Work Text:
Title: I Always Pegged You As A Minnesotan
Pairing: Sam/Dean, Dean/OFC
Disclaimer: Not mine
Rating: NC-17
Summary: Sam was admittedly nervous for this one.
Kink: Pegging
Sam had hung back when Dean chatted up the girl at the bar, slightly pacing back and forth, nodding politely at the other patrons. He had smiled when Dean and the girl both looked up, giving a small wave. He couldn’t hear either of them, but she smiled and nodded and Dean looked back and gave a thumbs up, so Sam guessed things were a go.
“Come on, Sammy, we’ve got shopping to do,” Dean said, walking by him, letting the girl lead the way.
“How did you know she’d go for it?” Sam asked softly, staying close to Dean.
Dean shrugged. “I’m gorgeous. You’re gorgeous. It’s just a threesome Sam, with a little extra help.”
“You really like this?” Sam asked, grabbing onto Dean’s jacket. “This isn’t something you’re just doing to make me happy?”
Dean sighed and looked over at the Impala, where the girl was climbing into the backseat. “Sammy, I’ve done this before you, and God forbid, I might have to this after you. It’s hot, just wait and see.”
“I don’t want her to do it to me,” Sam said as they began walking again.
“Fine then,” Dean said, climbing into the car.
Sam sighed and looked around the parking lot before finally just opening the car door, climbing in.
“Hi,” the girl said from the back, pushing herself up to offer Sam her hand.
“Hi,” Sam nodded, quickly shaking her hand. “Sam.”
The girl grinned and sat back, nodding. “Diane.”
“Great,” Sam murmured, turning back to the front. “Diane,” he said, glancing over at Dean.
Dean shrugged. “So where to, Diane?”
Diane leaned forward again, head appearing over the seat. “There’s really only place around here that would sell what you’re looking for.” She grinned. “Take a right down here, then the second left. You’ll see it.” She sat back and reached into her purse, pulling out her iPod.
Sam brought his thumb up to his mouth and watched out the window, looking over when he felt Dean’s hand on his thigh. He smiled weakly, looking back out the window.
* * * *
“That’s it?” Sam asked softly, grabbing onto Dean’s arm. “Christ, Dean, it doesn’t even look like a dick.”
Dean looked over at Diane, who was grinning down at the hot pink dildo with rotating beads, attached to purple harness. He looked back up at Sam, shrugging. “Come on, Sam, if I wanted real, I’d just get you to fuck me.” He began unbuttoning his shirt, before Sam grabbed onto his hand and stopped him.
“Why are you doing this?” Sam asked, keeping his grip on Dean. “Why do we have to bring somebody else into this? I mean, you’re right, I can fuck you. Why does she need to be here?”
Dean stared at Sam for a moment before yanking his hand out of Sam’s grip and he finished unbuttoning his shirt. “Are you gonna have a major freak-out or something, Sam? ‘Cause if you are, you can just leave.”
Sam shook his head, looking at Dean in disbelief. “I cannot fucking believe you, Dean.”
“So who am I using this on?” Diane asked suddenly, lifting her head.
“Me,” Dean said quickly, shrugging his shirt off. He pulled his t-shirt over his head then quickly undid his jeans, pushing them down. He stepped out of them then pushed his boxer-briefs down. He straightened up and smirked at Sam before walking over to the bed, laying down.
Sam sighed and swallowed hard, crossing his arms.
Diane watched Sam for a moment before climbing onto the bed, leaning down to kiss Dean.
Sam looked away from the bed and watched the wall, squeezing his eyes shut when he heard Dean moan softly.
Dean’s breath hitched when Diane’s mouth attached to his nipple and he reached over to the nightstand, grabbing the lube. “C’me here, Sammy,” he said quietly, holding the lube out to him.
Sam stood where he was, shaking his head slowly.
“Sammy,” Dean moaned when Diane’s mouth wrapped around the head of his dick and he reached out as far as he could.
Sam shook his head again but walked over to the bed, dropping down onto his knees, getting at Dean’s height. “What?” he asked sharply, trying to ignore Diane.
“Help her get me ready,” Dean pleaded quietly, handing the lube off to Sam.
“Dean, no,” Sam said. “I can’t.”
Dean leaned up and gave Sam a kiss, tracing Sam’s lips with his tongue before laying back down, smiling up at him dreamily. “It’s okay, Sammy. It’s okay to like it.”
“It’s weird,” Sam told Dean, shifting to sit on his bottom. “Isn’t it?”
Dean shrugged. “I think we do weird pretty well.”
Sam had to smile and finally he stood up, just to sit back down on the edge of the bed.
Diane grinned and moved out of the way, climbing out from between Dean’s legs and watched Sam pop the cap on the lube, pouring it on his fingers.
Sam rolled his shoulders and teased Dean’s entrance before slipping the first two in, closing his eyes, trying to forget that Diane was there.
