Crush
Dean Winchester x Reader (Y/N) & Sam Winchester (platonic)
Warnings: Fluff, Implied smut, body shaming, alcohol, trauma, nothing too extreme,
This story does not follow the SPN timeline.
Side note: English isn’t my first language. Words: 5166
Y/N is a high school crush/friend of Sam, when they were 16 y/o they attended the same school for a while. She was one of the only kids who didn’t made fun of him, they became friends pretty quick. Sam always thought Y/N was a nice, friendly and cute girl, a little bigger than most of the girls in school but cute. Sam spends his entire time hanging out with her, trying to ask her to prom, only one problem, Y/N likes another, older guy, he didn’t know the older guy was Dean.
Now years later the brothers path crosses again with Y/N.
~ Should I make it a part 2? Let me know! ~
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Dean looked at the menu in front of him, waiting for Sam, hoping he had more news over the case they were working on. Vampires, only this time the nest seemed big, they had killed a few they found, but somehow more and more people seemed missing. It looked like every time they took one down another one popped up.
“Dean? Dean Winchester?” The older brother heard his name and looked up, to see the waitress. “Yes... that’s me?” He answered reluctantly. “It’s me... Y/N. A high school friend of Sam.” He took a good look this time. - “Y/N?” Sam had just entered the diner. “It’s been so long! How are you!” He asked her while immediately pulling her in a hug. “I’m great! Too long I know. How are you?”
Dean witnessed the conversation, still not entirely sure who she was. He started to think about all the high schools they attended to. Sure he would have remembered it when Sam had a girl friend... definitely a girl this... hot. Unless he didn’t attend school anymore. And then he remembered.
“Thanks Dean, for driving us!” - “No problem sweetheart.” He winked at Y/N while she got out of the car. “Sam, wait a sec I need to talk to you.” He held his brother back. “Can’t this wait after school? I’m going to ask Y/N to the dance.” “Yeah, about the dance...” he mumbled under his breath. “Hey, Y/N wait up!” Sam rushed out of Dean’s car, he watched his little brother jog to the slightly chubby but cute girl, knowing he won’t be taking her to the dance.
Dean remembered, making him unconsciously interrupt their conversation, without filtering his words first. “Now I remember... Y/N the chubby friend from when you were 17!” - “What the hell Dean! ” Sam hit his shoulder, while he looked apologetic over to Y/N, who seem to be amused by Dean’s bluntness. “Yeah, well that’s what most people remember of me.”
“I’m sorry, you look great! You’ve changed... A lot!” Dean apologised in a yet flirty way, looking her up and down. “And you haven’t changed, have you.” Y/N laughed at his attempt. “Please tell me you’re staying in town a little longer this time?” She turned to Sam. “Eh, a few days at least.” - “Great...” she kept looking at him, “Jeez, almost forgot to take your order.” They talked a little more after they had their food and in between orders.
“Hey if you want, we can stay a little longer after the job is finished.” Dean told his brother. “Maybe you and Y/N over there can catch up some lost time.” - “I don’t know Dean, she seems to have a great life I don’t want her to be involved in ours.” - “Did you ever go out with her?” - “No, she eh, liked someone else.” - “Really who?” - “Don’t know, an older guy, didn’t attend our school.” - “ Oh really? I seem to remember she liked you.” Dean felt bad for his brother.
“You’re lucky again, Y/N.” Her co-worker said while they were making their orders. “What do you mean?” - “You always get the handsome or cute boys at your tables.” She nodded to Sam and Dean. “Old friend of yours?” - “I went to school with that one...” she pointed at Sam. “And that is his older brother. He, eh was the first guy I ever kissed.” - “Lucky you.” Y/N her mind drifted away to an old memory.
School dance was in two weeks, but Y/N still had no dress. All the dresses she tried on were either, too long, short or small. The popular girls who bullied Y/N for being overweight seemed to notice Y/N struggling in the store and decided to ad a little salt to the wound.
