I need help to take the next step.

Thank you everyone. I will take your advice. I have to say that right now it feels like it'd be easier and better to put the whole thing back in the closet.

Edited, I found links for the movie. See at end.

I think that one of the things that scare our SO's most is the concept that we want to transition or are gay. Yet, I can think of one instance where a lot of women were attracted to a crossdressed guy: The Rocky Horror Picture Show. I used to go see it often; and there were lots of girls who found Tim Curry very, very hot. It ties into another theory I read, that lots of girls are a little 'Bi' at least from the waist up, so even if they found other girls sexy, they probably never acted on it, also for the fear of homosexuality (the old, 'what if I like it? OH MY GOD!' But it would be ok if it were actually a guy! ). I never explored this concept, although in retrospect, I should have. So, if you haven't seen the movie, watch it with your SO, and ask her if it would be alright to dress up like Dr Frank'n'furter. Maybe even go to a midnight showing of the movie if they still have them, where lots of the patrons dress up as one of the characters in the show. Just an idea.
rocky horror website with show listings: http://www.rockyhorror.com/participation/showtimes.php

Found it on youtube, not a perfect version, but quite good. https://www.youtube.com/watch?v=iMezOkzKXa4

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Originally Posted by Krisi

I wouldn't try "introducing it in the bedroom" anytime soon unless she brings it up. Many women draw the line at that.

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I agree. I did that once and it sent us back A LOT. Things went from being a fun idea to having major doubts. She's trying really hard to get up for it but the lingering image of that one day gets in the way. I would say go slow and with caution to her feelings/needs.

Brilliant idea Sometimes_Miss!!

Thanks Katie01, we are in a better place now after a little talking. She's now making little suggestions like "would you like me to teach you to do make up" and "you look ok in that" when I wore my skinny women's jeans for her - mostly I respond non-commitally at the moment. Good progress though I think. I certainly feel better for it as it does feel nice to be starting to relax the hold on this big secret!