Tupac had disturbing early sexual experiences with a family member and a close friend of his mother, according to a new biography that sheds light on the late rapper’s complicated relationship with intimacy and identity.
In Only God Can Judge Me, journalist Jeff Pearlman collects more than 600 interviews to explore Tupac Shakur’s formative years, revealing disturbing details that contrasted with his public image as a confident hip-hop sex symbol.
According to the Daily Mail, Pillman wrote that Tupac’s first sexual experience occurred when he was 14 years old, with a cousin.
“Although Tupac went on to become hip-hop’s sex symbol, his earliest sexual experiences were dark,” Pillman said. “According to a conversation he had with a close classmate, and corroborated by his sister, Tupac’s first sexual dalliance occurred at age 14, when he had sex with a cousin. The girl was also a teenager, and it only happened once.”
His sister Sekyiwa “Set” Shakur confirmed the account and questioned why anyone would expect her brother to speak publicly about such painful memories. “Can you talk?” she asked. “Can you brag?”
According to the biography, Tupac’s second encounter occurred shortly after with one of his mother’s friends, former Black Panther Afeni Shakur. The experience left him emotionally overwhelmed.
He later told girlfriend Simi Cruise, “The next day I thought I was in love with my mom’s friend. But she ignored me. She was a woman and I was a boy. It changed the way I thought about sex. It wasn’t love. It was just sex.”
These early encounters occurred during a time when Tupac was struggling socially and romantically.
“In Dunbar [High School]Tupac faced a series of rejections. Girls were simply not interested in him,” Perlman wrote. “He was short, poor, funny-looking, and poorly dressed. A good person. It ate him up. Despite Tupac’s outward swagger, he felt like a loser when it came to the opposite sex. He knew he had a game, no one wanted to play it. “
That changed when he enrolled at Baltimore Art School at age 14. Pillman describes the school as a place where romantic experimentation was common.
“Not sex, but drunken and/or high-end party making out. One weekend it was a girl. Another weekend it was different,” Pillman points out.
There, Tupac formed his first meaningful relationship with 15-year-old ballerina Mary Baldridge. The letters the two exchanged are filled with emotion and sexual tension. Tupac wrote in a letter dated February 1, 1988: “I miss you! I love you! It hurts!”
Later that month, he expressed mixed feelings about physical intimacy. “All I wanted to do was have sex…I didn’t think we should do it yet! I changed my mind and we should!” he wrote. As they became intimate, he continued: “I can’t wait to have sex again 2U. I just wanted to tell you how much I love you!”
Baldridge eventually learned that Tupac was unfaithful during their relationship, but she still fondly recalls their time together. “But,” she told Pillman, “these memories are special.”
Pillman connects the rapper’s troubled early sexual history with his later legal difficulties and complicated relationships with women.
In 1994, the hip-hop star was found guilty of first-degree sexual abuse of Ayanna Jackson and was sentenced to up to four and a half years in prison, but insisted he was innocent and served only nine months.
In an interview with NPR, Pillman highlighted how the rapper’s upbringing contributed to his difficulties in intimate relationships.
“It’s heartbreaking,” Pillman said of the rapper’s experiences with women. “He had his first sexual experience when he was 14, with a cousin. His second sexual experience when he was 15, was with an adult friend of his mother.”
Watch AllHipHop’s Chuck “Jigsaw” Creekmur’s interview with Jeff Pearlman below.
