester

i do think that after they both experience hell, dean is a sadist and sam is a masochist. i think perhaps before hell they both sorta leaned that way but were switches when it came to that, and that engaging in sadomasochism was not a frequent thing

like from before s3 they were more "vanilla" (which, like, they're still fucking their brother which is not at all vanilla but in this context lmao) when it came to their sex life but after dean goes to hell it becomes more angry between them, sometimes at each other but sometimes just restless anger directed at everything and anything

and then when sam comes back from hell and his wall is broken I think he becomes more of a masochist bcuz he's so used to pain. I love the HC of sam needing more and more pain and stimulation after hell bcuz his nerve endings and threshold for pain and sensation are soooo fucked up <3

I think I'll go nice and broad here. It's pride month, so talk about absolutely any LGBTQIA+ headcanon you have for supernatural. How did the Winchester of your choosing discover they were attracted to the same gender? Which side character was definitely stealth trans? Who do you know in your heart was aspec or intersex? And etc. You have free rein to spread whatever gospel you want, whether it explicitly contains any wincest or not, as long as it is queer

-@schizosamwincester

HE/THEY/IT PRONOUNS FOR SAM !!! idk why but I just am really fond of thinking of him using those pronouns <3 I think in a world where he uses pronouns like this he'd identify as agender and pansexual <33

hmmmm i do enjoy a bi dean HC from time to time. and i love the idea of both dean and sam being transmasc, and the idea of them being transfem too !!!! idk they're just so fun to play with when it comes to gender :3

You know what's at the top of my mind today? Sadomasochism. So I'm going to ask about that here. Let me know your thoughts about sadomasochism in wincest.

And please note, the question is not "in wincest, who do you think is the sadist and who is the masochist?" because that's not the only way these things go. You're also welcome to think that neither of them are into it at all. That's a valid answer that isn't a cop-out or a non-answer, but a legitimate interpretation of the characters. Maybe only one is one of those things. Maybe you think they're both sadists or both masochists. Maybe one or both are switches. Or, of course, you can think that they're a traditional sadist/masochist pair. My point is, I don't want you to think this is a binary question or you have to give traditional/binary answers. Creativity is encouraged.

- @schizosamwincester

*pulls out the recs list* Yeah i have thoughts on that.

Dean is a masochist, Sam is a sadomasochist. Related to that, Dean is a sub and Sam is a dom, obviously this doesn’t always correlate but I’m adding it because it influences the way I’ll talk about it.

Pain makes Dean feel useful, firstly, and it also makes him feel anchored, present. When I wrote An Unknown Color there wasn’t supposed to be any masochism at first but it slipped in because to me it’s closely related to the way Dean deals with trauma. Pain can, depending on how it’s inflicted, pull him out of dissociation or just out of his thoughts in general, to bring him back to his body and to the present moment, back into feeling immediate sensations instead of being deep in his head. Pain also works as penance, which is why I mentioned that I see him as a sub, aside from just enjoying pain in itself he can also very much enjoy being punished (with physical pain or with more psychological sadomasochism), and it will make him feel better and forgiven.

Overall I think Dean is aware of his masochism quite early, and he accepts it. He’s not ashamed of it exactly, or maybe just when he’s younger, but he worries about the way it makes him vulnerable. And he doesn’t like talking about it. He’s fine with his partner seeing what he likes, he won’t pretend not to like something, but he doesn’t want / doesn’t know how to communicate verbally about it, unless it’s in a very specific context like going to a bdsm club and asking for something, because then it’s quite impersonal and it’s the purpose of the place. He’s aware that it is a huge part of him and it scares him sometimes.

Sadist Sam is a headcanon that is very dear to me, maybe because of how people in fandom don’t like to explore sadistic characters. But it makes sense for him. He has always been out of control, he has always had to obey, and he needs to take the reins now, he needs to be the one in control, the one to make decisions. That’s for domming. And inflicting pain specifically is about trust, being intimately trusted to hurt someone in many ways, sometimes extreme, and this person still loving him despite (for) it and thanking him after. It’s about being seen in his entirety including for what he thinks are the dirtiest and most repulsive parts of him, and being accepted like this.

