The demon was a bitch. Really. Who the fuck did she think she was? But worse than that she was a sadistic fucking bitch. It was obvious by the grin on her face. Dean wanted to wipe that grin off her face. But that was hard to do considering that he was chained to the wall behind him with Sammy chained beside him.

"So Dean, before brother dear wakes up, tell me, what do you want me to do with you two?" he said. The meat-suit he was wearing looked like some sort of librarian. It was a woman with glasses, long brown hair tied at the nape of her neck, with a long skirt and long sleeved shirt. She looked maybe twenty five.

"How 'bout you let Sammy go and do whatever you want with me, sweetheart," he said with a cocky grin.

"Oh no, no way, see, the Winchesters…I have to do something special. Because, well, whoever can break you two…well, they'll have a special place in hell from now on. So, I'm going to break you. And I know how to do it. Because more than anything else, you'll do anything for each other. And don't you think that devotion is a bit…strange?" she asked, walking up to Dean and stroking a hand over his face.

Dean snorted. "He's my brother. I'm supposed to fucking take care of him."

She tapped her chin. "No, I think it is definitely more than that. Kind of unhealthy if you ask me. You ever dream of fucking your little brother, Dean?"

Dean's green eyes flashed with fury. This was a new low even for demons. "What's your game, you hell bitch?"

"See, I see all these repressed feelings in you both, so we're going to have a little game, oh look, little Sammy's waking up," she said moving toward him.

Sam groaned, swimming to consciousness and heard voices. One was Dean and one was that bitch of a demon that somehow got the drop on him and smashed his head in. "Sammy!" he heard from beside him.

"Dean?" he said finally, blinking and raising his head, glancing at his brother, and realized they were both chained to a wall in some sort of abandoned warehouse that was dark and damp. "You okay?" he asked.

"Fine, Sam, just fine. But this bitch is pissing me off. I swear, when I get off here, I'm going to show you a new definition of pain…" Dean said, yanking against the chains.

"I was just telling Dean that I was going to break you both. See, talk about surprised when I found out no one thought of trying this. I mean, obviously, torture won't work on you two. But, there is something that will. I'm going to give you a choice Sammy. I'm going to slowly kill your brother in front of your eyes, your big brother who you love ever so much, perhaps too much, or…you're going to fuck him," she said with an amused smile.

Sam blinked. "What? And just how do you imagine that's going to work? Once I'm off this wall I'll rip your throat out for even suggesting something so sick and twisted," he said, frowning.

There was movement behind her and two black eyed men came into the room slowly and unhooked Dean from the wall. Sam struggled against his own chains as Dean fought with them but he was punched soundly and kicked several times, and Sam was sure he heard bones cracking.

"Stop!" he screamed at her. She smiled and the two men moved back, leaving Dean gasping for breath on the floor. He glared daggers at the two men.

"Now Dean, dear," she said, kneeling in front of him as she snapped handcuffs on his hands in his lap. "You have a choice too. You're going to let your brother fuck you, or I'm going to have these two," she motioned to the two men behind him. "They're going to take a turn beating him, then they're both going to fuck your baby brother while you watch chained to the wall. Then they'll gut him right before your eyes. And if you're really lucky he'll die. If you aren't he'll still be screaming by then. Is that what you want, Dean?"

Dean looked at Sam and his eyes were wide with the fear. He'd do anything for Sammy. Anything at all. And if it meant playing this bitch demon's sick game until they could get out, he'd do it. They were out of options. He felt at least two broken ribs, and if he wasn't careful one would puncture his lung. He blinked and nodded at her. "Whatever bitch, don't you fucking lay a hand on him."

She smiled, and the two goons grabbed him and yanked him over to a steel table. What was it with these demons and steel tables? Were the damn things standard issue in hell? Here, instructions on getting a meat suit, and here ya go, one standard issue steel torture table. Alastair had favored them. His thoughts were interrupted by being slammed onto his stomach on the table and his arms handcuffed to the bar above his head. He groaned as the ribs shifted. She was over him now, her hands running over his body and then slicing away his shirt from the back.

"Hum, makes me wish I'd taken a male…maybe I'll trade with one of my goons over there, what do you think, Dean? Ever had a cock up your ass? I know you like women, but oh, it is so much fun to play for the other team now and then. But I guess your baby brother would know that, wouldn't he?" she said and winked at Sam who had paled.

Dean blinked, craning his head to see his brother's expression. He knew that look. It was his dean's-gonna-hate-me look he got when he did something that he knew Dean wouldn't like. "Sammy, don't listen to her bullshit. You know I don't give a fuck who you've fucked. At least you won't stumble through this…go easy on me, Sammy, you aren't exactly packin' a small trouser snake."

Dean felt his hair gripped and his face bounced painfully off the table as blood exploded from his nose. He felt the bones cracking. "Still cracking jokes, Dean?" she hissed into his ear.

