Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/ works/455805. Rating: Explicit Archive Warning: Underage Category: M/M Fandom: Supernatural Relationship: Dean_Winchester/Sam_Winchester Character: Dean_Winchester, Sam_Winchester Additional Tags: Underage_Sex, Top!Sam Stats: Published: 2012-07-10 Words: 787 ****** How Many More Times ****** by myoldsupernaturalaccount Summary The first time Dean lets Sam fuck him, instead of the other way around. Sam is sixteen. Dean loved Sam.  Dean loved fucking Sam, his little ass clenching hard around him as his brother moaned like a five-dollar whore and drew him deeper with his ankles locked behind Dean’s waist.  Dean loved being on top. Dean also loved Sam’s cock.  It was beautiful, thick and long and especially large on Sam’s lanky sixteen-year-old frame, and Dean couldn’t stop thinking about feeling it inside him.  He fantasized about Sam fucking him when he jacked off in the lukewarm motel shower, one hand twisted behind him to get two fingers inside himself, but it wasn’t ever enough.  Dean wanted more, and he resolved to get it. Sam was on top of Dean almost as soon as they got inside the room after the endless car ride from the high school, all soft lips and roaming hands, and he tugged Dean down to the bed on top of him, shedding his clothes and immediately trying to get Dean’s hand between his legs, searching for his fingers to prep him.  Dean grabbed his wrist with one hand and pressed the other flat against Sam’s chest where the fabric of his shirt gapped open, half-unbuttoned. “Stop,” he said firmly, stomach twisting as Sam’s expression turned confused- hurt, and then his brother’s lips were parting in a little “oh” of understanding as he flipped them over so Sam was lying across Dean’s chest and Dean’s legs were splayed wide around him. “Fingers,” Dean reminded the stunned Sam, and that snapped him back to the present, a slow smile spreading over his face as he kissed Dean again and wet his fingers in his mouth.  Dean bit his lip in arousal at the memory of those pretty pink lips around his cock instead of long, slender fingers, but then Sam was pressing those long, slender fingers inside him, two at once, which burned a good burn that he pushed back against, lifting his hips up the mattress to give Sam a better angle, his head falling back against the pillows. Sam’s confidence grew by the moment, kissing over Dean’s chest, mouthing at his nipples and smiling every time his older brother gasped or moaned.  He began to tease, dragging his fingers in and out, scissoring experimentally, until Dean was all but writhing beneath him, whimpering unashamed little pleas for his baby boy to please fuck him already, please, please, oh God please. Dean always insisted they use a condom, because who knew what he might have and he didn’t want his Sammy catching whatever it was, and he was pleased that Sam remembered that rule.  Sam’s fingers were clumsy as he fumbled the condom on, taking way too long as far as Dean was concerned, but soon enough he was trying to get into a good position as Dean propped his own hips up with pillows - he knew Sam liked to fuck face-to-face the best. Sam grit his teeth and groaned as he carefully eased himself in, again taking way too long, but Dean was tight, very tight.  Dean felt like he was splitting in half by the time his baby brother was seated entirely inside him.  It felt a million times better than his fingers ever did.  He yanked Sam down for a kiss, fingers tangling in that stupid shaggy hair as they breathed hotly into each other’s mouths.  Dean rocked his hips, urging Sam to fuck him already, and his brother seemed to get the message, starting slow, almost like he was afraid to hurt Dean, but with more encouraging moans and hair pulling from Dean he got into it more and more, until their hips were slamming together with every hard thrust. Being a sixteen year old boy, it didn’t take long at all for Sam to climax, gasping against Dean’s neck as he came hard inside him.  Dean didn’t care that he hadn’t come yet.  This was for Sam.  It was always for Sam. Sam, however, did seem to care, because almost as soon as he’d pulled out and thrown away the condom he was wrapping his long palm around Dean’s dick, stroking him with a trembling hand.  It wasn’t the best hand job Dean had ever gotten, but it was Sam, and Sam was smiling against his lips and his cum soon dripped over Sam’s lovely fingers.  Dean was only dimly aware of Sam wiping his hand on a bunch of tissues and then he was curling up against Dean’s side, slender limbs tangling with Dean’s. They were silent for a long time, eyes closed, hearts matched beat for beat, and then Sam spoke. “I’m gonna fuck you every time I can get you alone,” he declared. Dean laughed.  “We’ll see about that, baby boy.  We’ll see.” Please drop_by_the_archive_and_comment to let the author know if you enjoyed their work!