Tupac Shakur was a strikingly attractive and charismatic musician who became a major cultural icon and sex symbol of the 1990s, thanks to his incredible talent.
Despite appearing confident and charming, he was a young man who found it difficult to form close relationships, and his first sexual experiences were troubling.
Sports reporter Jeff Pearlman’s new biography, Only God Can Judge Me, reveals many personal details about the late rap icon, based on interviews with over 600 people who knew him.
According to Pearlman, Shakur’s first sexual encounter came when he was just 14 — with a cousin.
Despite eventually becoming known as a hip-hop icon and sex symbol, Tupac’s first experiences with sex were actually quite troubling, according to Pearlman.
Based on what a close classmate told researchers, and his sister later confirmed, Tupac had his first sexual experience at age 14 with a cousin.
‘The girl was also a teenager, and it only happened one time.’
The rapper, who later became known for openly showing both strength and sensitivity, never discussed this particular event, and that’s understandable.
Tupac was usually very open about everything, but he never talked about this particular issue, except to say it stemmed from a lack of guidance from his parents, according to Pearlman.
Set, Shakur’s sister, gently asked if he would share his story. She wondered if he’d present it in a boastful way.
His initial experience was disturbing, but the second one made him question what closeness really meant.
Pearlman notes that the second time Shakur visited, he came with someone his mother, Afeni Shakur – a Black Panther activist – knew.
Similar to his initial attempt, Tupac didn’t often talk about it. However, he eventually shared details with a girlfriend named Simi Cruise.
The rapper apparently confessed to Simi that he’d had a sudden infatuation with his mother’s friend, but she didn’t reciprocate his feelings.
She was older than me, a woman and I was just a boy. That experience altered how I viewed sex, making me realize it wasn’t about affection or love, simply a physical act.
As a young person desperately wanting to feel close to someone, it was a really confusing time – I couldn’t always tell the difference between genuinely caring for them and wanting something more. It all felt so mixed up.
At school, Shakur was far from the confident ladies’ man he would later become.
According to Pearlman, Tupac experienced repeated rejection at Dunbar High School, as girls weren’t interested in him.
‘He was short, poor, funny looking, and shabbily attired. A nice guy. And it ate him up.
Despite appearing confident and cool to the world, Tupac felt insecure and unsuccessful with women. He believed he was charming, but felt like no one was interested in him.
His life shifted when he moved to the Baltimore School for the Arts at 14, which a friend jokingly referred to as a place where students were very interested in romance.
There, he would enjoy regular make-out sessions.
Pearlman describes a pattern of casual, intoxicated kissing – different girls at different weekend parties, but not sexual intercourse.
But Shakur soon experienced something deeper: real first love.
He quickly fell in love with Mary Baldridge, a 15-year-old ballerina he acted with in their school play, Firefly.
They fell in love by exchanging letters – some were sweet and gentle, while others were surprisingly intimate.
In a note from February 1, 1988, he discussed intimate details and expressed affection, writing, ‘I think of you! I love you! I am so sore!’
After seventeen days, he admitted he was caught between wanting to be intimate and feeling hesitant. He quickly changed his mind, saying, ‘I’ve been thinking about being close to you, but then I decided we shouldn’t wait!’
After dating for two months, they became intimate, and Shakur was eager to do it again.
‘I can’t wait to make love 2 U again,’ he wrote. ‘I just wanted to tell you how much I love you!’
But their romance fizzled soon after.
Baldridge would later learn Tupac had allegedly been unfaithful for much of their relationship.
‘Still,’ she told Pearlman, ‘the memories are special.’
Stories about Tupac Shakur’s early struggles with love and relationships seem very different from how he was later seen as a confident and successful womanizer – someone connected to celebrities like Madonna and his short-lived marriage to Keisha Morris. However, his complicated connections with women also contributed to difficult times in his life.
In 1994, he was found guilty of sexually abusing a woman, Ayanna Jackson, and received a prison sentence of up to four and a half years. However, he only ended up serving nine months.
Shakur maintained his innocence until his death. Even behind bars, his star power only grew.
In 1995, he made history as the first artist to reach the top of the Billboard 200 chart with an album released while he was in prison – that album was ‘Me Against The World’.
In an interview with NPR, Pearlman explained that Tupac’s difficult relationships were likely caused by feeling abandoned during his childhood.
Pearlman described Tupac Shakur’s relationships with women as deeply sad. He revealed that Shakur had his first sexual experience at the age of 14, and it was with a family member – a cousin.
At age 15, he had a second sexual encounter with a friend of his mother who was an adult.
‘He had no father around, his dad Billy Garland was not around for the vast majority of his life.
You know, it’s fascinating to me how perceptions change. This guy, who eventually became a huge sex symbol, had a really awkward upbringing. He honestly had no idea about relationships or how to connect with people romantically. Growing up, he was a bit of a late bloomer – think braces, a funny walk, and hand-me-down clothes. He wasn’t on anyone’s radar, and girls definitely weren’t lining up! It just goes to show you, confidence and how you carry yourself can make all the difference, and sometimes, the most unexpected people can become incredibly attractive.
According to Pearlman, the singer of ‘Changes’ lived a double life, presenting himself as both a charismatic womanizer and someone who felt like an outsider.
According to Pearlman, his life was full of contrasts – he was both a sex symbol and someone who felt like an outsider, both naive about sex and intensely involved in it.
Shakur’s life was cut short following a drive-by shooting in Las Vegas in 1996.
The shooting happened while Tupac Shakur was a passenger in a car driven by Suge Knight, a well-known record producer, after they had attended a boxing match at a casino.
People who saw the shooting said a white Cadillac drove next to the victims’ black BMW, and the shooter opened fire very quickly.
Tupac Shakur was shot four times – in the chest, arm, and thigh – with a .40 caliber handgun. He passed away from these injuries six days after the shooting.
Despite the case remaining unsolved for many years, Duane ‘Keffe D’ Davis was finally charged with the murder in 2023.
Duane Davis is accused of planning the shooting that killed Tupac Shakur, but he says he didn’t do it. He’s currently waiting for his trial to begin, and if found guilty, he could be sentenced to life in prison.
The Daily Mail reached out to the lawyer representing Tom Whaller, who manages the estate of Tupac Shakur, for a statement.
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2025-11-16 16:35