Dean Winchester Angst - Blog Posts

The Hookup Henley

Summary: Dean is struggling with the Mark of Cain. Y/N, his best friend, wants to make him feel better. Will she succeed? What happens when the mark takes over?

Pairing: Dean x female Reader

Category: Angst, smut, fluff, 18+

Word count: 5.1k

Warnings: Alcohol consumption, explicit sexual content, semi-public sex, penetrative sex, both protected and unprotected sex (Wrap it up!), MoC!Dean

Prompts: 

“I’m too old for this shit.”

Night club

Dean’s green Henley

Square filled: Friends with benefits @spnmixedbingo 

A/N: This story contains smut! Do not read if you are under the age of 18! I wrote this fic for @libre1rose8 300 Follower Celebration! Congratulations again, my friend! 💕 You deserve every single follower and so many more! 😘 I hope you enjoy my contribution to your challenge (that totally took on a life of its own) 💗 Dividers by the talented @talesmaniac89 😊

Dean Winchester Masterlist

SPN Mixed Bingo 2021 Masterlist 

“Come on, Dean, just try it! For me. Please?”

Dean tossed his head back, sighing in exasperation. “I’m too old for this shit.”

Y/N walked into his bedroom, coming to a halt in front of him. The older Winchester brother was sitting on the floor, leaning back against his bed, a stack of books and papers settled in his lap. Y/N placed her hands on her hips, gazing down at him with her tongue stuck between her teeth.

Afficher davantage

“Whispers of the Past.” [2]

Dean Winchester x Fem!OC

Series Summary: A Case gone wrong years ago for Evelyn and her old hunting team has Haunted her for years, the horrors of that fateful day still engrained into her mind; Meeting the Winchesters was just some slither of hope for Evelyn, distracting her from her own bloody Past. That is, Until one day her old mentor's Partner calls her up and mentions that someone is killing off the rest of the members from Evelyn's old Hunting Team, she feels the memories pooling back into her mind and she is forced to recount everything that she just tried so hard to forget to the two people she trusts the most.

Characters: Dean Winchester, Sam Winchester, Castiel, OC's.

Chapter Summary: After Madi Drops the Bombshell that Chris is Miraculously Still alive after falling off a 13 Foot Cliff Drop, and that he is Killing off the Rest of their old Hunting team, Evelyn Tries to Sneak away from the boys to take care of the Situation before they Find out her big Secret.

CW//TW: mentions of Murder, mentions of Insanity, mentions of mental disorders, mentions of Child abuse, Past Child abuse, Past Mentions of Grooming, Kidnapping, torture, Murder, mentions of Ghosts and a Vampire Nest, panic attacks, Nightmares, flashbacks, Hallucinations, Obvious relationship between Dean and my OC, concussion, head wound, visions, Convulsions, Evelyn murders someone, mentor OC goes insane, drugging, the Police think Evelyn murdered some of her teammates, Dean Defends Evelyn, Evelyn and Sam are best friends.

A/N: Credit for the Header goes to @valeska-25

“He’s Alive?”, Evelyn’s Voice echoed through the phone in disbelief, “Madi, How? he fell off a Thirteen Foot drop.” her voice was Bordering Concern and Fear, no one Human could Survive all of those Jagged Rocks on the way Down; Madi let out a Shaky Sigh, “It’s weird, when I saw him he had no wounds whatsoever.”

“He must have missed all those Jagged Rocks on the way down and Hit the water, Swam to the Surface.” Madi said; now that was Pure Luck with how Insane and Scared Chris was at the time of that Incident. “He Must still have the after Effects of that Demon within him, Otherwise he wouldn’t have Gone after the old Team.” Evelyn Voiced her thoughts on the situation, She Received an agreeable him on the other end of the Phone.

“I agree with you Lyn, I’ve Collected the Remaining Members of the Hunting team, right now There’s only eight of us left; We’re hiding down at the Safehouse.” Madi Explained, Evelyn Remembered that Old Safehouse, Chris had Introduced it to her when he first took her in and was Training her. “That’s good, you all need to Steer Clear of that Hunting Ground we were on during the Incident, he’ll probably Search there first.” Evelyn Remarked.

There was a Stagnant Pause for a Minute.

“Lyn, I’m concerned about you though.” Madi said, her soft tone almost made Evelyn wanna cave and tell Her exactly where she was; but that would only risk her life and the Winchester Brothers’ lives. “Don’t worry about me.” she spoke quickly and ended the call before Madi could Protest.

Evelyn Went over to her desk, Pulling Out an Old Map of the Hunting Grounds from that Night. She looked at the area’s She had Circled in Previous Research of the area, She was going to have to sneak out without alarming Both Sam and Dean, She Didn’t need them Involved in her Shady and bloody past.

