
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
Confessing Headcanons UT,UF,US!
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.
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More Posts from Cloudyskydreams
hey!! i see youve been posting about the sanses a bunch and i was wondering if you could write some cuddling headcanons? im mostly here for UF Sans but u can write for all 3 of them too if you prefer :o] whatever you want really
Hi thanks so much for requesting! I absolutely can do that for you I loved writing these so much, Red is absolutely one of my favorites he's sm fun to write I did end up doing all three cause why not ::3 Anyways I hope you enjoy!!

UNDERFELL: Red
•Red is a clinger he loves touching you in any form and capacity and cuddling means he can press your bodies as close together as he wants.
•He's can big or little spoon both works for him. When he is big spoon he likes curling up around you holding you to his chest. It's reassuring, but ohhh when you hold his head to your chest and gently rub his skull and wrap yourself around him? He melts he loves being the little spoon it makes him feel safe and loved.
•He runs warm so I hope you're ready for some heated cuddles. He likes to run his hands up your sides and trace little pictures into your skin and his hand is always nice and warm when he does.
•Red gets a bit touchy while cuddling but that's part of the experience, he won't do it if you're uncomfortable with it too. Just squeezing your soft bits or more teasing touches if you seem into it. He doesn't even do it in a lewd way at first he just likes touching you but then his thoughts catch up with his actions.
•Sleep cuddler all the way, he loves being close to you in his sleep and him seeing you by his side when he wakes up from nightmares always helps calm him down.
•PURRING, I am obsessed with them being able to purr this man specifically. Imagine falling asleep with him in your arms while you can feel the vibrations of his purr on your chest. Be proud he feels safe and loved enough to be able to do that!
Small drabble because why not:
Today was not a good day for Red, everything that could go wrong seemed to and it had left him on edge waiting for the next awful thing to happen. You being the dutiful partner as always noticed his mood change 5 minutes into him coming home and called him over to the couch.
"What's wrong baby?" You ask gently looking at the skeleton in front of you. His shoulders are tense and he's looking at the ground his usual smile strained.
"nothing ta worry your pretty lil head over doll, jus a bad day." He grumbles out and you frown. You reach over and gently take his arm he looks up from the floor to stare at you in confusion as you gently pull him forward. He follows your lead and eventually the skeleton is sitting on your lap as you wrap your arms around him. His shoulders drop from their scrunched place and he looks into your eyes as if searching for something. After a second he seems satisfied and lowers his head to your shoulder resting it in the crook of your neck.
"It's okay," you say softly as you trace his spine through his jacket, he sighs contently and nuzzles into your neck cuddling close you"This will pass, it's just a bad day and it will come to an end and tomorrow we'll do better " you continue to reassure him as you rock him gently back and forth. You make no comment on your shoulder wettening or his hold on you tightening and simply hold your bonefriend close, hoping to be a comforting rock for him in tough times like these.
Undertale: Sans
•He likes to cuddle has no preference on little or big spoon besides little spoon requires less work and he likes that. He likes to hold and be held so it depends on whatever mood you're in.
•His cuddles are almost always sleepy and even if you aren't he's feeling nice and relaxed enough he'll probably be passed out within ten minutes.
•One of his favorite positions is him on his back and you resting your head on his ribcage, he'll run his hands through your hair or trace small hearts and doodles on your back.
•Likes to use your squishy bits as pillows especially your legs, he'll wrap his arms around your thighs and burry his face there and be out like a light within the next few minutes.
Underswap: Blue
•Blue likes big spoon the best because it makes him feel bigger and like he's protecting you. He doesn't hate little spoon though and actually one of his favorite places to be in general is pressed into your chest.
•Another big purrer, his purr is loud and proud and he does it often when around you, especially while cuddling because he feels so safe and content.
•For videos where he doesn't have to show his face he likes having you sitting in his lap with his arms caging you in as he plays. He likes having you close to him while he works and plus a little extra motivation of having your partner in smooching distance for when you beat a hard boss is always nice. He likes having you sit like this for multiplayer games too.
•When cuddling he'll get the random urge to bite you and normally follows through with it by nibbling on your neck as he pins you down either with his body on top of you or arms wrapped around your waist. He attributes it to a form of cuteness aggression and being around you that close sets it off in him.
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.
SO on period UT,UF,US,HT!
Ive had this sitting in my notes for awhile wasn't super proud of it still ain't but I wanted to post something, I just had to slap the HT brothers on and boom new post.
Also I've been wanting to write swapfell but I don't know the difference between that and fellswap or really their personalities cause it's so different for each fanfic so if someone could pls explain 🙏
Anyways here y'all go hope you enjoy!

