Work Header

first time

Work Text:

"Dean?" Sam walked up beside the Impala, his hands shoved deep into his pockets and his long hair spilling over his forehead, almost touching his eyes. Dean pulled himself out from under the hood of the car and straightened up, quirking a brow at his younger brother. Even though they were four years apart, Sam was the same height as Dean and he found himself wondering when the kid had grown so tall. He smiled at Sam and grabbed a rag that lay on the front bumper.

"What's up, kid?" Dean wiped his hands on the rag and leaned against the front of the Impala, his eyes narrowed slightly as the sun beat down on them. Sam chewed his bottom lip and brought a hand out of his pocket, his fingers immediately going to his hair, running through it slowly. Quirking a brow, Dean slipped the rag into his back pocket and hooked his thumbs into his belt loops. As he watched Sam fidget - his fingers moving nervously from the back of his hair to his bangs, pushing them out of his eyes - Dean breathed in deeply and leaned his hip against the Impala.

"I just, uh, had a question but you're busy so I'll come back later.." Sam's hand dropped back to his pocket and Dean chuckled softly, shaking his head before turning to the car. His hands moved from his jeans to the edge of the hood and he lowered it slowly, letting it fall gently. "Now I'm not busy, so tell me what's on your mind, Sammy." Dean cracked a smile at Sam and their eyes met, before the youngest looked down at the ground again.

"Can we go inside and talk about this?" Dean could hear how nervous Sam was and he nodded slowly, clapping a hand against Sam's shoulder. The feel of Dean's hand against his shoulder made Sam smile a bit and he looked up, their eyes meeting once more. Nodding slowly, Sam turned and pulled away from his brother's touch, listening to the crunch of gravel as Dean followed him. The two of them walked up the stairs and to the room they shared, Sam walking in first, followed closely by Dean.

"So what's up, Sam? What's so important that we have to be inside to talk about it?" Dean teased slightly as he collapsed into a chair in the corner of the room. He kicked his feet up and laid them on the board at the end of his bed and watched as Sam sat on the edge of his own. With both hands, Sam pushed his hair out of his face and backwards, sighing deeply.

"I have a problem with…" Sam struggled to get the words out and he sighed again, gripping two handfuls of his hair. "Masturbation," he mumbled the word and felt his cheeks grow hot, his eyes downcast and set on the carpet beneath his feet. Silence hung in the air and Sam was afraid to look up; terrified to face Dean, in case the eldest thought it was funny, or wasn't taking him seriously. When he finally mustered the courage to look up, Sam stared at Dean, who was leaning forward, his arms resting on his thighs.

"What's the problem? You wait until I'm asleep, in the shower or out somewhere, and you just stroke it." Dean's forehead furrowed in confusion and he lifted a hand, brushing the palm of his hand against his stubble. "I mean, it's easy, Sammy." He laughed softly, studying his brother's eyes quietly before they dropped. Sighing, Dean stood up and walked over to Sam, sitting on the edge of his bed; their knees almost touching.

"When I do it, it doesn't feel good, and nothing on the TV, or those books you have help me… you know, get ready." Sam swallowed hard and nosed the carpet with the tip of his boot, picking at a hole in his jeans. He didn't have to look up to know that Dean was staring at him and he sighed, shaking his head. "Nevermind, it was a stupid question I'm sor—"

"No, it wasn't a stupid question," Dean interrupted as he moved a hand to the side of Sam's neck, pulling his gaze up. "It's just, kind of surprising, that's all." When Sam's eyes locked on his own, Dean smiled and dropped his hand, chewing on his bottom lip. "Tell you what, uh.." Swallowing hard, Dean chuckled and moved his hand to the back of his neck, scratching it lightly.

"How about these? Hold on," he mumbled and lay back on the bed, turning over onto his stomach after a moment, reaching underneath the bed. Sam watched his every move and bit his bottom lip, watching as his flannel shirt slid up slightly, showing the tanned skin underneath. He shifted his hands to the front of his lap and watched Dean sit up and face him again. In his hands, Dean held a stack of magazines that Sam had never seen before. "You can look at one, Sam, it's not going to bite you."

Nodding slowly, Sam reached out, almost reluctantly, and grabbed the magazine that lay on the top. When he brought it back, Sam flipped it open and looked at the pictures, surprised to see that they were only of men. After turning a few more pages, Sam looked up at Dean, who had a small smile on his face, his cheeks flushed slightly.

"You look at these?" Sam quirked a brow and looked back down at the magazine, his eyes scanning over the pictures. He heard Dean chuckle and it made him smile a bit, until he felt Dean's hand in his hair, ruffling it gently. Each time Dean touched him, it sent Sam crazy and he closed his eyes, sighing deeply. "I just didn't want you finding out - not anytime soon, anyway." Dean shrugged and dropped his hand onto his knee, the stack of magazines on the floor beside his bed.

"Tell you what, you look at them, and when you're ready… I'll talk you through it; tell you what I do to make myself feel good. Sound alright?" Dean watched as Sam ducked his head, his bangs falling in front of his face. Chuckling, Dean pushed the dark brown locks away and moved his hand to Sam's chin, cupping it gently before pulling his gaze up. "Don't be embarrassed, Sammy."

