SISSY SCHOOL (Reluctant Feminization, Crossdressing, First Time)

Aaron’s gotten more detentions than he can count, but they’ve never stopped him from getting into trouble all over again the next day—not until he gets caught by Ms. Hodgeson, the school principal, using some choice words about the cute new girl in class. Ms. Hodgeson isn’t going to let Aaron off the hook so easily.

She gives him a simple choice: spend the summer at summer school, or spend two days in the shoes of the new girl. The choice is easy, but pulling it off, not so much. Because there’s another condition to Ms. Hodgeson’s deal: No one can find out Aaron isn’t actually Casey, the cute new girl from out of town. He has to commit to the feminine character or the deal is off.

So now Aaron has to spend two days as a girl—how hard could it be?