Dean dropped Sam off at the library a few streets away, he had to run an arrance for his dad and decided to buy some magazines at the store for himself, the store he needed was across from the store Y/N was in. He noticed her, standing in front of a mirror, she looked good, but he noticed her cheeks were red, she was almost crying. Then he heard the 3 popular girls walk out “Can’t believe little piggy thinks she will find a dress that will look good on her.” - “No way she finds a guy to take her.” Another one added.
Dean felt bad for her since she was the only kid in Sam’s class who was nice to him, he walked in the store, the second she saw the older Winchester enter the store she fled to the fitting room. “Y/N? Are you ok?” He placed his ear next to the door, he could hear her sniff. “Yeah, yeah I'm great thanks.” - “Don’t lie to me sweetheart... Is it those girls?” - “They just make fun of me. Nothing special. I’m used to it.” - “It is if it makes you cry.” She didn’t answer. “Why don’t you show me your dress?” Y/N slowly unlocked the door, looking up with teary eyes, Dean still leaning on the fitting room. “They are right, I look ridiculous, I won’t find a dress that fits me.”
“What are you talking about? You look amazing.” He smiled slightly. “You just say that to make me feel good.” She felt her cheeks glow, afraid to look up. “No, no, no you look stunning in this dress.”, “This one maybe, the others are horrible.” - “Then buy this one.” - “Can’t, too expensive.” Dean’s heart broke. Y/N got back in the dressing room, changed and hung the dress back. “Hey, why don’t we go get some burgers?” Y/N was surprised. “You want to hang out with me?”
Dean never really wanted to hang out with Sam and her, he always felt too cool she thought, he always dated the ‘hot girls’ she knew he was a player from what Sam told her, but him being nice to her made her feel good. “Hey eh, why don’t you go in and order already. I have to buy some things for my dad, I’ll be right with you.” - “Sure... You know what you want?” - “I’ll take what you‘ll have.”
Y/N watched Dean drive off, only to see that the girls from before were at the same diner. Great, she thought. “Keep your head up Y/N, you can do this.” Little did she know Dean went back to the store to buy that dress she liked. He walked into the diner to see the girls standing around Y/N’s table. “ How much do you eat Y/N, no surprise no dress fits you.” - “It’s for not for me, it’s for Dean.” - “Did you really think a boy would want to be seen with you?” - “Yeah, especially Sam’s hot brother.” the 2nd girl added. Dean felt the anger boil inside him.
“There you are sweetheart.” Dean said a little louder than needed, he walked past the three teenage bullies. “Sorry, it was busy at the store.” He took the place beside her, pulled his arm around her, while his other hand holds her cheek. “Let me make it up to you.” Without warning he kissed Y/N’s lips. Leaving the other girls stunned. Then he turned to them “Friends of yours?” - “Not really” she said bold, that kiss and his arm made her confident. Dean waved them goodbye, while keeping his arm around her almost for the entire time.
Y/N her memory faded when she noticed Dean walking up to her. “Can I get the check?” He asked. “Sure” She smiled. “You know, I never got to thank you.” - Dean smiled confused, changing the subject “... hey, we are eh, staying in town a little longer. Why don’t you give us a call on your day off.” he wrote his number on a napkin and shoved it forward. “Well, I don’t know.” Dean still looked confused. “Are you planning on kissing me and then leaving me again, Winchester?” she flirted, leaving Dean startled.
“Ready?” Sam asked dropping a hand on Dean’s shoulder. “Eh, yeah, I-I'm ready.” By the time Dean got to the Impala he remembered every detail. He had kissed her to shut those mean girls up, he and Y/N stayed at the diner talked, laughed, way longer than he was planning, he just felt bad for her but the longer he talked to her the more he actually cared for her, by the end Dean realised why Sam likes her so much, she was really smart, funny and mature. She made him smile like no one had done in years.
He dropped her off at her house, but not before he kissed her again in the impala, “I, eh heard you have no date to the school dance yet.” He asked nervous. “No, I don’t.” Y/N’s heart was racing and her head spinning, is he really asking her what she thought? “Well, I-If you would like, I have no plans that night...” He looked up at her, she responded by pulling him in for another kiss.
He opened her door for her, pinned her against the car and asked her not to tell Sam yet. “I want to tell him myself.”
“Dean?” - ” Hm?” - “Why so quiet?” Sam asked in the car. “What? Oh nothing, nothing.”
