Random Supernatural one shots

Three is better than one

People always say don't bite off more than you can chew, that advice would've been wise to follow in this current situation.Somehow Dean had convinced you to let him and Castiel have their way with you, more or less a bet. Dean and Cas made a bet with each other, who could make you call out their name the loudest, who could make you cum first, hardest, and most, who could give you the most pleasure. Castiel was reluctant, but agreed seeing your confused face as you were sprawled out on the bed, half naked.Dean had you seated on his lap, and his lips on your bare neck. Castiel pressed a soft kiss to your clothed clit, making you squirm. Dean leaned to your ear.

"Be still for 'em baby." He whispered, nipping your ear. You turned your head to kiss him on the lips. Dean shoved his tongue in your mouth and groaned a little as your hips lifted to Castiel, then fell onto his erection that pressed against your ass. Castiel, unhappy at the no attention, moved your underwear to the side and sucked your clit in his mouth. You broke the kiss to moan loudly and push against his mouth. "Take her hips." He said to Castiel, who complied quickly pinning your hips to Dean's. Dean hooked his arms under yours, lifting them above your head, giving Castiel a perfect view of your body.

"Isn't she beautiful?" Dean asked huskily. This was slowly turning into sex, not a contest, but sex. Castiel lifted his head, much to your protest and gave a low groan.

"Gorgeous," He breathed. Castiel's eyes went from your body to Dean. In an instant he moved forward and kissed you, then moved to beside your head to Dean. You moaned lowly, hearing them kiss wetly and they both gave a grunt.

"Dean... Castiel..." You whined rubbing your legs together. Castiel broke the kiss with Dean and moved to you. Your lips collided, and Dean's lips bit and sucked at your neck. He released your hands and slid them down your naked torso. You moaned in Castiel's mouth. You hooked one arm behind you around Dean's neck, grabbing his hair. The other hand reached forward and grabbed Castiel's dark hair. Castiel took no time taking off your panties and sliding a hand along your mound. You threw your head back on Castiel's shoulder. Castiel moved to the opposite side of your neck. Dean and Castiel kissed your neck, until their mouths met. You moaned hearing them moan. One of Dean's hands moved to Castiel's hair, the other moved to his boxers, pushing them down slightly. Dean broke the kiss and Castiel snapped his fingers relieving all of your clothes.

You jumped feeling both their erections touch you, front and back. You closed your eyes and your stomach fluttered at the promise of both of them being inside you at the same time.

"Please, Dean Cas... I need you both." You whined. The Angel looked back at Dean, then looked back at you.

"Same time?" He asked. "Front or back?"

"Please yes thee same time, do both, please I need... just please." You whimpered moving your hips back and forth grinding on both men. The both moaned and Castiel snapped his fingers again. Dean's hand suddenly came to your 'back door' his hand was slick and warm. one finger traced around the hole then pushed in. You gasped and ground down slightly.

"C-carefuuuuull....I'm sensitive." You whisper causing Dean to groan and slowly push another finger in. You clench around him and moan highly at the odd feeling.

"Tell me if it hurts, god you're so tight." Dean groaned into the crook of your neck, now grinding against your lower back.

"(y/n)." Castiel grunt's your name. You turn your head to see a messy haired, wide eyed, pupils blown, lips wet and swollen. You moaned again and nearly came. Castiel smashed his lips against your and the hand in his hair tightened.

"Fuck, Dean." You whine breaking the kiss as he pushed in a third finger. It stung slightly, but when he started moving them it felt somewhat better. "I'm ready, please." You tug on Dean's hair, hoping to egg him on. Dean nodded and pulled his fingers out, leaving you empty.

"Wall?" He asked Cas. Castiel looked back and nodded. Dean moved you into Castiel's arms and he stood up. Castiel stood with him, and they moved to a wall to brace you against.With Dean's back against the wall, your back on Dean's chest, and Castiel's chest on your chest you were sandwiched between them. Castiel entered first and moaned lowly pressing his forehead against your shoulder. Dean leaned forward pressing a kiss to the top of his head. Next it was Dean's turn, he was careful, considering you'd only had anal once. Once he was in to the base, he nudged Castiel's head with his.

"C'mon Cas. Fuck (y/n) you're so tight." Dean groaned. Castiel moved up and kissed you fully his hips started to move. They started out as when one was in you the other was out, never having you empty. Eventually they decided to go the same quick pace.

"CASTIEL DEAN!" You cried out hitting your first orgasm. The tightness was too much for Dean and he quickly came. Castiel groaned and finally released last. Castiel heaved you off of Dean, Dean pulling out of you in the process.

"Stand for me, princess." Castiel whispered letting your legs drop to the floor. You were shaky, but were able to stand. Dean and Castiel switched places, to where Castiel's back was on the wall and Dean was in front. Dean hoisted your legs up around his waist and easied you to Castiel, who's arms wrapped under your ass to support you. Dean smiled and pressed his lips against yours, taking a minute to just kiss you. It wasn't until Castiel ground up to your ass and whined did you break the kiss.

"Sorry honey." Dean murmured and leaned forward kissing Castiel as he entered you. You gasped at how hard he was. Castiel pressed in and groaned. They began to move, as they did before starting out at different paces then matching up. The continued to kiss and you make the mistake of turning your head to look at them. It was probably one of the most sexual things you've ever seen. Both of their eyebrows were drawn together as they made out. You could see a slight bulge in Dean's mouth, where Castiel's tongue was sliding around in his mouth. The corners of their mouths glistened with saliva, some of it glistened on their chin. You moaned loudly and clenched around them coming a second time. Both men smiled and Dean opened one eye. He broke the kiss and his eyes flicked from Castiel to you.

Castiel got the message and somehow, someway, they pressed their lips together again and looked over at you, keeping intense eye contact. Your head tossed back on Castiel's shoulder, your body overwhelmed with scenes. They stopped thrusting and instead lifted your body on their erections. You fell forward onto Dean this time and moaned loudly into his neck, biting down. Tears brimmed your eyes.

"D-Dean... Cas.... I can't I-I can't," Your voice came out horse, whiny, and breathy. Dean moaned out syllables that you couldn't make out. Behind you Castiel was murmuring one word, it was possibly enochian.

"Ozien," Over and over again. You clenched again and came, tears of pleasure falling from your eyes. Dean came quickly after along with Castiel. You slumped and breathed hard, small whimpers. Behind you Castiel continued to whisper that word. Dean panted heavy and peeled you off of Castiel, they both pulled out of you, making you wince. Castiel snapped his fingers cleaning all three of you. Dean sighed and walked to the bed with Castiel trailed close behind.

Dean laid you down in the middle of the bed and crawled in beside you, Castiel crawling on the other side of you. You turned to kiss Dean, the Castiel, then they both leaned forward kissing each other. They wrapped their arms around you, both placing a kiss on your cheek.

"Cas?" You ask quietly. Castiel hummed."What were you saying?" Castiel sat up looking at you and Dean with a smile.

"You're both mine. No one else." He breathed. Dean groaned quietly next to you and squeezed you harder. Castiel kissed your forehead then Dean's.

"I love you both." You breath.

"Love you too." They both said.