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For a while, Castiel had thought that maybe there was something wrong with Dean Winchester.
The man seemed worryingly prone to non sequiturs in conversation. Castiel was concerned that this failure to communicate coherently was a sign of impaired brain function. A damaged frontal lobe could’ve been impacting Dean’s episodic memory, making him unable to construct a conversational thread in a sensical way. Alternatively, Dean may have been suffering from Wernicke’s aphasia as a result of a stroke, creating neologisms that made sense only to himself. However, Castiel couldn’t remember Dean ever having had a stroke, so perhaps it was not Wernicke’s aphasia. Brain damage due to blunt-force trauma to the head, however. That was much more plausible. The human brain is such a delicate structure. It would almost have been a shock if Dean Winchester, with his annoying propensity to throw himself through windows and to floors and in front of monsters, had no brain damage at all. And so at first, Castiel was fairly certain that Dean Winchester’s confusing turns of phrase were the result of a traumatic brain injury, or perhaps of many small injuries built up over the years.
In time, however, Castiel discerned that his initial conjectures had been completely off. Dean Winchester was simply very fond of incorporating references to human pop culture into his speech patterns. Due to Castiel's unfamiliarity with said culture, these references had instead been read as non sequiturs. In a way, this revelation was a relief, for Castiel did not want Dean to have brain damage on top of everything else.
Yet locating the source of a problem does not immediately fix it, and so Castiel still finds Dean Winchester's style of communication very frustrating at times. It is, however, a start, and Castiel is truly doing his best to decipher Dean’s non-non sequiturs. Castiel has by now realized that when Dean mentions pop culture, he does so because he can draw some sort of parallel between the media in question and his own current situation. To decode his references, Castiel just has to recognize the media in question, and then determine which aspect of it Dean finds similar to whatever real life event is occuring. Castiel has, indeed, become quite proficient in identifying when Dean is making a reference, rather than using metaphor or synecdoche, an accomplishment in which he takes not a little pride. Unfortunately, Castiel still doesn't know much about Earth's popular media after the fourth century, and as such, he has not had much luck in understanding Dean Winchester, even when he's able to recognize that Dean is making a reference.
This is one of those times.
He does not know who Bert and Ernie are.
But no matter. Maybe he can figure out Dean's meaning by analyzing the ancillary details of the statement.
Apparently these Bert and Ernie characters are homosexual men. Of course, Castiel thinks, Dean could've been using the alternate, slightly outdated definition of the word. But Castiel is fairly certain, given his experience so far with Dean Winchester’s vocabulary, that Dean is much more likely to have been using the term "gay" here to mean homosexual, and not joyful. Comfortable in that assumption, Castiel moves on.
Taking into consideration the conversation leading up to this point, Castiel concludes that Dean had intended to connect his reference to the issue of Castiel's virginity (Castiel briefly reflects that he had never, until now, considered his virginity an issue; in fact, he had not considered it at all. But Dean Winchester clearly seems bothered by it, and so it must be an issue after all). Dean had followed his mention of male homosexuality with a promise that Castiel would not die a virgin.
Did Dean believe Castiel was a male homosexual?
As an angel of the lord, Castiel has no preference as to the sex of his vessel. Over the millennia, he’s inhabited female as well as male bodies, and found them equally acceptable, each with their own social advantages and disadvantages. Castiel himself has no gender to speak of. Nor does he believe that he has (rather, would have) any preference as to the gender of his (hypothetical) sexual partner. After all, humans had proved that they could, as Dean might say, “make it work” for whichever combination of genitalia was involved. Castiel's vessel would (hypothetically) pose no physical boundaries to sex with men or women.
Castiel thinks that, probably, the intricacies of angel gender are not something Dean Winchester has given consideration. Dean exclusively uses female pronouns when referring to angels in female vessels and male pronouns when referring to angels in male vessels, and thus exclusively uses male pronouns when referring to Castiel. Most likely, Dean finds it simplest to see Castiel as a man.
Yet if Dean believes Castiel to be a homosexual man, surely there must be a reason for that as well?
Is there… something about Castiel's comportment that suggests male homosexuality? His vessel's clothes, or its grooming? He's unsure what else could be responsible for such an impression…
Castiel resolves to return to that particular issue at a later date.
So finally, Castiel arrives at the last part of Dean Winchester's pronouncement. Dean had implied-- no, he had, in fact, asserted-- a personal responsibility to ensuring that Castiel would lose his virginity this evening. It seems incredibly important to him.
Very perplexing.
Castiel puts all of his conclusions together, and realizes, to his immense shock, that Dean Winchester had clearly just proposed that the two of them engage in sexual intercourse.
For a few moments he is frozen solid, his thoughts whirling at an even faster speed than that at which they had been moving up to that point (which was incredibly fast), so fast that in fact they sort of blur together into a white nothingness, and Castiel simply does not know what he is thinking anymore.
Then Dean Winchester says, "Let's go," and, almost as though he has lost the ability to control his vessel, Castiel finds himself following Dean out the door. How could he do anything else? With Dean Winchester as his charge, his purpose–he would follow the man anywhere. Beyond Hell, beyond Heaven: he would follow Dean Winchester to the edge of reality itself, and if Dean dove off of that edge, Castiel would follow him there too. Following him out the door of the abandoned house drenched with the odor of holy oil, into the cool darkness of the night and towards Dean's beloved Impala– that's nothing in comparison. Perhaps, Castiel reflects, it is fitting that Dean Winchester be the one to take his virginity, if it really is such an important occasion; they already share a bond that few, if any, could claim or even understand, a bond that transcends time and space and the laws of Heaven itself. If Castiel has claimed Dean’s soul by right of conquest in Hell, it's a rather poetic mirroring, for Dean to mount his own sort of conquest of Castiel in return. Yes, if Castiel must lose his virginity before he perishes tomorrow, it feels right that Dean Winchester should be the one to take it.
The feeling that Castiel experiences when they arrive at the brothel is beyond words in any human language or Enochian alike.