Title: A Little Surprise
Warnings: Anal sex, panties, pushy bottom Dean
Summary: Dean's got a surprise under his clothes for Sam, but won't tell him what it is until later.
"Dean, hurry up!" Sam shouted through the bathroom door. Dean had been in there for 15 minutes, and they needed to hit the road if they were going to get to the next town before nightfall. Eventually, Dean meandered out of the bathroom, at his own pace.
"What were you doing in there?" Sam asked, shouldering his bag as they headed out the door.
"Nothin'," Dean said innocently, which was cause enough for suspicion. Sam eyed his brother questioningly, hoping for a little more information.
"Let's just say I was putting together a little surprise for tonight," Dean said, giving Sam a wink. Sam looked at his brother curiously, and then his eyes widened a little bit and he looked Dean over, from head to toe.
"You mean like, in bed?" Sam asked, unable to hide the excitement in his voice.
"Or over a table or pressed up against a wall. Whatever," Dean said, grinning mysteriously as he got into the car and started up the engine.
"Is it a new toy? Or a new game?" Sam asked, sliding in next to his brother, closer than was really necessary, and then being gently pushed back to his side with a firm hand and a stern look.
"It's a surprise," Dean said, and then silenced any more questions with a light kiss to Sam's lips.
After several hours of driving, and whining and pleading from Sam for a clue, night was falling, and the brothers were pulling into a motel to spend the night. Sam was quickly and eagerly unpacking the car so they could get into the motel room and he could see the surprise Dean had been teasing him about all day. The endless possibilities had left him half-hard as his mind wandered through the vast quantities of fantasies he could come up with involving Dean.
But Dean was a natural born older brother, hell bent on tormenting his little Sammy for as long as possible. So as soon as they entered the motel room and Sam tried to get all over him, Dean brushed him off curtly, and told him to clean the guns while Dean packed a few salt rounds. Sam knew that neither of these tasks were strictly necessary, but did as told anyway, though not without pouting a little, and trying to rub up against Dean whenever he could get away with it.
"All right, you ready for your surprise?" Dean asked after they'd been working for an hour. Sam didn't hide his excitement, and pounced on Dean, pawing at his clothes and claiming his brother's lips with abundant hunger. Dean allowed it, for a moment, but then pushed Sam off and ordered him to undress. Sam shed his clothes quickly and clumsily, and then reached for Dean's, but was put off again.
"On the bed," Dean rumbled, watching as his brother scrambled onto the bed and sat there, waiting, his legs casually spread and revealing his thick cock resting against his thigh, plumping up with interest. Dean smiled and started undressing slowly, making it a show for his brother, and teasing him more, of course. His own cock swelled as Sam's eyes raked over his body, hungry for him.
With his shirts and boots off, Dean toyed with his belt buckle, easing it open so slowly that Sam was starting to whine. He fidgeted on the bed and his fingers twitched, like he wanted to be the one working Dean's belt open and pushing his jeans down.
"It's actually two surprises," Dean drawled. He'd gotten the belt open, and popped the top button. He was fingering the fly, but not sliding it down. "I'm gonna show you the first one, but you have to guess the second one."
Dean finally let the zipper slide down, and Sam leaned closer, squinting, and then his breath caught in his throat. It turned into a full throated moan as Dean shimmied his jeans down, carefully, and then kicked them off.
"Like the color?" Dean asked, fingering a little pink bow that adorned the front of the ladies panties he was wearing. They were pink silk and lace, sheer through some parts, covering as little as possible. Dean's cock strained against the delicate material, almost too big to fit all inside, and leaving a shiny wet spot where the head of his cock was leaking with excitement.
"Yeah," Sam said breathlessly, licking his lips at the sight of Dean, all muscle and masculinity, tucked into a tiny pair of the girliest panties Sam could imagine. He wanted to lean forward, grab Dean, and pull him down on to the bed. He wanted to bury his face between Dean's legs, and suck him off through the silky material. He wanted to slide the panties over, just a little, to expose Dean's hole and shove his fingers into that tight heat and really make Dean squirm.
"Now you have to guess the second surprise," Dean said teasingly, edging closer to the bed, but still far enough away that Sam couldn't reach him without lunging. "Otherwise, you don't get to have it at all."
"Uhm," Sam said thoughtfully, looking Dean over to see if there were any clues. Dean wasn't wearing anything else, and he wasn't acting any differently. Sam scanned the room, but couldn't see anything else out of the ordinary. "How about a clue?" Sam asked.
"Hmmm, OK. But just one," Dean said. He finally eased down onto the bed, climbing on all fours until he was straddling Sam's hips. They were inches apart, but not touching yet. It took all of Sam's control not to reach out for Dean. "Tell me Sammy," Dean said in a husky whisper right against Sam's ear. "When your big brother wears a tiny pair of panties for you all day, what do you think you should do with him?"
Sam thought about that, his mind ticking around several ideas. He looked at Dean, then down at the panties, then back up at Dean again, until finally something clicked and his eyes widened with disbelief.
"F-fuck him?" Sam asked tentatively, the little stutter a mark of his complete disbelief.
