#bottom dean Winchester

[annmariethrush]

we were genuinely so cheated not to have Cas possess Dean. Hell! He could have possessed Sam and it still would have gotten the point across. Jensen would have put his whole jussy into the Cas/Dean hand off, and they could have had a whole convo before or after about how “it’s okay Cas, I trust you. You can have control.” And then references from then on to “when I was in you…” and with Sam? Don’t get me started. Dean being so fucking uncomfortable because Cas looks like his brother. Or the complete opposite where Dean so clearly just sees Cas and keeps having to be like “oh shit” when he gets too close and realizes it’s Sam’s body and it’s weird. So many possibilities and we got none of them 😭

[l1tw1ck]

bottom Dean x dom!top!amab reader

started watching supernatural and good lord they are hot. only writing for dean and sam atm, only on s2

cw: nipple play, orgasm denial, begging

It was late at night, so dark that Dean had to walk around the house with his lighter. He's staying over at your place while he hunts down another creature. He couldn't sleep so he's getting a glass of water. He thought he was being quiet but he thought wrong, he jumps when the light turns on. "Can't sleep, Dean?" You smile.

"Guess not. Didn't mean to wake ya."

"It's fine." You slowly walk over to him, towering over his slightly shorter frame. He leans back into the sink, intimidated for some reason. "I know a way to help you fall asleep."

He knows exactly what you mean. "Be gentle." He smirks.

Dean grips the edge of the sink and leans his head back, mouth agape as you bottom out inside him. You're bigger than anything he's ever taken. He's only used his fingers but still. "Fuh- fuck–" He moans.

"Am I too big for you, baby?" You tease him, sneaking your hands up underneath his shirt to play with his nipples. Dean gasps in shock, ass squeezing your cock in pleasure. "Oh, you like that?"

He grips the sink harder, a short and strained whimper leaving his lips before he bites on the lower one. He feels good but he still has pride.

"Don't be shy," You slowly pull out before slamming into him. He can't help but let out a loud, slutty moan. "I wanna hear you, Dean."

Dean moans uncontrollably as you roughly fuck him, his pre cum dripping onto the floor and a string of curses leaving his pretty wet lips. "Shit!" He cries out, your cock hitting his prostate. "There! Right— fuck~!"

"You wanna come, Dean?" You grip the tip of his cock, preventing him from getting release. "Beg for it. Beg for me to let you come like the whore you are."

"I'm no- not a whore!"

"No? Then why are you taking my cock like you are?"

He whimpers again. His pride isn't worth it. He wants needs to come. "Ple- please! Please let me come, [Name]~! I wanna come~!"

"Good boy." Dean comes right when you release his cock, cum splattering all over the cabinet and floor.

[sailorsallyart]

Starved (tap for HQ)

full piece available on my patreon 💦

wanna be on my tag list? Lmk in the replies!

[petxrpcrkedcar]

i actually cant get over this gif like. his lips???? r so perfect????? so pouty???? so fuckable???????????????? so soft!????

[literally-just-watching-spn]

*dean gets thrown up against a wall and smiles about it*

they really did just say this man is a bottom from the very beginning didn't they?

[thesupernaturallibrary]

sobrecogimiento — Ergonomic

Summary: Dean sees an advertisement for Sam's preferred brand of boxers, which claim that they're designed for those well-endowed in the genital area. Following this, Dean spends an inordinate amount of time obsessing over whether Sam's dick is bigger than his, and then just obsessing over Sam's dick.

more info: here

[masoena]

Summary:

Sam and Dean dabble in BDSM with Sam as the rigger and Dean as the rope bunny, they are both very pleased with the outcome. Sam perhaps a smidge more than Dean because he holds the key.

Day 2 of @spnkinkevents Kinky Dean Winchester Week

Rating: Explicit

Pairing: Sam/Dean (wincest)

Prompt filled: BDSM

[smolderingflame]

Oops I wrote a Supernatural Fic 'Take Me Home Tonight' (Castiel/Dean) By SmolderingFlame

Take Me Home Tonight by SmolderingFlame

Rating: Explicit

Archive Warning: Graphic depictions of violence

Category: M/M

Fandoms: Supernatural

WIP

Relationship: Castiel/Dean Winchester

Characters: Dean Winchester, Castiel, Sam Winchester, John Winchester, Charlie Bradbury, Gabriel, Michael, Anna, Balthazar, Crowley, Benny Lafitte, Bobby Singer, Ellen Harvelle, Jo Harvelle, Jody Mills

Summary: It seemed like it was going to be just another crappy night for Dean Winchester, stuck working the front desk at his father's garage thanks to antiquated ideas of Omegas lacking mechanic skills. That was until a gorgeous car driven by an even more gorgeous Alpha pulls up needing a new battery.

Before he knows it Dean's whole life starts to change and Castiel Novak (or at least that's the name he's given) is much more than meets the eye.

