Black Stiletto books in order

The Black Stiletto series by Raymond Benson follows a masked female vigilante in 1950s-1960s New York City, told through diary entries discovered decades later, published between 2011 and 2014.

Reading order

# Title Published Author Buy on Amazon
1 The Black Stiletto: The First Diary 2011 Raymond Benson Buy
2 Black & White 2012 Raymond Benson Buy
3 Stars & Stripes 2013 Raymond Benson Buy
4 Secrets & Lies 2014 Raymond Benson Buy
5 Endings & Beginnings 2014 Raymond Benson Buy

The Black Stiletto series tells the story of Judy Cooper, a small-town Texas girl who moves to New York City and becomes a costumed crime fighter. Set across two timelines, the books alternate between Judy’s diary entries from the 1950s and 1960s and the present-day story of her son Martin, who discovers the diaries while managing her care after an Alzheimer’s diagnosis. In the past, Judy takes on organized crime, corrupt politicians, and street-level threats while keeping her identity hidden.

Each book in the five-volume series covers a different period of Judy’s career as the Black Stiletto. The first novel introduces her origin story and her early battles against a Mafia boss. Subsequent volumes move through the civil rights era, Cold War tensions, and the social upheaval of the 1960s, with the present-day storyline adding suspense as people from Judy’s past begin to close in on Martin and his family. Benson wrote the series as a love letter to pulp fiction heroines, grounding the action in real historical settings.

Frequently Asked Questions

How many books are in the Black Stiletto series?

There are five books in the Black Stiletto series, published between 2011 and 2014.

What is the first book in the Black Stiletto series?

The first book in the Black Stiletto series is The Black Stiletto: The First Diary, published in 2011.

What is the Black Stiletto series about?

The series follows Judy Cooper, a young woman who becomes a masked vigilante known as the Black Stiletto in 1950s and 1960s New York City. The story is told through her old diaries, discovered by her adult son Martin in the present day, as he learns the secret life his mother led before developing Alzheimer’s disease.

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