Undertale:
Sans: I feel like sans is pretty knowledgeable so you didn't have to explain it to him. He takes it pretty maturely it's a natural part of life. The puns the horrible puns. He has so many specifically for this time of the month. He's always got your comfort snack on hand in his jacket pockets. He doesn't really change much he'll get off his ass if you ask him to but he sticks by your side mostly and lazes out cuddled with you while watching shows. Pretty good at getting products and snacks you might like he likes to get you some new snacks to try with him and he's good at guessing what you might like.
Papyrus: This man is prepared. After you tell him what it is he researches it and WOWIE he wishes he just asked you to explain but now he's over prepared with knowledge! He has hot water bottles and weighted blankets at the ready. Any snacks you want, heck you want a whole meal? He's on it and it's prepared with extra love. He carries around your products for you and always has pain medicine in his bags. Pretty good at picking them up from the store too and has no shame getting them.
Underfell:
Red: You gotta explain it to him and this man is bewildered for a bit. ya bleed from there for how long??? every month?! He's a little impressed?? Last he checked humans weren't supposed to lose huge amounts of blood but you're treating it like it's a normal thing. After he gets over his initial shock he'll try and help the best he can which is a little awkwardly. He makes a little nest for you out of blankets and pillows and makes sure you're comfortable. He and his magic run warm so he'll lay on your stomach and cuddle to help with cramps, pet his head and he might purr. He's pretty confused about products def one to send Babe what's your pussy size.
Edge: He's aware, he's done his research on his own when you were ovulating about the human "mating cycle". Not a fun experience but he takes it in stride. He listens to what you need and trys to deliver. Massages for sore muscles and heating pads for cramps. He'll make you comfort food while you relax watching a show and join you afterwards for some cuddles. He's pretty good at getting products for you and takes the ones you like into consideration but he's always looking for better healthier alternatives for you.
Underswap:
Stretch: Knows about it (blue taught him when he found out and Stretch showed interest in humans)and is a little awkward(traumatized from the talk with Blue). Hate to say it Stretch doesn't really know what to do he's not grossed out he just doesn't know how to handle it. He tries his best to be comforting giving snacks, heating pads, and cuddles. He's so awkward going to the store to get products plays it cool but has no idea what he's doing and definitely gets the wrong thing after his mind blanks while staring at all the products for too long. You just gotta train him he'll get better.
Blue: Also knows and he's handling it alot better. He takes it in stride and understands the biggest part is you're uncomfortable and he's going to do his best to help with that. He takes care of chores you don't want to do, makes you comfort meals, and always has a heating pad ready. Has so many two player comfort games lined up for you guys, he has stuff to do but most of his work stuff can be done at home! Which means he'll just be a shout away if you need anything . Pretty good at getting products and is one to carry some around in his bag just in case when you guys go out.
HorrorTale:
Axe: You have to explain it to him… Multiple times. He's confused as to why you smell like blood, he likes the smell but he's confused for a bit until he writes a note about it. He will not remember which products to get unfortunately. He's so confused staring at them you'll have to instruct him very clearly over a call and he still probably grabs the wrong one. Cuddles are supreme he's a giant so he'll engulf you in his form and his purrs practically shake your whole body. It's like a free massage chair whenever you want. He sticks closer by your side during this time of month knowing blood means your wounded and his protective urges flare up.
Willow: You'll also have to explain it to him and he's extremely worried when he smells blood. Even more so when he learns how long you bleed, he knows how much blood a human can loose and it worries him you're losing so much. After you explain it's a normal thing and a part of life he calms down slightly. He cleans and cooks a lot when stressed or worried so you constantly have something to munch on and you don't have to worry about any chores. He stays over stocked up on supplies, he doesn't like going out in public very often but for this he will because he deems it important enough. It's why he stocks up so much when he goes out. Mother hens over you hard and you might have to pull him into cuddles to get him to relax for a bit.
woopsies
cut my hand pretty bad and my roommate thinks I need stitches lol she's driving me to da hospital and I'm so woozy from blood loss so that's fun what a way to spend a Friday night
UT,UF,US Favorite Seasons
Undertale!
Sans: Spring •He enjoys the smell of rain and the atmosphere it brings it reminds him of waterfall.
•Lazy rainy days spent cuddled up in his bed with the sound of the rain against the rooftop and a soft blanket. Sounds perfect to him. It's hard to get him out of bed on these days and even if you do he's still pretty sleepy all day even more so than usual.
•He does enjoy the scenery and likes to stop and look at the flowers on the rare occasion he goes on walks, and if he does go on a walk it's going to be on a cloudy spring day with somewhat cool temperature.
•Lets not forget about his favorite holiday April Fools day! He goes hard on this day and his brother and the others try to steer clear of him but he always ends up getting them anyways. His pranks are normally practical but he sometimes whips out elaborate pranks. Most of the time people stumble upon whoopie cushions, bubble wrap under carpets, rigged air horns, and misplaced items for days after the holiday.
