#creepypasta toby

[ch3rry-l1m4d3]

BUCKSHOT ROULETTE (ft. Toby :3)

He'd find this game extremely funny I think.

[yellowflowrs]

Toeebeeee

[pink-key]

Your first date

[sm1lec1de]

I like to think I’m funny :3c

[apolloprophecy]

Can you tell I like angst with him?

Lmk what else you wanna see with Toby!!

[mcnotok]

you should draw them raiding the snack aisle of a convenience store

I may have had a little too much fun (so did they)

Ref images I used below the cut, they’re blurry lol

[rpggoro]

Got some unfortunate tendencies I see

.

I'm gonna cry why am I so bad at side profiles 😭

[seireitonin]

Dating Toby?? Like is he clingy, jealous or protective of his partner??

(I don't know....this is my first time doing these things.....)

Toby brain rot :3 this is how I see Toby mixed with some canon information! (I’m gonna try to keep it realistic)

What would it be like dating Toby?

Toby’s life is filled with tragedy

Abuse, death, murder, mental illnesses, being a slave to Slenderman

It’s all bad

So when he finds you, someone that accepts him and loves him despite all that, he’s not letting you go

He’ll do anything for you

I mean to the point it’s unhealthy

Because hes obsessed with you

Like really obsessed with you

He’s super touchy, not only because he likes to feel close to you, but it keeps him grounded

That’s important to him because his disorders/ mental illnesses cause him to hallucinate or space out

He’s not gloomy he’s actually upbeat but when he remembers something from his past or the current state of his life he goes through episodes of depression and mood swings

They can get really intense and as you’re with him you’ll learn how to support him through it

Just laying with him, making sure he has water and reminding him you’re here for him will help lots and lots of physical affection

If his mood swings get violent he’ll isolate himself from you but it’s heartbreaking to hear his suffering

His swings can go from extreme anger to intense sadness to reckless happiness

Since he hasn’t had much kindness or interaction in his life he doesn’t have the best social skills

He’ll say whatever is on his mind with no filter and that includes you too

So he’ll say mean things unintentionally a lot because he doesn’t understand how what he says can be hurtful

And he might try to call you sensitive for it too

“Ugh you’re overreacting I didn’t even say anything that hurtful. It’s just what’s on my mind”

He literally doesn’t understand how it can make you feel because he’s a bit detached with emotions

It’s gonna take a while for him to understand but he loves you so he’ll try to understand for your sake and will work on apologizing

He can also just be rude or a jerk sometimes in general

Toby likes just spending time with you to the point where you’re connected at the hip

He won’t say he loves you with words but he says it with his actions

He brings you gifts, holds your hand, goes on walks with you, holds you and try’s to be better for you (even though it’s really hard because he’s set in his ways)

He talks a lot so sometimes you’ll just listen and smile

Since he can’t feel pain, when he gets back from missions you’ll have to help him check for injuries to make sure he’s okay

He doesn’t say it but he appreciates it

Sometimes he’ll just stare at you because he loves you so much, taking in your every detail

He notices everything about you, from your body language, how you tan in the summer and lighten in the winter, he even knows how many times you breathe in a minute

Toby eats a lot of instant ramen so be prepared to eat a lot of that at first but you start to cook for him because he needs to eat better

Toby never expected to have a girlfriend since he’s a lot to handle but he liked the way you handle him

He’s full of himself literally thinks he’s gods gift to earth so sometimes he puts himself before your relationship but he’s trying to change that

He’s really funny especially if you like dark humor

He’s a jealous man. You’re his no one else’s

If someone even looks at you romantically he’ll go crazy on them

Remember, Toby is still a murderer and enjoys murdering

Chasing them down and threatening them and if it escalated kill them with a smile

He does it all for you. Everything is for you.

“You know I love you, right?”

He looks at you covered in blood

Toby likes it when you wear his sweaters

He wants a family one day and hopes you can give that to him

He’s possessive over you but does it out of intense love and obsession

He wants to keep you safe by any means necessary because he’s so used to losing the people he loves and he really doesn’t wanna lose you

Toby drives a pickup truck and likes to drive you around in it

He likes to sit in the back of it with you and look at the stars in an open field

Since Toby’s older his tics have calmed down but they’re still there and he still has the occasional tic attack

You’ll have to help him through those because sometimes he can’t even talk when he’s having one

Stuff he can squeeze, ice pack on his forehead and making sure he doesn’t hurt himself

He’s happy you don’t see him as a burden like everyone else did

He’s never letting you go

He didn’t know he could feel love this intense

[afterglow-evie]

Didn't you like pixel Toby back then? Ahaha. Damn, 4,300 notes on that art, I'm shocked.

