Pairing: Dean x Reader | Sam x Reader
Rating: 18+
Tags: oral fixation, over stimulation, praise kink, dom / sub relationship, sub sharing, oral sex (f rec), squirting
Word Count: 2.7k
Dating Dean Winchester came with a lot of perks. He was charming, funny, attentive, and sexy as hell. One of your favourite things about Dean was his hands. Dean loved having his hands on you; it didn’t even have to be in a sexual way, he was always initiating some kind of contact between you anytime you were in the same room. When it was about sex though, he really outdid himself. What that man could do with his fingers was downright sinful. What you’d never expected was to add Dean’s little brother Sam to this list of perks too.
“Sam’s coming to stay this weekend.”
“Okay…” You drew out the last syllable, not sure why Dean chose this moment to start talking about his brother. You already knew Sam was coming to stay this weekend; those plans had been made a few weeks ago.
“And you know, it’s his birthday next month,” Dean continued, apparently not in a rush to make a particular point.
“Yeah,” your answer came out more like a question.
“But he won’t be able to visit next month. So I thought maybe I could give him his birthday present early, this weekend.” Dean was still massaging your chest, tweaking your nipples every now and then, making you jerk and shiver against him any time he did.
“You already got him his birthday present? You never plan that far ahead,” you laughed and let your eyes slide shut. You chose to ignore the fact that it was weird to be having a conversation about Dean’s younger brother right now and just enjoy the attention you were getting.
Dean cleared his throat, as if he was unsure about continuing, before he answered. “I have an idea for it, but I wanted to check in with you about it first.”
“Why?” Curiosity filled you.
“Well,” Dean was stalling now, you could tell. “You know that thing we talked about a few months ago, with the whole… me sharing you out to other guys?” You could feel Dean blushing behind you, his chest growing hot against your back.You’d always found it amusing how different Dean was about your sex life when he wasn’t in ‘Dom’ mode. It was like he could be two totally different people. As your Dom, Dean was confident, unabashed, authoritative, but outside of that headspace Dean was much more hesitant talking about sex than you ever imagined he would be.
You remembered the night he was referring to all too well. After he’d gotten up the courage to ask for what he wanted from you, and you had enthusiastically agreed to the idea, you’d had an incredible night. Dean had edged you and eaten you out until you were almost screaming by the time he let you cum. Looking back, one of the reasons it stuck in your mind is you’d both had to face a very awkward Sam in the kitchen the morning after. He had been crashing with you and Dean that weekend and had clearly overheard your nocturnal activities.
“Sweetheart?” Dean’s voice shook you from your memories and you focused back onto the conversation.
“Yeah, sorry.” You groaned when Dean gave your nipples a harsh pinch in response.
“It’s not polite to daydream while I’m talking to you, baby,” Dean admonished, and just like that he slipped into his Dom persona. The awkward hesitancy of a moment before melted away. His touch felt surer, his breathing felt more even and controlled as your body moved up and down with his chest.
“Sorry, sir,” you whispered, “I remember what we talked about,” you reassured him.
“You’re still okay with that idea?” Dean pressed.
“Yes, sir.”
“Well, that’s what I want to get Sam for his birthday.” Dean tied all the threads together for you and you felt yourself inhale sharply when you finally understood.
“Oh,” was all you could manage to say at first, still trying to process. Your first reaction was to be weirded out that Dean wanted to share you with his brother. When he mentioned sharing you with someone else, it was made clear that he wanted to be there, whether or not he was participating. Would Dean really want to see his little brother naked, and fucking his girlfriend?
“Y/N.” Dean prodded, clearly expecting a better answer than the one you’d given.
“Are you sure Sam wants that?” you asked. Sure, you’d caught him looking at you a couple times when he thought you weren’t looking, but you’d chalked that up to curiosity, or a bit of jealousy born out of sibling rivalry, not much more.
“Oh trust me,” Dean laughed deep in his throat, “he’ll think he’s died and gone to heaven.”
“Okay,” you agreed tentatively, but you had to check. “And you’re okay with, y’know, seeing your brother’s junk and everything?” Dean snorted behind you, and you turned to look at him skeptically. “Because that’s sort of inevitable if we do this.”
“Don’t worry sweetheart, that won’t be a problem,” Dean reassured you but didn’t elaborate further.