"Fuck you, you black eyed bitch," he said swallowing the blood crawling down his throat.

She bounced his head off the table once more, ignoring Sam's yells for her to stop. She then slipped behind him where he was bent quite attractively over the table. She took her knife and sliced through the denim of his jeans easily, pulling them and the shredded remains of the boxers underneath off easily.

"Oh, Dean, you do have a nice ass," she said, running her hands over the newly exposed flesh. "I think I'll let Sammy decide how we proceed," she said, pulling the knife down the crevice toward the hidden entrance to Dean's body.

Dean tensed was completely still as he felt the tip of the knife digging into him where it was definitely not supposed to be. "Choose Sammy," she said. "My knife or your cock? Which is it, big boy? Somehow I don't think he'll survive a round with my knife."

"Stop!" Sam screamed, franticly pulling at the manacles above his head. "I'll do it, just get away from him!"

She leaned back, pulling the knife away and Dean visibly relaxed, nearly going limp on the table as the tension drained from his body. "Don't be stupid, though, boys?" she said, and a pair of bright red dots showed up on Dean's forehead. "You'll never get to them before he's shot through the skull twice. So don't fuck with me, sasquatch. You do what I say, and you both walk out of here. Well, Dean will walk funny for a few days…"

One of the other demons released Sam's bonds and he moved over toward the space where Dean was laid out and his heart thudded harshly in his chest. He had experimented before Jess, only a couple times, but he at least knew how this worked, and it was decidedly different than fucking a woman. There were so many more things that could hurt doing this. Though the other benefit was he knew how to make it less painful for his brother. If he was going to be forced into this, he'd at least give that to Dean.

He glared at the demoness and then turned to his nude brother. He swallowed hard. "Dean, I'm sorry…" he said quietly.

"Nothin' to be sorry for, baby boy," and Sam's blood rushed toward his previously uninterested nethers at the nickname as it fell from Dean's lips. Oh gods, he thought. If Dean knew…

The few times he'd experimented with men, he'd taken men who looked like his brother. Dark haired, built men that were strong on the outside but begging to be dominated within. He secretly wished that Dean would yield complete control to him after spending his life making sure Sam was safe. He wanted to be the one to make his brother come undone. And even if this wasn't the way he wanted to have it happen, he'd at least do his best, even if he knew his brother didn't want this from him, or from anyone.

"I swear to fuckin' god, Dean, if after this you start going out to find as many men to fuck you as you find women to fuck, I'm gonna tie you to the bed every night when we're at hotels…" he muttered as he ran his hands over Dean's back and felt the shiver run through him.

"You'd like that, wouldn't you Dean?" the demon asked, leaning back to watch the events unfold. "Tied at the mercy of your baby brother? Just like you always wanted…"

Sam jolted, wondering if the demon was messing with him again, but he heard the uptake in his brother's breathing and felt the rapid staccato of his heartbeat against his hands as he pressed into his back. Something about what she said was true, and damned if it didn't make Sam even harder. Were his carnal desires that he'd suppressed since they were kids shoved in lonely motel rooms returned? Oh, fuck, he thought, and his hands wandered down his brother's ass, squeezing the hard muscles. He groaned as his hands found their way downward and he brushed fingers downward and pressed lightly to the tight ring of muscles below. Dean jerked away bit, surprised.

"Shh, don't worry, De, I'll be careful," he said softly, leaning over his brother and pressing a kiss to the back of his neck.

He felt the shiver travel down his big brother's spine. He wasn't sure who was more shocked at the response, him or Dean. He licked a long stripe down his spine then, knowing what the bitch wanted out of them. And he was damn well going to make Dean's first experience as good as he could. So he had to do something to prep him, he knew that much, otherwise the pain would be nearly unbearable. He glared at her smiling at him as he traced his tongue all the way down between his brother's crevice, swirling it around the tight entrance. At the touch, Dean jerked violently, letting out a unmanly squeak. That…that was unexpected.

Sam grinned despite himself. He worked his tongue into the space and was surprised. He'd never actually done this, and thought it would be rather…gross. But he found it wasn't much different than sucking someone off. The taste was salty and musky and he thought that he would definitely be doing this again as he worked his tongue inside, loosening the muscles and trailing as much saliva on his entrance as he could. When he was satisfied he sat back on his heels and sucked his own fingers into mouth and laved his tongue over them. He swore the act of doing that and staring at his brother's ass presented like that nearly made him cream his pants. He stopped himself. He couldn't let them touch Dean, not like that.

He was satisfied and worked one of them into him. Oh, lord, he thought. He'd never been with someone who'd never done this before, and the muscles clamped hard on his intruding diget. He ran his other hand over Dean's back, but he couldn't take his eyes off what he was doing, he was too aroused by the very sight of what he was doing and knowing it was Dean he was doing it to. He shot a glare at the demoness again and finally Dean relaxed and he slipped a second finger into him, spreading them and doing his best to prepare him for his more than ample girth. A third and he heard the hiss of pain from Dean. He patted him and stood, leaning over him again.

