The Five Times Sam Tried to Kiss Dean and the One Time He Didn't

AN: I seriously love doing these five times fics. Also, I really need a beta. Help a girl out?

One.

Sam arched his back and groaned, frustrated that Dean's hands held his hips down making it impossible for him to thrust forward. He dropped back down with a sigh and fisted his hand in Dean's hair, pulling at the spiky wisps, growling as he bit his lip. He looked down at Dean, watching as his cock slid deeper and deeper into that perfect mouth, his brother's lips were swollen and Sam felt his whole body clench at the sight before him. He moaned loudly when Dean flicked his gaze up, his intense mossy green eyes locking on Sam's as he pushed himself lower over Sam's length.

"Fuck Dean…" Sam panted rolling his hips as much as the pressure of Dean's hands allowed. Sam's body went rigid and Dean gripped his flank, digging blunt nails into his skin and Sam cried out, falling back against the bed. Sam couldn't help but shout Dean's name as his body tensed and he came hard, Dean's mouth continuing to work over him as he rode out his orgasm. Still panting, he felt Dean shift on the bed and straddle his waist. The bed was shaking a bit and Sam heard Dean grunt before hot liquid spurted onto his chest and abdomen. Sam groaned; he loved it when Dean came on him, it was so territorial, so possessive and Sam knew that Dean didn't do this with his other conquests and that made the feeling even more intense.

Sam reached over the side of the bed and grabbed the t-shirt he had left there and wiped himself up before handing it to Dean. Dean wiped off his hand and then flopped on the bed next to Sam, who immediately curled up on his side next to his brother. Dean didn't tolerate cuddling, but he allowed Sam to curl up close to him which, Dean assured him, was more than he let anyone else do. Today though, Sam was feeling bold and he stretched his arm out and began tracing patterns on Dean's chest with his finger. Dean had his eyes closed and his arms bent at the elbow, hands resting under his head and Sam wanted to move closer, into the space that he knew would be perfect for him, but he held back, not wanting to be pushed away. He couldn't take the rejection. Not from Dean.

"Dean…" he whispered and a grunt came from his brother in response. "Can I…" he paused, not sure how he wanted to continue. Dean, noticing his silence, cracked his eyes open and looked down at him. Big, hazel puppy eyes were staring back up at him and Dean knew immediately what his little brother wanted.

"Ah hell, Sammy. Really?" he said but Sam just continued to look at him. Dean sighed; he had never had much will power when it came to Sam. "Fine." He conceded, "You get five minutes of this pansy bitch bullshit." He said grabbing the remote to the TV. He flicked it on and Sam smiled, sidling up to Dean and putting an arm around his waist before winding a leg over his brother's. Dean lowered his arm and Sam smiled in contentment.

He kissed Dean's chest in appreciation and trailed those kisses up to his collarbone, to his neck and finally his jaw. Sam shifted to get a better angle, but just as he leaned down, Dean coughed and turned his head and Sam's lips connected with his cheek. Sam felt ice pool in the pit of his stomach, but ignored the stinging rejection and finished the kiss on Dean's cheek before setting dejectedly against his brother's side once more. Sam tried to catch Dean's gaze, but he was staring determinedly at the television screen as though the Magic Bullet infomercial was the most interesting thing he had ever seen. Sam tried to keep his confusion contained as he rest his head back on Dean's chest. Apparently, kissing was out of the question too.

Two.

Sam pushed Dean back against the bed and very nearly snarled at him as he pinned his brother's wrists on the bed next to his head. Dean groaned and rubbed his clothed erection over Sam's and Sam bent down, nipping at Dean's neck with his teeth. Dean turned his head, giving Sam more access and he began placing hot, open mouthed kisses along the soft column of Dean's neck, sucking here and there, leaving small marks on the flesh. He caught Dean's earlobe between his teeth and licked the shell of Dean's ear, grinding his hips down, eliciting a sigh from Dean when he increased the pressure. When he turned to face Dean again, his eyes were hazy and rolling to the back of his head as Sam continued the slow rocking of his hips.

"Sammy…" Dean breathed and Sam smiled, releasing one of Dean's wrists to grip him under the chin and force his head up. Sam pulled Dean's lower lip in between his teeth and ran his tongue over it, getting so close to slipping his tongue into Dean's panting mouth, but suddenly found himself on his back instead. Sam had not counted on Dean being able to flip their positions so easily but coherent thought left him as Dean settled down on top and resumed the dizzying roll of hips, sending a glorious heat pooling in his groin. The friction sent shockwaves of pleasure through him and he growled low in his throat, throwing his head back.

