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andreafmn · 6 months ago

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Kinktober ⛓️ Day 26

Word Count: 4.0K Paring: Dean Winchester x Fem!Reader Requested by @elizabeth916: "Supernatural" Prompt @kinktober2023: Masturbation WARNINGS: SMUT 18+ (minors DNI), slight voyeurism, vaginal fingering, masturbation, joint masturbation

Summary: After a hard life and a close brush with death via vampire, (Y/N) is taken in by Bobby Singer and taught the way of the hunters, even if that was the last thing he wanted for her. Add Dean and Sam Winchester into the mix, and she's more involved in the hunter lifestyle than before. Now, Dean is always always at odds with the girl. Even if he was the one who asked her to join them, he's always the one getting in her way. Sam says it's because he's in love with her. (Y/N) just thinks he's stubborn. One way or another, she's gonna find out they're both kind of right.

A/N: whoop, still doing this, I will try to finish before this october 🫣🫣 I've only gotten to season 5 of Supernatural so sorry this isn't more canon-centric

MASTERLIST

Constantly being on the road provided little privacy. Being the only girl in a team of hunters made it harder to have some. Being the only girl in a team of hunters that were brothers made it nearly impossible to have any.

But (Y/N) couldn’t complain. The Winchesters were the closest thing she had to a family, and they needed her help.

She had lost her parents at a young age and had made a life for herself as best as she could. She was sent from foster home to foster home until, at eighteen, she met Bobby Singer by chance during one of his hunts.

A couple of days before, she had been kidnapped by a young vampire as she walked from work and took her back to his nest, where she was fed upon from the moment she arrived. She believed she’d die there with nothing to show for her life other than a rundown apartment and a shitty waitressing job.

But just as everything had seemed bleak, Bobby had come in swinging a machete around and killed every single one of the vampires that had resided in the abandoned warehouse. Seeing the girl who was barely clinging to life, the man took her back to his motel and waited until she had regained consciousness.

He was sure she would scream, try to run away, or even hit him. Yet all she did was flutter her eyes open and thank him. She wasn’t afraid, nor was she angry. She had simply accepted what had happened to her as something else she had to deal with.

“You really ain’t scared of everything I just told you?” he had asked her that night as they ate some burgers. “I mean, I just told you that you almost died because of vampires, and you were more surprised that they put pickles in your burger.”

“I’ve dealt with worse shit in my life to find the supernatural unbelievable,” she shrugged. “With how my life goes, dying from a vampire is the least of my worries.”

Bobby had only met one other teenager as nonchalant and used to peril, and he had not been able to help him as much as he wanted to. But he knew he would always regret if he left (Y/N) to her own devices after meeting her. So, Bobby offered her a chance at a different life. Going against everything he had ever believed, he offered her a room at his place and a new job. And she said yes.

That answer had changed her entire existence.

(Y/N) took to the hunting lifestyle rapidly, finding it easier than being an eighteen-year-old girl living by herself in a sketchy part of town. She invested all her time and energy to get stronger and faster, wanting nothing more than to become better and better.

Bobby tried his best to keep her life balanced, especially after seeing what the hunting life had done to John Winchester’s sons, Dean and Sam. For years, he pushed her to have a social life and do things normal young people would. Still, he couldn’t squander her determination. So, when Dean called her up one day to help him and his brother find their father, she quickly agreed, much to Bobby’s dismay.

But once her mind was set on something, there wasn't much he could do; all he could do was hope she’d one day come back safe and sound.

And that was the day she had lost all sense of privacy. The trio jumped from motel to motel, and there was not enough money for two rooms. Thankfully, there always were two beds and sometimes a rickety couch, not that it helped the choking sexual tension between (Y/N) and the older Winchester.

From the moment they met, there was an undeniable chemistry between them. Sure, Dean flirted with anything that walked on two legs, but it was different with (Y/N). He wanted much more than just a one-night lay with her. He wanted the entire package–the apple pie life he’d dreamed of.

