Chapter Text
“Dean!” Y/N moaned out at he brought her to orgasm with his tongue and fingers. He hummed in response, licking up her juices and smacking his lips at her delicious flavor.
“Love the sounds you make,” Dean hummed out happily as he kissed his way up her body to her lips, “Love how you look when you cum for me.”
She ground herself against his hard and leaking cock, desperate to be filled by him. With another deep kiss, he slid inside her, both of them moaning at the feeling of being connected. Y/N reached up and cupped his face in her hands.
“I love you, Dean,” she whispered and Dean groaned, capturing her lips once more.
Dean woke with a start and a gasp, groaning and wiping his eyes. It was another dream, just a dream. He had had them frequently. Sometimes it was sex, sometimes it was fixing things at the farm, sometimes it was watching movies or making dinner. But it was always her. Y/N never left his thoughts, asleep or awake.
Realizing he wouldn’t be getting back to sleep anytime soon, Dean shuffled off to the showers. He took himself in hand, working himself over as his favorite dreams and images flashed through his mind. It seemed to be how he started off every day since returning months prior.
I should have stayed, he thought, berating himself as he quickly got dressed for the day. But as always, the guilt of thinking of such a thing - of wanting something like that for himself - took charge and he brushed aside the thoughts of her once more. Not that it would last very long.
When they first returned to their world, Sam had tried ribbing Dean a bit on his newest fling. Dean was quick to correct Sam, anger lighting his features, as he explained in no uncertain terms that Y/N was so much more than a fling. It shocked Sam. He hadn’t seen Dean react to passionately over someone since he swore Sam to never bring up Lisa and Ben again.
As he watched his brother slowly become consumed by his grief over missing her, Sam realized just how serious it was. It reminded Sam of when he lost Jess. He still struggled with it, many years later. He didn’t want that for his brother. Especially considering Y/N wasn’t dead. She was just…somewhere else.
Sam thought things would change after they defeated Chuck. They were free. But Dean couldn’t, or wouldn’t, enjoy his freedom. He needed Y/N. With a sudden flood of determination, Sam began to make a plan.
Sam had packed a small backpack for the trip. Luckily, they had kept the grimoire from the witch that hexed Dean to begin with. He had told his brother he was going on a weekend sabbatical, planning to hit up a museum and theater nearby. Dean barely mocked him, simply acknowledging Sam’s intentions with nonchalance. It only reaffirmed Sam’s decision to carry out his plans.
Hunkered down in the small hunting cabin, Sam prepped the spell, seeing the portal open in front of him. He tucked the grimoire back into his bag, along with the needed ingredients should he need to try and open it again. Along with a few other necessities tucked away, Sam slung the pack on his back, securing the straps and letting out a long breath before walking through the portal.
“Come with me,” Dean whispered before she could speak, turning to face her with a pained expression, “Come with me, Y/N.”
“Dean,” she sighed, her heart swelling from his words, “I can’t,” she whispered with a broken voice, “You know I can’t. I would love to, I really would. But my life is here, my home is here-” she cut herself off, shaking her head as she lowered her gaze, trying to muster the strength not to cry.
“Then I’ll stay,” Dean stepped close to her, one hand finding her side as the other cupped her face, bringing her eyes back to his, “I’m not ready to let you go.”
“You have to go, Dean,” she smiled at him with watery eyes, “You’re needed there. Sam and Cas need you. That world needs you.”
He dropped his forehead to hers, his eyes closing as he let out a long sigh. He knew she was right, but it didn’t make it any easier. In the time he’d spent with her, he realized she was everything he’d ever wanted. He’d dared to think of more with her, a future with her.
But as with most things in his life, it was just outside of his reach.
“I know,” he finally admitted, opening his eyes and letting them take in every detail to be burned in his memory. He closed his eyes once more as he leaned in, giving her a sweet kiss, saying all he couldn’t in words.
She hummed, returning the kiss, allowing herself to get lost in the feel of him. As he pulled away, too soon for her liking, a quiet sob left her lips, the tears finally silently working their way down her cheeks. She was surprised to see a lone tear streak down his own.
“Goodbye, Sweetheart,” he breathed out, reluctantly releasing her and wiping his face. He gave her a tight, forced smile and a nod as he made his way to the portal.
Y/N woke slowly from her slumber on the couch. She wiped a stray tear from her eye as her mind so cruelly reminded her of possibly one of the greatest mistakes she’d ever made - letting Dean Winchester go.
She forced herself from the couch, tossing the throw to the side as she rubbed her hands over her face and through her hair. After Dean left, she tried to stay busy with the farm. She got a lot of work done around the property, bringing it near back to its full glory. But it never ceased the thoughts of Dean. Everywhere she turned she saw him - fixing the fence or tractor, sitting down to dinner after a long day.
A few days before, she had put the property up for sale. She knew she couldn’t keep up with it on her own. But a bigger part was that she saw Dean and their interactions everywhere. It was killing her.
I should have gone with him, she thought to herself for the millionth time. She was quickly becoming her least favorite person. Who the Hell says no to Dean Winchester?! She couldn’t even watch the show anymore because of her grief. Some fan you are!
A knock at the door pulled her from her musings. She jumped in place, as she always did when a knock came. They weren’t common and she always hoped that maybe it was Dean on the other side, coming back for her. Glancing down at her wrinkled pajamas, she shrugged, not caring a whole lot as she ran her fingers through her tangled hair in an attempt to tame it, before opening the door.
Her breath caught in her throat. There’s a Winchester on my porch. But it was the younger of the two. A quick glance around told her he was alone and she took a step back, silently welcoming him into her home.
Sam gave her a small smile before entering the house, looking awkwardly around the living room before turning back to Y/N.