Basically, I think a creature's soul has a "true form". Which is why a ghost or an afterlife form of a person turns up looking like the person, for example. Castiel, with his grace taken, is still a
fallen angel. He's bound to a human form in the lack of another to return to but he's never a human, because to be a human, you're born to be one, and even this doesn't work if you were formerly something else (Anna, for example, was genuinely born into her own body and still never became a human per se, despite experiencing a life as one, because in the end she still recalled her true self and even as a child protested to the idea of her father being her real father, therefore living in a conflict against her assumed new form and identity).
Demons are mutilated human souls (and fallen angels, actually, lorewise at least), so a cured demon has been, indeed, cured, and becomes what it actually was before. The state of being a demon is unnatural to a human, just like the state of being "human" is unnatural to an angel.
If it was dependent on what kind of a meatsuit you walk in, then an angel assuming the form of a human would automatically become human, and a skinwalker taking the form of a dog would stop being a skinwalker and become a dog instead, when in truth they still function with the mindset of a human. Castiel's main flaw in the sense of becoming human is that no human will ever live up to be older than life itself. Castiel already is. He cannot be a human when his whole existence is something that is completely different from that of a human. He wasn't created as a human, therefore, he will never truly be one, and his former life and experiences as well as the fact that he is an angel will fundamentally affect the way he experiences "humanity".
He can live and die as jimmyflesh but inside, he's still an angel.
Stretching from that, I also believe humans that become monsters are monsters by state or affliction, not design. Lorewise, purgatory is a place of purification between heaven and hell and once a soul has been purified, it moves on to the final destination. Therefore, I believe that when a monster dies in purgatory, it ceases to be a monster and comes out as a purified human soul. This would fit the lore on purgatory, but whether or not SPN agrees with me, we'll probably never know. There are true monsters such as the leviathans and alphas which were created as monsters and have never been human, and they're generally pretty impossible to ice, so who knows what the hell happens to them if they die. Maybe they can't die in purgatory. Maybe they'll just pop up again like souls in hell do after every time they die. Which would mean d**k Roman's in there still, somewhere. Hmm. I don't know, I'm not God, this is one of those questions again. 8|
ANYWAY
Angels don't actually get feelings when they enter vessels. This has been Castiel's "flaw", the "crack in his chassis", something that isn't supposed to happen, because angels don't feel. The other angels loved to blame Dean for this ("When he first laid a hand on you in hell, he was lost", "He has this weakness: he likes you."
wink , but in truth as Naomi implied, it's always been just who Castiel is. Like Samandriel said: "Too much heart was always Castiel's problem."
He's not like the other angels, but he isn't like humans either.
Boners are physical reactions to stimuli and have very little to do with actual sexual interest. The scene with the prostitutes is interesting, I'll never be able to figure out if it was the sex that scared him or if it was the thought of having sex with someone who might not want to have sex with him, which would probably be akin to violence for him. Probably the latter.
I don't know what Castiel's age is, but considering he was in the lead of a garrison, is a seraph - the highest rank an angel can be without being an archangel - and was respected enough to make other angels listen to him when he flatout suggested they should break free from what comes most naturally to them, obedience, and think for themselves, I'd imagine he isn't a fledgling by any stretch. He was sent to hell to fight an extremely important war and came out on top of it as the one who brought Dean back - which, by the way, is funny because he'd already defied orders before. Why they sent down a soldier who could not be trusted on a mission of this scale is... baffling. I guess he was fresh out of Bible Camp and supposedly functioning, and because the mission didn't involve slaughtering innocent babies, he had little reason to flip again.
Okay, ahem, I'm way offtopic again.
I can get social pressure, though. Everyone and their dog (read: his older siblings from Anna to Gabriel and his best buddy Balthazar, and his primary human example, Dean) was all over sex. Therefore, I can totally get him falling and, stuck as a confused bag of guts and poop, follows example.
I just don't think it's an interest for him. Even with Meg, he played along to a point but then came the major, MAJOR hesitation. I think he may have tried it out if the chance was actually presented, but this whole subject still ******** irks me, mainly because there are so many people around me just parading that YAY HE FINALLY BECOMES HUMAN AND HAS REAL HUMAN'S NEEDS. Like ******** you people I am human too, I was BORN as one, and I don't experience sexual attraction, go away. I'm real tired of being dehumanized and this isn't helping, so I'm angry. Yes. Castiel's basically been THE reflection point for me: his character is so close to how I feel in society, out of place, and the lack of sexual interest was something I have literally never before seen in a character on any show, anywhere, established like it was for Castiel. A character who had the opportunity but did not feel it was a priority and never stepped up to take it because there were so many more important things to do, you just never see that anywhere. And now I'm back to being a freak again. Feels nice, not.
So yeah, I'm biased. Way, way biased, and also very literal with my lore.