Hi, first time to give a comment here ... yes, all the questions you posted are quite thought provoking and have caused myself a sort of perplexity, too. So here goes, WARNING: VERY LONG POST! SO LONG I HAVE TO DIVIDE IT INTO TWO PARTS!
Then my question lies in just exactly WHY Brian is so particularly gentle with Justin during his first time. Earlier in the night, prior to the hospital, he seems to take joy in just playing with Justin, sure.
Brian could have been gentle, well maybe, because Justin did look like a fragile kid. He took joy in playing with Justin because somehow it lifted up the boredom. A kid who is innocent trying to act as if he is experienced and pretending to be brave can be quite entertaining. Or it can just simply be that he was quite struck by someone or something so different from the usual tricks. OR despite his bad boy or A-hole persona, Brian is truly a considerate, gentle man, kind even? as evident with how he is with Lindsay, Michael, Debbie, Vic.
So the fact that he sort of goes slow and gives him a full-on sex 'lesson' of sorts - "It's cold"/"It'll heat up" and "Does it always hurt?"/"A little bit; but that's a part of it" (Ok minus the ego-centric "No matter who you're with, I want you to always feel me" moment), I just find very interesting.
Maybe it was not a first time thing; ok don’t shoot me, just trying to touch base with all possibilities :-) BUT with Justin it was still different. Me, being ridiculously romantic, only when it comes to Brian and Justin, mind you, wants to believe that it was the first time and only time Brian did such an out of character acts. But assuming that even if it was not a first time for Brian to be with a virgin, right at that moment, the no repeat rule was unbroken. Justin might not be the first to be treated gently, given the extra care treatment and all those lines: I want you to remember this, etc. but then being Brian Kinney he does not have to do these things, being with him is enough right? And you are now one of the privileged.. BUT it was only Justin.. whom he broke the no repeat rule much later, the one he fucked more than once, albeit the resistance and trying to fight it every step of the way. He just can't help it :-) Ok going ahead of 101, sorry.
Either he really wanted it to be special for Justin (but then the question why again, what is special about the kid to bother with all that) or he suddenly felt so generous, an ahha moment, that he decided that he would share his ‘expertise’ to this kid, a possible protégé. But as you mentioned since he was bored before earlier in the evening, being a naturally impatient man, where did Brian got the supply of patience from, to take the time to mentor or tutor a very inexperienced kid? Yes very interesting indeed.
Of course we can also ask why Brian even bothers to take Justin to the hospital with him at all.
Yes, he could have dropped him off somewhere but then they do have some unfinished business to take care of ;-D I think Brian wanted to pursue. Before they were interrupted with the call, Brian was having a conversation with Justin (even if he was just playing him, Brian knew Justin knew close to nothing experience wise). But then it also struck me that while having this conversation, he was all the while looking at Justin (his face), even when he got the call and was on the phone, he cannot stop touching him, even if it is unconscious on his part.
In the hospital, even if he can’t remember Justin’s name, he consulted him about what to name his son. What is that? Ask an almost stranger, a trick to name your son. He must have been so high? Or completely out of it? Why did he not outright sided with Lindsay which would be an opportunity to irk Mel and why not ask his best friend Michael?