Dean stood there on his last day, in his last hour, anger flaring at what Ruby had just said.
"What! How the hell can you ask me to do something like that!" She stared at him stubbornly.
"Dean, trust me on this one. I need Sam to toughen up for this and for that to happen he needs to hurt, but not the way he'll hurt if you leave normally. I need you to hurt him so badly that he'll become cold inside, so he'll become a killer. So are you going to do it?"
He knew she was right, but it didn't make it any easier to accept what he had to do.
"Ruby do you understand what you just asked me to do! You can't just waltz in and say oh, hey Dean, can you do me a favor and rape Sam? He's my brother for fuck sakes! I love him way too much to let him be hurt like that!" He hated her now, wanted the colt, but unfortunately they weren't able to get it back from Bela, so his only weapons were words. He grinded his teeth as he glared at her, and she stared back with an equal stubbornness.
"Then he'll die. He'll die, and so will everyone else in this world, all because you were to brotherly to hurt poor Sam. Face it Dean, this is your only option. I need you to do this… believe me, I don't like thinking about this any more that you do, but its necessary in order for Sam to become the fighter I need him to be. You know this." There was less anger in her words now, and she almost sounded like he was pleading. He enjoyed that, liked how her plan depended entirely on him.
"So why rape? Can't I just shoot him or beat the crap out of him?" She put her hand on her forehead, grunting out of stubbornness.
"No Dean, you can't just physically hurt him. You have to betray him to the fullest extent that one brother can betray another. You need to make him feel scared; you need him to hurt more emotionally than he will physically. And what would hurt Sam more than big brother touching him in ways he shouldn't. You know it's necessary, so why are you trying to stop it from happening?" His urge to punch her was growing, and he clenched his fist. God, how he wanted her to suffer for even asking such a thing. How could he hurt Sammy, the Sammy he swore to protect from any kind of pain? He wanted her to burn for even suggesting it, but deep down he knew it would work. He knew deep down that it would turn Sam into the killing machine that he needed to be. He felt the bile rise in his throat as he tried to speak.
"I'm not going to be able to do this by my own will."
"I thought so, so I offered Lust a chance to help. It is her field of expertise, you know." Oh he knew Lust all to well, as he'd been giving in to her sin for years, girl after girl, fuck after fuck.
"Summon the bitch and get this over with. The sooner I die the better." Ruby frowned, she knew she was asking a lot of him but she had no choice. Her eyes turned black and suddenly a rush of black smoke surrounded her. It entered her body and she stared at Dean, a different look in her eyes.
"So my friend Ruby tells me you need some assistance. Raping Sam, I have to say, it sounds so enjoyable. Oh I just shiver thinking about how betrayed he'll feel. But let's get you ready, that was the deal." She sensually laid her hand on his shoulder, and whispered into his ear. "You really want to fuck Sam, don't you? You want him to feel pain, feel all the pain that you felt when he left for Stanford. You want him to feel bad and betrayed, so he knows that he belongs to you, don't you? You want to rape Sam, don't you Dean?" He looked up, her hand still gripping his shoulder. He felt her influence take over and he found himself thinking about how Sam's body would feel against his own, how he'd love to hear Sam pleading with him to stop. He felt his erection growing, and deep down he hated himself for thinking the thoughts he was, but he was also glad: glad that Lust was taking over, that these feelings weren't his own.
"Yes, I want Sam to feel pain, to feel me inside him and I want him to beg me to stop." Lust looked at him proudly, and released her grip.
"That's my boy. Now, go get him, and when you're done don't forget to leave, you only have an hour. So not too much foreplay." He smirked at her words, lust having completely mixed with his thoughts. He turned to the motel door and opened it, peering at Sam, who was lying on his bed, resting from their latest hunt. Dean walked over to him and grabbed his leg, causing Sam to jump up in surprise.
"Oh, hey Dean." He looked down and saw Dean's hand making its way to his crotch. He swallowed and looked at Dean, who was smirking at him. "Umm, what's with the hand?"
"Shut up." He punched Sam in the face with his free hand, and Sam fell backwards onto his bed, grasping his face. Dean used this opportunity to grab his little brother's hands and push them forward, rendering Sam virtually immobile. He started to grind his hips against his brother's, and Sam struggled for freedom.
"Dean, what the fuck are you doing! Let me go!" Dean punched him again and started unzipping his pants. He tore them off of Sam's struggling legs and started to feel the bulge in his boxers.
"Ooh, Sammy likes this huh?" He quickly tore off Sam's boxers, and grabbed his testicles, causing Sam to freeze with pain.
"Dean please let me go!" He could only struggle as his brother reached for a rope and wrapped it around Sam's hands, and then tied that rope to the bedpost. With that done he returned to Sam's hips, drinking in the sight that was his brother. He stroked his brother a little before he started pulling his own pants off, Sam screaming for release the whole time. He ignored his brother's pleas and took off his boxers, his erection growing painfully big. He lifted Sam slightly, enough to get his hands on his ass. With an evil smile he ran a finger along Sam's ass, and then thrust a finger into him. Sam gasped in pain, and Dean stroked himself and he absorbed Sam's gasps and felt his baby brother's insides. He then put another finger into Sam, and another, making the count three. He moved in and out rhythmically, and Sam screamed in pain, tears starting to run down his face.
