Harder.
Pairing : Sam x Reader x Dean.
Word count : 3,615
Warnings : Wincest!!, Oral, Anal, threesome, fingering, toy use, spanking, snowballing.
This was a commission.
Final part of The Winchesters and oral fixation.
âGet the fuck over here.â You smiled and moved towards him. âDean, find some lube.â He pulled you into a rough kiss, and you moaned softly tasting his come on his tongue.
âYou really gonna fuck me?â Dean seemed nervous.
âItâs not so bad.â You broke the kiss and looked at Dean sitting next to Sam, as Sam pulled you fully onto his lap. âNever done it before?â
âNot on the receiving end.â
âItâs going to be uncomfortable at first, but I can maybe help with the prep.â You smiled. âAnd if he hits right, heâll hit your prostate, and itâll be the best fucking orgasm of your life.â Dean glanced to Sam. âIf he doesnât, Iâm still sucking your cock, so itâll still be a fun time.â
Without a word, or even a nod, Dean gets up and heads for the bags on the floor by the bathroom and starts rummaging through them. You chuckle as his sudden eagerness, and Sam pulls you into another kiss.
âYouâll help with prep?â
âYeah, I might have something for that..â You bit your bottom lip, getting off his lap and head for your purse. âI went shopping before hitting the bar. Wasnât expecting to get this lucky tonight.â You pulled out a small plastic bag and tossed it next to Sam. âI donât mind sharing, this is worth way more than I paid for that.â
Sam opens the bag and a smile graces his lips as he starts to pull things out. Â âWhatâs that?â Dean asks, making his way over with a bottle of lube.
Sam glances at you and you nod with a smile. âVibrator.â He pulls the first item out.
âSlim, discreet, and powerful.â You smile and wink at Dean.
âButt plug?â Sam glances at you as he pulls out the box for a small plug with a pink jewel on the end.
âI like being full of cum, and I like feeling pretty when I am. Sue me.â Deanâs watching you with a whole new look, and Sam glances down at the box. âYou can keep that one if you want. I have a red one at home. You know, if you wanna plug your brother full of your come and make him feel like a pretty princess at the same time.â
Sam groans, fingers tightening around the box for a moment before he puts it down. He doesnât care what the last item is, he just tosses the bag aside. âGet the fuck over here, Dean.â
âOkay, but uh.. I- I was not expecting this-â
âRelax, Dean.â You smile at him, putting a hand to his lower back as you guide him closer to Sam. âIf you donât want this, just say so.â
âItâs not that..â He worries his bottom lip between his teeth.
âWant me to start you off? Iâll go gentle and slow. Sam can stroke you to help you relax.â You glance at Sam who shrugs.
âY-Yeah.. Yeah maybe..â He slowly gets on the bed. Heâs still obviously nervous, so you motioned to Sam while you grab the vibrator and take it out of its packaging.
Sam takes the lube out of Deanâs hand and guides him into position before handing it off to you. âJust stay still and relax.â Dean nods.
âCan I- uh..â Dean swallows nervously as he hears the squelch of the lube bottle. âMaybe, one day, if we do this again, you know.. Can I do you?â
âYou wanna fill my ass?â Sam sounds amused.
Dean gives a nod and a shrug. âYouâre about to fill me. Only fair.â He winces feeling the cold lube drip down between his ass cheeks, a preemptive hiss when he feels the vibrator against his puckered hole.
âRelax.â you coo softly from behind him, your hand rubbing gentle circles on his lower back.
Dean is watching Sam, waiting for an answer. âIâll consider it.â Dean seems to deflate a little, but nods. âRelax for me, Dean.â Sam leans in close so he can whisper into his brotherâs ear. âIâm more likely to say yes if you donât spill a drop of my come tonight.â
âFuck.â Dean breaths out, and you take that moment to push in. âFuck!â
âIâm going slow.â You promise, hand still on his lower back while the other pushes the slim vibrator in a half inch at a time.
âJesus, that feels-â
âLike you need to shit.â You chuckle softly, pushing it further and further. His forehead drops to the mattress. âYouâll get used to it. And itâll get better. I promise. Try to relax.â
âItâs hard.â He mumbled into the comforter.
Sam licks his lips, and lays on the bed so his face is close to Deanâs. He then reaches out, and runs a finger along the underside of Deanâs flaccid cock that sends a shiver down Deanâs spine.
âItâs all the way in.â You point out, and Deanâs head turns and gives Sam a confused look.
