It starts with Sam giving Dean a handjob. They had already been making out and jacking off for each other for a while by then (experience-wise). This night was no different from any other until Sam reached for Dean. Sam had tried before but finally realized not to ask, because asking lets Dean say "no" whereas doing it lets him touch Dean's cock.
The door was locked, it was just them and Dean was laying on his back over the covers, jeans unzipped and underwear shoved down, almost completely clothed. Dean's eyes were squeezed shut and his head was arched back. Sam's just suddenly reached out warpped his hand around Dean's cock. Dean jumped and his eyes shot open but no matter what he said Sam just kept tugging at him.
Sam slid over to sit on Dean's thighs for better access to jack him off. When Dean finally came it was all over Sam's hand and the bottom of Sam's shirt and the crotch of Sam's jeans because of the way Sam tugged (Because even back then he thought being covered in Dean's come was so hot).
That, understandably, broke Dean.
And after Dean came Sam wiped his hand on the crotch of his jeans, rubbing the come in and pressing against the bulge there.
He told Dean it was okay, Dean didn't have to touch him, he was fine. And then he proceded to unzip his pants, right there on Dean's thighs, and jack himself off.
And so for the next week or so Dean is completely fixated on the image of Sam sitting on Dean and making himself come.
And so the next time they have some alone time, which is about a week and a half later, Dean "corner's" Sam. Sam's sitting on the bed watching a movie and Dean grabs him by the ankles and pulls him to the edge. Sam's sitting on the edge and the movie's still on and suddenly before Sam can process Dean's got Sam's pants unzipped and his hand is pulling at Sam's cock, dragging it out and pulling him off.
Sam's all shakey and just kinda falls forward, hands on Dean's shoulders and head down, gasping as his big brother pulls at his cock and tugs and twists just right. It's only maybe a minute before Sam's coming, whimpering and shaking. Dean wipes his hand on the underneath of the blanket and presses a quick kiss to the side of Sam's head while he tucks Sam back into his pants.
Here's a story about the first time Sam jacked Dean off.
The door was locked, it was just them and Dean was laying on his back over the covers, jeans unzipped and underwear shoved down, almost completely clothed. Dean's eyes were squeezed shut and his head was arched back. Sam's just suddenly reached out warpped his hand around Dean's cock. Dean jumped and his eyes shot open but no matter what he said Sam just kept tugging at him.
Sam slid over to sit on Dean's thighs for better access to jack him off. When Dean finally came it was all over Sam's hand and the bottom of Sam's shirt and the crotch of Sam's jeans because of the way Sam tugged (Because even back then he thought being covered in Dean's come was so hot).
That, understandably, broke Dean.
And after Dean came Sam wiped his hand on the crotch of his jeans, rubbing the come in and pressing against the bulge there.
He told Dean it was okay, Dean didn't have to touch him, he was fine. And then he proceded to unzip his pants, right there on Dean's thighs, and jack himself off.
And so for the next week or so Dean is completely fixated on the image of Sam sitting on Dean and making himself come.
And so the next time they have some alone time, which is about a week and a half later, Dean "corner's" Sam. Sam's sitting on the bed watching a movie and Dean grabs him by the ankles and pulls him to the edge. Sam's sitting on the edge and the movie's still on and suddenly before Sam can process Dean's got Sam's pants unzipped and his hand is pulling at Sam's cock, dragging it out and pulling him off.
Sam's all shakey and just kinda falls forward, hands on Dean's shoulders and head down, gasping as his big brother pulls at his cock and tugs and twists just right. It's only maybe a minute before Sam's coming, whimpering and shaking. Dean wipes his hand on the underneath of the blanket and presses a quick kiss to the side of Sam's head while he tucks Sam back into his pants.