⋆ ˚｡⋆୨ 𝐨𝐧 𝐭𝐨𝐩 ୧⋆ ˚｡⋆
summary 𓂃 when you admit you’ve never been on top before, dean decides there’s no better place to learn than his bed.
warnings 𓂃 18+ mdni, explicit smut, established relationship, insecurity, first time riding, protected sex, praise, dirty talk, boob play, clit stimulation, missionary, soft aftercare.
word count 𓂃 3,468.
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You'd been pretending to watch the movie for at least fifteen minutes.
Dean had been doing a terrible job of pretending he wasn't staring at you for just as long.
It was a terrible performance on both sides, especially considering the laptop was still playing some action movie at the end of his bed, and neither of you could've named one thing that'd happened in the last ten minutes. You were tucked under his sheets in one of his old Briar shirts, the hem brushing soft against your thighs because your underwear was the only thing you'd bothered putting on after your shower, and Dean was lying beside you with one hand behind his head and the other low on your hip like he was trying very hard to act like a gentleman.
He was trying to behave, which was sweet, really, but not exactly successful.
"You're staring again," you murmured, not even bothering to look away from the screen.
Dean's thumb moved in a slow circle over your hip. "You're in my bed wearing my shirt. You can't really blame me."
"You gave it to me," you pointed out, like that was supposed to make him less smug about it.
"I know." Dean's mouth curved like he'd been waiting for you to say exactly that. "Great decision, honestly."
You rolled your eyes, but the smile breaking through kind of ruined the effect. "You're impossible."
"Yeah." Dean leaned in, his lips brushing your shoulder through the fabric of his shirt. "But you like me anyway."
"Sometimes," you said, though your smile made it sound a lot less convincing.
"Right now?" he asked, his voice dropping just enough to make your stomach flip.
You turned your head to answer, which was apparently all the invitation Dean needed, because then he was kissing you, slow and warm, one hand sliding up your side beneath the fabric like he'd planned the whole thing. It was easy to melt into Dean like that, a lot easier than you'd ever admit out loud. Dean kissed you like he knew exactly how much time he had, which apparently meant he had no problem spending it dragging every little sound out of you to see how much trouble it got him into.
His fingers slipped beneath the hem of the shirt, warm against your waist in a way that shouldn't have made you gasp as quickly as it did.
Dean smiled against your mouth, entirely too pleased with himself. "There she is."
"Don't start."
"I didn't even say anything."
"You were about to, and we both know it."
He laughed, low and entirely too pleased with himself, before rolling onto his back and tugging you over him like he already knew you'd follow. And you did, because apparently thinking was no longer part of the plan, one knee sliding across his hips until you were straddling his lap.
Then you froze beneath his hands, and Dean felt the change in you immediately.
His hands settled on your waist, thumbs brushing over your sides in a way that was soft enough to make your chest ache a little. "Hey."
You swallowed, suddenly very aware of the fact that you were in his lap with your thighs spread around his hips, his hard length pressing up beneath his sweatpants, and somehow his shirt still covering you didn't make you feel any less exposed.
"This feels like a lot of responsibility," you said, aiming for a joke and landing somewhere embarrassingly close to panic.
Dean's brow lifted like he wasn't sure whether to laugh or be concerned. "Responsibility?"
"I just..." You looked down, your fingers curling into the front of his shirt like that'd somehow make the words easier to get out. "I've never really done this before."
His expression softened, though that amused little spark in his eyes didn't go anywhere. "Been on top?"
Your cheeks warmed, which was annoying because Dean absolutely noticed. "Not really."
"Not really?" Dean repeated, thumbs still brushing over your waist like he was trying very hard not to look too pleased about that.
"Dean," you said, dragging his name out like a warning, even though the warmth in your cheeks made it pretty hard to sound threatening.
He smiled a little, his hands giving your hips a gentle squeeze like he'd decided to behave for once. "Okay. Not really."
"It's not a big deal," you said quickly, which was unfortunate because saying it that fast made it sound like it was definitely a big deal. "I just feel like I'd look stupid, or I wouldn't know what I was doing, and then you'd have to pretend it was hot, which is a very nice boyfriend thing to do, but also something I'd never emotionally recover from."
