guiltyandashamed

[guiltyandashamed]

I like seeing the brothers jealous soooo~

Brother's dealing with a demon trying to ask mc out, through them?

Like a demon asking for mc's number, asking the brother to set him up on a blind date, or ask if mc has a type.

What if the demon asked a brother to deliver a love letter to mc.

headcannons: using the brothers to ask out MC

Lucifer

If a lower-ranking demon asks him to pass along a love letter or your contact info, he stares at them like they’ve spat in his face.

“I see. And you thought I would entertain this?” he doesn’t yell, but the tone of his voice is enough to make the poor demon wither.

Might burn the letter in front of them. If he’s in a good mood, he’ll simply toss it in the bin and say, “I'm maintaining your dignity, your welcome.”

Later, he brings it up to you casually. “You do seem to attract attention. Be more mindful. Some demons don’t know their place.” He wraps his arm a little tighter around your waist.

Mammon

Offended “Huh?! Ya got a death wish or somethin’?!”

If someone dares ask him to set them up with you, Mammon scoffs and goes full-on territorial. “Why would I help you date them? The Great Mammon? You're out of your league.”

He absolutely reads the letter out loud in the dumbest voice possible before crumpling it and shooting it into the nearest trash can.

Might joke to you about it“Ya really got ‘em lined up, huh?”but he's sulking inside unless reassured.

Leviathan

Completely flustered and betrayed. “W-Wait, are you asking me to help you with MC? Do I look like a dating sim NPC?!”

Might accidentally take the letter and hold onto it out of confusion before panicking and burning it later.

Definitely assumes this means you're is going to fall in love with someone else now. Sulks in his room until you reassures him.

“I mean, I know you’re amazing, but that guy was like… an NPC side character. What if they’re better than me?!”

Satan

Barely hides his irritation. If a demon asks what you're type is, Satan gives them a riddle that makes no sense, just to mess with them.

“Their type? They like intelligent creatures… which you are clearly not.”

If handed a love letter, he smiles politely, folds it in half, and slips it into a book, only to be found much later, to that demon's embarrassment.

Later, he tells you about it offhandedly, mostly to watch your reaction. But don’t think he’s passive, he's already thinking of ways to make it obvious to others that you're his.

Asmodeus

Laughs so hard at the demon's audacity. “You want me to set you up with MC? Let's be realistic hon.”

If they ask what your type is, Asmo is blatantly obvious: “Hm, gorgeous, stunning, and Avatars of Lust.”

Might flirt with the demon just to throw them off the scent.

Keeps the letter only to read it aloud to you in a dramatic voice.

Beelzebub

Confused but polite. If someone asks for your number, he frowns a little. “Why would you need me to ask? You should talk to them directly.”

Doesn’t like the idea of being used as a middleman. Especially if the demon clearly doesn’t even know you well.

Will not give out any info. If given a letter, he just forgets about it. Crushed in his pocket beneath a protein bar.

Might casually tell you, “Someone wanted me to give you this. I didn’t think you’d be interested.” His tone says please don’t be. He's got sad puppy dog eyes until you disregard the note and reassure him.

Belphegor

Looks up from his nap like, “You serious?” He finds the idea of someone using him to flirt with you laughable.

If asked to deliver a love letter, he says, “Sure,” and then tosses it out the nearest window as soon as the demon’s gone.

If the demon persists, Belphie gives them a cold stare. “You're about as dull as a cloud. Get the hint, scram.”

Later, smirks and tells you, “If anyone asks again, I might just snap their neck.”

[guiltyandashamed]

closed requests for now!!

I'm going on a trip soon so won't be posting for a while (trying to churn out as much as I can today) so requests will be closing for now. Only because I already have a backlog of requests (and they're pretty good), so I wanna focus on finishing those before opening requests again. Coming back soon, don't worry. 🫡

[guiltyandashamed]

hi! this might be a strange ask but could I please get some headcanons of the obey me brothers with an MC who laughs a lot? MC laughs at the smallest and most random things in public (like insta reels) and their laughter is contagious too. just a thought bc I laugh a lot (and for a long time, I once laughed for 20 mins straight over a trolls meme LMAO) and it rlly confuses my friends.

headcannons: MC who laughs a lot

Lucifer

At first, he’s slightly confused when you laugh at mundane things, but over time, he finds it oddly grounding. You remind him not everything has to be serious.

He doesn’t always join in, but he watches you with a small smile as you cackle at your screen.

If your laugh disrupts class at RAD, he raises a brow and gives you “that look”… but doesn’t say anything unless it goes on too long. He's ecretly amused.

The first time you made him laugh, really laugh, it caught him off guard. “...You’re ridiculous,” he muttered, still smiling.

Mammon

You're his favorite kind of person. Your laughter gives him an excuse to mess around even more, just to hear it again.

Will go out of his way to send you ridiculous memes and out-of-context Devilgram clips to get a reaction.

If you start giggling in public, he immediately joins in even if he doesn’t know what you’re laughing at. “Heh—wait, what? What’s so funny?”

Acts like he’s not affected, but the way your laughter makes his chest feel warm? He’s addicted.

Leviathan

At first, he's self-conscious about your laughter in public, afraid people are watching, but when he realizes it's you being your genuine self, he softens.

Loves when you laugh at dumb video games or anime outtakes with him. Starts saving funny clips just for your reaction.

If your laughter causes him to spiral in embarrassment, he might hide behind his hands, but deep down, he’s thrilled to be the reason you're happy.

Once joined in with an awkward snort-laugh and then froze. You teased him for a week. He secretly loved it.

Satan

He’s observant, so he notices the way people smile when you laugh. He admires how light your presence is in the room.

Will start setting up jokes just to see if he can get that belly laugh out of you. Especially puns or dry humor, it’s a challenge he takes seriously.

Occasionally feigns being annoyed if you laugh too hard in the library, but the way his eyes soften gives him away.

“That laugh of yours is a kind of spell,” he says one day. “You charm everyone in a ten-foot radius.”

Asmodeus

Thinks your laugh is one of your cutest features. Absolutely obsessed with it, especially when your eyes crinkle or you throw your head back.

Will post reaction videos of the two of you watching funny content because your laughter is genuinely entertaining.

If you laugh at his jokes or jokes about him, he feigns offense for drama. but eats it up.

“You should come with a warning label,” he teases, “May cause spontaneous joy and uncontrollable laughter.”

Beelzebub

At first, he’s quiet about it, but he smiles every time he hears you laugh. Even stops eating sometimes to glance at you when he hears it from across the room.

Loves how free you are with your joy. Makes him feel like the world isn't so heavy.

Sometimes asks, “What’s so funny?” just so he can laugh with you, even if he doesn’t fully get it. He likes sharing the moment.

If you start laughing while eating together, he chuckles and hands you a napkin. “Careful. You almost choked last time.”

Belphegor

Your laughter sometimes wakes him up from naps. and instead of being annoyed, he just watches you with a soft smile, eyes half-lidded.

Absolutely the type to lean against your side while you’re doubled over laughing, just to soak up your warmth and joy.

Will occasionally deadpan something outrageous just to hear you wheeze with laughter. Pretends it wasn’t intentional.

“You laugh at the dumbest things,” he says. But then he watches you giggle until you tear up and he hides his grin in your shoulder.

[guiltyandashamed]

Helloo i love ur content so much , so entertaining to read and im exreamly greatful for it <3 , if its not too much of a bother could you write about how the brothers act when mc has curly hair and how she take care of it? I think that would be fun (totally not because im a curly hair gorly 👀)

headcannons: curly haired MC

(Consulted my curly haired friend for this, hope its accurate! Thanks and enjoy :))

Lucifer

At first, he doesn’t fully grasp the level of effort it takes, he assumes it’s just hair. But he notices the discipline in your routine and starts respecting it deeply.

Once tried to run his gloved fingers through it without thinking and learned quickly that you don’t do that without permission. His gloves have a tendency to make it frizzy, so you allow him only if he takes them off. 

Has offered to order expensive Devildom-grade conditioners (for his shower) and satiny pillowcases for his bed “for your convenience,” but it’s clearly because he likes how happy your good curl days make you. (And he wouldn't mind you sleeping over in his room more often.)

Mammon

Absolutely obsessed. Your curls are one of his favorite things, he’s always playing with them (until you tell him not to mess up your curl pattern).

Secretly tried to use your leave-in one day to make his own hair “bouncier” and it backfired hilariously.

He’ll join you on wash days, chatting happily while watching you go through your hair-care routine. Loves the intimacy of watching you care for yourself.

Sometimes you let him shampoo it and he loves it. Brings him the same joy a bubble bath would. He smiles as he looks down at you, hair in his hands. You trust him, almost feeling like a dog getting a good scratch.

Leviathan

Was nervous to touch it at first, thinking it was too delicate, but once you told him how to safely scrunch it or fluff it, he got obsessed.

He loves watching you slip a gaming headset on. Will gladly help you move your hair to make it sit comfortably, blushing the whole time. 

Will ask you to cosplay his favorite curly-headed characters. Dies if you do. 

Anytime he thinks about summoning Lotan, he remembers how furious you got the last time because it messed up your hair. So now, he takes a deep breath and reconsider. 

Satan

Reads up on curl science and protective styling so he doesn’t ask ignorant questions. Quietly observant of what you need on high-maintenance days.

