Sam opened the door to the cheap motel him, Dean and their father were staying at. John Winchester hadn't been seen for a week or so, and wasn't expected back for a few days. From the looks of the empty hotel room, Dean was also gone. They were temporarily enrolled in a new school. Sam hated moving around but he always put in effort in his classes. Dean on the other hand decided, since dad was gone and would never find out, he was not going to sit in some boring classroom. He told Sam he had found some college chicks to hang out with and they were "smokin' hot". Dean was probably the only 18th year old who could get laid by multiple college chicks.

Sam was 14 and very much a virgin. He had never even focused on masturbation. He tried a few times but he never got to the point of orgasm. From what Dean told him, white stuff was supposed to shoot out of him when he "came". It hadn't happened and Sam was in no real rush.

Pushing the thought out of his mind, Sam sat down to do his homework. After he finished he pulled out the book he checked out from the library and leaned into the musty couch. Several hours passed by and still no Dean. Sam began to worry as he peered out the hotel window. Nothing but dark sky. He sat back on the couch deciding to watch TV to keep his mind off all the horrible thoughts that started to swirl around. Dean is fine, he told himself. He's a good hunter. Better than good.

The woman on the TV caught Sam's attention. She was about twenty years older than him with large, bouncy boobs. Her thick, red lips curved deliciously as she talked. Sam whined as he felt his dick harden. He hated this so much. It would take hours for this to go away and it would painful. After a minute, frustration took over and he decided to try and rub his problem away. He unzipped his pants pulling out his rock hard cock. He wrapped his hand around it as he began moving up and down his shaft with very little rhythm. Like always he felt little waves of pleasure but nothing else.

Suddenly the hotel door banged open and Dean stumbled through. Sam jumped trying to cover himself. Dean took one look at him and burst into laughter.

"It's not funny," Sam complained.

"Sorry, Sammy." Dean slurred with a grin.

"Are you drunk?"

Dean shook his head crashing down next to him on the couch making Sam feeling even more awkward. "Buzzed. These girls were hot man. This one blonde – incredible ass – she went down on me for the first time. She couldn't get me off but God how her wet mouth felt wrapped around my dick –"

Sam whimpered as his cock twitched. Dean looked down at him with a grin. "Either put it away or finish the job, Sammy."

"I can't," he told him in a low voice.

"Sure you can. Think of a babe, stroke it a few times then bam."

Sam frowned, "Then white stuff, right?"

Dean cocked an eyebrow, "Yeah? Sammy – please tell me you've busted before?"

Sam wasn't sure why this term caused his dick to twitch again. He put his hand back on in.

"I can't get the motion right. I've tried so many times."

Dean ran his fingers through his hair sighing deeply. "Sammy, Sammy, Sammy – do I have to teach you everything?"

He placed his hand over Sam's forcing him to move it from the middle of his shaft to the head. "Like this," Dean purred lowly.

Sam pressed upwards moaning softly. Dean gulped loudly as he felt his own cock growing hard. He took his hand off his brother's cock quickly. Sam tried to mimic the motion but groaned in frustration when he lost rhythm. Dean rolled his eyes. "Here, watch."

He pulled his long, hard cock out of his pants. Sam stared at it thinking that it looked massive in comparison to his. Dean seemed to read his mind, "Don't worry. It wasn't this size when I was your age."

Sam nodded and watched as Dean began stroking his dick. He tried to mimic the motion. After a few minutes waves of pleasure were starting to wash over him much powerful than he was used to. His mouth hung open as he moaned loudly.

Dean stared at his little brother confused why his moans were turning him on more. He watched Sam aggressively pumping his dick and it completely undid him. His moans grew even louder than Sam's. Sam quickly looked over to see his brother throw his head back and that white liquid to squirt out of the head of his dick. This sent even more ways of pleasure over him but despite everything he still couldn't come. He beat his dick without mercy trying to force results.

Dean came down from his high and saw his little brother's struggle. He actually felt very sorry for him. "Here kid, move out of the way."

Dean batted Sam's hand away and took his cock into his hand. Sam moaned loudly bucking upwards.

"Yeah it's always good the first time someone else touches it," Dean cooed getting a few more groans from Sam's mouth. He knew he should feel bad for being so turned on by his little brother's sex cries but instead he focused on the pumping. "It's too dry."

He leaned over and let some spit dribble from his mouth. Sam whimpered as his body began shaking violently around him. It only took two pumps with the saliva for Sam to come on his hand.

"Dean! Dean!" he shouted as his very first orgasm rocked him.

Dean continued stroking him letting the orgasm run its course. After a minute Sam collapsed backwards taking in deep, ragged breaths. Dean grabbed a tissue cleaning them both up. He turned to Sam. "Don't expect that every time now. I know I'm good but you have to start doing this stuff on your own."

Sam laughed, "I need to take a nap."

Dean checked his watch, "Nap? You need to go to bed. You have school in the morning."

Instead of arguing, Sam simply nodded and stumbled to his bed. Within minutes he was asleep.