Is that him? Is that Derek?
Uh, sort of.
#I really have no idea why I’ve always found this scene SO cute #like #it’s so fucking cute to me #he probably doesn’t have any tooth paste #and he has no fresh water to rinse his mouth out #he just spits afterwards and calls it even #but it’s so cute #like #I’m this badass hunter #I kill things with no hesitation and known a million different ways to be sent to prison for life #I’m dangerous in every sense of the word #but dental hygiene is important #with my purple tooth brush #and dean has a matching blue one #I bet they bought them in a set #and dean gave him the purple one because ‘that’s the one for girls’
Everything about this scene is wonderful in my opinion. It’s mentioned in the show how often they live out of the Impala to the point of sleeping in it but they’ve only shown it in the show maybe a handful of times. But this scene doesn’t just show that, it shows a very realistic routine of Sam brushing his teeth without toothpaste, Dean waking up in an uncomfortable position, them being out of food, Dean having to toss an old sandwich. We usually see them in diners or motels and while we get a sense of their lack of home, without scenes like this it’s hard to grasp how they are actually homeless. It’s a very realistic glimpse of their lives and I love it.
Meg. Just here for moral support. I mean, after all, we go way back. Dean and me. Just met you, of course.
Dean Winchester wasn’t a bad person. He was a good person who just happened to get stuck in shitty situations.
It was Dean’s second time in prison. He was in solitary this time around, but not because he had done something bad. He was in SHU because the exact opposite. When Dean had been in prison the first time around, he had to serve 3 years. He joined a gang for safety, but it had only gotten him into more trouble. He was in lockdown, condemned to his cell for 23 hours a day, because he had quit said gang, and his head was now wanted by every other gang member in the prison. In the eyes of the gang, Dean Winchester was a dead man.
Dean didn’t really mind it though, and tried to use all his free time to learn. He had finished his GED, and was on his way to trying to get a college degree of some sort. He had 8 months left on this sentence, and he figured he could do something productive in that time. Dean heard the buzzer go off, and his cell door unlock. Shower time, he thought. He stood and grabbed his small bag of toiletries. There was one huge bonus to being in solitary; he got to shower alone. Showering in prison wasn’t as bad as they made it out in movies or TV shows, but it was still not enjoyable and Dean was just happy he didn’t have to keep one eye open anymore, so to speak.
He stood in front of the cell door, and was surprised to see not his normal guard, John, but a new one. The man was big and tall- taller then Dean, which meant over 6’1”- with silky brown hair that fell around his shoulders, slanted hazel eyes, and muscles that were obvious even under his uniform.
"Shower time," the new guard said, pulling out his transport cuffs.
Dean held out his wrists and as the guard cuffed him, Dean asked where John was.
"New schedule change. I’m Officer Wesson."
Dean nodded, following the officer down the hall and into the shower room. It was always cold in there, causing his nipples to stand erect under his shirt. Once Wesson had uncuffed him, Dean stripped and turned the water on, testing the temperature before stepping under the spray. He stood under the stream of water, taking his time lathering his body. Since Dean didn’t go out in the yard during his hour of ‘free time,’ he almost always used the whole hour to shower. It was his happy place.
Officer Wesson stood right outside the shower, watching him intensely. Dean figured normal people would be uncomfortable having a stranger watch them shower, but being in prison, you got use to having your privacy invaded real quick. However, the young guard was attractive and Dean could feel himself getting aroused. John often left the room for a few moments so Dean could masturbate and he wondered if the new guard would also do him this favor.
"John usually leaves so I can, uh, take care of things," Dean said, turning and gesturing to his cock.
Wesson chuckled and grinned, “Go for it, kid. I ain’t got no problem with it.”
Dean frowned, but turned and continued washing himself. He contemplated what he should do before ultimately deciding fuck it. Why should he care if someone watched him jack off? It’s not like it hadn’t happened before. Wrapping his fingers around the base of his cock, Dean began to stroke lightly. He closed his eyes, trying to conjure up some dirty fantasy when he felt cold metal slide between his thighs.
