He's lost count at this point, orgasm after orgasm. You started slow and loving but after while you decided that going slow wasn't really what he needed.
What he needed was to be taught a lesson on how not to make a bet on something he knew he was gonna lose.
Said bet being that, if he could cum seven times and still be able to form coherent and cohesive sentences (aka no brain mush) that you would never talk bad about his beloved music collection again.
Of course you both knew he would fail, he could barley handle three and that's without you whispering sweet nothings in his ear but alas, his pride wouldn't allow him to back down. So here you both are, dean on the verge of tears, which you always find hot, and you sitting sweetly next to him. Hand absolutely drench in sweat, pre-cum, and cum.
"I- shit baby please" Dean barley got out, forehead covered in sweat as one hand grabbing your wrist whilst the other digs into his naked thigh. It was a beautiful sight, not only because your winning a bet against him, you also just have a gorgeously pathetic man at your mercy. If you were to ask him to do absolutely anything for you, he would do it in a heartbeat.
Well maybe after he got cleaned up.
"I know baby, dont know what to do with that big brain of yours do you" He whined, a noise not often heard by you. It takes Dean a long time to act like this, emptyhead and vulnerable. It took much longer for him to show this side of him to you. Always focusing on the other's person's pleasure, never his own
You kept going faster and faster, edging him on but never keeping him there, it was a filthy sight. "S-shit w-wai-" he cut himself off with another loud moan, turning his head to this side in hopes for muffle the noises being made.
You kept going, refusing to slow down even after his protests. "You wanted this de, I'm just giving it to you" you said, condescendingly. You snaked your free hand up to Deans face, caressing his cheek as he leaned into the touch. So sweet you thought before bringing your fingers to his plush lips, lightly tracing his bottom one before inserting your middle and index finger inside his mouth.
He immediately start drooling, tongue coaxing both finger wet as he moaned. You could feel your own arousal dripping down your legs.
At this point he didn't care what he looked like, all he knew was that he felt good.
"P-pease I cnt" Dean slurred out, fingers hindering his speech as you continued, fingers going in deeper making him gag. Eyes rolling backwards. When you finally took them out, you had a thought and immediately acted on it.
There was rarely anything off the table for you both when it came to sex, naturally you've fingered him. It was a whiskey filled night when it happened and you both barley even remember it.
You brought both wet fingers down to his hole, circling it. Even if his brain was fried he knew what you were Implying. Giving you a quick ok in between moans and you slowly pushed in, breath hitching as you went deeper. Setting a neutral pace unlike the one you've set on his cock, the tip a bright red color.
"Last one last one" he pleaded as his hand grabbed your wrist, you decide to give him some form of mercy and let him cum just one more time. You started to speed up, finger pumping in and out as your layed your palm flat against the head of his dick, rubbing faster and faster.
"C-cummin- oh fuck oh fuck" he barley got out, thrashing around on the old motel bed as you curled your finger inside before taking it away. Leaving him empty and still wanting more, even after the amount of rounds y'all just went.
You quickly got up to go get a warm wet rag to clean him up with as he's definitely not able to shower right now.
"So I guess that means I win huh" you giggled while putting the rag on the night stand and leaning in for kiss.
"Shut up"
Okay so this is lwk ass BUT I just wanted this out of my drafts 🥲 uhhhmmm anyways dean I want you sexually.
this post contains links to explicit videos. Headphone use recommended. Do not open in public <3
MDNI, 19+
fav position, classic missionary
angel stamina means he could go until you faint
obligatory tie pulling…
absolutely fascinated with your toy collection, and will make you use it while he watches
human anatomy interests him and he will study you for as long as he feels necessary
CW: NEXT TWO HAVE SPANKING!!!
It’s my party and I can headcanon Cas having a spanking kink!!!
Acting naughty around an angel of the lord?! He will simply have to deal some divine retribution.
He enjoys punishing you, but aftercare is absolutely imperative. He could use his grace to heal you, yes, but you like to feel it after. He resorts to traditional methods instead.
disclaimer :: you need to be logged into twitter to access these!! pls do ignore the captions on most posts, they're pretty nasty..
a/n :: if any of the links stop working, let me know and ill try to find replacements!! i definitely have a lot more, i was just too nervous to add too much..
