Vtmb is on the brain as of late, had to draw my favorite guyyy, love me some Smiling Jack 😋 💕
no honesty I need him bad 👁️👁️
Anyways I’ve also been cooking up an oc for this game and hope to post about her soon but we’ll see I got a bit of stuff on the back burner as is haha..ha…
Jack is a lot of fun and he likes to have fun, don't you doubt it~
Smiling Jack was requested by Anonymous~
A = Aftercare (what they’re like after sex)
You have all limbs and not bleeding out? Good, that’s most Jack will care about after the act. Otherwise, he knows you’ll recover or you wouldn’t be bumping uglies with him in the first place. That’s not to say that he doesn’t care, but boinking Kindred has its perks and you being able to heal quickly is one of them. Pretty much same goes for comfort. He fully expects you to take responsibility for your own comfort and tell him before, not after, if something is not okay with you. If you don’t, well, he’s not taking the blame if you can’t communicate. However, he knows he can get pretty intense, so if he is the one to push boundaries or go a little harder than intended – then Jack will make sure that you’re alright afterwards and even apologize. He’s a tough guy, but still a nice one~
B = Body part (their favorite body part of theirs and also their partner’s)
While Jack is not a vain guy, he does mostly like his arms. Especially if he can pump them to make muscles look bigger so if you acknowledge how strong or tough he looks, you are guaranteed to draw his attention. During sex it’s even better. Cling to his forceps like your life depends on it and he will take notice of it. On you, well he’s a simple man, breasts. Size doesn’t matter to him much, but if they are soft and he can play with them, then that’s all he needs. Jack loves sucking on nipples, teasing them until they are so swollen and sore you start complaining and he also loves leaving bite marks on your breasts all over.
C = Cum (anything to do with cum, basically)
On you, in you, it doesn’t matter, just don’t ask him to use a condom. It’s a bother and a waste of time in Jack’s opinion and if you can’t handle normal things that bodies do (even kindred ones), then he’s not going to bed you the second time. For him, cum is as natural as a heartbeat, or the lack thereof, and he even finds it satisfying to leave you so filled that you’re overflowing. Or struggle to swallow it all down. All the same to him, as long as you’re thoroughly fucked by him.
D = Dirty secret (pretty self explanatory, a dirty secret of theirs)
A bit of a peeping tom, this one. He’s not going to go out of his way and stalk women in dressing rooms, but Jack won’t pass a chance if it comes his way. One look can’t hurt, right? It’s the naughtiness and the taboo of watching someone change or shower without them knowing is what gets to Jack and while he justifies it to himself as a little bit of mischievous fun, in truth it turns him on badly. If caught, he will deny everything, of course and that’s one little thing that he will never admit to how deeply he enjoys it.
E = Experience (how experienced are they? do they know what they’re doing?)
Jack’s been there done that. Nothing is new to him and he has heard, seen and done pretty much everything that is humanly and inhumanly possible. He likes to experiment and experience new trends just for the fun of it and to make eternity less boring. If he’s in a pranking kind of mood, he might even crash someone else’s orgy. But to put it shortly, Jack is every much a jack of all trades~
F = Favorite position (this goes without saying)
Truthfully, he doesn’t have a favorite position. Anything is good for Jack as long as he gets to fuck you, but if asked directly, he would probably just say that as long as he can toy with your breasts, then he’s one happy man. That’s one consistent thing with Jack, he will always try to paw at them no matter the angle and that’s honestly the only true preference he has when it comes to how in terms of positions.
G = Goofy (are they more serious in the moment? are they humorous? etc.)
Serious sex with Jack is pretty much impossible. He will also be all smug about it if he can keep you smiling through the experience. Nothing in life is permanent, even if you’re technically immortal, so why be serious when you can have fun? That’s the attitude he brings to the bedroom as well and even if you don’t appreciate it in the beginning, you will soon learn to enjoy the laidback attitude that Jack has about everything sex related. From filthy jokes, to making fun out himself and you during the act, everything goes as long as it’s not actually insulting or upsetting and will make it up to you if one of his jokes goes too far.
H = Hair (how well groomed are they? does the carpet match the drapes? etc.)
Grooming? What’s that? Besides showering, and even that not sought out consistently, Jack sees no reason to waste time getting all primped for it all to grow back the next evening. Since he lived through many centuries and started as a pirate, Jack prefers to go au naturel. Why waste time grooming one’s appearance when he can do something useful instead. So when you bed him, you get him as he is – hair, dirt on his hands and all. You can of course send him to the shower first and he will grumble how it’s ruining the mood, but won’t fight it too hard.
I = Intimacy (how are they during the moment? the romantic aspect)
While it’s already mentioned that Jack prefers to keep the mood light, he has a softer side that does come out if you spend enough time with him. Entire intercourse won’t be filled with soft words and promises, but there will be moments where Jack wants you to know just how exactly you make him feel. So he will reassure you, tell you how much you mean to him or that you’re everything to him. As long as you don’t push him to be more sentimental, Jack will show the depth of his feelings for you when he feels like it and when it’s the right time.
