Dean hadn't meant to embarrass Sam. He was pretty sure he'd never taken anything that big before and he could tell it was going to be a challenge. There was definite interest under the surprise, though. He wanted to do this. Wanted Sam to watch.

He paused to add more lube and slipped all three fingers back in, stretching himself as much as he could with just his fingers. Soon, it was obvious he was going to need more. He withdrew his fingers and reached for the cockring, fitting it in place and snapping it closed. He could count on one hand the number of times he'd put one on himself. It was kind of hot.

Once he was prepared, he laid back and looked at Sam with a hungry gaze, waiting for his next order.