But he wanted something different for her—something better than what he could offer. Like Bobby, he didn’t want her involved in the hunting business. He had even begged Bobby not to let her go. But Sam was right. If they had any chance of finding their father, it would have been with her by their side. Just because he had agreed to let her tag along did not mean he didn’t worry whenever they were on a mission. If he wasn’t making sure that Sam wasn’t hurt, he was worried that (Y/N) was, and more often than not, his concern came out more like hostility rather than worry.

Much like their latest case. The three of them were sat at a diner, a giant breakfast spread on the table before them, and the only one eating was Dean. (Y/N) and Sam had their noses buried in books and laptops, trying to gather all information they could about a particular nest of vampires that had made their home in a small town outside of Detroit.

The case was particularly personal for (Y/N). The vamps that had been running amok the town had been the same ones that had almost taken her life many years before. Just like Bobby had told her, they left an item of the person they abducted with a star drawn in their blood at the place they were taken from. The creatures looked for easy targets and always hunted in the darkest corners of the night.

Now, (Y/N) had a plan to get to their nest, but it seemed she was the only one who thought it was a good one. “I’m just saying that it’s worth a try,” she whispered as she sipped her coffee. “I can make myself a target, and they’ll think it’s fucking divine intervention that they got the one that got away. Then you guys can follow and kill them all. I don’t see what’s so bad about that.”

“Are you fucking serious, (Y/N)?” Dean seethed. “They could kill you on the spot. It’s too risky.”

“It’s the only plan we’ve got right now that could actually end this,” she countered. “Even Sam thinks that it’s good.”

“All I said was that it could technically work,” the younger Winchester defended. “But I also agree with Dean that it’s too dangerous.”

“I don’t care if I get hurt as long as we get them.”

“It’s not about you getting hurt, (Y/N),” Dean spat, slamming what was left of his sandwich onto the plate. “It’s about you fucking dying.”

“Well, it’s a risk I’m willing to take,” she countered with the same anger. “It’s my life we’re talking about here, Dean. Not yours.”

“You’re fucking unbelievable!” he exclaimed through gritted teeth as he got up, grabbing his jacket in the process. “I’ll be in the room. I need to cool off.”

Sam and (Y/N) watched as the older Winchester left the diner, a cloud of steam almost visible in his step. It wasn’t the first time he had stormed out that way; it was his standard practice when things weren’t going according to his plan. But that moment, in particular, felt different. The energy was different.

“Okay, he needs to get over himself,” the girl muttered as she slouched in her seat, her arms crossed across her chest. “You guys cannot be the only ones allowed to sacrifice yourselves for the greater good. I know I can get hurt. I signed up for this job just like you guys did.”

“I don’t know who’s more oblivious,” Sam snickered as he popped a slice of bacon in his mouth. “You seriously don’t understand why he acts like that with you?”

“Because he’s a total douche with a god-complex?”

“No, idiot,” he laughed. “Because he likes you and cares about what happens to you.”

“Oh, come on, Sammy. We’ve been through this before,” (Y/N) said. “The only things Dean Winchester cares about are his car and you. I don’t even fall in the top five.”

“Jesus, you’re both just so stubborn,” he sighed, rubbing his temples. “Go talk to him, and then tell me if he doesn’t care.”

“He’s just gonna fight with me.”

“Go, (Y/N),” Sam exclaimed. “And actually talk to him.”

“Fine!” the young woman finally relented. “But you’re getting stuck with the research then.”

“Like that’s ever changed,” he scoffed jokingly. “Now, go.”

(Y/N) took the short walk back to the motel as slowly as she could, kicking a rock in her step as she fiddled with the key. It wasn’t the first time Sam had hinted at Dean’s supposed feelings for her. It had become his one source of teasing material since they had met for the first time. But she had always taken it as a joke, nothing more—just a quip a little brother used to bother his older brother. There was no way there was any truth to it. And if going to the room proved that, then that was what (Y/N) had to do.