“Okay then. If that’s what you both want, then let’s do it.”
It turns out that that night Sam had stayed over had sparked a very specific fantasy for him, which he drunkenly admitted to Dean some weeks later. Sam loved going down on girls, and once he’d heard how responsive you were to Dean, apparently Sam couldn’t shake his desire to be the one to make you feel that way. Sam, however, was employing a very different tactic than what you were used to with Dean.
As your Dom, Dean liked to make you wait for things, earn your rewards, test your self control and see how far he could push until you broke and begged him for release; Sam, on the other hand, wasn’t making you wait for a goddamn thing. When he walked into the room with you waiting for him, naked on your and Dean’s bed, he didn’t even bother taking off any of his own clothes; he licked his lips and went straight in for his present. You came for the first time about a minute and a half later.
That must have been hours ago, and you honestly weren’t sure how many times you’d cum at this point. Some of the orgasms had definitely blended together as Sam relentlessly licked and sucked, even while you were spasming underneath him and begging him to stop. Once or twice you considered using your safe word, but you truly didn’t want this to end. Sam never stopped, never let you rest fuck, he barely came up for breath.
“Oh my god, Sam, I can’t – fuck – can’t take it anymore, please,” you whimpered, cheek pressed into Dean’s clothed chest as Sam continued his tongue’s assault on your clit. You squirmed helplessly between them; Dean had his legs hooked over your knees, keeping your thighs spread wide for Sam even when you desperately wanted to close them to stave off the stimulation. Your wrists were tied together behind your back, and Dean’s arms were wrapped firmly around your chest, holding you in place. He had you well and truly trapped.
“What, don’t wanna cum again, baby?” Dean’s voice was full of false sympathy, as it so often was when he teased you. “You’re usually so desperate for it, I thought you’d enjoy Sam giving you all this attention.” You whined in response, feeling the heat of Dean’s breath against your neck as he laughed at you.
“C’mon Y/N,” Sam pulled back to look up at you, a cheeky smile playing on his face, and the remnants of your orgasms coated his lips and chin. “Don’t make me stop now.” He slinked up your body, pressing wet kisses along your skin the whole way, licking up the sweat he found there, making you shudder against Dean. “Wanna make you cum again,” Sam whispered when he reached your throat. “Please,” he uttered against your lips, and at the same time he teased one of his long fingers inside you.
A small, mewling cry left your throat as Sam rubbed his finger gently inside you. The change in sensation was a much needed relief; finally having something inside you felt so good you thought you might cry. You’d been begging, pleading, with Sam and Dean to fill you: with their fingers, their cocks, whatever they wanted. You just desperately needed something inside of you. Sam had ignored your pleas for more, continuing to lick and suck and kiss; pulling you over the edge again and again with only his tongue and his lips.
“You’ve been so good for me, baby girl,” Dean’s voice rasped over the shell of your ear. “Been such a good girl, letting Sammy do what he wants to you.” Sam was dropping small kisses all over your face as he continued to lazily pump his finger in and out of you. “Let him make you feel good again, I know you can do it.” Dean nibbled gently on your earlobe, then dropped his lips to the base of your throat and began to suck a mark into your skin.
“I ca– can’t, Dean,” you moaned as Sam added a second finger to your weeping hole, keeping a slow and steady pace.
“Yes you can, baby,” Dean soothed, pulling his mouth from your neck and kissing into your hair. “You’re such a good girl for me, Y/N. Want you to be a good girl for Sammy too, yeah?” You nod weakly. “Just once more for him baby, I know you can do it.”
Dean’s words burned through your body, spurring you closer to another climax. You desperately wanted to be the good girl that Dean thought you were. You wanted to give him and Sam what they wanted. Sam began to thrust his fingers quickly, angling them to drag across the spongy spot inside of you that hadn’t received any stimulation so far tonight. The new sensation sent a shock through your body, making you shake in Dean’s arms as Sam ducked back between your legs and proceeded to kiss every bit of skin his lips could find.
“That’s it sweetheart,” Dean held you tightly against him. You knew it was partly to keep you grounded; make sure you felt safe knowing he was here with you. But his real motive was so you couldn’t get away from Sam’s tongue, now dancing over your entrance. “Just one more baby, you can do it, I know you can,” Dean encouraged. “It’s okay, you’re so close aren’t you? Just let it happen, let Sammy make you cum baby, come on.”
