So! Time for a poll.
He has instructed me that I'm to wear dresses or skirts when I meet him post-trip, whether that's here or in Boston. No problem. He likes short skirts, though, which I am unaccustomed to. I skirted the issue (blame Adam, puns are contagious) last time by wearing a long skirt before he voiced a preference for short skirts - before his instruction at all, actually. Anticipation of needs is Of The Good.
But I have short skirts now, because he bought them for me.
But I also have this really cute retro sundress. It's not long by any stretch of the imagination, but it's not above-the-knee. It has strawberries on it. I can wear the red lipstick with it. He likes the red lipstick.
Wear one of the above-the-knee-skirts, going for impeccable obedience?
Or wear the strawberry dress, going for retro flair and giving him something to spank me for?
Audience participation day!
What should I wear?
Skirt and top
EDIT: A note: Often he really does like being given a little something extra to spank me for! It's just a matter of evaluation.