Sam felt Dean grab his wrists and place them low on his waist and Sam gripped tightly and pressed down. He felt Dean squeeze his forearms as his rutting became more erratic and it was obvious that he was close. He looked down at Sam and fuck, did he look hot. Dean's face was flushed and his eyes were lidded as he chanted "Sam" so softly, Sam could barely hear. Sam watched as Dean reached down and undid both of their jeans and pulled their cocks out to rub together. Dean held them both in one hand and stroked upwards. He released Sam's other arm and leaned back a bit, giving Sam an unobstructed view.

"Oh fuck Sammy…"Dean rasped, "Fuck. I'm gonna…" Sam tilted his head back and groaned, biting his lips as Dean's hand sped up.

"Jesus fucking Christ Dean…" Sam groaned as he watched Dean come. Sam squeezed Dean's hips tighter as he followed him over the edge. Too soon, the feeling was gone and Dean was already moving off him by the time Sam came down from his high. Sam let him go, watching as Dean moved to the bathroom to clean up. He doesn't want to be around me right now. Sam thought with a frown. They had kind of fallen into a routine; they would have sex, use Sam's shirt to clean up, and then fall asleep together. Sometimes there was cuddling, sometimes there wasn't, but if Dean was changing that now, it wasn't a good sign. Something was making him uncomfortable and as Dean was a master avoider, Sam would just have to poke and prod until he found out what it was.

Three.

"Take me down to Paradise City where the grass is green and the girls are pretty..." Dean was singing again and Sam had to struggle to not cover his ears. He looked sideways at his brother and Dean looked back, shrugging. Mercifully, he turned the radio down. "What Sammy? Don't like Guns-N-Roses?"

"I like them just fine Dean, just not when you sing."

"Oh c'mon Sammy!" Dean said clapping him on the shoulder, "Just think, only three more hours of this and we'll be in Vegas!" Dean had a giant shit-eating grin on his face and as annoyed as Sam was, he couldn't help but smile back.

"That's what I'm afraid of. What the hell am I going to do with you in Vegas?" Honestly, Sam didn't want to go, at all, but Dean insisted.

"Town like that," he had said, "There are bound to be pissed off spirits there." Sam groaned at the thought. He really didn't want to go.

"Can't we just go somewhere else Dean? Vegas is so…"

"Awesome?" Dean interjected, "Yeah, I know."

"That wasn't exactly the adjective I was going for…" Sam trailed off, looking down at the map.

"We're gonna have a great time Sammy, trust me."

"Yeah sure…hey can you pull off? I gotta pee…" Sam asked and Dean laughed.

"Great Sam thanks for the info." Dean said sarcastically, but he jerked the Impala to the right onto the shoulder and Sam got out and moved to the line of trees. Dean was actually feeling a bit full himself so after getting out of the car and locking up, he followed behind Sam, moving somewhere off to the right. He might be able to suck his brother's cock, but he definitely did not need to hear or see him piss. Mid-stream, Dean heard a branch crack. His head snapped up and turned in the direction of the noise.

"Sam!" he called out but received no answer. Fuck. He though, I'm gonna get attacked with my fucking pants around my ankles and my dick out. Thankfully, he finished without incident and was pushing himself back into his pants when he heard more twigs snap, closer this time. He left his pants undone and pulled out the pistol he kept in his jacket's inside pocket. He clicked the safety off and cocked it, but before he could turn, a body was pressed against his from behind.

"Scare you?" Sam inquired hotly into his ear and Dean breathed out a sigh of relief.

"I should kick your ass Sammy." He said, but Sam's hands had reached his hips and pulled his ass into Sam's front and he could feel the erection bulging against him.

"Yeah, but you won't." Sam countered and Dean stashed the gun back in his pocket before reaching down to pull Sam's hands around him. Sam jammed his hand in Dean's pants and gripped his hardening shaft while licking a thick stripe up Dean's neck.