I think a lot about teenager Sam growing up and realizing that he is in love with his brother and that he likes thinking about hurting people, that it arouses him. The guilt! For many sadists it’s not exactly easy to realize and accept their sadism, and in Sam’s situation it would be much worse. His sadism is pretty extreme because of how much violence he has seen through his entire childhood, and he’s dealing with incestuous desires at the same time, all the while feeling like an outsider and believing that there is something inherently wrong with him. It would make him feel sick, make him worry he’s going to hurt Dean. And later, when he learns about the demon blood, he would probably think that that’s where it comes from, that he wants to inflict pain because a part of him is demonic. I think he would be very scared of his sadism because of how much he wants, he would be terrified of losing control and hurting his partner more than they want, going too far (and being trusted anyway, having someone firmly believe that he will not go too far, would mean a lot to him).

Both Sam’s sadism and Dean’s masochism are quite extreme (as in, the acts they can enjoy). They’ve been exposed to a lot of violence since a very young age, and they’re constantly getting hurt, so compared to what they face on hunts, a little spanking or flogging is often not going to be enough. I think they can enjoy pretty much anything, both physical and psychological, inflicted in many ways, with or without implements, with varying forms of pain. I think both of them can be scared of how much they want, of how nothing can be enough sometimes, and of course they can’t go too far because the injuries can’t interfere with hunts (and because no matter how much Sam loves to inflict pain and mark Dean, he obviously doesn’t want to injure him permanently!). One thing that would help a lot and would incredibly reassure Sam would be to have Castiel aware of what they are doing and willing to help heal Dean when it is necessary: it would mean they can go further than they would otherwise, and still be okay, have the pain be temporary instead of risking permanent issues.

For both of them it gets more intense after Hell, though for Dean it’s also more difficult not to get flashbacks sometimes, but it also helps him deal with it. He needs the pain more than before. And after the Cage, Sam needs even more control. Dean needs to recreate scenes from Hell with Sam hurting him instead of Alastair, because he trusts Sam, but he would need it to get further into consent play, not just simple CNC with a safeword but actual consent play re: being drugged, being unconscious through part of it, or negotiating the scene and consenting beforehand but not having a way out and Sam being the only one in control and reading Dean’s tells to decide when to stop. And that’s because it would mean Dean has no choice, that he does not have the responsibility to choose or to consent, unlike in Hell where every day he had to make a choice. Meanwhile, Sam had no choice in the Cage, no way out, no yielding and hurting someone else to make the pain stops, so topside he would need the control, the choice. I think Dean would gently push him toward recreating things that happened in the Cage but with Dean being hurt and Sam being able to choose what to do, turning the scenario around, though it would probably be difficult for him to agree to it because it would be more scary than usual, when he hurts Dean there is always the fear of becoming like Alastair, like Lucifer, like all the monsters, but then Dean’s trust and love help.

Now, I also believe Sam is a masochist, but it’s more complicated. It’s not as extreme, the type of pain he enjoys going through is not as intense as what he likes to inflict. It’s strictly about physical pain, not psychological, simply about enjoying the physical sensation of being hurt in some very specific ways, and he still needs to be the one in control / the dom if it’s a d/s situation. I think when he is younger and feels guilty about being a sadist, he turns to masochism to punish himself, but crucially this only makes him feel worse. Where pain and submission work as penance for Dean, the concept of punishment doesn’t work with Sam. He wants it to, he keeps looking for it, he wants to be hurt and to feel better afterward, but being punished only makes him spiral more about having done something wrong. It would be really easy for him to start a dynamic where he subs, and to become a lot more unstable and depressed because of it, because he would enjoy the pain temporarily but feel horrible about the whole thing afterward. What he needs, what works for him, are either scenes that do not involve any dominance/submission element (as in being with another sadomasochist friend and just taking turns hurting each other, but casually, without having a dom or a sub. I think he probably did this once or twice at Stanford) or, even better, scenes where he is the dom. I think most of the time this can just look like Dean pulling his hair and biting him when Sam is fucking him. But it can also look like ordering Dean to hurt him, though they would have to be careful there, it would be difficult for Dean with his trauma around coerced perpetration, but ultimately it might help him too, to see that it helps Sam, and that Sam is the one who wants it and tells him what to do. I think a more risky scene (for both of them, psychologically) they could do would be to recreate a torture scene that Sam went through in the Cage, this time still with Sam being hurt, but him being the one to tell Dean exactly what to do / what Lucifer did, and then having the power to tell Dean exactly when to stop, ending the scenario where he wants while in the Cage Lucifer just kept going anyway. I feel like that could do a lot for Sam to reclaim control, but the risk of it going wrong would be quite important.

