It depends on how close you are, how you crossdress, her background, your need for privacy, your plans for the future and more.
If you want to marry her or let her very very close to you, tell her.
If you are just dating (no real commitment) and she's very conservative when it comes to religion, no.
If you only dress for sex, then wait until sex comes up as a serious subject.
If you dress for stress definitely tell her.
in my opinion if u love her enough then u shud tell her if she loves u enough she will either, learn to live with it, or she might find it a bit of a turn on, many women do gd luck
I will answer in a question first... WHY?! Okay, well... From my eye-view don't... just don't. If you must KNOW... Just ask her to dress you as a girl... (reply might be in following catagories- NO!!!, WHY?!?!?, ARE YOU STUPID?!?!?, etc.)
be yourself ask them questions but don't act like you want to be their girlfriend dress good not nerdy
yes
first ask her how many boyfriends she has has. then she will ask you and you will reply.
ask her out to the movies or something!
you can keep from your girlfriend you want to buy her a dream dress she wanted
a dress
Will Mark Richardson ask Kylar Combs to be his girlfriend?
Fairbanks
Definitley ask her to the dance as a friend and not as a girlfriend. If you ask as a girlfriend it is a lot of pressure for the first time going out together.
Ask his girlfriend
all you have to do is ask her do you want to be my girlfriend