Surprise! I hadn't expected to be doing this again until Tuesday...but then the wife called and said she was delaying her return until this evening. So, despite some other errands and such, I have time for two dressing/photo sessions today!
I'm calling these two sessions "The Sissy Schoolgirl and Her Headmistress". You'll see why later.
The nautical top is by Cathy Daniels, bought at Boscov's in June 2011; the scandalously short pleated microskirt is a thrift shop find by Big Flirt, from April 2011; the shoes are Isaac Mizrahi black mary-janes from Target in November 2007. Other accessories are a big shiny bow, chunky and silver jewelry, and frilly socks.
A somewhat different portrait pose:
More pics on Flickr; the second outfit later on.