Dean isn’t attracted to anyone his age — oh, he has sex with women and he flirts like he gets paid to do it but his eyes tend to wander towards those a bit.. Younger. Freshman girls when they work cases, the too-young Jo at the Roadhouse, the hundreds of other poor things that have made him hate himself to the point of scarred thighs and wrists.
He’s 27 when Sam cottons on. He doesn’t know what gave him away because he’s always been so careful but his brother knows of his malady now and that’s enough to empty a clip into his own head.
He’s 27 when Sam comes onto him, all blushing virgin and little brother, and despite everything Dean knows about himself, he still gets hard and soaking in his boxers.
Sam’s far too old at the age of 23 but he does things to Dean no-one else of age has even gotten close to.
So, when Sam gets him naked and he’s in his lap, Dean knows he can take him and it’ll work but —
“Can you..” He doesn’t want to say it, not with Sam on top of him, the perfect picture of sex and love, and it’s nothing Sam doesn’t already know but to say it out loud? He nearly goes soft with embarrassment.
“Can I what?” Does that puppy head tilt and Dean whimpers, looking past Sam’s shoulder. “Dean?”
He sinks his teeth into his bottom lip before rushing the words out: “canyoupretendtobeyounger?”
Sam stares at him, slowly unraveling the words and when he does, his eyebrows raise a little but he doesn’t react more than that. Dean’s damn near about to call the whole thing off when Sam goes, softly, “how young?”
“I can go younger. If you need me to.”
Dean tosses his head back against the pillow and whines. Sam’s going to kill him if he keeps going on like this.
“No, Sam, you’re..” He rests his hands on Sam’s slim hips and smiles crookedly up at him, “you’re perfect.”