Truth or Dare, Princess
Summary: When the boys are stumped on a case he sends them to the reader. That one case leads to a more permanent relationship with the boys, and ultimately her falling in love with Dean…and Cas. There’s always been something about the reader they’ve loved and a game of truth or dare let’s them explore it.
Word Count: 4816
Author’s note: SMUT SMUT SMUT!!!! I absolutely LOVE this one guys!! Just as a warning the plot doesn’t 100% follow along with the shows plot. Tell me what you guys think about this one!
You’d been hunting with Sam and Dean for the past year, your paths crossed on Arachne case. Bobby had referred the boys to you, you weren’t a hunter but you focused on lore. After telling Bobby how confused they were he sent them your way, but you never knew how important that one small decision would be.
Bobby had set it up so the boys would meet you at the library you worked at, it was a cover for you. The first and second floors were all normal books, but the basement was specifically for lore and hunters. You had hunters file in and out, and you helped them the best you could.
When Bobby had first suggested you to the boys Dean smirked, “She seems like just your type Sammy, nerdy”. Bobby just smiled to himself about Dean’s comment, he knew the second Dean saw you he’d be sold. Sure you were smart and loved books, but you were also incredibly beautiful.
Sam rolled his eyes, “Dean you of all people should know not to judge someone off of what’s said about them”. Bobby continued telling the boys where they could find you, and how he’d set up the meeting. The boys were in need of help so they didn’t mind. Bobby placed a call to you and then the boys were on their way.
It was closing time, which meant it was just you. You were excited but nervous, Sam and Dean Winchester were legends. Before you knew it you hear the sound of a bell, and eventually two men walked in. Taking in their descriptions you knew it was Sam and Dean.
They made their way over to the counter, and the closer they got the more you realized how incredibly good looking they were. Dean leaned against the counter, “Hey princess, you must be (y/n)”. You felt your cheeks begin to redden, “Yes I am, and you must be Dean”. Hearing him call you princess set butterflies a flight in your stomach.
He grinned, but before he could reply his brother cut him off, “ Thank you so much for even helping us, so is this whole library yours?”. Dean rolled his eyes, his brother was cockblocking him. You smiled realizing how beautiful Sam was too, “Yes…kinda…my aunt left it to me when she passed”.
You had always been close with your Aunt, and she was a hunter. She’d be good friends with Bobby and she was the reason you were even in this lifestyle. Sam forced a smile feeling bad for bringing up something so emotional, “I’m sorry, losing someone is one of the worst things to go through”.
Placing a stray piece of hair behind your ear you replied, “It is, but it’s good to have this place. It reminds me of her and hunters always come in telling me stories. I mean we all know death is never really the end..but enough about me how can I help you guys?”. Sam tried not to laugh but he found you incredibly cute, especially how you babbled on.
Dean licked his lips, he had about a thousand different ideas about how you could help him, “We’re having trouble figuring out what exactly we’re hunting”. You smiled, “Well I think I can help, follow me”. You started to lead them down to the basement while Dean let his eyes roll to the back of his head mouthing, “Oh my god” to his brother.
Sam shook his head in annoyance, he believed there was a lot more to you and didn’t want you to become one of his brothers flings. When you finally got into the room you pulled out your laptop and set it on the main table, “Okay what can you give me?”.
Dean raised his eyebrows, knowing exactly what he could give you but once again Sam intervened, “One of the witnesses said the creature had mottled skin and double sided irises”. You knew exactly what it was, but you were sad things were over so easily. Both brothers pulled a chair up next to you and you felt flushed being in the middle of such an attractive sandwich, especially with the way Dean was looking at you.
You pulled up the file, “I think what you have is an Arachne I know they’re only-”. Sam chimed in, “located in Greece”. Dean wanted to throw up, it had been five seconds and you were already finishing each other’s sentences. He placed his hand briefly on your knee sending shivers down your spine, “So how do we gank the son of a bitch?”.
You bit your lip trying to stop your mind from where it was going. You hoped Dean hadn’t noticed but he did, and he grinned realizing his effect on you. Turning to him you explained, “Decapitation is the only way they can be killed, and Sam I think ever since the apocalypse creatures have started appearing…it’s strange but-”.
Sam laughed, “Strange has become a regular adjective to describe our life”. Sam was amazed, it took you about a minute to know what the monster was and only with a few details. You got up, “I guess that solves things, I hope I was worth it”.
Dean got up too, “Oh trust me, you were so worth it”. You blushed again, obviously picking up on what Dean really meant. Sam added, “It was incredible how quickly you knew what we were hunting, thank you so much”.
