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.
“Get the fuck over here.” You smiled and moved towards him. “Dean, find some lube.” He pulled you into a rough kiss, and you moaned softly tasting his come on his tongue.
“You really gonna fuck me?” Dean seemed nervous.
“It’s not so bad.” You broke the kiss and looked at Dean sitting next to Sam, as Sam pulled you fully onto his lap. “Never done it before?”
“Not on the receiving end.”
“It’s going to be uncomfortable at first, but I can maybe help with the prep.” You smiled. “And if he hits right, he’ll hit your prostate, and it’ll be the best fucking orgasm of your life.” Dean glanced to Sam. “If he doesn’t, I’m still sucking your cock, so it’ll still be a fun time.”
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.
“You’ll help with prep?”
“Yeah, I might have something for that..” You bit your bottom lip, getting off his lap and head for your purse. “I went shopping before hitting the bar. Wasn’t expecting to get this lucky tonight.” You pulled out a small plastic bag and tossed it next to Sam. “I don’t mind sharing, this is worth way more than I paid for that.”
Sam opens the bag and a smile graces his lips as he starts to pull things out. “What’s that?” Dean asks, making his way over with a bottle of lube.
Sam glances at you and you nod with a smile. “Vibrator.” He pulls the first item out.
“Slim, discreet, and powerful.” You smile and wink at Dean.
“Butt plug?” Sam glances at you as he pulls out the box for a small plug with a pink jewel on the end.
“I like being full of cum, and I like feeling pretty when I am. Sue me.” Dean’s watching you with a whole new look, and Sam glances down at the box. “You 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.”
Sam groans, fingers tightening around the box for a moment before he puts it down. He doesn’t care what the last item is, he just tosses the bag aside. “Get the fuck over here, Dean.”
“Okay, but uh.. I- I was not expecting this-”
“Relax, Dean.” You smile at him, putting a hand to his lower back as you guide him closer to Sam. “If you don’t want this, just say so.”
“It’s not that..” He worries his bottom lip between his teeth.
“Want me to start you off? I’ll go gentle and slow. Sam can stroke you to help you relax.” You glance at Sam who shrugs.
“Y-Yeah.. Yeah maybe..” He slowly gets on the bed. He’s 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 Dean’s hand and guides him into position before handing it off to you. “Just stay still and relax.” Dean nods.
“Can I- uh..” Dean swallows nervously as he hears the squelch of the lube bottle. “Maybe, one day, if we do this again, you know.. Can I do you?”
“You wanna fill my ass?” Sam sounds amused.
Dean gives a nod and a shrug. “You’re about to fill me. Only fair.” He winces feeling the cold lube drip down between his ass cheeks, a preemptive hiss when he feels the vibrator against his puckered hole.
“Relax.” you coo softly from behind him, your hand rubbing gentle circles on his lower back.
Dean is watching Sam, waiting for an answer. “I’ll consider it.” Dean seems to deflate a little, but nods. “Relax for me, Dean.” Sam leans in close so he can whisper into his brother’s ear. “I’m more likely to say yes if you don’t spill a drop of my come tonight.”
“Fuck.” Dean breaths out, and you take that moment to push in. “Fuck!”
“I’m going slow.” You promise, hand still on his lower back while the other pushes the slim vibrator in a half inch at a time.
“Jesus, that feels-”
“Like you need to shit.” You chuckle softly, pushing it further and further. His forehead drops to the mattress. “You’ll get used to it. And it’ll get better. I promise. Try to relax.”
“It’s hard.” He mumbled into the comforter.
Sam licks his lips, and lays on the bed so his face is close to Dean’s. He then reaches out, and runs a finger along the underside of Dean’s flaccid cock that sends a shiver down Dean’s spine.
“It’s all the way in.” You point out, and Dean’s 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. “Buried to the hilt.”
“I-It’s not so bad..”
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 Dean’s slowly hardening member with his fingers. “Ready?” You ask.
“For what?” You flip the little switch on the end, and the vibrator comes to life. “Holy shit!” Dean’s 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. “I was not fucking ready for that.”
“How does it feel?” Sam gets his brother’s attention again as you’re pulling it back.
“Fucking weird.” You angle it differently when you push forward and Dean’s whole body jolts again. “What the fuck did you hit?”
