Late last week, my girlfriend made a comment about needing to trim her toenails because they were catching on the sheets at night. She has a hard time reaching her toes because of a surgery, so she was basically asking if I would help her. I told her I would, and somewhat jokingly said that we should paint our nails while we're at it. She actually said, "ooh yeah, we should!"
I followed up and asked if she would really paint my nails and she was like, "yeah, sure!"
On Friday night, we did just that!
She said she was okay with it being on my toes since nobody else will know or see it, but didn't want me to do my fingers because we were going to be going out and about the next day. She doesn't yet know that I crossdress at home to the extent that I do (when she's not at home), but I'm feeling happy to be able to wear some color around the house barefoot and not have to hide it under my socks! I feel like this is a good step, but I will still proceed slowly.