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 🤕
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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.

