“Prostate, I think.” You chuckle softly. “You’re almost done with this. Switch?” You look to Sam.
“Wait.. wait..”
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. “He’s 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.” You chuckle softly. “But don’t worry. I’ve got you.” You reach a hand under and start to stroke his half hard dick.
He gives you a nod as Sam gets up. “And I thought you looked good with things in your mouth..” 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. “You’ll be full again soon.” You promise and turn your attention back to Dean. You place a gentle kiss on his lips as Sam gets lube on his fingers. “Ready?”
“Ready.” Dean nods.
“Good boy.” You watch as there’s a change in his eyes at the praise, and you store that little bit of information. “Praise kink, huh. I’ll remember that.” 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. “Taking two fingers like a champ.” Sam praises, confirming your suspicion.
“Fuck, Sammy.” His cock throbs in your hand and you give him a tight squeeze.
“Better work him open if you want him to come around you, Sam.” Your eyes are locked on Dean’s as you speak. “Bet Sam can’t wait to see you stuffed full of his cock.”
“Son of a bitch.” Dean groans again, and you chuckle.
“Fuck.” Sam curses. “So fucking tight. Can’t wait to get in there.”
“Both of you need to shut the fuck up.” Dean grumbles. He’s now at full length and girth in your hand. You can’t help but look back at Sam with a smile.
“Soon, Dean. I’ll be fucking this pretty little ass, soon.” You can tell by the flex in Sam’s forearm that he’s now scissoring his fingers to work Dean open more. “Just need you to take a bit more.”
“You can do it, Dean.” you praise as Sam pulls his two fingers out, and pushes three in. Dean whines, and his body gets tense. “You’re such a good boy.” You start peppering his skin with kisses, any bit of him you can reach. His shoulder, his bicep, his cheek. It’s 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.
“You’re both killing me.” He grumbles, forehead pressed into the comforter underneath him again.
Sam pulls out his fingers, and slaps Dean’s ass. “But what a way to go.”
Dean looks back at his brother and shoots him a glare. “Good to go?” You ask and sit up. Sam nods. “Alright.” You grab a pillow and pat Dean’s side. “On your back, handsome.” Dean drops to his side and shifts until he’s settled with his legs on either side of Sam. “Put this under you.”
“What? But what if- I mean-”
You chuckle and make him lift his ass so you can get the pillow under him. “It’s your first time, so you need to be as relaxed as possible. And I’d rather not be under you just in case your ‘what if’ happens.” You tease. “Besides, housekeeping has seen worse.”
“How do you know? What’s worse than-”
“I work here.” You smiled and leaned over to kiss his lips. “And you don’t want an answer to that. Trust me. Now relax, and let me suck your cock while your brother fucks you senseless. Okay?”
He nods. “‘Kay.”
“Whenever you’re ready, Sam.” You slowly start kissing down Dean’s skin while he shifts the pillow until he’s 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 brother’s 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 Sam’s lubed up member, gripped tight in his hand and just barely touching Dean’s hole.
Sam can’t help but enjoy the view for a moment. Who knows when or if he’ll see it again. And then he’s pushing forward. He’s fighting to go slow, but he can’t wait to be wrapped up warm in that tight canal.
Dean’s 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.
“Shit..” It falls from Sam lips, or maybe both of them, but it’s Sam’s 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.
That’s when you take Dean in your mouth.
“O-oh, fuck..” Dean’s 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 it’s music to your ears.
Sam’s holding Dean tight, and he’s leaning so far forward that his hair is brushing against your back, his breath fanning over your skin. “So fucking tight..” He mumbles.
“J-Just... “ Dean’s starting to find words again. The hand that held onto your waist leaves it, and finds Sam’s forearm instead. “Need- Need a minute.” You can feel Sam nod, and you hum around Dean. “Oh shit! You too.. Fuck.. just-” He lets out a shaky breath and his grip tightens on your hair. “Just a sec..”
He’s 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 Sam’s lips brush your skin.
“Come on, Dean. You can take it.” Sam’s muttering the words against your skin. “You feel so fucking good.”
You feel him swell a bit in response, and this time, you can’t fight the moan. You feel something on your back again, fingers ghosting over skin and for a moment, you think it’s Dean. That is, until the fingers trail between your ass cheeks, teasing at your hole for a moment before leaving completely, and that’s 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.
