"Dean, are you sure you wanna do this?" Sam asked, breathless, his older brother trailing kisses down his neck.

"Not really, but I wanna try." Dean murmured between kissing the too-warm skin on Sam's neck. Sam let out a small yelp when Dean softly nipped at his neck.

"Dean." Sam said, trying to chastise his brother, but failing because Dean's name came out sounding more like a moan. Dean snickered and continued nipping and kissing his younger brother. The older Winchester flexed his hips against the younger Winchester's, evoking a moan from both men.

"Sammy." Dean breathed against Sam's skin. He lifted Sam's shirt up to his chest, exposing the tanned and muscular body beneath the clothing.

"Why don't we just get rid of this?" Dean smiled at his younger brother through his long eyelashes. Deans heated emerald gaze excited Sam, and the younger brother bit his lip and nodded. Dean managed to pull Sam's shirt off, with help from Sam; skimming his fingers up Sam's body. Goosebumps rose on the younger Winchester's skin.

"Oh, Sammy." Dean appraised, looking at his half naked younger brother. Dean drank up the sight of Sam's muscled and tanned skin, dotted with scars acquired over the years; but Dean loved each and every one of them and found himself wanting to kiss every single inch of Sam's body. He couldn't help but think of all the times he has imagined doing this, yet he was nervous. Dean leaned down and kissed Sam passionately, both Winchester's parting their lips slightly.

"Ah...mmmph." Sam cried out when Dean reached down and palmed Sam through his jeans; but Dean cut off the noise with another heated kiss. Sam squirmed under Dean, bucking his hips, hoping to catch the slightest amount of friction.

"Stay still." Dean whispered against Sam's lips. Sam did as he was told, with great effort.

Dean pulled both his lips and his hand away from Sam and he let out a frustrated whine. Dean smirked and pulled off his own shirt; Sam watched Dean's muscles ripple with the movement and felt himself grow harder. Dean tossed the dark green garment across the room and resumed torturing the younger Winchester. He kissed up Sam's abs, while his hand went back to work.

"Stop...ah...being a...tease." Sam managed to gasp out; between Dean's hand and his lips, Sam was melting.

"I don't...know..what you're...talking...about." Dean smirked between kisses. He reached Sam's mouth and closed in. The kiss was intense and passionate; Dean tracing Sam's lips with the tip of his tongue. Normally, Dean would already be screwing the girl he was with and he would skip all the teasing, but this was Sammy and he wasn't sure about any of this so he was using this as an excuse to psych himself up.

Dean broke away and gazed down at his younger brother, asking permission with his eyes. Sam nodded and bit his bottom lip, so Dean moved his hand to the button on Sam's jeans and deftly undid it with one hand.

'I've had enough practice.' Dean thought to himself and rolled his eyes subconsciously. His heart was racing due to nerves and arousal, not quite knowing which one being the bigger factor. He used both of his hands to slide Sam's jeans off. His hands slid slowly down Sam's legs and Sam tilted his head back in pleasure. Dean could see Sam's erection straining against the fabric and palmed him yet again, but the feeling was more intense due to the loss of material between them.

"Ah...Dean." Sam moaned and wriggled beneath his older brother, flexing his hips against Dean's palm, pushing his erection farther into the skilled hands of his brother. Dean grew harder at his brothers moans and desperation. 'Apparently arousal.' Dean chuckled subconsciously.

"Oh Sammy." Dean breathed as he hooked a thumb into the waistband of Sam's boxers and pulled down. Before pulling the fabric past Sam's erection, Dean undid his own jeans and tossed them across the room.

Dean preferred compression shorts to boxers, and his erection was straining against the black fabric. The shorts only covered a few inches past Dean's ass, the fabric perfectly fit over it as well as his sculpted leg muscles. Sam looked at his older brother hungrily, wanting Dean to fuck him already.

"Dean, please." Sam begged pulling his blue boxers down the rest if the way, freeing himself. Dean looked at his younger brother's large erection and found himself losing rational thought. Dean removed his shorts and tossed them off the edge of the bed, wrapping his hand around himself, moving his hand a few times. He hardened further and Sam looked hungrily at his older brother. Sam couldn't help himself so he lurched forward and pinned Dean on the bed; quickly putting his mouth to the head of Dean's dick and sucking.

"Fuck! Sammy!" Dean growled out the younger's name as he writhed in pleasure. Sam flicked his tongue around the head and took all of his older brother in his mouth, which wasn't an easy feat considering how big he was. Dean was about seven inches, not as long as Sam, but he was thicker—much thicker.

"Stop. Sammy I'm gonna..." Dean couldn't finish his sentence because Sam bared his teeth and Dean lost it. He came into Sam's mouth and his body relaxed. Sam swallowed and licked his lips in a suggestive way.

"Delicious." Sam said in a deep voice and Dean smirked.

"My turn" Dean purred and sat up.

"Roll over." He commanded Sam. Sam rolled over onto his Stomach and prepared for what was to come.

'Holy shit, he is really gonna fuck me.' Sam's heart raced at the prospect.

Dean didn't bother with a condom, but he did get out the lube in the bedside drawer; he usually used it with women and always kept it handy, but he was looking forward to using it on Sam. He squirted a small amount on his hand and then slicked it over his length; The feel of the gel and his hand making Dean grow hard again. Sam's ass was up in the air, waiting somewhat patiently.

"Dean." Sam Mewled, growing impatient.

"Bitch." Dean chuckled and then placed the head of his length at the entrance of Sam's ass.

