
Hii! I'm Sam and I've had the itch to get into writing Fanfiction again recently! So this is for me to practice writing::3! Feel free to request it helps motivated me~
17 posts
How They Act When Crushing UT,UF,US!
How they act when crushing UT,UF,US!
This one was fun I might do a part 2 eventually because I love how people change their behavior while crushing on someone think next is gonna be confession head canons or a drabble. Anyway requests are open! Just wanted to put that out there I love getting them ::> and I'm pretty open to writing most things I love getting different inspo from different people. Anyways I'm done rambling hope y'all enjoy!

Undertale: Sans: Trys to make you laugh as much as possible. He loves hearing your laughter and is super proud when he can get you to full on laugh with his shitty jokes. He's a daydreamer and often daydreams about you when it's slow at work or he's in bed alone. He won't admit how nice he sleeps when he sees you in his dreams. You motivate him to get out of bed easier on days he gets to see you so that's a plus
Papyrus: He likes to be around you as much as he can. Like doing menial things together?? Oh you have a doctor's appointment, sure why don't I come and we get lunch afterwards. He just likes spending time with you! "Accidentally" making too much food for meals so he has a reason to see you and make sure you're eating something.
Underfell:
Red: Heavy denial before reluctantly accepting. He's a flirty guy he thinks it's all fun and games until he's thinking about you at 3 am with a blush in his face imagining a future and doing cute relationship things with you. He knows he's fucked. He doesn't really believe someone would like him so from his perspective it's one sided attraction all the way and that hurts. He still flirts but it kinda hurts him inside too. Teasing himself with something he thinks he'll never have. He doesn't distance himself but he's a bit rougher maybe trying to scare you off a tad.
Edge: Denial worse than his brother. He doesn't have time for crushes or anything of the sort. It's improbable that he does like you that way anyways it's just a passing attraction he simply likes the way you say his name, and the way your legs look when you walk and stretch out, and oh … He's fucked. He'll continue to deny it to himself until someone ,most likely his brother or his version of Undyne, points it out. Then he's trying to hide it, trying to play it off. The passing touches he lets linger too long, how even though his days are scheduled he still somehow ends up running into you occasionally.
Underswap:
Stretch:We got another daydreamer and he's 50/50 with risque and wholesome daydreams. He finds any excuse to touch you and let's the touches linger. He's flirty and loves if you flirt back, kind of easy to fluster flushing a gorgeous marigold shade as he nye he he's. He invites you over for gaming or movie nights, wanting to share his interests with you and find some shared interests in shows and such. He definitely has written a song about you that he keeps hidden in a folder in his closet. There's a doodle of you on the back of the page and he's a little embarrassed of it.
Blue: He can tell when he likes someone like that he's pretty intune with his emotions. He likes to hang around you taking time out of his day and dedicating it specifically to you. He writes you little notes and reminders and hides them around your space to find, knows where you hide when you're sad and hides a bunch there. He blogs about you on occasion never mentioning your name but simply writing about you. He likes to find two player games for you two to play together mainly team working puzzle ones.
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More Posts from Cloudyskydreams
Um hello, could I request Undertale Sans relationship headcanons with a female half angel half human reader? Sfw and nsfw, please and thank you! Hope you have a great day.
Hi! Thanks so much for being my first request I got so excited I had to tell my whole family as soon as I saw this in the inbox lol. I don't know a lot about angels but I had fun with this! I hope you enjoy ::3 NSFW under the cut!

SFW:
•Sans loves your wings he thinks they're gorgeous and would love to help you preen if you're comfortable with it, he's gentle and can reach all the spots that are hard for you to get to.
•He loves seeing you in white and gold, he thinks it makes you look even more angelic and it's a quick way to have him staring at you with a blush and dopey smile until you mention it to him and he busts out the angel puns.
•He enjoys having your arms and wings wrapped around him when hugging or cuddling. It makes him feel extra loved.
•PLEASE take this man out flying to see the stars. It's the perfect date idea and it's probably the closest to the stars he's ever been. Quick way to get this man to think of marriage lol.(Okay this is so cute I gotta write a small drabble ur being blessed today)
You chuckle as Sans clings to you.His face pressed against your chest. Currently you're flying over Ebott city with your bonefriend in your arms taking him to a supposedly special date you had set up. You called out to tell him you're almost there, having to yell over the wind howling. Once you escape the city and more importantly the light pollution you yell for Sans to look up. He does and his eyelights expand to almost fill out his sockets. His grin falters and he looks shocked before his entire face lights up. You think he says something but his baritone voice is hard to hear over the wind. He reaches a hand up as if he could reach out and touch the stars. You chuckle again and he says something else so you yell that you can't hear him. He leans up in your embrace and says in your ear
"i love you starlight" you smile as he kisses your cheek. He watches the stars as you approach as hill and land, the next few hours are spent stargazing with sans as he points out constellations and tells space puns.
•He has a dreamcatcher made with your feathers. He kept a few after helping you preen once and after finding out what dreamcatchers were he thought it would be a nice reminder of you when you're not around.
