To answer the first question, Part 1 was where I told my gf a few weeks ago that I cross dress and how I feel about myself. I told her a more personal version of when I introduced myself here. I didn't know about Susan's at the time.

https://www.susans.org/forums/index.php/topic,7863.0.html

it was difficult for me to tell her but needed to be done. We hugged as I told my story. When I am done, she again shows how great a women she is and says that she is ok with my cross dressing. She says that she is ok seeing me emfemme, but it does nothing for her. She tell me that she thinks it is great that I'm exploring my sexuality. Since I'm looking for a long term relationship, I felt that I needed to be open with her. She is the only person that knows this about me.

a little side note, since I know myself well enough and I knew when the time came to tell her that I would be too afraid to say what needed to be said, I  totally shaved my body the day before. I thought by doing this there would be no way for me to weasel out of telling her why. After telling her, she offered advice on shaving since I did a butcher job on myself. 

so my question is, how do I go about introducing Natalie to her in person? I feel if I do this wrong it will be a shock. Aka if I run out to greet her in full makeup in a little mini dress that may be too much. I guess it is a turn off to her, but she is being polite. Sometimes I feel like dressing a bit showy, I guess I need to warm up to that? I can hide this from her for a time since it is a long distance relationship for now, but when she moves to the area soon, it will be inevitable that sometime she will stop by when Natalie is there. I think a big help for me is learning to dress more casual too. Us gal's don't go running around in skirts and blouses all day.

I am trying to be sincere here. I really care about this woman. It seems that she really can accept me for me. But I know this could blow up in my face if done wrong.

Natalie

Hi Natalie,
   I am an IS and I know 'coming out' to the one we love is by far one of the hardest things to do. My wife also surprised me by being so supportive from the very beginning. The way I introduced Kim to my loving wife is very slowly. Allow her to adjust to each step before proceeding. For example, first step for us was total clothing (dress, hosiery, shoes etc). It's been roughly 9 months and we are up to make-up and all and are preparing for the next big step, society. I always wear hosiery and bra under my uniform and wear women's boots that I thought were not too obvious until I wore them on the day shift. Though nobody said anything I could tell by reactions and all that that I was found out. Since my wife works at same place I wear men's shoes on day shift now to save her the embarassment until we are ready to take on the world, so to speak, together.
   As for wearing skirts and blouses etc I wear all time at home and when out for now anyways I wear slacks and subtle blouses. When we embark on social outings I will wear same as at home. This is personal choice. I know other women who always dress this way and others who wear jeans etc.. It' s not a fashion statement just wearing what you feel most comfy in. I realize you may be far ahead in your transition but temporary sacrifices may have to be made to allow her to remain comfortable and supportive. Good luck,
                                                                            Kim

I find that showing pictures of myself dressed the way I like is beneficial.  It sort of mitigates the shock that some might feel when they see you en femme in person.  I also think that if you are dressed as you usually are and show a picture or two (or more, but let them choose how many) that it's easier for the person you're coming out to to continue relating and asking questions.  Their discomfort is usually at a lower level that way.  If you just pop out fully dressed some people may panic and run.  Don't laugh, this recently happened to me, albeit accidentally, when I surprised my spouse's friend.

If you have a bunch of pictures you can choose among the best ones to show too.  Looking your best in coming out situations helps too, I think.

This advice is free and worth every penny, as some might say, Natalie.  And whatever you decide to do and whatever the consequences, you can share with us.

hugs & smiles
helen

Opps, I guess I posted the original question in the wrong forum. I see that it "magically" moved here 

coming out slowly with a plan is the way to go. I have time to think this out and it will be time well spent. I really like the photo idea. That shows who I am but allows a bit of mental distance from the actual thing.

more on when I told her: she said how that explained a lot of things. Why I'm unlike any other person she has dated, why I'm so sensitive.

Also I was just thinking how that past GFs and the current were all tomboys in a way. i'm not sure what to take of that, but an observation.

sure advice is free but I really appreciate the insight and another point of view that I can get in a place like this.
Thanks
Natalie

My SO discovered my attire and confronted me looking for the other woman.... when I told her it was mine and that I liked to dress and act as a woman, she made me prove it, I did and I did it in a very conservative manner, full makeup, hair, body shave etc. I wore a black knee length dress, black nylons and 4 inch pumps. She chuckled at first then took a good look at me, so you were not lying to me about another woman you do look like a woman, that part was good. But she was turned off by what she saw and has not allowed me to dress again. (back to the closet) The funny thing is she did not toss my stuff, she did say she would rather not see me this way and that it made her sick.