The next day Sam and Dean split up again, Dean wanted to surprise Y/N after work now he fully remembered. But he saw Y/N and Sam walk out of the diner, holding a milkshake, she had her arm wrapped around Sam’s arm. They were laughing, too involved in their conversation to notice Dean at the corner of the street. He could see the two of them being the perfect item since they were so similar, he for some reason even forgot about her. He decided not to drag himself down and went for a drink at the local pub.
“You know, you never told me who the guy was who took you to the dance.” Sam casually asked Y/N while taking a seat at the bench in the park. “Wow, he never told you did he?” Sam looked confused. “Dean... He asked me.” - “Dean... my brother Dean?” - “Yeah... Please don’t tell me you’re going to mad at him? It was ages ago.” - “No, oh no not at all, it just makes sense.” Sam laughs sincere. “Why are you laughing?” - “He acted all weird yesterday morning, after seeing you and I can remember he spend all dad’s money, later he admitted it was on a dress for a girl, didn’t want to tell us who. And before leaving he snuck out.“ - “He brought that dress to our front door, with a note, telling you guys were leaving.”
The night of the school dance Y/N got nervous, she still had no dress but Dean told her not to worry. “Y/N!” - She heard her dad call out to her “Come down here honey.” The second she got the end of the stairs she saw her dad holding a bag, a black clothing cover. “I think this is for you.” He helped her open it. Y/N recognised the dress immediately. A little note dropped out of the bag. “I’m sorry sweetheart, our dad decided to move today. I wished I could see you in this dress, no doubt you will be the most beautiful girl. D.”
“Did you go?” - “Sorry?” - “Did you go?” Sam repeated the question. “No, I didn’t. I wanted but it wouldn’t be the same without my best friend.” She said bumping her shoulder to his arm. “You know, I really felt bad when you said you liked someone else.” He admitted looking shy at her. “But I’m glad it was Dean. He is a nice guy.” - “Ha, not what you said years ago.” - “Yeah, well in my defence he did get all the girls, even the once I liked back then.” He bumped her back. “I think he still likes you.” Sam casually said. “What? Oh, come on Sam. It was years ago, he didn’t even recognise me at the diner yesterday.” - “I’m serious Y/N he acts strange, his I like a girl but I'm afraid to say it, strange, call him.” - “You don’t mind?” She asked afraid of his answer. “No, not at all, to be fair, Jess is still in my heart and mind.”
Sam and Y/N walked back to the diner where she parked her car. “Oh my god... He still drives that impala?” She asked while crossing the street to see the car up close. “Dean’s baby.” - “Great memories.” She said looking inside the car. “Oh please don’t tell me... you two...” Sam looked disgusted. “What?” Then it hit her “Oh god, no Sam! Dean and I, we never did, never...” Sam looked relieved, he looked around “He is probably in that pub over there.” He pointed out. “It’s now or never Y/N.” He smiled like a child who had a secret. “Fine, I’ll talk to him.”
Y/N walked in, a little nervous, if Dean really hasn’t changed, he had found himself a hot girl by now. To her surprise he was sitting alone at the bar, drinking a beer while watching the game on the small tv above the bar.
“Hi stranger.” She smiled while taking the seat next to him. “Mind me sitting here?” Y/N asked when she saw his surprised face. “Yes, I mean no, no please sit.” - “I eh, I saw your car outside thought I’d say hello... Sam and I were at the park, reminiscing about high school. Would have been great if you were there” - “I saw you two when I walked to the diner, didn’t want to interfere your date.” - “Date?! Oh no Sam and I weren’t on a date.” -” Well, I think you two should.” Dean answered looking back at his beer. “Considering your history and both being really similar personalities and all.”
“I’m afraid a little too similar.” Dean looked up. “Don’t get me wrong, Sam still an amazing person... I like him, but I might still like his older brother a bit more.” Y/N was afraid to look directly in Dean’s eyes when she confessed that. “Even when he didn’t take you to the dance like he promised?” - “Even when he didn’t recognise me.” Dean felt his cheeks burn, “You have changed a lot.”
