#tim masky

[pink-key]

The boy grew up a bit Nobody can stop me drawing lanky Tobs, my art career lead me to draw lanky Tobs

[pasta-in-the-pudding]

SO IM SORRY IF THIS IS REALLY RANDOM BUT IF ITS OK COULD I REQUEST TICCI TOBY,MASKY,HOODIE,EJ WITH A TEEN!READER that's like shy but when the reader gets more comfortable around them, reader acts childish/shows their inner child bc they had to grow up quickly ifykwim

(this sounds so cringe >_< 😭)

Theres no such thing as bad cringe here, friend. Be as cringe as you'd like!

Thank you so much for requesting!!

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Toby

Meeting you was pretty normal for him

Most of the other kids around the manor are pretty shy too, so you being shy doesnt matter to him

But once you start getting more comfortable with him, and start opening up more, he notices that you aren't really all that shy, just kind of...yk...traumatized??

He is here for it though, and will do all the things with you

He'll get matching footie pj's with you, He'll get you your favorite childhood snack, you'll turn on your favorite cartoon and He'll help you make an awesome pillow fort

Or, if you prefer, a blanket coccoon for you to snuggle into while you watch your cartoons

He'll also get things that remind him of you

"Y/n i saw this squishmellow and thought of you! Also, i got you some more snacks in this new flavor we haven't tried"

Also, i feel like he'd be the one you go to if you wanna play any games

Lord knows that boy has too much energy for his own good

His favorite is hide and seek, but if you wanna play something else, he's fine with that too

I warn you though, he's very good at hide and seek...

Masky

Masky isn't terrible with kids, but he isn't the greatest

Teenagers are his favorite to babysit/watch, because he can just leave them alone for the most part, if they need anything, they know where to find him

So when you start to open up and show your more childish side, he is kind of taken aback

Not in a bad way, of course

Just shocked, is all

Mostly, he's just glad that you're finally opening up and being yourself

And i mean hey, if coloring in coloring books and eating fruit snacks makes you happy, then who is he to judge?

He won't partake in these activities himself, but if you wanna talk to him about it, then he's all ears

He'll show you his favorite cartoons he watched when he was a kid, he'll show you his favorite childhood snacks, and he'll tell you stories he picked up in his life

Like toby, he will also help you build a wonderful pillow fort

And tim, hes a real manly man, you know, good at building and hunting and stuff

So you KNOW that its gonna be less of a pillow fort and more of a pillow palace

Also, i feel like one of the creeps has a picture of him somewhere, all snuggled up into a pillow, nice and asleep inside your pillow fort while you watch tv

Its used as blackmail, of course

Hoodie

Hoodie loves kids

He's always wanted a kid of his own, he remembers vividly daydreaming about it as a little schoolboy

His occupation has put a bit of a hold on that dream, but the manor has plenty of children that are always begging to be played with

And so, it's probably no wonder you were drawn to him

He's just got such a good vibe, you know?

Like you know that you could tell him anything and he'd just smile and say "i think you should keep living your best life"

Like toby, he goes all out

He probably won't wear footie pj's but yk

He's not too terribly good at making pillow forts, but oh my god can he throw a tea party

And he'll let you do his hair and makeup too!

After his numerous tea parties with sally, he knows all the proper etiquette too

He'd also probably be the one on this list who'd spoil you the most

Literally just ask and he'll probably buy it/make it for you 😭

Eyeless Jack

From a medical standpoint he is very worried for you

His first reaction to you opening up was his eyes slightly widening and his thoughts going "good god who fucked up this kid??"

However, he understands that for a lot of people indulging in childhood interests is a coping mechanism that is very helpful

And it's not hurting you or anyone else, so why would he care?

