#chuckie sullivan headcanon

[notfault]

will hunting from good will hunting. headcanon based, alternate universes available. by zawn, 22, they/she. exclusive to nonpareil chuckie sullivan

rules[tba], pinterest

[classic80sand90smovieloves2]

NSFW Headcanons~ Chuckie Sullivan

(Not my gif)(Requested by anonymous)

- While Chuckie certainly has experience with random hookups and booty calls, he has a lot less experience with sex involving an actual girlfriend. In fact, the two of you may just start out at fuck buddies before you catch actual feelings and become a couple.

- Regardless, he’s definitely experienced and knows what he’s doing in the bedroom.

- He’s definitely more of a receiver. He’ll curse and hold your head as you go down on him. He’s also a bit of an ass so he’d like the idea of you giving him head; or cockwarming him with your mouth, while he “ignores you” in favor of a movie or video game.

- Though he does prefer receiving, he certainly isn’t against giving; though he’s definitely more of a hands rather than mouth kind of person. He’s more likely to slip his hand up your skirt or down your pants as he kisses you and your neck than he is to shove his head between your legs; not that that never happens too.

- Foreplay? Depends on the day. Sometimes he’ll spend an hour teasing you, other times he’ll be tearing his belt off the second you’re in the house.

- He’s a little shit and a dom which is both the best and the worst combination a person can have in the bedroom. He gets off on being a jackass and teasing you but you’ll probably enjoy it.

- He likes moving fast and being a bit rough with you. He’s not used to being all soft and loving but he would definitely try if need be. Sex is sex, right?

- He’s not romantic in the slightest but you can’t help but find his Boston accent and vernacular, and the way he grins when you surprise him with lingerie, endearing.

- He talks ...like a lot. He’s constantly teasing you, talking dirty, saying all those “yeah, you like that” types of phrases. It’s sort of annoying but you learn to love it.

- Role playing. He particularly likes the whole ‘boss and secretary’ one. He loves putting his hand up your dress/skirt or feeling you up as you stand beside him, watching your knees buckle as you play along and ask what he’s doing, calling him “sir”.

- Lowkey has a sir kink. He’s never really been called it before but dear god he could get used to it.

- Making jokes or breaking out into laughter at some part of your roleplay. That’s the minute he starts to realize he loves you: seeing you beneath him, laughing and smiling like a dork. His eyes soften and he just looks at you, a smile plastered across his own features as he decides that he’s going to marry you.

- He sort of gets off on the idea of a secret relationship or some other kind of ‘sneaking around behind peoples backs’ type of fantasy. He especially likes the idea of it being because your parents or friends don’t approve. He’s come to terms with the fact that he’s sort of trashy so screwing “a pretentious rich girl off her high horse” is sort of appealing to him.

- He’s sort of into public stuff. Abandoned areas late at night, in an alley or up against a chain link fence, his hand up your skirt under the table at a bar, bathroom quickies, things like that.

- A ton of touching. His hands are always all over you, groping and grabbing you however he wants.

- Be suspicious when he offers you massages because 90% of the time, he either has ulterior motives from the start or he can’t help but let his hands wander which, hey, you can’t deny that it helps you relax.

- Spitting kink. It may be him doing it, it might have been you doing it in retaliation for him spitting everywhere, either way, it gives him a confusing boner and shuts him up for a while.

- Cock worship. It makes him very smug though so be wary.

- Shower sex.

- He likes taking you from behind or having you ride him in reverse cowgirl. He likes being able to hold you by the hips and just go to town.

- Anal.

- Sometimes, he’ll just come home from work; or wherever, and ravage you, pulling you into a fiery kiss before moving to your throat as he works to undress you.

- He’s got a big dick and it’s the main reason he’s such a cocky little asshole so hey, at least you get something in exchange for putting up with his tomfoolery.

- He’ll wear a condom but he’d prefer not to. He’d much rather finish on your chest, face, or in your mouth.