Sam sits up and looks, pushes a finger against it just to hear Dean groan, then he lays back with a smile. âBuried to the hilt.â
âI-Itâs not so bad..â
You slowly and gently pull it out, and Dean whines at the empty feeling, making you chuckle. You apply just a touch more lube to the tip, and slide it back in, faster this time. In and out a couple times, while Sam teases the head of Deanâs slowly hardening member with his fingers. âReady?â You ask.
âFor what?â You flip the little switch on the end, and the vibrator comes to life. âHoly shit!â Deanâs whole body jerks, pulling away from you a bit, but you and Sam are both quick to get your hands on him and hold him. âI was not fucking ready for that.â
âHow does it feel?â Sam gets his brotherâs attention again as youâre pulling it back.
âFucking weird.â You angle it differently when you push forward and Deanâs whole body jolts again. âWhat the fuck did you hit?â
âProstate, I think.â You chuckle softly. âYouâre almost done with this. Switch?â You look to Sam.
âWait.. wait..â
You leave the vibratory in place and move to lay on the opposite side of Dean, making him turn his head away from his brother and to you. âHeâs not going to fuck you yet. That vibrator is much slimmer than he is. He needs to work you open better. And it would take far too many of my fingers for that.â You chuckle softly. âBut donât worry. Iâve got you.â You reach a hand under and start to stroke his half hard dick.
He gives you a nod as Sam gets up. âAnd I thought you looked good with things in your mouth..â Sam mutters and puts a bit of pressure on the vibrator making Dean cry out.
Sam works the vibrator a few times before deciding to pull it free. You glance back to see the smirk that plays on his face when Dean whimpers about being empty again. Â âYouâll be full again soon.â You promise and turn your attention back to Dean. You place a gentle kiss on his lips as Sam gets lube on his fingers. âReady?â
âReady.â Dean nods.
âGood boy.â You watch as thereâs a change in his eyes at the praise, and you store that little bit of information. âPraise kink, huh. Iâll remember that.â You purr against his lips with a smile before kissing him again.
He groans, breaking the kiss and his body shifts again, getting a bit tense, which tells you Sam has started to finger him open. âTaking two fingers like a champ.â Sam praises, confirming your suspicion.
âFuck, Sammy.â Â His cock throbs in your hand and you give him a tight squeeze.
âBetter work him open if you want him to come around you, Sam.â Your eyes are locked on Deanâs as you speak. âBet Sam canât wait to see you stuffed full of his cock.â
âSon of a bitch.â Dean groans again, and you chuckle.
âFuck.â Sam curses. âSo fucking tight. Canât wait to get in there.â
âBoth of you need to shut the fuck up.â Dean grumbles. Â Heâs now at full length and girth in your hand. You canât help but look back at Sam with a smile.
âSoon, Dean. Iâll be fucking this pretty little ass, soon.â You can tell by the flex in Samâs forearm that heâs now scissoring his fingers to work Dean open more. âJust need you to take a bit more.â
âYou can do it, Dean.â you praise as Sam pulls his two fingers out, and pushes three in. Dean whines, and his body gets tense. âYouâre such a good boy.â You start peppering his skin with kisses, any bit of him you can reach. His shoulder, his bicep, his cheek. Itâs then that you notice all the little freckles that litter his skin. You smile and kiss one on his shoulder, whispering more praise while you gently stroke him.
âYouâre both killing me.â He grumbles, forehead pressed into the comforter underneath him again.
Sam pulls out his fingers, and slaps Deanâs ass. âBut what a way to go.â
Dean looks back at his brother and shoots him a glare. âGood to go?â You ask and sit  up. Sam nods. âAlright.â You grab a pillow and pat Deanâs side. âOn your back, handsome.â Dean drops to his side and shifts until heâs settled with his legs on either side of Sam. âPut this under you.â
âWhat? But what if- I mean-â
You chuckle and make him lift his ass so you can get the pillow under him. âItâs your first time, so you need to be as relaxed as possible. And Iâd rather not be under you just in case your âwhat ifâ happens.â You tease. âBesides, housekeeping has seen worse.â
âHow do you know? Whatâs worse than-â
âI work here.â You smiled and leaned over to kiss his lips. âAnd you donât want an answer to that. Trust me. Now relax, and let me suck your cock while your brother fucks you senseless. Okay?â
He nods. ââKay.â
âWhenever youâre ready, Sam.â You slowly start kissing down Deanâs skin while he shifts the pillow until heâs fully comfortable. Your tongue is ghosting circles around his nipple when Sam finally lines up. Their eyes lock on each other and Dean is biting into his bottom lip, trying to keep himself relaxed but ready.
