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Things Don’t Always Go as Planned

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Sam Winchester is seriously questioning his life choices.

To be more specific, Sam is questioning a choice he made about an hour and a half ago.

It started out as a pretty awesome idea, actually. The new no more secrets, let’s be open about stuff policy that Sam and Dean have been trying to stick to in the past few months has cleared a lot of air between them, made things easier, brought them closer together somehow. And, because they’ve been applying it to all aspects of their relationship, it’s also led to mind-blowing sex on numerous occasions as they both started to talk about secret wishes or fantasies they hadn’t mentioned to each other before.

So this is where Sam’s genius-turned-stupid idea comes in.

This morning, when he and Dean were sitting in the bunker’s war room, looking for a new case or a way to fight Amara, Sam finally found the courage to say something that had been on his mind for years.

“I want to put a prostate stimulator in your ass,” he blurted out and hoped that he wasn’t blushing.

Dean looked up from his laptop, one eyebrow cocked, a smile tugging at the corners of his lips. “Wow, Sam, that’s a real strange way to call your dick.”

“No, I mean a real stimulator, you idiot.” He reached under the table, fishing for a moment in the paper bag he had put there earlier. “This,” he said and placed the item in question on the table in front of Dean.

“Huh. So you’ve been planning this for a while, I see.” Dean pushed his laptop aside and leant over to inspect the toy closely. “It looks kinda small,” he said eventually before taking it in his hand, turning it around, touching the black plastic, fingers tracing the curved shape.

“Don’t let the size deceive you. It’s gonna blow your mind, trust me.”

Still frowning critically, Dean put the stimulator down. “Why don’t you just fuck me like a normal person?”

“Because I want to watch you wear the thing during the day. While we’re doing normal stuff. Like right now.”

Dean’s eyebrows went up again, then he shook his head. “You’re fucking weird, man.”

Sam didn’t say anything, just kept looking at Dean.

Dean sighed. “Alright, alright.” He stood up, hands already opening his belt buckle. “You wanna do this right here?”

Which actually wasn’t originally part of the plan, but Sam definitely wasn’t opposed to changing plans when there was a better option. “Yeah. Bend over.”

Still shaking his head and muttering something under his breath, Dean complied, bending over the big table with the map of the world, hands braced on Scandinavia and Siberia, cheek resting somewhere in Ural. “Alright. Put it in me.”

“Hold on.” Sam bent down to rummage through the back pockets of Dean’s jeans, which were currently pooled around Dean’s ankles, until he found the travel-sized packet of lube that Dean always kept there. One finger, then two, no need for a third one this time. Sam lubed up the toy as well. “Ready?”

“Sure,” came Dean’s response, accompanied by Dean shaking his ass impatiently. “I told you. Just put it in already.”

So Sam did. Then, he watched with satisfaction as Dean quickly forgot all about his sarcastic comments the moment the toy was inside him, and only managed a stuttered “Oh, fuck…” when Sam turned the vibrations on.

“Feels good, doesn’t it?”

“Y-yeah.” Dean took several deep breaths before straightening up and turning around to face Sam. He was flushed, his pupils blown wide, lower lip plump and dark red with imprints of his teeth visible. “So now what? Want me to blow you?”

“Not exactly,” Sam sank down to his knees slowly, the position putting his face mere inches from Dean’s hard, weeping cock… which Sam ignored completely and went to grab the waist of Dean’s underwear and jeans, pulling them up his legs. “I want you to get dressed and get back to work.”

Dean’s mouth dropped open. “What? You were serious about that?”

“You heard me.” Standing back up, Sam patted Dean on the shoulder and gave him an encouraging smile. “Come on.”

Dean’s face showed that he was coming to realize Sam wasn’t kidding. “Why do I even put up with this shit?” But he was already doing as told, zipping up his pants and buckling his belt. “I gotta warn you though,” he jammed a finger into the center of Sam’s chest, “I’m not gonna be able to do anything useful like this.”

“I know,” Sam replied sweetly, and handed Dean a book on de-powering spells that they were hoping they could use on Amara. “But you’re gonna try. For me.”

“I hate you,” Dean said, took the book and sat back down, winced, wriggled a bit in futile search for a better position, sighed heavily and started reading. Or tried to, anyway.