Loves seeing you with a silk scarf or bonnet “it makes you look “regal,” he says.

Occasionally helps you finger-coil if you’re tired. He’s methodical, focused, and a fast learner.

Will write little poems or comparisons to nature about how your curls look in the candlelight, or how rain makes them swell. 

Likes when you lean on his shoulder while you read together, he can smell the products of your hair. It smells distinctively of you. 

Asmodeus

Absolutely a curl enthusiast. Thinks your hair is high art and treats it accordingly.

Constantly gushing over your volume, bounce, and texture. “Darling, your curls have more personality than most demons!”

Loves doing your hair with you, will sit behind you with a wide-tooth comb and detangler while you two gossip or listen to music.

Is always eager to try new hairstyles, occasionally weaving in ribbon or other fashionable accessories. 

He steals your products, all the time. But he makes up for it by giving you free hair-care products sent by his sponsors. 

Beelzebub

Thinks your hair smells amazing all the time. Is very gentle when he hugs you so he doesn’t smush it.

Always offers to help you on wash days, because you always say it makes your arms sore. It's sort of a workout, so he's intrigued. 

If your hair is frizzy or wild, he doesn’t mind, he thinks you look soft and warm, like a pillow.

He once asked if he could “pat it.” You let him. He was overjoyed. 

Fell asleep with his head on your curls once and called it the best nap ever.

Belphegor

Finds your hair fascinating when it's extra fluffy in the mornings. Has taken secret photos of you mid-sleep when your hair looks “cloudy.”

Constantly tugs at a curl while you’re talking just to watch it bounce. Smirks every time.

Loves napping with his face buried in it, even if it leaves your hair tangled and frizzy he doesn’t care. “You're soft. That’s all I need.”

Thinks it takes too much work to maintain. Says you should just use magic to do it. 

Will fall asleep holding your bonnet if you forget it on his bed.

[guiltyandashamed]

Not exactly a request but bro your Beel HCs and snippets are so in character and it makes me so happy 🥺🥺🥺😭😭 Do you have any miscellaneous HCs for him that you haven’t gotten a chance to share? I’d love to hear some!! 🥺💗

Thanks :) Hope u enjoy!

headcannons: beel

Beel is quiet, but not because he doesn’t have anything to say, he’s just thinking all the time. He listens before he speaks.

He genuinely doesn’t mind doing chores if it means keeping the peace in the House of Lamentation. Especially heavy lifting or errands that involve carrying things.

He’s one of the most observant brothers, especially when it comes to people’s habits. He notices when someone’s sad or tired, even if they don’t say anything.

He has a soft spot for animals and is surprisingly gentle with creatures much smaller than him. He once fed a crow with crumbs for a week and named it "Toast."

Beel and Mammon have a surprisingly good relationship. Mammon sneaks snacks to him in class, and Beel never rats him out. They have an unspoken food-based truce.

Satan once taught Beel about Devildom flora and which fruits were safe to eat, and Beel now brings him rare samples he finds while out hiking.

Lucifer relies on Beel for reinforcement, not to intimidate, but because Beel’s silent presence is enough to keep things from escalating when tensions rise.

Beel makes sure Belphie eats properly, even if it’s just nibbling on something. He often cooks extra and just leaves it on Belphie’s desk without comment.

Asmo’s the only one who can get Beel to sit still to do his hair or nails. Beel falls asleep during them half the time, and Asmo doesn’t mind “You’re like a golden retriever.”

Whenever Levi orders food packs in bulk, hoping to get a rare prize, Beel helps him go through them all. He does it for the free food, of course, but he enjoys seeing Levi's reaction to the prizes.

Beel always saves the last bite for you, no matter how hungry he is. If you're eating together, he instinctively offers you food from his own plate.

You get used to packing snacks for Beel, but he ends up sharing half of them. He thanks you every single time, even if it’s just a single chip.

Beel isn’t physically clingy unless you initiate, but once you do, he melts. He’ll wrap you in his arms and let you nap on his chest for hours.

Beel is fascinated by your cooking skills if you cook. If you can’t, he happily teaches you, even if it turns into a “we ate all the ingredients” situation.

If you give him food with a personal note, he’ll tape the note to his wall. Even the tiniest “eat well today!” becomes part of a small collection by his bed.

[guiltyandashamed]

hi! can i req the brothers with a gift giver mc? like really thoughtful, crafty handmade gifts. love your writing btw ^_^

headcannons: hand-crafted gifts from MC

Lucifer

At first, Lucifer is mildly surprised when you hand him a sleek, hand-cut card with gold ink, congratulating him on another successful quarter at RAD. He accepts it with a raised brow but keeps it. Then comes a small box with individually labeled tea sachets, each one with a handwritten tag “For when the paperwork’s unbearable” or “Take a break, you deserve it.”

It starts to accumulate. Quietly. In his desk drawer is a little section now, a handful of thoughtful things from you. One day, he finds a ceramic paperweight shaped like a wing with a note: “So you don’t have to carry everything at once.” He doesn’t show much emotion, but that stays right on his desk. Every time he sees it, he sighs a little less.

Mammon

You made Mammon a little keychain, a chibi version of him, colored and sealed in a handmade resin charm. You give it to him with a little note “To protect your keys like you protect me.” He turns red, says you didn't have to, but he keeps it attached to his D.D.D. at all times.

Thing is, you do this often. A tiny scratch-off card with “Best Demon Ever” under the heart. A little origami crow taped to his mirror. A duct tape coin pouch you stitched on a whim. Mammon doesn’t just keep them, he brags about them. He’s made a box for your stuff and adds to it religiously, even if he pretends he’s “just organizing.” When he’s alone, he takes it out and goes through each piece like it’s treasure.

Leviathan

You drew him a birthday card styled like the cover of his favorite anime, logo mimicked, your characters stylized like the cast. Inside was a friendship meter like a dating sim, maxed out with his name. Levi short-circuits. You handed it to him shyly, and now he’s pink to his ears, holding it like it’s a sacred collector’s item.

He tries to play it cool, but your habit of crafting him things,bookmarks with tiny tentacle tassels, quote cards from anime you watch together, stickers of you as an in-game character, completely ruins him. He has an entire display shelf just for your creations, right next to his rarest figures. He calls it his MC Loot.

Satan

Satan is given a recycled book spine bookmark with etched cat ears at the top and your initials burned into the back. “So you don’t lose your place,” you wrote. Satan accepts it like someone receiving a priceless relic. His fingers trace every imperfection like it’s proof of sincerity.

He keeps every card you make: a thank-you card with tiny paw prints, a birthday note referencing his favorite literary quotes, a hand-bound pocket notebook. One day, you hand him a small canvas with a painted library cat in Devildom green, and he actually stops mid-sentence. “You remembered I mentioned that… months ago.” He’s not just collecting them, he’s preserving them, cataloging them in a little drawer beside his best books.

Asmodeus

You made Asmo a hand mirror, glittering frame, embedded with tiny stones, and a message in your scrawl on the handle: “You're already perfect.” He gasps like you handed him a crown. “This is the sweetest thing I’ve ever been given!”

It’s not a one-time thing. You gift him bath salts you mixed yourself, sachets with stitched heart tags, little “confidence cards” with compliments for him to pull on bad days. He lines them up along his vanity, perfectly arranged, and even rotates them by mood. “I don’t care what anyone says, darling,” he hums, “nothing looks better on me than something you made.”

Beelzebub

You hand Beel a stitched snack pouch made from durable RAD uniform scraps, reinforced with little patches that resemble food logos. “To keep your snacks safe,” you say. He beams and hugs you carefully, because he doesn’t want to crush you or the pouch.

You’re always slipping him handmade granola bars with heart-shaped notes, or tiny hand-painted boxes filled with his favorite flavors. He keeps every wrapper that has your handwriting on it. One time, you gave him a crude crocheted plush of a hamburger. Surprisingly, he's never tried to eat it because the idea of losing something you made frightens him. It never fails to make him smile to be reminded that you make things for him.

Belphegor

You make Belphie a handmade constellation map, sewn with gold thread, into a soft pillow cover. “I charted stars of the night you first took me to the planetarium” you say. He tucks it under his arm immediately. “This is… seriously amazing.”

He acts nonchalant, but his room is full of your things. A dream journal you hand-bound and scrawled sleepy messages in. A cloud-shaped stress ball he squeezes when he can’t drift off. You keep making things for him, and without ever asking, he starts making space on his bed just for your gifts.

[guiltyandashamed]

hiii!!! could you do brothers + side characetrs with an mc who is famous on devilgram? like ever since they came to RAD they became super popular online :D thanx!!!!

headcannons: devilgram-famous MC (brothers + side characters)

From the moment you arrived in the Devildom, Devilgram became your outlet. You posted everything, your outfits, your food, funny observations about Devildom life.Your page quickly gained traction. Now you have brand deals, fans, and even the occasional paparazzi moment at RAD.

Lucifer

At first, he brushes it off. "If it doesn't interfere with your academic performance, I have no reason to be concerned."

Then he sees how successful you are—Sponsors reaching out for promotion or looking to get into business with you. He makes sure you aren't getting exploited, are promoting the right people, and maintain a respectable image.

