The Bet | Part 2
Part 1
Pairing: Dean Di Laurentis x Reader
Word Count: ~3.7k
Summary: Dean wants unlimited access to Beau’s Cape Cod residence for the summer following graduation. And Beau wants Dean to attempt monogamy for the last two months of their final semester. Dean agrees knowing Beau gets to pick the woman, but he didn’t realize Beau had already made his choice before they even shook hands.
Warnings: Smut, like a lot. Do not interact if you are under 18.
Author's Note: Let me know what you all think! I wrote a lot more for this part because the flashback kept going, but I promise the build up will make sense. Also, the other 3 will be in the next part.
Beau turns the radio’s volume down as you slip on your heels, tossing your vodka soaked work shoes into the back of the car without looking where they land. He clears his throat.
“So I talked to my parents about this summer.” You freeze rummaging through your purse, lipliner forgotten.
“And?” You ask, trying not to sound too hopeful.
“They said they’re fine with you staying at the Cape Cod house.” You squeal, lightly smacking his arm and repeatedly thank him. A quiet laugh escapes him before he puts up a hand telling you to wait. You cover your mouth, a huge smile underneath it as you stare at him. You wave your other hand at him in a “go on” gesture.
“If,” he starts in an exaggerated tone, “and only if, you tell him the truth by the end of the semester.” He looks over at you with a serious face before looking back at the road. Your hand falls away from your mouth and so does the smile.
“Beau, you can’t be serious,” you mumble, eyes flickering over his face trying to figure out if he’s joking. There’s no way he can be serious, you think.
“He deserves to know why,” is all Beau says before turning the volume back up, singing along. You stare out the window for the rest of the drive as you try your best to steady your breathing.
“Okay, but what if I just start the bet tomorrow?” Dean tries reasoning with Beau who currently has the world’s biggest shit-eating grin on his face. You had wandered off before the game ended to find the bathroom, still not having returned.
Beau and Dean were sitting in two lawn chairs around the fire, drinking and pretending they were paying attention to the other people around them.
“You really think I’m going to give you a last night of freedom? Also, Melissa already ditched your ass,” Beau says, sipping his drink.
“Melissa!" He exclaims, snapping his fingers, "I knew it started with an M.”
A second of quiet passes between them before Dean tries again.
“I'm offended you think Melissa was my only prospect. Your faith in me hurts, Beau." He lets out a sigh and begins rolling the cup between his palms for a second.
He leans towards Beau and whispers, "I mean, I could always see if [y/n] wou-"
"Yeah, about that," Beau starts, looking over at Dean. Dean's stomach drops instantly thinking back to the information he learned today. He prepares himself for Beau to tell him that he has been holding the same torch for you that he's been holding for over three years. He stares into the fire as he takes a heavy drink from his cup.
"She's your target," Beau finishes and Dean spits the tequila in his mouth out. It goes directly into the fire, which instantly flares under the spray for a brief moment causing Beau, Dean and everyone else around the fire to flinch back at the heat.
Dean shoots a “sorry” at the people sending him glares before focusing back on Beau.
"Beau, absolutely not, she already hates me," he pleads wiping off the leftover tequila on his chin.
"She sounds smart," he hears from behind him and jumps. You settle into the lawn chair next to Dean and drape your legs over the arm rest before cracking open the can you grabbed on your way to look for them.
“Sorry, did I scare you?” You ask, clearly not sorry in the slightest.
Dean barges into your dorm room at 11:31pm, hockey stick held like a baseball bat as the door smashes against the wall. You had texted him at 11:23pm “I’m so scared right now,” which he didn’t think to respond to for more information because he was too busy grabbing his hockey stick and sprinting across the quad to your dorm. He scans the room and sees your figure wrapped in a blanket on your couch with the lights in the living room and kitchen turned on. What’s clearly a horror movie playing on the tv.
At the sound of his intrusion you let out a high-pitched scream and throw the blanket fully over your head. He leans over to grip the back of your couch as he laughs so hard that tears start welling in his eyes.
“Sorry, did I scare you?” He asks in between gasping breaths.
You huff in annoyance as you rip the blanket off your head and glare up at him.
“I hate you.”
“No, you don’t. You would’ve blocked my number this summer if you did,” he counters. And you definitely could’ve blocked his number when he texted you at the beginning of this summer after you met him at the campus tour you both attended, but you knew as soon as you looked into those blue eyes that you would be stuck with him.
