I Don't Want to Be a Man (1918)

More of the Lubitsch silent movies from his German period.  This one stars Ossi Oswalda (the actress and the role have the same name) as a rambunctious young woman who is a bane for her uncle.  The movie opens with her smoking cigarettes and playing poker.  What to do?  The uncle turns her care over to a guardian who promises to take her in hand.

That sets Ossi's teeth on edge and she decides to pose as a man for an evening out.  During her time as a cross dresser she discovers that there are a number of downsides to the cultural expectations of men.  She decides that in the end she is happier with her life as a woman.  In the meantime, she has a little tryst with her guardian--we know and Ossi knows that she is actually a woman, but the guardian does not know that the man he thinks he is kissing is actually a woman.  Very risque indeed.