My boss is always very nicely dressed. She wears suits most of the time, with either pants or a skirt, and skyscraper heels. She was wearing pinstriped trousers this morning. She's been chatting with a fellow she met via eHarmony, and he called to say he was coming by the hotel to see her. Then she started to fret about her outfit, that she wasn't dressed to meet someone. She said she was glad she wasn't wearing her "hoochie mama" suit, with a pencil skirt. Without thinking, I said, "I used to own a pencil skirt."
She looked at me with a slightly raised eyebrow, and asked if I'm a crossdresser. I told her, "No, I'm trans." All she said was, "Oh, okay."
She asked if I had any pictures of myself. I didn't, and the only site I can access from work that has any of mine on it is here. so I pulled up my profile. Now she knows me as Jaye, and she's cool about it. *Gasp!*
Now I just need to talk to her about coming out/transitioning at work.