Archive of Our Own ^beta

Chapter Text

You had known the Winchesters since you were little, your dads would sometimes go on hunts and leave you at Bobby’s together. So, Sam and Dean became your best friends, you loved and cared for them both, but the eldest brother was always so much more to you. You don’t even know how long you had been in love with him but eventually, you both confessed your feelings and he became your first everything. First crush, first kiss, first time, first love, every significant experience in your life he was there with you. When you were almost of age your dad had a nasty fight with John, and you had been kept away from the Winchesters. Not seeing or hearing from either of them for years broke your heart but you slowly were able to move past it.

Surprisingly you ran into them on a werewolf hunt a few years after Sam left college and they asked you to stay with them, you couldn’t agree fast enough, happy to have your boys back. Unfortunately, being near Dean again caused all those old feelings you thought you had gotten over to resurface, but you pushed them back. He didn’t see you that way anymore and you had to accept that you were like a sister to him now.

Everything was going well; hunting was going as smoothly as it could, you had gotten just as close if not closer to your boys, and you were happy and then Sam died. Something felt broken inside of you after that and you coped by attaching yourself more to Dean than ever before, you couldn’t bear to lose him too. So, you chose to go with Dean and join his apple pie life, but he found Lisa there and that broke your world all over again.

***

God how you hated her, she was trying to take Dean away from you and he didn’t even realize it. It wasn’t just you being jealous either, she was honestly horrible to you. It was obvious she couldn’t understand why he thought of you as his best friend or how he ‘put up’ with you as she liked to phrase it She hated all the attention he gave you, how he would drop anything to come help you, even leaving her alone to do so. But she never commented on anything when Dean was in earshot, no she was smarter than that, but as soon as he left a room, she would go on about her hatred for you. You never said a word though, not wanting to crush Dean’s dream of being free and happy. If she made him happy, you could never interfere with that, he deserved everything even if it meant you dying every time you saw them together.

Today it was a specific sort of hell, Dean had dragged you with him and Lisa to a neighbourhood pool party. Dean didn’t want to be forced to be around all the gossipy neighbours by himself and begged you to come with. Lisa had rolled her eyes at the fact he had brought you, especially since Dean couldn’t seem to take his eyes off you in your short shorts and bikini. Not that you noticed, but she certainly did, and she was not pleased, making it obvious when the moment you arrived, she took Dean by the arm to go mingle with her friends and leaving you by yourself.

Rolling your eyes at her behaviour, you moved towards the food table. You had never felt such jealousy towards someone else before, why was Dean with her, didn’t he see you? What were you saying, of course, he didn’t, he thought of you as a sister. You had even overheard him tell Lisa one day when they were arguing about you, saying that he only saw you as his little sister and would never be with you in that way. Dean didn’t know you heard him though, as you managed to get out of there before either of them could spot you. Ever since then you had tried to create space between you, realizing you were around far more often than a friend or ‘little sister’ should be and you had to fix that. Maybe it was time you left Dean with his apple pie life and try finding your own.

“Hey, gorgeous!” A cute guy said as he came up to you and handed you a drink. He couldn’t have come at a better time, no better way to get over someone than by getting under someone new. You gave him an obvious once over, noticing his impressive abs before taking the drink with a smile. “Hey”

“I haven’t seen you around before, did you just move in?” He asked grinning down at you. He was no Dean Winchester, but damn was he cute.

“No, a friend of mine invited me to come. Said something about gorgeous looking guys living around here and how I just had to come meet them” You said staring into his eyes and biting your lip innocently. He smirked leaning in a little closer to you until you were almost touching, eyes looking right into yours.

“Oh really? Have you met any so far?”

“Well, there’s this one guy, that I can’t seem to take my eyes off.” You say licking your lips, watching him follow the movement. He stepped closer until your chest was touching his shirtless one.

“He can’t take his eyes off you either baby.” He said leaning down but you sidestepped and grabbed his hand, almost making him fall. Giggling at his shocked expression before pulling him into the house. Might as well have a little fun at this boring ass party anyway. Plus, Dean was too busy with Lisa to care about talking to you anyway.

“Let’s take this party somewhere more private.” You say leading him into the house through the kitchen. You were sure whoever owned this house would freak out if they saw you and knew of your intentions, but they were all too occupied with the pool party festivities to notice.

