Anything for Love (1993)

Chris constantly is pushed around by bully Kurt and his gang. When he has to change to the same school as them, he decides to disguise in women's clothes on his way to school to avoid his tormentors. However already the first morning he runs into two teachers when still dressed up as female - so he's bound to the role. He learns of the advantages soon, when he manages to become best (girl-)friend to cheerleader Marie. Only when his coach sees how much he enjoys cleaning the women's showers, she becomes suspicious...