Five Times Dean Told Sam to Pull His Pants Down

Title Five Times Dean Told Sam to Pull His Pants Down
Fandom Supernatural
Category Slash, Het
Rating Adult/Explicit/NC-17
Pairing(s) Sam/Dean/Castiel, Sam/OFC
Words 3078
Timeline Preseries through Season 8
Talk of STDs, Humiliating Circumstances, Genderswap, Incest, Incest while Genderswapped
Humiliation, Blowjob, Oral Sex, Cunnilingus, Genderswap, Voyeurism, Coming in Pants, Threesome, Kink Meme, Humor, Hurt/Embarrassed Sam, Offscreen Blowjob, Examination After Injuries
Sam, Dean, Castiel
Full Prompt
Everything that would make Dean say, “Sam, pull down your pants and let me take a look.”
Summary A five times fic that covers over a decade.

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1 The Lip Gloss Incident of 2001

“Sam, pull your pants down and let me take a look.”

Sam’s cheeks flushed, just like Dean knew they would, but it was his baby brother, damn it! Dean had changed his diapers, so he certainly wasn’t going to let a little thing like embarrassment get in the way of finding out why Sam came home wincing and walking with his legs spread very far apart.

Sam rolled his eyes. “You gonna come to California and fix my boo-boos too?” he snarked.

Dean felt a tightness in his chest. It was the same one he experienced every time Sam reminded him he was leaving them in a week. “I might have to, yes,” Dean said with a straight face, then pointed at Sam’s jeans. “Down,” he commanded.

“No,” Sam said.

“Does this have to get physical?” Dean threatened.

“Okay, look,” Sam said, arms out at his sides. “Kelly just blew me. She was a little rough and isn’t so good at keeping her teeth covered. That’s all.”

Dean shook his head. “I’ve been blown by a virgin before who thought guys actually liked to feel the scraping of teeth on their dick. But I didn’t walk around with my ankles five feet apart because of the pain. Now drop ’em.”

Sam sighed. “Fine,” he said, then gently undid his jeans and dropped them and his boxers to the floor.

“Dude,” Dean groaned as he leaned down and took a good look.

“Okay!” Sam yelped, taking a step back, though it wasn’t a big step because of the jeans around his ankles. “You’ve seen it. Now are you happy?” he asked as he pulled his boxers and jeans back up.

Dean put a hand on Sam’s neck. It was an affectionate gesture that always calmed Sam, and it worked this time too. “I’m gonna fill you in on a family secret.”

“Huh?” Sam said, forgetting about fact that his belt was still undone. “What secret?”

“Dad and I are allergic to Bonne Bell lip gloss,” Dean said, and he actually managed to do it with a straight face.

Sam’s face screwed up in confusion. “Huh?” he said again.

“Yeah, your girl was wearing lip gloss,” Dean said. “Ever since I came home with my dick looking like it’d been stung by twenty bees, I’ve been real careful about making sure whoever blows me doesn’t have lip gloss on.”

“You’re serious?” Sam asked, facial features shifting from confused to suspicious. “This isn’t some joke?”

“Totally serious,” Dean said. “You can ask Dad if you want.”

“Why didn’t you tell me before now?” Sam asked, a bit of a whine in his tone of voice.

Dean shrugged. “Allergies don’t always run in families, and I figured you’d made it to eighteen without a problem, so you probably didn’t have a problem with it.”

“Is there anything I can do about it now?” Sam asked.

“Take a shower,” Dean said. “Make it as cold as you can stand it and wash really well down there. You’ll still be a little itchy and sore for a day or two, but you’ll live.”

Sam sighed. “All right, shower it is,” he said as he turned to walk away.

“Was it still worth it?” Dean asked.

Sam turned around too look at Dean. “Hell, yeah!” he said with a grin.

“That’s my boy,” Dean said with pride in his tone of voice.

2 The Werecat Stitches Incident of 2005

“Sam, pull your pants down and let me take a look.”

“Fuck’ff,” Sam slurred as he dropped down onto the bed without bothering to pull the disgusting motel room blanket off first.

“C’mon, Sam, lemme check the stitches,” Dean said as he gave Sam a good shove to roll him onto his back.

“I say you ta fuck off,” Sam moaned, batting at Dean’s hands with uncoordinated arms.