It's helped you elevate yourself professionally, and he respects your hard work ethic when it comes to taking your position seriously.

Slightly more possessive in public when you're approached by admirers. A gentle hand on your back. A subtle glare that makes fans back off without realizing why.

Mammon

Loudly and immediately obsessed.

Starts posting with you constantly. Tries to leverage your fame for duo sponsorship deals “Get rich together, ya know?”

Deep down, he’s insanely proud. Shows your posts to his modeling friends like, “See that? That’s my human.”

But also gets jealous when fans get too flirty in the comments. Starts hearting every comment that mentions your relationship, even if you’re not officially dating.

Obsessed with fan edits of you. Tries to hide that he watches them, but you can see it in the reflection of his sunglasses.

Leviathan

Has an existential crisis. “You’re more popular than I am on Devilgram… you’re living the normie dream…”

Starts watching your follower count rise like it’s a real-time leaderboard. Gets nervous when you surpass his favorite stars.

Softens up when you post a photo of you two gaming together, calling him your “best coach.” You even tag him. He stares at it for hours.

Gets extra shy when fans recognize him in your videos.

Feels somewhat jealous that tons of people admire you, besides him. You comfort him, “All they see is a person on a screen. You get to see the real me,” which makes him smile and nestle a little closer.

Satan

At first: indifferent. “Social media isn’t exactly my scene.”

But once he realizes how cleverly you use your platform, highlighting Devildom culture, normalizing interrealm relations, he’s genuinely impressed.

“You’ve created a kind of social bridge. I respect that."

Gets incredibly flustered when you post a 3-second video of yourself with a cat. The public seems to go crazy over it, he does too.

Gets very defensive if anyone posts rude comments. He’ll never say it out loud, but you once caught him trying to trace a troll’s IP.

Has a folder on his D.D.D. titled “Their Best Posts.” You pretend not to see it.

Asmodeus

He's thrilled. “You’re famous? Oh, we simply must collaborate!”

Loves being seen with you, you're both beautiful, you both have fans, and you both know how to pose for the camera.

He understands attention better than anyone else, and he knows how intoxicating and isolating it can be.

Offers to help you with skincare routines, posing tips, PR strategy, partly because he wants to help, partly to stay close.

He also gets more clingy in private. “They all want you, darling... but you’re mine tonight, right?”

Beelzebub

He doesn’t really understand the whole Devilgram fame thing, but he gets that it makes you happy. That’s all that matters to him.

At RAD, when fans swarm you, he calmly stands between you and the crowd, not to block them entirely, just to make sure you’re safe and not overwhelmed.

He especially likes your food posts. Thinks it's cool that other people like to see food too.

You’re never just a screen persona to him. You’re someone who laughs with him at breakfast, helps him find rare protein bars, and brings him quiet peace in a world full of noise.

“I don’t care how many followers you have. You’re already important.”

Belphegor

Acts like he doesn’t care. “Tch. So what if you’re popular now? That doesn’t mean anything.”

But he watches from the sidelines more than you think. Lurking in the tags. Scrolling when he can’t sleep.

The moment you start getting approached at RAD, his mood dips. He doesn’t like strangers looking at you like they know you.

Despite the sharpness, there's a vulnerability underneath. He’s afraid of being left behind, forgotten in the blur of lights and fans.

He won’t admit it out loud, but he clings harder when you’re alone together. “Don’t let them take you away from here. From me.”

Diavolo

He thinks it’s fantastic. The Devildom needs more human-devil cultural exchange, and you’re a living ambassador.

His support is big-picture. He encourages you to use your platform wisely and offers official RAD sponsorships or protections if needed.

However, when he sees how people crowd around you or speak to you overly familiar, there's a flicker of protectiveness.

“You're doing wonderfully, but remember, you're not obligated to be available to everyone.”

Occasionally invites you for PR events or asks if you’d like to co-host a Devildom-wide livestream. Always gives you the option to say no.

Barbatos

He’s largely neutral outwardly, but very aware behind the scenes. He monitors your online activity and fan interactions like a hawk, purely to assess threats.

Subtly reroutes suspicious or overzealous fans before they get close. You may never know how often he's intervened.

He offers you quiet reminders: “It’s wise to schedule rest periods. Even stardom mustn’t replace self-care.”

Helps you manage time between your obligations and online work. If you have a shoot or sponsorship, he’s already rearranged your RAD schedule to accommodate it.

He doesn't compliment often, but when he does, it’s precise: “You handled that interview well. Controlled, charming, and sincere. Admirable.”

Solomon

Oh, he thinks it's hilarious, and impressive. “Guess I’m not the only famous human in the Devildom anymore.”

Loves to tease you: “Should I start calling you 'Your Influencer Highness'?”

But he also offers practical help. He’s seen what fame can do to people, and he quietly checks in if your confidence falters.

“Fame’s a fun illusion. Just don’t forget who you are when the lights are off.”

When fans push too far, he’s not above sending them a politely cursed message.

Simeon

Supportive in a very grounding way. “Your success is lovely to see, but more lovely is the kindness you still show.”

Watches your rise with a gentle fondness, like a proud mentor or older brother.

Offers advice if you ever feel overwhelmed by the attention.

Helps you sort through fan mail, especially when it becomes too much. Keeps you emotionally anchored.

He makes sure you still have private, sacred spaces where you can just be yourself, with no cameras.

Mephistopheles

Incredibly bitter that you're more popular than the RAD newspaper he runs. “So you take selfies and suddenly you’re Devildom royalty?”

Has tried (unsuccessfully) to get you to guest-write an article for the paper to boost his own traction.

Occasionally shows up in your tagged posts looking way too smug.

While he pretends it’s all business, he gets quietly flustered when fans ship you two.

Thirteen

She's amused by the whole thing. “You? A Devilgram star? Never thought I’d see the day.”

She makes fun of you constantly for being famous, but secretly watches every story.

Teases you like: “Careful, don’t trip over your fanbase on your way to class.”

If you ever feel down because of rude comments or pressure, she’s the first to call it out.

“Want me to rig their phone with exploding hexes? No? Just say the word."

Doesn’t treat you differently and likes that you are still you, despite the fame.

Raphael

Skeptical at first. “Why do so many people need to see what you ate for breakfast?”

Doesn’t understand the appeal of social media, but respects that it makes you happy.

Has to learn to be okay with the attention you get, he's the type to walk just a little closer when fans crowd you, not possessive, just… present.

If you ever express that you're tired of the pressure, he listens seriously and offers calm advice.

“Then take a step back. You’re not obligated to be seen constantly to be real.”

[guiltyandashamed]

Hi! I hope you are having a nice day ^^ I would like to request headcanons for the secondary characters with an MC who is an insect collector?

headcannons: insect collector MC

(side characters)

(I have an immense fear of bugs, but I respect the grind nontheless.)

Diavolo

Immediately fascinated by your hobby. “You mean you willingly pick them up? With your bare hands?”

Orders the creation of an official RAD Insect Observation Club with you as president.

Tries to help catch some... but ends up chasing one through the palace halls and crashing into furniture. Barbatos wasn't very happy.

Genuinely impressed by your knowledge and the delicate care you take with each specimen. “There’s something noble about appreciating the smallest lives.”

Once brings you a massive, iridescent beetle as a gift. He’s proud until it escapes in your room and disappears for three days.

Barbatos

Already knows every species in the Devildom and their ecological role, but he lets you explain things anyway, listening patiently.

Brings you rare specimens from deep within the castle gardens or other extreme areas.

Joins you on quiet collecting walks through the forest. You speak very little, but there’s comfort in the silence.

You once caught him smiling faintly as you held a glow-winged moth to the light. He didn’t say anything, just watched.

Solomon

Casually mentions he once turned into a bug by accident during a spell gone wrong. You’re horrified. He’s amused.

Offers to enchant your collection cases to prevent decay, or worse, escape.

Gets a little too enthusiastic helping you collect one night and accidentally releases a pheromone that draws thousands of love-drunk beetles.

Thinks your nerdy joy is adorable. “I don’t know how you make bugs look charming, but here we are.”

Simeon

A little squeamish at first, he’s used to birds and flowers, not six-legged critters, but he warms up to it when he sees how gentle you are.

Loves hearing you talk about what you’ve found. “There’s something sacred in the way you appreciate them.”

Tries sketching them with you, though his insects look more like abstract art.

Worries for your safety when you go deep into Devildom terrain. Sends you off with snacks and a warning: “Don’t go too far. Come back safe.”

Mephistopheles

“You collect what?” Followed by a dramatic sigh and an eye-roll. Still ends up funding a grant for your new club at RAD.

Accidentally reveals he’s afraid of bugs when one lands on his lapel. Screams like a noblewoman.

Peeks into your collection when no one’s looking. You catch him staring at a glowing purple scarab. “It’s hideous,” he lies.

Secretly brags about you to others: “My associate is conducting original ecological research, actually.”

Thirteen

LOVES it. Immediately begs you to take her on bug-hunting trips. “You know some of these things are venomous, right? This is my kind of danger.”

Builds you small traps to cautiously catch the bugs that are dangerous to handle.

Names the bugs ridiculous things like “Bitey Jr.” or “Glitter Scab.”

Tries to prank you by placing fake bugs around your room, but you recognize them as fakes instantly.

