Summary: Sam's in a bit of a predicament because he lost a bet with Dean.
Disclaimer: This story is based on characters and situations created and owned by WB and Eric Kripke et al. No money is being made and no copyright or trademark infringement is intended.
Author's Notes: Thanks to Soph for the beta. This is 26 out of 31 short fics, all involving masturbation in honour of the Merry Month of May. All fics were written with knowledge up to Hell House, no canon after that was used since that's as far as I've seen.
Word count: 1,047
Link: to other mmom fic
Dean watched Sam squirm for what had to be the hundredth time since they had sat down with the victim of the haunting to ask her a few questions. It made him smile every time. Seeing his brother so hot and bothered was amusing and arousing in equal measures; and the ultimate fun was that he knew he was the cause.
The bet had been a stupid one born of too much adrenaline and bravado and Sam had lost. Dean had bet Sam that he could get him off first if they gave each other a hand job and Sammy had been stupid enough to take it. That in itself had surprised Dean, Sam usually didn't let him get away with these types of things. Sam had of course come first since Dean had jerked off in the bathroom before even instigating the bet; no challenge really. The forfeit had been Sammy's current predicament.
That morning Dean had had the great pleasure of rolling Sam onto his front, lubing him up and pushing a good sized butt plug up his brother's ass. They didn't play with toys too often, but they still had a small stash and the look on Sam's face when he'd tried to get dressed had been enough to justify their existence as far as Dean was concerned. Sam had to be in over stimulation hell and by the rules of the bet the only one who could remove the plug or help Sammy out was him.
When they finally stood up to leave Sam looked somewhere between relieved and aghast that he had to move; Dean almost laughed. He was impressed that his brother managed to walk in a straight line to the car and Sam's baggy jeans did nothing to hide his state from Dean since he knew what he was looking for. Sam was turned on to the nth degree and Dean had been wandering around all day half hard just at the thought.
"Dean, please," the way Sam begged as soon as they had driven away from the built up area sent shots of arousal straight to Dean's groin.
When he looked over at Sammy he could see that his brother was completely desperate and the little light in Sam's eyes told him that his brother was two heartbeats away from snapping, bet or no bet. There was only so far Sam could be pushed and Dean knew exactly where the line was. He grinned and let his brother suffer for a few minutes more before pulling onto a dirt track into an abandoned parking area.
"You're so incredibly hot when you beg, Sammy," Dean said with a leer.
Sam was too far gone to even complain about the nickname, he just groaned and sank down into the front seat and Dean congratulated himself on that victory as well.
"What do you want, little brother?" he asked, his voice low and husky from just watching Sam writhe.
"Please, Dean," Sam seemed to have lost any inhibitions about begging just as Dean had hoped, "I need … please."
And incoherent as well; an added bonus as far as Dean was concerned. He considered torturing Sam some more and making his brother form an actual thought to ask for exactly what he wanted, but that might cross the line. Sam's hands were already gripping the seat in a death grip, clearly to stop himself from touching what Dean had forbidden him to touch and Dean was impressed with Sam's stamina.
Reaching out he unhooked Sam's belt and quickly opened his brother's fly. Sam melted the moment Dean touched him, sinking even further down as if he had no control over his body what so ever. Dean felt himself hardening at the long wanton groan that accompanied Sam's movement. He could only imagine what the move had done to the plug stuck up Sam's ass.
"Oh god, oh god, yes," Sam was whimpering and Dean suspected his brother had no idea what he was saying.
Turning Sam into such a complete wreck was a rare and wonderful treat and Dean slowly stroked the pre-come off the head of Sam's cock with his thumb. Sam's eyes were closed and his head was back and there was a look of complete bliss on his features that made Dean want to keep this going forever. When Sammy gave up control he looked completely free and that was one of the most precious things Dean could ever find.
With carefully speeding up and slowing down of his strokes Dean kept Sam on the edge for long minutes until the words falling out of Sam's mouth were completely nonsensical. Then he leant forward more, picking up the tissues he had pulled from his pocket when Sam was too far gone to notice.
"Come for me, Sammy," he said in little more than a whisper and Sam bucked up instantly.
Dean deftly prevented any evidence ending up on the leather or Sam's clothes and then just enjoyed the sight of his baby brother shuddering in his hand. If he thought Sam had been in a boneless sprawl before it was nothing compared to the pile of long limp limbs his brother had become now.
Dean just sat there watching and waiting as Sammy regained his wits. Then Sam moved and the gasp made Dean grin like a Cheshire cat.
"Dean," Sam all but squeaked, "you can't leave me like this."
In response Dean just threw Sam another tissue and went to start the engine. Sam made the most incredible sound as the vibrations of the car reached him.
"Y'know I'm not stupid," Sam's voice was low when he spoke just as Dean was about to put the impala in gear, "I know what you did in the bathroom before the bet last night."
Dean turned and looked at Sam and his brother's eyes were smoldering. Sam could have been naked and he wouldn't have looked sexier.
"I'm doing this because I know you love it, not because I have to," Dean felt his cock throb at the words, "but I know you'll love it more when you're drilling me through the mattress."
Dean put the car in gear, suddenly the motel seemed like it was far too far away.