I cannot stress enough how much I don’t believe in sadist Dean. He was forced and tortured into becoming a torturer and the only way he could cope with it was to enjoy some of it, and it is said very clearly that it’s because of how much pain he had just gone through. He had learned to associate pain and pleasure even more than he already had, to survive, and then Alastair uses that to push him into also inflict the pain. He feels horrible about it. It’s not just regular guilt about being a sadist, it’s guilt about having "let" himself be forced into this when it goes against everything he believes and wants. Even if he had had some sadistic inclinations before Hell, the trauma would have made him unable to do it and enjoy it afterward. Sometimes he gets too angry during a hunt and ends up finding too much pleasure not just in killing monsters but in making them hurt, and I think even that terrifies him. Again, the only way I can see him inflicting pain on a partner and not breaking down afterward would be if he was directly ordered to do so, if he was not in control of the situation, if he did not have to make any decision about it.

I think I'll go nice and broad here. It's pride month, so talk about absolutely any LGBTQIA+ headcanon you have for supernatural. How did the Winchester of your choosing discover they were attracted to the same gender? Which side character was definitely stealth trans? Who do you know in your heart was aspec or intersex? And etc. You have free rein to spread whatever gospel you want, whether it explicitly contains any wincest or not, as long as it is queer

-@schizosamwincester

You know what's at the top of my mind today? Sadomasochism. So I'm going to ask about that here. Let me know your thoughts about sadomasochism in wincest.

And please note, the question is not "in wincest, who do you think is the sadist and who is the masochist?" because that's not the only way these things go. You're also welcome to think that neither of them are into it at all. That's a valid answer that isn't a cop-out or a non-answer, but a legitimate interpretation of the characters. Maybe only one is one of those things. Maybe you think they're both sadists or both masochists. Maybe one or both are switches. Or, of course, you can think that they're a traditional sadist/masochist pair. My point is, I don't want you to think this is a binary question or you have to give traditional/binary answers. Creativity is encouraged.

-@schizosamwincester

funnily enough i was just thinking about something similar—

so buckle in for some character analysis

it’d be easy from a wincest standpoint to say “sam is a masochist and dean is a sadist” which i don’t think is untrue, i just think its unfinished

with sam, he changes over the seasons. we see him full of rage and power and frustration in the earlier seasons but later seasons he’s subdued and compliant. early seasons, i could see sam dishing it out, a sense of due justice maybe, but it’s murky. this would also probably be the only time i could see sam enjoying masochism. i’m not even sure if masochist would be the right term as he’s more able to simply accept and handle pain (pain scale completely fucked cus of the cage), rather than enjoy it. maybe he does enjoy it, maybe pain gives him comfort and reminds him of the centuries spent with lucifer—fucked up stockholm, who am i to really say. but i’m not confident saying he’s a masochist, earlier or later seasons.

You know what's at the top of my mind today? Sadomasochism. So I'm going to ask about that here. Let me know your thoughts about sadomasochism in wincest.

And please note, the question is not "in wincest, who do you think is the sadist and who is the masochist?" because that's not the only way these things go. You're also welcome to think that neither of them are into it at all. That's a valid answer that isn't a cop-out or a non-answer, but a legitimate interpretation of the characters. Maybe only one is one of those things. Maybe you think they're both sadists or both masochists. Maybe one or both are switches. Or, of course, you can think that they're a traditional sadist/masochist pair. My point is, I don't want you to think this is a binary question or you have to give traditional/binary answers. Creativity is encouraged.

-@schizosamwincester

Oh boy, an opportunity to share one of my more nuanced and likely controversial opinions: I think Dean genuinely, sadistically enjoyed torturing souls in Hell AND I don't think he's a bad person for it

I think it's a very human thing to find a vicious sense of catharsis in hurting others and I think that's what Dean experienced, not just relief from his own torture, although I'm sure that's why he initially did it. Sadistic catharsis being normal doesn't make it okay to hurt others without consent, of course, but acting on it in very traumatic extenuating circumstances doesn't make him a bad person

I don't think he's sadistic with humans, and while he does enjoy fighting and killing monsters, I figure it's more about the physicality of using his body to accomplish something (see: his cheerful lawn mowing in the djinn dream and being a builder I'm pretty sure at the beginning of s6)