As soon as you walked in, he pushed you against the wall roughly, making you giggle in excitement. He chucked as well as he leant down to finally kiss you. His lips grazing against yours before he was ripped off of you.

“What the hell, Dean!?” You scream as soon as you saw who it was that ruined your fun, of course, he would ruin this for you too. He was standing in front of you looking angrier than you’d seen him in a while and the cute guy, whose name you still never got or asked for, was standing behind Dean looking mad at being interrupted as well. It was, of course, nothing close to Dean’s anger, he had the same look in his eyes that he usually got when he was in front of a monster he was about to kill.

“Dude, piss off, you’re interrupting us.” Cute guy told him, giving a slight push as he said it. Dean snarled and whipped around to deck cute guy in the face, knocking him out cold in one punch.

“Dean!” You yelled. He couldn’t even let you have this, you needed to get fucked to forget him and he wouldn’t even let you. Taking a deep breath and running your fingers through your hair “I can’t do this anymore”

“What are you saying” Dean asked going still at your words.

“I don’t want to do this anymore Dean, I need to leave, and I don’t mean this party.” You say looking away from him missing the look of pain flash across his face.

“You want to leave me” He said emotionless.

“I need to find my own apple pie life Dean and stop interrupting yours. Look it's obvious Lisa hates my guts and I’m not fond of her either but she makes you happy Dean and that’s enough for me. I want to be happy too Dean, and you can’t give me what I’m looking for” You say almost revealing your feelings, you weren’t even brave enough to look him in the eye as you said all this to him. You knew cute guy would be fine as Dean didn’t do that much damage, so you left him passed out on the ground and moved around Dean planning to leave the party and hotwire a car out of this town. Stopping beside him you place your hand on his shoulder and kissed his cheek before moving toward the front door. “Goodbye Dean”

Dean grabbed your body and moved you against the wall, caging you in with his arms and body pressed up against yours.

“What are you doing?!” You ask, shocked you could get the words out with your heart beating so quick and him staring at you like that. You hadn’t seen that look on his face directed at you since you were teenagers.

“Something I should’ve done a long time ago.” He said leaning down to kiss your lips. You stood frozen in shock for a few seconds before managing to respond, bringing your hands up to grab his hair and shirt. Separating your mouth from his you pulled his head to the side to bite at his neck, causing him to release a surprised moan and place his hand on the wall behind your head.

After a few minutes of becoming familiar with each other's lips, he grabbed your legs and hoisted you into his arms, pushing you against the wall once more. Wrapping your arms around his neck, and legs around his waist, you lean down to kiss him, grinding down on his dick through his swimsuit trunks as the kiss gets more passionate and needy.

Biting at your lips as he moved your short shorts to the side and ran a finger up your slit. Finding you soaking wet for him, he couldn’t help but groan and remove his hand from your pussy lips to taste you on his fingers.

“Fuck Y/n, you taste even better than I remember. Next time I want to taste you until you can’t move but right now, I can’t wait” He said as he pulled his trunks down and you helped him remove it with your feet. Your mind freezing as you processed his words, next time, did that mean he wanted this to happen again.

When he got his trunks past his cock, he grabbed himself and rubbed it down your slit a few times to get it wet and tease you. His actions caused you to shiver and make you come back to the moment, you would worry about his words later. Now you wanted to focus on him as he finally pushed himself inside you, and you both couldn’t help but moan at the feeling. It felt as it did when you were young and in love, but at the same time it was new and different, better than it was. You could never get over that first feeling of him sliding inside you, no matter how many times he did, especially not this time when you hadn’t felt it in years.

Dean had to stop once he was fully inside you, the feeling of you wrapped around him was going to make this be over a lot sooner than he wanted and god did he want to last as long as he could with you. How did you manage to always make him feel like an inexperienced teenager around their crush. Breathing deeply for control, he rested his forehead against yours as you adjusted to his girth. When you were ready you only had to look him in the eyes and he began to move his hips into you slowly at first, making you feel every move he made. You needed more and reached up, bringing his lips back down to yours, wanting to feel him everywhere.

He started to move a little faster but just enough to tease you without letting you cum. You couldn’t help but moan at the feeling even if it wasn’t enough to get you there, it still felt amazing. Gripping onto his head, you look over his shoulder, feeling yourself getting wetter at seeing the cute guy still knocked out. You were surprised it turned you on knowing he was there and could wake up at any second and see you two fucking.