As she neared the motel, she caught a glimpse of Baby, and a slight chuckle bubbled in her throat. That car was Dean’s one true love, and she knew that. He treated his vehicle better than any of the women he paraded in and out of their motel rooms or even the ones who never made it out of the bars. Hell, he treated it better than her or Sam at times.

That was the reason she had never admitted her feelings in the almost eight years she had known him. (Y/N) knew they wouldn’t be reciprocated. Dean had never given a single indication that he’d ever share her sentiment. Well, other than Sam’s words. But who could believe him then?

All she needed was one sign. A simple whisper from the universe that he did share in those feelings. That the reason he fought with her so much was because there were so many emotions bottled up inside him that he couldn’t help how they came out. Just one sign.

“(Y/N),” she heard an exhale as she neared the motel door. It was raspy and guttural, and she knew it had not come from the wind. “Fuck, (Y/N).”

She could have been dreaming. In the supernatural world, anything was possible. But the metal doorknob felt too cold in her hand, and the key turned too loudly for it to be her imagination. Behind that door, a scene was unfolding that surpassed her wildest fantasies, and she was the main character without knowing it.

(Y/N) opened the door slowly, pulling it upward to avoid the whining of the hinges, and she came face-to-face with something she could have only dreamed of. In fact, she was sure she had dreamt it before.

Dean was splayed in the middle of her bed, his hard cock in one hand and a pair of her underwear in the other. He ran his hand up and down his length, easing his pumping with the leaking precum that stained him. After every few strokes, he’d bring the piece of fabric to his face, taking a long drag before muttering (Y/N)’s name once more.

His eyes were pressed shut, and his movements were erratic. Dean was close, that much she could tell. She could see it in the way he breathed, in the way his hips stuttered, and the way his skin had grown red and flushed. Dean was reaching his climax with her name spilling from his tongue.

“So fucking stubborn,” he croaked out as his seed spilled all over his stomach. “(Y/N), fu~uck.”

“Good to know my underwear didn’t just disappear three months ago,” she grinned as she finally made herself known. “Didn’t take you for a panty sniffer, Deanie.”

“What the fuck are you doing here?” Dean exclaimed as he tried his best to cover himself. He pulled the sheets from under himself, pulling too hard and falling to the floor with a loud thud. “How long have you been there?”

“Long enough to know who you were thinking about,” (Y/N) taunted as she approached him. His legs were still on the bed, and his jeans pooled around his ankles while the sheet covered the rest of his body. At any given time, she would have made fun of him; tease him until he begged her to stop. But the heat that pooled between her legs had blurred her mind, and all that she wanted was to replace the hand that was working him. “Something you wanna tell me, Dean?”

“God, you’re insufferable,” Dean huffed as he tried to get up. “It’s not what you think.”

“And what do I think, Deanie? What did I just walk into?”

“I just needed to relieve some stress.”

“Oh, and do you always relieve your stress thinking of me?” (Y/N) mewled as she knelt down, her breath hot on his skin as she whispered in his ear. He stiffened up at her closeness, trying his best not to touch her. “See what I think, Deanie, is that what Sam’s been telling me is the truth. That you like me and that you care about me. And since daddy never taught you how to express yourself correctly, you just let everything out when you’re angry.”

Those words ignited a fire in Dean. He no longer cared about his lack of clothing or the situation (Y/N) had caught him in. All he wanted was to regain control. “You think you’re funny, huh?” he growled as he flipped her onto the ground and towered over her. “You think that just because you caught me like this, you know everything now?”

“I know enough,” she smirked up at him as she fought against his grip. “Matter of fact, I can feel it against my leg right now.”

“And you think it’s for you? You think you’re the only (Y/N) out there?”

“I’m the only one you know,” she teased. “And I’m the one whose panties you were sniffing.”

“It’s just a matter of convenience, (Y/N),” he shrugged. “You’re here. That’s that.”