Dean grinned, “You know we should get your number for future cases, you’re a lot easier to look at than Bobby” he finished his sentence with a wink. You laughed, “I don’t know Bobby does have this vibe to him…”.
Both brothers laughed but you finally said, “ I’d love to hear how the case goes, and I’d love to help out again”. You leaned down to write your number on a piece of paper and Dean raised his eyebrows to his brother again, signaling how good at this game he was.
That case started the relationship you had with the Winchesters. They called you to tell you how the case went, and then to ask for help on the next one, and then the next. Finally after a couple months you decided it would be easier to move into the bunker.
Bobby found someone to take over the library for you, a friend of his named Garth. You were happy to move in the Winchesters, the library had become the only family you’d had but at the end of the day it was just a building. It was a place filled with memories, but none that truly belonged to you.
Sam had become a close friend, while Dean had become somewhat of a love interest. Which meant; you were hopelessly in love with him but you weren’t sure how he felt. He flirted with you, but you never took it seriously because you soon learned Dean flirted with everyone.
On some cases you worked with their friend Charlie, she was similar to you. She loved fictional worlds, and shared your nerdy tendencies. A friendship soon formed, and you were thankful to not always be the only girl in the house. You told her everything, especially your feelings for Dean.
There was one other person you became close with, Castiel. You were working on a case about angels and Sam called him in to help you. From the moment you saw those piercing blue eyes you were sold, your heart confused at what you felt for both him and Dean. You justified what you felt with the fact that you didn’t even know how Dean felt.
You still remembered the first time you’d met him. You were in the library all alone when he walked in, a determined look on his face. His voice was low, “You must be (y/n) from Dean’s description but you don’t look hot you look of normal temperature for a human”. You laughed instantly, so this is what angels were like.
You stood up, “I’m guessing you’re Castiel-”. You lost your train of thought when you looked into his eyes, mesmerized by their intensity. Finally you caught yourself, “I’m sorry I’ve never met an angel before I-”. He smiled, “It’s okay, I haven’t met a human like you before” he said looking you up and down.
With the pressure of his gaze you felt uneasy, “Would you like to get started, I think we might be dealing with an archangel but I’m not sure”. Castiel sat down next to you and you couldn’t help but think about how close his body was to yours. Your mind started to drift so you tried to pull yourself back, but out of the corner of your eye you saw Castiel smirk.
You needed to bring your mind back, “What does this look like to you?”. Again Castiel grinned, but you just ignored it. He placed his arm over your chair and leaned forward looking at your computer screen, “I think your assumptions might be correct, but we need more evidence”.
You felt relieved that you knew what you were dealing with, until you realized your mind was drifting again. There was so many questions you had about angels; did they have sex or was that a sin, what can they really do with their grace, could angels even get hard?
You were too busy to notice the way Castiel was looking at you. The thing was you’d forgotten one essential thing about angels, they could read minds. Castiel heard every impure thought you’d had, and he was amused by them. On the outside you were so innocent, but he was starting to know how much your desires changed you.
This was something he could use to his advantage, you still thought he was innocent too. He rubbed your thigh lightly, “Are you okay (y/n), you seem distracted?”. You snapped out of your thoughts, but nearly went right back in when you realized how he was touching you. Trying to play it off you forced a laugh, “Yeah sorry, this has been a lot….the case”.
Castiel just smiled, you would be fun. From that moment on Castiel became very interested in you, but you never knew what he was really thinking. Could angels even flirt, could Castiel even flirt? You were in a constant whirlwind of emotions between him and Dean.
You were in the library with Charlie and Sam, obviously researching, when Dean walked in. Castiel trailed behind him, they both looked happy. Dean sat next to you, “Hey princess, what do you say we do something a little more fun?”.
Your heart started to race thinking about what fun could really mean so you missed the look Castiel gave Dean. After a second of letting you go crazy Dean added, “WE all could do something a little more fun”. Finally your heart slowed down, he was talking about everyone.
Charlie was excited, “Okay Dean what did you have in mind?”. The look that formed on Dean’s face sent shivers down your spine, he was up to something. He grinned, “We’re going to play good ole truth or dare….but sexual”.
Sam rolled his eyes, “Really Dean, what are we 16?”. You laughed at Sam’s comment, this did seem a bit juvenile. Dean put his hands up defensively, “Come on Sammy I think we’re all dying to know how innocent (y/n) really is”.
Suddenly all eyes were on you and you felt your entire face turn red. You smiled sheepishly, “Uh-”. Charlie cut you off, “ We’re in” she winked at you. You gave her a look but she didn’t care, she knew this might finally push you to do something with Dean.
