Timeline No Particular Season
Sam was smirking as Dean walked out of the bathroom, freshly showered and a towel wrapped around his waist. Sam wasn’t gloating. Yet. Just keeping an eye on his brother.
Dean walked over to his duffel bag and pulled out some clothes, but instead of yelling at Sam for changing out all his underwear for pretty little lacy panties, he started pulling a pair on.
Sam frowned, trying not to be too obvious about it. Okay, so fine. He’d underestimated his big brother. He should’ve known better, and really he only had himself to blame for whatever Dean would do to him in retaliation.
Sam rolled his eyes and resumed his search for hunts in the area.Dean
Dean had forgotten how much he enjoyed wearing panties. He stood in the bathroom that night after Sammy fell asleep and looked at himself in the mirror, wearing nothing but the panties his little brother had bought him.
He traced over the bulge with his index finger, gasping as his cock jerked. The panties were his size, but of course his erect cock didn’t fit anymore and was poking out the right leg hole. Dean ran his fingers over the material stretched by his balls with his left hand while he rubbed just underneath the head of his cock with his right thumb.
He didn’t last long, and he was actually disappointed when he came in under a minute. His knees nearly gave out, and he steadied himself with a hand on the counter, breathing heavily as he rubbed his jizz into the material of his pretty little panties.
Dean grinned at himself in the mirror. If Sam wanted to prank him into wearing cute panties, so be it. He knew his little brother, and Dean could give just as good as he got. Sam was going down.Sam
Sam watched as Dean was thrown across the room by the very disgruntled ghost who’d really had enough of kids trespassing on his property. Sam lit the lock of hair on fire and grinned as the ghost vanished. He walked over to Dean, ready to give his brother a hand up, but he froze, staring down at the red lace peeking out over the top of Dean’s jeans.
“Dude!” Dean barked, holding a hand out.
“S-sorry,” Sam said, shaking his head and helping Dean up.
“I get the first shower tonight,” Dean said as he walked out the front door. “And I’m using up all the hot water,” he shouted.
Sam adjusted his jeans and followed Dean.dean
Dean wore the panties to bed that night. He turned onto his stomach and lazily thrust against the bed, rocking himself to sleep with a smile on his face and a semi that wasn’t nearly as urgent since he’d jerked off again in the bathroom.Sam
“Burgers!” Sam announced as he walked into the motel room and kicked the door closed behind him.
“I’m comin’,” Dean said from the bathroom.
Sam pulled the burgers and fries out of the bag and set the drinks down on the table. He flopped down onto the chair and bit into his burger, then promptly choked on it when Dean came out of the bathroom in nothing but the sheer green boyshorts Sam had put in Dean’s duffel bag.
“You okay?” Dean asked as he thumped Sam on the back a couple of times.
Sam nodded, eyes watering as he reached for his drink and took a swig. “Fine,” he said, then coughed again. “Just went down wrong.”
“If the burgers are that good,” Dean said with a smirk as he pulled his jeans on, “you should’ve gotten us extras.”
“Well, ah, we’re in town for another night,” Sam said, wiping at his eyes, “so I’ll grab more tomorrow.”
“Awesome,” Dean said as he sat down and took a huge bite of burger, then groaned in appreciation. “Yeah, definitely bring back at least two for me next time.”
“You got it,” Sam said.
They’d grown up in motel rooms, so when Sam jerked off after dinner, Dean politely didn’t say a word about it.Dean
Dean had forgotten what it felt like to wear panties under his jeans while he was walking around in public, acting as if nothing unusual was happening. Sam had noticed. Of course he had. Because Dean had made sure to bend over in front of him as he grabbed his knife out of the trunk.
He smirked as he heard Sam let out a strangled noise. Yeah, Sam had seen the purple lace.Sam
“Oh, my god,” Sam groaned as he stared into the duffel bag.
It was his week to do laundry, and apparently instead of ditching all the panties and buying new underwear like any normal guy who’d been pranked, Dean had kept them. He’d worn them. And now they were all dirty and waiting for Sam to throw them in the washing machine.