- He definitely does this strangely endearing little shake/twitch when/after he cums and probably gives a “jesus, thank you” after he’s finished which always makes you laugh.

- Not the best at aftercare but he’ll try if it’s necessary; he’s just not used to girls sticking around after they’ve both finished. He’s a big mush when it comes to you so he’s happy to cuddle you; he’s just awkward about it if things between you are “casual”, like, is he allowed to? He snaps out of his awkwardness after you became a real couple.

- He does need a hot minute to catch his breath once you’ve finished though, so you’ll have the opportunity to cuddle into him if you’d like, and he’ll probably get up to “take a leak”; as he puts it, so that’s your chance to ask him to get you something.

[silentcrowsilentravens]

Who I write for + rules + masterlists

Please don't ask for smut.

By default, I write things as gender ambiguous, but you can request for the reader to be a specific gender identity.

I'll do up to eight characters per request.

Requesting dark things with violence/blood is fine. Angst is fine as well.

Requesting completely goofy/stupid/shitpost-y things is fine.

Requesting something poly is fine.

Requesting platonic things (whether familial or friendly) is fine.

Don't be afraid to be specific! : )

With Resident Evil prompts in particular, if you don’t specify a game or movie alongside a character (e.g. 3 REmake Jill or WTRC Leon) then I’m just going to assume that you’re leaving it up to me to choose.

Games include any Resi title released between the original's debut in 1996 and now, even the non-canon ones. You can also ask for it to take place in the Dead By Daylight universe. Movies include all of the CG releases, the Anderson movies, and Welcome to Raccoon City.

Things I write:

Prompt-based x reader ficlets. Send in a scenario and I'll write a short fic about it. If you want it to be platonic, please specify.

Reactions. Send in something you'd like to see a particular character's reaction to (e.g. reacting to a reader with a particular interest/trait, reacting to a reader ending up in a particular situation). I'll write a bulleted list. If you want it to be platonic, please specify.

Headcanons. Send in specific or general headcanons you would like about one or more characters. I'll write a bulleted list.

If you don't name one of these things in your ask, I'll just assume that you're leaving the format up to me.

Resident Evil

Ada Wong - masterlist here!

Albert Wesker - masterlist here!

Alcina Dimitrescu - masterlist here!

Alex Wesker - masterlist here!

Alyssa Ashcroft - nothing yet.

Alice - masterlist here!

Ark Thompson - masterlist here!

Barry Burton - masterlist here!

Becca Woolett - nothing yet.

Bela Dimitrescu - masterlist here!

Billy Coen - masterlist here!

Brad Vickers -masterlist here!

Bruce McGivern - masterlist here!

Carlos Oliveira - masterlist here!

Cassandra Dimitrescu - masterlist here!

Chris Redfield - masterlist here!

Claire Redfield - masterlist here!

Daniela Dimitrescu - masterlist here!

Daniel Fabron - nothing yet.

Donna Beneviento - masterlist here!

The Duke - nothing yet.

Edward Dewey - masterlist here!

Elena Lupu - masterlist here!

Emily Berkhoff - masterlist here!

Enrico Marini - masterlist here!

Ethan Winters - masterlist here!

Finn Macauley - nothing yet.

Fongling - nothing yet.

Forest Speyer - masterlist here!

Hector Hivers - nothing yet.

Helena Harper - masterlist here!

Ingrid Hunnigan - nothing yet.

Jack Krauser - nothing yet.

Jake Muller - masterlist here!

January Van Sant - masterlist here!

Jessica Sherawat - nothing yet.

Jill Valentine - masterlist here!

Joe Baker - masterlist here!

Joseph Frost - masterlist here!

Josh Stone - nothing yet.

Karl Heisenberg - masterlist here!

Karena LesProux - nothing yet.

Kenneth Sullivan - masterlist here!

Leon Kennedy - masterlist here!

Lucas Baker - masterlist here!

Luis Serra - nothing yet.

Mia Winters - masterlist here!

Moira Burton - nothing yet.

Mother Miranda - masterlist here!

