Yes or No

They should have left yesterday. Instead, Dean wanted to stay one more day for an underground poker game. He made good money and was in a pretty good mood when the brothers left town.

Just before they left city limits, they came up to a roadblock. Sam was surprised to hear Dean swear loudly.

“Dean?” Sam looked down the road at the seven motorcycles lined up in front of them.

“Bunch of sore losers,” grumbled Dean. “Lock your door, Sam.”

A tall man boldly came up in front of them and pointed a shotgun right at them.

“Then again…”

Eddie was not a happy man; losing in pool in his home turf did not make him happy. He glared at the two brothers his gang worked over. Dean didn’t have his money, already spent on their much needed supplies.

“You’re going have to repay me another way,” he threatened.

Dean just scoffed. He spat out blood from his cut lip.

Eddie studied them. Slowly, he smiled.

Dean didn’t like the way the leader looked at him or Sam. He gave his brother a signal and they both swung into action, breaking free. But there were too many of them and soon, they laid unconscious sode by side on the ground.

When Dean came to, he was horrified to see Sam bent over the hood of his car, his hands bound and tied to a Y, looped through the front. They’d stripped him. Sam laid there, shivering as the night air touched his bare ass.

The men whistled. Sam’s ass was pale, tight globes and looked absolutely fuckable in front of Dean. Thankfully, Sam was still unconscious; he couldn’t see the men reaching out for a touch. They only laughed when Dean cursed and threatened them.

“What the hell do you want?” Dean spat out when Eddie appeared before him. Dean struggled with his bonds in front of him. But they were tight around his wrists and the gun poking him on the back of his head stopped him from trying.

“Thought of a way you can pay me back.” Eddie smirked and gestured towards Sam. He leaned over to Dean.

“Your choice,” the foul voice whispered in Dean’s ear. “You do it or my men will.”

Dean reared back. “What? No!” They can’t be serious!

Eddie glared at him. “Then either pay up the two grand or do a little show for me and the boys!”

“Two grand? I won one!” Dean snapped.

“Interest,” Eddie smoothly explained. He went over and placed a hand on Sam’s ass and gave the right cheek a squeeze. Sam moaned but didn’t wake up. Amused, Eddie put on his leather gloves and began probing Sam’s hole.

“Stop! Leave him alone!” Dean watched horrified as Eddie dry finger-fucked Sam with his gloves. Sam whimpered and fidgeted uncomfortably.

“Your choice.” Eddie pulled out his fingers and patted Sam’s ass. “Go ahead. Say no. My boys will have a lot of fun with him.”

“He’s my brother!” Dean protested.

Eddie snorted. His men laughed. “Just look at him. Don’t tell me you never fantasized it.”

He did, but only in his darkest dreams. Dean refused to say anything and kept glaring at the biker. Eddie wasn’t intimidated.

“Yes or no.”

Dean looked at the huge bikers surrounding them with eager leers. They would tear Sam apart. “I’ll do it,” he croaked out. Dean prayed Sam would stay unconscious for this.

Everyone laughed as Dean was marched up to Sam. One of the men unzipped Dean’s jeans and hooted when Dean reluctantly pulled himself out in front of them.

Sam felt hot and smooth under his touch. He stirred, murmuring “Dean?” before he realized where he was. Sam tensed. “Dean?” his voice was unsteady.

“Don’t worry, Sammy,” Dean whispered, his tied hands on the back of Sam’s thighs. “It’s either me or them. Try to relax. I don’t want to hurt you.”

“You won’t,” Sam was certain. Still, he gasped when he felt Dean’s fingers brush against his tight hole.

“No.” Eddie angrily gave Dean a push. “Take him dry.”

Dean flinched and felt Sam do the same. “Let me at least prep him. He’s never done this before!”

Eddie nudged Dean back. To his horror, Eddie positioned himself and reached for his zipper.

“Dean!” Sam shouted in panic when he felt Eddie behind him. “It’s okay!”

“Well?” Eddie challenged.

Dean nodded, his mouth was dry.

Dean was back behind Sam again. Dean jerked off until his cock was hard and slowly pushed through Sam’s tight opening. He went slowly, groaning as he felt the hole stretching, trying to let him in. at first, it felt like it wouldn’t let Dean in, but finally, the muscles relaxed and Dean carefully forced his way in. Sam whimpered when Dean finally breached him. He calmed when Dean placed a hand on his back, instructing him to relax. He continued inch by inch. Sam was so tight. Dean closed his eyes and moaned. He couldn’t help it. Sam felt incredible around his dick; his shaft was hardening further as he moved in deeper.

“You’re taking too fucking long,” Eddie growled, suddenly behind Dean.

Before Dean could do anything, Eddie yanked his boxers down and roughly penetrated Dean. Dean jerked at the hard rod punching through to his ass. Shit! That fucking hurt!

“Dean?” Sam tried to turn around when he heard Dean grunted. He grew nervous when he felt Dean’s cock, only a third in, moving faster.

Dean gritted his teeth. Eddie wasn’t big, but he was long and the biker kept pushing and pushing until he was all the way in. Dean could feel the burn and he tried to stay as still as possible because he was still in Sam.

“Hurry up,” Eddie barked and gave a hard push with his hips.

Sam screamed when that last push sent the rest of Dean’s cock all the way in at once.

Dean yelled, horrified, when Eddie began to thrust, forcing Dean to pound into Sam even harder. The more Dean tried to push back, the more powerful Eddie slammed into Dean harder, forcing the hunter to ram into Sam. The weight of the two men was in every thrust and Sam’s ass couldn’t take it. He screamed and screamed until someone climbed up the hood by his head.

“This will shut you up.” A huge weeping cock forced its way down Sam’s throat, cutting him off.

“No!” Dean cried out when he heard Sam gagging. Eddie was filling Dean up, expertly scraping against his prostate. Dean moaned, his hips forced to jerk faster and harder into Sam. He arched his back; Eddie’s cock gliding in him and Sam’s hot, tight hole squeezing his cock was too much. He didn’t want to take Sam like this. But it felt so good around his dick and Dean found himself in pace with Eddie, eagerly sliding in and out of the swollen muscular ring.

Pretty soon, Dean came and Eddie came when he felt Dean shudder. Up front, Sam could be heard gagging as the biker came hard in his mouth. Sam spasm as even then, the large biker wouldn’t leave; pounding in his dick so hard, everyone could see it jackhammering inside Sam’s throat.

The men didn’t let Dean stop. Even when Eddie left his bleeding ass, others held Dean’s hips and slammed him into Sam like a hammer. Sam choked as they took turns raping his mouth, tears on his face as Dean unwilling brutalized his virgin ass. Sam screamed for them to stop, for Dean to help him. The others just filled his mouth with their engorged cocks to shut him up. The others hooted and howled out score.

It took a while but when Sam came with a pained scream, they finally let the brothers go. Eddie gave Dean a pat on his ass before he left the two brothers spent and Sam bent over the hood, cum and blood dripping down the bumper.

Dean carefully tried to pull himself out, but it wasn’t gentle enough. It was stuck inside with dry blood and Dean needed to give a yank. Sam whimpered again. He could barely move and needed Dean to help him off the hood. Sam staggered stiffly to the passenger seat of the car, and shakily put on his clothes. When Sam passed out from the pain in the front seat, Dean turned his head to the side and vomit. He couldn’t believe he came, raping his little brother.

Dean staggered to the car. He painfully got in, groaning as his sore ass sat down. Dean carefully rearranged Sam so he was lying on his side on the seat and Dean drove out of the city. He wanted to be away from this place now.