#insertion cw

Knowing he wasn’t going to win and feeling the need to prove Cas wrong, Dean gave in. “Fine. We’ll try it, and when it doesn’t work I don’t want you pouting, got it?”

Cas grinned as Dean grabbed the lube and scooted down the bed so he could prep himself. It was difficult to get into the mood as every finger he slipped inside just made Dean think that he wouldn’t be stretched enough to accommodate Cas’s body—he wanted to win, but he didn’t want to hurt the stubborn bastard. He went to three fingers and would have gone for the fourth if Cas hadn’t started yelling at him impatiently.

"Yeah, yeah, c’mere,” Dean grumbled, scooping Cas up and bringing him over to the bed. He slicked the condom up as well as he could and gave in to the urge to ‘accidentally’ swipe a lube-wet finger over Cas’s face. “Oops, sorry.”

"I’m sure you are," Cas snarked back and kicked his feet out. “I’m ready, put me in.”

Just think of it like you’re putting in a dildo, he thought to himself, lowering Cas to his hole. A noisy, annoying dildo.

He felt the tip of the condom and sucked in a breath when Cas straightened his legs out, kicking him lightly. “Let me know if it hurts too much, I mean it.” He slowly pushed Cas in, stopping every inch to let Cas adjust. The angel gave a sharp squirm that sent his knees into Dean’s prostate and he let out a surprised moan, just barely stopping himself from closing his hand around Cas.

And then Cas did it again. And again.

"Quit it, you’re not even the whole way in yet," Dean panted, guiding Cas in the rest of the way once he calmed down.

He felt the end of the condom on his fingers and stopped there, closing his eyes at the realization that there was five inches of determined angelic boyfriend inside of him. Very determined, if the way Cas immediately started to move was any indication. He was shifting and stretching and it was like the tiniest thrusts imaginable but they were still there. That and the constant attention to his prostate helped his dick get on board and he hesitantly reached down to stroke himself with his free hand.

It was slow torture made even more hot by the fact that Dean could just imagine Cas down there giving it his all, wearing himself out while Dean just rode the easy-going waves of pleasure.  He’d told Cas it wouldn’t be as easy as he thought. He closed his eyes and just relaxed, lazily bringing himself off but being careful to keep an ear out in case Cas finally called to give up.

Dean didn’t know how long they’d been at it when he suddenly tipped over the edge and came, moaning low and unable to keep from clenching around Cas’s still active body. Cas pushed him through his orgasm, slowing down and stopping only when Dean’s body went limp.

"Well, it worked," Dean announced, gently easing Cas out of him. "Looks like you win."

He sat up a bit and brought Cas closer, tugging the condom down his body. Cas was panting and immediately sprawled out as soon as his limbs were free; he was covered in sweat and looked exhausted. Dean just chuckled and grabbed a tissue to start drying Cas off.

"You all right there, buddy?" he asked, relieved when Cas nodded.

"That was just," Cas drew in a deep breath. “Much more physically demanding than I expected.”

"Hey, you did a great job." He shifted and put Cas down on the cool pillow, chuckling at the happy sigh Cas gave. "But now will you listen and wait for any big stuff until you’re…y’know, big?”