ೄྀ࿐ ˊˎ- Dean W.
the impala has seen and heard many things.
pre!seasons dean.
dean's always been open to trying more.. risky things. (of course, it wasn't loaded.) // c:w - gunplay
that one episode with him as a gym teacher..
ೄྀ࿐ ˊˎ- Sam W.
usually sam is the polar opposite of his brother. public sex is too risky for him, but sometimes, even he has his limits.
sammy doesn't need anything in return, pleasing you is what he likes best.
hes tall, sure, but that doesn't mean hes lacking in inches..
dean want to grab something from the gas station, giving you a few minutes alone..
ೄྀ࿐ ˊˎ- Soldier Boy
ben was known for being.. mean.
ben found out you'd been using a toy to get off. safe to say, he wasn't happy.
bonus :: the winchester brothers dont mind sharing.
𝐖𝐀𝐑𝐍𝐈𝐍𝐆𝐒: smut , closeted dean winchester , m4m , shy!dean , sub!dean , sexual identity crisis , semi-public (bathroom stall) , messy blow job [dean receiving] , 18+ NO MINORS
𝐖𝐎𝐑𝐃 𝐂𝐎𝐔𝐍𝐓: 1400
#𝐍𝐎𝐓𝐄𝐒: not a dude , so pardon my interest on this topic. no details of the guy dean's with , so up to your interpretation !! also this was supposed to be a short fic but I got carried away like usual. lightly edited cause im #lazy
early seasons dean winchester never realized he was playing for both teams all at once. it wasn’t a sudden epiphany, but something that crept in under his skin and stayed there, picking at him until he couldn’t ignore it anymore.
it all started on the night a hunt went sideways... forty-eight hours of grime ground into his clothes, dried blood stiff at the edges of his sleeves, exhaustion sitting heavy behind his eyes.
so once him and sam got back to the motel, and cleaned up, dean did what he always did, finding the nearest, cheapest bar to drink away his feelings.
as he sat there alone, his eyes idly scanned the room, trying to find a distraction. he caught the eye of a pretty girl a few seats down. and like most nights, that would be a cue to turn on his classic charm. but tonight his eyes didn’t stop there.
they drifted past the sweet blonde and locked onto a group of guys around his age sitting at a booth. one of them matching his stare, just a few seconds too long.
a strange, overwhelming rush of warmth hit dean's lower belly. his mind scrambling to process why a guy looking at him like that was making his cock start to grow against the denim of his jeans.
it was the first real time; the sultry focus from another man was sending an electric jolt straight to his groin. the idea of being wanted by a man was something new.
downing the rest of his whiskey in one sharp swallow, dean practically threw himself off the stool, rushing straight into the dim men’s washroom.
dean stumbled over to the sink, placing both hands down on the porcelain edge. he stared wide-eyed into the cracked mirror at his own blown-out pupils and flushed face, his breathing soft and strained.
slowly, his gaze drifted downward to the undeniable, hard tent stretching the front of his jeans. poor dean was nervous— completely out of his depth. his thumbs fidgeted anxiously inside his pockets as he tried to figure out how the hell to make it go away.
all the older brother needed was an easy pickup line, a confident smirk, and a girl whose name he’d forget by morning. he knew how to play that game in his sleep. but this? his brain racked over how to even approach a situation like this, or if he even wanted to.
dean turned the taps on the sink, trying focusing on "non-sexy" things— the mechanics of the impala's engine, the salt lines they needed to pour, cold lore books, anything to make his swollen cock go down. but every time he thought he had a handle on it, he imagined rough hands on him, instead of soft ones. the scrape of stubble against his throat. a deep voice telling him how good he's being.
his hand slid down the front of his jeans, palms smoothing over the undeniable, rigid bulge straining the denim. with his eyes squeezed tight against the glaring fluorescent light, he gently ground his hard length into his palm, a soft, helpless whimper catching in his throat at the pressure.
the man from earlier walked into the bathrom, stopping a respectful but close distance behind dean, looking at him through the glass.
"hey," the guy asked softly, his voice quiet. "you okay?"
dean stared at the ground, his voice barely a whisper. "fucking hell— yea i'm fine."
