You decide not to lie to yourself. You've always wanted to see how it feels to wear one, but you don't have any siblings, and you don't feel obligated to go through your mother's things, so... the skirt it is.
The temptation is too strong, and your curiosity overwhelms you as you take a long look around, make sure that no one else is looking at you, and then snag the skirt and stuff it into your pocket. A chill runs up your spine as you feel the cloth against your hand. It's smooth and soft, and you can feel a slight stretchiness to it.
Following the events of the lost and found, you head to your first class. You sit down and listen to the teacher drone on and on about math or history or whatever class you happen to be in. As you begin to fall asleep, your mind wanders, and you start to wonder if you should try it on at school or after school...