does. Charles. know. that pointy boy loves him with all his disgruntled little pangolin heart.

Chaz is indeed aware of this very important fact, though of course neither one of them put that sort of thing into words. Partly because doing so makes things a little too real and a little too – vulnerable – which is not an emotion either one of them enjoys enduring for any reason. And partly because neither one of them fully knows how the other will react to such a fact being granted a vocal platform.

But he does know and he does grant Jack liberties that no other man ( or human in general – or pangolin, in fact ) has access to. Like calling him Chaz for one thing, to the point that it is the only nickname he accepts, though you have to be a Rackham level friend to unlock the right to it and thus far Rackham is the only one on that level and so here we are.

{ Tragic Honesty }

Name one of the traits you hate most about yourself, why do you hate it? = Charles from @harriedwritings

Charles actually answered this in an offsite roleplay, in two particular methods. What I am going to do is transcribe both of them over and then unpack them – this isn’t something he would answer honestly without being pressed into very specific corners, so this is going to be more along the lines of mun analysis than character response – but as the pieces involved are his exact words it will still have ‘the vibe’ I hope. So, without further ado:

Part One:

“I don’t need a saviour.” He would not live in that kind of debt to any man. Ever. “My submission and obedience was fucking tactical, no matter what it fucking cost me to give it. You don’t get to pity me for doing what was necessary for your gambit to play out, and you don’t get to judge me either. And you sure as fuck do not get to consider me weak because the weakness England bred into me served you until it was too much for your morals to take. I did what needed to be done – you took the shot, you made the choice and I offered you a means to keep playing your game if you’d wanted it. But don’t think you saved me or that you can punish me for pushing your hand when I was doing exactly what needed to be done!”

This one is actually pretty easy to unpack because Charles spells it all out in how he emphasizes matters and at what point. One thing Charles hates about himself is “the weakness bred into him by England” – in other words, the fear of being a slave, the terror of being back in chains and forced into a position of subjugation and subservience. This is covered more in part two – but in short, Charles hates that he is still afraid.

On top of this, Charles hates that this fear, and his ability to submit, to genuinely bow his head, can be perceived as weakness or something worth pity. Being looked down upon or seen as lesser on account of what he has survived is one of the biggest insults Charles can come up against, and it infuriates him that those with no experience being stripped of their autonomy and freedom think they can pass judgement on those who have when they make particular choices or show certain vulnerabilities.

The harder point to unpack is the fact that Charles himself is vulnerable to certain kinds of fear, and does need to be comforted and cared for like any other human being, but feels obligated to conceal that need in order to appear strong and better avoid being degraded in any way. He does want someone to rely on – he does want to feel safe and at times, when the trauma is at the surface, he does want to feel like he has someone who can and will protect him. He hates that there is a part of him that desperately, horribly needs to be able to rely on and trust others – because it’s actually terrifying to reveal being vulnerable even when your reputation doesn’t revolve around being the scariest fuck in town.

He wants to rely on people, but he is too aware of how that can be manipulated and abused. He hates that he fears being punished as much as he fears being seen as weak, and he combats it preemptively in order to better protect himself from pain.

Part Two:

“I hate that there’s a part of me that’s still afraid.” He let that hang a moment, then, “I hated every fucking minute that man was on this ship, and I hated telling myself that — that the fear and the submission, that the bowing was just — temporary. Because it’s not. That shit’s always going to be a part of me, and that’s why I can’t fucking stand it."

As previously mentioned – Charles deepest point of self loathing is the fact that he is still afraid – but also, with that, the awareness that it will always be a part of who he is, a point that motivates him, a vulnerability that can be exploited and soothed in turns – but never wholly eradicated from what makes Charles Vane, Charles Vane.

I was gonna say more but honestly lads that about sums it up!

FMK for Charles: Eleanor, Flint, Max

{ FMK Meme }

“Fuck you again I guess,” He replied dryly. “Kill Eleanor.” He’d already fucked her, and she him, enough times to know that was the only acceptable answer. “Fuck Max, if she allowed it,” Which he highly doubted, she seemed a woman’s woman, “Marry Flint – even saying it sounds fucked.”

FMK for Charles: Jack, Anne, Teach

{ FMK Meme }

“Fuck you, Sky.” This was bullshit. The fuck kinda question – ? “Well I ain’t fuckin’ or marryin’ Teach.” So sure, let’s kill the man who made him the pirate he is today, why the fuck not? “And I ain’t stupid enough, or cruel enough, ta marry Anne.” The woman had enough shit in her life – not that she’d enjoy fucking him, which made the answer even worse. “Which leaves Rackham, who’s practically my wife anyway.”

