Started in High School with AD&D 2E and Marvel Superheroes Advanced.

Despite being the only guy that hadn't played before, I wound up as the DM where I have largely remained.

It was all quite good enough that I still do it to this day...though I know longer play either of those games, and instead just have fond memories of them.

I attended a multi-denominational Christian Highschool. Everyone was fine with roleplaying except for the token Romans 2:24 Christian who was, of course, a guidence councelor.
 
She was against roleplaying but wasn't able to get any traction from the staff. Then one year in the late 80's she got enough support from parents to officialy ban "Syberpunk, Meck warrior, Dungeons and Dragons, Paranoia and other Roll playing games." Which could have been the end of gaming except that our roleplaying 'xp' prepared us for just such a fight against the machine.
 
Any roleplayer: Teacher? Could me and my seven friends lock ourselves in your classroom and tape posters over the windows durring lunch?
 
Any teacher: Certainly. Just don't let the less trustworthy students know you're in there. Some of your peers are not as responsible.
 
That plan worked until we got girl gamers. After that we had to do it behind the groundskeeping shed.