Dean stared at you for a beat, then laughed in this soft, disbelieving way that only made your face feel warmer. "Baby, I'm hard because you're sitting on my lap in my shirt. You could sneeze right now, and I'd find a way to be into it."
You blinked because, annoyingly enough, it had worked. "That was weirdly comforting."
"I'm great at comfort."
"You're absolutely not."
"I am when you're half-naked on top of me."
You tried to bite back a laugh, but it came out as this breathy little sound instead when Dean's hands guided your hips down, showing you exactly how slowly he wanted you to move over him. The pressure caught against your clit through your underwear, warm and steady enough to make your thighs tense before you could stop them.
Dean's eyes darkened like he'd felt the way your body reacted. "Does that feel good?"
You nodded, your thighs still tense beneath his hands.
His mouth curved. "Words, sweetheart."
"Yes," you breathed, because apparently that was the only word your brain had left to offer.
"There you go," Dean murmured, his voice soft enough to make your stomach flip.
The next kiss was messier, mostly because Dean kept guiding your hips over him like he had all the patience in the world, dragging it out until your underwear was damp, clinging to you, and making it pretty impossible to pretend you weren't affected. At first, the sounds you made were small and half-swallowed against his mouth, but Dean noticed every single one like he'd been waiting for them.
"Don't do that," he murmured.
You blinked at him. "Do what?"
"Hold back." His fingers tightened on your hips like he was making sure you couldn't pretend you didn't know what he meant. "I like hearing you."
Your stomach flipped, which was annoying because Dean absolutely felt it, and then he kissed you again until the friction dragged a moan out of you that you finally let him hear.
Dean groaned, as if he'd heard you'd done something terrible to his self-control.
That helped more than anything else could have.
By the time Dean had pushed his sweatpants down and rolled on a condom, your underwear was shoved to the side, your hands were planted on his chest, and the shirt was still hanging over you like a very pathetic attempt at feeling covered. Dean didn't try to take it off, which somehow made your chest feel tighter. He just held your hips, eyes fixed on your face as he guided himself through your wetness.
"Slow," he murmured. "Take your time."
You lowered yourself carefully, trying to take your time like he'd told you to, but your mouth still fell open the second the head of his cock pressed inside you. The stretch was familiar and different all at once, deeper like this, more intense because you were the one in control, which sounded nice in theory and felt a lot more terrifying with Dean watching your face like that. You sank inch by inch, trying very hard to look like you had any control over yourself, but the second he filled you, your fingers curled against his chest, and a shaky whimper slipped out before you could stop it.
Dean's jaw tightened. "Fuck."
You froze immediately. "Bad?"
His eyes snapped to yours as you'd just said something insane. "Are you joking?"
"You made a face."
"Yeah, baby, because you feel so good, I'm trying not to embarrass myself."
Your cheeks warmed, which was embarrassing enough on its own, but the praise still settled low in your stomach like your body had decided to enjoy it before you could overthink it.
"You're not just saying that?"
Dean's hands slid up your thighs, grounding you in a way that made it annoyingly hard to spiral. "Move once, sweetheart, and see if I sound like I'm lying."
So you did, moving slowly at first.
Your hips lifted, then sank back down, and Dean's head tipped against the pillow with this rough, helpless groan that made it pretty hard to believe he'd been lying about any of it.
"Oh," you breathed, and the second you moved again, it turned into something closer to a moan.
Dean's eyes opened, heavy and dark, like he'd been waiting for exactly that. "Yeah?"
"Feels good," you said, already sounding a little wrecked.
His hands squeezed your thighs. "Then keep going, sweetheart."
Your movements were awkward at first, mostly because your brain wouldn't shut up long enough to let your body figure it out, too busy worrying about the rhythm, whether you were doing enough, and whether you looked ridiculous hovering over him in his shirt with your thighs trembling.
Then Dean's hands tightened on your hips like he could feel you spiraling. "Stop thinking."
"I'm trying."
"No." His voice dropped, rough around the edges but still gentle. "You're trying to look good, which is insane, because you already do. Just move how you want."
The words hit harder than you'd expected, mostly because Dean sounded like he meant them, so you tried to believe him.
You rolled your hips instead of lifting so high, chasing the angle that made your clit catch against him every time you sank back down, and the moan that left you was loud enough to make Dean's cock twitch inside you like he was having a very hard time staying calm about it.
