Have you ever dressed in the opposite genders clothes? And if so, Why?

Yes everyday now. I started wearing some of my mothers clothes at 8 years old. I am now an open Cross Dresser.

Well considering most women's clothes were originally men's clothes in the past, yes I have.

I like wearing my hubbys old flannel shirts ...they are super comfy

I wore men's worn out levi jeans in high school.They looked great on me.

Yes — different reasons.

Boys jeans fit better

yeah, for a costume party. And several times at the request/insistence of my girlfriend at the time

A lot of my clothes are mens

yes. pretty often.
and i used to for a long while when i was younger. and it was because i wanted so badly to be male.

Yes I have and still do quite often depending on how I feel on any given day. Some days it’s loose during men’s clothes other days it’s dresses and heals or a top and leggings. Now matter how I dress I still wear panties and need to wear a bra to support my breasts

Yes I have been dressing for more than 10 years. I have a female body so I am passable.I have a lot of females clothes .I spend about 90% of my time as a female. I am also a sissy