“Good girl.” You can hear his smile. “Think we can make him cum just like this?”
“Fuck you.” Dean whines, making Sam laugh. “Just fuck me already.”
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. “My fucking pleasure.” Dean’s hips jolt when you cry out around him, but Sam just pulls out his fingers and slaps your ass hard before he’s grabbing hold of Dean again and starts rolling his hips out and then in.
Dean’s grip lets up on your hair enough for you to move again, so you try to match Sam’s pace. “Shit.” You opened your eyes, and Dean’s head is back, eyes shut as the curses come out one after another. “Fuck. shit. Shit. Holy shit..” Then he’s biting his lip and whimpering. “Fuck, Sam. I can’t- I can’t…” His fingers in your hair tighten again and he’s pushing you down further on him.
“Can’t what?” Sam asks.
“I can’t..” Dean whines. “I can’t take it.. Fuck.”
“Want me to stop?” He doesn’t stop his movements when he asks, instead he waits for Dean to say the words.
“Want you to hurry the fuck up and come.” The next thing past Dean’s lips is a whimper. “Please, Sam..” You groan around him as he begs, and it only makes him sound more desperate. “Harder, fuck, harder. Please. Pleasepleaseplease..” There’s 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.
Dean’s hips stop moving when Sam pushes them down again. “Then stop fucking yourself on my cock like a desperate whore. Just tell me what you want.”
Dean lifts his head and yells at his brother. “I want it fucking harder! Bitch!” You chuckle around him, and he just pushes your head down again, making you gag around him before he lets up.
“That’s all you had to say, Jerk.” Sam pulls back and slams forward again, his hip bones slamming Dean’s thigh into your shoulder.
“Fuck!” 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. Dean’s 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.
“I’m gonna fucking come.” Sam tells you both, or himself, you don’t know anymore. There’s a chorus of sound filling the room and you can’t tell who’s 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. “Come on, Sammy, please.” His hips are moving again. He’s 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.
“Oh fuck.. Sammy..” His brothers name comes out a desperate and needy whine, and that’s 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 hadn’t had time to swallow.
“Fuck, that’s hot.” Sam pulls you up to him, licking a stripe of come off your chin before his tongue thrusts into your mouth.
“Fuck.” Dean sighs, his body lays limp on the bed and he looks every bit the fucked out mess you know his is. “Best fucking orgasm of my life…”
You and Sam chuckle together before you pull apart. “I told you.” You ran a finger over his flaccid member and he hisses and shifts away from your touch. “Sorry.” You smile.
Sam drops to the other side of Dean and sighs in contentment. It’s quiet for a bit, but then Dean speaks. “I need to shit.” He pulls himself up from the bed and you can’t 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. “You forgot to plug him up.” you tell him
Sam’s eyes come down and he watches you hold up the box. “Oh shit..”
You smile and shake your head. “Keep it. First time might not be the best time for it anyways.”
“Thanks.” He watches as you start grabbing clothes. “Where you going?”
You look up at him again as he gets up on his elbows. “Home?” You furrowed your brow. “Figured you’d want a bit of alone time..” You glance to the bathroom, where you can hear Dean grumbling behind the closed door.
Sam licked his lips. “Stay.” Your eyebrows shot up. “Least we can do after a night like this is buy you breakfast in the morning.”
You shook your head, cheeks heating up a bit. “You don’t need to-”
“Want to.” He corrected. “Come on.” He shifted so his head was on the remaining pillow, tossing the one that had been under Dean to the floor.
“You sure?” 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.
“What are you doing?”
Dean turned and saw Sam watching him. “Crashing. What else would I be doing? I'm fucking tired.”
“Get in here, Idiot.” Sam pulled away from you and left an open space in between for Dean. “Leave those on the floor.”
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.
“Get some sleep, Dean.”
Dean nodded. “Night, Sammy.” there was quiet for a moment. “Sam?”
“Hmm?”
“Do I know how to pick ‘em, or what?”
Sam chuckled. “Yeah. You got damn good taste.” Sam shifted enough to kiss Dean's jaw, a move Dean never expected, and then he settled back down. “Night, Dean.”
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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