J = Jack off (masturbation headcanon)
Loud and proud about it. Jack won’t hide the fact that he likes jerking off and does it often as well. What is eternity if you don’t enjoy yourself, right? Well, he makes sure to enjoy it in all ways possible, so it won’t be rare to find him with his cock in hand. What’s more, he really really likes watching you touch yourself as well, or masturbate together. Just don’t be shy about it, Jack wants to see and show everything.
K = Kink (one or more of their kinks)
And while on the topic, Jack’s kink is definitely watching you masturbate in his presence. If you do it slow, sensual and show him everything, tell him how exactly you’re making yourself feel, that will make the man absolutely feral. He will try to hold back until you make yourself come, but that’s quite rare for him to have this kind patience. More often than not, if you prolong it long enough, Jack will be on his knees before you, your fingers pushed aside and his mouth replacing them. So lay back and relax, he will take care of you.
L = Location (favorite places to do the do)
Somewhere risky and with a chance of getting caught is what makes Jack’s cock hardest. He likes the thrill and excitement so much, he will prefer a filthy club bathroom over the comforts of bedroom and a soft bed. With you bent over the toilet bowl or sat on a sink, it doesn’t matter, and that’s just one example. Dark alleyways, under bridges, in the forests, in wet meadows, if there’s even a fraction of a surface and as long as it’s not boring, Jack will fuck you on it. And even more so because he does not ignore his urges. So if he suddenly gets desire to fuck you right here, right now? That’s exactly what he will do. Your feeble protests about being seen does not affect him whatsoever and if anything, they arouse him even more.
M = Motivation (what turns them on, gets them going)
A random thought of you moaning his name will get Jack going and you’ll quickly find yourself being pulled away to the side or, if you’re somewhere in relative privacy already, immediately with your underwear around your ankles and his cock inside you. In short – what turns Jack on is pretty much a random thought that will get him all worked up and needing immediate release. He’s not immune to your teasing and flirting either and is quick to stop the games and fuck you. When it comes to Jack wanting to fuck, he’s like a match, ready to be lit at any time.
N = No (something they wouldn’t do, turn offs)
While Jack’s game for almost anything, surprises included, heavier kinks is something that he would prefer if you talked to him about prior and he will do so as well. Sex is about fun for him, fun of pleasure and the experience, so being thrust in something uncomfortable or even potentially dangerous, will make him nervous and less willing to trust you again. To Jack, consent and boundaries are sexy and he will expect you to be of the same mind.
O = Oral (preference in giving or receiving, skill, etc.)
Giving, getting, it is all the same to Jack as long as you are both having fun. Point to be made here is that he enjoys oral as much as he enjoys penetration, so both are equally good and he will eagerly participate in it. As someone who knows exactly what he’s doing, Jack will make you feel pleasure unlike any before and if needed, will guide you through how to pleasure him. He’s also absolutely willing to let you find those things on your own as well, it’s part of the journey for him and maybe even more fun than just to tell you how to suck him off and where.
P = Pace (are they fast and rough? slow and sensual? etc.)
Whatever suits the mood. Jack is versatile enough and he will let the setting guide how sex is going to proceed. Generally, though, it really depends on what aroused him. If it was you flashing him – then he will be fast and rough, wanting a quick relief for you and himself. If his desire is driven more by feelings rather than just a hard cock, then he will take things slower, relishing every moan and every shudder he can entice out of you. Jack is also not averse to being asked to slow down either and will comply gladly, as long as you two are on the same page and comfortable.
Q = Quickie (their opinions on quickies, how often, etc.)
Big fan and while he doesn’t specifically try to arrange things for them to happen, it just sort of… happens. With Jack, when sex happens is pretty much unpredictable, and so you will find yourself in some corner, with Jack’s hand around your mouth to muffle your moans, pounding into you, without as much as a prior notice. Even if you try to tell him about possible effects for taking such risks or even getting caught, he will just laugh and dismiss it, while asking you what you have to be ashamed for. For him, sex is one of the experiences that he partakes in freely and he absolutely thinks you should too, without shame, embarrassment or worrying about consequences.
R = Risk (are they game to experiment? do they take risks? etc.)
As established before, Jack is very much into experimenting and experiencing everything sex can offer. While yes, he does very much prefer if more challenging things get discussed in advance, he will still be game for nearly everything. Just don’t damage him permanently and don’t get too freaky with blood magic (if you possess it) and he’ll be willing to try even most eyebrow-rising things.
S = Stamina (how many rounds can they go for? how long do they last?)
