Notes

‘What goes around comes around Y/N’ the words fell from Dean’s lips, smug smile plastered across his freckled face as he pulled you close to his chest.

You were an adamant believer in said phrase, constantly using it when you had found out a victim of a vamp attack actually was an asshole or when admonishing the boys for hustling pool. But having it thrown back at you, and after the hell you had put Dean through this week, between the merciless pranking and various other dares you would place on him, only caused you to be on high alert.

It wasn’t that you were being mean, okay you enjoyed it a little bit, but if anything you loved to see the horrified look on his face followed by that beautiful, heart ravishing laugh of his. When he’d throw his head back, full body vibrating from his laughter. He’d fall forward sometimes, watery eyes and full white smile, placing his hands on his legs, as if you had invented the word ‘funny’ and all that it entailed.

In a way it was selfish; purposefully jumping out from behind doors, or the time you covered the Impala in post-it-notes; it wasn’t for the prank, but rather the look he’d give you after; the one where your breath would hitch in your throat, the one where his emerald eyes would shine as he’d tell you how lucky you were that he loved you, the one where those small crinkles would form around his eyes as he laughed about it later that night. That look.

The pranks quickly turned into ‘Truth or Dare’ by the end of the week; a game Dean never took lightly, always choosing dare, the little bad boy lived on in your boyfriend and you couldn’t hate him for it. The dares, however, slowly became more and more sexual, not that either of you were complaining.

The week had culminated in you daring him to leave a detailed voicemail for Castiel about the weather forecast for the upcoming week…while you went down on him. The small gasps and tiny moans he made were victory enough as he discussed what the humidity would be on Thursday and the heat index for Friday. He moaned your name loudly as he came hot into your mouth, Saturday’s weather forgotten as he quickly hung up the phone.

He gave you that look then afterwards as you both laid in post-coital bliss, and the look continued even as he tried to explain to Cas the next day about the voicemail.

–

“So remember how I said you were gonna pay?” Dean’s voice startled you, his body leaning against the doorframe to your room. You smirked at him as you returned to your book,

“Sure Dean, I remember,” you sat up on your bed and crossed your legs. Closing the book, you gave him a bright smile as he continued to appraise you. “Wanna tell me how Dean-o? Or am I supposed to guess?”

Dean smiled back and walked into the room and sat down on the bed, it dipping from his weight. Only now did you realize he was holding a small box, piquing your interest.

“We’re still on for game night right?” he laughed, his eyes glancing down at your lips before moving back to your eyes.

“I hope so, I just spent a good 3 weeks reading all these damn Harry Potter books so Charlie leaves me alone…” you rolled your eyes and Dean gave a soft chuckle.

“Fantastic,” his hand moved to your knee, rubbing it gently. “So wanna play a little game before they all get here?” Dean licked his lips and you couldn’t not give in to his devilish smile and smoldering eyes, plus he was rubbing your knee…

“Okay Dean, I’ll play,” your eyes still casually darting to the box he still held.

“Truth or Dare?”

“Really Dean? This is the big payback?”

“Answer the question,” his voice was low and you stopped laughing thanks to his eyes, he wasn’t amused.

“Fine…fine” you held up your hands, “you got me..I’ll play, so how about dare?”

“I dare you… to wear whatever is in this box tonight,” his eyes glowed and your stomach dropped,

“Dean,” you were apprehensive, but his smile only spurred you on, couldn’t be that bad right? “Bring it on Winchester,” and you ripped the box out of his hands. You tore the side open and were left wide-eyed and gaping as he nearly fell of the bed laughing.

“Vi-vibrating panties?” shock was the word as you smiled widely, “Here I thought I was kinky enough for the both of us,” you hid your absolute panic, knowing that was exactly what he wanted.

“Yes mam, and I’ll have control of it..” he waved his phone at you, wide smile still across his god-damn freckled face.

“You gonna call it every 5 minutes or..?” you sneered, crossing your arms.

“Nope sweetheart, just a little app right here,” he pointed to a screen that said ‘Messages’, “looks like I’ll just be texting or checking my phone, but in reality I’ll be seeing how long you can go before you beg me..” he stood up and winked, god-damn bow legs and god-damn ass walking away from you. You could sense his smugness just from his cocky gait.

“I won’t be begging for anything” you shot back, no way in hell could he win this round.

“We’ll see,” he looked over his shoulder, “better get changed since they’ll be here soon, or you too chicken?”

