Hi Kelly, welcome!

Thank you so much for bringing this up. I've been here for awhile and this is the first time I've seen this topic discussed. I haven't even experienced it with my own BF, so I'm glad to be reading all the responses. I do have some thoughts about a few things you said, and I hope they help:

Quote Originally Posted by KellyV GG View Post
Sure wish I had a "happy place" to change in to.
You and I are not transgendered, so we don't have that side of us that feels precarious and vulnerable where we don't know how to process certain emotions. So there is no need for us to escape out of our gender if we run into a situation that we simply don't know how to deal with. As the other TGs said here, it will take time for your BF to reach the same level of confidence with his femme side as he feels with his guy side.

Quote Originally Posted by KellyV GG View Post
that it was OK to emulate me and my gender until there was a real issue to deal with
Your BF is not trying to emulate us. He does want to learn from us because he hasn't been socialized to know how to express his femme self, but he really is trying to be herself.

Quote Originally Posted by Joni Marie Cruz View Post
It's even worse in some ways to be given freedom to be yourself if you've been closeted up for years and learning how to deal with that freedom is kind of tough.
Joni Marie, hope you won't mind my take on what you said, but to explain to Kelly, I understand you to mean that it is much easier learning how to process feelings as a woman if you've had the freedom to do so all your life, than it is to learn how to do this all at once, when you suddenly have or give yourself that freedom.

Quote Originally Posted by KellyV GG View Post
What are the right questions to ask without sounding like I'm accusing him of something and without him getting defensive? It's very uncomfortable even going there..I'm not sure that he knows how he feels and I don't want to push it but I know that we REALLY need to talk about it.....thanks!
It's not so much the questions as the frame of mind you both are in when you discuss things. It is best to remain objective and positive, as if she is the teacher and you are trying to learn. Talking about the fundamentals of being femme is hard and your BF might not have all the answers. He hasn't needed to define it in words for himself. So asking questions like "what makes you want to dress" is like asking someone "why do you like apples better than oranges".

You could ask her his history; when she began, how she felt while reassuring her that you understand the concept of having felt scared or ashamed when she was younger. You could ask her if she or he feels sad for not being able to do certain things, or maybe sad that she couldn't show herself to her parents. You could ask her about one of her best experiences while dressed. And ask her what her dreams are, what she would like to do, all the time keeping an open, not judgmental attitude. And lots of cuddling. And the converstation will go from there!