You may as well not even bother counting how many rounds Jack can last. He has the science of stamina usage down to perfection and if there are “refreshments” option during the night (such as a bloodbag or similar), then you two might go for days if you didn’t need to rest during the day. So he can go as often and for as long as he wishes, as long as you are capable of it. That’s not to say that Jack doesn’t get sore if it takes too long, but with right motivation and arousal, he will outperform many younger kindred by a mile and then some.
T = Toys (do they own toys? do they use them? on a partner or themselves?)
Toys, no toys, fingers, mouth, on you, on himself, on whoever else is present, as long as it’s exciting and pleasurable, then Jack will agree to it or may even suggest first. He doesn’t own toys though, preferring to have sex in spur of a moment rather than plan it and thus he is not the one to just have dildos lying about. But if you are willing to take the responsibility of assembling and managing the arsenal of sex toys, then he won’t say no to that either, maybe even contributing with an item or two of his own choosing. However, you will be the one to clean them afterwards as well, so better be ready for that.
U = Unfair (how much they like to tease)
Jack is all about teasing, but especially loves when you do it. There’s something so arousing about his partner going all out, trying to make him beg for release. Completely confident in you, Jack is rejoiced when you take initiative just as much as he does and will let you do whatever it takes to have him pleading for your touch or for an orgasm. It’s all part of the fun and he’s comfortable reversing the relationship dynamic that usually has the scale leaning to his side.
V = Volume (how loud they are, what sounds they make, etc.)
Shutting him up is the challenge here. Jack does not really care who hears him or yourself, even if being loud might lead to you getting caught or exposed. And he cares even less if getting caught might lead to actual trouble. If anything, it’s the thrill that makes Jack overeager to not be ashamed or hide away from expressing himself. Even more so because he thinks a good partner should let their lover know if and how much they are enjoying the act. Growling, moaning, hissing are all the things you will hear and Jack won’t be embarrassed about them at all.
W = Wild card (a random headcanon for the character)
Jack is very much into roleplay and that includes dress up. As already established, he likes to have fun and especially when having sex, so playing around in different costumes and throwing cheesy lines at each other is what combines both for him – the fun and the sexy. He will have especially lots of fun buying and wearing cheapest sailor or pirate costumes, poking fun at himself, even more for his own amusement than your own, but in the end it’s just good times with him.
X = X-ray (let’s see what’s going on under those clothes)
Bigger than average, but not too much. He’s not going to split you in two but can still give a very good wienering, especially because he doesn’t think that only his cock is enough to pleasure his partner. It’s equally even in thickness, curved to the left and when Jack is aroused, the veins along the shaft show quite prominently.
Y = Yearning (how high is their sex drive?)
Pretty high sex drive but only if he’s having a good time with you. If he’s single, so to speak, he won’t be going around looking for simple hookups all too often, but with a right person Jack not only can relax because he trusts you, but also he doesn’t stick around someone he doesn’t truly like, therefore his sex drive will definitely increase simply because he doesn’t have to be cautious.
Z = Zzz (how quickly they fall asleep afterwards)
Absolutely first to sleep, slipping into his daysleep before you even get out of bed to clean up. Things like that can wait until the evening for Jack and he will be out like a light the moment his eyes close. He’s a late riser too, and sometimes you even have to wake him so that you can go about your business for the night. But one thing is always consistent with him – you will fall asleep and wake with Jack’s arms around you.
Jack, Strauss, Andrei, Velvet, Nines and Beckett with a hunter who tries attacking them with a string of garlic bulbs?
[I am so so sorry this took so long to write! I had to take an impromptu break for a month or so.]
Jack- Eats it. Not really, but makes you think he does. The order of events goes: you're both fighting, you hit his face with the garlic, he bites some off mid-hit to show you how stupid it was to think garlic works, then he decks you in the face, knocking you out cold. He'll leave you alive though. He thinks the whole thing was hilarious and sort of hopes it will happen again.
Strauss- It's like he got a grocery delivery for his next rite. Garlic, various other supplies, and a whole person's worth of blood? He'll be good for at least a week!
Andrei- If you could manage to get close enough to him to even do this, he'll be somewhat impressed. He would have you embraced (by someone else, certainly not by himself). Not only would that add to his hoard of grunts, but also he is amused by the thought of you now being a low level vampire being stalked by those who were once your fellow hunters.
Velvet- How dare you?! The scent of garlic does NOT match her perfume! Real talk, while she could defend herself if she had too, she is also Isaac Abrams' adopted childe. That probably means that if you were to get that close to her, there would be so many of his people on you in the blink of an eye. Being from one of the more sensitive clans, the strong scent might make her nauseous, but that's about it.
Nines- Breaks your arm and walks away. Completely deadpan, expressionless face; he grabs the arm you just swung at him, crunches the radial, turns around and leaves. If using garlic is the level of stunt you're pulling, then you won't be a problem for him anytime soon.
Beckett- Hits you back with the garlic, turns into a wolf while you're dazed, and bites you. Short, sweet, and to the point.