Sam breaks the eye contact, his eyes running down his brotherâs body, first stopping where you are teasing a nipple with your tongue before your lips seal around it in a gentle open mouthed kiss. Then his eyes continue south, over the curve of his brothers cock, gently being stroked by your hand. Your fingers are barely holding him, your palm just running up and then your thumb teases at the slit before moving back down. And finally, they settle on the shiny head of Samâs lubed up member, gripped  tight in his hand and just barely touching Deanâs hole.
Sam canât help but enjoy the view for a moment. Who knows when or if heâll see it again. And then heâs pushing forward. Heâs fighting to go slow, but he canât wait to be wrapped up warm in that tight canal.
Deanâs hands start grabbing as his body tenses. One hand in on your side, fingers digging into your waist, and the other is tangling in your hair as your tongue tease at his belly button.
âShit..â It falls from Sam lips, or maybe both of them, but itâs Samâs strings of curses that you hear as he leans forward, hovering over you as he pushes in the rest of the way, burying himself to the hilt.
Thatâs when you take Dean in your mouth.
âO-oh, fuck..â Deanâs hips fly up, pushing him deeper in your mouth until he hits the back of your throat. His mouth is open, sounds coming out but none of them are words anymore. They the start of words, or maybe the ends of them, all strung together incoherently, yet perfectly, given the situation. They sound like the perfect reaction to being over stimulated like he is, and itâs music to your ears.
Samâs holding Dean tight, and heâs leaning so far forward that his hair is brushing against your back, his breath fanning over your skin. âSo fucking tight..â He mumbles.
âJ-Just... â Deanâs starting to find words again. The hand that held onto your waist leaves it, and finds Samâs forearm instead. âNeed- Need a minute.â You can feel Sam nod, and you hum around Dean. âOh shit! You too.. Fuck.. just-â He lets out a shaky breath and his grip tightens on your hair. âJust a sec..â
Heâs not letting you pull back, so you find yourself sitting there, cock as far in your mouth as you can take. Your breathing is controlled and through your nose, trying not to move, not to swallow or gag around him. You almost hum again when Samâs lips brush your skin.
âCome on, Dean. You can take it.â Samâs muttering the words against your skin. âYou feel so fucking good.â
You feel him swell a bit in response, and this time, you canât fight the moan. You feel something on your back again, fingers ghosting over skin and for a moment, you think itâs Dean. That is, until the fingers trail between your ass cheeks, teasing at your hole for a moment before leaving completely, and thatâs when you feel a minor shift from Sam, and then the fingers are back, but wet with saliva and moving over your clit. You body jolts and once more, you moan around Dean.
âGood girl.â You can hear his smile. âThink we can make him cum just like this?â
âFuck you.â Dean whines, making Sam laugh. âJust fuck me already.â
The fingers leave your clit, and you expect his hand to leave all together, but you find yourself crying out as he shoves three fingers in. âMy fucking pleasure.â Â Deanâs hips jolt when you cry out around him, but Sam just pulls out his fingers and slaps your ass hard before heâs grabbing hold of Dean again and starts rolling his hips out and then in.
Deanâs grip lets up on your hair enough for you to move again, so you try to match Samâs pace. âShit.â You opened your eyes, and Deanâs head is back, eyes shut as the curses come out one after another. âFuck. shit. Shit. Holy shit..â Then heâs biting his lip and whimpering. âFuck, Sam. I canât- I canâtâŠâ His fingers in your hair tighten again and heâs pushing you down further on him.
âCanât what?â Sam asks.
âI canât..â Dean whines. âI canât take it.. Fuck.â
âWant me to stop?â He doesnât stop his movements when he asks, instead he waits for Dean to say the words.
âWant you to hurry the fuck up and come.â The next thing past Deanâs lips is a whimper. âPlease, Sam..â You groan around him as he begs, and it only makes him sound more desperate. âHarder, fuck, harder. Please. Pleasepleaseplease..â Thereâs no pause between the words anymore. His hips are moving, trying to figure out which way to go. Up and deeper into your throat, or down to get Sam deeper.
Deanâs hips stop moving when Sam pushes them down again. âThen stop fucking yourself on my cock like a desperate whore. Just tell me what you want.â
Dean lifts his head and yells at his brother. âI want it fucking harder! Bitch!â You chuckle around him, and he just pushes your head down again, making you gag around him before he lets up.
âThatâs all you had to say, Jerk.â Sam pulls back and slams forward again, his hip bones slamming Deanâs thigh into your shoulder.
âFuck!â Dean cries out again, head going back.