“It’s ok, deep down I knew it wasn’t the same for you like it was for me.” Y/N said without feeling any grudges. “At the beginning maybe, but after that day at the diner, after that first kiss...” Dean felt bold admitting this. “Please don’t tell me that you fell for the chubby girl?” - “I did.” - “You never do.” - “Oh I did, I fell hard, I used my dad’s money to buy you that dress! He was pissed!”
“Sam told me, you didn’t have to get into trouble for me.” - “at least you were the prettiest girl at that dance.” - “I didn’t go.” - “What!” Dean dropped his beer back at the bar. “My date and best friend were abducted by their father, I didn’t want to be alone.” She joked but was serious about the alone part.
After a few beers Y/N and Dean found themselves still at the bar. Laughing, joking and even flirting.
“As much as I don’t want this night to end, I have to go. I have an early shift tomorrow.” They both stepped out realizing it was late, the sun had gone down. “Let me drive you.” - “Don’t you think you had a little too much to drink?” - “Bullshit, I can drive get in.” He said while holding her door. Y/N got in and immediately recognized the same smell as all those years ago.
While driving Dean remembered their last night together.
Dean had asked Y/N to go to the movies with him; to his surprise she accepted. During the movie he couldn’t keep his eyes on the screen. He kept looking over at Y/N wondering how to tell Sam he fell for his best friend, for his crush. He felt guilty but couldn’t keep sneaking around with her. “Sam asked me to the dance Yesterday.” She whispered without looking at him. "What did you say?” Dean asked, shifting in his seat, feeling a little nervous. “That I liked someone else.” He could see her cheeks blushing. While his heart made a jump.
“Oh really?” - “Uhu, he is handsome, a little older, a real prince charming, I didn’t tell all that to Sam, obviously.” - “Well, tell me who is this prince I need to fight?” he joked while playfull attack her, kissing and licking her neck, which made her giggle. His lips found hers, the kiss deepened “Let’s get out of here.”
When they walked out of the theatre, holding hands, he saw his dad outside. He pulled her back hushing her with his hand on her mouth. “He has no idea I’m here.” he whispered in her ear. When he was out of side they ran to the car, and Dean drove them to an open spot next to the football pitch at their school. He pulled her closer to him, immediately kissing her again, seemingly not getting enough of Y/N.
His hand moved under shirt, over her stomach, making her clench up and pulling back.
Dean let go of her “Did I do something wrong?” - “I’m just not really comfortable in my skin.” She admitted shy. “Oh, I'm sorry sweetheart” - “it’s ok, I-I just never. No guy ever touched me like that. Probably because of my... size.” - “Don’t be ridiculous, you look amazing. I don’t get it why no guy ever took a change to be with you before.”
But Dean held back the rest of the night, making her comfortable again. Keeping it to kissing and touching above the clothes. He didn’t want to push her away, thinking she deserved to know not all man are the same.
The drive home was quiet and filled with tension. Seeing Dean driving his car made Y/N feeling warm and safe again. He looked the same but at the same time different, broken. He looked at her, noticed her staring. “Like what you’re seeing sweetheart?” She blushed, looking at her hands that were folded on her lap. “Sorry.” - “Don’t be, I like it, reminds me of the good old days.” he jokes.
“Here we are.” Dean said trying to sound neutral, but his heart beats fast. “Why don’t you come inside for a second, I have something to show you.” Y/N said very enthusiasts. Dean followed her up to her apartment giving himself a peptalk, thinking this may be the moment. “Wait here.” Y/N’s voice pulled him out of his thoughts.
He looked around, no pictures or signs of a man. “Great!” he mumbled. “What was that?” she asked? Dean flinched “Nothing!” He turned around to see Y/N in the dress he bought for her.
“Wow” Was all he managed to say. “It’s a little big, I know but I kept it.” She said while looking down at herself, not noticing Dean getting closer, “The first boy I ever loved gave it to me.” She looked up, meeting Dean’s eyes. Feeling the air shifting. “I never thanked you for the dress, did I?” Dean’s eyes flicked from her lips back to her eyes. “No, not really.” his lip pulled up in a half smile.