Nikolai Zinoviev - nothing yet.

Parker Luciani - nothing yet.

Piers Nivans - masterlist here!

Rachel Foley - masterlist here!

Raymond Vester - masterlist here!

Rebecca Chambers - masterlist here!

Rain Ocampo - nothing yet.

Richard Aiken - masterlist here!

Salvatore Moreau - masterlist here!

Sheva Alomar - masterlist here!

Zoe Baker - masterlist here!

Child’s Play - masterlist here

Charles “Chucky” Lee Ray

Nica Pierce

Tiffany Valentine

Bendy - masterlist here

Alice Angel (cartoon)

Allison Pendle/Allison Angel

Audrey Drew

Susie Campbell/Twisted Alice

Miscellaneous

Amanda Young - fluff alphabet

Abe Sapien (I no longer write for this character) - masterlist here!

Charlotte Deshayes - masterlist here!

Hellboy (I no longer write for this character) - masterlist here!

[classic80sand90smovieloves2]

Meeting and Dating Chuckie Sullivan

(Not my gif)(requested by anonymous)

- You met Chuckie because you lived next door to him and his mother. Every now and again you would have a conversation with the old woman where she would occasionally mention him but you never actually met the boy; that is until his mothers mail got mixed in with yours.

- You knocked on her door to fix the mistake but were caught off guard when you were met with the tall young man instead of his mother. It was almost comical when you looked up from the envelope and were just met with a chest instead of a kind face.

“Oh, uh hi…? I live next door and your mail got mixed in with,” you notice that he’s wearing boxers and pause a little. “…with uh, with mine. So…here.”

- You want to slap yourself with how awkward you’re acting but you were not prepared to find out that Ms. Sullivan’s son is at least half a foot taller than you and has the face of a model. You were also not expecting to meet him for the first time while he’s still wearing his boxers and sleeping shirt.

- He chuckles a little and takes the mail from you while scratching the back of his neck. He’s about to try and make conversation with you before he realizes he’s only partially presentable and should probably put on pants before he tries to woo you. (It’s enough that he lives with his mom, right? He doesn’t want you to think he’s unsound.)

“Right! Well thank you, nice meeting you, see you around.” He rambles while he shuts the door with a unreasonably charming smile.

- Chuckie knows he’s handsome and he’s used to girls falling into his lap but those are girls who don’t know him and don’t know that he lives with his mom (which he’s quite embarrassed about). He’s not sure how to make himself seem worth your time now that he can’t lie and say that he’s something far more impressive than he thinks he is. 

- He has to find an entirely new way to impress the girl who lives next door and he’ll admit that he hasn’t the slightest idea where to start. The instant he sees you he tries to “act cool”, leaning against the nearest surface and greeting you with a smirk plastered across his ridiculously handsome face. 

- He has quite the embarrassing/awkward conversation with Skylar in an attempt to get some real advice. She tries her hardest not to laugh when he rambles out his questions and the things he likes about you. In the end she just tells him to be himself and get to know you before he tries to get in your pants.

- He decides to trust her and does just that. The next time he sees you he invites you to take a walk with him while the two of you get to know each other better. The both of you are sort of surprised that the other is giving you the time of day.

- When you get back to your houses and are about say goodbye his mother pokes her head out and invites you to dinner. Later that day you get to hear a bunch of embarrassing stories about Chuckie while he sits in utter embarrassment and tries to shut his mother up when you’re turned the other way. She nearly breaks out the baby pictures but he manages to stop her.

- He offers to walk you home when you’re finished eating and talking (even though you’re just a few yards away from your house). You accept and he joins you outside for the quick journey to your front door. When you get there he starts to apologize for his mother but you stop him and say you had a fun time, kiss him on the cheek and say goodnight before you go inside your house. He stands there for a minute in disbelief before he smiles and fist pumps, racing back to his house. He can’t even be mad at his mom because he’s so happy that you don’t think he’s a total loser.

