The show is Ned's Declassified School Survival Guide. Cookie pretends to be a girl named Simone to find out what his crush Lisa likes. "Simone" shows up in a couple episodes and the bully Loomer ends up developing a crush on this "girl". It's a tranny's trapping fantasy brought to life, only back then they knew that men can't become women so they made it funny.
The show is Ned's Declassified School Survival Guide. Cookie pretends to be a girl named Simone to find out what his crush Lisa likes. "Simone" shows up in a couple episodes and the bully Loomer ends up developing a crush on this "girl". It's a tranny's trapping fantasy brought to life, only back then they knew that men can't become women so they made it funny.