"What the fuck?"
Dean tried to turn but Wesson’s strong arm was suddenly holding him in place, thrown across his back.
"Stand still, inmate. You don’t want to do this the hard way."
Dean swallowed and nodded, feeling the cold metal of the officer’s baton press up against his balls.
"You have a nice ass, Winchester. You ever let anyone fuck it? Ever been anyone’s prison bitch?"
Dean shook his head and felt his cock twitch at the guard’s dirty words. He heard the unzipping of pants and the rustle of clothing before he felt Wesson’s warm, nude body press against his.
"Well, sweetheart. You’re going to be mine.”
Dean moaned, as the officer slid to his knees behind him, and spread his ass-cheeks wide. Dean leaned forward, pressing his cheek to the cool tile, and officer Wesson squeezed his ass in big hands.
"Fucking perfect little ass," he whispered, running his thumbs over Dean’s furled hole. Dean whimpered, and pressed his ass back automatically, head clouded with lust. His skin felt hypersensitive; he could feel every warm puff of the man’s breath against his ass, every rivulet of water running down his body. He hadn’t had this much physical contact with someone in nearly a year, and it was almost too much.
Dean bit back a sob as Wesson ran his tongue across his hole, and he heard the guard chuckle. “You like that, sweetheart? Hmm? Like my tongue on your sweet virgin hole?”
Dean nodded, and whimpered, as the officer’s tongue continued to assault his hole; long slow licks, fast kitten licks, back and forth, back and forth.
He held two fingers up to Dean’s mouth. “Suck.”
Dean followed orders, Wesson’s authoritative tone affecting his cock in a way that no one had before. He licked and laved at Wesson’s fingers as though he was giving head. When the officer was satisfied that he had gotten them good and wet, he pulled them out of Dean’s mouth and massaged one of them over Dean’s hole.
Wesson gently pushed one finger in, reveling in the moan that escaped the inmate’s mouth.
"Does that feel good, Winchester?"
Dean nodded, and a litany of “more, more, more,” fell out of his mouth when the officer’s finger tip rubbed over that tiny magical button inside of his body. “God, that’s so good.”
Officer Wesson grinned, and slid a second finger inside the willing man, scissoring them and stretching the tight muscle. “Actually, you can just call me Sam.”
He grabbed Dean’s bottle of shampoo and added a little to three of his fingers to make them more slick- it wasn’t ideal, but it would work for now, and Sam made a mental note to bring lube on his next shift. He gently slid three of his fingers in, preparing the man quickly, but making sure he was well stretched before pulling back. After all, Sam wasn’t exactly little and the last thing he wanted was to tear Dean.
Dean whimpered in loss when he felt Sam’s fingers leave his body, but the big guard just shushed him and pressed a soft kiss to his neck. “Calm down, sweetheart. I’m going to take care of you. Do you want me to fuck you, Dean?”
Dean nodded furiously, almost screaming in relief when he felt the blunt, slick head of Sam’s cock nudge his hole. He bent over further, spreading his legs to give the guard better access to his body. Sam gently rubbed his back as he slid his cock in. The burn was unbelievable - a mix between it being Dean’s first time and the shampoo as lube- but Sam’s (surprisingly) loving words and gentle touches made it bearable. Dean felt full like he never had before, and when Sam was fully in him, balls pressed against Dean’s ass, he clenched his hole tightly around Sam’s cock.
"Fuck, baby. You are so fucking tight."
Dean moaned as Sam shifted, pressing the length of his cock against his prostate. “Fuck, Sam. Move, please!”
Sam growled and bit into Dean’s shoulder before pulling his cock back and thrusting back in, hard. Both of the men were panting hard as Sam fucked his cock into Dean, the inmate pressing back into each thrust just as hard. Sam leaned forward and wrapped one of his big hands around Dean’s cock, stroking it in time with his thrusts.
"Come for me, baby. Come on, Dean. Come."