Dean clapped his hands together, “Good, now who should go first…”. Again the whole room looked to you and you just shook your head. You rolled your eyes, “Okay, me I guess”. Dean looked to Castiel before looking back to you.
He grinned, “So truth or dare?”. You felt like you’d be screwed either way, “Dare”. Dean’s jaw dropped and the entire room cheered at your decision. Dean licked his lips, “I’ll start easy; I dare to tell you to tell me one of your kinks”.
Charlie started laughing and the rest of the gang became a thousand times more interested in what you were about to say. To the gang you were the innocent one, but if only they knew how you really were. You closed your eyes summoning up the courage, “Well you guys can’t judge me”. Dean had a weird look in his eyes, “I wouldn’t dream of it princess”.
Maybe it was because it was already extremely late, or the fact that you’d been thinking about Dean all day, regardless you told them the truth. For once you had the courage to let them know just how “innocent” you were.
You exhaled, “I like when people are really dominant…not just telling me what to do but just reminding me I’m yours..you know…like I better listen to….”. You decided to quit while you were ahead and you hid your face in Charlie’s shoulder. Charlie grinned, “Daddy…she was going to finish the sentence with daddy”.
You wanted to kill her, you weren’t embarrassed of what you liked it you were just shy. Dean tried to hide his excitement, he was so instantly turned on. Finally you looked up and you felt on fire between the looks Castiel and Dean were giving you.
Dean smiled, “Don’t be shy about it princess, to make things fair I’ll tell you one of mine”. You bit your lip in anticipation, there was no way to keep your thoughts pure now. He grinned, “We go hand and hand, I like being called Daddy and knowing I have a good little girl who listens to me”.
You squeezed your thighs together tried to stop the throbbing. Sam got up, “I didn’t need to hear that I’m gonna-”. Dean laughed, “Don’t act so pure Sammy we share a wall so I know what you’re up too”.
Sam looked from his brother to you and his whole face became a deep shade of red. He ran a hand through his hair, “Fine Dean, but I also don’t feel like hearing what gets you going”. Dean winked at you before saying, “Fine Sam, but I have a feeling the rest of the room is extremely interested”.
You felt yourself already getting wet, Dean was obviously talking about you. Sam rolled his eyes and excused himself. Dean didn’t skip a beat, “Alright princess, now it’s your turn to ask someone”. You decided that you wanted to ask Castiel a question. You grinned, “Castiel, truth or dare”.
Reading your thoughts Castiel knew picking truth would be a lot more entertaining, “I chose truth”. You tried not to blush, “Do angels have a sex drive or is that a sin?”. Castiel smiled, this would be so easy.
He looked to Dean and then you, “I have a sex drive, I may be an angel but I can be as sinful as I want”. Castiel looked you over while saying the second part, and the intensity of his gaze sent shivers down your spine.
Charlie spoke up, “Guys I know I don’t bat for your team but don’t bench me!”. Castiel turned to her and asked a question, “What is your favorite part of a woman?”. Charlie thought it over for a second before giggling.
She shrugged, “I’m a tits kinda girl I guess”. The boys both laughed and so did you. Somehow Charlie could make the most weirdest situations funny. She held up a finger, “I almost didn’t notice Cas but you didn’t ask me truth or dare, which makes that a clear violation. Which means you must now do what ever dare I chose”.
Cas nodded his head, he was a man of rules. Charlie giggled again, “Since you’re as sinful as you want I dare you to whisper the dirtiest sentence you can think of into (y/n)’s ear”. You jaw dropped a little, would you be able to handle that?
Castiel just nodded his head again and within a second he was next to you. With one hand he delicately moved your face towards him, and trailed the other up your thigh. You closed your eyes and felt his lips graze your ear, “I want you to be a good little girl for me and let Dean fuck that pretty little pussy of yours while you suck my cock”.
You bit your lip hiding a moan, you wanted so badly to say, “Yes daddy” but you remembered where you were. To your surprise after he was done speaking he kissed you below your jaw. Charlie and Dean were going wild.
Just like that he returned to his seat, leaving you wanting more. Charlie raised her eyebrows, “From how (y/n) is reacting I guess you weren’t lying”. Feeling all eyes on you, you were eager to divert the attention. You looked to Dean, “Truth or dare?”.
He leaned forward, “Dare princess”. You gulped, unsure of what to ask. You wanted to dare Dean to take you right there on the table, but you needed to control yourself. Smiling you said, “I dare you to tell me why you keep calling me princess”.