"Okay.." Sam nodded and felt Dean's hand fall away, listening to the bed springs squeak as he got up, the soft pad of his boots signaling that he was walking away. Swallowing hard, Sam stood and undid his jeans slowly, kicking his boots underneath Dean's bed as he shoved the denim down his legs slowly. He kicked them away and tugged his shirt off, tossing it onto the bed behind him. Once he was standing in only a tank top and boxers, Sam sat on the mattress and moved back, leaning against the headboard.

Spreading his legs slightly, Sam flipped through the magazine for a few more minutes, one hand turning the pages while the other moved against the front of his boxers. Soon, he was fully hard and panting lightly, completely unaware of Dean sitting in the chair, watching his every move. Swallowing hard, Sam tossed the magazine onto Dean's bed and their eyes met for a second. Dean smiled at Sam and leaned back against the chair, his legs out-stretched and crossed.

"Boxers off, Sammy." Dean's voice was soft and Sam shivered when he heard it, hooking his thumbs into the waistband of his boxers, tugging them down. He kicked them to the end of the bed and lay his legs flat on the bed, his bottom lip between his teeth. Swallowing hard, Dean let his eyes roam over Sam's body and he sighed heavily, his eyes moving up until they met Sam's once more. "Now, grip the base of your cock - yeah, just like that."

Sam wrapped his index finger and thumb around the base of his cock while Dean spoke and felt his face, neck and chest grow warm. He'd had dreams about doing this, watching him masturbate, and to know that it was really happening only made Sam harder. Dropping his eyes from Dean, Sam looked down at his cock and ran his free hand up and down the inside of his thigh, shivering lightly.

"Now, stroke up and down slowly, wrapping your other fingers around the shaft." Dean almost sighed the words out and Sam looked up, their eyes locking for a moment before the youngest nodded, obeying. He wrapped his fingers around his cock and stroked up and down slowly, his breath hitching in his throat as he tipped his head back. Parting his lips, Sam moaned lightly and scratched the inside of his thigh, dragging his nails up lightly.

Across the room, Dean shifted positions, sitting on the edge of the chair with his elbows bent and resting on his knees. His eyes were glued on the scene in front of him, taking in every inch of Sam's gorgeous, perfect body. Swallowing hard, Dean moved a hand to his jeans, pressing his palm against the front slowly, his other hand resting against his jaw. In the back of his mind, Dean knew that it was probably wrong what they were doing, especially seeing as they were both enjoying it, but he didn't care. All he wanted to do was crawl onto the bed with Sam and push his hand away, replacing it with his own as they kissed.

"Good, now move that hand," Dean tipped his head toward the hand on Sam's thigh, as if the kid could see him, "to your balls and cup them gently.." He watched as Sam did everything he said; his large hand cupping his balls, his fingers kneading them slowly. Growling softly, Dean chewed on his bottom lip and leaned against the back of the chair, both of his hands moving to his jeans. As he watched Sam's hands go to work, Dean undid his jeans and slipped his hand in, palming his own cock through his boxers.

"That's good, Sammy.." Dean moaned out, bucking his hips against his hand, watching as Sam tipped his head forward, his bottom lip between his teeth. Chuckling softly, Dean lifted his hips and slid his hand out of his jeans, gripping the pant legs before tugging them down. With his pants around his ankles, he slipped his hand back to his boxers and stroked himself through the thin cotton, breathing deeply.

"Dean…" Sam sighed the words out as his eyes moved from Dean's to his lap, watching his fingers wrap around his covered cock. Shivering, he pushed himself away from the headboard and sat on the edge of the bed, his hand still wrapped around his own cock. Without thinking, Sam stood up and walked over to the chair Dean was sitting in, straddling his legs.

"What are you doing, Samm-" Dean's words were cut off by Sam's lips pressing against his own and he groaned softly at the interruption but didn't protest. Swallowing hard, Sam closed his eyes and moved one of his hands to the back of Dean's neck, gripping it gently as he slipped his other hand down. His fingers ran along the underside of Dean's cock and Sam felt his hands move to his hips, gripping them tightly.

The kiss was slow at first as Sam tested the waters and grabbed Dean through his boxers, a muffled moan filling the space between them. Smiling, Sam pulled away and licked his bottom lip before taking it between his teeth, his hand stroking Dean slowly. He watched as Dean tilted his head back and closed his eyes; listened as he breathed in deeply, his hands gripping Sam's hips even harder than before. As Sam leaned forward, he felt one of Dean's hands move down his thigh, fingers splaying against his skin as he ran them up slowly.

"Dean, I want you to touch me, please.." Sam whispered the words out and listened to Dean moan as he pulled his head forward, eyes locking on Sam's. Smiling softly, he nodded and moved his hand toward Sam's cock, his fingertips barely brushing along the base as the pad of his thumb ran along the underside of his shaft. Sam moaned and closed his eyes, chewing on his bottom lip as he felt Dean's rough, calloused skin rubbing against him.