Your moans kept getting louder as Dean started increasing his pace and really started pounding into you. The music from the party outside drowned all your noises out though, so no one heard a thing. That thought made you realize Lisa was outside, probably bragging about her relationship with Dean to all the neighbours, while you were standing 10 feet away from her, fucking her boyfriend against the wall. Fuck you wish she could see you, clenching around Dean at just the thought of it happening, causing his pace to falter.

“Fuck princess, don’t do that, I’m going to cum right away if you do.” Dean mumbles as he sets you on the floor and removes himself from you. You are so distracted you don’t even question him, your heart skipping a beat at hearing that nickname, he hadn’t called you that since you were together. You didn’t realize how much you missed hearing it, but you had no time to think further on it as he quickly turns you around to face the wall. You place your hands on the wall and he shoves his dick inside you once again, making you whimper at the feeling of him entering you at a much deeper angle this time. He doesn’t allow you to adjust and starts fucking into you hard. Probably leaving bruises in your skin with how tight his grip on your hips was.

His hand came down on your ass a few times as he fucked into you, causing you to almost scream at the sensations, you loved when he spanked you. Moaning his name as his hips start to stutter a bit signalling he was close.

“Fuck sweetheart scream my name” He moans, his chest leaning over your back as one hand reached up to your nipple and the other reached around to rub your clit.

“Dean!” You yell, his fingers giving you the push you needed to finally cum all over him. Feeling you clench down and soak his dick made him lose it and push his head into your neck, groaning out your name as he spilled inside you.

You both stood there for a few minutes, catching your breath before he pulled himself out and began pulling his trunks back on as you heard and felt his cum fall from inside you and onto the floor.

He swore and turned you around to kiss you passionately. Getting really close, your bodies intertwined as you made out, enjoying the feeling of Dean all around you.

“What was that?” You ask him as your lips separated, you didn’t want to ruin this perfect bubble you were in right now, but you were both standing in your swimsuits, freshly fucked in a random person’s kitchen, with his girlfriend outside and a passed out man on the floor.

“I told you sweetheart, something I should’ve done a long time ago” Dean said smiling down at you, tucking your hair behind your ear. You blushed at the motion, before looking back at him “So, you don’t regret it? It’s not because I told you I was leaving?”

“No, it wasn’t that. Don’t get me wrong I don’t want you to leave me Y/n/n, I can’t stand the idea of you not in my life but that wasn’t why I did that.”

“I thought you only saw me as a sister”

“Not even a little bit, I love you sweetheart and not in a sister way. You’re the only girl I’ve loved and wanted since I was 10 years old and that won’t ever change.” He said leaning down to give you a kiss. You smiled up at him but then frowned and stepped back. He looked confused at your movements and pouted, wanting you to never leave his arms again.

“That’s not what you said before”

“What are you talking about?”

“I heard you and Lisa” You said crossing your arms over your chest. He chuckled, you looked so cute when you pouted, but he knew what conversation you must have heard and how wrong you were.

“Sweetheart, I lied to her. She was always bitching about you and how close we are, I told her that to shut her up. I couldn’t have her know that she means nothing compared to you, not when I thought you didn’t like me that way anymore and I had no chance with you.”

“What? Dean, I’ve been in love with you since you gave me my first kiss” You shyly smile at him, your face turning a little red at the admission. It was worth it though to see his whole face light up, you hadn’t seen him look so happy in years.

“Let’s get out of here” Dean said grabbing your hand and moving to the front door, avoiding the party altogether.

“Where are we going?” You ask as you followed him. He didn’t give you an answer until you were both inside baby.

“You’ve always wanted to check out New Orleans haven’t you” He said grinning, already knowing the answer. Your eyes widen as you hear this and all that would imply.

“Dean, are you sure?” You ask not wanting him to regret his choice to leave it all behind for you.

“Never been so sure about anything in my life, I don’t need anyone else when I got you, princess. You’re the only girl I’ve ever wanted.” He said smiling as he wrapped his arm around you, causing you to snuggle closer into him as you left it all behind you.

Driving away as it always should’ve been, the two of you together, forever.

