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He doesn’t do it for the sex.
Nobody would believe that, especially not Sam, and there’s no way he’d tell them (him); but it’s true.
Okay, sure, the sex is good – how can sex not be good? – and he’s not faking it when he gets all excited, every time their job takes them within sniffing distance of a strip bar. He’s only human, after all.
But what he really craves, what really keeps him chasing tail when in truth he’s so darn tired after hunting that the first thing a bed says to him is ‘sleep’ and he’s not even sure he’ll be able to get it up (not that that’s ever happened…) is the simple closeness of another human being. A warm body wrapped tight in his arms, a night when he doesn’t have to sleep alone.
It’s just easier for everyone concerned if he pretends it’s about the sex, because then they’re not surprised or hurt when he heads off in the morning with a wink and a grin. Because it doesn’t matter who he curls up with under the covers, as long as there’s someone. He doesn’t objectify women, he’s not that shallow, well not in that way; but maybe he does in another, in this need for softness and closeness no matter how little time they’ve known one another.
That chick back in High School got pretty near to the bone, and he knows it’s pretty jerky behaviour, but it’s just another aspect of his game face. Dean the womaniser, Dean the tail hound, Dean who loves sex like he loves food. People (Sam) can laugh that off and shake their heads in fond exasperation, make allowances, think they understand.
But it’s why, those few times when he does get close to a woman, close in the emotional sense, he falls hard. Cassie, Lisa, even Carmen, the woman of his dreams who never existed outside a monster-induced hallucinatory coma. And it’s why, whenever a woman they’ve saved gets all grateful and her eyes go soft and she looks at him like he’s a hero, and maybe she kisses him on the cheek, and he knows that he could, if he only asked for it – he grows suddenly, unaccountably (to Sam's mind) bashful, because then it’s no good. It wouldn’t be just about the sex any more, and it couldn’t be about anything closer.
Because he knows he can’t have this, wouldn’t wish this life on any woman, least of all a woman he loved. So it’s safer not to get close, except in the physical sense; to use them and move on, new town, new body in his bed. It’s safer for everyone, and if it means he has to use sex as an excuse for their company, well, that’s certainly no hardship.
But it is lonely. And it gets lonelier, as his path grows harder, and especially after Hell, when the loneliness shuts him in with his too vivid memories. At those times he’d take anyone, even an ugly chick (okay so he is shallow; but if sex is gonna be involved, he has standards, doesn’t everyone?); hell, he’d even take a man.
Even an angel, and he’s caught himself looking at Castiel that way sometimes, when he’s really hurting, because Cas seems pretty sympathetic, as angels go, and at least he wouldn’t have much explaining to do.
But what he tries not to admit even to himself is that really, deep down, if he could, the person he wants most in his bed is Sam.
Because Sammy’s his brother, they’ve been together through everything, shoulder to shoulder, hip to hip, and if anyone could truly understand, then it ought to be Sam.
But Sam’s the last person he can admit his failings to, because he needs Dean. Needs him to be the stronger older brother, needs to be able to rely on him, his rock and his anchor; and if the game face slips, even for a moment, then the very foundations of their relationship will be overturned, and that terrifies him even more than the nightmares.
Because that’s just a comforting lie, harking back to their childhood, when Sammy was smaller and the only Big Bad in his life was the regular, unavoidable absence of their father. Sammy doesn’t need him anymore, not really; he’s doing just fine on his own, and increasingly exasperated by Dean’s unwillingness to forge ahead with him into fire and darkness. And now he’s afraid that if he lets Sam in, lets him know the hollow place in Dean’s heart, not that Sam will be lost without his big brother, but that he won’t understand; and Dean will be lost without him.
So he doesn’t do it for the sex.
He does it because he can’t have Sam.