Your eyes flicked to his face, and Dean looked so wrecked that it made it pretty hard to keep worrying about whether you were doing it right.
His lips parted, jaw tense, and his hands kept flexing on your hips like Dean was having the world's hardest time remembering he'd told you to move how you wanted.
"You like this?" you asked, and even though your voice shook, it still came out bolder than before.
Dean laughed once, rough and breathless, as the question had actually offended him. "Like it?" His hips jerked up into you, dragging a gasp out of your mouth. "Baby, I'm trying not to lose my fucking mind."
That did something to you, mostly because Dean sounded like he meant it, and apparently, your body liked knowing you could mess him up that badly.
Your next movement was smoother, more confident, and the moan that came out of you wasn't even close to quiet, which Dean clearly noticed because his hands tightened on your hips immediately.
"Dean—fuck," you moaned, and the way his eyes darkened made it pretty clear he'd liked hearing his name like that.
"That's it," he murmured. "Let me hear you."
You rode him slowly at first, then a little faster once you realized your body had apparently figured out what your brain kept trying to overthink, your hands sliding up his chest as his shirt rode higher over your thighs. Your cunt was soaked around him, every movement making it easier, wetter, and a lot harder to feel shy about, especially when Dean looked down to watch where you were taking him and groaned as he'd just lost whatever was left of his self-control.
"God," he muttered, hands tightening on your hips. "You were worried about this?"
You tried to laugh, but it came out closer to a whimper when he helped you grind down harder. "Maybe."
Dean looked like that answer personally offended him. "You're killing me."
His fingers tugged at the hem of the shirt, and you slowed immediately, like your body had decided to panic before your brain could tell it not to.
Dean noticed immediately, because, of course, he did, his eyes lifting back to yours, as if taking the shirt off suddenly mattered a whole lot less than making sure you were okay. "Can I see you?"
Your stomach fluttered.
His hands rubbed up your thighs, warm and steady. "You can keep it on if you want."
You hesitated for only a second before lifting your arms, which felt a lot braver than it probably looked.
Dean pulled the shirt over your head and tossed it aside, leaving you in your bra and still moving over him like your body hadn't quite figured out whether to be nervous or proud. His eyes dragged over you slowly, and for once, Dean Di Laurentis had absolutely nothing to say.
That made your chest tighten, mostly because Dean looking at you like that was a lot harder to handle than any stupid comment he could've made. "What?"
His hands slid up your waist, warm and certain. "You're so fucking pretty."
Your breath caught the second his palms covered your breasts through your bra, thumbs brushing over your nipples beneath the thin fabric, and your rhythm faltered immediately, because apparently, Dean touching you there made moving and thinking at the same time impossible.
"Oh—Dean."
His mouth curved, entirely too pleased with himself. "No, don't stop."
"You're distracting me."
"Good." His thumbs circled again, making you clench around him like your body had decided to prove his point. "Keep riding me anyway."
You moaned louder this time, hips rolling as his hands played with your tits through your bra, and every touch made you stutter in a way Dean very clearly noticed. Every bit of praise made you wetter, every look on his face made you a little bolder, until the embarrassment started slipping away as your body had finally decided to stop fighting him.
"Tell me," he said, voice rough. "Tell me what feels good."
You swallowed, still moving over him because apparently stopping would've been the worst idea. "Your hands."
"Yeah?"
"And your cock." Your voice was breathless enough to be embarrassing, but you said it anyway, and Dean's eyes went so dark that it made the embarrassment feel worth it. "Feels good when I move like this."
You rolled your hips harder to show him, and Dean's head dropped back as you'd just ruined him on purpose.
"Fuck," he groaned. "Don't stop doing that."
Hearing Dean sound like that ruined something dangerous to your confidence, mostly because it was a lot harder to feel embarrassed when he sounded like he was the one barely holding it together.
Your hands moved behind your back, unclasping your bra before your brain could show up and ruin the moment. It slipped down your arms and fell somewhere between you, and Dean stared as you'd just done something genuinely unfair to his ability to breathe.
"Look at you," he breathed, and the way he said it made your whole body feel warm.
The words made your chest warm in a way you weren't sure what to do with.
