A/N: This is my first ever fic, so concrit is more than welcome. :) Please let me know if you think I should add any other tags.

Dean threw his bag down on the motel floor and shrugged his jacket off. They had just wrapped up a case and he was exhausted.

"I'm going to grab some food," Sam announced, grabbing the keys and heading out the door.

"Later," Dean said, cracking open a beer and sitting down on the bed.

As the sound of the Impala faded into the distance, Ruby walked over to the table, pulled out a chair, and sat down. "So...question."

"Shoot," he replied, taking a sip of his beer.

"What is your opinion on... polyamorous relationships?" she asked.

He stared at her blankly for a moment. She rolled her eyes and reiterated, "Polyamory, as in 'more than one lover'."

"Ah. Well, as long as everyone's cool with it, I see no issue." He took a sip of his beer, then looked back at Ruby, confused. "Why do you ask?"

She stood up and walked over to him, leaning down so they were eye-to-eye. "I like you Dean," she admitted. "And I know you like me, too." She smirked. "I see you sneaking peeks when I'm in a towel, and I see you checking out my boobs... and my ass... all the time."

Dean chuckled, looking around nervously. "Well, I won't lie, I think you're very attractive." He met her gaze. "But you're my brothers girlfriend."

Ruby sat down on the bed to Dean's left. "Dean...Sam and I have discussed this," she said.

"You've discussed...seeing other people?" he asked, shocked.

"A bit more specific than that, but, yes..." She turned to him and put her left hand on his chest. "Dean..." She softly finished with, "It's okay."

She slowly ran her fingers down his chest, stopping at his waist and kneeling down in front of him.

He gulped as she brought her other hand over to unfasten the button of his jeans.

Ruby slowly unzipped his fly and shimmied his pants down a bit. Through his boxers she could see his large bulge. "I knew you'd be excited." She smiled, gently sticking her fingers in the waistband of his underwear and pulling them down.

There it was- Dean's dick, in all its glory. She'd been waiting for this for a long time. As soon as she and Sam had gotten together and she started getting to know Dean better, she'd wanted him as well. She put her left hand on Deans waist, rubbing his side, as she slowly took his cock in her right hand and, leaning down, gave the tip a small flick with her tongue.

Dean shuddered and let his head fall back as he tried to stifle a moan.

"You can't hide your pleasure from me," she smirked. She touched the tip of his cock with her tongue again a few more times before taking his head in her mouth.

Dean looked down at her, biting his lip. The inside of her mouth was so wet and warm, and it had been so long since he'd had his dick sucked.

She sucked and teased for a few minutes before suddenly taking as much of him in her mouth as possible.

Dean gasped, throwing his head back again. "Shit.."

Ruby moved her head forward and back, running her tongue along the underside of his shaft, continuing to rub his side with her fingers. She then ran her right hand along the inside of Deans thigh, gliding her fingers towards his balls. Dean shivered. Just as she started playing with their underside, the hotel door flung open.

"Forgot my- What the hell?"

Ruby jumped up and spun around to face Sam, who was standing in the doorway in shock. "Sam!"

As fucked as this situation was, Dean couldn't help being really

turned on by the whole thing. He frantically shoved his erection back into his underwear and stood up to button his pants.

"Sam, man I'm sorry, she said it was cool with you, and before I could even-" Dean stammered.

"Cool with me?" Sam exclaimed.

Ruby moved towards Sam. "Baby, you know how sexy I think your brother is. Although not as sexy as you of course." She leaned in to kiss him and their tongues danced for a minute before she pulled back. She then put her head on his chest and he put her arm around her.

Dean stood there in shock. "What the hell is going on here?" He tried to get the image of his cock in Ruby's mouth immediately before she kissed his brother out of his head.

Sam looked at Dean, then back at Ruby. "Babe, I know we talked about this, but I hadn't found the right time to talk to Dean about it yet. I didn't think you were just going to go for it!" He raised his eyebrows and looked at Dean. "And I was certain Dean wouldn't go for it."