Hidden behind his own internet research, Sam watched Dean sweat and squirm in his chair, drinking in the blink-and-you’ll-miss-it expressions and small sounds of increasingly frustrated pleasure that Dean couldn’t help making as he flipped through the book absent-mindedly, moved across the room to get a folder from a shelf or bring coffee from the kitchen.

And here’s where Sam’s genius idea turned kind of stupid: he decided that the only thing better than watching Dean sweat and squirm would be to watch Dean sweat and squirm in public.

“Let’s go shopping,” he declared, snapping the book he was supposed to be reading – though he hadn’t been able to concentrate on the words at all, nearly as affected by Dean’s predicament as Dean was – and getting to his feet.

Dean looked up at him with shock in his eyes. “What?”

“Well, there’s nothing in the fridge and I’m hungry. Besides, we should stock up on some supplies. Our med kit is almost empty.”

“Alright. Let me just, uh…”

“Oh no.” Sam caught Dean before he could scurry off. “It stays in.”

“No way!”


“Sam...” Dean looked around the room as if searching for something to help him plead his case before turning his gaze back to Sam. “It’s fucking distracting. And look, I can’t go out in public like this!” He pointed down at the front of his jeans, where his hard-on was clearly showing through the denim. “Neither can you, by the way.”

“Long shirts and jackets hide a lot,” Sam dismissed the objection easily. “If they can hide guns and knives, they’ll hide boners too.”

“But the damn thing is buzzing! Someone’s gonna hear.”

Sam fought the urge to roll his eyes. Who’d have thought that out of the two of them, Dean would be the one objecting to a little adventure? “It’s not that loud. And it will be barely audible once we’re somewhere with a lot of people around.”

“That’s not any better!”

“Dean, come on, just… Just do it, okay?”

A pause. Then Dean made up his mind. “Fine. But if something embarrassing happens, it’s your fault and I have the right to keep bugging you about it for the rest of your life.”


“Wanna seal it with a kiss?” Dean asked, and pressed his lips to Sam’s without waiting for an answer. “Let me get my jacket,” he said when he pulled away half a minute later.

They drove to the farmers’ market that was held every Saturday on the outskirts of Lebanon, parked the car and dove into the loud, milling crowd.

At first, Sam was so occupied with watching Dean struggle with trying to act normal while bumping into people and being bumped into, making small talk with the cute blonde who made eyes at him every time they went here, checking out the goods and haggling over prices, all the while wearing a vibrating toy in his ass just because Sam told him to, that it took him a long time to realize that there was a major flaw in his plan. The place was packed, full to bursting, the line to the stand that had Sam’s favorite 100% organic apples seemed endless, and it was clear that they were pretty much stuck here.


“Hey, I’m thinking we should split up,” Sam told Dean, who couldn’t really understand him over the noise of a tiny toddler with opera singer-sized lungs shrieking nearby. “We should split up,” he repeated, leaning over to Dean, his mouth brushing Dean’s ear as he spoke. This up close, he couldn’t miss the scent of Dean’s sweat nor the tremors that were running through Dean’s entire body. “You take the car and go to the pharmacy, I’ll stay here. You come pick me up when you’re done.”

Dean nodded quickly. “Okay.” He made to leave, but Sam caught him, a firm grip of his fingers around the tight muscles of Dean’s upper arm.

“Oh, and Dean,” he said, leaning close to his brother again, the space between them practically non-existent and probably inappropriate even in such a crowded place. Sam didn’t care. “The stimulator stays in, alright? And no touching this,” he sneaked a hand between their bodies to lightly touch Dean’s crotch, making Dean gasp against him. “Are we clear?”

It took Dean a few seconds before he collected himself enough to be able to answer. “Yeah,” he rasped, licked his lips, then cleared his throat and raised his head to glare at Sam. “You so owe me for this,” he grumbled before he walked away, his gait slightly off to Sam’s trained eyes.

The problem is, that was about an hour ago.

Now, Sam is standing in the parking lot outside the farmer’s market, paper bags in one hand, his cell phone in the other, and neither the Impala nor Dean are anywhere in sight. He’s not answering Sam’s calls either – not the ones Sam made to his regular phone, not the ones to Dean’s other phone or his other other phone.

Which can only mean one thing: something’s wrong. And Sam is slowly starting to freak out.

