#helluva boss headcanons

[vikkirosko]

Headcanons of how would Stolas, Fizzarolli, Asmodeus, Sir Pentious, Husk, and Alastor react to their crush asking "Why me?" after he confessed to them? Not because they don't like him back but they feel like he deserves someone better than them!

Headcanons Why me?

📻 Alastor x Reader 🎙

Getting a confession from Alastor was the most unexpected event in your life. Even though you had feelings for him, you would never have thought that such a thing was even possible. He continued to look at you with his usual smile, waiting for at least some kind of answer from you, and you could only ask why you

Your question made him laugh, as if you had asked something so obvious that it was even funny. He asked you directly what you meant, to which you confusedly told him that you were an unsuitable partner for such a charismatic person as Alastor. Your answer made him laugh again, which made you even more embarrassed

Alastor did not torment you with suspense for a long time and told you that it was his choice and if it were not so, you would not be having this conversation now. He was sure of what he was experiencing and was only waiting for your answer

You didn't know how to react. You weren't completely sure that it wasn't a joke or something like that. The only way to find out the truth was to take a chance and tell him how you felt about him

🃏 Husk x Reader 🥃

Husk didn't admit even to himself for a long time that he had feelings for you. He denied them, but eventually admitted to himself that he really likes you. Now he had another difficult task, namely to tell you how he felt about you. He did it quickly, abruptly, when you were alone in the bar. However, your reaction was not what he expected and it put him in a dead end

You only asked him one question. Why do you. You claimed that Husk, despite all his rudeness, was a good man and deserved a good partner, which you did not consider yourself to be. Husk was frankly surprised that you saw him in a completely different way than he perceived him. Perhaps it was because you were in love with him, but Husk was not going to go back on his words because you considered yourself unsuitable for him

Husk directly told you that he feels these feelings not for someone else, but for you, which means he was not going to give up his feelings so easily, especially if the only reason for this was that you did not consider yourself a suitable partner for him. He asked you directly if you had the same feelings for him as he had for you, and when he received an affirmative answer, he nodded with satisfaction

He understood that you were worried about him, but Husk intended to decide for himself who was the right partner for him and who was not, and you were the person he wanted to see next to him, and if you felt the same way about him, then there were no reasons why you couldn't be together

🐍Sir Pentious x Reader 🎩

Pentious took a long time to tell you about his feelings. His feelings for you were strong and he sincerely wanted to tell you about them, and his subordinates often supported him in this, so he was able to muster the courage to tell you everything. But when he confessed to you, he saw how quickly the emotions changed on your face. You were surprised, confused and excited

You asked him why you. You stopped talking, so he asked what you meant. To his question, you took a deep breath and spoke. You said he was smart, brilliant, funny and sweet. In your eyes, he was wonderful, despite the cute oddities in your opinion, and he deserved the best partner, which you were not, at least that's what you said yourself

When you looked up at him, you saw tears in his eyes. He was ready to cry. He couldn't remember the last time someone had said such words to him, especially the person he really liked. Pentious asked you if you had mutual feelings for him, and after receiving your affirmative nod, he hugged you tightly

He was happy that you reciprocated and now you could be together. Pentious was as happy as ever, rejoicing that he was able to confess his feelings to you. He was sure that no matter how gloomy his day was, it became brighter next to you

🦉 Stolas x Reader 🎩

Stolas had few opportunities to experience real feelings. That's why when he realized his feelings for you, he decided not to delay the confession. He knew he could have missed his chance, so he decided to take a chance, but your reaction surprised him

You were very confused and started talking fast. You told him that you weren't the right partner for him, even though you felt the same way about him, and it wasn't about social status. You thought he was wonderful. He was handsome, smart, kind. He deserved the best partner. Better than his almost ex-wife and better than you, at least that's what you claimed

Stolas listened to your monologue with surprise, after which he smiled gently and took your hand in his. He told you bluntly that there weren't many pleasant moments in his life, but after meeting you, his life became brighter and he hoped that there would be even more of these moments

He felt warm in his soul when he saw your embarrassed expression. Stolas was glad that his feelings were mutual, because you said it yourself, but he was even more pleased that you sincerely wished him happiness. He hoped that together you could become happy

🐓 Asmodeus x Reader 💕

Asmodeus has been planning to confess his feelings to you for a long time. He wanted everything to go beautifully, because you deserved the best, which is why he prepared a romantic dinner for the two of you, cooking the food himself. Ozzie behaved gallantly and politely when you came, sincerely hoping that you liked everything, and when dinner came to an end, he honestly told you about his feelings for you, but your reaction surprised him

You asked him why you. Asmodeus didn't have time to answer you when you started talking. You thought he was wonderful. He was smart, handsome, talented and more, and he deserved someone better than you, much better than you, at least that's what you said yourself

When you finished your monologue, Asmodeus couldn't help but laugh, after which he hugged you. He was glad that you had such an opinion of him, but he knew that he loved you and in his eyes you were the best and he wanted to see you next to him and not someone else whom you considered better than yourself

Ozzie hoped that you would be able to believe in yourself and not continue to deny his feelings. He saw that his feelings were mutual and it made him happy. Asmodeus was sure that you would be really happy together

🎪 Fizzarolli x Reader 💟

You and Fizzarolli have been friends for a long time and he knew that he was in love with you. Fizz didn't know how to tell you that he liked you, and so he was silent for a long time, but he realized that he couldn't keep silent anymore, so he decided to confess to you about all his feelings that he felt for you

