Of all the bad things Dean Winchester could attest to doing in his life, there was only one that felt like a bridge too far—something he couldn’t confess proudly, something he’d consider for a few seconds before deciding if he even wanted it out in the open or not. It festered in the back of his mind and he struggled to admit it even to himself, but the truth was this: Dean Winchester’s biggest kink was listening to his brother cry.
It was an organic discovery from all the way back when Jess died. Those first few nights on the road Sam stayed stoic, he tried his best to come off reserved, but every night Dean would hear him whimpering and sobbing when he found any sort of privacy. It was late at night, and Dean was already in the middle of his process of getting himself to sleep, so he just tried to tune out Sam’s crying.
It continued on the next few non-consecutive nights: Dean would choke the chicken while Sam grieved in as much privacy as he could get in a tiny motel room, seemingly unaware of what Dean was doing only a few feet away.
The grieving process came and went, Sam returned to his normal brooding self, and Dean completely forgot about the cumulative two weeks he spent jerking off to the sound of Sam crying.
That was, until they properly hooked up for the first time.
Dean tried his hardest to teach Sam to beat off when they were younger, but all of his knowledge of fingering seemed null to Sammy. They had a frenzied grinding session in Baby’s backseat after a shared near-death experience that ended abruptly when they both realized what they were doing, and Dean had watched Sam masturbate properly when he thought Dean was asleep. Now, Dean was wedged against Sam’s body and Baby’s backseat and he was doing Sam’s soaked thighs.
Sam’s hands were braced against the front seats and the back window and he panted and sighed when Dean thrust into the tight slot. He looked thrilled, his dark eyes fixed on Dean when they were open and he actually laughed as he got close. He hadn’t seen Sam this happy in months.
But then he was reminded of something he’d almost forgotten when Sam did come, soaking Dean’s cock with slick: he forgot about the tears.
“What’s wrong?” Dean tried to console him, but his hardening cock sliding against his slit probably wasn’t helping.
Sam wiped them away with the heel of his palm, smiling uncomfortably. “Nothing, it’s fine.”
Dean wanted to pull his cock away and give Sammy space, he really did, but he was already so close; Sam was practically drooling onto him and he struggled to think when Sam’s face was flushed. Dean was amazed by how soft he looked with tears in his eyes.
He moved his cock around until he found purchase, sliding in with ease as Sam moaned and whimpered in the same breath.
Dean was torn, but he finished inside Sam after a minute at the sight of fat tears rolling down his cheeks. He leaned up and kissed Sam, tried to thank him, but he couldn’t shake how wrong it felt, the darkness behind Sam’s eyes as he redressed. Sam didn’t shy away, but he shrinked like Jess had died all over again. Dean drove all night while Sam slept in the backseat, crunched and curled up like he was trying to comfort himself.
He hoped that wherever Dad was, he hadn’t seen this.