Chapter 1 begins with the family's arrival in Havana and an extended flashback to the complicated events that brought them there. Anna, named Connie in the book, is placed in high school and within months is seduced by a classmate, Maritza; they begin a year-long secret relationship. Confused and tormented by the fear of being outed, Connie tries to get back "on track" and go straight with a Chilean boyfriend, while the revolution's political events swirl through Cuban society, enveloping everyone. The October Missile Crisis, the purges of the old guard Communist Party, the Marquitos show trial, and Fidel Castro's consolidation of power are the crucial political events shaping Cuban life at this time.
Chapter 2 describes Connie's life at the University of Havana, where, after a brief relationship with a handsome Angolan exchange student and former MPLA guerrilla fighter, Connie is dazzled by Monica, another student, and becomes her girlfriend. Surrounded by a circle of friends, mostly gay and some straight, Connie is introduced to the underground world of gay Havana and Cuban bohemian life. Meanwhile, by 1965, the increasingly militarized society around them unleashes purges that sweep through the university, the country's high schools, and many cultural institutions in the hunt for lacra social (social scum) and counterrevolutionaries.
Chapter 3 takes place in the Sierra Maestra mountains, where Connie is stationed with a team of university students deployed to conduct surveys of the peasants' political opinions and their living conditions. Connie organizes and directs an amateur puppet troupe that performs for children and teachers in tiny hamlets in the mountains. This is a magical oasis away from all the turbulence in Havana.
In September 1967, Connie and Martugenia go to the movies one night, stroll along the seaside Malecón, and are brutally attacked by a pair of thugs who beat them while hurling homophobic obscenities. Police arrive suddenly. Connie, Martugenia, and the assailants are whisked to a police station, where the attackers become their accusers. Martugenia and Connie are charged with escándalo público (lewd public behavior). This is the beginning of a long nightmare that lasts well over a year. They are put on trial twice, suffer public humiliation and shame at the university, survive, and hang on for dear life, waiting for the political pressures to ease at the university and beyond. Martugenia keeps her job but loses a precious scholarship to England.
The 1968 arrest and trial of the Microfracción, an alleged conspiracy hatched by pro-Soviet Cuban communists accused of being more loyal to Moscow than to Fidel Castro, sets the stage for an aggressive political purge throughout the country. Ted is fired from his job. Connie's family prepares to leave the country, but Connie is determined to stay and finish her studies. The Revolutionary Offensive, another major political upheaval, sweeps the country, and Havana nightlife comes to a halt. All small businesses are nationalized; nightclubs and cabarets are shuttered. After her family leaves, Connie moves to her last home in Havana, a small room in Nuevo Vedado. She and Martugenia team up with friends, a gay male couple, and pass as straight couples in public. For a couple of years after Martugenia and Juan's sham marriage, the four enjoy freedom from their parents' rule.
In 1970, Connie makes a trip north on a Soviet freighter to visit her family via Canada. In New York she discovers the women's liberation movement and the gay liberation movement, and she meets radical feminists. Before leaving for Canada and the trip back to Havana on another Soviet cargo ship, she gets a taste of New York mafia violence in a lesbian bar. The trip gives her much to think about and time to contemplate her future, as she ponders where she can possibly fit in. She wants to stay with Martugenia, but living in Cuba has become increasingly problematic, and she has no job prospects there.
Connie presents her oral thesis at the university, graduates at last, tries and fails to get a job. Martugenia and Connie struggle with their dilemma. Martugenia is offered another scholarship in England. Connie persuades her to think the most forbidden thought of all—to run away together somehow in England. Martugenia has doubts and fears but agrees at last. They plan carefully. Connie books a berth on a ship months before the scholarship will begin, dismantles her home, and packs their books and papers together in homemade crates fashioned from Connie's furniture. Their plot fails in the end, and they are separated forever on the same dock where Connie had first arrived. Connie sails north, on the last ship before her life after Cuba begins. The book ends with a short epilogue.