When he stopped talking, he saw how red your face was. You were confused by his confession and clearly started to worry, but instead of responding to his feelings, you asked why you. You were talking fast, embarrassed, obviously nervous, but you kept talking. You told him that he was a wonderful man, he was funny, handsome, talented and deserved the best partner, much better than you

When you finished speaking, you saw that Fizzarolli was as confused as you were. He was embarrassed that you thought he was so wonderful, because he didn't think he was as wonderful as you said. He gently took your hands in his and shyly said that his feelings for you were sincere and that you were the most wonderful person he had ever met

Fizz was genuinely glad that his feelings were mutual. He wanted you to be happy, especially after you expressed your uncertainty about his choice. He wanted to do as much for you as possible, at least as much as his powers allowed him

[inferno-0]

⌞ SATAN X READER ⌝ ── | Tranquillity |

Guys, I'm not turning him into a dog, I'm just giving him what he wants most...

➤ Satan's wrath was familiar to many of the inhabitants of hell, his roar and flames burning from all four eyes sent him straight into the very heat of fear, the victim of which could die without even feeling any blow from his side. This is, let's say, an influence that has been worked out for several hundred years. Even those who are already used to seeing and feeling this cannot keep themselves under control to create a mask of neutrality, they still bend their knees and shrink into themselves, just not to see this elongated muzzle full of sharp teeth. Satan is used to this kind of environment, and sometimes he can get really angry about it. It's just that not being able to control himself makes him turn into a monster even more. The lack of calm and all that, again, unsettles him.

➤ The warm air from his nostrils has already come out several times, enveloping you from all sides. He does this when he tries to calm down, closing his own mind full of devils, and just enjoy your being next to him. Satan feels your hand moving unwaveringly above your jaw, tracing various patterns on the scales, accidentally stopping at impassable joints. His massive muzzle was on your lap, pressing right against your stomach. The vibration echoed from his body as your fingers gently wrapped around his horns and returned to the same place again. Thick claws wrapped around your sides like a toy, pressing even closer. Yellow eyes watched your surprised sigh, waiting for some fear or sign of it, gradually understanding what exactly it should do in the end, but instead it gets a bright smile on your face and another gentle touch, from which it could possibly melt despite its structure full of magma.

➤ This moment only makes him enjoy and not let you go. Satan could never have imagined that his complex temper could actually descend with anyone other than Yoirt. Honestly, the Sin of Wrath is pleasantly surprised by this state of affairs and is unlikely to be able to let you go in the near future. The softness of your hand sends him straight to sleep, where it is even calmer and better than among the demons of hell. But he prefers to enjoy the moment with you and share the peace that you give him without wanting to get something in return. Your resilience in front of his character excites and makes him love even more, get used to your presence and just tie himself in a strong knot. Satan finally finds temporary rest. His silence was long and clear to you, as you knew that he absorbed all the moments with you, enjoying the caress.

[thepenguinwriter]

Mammon x m!reader, where reader is just someone who's really apathetic all the time and isn't hurt easily by anything but has anger issues, and when someone messes with his partner or him reader gets really aggressive/angry? Please and thank you!

`` 𝐒𝐦𝐢𝐥𝐞! ``

╰┈➤✮ 𝐌𝐚𝐦𝐦𝐨𝐧 𝐱 𝐦!𝐫𝐞𝐚𝐝𝐞𝐫

╰┈➤✮ 𝐇𝐞𝐚𝐝𝐜𝐚𝐧𝐨𝐧𝐬 : 𝐚𝐩𝐚𝐭𝐡𝐞𝐭𝐢𝐜 𝐫𝐞𝐚𝐝𝐞𝐫 𝐰𝐢𝐭𝐡 𝐚𝐧𝐠𝐞𝐫 𝐢𝐬𝐬𝐮𝐞𝐬

╰┈➤✮ 𝐂𝐨𝐧𝐭𝐞𝐧𝐭𝐬 : 𝐦!𝐫𝐞𝐚𝐝𝐞𝐫, 𝐚𝐩𝐚𝐭𝐡𝐞𝐭𝐢𝐜!𝐫𝐞𝐚𝐝𝐞𝐫, 𝐫𝐞𝐚𝐝𝐞𝐫 𝐰𝐢𝐭𝐡 𝐚𝐧𝐠𝐞𝐫 𝐢𝐬𝐬𝐮𝐞𝐬, 𝐩𝐞𝐨𝐩𝐥𝐞 𝐠𝐞𝐭𝐭𝐢𝐧𝐠 𝐛𝐞𝐚𝐭𝐞𝐧 𝐮𝐩, 𝐛𝐫𝐢𝐞𝐟 𝐦𝐞𝐧𝐭𝐢𝐨𝐧 𝐨𝐟 𝐢𝐧𝐣𝐮𝐫𝐢𝐞𝐬

- ☆ At first, Mammon didn't like you. At all.

- ☆ You were always so weirdly unemotional, he could never figure out what was going on with you

- ☆ You were just a simple bodyguard to him, so he honestly didn't pay much attention to you

- ☆ Until one day, a random imp started yelling at you because he wanted to see Fizzarolli

- ☆ You handled the situation well, not reacting at all until the imp started insulting you and your family with very harsh words

- ☆ Mammon watched as you punched him, then, before he could react, twisted his arm and left him screaming in pain

- ☆ Safe to say, he was impressed and wanted to know more about you now

- ☆ You obviously noticed the change in his behavior, how he wasn't as rude or dismissive of you now

- ☆ In fact, after a while, you'd be sitting right next to him on shows, his arm wrapped around you

- ☆ Of course he was the one to bring up dating first as if it was nothing

"You're really hot, you know. If you were a doll, you would be sold out in a day! So-"

"I'd rather not be one of your bots."

