I'm pretty sure Dean's issues with Sam's sexuality started with Ruby. He doesn’t seem to be concerned that Sam would sleep with Ruby in S3. He had other Ruby issues, but not that. I don’t recall him having issues with Sam sleeping with Madison. In S1 Dean was the one pushing for Sam to get involved with women.
And while Ruby being a demon made those issues 231 times worse, Dean was actually having issues when he thought the demon was a human one-night stand. In Lazarus Rising, Dean, seeing a bra that Ruby had left in Sam’s motel room, says, “Oh yeah. I really feel your pain.” Dismissing Sam's grief over Dean being in hell. Implication being that Sam was busy screwing hot chicks and not being sad about his brother. And Sam basically beeps over that, being the kind of person that he is, as he will essentially beep over Dean’s accusation about “banging monsters,” as he will eventually beep over Dean’s sex/rape jokes about Gadreel in Sharp Teeth.
(As a side note, I think Sam Winchester’s sexuality fascinates me more than that of any character I’ve encountered since Torchwood’s Toshiko Sato.)
We see this again in the fairy episode, when soulless has a one night stand while Dean's in the fairies' clutches. Of course, soulless really DOESN'T care, but Dean's reaction is remarkably similar: “I was abducted. And you were banging Patchouli.” And Dean said that Sam should have “[sat] in the dark and [felt] the loss.”
(“Absolutely! But couldn’t I just do all that and have sex with the hippie chick?” Oh, soulless. Quite possibly the funniest line in all of Supernatural.)
We see it again in S8, when Dean blames Amelia for the fact that Sam didn't look for Dean when Dean was in Purgatory. “You left me to die for a girl?”
So, what changed? Why this sudden hostility towards Sam's sexuality?
What, exactly, did Sam think was happening to Dean while he was having sex with Sparrow?
What, exactly, was likely happening to Dean while Sam was having sex with Ruby?
Sam was having consensual sex with a demon while Dean was being raped by demons.
Sam was having consensual sex while he explicitly believed Dean was being raped by aliens.
I’ve noticed that a lot of soulless Sam’s apathy that bothers Dean so much involves rape. That’s the running joke in CYHIYB. In Caged Heat, Meg is threatening Dean in a highly sexualized way when Sam laughs, and Dean is clearly not okay with this (even though he cracked a joke in Shadow when Meg was sexually threatening Sam…but of course that was a whistling in the dark sort of thing, not an I don’t particularly care sort of thing…).
Even when Dean is turned into a vampire, Boris threatens him in a sexualized fashion. He refers to Dean as “pretty” before turning him, which causes Dean, in his usual sexualizing everything fashion, to retort, “Yeah, sorry again, pal. I don't play for your team.” Dean may have thought that being raped was a real possibility in that encounter. It is not just that soulless does not give a fuck about Dean being traumatized. It’s that soulless, specifically, does not give a fuck about Dean being sexually threatened or raped. Which is super interesting given that soulless, himself, has been raped. Which was almost certainly not true of Sam previously (although he had been sexually threatened, of course). In fact, I’ve heard some pretty convincing arguments that soulless’ promiscuity was in some ways about regaining ownership of his body. Which is especially interesting in light of the fact the souled Sam basically never has sex again (at least through the end of S10). Excepting Amelia, of course. I’m telling you, this guy’s sexuality fascinates me.
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