"Ready?" Dean asked, trying to hide his nervousness.

"God yes." Sam was ready, but also nervous considering this would be his first time doing anal. Dean slipped himself slowly inside of Sam at his younger brothers permission. He only went in part way because Sam tensed underneath Dean and clenched the sheets in his fists.

"Sammy." Dean's voice was thick with lust but worry at his brothers reaction.

"Don't. Stop." Sam gasped out into the mattress. Dean continued, but slower. He fully sheathed himself inside of Sam and Sam let out a breath of relief beneath him. Dean felt him relax. Dean was fully sheathed inside the tight heat of his younger brother and he couldn't help but pull out and slide back inside, moaning.

"Ah!" Sam gasped but tensed up again.

"Shit. Sammy I'm sorry." '

Way to go asshole, how stupid can you be.' Dean chastised himself and was about to pull out but Sam asked him to stop.

"Please no. I can do this." Sam begged, his voice muffled by the pillows.

"You don't have to." Dean soothed the younger Winchester.

"But I want to."

"It's ok. We can go slower." He wanted Sam, now, but he was willing to wait as long as Sam wanted. Dean kissed Sam's back but still stayed inside of him. Sam rocked his ass back against Dean's hips and moaned; whether out of pain or pleasure Dean couldn't tell.

"That's it Sammy, go slow." Dean purred and kissed Sam's shoulder.

Sam repeated the movement and relaxed.

"I can't." Sam stopped and Dean pulled out slowly at those words.

"I'm sorry." Dean's voice was slightly panicked.

"It's ok. It's just too much to fast." Sam consoled.

Dean threw on his shorts and slid behind Sam, wrapping his arms around his younger brother.

"Well this sucks." Sam let out a defeated sigh.

"What?"

"I...well..." Sam hesitated and Dean could tell he was embarrassed.

"Sam, what?" Dean prodded.

"Well...I'm still...unsatisfied." Dean saw Sam's tanned skin turn pink.

"Well, we will have to fix that won't we." Dean smirked and bit Sam's earlobe causing Sam to gasp in surprise at the feeling.

"This is gonna be fun." Dean smiled lecherously at Sam who was now on his back and staring into Dean's bright, green eyes.

Dean slid down the creaky hotel bed so his face was even with the younger Winchester's hips. Dean's eyes sparked with a deep, primal hunger; taking his hand and running it slowly down Sam's length, still hard. Sam tilted his head back slightly and his mouth formed and 'O' shape. Dean pumped his hand faster and faster, circling his thumb at the head. Sam bucked his hips into Dean's palm, pushing his length into Dean's firm grip.

"Fuck, Dean—oh, God." Sam moaned loudly. He stiffened, teetering at the precipice of release, but Dean stopped just before Sam could come.

"What?!" Sam looked up at Dean outraged. He tried to reach down and touch himself but Dean grabbed his hands and pinned them above his head. With the other hand Dean deftly slipped off his shorts and prepared himself physically and mentally.

'I want this to be special.' Dean said to himself—breathing deeply to try and relax. He braced himself and then sunk down onto Sam's considerable length. Sam was a little over eight inches and considerably thick; not as thick as Dean but still considerable. He ignored the sharp, deep pain for Sam. Sam was so close and Dean could feel it—the younger Winchester's cock was pulsing inside of Dean. Before Dean moved, he ran his hand along his own member, teasing himself and finally setting a rhythm—his hips involuntarily moving and grinding down onto Sam's dick.

"Oh, Sammy." Dean growled out Sam's name and started to rock his hips harder against his brother, putting his hands on Sam's chest and arching his back.

"Oh...God...Dean...I'm.." Sam gasped between thrusts—looking up hungrily up at the gorgeous man writhing on Sam's dick.

"That's right, fuck yourself on my cock." Sam's voice was like silk caressing over Dean's sweaty skin. Dean pushed against Sam's chest and raised his ass fractionally upwards on Sam's shaft, sinking back down with a pinch—to be honest, he liked the pain. Dean rose up again but this time Sam slammed his hips upwards into Dean and pleasure erupted inside of him, like nothing he had ever felt.

"Fuck!" Dean gasped and threw his head back—his muscles twitching and winding tighter, like a rubber-band waiting to snap.

"Give it to me, Sam." Dean growled in time with each thrust and Sam grabbed Dean's hips—his fingers pushing into Dean hard enough to leave bruises. Sam fucks into Dean again and again, no doubt causing pain, but at this point neither of them cared—Sam too close to release to care and Dean perversely enjoying the pain.

Sam came inside of Dean's tight ass and filled him to the point of overflowing, some spilling out around Sam's cock and sliding thickly down Dean's ass cheeks, leaving a sticky white trail that could have been hot enough to burn.

"Oh, fuck! Sammy!" Dean gasped out his brother's name and came all over the both of them, his fingernails leaving livid, red lines on Sam's chest and his cum splattering across his chest and stomach and dripping down onto Sam. He fell over top of Sam, only barely managing to prop himself up on his forearms—his chest heaving with ragged gasps. After a few moments filled with panting, Dean rose off of Sam and rolled onto his back, wincing at the unfamiliar empty feeling.

"That was—" Sam started.

"Fucking amazing." Dean breathed and locked his green gaze onto Sam.

"I can definitely get used to this." Dean smiled. Sam chuckled and kissed Dean softly. Dean knew he was going to be very sore in the morning—and he dreaded having to sit in the impala and drive anytime soon—but he didn't care. The smile on Sam's face and the pleasure he just experienced was well worth it.