"Would you be my boyfriend, though?"

- ☆ From then on, Mammon was your no. 1 priority

- ☆ You were always by his side, making sure no freaks could get him away from you

- ☆ And if anyone ever tried to hurt him or do anything like that, you would beat them up without shame

"Ya know, it wouldn't hurt for you to smile once in a while!"

"Like this?"

"....nevermind."

A/N: Woo, my first Mammon request!! It was fun to write for this guy. Though I do feel like he might be a lil ooc here too.. lmk! Also, the last dialogue is a reference to something.. idk how many of you will get it, buuut if you do, ily. Thanks so much for requesting! <3

Divider by @/rookthornesartistry

[drgarrisonandpaul]

Rolando~

(( Minors DNI, slight NSFW ))

I haven't seen any x reader headcanons about this beautiful man yet, so I have decided to throw my hat in with some suggestions

(The picture is this video's thumbnail: https://youtu.be/2MuIZ9r64fE?si=0xGxufq_Zn7Z-Pla )

As a partner, it doesn't really matter if you met in human form, demon form, in Hell, on Earth, or whatever else: he liked you because you stood out a little bit. Something about you was interesting enough for him to bother you. His mechanism of romance comes off as harassment at first and, hell, it might just straight-up BE harassment. How you react to his attention is the key, but he wants to make you squirm and shiver a bit. Maybe lean away from him so he can lean it. He is, in all senses, a creep and a bastard

He seems like the eccentric type that hates to be ignored. If you act like his attention is normal or okay at first, it'll piss him off... but it'll also intrigue him to keep going

On a date, Rolando is surprisingly awkward, but only because he has no idea what to do with his hands. How does he sit? Why is he even here??

That tongue thing we saw is PERSISTENT in his relationships, you might as well make What's Your Fantasy by Ludacris his theme song because he WILL lick you from head-to-toe like a needy cat, just... much slimier

Not much is known about eels and their lives, their mating habits, etc. Every time we think we know something about them, we get blindsided by crazy shit like 'these 4 are actually the same species' or 'they only bang in the deep dark' and Rollo is no different. Every time is VASTLY different. Rough? Why not rougher. Why not so soft and slow that it leaves you breathless and unsatisfied. Why not Zoidberg?

He doesn't care for meeting your parents or getting married and he WILL leave you on read just to fuck with you. Mixed messages are his specialty in a relationship, you'll be love-bombed and then promptly not hear about him for the next 2 weeks

Most of his nicknames are a little mean, he has a degradation kink FOR SURE. The type to call you 'porky', 'mouse', 'scatterbrain', or something, mean it with his whole chest, and love you anyways

Avoidant attachment style. Probably in denial that 'love' is a thing he can feel. Will kill more people in the meantime while he figures out his emotions

I see him as a switch in the most confusing sense possible. I see everything he does as a little mysterious and without reason. Just for the fuck of it, just for the thrill. He'll happily start out as a dom, but as soon as you tilt that beautifully underbitten chin towards you and tell him you hate him, he has no idea what to do

It's been a while since I've written headcanons, please excuse my writing, I know it's not the best quality. But I do LOVE this character

[xfangheartx]

Fizz and Ozzie adopt Oliver headcanons

I'm sure a lot of us have had thoughts of Fizz and Ozzie adopting this cutie patootie:

Well, here are my headcanons on what happened when Fizz and Ozzie adopted little Ollie!

It happened about more than a week after Fizz quit being Mammon's brand boy.

Fizz just fell in love with Oliver since the moment he met him at the clown pageant and he hadn't gotten him out of his mind since.

In fact, not knowing what happened to Oliver or whether he was safe made Fizz restless and worried for days, which Ozzie noticed.

After a while, Fizz asks Ozzie if they can do some digging around, and they eventually find out that Oliver is an orphan. His parents gave him away because they didn't want to deal with having a deaf child.

Thankfully, his caretaker is very nice.

Fizz gets everything prepared for having a child in the house. He makes a separate room for Ollie, buys him all kinds of toys, and even helps Ozzie learn sign language.

They also try to hide all the sexy stuff. Even if it's Hell, Ollie is still a little kid and they don't want to expose him to that until he's at least 13.

Ozzie is actually a bit nervous about having a child. He may have looked after Charlie when she was little, but he still thinks that he might not be ready for one. He ends up going to Lucifer and Stolas for advice since they're both fathers.

They say that parenting is a lot of work, no matter how old your children are, but in the end, it's worth it, and Ozzie takes this to heart.

Eventually, they arrive at the orphanage where Oliver lives in Greed. The other kids get along with him pretty well, too. Some of the children even talk to him in sign language so that he feels included.

When Fizz walks up to Oliver, he's surprised, but he's also very happy. When he asks him what he's doing at the orphanage, Fizz signs to him that he and Ozzie are going to be his new dads and are taking him home with them.

Oliver is so surprised and happy, that he just starts crying, but Fizz hugs him tightly, and so does Ozzie.

After the paperwork is all signed, Oliver is officially adopted.

He loves his new home and his new dads, who spoil him rotten (Fizz more so than Ozzie).

Verosika even comes to babysit, once in a while. She's surprisingly good with children!

Also, Ozzie made Oliver some cochlear implants so that he could hear a bit better, but he and Fizz told him that he could still use sign language.