"Fuck Sammy…" he ground out and Sam raised one hand to turn Dean's head toward him. As soon as Sam's lips reached his chin, Dean jerked his head out of his grasp and Sam pushed him away in frustration. Dean stumbled backwards from the abrupt release and turned to voice his displeasure, but Sam was already passed the tree-line, walking back to the car. Dean hitched his pants up and followed. He knew what Sam wanted, but there was no way he could give it to him. He could see the hurt and frustration on his face, but Dean forced himself to look away, forced himself to believe that he could handle it, that Sam's need for more didn't affect him and that he wasn't wanting the same thing. He had to believe himself indifferent or else what was the point? It's not like they could ever have a normal relationship, he should have stopped a long time ago, when he realized what he felt went beyond sex, but he couldn't, he had wanted Sam too much and now, he was fully addicted.

Four.

There were no words, absolutely none to describe his frustration at this point. Sam watched Dean flirt from across the bar and he could feel the searing tendrils of jealousy snake through his veins. He gripped the base of his neglected beer and tried to keep his eyes off his brother and the blond skank that was all but dry humping him at the table. He cleared his throat and looked away when Dean thanked her, getting a hearty smack on the ass when he walked away, and stepped up to Sam.

"So Tanya over there seems to think that Mr. Johnson wasn't your average run of the mill funeral director. Seems he had a bit of a fetish." He grinned and waited for Sam to reply. When Sam didn't say anything, he continued. "With dead people," he chuckled, grabbed Sam's beer and held it to his lips, "sick bastard." He took a swig and still, Sam remained silent. "What's your problem Sammy?" Dean asked leaning over and entering Sam's personal space (if he even had any when it came to Dean) Dean lowered his voice, "I just told you that our prime suspect likes to fuck corpses and you're completely stone-faced. What the hell?"

"Eww gross…dead people." Sam whined petulantly while peeling back the label of the beer Dean returned to him.

"What the hell Sam?" Dean scrunched his eyebrows together and Sam huffed before hopping off the barstool and exiting the bar. "Sam!" Dean shouted once they were outside. Sam didn't slow down, just kept walking quickly to the Impala. "Sam!" Dean yelled again but this time, Sam didn't have anywhere else to run to. He had reached the Impala and Dean slammed him up against it, pressing against him from behind.

"Get off me Dean." Sam said twisting in his brother's hold. He tried to push Dean away, but Dean had better footing and was angry.

"What the hell is your malfunction man?"

"You Dean. God, seriously? You're fucking blind! You're my problem!" Sam shouted back in his face and the surprise that registered upon Dean's countenance was enough to tell Sam that his brother really didn't understand what he had done. Sam rolled his eyes and elaborated, "In the bar…that…that…who-woman. The way you just let her…and then she…Christ Dean. I was right there!" he said and his eyebrows rose imploringly. Comprehension dawned on Dean's face and he looked at Sam's sad eyes, his mouth falling a little slack.

"Fuck Sammy, were you…are you…jealous? He pushed away from Sam and backed up a few inches. Sam's silence was enough to confirm his suspicions. "Fuck." He swore again, moving back towards his brother, "Sammy, that was an act, you know that. You don't actually think I could…right in front of you…do you?" Sam just looked at Dean and Dean's hurt finally mirrored Sam's. "You don't even trust me…"

"I know you still sleep with other people…" Sam said and Dean's head dropped.

"Yeah Sammy, I know you know."

"Then why do you still do it?" Sam whispered and Dean shrugged.

"I don't know. Maybe to prove to myself that I don't need…" Dean cut himself off and swept his gaze over Sam's clearly pained face. His eyes were swimming and he couldn't meet Dean's gaze.

"To prove that you don't need me." He finished when Dean couldn't and Dean nodded.

"Yeah." He whispered.

"Then why…"

"Can we just drop it Sam?" Dean asked and Sam looked up in angry surprise.

"No, Dean. We can't just drop it."

"Then what do you want to know Sam?"

"Why you don't just end things with me?"

"Sam…"Dean nearly begged, trying to back away but Sam wouldn't let him.

"Why?" Sam repeated. Dean's eyes were red now and he sighed before answering.

"Because I can't." he voiced so softly Sam almost missed what he said, "And that scares the hell out of me man." Whatever Sam had been expecting, it wasn't that and he raised his hand to cup Dean's cheek. He leaned in, but Dean gently turned his face away and Sam ended up placing his cheek against Dean's instead.

"Dammit Dean." He whispered.

"I'm sorry Sammy."

Five.

