So, I put my little toe out of the closet today. I told someone close to me that I crossdress. My friend, we'll call her Abby. Abby and her family dropped by today to visit and pass the time. After a while, we decided to all have dinner. Abby's husband (we'll call him Bob) suggested he run back to their house to get some stuff to fix for dinner. I wanted a chance to talk to Abby alone, so I took him up on it.
I've known Bob for a long time, probably close to 16 years by now. Abby and he got married around 10 years ago, and I stood for him at their wedding. Abby's a sweet, loving, compassionate person of decidedly liberal bent. She has many friends of varying degrees of non-normativity. Honestly, I rather figured she'd be the best first person to tell, and she could help me find the best way to tell my wife, as well. (Note: We both decided that, "Honey, please pass the salt. Oh by the way, I'm wearing panties," would probably not be too good.)
She and I stepped out on the porch while Bob was gone and we talked. I told her about my explorations into bisexuality, and finally, hesitantly, about my dressing. She was so very good about it. I told her that I needed to know I would have at least one friend that wouldn't walk away from me for this, and that I really needed her advice and friendship, as a girl, just like we'd always been friends with me as a guy. One of the first things she did was offer to be my shopping buddy :)
We didn't talk too long since it wasn't going to take Bob long to get back, but I feel so good, so positive about this now. We're planning on getting together later this week to talk more, and just hang out.
I'm so relieved at how well this went, and I'm smiling ear to ear.