“Not too late for me to. Are you done?” You ask, crossing your arms. He lets out a deep breath before standing fully as he wipes the tears from his eyes.
“Yeah, yeah, I’m goo-“ he begins to say until he glances down at you. You’re in the shirt that he gave you last week, and he’s so not good.
“Dean? You okay?” You chuckle concernedly and bring your hand up to wave in his face. He blinks and drags his eyes away from the fact that he can see your hard nipples through his shirt. His shirt.
“You wearing my shirt, sweetheart?” He asks, his voice strained. And thankfully he’s standing behind your couch right now because his sweatpants aren’t hiding his growing problem.
“It smells like you,” is all you are able to say before the music in the movie blares during a jump scare, which makes you tighten the blanket further around you. Dean swallows the laugh he wants to release at the complete fear painted on your face. After steadying your breath, you wrap your hand around his wrist.
“Want to watch with me?” Dean looks towards your roommate’s room.
“My roommate is gone for the next two nights,” you offer. Dean forces his brain to work and finally nods at you. You let out a relieved sigh.
“Only if we watch this like it was intended to be watched,” he counters, finger already flicking the lights off, plunging the living room into complete darkness. The only light now coming from the tv. You reposition the blanket over your lap and hold up the side of it for him to slide under. Your eyebrows furrow as he awkwardly walks around the couch with his hands interlocked in front of him but decide not to question it.
Once he’s settled under the blanket, you restart the movie and lay your head against his shoulder. You force your breathing back to normal after Dean wraps his hand around your thigh and leans his head against yours. Halfway through the movie, listening to Dean’s sleepy voice and feeling his thumb rubbing circles on your thigh, you’re sure your underwear are showing evidence of how wet he’s making you.
About twenty minutes before the movie ends, you look up after not hearing Dean make his usual commentary in the last few minutes only to see he’s battling to stay awake. His eyes are drooping heavily, but still open. You give him a poke in his side as you giggle.
He looks over at you realizing he’s been caught. A tired smile crosses his face. He pulls his phone out of his pocket to check the time. 1:01am it shines into the dark living room.
“I should probably go,” he says through a yawn as he rubs his eyes. Panic sets in your stomach realizing you’ll be all alone in your empty dorm.
“Can you stay, please?” You ask, trying your best to not sound like you’re begging but knowing you will if you need to. He stares into your eyes which are clearly filled with fear, and he gives you one slow nod.
“Sure, sweetheart. I can sleep on the couch, make sure no monsters get you while you’re sleeping,” he jokes. You shake your head.
“You can sleep in my bed. I just really need someone in the same room as me,” you explain. He lets out a scoff.
“Someone?”
“Fine, you.”
Dean goes still.
“Fine, me,” he says to himself standing up, stretching his hand out to you. You turn off the tv and stand as you place your hand in his. He lets you lead him to your room, his eyes dropping to watch as his shirt tugs against the shape of your ass for a second before forcing himself to look away. He tries to stop himself from wondering if you have anything on underneath it.
Once in your room, you circle around him and playfully push him back towards your bed. He falls down on it before propping himself up on his elbows.
“And where are you going?” He asks, watching you walk towards your closet.
“I figure I probably shouldn’t make it a habit of sleeping next to you half naked, you know? Two times is kind of pushing it,” You call over your shoulder as you bend down to open your dresser’s bottom drawer. Dean goes quiet, his eyes fixed on his shirt sliding up your back as you search. He pulls his bottom lip between his teeth, your underwear covering barely anything, your ass fully on display for him.
Before you can turn around and see how hard you’ve made him without even laying a hand on him, he adjusts himself and settles into the bed.
“I mean, it’s only two nights,” he mumbles as he pulls the comforter over his lap.
“Huh?” You stick your head out of the closet, looking at him.
“Can you just come lay down?” You roll your eyes, a smile spreading on your face as you abandon your search for shorts. Turning the lights off, you stroll over to the bed and crawl underneath the covers.
Reaching behind you, you give Dean’s hand a squeeze before pulling your hand back and tucking it under your head. You make sure to give him space, facing away from him.
“Goodnight, Dean.”
You barely register that you don’t receive a response as your eyes slowly fall closed.
You wake up, slowly coming to, realizing you can’t move. Dean’s arm is firmly wrapped around your waist, pinning you against the front of him. You turn your head trying to catch a glimpse of him, which causes your hair to brush against his face. He scrunches his nose, his hand around your waist tightens. And that’s when you realize his hand isn’t on top of the shirt, it’s underneath it, against your bare skin. Worse yet, his thumb is pressed against the underside of your boob. You suck in a breath, trying to tell yourself that he didn’t mean to do it and there’s absolutely no reason for you to be turned on. It doesn’t work.
