Should I Tell Her?

So since i was 14 i liked the concept of crossdressing and being a sissy and i always wear my mother's clothes and it kept going till on day i talked to this guy online and decided to meet and ended up bending over for him while wearing mini skirt.
So I'm 21 now and have a close friend she's very open minded about gays and a lot of other things, and well i was wondering if I should tell her that I'm a guy who likes to crossdress and wondering if she can help me become more girly and feminine or avoid doing it