"Oh some on Sammy, you know you want this, and it might hurt but there's so much pleasure in pain. And besides, this isn't the worst of it…" he laughed mockingly as Sam squirmed, but no matter how hard he tried, Dean was in full control of the situation. He removed his fingers and rubbed Sam's cock, hoping to at least stimulate his brother, even if this was rape. With Sam loosened he lifted his hips, and Sam struggled harder than ever, knowing what Dean was going to do. He screamed at Dean to stop, but Dean simply laughed at him and pushed himself inside Sam. Sam lost all his breath, pain surging through his body. He gasped continually as Dean moved all the way in; making sure his baby brother felt him. "Oh Jesus Sammy you fell so good!" Dean moved in and out of his brother, and all Sam could do was gasp in pain and cry as he was violated by his older brother.
"Dean why are you doing this?" Dean kept his pace but stared into Sam's eyes.
"Because I'm sick and tired of not being able to touch you, I want you to feel all the pain I felt when you left home for Stanford, all the pain you put me through when you died. I was you to hurt, Sam!" He sped up his pace, and moaned in pleasure as his brother cried, helpless to Dean's actions. Dean started to moan louder, and he pulled out, not quite ready to finish up with Sam. He ran his tongue over Sam's cock, and watched as it was forcefully hardened. He started to suck, hoping that Sam would at least enjoy some part of this, and he started to finger Sam again, using the same three fingers as before. Sam groaned in pain as he struggled to get out of the rope bonds, but they were tied too tight, and Dean's grip was too strong right now for him to break free.
Dean sucked his brother's cock hungrily, forcing it into the back of his throat. He fingered harder, and Sam gasped louder in pain, tears covering his face.
"Dean, please! Stop it Dean, I'm begging you!" Dean watched in amusement as Sam cried, terrified by what he was doing. He pushed his fingers in deeper, enjoying the painful gasps Sam let out. He continued to suck Sam's hard cock, but he knew it was only hard because it was being sucked. But that didn't matter: he was going to hurt his brother, and he was going to make sure Sam remembered this hurt, the same feeling he left Dean with when he left for Stanford. Dean stopped sucking and took his fingers out of Sam, who was trembling with fear and pain. He crawled higher on the bed, aligning his hips with Sam's. He moved for a kiss but Sam pulled his face away, and Dean smiled, using a hand to pull his face back into Dean's path. He forced his brother's mouth open and let his tongue wander, exploring every inch of Sam's mouth. Sam whined, desperate for his brother to leave his mouth. Dean let him go, making sure Sam knew his taste, and moved back down his body, inching toward his cock. He played with it a little before he lifted Sam's hips again, slowly moving to fuck him. He entered Sam once again, and got a similar gasp of pain as before, but this was more pitiful, as if Sam had given up all struggling and simply accepted that his brother wanted to hurt him. He tried a faster, rougher rhythm, and he got a more raspy gasp from Sam, causing him to smile.
"Aww, what's the matter Sammy? Is big bro Deanie hurting you? Well too bad, there's nobody here to protect you. You're all mine now Sammy, all mine." He pushed harder into Sam, who responded with louder gasps and more frequent sobs. He continued this rhythm, enjoyed that Sam was hurting from it. A few minutes passed, and he could feel an orgasm coming. "So Sammy where do you want it, your face, chest, or up your ass? The choice is your buddy." Sam groaned in pain as Dean slowed, sustaining the pleasure before his orgasm. "Alright then, I guess I shoot it right up your ass." He sped up again, and soon he started breathing heavily. He pushed himself as far into Sam as he could when he shot his load, filling Sam with his sticky mess. Sam yelled in pain as he felt his brother push, and soon he was pulling out, leaving Sam shaking and broken. He put on his clothes and walked up to Sam's face, gently rubbing him before he walked out the door. "See ya Sammy." He smirked as he walked out the door, but his smirk was soon replaced with a look of disgust. He looked at Ruby with hatred. He wanted to hit her so bad for making him do that to Sam.
"Dean I know that was hard, but it had to be done. This experience will turn Sam into the heartless killer I need him to be, and it's going to end up saving lots of lives." She looked down, trying her hardest not to let Dean see the tear that brushed her eye. "Now, I'm your escort, so let's go. Take my hand." Dean looked back at the door, knowing that inside Sam was terrified and broken. He took ruby's hand and she guided him to Hell, his new home, and he chuckled, seeing it fit for what he'd done.
Sam did use that experience to win the war. He used the rage he gained from it as fuel to plunge the bullet into Lilith's heart, ending the war once and for all. Ruby would never tell him that it was her decision to have Dean rape him, and she'd never tell him that Dean did it for his brother's good.