Sam looked around the laundromat to make sure he was alone, then reached in and grabbed them. They were all soft, some frilly and some lacy, and every single one of them had been used. Sam looked around one more time, then held them up to his nose and took a deep breath.
“Fuck,” he breathed, eyes closing. That was definitely his brother, and if he wasn’t mistaken, Dean had even come in the pink panties with little white hearts all over them. “Shit!” Sam hissed as the bell over the door rang.
He quickly shoved all the panties into the washing machine and pushed more clothes in on top of them before setting the washing machine to delicate and using the mild soap. No way was he going to hand wash the panties, but he wasn’t an idiot. His time living with Jess had taught him that panties like that can’t be washed on the heavy duty cycle.
When the laundry was done, Sam gently folded each pair of panties and put them back in the duffel bag.Dean
Dean’s cock was chafed and sore, but the ruined panties felt so good on his shaft that he didn’t care. At least until after he’d come. He hissed as he pulled the panties away, his dick red and still half hard. He leaned back against the tank of the toilet and held the panties up as he licked his come from them, sucking on the fabric to get it all.
His dick felt a little less sore after he took a shower, but that didn’t stop him from putting another pair of panties on before he put his jeans on.Sam
Sam had been walking around with what seemed like a constant boner for three weeks. His stupid brother with his stupid panties and his stupid nonchalance over the whole thing was driving Sam crazy.
He’d heard Dean groaning his way through an orgasm. He knew Dean was using the panties to get off. And if something didn’t give, Sam was going to die of the worse case of blue balls ever soon.
Dean came out of the bathroom, already in his jeans, and something inside Sam broke. Shattered. He could see the pink lace peeking out from under the jeans, and he’d reached his limit.
“Holy fucking shit, Dean,” Sam whimpered as he fell to his knees and crawled to his brother, clumsy hands yanking at the jeans.
“Fuck, Sammy,” Dean gasped as Sam mouthed at Dean’s cock through the jeans even as he unbuttoned them and pulled them down, leaving the panties in place.
“Dean, I…,” Sam started as he stared at the panties. “I…, fuck,” he breathed.
Sam hadn’t bought those panties. He knew he hadn’t. There was a cute little pink bow in the center of the waistband, and none of the panties he’d bought had a little pink bow. That means Dean bought these for himself. He’s fucking gone out and shopped for his own panties, spent his own money to buy a pair of panties just for himself. Sam nearly came in his jeans right then and there.
“You like my panties, Sammy?” Dean asked.
Sam looked up at Dean, panting with desire and nearly drooling. “Please,” he said as he rubbed his lips over the panties.
“I’m fuckin’ sore,” Dean said with a chuckle. “I’ve jerked off with these panties three times today.”
“Fuck,” Sam groaned, closing his eyes and shoving his nose into the fabric, smelling the evidence of what Dean had just admitted to doing. “Please, Dean. Lemme suck you,” he begged.
“I dunno,” Dean said.
Sam frowned up at Dean, brain already too far gone to understand why Dean wasn’t totally on board with this. “Huh?” he asked.
“I don’t know if I should let you suck me off,” Dean said as he ran a finger over Sam’s lower lip, “when the only reason we’re in this situation is because you pulled a prank on me.”
Sam whimpered. “I’ll do laundry and wash the car on a weekly basis for the next two months if you forget that this started out as a prank.”
“Make it three months,” Dean said.
“Done,” Sam replied immediately.
“I wasn’t done yet,” Dean said with a smirk.
Sam huffed. “Fine. What else do you want?”
“Tell me which pair of my new panties are your favorite,” Dean said as he pushed his thumb into Sam’s mouth and rubbed the pad of it over Sam’s tongue.
“These,” Sam mumbled around Dean’s thumb. “These are my favorite. I like these.”
Dean chuckled. “Tell me why you like ’em,” he said as he pulled his thumb out and used the spit to slick the tip of his dick, which was already poking out over the top of the panties.