“Hm. In that case.” Y/N’s hands moved over his shoulder, neck, to the back of his head, feeling his hair move between her fingers. Pulling him closer. “Thank you.” she whispered against his lips before closing the space with hers. Dean still tasted the same as she remembered, his full lips felt even better than before. Dean’s hands moved up to hold her ribs, pulling her closer to him but letting go of her lips. “Remind me to buy you more dresses.” she smiled before he finds her lips again.
After a long passioned kiss Y/N spoke again, “I’m going to put on something more, comfy, mind helping me with the zipper?” She asked while turning her back to Dean. Knowing very well what she was doing. Dean moved her hair to one side of her shoulders, kissing the one that was showing, while unzipping her dress, letting it fall on to the floor. His hands roaming over her body, Y/N’s head fell back, letting out a deep breath, while he moved over to that one spot behind her ear.
“Still as beautiful as I remember.” He whispered in her ear while he held on to her hips. Y/N turned around finding his lips again, walking him back to find the couch. Dean sat down slowly, while Y/N took a seat on his lap, straddling him. Dean’s hands holding her hips, his finger brushing over her ass, it was the first time she paid no attention to her own body, she usually was very well aware of the stretchmarks she had from being fuller, but for some reason Dean made her forget all of that.
Their kisses deepen, hips grinding, breaths getting heavier, hands roaming each other's body, hungry for more... Until they were interrupted by the sound of Dean’s phone. Dean searched for his phone, “It’s Sam. He can wait.” Dean said tossing the phone on the other side of the couch, only to pull her back in for more, but his phone rang again. “D-Dean, maybe you need to pick up.” Y/N said between kisses.
Dean sighs picking up the phone, “Sammy?” - “Dean? I found the nest, where are you, I need back up.” - “I eh, I am... I’m on my way.” He said, while looking apologetic to Y/N. - “Brother in need?” she asked still sitting on his lap. “I’m sorry, I really need to go.” He kissed her, holding her face in his hands. “I promise I’ll make it up to you.” he said looking deep in her eyes, just to be sure she knew he meant it. She nodded.
"I’ll see you tomorrow.” Y/N kissed Dean and closed the door behind him, slightly hating Sam for ruing the moment, but over the moon, feeling the same butterflies as she felt all those years ago. Y/N got ready for bed, Dean promised to have breakfast at the diner tomorrow and to pick her up after her shift, so there was no reason not to get in her pj’s.
But by the time she got to the bathroom she heard a knock on the door. Smiling she yelled “Forgot something, Dean?” Only to open the door seeing no-one. She stepped outside to feel a presents behind her...
Dean pulled over at the motel he and Sam stayed, so he could pick up his brother, before taking down the vamps nest. “Really Sam, fighting a nest in the middle of the night, smooth timing!” - “I thought the fast we take them out the quicker we can move on.” the younger brother looked at his sibling putting the weapons and the machetes in the car. “Unless you have a reason to stay.” Dean gave his brother a dead stare before closing the trunk.
“Did you talk to Y/N yet?” Sam was curious. “Well, since you ask so nicely. We were in the middle of a... conversation, when you called.” he emphasised but keeping his eyes on the road. “That escalated quick.” Sam smirked. “I really think you should give her the benefit of the doubt and think, maybe, just maybe she is your ticket out of this life.” - “And leave you alone? No way.”
“Think about it Dean, we liked living here. This town, the people we were mad at dad for leaving, again.” - “You were always mad at dad, you left for college.” - “Y/N’s idea.” - “Really?” Dean looked over to his brother this time. “Y/N told you to go study law?” - “No, she told me that we were more than our dad wanted us to be. That we could do what we wanted. Bet she didn’t want you to be in dad’s footsteps.”
The rest of the ride the brothers were quiet. Sam’s words lingered in Dean’s head. Maybe there was a way to be with Y/N. He could tell her everything, no there was no way he would let her in to this life.
The Winchesters arrived at the old warehouse where the nest was. When they entered, they immediately saw Y/N tight up to a chair at the back, unconscious. “Good for you to show up, I figured since you two killed my girl, I might just take yours.” One of the vamps spoke. “It’s remarkable how the smell of humas linger on our dead. So easy to track them down. And like today we were very lucky to find us a little surprise.” - “Let her go you son of a bitch!” Dean growled.
