Ask her to lend you that pretty little Halston you've had your eye on
She probably already knows
You never know
Somehow have a general discussion about the subject, saying that people must really want to do it, see how she responds
It's perfectly acceptable for a woman to wear men's clothes.
I guess it all depends on your relationship with your stepsister. Only you can decide if you are close enough. My stepsister first introduced me to dressing up in skirts as a game when I was quite young. 12 years later, there are only dresses, skirts and blouses in my closet.
It was very difficult but I finally worked up the courage to tell my children I a transgender and prefer to live as a woman from now on, they took better than I even hoped for and they both support me
ill wash your dress in the morning sorry