Hey so. What are Charles’s favourite foods? Is there any food he particularly dislikes? Is there a type of food he’d probably like but hasn’t gotten to try yet? What’s the weirdest thing he’s eaten?

Listen, it is canon that this big lad loves himself a good and crispy apple. While he couldn’t exactly say why, fact of the matter is that cronch is what makes an apple so satisfactory. In general, he is a big fan of fruit and dried meat, fish, and cheese. That said he won’t say no to soup if it’s what’s available.

While he will eat just about anything that is put in front of him as a general rule, he actually tends to veer away from foods that are rich and heavy with creams and butter – sauces, in general, tend to make him suspicious. He likes to know exactly what he is eating and tends to consider sauces to be dishonest means of concealing bad food.

Charles has never had a mango but I don’t doubt that if he did he would not only love it he would knock a man out for the last one, jussayin.

Probably seal. Don’t judge him.

vane + smash or pass one (1) billy mcfuckin bones

{ Smash or Pass }

“Depends on whether or not he’s still a loyal man.” That’s delightfully vague, but he’d be lying through his teeth if he acted like there wasn’t some form of interest in Billy that went beyond fucking. He was a damn good pirate – a benefit to any crew, in fact, because of that damn dogged loyalty of his – but if he was still loyal, then absolutely not. Charles wouldn’t trust a Walrus man in his bed if his life depended on it – but a man who has a vested interest in keeping Nassau free, no matter the cost? Worth a smash.

QUEEN ANNE; smash or pass (for charlie boy)

{ Smash or Pass }

“How the fuck should I know?” Considering what little he knew of the woman amounted to a warmongering tyrant he hardly imagined an opportunity might arise in which he’d be finding out. Unless this was something he was supposed answer based on looks – in which case, he still didn’t fucking know, because when the fuck was he supposed to have seen a goddamn queen? “Probably a pass – I can’t see an English noblewoman being near entertaining enough and frankly, I’ve had my fill of their castaways enough to know the ones deeply embroiled in the idea of their importance will only annoy the fuck out of me.”

icb nobody has asked vane if he’d smash or pass the carrot top

{ Smash or Pass }

“That would be because nobody here is that fucking stupid, I would imagine.”

——Mun is going to interject here on Charles’ behalf because this is a very situational dependent one! And unlike Gates this boy respects the fourth wall for now and for the love of all things fluffy, let’s keep it that way.

In That Verse the chances are he might smash depending on circumstances and how it all played out. He may also take a smash in the verse where he fucks off to Lamara.
Pretty much everything else is a pass, mainly because they tend to always be on the opposite ends of the spectrum. However stranger things have certainly happened.

Vane: Smash or pass + rACKHAM I’M SO SORRY

{ Smash or Pass }

“What the fuck?” Alright first of all, who was the worthless sack of shit that plied Flint with enough alcohol to make him this kind of stupid, and secondly what did they put in the drink to ensure he would be the right side of reckless to voice that much stupid? Thirdly, “Pass, Jesus,” That was a visual nobody needed, least of all himself. “You think I’m going to fuck with Anne’s mess?” As a man with a healthy respect for what that woman could do with a knife, there was no way in hell he was letting his dick fly loose in an area she might be lurking – and if Jack was getting fucked, chances were, Anne would be lurking.

❌❌❌❌❌ Charles!

{ Sunday Kinkuisition }

Due to the fact I have covered a lot of this already in other headcanon requests cause ya’ll straight up have a favorite in this house, I am going to short form this real fast.

Confident partners. IDK if that counts as a kink but listen he has no interest in simpering or weakness in his life and that damn well includes in the bedroom.
Taking his time. He doesn’t get the opportunity to due this very often? For the most part its a very grab and go situation, especially with people who are straight up using sex as a manipulative measure. Letting the man actually fucking enjoy himself rather than immediately perform on your time goes a long way.
Slightly exhibitionist. Like very slightly and not really deliberately – he just really likes having sex where he can see the stars, which usually means more or less in the open and thus risking the chance of being seen, which doesn’t bother him in the slightest, so there is that.
Cleanliness. Is this a kink or a preference, who knows anymore? That said, baths and swimming being involved at any point is generally a win here.
Aftercare. Honestly he prefers partners who stay for the cuddles afterward. He’ll never fucking admit it, but that shit’s 90% of the reason he fucks in the first place, so….