“Are you sure, Dean? Because I’ve never seen you hoard the underwear of any of your past playdates. So, why mine? And why were you jacking off with my name rolling off your tongue?” (Y/N) propped her torso up by her elbows, pressing the tip of her nose to his, testing the waters before diving in. “And what if I told you I felt the same way, Deanie? What if I said that I’ve thought of you with my own hand down my pants? That I’ve edged myself for hours thinking of what you could do to me. And it’s not a matter of convenience for me, Dean. It’s the real deal.”

Dean couldn’t believe what the woman under him was saying. He’d gone so long thinking his feelings were one-sided that Sam only told him the things he wanted to hear. To him, (Y/N) was too smart and too beautiful ever to want to be with him. He wasn’t what she deserved, but now he knew he was what she wanted.

“Tell me you’re messing with me,” he grumbled. “Tell me this is just one big joke.”

“Why do you want me to lie to you, Dean? Is it so hard to believe that someone can feel something for you? That I love you?”

“You don’t mean that,” he continued. “How would you know what you feel is real? It’s not like you have a lot of options on the road.”

“Because I’ve felt like this from the moment I met you, Dean,” she confessed. Her heart had begun hammering inside her chest, begging for a moment of rest. But that was the last thing she wanted. It was the last thing she needed. “Why don’t you want to believe that I could feel this way about you?”

“Because you deserve better, (Y/N),” he muttered softly, almost like he didn’t want her to hear it. “I’m not better.”

(Y/N) knew words were not enough to calm the doubts that drowned his mind, but she knew how she could show it. With a smile on her face, she pulled one of Dean’s hands with her own as she unzipped her pants with her other. She moved their interlocked hands to the wetness that had pooled in her core, pressing his calloused fingers on the aching bundle of nerves that had been begging for attention. “I know what I deserve,” she hissed. “And I know what I want, Dean. I want you.”

“You don’t know what you’re saying,” he argued. But his fingers were telling another story. As if by instinct, his digits had started circling her clit, rubbing circles and shapes over the bud. “I’m damaged goods, (Y/N). I’m no good.”

“And I’m not better,” she added. “We all have a past, Dean. It can’t stop us from living in the present.”

“Is that what you’re doing, then?” Dean chuckled. “Living in the present?”

“We both are, Deanie,” (Y/N) grinned mischievously, knowing she had won him over. “As soon as you give in, baby.”

“You win, then,” he smiled. “For now.”

Dean pressed his lips to (Y/N)’s, savoring their softness and their warmth. It was everything he had imagined and more. They moved perfectly in sync, fitting into each other’s empty spaces like they had been crafted for each other. And maybe they were. Maybe they were part of some divine plan and had no idea. But at that moment, it didn’t matter. It was the fact that they were together that made everything just right.

“So, is this all because of me?” Dean taunted as he teased her folds. “This how you always are?”

“Yeah,” she sighed in pleasure. “I can’t help it when I’m with you.”

“Wish I had known earlier,” he grinned deviously. “I would have been taking care of you, (Y/N).”

“I think we’ve been taking care of ourselves quite well,” (Y/N) teased. “I mean, from what I saw today, you got your system down.”

“Oh, is that so? That mean you got your system too?”

“Well, I have not heard any complaints yet,” she chuckled. “I kind of know my body quite well.”

“Show me then.”

“What?”

“Did I stutter?” Dean smiled. “Get up on the bed and show me how you touch yourself thinking of me, baby.”

Dean slipped an arm under her legs and another on her back and carried her to the bed, where he laid her body softly on the mattress. He kissed his way down her body as he rid her of her clothes, revealing the valley of her skin and marking his path with his mouth.

“Show me,” he said as he kissed down her legs. “Show me what you do.”

“You gotta get off me first,” she chuckled. “Or are you gonna do the work for me?”

“As tempting as that sounds, baby, we gotta even the fields here. And we don’t have much time.”

With a slight chuckle, (Y/N) situated herself comfortably on the bed, propping her back up with a few pillows. Just enough so she could see Dean’s form. He had dragged a chair and rested it just at the foot of the bed, his eyes firmly trained on the woman’s body.