Dean gasped slightly and thrust his hips down onto Sam’s hand, shifting on the bed.
Sam twisted his fingers and curled them upwards, Dean crying out loudly. “Shh, s’okay, Dean,” he whispered, rubbing Dean’s stomach with his other hand.
Dean nodded and whimpered, clutching at the sheets. His head lolled over to look at Diane, and the strap-on, and he looked back at Sam. “Better make it three.”
Sam smiled gently and slipped his fingers out, pushing three in the next time.
Dean gasped again, loudly, and his eyes squeezed shut. “God,” he muttered, “right there.”
Sam worked the three fingers in and out slowly, twisting them in Dean, rubbing his prostate. “Okay?” he asked.
Dean nodded eagerly and groaned, low in the back of his throat when Sam slipped his fingers out.
Sam stood up and walked to the head of the bed, leaning down to Dean a kiss, slipping his tongue into Dean’s mouth. “I love you,” he said softly, smiling down at him.
Dean tilted his head up and kissed Sam again, nodding. “Love you.” He sat up and flashed a quick smile at Diane before rolling over onto his stomach and pushing himself up on all fours.
Sam took a deep breath and glanced back at Diane, watching her press her hips forward, Dean letting out a long groan as she entered him. He dropped his eyes down to the comforter, picking at it absent-mindedly.
Dean moaned and pushed his hips back, taking more of the dildo in. His eyes opened slowly and he met Sam’s gaze, tongue coming out to wet his lips. “C’mon Sammy, take it off.”
Sam’s eyes opened wide and he shook his head, looking back at Diane. “I can’t, Dean.”
Dean smiled and shifted his weight off one of his arms and reached out, tugging on Sam’s shirt. “Please?”
Sam nodded jerkily and his fingers slowly began to work, undoing the buttons. He shrugged off his shirt and looked back at Diane again, who was watching Sam out of the corner of her eye.
Diane thrust in hard and Dean jerked, crying out loudly.
Dean gasped and worked his hips back against hers, fingers digging into the sheets. She hit his prostate on the next thrust and he bit down on his lip, trying not to cry out again.
Sam stood up and toed off his sneakers, pushing his jeans and boxers down. He stood there dumbly, waiting for Dean’s next command.
Dean gasped loudly and lifted his head, looking back at Diane. “Sit-- back on your heels.” Diane did as she was told, and sat back on her heels. Dean followed her and sat back on Diane’s thighs, leaving plenty of room for Sam to sit in front of Dean.
Sam climbed onto the bed in front of Dean and smiled nervously, leaning in to give Dean a kiss.
Dean jerked into Sam, reaching out to grasp onto Sam’s arms, trying to keep his balance. He moaned into Sam’s mouth as Diane swiveled her hips up. “Okay?” he asked Sam, pulling back.
Sam nodded, keeping his eyes on Dean. He reached down and wrapped his hand around Dean’s cock, jerking him a couple times.
Dean moaned and thrust up into Sam’s hand before thrusting down onto Diane, fingers digging into Sam’s arms. He let one hand trail down and he reached out, grasping onto Sam’s dick, jerking him to the rhythm of Diane’s thrusts.
Sam shifted on the bed, getting as close to Dean as he could and leaned down, burying his head in Dean’s chest, working his hand with Dean’s, thumb swiping across the head on the upstroke.
Dean’s head dropped and rested on Sam’s, holding him close with one hand, jerking Sam quickly with the other. He pressed a kiss to the top of Sam’s head, smiling against him.
Sam worked his hand furiously, tilting his head to press kisses across Sam’s chest.
Dean moaned loudly at a particularly hard thrust and jerked into Sam’s hand, coming.
Sam licked at Dean’s sweaty chest and thrust his hips up into Dean’s hand, biting into Dean’s skin when his toes curled and he came, shooting onto Dean’s stomach and hand. He lifted his head and kissed Dean, running his hands up and down Dean’s arms, tongues playing at each other. He broke the kiss and laid down on the bed, head hitting the pillows. Under the sound of their heavy breathing and Diane’s hips still working, Sam heard a quiet buzzing noise. “Whassat?” he murmured, reaching up to rub at his eyes.
Dean grinned and pushed back onto Diane, biting at his lip. “That would be her.”
Sam frowned and sat up quickly, glancing back at Diane. “Where is it?”
“In the strap-on,” Dean replied, glancing back at Diane. “What do they call it, Diane?”
Diane thrust up, taking a couple second to get her voice to work again. “Uh…vibrating egg?” she asked, voice rough.
Dean nodded and grinned, turning back to Sam. “Vibrating egg.”
Sam rolled his eyes before flopping back down to the bed. “God. Sex is getting too technical for me.”
Dean laughed and reached down, wrapping his hand around Sam’s half-hard dick. “Well, we’ve still got awhile for you to figure it all out, Sammy. Don’t worry.”