azaliaplain

[azaliaplain]

Hiii do you have a list or anything of headcannons that you are comfortable writing? Cause I have a request but I’m not sure if it would be ok.

Thank you for asking! I was thinking of making something like that actually to make requesting a little easier for people who would like to. I’m also working on a masterlist for headcanons I’ve already done. As for your question - I’m fine with writing anything as long as it’s SFW as I don’t really think I have enough writing experience to do anything too smutty with confidence and I’m a minor myself (16). That being said - I’m okay with writing some stuff that could be suggestive but not outright NSFW.

[azaliaplain]

guys i saw this on pinterest yesterday and it’s literally perfect down to the names and everything so i made something lol.

i imagine jimmy sent this to gary as a group text with the clique leaders.

[azaliaplain]

Can I request headcanons for Hal Esposito or Lucky De Luca being a caretaker, please?

thank you for the request, honey! (i decided to do some headcanons for both, i hope that’s okay.)

🚬 Caregiver!Hal Esposito & Lucky De Luca x Regressor!Reader HCs 🚬

Hal Esposito (Caregiver):

- Hal is surprisingly gentle when it comes to taking care of someone who regresses — he knows what it’s like to carry insecurities and tries his best to make you feel safe and loved. He’s constantly checking in with you, asking things like, “You good, kiddo? Need anythin’?” to make sure you’re doing alright.

- He really likes when you sit and eat with him because food is one of the ways he shows care. He’ll happily share snacks with you, especially cheeseburgers, but if you’re not into greasy food he’ll awkwardly try to find something softer or more comforting for you (like mac & cheese or pudding cups).

- Hal thinks being a caregiver is mostly about keeping you safe, so he gets very protective to the point of threatening anyone who teases you — he’ll throw around lines like, “You want me to sit on ya? Thought not.” to chase bullies away.

- Despite his tough-guy Greaser image, he actually melts when you ask him to read to you or watch cartoons together. He might act embarrassed about it at first, but deep down he loves having an excuse to enjoy “kid stuff” without judgment.

- If you ever get insecure while regressed, Hal is quick to reassure you. He knows what it’s like to feel different, so he’ll squeeze your hand and mutter, “Don’t let nobody make you feel down, alright? You’re perfect the way you are.”

- He would also absolutely use his big frame as a sort of “fort” for you — letting you curl up next to him or even hiding you behind him if you’re feeling shy.

Lucky De Luca (Caregiver):

- Lucky takes his “responsibilities” super seriously, so he slips into the caregiver role naturally. He thinks it’s like holding down an honest job: if you’re going to do it, you do it right.

- He insists on setting routines, like nap times, snack breaks, or even a daily walk. If you try to argue, he’ll give you the most smug little lecture about “structure builds character” before tucking you in anyway.

- Lucky loves practical caregiving acts: making you sandwiches, tying your shoelaces, carrying your bag, because it lets him feel useful and dependable. He’ll likely also brag about being “the best caregiver you could ask for”, half-joking, half genuinely convinced. He definitely thinks he’s acing it.

- He gets easily irritated if anyone teases you while you’re regressed. He’ll puff up and act like he’s about to throw hands… even though his fighting skills are just okay. (It’s the thought that counts!)

- He’ll hype you up constantly, saying stuff like, “You’re doin’ so great, kiddo”, because he genuinely believes encouragement can change the world.

- Deep down, he likes how being your caregiver makes him feel more mature than the other Greasers. It’s his little way of proving he’s not just another tough guy hanging around the shop class lot.

- In the end, they’ll both swear up and down they’re just “lookin’ out for ya”, but everyone knows they’ve got a soft spot a mile wide when it comes to you.

[azaliaplain]

Got bored and I dunno how to draw so I made Jimmy Gary and Pete in Pony Town!!

I made Pete first and was too lazy to make a new skin so I just used the same one for Jimmy and Gary but I will definitely make them their own skins later!!!

So far only like two people have actually recognised them so I don’t think there are many Bully fans on Pony Town but I will persevere. 🥲 These are a WIP so any feedback is of course appreciated!!

