So I've been thinking about telling a friend about my crossdressing but here's some background info first. I am a 34yo and two of my best friends are females close to 50, up till a few weeks ago I was their boss. But within a few days I lost my wife and my job back to back, they have been very supportive of me like family. The one I'd like to open up to recently told us she was in a relationship with another woman for 14 years. and her good friend and neighbor now is a lesbian. I felt like this was important information because it shows her outlook on things. But here's where it gets terrifying, I've never told anybody I know. And I do care for her as she does me, strictly as great friends though. And I cannot let it get out that i crossdress, my family and ex-wife whom I share a child with could never find out. And I dont want her to freak out and feel weird either.
So my questions are,
1: should I even tell her?
2: how would I bring it up?
3: what if it all goes wrong?
I've always read that older women are more open to odd "sexual" things. Not that I want to have sex with her but I mean she would hopefully be more understanding than a younger woman. Long story short. I would love it if they were both open to my crossdressing now that I'm not their boss and I am separated from my wife. But I'm so terrified they will think I'm crazy and weird. I'm open to any advice but I really want a GG's take on this.
Thanks!
Jessi