Soon enough, (Y/N)’s hands set off to work instinctively. They roamed her body sensuously, squeezing and kneading her most sensitive spots. As they worked their way through her skin, one rested upon her breast as the other made its way between her legs. She spread her limbs wide, giving Dean the show of a lifetime as her digits spread her folds and gathered her wetness before landing on her aching clit.

She knew it was her hands that were touching her, but her mind quickly tricked her into thinking it was Dean’s calloused fingers running across her body. In her head, it was him that was toying with her clit, it was him that was pinching her hardened nipples, it was him that was bringing her closer and closer to her awaited orgasm.

But it was clear that it wasn’t. Where he sat, Dean had taken his hard cock back into his hand, pumping at the same rate (Y/N) was touching herself. He slid his hand up and down his length, using his thumb to circle the head as precum coated him. In his head, it was her hand wrapped around him, squeezing softly as he tried to ride out his climax as long as he could.

“Fuck yourself, baby,” Dean groaned out. “I’m getting close here.”

“I always knew you were always too fast to the finish line,” she teased, concealing a moan that burst through. “Might just call you two-minute Dean.”

“You really know how to shatter the fantasy, (Y/N),” he sighed. “Just do it, baby.”

“Alright, but stop talking, Dean. You’re wrecking my fantasy here.”

After Dean finally quieted, stifling a moan that was bubbling, (Y/N) continued with her work. The hand that had been touching her chest slithered down her body, sinking into her core as her other hand continued her attack on her clit.

Moans and pants left her as she pistoned into her cunt, her digits curling at the end to bring her that much closer to her climax. She could see how hard it was for the man before her to keep up with her speed. His skin had started to redden and beads of sweat had formed across his body. His chest heaved quickly, and his movements stuttered as he held onto whatever resolution he had left.

“Fuck, Dean,” she moaned. “I’m so close, baby.”

“Me too, sweetheart,” he stammered. “Keep going. Cum for me, baby.”

(Y/N)’s picked up speed as she felt the tight coil in the pit of her stomach threatening to snap. She had done that dance many times before, searching, pushing, beckoning her orgasm to the brink. But it was the first time the Dean that was before her was real, close enough she could touch him. Close enough he could touch her.

It was that very thought that had her yelling out his name as her finish washed over her body, drenching her hands in her essence. Close behind, Dean burst across his stomach with her name dripping from his tongue, his eyes firmly trained on hers.

Dean took her into another rough kiss as they came down from their respective orgasms, her lips so irresistible he didn’t care how out of breath he was. “God, you’re perfect,” he panted. “So fucking perfect, baby.”

“Was that everything you had dreamed of?” (Y/N) teased with a grin. “Was that what was running through your head when I caught you?”

“Something like that,” he chuckled as he caressed her cheek. “It was more of a contact sport, if you get what I’m saying.”

“Well, we still got some time to kill before nightfall,” she offered. “And I’ve got enough for a round two.”

“Don’t threaten me with a good time, baby.”

As Dean kissed his way down (Y/N)’s neck, a knock on the door startled them apart, sending them scrambling for their clothes.

“Guys?” Sam called from the other side of the door. “Is everything okay with you two? We really need to get ready for tonight.”

“Fucking Sammy,” Dean grumbled quietly, his eyes rolling as he slipped his t-shirt on. “We were just getting done talking.”

“No fighting?”

“We were very civil, Sam,” (Y/N) called out, trying her best to swallow the laughter that was bubbling in her throat. The pair had gotten dressed in record time, fixing the bed and brushing their hair. She was slipping on her boots when she whispered to Dean, “We are definitely getting a raincheck on that round two, Dean.”

“Oh, you betcha, baby,” he grinned. “Don’t think I’ve ever been so grateful to be caught in the act.”

“Just be grateful it was me and not Sam,” she smiled before kissing him once more. “Now, let’s go kill us some vampires.”

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