Chapter Text

You had known the Winchesters since you were little, your dads would sometimes go on hunts and leave you at Bobby’s together. So, Sam and Dean became your best friends, you loved and cared for them both, but the eldest brother was always so much more to you. You don’t even know how long you had been in love with him but eventually, you both confessed your feelings, and he became your first everything. First crush, first kiss, first time, first love, every significant experience in your life he was there with you. When you were almost of age your dad had a nasty fight with John, and you had been kept away from the Winchesters. Not seeing or hearing from either of them for years broke your heart but you slowly were able to move past it.

Surprisingly you ran into them on a werewolf hunt a few years after Sam left college, and they asked you to stay with them. Something you couldn’t agree to fast enough, happy to have your boys back. Unfortunately, being near Dean again caused all those old feelings you thought you had gotten over to resurface, but you pushed them back. He didn’t see you that way anymore and you had to accept that you were like a sister to him now.

Everything was going well; hunting was going as smoothly as it could, you had gotten just as close if not closer to your boys, and you were happy… and then Sam died. After that, something felt broken inside of you and you coped by attaching yourself more to Dean than ever before, you couldn’t bear to lose him too. So, you chose to go with Dean and join his apple pie life, but he found Lisa there and that broke your world all over again.

***

God how you hated her, she was trying to take Dean away from you and he didn’t even realize it. It wasn’t just you being jealous either, she was honestly horrible to you. It was obvious she couldn’t understand why he thought of you as his best friend or how he ‘put up’ with you as she liked to phrase it. She hated all the attention he gave you, how he would drop anything to come help you, even leaving her alone to do so. But she never commented on anything when Dean was in earshot, no she was smarter than that, but as soon as he left a room, she would go on about her hatred for you. You never said a word though, not wanting to crush Dean’s dream of being free and happy. If she made him happy, you could never interfere with that, he deserved everything even if it meant you dying inside every time you saw them together.

Today it was a specific sort of hell, Dean had dragged you with him and Lisa to a neighbourhood pool party. Dean didn’t want to be forced to be around all the gossipy neighbours by himself and begged you to come with him. Lisa had rolled her eyes at the fact he had brought you, especially since Dean couldn’t seem to take his eyes off you in your short shorts and bikini. Not that you noticed, but she certainly did, and she was not pleased, making it obvious when the moment you arrived, she took Dean by the arm to go mingle with her friends and left you by yourself.

Rolling your eyes at her behaviour, you moved towards the food table. You had never felt such jealousy towards someone else before, why was Dean with her, didn’t he see you? What were you saying, of course, he didn’t, he thought of you as a sister. You had even overheard him tell Lisa one day when they were arguing about you, saying that he only saw you as his little sister and would never be with you in that way. Dean didn’t know you heard him though, as you managed to get out of there before either of them could spot you. Ever since then you had tried to create space between you, realizing you were around far more often than a friend or ‘little sister’ should be, and you had to fix that. Maybe it was time you left Dean with his apple pie life and tried finding your own.

“Hey, gorgeous!” A cute guy greeted you, as he came up and handed you a drink. He couldn’t have come at a better time, as there was no better way to get over someone than by getting under someone new. You gave him an obvious once over, noticing his impressive abs before taking the drink with a smile, “Hey”

“I haven’t seen you around before, did you just move in?” He asked grinning down at you. He was no Dean Winchester, but damn was he cute.

“No, a friend of mine invited me to come. Said something about gorgeous looking guys living around here and how I just had to come meet them” You said staring into his eyes and biting your lip innocently. He smirked leaning in a little closer to you until you were almost touching, eyes looking directly into yours.

“Oh really? Have you met any so far?”

“Well, there’s this one guy that I can’t seem to take my eyes off.” You say licking your lips, watching him follow the movement. He stepped closer until your chest was touching his shirtless one.

“He can’t take his eyes off you either baby.” He said leaning in, but you sidestepped and grabbed his hand, almost making him fall. Giggling at his shocked expression before pulling him into the house. Might as well have a little fun at this boring ass party anyway. Plus, Dean was too busy with Lisa to care about talking to you anyway.

“Let’s take this party somewhere more private.” You say leading him into the house through the kitchen. You were sure whoever owned this house would freak out if they saw you and knew of your intentions, but they were all too occupied with the pool party festivities to notice.