You figured that would be an easy question and that maybe the throbbing and desire you felt would stop, but you were wrong. He licked his lips, “I like how worked up it gets you, from the first time I called you it I saw what it did to you”.
You felt yourself beginning to blush again, unsure of what to say. Suddenly Charlie got a text and her entire demeanor changed. She sighed, “The bat signal has gone off guys, looks like my night is done”. You were sad that Charlie had to leave, and nervous that you’d be left with the boys.
She hugged you and everyone gave their goodbyes. Getting up you said, “Well that’s my night too, sorry to disappoint boys”. Dean looked up at you smiling, “You never disappoint princess”. You found yourself smiling but before you could walk out Castiel got up.
He reached out a hand, “The least we could do is walk you to your room”. That would be nice, and it seemed innocent enough so you agreed. They got up and gave each other weird looks, which made you rethink your decision.
Pushing it to the back of your mind you continued walking forward. It was a short walk to your room and before you knew it you were there. You opened the door and they both leaned on either side of the frame, “Well thanks guys, I guess I should go to bed”.
The truth was that you didn’t want to go to bed, you wanted the both of them like Castiel had suggested. You were too shy to act on it so for right now it just occupied your thoughts. They looked to each other and Castiel spoke up, “Your mind suggests otherwise (y/n)”.
You were confused, “My mind?”. They grinned now, a look of satisfaction on their faces. Castiel explained, “You’re a very intelligent girl (y/n), but you’ve been incorrect about the most fun part of being an angel; reading minds”.
There was no hiding it, your face turned bright red. You tried to remember everything you’d been thinking about, especially the dirtier stuff. Castiel laughed, “Yes, I’ve heard everything…you’re a dirty little thing”.
Now Dean chimed in, “I can’t believe I thought you were so innocent, I think it’s time we treat you like the dirty girl you are”. Your mouth just opened as you felt your desire growing, unable to respond.
Castiel got closer to you and again lifted your chin up with a finger, “Be a good girl and answer us”. Somehow you found the words and said, “Yes Castiel”. He turned to Dean smiling, everything was falling into place. They followed you into your room as Dean closed the door behind you.
Castiel added, “I want you to call me commander, think you can do that baby?”. You nodded your head but remembered what they wanted, “Yes commander”. Dean grinned, “Look how quickly she catches on, this will be fun”.
You just gulped, waiting to see what their next move would be. Castiel shook his head, “I can still read your thoughts (y/n), so eager”. Biting your lip you still waited to see what they’d tell you.
Dean looked you up and down, “I think I wanna play with her for a little while you watch, is that something you’d like princess?”. Your breathing became more rapid, “Yes daddy”. Dean lead you towards the bed, your back against the headboard.
He bit his lip, “Let’s get you out of those clothes”. You started to lift the dress you’d been wearing, leaving you in just your baby blue bra and panties set. Dean groaned, “Fuck Cas, look at how beautiful she is”.
By now Castiel had sat in your desk chair, lightly palming himself through his jeans, “Breathtaking…”. You felt yourself getting wetter with all the attention and anticipation. Dean turned your head towards his, “I’ve wanted to do this since the first day we met”.
He lightly placed his lips on yours while his hand cupped your cheek. The kiss ignited a flame of desire in your core, you wanted more. When it was over he slowly dragged down your bottom lip with his thumb, “Fuck you’re amazing”.
You were so needy, “Dean..I-”. He shook his head and brought his hand to lightly grasp your throat, “Daddy”. It made your breath hitch and your core soaked. You blinked, “Daddy, I need more”. He removed his hand and kissed your forehead, “Good girl”.
His hand trailed down your stomach and slipped under your panties, he slowly inserted one finger inside of you and you moaned. Dean took his finger out and sucked on it, “You taste so good princess”. You watched him with your mouth wide open, so turned on.
Dean moved down the bed, bringing himself closer to your core. He slowly took off your panties, “No need for these doll”. After that he spread your legs and you bit your finger unsure of his next move. He licked his lips, “So fucking beautiful princess”.
His praises were turning you on even more. Dean licked up your folds and you moaned at his touch. He flicked his tongue lightly over your clit, sending shivers down your spine. Looking to your left you saw Castiel was now fully exposed, stroking his shaft.
Seeing Castiel made you even more needy, he looked so good. Dean spread your folds with his two fingers, exposing you further. He started to trace patterns over your clit with his tongue, “Fuck daddy that feels so good”. Castiel groaned, becoming more turned on too.
You bucked your hips, needing more, but with his hands Dean held you down. You loved the feeling of having no control, your pleasure all up to Dean. He moved his head faster and you felt yourself getting closer, “Daddy please I’m-”.