You feel his breath on the top of your head, confirming to yourself that it’s even. A quick glance at the alarm on your bedside table tells you it’s 9:07am. You don’t work Sundays or have classes, but you also know you don’t want to spend your Sunday with Dean waking up and feeling awkward at how the two of you had found each other while sleeping. You begin forming a game plan.
Your legs, you come to find out after trying to stretch them, are completely intertwined with his. You slowly try to unwind them from his, pushing your body further back against him for leverage to pull your left leg up at the right angle. Before you even attempt to pull your leg, you still. And then you realize, pushing yourself back against him again, that you can feel he’s completely hard. Your eyes widen.
“I’m begging you to stop moving,” you hear him moan, his voice thick with sleep. Your breath catches in your throat.
“I’m sorry,” you whisper.
“You’re okay, sweetheart. Never took you for a tease though.” He buries his face in the back of your neck.
“Mm and what’d you take me as?”
“Someone who took what they needed when they knew it was being offered.” His hand moves down to grip your hip as he grinds his cock against your ass. You whimper before quickly turning and shoving your palm against Dean’s chest so you can force him onto his back. Throwing your leg over him, you straddle him and plant your hand against his chest once more. The way Dean is looking up at you like he wants to fuck you into your mattress has you grinding down against his dick. A hiss leaves his mouth, his pupils completely dilated as he watches your hips moving against his.
His hand comes up and wraps around the back of your neck, pulling you down to his mouth. He kisses you desperately and you grind down on him harder when he moans against your mouth.
“Please,” you whine into his mouth.
“Please what, sweetheart?” His hands cup your cheeks and he pulls your face away from him, his eyes flicking between yours. You slowly slide your hand down his chest until you’re palming him through his sweatpants. He groans, his eyes closing for a second.
“Take these off. Need you, Dean,” and at the sound of his name coming out of your mouth, he’s desperately pulling his sweatpants down. His cock lands against his stomach, precum leaking on his abs. He holds his breath as he watches you seeing him for the first time. His cock twitches as you drag a finger through his precum and make eye contact with him. Staring, you bring your finger to your lips and slowly suck it off your finger, letting out a soft moan at the taste.
“Fuck.”
“You okay, baby? I thought you wanted me to take what I need,” you tease as you wrap your hand around his cock. He groans at the contact, eyes trained on you as you bring your mouth down to the head of his cock and give it a slow lick before spitting on it. You use it to stroke him, the muscles in his stomach strain and his fingers dig into your hips as he tries to hold himself back. He’s thick, and all you can think about while looking at him is how bad you want to feel him stretch you out. You feel yourself squeeze around nothing at the thought, but then your hand tightens around his cock briefly as his fingers slip into your underwear.
“You’re so wet,” he groans, sliding two fingers through your folds before pushing them slowly inside of you. You try to hold the moan in your throat as he slides his other hand off your hip, his thumb rubbing circles on your clit. His blue eyes stare up at your face, memorizing every reaction you have to him. The pressure in your lower stomach is building, and you know by the sounds Dean is making that he’s struggling too, so you quickly stop stroking him and reach down, shoving his hands away from you.
“Wha-?” He starts to protest before realizing you’ve moved your underwear to the side. You drag the head of his cock between your folds a couple times before lining him up with your pussy. You’re about to look into his eyes to confirm he wants this when you feel him place his hands on your hips. He pushes himself off the bed, the head of his cock pushing inside of you. You bite down on your lip as he pulls your hips down with him as he settles back on the bed, pulling you all the way down until he’s buried in you. He moans your name, fingers digging into your hips so hard you know there will be bruises left.
You hiss at the stretch and push down on his stomach to still him for a second while you adjust. His eyes close, his breaths ragged as he holds you in place.
“Fuck, I don’t think I’m lasting long.” The sound of his raspy voice, the heat of his hands burning into your skin and the feeling of his cock being that deep in you makes you unintentionally clench around him as you let out a whimper.
You slide your hand up to his chest as you slowly raise yourself up—his eyes fluttering open to look down at where you’re connected—letting his cock catch on the entrance of your pussy, you sink back down on him. The rhythm you set is rough and fast, both of you not trying to be quiet anymore as he tries to hold it together. You’ve only been riding him a minute or two before he grabs you and flips you both over.