Dean chuckled. Sam hadn’t been so drunk as to totally fuck up his sentence structure in a long time. “You never did do well mixing pain meds and tequila shots,” he said as he unbuckled Sam’s belt.

“Doesn’t hurt,” Sam mumbled as his eyelids drooped and he finally closed his eyes, snoring only a second later.

“Yeah,” Dean agreed, even though he knew full well that Sam was out of it, “that’s why I wanna check the stitches, you idiot.”

Dean gently pulled Sam’s jeans and boxers down, breathing a sigh of relief when the bandage on Sam’s left upper thigh was still clean. He pulled the dressing back and checked anyway, then taped it back down when he saw everything was still intact.

By the time he was done wrestling Sam’s clothes off and getting him under the covers, he was ready for bed himself. He salted the windows and door, then pulled his own clothes off, tired from the events of the last few days and worrying about Sam.

Sam’s obnoxiously loud snores lulled him to sleep faster than they really should’ve, but it was a reminder that Sam was still alive and breathing.

3 The Broken Condom Incident of 2007

“Sam, pull your pants down and let me take a look.”

“No,” Sam said.

“Do you want your dick to fall off?” Dean asked.

“It’s not gonna fall off,” Sam said, rolling his eyes.

“Do I need to bring up the STD website on your laptop and show you pictures?” Dean threatened.

“I’m an adult,” Sam snarled. “I can look up my own dick pics and compare them.”

“Yeah, and then you can sit there and freak the fuck out and wonder if you should go to a clinic or just wait it out and guess at an antibiotic,” Dean said.

Sam sighed. “I don’t even wanna know why you think you can diagnose an STD and match it up with the correct antibiotic.”

Dean grinned. “My dick and balls are very important to me,” he said, then shook his head, a frown on his face. “I have absolutely no idea why people don’t try to learn this shit. You like your dick? It’s not that hard to find out everything that can go wrong with a dick so you can be prepared.”

Sam snorted, then chuckled. “Okay, yeah, that’s a better explanation than saying you’d had so many STDs that you can tell just by looking.”

Dean gasped over-dramatically. “I have never had an STD!”

“Seriously?” Sam asked, surprised.

Dean scoffed. “No, I haven’t. And you wanna know why?”

Sam shrugged. “You always told me to cover my dick, so I figure you do too.”

“You can still get STDs even when you wear a condom and yours broke,” Dean said. “I taught you better than that.”

“Yeah, I know,” Sam drawled. “I just meant in general.”

“Okay, so the reason I’ve never had an STD is not only the condom thing, but also because the only thing that comes close to my love of my junk is my love of other people’s junk,” Dean said with a smirk.

Sam snorted. “So, what, you give them an examination before you touch ’em?”

Dean’s eyes widened. “You don’t?”

“Yeah,” Sam said as he chuckled, “that’s why all the girls go for me, because I whip out the stirrups and gloves before I touch them.”

Dean sighed. “You don’t have to be ridiculous about it. Girls like it when you take your time with them. And if things look a little funky, I have no problem getting them off with my fingers and calling it a night after I hump their leg.”

Sam let out a bark of laughter. “That’s awesome!”

“I know I’m awesome,” Dean said with a smirk. “And I’ve also never had an STD. Now drop your pants and lemme look at the sore on your dick.”

4 The Downed Tree Incident of 2011

“Sam, pull your pants down and let me take a look.”

“Dean, I can’t even move,” Sam said through clenched teeth as he very carefully made his way to the motel room bed, legs spread wide and arms out to his sides. “So don’t even think about making me take my pants off.”

Dean wrapped an arm around Sam’s middle and grabbed one of his arms, helping him to the bed and lowering him gently.

“Dude, I mean it!” Sam growled as Dean started to unbuckle Sam’s belt. “Leave me alone!”

Dean frowned down at Sam. “Do you wanna lose your balls?”

“I’m not gonna lose my balls,” Sam said, then winced as he shifted a little on the bed.

Dean snorted. “You’ll lose ’em if you’ve given yourself a case of testicular torsion.”

Sam blinked up at Dean. “How do you know what that even means?”

“Have I not said my junk is important to me?” Dean said incredulously. “We get knocked around on a regular basis in our line of work. Why wouldn’t I know that a good knock to my crotch might twist one of my testicles to the point where the blood supply is squeezed off? You very recently fell balls first onto a downed tree!”