Fizz teaches Oliver some circus tricks in their downtime, knowing that his newly adopted son still wants to be a clown.

However, he warns him not to sign up with Mammon. He will NOT make the same mistake twice.

[nightqueen1221]

Can we please get Loona General Relationship Headcanons please? Thanks for your time!

I am so unbelievably sorry this is so late.😭😭😭 I was going through some mental shit, it was difficult, but I'm getting back on track.

-She is very rusty on how a relationship works. She hasn't had a very healthy relationship with most people in her life, even though Blitzø tries his best to be a good father.

-She steps into it very nervously. She is super cautious on everything she does.

-She is clearly doing her best, even at moments of outrage, she'll come and apologize a few hours later.

-She texts about every week if she can't be near you. Mostly little things like, "How r u? Miss u❤️"

-While she absolutely loves going out to eat or shopping as dates, her favorite are watching movies, all cuddled up in a blanket with popcorn on the table. (Blitzø totally isn't taking a billion pictures behind her back.)

-Head nuzzles are a must. Both her hands on the side of your face with your foreheads pressed against one another. She would whisper words of love and adoration.

-She is totally fine with sharing things like clothes or makeup with you, as long as you give it back.

-Half of the photos in her phone are of you or the two of you. She often looks at them before she goes to sleep or after a phone call. (She would kill before she would admit this.)

-Is honestly very chill about all of this on the outside, but can internally be very panicked. She doesn't want to break up over a mistake or misunderstanding, even though this is a normal fear, she's experienced it far too much in her life.

-She says that she doesn't talk about you too much, but she'll talk about you to anyone who wants to listen.

-The downside might be Blitzø. She will be very careful about how the two of you meet. She would take weeks just to convince Blitzø to not make himself look like an idiot infront of you.

-He doesn't have an issue with you, but meeting him would start off with a handshake and him saying, "Hi there! Name's Blitzø, the 'o' is silent." Before pulling you closer for a 'private conversation' going something like, "If you ever break her heart, no one will be finding your body." Before he goes back to being more cheerful.

-I wouldn't say she's jealous, but she is definitely protective of you. Seeing someone flirt with you makes her angry but also a little insecure sometimes. She thinks that maybe you'll find someone better.

-She usually just drops very non casual hints that you're with her, while she stares at the person hitting on you.

-While she might want to punch someone's lights out for they way they talk about you, she won't get physical until they do. Then I don't think anyone could really tear her off them.

-Her tail sometimes wraps around you unconsciously. Mostly around the legs or rarely hip.

-She doesn't kiss all the time, but likes to do at as a form of greeting or goodbye. As I said earlier, it's head nuzzles that she loves the most.

-She's more carefree around you. It's like a breath of fresh air to be with someone that really loves her, besides Blitzø.

[pinejayy]

Striker Headcanons

Some SFW and NSFW Headcanons of this sexy man my lord.

SFW

Striker was quite harsh when you guys first started dating, he didn’t want any of that lovely dovey couple stuff. Such as no hand holding, no cuddles, no kisses and no nicknames. Honestly you were double guessing yourself why even be with this guy.

But as time passes by you grew onto him. He absolutely adores you now. He always wants to be by your side. And yes he’s still quite harsh with you, but he’s toned it down. He’s more like playful rude with you.

But if anyone dares to flirt with you or even lay a eye on what’s his he’ll give them a slow painful death. No one and I MEAN NO ONE can take away his prize.

Striker loves giving you kisses, especially around your neck. He loves the way you react. Especially the little whimpers and giggles. “Stop that tickles!” You would giggle out, and it would always make him smirk.

You like using cute pickup lines on him! “You're under arrest! For stealing my heart.”

Since you’re his prize, he loves to spoil you rotten. Buying you expensive gifts and he loves taking you out on dates. He definitely loves showing you off to the other imps.

You on the other hand get flustered when he shows you off. A sexy man showing you off? I mean who wouldn’t get flustered.

You love the way he talks to you. “Come on sweetheart, let daddy treat you.” It gives butterflies. It makes your knees weak.

LIKE HIS VOICE AHHH!!! IT MAKES YOU WEAK.

A lot of nicknames!! He loves calling you Sweetheart, that’s his main nickname for you. But he also calls you Sugar Lips, Babe, Darling, Sweet Cakes, Hot stuff and My Love.

You also have a few nicknames for him. Honey, Amor, Baby, Dreamboat, Hot Stuff, and My Cowboy. But person favorite nickname to call him is “Daddy” you love his reaction whenever you call him that.

He loves to cuddle you now, he can’t get enough of you. He loves you. He loves your smile, your laugh, your eyes and the way you smell. And with cuddles he can hold you close against his body and fully take you in.

He loves giving you kisses! He can’t get enough of your lips against his. It makes him feel complete.

He’ll always protect you, protect his prize. And if you were ever to leave him he’ll make you regret it. So you better not leave him, unless you have a death wish.

NSFW

Remember when I said he loves your kisses? Well he loves kissing every inch of your body. He loves dragging his tongue against your warm soft skin. And the way you whimper out makes him hard.

He wants to grab every part of your body. He either wants to squeeze you or run his fingers all over your body. Feeling every curve.

His kisses are filled with passion, he loves the way your lips move against his. How soft your lips are against his. And when you guys are making out he loves to grab your thigh and squeeze it making you gasp and also making it a perfect opportunity to sneak his tongue inside your mouth.

Considering his voice makes your knees weak he uses this to his advantage. He loves to talk dirty with you. “How about you ride me Sweetheart.”

