«The Extra Man» by Jonathan Ames

Jonathan Ames, whose debut novel I Pass Like Night was enthusiastically praised by Philip Roth and Joyce Carol Oates, has followed up with a brilliant and comic second novel.
Louis Ives, the narrator of The Extra Man, fancies himself a young gentleman fashioned after his heroes in the books of F. Scott Fitzgerald. He dresses the part – favoring neckties, blue blazers, and sport coats. But he also has a penchant for women's clothing, a weakness that causes him to lose his job as a teacher at a Princeton day school after a bizarre incident involving a colleague's brassiere. Thrust out of Princeton, he heads to New York where he rents a cheap room in the madly discombobulated apartment of Henry Harrison, a failed but brilliant playwright who dances alone to Ethel Merman records, sneaks into Broadway shows, and performs with great style the duties of a walker – an escort for the rich widows of the Upper East Side.
The two men, separated in age by more than forty years, develop a relationship that is irascible mentor and eager apprentice, and they form a bond the depths of which neither expected. But Louis, when he's not with Henry, has fascinations that lead him to an unusual community on the fringes of the sex world of Times Square. He develops a secret life there, which he fears will be his undoing and which he must keep hidden from Henry at all costs.
A hilarious yet moving story about friendship and longing, The Extra Man is an original and unforgettable novel by one of America's most talented young writers.