As soon as you walked in, he pushed you against the wall roughly, making you giggle in excitement. He chucked as well as he leaned down to finally kiss you. His lips grazed against yours before he was forcibly ripped off of you.

“What the hell, Dean!?” You scream as soon as you saw who it was that ruined your fun. Of course, he would ruin this for you too. He was standing in front of you looking angrier than you’d seen him in a while and the cute guy, whose name you still never got or asked for, was standing behind Dean looking just as mad at being interrupted. It was, of course, nothing close to Dean’s anger, he had the same look in his eyes that he usually got when he was in front of a monster he was about to kill.

“Dude, piss off, you’re interrupting us.” Cute guy told him, giving a slight push as he said it. Dean snarled and whipped around to deck cute guy in the face, knocking him out cold in one punch.

“Dean!” You yelled. He couldn’t even let you have this, you needed to get fucked to forget him and he wouldn’t even let you. Taking a deep breath and running your fingers through your hair, “I can’t do this anymore”

“What are you saying?” Dean asked, going still at your words.

“I don’t want to do this anymore Dean. I need to leave, and I don’t mean this party.” You say looking away from him, missing the look of pain flashing across his face.

“You want to leave me” He stated emotionless.

“I need to find my own apple pie life Dean and stop interrupting yours. Look, it's obvious Lisa hates my guts and I’m not fond of her either, but she makes you happy Dean, and that’s enough for me. I want to be happy to Dean, and you can’t give me what I’m looking for” You say, almost revealing your feelings, not brave enough to look him in the eye as you said all this to him. You knew cute guy would be fine as Dean didn’t do that much damage, so you left him passed out on the ground and moved around Dean, planning to leave the party and hotwire a car out of this town.

Stopping beside him, you place your hand on his shoulder and kissed his cheek before moving towards the front door, “Goodbye Dean”

Dean grabbed your body and moved you against the wall, caging you in with his arms and body pressed up against yours.

“What are you doing?!” You ask, shocked you could get the words out with your heart beating so quick and him staring at you like that. You hadn’t seen that look on his face directed at you since you were teenagers.

“Something I should’ve done a long time ago.” He replied, leaning down to kiss your lips. You stood frozen in shock for a few seconds before managing to respond, bringing your hands up to grab his hair and shirt. Separating your mouth from his, you pulled his head to the side to bite at his neck, causing him to release a surprised moan and place his hand on the wall behind your head.

After a few minutes of becoming familiar with each other's lips, he grabbed your legs and hoisted you into his arms, pushing you against the wall once more. Wrapping your arms around his neck, and legs around his waist, you lean down to kiss him, grinding down on his dick through his swimsuit trunks as the kiss gets more passionate and needy. Biting at your lips, he moved your short shorts to the side and ran a finger up your slit. Finding you soaking wet for him, he couldn’t help but groan and remove his hand from your pussy lips to taste you on his fingers.

“Fuck Y/n, you taste even better than I remember. Next time I’m gonna taste you until you can’t move but right now, I can’t wait” He said as he pulled his trunks down and you helped him remove them with your feet. Your mind freezing as you processed his words, next time, did that mean he wanted this to happen again.

When he got his trunks past his cock, he grabbed himself and rubbed it down your slit a few times to get it wet and tease you. His actions cause you to shiver and force you to come back to the moment. You would worry about his words later. Now you wanted to focus on him as he finally pushed himself inside you, and you both couldn’t help but moan at the feeling. It felt as it did when you were young and in love, but at the same time, it was new and different, better than it was. You could never get over that first feeling of him sliding inside you, no matter how many times he did, especially not this time when you hadn’t felt it in years.

Dean had to stop once he was fully inside you, the feeling of you wrapped around him was going to make this be over a lot sooner than he wanted, and God did he want to last as long as he could with you. How did you manage to always make him feel like an inexperienced teenager around their crush? Breathing deeply for control, he rested his forehead against yours as you adjusted to his girth. When you were ready you only had to look him in the eyes and he began to move his hips into you, slowly at first, making you feel every move he made.

Needing more, you reached up and brought his lips back down to yours, wanting to feel him everywhere. He started to move a little faster but just enough to tease you without letting you cum. You couldn’t help but moan at the feeling even if it wasn’t enough to get you there, it still felt amazing. Gripping onto his head, you look over his shoulder, feeling yourself getting wetter at seeing the cute guy still knocked out. You were surprised it turned you on knowing he was there and could wake up at any second and see you two fucking.

