omg you make such a good point about maroni being too confident in himself, boisterous and using more brute force than manipulation. I need to keep that in mind, 100%. and absolutely being nasty and rude will be something I will play up as well, that'll be fun 😈
I had the idea of him figuring very early on that Jim has feelings for Oswald and I do like that because that way he has leverage against both of them should he need it. but maybe I'll change that to him finding out later. will see
as for him playing out both options: the idea I had was that to oswald individually he could take the transphobic route but then to Jim individually the homophobic route. and when he interacts with both of them together (which is something I've partially written) I'm not fully sure yet. for now I wrote that as him trying to drop hints so that each of them figure out the thing the other doesnt want him to know about and getting increasingly obvious to make them uncomfortable or provoke them.
I'm thinking specifically with that bit in s1 somewhere where he takes oswald to that remote cabin. he does show signs of intelligence and planning and insight there, so to an extent it's not out of the question.
another idea I already had was that I definitely need him to misjudge how Jim would behave when finding out that it's Oswald who he's been dating and/or that Oswald is trans. and what you've said about Maroni not being the best at reading people actually works miraculously well for that. so if I lean into that angle that actually gives me a really good reason why certain things wouldnt occur to him.
as for Jim recognising Oswald: there is a separate version I started where after a pretty short time, Jim realises it's Oswald but plays along because he has found out that Oswald is bugged and tries to figure out what the motivation/reason is.
for this version however Jim has to remain clueless until Maroni sends someone to drop hints to Jim that who he's seeing is a man and/or Oswald. so I will need to find reasons xD
one is definitely that Oswald would be wearing a wig, maybe one that's a different haircolour than his natural hair. and of course the effect of make-up cant be underestimated, specifically contouring can really do a lot to change someone's faceshape. (I'm thinking of that video thats like "if men find out we can shapeshift, they're gonna tell the church" xD)
I'm definitely imagining that Maroni would find someone to do Oswald's makeup to get him ready for the date nights. Oswald on his own probably isn't particularly good at doing makeup in a feminine style and he needs to look really good. I'm thinking that they're gonna put him in 2010s style full glam makeup xD
what you said about Oswald scheming made me realise that that's really not something I've accounted for. I've mostly written Oswald being scared due to the blackmail and threat of violence that Maroni holds over his head.
but Oswald is always scheming something xD so I will need to find ways to incorporate that and what it could be. maybe have him try and fail a couple of times to get away or something. he does fail a lot in his attempts because he often acts too impulsively.
or maybe he could purposefully try to give false information in hopes of getting some important men of Maroni's killed but it backfires on him and he has to deal with the consequences of that (physical violence to an extent as well as being shouted at and berated). or he hears from Jim that the police are getting ready to raid a specific warehouse or spot and doesnt tell Maroni about it. and for some reason Oswald comes with them there, cause maybe he has the hope he will be able to run away once the police arrive to make arrest, maybe his secret hope is that Jim will be there. but either Maroni himself or one of his men notices Oswald behaving oddly so they change their plans last minute without informing Oswald.
from what I have so far (there's several options), Jim desperately wants to help Oswald to get him out of Maroni's clutches because he has feelings for him and has also started feeling protective (this is where how protective Jim gets about women he's dating could come in, in that he still partially sees Oswald as a woman because of how they met when they started "dating")
I dont have any concrete ideas yet how they will ultimately make it work. that is definitely the plan. but no clue so far (you're welcome to say if you have any ideas)
one plot point is that there's a conversation Maroni has with Jim and Oswald together after Jim has found out that Oswald is the "woman" he's been dating. as a recociliation offer to Jim (that's what he frames it as anyway) he makes Oswald go with Jim to stay with him for a few days, if Jim refuses he threatens to have Oswald beat up really badly. he hopes that while Oswald stays with Jim, Jim will realise that Oswald is trans and whatever fallout will come from that.
but what actually happens is that they talk and realise they do in fact have feelings for each other (but Jim still doesnt know Oswald is trans because he keeps that very well hidden). and when its time for Oswald to go back to Maroni Jim doesnt want to let him but Oswald expresses he doesnt have a choice.
so then Jim tries to make him say what it is that Maroni has on him but Oswald refuses. they argue about it and leave on bad terms basically. or at least from Oswald's side. Jim might get over his frustrations pretty quickly but I think Oswald would stay upset for a while that Jim would try to pressure him so much.
I'm having so much fun with this <3 <3