Dean shivered, body tensing as his cock pulsed out his hot release. He felt his hole flutter around Sam’s cock, and the guard moaned, low and deep as he filled Dean’s hole with his come.
They stood like that, Dean bent forward, face pressed into the tile, and Sam bent over him, until Sam’s cock went limp and gently slid out of Dean’s body.
Dean whimpered as he straightened up, a sharp pain running through his ass. Sam frowned and kissed Dean lightly on the cheek.
"Sorry, sweetheart. Didn’t mean to be so rough."
Dean nodded, and let the guard gently clean him off. This wasn’t what he had expected from the bigger man, but he wasn’t going to complain; he hadn’t gotten affection like this in years.
When the hour was up, Sam walked Dean back to his cell, and helped him lay down in bed, covering him with his blanket.
"I’ll bring you your dinner in a bit, alright?"
Dean nodded. Sam pressed a last kiss to his cheek before brushing his hair back and leaving the cell, door locking behind him. Dean curled up into a fetal position, pulling the scratchy blanket up to his chin. He felt his chin wobble, and a tear escape his eye. He couldn’t let himself dare to think that this had been more than a fuck, but Dean so desperately wanted that. The way Sam had touched him, washed him, tucked him into bed…There was too many emotions floating around him right now, and he was too exhausted to sort through them. He closed his eyes, let himself cry, and just waited for Sam to come back.
When Sam left the cell, his hands were shaking. He felt nauseated at what he had done. Dean was a prisoner-The man couldn’t legally give consent. That thought alone had Sam running to the nearest trashcan and heaving up his lunch.
One of Sam’s co-workers, Officer Collins, walked past and whistled. “Doin’ okay, kid?” The man was far shorter than Sam was, with blue eyes so bright they felt as though they could see into Sam’s soul.
Sam spat into the trashcan before looking up and nodding. “Yeah, just been a crazy day.”
Collins nodded and pulled out a pack of gum, offering it to Sam who gladly took a piece. “It only gets crazier,” the man said, “just wait. Lunch for the inmates is in an hour…you’re lucky you got SHU, general population is madness.”
Sam gave a wry laugh. “Yeah, I can only imagine.”
The shorter man smiled and clapped his hand on Sam’s shoulder. “It’ll get easier.”
With that said, the man left, walking down the dimly lit hallway. Sam sighed and rested his forehead against the cool wall.
Today was going to be a long one.
When Dean woke up, it was to the sound of his cell door sliding open. He glanced over to see Sam standing at his open door, tray in hand. “Dinner’s here.”
Dean whimpered as he sat up in bed- His ass was so sore, sending shooting pains along his spine. He knew his eyes were rimmed red and swollen without even looking in a mirror and he kept his gaze fixed on the bedsheets.
"Here you g- Dean? Oh my god, are you okay?"
Dean shook his head, a sob making its way out of his throat. Dean felt weak- far weaker than he had in years. He felt like the little boy again that had watched his father being arrested all those years ago.
Sam walked further into the cell, placing the tray on the bed beside the inmate. He kneeled between the inmates legs and took his hands in his. “Hey, Dean. Come on, talk to me. Are you hurt?”
Dean shook his head. Sam’s voice was so comforting, so loving and sweet, that it made Dean’s heart throb. “Not hurt. Just a little sore. I’m fine.”
Sam frowned, “You were crying. I can tell.”
Dean gritted his teeth and pushed the guard away from him. “Stop acting like you care. Just leave, please.” Dean couldn’t afford to fall for him. It would hurt him so badly when Sam denied him.
The guard sighed, and kissed Dean on the cheek gently before walking back out of the cell. Dean didn’t look up, but he heard the cell door close and lock.
He’d never felt like this before. Dean had spent nearly his whole life alone. Sure, he had some hookups, even a few short term girlfriends, but never anything like this. He felt like shit. His heart felt like it was ripping in half. It would have been fine if it was just sex. But it wasn’t. Sam had…taken care of him after.