- In the beginning you don’t really label what you have you just hang out, do borderline romantic things, and stumble over awkward goodbyes. After some time you start to kiss and fool around a little but it doesn’t really feel like a “real relationship” and neither of you are brave enough to ask what you actually are. Plus he’s good in bed so you don’t mind all that much.

- It’ll feel like you’re friends with benefits for a while before he starts to get all boyfriendy with you. Cuddling, hugging, cheek kisses, hand holding, etc; he just won’t be able to help it after a while. After about a month of you acting like a couple he’ll finally ask if you’re together like~

“We are dating right?”

“I would hope so.”

“Alright cool, good, great, wonderful,-” “Chuckie?”

“Yeah?”

“Shut up.”

- You kiss a lot after that. You can’t stop him. He’s a mad man after one thing and one thing only: the smooch.

- You move in together (well he moves into your house) maybe a little too early on in the relationship but you lived next door to each other so the move wasn’t a big hassle. Plus he makes some good money when he works hard so it makes paying the bills a lot easier for you.

- Hes kind of just happy to move out of his moms house even though he’s a little scared of commitment. But he thinks that maybe with you he doesn’t have to be scared.

- Cute nervous chuckles when he isn’t sure what to say or is a little flustered, especially when you’re getting to know each other.

- His friends try to embarrass him and tell you he’s whipped every chance they get especially when you first meet them.

- Hes not the greatest at comforting you. He’s a rough and tough kind of guy that’s not use to showing emotions or being around people that do so chances are when you rant to or tell him about something he’ll just pause and say “well that sucks”.

- Sneaks little glances at you when he thinks you aren’t looking.

- Watching morning cartoons with him. 

- Sleepy hugs and snuggles in the kitchen while you’re making food after a long day.

- He’s pretty much in his boxers whenever he can be so be prepared to have to remind him to put on some real clothes every now and again. 

- Lays his head on your stomach as you thread your fingers through his hair; he loves it especially after work.

- He falls asleep on you a lot when hes not working. He’ll just collapse on the couch beside you, laying his head on your thigh or stomach thinking ‘wow this is so…comfy” and before you know it he’s passed out and borderline snoring.

- He rests his hand on your boob a lot. It’s not even a conscious decision, his hand just always ends up on your chest whenever he has his arm around you. In his mind he’s just thinking “warm…soft…resting place.”.

- Late night dates since he works long shifts.

- Pizza dates.

- Visiting him on his breaks.

- Making fun of his accent, you're the only one he lets insult him without much retaliation. He thinks you’re a cute little bastard. 

“You’re lucky your smiles so cute or I woulda knocked ya teeth out for that one.” you give him the nicest smile you can and he just shakes his head, pulling you into his side. 

- But you do make constant jabs at each other. The two of you go back and forth with clever little comebacks/burns that force you to break the serious act you were putting on. He usually lets you win you’re little insult battles. 

- Hes naturally sort of a flirt but he tries his absolute best to stop because he doesn't want to lose you.

-Sharing a few beers after the two of you get home.

- He does pretty rough work so you tend to give him massages when he gets home. You make him sit in front of you on the couch or lay on the bed while you straddle him. He’ll try to insist that he’s fine the first time you try to do it because he wants to seem tough but the moment you start to massage him he literally moans. He’ll never pass up the opportunity again and he likes to return the favor although his massages usually take a more sexual turn.

- He’s a little insecure even though he tries his best to hide it from the world. He thinks he’s sort of a loser compared to you (and Will) and is worried that he’ll end up going nowhere in life. He’s also worried that you’ll see him for what “he really is” and decide that you don’t want to put up with him anymore. 

- When you fight he rarely yells but he does make you angry; avoiding the subject, lying or just not admitting that he was wrong. You’ll most likely try to make him sleep on the couch, whereupon he’ll just go to his moms or Wills and mope around for a while while he pretends that he doesn’t care.

- He tries to apologize and explain himself when he can’t stand not seeing you anymore but he rarely ever helps his case cause he says shit like~

“I lie to women all the time and it don’t mean nothin it’s just the way I do business you know, it’s just the way.”