Becomes unusually gentle when helping you catch something rare. “We gotta respect the creepy-crawlies, yeah?”

Raphael

Stoic, silent, and watching. Initially doesn’t comment at all, but never stops you.

One day, quietly places a jar with a winged insect on your desk. “It’s native to the area around Purgatory Hall. You’d appreciate it more than I do.”

Stands watch while you crouch in strange areas to collect specimens, keeping you safe from lurking predators.

You once catch him observing a caterpillar in your terrarium for ten minutes straight. He doesn’t explain why. You don’t ask.

[guiltyandashamed]

beach day with brothers + dateables!!!

headcannons: beach day (brothers + side characters)

Diavolo had the brilliant idea to host a full-day beach getaway at his private artificial beach. It features shimmering white sand, crystal-clear saltwater waves, and a state-of-the-art sun that mimics the perfect warmth of a human-world summer day. Everyone was invited. Swimsuits, drinks, games, and even a fire pit for roasting food by moonlight (the artificial sun does set eventually). It’s rare to have everyone relaxed in one place, so the day is something special.

Lucifer

At first, he's very much the dad of the trip. Clipboard. Schedule. Trying to make sure everyone packed sunscreen, water bottles, and spare towels.

Arrives in black swim trunks and a crisp, partially unbuttoned linen shirt he refuses to take off for the first hour.

Stays under the large shaded canopy with a drink in hand, sunglasses on, pretending to read but mostly watching over everyone.

You convince him to go for a swim. Eventually. He gives in only because it’s you, and ends up surprisingly graceful in the water.

If you splash him, expect revenge but in the most calculated way. He’s not above dunking you playfully. If Mammon tries splashing him he's holding his head underwater for a concerning amount of time while Mammon thrashes about.

Ends up walking along the shore with you when the sun starts to set, a rare soft expression on his face as he listens to you ramble.

Sighs dramatically when he sees the shenanigans his brothers are involved in.

Mammon

The first one to run into the water, yelling “BEACH DAAAAAAY!” at full volume.

Hawaiian shirt open, board shorts, and designer sunglasses.

Tries to impress you with backflips off the dock. Fails. Pretends it didn’t hurt.

Is constantly trying to initiate beach games—volleyball, frisbee, tug of war, sandcastle competitions. Loses half the time. Doesn’t care.

Suggests burying someone in the sand. Ends up being the one buried after losing a bet. You sit and talk to him for a while, picking sand out of his hair.

Pulls you into the ocean, especially if you’re standing too close to the edge. “C’mon, don’t be boring! The water’s perfect!”

Gets extremely jealous if he sees anyone else putting sunscreen on you. Immediately demands to do it himself. Badly.

Buys matching seashell bracelets from one of the vendors. Won’t admit it’s cute, but he's always making sure you're wearing it.

Leviathan

Wears a rash guard and swim trunks with anime character print. Brings floaties. Even though he can swim.

Spends the first hour hiding under an umbrella with his phone and a cooling towel. Eventually, you coax him into the water.

Loves snorkeling once he gets going. Spends half the day with a snorkel mask and fins, pointing out coral and fish with excited gestures.

Brings waterproof game consoles and challenges others to Mario Kart in the shade.

Gets shy around you in a swimsuit, especially if it shows a lot of skin. He tries not to stare. Fails. Blushes violently.

If you play in the tide with him, he relaxes into it, laughing when you chase each other around the shallows.

Builds a sand sculpture of Henry 2.0 and acts like it’s no big deal, but beams when you praise it.

Satan

Shows up with a good book, sunglasses, and a sunhat that somehow looks annoyingly classy on him.

Picks a spot slightly away from the crowd, claiming it’s for “peace and quiet,” but you notice he keeps looking your way.

Wades into the water calmly, then ends up challenging Lucifer to a swimming contest just to stir the pot.

Spends part of the day collecting interesting shells and smooth stones. Gives you the best ones without saying much.

If you sit beside him to read, he will occasionally murmur commentary to you, low and intimate.

Secretly loves the idea of you in beachwear but keeps his reactions well hidden, until someone else comments, and then he's suddenly standing very close to you.

Helps the Little D's build sandcastles and explains the physics of how sand holds shape. Somehow, they love it.

Gets very competitive when involved in the beach games. Especially if Lucifer is involved.

When you lie down beside him near the end of the day, he traces a small circle on your back with a lazy finger and says, “This wasn’t a bad idea after all.”

Asmodeus

Fashionably late but impeccably dressed. Swimsuit? More like a full beach look: designer shades, sheer sarong, glitter sunscreen.

Gasps when he sees you. “Darling, you look stunning—but next time, let me style you too!”

Spends most of the day posing for selfies, dragging you into half of them, applying lip gloss like he’s on set.

Teaches you the “perfect beach photo angles,” then takes a scandalously good photo of you and makes it his lock screen.

Flirts nonstop, both playfully and sincerely. If you look even slightly sun-touched or flushed, he fawns over you.

Starts a tanning circle with fancy drinks and gossip. Pulls Simeon in for juicy stories, much to the angel’s dismay.

Tries every water activity but hates getting his hair wet. “Beauty before fun, babes.”

At sunset, he grabs your hand and leads you to the water’s edge for a photo. He says the skies beauty is nothing when in comparison of you. You hold hands while walking along the shore.

Beelzebub

Shows up early to help carry the food, grills, umbrellas, everything. Walks shirtless without even noticing the effect.

Wears blue swim trunks with little hamburgers printed and a big smile. Greets everyone like it’s a family reunion.

Immediately scouts the food tables. Devours an entire platter of sandwiches before lunch. Apologizes sincerely.

Loves beach sports. Volleyball, swimming races, tug-of-war—he’s game for all of it. You team up with him, and you always win.

Brings you drinks without you asking. Wipes the sweat from your temple with a towel like it’s nothing.

Offers you his giant towel to sit on if yours gets sandy. Doesn’t mind sharing it, actually, he prefers it.

If you seem tired, he lifts you up bridal-style and takes you to a shady spot without hesitation.

At the end of the day, he shares a bite of grilled pineapple with you, his voice low and content: “Days like this are the best, huh?”

Belphegor

Complains the whole way there, dramatically yawning and dragging his feet. “Sun? Sand? Effort? No thanks.”

Ends up stretched out under an umbrella within ten minutes, asleep with a straw hat over his face.

Wakes up when he hears your laughter. Watches you from his shaded spot for a while before pretending he wasn’t looking.

Eventually joins you in the water, floats on his back, eyes closed, just listening to your voice. “This is... kind of nice.”

Builds lazy little sand mounds around you while you sit. Calls it a “defensive perimeter.”

Gets annoyed when others flirt with you. Won’t say anything, but suddenly appears at your side, shoulder to shoulder.

Asks you to take a nap with him in a hammock strung between two palm trees. When you say yes, he hums softly as you both sway.

Murmurs, half-asleep, “You make this whole place better. Just so you know.”

Diavolo

Absolutely thrilled by the beach idea. He personally arranged the sun, weather, and waves. “It’ll be fun!” he says, grinning like a golden retriever.

Wears brightly colored swim trunks and insists on matching floaties. Looks ridiculous but makes it charming.

Tries every single beach activity, from surfing to grilling. He's not particularly good at any of them, but his joy is contagious.

Drags you into water games with him, laughing when he falls over and splashes you.

Organizes a sandcastle-building competition, with prizes, and names you a judge.

Hands you a drink halfway through the day and earnestly says, “Thank you for spending this time with me. It means a lot.”

At sunset, he quietly watches the sky shift colors. You sit beside him, and he nudges your knee with his. “We should do this again. Just the two of us.”

Barbatos

Shows up perfectly prepared: picnic basket, umbrellas, refreshments, towels—all color-coordinated and neatly packed.

Wears modest swimwear and sandals. Somehow still looks graceful.

Spends most of his time setting things up and making sure everyone else is comfortable. Doesn’t ask for anything in return.

Brought the Little D's to help set up and to serve food, but let's them play around in the meantime as long as they don't cause trouble.

You catch him once, standing alone in the shallows, pants rolled up, letting the water rush around his ankles. He looks... peaceful.

He lets you coax him into sitting for a moment. You feed him fruit, and he smiles, truly smiles. “You bring out my softer side, it seems.”

Makes you the perfect drink to cool down, garnished and all. Later slips a shell into your bag with a quiet note written on parchment.

Tucks your hair behind your ear if the wind blows it around. Doesn’t say a word about it.

Solomon

Wears a half-buttoned linen shirt and swim shorts that are probably enchanted. Looks like he walked out of a resort magazine.

Is weirdly good at beach volleyball. Smirks every time he scores. “Want to play doubles? I always win with you.”

Teaches you how to draw magical sigils in the sand that animate briefly before washing away.

Starts a bonfire using a snap of his fingers, then sits beside you, playing with the firelight and your shadows.

Laughs at Diavolo’s antics but sneaks you away from the crowd just to walk along the water’s edge. “I like when it’s just us.”

Gets a little possessive if someone flirts too much with you, he’ll suddenly show up at your side with a casual arm slung around you.

Asks you to dance with him in the sand after most have gone home. No music, just the sound of waves.

Simeon

Wears tasteful white swimwear and brings an oversized sunhat that somehow makes him look angelic and rich.

