Megan Atwood 
Raise the Stakes [PDF ebook] 

The prize: $10 million The rules: Be the first to complete ten tasks assigned by the Benefactor. Do not ask questions. Do not tell anyone what you’re doing. Do not fail. The consequences: Unknown Colin wants out of the Contest. Each task he’s assigned by the Benefactor leaves him more convinced that he’s part of something shady. Not to mention his every move is being tracked. But the prize money would help Colin’s transgender sister, Danni, afford surgery. Can Colin find out what the Benefactor is really up to without ruining his chances to win the Contest?