(Also, to those who have sent requests for HCs, I promise you I’m working on them! I should hopefully be able to finish and post them by tomorrow or monday at the latest. 💕)

[azaliaplain]

out of all the students in the game, tad feels like the most likely to be a regressor in my mind, assuming its not canon already with some of his more uncomfortable lines. can i request some softer hcs for him regressing?

thank you for the ask, angel! (you are so real for this i totally agree and i apologise for the wait!)

💎☕️ Regressor!Tad Spencer x Caregiver!Reader Headcanons ☕️💎

- Tad tends to regress to a very young age — around 3 to 5 years old. Growing up in a household where affection was rare and always conditional (if it existed at all) left major gaps in his emotional development. He slips into that little headspace craving the love and safety he never got to experience.

- The first time you stumbled upon him regressed, his first instinct was to panic. Every cruel word his father ever spat at him — calling him weak, too sensitive, embarrassing — came rushing back. He tried to shut down, hide, apologize. But you only opened your arms and told him softly, “You don’t have to be strong with me, sweetheart.” That was all it took. He broke down crying in your embrace, clinging like he was afraid you’d vanish.

- Once he gets used to being little around his new caregiver, Tad will follow you around like a baby duckling, always wanting to stay close. If he’s not tucked at your side, he’s either holding onto your sleeve or curling up in your lap.

- You're endlessly gentle with him. You never raise your voice or give demands. Instead, you offer choices — “Do you want your bubble bath now, or after your snack?” — so he feels safe and in control, something he rarely experienced growing up.

- His comfort foods are all about texture and familiarity: butter cookies, fresh fruit slices, tiny sandwiches cut into little shapes. You serve them on delicate porcelain saucers because he still likes everything to be posh and perfect — true to his Prep roots even in a little headspace.

- Bedtime stories are a non-negotiable. He adores picture books about woodland creatures in waistcoats, classic fairy tales, or anything involving castles and princes. Alice’s Adventures in Wonderland is his favorite — he’ll fight sleep just to hear you finish the story, even though he’s heard it a hundred times.

- You once gifted him a wind-up music box that plays Clair de Lune. Every night, he winds it up himself before bed, hugging a well-loved stuffed dog close as the soft notes fill the quiet. The stuffed dog in question, Sir Barkington III, is a bit threadbare and missing an eye, but he was a gift from a kind nanny Tad had briefly as a child and he won’t sleep without him.

- Praise means the world to him. When you call him your brave boy, your sweet prince, or tell him how proud you are of him, he gets misty-eyed. It still feels surreal to be spoken to with such tenderness — but slowly, he’s starting to believe he’s worthy of it.

- For Tad, regression is a way of healing. With you as his caregiver, he’s finally discovering what it means to be wanted, not just tolerated. Every moment of gentle affection, every whispered reassurance, slowly chips away at the cruel voice in his head that says he doesn’t deserve to be looked after.

[azaliaplain]

hii can i request some ted headcanon as a caregiver/caretaker

thank you for the request, lovely!

🏈 Caregiver!Ted Thompson x Regressor!Reader Headcanons 🏈

- Ted isn’t the most emotionally expressive guy at first, but when he realizes you feel safest and happiest in your little space, he steps up without hesitation. He might not always understand why you’re regressing, but he doesn’t need to. Ted’s very much “you’re small? okay, then I’ll be big for you.” Zero judgment, full support.

- Very “acts of service” type — he shows care by doing. Warm milk ready without asking, cozy blankets straight from the dryer, and he keeps snacks on hand in his gym bag just in case you get pouty or need a pick-me-up. He always acts like it’s just coincidence, but you know he carries your favorites on purpose.

- He’s really good at routine — if you need a consistent bedtime, snacktime, or wind-down time, he’ll make sure it happens. He’ll even carry you to bed on piggyback if you’re too sleepy. No hesitation. He says it's “good training for carrying a teammate off the field.”

- He’s not the type to call you pet names constantly, but every so often, a soft “kiddo” or “champ” slips out when he’s extra soft on you.