Overall Striker is a rough top. He’s loves to mark you and that includes biting, scratching and love marks. And when you guys go out in public you better not cover those marks, he wants people to see you, he wants people to see what’s his. And if you do cover your marks he’ll make sure to punish you.

Striker always puts your pleasure first. Yes he’s rough but not selfish. He especially loves going down on you. He loves hearing you moan his name. “Mmm Striker…” It makes him feel proud, and the way your eyes roll back makes it even better.

Striker is a very kinky guy. He loves using rope. He loves tying you up. And when he does tie you up he’ll make sure to blindfold you. He’s a huge tease! So buckle up buddy!

This guy loves blowjobs. Give him one when he comes back home from a long day of work and he’ll love you. He loves the way your head bobs up and down into his shaft. He’ll also be a dickhead and push your head down more. Smirking to himself if you choke or gag.

When you guys are making love he’s usually on top. He loves to whisper things against your ears. “Come on Sweetheart, you’re doing a good job for Daddy.” And this would make you go crazy, crazy for him. And when you’re about to finish he would whisper again. “That’s right Sweetheart. Cum for me. Cum for Daddy.”

He loves choking you, he loves it when you’re begging for him. But he always makes sure he doesn’t hurt you as bad. He doesn’t want to accidentally snap your neck.

And for whenever you’re a bad little imp he’ll make sure to give you a punishment. This could either be rough sex or edging. Depending on his mood.

His favorite thing is when you wear his Cowboy hat. Just the hat. He loves seeing your naked body with his hat on, it just makes it better. And he’ll make sure you won’t be walking properly for the next few days.

Striker loves to hold you whenever you guys are done with the dirty deeds. He loves praising you, he tells you that you did a good job. He’ll hold you close and cuddle you. He’s great with aftercare.

Overall Striker loves you okay, yes at first he was quite rude to you but now he can’t get enough of you. You’re his everything and no one is going to hurt you. Not on his watch

[mintaikk]

Striker having a statue of himself having a massive dick could just be a background joke and because he's egotistical, but I also found a headcanon a while ago that it was a fan gift that he just used as a coat rack and honestly, that's so much funnier.

Like, we know he has fans in canon. That one imp lady in Harvest Moon Festival (who was a character designer impsona pffft) running up to him, the entire crowd screaming hid name, and that one band making an entire theme song for him. And he doesn't like ANY of it. I mean, he likes to confidence boost, but he doesn't like it when fans get too weird. He kicks Calis (imp girls name btw) away, and he goes off on the band for making s song about him. Plus, he's sex repulsed. He hates it when people are horny over him.

So there's two thoughts I have. One; he hates it when people are horny for him but is still going to be horny over himself and get statue of himself with a large dick as an ego boost (self love ig) and two, a fan gave it to him, he didn't know what to do with it, and it was too hard to get rid of, so he just kept it and sometimes uses the dick to hold things.

[ravenwitch45]

hey i’m just asking maybe could you do dating head canons for crimson from helluva boss? nsfw or sfw i don’t mind <33

Oh! Okay! I've never done romantic hcs before but I'm happy to try! Not great at nsfw so probably just sfw hope you like it! And feel free to ask for more, I'm in a Helluva Mood.

Also I went with this being before ep 3 just to clarify.

Dating Crimson Would Include<3

Dates out to Restaurants barely anyone can afford, nothing but the best for his partner after all.

Talking through text a good bit, as he's a busy man, and noticing he's up incredibly late, forcing you to tell him to go to bed, he reluctantly complies if he can.

Being left in the dark about the whole Mob Boss thing, his last partner got too involved and he did something about it, which he really doesn't want to have to do to you.

Chaz teasing you about it but also shipping it when he's around.

Not being allowed in certain rooms in the mansion, of course he's happy to share the bedroom with you, but he has a completely separate lounge, without any of the morbid trophies or the family portrait and your only allowed in that one.

Getting spontaneous presents, since he's so busy all the time, he wants to make sure your still spoiled. These include clothing, jewelry, and perfume and or cologne, whatever you use. Plus just random utilty stuff he remembered you mentioning would be nice, he's a very good listener.

Him asking you if you like one of things he got you the next time he sees you, and just kissing you passionately if he sees you wearing one, saying "See? I knew it'd look great on you"

Him being awkward if your not a woman, but he still loves you, it's just confusing for someone who's had a very binary thought process when it comes to attraction and gayness.

Getting to know all the buisness associates he has even if you don't know what they do, a lot of them aren't too chatty (Mainly cause he's warned them if they spill the secret to you they'll be joining the wall) but some meet you halfway and chat with you a little. Chaz ironically enough is very chatty with you, calling you "The Boss's Sweetheart" and such.

Getting treated to his expensive alcohol collection, half of which the names you can't pronounce, and your always surprised he can do it and flawlessly to boot.

Him dropping everything the moment you drop by if he's doing something, often rushing everyone out so you can be alone together (Also less chance, someone will slip on hiding all the crime going on but mainly for you)

Okay! Hope you enjoyed that, it was fun! I'd love to do more but for the moment here you go!