Dean slammed his fist into the cell wall, over and over again. He felt his knuckles break, hand smashing into the wall continuously. He didn’t care. Nothing could hurt as much as this empty feeling he had inside.
Sam’s shift ended just before dinner and he breathed a sigh of relief as he walked out of the prison. The December air was crisp and cold against his skin and it felt good. He’d needed this all day, this refreshment. He was still so conflicted about Dean. The man was so beautiful- sinfully so- but something about him was innocent, broken. Sam wanted to fix him, to care for him…to love him.
Sam was screwed.
Dean saw the guard the next afternoon. It was shower time again. Dean had been in bed all day, hand mangled and throbbing. He hadn’t told any guards- he didn’t need to be put into the psychiatric ward of the prison. Been there, done that. They just cuffed him to a bed for a week and gave him a shit ton of sleeping pills. When he wasn’t sleeping he was drifting just on the cusp of consciousness listening to other inmates scream, yell or cry. Not something he wanted to repeat again.
"Dean? It’s time to shower."
Sam’s voice was gentle from the door of the cell- Dean hadn’t even noticed it being opened.
Dean rolled over in the bed, and got out from under the covers. Without making eye contact, he held out his wrists for the guard to cuff him. Sam’s eyes went wide as he took in Dean’s hands- the swollen redness, the black and purple bruises that covered his knuckles.
"Shit, Dean. What the fuck happened, oh my god."
Sam grabbed Dean’s hand gently and ran his thumb over the bruised and broken knuckles. Dean winced but held in the groan he wanted to release- he didn’t need Sam’s pity.
"You did this to yourself?" Sam grabbed Dean’s chin and tilted his head up to stare him in the eye.
"Well, who the fuck else would have done it?" Dean snapped, pulling his hand from Sam’s grip. Sam frowned, and gently pushed the inmate to the bed.
"I’m going to take you to the infirmary, then you will shower, and then we are going to have a long talk about this. Understand?"
Dean stared at the floor hard, and didn’t respond. Sam just sighed and pulled him to his feet. He slid the cold, metal cuffs around Dean’s wrists, being careful to avoid hitting the knuckles.
"Come on, Dean."
Sam stood outside of the shower, and watched Dean bathe. His hand was wrapped in thick white gauze, and he seemed to be having trouble washing without getting it wet.
The inmate continued to stare at the ground and attempted to wash his hair.
"Dean. Let me help you."
"I can do it," Dean grumbled, clenched his fist.
"Please, Dean. I won’t…I won’t touch you again. I just want to help you."
"I don’t need your fucking help!"
Dean threw his washcloth at Sam and dropped to the ground, collapsing in on himself. Sam was shocked- this was so unlike the Dean he had fucked in this very shower the day before. He could hear Dean’s uneven breathing and felt his own heart sink to his stomach. What was going on?
"Hey, Dean? God, Dean. Come here, please?"
Sam grabbed the towel from the rack and turned the water off, soaking the sleeve of his uniform. He knelt onto the floor and wrapped Dean in the towel. The inmate was silent, tears rolling down his face, but no noise coming from him anymore. “Talk to me,” Sam pleaded, “I’m fucking worried.”
Dean just shook his head, eyes squeezed tight.
Sam sighed in resignation. “Come on, Dean. I’ll take you back to your cell.”
Sam took the inmate back to his cell, and closed the door behind them. It was strictly against protocol, but something about Dean made him not care. Sam carried Dean back to his bed and laid the man gently out on the bed, covering him with the coarse grey blanket.
“Do you want to talk?” he whispered, fingers stroking the softness of Dean’s cheek.
Dean shook his head, but then nodded.
“I’m scared,” the inmate whispered, face half pressed into the pillow. “You…make me feel. I don’t know if I like it. I don’t know what to do about it.”
Sam could see the tears welling in Dean’s eyes, and he quickly brushed them off his cheek. “Dean…”
“Let me finish, please. Sam…I…Sleeping with you was amazing. But…I’m in here. I’m in fucking prison. What the fuck is this?”