I absolutely don't think he's a sexual sadist and I'd wager that even pre-Hell he would really struggle to accommodate a partner who wanted him to hurt them. He might be able to stomach playfully spanking someone during roleplay but otherwise nah

I do think he's mildly sexually masochistic due to the "slapped in the face by a woman wearing a zorro mask" comment 😆 I think he's pretty subby and would like a lot of things if they were framed as putting him in his place. I think he'd get charmingly wiggly and tingly as the bottom in wax play 👀

I don't think Sam is a sadist or masochist. I do think he's Dom-y as hell and would have an easier time not-playfully hurting a masochist for kink/sex purposes than Dean would once he's sure it's wanted. I think he'd still angst about being able to do it meaning he's evil

You know what's at the top of my mind today? Sadomasochism. So I'm going to ask about that here. Let me know your thoughts about sadomasochism in wincest.

And please note, the question is not "in wincest, who do you think is the sadist and who is the masochist?" because that's not the only way these things go. You're also welcome to think that neither of them are into it at all. That's a valid answer that isn't a cop-out or a non-answer, but a legitimate interpretation of the characters. Maybe only one is one of those things. Maybe you think they're both sadists or both masochists. Maybe one or both are switches. Or, of course, you can think that they're a traditional sadist/masochist pair. My point is, I don't want you to think this is a binary question or you have to give traditional/binary answers. Creativity is encouraged.

-@schizosamwincester

Happy Wincest Wednesday!! (Yes it is Friday now, shhhhhhhh ignore that)

I feel like Sam and Dean both have moments where they can be switches, but in general I might be one of the few people on this app who thinks Sam would be more of a sadist and Dean more of a masochist.

I think Sam's sadism stays in the bedroom for the most part, or he tries to keep it there anyway. With less inhibitions when he lost his soul obviously it was a lot more prominent in other situations too. With Jess I think he really tried to avoid that side of himself, because he knows he's big and intimidating and doesn't wanna be that guy, but with Dean? Different story entirely. Their relationship has always had some violent undertones at times, and Dean definitely shows that more outwardly in the show, but in private Sam revels in having that kind of control.

Dean's masochism, on the other hand, is a much more fundamental part of his daily life. Before he went to hell, it mostly had to do with the guilt he felt in basically everything he did (usually surrounding Sam). Failing to protect him, dragging him back into the hunting life, having perverted feelings for him (even though he knows Sam feels the same way). The pain is a form of atonement for him, and it's even better when Sam's the one inflicting it. After he came back from hell, I think part of it also became just trying to feel something. Soft touches barely register to him anymore, the pain is the only thing that can keep him tethered, the only thing that he can really feel at all. That becomes pleasurable in itself, and eventually it gets to the point that Sam has to give Dean a serious talk, because he's intentionally letting the monsters they fight get hits in on him. Sam compromises with him, gets even rougher with him when they're in private to satisfy his need for pain. Sam doubts its healthy, but he can't complain too much since he also gets off on it.

It's my birthday today, so let's shake things up. Instead of me asking you something, respond to this with a question that you want me to answer! And I will get to talk everyone's ears off all day. No limits or anything; just go for it.

- @schizosamwincester

OH OH OH I want all your thoughts on fem!Dean (including transfem if you have thoughts on that) and stanford years John/Dean, as hunting partners, more, less, gimme it all. Finally give me your top 5-10 Sam headcanons that you don’t talk about as much.

Trans femme Dean? Well, god, I've said A Lot about that concept. If you haven't seen, I have just a few fics about the concept. I am 110% on board with the idea that Dean's performative masculinity is very much overcompensating for internal transfemininity.

Actually, if we're asking about fem Dean in general, I have what I feel like is a hot take: I generally do not think fem!Winchesters works because toxic masculinity is such a central theme of the show. Like, I'm fine with trans femme headcanons, I love those (and trans masc ones although that probably goes without saying) because that does still come with a huge connection to masculinity and its roles in society because, you know, if you're a trans femme you're expected to act like a man and fill that role for the first however many years of your life, but with cis female winchesters? You just completely lose that theme of fitting into patriarchal expectations. Like... So much of the show is about Sam filling the role of that prototypical masculine hero avenging his girlfriend's death (and later his other girlfriend Dean's death, lol) and trying not to fall into the footsteps of his angry/vengeful hunter father. So much of Dean's character is about trying to live up to that tough masculine archetype he sees in John, even when that isn't actually who he is. The show is about struggling with repression because men aren't supposed to express their feelings in society. It's struggling with the way that manifests in the family in particular. It's dealing with the idea that the only acceptable outlet for men's feelings is violence. And so if you do an AU where they're cis women... I'm someone who uses fic primarily as a means of exploring the themes already in the text. That's what I like to do. I don't think I'm superior to other people in fandom for having such a literary approach to it (honestly I think it often confines me a bit) but that's how my brain works and what I enjoy. And so when they're women, that gives them an entirely different set of struggles and expectations that aren't what Supernatural is originally about, and I don't know what to do with them anymore. I like Sam and Dean because I like those particular struggles with masculinity. Cis genderswap them, and they aren't my favorite dolls anymore.