Papyrus: Summer •Paps loves being out and about under the summer sun when the temperature is nice and he can show off in his cropped shirts. He owns a bunch of them, his closet is sorted by season and his summer one is mostly cropped shirts with the occasional tank top and short sleeved shirt.
•Owns atleast 15 pairs of sunglasses that he tapes to his face when going. He has a collection of different tapes for this and chooses a different one for each mood. Made the mistake of using duct tape one time and had gunk stuck to his skull for days so he uses washi tape now.
•Definitely owns a straw sun hat and on the topic of hats I feel like he would love bucket hats too.
•He doesn't have the biggest sweet tooth but he enjoys the sweet treats that come with summer too like nice cream and watermelon.
•Will get into the shallow end of the pool (skeletons sink) and splash around with Undyne until Undyne gets to excited and tosses him into the deep end making him stuck at the bottom for the next ten minutes till she stops laughing and drags him out.
Underfell!
Red: Fall •Dont tell anyone but he's a pumpkin spice enjoyer
•He loves the changing of the leaves and the crunch of the fallen ones under his boots. Plus fall is the best time to show off his leather jackets and sweaters.
•Pumpkin carving is one of his favorite activities and he gets pretty intricate with his designs. He always places them outside their door and gets blushy and sweaty over compliments he's really proud of his work just not used to recognition.
•Loves the chill in the air and let's not forget Halloween and spooky movies. He absolutely loves Halloween and he definitely goes to haunted houses. He tried to drag his brother along one time and Edge almost punched someone in the face so now he goes alone or with friends.
Edge: Fall •He's a Spider Cider drinker. He loves the warmer hot drinks and a nice cup of Spider Cider and fall itself for some reason he can't place makes him feel nostalgic and while his childhood wasn't the best he does like thinking about the good memories with his brother.
•Enjoys going for walks in the park and the crisp fall air especially at night. He has a strict sleep schedule but he extends it by a small amount to enjoy the fall night weather.
•Not big on horror movies it's not that they're scary they're just pretty boring to him. He does enjoy occasionally watching them with his brother but would never watch one by himself. He just likes spending time with his brother when he gets the chance, something he'd never admit.
•He loves Halloween decorations, skeleton ones do make him uncomfortable sometimes especially if they're naked but he finds them humerus (hehe) after a short adjustment time his first year. Red got a skeleton and changed it to Edges likeness on year. Edge rolled his eyes at it but he keeps the skeleton in his closet and thinks it's pretty funny to dress up sometimes.
Underswap!
Stretch: Spring •Stretch also enjoys April Fools day as this man is a practical pranker all the way. Often teams up with Sans to tag team the others but all's fair in love and war and the truce is often broken by Stretch himself. He just can't help it.
•Bees start becoming active in the spring and Stretch is a big fan of the little pollinators. Not only do they make honey they're adorable to him and help the ecosystem to continue functioning by spreading pollen.
•I know it's been clarified his cigarettes are not weed but as a stoner I'm making one of my favorite boys a stoner in my au. He celebrates 4/20 with a joint or two and some major munchies while watching the midnight gospel.
•Stretch enjoys the rain as well but more thunderstorm rain while sans enjoys light drizzles. He likes the lightning and can often be seen chilling outside while a thunderstorm is happening storm watching. His first thunderstorm was a mess as him and Blue had never experienced thunder before and were rightfully scared but when he saw the lightning for the first time he was mesmerized. He got over his fear by counting the seconds in between the lighting and thunder and continued to do so for the next few storms but isn't really afraid anymore.
Blue:Winter •Blue loves the snow, it reminds him of Snowdin and there's so much fun stuff you can do in it. He always builds a snow version of himself to stand proud outside their house when winter comes.
•He's a hot cocoa drinker and does enjoy having a little peppermint stick in it as well as some whip cream. He owns a few different types of hot cocoa but his favorite is the one made of real chocolate and milk. He enjoys all the cookies and sweets that come with the season as well. He likes to bake cookies to share with his neighbors.
•Always starts his Gyftmas gift list months ahead of time and does his Gyftmas shopping early as well. He likes to be prepared even though he often buys surprise little gifts he uses as stocking stuffers. Speaking of stockings he and Stretch decorated theirs themselves and Blues definitely has a lot of glitter on it.
•His favorite holiday is Gyftmas and he always over decorates the house. He just gets into the spirit really easily and when he sees something in a store he likes he has to get it to decorate the house with, he's a little bit of an impulsive shopper. He has a little miniature Gyftmas village he always adds a little to each year, it's a tradition he started his first Gyftmas on the surface after Stretch made a joke about using one of the miniature trees as their actual Gyftmas tree