Always glad to see another imagine blog! Your enthusiasm is infectious! I'll request some modern headcanons for Itachi, Sasuke and Shisui, SFW/NSFW. Good luck with your blog, though I'm sure you're too good to need it :D
This one is really long and I waited until I released all the SFW and NSFW for Itachi, Sasuke and Shisui before doing this one, the NSFW ones are a little shorter since I’ve written some headcanons for that already! I totally love modern AU questions and for such great characters too, they are so fun! Thank you anon!! :)
Shisui, Itachi and Sasuke Modern AU SFW and NSFW
Shisui would likely be a middle school or high school teacher, he just loves teaching people and entrusting knowledge to the future generations – he fundamentally understands how important they are. He gets along with people and is very social in almost all aspects of his life. Loves his students to death, and he’s the teacher that brings his students candy, stays after class to help them and he will guide them in any way needed. Shisui encourages his students to talk to him if there is ever a problem or they’Re being bullies, he can be pretty protective.
He would definitely be in after work football leagues with his co-workers and friends – he always makes sure Sasuke and Itachi are invited. He just enjoys competing and he can get a little obnoxious about playing by the rules. But he definitely has the most sportsmen like conduct when it comes to playing games.
When Shisui finds a partner he’s extremely loyal to his partner, he would almost rather die than even consider cheating on them. When his partner is there, nothing else matters, he wouldn’t even care if he got a hundred texts, he wouldn’t bother to read a single one if his s/o is in his presence. He is a really good listener and enjoys the stories his partner has to tell. Of course, sometimes Shisui does put his career first because he’s dead serious about being a good teacher, so he might need someone that is willing to understand that.
He’s not shy about spending money and wants to treat his partner like a queen – to him, they deserve the absolute best of everything. Of course he does have to worry about not breaking the bank, so anything within reason is good.
Shisui loves having sex around different places in the house. He sometimes will take his partner while they are on the couch watching tv. When he’s on the couch he is a fan of being more on top, he really enjoys having his partner’s legs wrapped around his waist so he can thrust deeper. Again, he loves loud sex so the more he can hear his partner and the less he hears of the tv the better.
When he’s giving oral he likes to leave tiny bits and licks on his s/o’s inner thigh. The bites aren’t enough to break the skin, but enough to leave a little reminder that he was there.
Sometimes he will have sex in the shower, he finds it sexy and it also means no cleaning up, which is a plus. He kinda has to pin his you to the wall so you don’t slide around, but he still enjoys the feeling of your wet, hot skin against his own.
Itachi really wanted to become a teacher just like Shisui, but his father refused to allow him to do that. Fugaku told Itachi that ‘he wasn’t going to allow his son to be a glorified babysitter.’ Instead Itachi was pretty much forced to go to business school, which was very simple for him since he was a gifted academic. Currently he’s the Vice President of Finance at some average sized corporation that makes cleaning products. Even though he’s the best Vice President the company has had in fifty years, he secretly hates his job.
He spends the majority of his free time with Shisui or Sasuke. When Itachi isn’t working late he goes to pick-up games with Shisui and plays football with him. If him and Shisui are on opposing teams, Itachi usually loses – he doesn’t mind because he isn’t as competitive as Shisui. Afterwards they usually go out for a few drinks and swap stories about their week – Itachi loves all the funny stories of Shisui’s students.
If Itachi finds a s/o he will pick only the kindest person, and they definitely have to be someone that Sasuke would approve of. He would probably take them over for dinner at his parent’s house frequently, Itachi really emphasizes the importance of family, he feels it’s an essential pillar in his life. His mother would have to love them, but it wouldn’t break the relationship if Fugaku didn’t approve, Itachi knows his father is a hard man to please.
Itachi is the type of man that makes women believe chivalry isn’t dead. He’s the most polite gentleman around his s/o and he treats them like a goddess on a date. He always brings flowers with him, uses his ‘please’ and ‘thank yous,’ he holds the doors open, and he always picks up the tab. He really enjoys listening to his partner and he never interrupts or tells his partner their opinion is wrong because he respects them deeply.
His favorite thing is finding new ways to seduce his partner. Sometimes Itachi tries some dirty talk or whispering very sensual things into your ear about how sexy you look tonight. Often he will start slowly undressing in front of you, usually starting with his jacket and shirt – and he will walk around a lot shirtless to keep you entranced and gawking.
Loves fingering his partner when it comes to foreplay – he also will add a little bit of tongue action in there. But Itachi likes the feeling of being inside his s/o is probably one of Itachi’s favorites, especially when they have an orgasm while he’s fingering them.
Itachi has a weakness for really good handjobs. Like he won’t try for them or anything, he doesn’t like forcing his partner to do anything, but he is so elated when his partner does them.
Sasuke would probably be some type of FBI agent or police officer. He likes how nitty-gritty and cutthroat things can get when tracking criminals or catching people committing crimes. He wouldn’t tell anyone but he thrives on that drama – the whole idea of bringing people to justice really motivates him.
Naruto is definitely the person Sasuke spends the most time with – they usually get drinks together, and Naruto gets really obnoxious and hammered at the bar so Sasuke has to drag his ass home. But that’s only when their schedules coincidence; Sasuke works night shifts often so he doesn’t get all the time in the world. If he isn’t with Naruto, Sasuke’s with Itachi and Shisui. He does pick up games of whatever sport his brother feels like going to.
I don’t think Sasuke would really try to find a special person in his life, it would have to happen naturally. Like Sasuke would just start hanging out with you and then it would happen more frequently. Things would eventually get intimate and then he’d probably be like ‘we’re dating, just so you know,’ and it would just continue from there.
He can sometimes be really attached to his phone, mostly because of work and the fact that Naruto is always texting him the stupidest shit, but he has a bad habit of being on his phone a lot. He works really hard to break the habit when his partner is around though – he knows it’s unbecoming.
If things are in the heat of the moment, Sasuke will go straight for having sex against the wall. He finds it exhilarating and he really likes being in control of how things are progressing – also he can kiss your neck while he has you pinned against the wall.
Sasuke has a bit of a kink where he likes to cum on his partner’s chest or stomach. He likes to see how his cum looks on them and he can see their reaction too. He’ll only do it if he thinks they will be okay with it, otherwise he won’t – and of course he’ll help clean up afterwards.
Is a little curious and wants to try anal once, but doesn’t want to tell his partner. Sasuke doesn’t like directly telling his partner what he wants. Plus, he doesn’t like the thought of his s/o not liking or enjoying the experience.
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