Let's Make a Deal
Inspired by this from kansaskissedlips on Tumblr:
You don't even understand how hot it is when Dean lifts his taller, bigger little brother onto a counter, table, dresser, etc, and just goes to town, making Sam squirm and writhe and his legs are wrapped around Dean and he's biting his lip and whimpering and pleading and bargaining for an orgasm
"Fuck, Dean, c'mon."
Dean's mouth, pressed hard against Sam's neck as his teeth bit down, curled into a smirk. "Not 'till I say, baby boy." He worked three fingers back and forth inside Sam nice and slow, fucking him like he had all night.
And he did.
Sam's body was sheened with sweat, little hairs sticking to his forehead. Dean had been at this sweet, slow sexual torture for exactly one hour and fifteen minutes, by the clock on the wall.
One hour and fifteen minutes of Dean pulling out all the stops, making Sammy lose his fucking mind—and not letting him come.
Sam grabbed the headboard and pulled so hard it bent it forward, fucking himself onto Dean's fingers. "Come on. Please. I can't take anymore."
Dean twisted his fingers inside Sam, and ghosted the fingers of his other hand over Sam's cock, so hard for so long the head was nearly purple. "Poor baby. Wanna come so bad it hurts, doesn't it. Feels like you're gonna die?"
Sam gasped, "Yeah."
Dean grinned. "So… what'll you do if I let you come?"
Sam whispered, "Anything."
"Uh-uh. Not good enough. Give me specifics."
Sam's eyes opened wide in astonishment.
"What. Will you do. If I let you come? How much is it worth to you, Sammy?" Dean scooted down, blew a breath of air over Sam's cock, making him shudder and thrash his head back and forth.
"I'll wash and wax the car."
"Oh, I think you want to come really bad, Sam. Worth a lot more than that."
Sam choked back a sob. "I'll detail it. Fucking detail it, man."
Dean kitten-licked the tip of Sam's cock—and pulled his head back immediately as Sam slammed his hips up, desperate for more sensation. "Ok… and what else?"
"Goddamn it, Dean, anything, I'll do anything you want, just name it, I can't fucking THINK…"
"Sam, I had a big lunch and a nice long nap. I can do this to you all night. I'll tie you down and tease you until you're sobbing, and I'll keep teasing you until you get pissed off, and then I'll just keep teasing you. Unless you sweeten the deal. Right now. And make it good."
Sam bit his lip, knowing that Dean would do everything he said. "I'll do blowjobs on command for two weeks, anytime, anywhere, as many as you want—on top of whatever else we do."
Dean groaned. "I like that one, Sammy. But I think you want to come so bad you're actually wondering if you can get permanent damage from me not letting you come for so long. And I know for a fact I can make you come harder right now than you've ever come in your life. So… one more thing."
Sam's eyes fluttered shut, and when they opened, they were nearly black, pupils dilated like he'd just taken a hit off an opium pipe. "24 hours. Anything you want. Literally anything you want. Nothing out of bounds." Dean's breath caught in his throat. "Literally. Anything. Wear a dress. Strip and dance naked for you. Lick my come out of your ass. Let you fuck me while people watch. Take your whole fist. No limits, Dean. You set the stopwatch, and for 24 hours, any command you give me, I'll do it. No questions, no trying to get out of it, no matter what you want. Not just sexual stuff, either."
Dean had never even dreamed Sam would offer so much. He couldn't even speak at first.
"Fuck. Sammy. Yeah. Ok. Deal."
Sam gripped Dean's shoulders hard. "Now let me come, you sadistic son of a bitch, before you fucking murder me with blue balls."
And Dean was as good as his word. He lowered himself down on Sam's lubricated cock, locked his mouth over Sam's, gripped Sam's long hair in his right hand and tugged at Sam's nipple with his left, and he rode Sammy good and hard, squeezing his ass tight around his cock. He lifted himself up and slammed back down on Sam, taking him deep, fucking him so well that Sam screamed his orgasm into Dean's mouth, body bowing off the bed, lifting Dean completely off the mattress—and then screamed again as the real orgasm hit, jolting his body like an electric shock, eyes rolled back in his head, unable to breathe, coming so hard he actually passed out.
When he came to, Dean was holding him, stroking his cheek, whispering, "Wake up, Sammy. Come on, baby. Wake up." And Sam broke into tears. The kind of tears that spill out of you uncontrollably when you come so hard and so long, it feels like your whole life was just a build-up to that one moment. The kind of orgasm that makes you think you could genuinely die happy. The kind of orgasm only Dean could give Sam.
Dean held Sam until he had cried himself out. They slipped into half-slumber for a while. Then Dean roused, settled them both under the blankets, and gave Sam a drink of water from the glass on his end table.
"I meant it, Dean. What I said. I'll do it."
"Can't wait, Sammy." Dean let Sam cuddle him, listening to Sam breathe, feeling his heart beat, wondering how, even with everything they had lost and all they had suffered, how on earth he ever got so lucky.