Dean kept up his monologue of encouragement as Sam brought you closer and closer to yet another orgasm. When it finally hit, Sam’s fingers fucking you deep and hard, and his lips sealed around your clit, your whole body seized up as the tension rocketed through you. You could feel the scream that left you deep in your chest, in fact, you felt it more than you could hear it.
White bursts filled your vision and static clouded your hearing and it took a moment before you returned to yourself. You heard Dean’s praise in the background but nothing would process as words, everything was fuzzy, and all you could register was the fact that the sounds were comforting, and that you felt amazing – if exhausted.
“Good job baby, good girl,” Dean was soothing you, “such a good girl.” His hands traced over your body to calm down the tremors that were still shaking through you.
You groaned when Sam licked against your clit again. Everything was so sensitive it felt like your skin was buzzing. You could barely feel Sam’s tongue against you anymore and at the same time it stung. If your hands weren’t tied behind your back, you’d try to push him away.
“No Sam, please,” you murmured, but Dean didn’t let you pull away from his little brother. Again, for the smallest moment you consider using your safe word, but you trusted Dean to know your limits. He held you still, pressing his hips behind yours to keep you anchored to Sam’s mouth. Sam just didn’t want to stop. It was almost like he couldn’t. You started to wonder if this was your life now – trapped between them, held hostage by Dean’s arms and Sam’s lips.
The overstimulation brought tears to your eyes, and Dean must have felt them dripping off your cheeks and onto his hands, which were placatingly massaging your breasts. He was still whispering to you, keeping up his litany of praise, and then falling back to the phrase ‘just once more.’
“P-p-please, ple-” you stammered, begging Sam to stop but not even able to get through your objection, the pain and pleasure surging through you were too overwhelming.
“Sounds like she wants to cum again, Sam,” Dean laughed, pinching your nipples.
“No, no,” you tried to protest but your words sounded weak, even to you.
“C’mon, Y/N, just one more time. Please,” Sam peeked up at you through his lashes, eyes bright and high. “It is my birthday…”
“You’ve been so good, baby, just one more time for us, okay?” Dean gently pushed again.
“No, De, please, I- I can’t. It’s too much,” you begged. You really didn’t think you’d be able to cum again, it just seemed impossible at this point. But Sam didn’t let up, teasing the tip of his tongue around your clit, and fucked his fingers against your g-spot you felt your body spiralling, any kind of self control you had being completely obliterated.
“Yeah, there y’go,” Sam encouraged when he felt you clenching around his hand, voice muffled because he refused to tear his mouth away from you. “Fuck, taste so good.” Lick. “Fucking love doing this to you.” Suck. “Love tasting your cum. Fuckin’ dripping baby.” Sam’s tongue joined his fingers at your entrance, lapping at the slick that was dripping onto the sheets beneath you.
“Ohmygod,” you squealed as something strangely familiar and desperate curled tight in the base of your stomach. Panic filled you when you realised what it felt like. “Fuckfuckfuck, no, no,” you groaned but you couldn’t stop it, climaxing yet again with a liquid gush between your legs, soaking Sam’s face, hand, and the bed. Sam kept fucking you through it with his fingers and tears slid hotly down your cheeks as you collapsed into Dean, no longer fighting, just letting Sam ruin you.
“Fuck,” you faintly heard Dean groan behind you.
“S- sorry, so sorry,” you whimpered, too embarrassed to open your eyes and see the damage you’d done.
“Holy shit,” you heard Sam groan, strained, and you vaguely registered the bed shaking beneath you before it suddenly stilled. “Oh my god.”
Dean laughed behind you. “Happy birthday, Sammy.”
“Fuck dude, told you I could make her squirt.” Sam bragged as he leaned in and lapped at the residue coating your skin. You no longer had the energy to shiver away from him, you just lay there and let him do what he liked.
“You have a problem man,” Dean teased Sam from over your shoulder, and he must be watching Sam still licking incessantly at your folds.
Internally, you had to agree with Dean that Sam’s obsession with eating girls out went a little too far, but you let it slide for the moment as you felt yourself drift off to sleep in Dean’s arms; exhausted, sated, and oddly comforted by the warmth of Sam’s breath still between your legs.
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