Your moans kept getting louder as Dean started increasing his pace and really started pounding into you. The music from the party outside drowned all your noises out though, so no one heard a thing. That thought made you realize Lisa was outside, probably bragging about her relationship with Dean to all the neighbours, while you were standing 10 feet away from her, fucking her boyfriend against the wall. Fuck, you wish she could see you, clenching around Dean at just the thought of it happening, causing his pace to falter.

“Fuck princess, don’t do that, I’m going to cum right away if you do” Dean mumbles as he set you on the floor and removes himself from you. You are so distracted, that you don’t even question him, your heart skipping a beat at hearing that nickname. He hadn’t called you that since you were together. You didn’t realize how much you missed hearing it, but you had no time to think further about it as he quickly turned you around to face the wall. You place your hands on the wall and he shoved his dick inside you once again, making you whimper at the feeling of him entering you at a much deeper angle this time. He didn’t allow you to adjust and started fucking into you hard. Probably leaving bruises on your skin with how tight his grip on your hips was.

His hand came down on your ass a few times as he fucked into you, causing you to almost scream at the sensations, you loved when he spanked you. Moaning his name as his hips start to stutter a bit, signalling he was close.

“Fuck sweetheart, scream my name” He moans, his chest leaning over your back as one hand reached up to your nipple and the other reached around to rub your clit.

“Dean!” You yell, his fingers giving you the push you needed to finally cum all over him. Feeling you clench down and soak his dick, made him lose it and push his head into your neck, groaning out your name as he spilled inside you.

You both stood there for a few minutes, catching your breath before he pulled himself out and began pulling his trunks back on as you heard and felt his cum fall from inside you and onto the floor. Swearing, he turned you around and kissed you passionately. Your bodies intertwining as you made out, enjoying the feeling of Dean all around you.

“What was that?” You ask him as your lips separated, you didn’t want to ruin this perfect bubble you were in right now, but you were both standing in your swimsuits, freshly fucked in a random person’s kitchen, with his girlfriend outside and a passed-out man on the floor.

“I told you sweetheart, something I should’ve done a long time ago” Dean said smiling down at you, tucking your hair behind your ear. You blushed at the motion, before looking back at him “So, you don’t regret it? It’s not because I told you I was leaving?”

“No, it wasn’t that. Don’t get me wrong, I don’t want you to leave me Y/n/n. I can’t stand the idea of you not in my life, but that wasn’t why I did that.”

“I thought you only saw me as a sister”

“Not even a little bit, I love you sweetheart and not in a sister way. You’re the only girl I’ve loved and wanted since I was 10 years old and that won’t ever change.” He said leaning down to give you a kiss. You smiled up at him but then frowned and stepped back. He looked confused at your movements and pouted, wanting you to never leave his arms again.

“That’s not what you said before”

“What are you talking about?”

“I heard you and Lisa” You replied crossing your arms over your chest. He chuckled, you looked so cute when you pouted, but he knew what conversation you must have heard and how wrong you were.

“Sweetheart, I lied to her. She was always bitching about you and how close we are, I told her that to shut her up. I couldn’t have her know that she means nothing compared to you, not when I thought you didn’t like me that way anymore and I had no chance with you.”

“What? Dean, I’ve been in love with you since you gave me my first kiss” You shyly smile at him, your face flushing with heat at the admission. It was worth it though to see his whole face light up, you hadn’t seen him look so happy in years.

“Let’s get out of here” Dean said grabbing your hand and moving to the front door, avoiding the party altogether.

“Where are we going?” You ask as you followed him. He didn’t give you an answer until you were both inside baby.

“You’ve always wanted to check out New Orleans, haven’t you?” He asked grinning, already knowing the answer. Your eyes widen as you hear him and all that would imply.

“Dean, are you sure?” You ask, not wanting him to regret his choice to leave it all behind for you.

“Never been so sure about anything in my life. I don’t need anyone else when I got you, princess. You’re the only girl I’ve ever wanted.” He said smiling as he wrapped his arm around you, causing you to snuggle closer into him as you left it all behind you.

Driving away as it always should’ve been, the two of you together, forever.