I think they probably both had feelings for each other when they were younger, though it's sometimes hard to say if those feelings were ever truly realized and accepted or if they were repressed and just not thought about. But I've also read some FANTASTIC and beautiful pre-series fics (in fact, my all-time fave fic is pre-series, and one that I think you recced in the comments of your first post - To Wish Impossible Things), and in a way, I *could* see it happening where Dean allows it but never lets it get to a point where the intimacy is there. I think it would just be about sex to him at that point (even though I think he'd FEEL differently, but wouldn't let Sam get that involved), and at some point he'd end up breaking it off, which would lead Sam to leave for Stanford. I could see that...as far as reading fics goes. But for my own personal fanon beliefs based on the whole series, I'm sticking w/ my post-season 2/season 3, lol. ;)
Dean was SO broken after John died, and he even admitted to Gordon in Bloodlust that he couldn't talk to Sam about it. I think it was pretty obvious that he turned to anger and brutality in hunting for a while there to deal w/ losing John. I mean, he smashed up his BABY cause he was so frustrated and hurt and angry. So that leads me to think that any sex going on at that point would be angry sex. And...that's probably why I wouldn't want to see their "first time" happen in that time frame, cause I'd want their first sexual experience to not be just a physical thing to erase the pain, but more about *them* and about how they need each other and love each other. But then again, I'm a complete romantic like that, so that may skew my bias a bit, lol.
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Dean was SO broken after John died, and he even admitted to Gordon in Bloodlust that he couldn't talk to Sam about it. I think it was pretty obvious that he turned to anger and brutality in hunting for a while there to deal w/ losing John. I mean, he smashed up his BABY cause he was so frustrated and hurt and angry. So that leads me to think that any sex going on at that point would be angry sex. And...that's probably why I wouldn't want to see their "first time" happen in that time frame, cause I'd want their first sexual experience to not be just a physical thing to erase the pain, but more about *them* and about how they need each other and love each other. But then again, I'm a complete romantic like that, so that may skew my bias a bit, lol.