- But sometimes you miss him just as much and just forgive him so you can have him back in your life. You do give him a firm punch on the arm and tell him that if you catch him lying or whatever again that you’ll wreck his car.

- Holding hands as you walk together on the streets. 

- Has definitely gotten into at least one drunken (or sober) fight at a bar when someone tried to hit on you or managed to smack you on the ass. You were probably banned or kicked out afterwards.  

- You have to hold him back when someone catcalls you. 

- He’s jealous and possessive. You’re the one thing he really has for himself, that he’s proud of and really cares about so when someone (in his head) threatens to take you away

- Likes to keep his hand in your back pocket.

- He tries his best to be at least a little romantic with you. 

*laughs*

“What?”

“Chuckie these are weeds not flowers.”

“You’re shitting me!” 

- So out of his element when you drag him to boutiques or perfume shops. It’s honestly kinda cute, he’s like a lost puppy surrounded by all that pink, bows and lace. 

- You’re a godsend to him if you know how to cook. He would quite literally survive on cereal and fastfood if you didn’t know how. If you don’t know how than you can try to learn together, can’t promise it will go very well but it’s cute to see each other struggle.

- Helping him clean dirt and grease from his face after he gets home from work. 

- He honestly just loves when you touch his face, like your hands are just? so soft?? So nice??

-You think he’s phased when you ask him to buy you pads? He’s a grown ass man doing grown ass things and he’s gonna do what he has to do to make your life easier.

- He wants you to have the best out of life no matter what. Sometimes he’ll try to sabotage your relationship if he thinks he’s holding you back but you always assure him that if you’re going somewhere, you’re going somewhere together.

- You get close with his friends. You sort of have to, they’re a big part of his life.

- Hes not the greatest with compliments so you usually get the creative “you look hot” or something similar.

- He tries to be a little gentlemanly but that mainly consists of him giving you his jacket or opening his car door for you.

- He picks you up and throws you over his shoulder while he gives your butt a smack.

- He avoids marriage talk. Not because he doesn’t want to marry you (he certainly does) but just because it makes him uncomfortable. He’s not used to having an actual girlfriend who really cares about him.

[classic80sand90smovieloves2]

Masterlist

A list of my old writing that you can request I revise

Song Prompts

Meeting and Dating Headcanons~

Pretty in Pink

Andie Walsh

Duckie Dale

Blane McDonagh

Steff McKee

Sixteen Candles 

Jake Ryan

The Lost Boys

Paul

Dwayne

Poly Lost Boys

Edgar Frog

The Breakfast Club

Brian Johnson

John Bender

Andrew Clark

The Outsiders

Sodapop Curtis

Dallas Winston

Two-Bit Mathews

Rumblefish

Steve Hays

Ferris Buellers Day Off

Cameron Frye

Karate Kid

Daniel Larusso

Johnny Lawrence

Dutch

Heathers

Veronica Sawyer

Jason Dean

Fast Times at Ridgemont High

Jeff Spicoli

Brad Hamilton

Better Off Dead 

Lane Meyer

Weird Science

Gary Wallace

Wyatt Donnelly

Dream A Little Dream

Dinger Holfield

Bill and Teds Excellent Adventure

Bill S. Preston Esquire

Ted Logan 

Dating Poly Bill and Ted 

The Princess Bride

Inigo Montoya

Interview with the Vampire

Louis de Pointe du Lac

Children of the Corn

Malachai Boardman

National Lampoons 

Rusty Griswold (European Vacation)