Offers to help Barbatos serve drinks and snacks. He’s the charming host type, complimenting everyone with that soft voice.

Watches you with a fondness that’s easy to miss unless you’re looking for it.

When you join him under the umbrella to rest, he hands you a cold drink and says, “You look radiant in this light.”

Is incredibly flustered if you tease him about his beach body. Turns red but covers it with a laugh.

Later, walks with you at the edge of the water, letting the foam rush over your feet. “Moments like this feel... timeless.”

Offers to rub sunscreen on your back in the most respectful and innocent way, but that little smile he gives when he touches you says otherwise.

Mephistopheles

Shows up overdressed, insists the beach is “beneath his status,” then proceeds to enjoy it more than anyone else. He'll talk someone's ear off about Diavolo's ingenuity in setting the whole thing up.

Wears old-fashioned striped swim trunks and carries an umbrella he refuses to share unless you ask nicely.

Complains about the sand but helps you build a sand sculpture of the RAD tower anyway.

If you’re in a swimsuit he likes, he gets tongue-tied for a split second before scoffing and looking away.

Brings sunscreen from the human world and brags about it. Offers it to you like he’s doing you a favor.

Gets into a ridiculous water fight with Mammon and drags you into it as a “shield.”

Pretends he doesn’t care if you sit next to him on his towel, but adjusts his posture to be closer to you as the day goes on.

Thirteen

Immediately sprints toward the water, dives in headfirst, and does a backflip just to show off.

Wears a two-piece swimsuit with skeletons and pastel flames on it. Carries a surfboard even though she can’t surf.

Dares you into games and races. “Loser owes the winner a favor. You scared?”

If you wear something cute, she whistles. “Looking good, human.”

Buries Mammon in the sand while he naps. Writes “Dunce” on his forehead in seaweed.

If she catches you getting tired, she drags you onto a floatie and pulls you around the water like a lazy river.

Hogs all your snacks but shares her favorite juice with you. “You’re the only one I’d share this with. Feel special.”

Raphael

Shows up with zero fanfare, dressed simply, and settles in the shade with a book.

Declines most invitations to play or swim. until you ask, and then he quietly obliges.

Very protective. If the waves seem too strong or someone splashes you, he steps between without comment.

Doesn’t flirt, but the way he towels off your hair or hands you water feels deeply personal.

When you sit beside him, he lets his guard down just a little. “You seem happiest here,” he says softly. “That’s worth more than any mission.”

Wades into the shallows with you and silently watches the sky, arms crossed. He’s not the type to say it, but he enjoys your company immensely.

During beach activities, he rarely puts in effort but he does surprisingly well. Almost wins the sandcastle competition.

At the end of the day, gives you his towel without being asked and waits to walk back with you.

[guiltyandashamed]

THIS IS SP VAGUE BUT maybe MC who only ever wears skirts? You can ignore this if you want, btw I love your writing soooo much! 💗

headcannons: MC who wears skirts

(thx! this is such a cute idea thanks for giving me creative liberty)

You're a fashion-forward MC who wears skirts regularly, favoring shorter styles but always dressing with intentionality and flair. Whether it’s a casual mini, pleated tennis skirt, or a tailored high-waist piece that ties the outfit together, you make it work and make it look good. Your style is confident, expressive, and sometimes a little flirty without needing to explain itself. This is how the brothers react:

Lucifer

Lucifer is the type to notice everything, but he’s also impeccably restrained. He doesn’t show it, but he notices the way the fabric of your skirts sways with every step you take, how they highlight your legs in a way that makes him momentarily lose his train of thought. He’s a little protective, especially in public situations where he feels you might attract unwanted attention. If anyone dares comment on your outfit in a negative light, they’ll find themselves dealing with his cold glare. He won’t voice it, but he likes seeing you in skirts, it suits you, and there’s something about the way you carry yourself that makes the outfit look refined rather than overly flirtatious. Behind closed doors, he may even make a comment about how “those skirts seem to attract a lot of unwanted eyes." But it’s clear he’s protective in his own quiet way.

Mammon

Leviathan

You're killing him. Full stop. Every time you walk past in one of those short skirts, he’s internally combusting. His eyes dart, his brain short-circuits “D-don’t bend over like that, human! You tryin’ to give me a heart attack?!” He’s obsessed with your style and insists he’s just “lookin’ out for ya,” but let’s be real: he’s mesmerized. Jealous of the wind, even. He’ll end up buying you more skirts, too, under the excuse of “Ya looked cute in that last one so… here, whatever.” He’s mesmerized by how effortlessly confident you look, especially when you spin or twirl in a skirt. There’s something about the way you wear it that makes him feel both proud and possessive. If you wear a particularly flirty one, he may try to joke about it. “Gotta be careful with that one, yeah? Or I’ll be carrying you around all day to keep those other demons from looking.” As much as he likes the view, he’s also keen on making sure no one else gets too close

Levi’s not okay. He’s so used to fantasy characters wearing short skirts and now here you are, real-life, looking like an anime protagonist and walking next to him. He stares, then gets flustered, then tries not to stare. It’s a loop. He won’t say anything at first, but when you catch him sneaking glances, he practically folds in on himself. “Y-you’re seriously just gonna wear that? Like it’s n-no big deal?!” He lowkey loves it though, he just doesn’t know how to survive it. He’s embarrassed but can’t stop looking. He tries to distract himself by playing a new game or binge-watching anime, but no matter what, his eyes wander to the way your skirt fits. He tries to hide behind his computer screen or his manga, but the truth is, he’s a little in awe. The idea of you wearing skirts seems to match perfectly with his image of you as someone from a world that’s somehow more perfect than reality. He’ll ask if your willing to cosplay as some of his favorite skirt-wearing characters, and if you do, his brain blows a fuse.

Satan

Satan’s reactions are more subtle, but he’s definitely not immune to the way you carry yourself in a skirt. He watches you from across the room, admiring the way you can move freely, the skirts adding a graceful and almost playful quality to your every step. Satan’s the type to compliment the structure, the color coordination, the tailoring. But if your skirt’s especially short one day and you’re reaching for something on a high shelf? Yeah, he’s quietly gripping his book a little tighter. He won’t make crude comments, but he will murmur something like, “You enjoy turning heads, don’t you?” with that faint smirk of his. He’s far too composed to be obvious, but that doesn’t mean he’s unaffected. Sometimes, he’ll find himself absentmindedly running his fingers over the fabric if you sit near him, but he quickly catches himself. There’s no doubt that Satan finds it attractive and irresistible.

Asmodeus

Beelzebub

Asmo is all about skirts. He’s completely enchanted by the way they highlight your legs, and he's got no problem vocalizing it. "Darling, those skirts are a look—and it’s not just the fabric I'm noticing," he teases, his voice dripping with flirtation. If you wear skirts frequently, he’ll be ecstatic, constantly complimenting your outfit and suggesting even more glamorous ones he thinks would look perfect on you. But Asmo’s mischievous side kicks in, he'll “borrow” or “swap” your skirts for ones he deems a better fit. “You’re never going to wear that skirt again, darling,” he’ll say as he gives you something more revealing or sparkly. He’s a little sneaky with his admiration but always makes sure you know how divine you look. In fact, he might ask you to model them for him, just so he can see you twirl in the most attention-grabbing outfit possible.

Belphegor

Beel doesn’t say much, but he notices. Especially when you're walking ahead of him. He’ll glance down, tilt his head slightly, then snap his eyes forward like a gentleman. He’s protective without being overbearing, walking on the outside of the street, standing behind you in crowds. When others stare, he narrows his eyes. He doesn’t mind that you wear skirts; he minds that other people forget how to behave when you do. Still, when you ask him if it looks good, he’ll blink and say, “It looks really good on you,” like it’s the most obvious thing in the world. If you're ever a bit uncomfortable, or frequently pulling your skirt down in public, without a word he'll take his jacket off and wrap it around your shoulders. It's chivalry you'll willingly accept.

He teases you, of course. “Another skirt today? Trying to distract me from my naps?” But he’s a fan, even if he pretends not to be. When you wear something especially cute, he’ll tug you onto the bed and bury his face in your lap, mumbling, “Comfy and pretty. Nice.” He’s the one who’ll idly play with the hem while the two of you lounge together, eyes half-lidded, watching you from under long lashes. He likes how you express yourself, even if he pretends he’s too sleepy to care. He enjoys watching you move around the house, your skirts flowing with your every motion. If you catch him looking, he’ll roll his eyes, but there’s a flicker of admiration in his gaze. If he ever feels jealous or protective, he’ll only show it in the most passive-aggressive way, something like, “You really should change out of that before someone else starts staring, don’t you think?” But when he says it, you know it's his form of caring.

[guiltyandashamed]

Hihihi! My request is something a little unusual and you can ignore this if you want, but how would the om characters react to an MC who's a celebrity singer and performs like Sabrina Carpenter :) iykyk

Bonus ask! Who's your favorite celebrity?

headcannons: MC who’s a celebrity singer

Known for your charisma, flirtatious stage presence, and clever, theatrical performances, you're confident under the spotlight but still down-to-earth offstage. Your drive the crowd, and the brothers, crazy.

(My fav singer is Fiona Apple but celeb/actor is Jon Bernthal. The duality of man.)