[fr4nkie0stein]

Moxxie dating someone who is very overprotective of him and always stands up for him whenever he gets made fun of by blitz, etc

Perfect for him! We all know he needs someone to have his back

Moxxie dating an overprotective reader headcanons (gender neutral)

Content warning(s): mention of bullying/name calling, mentions of weapons/threatened violence, brief mention of Moxxie's traumatic childhood, I think that's it?? If not please lmk

Moxxie's not very good at standing his ground when people make fun of him (*cough* Blitzø *cough*) so you'd be the perfect person for him, other than of course Millie

He's a bit of a pushover, and won't often speak up in defense for himself. Even when he does, his soft spoken and anxious manner means his concerns get brushed over

You, however, will not let any sort of disrespect towards him slide, meaning people who know you well are mostly too afraid to say something about him with you there. You're not above threatening people who dare to speak bad about him, whether it's with a gun, knife, or even a pen if need be

When I.M.P. went to the Greed circle of hell you absolutely did not take any sort of disrespect from his dad, whether that was towards Moxxie or you. Imagine the scene in that episode where Millie attacked all the demons at the "wedding" except it was both her and you (for the sake of these headcanons, let's just say she's a close friend)

Not even Blitzø is immune or safe from your threats. One time he said something only mildly offensive to Moxxie but because you were already having a bad day you threatened to strangle him with his own tail if he said it again

Moxxie is really lucky to have such a protective and loving partner like you, even if you do tend to occasionally go a bit overboard

♡ Send in more requests here ♡

[vikkirosko]

The last story was amazing, hope you can get this one in before the holdidays, and have a nice vacation. And just a great next few months on top of that! But I was wondering ( sorry this may be long ) if you could do a headcanon of alastor, lucifer, Angel Dust, lucifer, fizz + Ozzie, and Rosie? ( sorry if that's to many characters there all just great characters ) x a reader who has CIP ( the inablility ) to feel pain? Thank you! Also how have you been?

I'm all good. I haven't had much free time lately, so I'm a little behind schedule on writing requests, but I still don't lose hope that I'll be able to finish everything before the end of the year. And how are you doing?

Headcanons CIP

🕷 Angel Dust x Reader 💖

You and Angel have known each other for a long time. You knew that he often got into various scuffles and always reminded him to be careful. One of the times you knew for sure that he was going to get into trouble, you went with him. You were right and helped him cope and not get hurt, but there was something that caused him concern. You were hit by several bullets, but you didn't seem to pay any attention to it at all

Only when you noticed the blood on your clothes did you say with irritation that you had ruined your favorite sweater. Angel jumped up to you, worried about your wounds, but you didn't seem to feel the pain, which you soon informed him about. That's why Angel took you back to the hotel, where he treated your wounds. You told him that you had a CIP. You haven't felt pain since you were born, even when you were human, and even in Hell, the absence of pain has remained with you

Angel was surprised that for so long he didn't know that you don't feel pain at all. You had to pay attention to little things so as not to harm yourself, for example, be careful about hot dishes, because you might not notice how hot the soup could be or how hot the cup of coffee was. Angel listened attentively to you, surprised that he didn't notice it

Angel has become more attentive towards you. He didn't constantly take care of you, but sometimes he reminded you that the food or drink was hot, that you held the knife too close to your fingers, or that you were injured. Angel understood that even if you didn't feel pain, it didn't mean that the wounds didn't hurt you, which is why he tried to take care of you at least a little

📻 Alastor x Reader🎙

Alastor found out that you don't feel pain when he noticed that you returned to the hotel with an injured leg. You weren't even limping. You just went to your room like everything was completely normal. He didn't know any other reason for this. He went to your room with a first-aid kit and you did not hide from him either your own wound or the fact that you really did not feel pain

Alastor stayed in your room while you treated the wound on your leg. You told him that even when you were human, you didn't feel pain. You assumed that at least in Hell this would change, but it turned out not to be so. Because of this, you didn't notice the wounds you could get until you noticed the blood on your clothes

The origin of the scars on your skin was now clear. He understood that you probably got these scars in Hell. On your palms, hands, and obviously not only there. You really weren't very worried about your own health, and the lack of pain only made it harder for you to take care of yourself

Alastor understood that in Hell there was much less harm from this for you. Dying in Hell was much more difficult for a sinner than when you were alive, so Alastor didn't worry too much about you. He knew you'd be fine, but he still left a first-aid kit in your room in case you needed it

💀Rosie x Reader 🌹

You were a frequent guest at Rosie's and helped her with some problems at her store. You often stayed at her house for weeks at a time, but Rosie was only too happy to spend time with you. Sometimes you came in with wounds after fights, but Rosie was sure they weren't that serious, so you didn't pay attention to it. However, when you came in seriously injured but behaved as if everything was fine, she became worried

Rosie insistently asked you to sit down and brought a first aid kit. She was in no hurry to ask questions or jump to conclusions, primarily focusing on your wounds. You didn't make a sound when she was treating your wounds, which gave Rosie certain thoughts

You honestly told her that you didn't feel pain at all. Even before your death, you had CIP and you learned to live with it, but in Hell you became more relaxed and took much less care of your own health, which led to your injury. Rosie listened to you carefully, then gently stroked your hair and asked you to be careful

Rosie didn't want you to try. She knew that you tried to be more attentive to yourself and tried to avoid new wounds. You didn't want to upset Rosie and make her worry, which is why you tried not to put yourself in danger, not even realizing that Rosie was ready to show those who would harm you why she was overlord

🍎 Lucifer Morningstar x Reader 🐍

Lucifer knew perfectly well that you didn't feel pain. You've known each other for a long time and he often saw you after fights. You didn't pay attention to the wounds, just talked irritably about stained or torn clothes. You both knew that the lack of feeling pain had its own characteristics, so you made sure that the wounds were treated, and Lucifer made sure that no one dared to hurt you