Cant Buy Me Love

Kenneth Wurman

The Chocolate War

Jerry Renault

Archie Costello

The Mighty Ducks

Fulton Reed

Dean Portman

Adam Banks

Les Averman

Porkys

Brian Schwartz

Anthony ‘Meat’ Tuperello

Tommy Turner

Tim Cavanaugh

Mickey Jarvis

Just One of the Guys

Terry Griffith

Greg Tolan

Dead Poets Society 

Neil Perry

Todd Anderson

Charlie Dalton

Knox Overstreet

Steven Meeks

Earth Girls are Easy

Mac

Combat Academy 

Perry Barnett

Waynes World

Garth Algar

Austin Powers

Austin Powers

Toy Soldiers

Ricardo Montoya

Good Will Hunting

Chuckie Sullivan

10 Things I Hate About You

Joey Donner

My Bodyguard

Ricky Linderman

Melvin Moody

Stand and Deliver

Angel Guzman

Something Wild 

Ray Sinclair

Three O’Clock High 

Buddy Revell

Intruder

Randy

Young Guns

Jose Chavez y Chavez

Billy the Kid

Doc Scurlock

Dazed and Confused

Benny O’Donnell

Don Dawson

Kevin Pickford

Randall “Pink” Floyd

Fred O’Bannion

Mitch Kramer

Ron Slater

Shavonne Wright

Dogfight

Eddie Birdlace

Ladybugs

Matthew

Goosebumps

Sticks

Freddy Renfield

Twister

Robert ‘Rabbit’ Nurick

Stand by me 

Ace Merrill

School Ties

Rip Van Kelt 

Chris Reece

The Untouchables

Eliot Ness

The Godfather

Tom Hagen

(Young) Vito Corleone

(Old) Vito Corleone

Goodfellas

Henry Hill

Little Shop of Horrors

Seymour Krelborn

Newsies

Specs

Near Dark

Severen

Friday the 13th

Jason Voorhees

Scream

Billy Loomis 

Poly Billy and  Stu

Stu Macher

The Craft

Nancy Downs

Hocus Pocus

Max Dennison

Thackery Binx

Beetlejuice

Lydia Deetz

Adam Maitland

The Crow

Eric Draven

Ghostbusters

Ray Stantz

Aliens

Bishop

An American Werewolf in London

Jack Goodman

Sleepaway Camp

Ricky Thomas

Re-animator

Herbert West

Silence of the Lambs

Clarice Starling

Fright Night

Jerry Dandridge

Candyman

Daniel Robitaille

The Evil Dead

Ash Williams

Sabrina the Teenage Witch

Harvey Kinkle

Buffy the Vampire Slayer

Spike

Full Metal Jacket

Sgt. Hartman

Joker

Animal Mother

Pyle

Preference~ the boys with an s/o whose ex stalks them

Grease

Kenickie

Labyrinth

Jareth

Total Recall

Douglas Quaid

Requested “Would Includes” and Imagines/Fics~

Darry falling for Johnny’s sister

Allison Reynolds dating a shy nerdy girl

Starting a family with Cameron Frye

Making out with Cameron Frye

Cameron Frye comforting you when you’re upset

Getting drunk with the Ferris Bueller crew

Gary Wallace dating a tall girl

George Mcfly with a dominant flirty s/o

Comforting and being comforted by Will Hunting

Will Hunting having a crush on you

Being apart of the good will hunting gang

Armand with a virgin s/o (including nsfw)