[strawberri-acidd]

IS THAT TOBIAS ROGERS

yes it is 🥰🥰

he wasn’t a personal favorite of mine growing up but he was my best friend’s!! so in honor of her he has a personal headcanon that he’s obsessed with and loves bugs (they also love bugs).

[kousomii]

hehe tobito !! <3

[chocolette-art]

[waywardvoidpoetry]

people have told me my interp of Jeff drives them up a wall but in actuality he's a Alan Watts over Vaporwave Bisexual

[pink-key]

[creepzkilla]

No because those EJ headcannons 😳 are so good aldhworjeoejekr you wrote him so perfectly 😫

If it's ok, can I request some NSFW Creepypasta Toby headcannons? You can make them as dark as you like, but DAMN I have to admit the way you write characters is so gooooodddd 💖💖💖

↳˳⸙;; ❝ TICCI TOBY KINK HC'S! + BONUS ᵕ̈ ೫˚∗

[A/N]--tyty i always enjoy slasher creepypasta-- the more realistic version of the fandom. its always been more entertaining for me... the mansion kinda HC never really stuck with me unless portrayed really good? its so hard to find fics that are like that... but anyways wtf my first ask this deserves a bonus smut at the end?!?!?! sry for the delay too i’ve had writers block wtf… the second half is shit ngl

NSFW. warning— NOT PROOF READ fem! anatomy, dub-con, somnophilia, toby being a perv, sadist, bondage,breeding, exhibition

TOBY IS A CLOSET PERVERT--

he remembers when he first started stalking you. when he first snuck into your house while you were fast asleep as he kept a watchful eye over your sleeping form. you were ethereal, he couldn't help himself following you home- or going through your panty drawer. you couldn't blame him, really, you couldn't. you look so cute in your satin pink thongs that he just had to steal one. or three.

sadist-- toby just adores watching you contort underneath his touch as you squirm away from him. he won't hesitate to leave harsh slaps across the meat of your ass or dark bruises made from his belt into makeshift handcuffs

bondage-- he loves tying you up in all sorts of different lewd positions. toby takes pride watching you whimper under his calloused hands begging for your hands and/or legs. he knows that those whimpers are only for him.

breeding-- toby has family issues... at first, he wouldn't want kids. he would dismiss the thought of ever having any kids in the first place... not wanting to turn into his dad. he was terrified. that was until he came in your pussy the first time. it was fucking life-changing. he loves the feeling of spilling his seed into your pretty pussy... he just can't go back after that. why buy condoms when he could watch his cum seep out of your pussy? he wouldn't mind having a kid or two.

mutual masturbation-- he goes wild watching your hands disappear into your heat as your mouth lets out a barrage of whimpers and moans. toby can't help but join in. whether you know if he's watching or not.

exhibitism-- this man just dont give af. if he wants you, he wants you. anytime, anyplace.

oral(fem receiving)-- this could be considered a kink because toby could probably cum buy just eating your pussy. he just cant get enough of it. he gets so painfully hard when he goes down on you. so you cant blame him when he paints his pants white.

corruption— this is a big one..you were a virgin, with little to no experience before you bet toby. something about that innocence he just had to protect… something he just had to corrupt. toby remembers when he first taught you how to give a blowjob. he could just cum by the perverted memory.

TOBY DEFINITELY JERKS OFF WITH YOUR PANTIES—

there’s no way he doesn’t. he fucking obsessed with the taste and smell of your pussy. the nights where he can’t come and visit you bet you can find a pair of your satin panties wrapped around his cock. toby just can’t help himself. he loves feeling the feeling of your juices rubbing up against his cock as he imagines runtting against you. it’s his dirty little secret… well it’s not much of a secret when your prairies start showing up stained with a white excrete.

HES SURPRISINGLY KINDA BIG—

now don’t get me wrong… toby isn’t a petite guy, he’s rather tall standing at 5’11 or 6’0. he’s a pretty built guy—he kinda has to be. so when i say surprisingly i mean you wouldn’t really except him to be a whopping 6’0 inches. his girth is on the skinny size but he makes up for it when hes hitting places you never knew existed. his tip is a dark pink, and the prettiest dick you’ve ever seen. you never thought that you’d be saying that about a dick or specifically a serial killers dick; but here you are… your not exactly complaining.

—-ˋˏ [‘Ill give you everything’] ˎˊ

—(Toby couldn’t help himself. He really couldnt. You just looked so gorgeous in your pink satin panties— which are your favorite pair— he couldn’t help but rub against the cotton material. It’s not like you’d mind anyways…you’ve always asked him to fuck you awake before, why not take you up on that offer?

