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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

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15y ago
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12y ago

are you a male wanting to be a female? I just straight out told my boyfriend i was a transgender (girl wanting to be a boy) he said he accepted that even though it was hard....and he sees me as a girl but he loves me beyond gender.

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10y ago

step 1: so, this is quite a conundrum. what you have to do is gradually, over time, make remarks about how womens clothing looks better than your own. she will probably respond to this positively.

step 2: buy a gimp suit (full body)

step 3: wear said gimp suit infront of gf and, if possible, her family.

step 4:front here forth, wear only womens clothing. this should make it very clear to your gf, that you are a bi-sexual tranny.

step 5: stay protected and have fun ;)

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Wiki User

15y ago

Get your info together, be ready to answer ANY questions and be clear

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14y ago

You can start off by asking them what are they wearing, or tell them what you are wearing. If she resonds then ask her if she have something similar and if she didn't mind to dress like you

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Q: How do you ask your girlfriend to cross dress with you?
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