Lucifer was much stronger than you, and when you were together, no one dared even try to look at you askance, but sometimes you got involved in fights, especially when it was the end of the year. You didn't want to hide, even though you knew you could have died. Every time Lucifer found out that you were fighting again, he watched, taking his time to intervene. It was only when he saw that you were seriously injured that he intervened

Lucifer sometimes offered to pick up personal guards for you, but you kept telling him that it wasn't necessary. Just because you didn't feel pain didn't mean you were reckless. You tried not to put yourself in excessive danger, realizing that even in Hell you could die

You didn't know how long you would be in Hell and whether it was possible to leave Hell at all, but while you were there you weren't going to let yourself die again, especially because you didn't notice any wound and Lucifer didn't mind helping you with it

🎪 Fizzarolli x Reader x Asmodeus 💕

In your relationship, Asmodeus has always tried to take care of Fizzarolli and you. He had sincere feelings for both of you, and you responded in kind, but if Fizzarolli really tried to be careful, then you got into trouble more often. They both saw the wounds healing on you, but you always said it was just a small accident and they had nothing to worry about. This went on until you returned with bloodstains on your clothes and serious wounds that you didn't pay attention to

They immediately rushed to you, both very worried. You convinced them that you were fine, but this time it was obviously not the case. Asmodeus treated your wounds, after which he seriously asked who did it. To his question, you smiled gently and said that they were much worse off than you, so you shouldn't have worried about it. However, there was something that did not escape their eyes. It's like you didn't feel the touch of your wounds

When Fizzarolli asked you if you were in pain, you were confused and said that you didn't feel any pain at all. You've had CIP and you've never felt pain in your entire life. There used to be problems because of this, but now you have learned to avoid serious problems, at least you tried

Asmodeus and Fizzarolli weren't going to leave you alone until your wounds were completely healed. They both surrounded you with care, worrying about you, to which you laughed softly and hugged them. Even in Hell, you were able to find those who gave you the warmth that warmed your heart and soul

[cheeseanonioncrisps]

I get that Helluva Boss and Hazbin don't and aren't planned to have much overlap, and for the most part I appreciate that separation and the way that it makes the world seem that bit larger.

The one exception being this: I am convinced that Angel Dust and Fizzarolli are at least acquaintances, and quite possibly friends.

No, listen, hear me out.

Angel supposedly died in the forties. We don't know exactly when he was picked up by Valentino, but I think it's fair to assume he's been working in Hell's sex work/stripping/porn scene for at least a few decades before he joins the Hotel.

Fizz's backstory is obviously more detailed. We know that he was either born in the Pride Ring or came there at a very young age, because he was already working there as a circus performer when he was a kid.

By the time Helluva Boss starts, however, he's obviously moved on to operating primarily in the Greed and Lust rings, as Mammon's star performer and Asmodeus's boyfriend platonic PA who he occasionally has totally unemotional bang-sessions with.

In between these two points is the accident, which seems to have happened when Fizz was in his late teens. The last time he saw Blitz before that night in Ozzies.

So, here's where the only concrete canon 'evidence' for my theory kicks in: in Oops, Blitz claims that he and Fizz have “been in each other's relative vicinity twice in the last fifteen years” (referring to Ozzies and just now when they bumped into each other in Greed).

However in The-Mammon-Episode-With-Too-Long-A-Title, everyone can't stop talking about how Fizz has consistently won Mammon's clown pageant every time he's entered. For the past ten years.

That gives us five whole years of Fizz's life that are completely unaccounted for. We know that he started this period off in the Pride Ring with his circus destroyed and a brand-new permanent disability to get used to, and ended it in Greed working for Mammon, but we have no idea what happened in between.

So, here is where evidence ends and rampant speculation begins.

As a former child performer, Fizz is unlikely to have had much experience doing anything else. In fact, given that they were travelling with the circus, it seems unlikely that him and Blitz would even have ended up with a steady education.

Blitz obviously managed to found his own business after the accident, but Blitz had been dreaming of doing just that since he was a young child, and it was his Dad who was actually handling the business-side of the circus, so I don't think he's a fair comparison. Fizz probably spent his early years assuming he'd just keep performing forever, and so it makes sense that he'd go back to that.

On the other hand, Fizz had just lost all his limbs, and would have been having to adjust to his prosthetics. (Most likely lower quality prosthetics that he ended up with later, since those seem to be a gift from Ozzie.)

His clown act was mostly physical. Acrobatics require a sense of balance and spatial awareness. Balloon animals and juggling require fine motor control. Literally replacing all four of your limbs— even with magical Hell-prosthetics— is going to cause issues with all these skills, at least temporarily.

So. What industry in the Pride Ring is related to entertainment, but doesn't necessarily require any complex acrobatics, and would most likely welcome a fresh amputee with severe facial scarring? (For fetish reasons, if nothing else?)

I'm not saying Fizz would have done sex work, since he seems so uncomfortable with the idea, but stripping? Maybe doing some soft core porn? I could see that. He's clearly not too fussed about adult entertainment in general, because he's totally okay performing at Ozzies.

He's also probably insanely handsome by imp standards. Like, dude ends up becoming a major sex symbol throughout the rings and has the embodiment of Lust falling madly in love with him. (Plus, as a kid and teenager, he got more attention as a performer than Blitz— the guy who briefly dated a succubus pop-star and now has an ars-goetia prince begging him for a pity-fuck at every opportunity.)