Tags: Alternate universe, Assassins and hitmen, John Winchester being an asshole, Russian Mafia, Minor Character death, Crossdressing, Feminization, Russian Castiel, Omega Dean Winchester, Alpha Castiel, Bottom Dean Winchester, Top Castiel, Twink Dean Winchester, Slutty Dean Winchester, Tattooed Castiel, Protective Castiel, Good brother Sam, Sexism, Slutty clothing, Rough sex, Castiel loves Dean (and vice versa), Butt Plugs, Claiming, Knotting, Mating Cycles, Possessive Castiel, Romance, Comedy, Sugar Daddy Castiel, Sugar Baby Dean Winchester, Dean Winchester deserves nice things, Slut shaming, Cock slut Dean Winchester, Castiel/Dean Winchester first kiss, Crime Lord Castiel, possible Mpreg, Older man/younger man, Daddy Kink

[gwiyeounsonyeon]

Can’t stop thinking about getting Dean Winchester to wear a vibrating plug, (I’m thinking of season 1-2 Dean) he’d look so pretty lips red and swollen eyes all glazed over, if you tease him enough he would definitely beg for you,

I’m so horny help-

[sweet-heart-jack]

Can anyone give me season 4 destiel smut please with maybe top! Cas/ bottom dean please

[l1tw1ck]

dean winchester consumes my mind LAWDDD I beg for anything with that man, surviving off of scraps looking for more top male reader x dean 🤕

- 🛸

No Longer a Mentor

Sub!Bottom Dean Winchester x Top!Male Reader

☆ Word Count: 1,512 ☆

After spending his young adult years with you, his mentor, more than his father, Dean found himself falling for you. He eventually made a move and forever changed the dynamic of your relationship

🕯️: well luckily for u, i just finished this draft :3

CW: Age Gap, First Time Bottoming, Blowjob, Fingering, Frottage (Sort Of), Creampie

Dean’s known you for a couple years, you're a friend of his dad’s and a fellow hunter. You became his mentor in place of his father, who often hunted on his own and left Dean in your care. You liked to stay in your state since the area was basically a supernatural magnet while his father preferred to travel the country so he chose you to finally allow Dean to stay in one place for more than a week. If you were anybody else, Dean would've been annoyed that his dad didn't take him along despite his age and experience. Instead of going to college, Dean spent those years learning to hunt with his father and mostly you. Thanks to all the time you spend with each other, his allegiance to you is almost stronger than his allegiance to his father. He hangs on your every word and treats you like a god. It's thanks to you that he finally accepted his bisexuality. But he doesn't want to tell you that.

He first started feeling differently towards you when you started to become more physical with him. You often hold onto his shoulder with your strong hand or pull him out of the way by his waist and it drives him crazy. He so desperately wants to feel your hands on other parts of his body and vice versa. Your voice makes him weak in the knees and you sound especially attractive when you've found your prey. You're much older than him but he can't get rid of his feelings for you. He tries his best to be content with just having a crush.

After you two had dinner, you decided to drink with him. The two of you laughed and talked over a few cans of beer and deepened your relationship further.

“You ever been in a relationship, [Name]?” Dean asks, slightly tipsy.

“A few. I mostly slept around in my college years and experimented a bit with other hunters but in the end I decided to marry my job instead.”

“Why?”

“I wanted to marry someone I could tell everything to so I tried dating within my circle but none of the hunters seemed to click with me in the ways that really matter.”

“That makes sense…then you probably haven't…” He trails off.

“I probably haven't what?”

“Had sex…lately……”

You laugh. “No, I haven't. Honestly, I think getting laid would really help me. It's been a rough couple weeks.”

“I…” Dean gulps. “I could help with that….if you don't mind…….being with a guy..”

You look at him in surprise. “You're drunk.”

“I’ve only had two cans and a half…You know I don't get drunk that fast.”

You look at him differently, no longer with the eyes of a mentor. “You’ll bottom?”

Dean nods.

You smile in amusement. “I might be a little rough, can you handle that?”

He nods again, more enthusiastically this time.

“Come here.” You motion for him to come over to your side of the table. He stands in front of you. “Kneel.” You order. Dean immediately kneels, his cock steadily growing in size. You unbuckle your belt and pull down your underwear. Dean stares at your cock in awe, body heating up as he watches you jerk it to its true size.

“Fuck. You’re big.” He breathes out.

“Too big?”

“I can handle it.” He says, licking his lips.

“Attaboy.” You run your hands through his hair. Dean blushes. “Ever done this before?”

“Never..” His eyes are trained on your length.

“Is this your first time with a man?”

“Yeah…”

Your gaze changes. Dean shivers in arousal. “How long have you wanted this?”

“A long time…I’ve been…fingering myself, in case we….” He looks away.

You grin, turned on by the thought of that. “You'll have to show me that some day.”

Dean’s face gets redder.

“Now, let me see how you suck cock.”

He's so hard right now. He opens his mouth and slowly swallows your length. He makes a dragged out moan in pleasure as he feels your thickness enter him. Pre cum leaks out of his cock as he imagines how it’ll feel in his ass. He bobs his head up and down enthusiastically, mimicking his past girlfriends by simultaneously swirling his tongue around your shaft.

“Fuck–” You moan. “That's it– good boy.”