Sam not only goes harder, but faster. You do you best to keep up, taking Dean deep every time Sam pushes forward. Deanâs completely incoherent again whenever he does try to talk. The rest of the time, his mouth is open in a silent scream. His nails dig into your scalp, so you let yours dig into his thigh.
You jolt when another slap falls on your ass, and Sam chuckles softly. The next slap falls lower and you cry out around Dean as your pussy clenches around nothing when it starts to sting.
âIâm gonna fucking come.â Sam tells you both, or himself, you donât know anymore. Thereâs a chorus of sound filling the room and you canât tell whoâs talking to who, or even what half the words are anymore.
Dean understood the words. You could tell by how he swelled against your tongue. âCome on, Sammy, please.â His hips are moving again. Heâs holding you down and fucking up into your mouth. His hips going up every time Sam pulls back so he can push down on the cock he desperately wants to fill him.
Sam shoves his fingers back in your sore cunt once more, and you moan around Dean.
âOh fuck.. Sammy..â His brothers name comes out a desperate and needy whine, and thatâs what starts the chain reaction.
Sam slams home with everything he has and when you glance in his direction, you can see his abdomen tense as he spurts load after load of come deep in his brother. But the second Sam started, Dean cried out and swelled against your tongue, his own load coating your throat and mouth, warm and salty. And as soon as Sam is coming down, his wet fingers pull free of you and he gives you one more slap, those wet warm fingers landing right across your clit, and it throws you over as well.
You pull of Dean with a cry, cum dribbling down your chin to drip onto Dean, since you hadnât had time to swallow.
âFuck, thatâs hot.â Sam pulls you up to him, licking a stripe of come off your chin before his tongue thrusts into your mouth.
âFuck.â Dean sighs, his body lays limp on the bed and he looks every bit the fucked out mess you know his is. âBest fucking orgasm of my lifeâŠâ
You and Sam chuckle together before you pull apart. âI told you.â You ran a finger over his flaccid member and he hisses and shifts away from your touch. âSorry.â You smile.
Sam drops to the other side of Dean and sighs in contentment. Itâs quiet for a bit, but then Dean speaks. âI need to shit.â He pulls himself up from the bed and you canât help but chuckle as he hurries off to the bathroom.
Sam has a big grin plastered to his face as he stares up at the ceiling. âYou forgot to plug him up.â you tell him
Samâs eyes come down and he watches you hold  up the box. âOh shit..â
You smile and shake your head. âKeep it. First time might not be the best time for it anyways.â
âThanks.â He watches as you start grabbing clothes. âWhere you going?â
You look up at him again as he gets up on his elbows. âHome?â You furrowed your brow. âFigured youâd want a bit of alone time..â You glance to the bathroom, where you can hear Dean grumbling behind the closed door.
Sam licked his lips. âStay.â Your eyebrows shot up. âLeast we can do after a night like this is buy you breakfast in the morning.â
You shook your head, cheeks heating up a bit. âYou donât need to-â
âWant to.â He corrected. âCome on.â He shifted so his head was on the remaining pillow, tossing the one that had been under Dean to the floor.
âYou sure?â you asked nervously, and he motioned again for you to join him. You gave him a nod and climbed into bed next to him, eyes starting to drift close as soon as your body relaxes under the covers.
Sam chuckles softly and waits for Dean.
By the time Dean emerged, you were sound asleep  next to Sam, and as far as he could tell, Sam was out cold as well. Dean was disappointed. He figured he'd be the one getting cuddled tonight. A small part of him had even hoped you would leave and he could get wrapped up in Sam.
With a soft sigh, Dean walked towards the other bed, the one he'd fucked you in. He grabbed a pair of boxer briefs off the floor, not caring if they were his or his brothers, given the events of the night, and pulled down the blanket.
âWhat are you doing?â
Dean turned and saw Sam watching him. âCrashing. What else would I be doing? I'm fucking tired.â
âGet in here, Idiot.â Sam pulled away from you and left an open space in between for Dean. âLeave those on the floor.â
Dean smiled at his brother and quickly climbed over him to get in between. As soon as he was in, you snuggled into his side, wrapping an arm around his waist. Dean glanced down at you as Sam settled against his other side.
âGet some sleep, Dean.â
Dean nodded. âNight, Sammy.â there was quiet for a moment. âSam?â
âHmm?â
âDo I know how to pick âem, or what?â
Sam chuckled. âYeah. You got damn good taste.â Sam shifted enough to kiss Dean's jaw, a move Dean never expected, and then he settled back down. âNight, Dean.â
Dean smiled, a big goofy grin, and closed his eyes.
As he drifted off to sleep, his mind replayed the night, and his imagination ran wild with possibilities of what could come next.
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