The sudden break-up with his long-term partner along with the untimely death of a close friend sent cultural critic Daniel Harris—a top gay journalist whose literary and cultural criticism has been praised by Janet Malcolm, Alexander Cockburn, Dale Peck, and Gary Indiana—into a deep depression. Complicating matters was his accompanying mid-life crisis, which entailed facing up to the harsh realities—and daunting challenges—of an aging gay man finding a new partner in today’s youth-worshipping gay world. Then Harris discovered for the first time dozens of men of all ages and sizes online shopping for sex partners in cyberspace. But he soon found that more than just gay men trolled gay sex sites; plenty of “straight” guys sought male sex buddies online, too, but often with one proviso: their male partners had to dress in women’s clothing. Although Harris had never before done drag and had no prior interest in women’s accessories, he set to work learning the ropes of cross-dressing once