"Got it in one, baby boy," Dean said with a smoky, charming smile. He then leaned in to kiss Sam, slow and deep, like Sam had been wanting all day. Sam's hands went immediately to Dean's hips and ran feather soft over the silk as it rippled underneath Dean's muscles, undulating as Dean shifted slightly back and forth.
"I'm gonna ride you, Sammy," Dean said, his voice still rumbling as he put a bottle of lube into Sam's hands. "Wanna feel that big cock of yours splitting me open."
Sam groaned. Dean was more often the top when they were in bed, eager to take control and get exactly what he wanted from his little brother. But even on rare occasions like this, when he let Sam top, it was only in a very technical way. Dean was still the boss.
"Hurry up. Three fingers," Dean commanded several minutes later, squirming and bucking on top of Sam as the younger Winchester fingered him open, fast and hard like Dean wanted. Sam had wanted to savor it, feeling Dean up in his silk panties and taking his time, but with Dean barking out orders and Sam's cock already leaking dangerously, he couldn't help but obey.
"You ready for this, Sammy?" Dean asked teasingly as he hovered over Sam's cock. He'd tugged the panties to the side like Sam had imagined and was rubbing Sam's cock head against his loosened hole. "Don't go shooting off as soon as you're in me. I'll be really annoyed."
"I won't," Sam said, his voice already a little strained from the way Dean had been writhing around on top of him.
Dean grinned, and then leaned back, sliding down on Sam's cock in one smooth motion that belied his experience as a receiver in bed. Sam might've been the younger brother, but he was certainly bigger than Dean in more ways than one. He was thick, and long, and Dean shuddered as he took his brother in, inch by inch, but without pause. Finally, shaking and panting from the effort, Dean rested his full weight against Sam's hips, squeezing lightly around the full length of Sam.
"God, Dean," Sam groaned as Dean enveloped him. His face was screwed up from the effort not to go off, just like Dean had warned him. Dean was in playful mood that night, and Sam didn't want to spoil it by coming too soon.
"Now, you tell me when you're ready, Sammy," Dean said, saying Sam's nickname with love while he squeezed around his cock again. "'Cause I'm gonna ride this dick like a wild pony. Go on thinking about baseball and picking locks and stuff and try to last as long as you can, OK baby boy?"
Sam whimpered but nodded his head. He was as ready as he was going to get and Dean on top of him wasn't going to make him any more ready. So he braced himself as Dean drew up on his knees, leaving just the flared tip of Sam's cock nestled in that tightest ring of muscle. Dean held that position for a moment, and then slammed back down again, swallowing Sam inside again, and jamming his brother against his own prostate. Both brothers let out hearty groans, and continued as Dean wound up again for another deep, hard thrust.
Sam held on for all he was worth, gripping the head board of the bed and keeping his eyes shut against the arousing image of dean bouncing on his cock in a pair of pink panties. But it wasn't much relief as Dean rode him hard, squeezing him with his inner muscles, and then letting the filthiest dirty talk out of his mouth, which Sam couldn't block out, no matter how much he tried.
"Goddamn Sammy, you got a fat cock," Dean gasped from on top of his brother. "Nice and swollen for you brother in his little panties, huh? Really chubbed up at the thought of sticking your dick in me, didn't you? Bet you wish you could do this to me every night, huh Sammy? Wanna fuck your brother? Ream out my ass? Pound me in the back of the Impala?"
"Yes!" Sam growled, reaching up from the headboard to grab Dean's hips and grind him harder against his dick. Dean let out a shout of pleasure and let Sam manhandle him, lifting him up and slamming him back down again. Dean's hand went to the front of his panties, worked inside, and let his cock slide out in the front. For a moment, it slapped against his belly as Sam worked him over, but then he grabbed it and started jerking, just as fast and hard as he was riding Sam's cock.
"C'mon, Sammy… Harder… Give it to me," Dean gasped out between strokes, his hand jerking wildly and squeezing around the tip. He was starting to splatter pre-cum all over Sam's belly, his hand shaking the droplets loose as he drew close to orgasm.
"Gonna blow, Sammy, you ready?" Dean asked, breathlessly. Sam nodded in response and jerked his hips up even harder, trying to push his brother over the edge.
Dean's hips moved faster, his hand was like a blur, and his breath came out in shaky, broken gasps until finally, he was spilling, shooting his come all over Sam's belly and chest, making a mess of him. His body tightened around Sam, squeezing him rhythmically with each spasm of his cock. Soon, Sam followed his brother, and with an almost painful groan from the effort, he came, shooting up inside Dean. Dean murmured happily as he felt Sam filling him up with come, and slid down to rest his head on Sam's shoulder, cuddling up with him despite the mess coating their bodies.
"Damn, Dean," Sam said, still breathless as he reached up to stroke Dean's hair, pushing his sweat soaked locks away from his forehead. Dean nuzzled into the touch, rubbing against Sam with a contented sigh. "That's the best surprise you've come up with in awhile."
"And it ain't even over yet," Dean said, lifting his head to smile smarmily at his brother.
"It isn't?" Sam asked.
"Nope. So you start thinking about your brother, and reaming his ass, and these pretty pink panties until you're nice and hard again and then I'm gonna have myself another ride," Dean said, satisfied when Sam groaned, as though he were in pain. But Dean knew better. He knew his brother was going to keep loving his surprise all night long.