"C'mere, Sammy.." Dean moved his free hand to the back of Sam's neck and pulled him closer, their lips instantly touching. Inhaling deeply through his nose, Dean wrapped his hand around Sam's cock and stroked it slowly, his tongue lapping against the youngest's lips. Whimpering, Sam parted his lips and slipped his tongue through them, the tip barely grazing against Dean's, sending shivers through his entire body.

Dean wrapped his tongue around Sam's and tilted his head slightly, holding Sam in place as he pushed himself into the kiss. Ignoring the voice in the back of his head, he pushed his hips against Sam's hand, grinding against it as they kissed. Sam could feel his body grow warmer with each stroke of Dean's hand and he moaned into the kiss, slipping his hand under the waistband of his brother's boxers.

Feeling Sam's fingers brushing along his cock, Dean bit his tongue lightly and moaned, pulling away from the kiss and tilting his head back again. It had been too long since he'd felt the touch of someone other than himself, and knowing it was Sam that was touching him, only made Dean throb harder. Swallowing hard, Dean gripped Sam's cock tightly and stroked it harder, listening to him inhale sharply.

"Come for me, Sam…" Dean half-moaned the words out, his fingers tangling in Sam's hair, tugging it gently. He listened to Sam moan louder and gasp for breath, whimpering ever few minutes - when Dean would squeeze his cock. Smiling, Dean wrapped an arm around Sam and shifted them to the edge of the chair, moving his hand off of Sam's cock for a minute. "Wrap your legs around my waist," he whispered, pressing his nose against the base of Sam's throat, feeling his legs slide against his sides.

Breathing deeply, Dean slipped his hand underneath Sam's ass and stood up, staggering a bit before getting a hold of his footing. He walked slowly to the bed, taking small steps until his knees his the edge of the mattress. Reluctantly, Dean leaned down and laid Sam on the bed, pulling his hands away before moving them to his boots, yanking them off quickly. The jeans came off after his shoes, and finally his boxers fell to the ground, before Dean was sitting on the bed, leaning against the headboard.

He spread his legs and smiled, pulling Sam toward him until he felt Sam's shins resting against the back of his thighs. Swallowing hard, Dean moved his hand from Sam's hips to his cock, gripping it once more before stroking it slowly. Sam let out a cry of pleasure and moved his hands to Dean's legs, his fingernails digging into his skin. Dean bit his lip and watched Sam carefully; his eyes were darker than before, and blown from lust, and he grinned slightly.

"Come for me, right now," Dean growled the words out and watched Sam's head fall back, his throat exposed as his hands ran up and down Dean's thighs slowly. His entire body shook as Dean stroked his cock harder, whispering and moaning in encouragement. With one final groan, Sam let loose; coming hard all over himself, Dean, and the bed. Panting heavily, he fell back against the bed and listened to Dean chuckle, feeling his hand fall away.

"Good job." Dean crawled over Sam's body and placed a kiss on his lips before pulling away, wrapping his hand around his own cock. "Wanna make me come, Sammy?" he whispered, moving his lips up and down Sam's neck slowly, listening to him pant and groan. When he pulled away, Dean saw Sam nodding slowly and he grinned, returning the gesture before falling back against the headboard.

Pulling his hand away, Dean spread his legs again and watched as Sam sat up and hunched forward, his hand crawling toward his cock. Shivering in anticipation, Dean chewed the inside of his cheek and kept his eyes on Sam; moving his gaze from Sam's slightly messy hair to his hips, ass, and even his back. Swallowing hard, he lifted a hand and weaved his fingers through the teen's hair, feeling his palm against his shaft.

"Fuck, Sam.." Dean tilted his head back and closed his eyes, his lips parting as he moaned, feeling Sam's hand wrap around the base of his cock. It didn't take long for his body to react to Sam's touch; his legs shook from the moment he felt Sam's warm skin against his cock. Swallowing hard, Dean gripped Sam's hair harder and bucked his hips up when the teen started stroking him.

The seconds turned to minutes and Dean was holding out; making himself last so he could feel Sam's touch even longer. But when he felt hot breath against the head of his cock, Dean moaned loudly and held Sam in place, moving his hips against his hand. Groaning, Dean shoved both of his hands into Sam's hair and gripped it tightly, feeling the teen's tongue against his cock.

"I'm coming.. Sam, oh fuck..!" Dean nearly screamed as he came, getting some of it on Sam's tongue, face, and hand. Panting, he pulled his hands away from Sam's hair and placed them on his shoulders, groaning as his orgasm subsided. Sam chuckled and pulled away, sitting back on his heels as he licked his lips. Breathing deeply, Dean opened his eyes and tipped his head forward, smiling softly at Sam.

"Wow," they both said at the same time and Dean laughed, shaking his head as he grabbed the bed sheet, cleaning Sam's come off of his hand. He handed the sheet to Sam and watched as he wiped his face and hand, a small smile on his face. "Well, now you know how to make me come," Dean whispered and chuckled as Sam dropped the sheet, sitting at the foot of the bed, his cheeks flushed slightly.