In his book Pimp: The Story of My Life, Iceberg Slim recounts his personal autobiography as a intellectually-gifted teenager growing up in the world before desegregation. Through various events in his life, he ultimately becomes a pimp in between jail stints.

Ultimately, Slim's novel is a book about the choices a black man has in the world before desegregation. He recounts his childhood and the choices he made that led him to become a pimp at the age of nineteen, after a stint in jail. Originally, Slim is little more than a con man in the streets, but after learning and listening from the other men in the jail who used to be pimps, he is enticed and decides to take on that lifestyle for his own.

As soon as Slim is born, he has problems. As an infant, his father becomes enraged and slams his body against a wall, walking out on the family. From then on, his mother tries to raise him on her own, but since there is only one parent and she is responsible for supporting them both, Slim is often left alone as a child. He is left alone with a babysitter named Maude who sexually abuses him when he is only 3 years old.

Slim and his mother move to Indianapolis afterwards and a man visiting his relatives, Henry Upshaw, immediately falls in love with Slim's mother. Henry is the only father figure Iceberg has in his lifetime and is the best person in his life. Henry reciprocates the affection and loves Iceberg and his mother immensely. Slim's mother, however, falls in love with a scoundrel named Steve. Giving Henry a weak excuse that they will return again soon, Slim's mother packs up Iceberg and meets up with Steve. Iceberg is destroyed by leaving Henry and cries as hard as he can. He misses Henry for the rest of his life. Henry dies a year after Slim and his mother leave him.

Steve and Slim's mother plot to take revenge on Slim's father. Telling his father Steve is a cousin, they literally rob Slim's father of everything he owns in order to pay him back for leaving her all those years ago. Living with Steve is a nightmare for Iceberg. At one point, Steve even smashes Slim's kitten against a wall for defecating on the floor. Slim's mother leaves Steve and they go to live in a hotel. Slim's mother misses Steve although they have separated until Steve sees her and assaults her physically. Slim waits for Steve by his apartment with an ice pick to kill him, but he never reappears. Years later, Iceberg spots an older Steve working as a garbage man and run to the street with his gun in his hand to kill him, but not even noticing Slim, Steve moves out of range as he is doing his job of collecting the garbage cans.

Slim meets a hustler named Party Time. Together, Party Time and Slim work a small-time con with Slim dressing up as a woman and pretending to be a black hooker to entice white men to meet "her" down an alley. They pay Party Time to meet the mysterious hooker, but by the time they walk down the alley, Slim takes off through the alleyways. Eventually, Party Time is busted and goes to jail for a year, though he never reveals Slim's name to the police.

By this time, Slim is 15 years old and graduates high school with a near-perfect 98.1 grade point average. He is recruited to go to Tuskegee University, but drops out after getting into a scandal with the local college girls. He has a relationship with a girl and asks her to turn a trick for him. They are eventually busted and this setup sends Slim to jail for the first time at age 17. He is released and meets a woman at his mother's beauty salon named Pepper. Pepper teaches Slim many of his "freaky" sexual tricks he will use on women in future years. Through a con of her own, Pepper sends Slim to jail for the second time.

Slim is released from his second stint in jail just months from his twentieth birthday. He listens and learns from former pimps in jail and wants to start pimping on his own. He scores his first hooker Runt shortly after leaving jail. Runt eventually sends him to another stint in jail through a betrayal of her own.

Slim grows in popularity and has a growing number of hookers working for him over the years. After Runt and Ophelia send Slim to jail, he is reduced to nothing and has to again start from scratch. He tries to regain his glory, but is quickly sent to jail again, shortly after his release, for robbing a drug dealer. He escapes from jail while serving this sentence.

Slim goes to his aunt's home, finds another hooker and starts trying to pimp again. He gains a number of whores, including Rachel who will work with him for 13 years.

Slim gets busted for being in a hotel room with an unmarried woman in Montana and they discover the escape charge on him. They send him back to prison. There, he finally decides to give up pimping and drugs for good. He studies the law and gets an early release. He hurries back to see Mama who lives only 6 more months before dying.

The novel ends and the Epilog(sic) tells us Slim is now a happily married man with two children. He works as a salesman and lives an average, normal life.