Sam licked over the trim on the waist of the panties, tasting Dean and enjoying the lacy material tickling his tongue. “The bow,” Sam said, then sucked she shaft of Dean’s cock through the material. “The pretty little bow and the cute little pink polka dots all over. Fuckin’ hot. So fuckin’ hot,” he said, then sucked on the shaft again.
Dean bucked into Sam’s mouth. “Fuck, Sam,” he breathed, resting his hands on Sam’s head.
“And you picked ’em out yourself,” Sam said as he mouthed his way over the material, gently nibbling at Dean’s balls. “Do you have any idea how fuckin’ hot it is that you… Fuck, Dean, you went into a store and bought these!” he said as he pulled back and looked up at Dean. “Did you tell the salesgirl you were buying ’em for your girlfriend?”
“Nope,” Dean said with a smirk. “Told her they were for my boyfriend, ’cause he gets a huge kick out of it when I wear ’em under my jeans.”
“Fuck,” Sam growled as he leaned forward and wrapped his lips around the head of Dean’s dick, sucking as he ran his fingers over the lace of Dean’s panties.
Dean groaned, spreading his legs wider so he’d have a better chance of staying upright. “You should’a seen her face. She probably had to change her panties after I left. She tried to play it cool and help me find what I wanted, but she was really distracted and dropped my change when she was handing it to me.”
Sam grabbed an ass cheek in each hand and pulled Dean closer to him, sucking harder and pushing his forehead against Dean’s stomach.
“She probably would’a said yes if I asked her to come back to the motel with me,” Dean said, eyes closed and voice breathy. “But all I could think about was the look on your face each time you realized I was wearin’ panties.”
Sam moaned around Dean’s dick, knee walking the two of them closer to the bed, glad that Dean was far enough gone that he just kind of stumbled along, letting Sam direct them. As Dean’s legs touched the end of the bed, Sam surged up, pushing Dean onto the bed. Dean flopped back, his legs spreading wide as Sam crawled between them.
“Fuck, Sammy, yeah,” Dean said, his hands going to his hips as he ran his fingers over the lace. “Suck me, c’mon.”
Sam pulled the panties down a little in the front, just enough so he could get all of Dean’s cock in his mouth, then started bobbing as he pulled the fabric of the panties, letting it drag over Dean’s balls and hips.
“Gonna come, Sam,” Dean warned. “Gonna come. Fuck, I’m gonna come and wanna see it all over your face.”
Sam would’ve teased Dean about his lack of stamina if he hadn’t been about to come without ever having touched his own cock. He pulled off at the last second, just in time to close his eyes and hold Dean’s cock so he could get a face full of come.
“Fuck! Sam!” Dean yelled as he came, eyes open wide as he watched his little brother take a load all over his face.
Sam waited until Dean was a panting mess of boneless contentment before he pushed his face against the panties and wiped the jizz all over, mouthing at the material even as he got the panties messier than they already were.
He reached down and unbuttoned his own jeans, freeing his own erection before he grabbed Dean’s hips and pulled until Dean’s ass was hanging off the end of the bed. Sam grabbed his own cock and smacked it down between Dean’s legs, right over his balls.
“Dude!” Dean yelped as he flinched. “What the fuck did you do that for?”
Sam snorted, then started thrusting, his cock dragging over the pretty pink panties. It burned, but felt amazing. He didn’t care if he chafed his dick, and by the way Dean was staring at him, mouth open as he watched him carefully, Dean was into the idea too.
Sam growled as he came all over the panties, fingers leaving bruises in the skin of Dean’s hips as he nearly pushed Dean off the side of the bed. Sam flopped down on top of Dean, knees still digging into the carpet but his top half splayed out on Dean.
“So,” Sam drawled, “did you just get the one pair?”
Dean chuckled. “Nope.”
Sam groaned, too sated to do much about it, but still appreciative. “Do I get to see ’em?”
Dean tugged on a lock of Sam’s hair. “I got some in your size too, Princess,” he said cheerfully.
“Oh, fuck,” Sam whimpered as his dick twitched.