And I thought MY thoughts were long...I'm kidding of course. I'm really glad you chose to come give your first comments, and they were really insightful! Thanks for sharing!
A kid who is innocent trying to act as if he is experienced and pretending to be brave can be quite entertaining. Oh absolutely, I agree. Watching Brian's face when Justin's trying so hard to talk big is hilarious. From the streetlamp Brian must realize he's totally full of it. I definitely think he pushes him for his own amusement: "Then get to it." ..."Uhhh, what exactly do you mean?"
And I totally call B.S. on the second half of "Well I guess we're all a little scared our first time" *pause* "but I don't remember anymore." Whether or not it being Justin's first time was the whole motivation for his carefulness is clearly what we're discussing here, but hands down Justin's virginity is definitely a factor.
he suddenly felt so generous, an ahha moment, that he decided that he would share his ‘expertise’ to this kid, a possible protégé There's an interesting point - a possible protege. Justin pretty much becomes his protege ultimately, but I feel that is after quite a few times of them being together. It's only about 106 ("High School Confidential"/Sean/You couldn't do better/"You Look So Fine") that he really gains that much confidence in his own sexuality to 'push' Brian back and challenge him. Although we know by 103 he at least knows how to get what he wants. But I can see what you mean - maybe he saw Justin's potential (He's been around the block, and he's also in advertising - he knows what the boys like, and Justin's definitely hot) and wanted that ego trip of going "I taught him the ropes." Definitely a possibility.
Why did he not outright sided with Lindsay which would be an opportunity to irk Mel and why not ask his best friend Michael? YES! This part always got me, especially with as close as we see that he and Lindsay are, and how much we see Melanie hates him (and the feeling's mutual). He was WASTED, but still had enough wits about him to call Michael, drive to his place, drive to the hospital, find out what room Lindsay was in - so why not consult him if necessary or simply go with Lindsay.