So, given all that, and given his future success, it makes sense that he'd have been popular. Which immediately puts him in range of one of the Pride ring's other hugely popular adult performers: Angel Dust.

And I could see these two getting along. Since Angel is more of a sex worker whereas Fizz is more of a performer, and since Angel would probably be mainly catering to sinner demons and Fizz to hellborn (though no doubt there'd be some overlap), chances are they wouldn't be in direct competition with each other.

They have similar senses of humour and similar personalities. They both like small, cute animals. They both genuinely care about the quality of their performances, even in circumstances where they might not be expected to. They both have a tendency to mask their emotions with sex-related jokes.

Plus there's the fucking angst potential of Angel befriending Fizz when he was an independent performer, and then watching— helplessly— as his friend starts talking about this new job offer with Mammon.

Like people have already made posts about how Angel might feel watching Fizz's performance in Two Minutes Notice and comparing it to his own situation with Valentino, but fuck imagine it from the other end of Angel watching his friend fall into that situation.

Trying to talk him out of it during the initial love-bombing phase and getting told he's just jealous. Not even being able to visit Fizz when it all goes wrong because sinners aren't allowed to leave the Pride Ring.

Also, as a secondary detail, imagine Angel Dust finding out that his new friend's life-changing injuries were caused by Blitz, seemingly a pretty well-known figure in the Pride Ring.

Imagine Blitz finding out that Hell's most famous porn actor has genuine beef with him and having absolutely no idea why.

(Millie, Moxxie and Loona— based on the Verosika thing— all assume it was a bad breakup, despite Blitz insisting otherwise.)

[almacambiondaughterofsaleos]

Emberlynn AU Headcanon Where She Joins IMP

She actually gets along with Moxxie and finds his musical interests awesome.

She ships Moxxie and Millie hard. She doesn't stalk them, but she does make fan art of them which Millie loves.

She wants to get along with Loona but she takes a long while to warm up and finds her annoying.

She is no deterred she is around the same age as Loona because she so loves age gap romances.

What starts them really personally bonding is her finding out he's into horses and it begins her finding a normal relationship with him. Totally starts buying him pony stuff to get on his good side.

Since she can't go into other rings, she will stay in the office to hold the fort if they need to.

She finds out who put the hit on her and she forgot she even argued with her/him since it's been years.

[redr0sewrites]

Helluva Boss Masterlist

Striker

Striker x reader General Hcs - sfw/nsfw

Rough Sex/Gun Kink Striker x reader smut - nsfw/smut

Mammon

Yandere!Mammon Hcs - sfw

[drgarrisonandpaul]

Rolando 'Fluff' Headcanons

Minors DNI, as per usual

Well! The other one went nicely, so maybe I ain't half bad at this. Might as well keep it flowin

The scenario is on a fourth date... or is it the fifth? They're so spaced out due to his shitty scheduling that you have no idea anymore.

You decided to go to his place though, which is really just his own room in his own Hotel. Why bother having a whole separate place when he owns a whole damn building of rooms to stay in?

He may be unconventional as a partner, but that doesn't mean he's any less of an old-timer. I mean, do you SEE those tacky, tinted glasses? He picked out a horror movie to lounge with. Grabbed some popcorn. It's a classic date idea

You were an interesting human... he'd found himself attached to you and unable to tell you what he was. Not really sure if he wanted to tell you at all. That constant tick in the back of his mind, trying to separate you from prey was... weak. You were still a toy to torment in some ways, just maybe not as aggressively. There are romantic ways to mess with someone

He lets you snuggle up to his side and watches with a toothy smirk as you yelp at the occasional jumpscares in the movie, glad that he'd picked a good one

"You holdin' up there, fidget?~"

His voice is always so teasing. Maybe even a little rude, making you scoff and grumble as you clutch his arm for security. The way his legs are spread makes it a little difficult for you to snuggle up to him in exactly the way you want to and that is 100% purposeful on his end. Watching you reposition every few seconds, unable to focus properly

Regardless of form, his expressions are very toothy and wide, so you KNOW that he's smirking down at you with those smug-ass eyes

After the movie, he'll let you snuggle him more properly, just... on his own terms. Maybe in his leather chair instead of the couch, making you straddle him awkwardly

He does still love you, even with how strangely unpleasant he can be at times. He's not the 'I love you like the moon loves the sun! Never touching and yet complimentary in every way, my darling!!' type of man and he LOATHES that gushy shit. He's been a player in the past and this is... his version of trying. He IS trying, just maybe not in the best, most healthy way

[xfangheartx]

Fizzarozzie headcanons because I'm bored.

When Fizz feels lonely or needy or had a bad dream the night before, Ozzie carries him around inside his suit. The palace staff think it's adorable, and truthfully, Ozzie likes it, too. It helps him feel calm.

Fizz started living with Ozzie after winning the clown pageant the second time. Fans were getting particularly rabid back then, and Ozzie didn't like the idea of Fizz living in the Greed Ring alone.

Whenever Ozzie has a particularly bad day at work, Fizz cheers him up by telling him jokes and massaging his shoulders.

When Fizz was nervous about having his first time with Ozzie, Verosika was the one who gave him advice and even got him a few toys to try out. She has known about them since day one and has been an avid supporter. She took them out for drinks when they made their relationship public, in fact.

One time, Fizz got his prosthetics wet and he was left paralyzed in the rain for an hour. This is what gave Ozzie the idea to make his prosthetics waterproof.

When Fizz feels needy but isn't really frisky at night, he and Ozzie just cuddle on the couch together and watch TV until Fizz falls asleep.