- He lets you wear his letterman jacket and loves reading to you while you're cuddled up in it, even if it’s just his playbook because “it’s all I’ve got right now.” His voice is so soothing you don’t even care what he’s reading.

- Big on quiet time together. He’ll let you lay across his lap while he rubs soft circles into your back or traces your face with his thumb until your breathing evens out. Sometimes he falls asleep too, chin resting on your head, arms wrapped around you protectively.

- Has no patience for anyone who doesn’t treat you gently. If someone even looks at you funny while you’re regressed, Ted’s instantly in front of you, shielding your space and telling them to back off. No one messes with his little one.

[azaliaplain]

Hi can I request some headcannons of Beatrice regressing and how it goes :)

thank you for the request, honey! (and apologies for the wait.)

🧪📚 Regressor!Beatrice Trudeau x Caregiver!Reader Headcanons 📚🧪

- Beatrice is a very shy and private regressor at first. She only feels comfortable regressing around a tiny, trusted circle — and even then, it takes time. But with a patient and gentle caregiver (you), she slowly begins to feel safe enough to be little around someone else.

- Her regression age usually sits between 5–7. It’s a cozy in-between: old enough to explore, ask questions, and flip through books on her own, but still young enough to need cuddles, comfort, and lots of reassurance. Her biggest triggers are school stress and social pressure as being so academically gifted means there are always expectations from teachers, classmates, and even herself. Then when it all becomes too much, her brain gently says: “Okay. Time to be small now.”

- Even when she’s little, Beatrice is a total bookworm. Her favorite thing is flipping through picture books — especially science-themed ones. She loves reading them aloud to you and absolutely beams when you praise her. If you clap and say, “Wow! Your pronunciation was perfect!” she’ll go all pink and bashful and hide her face behind her sleeves like “Oh... it was nothing, really…”

- She adores pretend play and takes it very seriously. Her favorite game when regressed (and even sometimes when she isn’t) is playing doctor with her dolls lined up in neat rows on the bed. She wears a toy stethoscope, scribbles notes in a notebook, and diagnoses each of her “patients” with intense concentration. If you’re around, she’ll ask you to join in as her assistant nurse.

- You can tell she’s starting to get sleepy when her sleeves droop past her hands, her glasses slip down her nose, and her voice gets all soft and mumbly. She’ll crawl into your lap mid-sentence and start listing half-remembered science facts like, “Did you know your brain has… eighty… eighty-something billion neurons…” before her words slow and she nods off on your shoulder.

- More than anything, regression helps Beatrice feel safe, accepted, and unconditionally loved. You read her stories, brush her hair behind her ears, and remind her gently that she doesn’t have to be perfect — she just has to be herself.

[azaliaplain]

Hiiii, ive got a Request for headcanons about leon from bully as caretaker.

I like the thought of him regressing especially since knowing that leon calls for "mommy" in his crying dialogue.

thank you for the request, angel! (and apologies for the lack of pictures this time, i literally couldn’t find a single one except for the one on his wiki page 😭)

🧸✨ Regressor!Leon (Townies) x Caregiver!Reader Headcanons ✨🧸

- Leon is very small when he regresses — emotionally around 3-5 years old. Not much talking unless he feels safe. Lots of hiding his face in your chest, wrapping his arms around your middle, and tugging at your clothes for comfort.

- He doesn’t regress super often, but when he does, it’s usually triggered by stress or sensory overload. When the Townies’ hideout gets too loud or overwhelming, he’ll wander off until he finds you.

- You keep a soft sweater or blankie with you just for him, and the moment you wrap it around his shoulders, he clings to you and lets out the tiniest sigh like he’s finally home.

- He loves being rocked or held — especially when you hum softly in his ear or trace gentle shapes on his back. It’s one of the only ways he can fall asleep when he’s regressed.

- He gets sleepy so fast when he’s little… you’ll often find him rubbing his eyes with his sleeves, curling up in your lap without a word while you read to him or just play with his hair.