Has some monster jumped Dean? But the bunker’s radar showed no signs of demonic activity in the area this morning. Has Amara found Dean and took him God knows where? But she hasn’t made a move since the angels tried to nuke her, so hopefully that's not it either. Has Dean crashed the car because the stupid stimulator proved to be too much of a distraction? No, that can’t be it either, Sam silently reasons with himself. He’s seen Dean drive that car in conditions that would put other people in the hospital.

Dean is fine. Dean must be fine.

“Where the hell are you, Dean?” Sam mutters and dials Dean’s number again. Still nothing. “Damn it!” He yells at the phone screen, ignoring the glares people around him are giving him.

Just then, he hears the Impala’s familiar roar and a second later, he sees the car pull up next to him. Dean’s sitting behind the wheel, a bruise blooming on his chin, and he's bleeding from a cut just above his left eye. The relief that Sam felt is immediately replaced by more concern, especially when Dean barks, “Get in,” in a tight voice full of distress.

The moment Sam’s inside the car, Dean takes off, tires squealing and kicking up dirt behind them.

“What happened? Are you okay?”

“I’m fine, quit touching me!” Dean bats Sam’s hands away, scowling at the road before him.

“You’re hurt!”

“Yeah, I noticed. It’s nothing I can’t handle, so just chill already, will you?”

Sam doesn’t think that It’s nothing I can’t handle is comforting at all when coming from Dean’s mouth, but a quick visual inspection indicates that Dean doesn’t seem to have sustained any serious injuries, so Sam chooses to believe him for now. “What happened?” He demands again. “Why are we in such a hurry?”

“Well, I’ve got one fed in the trunk and another one on the backseat.”

“What?” Sam turns back, and yes, the blanket-covered lump on the backseat definitely looks human-shaped. “You killed two FBI agents?”

“What? No!” Dean sounds offended. “Knocked them unconscious. Man, who do you think I am? Wait, don’t answer that.”

Still leaning over the backrest, Sam lifts one corner of the blanket to take a look at the man underneath. He’s got a black eye, a split lip and there are dark strangulation marks around his neck, and his hands are cuffed behind his back.

“His own cuffs,” Dean announces proudly. “Bet the son of a bitch won’t be able to get out of them like I did.”

Sam covers the man with the blanket again and turns to stare at Dean. “Look, how about you just explain what went on? And start at the beginning this time, please?”

“I was on my way to the pharmacy when these two pulled their guns on me. Cuffed me, then knocked me out, locked me up in the back of their stupid car. Not a lot of room in there, by the way. Why would anyone buy such a fucking small car? It’s not like we’re in Europe.”


“Yeah, alright, alright. So, the feds weren't really looking for me, but one of them recognized me from the good old times when the Leviathans were wearing our mugs while slaughtering people. Thought I was a sick psycho. Apparently wanted to have some more fun with me before he called his superiors.”

“So how did you–“

“Just let me tell the story, damn it! I’d be done already if you didn’t keep interrupting me.” Dean makes a dramatic pause for extra effect before he continues. “When they dragged me to their motel room to do some ‘questioning’,” Dean lets go of the steering wheel to make air quotes with both hands, scraped, bloody fingers and all, “I got out of the cuffs, kicked their asses, went back for the Impala and went to get you. We gotta take them to the bunker.”

“You want to keep them locked up in the dungeon?”

Dean sends a very judgmental look Sam’s way. “No! Come on, Sam! I figured we’d dig up some memory loss spell, make them forget they ever saw me, splash them with alcohol and dump them in a ditch somewhere.”

“They’ll wake up and think they got drunk and got mugged,” Sam nods, already wondering which spell book to look into first. There was one written by a Canadian Man of Letters in the 1920’s that should have what they’re looking for.

“Yeah,” Dean nods. He makes a turn to the bunker. “And even if they think something fishy’s going in, they’ll be too embarrassed to admit it, so they’ll probably keep their mouths shut about the whole thing anyway.”

“Good thinking.”

“I’ve got the brains and beauty,” Dean cracks a grin at Sam and parks the car in front of the bunker’s entrance. “Now, will you help me get them downstairs? They’re a bitch to carry.”

“Getting weak in your old age?”

“Shut your mouth. I’m not the one with grey hair here.”

You shut your mouth.”

Together, they drag the feds down to the basement, where they lock them up for the time being, just to be safe. Neither of them is exactly fond of chases through the bunker's corridors.