NSFW:
•He gets worried about hurting your wings a lot when boning so he normally prefers for you to ride him, he also really enjoys the scene of you cumming on his cock your wings stretching to their full glory from the orgasm. It's a sight to see.
•The uncommon position switch normally has you in doggy style. There was one time where Sans came so hard he grabbed onto the scapulars(base) of your wings to brace himself. He thought it was extremely hot to use them as handlebars but was so worried he had hurt you.
•Body worship, it just feels right for him to worship you a little. You're just so angelic and perfect to him he wants to do all of it kissing up your legs, massaging your back and wings, running his fingers through your hair as he kisses you. He just loves you so much and he's going to make sure you feel how much he does. It's one of the few times he really puts effort into something.
•Feather play, Imagine him dragging your own feather across your thighs and teasing your nipple with the tip of one as he squeezes your other breast. Sometimes he'll just tickle you during sex, pelvis deep inside you and this man has a feather tickling your sides cause he thinks your laugh is hot.
S/O falling asleep on him UT,UF,US
Undertale:
Sans: He does this all the time to you. Doesn't really mind and will pull you close making sure you're nice and comfy before taking a nap himself. He loves this if it's a common occurrence.
Papyrus: Depends on how common the occurrence is. If it's an all the time thing he'll let you nap 30 minutes tops before he has to get up and do something. If you're just super tired it's more like an hour and a half because he's a little worried and you probably nodded off mid activity with him.
Underfell:
Red:Pulls you close and might grab the squishy bits a little "on accident" but he's not gonna really perv you up in your sleep unless you're into that. So he settles for some nice cuddles, running his fingers through your hair, dedicating every facial feature to memory, thinking how lucky he is you chose him.
Edge: Thinks it's cute and will hold you for a while gently tracing shapes in your skin, he has a scheduled day though and stuff to do so he'll gently move you off and let you continue napping while he goes about his business.
Underswap:
Stretch:Oh he loves this, lazy days with you are great. He snuggles up with you curling up around you and def squeezes the squishy bits and probably leaves his hands there as he's cuddling. He falls asleep pretty quick and sleeps pretty good which he's thankful for.
Blue: Thinks you're adorable and takes a picture of you and then you two together. The latter becomes his phone background. He works on editing some videos for his work so he can feel productive and his phone is full of those ad games ,he can't help himself when he sees them especially puzzle ones. He doesn't start fidgeting after a bit and accidentally wakes you up at some point.
A little doodle of Stretch and Blue!
Some doodles I did today, really proud of Blue! I struggle with the papyri still but I'm pretty proud! I might switch to digital to colour them if I have the time!



Confessing headcanons UT,UF,US!
This is not my favorite so far. Oh well though my internets spotty and I wanted to get something out while I know I have some. Reds is by far my favorite I love him sm. As always hope you enjoy!

Undertale:
Sans: It'd have to be you confessing. Sans has his insecurities and doubts and they would hold him back from confessing. He might make hints more known like more flirty jokes than normal and he's a bit more protective of you but he won't outright confess when crushing. If he does it's accidental and happens because he got too comfortable. He probably whispered it or said it too quite to hear all the way and you have to ask him to repeat himself. Que a joke while sweating.
If confessed to: He's a little shocked, are you…sure? He doesn't know what to say all jokes he's ever learned slip out the holes in his skull lost to the void. You probably have to break the silence by repeating yourself or assuring him you mean it and he tears up slightly. He never expected you'd actually like him back he's a little overwhelmed just let him ride it out and you can cuddle and kiss his tears away afterwards.
Papyrus: Very likely to confess first. He's a straightforward man he knows he's got feelings he's gonna share them! He plans it all out and definitely looks up a wikiHow or some other manual on the perfect date just because it helps him feel better prepared. He'd wait till a lull in the activities to confess maybe after dinner or after a movie. He's nervously waiting for your response but he's just happy he finally let you know how much he truly cares for you.
If confessed to: He's overjoyed!! He'll reciprocate and give you a big hug maybe a smooch on the cheek. He basically sweeps you away and says you have to celebrate with a date. He definitely takes a picture to celebrate this man scrapbooks.
Underfell:
Red: This dude confessing? Yeah right he believes he has absolutely zero chance with anyone and feels like that would be setting himself up for the ultimate failure. He's happy to live with his delusions and daydreams thank you very much. That doesn't stop accidents from happening and he might have said something a little too sweet about you. Something about how much he loves your laugh or something about your smile or eyes. He's sweating hoping you didn't catch it. He might even teleport out if your reaction is big enough.
If being confessed to: He's actually a little angry and defensive at first. He thinks you're playing a prank on him he doesn't understand. Out of everyone why him he's a piece of shit, pervert, couldn't raise his brother right, can't do anything right… He starts spiraling. Reassure him maybe with some light physical touch it'll help ground him. He'll calm down and play it off but keep showing you're interested and he'll come around.