Y/N heard Sam’s voice in a distance. “Y/N? Y/N wake up.” She slowly opened her eyes. “S-Sam? What happened. W-where am I?” She looked around, the haze in front of her eyes disappeared, she saw Dean chopping of the head of the last vampire, making her scream. “Hey, hey sweetheart, you’re ok.” He came running towards her. Y/N was too afraid to react, trying to wrap her head around the things that happened. Only moments before she lost consciousness again.
Dean carried Y/N to the car, the vampire drank so much blood she felt too weak even to stand on her legs.
The drive home was filled with awkward silence, Sam kept looking back at her trying to see how she was doing, but Y/N kept looking outside the window, trying to hold back the tears. Dean parked outside the motel they were staying, while Sam tried to help her out of the car. “What are we doing here? I thought you would bring me home?” Dean could hear the fear in her voice.
“Home isn’t safe now sweetheart.” - “And this motel is?” - “It’s just for the night, tomorrow we check out your place and if it’s safe we can take you home.” Sam answered in his sweet voice.
Sam supported her while they walked inside, her eyes roaming the place. “If there is anything we can...” - “I would like to take a bath.” She interrupted Dean, still not giving him a look. Y/N grabbed Sam’s arm again, “Can you give me a hand?” Sam looked over at his brother, hesitated before he answered “Eh, yeah sure.”
Sam filled the tub before helping her with her clothes, in any other situation Y/N would have felt embarrassed but after tonight she didn’t care anymore. Sam held her arm when she stepped in the bath. She could feel the warm water touching her skin, stinging at the small bite marks that covered her body. “Are you going to be ok?” Sam asked before leaving her alone for a minute. “I’m fine Sam, thank you.” Sam left de door slightly open, Dean still stood in the middle of the room, he looked at her while his brother walked toward him, seeing her back all bruised.
Y/N heard the brothers talk, “Why won’t she talk to me Sammy?” She could hear the pain in Dean’s voice. ” One, she just got ambushed by vampires. And two she saw you chop off someone’s head.” Sam took a deep breath. “She is probably traumatised, look at all the bite marks and bruises on her, they drained her, to the point of fainting. Give her some time.” He whispered knowing Dean meant well. “I’m going to get some painkillers and bandages for her.” He padded his brother’s shoulder. “Be right back.”
Dean leaned against the bathroom door. “Y/N?... May I come in?” He waited for an answer, but she didn’t respond. Dean slowly walked in kneeling next to her. He slowly lifted his hand to caress her hair. At first, she flinched but the second she truly felt his soft touch, she couldn’t hold back her tears. Dean shifted on to the side of the tub, her head fell against his thigh. He held her hand and stroke her hair with the other, while he whispered to her over and over reassuring words “Shh, you’re going to be ok, I’m here.”
By the time Sam got back he heard Dean and Y/N talk in the bathroom. As he walked over to take a peek, he saw Y/N in one of Dean’s old shirts while he towel dried her hair, or at least he was trying to. She was asking him questions about what happened, and he answered them honestly. Dean walked Y/N out of the bathroom towards his bed. “You need some sleep, take my bed. I’ll sleep on the couch.” he said while tucking her in. “Are you sure?” her voice was still very shaky. He kissed her head in response.
Later that night Y/N woke up from a bad dream or was it a memory. She looked around the room to find something to recognise, seeing Dean sleeping on the couch he looked so peaceful yet in a very uncomfortable position. “Dean? Dean?” She whispered, by the third time he woke up. “Dean?” He woke up startled rushing over to her. What’s wrong?”
Y/N opened the blankets, gesturing him to lay down next to her, doubtfully he crawled into bed next to her. For a second, they were looking into each other’s eyes. If the circumstanced where different he would have kissed her now. But instead, she pulled herself closer to him, her face was snugged against his shirt, she could hear his steady heartbeat. Dean’s chin touching her hair, he tugged an arm around her pulling her close. She let go of a sigh “I had a bad dream.” She confessed. “I’m here, try to get some sleep.” he kissed her head.
