"Sammy, please." It was barely more than a breath. They'd been at it for hours, and Sam was still showing next to no signs of wearing down, so Dean was reduced to begging. Which always happened. Always. Every. Single. Time.

Sam gave him a small smile, almost a glint of sympathy in his eye for about half a second, but he covered that up as quickly as it appeared. "What's wrong, big brother? Had enough?"

The nearly strangled sound that pushed itself up from Dean's throat seemed to cut deeper into the marks left on his back and the insides of his thighs by Sam's knotted whip. That was at least an hour ago, maybe two, but they still stung. Now, though, Sam was just teasing. Nothing rough, just not giving him what he needed. What they both needed. "Y-yeah," he panted in response to Sam's question, knowing it was rhetorical and his answer didn't really matter, but also knowing that there would be punishment if he didn't respond when he was directly asked to.

Sam's thumb circled his entrance for what felt like the millionth time and pushed very lightly but didn't even start to breach the surface. "Well, that's too bad. 'Cause, see, I'm having quite a bit of fun back here."

Dean whimpered, unintentionally pushing back against Sam's finger, and repeated, "Please." This time, his voice actually wavered. Almost like it was about to break, the way that it would if he were crying.

Sam froze. "Did I hurt you?" he asked sincerely after a moment, full well ready to kick Dean's ass if he hadn't said when it was too much.

"No, no," Dean assured him quickly, gaining back a little hold on himself when he heard the nervous/angry/concerned tone in Sam's voice. "Nothin' I couldn't take. Just kills me when you drag it out like this."

Sam relaxed a little upon the information that Dean was, in fact, okay, but recognized still that it wasn't a situation to just brush off. Regardless of the cause, Dean had sounded fairly unstable, more so, even, then when he usually begged. "Okay," Sam gently agreed, hands running up and down the backs of Dean's legs. "Okay, I'll give you more." This time, the tip of Sam's middle finger met Dean's hole rather than his thumb, and he rubbed in small circles at first, then back and forth, then up and down, until, finally, Dean opened up to him enough to slip up to the first knuckle inside.

Their moans were almost entirely synchronized, Dean's slightly lower, which he noted and took pride in considering that he half-expected himself to emit another of the pathetic sounds he'd been making before. He squeezed his eyes shut, physically forcing himself not to tighten up again, and let out a long, steady breath through his nose. His entire body was in overdrive, all thanks to Sam taking his sweet fucking time, and he tried to focus more on the feel of the scratchy sheets against his knees than rushing his brother. He knew that'd only slow the process down more.

"Gotta try to calm down for me." Sam's voice was almost soothing now. The switch inside him had always been so, so easy for Dean to flip, and this situation was no exception. The second Sam could tell that Dean was about to reach a breaking point - in any aspect, not just pain - he would back off. "Gotta try to relax a little bit or this is gonna be real hard, okay?"

Dean just nodded, biting down on the insides of his cheeks and thanking god Sam was finally taking some mercy on him.

"Good," Sam praised when Dean forced as much tension as he could to release itself from his body. "That's good, baby." Sam worked his finger in slowly, not to be an asshole this time, just to keep from hurting Dean.

"'M not gonna break," Dean panted, twisting his hips a little but not forcing Sam in further, because he knew Sam would do that on his own if and when he wanted to. "Gotta be careful," Sam reprimanded, holding Dean still with his free hand. "We'll get there." And they did. Slowly - god, so fucking slowly - Sam worked in two fingers, dry, because that was what Dean had been asking for from the beginning (god, Sammy, just wanna feel you, no lube, not this time, I can handle it) and started to scissor them apart.

Dean dropped his head to the mattress, face damn near completely flushed, opening up like he was made for it.

It was taking all of the willpower Sam had not to start fisting his own cock while watching. "So fucking good, big brother. Ready for me?"

Dean thought he might pass out. They'd spent half the fucking day leading up to this and now Sam was asking like there was a possibility that he'd get a 'nah, not yet, lemme wait just a little longer.' "Jesus, yes," is what Dean said, rather than the million profanities attempting to claw themselves from his lungs.

Sam's fingers were out remarkably quickly, replaced by the head of his cock. Now, this, this made him nervous. They'd only gone all the way with no lube one other time. Not that it had been disastrous, it was just that it took a fair amount more time to adjust to and some degree of pain - not too much, but still, some - was inevitable. Dean knew what he was in for, though. And he'd asked. So Sam was going for it. It took him damn near a full fifteen minutes (I know, baby, I know, but I don't wanna hurt you) to push gently inside. But once he did, god, was it worth it.

"O-oh, fuck, baby boy. See? See how much better?"

Fucking shit, yeah, Sam did. Between the sounds it was driving out of his brother and the full, complete effect of nothing but skin on skin, as close to each other as they could possibly be, he was in heaven. He was still cautious, but each thrust of his hips was like an explosion, sending fire through his entire body. He was trying hard to pace himself, and only that focus was keeping him off the edge. They'd been spending so much time building up to this that it wouldn't be unacceptable for either of them to come at any given time, but he wanted it to last. Wanted to make it good for Dean.

The problem, however, was that since Sam was setting the pace, Dean had nothing but the feeling to focus on, and the first time that Sam full-on slammed his prostate rather than just rubbing against it, he was done. The sex itself was over faster than the manual preparation. But the orgasm was so good it didn't even matter. Dean felt it start in the balls of his feet, a quiet numbness nagging at him until he had no choice but to pay attention. It wasn't like a tidal wave, didn't rush over him, but eased in at almost a languid pace. It spread up his body, inch by inch, leaving everything in its wake unfeeling and then tingling, as if each limb was accordingly falling asleep. When it reached his cock, the come began spurting out onto the bed beneath him in short bursts and kept right on going until the sensation had swept over every individual cell inside him, the very top of his head losing feeling at last and deeming him unable to hold himself up any longer.

Somewhere through Dean's extensive orgasm Sam's hit and finished, and he was alert enough by the time that Dean collapsed to pull out with as much grace as he could manage and wrap his brother in his arms so that they could let unconsciousness simultaneously overtake them.

For the next four days, Dean was sore.

On the fifth, he demanded that they do it again.