First, Sam cleans the cut on Dean's forehead and puts a butterfly bandage over it, despite Dean's objections that it can wait. "Stop being so impatient," he admonishes Dean, who can't seem to stop squirming and sit still.

"Easy for you to say."

When Sam is done fixing Dean's face, they go to the library and find the short-time memory loss spell in the first book Sam suggested. Since they’ve got all the necessary ingredients, there is no reason not to cast it right now. The spell comes with no cool special effects, just a little spark going off above the two men’s heads, which Dean deems unacceptable and adds to his long list of reasons why the Men of Letters were stuffy glorified librarian douchebags.

“Just be glad it worked,” Sam tries to mollify him when they drop the still-unconscious feds off at an unfrequented backroad, because he’s growing tired of the grumbling Dean’s kept up for the past ten minutes.

“Yeah, but it’s still lame,” Dean insists and splashes cheap whisky on the men liberally. He steps back to examine the scene critically before giving a satisfied nod. “Alright, I think it’s cool. Now that these two morons are dealt with, can I finally take that damn thing out of my ass?”

For a second, Sam forgets how to speak, or even how to breathe. “W-what?” He stutters out when he finally finds his voice.

“The fucking prostate stimulator,” Dean enunciates slowly and carefully, as if talking to a small child. “Can I take it out, please?”

In the silence, Sam realizes that yes, now that he’s looking for it, he can still hear the faint buzz of the thing. “You… You kept it the whole time?”

“I was kinda busy being arrested and being unconscious and getting out of the cuffs and fighting two angry armed feds, yeah,” Dean is raising his voice now. “And I can tell you, it’s pretty confusing, doing all that with a fucking hard-on and a vibrating toy in your ass.”

Again, it takes Sam a while to find words. “But… But once you got free, you could have…”

“You told me not to,” Dean says simply, as if that explains everything.

And then it hits Sam: to Dean, it really does. Sam told him not to take it out, so Dean didn’t.

Knees buckling, Sam reaches out to grab Dean’s shoulders for support. He stares into Dean’s green eyes, so open and trusting. “Jesus fucking Christ, Dean…”

“God, what now?”

Instead of replying, Sam kisses Dean hard, tongue slipping right past those soft, plump lips to invade Dean’s mouth, arms wrapping around Dean’s body to bring him closer. They both moan when their erections press together, and without breaking the kiss, they start opening each other’s pants.

Sam walks them back to the Impala, where they break apart for a short moment in which they both push their pants down with speed that speaks both of practice and urgency, and then Sam is bending Dean over the Impala’s front, pulling the stimulator out of Dean’s hole and replacing it with his cock in one smooth move.

“Fuck, yes,” Dean groans, pushing back, trying to take Sam even deeper. “Sammy, you gotta–“

“I know.” Sam pulls out a bit, then snaps his hips forward, making Dean yell out and the Impala creak beneath their combined weight. “I’ve got you, Dean.”

“Then make me feel it,” Dean growls.

“Oh, you’ll feel it,” Sam promises knowingly.

It doesn’t take long, and there’s not a lot of finesse to it, just Sam fucking Dean hard and fast and Dean spurring him on to go even faster and harder until his words become incoherent sounds and then suddenly he clenches up around Sam, going absolutely still for a second before spilling all over Sam’s hand. “Sammy,” he whispers, sounding blissed out and wrecked at the same time, and Sam has no choice but to follow him over.

They lie there, Sam draped over Dean, trying to catch their breath, until Dean starts squirming under him. “Hey, get off me, Sasquatch. You’re crushing me. Let’s go someplace more comfortable.”

Sam doesn’t really want to move, but Dean’s got a point, so he wills his arms to hold him up until he’s sure his legs will carry him, and reluctantly steps back and zips up his jeans.

Dean turns around to do the same, but freezes with his pants midway up his thighs. “Uh, Sammy?”


“We got more of that memory loss spell stuff around?”

“Yeah, why?”

“I think we’re gonna need it,” Dean points at the two feds who stare at them all googly-eyed, disgust and horror written all over their faces.

“Incestuous homosexual mass murderers,” one of them says, raising a shaking finger to point at them accusingly.

Dean rolls his eyes, unimpressed. “Yeah, like we haven’t heard that one before. Hey, little brother, would you take care of these two while your big brother finishes getting dressed?”

Sam grins at him. “Sure thing, honey.”