The Berry Coolest

- Multi Fandom Headcanons - •Minors DNI •Suggestions Welcome •Occasional 18+ Themes •X Reader and General Headcanons

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Undertale Skelebros Headcanons - First date (WIP!!)

Read my bio!

Sans:

Papyrus:

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Undertale Skelebros Headcanons - Asking You Out

(WIP)

Sans-

He’d been contemplating this for a while.

Papyrus-

• The great Papyrus will settle for nothing less than the perfect first date. And that’s why it’s going to be at his house eating spaghetti he’s cooked himself. Wether or not there’s a second date is going to depend on how much you think you can tolerate some creepy pasta

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Underswap Skelebros Headcanons - General Ideas

(WIP!!) Check Bio

Blue-

Acts more youthful than his younger brother, but still knows when to be mature when he needs to.

Creates puzzles in his free time, incorporating them into his Royal Guard duties to deal with potential human threats.

Cooks so much because he spent most of his childhood caring for, and therefore cooking for a baby Stretch.

Stretch-

Always has one of those plastic bear shaped containers of honey on his person.

Very smart but plays it off. He’s done using his brain.

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Papyrus next 👀

(WIP!!) 18+

Undertale Papyrus Headcanons - The Great Orange Light Saber

How it looks:

He’s VERY shy about it.

As an extension of his soul, it’s one of the most vulnerable parts of his body. Emotionally and physically.

What if it’s not as great as something apart of him should be?!?

It’s mostly proportional to the rest of his body. Average sized and thin-ish.

His habits:

He doesn’t really touch himself very often, it’s not a very knightly thing to do. In his own, self-deprecating opinion.

When he does, the conditions have to be just right.

No Sans in the house. He’ll have to be at Grillby’s, that way he knows Sans won’t just up and come home unexpectedly.

He’s gotta be itching for it too.

He’ll be waiting for Sans to leave all day and bemoan his shameful desires (in his head) for another night if his ketchup loving brother gets his fix of the red stuff at home instead.

[berry-coolest]

I want Sans nsfw NOW

(WIP) 18+ Minors, please block me!

Undertale Sans Headcanons - The Blue Lightsaber

How it looks:

His manhood is an extension of his very soul. How poetic.

Because he’s a skeleton, it’s not apart his natural body.

It manifests when he’s aroused and disappears when he’s not anymore or after climaxing.

The light shines through his pants, unfortunately.

Despite what you may have been led to believe, he has a modest size.

Where the man really shines (pun intended) is the girth.

His width is similar to one of those ketchup bottles at Grillby’s, very fitting.

His habits:

Sans doesn’t really feel ashamed of touching himself.

He’ll do it when Papyrus is out of the house, or when he’s pretty sure he won’t be interrupted or heard.

The only time he’s kept up with cleaning his socks is when he once “used” one.

How he likes to be touched:

He is not picky.

Cup him through his shorts, straddle him, bump your ass against his pelvis, blow on it-

Not even blowing him, blowing on him.

Sans will enjoy most any attention he can get from you.

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Undertale Skelebros Headcanons - They Have A Crush On You

(WIP!!)

Check my bio

Sans -

Pretends that he doesn’t. If anyone asks? It’s a casual denial.

*what? me and (Y/N)? as humerus as that would be, we’re just friends.

He makes an effort to keep you from hearing about any speculation, if someone suspects it that is.

Sans is good at keeping his true feelings hidden a majority of the time. Not even Papyrus knows, but of course, he pries about everything.

A part of why he keeps it to himself is because he assumes it’ll never happen. Why the hell would anyone want to date a chronically lazy skeleton? He can’t even be bothered to pick up his own socks, he’d be a horrible boyfriend.

But, he loves your company.

He’s always popping out of nowhere to “surprise” you.

It’s more or less an excuse to try to weasel his way into spending time with you.

He’ll show up with those god damn “water dogs” or another gag food item to try to get a rise out of you.

Dear God, does he love getting a rise out of you. It’s his version of some kind of self-destructive flirting. Plus, he loves seeing you react in any kind of way. Frustrated, confused, endeared or entertained.

He thinks about you a lot despite trying not to.

Has contemplated intentionally reading your emotions to see if you feel the same but never has. That wouldn’t be fair.

The skeleton is facing a lot of internal conflict, okay?

Doesn’t want to see you get hurt, even if that might mean never expressing his true feelings.

He might be using “protecting you” as an excuse not to be vulnerable too. But who knows, right?

Laying his true emotions bare in front of you sounds like a recipe for disaster, and he’s already been dealing with Papyrus’s cooking everyday for many years.

Papyrus -

When Papyrus likes you, you’ll know.

He’s always around, he’s always trying to talk to you or show off.

Puffs out his chest a lot

If any of his friends asks if he likes you, he’s not going to deny it. He is going to get into dramatics about how wonderful you are.

He’s taken up reading books like “Dating 101” and “How To Attract Your Soulmate In 30 Days”

His new literary interest starts bleeding through the way he talks too. Based on what the books say, it should be more attractive!

No matter where you guys are or who you’re with, if it doesn’t step over anyone else’s toes, Papyrus is going to be opening the door for you.

You show the slightest interest of going somewhere or leaving? He’s jumping to swing it wide open for you.

He often offers for you to come over to his house. Playing host is the perfect opportunity for him to show you what a domestic life with him would be like.

He’ll cook for you (always spaghetti), clean for you before you even have time to finish making the “mess”.

And you better believe he has every intention of keeping that up if he manages to woo you. Not that you’re asking for it in the first place.

Sometimes, when he thinks you won’t notice, he’ll just stare at you and imagine what it would be like to kiss.

Yes, he has the most stupid look on his face when this happens.

He wants a shower of kisses from YOU!

For months, he’s been trying to find a way to tell you how he feels. Nothing ever seems to feel adequate enough though. The depths of his feelings are TOO GREAT for the words he’s tried to use.