To earn money to support her painting, Admiral worked for Nin one evening a week as a typist, transcribing her notoriously decadent diaries for 10 cents a page. Nin, who lived in Greenwich Village with a pet monkey, was hired by a "collector" — described by his emissary as an "old millionaire down South" — to write erotica; she was paid $1 a page and was ordered to churn out a minimum of a hundred pages per month. Admiral would type those pages up, too. Nin prided herself as a corruptor of youth and saw Admiral’s secretarial job as part of that project; she claimed that Admiral had been "liberated by my writing and our talks."

The "collector" soon tired of Nin’s poetic descriptions and requested she send only sex scenes, omitting the wasteful narratives that linked them. Hard pornography soon became, in Nin’s description, "hard labor," and in 1942 she recruited her young protégés to help. Nin referred to herself as "the madam of this literary, snobbish house of prostitution-writing": "I gather poets around me and we all write erotica," Nin boasted of the "epidemic of journal writing" she’d started. De Niro, a lapsed Catholic, wasn’t a particularly skilled or prolific member of this bookish vice ring and soon gave up the task. "It was very hard work," he recalled.

During the summer, De Niro and Admiral’s bohemian circle would decamp to the New England coastal village of Provincetown, where the painters would enroll in Hofmann’s summer school and experiment with landscape painting. Located on the tip of Cape Cod, Provincetown had a Portuguese fishing population, and in the summer the small cottages that were used to store fishing nets were leased to visitors; some artists, called "washashores" by the locals, set up camp in the dunes. "The whole lunatic fringe of Manhattan is already here," wrote Tennessee Williams, who waited tables with De Niro at the beatnik resort. "Such a collection could not be found outside of Bellevue or the old English Bedlam." For some, the scene was more social than productive; one year, Lee Krasner complained that the roll of canvas that she and Pollock had sent on ahead of them remained unpacked for the whole summer. De Niro, less well off than most, sometimes worked at a factory cleaning fish to pay his way.

"There are shoals and shoals of homosexuals here and no one for me," Nin complained in 1942 to Duncan, who was in military prison after having declared himself homosexual to evade the draft. ("I am an officially certified fag now," Duncan joked.) According to Deirdre Blair, in her biography of Nin, Duncan seduced both Admiral and De Niro, and bragged about each conquest to the other. In the summer of 1942, De Niro and Admiral were sharing a studio inland, a shack on a Provincetown backstreet with very thin walls. Nin writes in her diary that they were overheard by a neighbor arguing over Duncan: "‘I have been listening to you,’ the neighbor shouted back, ‘I have been weighing all your arguments. I think that Virginia is absolutely fair and right, and the behavior of Bob and Robert treacherous and ugly.’"

Nin goes on to write that De Niro, horrified at having been inadvertently outed, knocked on the door hoping to be able to explain himself. Three painters lived there, but no one answered. De Niro wandered the town, peering into people’s faces, wondering if they were the ones who had accused him. "He walked with shoulders bowed. He was silent. Haunted."

The close-knit group of the "last nursery" disintegrated. "Among my friends, love is a great sorrow," Duncan wrote in a poem published before he left for California, where he became a leading luminary in the San Francisco renaissance. "It has become a daily burden, a feast / A gluttony for fools, a heart’s famine."

Robert De Niro Jr., called "Bobby" by his family, was born in August 1943. The De Niros moved to a building in Greenwich Village that was big enough to accommodate two studios. De Niro Sr. had a part-time job as a guard at the Museum of Non-Objective Art (which became the Guggenheim Museum), where he worked alongside his friend Jackson Pollock. His relationship with Admiral ended soon afterward, before his son was two and despite the interventions of a Freudian analyst. He never remarried.