Lestat and Louis dating a girl who loves horror movies

Making out with Duckie Dale

Duckie Dale cheering you up

Cliff having a crush on you

Making out with Cliff

Making out with Bryce

Bryce having a crush on you

The Lost Boys with an s/o having an anxiety attack + fighting depression

The Lost Boys with a sweet and innocent s/o

The Lost Boys with a curvy mate

The Lost Boys fighting with their mates

The Lost Boys dating a shy short girl

The Lost Boys taking care of you when you’re hurt

Getting drunk with the Lost Boys would include

David x Laddies older sister

Making out with Edgar Frog

Being Married to Archie Costello

Going to the beach with Archie Costello

Making out with Archie Costello

Darrys girlfriend landing a job at a local cafe as a singer

Making out with Kenneth Wurman

Being Cindys friend and Ronalds crush

Harold Sherbico having a crush

Kim Kelly dating her polar opposite

Neil Perry dating an artist

Making out with Charlie Dalton

Jealous Charlie Dalton

Jealous Knox Overstreet

A study date with Steven Meeks

Spending the winter season with Neil Perry

Comforting Charlie Dalton after he gets expelled 

The dead poets walking in on Charlie and his secret, shy girlfriend 

Simon Boggs having a crush on Laneys friend

Faking It-Cindy Mancini falling for the girl who paid her to be her friend

Spike having a crush on you

Steff McKee having a crush on you

Marko having a crush on you

David having a crush on you 

Paul having a crush on you

Dwayne having a crush on you

Dwayne x vampire reader who dresses like Stevie Nicks

Making out with Keith Nelson

Meat having a crush on Peewees sister

Admit it- Mickey Jarvis and his future s/o having crushes on each other

Being a part of team USA and meeting Adam and Charlie

Dwayne Robertson having a crush on you

Sleepover with Bill and Ted (including nsfw)

Being pregnant with Ted Logans child

Starring in the schools Romeo and Juliet with Ted Logan

Ted Logan asking you to be his valentine

Spending Valentines day with Steff McKee

Spending Valentines day with Steven Meeks

Spending Valentines day with Keith Nelson

Spending your first Valentines day with Bryce

Wishing I Was Her (Nick Andopolis)

If You Want Out Just Say It (Ace Merrill)

Going on the Ferris adventure

Going on your own adventure with Cameron Frye

Making out with Randall ‘Pink’ Floyd

Travelling back in time with Marty McFly

Tommy Devito dating a chubby artist

Years Gone By (Michael Corleone)

Sonny Corleone dating his opposite

Phillipe Gaston x reader~ Fairy Tale 

Being Fulton's sister and Dating Dean Portman

Comforting Todd when he’s upset

Being married to Bill S. Preston Esquire

Being married to Ted Logan

Spending Halloween/October with Knox Overstreet

Making out with Knox

A will they, won’t they relationship with Seth Brundle

Falling in love with Edward Scissorhands

Dwayne Hicks with an Android!Technician s/o

Private Joker dating an artist 

Jareth falling in love with you

Being married to Matt Hooper and going to Amity

The way you make me feel~ John Bender

Being in a long term relationship with JD

J.D. with a chronically ill s/o

Archie with a chronically ill s/o

Making out with Ted Logan

Archibald Craven falling in love

Andy Dufresne falling in love

Nsfw Headcanons~ 

Group sex with the lost boys

Sam Emerson

Threesome with Obie and Archie

Armand

Archie Costello

(sub) Archie Costello

Obie

Johnny Cade

Cameron Frye

Duckie Dale

Blane

John Bender

Randy (Intruder)

Joey Donner

Kenneth Wurman

Keith Nelson

The Dead Poets Kinks

Knox Overstreet

Charlie Dalton

Steven Meeks

Todd Anderson

Neil Perry

Gerard Pitts

John Bender taking your virginity

Louis de Pointe du Lac

Dinger Holfield

The Lost Boys

JD

Randall ‘Pink’ Floyd

Benny O’donnell

Fred O’Bannion

Cliff

Bryce

Johnny Walker

George Mcfly

Brian Moreland

(sub) Perry Barnett 

Bill S. Preston Esquire

Ted Logan

Randy Meeks

Michael Emerson

Nancy Downs

Ray Stantz

Egon Spengler

Spike

Angel Guzman

Sgt. Hartman

Brad Hamilton

Douglas Quaid

Chris (night of the creeps)

Sonny Corleone with a shy, virgin s/o

George Mcfly getting jealous and being dominant

Grease Monkey (Keith Nelson smut)

Sins of the flesh and matters of the heart (David x reader + Dwayne smut)

[classic80sand90smovieloves2]

Idk if you’re still taking requests, but I saw a NSFW headcanon request for Will Hunting and I was wondering if you could also do one for Chuckie Sullivan! <3

Since I’ll probably be watching; at least, clips from the movie, I’ll throw yours in the up next bunch too. Thanks for the request!💖