Tupac’s Shocking Untold Story of Losing His Virginity

Handsome, magnetic and with a generational musical gift, Tupac Shakur became one of the defining sex symbols of the 1990s.

But behind his swagger and charisma lay a teenage boy who struggled with intimacy — and whose ‘earliest sexual experiences were dark ones.’ 

That revelation is among the many personal details unearthed by sports reporter Jeff Pearlman in his explosive new biography Only God Can Judge Me, for which he interviewed more than 600 people connected to the late rap icon.

According to Pearlman, Shakur’s first sexual encounter came when he was just 14 — with a cousin.

‘Although he would later become a hip-hop sex symbol, Tupac’s earliest sexual experiences were dark ones,’ Pearlman writes.

‘According to conversations he had with a close classmate, and confirmed by his sister, Tupac’s first sexual dalliance had come at age 14, when he had intercourse with a cousin. 

‘The girl was also a teenager, and it only happened one time.’

It was an episode the rapper — who would later become a symbol of raw masculinity and vulnerability — understandably never spoke about. 

‘As the years passed, Tupac — an open book on most subjects — never discussed the situation, save to note it was an offshoot of limited parental supervision,’ Pearlman continues. 

‘Would you talk about it?’ asked Set [Shakur’s sister Sekyiwa ‘Set’ Shakur]. ‘Would you be bragging?’ 

If his first encounter left him shaken, his second would complicate his understanding of intimacy even further.

‘His second time came with a friend of Afeni’s,’ Pearlman adds, referring to Shakur’s mother, Black Panther activist Afeni Shakur.

‘Like his first try, Tupac rarely discussed it. But he later confided in a girlfriend, Simi Cruise.’

The rapper reportedly told Simi: ‘The next day I thought I was in love with my mom’s friend. And she ignored me. 

‘She was a woman, I was a boy. That changed my way of thinking about sex. It wasn’t love. It was just sex.’

For a teenager yearning for connection, the experience blurred the lines between affection and desire.

At school, Shakur was far from the confident ladies’ man he would later become.

‘At Dunbar, Tupac had faced a steady string of rejections. Girls simply didn’t take an interest in him,’ Pearlman writes.

‘He was short, poor, funny looking, and shabbily attired. A nice guy. And it ate him up. 

‘For all the outer-leaning swagger, with the opposite sex Tupac felt like a loser. He knew he had game, only nobody wanted to play it.’

Things changed when he transferred to the Baltimore School for the Arts aged 14 — described by one friend as a ‘horny school.’ 

There, he would enjoy regular make-out sessions. 

‘Not sex, but drunk and/or high party make-outs. One girl one weekend. Another a different weekend,’ Pearlman writes. 

But Shakur soon experienced something deeper: real first love. 

He fell hard for classmate Mary Baldridge, a 15-year-old ballerina with whom he performed in the school’s production of Firefly. 

Their romance unfolded through a series of passionate love letters — some tender, others shockingly explicit.

In one note dated February 1, 1988, he wrote about his genitals, adding ‘I think of u! I love u! I am so sore!’

Seventeen days later, he confessed: ‘I’m so preoccupied with thoughts of making love… I don’t think we should do it yet! I changed my mind, we should do it!’

Two months into their relationship, the pair finally slept together — a moment Shakur couldn’t wait to relive. 

‘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.’

The tales of Shakur’s early sexual confusion and heartbreak stand in stark contrast to his later reputation as a hip-hop lothario — a man linked to Madonna and actress Keisha Morris, whom he briefly married. But his complex relationship with women also led to darker chapters. 

In 1994, he was convicted of first-degree sexual abuse against a woman named Ayanna Jackson and sentenced to up to four and a half years in prison — though he served just nine months.

Shakur maintained his innocence until his death. Even behind bars, his star power only grew. 

In 1995, he became the first artist ever to have an album debut at No 1 on the Billboard 200 while incarcerated — Me Against The World. 

Speaking to NPR, Pearlman said Tupac’s troubled relationships stemmed from an upbringing marked by abandonment.

‘It’s heartbreaking,’ Pearlman said of Shakur’s experiences with women. ‘He was 14 years old when he had his first sexual experience, and it was with a cousin. 

‘When he was 15 years old he had his second sexual experience and it was with an adult friend of his mother.’

‘He had no father around, his dad Billy Garland was not around for the vast majority of his life. 

‘He never learned about sex, never learned about how to treat people in that way. And he became this guy known as a sex symbol but throughout his youth, throughout middle school, and much of high school, he was a kid with gap teeth, really bad braces, he walked like a duck, he wore thrift store clothes. He was not a guy the women were interested in.’

The Changes singer straddled two worlds – one in which he was a Don Juan, and another in which he was ‘an ugly duckling,’ according to Pearlman. 

‘And his whole life was kind of a yin and yang, of being a sex symbol, being an ugly duckling, being a guy who didn’t understand sex, being a guy who dove into sex,’ Pearlman added. 

Shakur’s life was cut short following a drive-by shooting in Las Vegas in 1996.

The shooting took place while Shakur was being driven by notorious record producer Suge Knight after watching a boxing match at a casino. 

Witnesses described seeing a white Cadillac pull up alongside the pair’s black BMW – from which the assailant then carried out the shooting in a matter of seconds.  

Shakur was struck in the chest, arm and thigh by four .40 caliber rounds fired from a pistol. He died in hospital from his wounds six days later.

For years, no one was arrested for the death – but in 2023 Duane ‘Keffe D’ Davis was charged with the murder. 

Davis has been accused of orchestrating Tupac’s fatal shooting but maintains his innocence. He is still awaiting trial. If convicted, he could spend the rest of his life in prison. 

The Daily Mail has contacted lawyers for the executor for Shakur’s estate, Tom Whaller, for comment.