Dean stopped what he was doing, “I know princess, but I want to feel you cum around my cock”. He moved back up next to you and called over Castiel. You felt the bed sink down as Castiel sat next to you.
He placed a stray strand of hair behind your ear, “You look so beautiful when you’re so worked up”. Before you could reply he crashed his lips into yours, his dominance surprising you. Castiel knew what he wanted and didn’t hesitate to take in.
During the kiss Castiel shifted your body, bringing you ontop of him. Dean now kneeled behind you, and brought your ass to press against him. Once the kiss was over Castiel said, “I want to see those pretty lips wrapped around your commanders cock”.
You nodded, “Yes commander”. Dean groaned, “She’s such a good little girl”. Getting on all fours your ass pressed against Dean and your lips hovered over Castiel’s cock. You licked slowly up Castiel’s shaft, swirling your tongue around his tip causing him to moan.
You felt Dean’s tip press against your pussy, “Please daddy”. He slapped your ass, “Not until you start to suck his cock”. You nodded your head and finally took Cas in your mouth. Finally when you took as much of Castiel as you could you felt Dean enter you.
You moaned against Castiel’s cock which caused him to buck his hips forward. Dean started to enter in and out of you, stretching your walls. Following his speed you started to bob your head up and down. Castiel got a fistful of your hair, pushing your head down lightly.
Cas moaned, “Fuck this feels so good”. Dean slapped your ass, “Damn straight”. You liked the slight tang of pain you felt when he slapped your ass. Dean placed his hands on your hips, thrusting himself deeper inside you. You moaned against Castiel’s cock again, “Fuck Dean, keep going..it feels so good when she moans against my cock”.
Dean went faster, “That’s it princess, you look so good with a mouthful of his cock”. You took even more of Cas in your mouth, the feeling of being completely filled so intoxicating. With your hand you started to play with his balls, making Castiel moan even more.
You knew you were getting close and Cas let Dean know, “Our good little girl wants to cum”. Both boys were just as close as you were, everything was so intense. Dean felt himself getting sloppier, “Fuck princess, I do too, cum when we tell you”.
Castiel started thrusting himself into your mouth, “You’re gonna make your commander cum all over those pretty lips”. Dean was thrusting so deeply into you he was hitting your g-spot every time. You felt like you were going to explode, and you didn’t know if you could hold on any longer.
Dean was moaning so loudly, “Shit this feels so good, doesn’t it babygirl”. Castiel was just as close, “Let’s let the good little girl cum for us Dean”. Suddenly both boys started thrusting even deeper, and you felt your senses become flooded.
Dean nearly yelled, “Cum for us princess, fucking cum for us right now, be a good girl and fucking cum”. That was all you needed, you let yourself go. Your body shut down, the only thing you could process was the pleasure.
It was like a bomb that went off in your core and shook through your entire body. All you could do was moan, but you mouth was filled. You moans sent vibrations against Castiel’s cock, and then he was cumming too. You felt his hot load shoot to the back of your throat, but you continued sucking.
Castiel moaned so loudly, “Fuck she’s still sucking…shit I’m so sensitive..fuck”. This was all enough to set Dean off too. He felt your walls clench against his dick and he thrusted even harder. The moans that filled the room caused his own orgasm.
He exploded inside of you, filling you up. You groaned as you felt him twitch inside of you. All the sensations were so intense, all you could do was moan. As he came Dean held onto your hips tighter. Finally you were left shaking, as both boys pulled out of you.
Castiel pulled you up towards him, placing a his lips on yours. You felt the bed shift again as Dean sat next to you both. When you were done kissing Castiel, Dean pulled you in for a kiss. Castiel laughed, “What about sharing Dean?”.
Dean smiled against your lips ending the kiss, “It’s just so hard when it comes to (y/n)”. Smiling aswell you finally spoke up, “ I am all for sharing”. Castiel pulled you so you were perfectly in between the both of them.
They each started to caress your body, sending shivers down your spine. Dean nibbed on your ear, “Fuck you’re so perfect”. Castiel whispered in your other year, “So incredibly perfect”. You sat there feeling the happiest you’d ever felt, in between two of the people you cared for the most.
Dean finally said it, “I love you princess, always have always will”. He kissed you again, preserving the moment with your bodies. While the kiss continued Castiel whispered in your ear, “I love you too (y/n), I didn’t know I could”.
When the kiss was over you were left panting, “I love you both so much”. They just smiled, just as content with life. They were incredibly excited for what your future together held, even for what rest of the night held.