Words can't express how happy Dean gets when you praise him.

“You're better at this than I expected, baby.” You smile at his cuteness. He can't hide how pleased he is. “You like sucking dick, don't you? I never thought you’d be a cock slut, Dean.”

He moans. He’ll happily be your cock slut. He pulls away and licks your length in a very sexy way, gaining more confidence thanks to his elevated horniess. “I love your cock, sir.”

“Of course, you’re my cock slut.” You press your hand against his cheek. “Stand up and take your clothes off, I wanna use your other hole.”

Dean’s cock throbs even more. He stands up and quickly removes his clothes, shivering under your hungry and lustful gaze. You pat your lap and he quickly sits on top of you, your shafts pressed against each other.

You grope his ass. “I don’t have any lube..” You trail off, mesmerized by his soft butt.

“I already fingered myself earlier.” He smiles.

“Good boy.” You praise him. “Then spit’ll be enough. Say ‘ah’.” You bring two fingers into Dean’s mouth. He sucks on your fingers in the sluttiest way he can before you take them out and gently push one of your saliva covered fingers inside his soft hole. You give him a moment before adding the second, then you start to finger him.

Dean lets out the prettiest moan you’ve ever heard. “[Name]~” He arches his back and subconsciously thrusts his hips, his cock rubbing against yours. “Your- yours feel so- fuck~” He groans. “So much better!”

You moan as well thanks to the sudden friction. You bring him into a sloppy kiss, the temperature between the two of you steadily rising. Dean pulls away first, more desperate for air, and presses his forehead against your shoulder. “Don't stop– mm- gonna come~” He whimpers. Your fingers find his prostate, an immediate gasp of pleasure leaving Dean’s lips. He throws his head back. “There! Yes!” He moans, grinding against your cock even faster. The combination of his moans, his expression, and his cock against yours all contribute to bringing you to closer your orgasm.

Dean comes first, cum splattering over the two of you. Yours comes second thanks to the amazing look on Dean’s face.

“You're so fucking sexy, Dean, you know that?” You take your fingers out and knead his ass.

“I know.” He gives you a kiss. “I want you inside me.”

You lift Dean up and slowly lower him down on your cock. You both let out noises of pleasure as you penetrate him. He bites down on his lip, thoroughly enjoying the feeling of his ass stretching to accommodate your girth. Once you bottom out, you give him time to get used to it. “Your cunt feels fucking amazing.” You groan. It's hard to hold yourself back but thankfully for you, Dean has no intention of waiting any longer. He places his hands on your shoulders and starts riding you. He quickly loses his momentum as the pleasure begins to overwhelm him. You help him out by grabbing his waist and doing the work for him, allowing Dean to fully enjoy himself.

He knew anal sex would feel good, especially because it's anal sex with you, but he never really had an idea of how good it’d feel until now. Now he's completely blissed out and only able to moan like a slut. It's especially thanks to your quick and rough speed that he's unable to think properly. You couldn't get yourself to go slower even if you tried. His ass just feels way too good.

“Your ass is perfect, Dean–” You groan. “So fucking good-” You hold him and stand up then gently place him on the table after clearing it of the empty cans. You rut into him like a monster, so horny that you feel like you could fuck him all night. You can never get enough of him.

Dean arches his back and shakes as ropes of cum spurt out of his dick. You know you should stop, or at least slow down, but you can't. “‘M sorry baby, fuck–” You moan, hanging your head low as you find your orgasm approaching. “‘M gonna come inside, okay? Gonna fill up your tight fucking cunt with my seed–”

Dean’s conscious enough to understand you. “Ye- yes!” He grins. He's been wanting to know what it feels like to get creampied. “Co- come inside!”

Encouraged by his words, you spill your cum into his warm and welcoming hole. Your thrusts come to a stop and the two of you start to catch your breaths.

“That…was so fucking good.” Dean says, leaning back.

[monsterfluffersrus]

Double the pleasure, double the fun

My first contribution to the MONSTERFUCKER fest.

[petxrpcrkedcar]

dean winchester so pretty when he cries

[bottomdeanbigbang]

sign ups open!

Since this mod has been slightly sleep deprived, Author Sign Ups for this years Bang will remain open until midnight EST on March 19th!

With that being said there are a few minor changes in schedule, just giving more room for this clerical error, but it works out in our authors favor! Below is the updated schedule!

[thesupernaturallibrary]

Heaven's Full And Hell Won't Have Me by whiskeydays

Summary: Knight of Hell Dean is on a killing spree throughout the Midwest when he makes a pit stop in a town that turns out to be much more interesting than Dean would have thought. Who is the mysterious Father Winchester and why does he seem to be immune to Dean's powers?

[masoena]

Dean deals with his storm of emotions by forgoing booze in favour of finding himself a Dom to regain his equilibrium after he and Sam split ways following the horsemen debacle and Sam's questionable choice of demon blood as a drug of choice.

This is day 1 of Kinky Dean Winchester week @spnkinkevents

Rating: Explicit

Relationship: Dean Winchester/Original Male Character

Prompt Filled: Cockwarming / Fuck Buddies