Ruby shrugged. "I couldn't wait," she chuckled, winking at Dean.

Dean shook his head in disbelief. "Wait a minute, you mean you've discussed her making a move on me? Am I the only one who thinks this is crazy?"

Sam laughed, walking away from Ruby and towards Dean. "Dean, I guess it's time I told you this, but I'm a little more..." He paused. "...adventurous, than you would think."

Dean stared at him blankly. "I don't understand."

Ruby walked over as well. "Dean..." She looked him straight in the eye. "Share me with your brother."

"What?"

"Come on, we can all hunt together by day, have amazing sex by night..." She started to unbutton her shirt.

God, she had great tits. He looked at Sam who smiled and gave a small nod.

As embarrassed as Dean was, he couldn't ignore how turned on he was as well. The boner painfully pushing against his jeans wouldn't let him deny that. He looked around nervously, threw his hands up, and said, "As crazy as this all is... how could I say no?" He chuckled.

Sam smiled and walked over to the table, picking up his wallet. "Well, I'll let you two finish getting acquainted. I'm going to go get dinner."

He gave Ruby a quick kiss, smiled at Dean, and left.

Deans eyes followed Sam out the door, then they focused on Ruby. "Well that was weird," he said aloud to himself.

She smiled and walked toward him, putting her arms around his neck, kissing him. He hesitated for a moment, then put his hands on her sides and kissed her back. Her hair was soft and smelled like strawberries. He pulled her shirt off and broke free from the kiss, looking down at her perfect tits. He placed one hand on each one and squeezed them, leaning forward and kissing her neck, down her collarbone, stopping right above her breast. "God, you're fucking beautiful," he growled.

She giggled and pulled his shirt over his head. He quickly undid his pants and kicked them off, instantly appreciating the release of pressure on his erection. He then turned his focus to her pants, sliding them down. She pulled them off and threw them on the floor. She then turned around and Dean reached up and unhooked her bra. She turned back around and slowly peeled it off. Dean bit his lip as she revealed her perfect, round breasts. He grabbed her waist and kissed her hard, moving the both of them towards the bed. She laid down and he climbed on top of her, pulling off his underwear as quickly as possible and throwing it to the side.

Dean leaned forward and nuzzled her neck, inhaling her scent. She was so sexy and smelled so good. He started kissing her neck again, making his way down past her collarbone, to her nipple. He squeezed her boobs as he licked and sucked on her left nipple. She gasped and he could feel her moving her hips beneath him. He ran one hand down her side, down her thigh, and in between her legs.

Ruby bit her lip and let out a little sigh. Dean slowly inserted a finger between her, where she was nice and wet, and started slowly playing with her clit. She moaned, trying to hold back. "You can't hide your pleasure from me," Dean mocked. He stuck two fingers inside her and she quivered. He played with her with his right hand and he kissed her and played with her right breast with his left hand. She pulled away from their kiss, and looked Dean in the eyes. "Please, I want you to fuck me."

Dean wanted to wait but he couldn't. Hearing her beg to be fucked like that was too much for him to handle, especially with how long it had been since he'd gotten lucky. Hunting took up a lot of time and energy.

He grabbed her shoulder and rolled her over onto her stomach. He then grabbed her waist and she inched her ass up in perpetration for doggie style.

Dean kneeled behind her and stroked his cock. Ruby had such a perfect ass and her pussy was beautiful. He leaned down and gave it a quick lick.

She bucked and gasped. "Dean, please!"

He definitely couldn't wait anymore. He grabbed her by the waist and slowly inserted the tip of his dick into her. She let out a wavering moan. As soon as the head was in, he slammed the rest in, filling her up. She gasped and grabbed the sheets and he moaned, throwing his head back. "Oh fuck, Ruby, you feel so good," he said through gritted teeth.

He pumped vigorously, squeezing her ass so hard he was sure he would leave a series of small, fingerprint-sized bruises. Ruby buried her face in the pillow, moaning. "Harder, Dean," she gasped, and he happily obliged.

