a/n: My friend gave me this fabulous headcanon the other day and I cannot stop thinking about it so here it is, my first ever Wincest fic. Enjoy!


John, Sam, and Dean had been on the road for a few days chasing after a demon case in Oregon and finally stopped to stay in a motel for a few hours so John could get some real shut eye. John was asleep in one of the beds; Sam was sitting up and reading in the other. Dean soon figured out that day-time television was awful and decided to skip out for a while. He had quietly grabbed his jacket and was halfway out the door when he turned back to Sam.

"If Dad wakes up, tell him I went to get a soda," he whispered.

Sam looked up from his book. "Where are you going?" he whispered back.

Dean smirked. "I saw some girls a few rooms over when we were driving in." He saluted with his first two fingers on his brow. "Wish me luck," he added cockily before ducking out. Sam stared at the closed door and shook his head lightly, muttering a quiet "whatever" before returning to his book.

Dean slunk back into the room a few minutes later with a grim look on his face. He glanced at the beds and noticed one was empty.

"Sam?" The younger Winchester hummed in acknowledgement. "Where's Dad?"

Sam shrugged. "Said he needed a drink, woke up right after you left," he answered without looking up from his book. "So how'd it go?"

"With the girls?"

Sam closed his book and tossed it onto the table between the beds. "No, the earthquake," he quipped sarcastically.

Dean sighed and rubbed the back of his neck. "She said she wanted someone more 'experienced.'" He plopped down on the bed next to Sam. "What does that even mean?"

Sam chuckled and shook his head. "How many girls have you even kissed Dean?"

Dean's eyes darted around the room and he turned his head to hide the furious blush that was forming on his cheeks. "U-uh, tons, Sammy," he stuttered. Dean hadn't really been able to get with that many girls because of their family's travelling.

But then it occurred to him. There was someone he could "gain experience" with and he spent more time with that person than with any girl he'd ever met.

And he was sitting in this very room.

On this very bed.

Mere inches away.

Dean grabbed Sam's shoulders and before either of the brothers could really process what was going on, he planted his lips onto Sam's rather forcefully.

Sam froze for a moment before pushing his brother away with a shove to the chest.

"What the hell, Dean?!" Sam shouted as he scooted away and dramatically wiped his mouth with his forearm. Dean stepped away so fast he fell off the bed before he could catch himself. He looked up at his younger brother from the floor, tears daring to spill from his eyes.

"I'm s-sorry, I just…" Dean muttered. He should have figured that Sam wouldn't let him practice on him. It's weird to kiss your brother, he knew that now. Dean sighed and stood to leave but as he turned he felt a hand on his arm, stopping him.

"Sam, what are you—" Sam cut off his question with a gentle kiss. The younger Winchester pulled back with a smirk and stared at Dean who was completely dumbfounded.

"You really haven't kissed that many girls," Sam said matter-of-factly.

Dean quirked an eyebrow at Sam. "What?"

Sam chuckled; hand still on Dean's arm. "You don't just attack," he instructed, taking a small step closer to his brother. "Gently, Dean," Sam whispered before softly pushing his lips back on Dean's. Dean kissed back fervently and Sam stopped.

"You never listen." He slid a hand onto Dean's jaw and brought his mouth back to his own. "Gently," he repeated with emphasis. Dean nodded shortly and slid his eyes closed as he kissed his brother again, taking into consideration Sam's instructions. "That's it," Sam whispered before letting Dean kiss him again and again.

Hours passed in time that felt like minutes, Dean and Sam still wrapped in each others' arms on the bed, kisses moving from lips to necks to shoulders to chests. Dean was nipping the skin above Sam's waistband when the roar of an approaching engine split the two. The brothers scrambled to locate their discarded shirts as the jingle of keys could be heard from the door. Dean had just pulled his black tee over his head when John came into the room.

John placed the six pack of beer on the table with a thud. "We're heading out after dark," he announced unceremoniously. Dean and Sam nodded and began packing the semi-freshly cleaned weapons into the duffels, ignoring the blushes on each others' faces.