This is the first of many possiable chapters. If theres anything you want to see happen let me know. Smut. Not smut. Gay sex. Crossovers. Anything you name it it will happen. Review or PM with comments or anything xoxo

Summary: Dean finds himself alone on a hunt after Sam is badly hurt and resting. After he is taken captive Dean is rescued by a sexy Demon who is an old friend. Smut. Rating-M

Dean watched as she moved, there was something in her movements that showed she wasn't human. The way she fought, the way she moved. There was a glint in her hard, demonic, black eyes that had Dean curious. She brought her long curved blade into the chest of the demon that Dean had been hunting, sending it back to hell.

She paused for a moment, trying to hear any movement. When she decided that there was nothing there she turned to Dean who was tied to a rough metal chair by rusty chains. "Dean," She said, pausing to break the chains, "Winchester. Fancy meeting you here."

"Do I know you?" Dean drawled eyeing the woman who just saved his ass from a five on one demon fight.

"No," She admitted, "But I know you. We all do. I just don't hate you. My name is Cassi," She stuck out her hand to Dean, "I was sent to give you a hand. Since Sam is taking a break."

Dean looked her over once more, Sam had decided to take short break from hunting after having to get a bullet removed from his head, and one from around his heart. Dean had encouraged this break, making Sam stay in a small apartment and just do research for Dean.

"Who sent you?"

Cassi smiled slightly, "John and Jo did, they insisted that I had to go make sure you didn't kill yourself in a crazy ass hunt like this."

Dean paused to take in the woman before him. She was tall and had amazing curves. Her hair was dark auburn and waved down her back and shoulders, she had big green eyes that captivated Dean when they weren't covered by the black of being a demon. "Will you accept my help Winchester?"

"Who's to say you won't just fuck me over?" Dean asked, standing up, he rubbed his sore wrists, which were bloody from the chains he had struggled against.

Cassi smiled, "I'm offended Dean. Don't you remember me?" She purred, "Lets see, May 22 to the 29th, 2014. Does that week ring any bells?"

Dean thought back to May, 2014. He had been in the hospital because he got pretty roughed up. One of the nurses had been a hunter in her spare time. Her name was Cassiopeia and she spent a lot of time with Dean, even breaching hospital code to sleep with him multiple times. She wanted to go hunt with Dean and Sam but she was consumed by a black smoke that Dean found out later to be a very old powerful demon. He thought she'd be gone forever.

"Is that your old meat suit?" Dean asked with a quirked smile.

Cassi laughed a bit at that, "Yeah I put in a special request for it," She smiled.

Dean looked at her, before he smiled a bit. "Wanna get outta here?" Cassi smiled and nodded.

She and dean discarded the bodies before leaving in the Impala, dean driving. Dean and Cassi went on a few more hunts, tracking demons for a few weeks, while Sam was recovering. Dean adjusted to hunting with someone who was supernatural rather well. Cassi and Dean worked well together, Dean felt like she was almost human, that she wasn't completely demon.

Sam wasn't so thrilled that Dean was hunting with a demon, not after Ruby. But if Cassi wanted Dean dead she could have not saved him that day at the hunt where he was outnumbered.

Sam expressed his dislike on the phone while Cassi was out to get food.

"I don't like it Dean, what if she has an alterior motive?" Sam asked for the hundreth time.

Dean sighed, "Don't worry Sammy, you'll be back soon," Dean said, "Just heal. I'll be fine."

Dean could see Sam now, sitting on a hard kitchen chair rubbing the bridge of his nose and sighing at his older brother. "Okay Dean," Sam said, "I'll see you soon right?"

"Course' Sammy. Since your cleared for physical activity i'll be picking you up in a few days when get to L.A."

Dean hung up just as the Motel door opened. "We're leaving to get Sam tomorrow aren't we?" Cassi asked when she locked the door behind her. Dean opened his mouth to say something but was cut off, "He doesn't like me. I'll drive with you to California, but i'll depart from there. Since Sam doesn't like me. I'll always be a call away though."