A few minutes passed and Dean was pumping away, and he started to feel himself getting close. He slowed down a bit. He wasn't ready to come yet. "Faster," she begged.

"I don't want to come yet," he said, pulling in and out, nice and slow.

They heard the engine of the impala pull into the parking lot.

"Shit!" Dean exclaimed.

"No," Ruby said, "don't stop."

"But Sam-" he protested.

"Trust me!" Ruby gasped, "keep going." She clenched her vaginal muscles around his cock.

Dean shivered and let out a pleasurable sigh. "Holy shit..." He started pumping again.

The doorknob turned and Sam walked in, closing the door behind him. Dean froze.

"Don't stop on my account," Sam laughed. He set everyone's dinner down on the table. "I see you two are working up an appetite," he joked.

Dean started again, slowly. "Dude, how are you ok with this?"

Sam walked over to where they were fucking on the bed. "What can I say, I like watching her get fucked by other men. Don't I, Ruby?"

"Mhmm," she mumbled in agreement.

Dean stared at his brother in shock, but quickly turned away when he remembered he was balls deep in Sam's girlfriend and eye contact was proving to be extremely awkward. He was starting to go soft; talking to his brother was kind of ruining his mood.

Sam grabbed Ruby's hair and lifted her head up, kissing her hard. Deans eyes widened. That was more arousing than he expected... He felt himself getting hard again, and he began thrusting again. Ruby moaned into Sam's mouth, and in turn Sam grabbed one of her tits, giving it a hard squeeze. He then stood up and started undoing his pants.

"Whoa whoa whoa, what are you doing?" Dean asked nervously. But he didn't stop thrusting.

Sam looked up at him. "When she said share, she wasn't joking." He smiled as he pulled down his jeans and underwear, revealing a cock larger than Deans. Dean felt a little inadequate, but he kept it to himself. Sam roughly grabbed Rubys hair again and lifted her head. "Open."

Ruby obeyed and Sam shoved his dick into her mouth. She started sucking and licking as Dean continued thrusting from behind.

As much as he didn't want to admit it, Dean was extremely aroused by he and his brother sharing the same girl. Filling Ruby from both ends...it was driving him wild. Her pumped harder as Ruby moaned onto Sams cock. The vibrations made Sam shudder as he fucked Rubys face.

A week ago when Ruby suggested this whole thing, it had turned Sam on like mad, but he never thought Dean would go for it. And now here they both were, fucking Ruby from both ends. He felt his dick hitting the back of her throat and he threw his head back, moaning.

Dean felt himself nearing orgasm. He tried to slow down but Ruby wouldn't allow it. When he did, she thrust her hips onto him, fucking herself on his dick, so he figured he might as well just finish.

He leaned forward. "Are you ready? I'm gonna come," he gasped.

She nodded, still sucking hard on Sam's dick. Dean couldn't believe how much she could fit in her mouth.

He thrust harder and faster for a few seconds and he felt that familiar feeling in his stomach, before exploding inside Ruby. He shuddered. "Oh, fuck..." He froze for a moment before slowly pulling out.

Sam was approaching climax too. He had fantasized about this the entire time he was getting dinner, waiting for their food with an uncomfortable boner. He thrust one last time, hard, emptying himself into Rubys mouth. He moaned loudly and slowly slid out of her mouth. She licked the last bit of cum off his cock and swallowed. "Mmm, so good, as always, Sammy." He grabbed her hair and leaned down to kiss her, tasting himself on her tongue. "I fucking love you," he said through clenched teeth.

"I love you too, Sam," she purred, lying back on the bed.

Dean was already getting dressed. The heat of the moment gone, he was already starting to feel embarrassed.

Sam pulled up his briefs, then his jeans. As he buttoned them up, he asked, "So Dean, how did you like it?"

Dean stared at him for a minute before shaking his head and saying, "That was insane. I can't believe we just did that."

"So what do you say? Wanna make this a thing?" Sam asked.

Dean got up to grab another beer. He cracked it and turned to Sam. Smiling, he took a sip, and said "How could I say no?"