He studies you intently

He won't actively indulge in your activities like everyone else

He mostly just sits somewhere close by and watches your behaviors

He wants to know what is normal for you and what isn't, that way if your mental health takesa negative turn, he can get on it as quickly as possible

The last thing they need is a kid having a mental breakdown

Maaaybe of you ask nicely he'll watch cartoons with you

Maybe

[c-horror-angel]

tim masky as tobys dad is my favorite headcanon ,,,

IDEA FROM @cupid-la-beaux LAWL

[bimbvx]

punks not dead (but you will be) closeups under cut :))

...also i wasn't thinking while drawing this so uhhh in this au tim and toby are left handed ok

[kousomii]

yaa ! dont really like this piece anymore but thought id post it anyway. tim retweeted this actually, i was so happy getting recognized by him LOL shame i dont like it that much. maybe ill do one better someday ! 

[cyberghouleo]

Proxy twitter au

part 2

[tiss-mushroom]

For the first time in a long time I drew on paper

[rebisrot]

jay: hey, tim, do you still have your meds?

masky: ah, eto... bleh.

[eyygee]

I summoned them out of their graves.

(Rook is my creepypasta OC)

[juniper555]

The core mentally insane four!

[rubyafton]

Tadaaa✨ I made a Toby Coralie doll! I've gotta say, it was so good working on him. Maby I'll make some goggles and axes too~

[peachpopsstuff]

Masky !!! ^_^

[greydrit]

bifurcation

[ensegnity]

I made this last year in August. Decided to post it because why not.

It’s Tim throughout the years. You can probably guess which was from Entry #9 and which was from his later adventures with Jay.

[creek-ink]

I couldn’t help myself

[odin-hatesu]

Could I get a Masky x Fem!Reader x Hoody nsfw head canons? It's okay if not! :)

Yes anon yes you can🤭

Masky x Hoodie x Reader Hcs (NSFW)

Masterlist / Requests

Rating: THIS SHIT AINT RATED NO MOTHER FUCKING PG! THIS SHIT RATED- PORN

Parings: Masky x Hoodie x Reader

Warnings: threesomes, smut obviously, throat fucking, double penetration, oral m and f receiving, they’re sadistic, knife play, blood play,

Spit roasting.

Both fight for your attention, pulling your face to look at them, smacking your thigh so you can watch as masky fucks your over sensitive pussy :(

They both argue about how much better they’re making you feel and how the other will never make you cum that hard.

If you piss them off or need to be punished, thats when they work together. Hoodie fucking your throat, while Masky ruins your cunt. If you really REALLY made them mad, they’ll both fuck your pussy at the same time degrading you when you say it hurts.

They love cutting off your clothes.

They buy you two pairs of the same lingerie so they can ruin one and you can keep the other.

They LOVE roleplaying. Keeping their masks on, and pretending you’re a victim is their absolute favorite thing, especially when you have a bit of fear in your eyes.

Knife play. They love holding a knife to your throat while they roughly make out with you.

Masky likes leaving small cuts along your body so Hoodie can lick up the blood

They dont give a fuck if you’re on your period. Sex helps with cramps is their main point when they really just wanna see their cocks covered in your blood.

Hoodie is a lot softer than Masky. He will pet your hair as you suck him off, giving praises telling you how good you are for him.

Masky will grab your head forcing you down on his cock, grabbing your neck so he can feel how his dick bullys your throat.

Hoodie gently rubs your thighs as he devours you. Masky sitting behind you marking up your neck, and holding your hips in place. “Be a good slut. You wanted this, so take it.”

Masky is rough and loves over stimulating you. He doesn’t listen to Hoodie when he tells him to be gentle with their darling :(

They wanna chase you through the woods, and fuck you once they find you.

If Hoodie gets you to himself for a quickie without Masky, He will get extremely jealous, punishing you for “being a fucking slut for him and not even thinking about me.” He gets very vocal, asking shit like, “Did his cock feel this good? Did you moan as loud as you are right now?”

If a job from slender goes well, they’ll celebrate by fucking their darling.

Sometimes they’ll have you on your knees all day, sucking them off barely paying attention to you, hoodie always breaks first, telling you how good you’re being for them.

Hoodies usually the one cleaning you up after sex, while Masky goes out to smoke. As i stated before hes not the best with aftercare, but he’s trying:(

They take pride when you have trouble walking, or when your throats corse and sore.

I hope you guys liked this 🤩 im thinking of making a whole fanfiction about them