- His favorite little snacks are the soft ones — applesauce pouches, fruit chews, and occasionally those little animal crackers you keep in a tin just for him. He lights up every time you surprise him with a treat.

- Even the other Townies (especially Zoe and Jerry) get quieter when they know he’s regressed. They’ll ask where you are if Leon starts to look fussy, and Otto once offered him a plushie he found “so he’d stop snifflin’.” It was honestly really sweet.

[azaliaplain]

hiii!! could u pls do jimmy gary and petey feeling sad or acting out when they r regressed or caring for a reader whos feelimg sad or acting out? tyy xx

thank you for the ask, sweetpea! i was inspired so this is kind of a long one

Jimmy, Pete, and Gary as a regressor/caregiver when sad or acting out HCs!

Jimmy Hopkins (Regressor):

When Sad:

- He bottles everything up until it explodes. One minute he’s stoic, the next he’s curled up in your lap like a toddler trying not to cry.

- His regression is subtle at first—he starts dragging his feet, mumbling, using simpler words, not wanting to be left alone.

- Clings to you and says things like “Don’t go. Just... stay, please.”

- Cries into your hoodie if you let him.

When Acting Out:

- Picks fights and breaks stuff when he feels out of control. He needs someone to put the brakes on.

- Once he’s burnt out, he crashes into little space hard — doesn’t want to talk, just wants to be held and babied.

- He’ll mumble “Sorry…” while playing with your fingers, then fall asleep mid-snuggle.

Pete Kowalski (Regressor):

When Sad:

- Withdraws. Becomes extra quiet, shaky hands, glassy-eyed stares.

- Slips into a very small headspace quickly — lots of thumb-sucking, hiding behind you, or needing his favorite stuffed animal.

- Needs gentle comfort: soft cooing, rocking, blankets.

- Will whisper ���I’m not okay…” and feel safe once you scoop him up and tell him it’s okay to be little.

When Acting Out:

- Rare but happens when he’s overwhelmed or pushed too far — he might yell, slam doors, or even snap at Gary/Jimmy.

- Regression kicks in right after — he immediately feels guilty, curls up under a desk or in a closet.

- Needs you to help him feel better. Gentle affirmations work wonders.

Gary Smith (Regressor):

When Sad:

- Refuses to admit he’s hurting, but it leaks out as sarcasm and lashing out.

- When regression kicks in, it’s like a light switch: suddenly he’s curled into a ball with his knees to his chest, repeating things like “It’s stupid. I hate it.”

- Pouts, throws small tantrums, but you can tell he just wants someone to love him without judgment.

- Needs to be swaddled in a blanket and reassured that he’s safe.

When Acting Out:

- CHAOTIC. Manipulative, loud, sharp-tongued—and then completely shuts down after a meltdown.

- Regression after an episode includes clinging to your side and whispering things like “Don’t leave like they did…”

- He pretends to hate baby talk—but melts when you call him things like “my grumpy little guy.”

Jimmy Hopkins (Caregiver):

- Protective and hands-on. If you’re sad or acting out, he lifts you into his lap, rocks you, and says “Hey, shh… I got you. Just breathe.”

- Will absolutely punch a student (or a prefect) if they upset you while you’re little.

- Takes you outside for fresh air, carries you around, or helps you color when you’re quiet.

- Talks to you like a cool older brother: “You’re the strongest little one I know.”

Pete Kowalski (Caregiver):

- The gentlest. He doesn’t get mad when you cry or act out — he just holds you and says “It’s okay, let it out, I’m here.”

- Brings you your favorite snacks, your comfort item, and sings to you softly.

- Gives the best cuddles—he radiates warmth and always smells like clean laundry.

- He tells you, “You don’t have to be big right now. Just be my little one, okay?”

Gary Smith (Caregiver):

- He's controlling but effective. If you’re spiraling, he immediately takes charge: pulls you into his arms, hushes you, wraps you in a blanket.

- Will quietly say, “You’re safe. I’m not gonna let anyone hurt you, not even you.”

- Does NOT tolerate anyone upsetting you. Threatens people who even look at you funny.