Edge: Hes pretty straightforward with it all. He thinks that's the best way to get it done. He invites you over for a home cooked meal because why settle for less than the best when he's trying to impress someone. Not that he should have to try to impress you he naturally does he reminds himself to ease his anxiety. He's definitely not extremely anxious over this whole thing. He presents the meal to you and takes compliments in pride they also help soothe this anxiety. Once the meals over he'll confess offering you your favorite flowers. He's blushing a carmine red and is struggling to maintain eye contact.
If confessed to: Takes it in stride. Of course you would have affections for someone as great and terrible as him. He's blushing and screaming internally but don't point out the blush or he'll deny it and sweep you away. He declares since you're in a relationship it's important you stay by his side so other monsters know not to mess with you. He likes feeling like he's protecting you even if it's just being in your company.
Underswap:
Stretch:He's worked himself up for this hella. He's a little nervous because if he's actually into you it's a whole nother ballpark. He's a bit of a flirt that's for sure but he's not used to anything besides flirting and lustful glances and stuff romance is something else entirely. He sets up a cute scenario maybe finds a way to play you his guitar because he's a dork and he'll stutter a bit while confessing.
If being confessed to: Is super happy and sweeps you into a hug. This takes the pressure off of him to do it and he's honestly flattered someone would confess to him. Impressed you had the balls to do what he was struggling with. He wants to celebrate with a game night at his house and he excitedly tells his brother what happened that night.
Blue: He's got it all planned out. He asks you on a date he'll know you'll be most comfortable on and actually enjoy. Dresses up slightly and gets you one of your favorite flowers. The date goes smoothly and he confesses at the end when taking you home after telling you he had a goodnight. He hopes you'll accept and if you do you get a cheek kiss and a very happy Blue. He definitely blogs about it later on
If being confessed to: He's impressed you beat him to he, he's quick with it once he realizes you return his affections. He happily accepts and smooches your cheek while pulling you into a hug. A sleepover is a must and he invites you back home so he can cook dinner and you guys can have an at home date.
UT,UF,US First Date headcanons!
These were fun to write! I struggle a bit with the Fell brothers but it's good practice to get used to their personal! Hope you guys enjoy ::3
Undertale:
Sans: Somewhere and something comfortable to him. He's a little awkward getting to know people and on a first date he wants to have as many cards in his hand as he can get. So expect to be invited to grillbys or over for dinner if he likes you enough. He's gonna be laying the puns on thick. He normally does when he's comfortable with people too but this is a whole nother level. It's another safe thing to him so hope you like puns and knock knock jokes. If the night goes well and he feels more comfortable he might lay off of them a little and you can see his real smile and laugh. At the end of the night the most he'll do is a hug it might be a little awkward too but hey a hug is a hug.
Papyrus:A nice lunch and an escape room. He gets to share his love of puzzles and what better way to get to know someone than being locked in a room with them trying to bust out? It's a good way to see how well you work together and you can bust out a game of 20 questions while you solve the puzzles around the room. He might get you a flower or a treat he knows you like because Papyrus would know you before hand on a friend level atleast for sure. I could see Paps holding your hand and hugs for sure.
Underfell:
Red:A nice restaurant and a moonlit walk after he loosens up. He's a sweaty nervous guy and has a hard time accepting someone might actually be into him, he likes to flirt but it's all just a game to him so a serious date, he's actually trying and he's nervous. Give him a little bit of time to get used to everything. Expect a lot of avoided eye contact and really bad jokes on the first date. He's pretty smooth when he wants to be so when he finally gains confidence he'll have you swooning and the walk back is filled with comfortable conversation getting to know one another. Give him a smooch on the cheek or lips if you're daring and say goodnight and he'll be thinking about it all night unable to sleep.
Edge: Wine tasting or a Fancy restaurant. Edge has a refined taste and for his first date he's going to go all out pulling out all the stops. He dresses nice, gets you flowers, opens doors, pulls out chairs. Perfect gentlemen. He's definitely not nervous and definitely did not research how to impress a date last night. He's a little awkward to talk to as he doesn't open up easily but he's interested to learn about you and a little bit of wine will open him up slightly. He wants to impress you even if he's a little aloof.
Underswap:
Stretch: Picnic or a Game night at his house. He's another one going for comfort here and he's just not one for big showy things. He's a little awkward and stumbles on his words occasionally but I feel like he warms up pretty fast. He puns a bit especially after meeting the other lazier skeletons but he's more of a practical pranker so there's a few jokes and he also has a fake spider on a string to try and scare you with. I can see him trying to serenade you with his guitar if he feels comfortable enough because he's a dork like that. A kiss on the cheek is the farthest he'll go he's a virgin y'all.
Blue: Scavenger hunting or Geocaching and a sit down dinner. Blue finds these so fun and you guys can enjoy a nice little walk while chatting and then puzzle out where it's hidden together. He feels a sense of accomplishment for each one he finds and has his name signed in a bunch all over the city. After you find it he takes you out to eat to celebrate at a casual sit down restaurant. It's a good time and you spend it getting to know one another over shared food and laughs. He'll take you home afterwards and surprise you with a kiss on the cheek telling you he had a wonderful time.