Then his mouth was on you, lips closing around one nipple while his hand covered your other breast, and you cried out so quickly it would've been embarrassing if Dean hadn't groaned like it'd done something to him. Your fingers slid into his hair, hips moving faster now as pleasure started building low in your stomach.
"Dean, I'm—" Your voice fell apart into a whimper when his thumb found your clit, because apparently your body had no interest in letting you finish a sentence. "Oh my god, right there."
"There?" he asked, smug in a way that would've been annoying if he didn't sound so wrecked.
"Yes. Fuck, yes."
He rubbed slow circles over your clit while you rode him, his other hand on your hip and his mouth moving from your breast to your throat like he wasn't already making it impossible to focus. You were close, so close your thighs had started shaking, but the rhythm was getting harder to keep, your moans turning messier and needier as frustration tangled with the pleasure your body kept trying to chase.
Dean caught it instantly, like every little shift in your body was something he'd been waiting for.
"Come here," he murmured.
Before you could even think about arguing, Dean rolled you beneath him and pulled the sheets over both of you, settling between your thighs without slipping out like he'd decided you'd done enough thinking for one night. The new angle made you gasp, your legs wrapping around his waist as he pressed deeper.
Then Dean caught both your hands and laced your fingers together, pinning them above your head so gently it made your chest ache a little.
Dean kissed you, slow and messy, like he had every intention of making good on that promise. "Let me finish what you started."
"Please," you whispered, and it came out a lot needier than planned, which Dean absolutely noticed.
Dean's expression flickered. Then his hips started moving. Slow, deep, steady thrusts that had you moaning into the space between you, thighs locked around his waist, your hands crossed with his over your head. The sheets tangled around your legs, heat building under the blanket, his body heavy and warm over yours.
"You did so well," he murmured, his mouth brushing your jaw like he knew exactly how badly the praise was getting to you. "Looked so fucking good on top of me."
"Dean," you whimpered.
"I know." His hips rolled deeper, pulling your back into an arch. "I've got you."
His hand slipped between your bodies again, thumb finding your clit like he already knew exactly what you needed, and your whole body tightened around him.
"Oh—fuck, don't stop," you gasped, which was probably unnecessary considering Dean looked like stopping would've killed him.
He groaned anyway. "Wasn't planning on it."
The pleasure snapped through you suddenly, hot and sharp, and your moan broke against Dean's mouth as you came around him. Your thighs locked around his waist, fingers tightening in his above your head like you needed something to hold onto while your body shook beneath him.
Dean followed right after, his thrusts going uneven as he'd finally lost the last of his control, face buried in your neck as a rough groan broke out of him while he held you close and came.
For a while, neither of you moved, both of you too warm and tangled beneath the sheets to do anything other than breathe.
"You okay?" he asked softly.
You nodded, still trying to catch your breath. "Yeah."
His grin appeared slowly, which was never a good sign. "So."
"No."
"I didn't say anything."
"You were about to."
"I was just gonna say you're definitely not bad at being on top."
Your face warmed, and you turned it into the pillow like that might somehow save you. "You're so annoying."
"And you were so loud."
"Dean."
"I liked it," he said, kissing your cheek like he hadn't just made you want to disappear into the mattress. "A lot."
You tried to glare, but it came out pretty weak, especially when he slipped out carefully and disappeared to clean up like he hadn't just ruined your ability to function. When he came back, he helped clean you with a warm towel, gentle when your thighs twitched, before pulling his shirt back over your head as it belonged there.
"Putting me back in this?" you asked, glancing down at the shirt.
"Obviously." Dean climbed into bed beside you and pulled you into his chest, looking far too pleased with himself. "It's my new favorite thing now."
You laughed softly, settling against him while his arm wrapped around you like he had no plans of letting you go anytime soon.
For a minute, Dean only rubbed slow circles over your back like he was trying to make sure you'd fully melted into him. Then his voice came again, softer this time, though obviously still teasing because it was Dean.
"So..." His mouth brushed your hair, and you could hear the grin in his voice before he even finished. "You wanna do that again sometime?"
You pinched his side, which only made him laugh because apparently even that wasn't enough to make him less pleased with himself.
Dean laughed and pulled you closer, sounding far too pleased with himself for someone who'd just been pinched. "I'll take that as a yes."
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OH MY GOD