Sam sighed, and ran his hand through his hair. “I don’t know, Dean. I honestly don’t know. It was…it was sex, at first. But now…I don’t know. I want more, Dean. I want more.”
Dean sighed and rolled onto his side, curling into the mattress. “Okay.”
Sam was frustrated, and if he was being honest, a little heartbroken. He stood, and started walking to the cell door, when he heard Dean whisper.
Sam stopped, and turned, looking at the inmate who was still curled facing the wall.
Dean sat up and pulled off the shirt he was wearing. “Don’t. Leave. I want you, Sam.”
Sam could see the outline of Dean’s erection through his loose fitting pants and he growled.
He quickly pulled off his uniform- They probably needed to talk more about this but Sam just couldn’t wait. He needed Dean so bad, needed to show the other man how much he truly did love him. He grabbed the lube he had put in his pocket before his shift out and set it on the bed, before pulling Dean’s face to his.
Dean moaned, and fisted his hand in Sam’s hair.
“Fuck, Dean. I need you.”
Dean growled and raked his nails down Sam’s back. “Take me, please, Sam, please.”
Sam nodded, pulled down Dean’s pants and grabbing for the lube. He slicked up three of his fingers and opened the inmate quickly. He knew he should spend more time opening Dean- he had only lost his virginity yesterday- but it seemed neither of them could wait. By the time Sam had gotten 3 fingers inside his lover, Dean was begging.
“Sam! Please! I need you, right now! Fuck me, please.”
Sam growled and slicked his cock, before pulling Dean’s legs over his thighs. He pushed inside the man with one long thrust and they both cried out.
“Fuck, you feel good.”
“More, Sam, more!”
It was quick and hard. Sam’s pace was punishing, and they both came too quickly, but it was perfect; everything they both needed.
Dean collapsed onto the bed, and curled his arms around Sam’s waist.
“Dean, come on baby. I have to get back to work.”
Dean grumbled, but let go of his lover, before curling into the warmth he left behind on the bed. It felt so strangly domestic and Sam wished he could just pretend that they were in his apartment- Sam getting up for work and leaving his lover in their bed.
“I’ll see you tomorrow. Dean…Whatever else happens…I’ll wait for you. I promise.”
Dean was already asleep, so Sam pressed a gentle kiss into his forehead and pulled the blanket over him.
“You won’t have to be alone again.”
The guard closed the cell door and locked it, before leaning his forehead against the cool metal. Only 8 months left on Dean’s sentence.
They could do this.
8 months later
The fresh air against Dean’s face made him nearly break down into tears. It had been so long since he’d felt the wind, tasted the clean air…
“Sam,” he whispered, squeezing his boyfriend’s hand in his own. The taller man gave him a huge grin and squeezed back.
“It’s okay, Dean. How do you feel?”
Dean glanced over his shoulder at the prison and suddenly let out a loud laugh. “Amazing,” he whispered. “Just amazing.”
Sam smiled and pulled his lover in for a quick kiss- their first kiss since Dean became a free man. “Come on, Dean. Let’s go home.”
Sam’s home was small, but warm- the type of home that Dean had always dreamed of having. They cooked their first dinner together- spaghetti and meatballs- and then curled up on the couch to watch TV together with Sam’s dog, Sadie, curled up at their feet. It was so perfect and Dean never wanted it to end.
Sam’s fingers trailed along Dean’s spine, twisting around each knob, and Dean hummed happily, leaning into Sam’s broad chest.
“Hey, baby?” Dean asked, tugging on the bottom of Sam’s shirt.
“Lets go to bed,” Dean whispered, standing and tugging on Sam’s hand. His lover happily agreed, scooping Dean up and carrying him up the stairs in a fireman hold.
Oh yeah, Dean thought. I’m going to adjust just fine on the outside.
Because he had Sam, and in the words of John Lennon, all you need is love.
Dean, my sweet summer child…
i made an au. and i am going to roll around in it forever.
it’s a ’60s endverse!au so it’s really depressing(◡‿◡✿)
keep my eyes fixed on you…..