“You’re ON!” you shouted at his back as he walked down the hallway.

–

Besides not being your color (you were not big on bright green underwear) the ‘panties’ actually weren’t that uncomfortable. Dean had yet to press any buttons and you were well into your 3rd beer, waiting anxiously for his attack, constantly fidgeting and sweating nervously.

“Y/N .. you’ve had like 2 or 3 beers, why are you so flushed?” Sam smirked, as he opened the board game Charlie insisted you play.

“Haha, no reason Sammy, just a little hot I guess,” you took a swig of beer, avoiding those damn green eyes at all costs.

Kevin, Charlie, and Cas were all discussing which board game they thought is the best; Charlie insisting that Settlers of Catan was light years above Sorry!; Kevin just rolled his eyes as he turned to you,

“So Y/N .. Dean tells me you guys may have a lead on another tablet,”

As you opened your mouth to reply, a sudden vibration went off right on your clit causing you to gasp out loud, hands automatically going to your crotch. You stopped though as you saw the others look at you in horror. Dean smirked widly,

“Baby you okay?” he leaned over to touch your shoulder but you brushed him off, glaring at him hard.

“Fine, babe….Anyway, yea Kev, we were torturing a demon a few states over and he managed to tell us tha-” vibrations went off again and you grasped the edge of the table. They didn’t stop however, slowly moving circles around your sensitive clit. You closed your eyes and bit the inside of your mouth.

You can do this, get your shit together Y/N

Opening your eyes Kevin was looking at you mortified, “Hey if you’re going to be sick.. maybe you shou-” but you held up your hand silencing him, trying to steady your voice.

“N-no it’s okay, it’s fine. We going to start this game anytime soon?” you looked pointedly at Sam, who then hurried to finish setting up the board.

“Okay guys, good old fashion monopoly..” Sam grinned as he held up the empty box, your eyes slid to the game board on the table.

You groaned loudly both at the continuous vibrations and the fact they of course, OF COURSE, they’d pick the longest game known to mankind.

“Seriously?! Who the hell th-thought monopoly was a good idea?” your nails were digging into the side of the wooden table.

“Actually I thought it’d be perfect..” Dean shrugged his shoulders, eyes meeting yours and you almost jumped across the table; you weren’t sure if you wanted to beat the shit out of him or rip his clothes off…still 50/50.

Your body shivered as the vibrations suddenly stopped; you had been almost close the edge, your body was covered in a thin sheen of sweat, and you continued to let out long sighs to mask your moans.

Dean continued this for a good 15 minutes, bringing you close to the edge and somehow magically knew just when to turn it off, driving you absolutely crazy.

In the middle of talking to Charlie about the fact the Snape killed Dumbledore, a huge plot twist in modern young adult fiction, Dean started it again, but this time it was quick fast vibrations that would come and go along the whole lining of the underwear.

“Didn’t realize Snape made your lady parts quiver..” Charlie winked as Castiel insisted that Sam was stealing money from the bank, ‘Am not Cas!’ ‘Sam..I’ve raised you from perdition, I’ll send your cheating ass back!!’

“A-am not turned on,” you laughed louder than necessary, trying to maintain your breathing. Charlie’s face morphed into realization; her face darted to Dean’s and that bastard gave her a small wink in acknowledgement.

“Oh my god,” she leaned into you, whispering now. “You two are so kinky,” she nudged your arm and the contact made you close your eyes in bliss. Jesus Christ.

“Y/N, your turn,” everyone was looking at you as Sam passed the dice, just as you rolled the vibration was so high that you clenched your thighs together, “OH MY GOD,” you leaned forward as you shouted, and noticed that Cas, Sam, and Kevin were eyeing you as if you had lost your damn mind, “oh my god as in, why can’t I land on boardwalk…am I right?” you gave them your best smile.

“Sure Y/N.. just move your player,” Kevin took the dice. Go to Jail. You kept your legs clenched tight together, already disturbed by how wet you had become. Dean’s ministrations continued but not much until you finally got out of jail on doubles. As you went to pick up the iron piece that Castiel insisted reminded him of you, the trembling in your hand caused you to drop it a few times as the vibrations had now become a dull pulsing through your entire body.

“Y/N..I don’t mean to be too forward, but you look dreadful; your heart rate is spiked, your flushed and by the looks of it you are sweating, I suggest maybe going to lay down..” Castiel offered, his eyes bright blue orbs of worry.