Trans genderswap them, though? Well that's an even better way of exploring masculinity. Now they're actively dealing with its place in their lives instead of taking it for granted and as a given.

But to me, the core appeal of trans woman dean isn't actually gender at all. It's that Dean as a character is someone who isn't allowed wants and needs and desires. Hunting and family and the life always come first. All his life, he's never gotten to have dreams and aspirations. He's had to save other people and put them first. Anything he wants or needs gets buried way the hell down. And so you give Dean gender dysphoria, and that's something that she'll try to treat the same way. She'll fight it and bury it, especially because so much of being a hunter is being able to blend in with "normal" people and especially circa 2005-2010, a trans woman is going to stand out. I mean, they very much still do. Dean Winchester and all his performance masculinity is already a costume that he puts on, a costume he wears for so long that he eventually becomes it, and it only draws attention to all of that and strengthens it to put a woman underneath it.

Anyway. That's my major thesis. The one real new thought I have lately is that @19catsncounting floated the idea of trans woman Chuck to me as basically a joke, because we were saying you can trans any supernatural character, and we have both realized actually that's very good and we're quite obsessed. And I won't go into all the particulars of that right now because I'm trying to save them for a fic. But. I will say this plays along great with the idea of Sam and/or Dean as Chuck's self inserts. So if they're repressed trans women, well it only makes sense that Chuck is too. Dean is her favorite plaything because she too is a woman who is trying her best to ignore all that.

Sam headcanons that I don't talk about... Hmm... See the problem with this is that I talk a lot. If I haven't been talking a lot about a headcanon, it's only because I've done it in the past. I do not shut up and I don't keep anything to myself. Well. Let's see what I've got.

1. Trans woman Sam finds that out in part because Jess has a trans sister. Which I guess is more a Jess headcanon than anything, but shhhh.

2. Sam Winchester was a fat kid! Which I do talk about but not enough because there is no such thing as enough! "Sammy is a chubby twelve year old" implies that Sam was a chubby twelve year old and the casting department are cowards for not actually doing that!

3. Sam is a dom. Well... okay in general my take is that most people, the Winchesters included, don't engage in BDSM as often as people in fandom portray them as. So I do think mostly Sam and Dean have vanilla sex in that regard. But. If there is BDSM? Sam's themes over and over are about him struggling for control. Domming is a great way for him to get that.

4. I also really like the headcanon of Sam as a sadist. As someone who has been a sadist for my entire life, including as a child, you do feel dirty and wrong as a child when you're deriving pleasure from killing off characters in video games or your favorite story characters in your head. It makes you feel unclean and guilty. You don't really know what you're feeling, but you know that the idea of slow and painful death isn't supposed to make you tingle down there. And you feel wrong and evil about it. And that fits so well with Sam.

5. I know no one else on this website cares, but Sam and Dean do in fact do and like messy anal and Sam loves the sight of Dean's pure white skin all smeared in shit from it. The depravity of the sight really gets him off. It's dirty and filthy and hot.

6. Sam was hanging out in online chatrooms as a teenager. As someone who did the same thing. I know my kind when I see it. You were hanging out in IRC just like I was, Sam.

7. Omega and beta Sam loves teaching alphas the cool fact that they have bigger prostates than omegas and betas, and so they'll get way better orgasms from anal. Alphas in particular are all so convinced that because they have knots they're supposed to use them, but they also produce ridiculous amounts of cum, which means huge prostates, which means they're made to be topped. And to Sam that is a really cool fun science fact that he enjoys sharing. Generally by topping them.

8. Intersex Sam is really fun and I'll never get around to writing my omegaverse intersex!Sam AU but I wish I would.