The idea of using pin-up calendars as fund raising tools is hardly unique, and even the idea of putting men in pin-up drag has been done before. The twist here is in picking one lucky boy from campus, getting to know him, and learning precisely how to either entrap him or entice him into participating. It's not just an afternoon of cheesecake poses, either - a proper transformation takes weeks of public humiliation, involving everything from shopping for shoes and lingerie, to getting a public makeover.
As for poor Brandon, we learn just enough to justify him as a target for the efforts of Jennifer and her sisters. He's short, skinny, and physically unimposing - an opportunistic gigolo who uses the freshman register to fake an interest in the likes and hobbies of the women around him. Beyond that, he exists only to be controlled, blackmailed, humiliated, and feminized. It's Jennifer who dominates the story, turning an awkward sorority project into first a passion, and then a lifestyle.
"I have discovered a part of me that I never knew existed before. I like being in charge and I like having power. Even more surprising, I enjoy the humiliation of the male of the species, something that Craig has discovered on those numerous occasions where I have mounted him with my strapon."
It's a fun story, humiliating for sure, but never entirely cruel (in fact, there's even a mention at the end that Brandon has come to enjoy the humiliation). If you're a fan of the genre, and are curious to step outside the submissive sissy and enter the mindset of a dominant woman, then Calendar Girl is well worth a read.