He carefully moves the comforter from your shoulders, peeling it back allowing him to slip into your bed behind you . Toby sinks into the bed, spooning your relaxed body as the curve of your ass pressed into him.Almost instinctively your body pressed into the slasher completely, being enraptured by his warmth. You were oblivious to what you were doing to him.

His aching boner stretched against his pants, and fuck it was painful (from aching not actual pain) as he rubs up against your panties. It was almost like you wanted him to do this. Sleeping in only your underwear? It was like you’re asking him to move your panties to the side and fuck you.

His cold finger tips brush against your damp panties, hooking his finger on the seam of fabric, slowly and carefully pulling them down. toby was careful not to wake you—-not yet. He wants to savor this.

It was so unbelievably hot in your bedroom, almost like a sauna. If anything he was helping you cool down. You should appreciate his kind and just actions by taking of your clothes before you got too hot. He chuckled at that thought, ghosting his finger tips over your exposed shoulder, leaving goosebumps in his wake.

His lips hovered above your exposed neck, sending chills down your spine. Dark bruises soon began to litter your neck, ruining its once pristine image as Toby sunk his lips deeper in your skin, all while his other hand disappeared into your cunt.

You were so incredibly wet, so incredibly tight. His calloused hands slid in and out with ease, your walls sucking him in ever time. Toby was enraptured with your beauty, your flushed cheeks, your rosy lips, the soft whimpers that left your mouth; utterly gorgeous.

“Toby?” You awoke to nothing but darkness with an uncomfortable feeling in your stomach, an all too familiar one. A warmth spread throughout your body like wildfire as the prevalent feelings grew. The sensation— that you couldn’t put a finger on—- just felt so good, you couldn’t help but melt into it.

Toby hummed in response, too busy on concentrating on the task at hand; fingering your tight cunt. The lewd sounds that gushed around his hands was deafening; almost forgetting that you were awake.

“Are you e-enjoying yours-self?” He laughed, curling his fingers inside of you, rubbing up against a patch of sensitive nerves.

You yelped, now being fully awake, clearly aware of the sensation— that is being full. You could only moan in response as his fingers continuously plunged in and out of sopping cunt as your core tightened.

Toby’s lips attached to the crook of your neck once again, tracing over the dark bruises that began to form— biting ever so slightly on your sweet spot (that only he knows of). His unoccupied hand, cupped the meat of your thigh, lifting it up to gain better access for his other hand that was moving at an insatiable speed.

“P…Please, I need you…I want all of you.” A barrage of moans left your lips, as your hand curled behind you to grip the man’s hair that assaulted your skin. Your sharp nails dug into his scalp, tugging on tuffs of his unkept brown hair—signaling your desperation.

Suddenly, he was on top of you. Straddling your exposed bottom half with his thighs, a lustful glint ever so present in his eyes. His lips were a cherry red, presumably from his attack on your neck as well as his hands that were slick with your cunt. You take immediate notice of the large tent swelling in his blue jeans, you could only guess at how painful it was.

“A-are you sure?” Toby hummed, his scarred hands tracing over your waist, “I’m not g-gonna go easy on you.” His voice came out as a whisper, as if it was some horrible secret—a taboo. To which it was, not like you knew or anything— but toby has a secret, commmited horrible sins that can never be reversed— you shouldn’t be doing this with him… He feels guilty almost— yet it’s so enticing… His hands devouring your body as if his hands weren’t covered in blood merely hours before.

But you’ll never know, right?

“I want all of you, Toby.” He looks down at your delicate form, such innocence. Your skin was practically glowing in the moonlight that shone threw the raked blinds, making you look almost angelic. He was scared to touch you, like you would crumble under his touch. Like you would see him for the monster— the pyschopath he truly is, a devil.

Yet, that’s what makes it so exciting, so enticing to see your angelic body beneath him. The danger, the corruption. It only added fuel to the fire, and soon it would become a wild fire.

Your body; merely heaven and earth wrapped into one.

He; the virus, a plague that never stops— pollution your body and everything in between.

Is it really worth it? If he really loved you— he would let you go— right?

“I’ll give you ev-verything. Anything you w-want.” Toby whispers, his hands on your waist crawling towards your chest—drawing secret messages that only you would know. His usual ice cold hands, were anything but cold. They were warm. His hands roamed your body, and spread throughout your body like a flame— he devoured everything in his path.

Your body reacted to him like a magnetic. His name fell off of your lips along with whispered promises and wonton moans. You were meant for him— maybe poisoning you isn’t so bad. Maybe—just maybe, it was meant to happen.

[apolloprophecy]

On my grind with him recently LOL

Please leave asks and suggestions you want of him!