It had been three weeks since the night at the bar when both Sam and Dean had admitted a bit more to each other than they meant to. Since then, they hadn't discussed what had happened nor had they touched if it didn't involve something to do with the Hunt. One time, just to test out the theory and because he was aching to touch Dean so badly, Sam reached over to his hand while they were driving through Kentucky and Dean jerked away from him so quickly, he swerved into on-coming traffic and almost ran into a Ford pickup loaded with hay. After that, Sam withdrew into himself and would only speak to Dean to ask or answer a question about the Hunt or food. Dean seemed content and Sam wasn't going to pressure him, if he wanted Sam to stay away, then he would not matter how much it hurt. And God did it hurt, especially tonight.

"Hey Sammy," Dean called as he stepped out of the bathroom. Sam looked up from his laptop, glad that Dean was finally addressing him, and his jaw dropped. Fuck, Dean looked hot. He hadn't done anything special, but he was freshly shaven, wearing slim fitting dark denim jeans with a long sleeve black button up. The sleeves were rolled up to show his strong forearms and his hair was spiked up in front like he did when he was trying to impress someone. Sam was hoping that this was for him, that it was Dean's way apologizing and fuck, did he want it, but that thought was shot to hell when Dean grabbed his coat and keys. "I'm going out. Don't wait up, 'kay?" Sam's mouth went dry and the bottom seemed to fall out of his stomach, but he managed to nod. Dean patted himself down and stuffed his wallet in his back pocket before moving towards the door.

"Dean…" Sam called just as the door swung open.

"Yeah?" he asked not looking at Sam.

Don't leave. "You look good." He said and Dean's lips formed a straight line and he left without a word.

And now, it was nearly four in the morning and Sam sighed in relief as he heard the scratch of the key as an exceptionally drunk Dean tried to fit it into the lock. After a few minutes of failed attempts, he finally just began knocking on the door and yelling Sam's name. Sam rolled his eyes and jumped out of bed, throwing the door open. Dean had obviously been leaning against it for support and so he tumbled into Sam's arms when it was removed.

"Hey Sammy." He slurred smiling up at his brother and Sam rolled his eyes again. He steadied Dean on his feet and went back to lie on his bed, but Dean fell in it first.

"That's my bed Dean. Move to yours." Sam said attempting to push his brother off.

"It's gonna be cold. Yours is warm. Wanna stay here." Dean garbled into the pillow. Sam sighed and picked up his lap top before moving over to Dean's bed. He didn't get far, however, because Dean's hand closed over his wrist. Sam closed his eyes and breathed in deeply, trying to ignore the flares of heat coming from the spot Dean touched. When he turned around, he was shocked to see Dean looking up at him with surprising lucidity. "I couldn't do it Sammy." He said leaving no doubt as to what he was talking about. "We went back to her place and had a few drinks. I was already sloshed, I had to be…I kept thinking about you…and she took her clothes off."

"Dean…"Sam protested, trying to pull away, but Dean held still more tightly.

"No, I need to tell you. She took her clothes off and shit, she was hot. Round, perky tits, ass you could bounce quarters off of, cute compact body… brunette…just my fucking type and I couldn't fuck her. She tried to blow me, gorgeous fucking mouth and I couldn't even get it up."

"You're drunk." Sam said and Dean nodded.

"Yeah, Sammy I am. But its more than that. I just kept thinking about you, how I knew you'd be here…waiting even though I told you not to. About how I know you'd look at me with those sad fucking eyes of yours because you knew, you fucking knew what I was doing and it hurts you so fucking bad and Sammy, I'm sorry. Shit, I don't deserve to have you." Dean's voice broke and Sam bent down to sit in front of him, pulling his big brother into a hug. Sam turned his head and unwisely tried to capture Dean's lips, but instead Dean buried his face into the crook of Sam's neck and kissed the skin there. Sam stiffened as the mood changed and Dean's lips wandered more over his exposed skin. It wasn't until his shirt was pulled over his head that Sam even noticed Dean's hands had strayed. Dean pulled Sam up to the bed and rolled over to cover his body with his own. Dean unbuttoned his shirt and Sam pushed the sides apart and off his shoulders as Dean leaned down to mouth at Sam's chest. He pulled a nipple into his mouth with his teeth and sucked lightly before moving lower to trail searing kisses down Sam's abdomen.