Sam winced. “Yeah, I remember that part.”

“Okay, then let me look at your balls!” Dean said as he went back to unbuckling Sam’s belt.

Sam sighed, throwing his arms out to his sides and letting Dean do whatever he wanted. “Can you at least be a little gentle?”

Dean snorted. “As compared to all the other times I’ve been rough with you when you’re injured?” he said under his breath.

“Ah, fuck,” Sam hissed as Dean pulled his jeans and boxers down. “Hey!” Sam yelped, eyes wide as Dean very delicately wrapped his hand around Sam’s balls and used the pads of his fingers to examine Sam’s spermatic cords.

“You’re such a prude, Sammy,” Dean teased.

“Says my brother as he’s holding my balls,” Sam snarled.

Dean chuckled as he finished up his examination. “You really shouldn’t be such an asshole when I’ve got your bruised balls in my hand.”

Sam covered his face with his hands, rubbing his eyes and trying very hard to ignore the fact that his balls were throbbing.

“Okay,” Dean said as he let go of Sam’s balls, “you’re gonna live.”

“Thanks,” Sam mumbled.

“I’m gonna go get some ice from the machine,” Dean said as he snagged the ice bucket from the dresser.

“I want a soda,” Sam yelled as Dean opened the door.

“You got it,” Dean said with a smile.

“And a candy bar.”

Dean chuckled. “I’ll get you a candy bar.”

“And some chips.”

“I’ll get you chips.”

“And a sandwich,” Sam yelled as Dean closed the door, then he smiled as he heard Dean yell back, “And I’ll get you a sandwich!”

5 The Incident That Shall Never Be Mentioned Again of 2013

“Sam, pull your pants down and let me take a look.”

“No. Fucking. Way,” Sam growled.

“Dude, please!” Dean practically whined, eyes wide, body nearly vibrating with excitement.

“No,” Sam said, backing up. “You’re sick. I’m not showing you.”

“I won’t touch!” Dean promised. “I just wanna see!”

“No,” Sam said, shaking his head and crossing his arms over his chest. Then he frowned. It was harder to cross his arms over his chest when two fairly large and very nicely-shaped breasts were in the way. “You’re not looking, I’m not looking, and we’re just going to wait this out.”

“Oh, dude, that’s just… No! You can’t just wait it out!” Dean said rather loudly. “I can understand you not letting me see or touch, but it would be a crime against humanity if you didn’t at least test drive that thing while you’ve got it! Cas, tell him he has to use it!”

Cas stood there, confused frown on his face. “Why do you want to see it? You’ve seen many vaginas, and you’ve also “used” many vaginas,” he said, and Dean could just hear the air quotes on that one.

“But it’s brand new!” Dean said, waving his hands in the general direction of said vagina. “It’s never been used, never been touched!”

“Dude, think about what you just said,” Sam hissed.

Dean pulled a face. “You know what I mean! It’s not like it’s a young vagina, it’s just… Quit changing the subject!”

“I didn’t change the subject!” Sam said. “The subject is and has been my vagina!”

“Please let me see it!” Dean begged, going to his knees and trying his best ‘I’d really like to see your vagina’ face. He’d only just now made it up, but he hoped it would do the trick.

Cas shook his head. “I don’t understand why you want to see it so badly.”

“Because I’m a guy!” Dean whined. “Please!”

Sam sighed as he ran his fingers through his hair. “If I do this…,” he started.

“I’ll do anything!” Dean said, then wondered for a brief moment if that had been a stupid thing to say.

If I do this,” Sam started again, “you are not to touch,” he said, waiting until Dean nodded enthusiastically, “you are not to get closer than twelve inches from my crotch,” Dean nodded again, “and you’re to go to the bathroom to take care that,” Sam said as he pointed to the tent in Dean’s jeans, “by yourself after you’ve had a good look.”

“I accept all your terms,” Dean said with a nod. “And I want to reserve the right to use it as a jerk-off fantasy in the future.”

“Agreed,” Sam said.

“Yes,” Dean said under his breath, then waited with eyes wide as Sam unbuttoned his jeans and let them drop. Dean let out a squeak as Sam slowly lowered his boxers.

“No noises,” Sam hissed.

