Definitely something to the top/bottom gender connection you mention. Just like there is so much less of an outcry when a female teacher has sex with a young male student than there is when the genders are reversed. Clearly, there is a weird bias in the community where you need to be much more mature to take it than to give it-like there is this great burden that comes with being penetrated that is not there if you are the penetrator. And we consider ourselves so liberated-ha. So, make the bottoms of the world happy and have him take it first (and soon, go ahead and generate a little outrage!). Or not, either way your work has been of such high quality the story will be worth the journey.
P.S. Sorry for totally missing the time of this story by a decade. I was an avid reader for a long time, but then lost connection with your work for a while, and just came back. Still, a disrespectful oversight for which I apologize. If I might add one additional observation, I grew up (and am still a part of) wealthy California (though, sadly, not with the kind of gay friendly support that the CAP clan has built together, if only!). I can say that even in 2000, while the rest of the world was turning more conservative, the attitudes towards sex, drugs, etc…, that Will would be around, a lot of people would find surprising. Not just by the families, but also by community (even the police if you live in the right neighborhood). A little bit of tutoring and a lot of money, and a first rate university is guaranteed, and as long as you don’t f**k up too badly most peoples teen years are sort of considered do as you please time, as you will never have the kind of freedom again you have now.