Lucifer

He admires your professionalism first and foremost. Lucifer sees how you command the stage with ease and grace, how every glance, lyric, and pause is deliberate. He’s not the type to swoon openly, but backstage, he always makes sure there’s water, a towel, and a quiet space waiting for you. If someone talks about your performances in a less than respectful way, they’ll have him to deal with. He won’t say it, but his eyes never leave you when you're up there. You’re dazzling, and he’s quietly, fiercely proud of you.

Mammon

Jealous? Starstruck? Obsessed? Yes, yes, and yes. Mammon loses his mind watching you perform. You flirt with the crowd? He swears you're looking at him. Every lyric feels personal. He brags nonstop—"That's my superstar up there!"—and practically gets into fights with fans trying to get your attention. He’ll try to act chill but turns bright red whenever you dedicate a line to him. After the show, he’s clinging to you like a backstage pass, grinning wide, begging for private encores and whispering, “Ya were incredible, babe.”

Leviathan

Levi's flustered beyond repair. You step on stage, lights hit, and suddenly you’re a completely different person, confident, magnetic, unreal. It baffles him, in the best way. He’s convinced you’re too cool for him, but also can’t look away. He live-tweets every set (“MC just did that thing again, I’m dead”) and collects fan edits like treasure. If you so much as wink at the camera, he short circuits. “Y-You’re like… an idol in a dating sim,” he mumbles, eyes wide. You remind him why he loves performance art to begin with.

Satan

He studies your lyrics, watches your performances like someone watching a play for its subtext. Why you're wearing what you're wearing, the meaning behind your performance, everything. You’re clever, teasing, layered, Satan’s captivated not just by the spectacle, but by the intent. He loves when you weave in double meanings or put bite behind the sweetness of a line. When you give the audience that smug little smile? He mirrors it unconsciously. He might act unaffected, but you’ll catch him listening to your songs with his eyes closed, mouthing the words. To him, you’re poetry in motion, and he’d kill to see the behind-the-scenes drafts.

Asmodeus

Oh, he lives for it. The lights, the flirting, the way you toss your mic like you own the world, Asmo eats it up. He’s front row, screaming every word, wearing your merch and crying about how pretty you look under the spotlight. “You’re like a love spell with a beat,” he sighs, fanning himself. He adores how unapologetically you you are. After shows, he’s clinging to your arm, hyping you up, helping with makeup removal while gushing. Asmo knows performance art when he sees it, and he thinks yours is divine.

Beelzebub

He doesn’t fully get the industry stuff, but he gets you. He’s there, watching from backstage or sitting quietly in the audience, eyes on you the whole time. Your energy makes his chest feel full. You sing like it matters, like you're speaking to every person in the room, and especially to him. He notices the subtle ways you look for familiar faces in the crowd, how you seem to calm a little when you spot him. Afterward, he always brings food and hugs you tight, saying softly, “You looked happy up there. I like that.”

Belphegor

He’s not impressed by celebrity status. But you? You intrigue him. You can be a chaos-bringer onstage, spinning the audience around your finger, and then curl up beside him afterward like none of it happened. That duality fascinates him. He’ll tease you: “So, superstar, still remember us little people?” But the truth is, he watches from the shadows, taking note of the way you smile after hitting a difficult note or the way your fingers twitch with nerves before going onstage. He gets it. And in his own quiet way, he’s always cheering for you.

[guiltyandashamed]

hiii i hope ur having a good day!!! if it’s okay can i request nsfw hcs of the brothers? thank u!!

Yes

I will do anything I am comfortable with. Will automatically be GN unless specified. Go crazy (within appropriate bounds)!!

[guiltyandashamed]

brothers with a shopaholic mc…

headcannons: shopaholic MC

You love browsing, impulse buys, dragging the brothers to stores, and you always have a package on the way. This is how they react/adjust to your favorite expensive pastime:

Lucifer

He’s composed on the outside, but inside? A quiet scream. The endless boxes arriving at the House of Lamentation test even his patience. It's always been bad because of Levi's habits, but along with your influx of shipments, it's overwhelming. He’ll give you a stern look when your fourth new outfit of the week arrives, arms crossed, brow raised. “Again?” he’ll ask, voice dry. He might act annoyed, but he keeps a mental note of your favorite stores and occasionally drops hints about upcoming sales. Once, he even used his Devildom connections to get you on a luxury boutique’s VIP list. “Just… control yourself.” He says, handing you the exclusive invite.

Mammon

Soulmate behavior. He enables you to the maximum. You say “shopping,” and he’s already halfway to the mall. The two of you are a dangerous duo; he’s scheming coupons while you’re scanning racks. Mammon loves matching outfits, trying on sunglasses for fun, and posing with you for mirror selfies in changing rooms. The only time he complains is when you spend too much without him getting anything. “Oi! What about me?! I'm here too!” But honestly? He’s obsessed. He brags about your sense of style and secretly loves seeing how excited you get about small things.

Leviathan

He does not understand the appeal when it's “normie stuff.” But he doesn’t protest too much, especially when you show off your haul in a little fashion show just for him. He sits cross-legged on his bed, blushing furiously, muttering praise into his hoodie. He’s especially into it if you start collecting fandom merch, he’ll even start showing you limited-edition Ruri-chan accessories and figurines. “I guess… if you’re gonna waste Grimm, you might as well waste it on good stuff.” He won’t say it out loud, but he keeps all the little keychains you buy him.

Satan

He pretends to be indifferent. “Material things are fleeting,” he says, flipping a page of his book. But then you mention a charming little antique bookstore or a pop-up stall selling first-edition classics, and suddenly he’s throwing on a coat. Satan appreciates your eye for unique items, he even likes how enthusiastic you get about the aesthetics of it all. He starts buying you thoughtful trinkets to add to your collection, never calling it shopping, always calling it “curating.” If someone judges you for it, his temper flares: “MC’s not wasteful—they just know what they like.”

Asmodeus

You and him are like a match made in heaven hell. He sees your shopping addiction as an art form, a lifestyle. “We need to go together, darling. That way we can be fashionable and iconic.” Asmo helps you plan outfits, takes photos of you in every one, and knows exactly how to style accessories to match your mood. He’s constantly sending you links to “things that reminded me of you,” and half your wardrobe ends up coordinated with his. He thinks your packages are little gifts from the universe and treats each one like an event. Honestly? You two are menaces in malls.

Beelzebub

He doesn’t really get fashion, but he’s the best shopping companion ever. He’ll hold your bags, carry you if your feet hurt, and stay by your side patiently the entire time. Beel never complains, even when he doesn’t understand the appeal of spending so long trying on shoes. He does get excited when shopping involves food, though, you’ve definitely bribed him with snacks. He likes seeing you happy, and if buying stuff brings you joy, then he’s all for it. He doesn’t say much, but he watches you glow as you browse, and it warms something in him.

Belphegor

He’s not moving unless he has to. If you manage to drag him out, he’ll drape himself over benches or lean dramatically against store walls with a yawn. “Can I go back to bed now?” Still, he has a sharp eye for what suits you. He won’t admit it, but he quietly likes watching you try things on. He’ll mumble, “That one looks good,” while pretending not to stare. Occasionally, he’ll sneak something into your cart when you're not looking, usually something soft and cozy. “You’ll like it,” he says, and he’s always right.

[guiltyandashamed]

headcannons: insecure about yourself after seeing someone else (brothers + side characters)

(2.7k words) It happens on one of those rare, quiet afternoons when the two of you are out in the Devildom, The conversation is easy. Until it isn’t. She passes you like she owns the street, tall, poised, beautiful in a way that feels otherworldly. A succubus, maybe, or a siren, or some other kind of woman with an enchanting beauty, with the kind of confidence you’ve never had. Her smile lingers on them for a second too long, and though they barely glance her way, your stomach sinks. You know it's irrational, but suddenly you're hyper aware of everything you're not. You laugh a little too quickly at his next joke. You nod without really hearing. You hide it well, at least, you think you do.

Lucifer

He catches the shift in you almost immediately. The falter in your tone, the way your gaze drops to the ground, hands suddenly too still. He’s attuned to subtle changes, he’s had to be, as the eldest, the one who notices when things go unspoken. And when he sees you look at that passing woman with something quiet and sharp in your eyes, it clicks. He doesn’t comment right away. Instead, he adjusts his pace so that you’re closer to his side. The back of his hand brushes yours.

“You know,” he says softly, “I’ve spent centuries surrounded by beings who try to manipulate attention. But I’ve never once been distracted from what I choose to keep close.” He pauses, turning his head to look at you. “And that’s you.”

Lucifer isn’t always good at emotional tenderness. But when he sees you shrinking into yourself, it rattles him more than he shows. He doesn’t press for explanation. He simply gives you his steadiness, his presence, and a hand that lingers a little longer when he reaches for yours.

Mammon

At first, he doesn’t get it. You go quiet, your smile fades a bit, but you’re still walking next to him, still laughing at his dumb jokes, just a little less like yourself. Then it hits him. He remembers the look you gave that other woman, the way your eyes followed her, then dropped away like you didn’t want to be caught comparing. Mammon isn’t the best with emotional nuance, but when it comes to you? He notices everything.