“Can you lift your hips for me, sweetheart?” You nod eagerly, making room under you as he slides a pillow to rest under your hips.
He cups your chin with his hand and his mouth is on yours in a bruising kiss as soon as he has you on your back. Your legs wrap around his waist as he starts pounding into you at a pace you know will leave you sore for the rest of the day.
“You’re being so good for me, listening so well,” he praises as he leaves a trail of open-mouthed kisses down your throat before reconnecting your lips. His fingers find your clit again, rubbing frantically. You gasp as you feel your orgasm sneaking up on you, and he takes the opportunity to slip his tongue in your mouth. The coil in your lower stomach starts tightening. You push up against his chest, breaking the kiss.
“I’m, I’m goin-” is all you can get out before you feel your pussy tightening around his cock, eyes rolling into the back of your head as you have the most mindnumbing orgasm.
“You look so pretty cumming around my cock.”
He’s thankful in that moment that you don’t see his face, see the way he’s staring at you like you’re the only thing he’ll ever care about as he watches what he’s done to you, knowing he wants to do it again and again. He grabs your calf and pulls it away from his back as he continues to fuck you through your orgasm.
“Where do you want me to cum, sweetheart?”
“Wherever you want, baby,” you say, breath hitching as you realize what you said.
“Just want you to cum for me, please,” you whine.
“Pull up your shirt,” he orders you. You pull it up as far as you can. He’s finally sent over the edge by the way your boobs bounce as he fucks you.
Dean pulls out of you and strokes himself a few times before cumming across your chest and stomach. And as he looks down at you wearing his shirt, the blissed out look on your face, he swears he feels his heart stutter. Before he can say anything he regrets, he leans down to give you a kiss. You giggle against his lips, your face going warm.
“Let me get a wet towel for you,” he whispers, giving you another quick kiss before getting up.
“Just surprised you can stand being so close to me, sweetheart,” Dean teases, taking another sip from his drink.
“Don’t call me that,” you demand, voice cold as you look into his eyes. His body freezes.
He nods once, almost robotically, before standing.
“I’m going to check what’s happening somewhere else.”
“Dean,” Beau calls after him as he opens the sliding glass door and disappears inside. Beau sighs looking over at you before moving over to the seat Dean had been sitting in.
You look down at your can, flicking the tab as you try to ignore his stare.
“Why would you do that?”
“He doesn’t get to call me that anymore,” you mumble.
“Look at me.” You slowly lift your head and hope Beau doesn’t see the tears you’re trying not to shed. He sees them instantly, the fire reflecting in them, and it causes the frown on his face to deepen.
“Let me take you home,” he offers. You wipe the tears before they can fall and suck in a breath.
“You’ve been drinking,” you nod towards his cup.
"This is water and I only had a sip of the drink you got me," he says, tipping his cup toward you.
“Yes, please,” you whisper after a second.
You don't see Dean on your way out of the party, and you can't decide if that makes you feel better or worse.
Beau drops you off at your apartment, the car ride completely silent as you turned the radio's volume up as soon as you got into the passenger seat.
"Just think about what I said. You know I say it because I love you," he tells you, kissing the side of your head. You thank him, tell him you love him too and to text you when he gets home safe, and then give him a hug before making your way out of his car and into your apartment.
As soon as the door closes behind you, you feel the tears fall from your eyes and wet your cheeks. You kick your heels off and head for the bathroom. After taking a long shower and scrubbing your makeup off, you wrap a towel around you and trudge toward your dresser. Digging through your pajamas, you finally find it at the bottom of the drawer.
You pull his shirt over your head, letting it flood you. Turning around, you lean back against your dresser, pulling out your phone. You pull open the text thread you keep finding yourself coming back to.
You type out "I'm so sorry." After staring at it for a moment, you send it. The same red "Not Delivered" alert pops up underneath the message bubble, just as it has a countless number of times before tonight. Opening his contact, your finger hovers over the "Unblock This Caller" button before you decide to swipe out of the screen and lay your phone face down on the dresser beside you.
The following week, you walk into the class you share with Beau and Dean, debating how you'll deal with Dean when he sits next to you again. You freeze in the doorway of the lecture hall. Dean and Beau are already seated in the front row, the seat next to Dean already filled. He’s never early to class, you think. His eyes are fixed on his phone.
Your eyes slide over to Beau who is already looking at you. He gives you his best comforting smile. You give him a tight smile back, and then you turn on your heel and walk straight out of the lecture hall before Dean can see you.
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