“Hahaha.. I think your right Cas..” and you stood up, legs shaking badly. You hastily made to leave the room but any quick movements only further tortured your poor over-sensitized clit. You made it to the doorway when Dean must have put on the highest number.

“UNGH, OH MY,” yours legs nearly collapsed under you as you clutched the doorframe for help, you hadn’t even noticed you were whimpering. All you could hear was Charlie cackling in the background and worried ‘Are you okay?’s’ from Kevin and Sam. Without even turning your head, yous strangled voice told them you were fine as you made your way down the hallway to your room.

Slamming the door shut, you immediately ripped off your pants and quickly tore the panties off of your body. Next you ripped of your shirt, black bra staying in place as you had become frustrated with the clasps.

You threw yourself onto the bed and immediately let your fingers ease the ache, hips lifting off the bed, slowly building back up the tension that had yet to break. You were breathing hard and fast as you deftly made quick time, the edge right there in plain sight just as the door had opened to a very self-satisfied Dean. He quickly shut the door, eyes wide and lustful as you came hard and silently around your fingers, your eyes meeting his as your body convulsed.

Dean began tearing off his clothes as he made his way over to you; you laid on the messed up bedsheets, writhing from your orgasm and still heavy with need.

“Dean … that was…” you breathed as he leaned above you, now only in his boxers.

“Fucking hot?” he laughed as he leaned down and kissed you, his tongue pushing into your mouth, lavishing every inch and memorizing every area. He pulled back and wiped the sweaty hair off your face, pushing it behind your ear slightly, “Was that okay? Are you okay?” his questions sincere, eyes wary.

“Dean it was…amazing..” you breathed as you grabbed his face down to yours, kissing him again as teeth crashed violently and sloppily. He pushed his weight down into you and you felt his erection digging into your belly. His calloused hands roamed your sides, ghosting lightly over the goosebumps you still had.

“What do you want to do baby girl?” he growled low into your ear, as he moved down your neck, biting and nipping.

“Y-you..” you whimpered as you hooked your legs around his waist. He bit down hard on your collarbone, licking the spot with his tongue as let out a low moan.

“Do you understand how it feels now..? How much you constantly turn me on and then leave me hanging?” he smirked into your skin as his hands fondled your breasts through the bra. Bucking your hips up into him, you whined as he continued to slowly work his way down your stomach. Your hands threaded through his blonde locks as he kissed you above your navel.

“Dean, please..please..”

He pulled back and held himself up on one arm as his other went down to his erection. He stroked himself, biting his lip.

“You want me? All of me?” Dean closed his eyes, as your hand took over for his, you slowly moved up and down, wetting him with his precum.

“Just fuck me already.. please..” you let go as his hand suddenly grabbed your wrist and moved it above your head,

“Thought you didn’t beg?” his breath was hot as he kissed your cheeks, and you writhed under him, desperate for friction.

“I-I lied..” and suddenly he pushed into you, slowly stretching and filling you. You gasped and lulled your head back, thankful for the fullness of it all. You opened your eyes to see Dean staring down at you, breathing sporadic as he tried to calm himself.

“Fucking make me lose it with all those whimpers,” his words thick as he began to move in and out of you, achingly slow. After several moments of this, you tried to use your feet to push him in faster and deeper.

“Dean..faster… oh my god,” your arms gripped his biceps tightly, Dean pulled out and then slammed into you, going deeper this time, tip brushing your spot.

“YES,” you screamed as you met his mouth again, his relentless pounding began to rebuild that previous tension, building higher and higher until moments later you were stuttering your warning, which Dean silenced with his mouth. Your walls tightened around his dick and your body bucked up into his, endless litany’s falling from your mouth, all involving Dean. Several thrusts later, as he milked you through your orgasm, he came inside of you, his hips stuttering erratically. He fell down into your neck, leaving little kisses on your neck, both of your breathing loud and quick.

Dean pulled out and went to move to the side when suddenly there was a loud bang on the door.

“Guess Y/N is doing fine then,” Sam’s voice was by the door, accompanied by Charlie’s loud laughter.

You smiled and turned to Dean, “You’re so dead next time,” you winked as you pulled him in for another kiss. His freckled face and blazing green eyes looked at you, that same damn look as before; but then he quickly got up and forced on his clothing, “SHIT! Sammy’s gonna steal my money!” he looked back at you on the bed, extending his hand for you to come with him.