Dean walked over to where the brunette stood, he put one hand on the back of her head and curled his fingers around her hair. In one swift motion he brought her to him and kissed her full on the lips. He'd wanted to do so for a long while but never had the guts.

Cassi reacted right off the bat and wraped her arms around Dean's shoulders, Dean's hands drop to Cassi's ass, at first cupping it, then pulling Cassi up so her legs were wraped around his waist. Dean brought Cassi to the bed and gently threw her down onto the bed.

Dean pulled off his shirt and slid off his belt. Cassi quickly removed her shirt and jeans. Revealing matching black lace underwear. Dean smiled a cocky smile, "Hotter then I remember," He said appraising her curves, her full chest, her grab-able hips with lustful eyes.

"Stop staring and fuck me Winchester," Cassi said impatiently.

Hasty Dean removed his jeans and slid out of his boxers. He fell to Cassi's lips kissing her had and biting at the bottom one with hard teeth. HIs hands slid to her back and quickly dealt with her bra, he slid down the bed and squeezed her breasts together before attacking the left one with kisses and light nibbles. He made sure each got enough attention before sliding down the bed further, bringing the black lace down with him.

"Well aren't we wet," Dean said before he inserted a finger inside of her. Cassi arched her back as Dean's tongue swirled around her clit. She moaned a happy giggle before she pulled Dean up to her lips. "Come on now Sexy. We've waited long enough, get inside of me," Cassi said with serious eyes.

Her eyes were dark green but glinted with black, normally that would have bothered Dean but he was too consumed by lust to worry that he was about to have sex with a Demon.

Dean did as she asked and entered her, Cassi arched her back at the sensation, her nails dug into Dean's back and she brought her lips to his skin. Dean trusted in and out of Cassi, who was moaning louder with every coming thrust. One thing Dean had always liked about the georgus bombshell of a woman was that she was a screamer, let you know when you were doing a good job.

Cassi brought her nails hard into Deans back, scratching as he thrust into her, Dean brought his mouth to the Demon womans neck and took the soft skin into his mouth. Dean continued to thrust until he felt Cassi constricting around him, her walls getting tighter, that sensation sent him over the edge, they rode out their orgasms together.

Dean rolled off of Cassi and pulled her into his side, she used him as a pillow and they laid there together. Dean falling asleep very fast.

When Dean woke up Cassi was on the phone, "No I didn't kill him Sam, he's asleep. Like he has been for the last five phone calls you made," Cassi said sounding annoyed. Dean stood up and took his phone from Cassi.

"Sam, I am fine. I'm taking a shower, then leaving. I'll be there soon. Don't get your panties in a knot."

Dean could practically hear Sam roll is eyes, "Fine, drive fast."

"Don't I always?" Dean asked, a smirk in his tone.

Once he hung up Dean looked at Cassi, "Shower. Now."

Cassi giggled and stripped off as she hurried to the small glass shower. She turned on the warm water and waited for Dean. When he came in he was fully erect and lust filled his eyes. He grabbed Cassi by a handful of dark Auburn hair and kissed her fiercely. With one hand he took both of hers and pinned them behind her back before he pushed Cassi up against the glass shower wall.

Dean entered her from behind and started to massage her breasts as he pushed in and out of her. Dean fucked Cassi against the glass wall of the shower, his motions were hard and fast, and Cassi was moaning harder with each coming pump.

Dean and Cassi once again finished together, then cleaned themself off using the bland smelling Motel soap. Once they were out and dressed Dean gathered his things so he could go to Sam.

It only took Dean two days to get to California, once he got there he and Cassi parted, she requested to be dropped off at a bar in the sketchier side of town before Dean went to Sam's apartment.

When Sam opened the door he looked Dean over, "You slept with her didn't you?" Sam asked.

Dean rolled his eyes before hugging his younger brother, "I missed you."

"No chick flick moments, Jerk," Sam said as he excepted his brothers hug.

"Can If I wanted, Bitch."

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F.L, Carry on my wayward sons.