“you were staring pretty hard out there,” the man said quietly, eyes flicking over dean’s flushed face. “couldn’t help noticing. you looked like you wanted something.”
dean’s throat worked around nothing. he tried to find some smartass comment, but there was no mistaking the yearning in his emerald eyes. the raw, unspoken yes he couldn’t force himself to say out loud.
the man took one slow step forward, then another, until he was right in front of dean.
“have you ever…?” his hand lifted, smoothing a broad palm on dean’s chest, right over the frantic thud of his heartbeat.
dean shook his head, quick and small. “no,” he whispered. “never.”
the guy hummed, low and pleased. his eyes dropped lower, taking in the obvious, bulge still straining against dean’s jeans. leaning in far enough until his lips were barely a breath away from dean’s.
“did you ever think about being with one?” he murmured. . “y'know a man touching you , tasting you...”
dean’s breath stuttered. his cock twitched at the words, leaking against the inside of his boxers. shame and want twisted so tightly in his chest he felt dizzy.
“i… i don’t fucking know,” dean lied, barely audible. but his body betrayed him. he leaned forward just slightly, chasing the heat of the man’s body.
the guy’s hand slid lower, fingertips brushing over the waistband of dean’s jeans. “wanna be a good boy and let me to show you?”
dean’s answer was a broken, barely-there nod. his eyes fluttered half-shut, submissively, silently pleading.
the guy took dean’s hand and tugged him into the last stall, locking the door with a quiet click. as soon as they were closed in, he dropped to his knees on the dirty tile.
he yanked dean’s jeans and boxers down in one rough tug, freeing his thick cock. it bounced out heavy and leaking, the flushed head smearing a shiny trail of precome across the soft pudge of dean’s belly. his dark, unkempt bush curled at the base, damp with sweat.
“fuck, look at this pretty cock,” the guy breathed. “keeping something this nice away from guys like me— that’s a goddamn sin.”
dean’s face burned. “shut up— ah fuck,” he hissed, but the words died in a broken moan as the man leaned in and dragged his tongue slowly up the underside of his veiny shaft, collecting the bead of precome at the tip.
the first deep suck pulled a loud, desperate sound out of dean. “oh fu— fuck.” his hand shot to the guy’s hair, fingers twisting tight in the strands. the man’s throat relaxing as he took dean deeper, nose brushing against the sweaty, musky bush at the base. spit traveled down dean’s balls, and dropped onto the jeans at his ankles.
and then the bathroom door opened. two drunk guys walked in, laughing loudly, taking their time at the urinals. dean’s eyes snapped open, panic cutting through the pleasure.
“wait— there's people,” he whispered frantically, even as his cock twitched harder in the man’s mouth. the guy didn’t stop. he just looked up at dean with dark eyes and took him even deeper, throat squeezing around the head while spit ran messily down his chin.
dean bit his lip hard, trying to stay quiet, but soft, helpless whimpers kept escaping. “fuck i’m gonna—” his free hand pressed against the stall wall, knuckles white. sweat slicked down his lower back. every time the guy swallowed around him, gagging softly but never pulling off, dean felt his orgasm barreling closer.
the sloppy sounds mixed with the thigh pressure made dean unravel. he barely got the warning out before his cock pulsed hard, thick ropes of come spilling straight down the guy’s throat.
dean’s head fell back against the stall with a dull thud, a broken moan tearing from his chest as he came harder than he had. the guy kept sucking him through it, swallowing every drop, milking him with slow, lazy pulls until dean was shaking and oversensitive.
when the guy finally pulled off, lips glossy with come, he stood up slowly. before dean could catch his breath, the man cupped the back of his neck and kissed him messily. dean could taste himself on the guy’s tongue, salty and bitter, and it made his spent cock twitch weakly between them.
“you ever come around here again, ill be here,” he murmured against dean’s lips. then he stepped back, gave dean one last heated look, and slipped out of the stall.
dean stayed behind, back pressed to the wall, chest heaving. his lips felt bitten off. the taste of himself still sat heavy on his tongue. shame and confusion crashed back in hard, but underneath it all was a warm, secret thrill he couldn’t ignore.
“fuck,” he whispered into the empty stall, dragging a hand down his face.
dean knew it wouldn't be the last time.
do not feed my work into AI bots , repost , translate , or alter in any way shape or form.
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