- He reads to you in funny voices or lets you hold his sleeve while you walk together.

Bonus: Group Dynamic

When all three are regressors at the same time:

- You’re buried in a cuddle pile. Pete is sniffly, Jimmy is trying to be tough but is holding your hand, and Gary is curled at your side mumbling nonsense.

- You have to rotate between soothing them: reading for Pete, rocking Jimmy, brushing Gary’s hair.

- They get competitive for your attention but eventually settle into a sleepy tangle with you in the middle.

When you’re the regressor:

- Pete gets snacks, Jimmy guards the door, and Gary reads a story while secretly recording it for you to replay when he’s not around.

- You’re swaddled in all three’s arms, surrounded by warmth, and not allowed to lift a finger.

[azaliaplain]

Gary, Pete, and Jimmy regressor/caregiver HCs!

Gary Smith (Regressor):

- Reluctant regressor. Gary absolutely hates showing vulnerability, so if he slips into a regressed state, it's usually triggered by severe stress or emotional breakdowns.

- When regressed, he tends to act like a grumpy 5-year-old: moody, demanding, and sometimes pouty if he feels ignored.

- Needs a safe, quiet space and a very patient caregiver (you) to calm him down. Soft touches and repetitive reassurances help.

- He refuses to admit he likes stuffies but ends up stealing Pete’s when he’s not looking.

- Will want to be held but act like he's doing you a favor by letting you cuddle him.

- Favorite comfort item: an oversized hoodie (yours), snacks like PB&J, and old cartoons.

Pete Kowalski (Regressor):

- Pete is the most naturally regressed of the three. His regression is gentle, quiet, and happens when he’s overwhelmed or feeling neglected.

- Acts around 4-6 years old. Loves coloring, stuffies, and being tucked in at night.

- He clings to his caregiver (you) like a baby duck. Might quietly say “I need cuddles…” when he’s slipping into a little space.

- Likes when you read to him or play soft lullabies. He’s not demanding, just very affectionate.

- His regression can be triggered by raised voices or conflict (especially if Gary is spiraling).

- Favorite comfort item: a soft stuffed bunny, hot cocoa, and finger painting.

Jimmy Hopkins (Regressor):

- Jimmy’s regression is rare and kind of accidental. It might happen after intense physical fights or when he’s trying too hard to be tough.

- Acts like a toddler with a big ego — he’ll want attention, praise, and lots of cuddles but will pretend he’s “fine” until he just melts.

- Likes being rocked, eating snacks from your hand, and falling asleep with his head in your lap.

- Is soothed by physical touch: back rubs, forehead kisses, and holding hands.

- Beam cola makes Jimmy hyper when regressed, so try to keep it away from him.

- Favorite comfort item: warm blankets, juice boxes, and you (he gets clingy).

Gary Smith (Caregiver):

- Surprisingly good at it when he’s in the right headspace. Very controlling, but it makes you feel safe.

- Will give you “strict” routines: snacks, naps, playtime — no negotiations.

- Teases you lightly (“Aww, is baby feeling cranky?”) but is always watching to make sure you’re okay.

- He genuinely cares but pretends it’s all for his own amusement.

- Reads you creepy fairy tales in dramatic voices and builds pillow forts with you.

Pete Kowalski (Caregiver):

- Softest, gentlest caregiver. He speaks quietly, coos at you, and makes sure you always feel seen and loved.

- Very emotionally intuitive. Knows when you need touch vs. space.

- Will bring you little treats from the store and tell you it’s “because you’re the best little one ever.”

- Loves to brush your hair, play soft music, and cuddle with you under a weighted blanket.

Jimmy Hopkins (Caregiver):

- Kind of like a big brother caregiver at first — playful, goofy, teasing.

- But when you’re fully regressed, he takes it seriously. He’ll scoop you up and carry you if he has to.

- Gives the best piggyback rides, helps you pick out your favorite snacks, and will show you his comics.

- Gets flustered when you cry, but he’ll wrap you up in his arms and say “Shh, I got you. I’m not going anywhere.”