Dean was flushed, sweat beading on his forehead, and he wasn't sure what was worse, Sam leaning over him, or Sam doing that wicked thing with his tongue. Holy hell… If he ever found a woman that would do that he'd marry her in a second. Sam removed his fingers then and he heard his clothes rustling and he knew he was going to do it then, and he squeezed his eyes closed, sure that all the pleasant parts were over. Surely. After all, it wasn't like he had any stimulation on his straining cock at the moment.

"Dean, relax, please," Sam said, softly and reached in front and grasped his cock finally, making Dean buck his hips downward in an attempt for some friction. The motion did what it was supposed to and Sam pressed forward, sheathing himself while Dean was relaxed from the pleasure shooting through him from the stroking.

The pain was sharp, though, as he tightened painfully around Sam. Sam groaned, almost going off then, but he wouldn't, and he was going to do this right. "Shit, De," he muttered. "Fuckin' relax!"

He heard Dean's breath ragged under him, and he felt his erection deflating under his hands. Shit. He knew it would hurt. He was too big to take him with spit for lube. He could already feel the burning friction on his own cock and knew it had to be worse for Dean. He stroked him back to hardness though, whispering in his ear, promising to make it better. He had to get this over with because he was about to come undone, and he had to satisfy the demon bitch that he'd done what he was supposed to do. He pulled backward and gently slid back in, wincing as it became smoother, knowing he'd torn something and it was blood slicking his passage now.

Dean felt something give with a sting and he groaned. That fucking hurt like a son of a bitch. But to his surprise the burning sensation gave a little, and it didn't hurt quite so much. Well, at least he knew that lubed this wouldn't be so fucking painful…otherwise why would anyone fuckin' do this? Not like he had any experience in the receiving end of this.

Sam changed the angle then, and Dean was extremely surprised to have an intense jolt of pleasure shoot through him. He gasped, jerking hard against the bindings.

"Hm, there," Sam muttered, hand wrapping around Deans cock tighter, pumping him.

"Fuck!" he said as Sam brushed against it again. "The fuck is that…oh…"

Sam smirked against Dean's back, shifting a little so less weight was on him. "Can't be all bad, De," he said, breathless now.

Sam groaned and he pulled back and set a rhythm, stroking with his hand at the same pace. Every stroke to his brother's prostate sent a jolt through his cock, and before long he was groaning under him from the dual stimulation. The rest of the room had disappeared for them both, demons or no demons, didn't matter. All that existed was the moment, and the pleasure that was overriding the pain. Dean went suddenly, gasping in surprise as the orgasm hit him like freight train. Same felt the passage tighten until he couldn't move and he was tipped over the edge, amazed at the incredible sensation.

He slumped forward, gasping as hard as Dean underneath him and turned to the grinning demon bitch. "Happy, bitch?" he growled at her.

She grinned and snapped, the shackles releasing Dean and then simply left.

Sam slid and fell to the ground, followed by Dean who practically landed in his lap, exhausted.

Sam ran a hand over his brother's short black hair. "God I'm sorry Dean…"

Dean shook his head. "Nah, s'okay, baby boy."

If Dean hadn't been sitting practically on Sam's lap, he wouldn't have felt his cock twitch at the word. He frowned and looked at his brother who's eyes had gone wide. "Ah…"

"Sam?" he asked. "Something you wanna tell me?"

Sam bit his lip. "Um, well, I guess I wasn't that opposed to that…but would have rather it been more…comfortable. Especially for you, De, I'm sorry…you must be disgusted by me, I mean, we're brothers…but…sicne when are we ever normal, especially me…"

Dean looked at him thoughtfully. Then to Sam's surprise, he leaned over and planted a chaste kiss on his lips. "Yeah, not normal with us."

Dean stood on shaky limbs and found his clothes. "For something she wanted to be painful, you did a good job making it feel pretty damn good," he admitted, shrugging into his jacket as he turned back to Sam.

Sam smiled. "Yeah, well it's better with things like lube…" he admitted.

"Oh, and you would know how?" he asked.

Sam rolled his eyes. "I went to college. I experimented here and there. So it just so happens all the men were dark haired."

"Sammy…well, let me tell you this…you breathe a word that I'm the bitch in this…I'll cut yer balls off. Got it?" he said, eyes narrowed.

Sam nodded. "Now about that better thing…" Dean continued, grabbing his brother by the hand and leading him out of the warehouse.

The demon watched then shimmered into another form, this one slightly angelic, and cupid-like… Some soul mates were so hard to get together… It wasn't like it was their fault they were born brothers. Oh well…