He panics a little internally. Did he say something wrong? Did someone look at you weird? Why’re you suddenly not smiling the way you usually do when you’re with him?

So he stops walking, right in the middle of the street. “Oi. What’s with the face?” he asks, softer than usual. “Don’t think I didn’t notice.” You try to wave it off, but he shakes his head. “Look, I don’t care who walks by. You think anyone else even exists when you’re around?” His voice cracks a bit from the sincerity. “You’re it, alright? You’re my favorite damn view.”

Then he grabs your hand and keeps walking like nothing happened, but his grip stays firm the rest of the way.

Leviathan

Levi doesn’t catch on at first. He’s too in his head, muttering about a limited-edition figurine he spotted in a shop window. But when he looks over and you’re not reacting like you normally would, he stumbles. “Did I… say something weird?” he asks, immediately assuming it’s his fault. Then he remembers her, the siren who walked past with all the self-assured grace he thinks he’ll never have. And he sees how you looked after her, the quick withdrawal into yourself. His stomach turns. He knows that feeling. He lives that feeling. Being second-best. Invisible. Not enough.

So he sidesteps his usual awkwardness. “Hey, um… if you’re feeling... y’know, weird or off or like, not... good enough or whatever... can I just say—that’s a total crit fail on your perception roll.” You blink, caught off guard, and he rushes on, red in the face. “You’re like... S-tier. I mean that. You’re the only one I feel like I can be this version of me around.” He offers you his sleeve to hold instead of his hand, because he’s still Levi. But the sentiment couldn’t be more real.

Satan

It’s a fleeting moment, but he sees it. The stillness in your expression after the woman passes, the way your voice flattens ever so slightly. You think you’re hiding it well, but Satan knows you too intimately not to notice the cracks. And what really cuts is how you don’t say anything. You just swallow it down like it’s not worth bringing up. He walks in silence for a beat, processing. Then, softly: “She wasn’t even half as radiant as you are when you talk about something you love.”

You glance at him, surprised, and he meets your gaze without flinching. “I know you won’t tell me what you’re thinking. But I want you to know... I saw it. And I see you.” He reaches for your hand, not to pull you along, but just to hold it in his own. “You don’t have to be louder, or flashier, or anything other than who you are when you’re with me.”

He doesn’t push the topic, doesn’t ask you to explain. He just slows down his pace, like he’s willing to match your mood and walk with it for however long it takes.

Asmodeus

He absolutely notices the woman. It’s hard not to, she’s practically dripping with seduction magic. But Asmo’s glance is automatic, casual, already forgotten… until he sees the way you tense beside him. You mask it well, but not to him. You go quiet. You stop making eye contact. His heart sinks. “Oh, darling,” he says, suddenly stopping short and turning to face you. “You felt that, didn’t you?”

He can feel the shift in your energy, the way you’re pulling into yourself. His voice gentles, loses the usual lilt. “You don’t have to pretend with me, you know. I know what it’s like to feel like you’re not enough. Even I get insecure sometimes.” He offers a small, honest smile. “But when I look at you… there’s no one else I’d rather have beside me.”

Then he does something uncharacteristically quiet: he leans in, rests his forehead against yours, and whispers, “You’re beautiful. In ways she’ll never understand.”He doesn’t need you to say anything back. He just slips his arm around yours and holds on, tighter than before.

Beelzebub

He doesn’t notice the woman at all. He’s too focused on whether you’ve had enough to eat, if your shoes are comfortable, if you’re enjoying the walk. But he notices you, how your energy shifts, how your smile fades into something tight and practiced. You try to hide it, but Beel knows the rhythm of your emotions like he knows the beat of his own heart.

He slows his steps, gently bumping your shoulder. “You okay?” he asks, voice low and careful. You nod, of course. You always nod. He stares ahead for a while, chewing on the silence like it’s something hard to swallow.

“I don’t really care what anyone else looks like,” he says eventually. “I care about you. I care about how you laugh, and how you sit beside me even when I’m eating enough for five people. That means more than anything." Then, in that gentle, unwavering way of his, he takes your hand and carries the silence for you. No pressure. No expectations. Just warmth. Just Beel, anchoring you when you start to drift.

Belphegor

He sees her. He sees you seeing her. And he sees you instantly pull away from him in that quiet, invisible way: how your hand doesn’t quite brush his anymore, how your expression dulls like you’ve slipped into some private shadow you don’t want to name.

Belphie gets angry about it, not at you, but at the world that made you feel like you had to compare. That made you feel like less. His hand finds yours again, firmly. “You thinking dumb shit again?” he murmurs, voice heavy with sleep and something else… something protective.

You try to brush it off, but he doesn’t let go. “You’re not allowed to hate yourself around me,” he says simply. “That’s the rule.” He tugs you just a little closer, leaning his head on your shoulder as you walk. “If you’re gonna shut down, I’m still staying right here. Might even take a nap standing up just to prove a point.” It’s his way of saying: I see you. And I’m not going anywhere.

Diavolo

He notices the other woman, sure, but only because your hand suddenly feels smaller in his, your steps a little slower. You don't say anything, but Diavolo's joy dims as he watches you retreat into yourself. He’s not oblivious. His life has been full of people trying to catch his eye, but yours is the presence he’s grown to crave.

“Hey,” he says gently, stopping the both of you. “Look at me.” When you do, reluctantly, quietly, he leans down a bit to meet your gaze. “There is no spell, no charm, no allure that compares to you.” His tone is softer than usual, reverent even. “Do you think I fell for you because of some illusion? I’ve ruled a kingdom for centuries. I’ve seen beauty in a thousand forms. But no one has ever made me laugh the way you do. Or made me feel understood.”

He brushes a hand against your cheek with heartbreaking gentleness. “You don’t have to say what you’re thinking. Just… let me remind you of who you are to me.” He tucks your hand into his arm like it belongs there and walks on, making the whole Devildom feel like it orbits around you.

Barbatos

He senses the change in your mood before you even feel it fully. Your steps become measured, your energy tight. Barbatos is deeply attuned to the unspoken, and though he notices the woman too, he’s far more focused on how you subtly retreat into yourself. He doesn’t draw attention to it immediately. He simply shifts his body closer to yours, not pressing but present.

Then, after a quiet beat, he speaks. “It’s interesting, isn’t it?” he muses aloud. “How easily we mistake someone else’s flash for our own dimness.” You glance at him, startled, but he offers only a small, knowing smile.

“You shine differently. Not loudly. Not demanding. But with depth. Grace. Thoughtfulness. Anyone can catch the eye, but not everyone holds the heart.” Barbatos pauses, as though considering time itself. “And you hold mine.”

He doesn’t say much more, he rarely needs to. But when he offers you his arm again, you feel the strength of it, a quiet anchor reminding you: he chose you. And he always would.

Solomon

He notices everything, the woman, your reaction, the subtle shift in your posture. You’re trying so hard to hide it, but he knows the signs. He’s been around long enough to see that kind of pain wear grooves into people.

He doesn’t call it out directly. Instead, he tilts his head and says, “You know, I’ve met sirens who could stop armies with a single glance. But not one of them has ever made me want to stay.” He lets that hang in the air for a moment before adding, “You do.”

When you blink, unsure how to respond, he offers a rare, genuine smile, less teasing, more honest. “You’ve got a stubborn light in you. The kind that doesn’t need to scream to be felt. That’s what caught me.”

He’ll nudge your hand, light against his own, as if offering you the choice: speak or stay silent. Either way, he’s not going anywhere. “Come on,” he says, softer now. “Let’s go somewhere quieter. Just us.”

Simeon

He notices, not just the other woman, but the way you go quiet. How you withdraw without a word, folding into yourself like a page creased by habit. His heart aches, not just for your sadness but for the effort you make to hide it.

He slows his pace to match yours, letting the quiet settle before saying, “There’s a kind of beauty no glamour can touch.” You glance at him, unsure whether to brush it off. He offers you a gentle smile, the kind that makes it feel like the sun’s peeking through your clouds.

“I’ve lived among angels, watched starlight bloom in the Celestial Realm… but none of it has ever made me feel the way I do when I see you.” His words are soft, unflinching. “And I see you. Even when you try to disappear.”

Then, without asking, he loops his pinky with yours, quietly grounding, quietly sincere. “You don’t need to say anything. But I’m here. Always.”

Mephistopheles

He doesn’t notice right away, too busy monologuing about something minor and theatrical, until you suddenly stop contributing. It takes a few seconds for the silence to register, and then he glances at you. Your face is neutral. Too neutral. “Oi,” he mutters, nudging your side. “Where’d you go just now?”

You give him a practiced smile. It’s almost enough to fool him. He follows your gaze, sees the woman walking away, and instantly connects the dots. His jaw clenches, not out of jealousy, but fury at the self-doubt flickering in your eyes. “Pfft,” he scoffs, too loud on purpose. “Overdressed and underwhelming. Wouldn’t last a second in a real conversation. You? You could destroy me with one look, and that’s before you’ve had your morning tea.”

He says it like a joke, but his eyes betray the sincerity. “Next time your thoughts try to trick you like that… just tell them to shut up. Or let me do it for you.” Then he threads your arm through his dramatically. “Now come along, my love. You’ve got a face worth showing off.”

