Jenn, somewhat similar to you I have a very, very close friend who is an ex-fiance of mine from >30 years ago (wow...has it been that long?). She and I are close enough that a lot of people would say I'm emotionally cheating on my wife. I'm not; my wife knew about her from early on, and has always accepted her presence in our lives. My wife knows everything and I'm 100% honest with her. My wife and this friend sometimes jokingly refer to each other as sister wives. Anyway...
Years ago when I was dating this woman, I wore pantyhose for her at her request. To this day, she doesn't know why she asked me to do that. When I went over to her place undressed thus, I was trembling like a leaf. I'd never told ANYone about my crossdressing, and I was terrified that my girlfriend was going to lose it, even though she requested to see me in pantyhose. She saw how nervous I was, and I blew it off saying "I was worried you'd think I was gay". I never told her then that I was a crossdresser.
Fast forward to ~5 years ago, and I finally told her. She's only the second person (after my wife) who knows everything about me. I couldn't be the friend I claim to be to her without telling her. So, I told her. She was quite taken aback by it, and had difficulty wrapping her brain around it. Nowadays, she's accepting of it as being part of me. She's never seen me dressed in any respect, and has never helped me with anything crossdressing. But, she is accepting.