Reaching Sam's hips, he untied the string holding his pajama pants up and pushed them down, tonging the deep-v Sam's hips made before sinking below his boxer briefs. He felt Sam's hands fist his hair as best as he could, groaning slightly as Dean took his hardened shaft into his mouth. Sam's hips thrust up and Dean took that opportunity to sneak his hand under his body and press a finger into him. Sam bucked at none too polite intrusion, but allowed it because this was Dean, and Sam would never push him away. Sam was keening by the time Dean added another finger, rolling his hips and moaning as Dean hooked his fingers slightly to hit Sam's prostrate sending maddening pleasure coursing through his body.

He felt Sam's cock twitch in his mouth and Dean knew he was close. He pulled away and rose to his knees, pulling Sam to him and wrapping his legs around his waist but something clunked against his head and landed on Sam's abdomen. He looked down in confusion and then back up at Sam who was looking pointedly at him. Dean sighed and picked up the lube and squirted a healthy dose into his hand before slickening up his shaft with the stuff. He rubbed the rest on Sam and sheathed himself inside without much preamble. Sam cried out and instinctively squeezed Dean with his legs, holding him in for just a little while before he relaxed and Dean was able to move.

He took it slow at first, watching Sam's face for signs of discomfort, but all he could see was pure, unadulterated bliss. Dean smiled, genuinely smiled at the happiness on Sam's face and he pressed a soft kiss to his chest before continuing to move. It didn't last long, but it was passionate and when Dean came, Sam's name was all he could think to say. Sam followed him soon after, closing his eyes and tossing his head back, whispering Dean, Dean, Dean… over and over until he fell back flat against the bed. Dean pulled gently out of him and slid up Sam's body. Though they were both thoroughly satisfied and beyond exhausted, their cocks were still hard and they moaned in unison when the sensitive flesh brushed together. Sam wrapped his arms around Dean as Dean pulled the blanket over their bodies.

Sam, testing his luck again, put his hand under Dean's chin and tried to lift up, but Dean fought him.

"Not yet Sammy." He said and Sam's arms fell away in frustration.

"Why not?" he asked, but Dean had already begun to snore.

Six.

"You're what?" Dean stood in front of Sam, absolutely frozen stiff with shock.

"I'm done, Dean." He said softly, "I can't take it anymore. I'm just…tired. We have to stop." Sam looked up at him and what he saw reflected in his hazel eyes made him hate himself. Dean had convinced himself that it was only his heart the he was risking in this. That Sam would eventually grow tired of being with him and settle down and have a normal life. God knows the kid deserved it.

"Sammy…" he whined and he knew it sounded pathetic, but he couldn't help it. He was facing losing his brother and the thought broke him so completely, he was surprised that he was still standing. But just as Dean felt like falling, Sam stood and began walking towards the door.

"I'm gonna get my own room from now on. I'll try to find the closest one possible." Dean watched as Sam turned his back. It was at that moment, Dean had the veil lifted and he could see the severity of the situation with startling clarity. This couldn't be, would not be, the end of this. Dean crossed the room in three large strides wedging his body between Sam and the door. Sam had just reached out to grasp the handle and instead, Dean grabbed him by the collar of those stupid shirts he wore that Dean hated and brought their bodies flush together. There was only a moment of hesitation before Dean arched up and pressed his lips against Sam's. He could feel the want pouring from Sam as his hand immediately grasped Dean's face, pulling him closer, forcing him to deepen the kiss. Sam's tongue slid against his slippery and warm and a moan escaped his lips before he had the chance to quell it. Sam moved his body closer, effectively pinning Dean against the door as Dean's hands slid up Sam's neck to tangle in the mass of wavy brown locks, fisting them and pulling a bit, just how he knew Sam liked. Sam bit Dean's bottom lip and pulled back, sucking it a bit before releasing it and looking into Dean's eyes. They were both panting heavily and Sam leaned their foreheads together.

Sam smiled, his hands were still on Dean's face but he dropped them to his rest low on his hips when the kiss ended. Dean, however, refused to move his hands from Sam's hair.

"There." Sam whispered, "Was that so hard?"

"Shut up bitch." Dean said, pulling Sam to him again.

"Jerk." Sam smiled against Dean's lips, leaning into him again.

AN: Thanks so much for reading. I hope you enjoyed it. Any reviews are greatly appreciated. Also, I was serious earlier. I really need a beta. If you're interested, please feel free to PM me. Thanks!