So Evelyn Started packing a Bag, Filling it with her Weapons and the Most Important things before Grabbing her heavy Jacket because in that area of Kansas it was specifically cold and snowing, she Quickly Left a Written note to Dean, Apologizing for what she had to do now; and then she Unlocked the latches of her window and Hopped out.

And then She Just Started Running.

←←→→

Dean and Sam found her note an Hour after she Snuck out, Reading the Contents of it made Dean’s Heart Clench Painfully for Evelyn.

‘Hey boys, I know you must be super confused Reading this, but I trust that you’ll trust me to do this on my own; I have to do this, There are things about my past that I haven’t told you, Dark and Bloody things. Now I know this probably won’t keep you guys away, because both of you are Stubborn as hell; but If you do follow me, Just know that I am sorry for everything that you’re about to find out.’

Of course as Expected, Dean Proposed the Idea to Track her down and Follow her wherever she was going off in Such a hurry; Even though Sam was Hesitant because it sounded like She wanted to do this alone, he agreed because She also might be heading into Danger.

So they Both Started Searching Evelyn’s Room, Sifting through all of Her Obviously Personal Belongings.

Finally Dean found the map that you had Haphazardly tried to hide in your Clothes Drawer, he Pulled it out looking at the spots you had Circled. “Hey Sam, Over here. I found something.” He called Sam over.

She were heading for your Old Hunting Grounds, Which she had mentioned in some Drunken Stories completely by accident.

Sam Noticed her Unlatched Window, “And it looks like she’s Going there by foot.” Sam Noted.

“Well let’s Jump in baby, and get over there now.” Dean said, he wanted to get to Evelyn Fast before anyone bad did.

←←→→

Evelyn had made it Halfway by the Evening, the sun Just setting, she was sure both Dean and Sam had already Started on the way to these old Hunting Grounds with the Impala.

She Internally Snorted at how stubborn the Two were, always Causing Trouble.

Evelyn Settled Down at a couple of Trees to stop for the night, if she kept going like this she’d only Burn herself straight to Exhaustion and never reach the hunting Grounds, fortunately she found it pretty easy to fall asleep.

Already tired from the Day’s Events, Her Eyes slipped closed and She fell into a Deep Slumber using her bag as a pillow.

“Now Hold it Steady, Lyn. Don’t mind the Kickback, I’ll catch you kid.” Chris’ Voice Flowed through the cold air, a younger Version Of Evelyn Pointing a Gun at a Target Painted onto a Tree, he was currently teaching her how to fire off a Gun correctly and have Perfect aim. Evelyn was Nervous, but she Slowed her Breathing closing her eyes for a Solid Minute, Calming her racing Heart.

Bang!

Evelyn had Shot a Bullet from the Gun so Smoothly, Seeming so easy to do, even Chris was Impressed with her Output. “Damn Kid, I knew you had Potential in you. You’re a Damn good Shot.” Chris Praised her, Evelyn practically beamed at the Praise not even noticing Madi right behind her who had a Proud Smile Plastered on her face, seeing Her as the child she never had the chance of having.

Once again though, the Seemingly Perfect and happy Memory was Changing again, the sky Turned into a Blood Red once more as Chris’ Eyes Turned Black like a Demon’s eyes; his Voice was Strangled And Gravely, a wound was open in his neck, in the shape of a bite wound from a Demon; his Vocal cords torn and Ripped half way out of his Throat. “You’ll never be able to save him, Evelyn. He Belongs among us now, your Precious Mentor is a Demon.” the Voice hissed.

“And it’s all your fault.” the Voice said once more before it let out a Horrible snarl, Lunging at Evelyn Just about to bite into her—

Suddenly Evelyn Launched awake again, Sweat rolling down her face. Another Nightmare, once that changed her happy Memories again; Evelyn looked up realizing it was Early in the morning, it was time for her to get to walking again; She didn’t know if the boys were Close to her yet.

Evelyn Gathered her things and kept on Marching Straight through the cold Ground, her boots Crunching as She did so, the smell of the old Hunting Grounds nearby always Brought back Simpler times back to her, when Chris was just her Friendly Mentor, before Everything went down.

And She didn’t just mean when the Demon Screwed with his head, she had always Sensed something a little off with Chris, Always being Close to her, having his wife teach Hailey Instead Of Teaching her Himself, Chris almost demanded to be close to Evelyn every second of Every Day; Had Evelyn Just Listened to Lucas’ Warnings she would of Realized that Chris had Been Grooming her the Entire time.

It made her sick to her stomach to remember that every sweet praise that left his lips was just to get her closer to him, he couldn’t go one day without being close to Evelyn, or Touching her.

