Gaitskill attempted to find a publisher for four years before her first book, the short story collection Bad Behavior, was published in 1988. The first four stories are written in the third person point of view from the perspectives of male characters. The remaining five stories are written from the perspectives of female characters. Secretary is the only story in the book written in the first person point of view. Several of the stories have themes of sexuality, romance, love, sex work, sadomasochism, drug addiction, being a writer in New York City, and living in New York City. A Romantic Weekend and Secretary both explore themes of BDSM and psychological aspects of dominance and submission in sexual relationships. The story Connection is about a female friendship. Gaitskill's fiction is typically about female characters dealing with their own inner conflicts, and her subject matter matter-of-factly includes many "taboo" subjects such as prostitution, addiction, and sado-masochism. Gaitskill says that she had worked as a stripper and call girl. She showed similar candor in an essay about being raped, "On Not Being a Victim," for Harper's. Gaitskill's 1994 essay in Harper's also addresses feminist debates about date rape, victimization, and responsibility. She describes ways that individual subjectivity influences all experiences, making it impossible to come to "universally agreed-upon conclusions." The film Secretary is based on the short story of the same name in Bad Behavior, although the two have little in common. She characterized the film as "the Pretty Woman version, heavy on the charm," but observed that the "bottom line is that if made you get some money and exposure, and people can make up their minds from there." The novel Two Girls, Fat and Thin follows the childhood and adult lives of Justine Shade and Dorothy Never. Justine works through her sadomasochistic issues while Dorothy works through her up-and-down commitment to the philosophy of "Definitism" and its founder "Anna Granite". When journalist Justine interviews Dorothy for an exposé of Definitism, an unusual relationship begins between the two women. In an interview, Gaitskill discussed what she was trying to convey about Justine via her sadomasochistic impulses: The novel The Mare, published in 2015, is written from the perspectives of several different characters. The primary characters are named Ginger and Velvet. Ginger is a middle-aged woman who meets Velvet, a young adolescent, through The Fresh Air Fund. Other characters whose perspectives are featured include Paul, Silvia, Dante, and Beverly. Gaitskill's honors include a Guggenheim Fellowship in 2002 and a PEN/Faulkner Award nomination for Because They Wanted To in 1998. Veronica was a National Book Award nominee, as well as a National Book Critics Circle finalist for that year. The book is centered on the narrator, a former fashion model and her friend Veronica who contracts AIDS. Gaitskill mentioned working on the novel in a 1994 interview, but that same year she put it aside until 2001. Writing of Veronica and Gaitskill's career in Harper's Magazine in March 2006, Wyatt Mason said: Gaitskill's favorite writers have changed over time, as she noted in a 2005 interview, but one constant is the author Vladimir Nabokov, whose Lolita "will be on my ten favorites list until the end of my life." Another consistently named influence is Flannery O'Connor. Despite her well-known S/M themes, Gaitskill does not appear to consider the Marquis de Sade himself an influence, or at least not a literary one: "I don't think much of Sade as a writer, although I enjoyed beating off to him as a child."
