The sissy secretary has always been a favorite of mine. I'm not sure why, either. Maybe it's because of the stereotype associated with secretaries, that they're often employed because of their looks or because of "favors" for the boss. Or maybe it's just that secretaries are one of the last true bastions of old gender inequality, and I like the idea of making a male experience that inequality.
There are quite a few good stories and captions focusing on this sub-sub-genre, but the best I've seen was a story/interactive slideshow produced on a (now-defunct) blog called The Sissy Trainer. All of his/her work was quite good, but for some reason or another, I really enjoyed the one titled Pink Slipped, about a man who loses his job and is persuaded to go to work with her as a secretary. Of course, this leads to his feminization. One of the best parts about it, however, was the way the woman introduced him to femininity. She dressed him in shorts, a blouse, and tights. This picture reminded me of that, so I decided to make a tribute caption.
Oh, and if anyone knows where I can find Sissy Trainer's work, please let me know. I'd love to see it again.
Anyway, here's the caption.