Evelyn shook her head, Ridding herself of that Horrid Memory that was stuck in her brain; she Tried to focus on something else but Her brain Couldn’t help but go into another Flashback.

“You’re so Pretty Lyn, you know that?” Chris had said one day while coming into her Private room, while she was trying to sleep; Evelyn didn’t know what to think, she was still a Teenager who was Vulnerable at this moment. “So much prettier than my wife.” he added, Sitting on the edge of her bed.

Evelyn was Pulling the Covers closer to her chin, Chris was acting weird, he wasn’t usually like this. Chris Chuckled, Using his hands to Snatch the Blanket Right from her body Revealing her in a nightgown; Evelyn Swore she heard Chris Growl right then.

“Do you always have to be so Tempting, Darlin’?” What was he Talking about, when Had she ever Been Tempting anyone; how was a Teenager Tempting him with anything at all, Chris shouldn’t even be Tempted by this at all. “God, I bet you want it too, Don’t ya?” he asked, his Hand Reaching To Touch Evelyn’s Upper Thigh before Madi Busted through the Door.

“Chris, What the hell are you doing!” She screeched, Mortified at what she was seeing, Her Stomach Curling In disgust at the Sight, “Get your Disgusting hands off of that Girl!” she yelled, Dragging him off by his hair, roughly letting go causing Chris to Bash his head against the wall. Madi gave Evelyn a soft, caring look as she covered her back up.

The only Thing Evelyn saw through teary eyes was Madi Dragging her Husband by his hair.

Once again Evelyn Shook the memory again, She doubted Chris Ever Loved her like a Daughter; he only Felt Sexual Things for Her.

Evelyn’s Thoughts were Interrupted When She heard Two Pairs of Footsteps barreling Right towards her, before she could turn around someone Wrapped their arms around her and Tackled her to the Ground, she was Twisted around to See it was Dean Straddling her.

“Can’t Outrun us, Sweetheart.” Dean Said, with a Smirk Plastered on his Face, Meanwhile Sam was Rolling his eyes at Dean’s Obviously Childish behavior.

Evelyn Shoved Dean Off of her before Standing up, “You Guys Can’t be here, you’re gonna Put everyone in danger!” she hissed at them, Swatting Dean’s Hands away from her face.

Before Dean Or Sam Could ask her Who she was Talking about, a familiar female Voice was Heard a few feet in front of them.

“Lyn, are these those Winchester Boys you were talking about?” they all turned to see it was Madi Who was talking, Still alive and well.

Evelyn Glanced back to see Dean and Sam looking at her with Arched Eyebrows, as She Awkwardly chuckled.

She had a lot of Explaining to do.

«»

Madi Gratefully led them to the Safehouse, if the Winchester Brothers were Out here now in their Old Hunting Grounds, then it was safe to say Chris was going to make them a Target as well, Sam and Dean Didn’t argue with Madi seeing as it would be no use since Madi was a mother Hen.

Stepping into the Old Abandoned Cabin, Evelyn saw the rest of her old Hunting Team, Gathered together amongst a few Children as well, they were cuddled up to a Couple of the Adults who were keeping them cozy and warm.

The first one to remember Evelyn was a young Adult named Lana, Who immediately charged at Evelyn, Hugging her tight. “Lyn! You came back!” She Screeched With Happiness; Evelyn Returned the Hug, rubbing Lana’s back as she did.

“Yeah I did, I’m making sure You’re all safe.” She said, Lana was the Newest member of their old Hunting Group, after the incident Madi wanted to keep the team going, possibly train younger members who wanted to be Hunters without the Trauma that Chris would always Project onto his ‘Students.’ Madi would Always send letters from Lana.

“Who are they?” Lana asked, motioning towards Dean and Sam who were just standing Awkwardly at the Cabin Door, Dean had a Look of Slight Betrayal on his face while Sam had that Same Puppy Dog look in his eyes staring at the young Hunters and Children all gathered around the fire. Evelyn gave Lana a smile, Perhaps it was time for her family to meet the two most Important Guys in her life.

“Well the Big tall Guy is Sam Winchester, He’s My best friend; I would Trust him with my life if I had to.” She Responded, Smiling back at Sam before moving on to Introduce Dean. “And this is Dean, my best friend and my Absolutely lovable Boyfriend; I would also Trust him with my life.”

“Wow, you have a boyfriend now? Shocker.” Someone else, with a Cold Mannered Voice said from the corner of the room in the Darkness; a Woman with Straight black hair tied up in a Ponytail and Snake Green eyes.

Evelyn Immediately Recognized her, one of her Rivals; and She Recognized her on a Personal level. The woman’s name was Blaire Thompson, same Age as Evelyn.

Chris’ Niece.