Thirteen

Thirteen clocks the siren in an instant, and rolls her eyes so hard it’s a wonder they stay in her skull. But when she looks back at you and sees the way you’ve suddenly gone quiet, the light dimmed in your expression, she stops dead in her tracks. “Hey. Don’t do that.”

You blink at her, startled. “Do what?” She squints at you, then squints harder. “That thing where you act like you're fine but you’re actually spiraling over some glittery bitch who couldn’t outsmart a single one of my traps.” You try to brush her off, but she doesn’t let you.

“Seriously,” she mutters, moving to stand in front of you. “I’ve seen you face down demons, chaos, me—and that’s what gets you? That?” She jerks her thumb back toward the siren. Then, more softly, “You don’t see it, but you level me. Every time you laugh. Every time you keep showing up.” She nudges you with her elbow. “You don’t gotta talk. Just… don’t disappear, okay?” Then she throws her arm around your shoulder and grins. “Let’s go cause trouble. Hot people like us can get away with anything.”

Raphael

He notices the subtle shift immediately, your quiet withdrawal, the way your gaze drops when the other woman passes by. He’s always been keen on observing the small details, and this one pulls at something deeper in him. Raphael rarely speaks out of turn, preferring to keep his thoughts measured and precise, but when he senses your mood darkening, he allows himself to be a little more direct. “Is something troubling you?” His voice is calm, steady—a gentle anchor in the swirling discomfort you feel.

You try to brush it off, but he doesn’t press. Instead, he stays close, matching his pace to yours as you walk. “You often doubt yourself,” he says quietly, “but I see strength in you that you don’t even realize you have.”

He pauses, looking at you with unshaken sincerity. “The world might throw illusions of beauty your way, but what matters most isn’t what you show on the surface. It’s the kindness you carry, the care you give, the healing you inspire. Those things don’t fade, no matter who passes by.”

Raphael offers you a small, rare smile, not the serene healer’s smile, but a warmer one meant only for you. “You are more than enough. And I am here, always ready to remind you of that.”

[guiltyandashamed]

headcannons: the moment they fell in love

You’d been with the brothers for some time now, long enough to recognize their habits, their moods, the way each of them loved in their own unique language. They didn’t fall all at once. It was gradual, quiet in some cases and impossible to ignore in others. Each of them warmed up to you at their own pace, but when it hit, when they realized they’d fallen for you, they fell hard. And there was no going back.

Lucifer — Slow-burn, recognition over time

Lucifer doesn’t fall easily. He resists the idea of being emotionally compromised. For him, it wasn’t a dramatic moment, it was a gradual accumulation. He notices how you hold your own, how you work hard without necessarily being noticed, how you ease the burden of handling his brothers, and how you effortlessly calm him during times of stress. But the moment hits one evening after a long council meeting. He comes home and finds you waiting for him. The house is quiet, no chaos, seemingly you took care of everything so he could come home to peace. You smile and hand him a cup of tea. No words, just an understanding. His eyebrows lift ever so slightly, he takes the tea and gives you a soft thanks. He feels it then: a rare warmth that makes the silence between you more comfortable than any conversation. He doesn't panic, but he does retreat, quietly adjusting his cuffs, unsure what to do with something so... human. He'll often just stare at you, thinking to himself about his feelings. If you meet his gaze he'll look away briefly, clear his throat and pretend to do something else. How has a human infiltrated his heart and mind like this? Ridiculous, he mutters to himself, but the way his chest tightens says he believes otherwise.

Mammon — Love at first sight, but he doesn't know it yet

The second he lays eyes on you, he knows you’re different. But he brushes it off, calls it curiosity, interest, maybe even a small crush. He's always in your room, invading your privacy, being clingy, he never asked himself why he liked being around you, because he was scared of the answer. It’s not until he finds himself instinctively stepping in front of you during a threat, heart racing, fists clenched, that it clicks. He’s terrified by how badly he wants to protect you. His reaction? Defensiveness. Lots of “It’s not like I like you or anything!” and awkward attempts at distancing himself, which only pull him in closer. The realization hits him fully when you defend him, a moment of unexpected loyalty. His heart stutters, and he can’t look you in the eye. “Damn it,” he mutters under his breath, voice shaky, “Why do you make me feel this way?” A few weeks pass and you notice his face turns red if you stare at him too long. Sometimes he just paces around his room internally panicking after an interaction with you, thinking you know his secret–his love for you–as if it isn't blatantly obvious.

Leviathan — Slow-burn, denial stage included

Levi thinks he’s not the kind of person people fall for, so he never lets himself consider falling for someone either. At first, he tries to categorize his fondness for you like he would a favorite character: someone cool, rare, different. But when you stay up with him during a new game release, and he looks over to find you curled against him, your gentle presence grounding him in reality, it hurts a little. It's too real. His chest tightens and he looks away fast, slinking deeper into his hoodie to hide the color rising in his face. “You’re just... too good at co-op,” he mutters. But in his heart, he knows it’s more. He doesn’t understand how someone like you, someone real, could sit beside him and make the world outside his screen feel more important. He falls quietly, helplessly, and never stops. He tries to convince himself later, when he's alone, that his love for Ruri-chan is enough for him, but when he remembers how lonely he felt before meeting you, he knows there's nobody else he'd rather fall for.

Satan — A gradual slide that becomes undeniable

For Satan, love is built on intellectual connection and emotional honesty. You win his attention when you match him in wit, push back when he's teasing, and listen when he's serious. Normally people find him brash or rude, but you seem to soften his edge. You're not put off by him as others are, so he's always respected you for it. But the moment he falls is much softer. You're helping him reorganize his library after a particularly bad outburst. He’s frustrated with himself, expecting you to be wary of him, but instead, you smile and ask if the fiction should go alphabetically or by theme. Your calm in the aftermath of his rage, your easy presence among the ruined books and sharp silence, feels like a balm he didn’t know he needed. The way you normalize his worst parts, without pity, undoes him. He realizes then that he wants your presence in both the quiet and the chaos. His reaction? A thoughtful pause, followed by a soft, genuine smile he rarely shows. He doesn't say anything right away, but from then on, he looks for more excuses to spend time with you.

Asmodeus — Instant attraction, deeper love over time

Asmo knew you were different when he realized his magic charm didn't work on you. People were easily enamored by him, but you? He flirts, of course, testing boundaries with a twinkle in his eye. But when you don't play into it the way others do,when you're gentle with him as a person, not just a pretty face, he becomes genuinely curious. You listen when he talks about the things no one else cares to ask, his insecurities, his quietest dreams,and he finds himself saying more than he meant to. The moment it turns to love is intimate: you catch him in his room late one night, makeup half-removed, smile nowhere in sight. As much as Asmo portrays himself as unbothered, he's not immune to negative emotion. You ask if he wants company without expecting anything. There’s no performance in your voice, no angle, just care, and he realizes he doesn’t know how to protect himself from that. When he nods and you sit beside him, just being there, he leans into your shoulder and thinks: This must be what love feels like. Even in silence, he feels adored, not because of how he looks, but because of who he is. It terrifies and thrills him. He clings a little tighter that night.

Beelzebub— Slow, steady, and deeply rooted

Beel falls in love the way trees grow: quiet, strong, and always. It starts when you offer him food without fear or judgment. It deepens when you sit beside him in silence, content just to be near. But the moment hits him one day in the kitchen. You’re making something for everyone, humming to yourself, flour dusting your sleeves. He sees how happy you look caring for others, and his chest feels warm in a way hunger can’t explain. You offer him a spoon to taste and smile like it's nothing, but to him it feels like everything. He watches you move around the kitchen like you belong in his world, like this moment was always meant to be. It’s not loud or dramatic, but it settles in him so deeply he knows it won’t leave. He doesn’t say the words, but from that moment on, he’s all in. His love is simple: he shows up, carries your weight, and never lets go. He’d protect that quiet kind of joy you bring with the same devotion he gives his family.

Belphegor — Reluctant love, but impossible to ignore

Belphie fights it. Hard. After everything he’s done, he doesn’t think he deserves your kindness. At first, he pushes your affection away with sarcasm, trying to keep you at arm’s length. But the moment he falls is unexpectedly vulnerable. You find him asleep in the planetarium, clearly exhausted and wanting to get away from the chaos inside the house, and instead of waking him, you sit beside him and stay. When he wakes, still half-dreaming, he sees you there. head resting on his shoulder, trusting him enough to fall asleep too. It breaks him open. You didn’t ask for anything, didn’t pry or judge, just chose to exist quietly with him, and that choice mattered more than he could ever say. The ache in his chest wasn’t guilt this time, but something heavier and gentler all at once. He doesn't speak, just watches you breathe for a moment, and something soft and sharp settles in his chest. He falls quietly, but it hits like gravity. He’ll never admit it out loud, not yet, but from that night on, he sleeps better knowing you exist. He starts finding more reasons to linger near you, even if it’s just in the same room, like your presence tethers him to the better parts of himself.

[guiltyandashamed]

100 followers!!

Feel free to request anything on this post, I'll do headcannons, personal quick stories, or other scenarios, fluff, nsfw, etc. (Make sure to specify, especially if you want something specific or more broad).

Thanks for liking my stuff :)

[guiltyandashamed]

I was hoping no one noticed (H was missing too)

satan found a cat font

and now he sends you messages with it

you barely decipher what he's saying