a loose outline of the prince of hell / boyking au in regards to season four.
in the season three to four gap, please note that sam remains feminine presenting the entire time regardless of pronouns. deans dead so why should they care about their visual presentation, plus they're largely dissociating that first month.
after they start the crazy summer affair with ruby and progress is still too slow, ruby makes a little suggestion. just a small innocent idea while sams drinking her blood.
if sam takes the throne from lilith like azazel had wanted, then they would have her contracts. if they have the contracts, they have deans. and then they can bring dean back.
it takes a month for ruby to crack them (in more ways than one), and the following two months are dedicated to bringing together the ranks of hell that would follow them. they make a lot of progress for the throne honestly.
of course castiel still pulls dean from hell after the first seal is broken. which really makes sam spiral hard considering the path theyve gone down just to save him. but here we are too late to back down, they already have a cult made up of fanatics and azazels loyalists.
ruby is, of course, working with lilith to conveniently send them more loyalists with no one the wiser. gotta have enough capri suns in waiting.
bobby and dean do not know what sams been doing this whole time yet, but unlike canon sam isn't at some motel dean can find. there's a wild goose chase trying to find sam, whos left a lot of false leads for lilith to follow, and also juggling the whole angel of the lord cas thing.
after 4x3, dean is taken directly to a gathering of demons where he manages to get one to talk and admit that sam has taken their prince of hell title and is using their powers to fight lilith.
4x4 metamorphosis brings the winchesters together due to travis contacting them both (sam directly, dean via bobby since word hes alive isnt out yet) for help with the rugaru case. while sam knew that dean was back, they couldn't face seeing him yet as they knew he'd disapprove of the whole cult business.
they have their little canon argument about the path sams going down, sam purposefully doesn't tell him much beyond what he knows (aka sam using their powers, going for the throne) so the argument doesn't end with them going their separate ways yet. they part at the end of the ep making it clear that sam won't stop using their powers and dean can't accept that.
at this low point, ruby tells sam the full truth about mary and azazel. that even if he stopped the blood, he can't undo the truth of his birth. the crashing out gets worse, the cult gets emboldened.
as of 4x9 i know what you did last summer, it's revealed in it's the great pumpkin by cas and uriel that sam has a cult now. and that cult is getting worse. ruby and sam approach dean at a bar to tell him that liliths demons are going after anna. they do not know that dean already knows about the cult or that annas an angel. so thats a surprise.
sam and dean go for a talk away from angels and ruby. which is a tough sell since she's their right hand man. they argue again. sam attempts to explain themself and the cult, it doesn't sound great honestly. sam and ruby discuss how they're breaking seals to try and "control the fallout" and get ahead of lilith. they agree dean cannot find out about this.
sam explains a very edited version of what happened while dean was dead, and exactly why they started going after the throne. everyone wants lilith dead, and if sam has control of hell they can stop someone worse. the cult is an accident they totally hate.
of course they dont have cult robes haha......
anyway thanks to the shittiness of angels, the alliance continues for another few days to help anna. the angels freaking hate it. dean tells sam about the rack and alastair at the end, which sam wrongly takes as a sign they're doing the right thing.
not relevant for this, but 4x13 after school special still happens. but this time sam can honestly say that yes theyre happy. dean hears this and leaves without a goodbye.
they don't see each other again until 4x15 death takes a holiday. sam is already in town for the reaper sacrifice and is trying to beat alastair to the punch. while sam tries to hide this from dean through the episode, dean obviously knows something is going on here, plus alastair mocks him with what his baby siblings up to.
thinking deans already left town, it's revealed that sam and ruby still have one reaper. dean unfortunately finds their cult gathering and sees sam break the seal. cas probably stops him from storming in there and starting a fight, but barely.
come 4x16 on the head of a pin, the winchesters have not spoken at all. dean knows. sam knows dean knows thanks to some very nasty phone calls. but sam hears through the cult vine that alastairs been captured by angels. which sounds a bit off. then she can't get a location on dean. which is even more concerning. they don't trust angels, they don't think alastairs that easy to kill. its basically ruby saying not your circus not your monkeys and sam realising deans involved and pointing out it IS his monkey.
alastair reveals to dean during the whole reverse torture that all the upper ranks of hell know sams azazels child. oh wdym you didn't know that buddy, did sam not tell you? which leads to more conflict with the angels since they knew too and didn't tell him. literally no one is looping dean in to the gossip.
anyway, sam still turns up at the end to finish alastair off. partly as a blow to lilith, mostly because they are not letting dean die again after this whole mess.
dean summons sam, literally, at the start of 4x19 jump the shark to have a "talk" about things. hes just met chuck and been reminded of their happy days, has been given weird therapy by angels. it's time they sit down, y'know? except nah they get the call from fake adam before they can resolve a single thing.
literally nothing gets resolved. at all. things are actually worse by the end of the episode with them both talking a lot of shit about john and azazel.
then comes 4x20 the rapture. jimmy is being chased by demons and sam has a demon cult. its only logical that dean leaves sam a voicemail telling them to get control over their fuck ass demons. mind you, sam's demons have better things to do than kidnap and torture jimmy.
sam also takes this as an invitation to go help out. it was NOT an invitation at all. dean is not happy about this. hes even less happy when he catches sam having a little mid fight demon snack.
an important note here is that sam is getting deeper into this cult despite claiming they have it under control. with rubys guidance, they go from believing that they need to control what seals are broken to stop lilith and set a trap for her, to thinking its not that bad if lucifer gets free. that lucifer would care for and reward them. thats something theyll deal with after killing lilith though dw.
theyve also bought their own prince of hell hype thanks to the the cult unfortunately. sam, canonically resentful of always taking orders and being treated as a kid by john and dean, is a little high off of being powerful. being in charge. having demons that do as they say. do they really want to rule hell? no but they have ruby to help with that and if lucifer gets free then theyre just the prince......
which takes us to 4x21 when the levee breaks, where bobby and dean still trap sam in the panic room attempting a come to jesus moment since nearly all the seals are broken. again, none of them know lilith is the last seal. they think if they can kill lilith and detox sam, he will leave the cult business behind and get better.
bobby keeps confronting dean with the fact sam can't die human, because now they know he's never been. dean does not listen to this.
either way after killing lilith, sam does not help dean kill ruby. while not buying into the same fanaticism as the demons theyre leading, sam is hooked into a different kind. more about their own strength and heaven vs hell and lucifer. so are they mad ruby has been lying to them? yes. but she was doing it for the ultimate vision.
the arc ends in one of two ways after ruby gets away alive. either sam goes with her and struggles on his own in s5 over not wanting to be just a vessel and the new hierarchy of hell, or they stay with dean after realising they definitely didn't want to free lucifer and a lot of season 5 involves demons and lucifer trying to sway sam back while she and dean (and cas) try to rebuild trust.
either way throughout season five, sam is prince of hell which is a very different role to king of hell and will be explained at a different time.