#deanjack

[sisterwifesam]

can we agree that becoming the worst version of his father AND loving it is the sexiest thing he's ever done.

[sdfrot]

winkline - family line

[m0msonsamjackfanatic]

https://www.tumblr.com/m0msonsamjackfanatic/806159571691470848/jack-you-have-to-be-gentle-with-your-mommy

Okay but Dean walking in on them…jealousy issues ensue because Dean wants to be the only alpha who fucks omega Sam and also gets to call Sam “mommy”

I can totally see this, Dean coming in mad screaming at jack “no… no touching” as he walks across the room going behind jack trying to pull him off of sam

Jack whimpering as he tightens his grip around Sam’s waist, still trying to thrust into him, as Dean is still trying to pull him off

And Sam’s weak protest through moans as he tires to tell Dean to stop, but it’s useless as the alphas continue to argue— Dean saying “no Jack, you don’t get Sammy, he’s mine… only I get to fuck his holes, only I get to call him that— he’s mine” Jack struggling to maintain his grip “no Dean… Sam’s my mommy too” jack says his words slurring

Sam releases more pheromones thinking it will help calm the alphas, but it just makes it worse as he hears them both growl at this

[perverted-asexual]

Sam and Dean taking turns fucking Jack whilst Cas is dead.

He reminds them of him so much, so unsure yet curious, so wanting. He just wants to make them proud and learn everything he can. Just like Cas when he first fell into their lives.

They can feel the power flowing through him, different and stronger thar Cas' ever was, but not unlike him either.

They have to teach him, talk him through everything and its just like those first few times with their angel. Being with Jack, who somehow looks so much like Cas, who is the only thing they have left of him... its almost perfect.

Having an angel under them, just like they're meant to.

[samdeanjohn]

happy wincest wednesday! i like voyeur sam 🥹 do you think he'd ever allow a guy fuck dean if they were like established tm (let's say later seasons vs earlier seasons) ?

such an excellent question. forgive me for answering it a year later and on a sunday.

voyeur sam is canon but so so complicated. it's not usually a fun activity for him and he tends to be tortured about it. and i do think it started in his teenage years and a lot of his early knowledge of sex comes from secretly watching (or hearing) dean (solo, with women, with men, with john..any or all flavors). so the shame is a big part of it and a big part of what turns him on about it and the more he hates himself the better.

i tend to keep my wincest headcanons as close to canon as possible so based on that it doesn't seem like they could be exclusive until later in the bunker era (season 13?). but it doesn't seem like they hook up with others often in the second half of the show and some seasons go by without even a mention of it. and we see sam be more supportive of dean hooking up in seasons 11 and 12 even though he'd possibly prefer it if he didn't. there's just something very tender about it.

but you asked about men specifically and to that i'd say it does seem like he would be supportive of dean sleeping with his wrestler crush ("groupie much?") and i'm sure dean would approve of him sleeping with the presenter lady if it worked out for him. but it can be casual fun with those people because they're not part of their lives. and gunner was not a threat like amara was in that same season with her mental bond to dean.

all this to say sam matures a lot from his earlier years, especially when it comes to his attitude towards dean's sex life. and i don't think he's entirely clueless as to why dean has difficulty returning to his old ways after hell. it's the kind of thing that gives you perspective.

but as judgemental as younger sam always acted about dean and women he was especially jealous and possessive when it came to dean and MEN and that didn't really get easier in the post-kripke years. men who could potentially replace him, steal dean from him, corrupt him, change him.. dean teaming up with ketch late s13 brought back those insecurities so if dean felt like fucking ketch sam would have a huge problem with that. obviously. and do i think he pictured it and got hard about it no matter how much the thought disgusted and hurt him? absolutely. same thing happened when dean was off having actual affairs with benny and crowley.

so a stranger if dean asked late into the show? maybe. but i don't think dean has much interest in sleeping with strangers after a certain point. it definitely would feel validating to sam to be asked for permission though. i think generally by the end of the show they prefer to be mostly exclusive outside of dean's relationship with cas and sam's relationship with rowena. and they're both essentially family at that point so they MAY potentially get over their jealousy and hangups enough to be okay with that. it depends. a wincestiel threesome to confront his fear.. as long as it's not easy and uncomplicated.

the one guy i controversially think sam himself would push for dean to sleep with (in his presence with his encouragement) is jack. i've talked about it before but sam was just overidentifying with him to the extreme. and he was intensely weird about dean's role in relation to jack. he saw jack as a version of himself that could avoid even being tempted to go down a dark path away from his family and as long as he had dean's complete love and trust, he could be saved. so naturally, he would have to become a man and a winchester between dean's legs too. it's how it goes. and since it's all his idea from the start, it's safe.

[babydollsammy]

What’s your opinion of Jack with Sam and Dean?

I haven’t watched the later seasons yet so I don’t know details but I’m a huge fan of his presence in their relationship.

I don’t care whose he actually is, that’s Mommy Sam and Daddy Dean’s kid.

Dean puts him in the corner and makes him watch Daddy fuck Mommy so he understands the dynamics of their fucked up little family. Sam takes it like the good little brotherwife he is because he has to teach him how Jack is expected to service the patriarch of their household.

very yummy 🥰

[vampzmeel]

Would you draw winkline?

i have been thinking about drawing them for a while so thanks for the motivation anon lolz

[holyfreaks]

deanjack where dean makes jack cockwarm him facing forward in his lap while dean looks at his phone or does some research, not paying attention to him, and jack starts to get squirmy and whiny as minutes upon minutes pass, aching to move and get off, and he shifts his hips just slightly, but enough for dean to grab him by the nape of his neck and tells him to sit still or he'll make sure he won't be able to sit