“You didn’t say I couldn’t make noises!” Dean growled, eyes glued to Sam’s crotch, even though Sam’s boxers were still in the way.

Sam sighed. “Okay, you can make noises. Just don’t say anything that’ll give me nightmares.”

“Agreed,” Dean said, then gasped as Sam dropped the boxers.

In the silence that followed, Cas got a good look as well, but Sam didn’t mind. The curiosity on Cas’ face was much easier to take compared to the look of awe on Dean’s face.

“It’s perfect,” Dean whispered. “It’s fucking perfect.”

Sam gasped as his clit twitched, his eyes going wide.

“Oh, fuck,” Dean moaned. “Your clit twitched. Didn’t it!?!”

Sam nodded. “Uh, yeah, it did.”

“Have you changed your mind on giving it a test drive yet?” Dean asked with a smirk, even though his eyes were still focused on Sam’s crotch.

“Totally,” Sam admitted.

“You said I couldn’t touch, and I’m not asking to touch,” Dean said, finally looking up at Sam. “But would you consider spreading your lips? Please? I really will do anything, and I mean fuckin’ anything, if you do that.”

“Laundry for a month,” Sam said without hesitation.

“Make it two months,” Dean said.

“And I get to pick where we eat for the next two months,” Sam said. “Every meal. No complaining from you.”

“Done,” Dean said.


Sam nodded, then reached down with his right hand. “Oh, I’m so gonna test drive this,” he whispered as he ran his index and middle fingers down either side of his pussy and gently spread himself for Dean.

“Ah, fuck,” Dean groaned as he pushed the heel of his hand down on his crotch. “I’m not getting myself off, I promise. I’m just tryin’ not to come in my jeans.”

Sam chuckled as he looked at Cas. “You know how to take care of that, Cas?” he asked as he nodded toward Cas’ crotch, which was very obviously tented.

Cas looked down at his vessel’s body as if he had no idea Jimmy’s penis could have a mind of its own. Cas looked back up at Sam, a small frown on his face.

“If I come in my pants,” Dean said, nearly breathless, “are you gonna kill me?”

Sam couldn’t stop caressing himself, fingers probing a little deeper. “Clits are awesome,” he moaned as he ran the pad of his index finger over his clitoris.

Dean looked up at Sam, a sly grin on his face. “Wanna know what it feels like to have your clit sucked?”

Sam froze, his eyes widening. He glanced over at Cas, who was grimacing and doing something strange with a hand down his pants. “We never speak of this again,” Sam said, glaring at Dean.

“Never,” Dean agreed even before Sam was done with his demand.

“Fuck, yes!” Sam said as he leaned back against the wall and spread his legs as much as his jeans would allow.

Dean crawled over to Sam and started licking around Sam’s fingers, moaning as he got a taste of Sam. Sam’s thighs were shaking and Dean heard his head hit the wall as he ran his tongue over Sam’s clit.

“Ah!” Cas yelped. “Oh, oh, oh,” he moaned, but neither Dean or Sam paid attention to him.

“Oh, fuck,” Sam gasped as he reached up under his T-shirt and started playing with his breasts. “Suck it harder!”

Dean wrapped his hands around Sam’s knees for leverage and closed his eyes, letting his tongue work over Sam’s clit even as he sucked.

“Dean!” Sam yelled, head hitting the wall again and his knees buckling.

As Sam crumpled to the floor, Dean went with him, never once losing his grip on Sam’s legs or the suction of Sam’s clit. As Sam shivered and shook on the floor, Dean licked him, keeping the pressure going as long as Sam could stand it. Dean came with a yelp that made Sam squeal, smacking Dean in the head pretty hard with the heel of his right hand.

“Dude!” Sam barked. “Sensitive!”

Dean pulled back, face shiny with slick and a huge grin on his face. “That was awesome,” he crowed.

They heard a sigh and both turned to look at Cas, who was on his knees, eyes half-lidded, a dreamy smile on his face as he pulled his hand out of his pants, a large wet spot clearly visible to the left of the fly.

“How much longer am I gonna be like this?” Sam asked.

“Three days,” Cas said, his voice almost a whisper.

“New deal,” Sam said, looking at Dean.

“Okay,” Dean said, shrugging.

“At the end of the three days, we agree never to speak of this again,” Sam said. “Ever.”

“Deal,” both Cas and Dean said.


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