looking for a story

Okay I have been searching for ages for a story.

Setting: boys boarding school
Character: Unsure of Tom possible Tammy/Tamara
I though last name might be Smart or something similar but could be mistaken.
Age 16/17?
Parents rich and away a lot.

Tom goes to town on a weekend dressed (en-femme?) not sure

Women's clothes shop owner spots Tammy/Tamara and ends up giving job on weekends.

Eventually Tammy/Tamara leaves school and lives with shop owner.

At one point Tammy/Tamara helps at a theater not sure but I think she ends up as leading lady.

At another point finds some rich estranged family nearby with her dad and is bridesmaid for a cousin or something.

If anyone has an idea of what story my ramblings refer to I'd be happy if you could let me know.

Big hugs n Thanks

Lizzie :)