Madonna's original 'boy toy': Insiders reveal intimate new details about decades-younger lover she 'stole' from friend… her insatiable demand for sex… and the night he faced Sean Penn's jealousy

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By EILEEN RESLEN, US SENIOR SHOWBIZ EXCLUSIVES REPORTER

Published: 21:41 EDT, 2 August 2026 | Updated: 12:48 EDT, 3 August 2026

Wearing a cleavage-baring corset and knee-high metallic boots, Madonna took center stage at the FIFA World Cup halftime show in front of thousands of fans in July.

Among those in the stands was her much-younger boyfriend of two years, Akeem Morris, 30, who cheered on the 67-year-old pop icon alongside her kids – most of whom are closer to his age.

While some struggle to make sense of their nearly 40-year age gap, for Madonna, a May-December romance is nothing new. In fact, it's been her preference for decades.

Because before Morris or even her first child's father Carlos Leon, there was Bobby Martinez.

Martinez's name does not often appear in Madonna's documented dating history, but according to sources, he made a profound impact on the Material Girl.

In the early '80s, the rising pop star met the rough-around-the-edges 'street kid' when she moved to New York City and they snuck around together for years.

Over the years, Madonna has dated several men who are decades younger than she is

The 67-year-old pop star's most recent boyfriend is 30-year-old Akeem Morris, seen above wearing a black New York Mets hat and Adidas shirt

Morris and Madge have been dating since 2024

Martinez was a handsome young man of Puerto Rican descent who came from a humble upbringing on the Lower East Side of Manhattan.

But in his teen years, he got a taste of Hollywood when he landed a part in a movie called Mixed Blood, which had recruited young locals for filming in the Big Apple.

'There was a lady who was basically going to these people living on food stamps, giving them a chance to make some money as an extra in a movie,' the film's casting director Leonard Finger told the Daily Mail.

The recruiter was Lupe Garnica of CHARAS/El Bohio, a non-profit cultural and community center organized to give disadvantaged youths a better life. Martinez, who was also known by his graffiti artist name 'RP3,' was cast in a non-speaking role.

According to Finger, Madonna was never seen on the set of the dark crime comedy, but Martinez had reportedly started getting close to the singer around that time.

Sometime around 1983, the teenaged graffiti artist was introduced to the songstress via legendary artist Keith Haring, a close friend of Madonna.

'Bobby - in his day - was like this absolutely gorgeous poster boy for what Keith’s ideal was. Madonna’s taste for young men at the time was exactly the same as Keith’s. Young, Puerto Rican, hot, straight boys,' Gil Vazquez, Haring's longtime friend and former executive director of the Keith Haring Foundation, told the Daily Mail.

'So what happens? Madonna enters the picture. The way Keith would tell the story is that Madonna "stole Bobby" from Keith,' he added. 'It’s hard to blame Bobby - it was Madonna. She’s the hottest pop star in the world.'

Sources gave Daily Mail exclusive insight into Madonna's original 'boy toy,' Bobby Martinez

Martinez, far right, was still a teenager when he hung out with Madonna, according to sources

At the time, Madonna was about 25 years old and her star was already on the rise, with hits like Borderline and Lucky Star climbing the pop charts. And while there is some debate as to exactly how old Martinez was at the time, multiple sources agree that he was likely in his mid-teens.

During a 2015 Ellen DeGeneres Show interview, in which she discussed courting younger men, Madonna admitted: 'When I moved to New York, I dated a 16-year-old.'

DeGeneres quickly interrupted and said, 'That was when you were, like, 18,' with a big smile on her face. Madonna looked away and said in response, 'Yeah. Um, anyway.'

In a February 1983 interview with the Record Mirror, Madonna also spoke about her preference for 'effeminate looking men and young boys.'

'There are a lot of very sweet Puerto Rican boys where I live and if it outrages people when we go out together, that's fine by me,' the then-24-year-old told the magazine. '15- or 16-year-old boys are best and I like smooth thin men who aren't afraid to show their emotions and cry. I want to caress a nice smooth body, not a hulk.'

Vazquez told the Daily Mail of the questionable age gap between Madonna and Martinez: 'I can’t say with any certainty about how old anyone was at that point.

'Going out in the '80s - we look at it a lot differently now than we did then. These kids were going to, like, nightclubs. Certainly not old enough to drink at that point. That was just sort of par for the course in New York City in the '80s, it just was.'

But what is certain is how much Madonna enjoyed Martinez's company.

Archival footage taken in 1984 from the set of Desperately Seeking Susan, in which Madonna landed one of her first big acting roles, showcased the entertainer walking around with Martinez standing closely behind her.

Dressed in a tight white tee and jeans, he could be seen puffing on a cigarette and speaking softly to Madonna. At one point, they went into her trailer and then walked out onto the New York City streets together for a stroll in-between scenes.

Martinez is not credited for any parts in the crime-thriller, so it appears he was only on set to be by Madonna's side.

That same year, the pop superstar continued to ride the wave of success with her hit single Like a Virgin. And when it was time to film the music video, she chose the now-iconic all-white look that featured a very telling accessory: a belt that read 'Boy Toy.'

New York-based graffiti artist Cost, who personally knew Martinez, once told the blog Vandalog: 'If you look at her old videos, she used to wear a belt buckle tag around her waist that said “BOY TOY.” Boy Toy was that guy RP3. He used to write Boy Toy and RP3, and that was her boyfriend at that time.'

Madonna even brought Martinez to the set of her film Desperately Seeking Susan in 1984

Archival footage showed the pair walking around together as Martinez puffed on a cigarette

Madonna wore a 'Boy Toy' belt in her Like a Virgin music video. The accessory was reportedly a secret homage to Martinez, her young lover at the time

Madonna's good friend, the late Andy Warhol, also chronicled the singer's rendezvous with Martinez – and even suggested she allegedly had an affair with him.

He wrote in the Andy Warhol Diaries: 'Madonna arrived and she had just seen Paul [Morrissey]'s movie Mixed Blood because that friend of hers is in it. Bobby.

'She said she was so relieved her husband Sean [Penn] wasn't with her so she could really have fun.'

Madonna and Penn had met in January 1985 while filming her Material Girl music video. They tied the knot just a few months later, in August, and the Mixed Blood premiere was shortly after, in October.

According to a 1991 Seattle Times report, citing an excerpt from Christopher Andersen's book, Madonna Unauthorized, Penn would become enraged over Madonna's alleged infidelities, as she 'did not stop seeing her old friends and lovers.'

'One night a jealous and intoxicated Penn stalked Madonna's old boyfriend Bobby Martinez with a gun,' the report further claimed.

'I was at the Palladium,' Martinez – who was interviewed for the book – reportedly stated, 'and I heard that Sean was looking for me.

'He walked up to the deejay and I was right behind him, but it was dark and there were a lot of people and he didn't see me. When he pulled back his jacket, I could see he had a gun. And he looked really nuts, man. So I got the hell out of there.'

Penn does not appear to have addressed the allegations when they first came out, and his representative did not return the Daily Mail's request for comment.

However, in a 2015 defamation trial for a lawsuit Penn filed against director Lee Daniels, Madonna testified that her ex-husband never physically abused her, quieting claims he was a violent individual.

Penn and Madonna's tumultuous marriage came to a halt when the latter filed for divorce in 1987. It was finalized in 1989.

Madonna then began dating her co-star Warren Beatty, whom she met on the set of Dick Tracy in 1989. But Martinez, we're told, never fully went away.

Madonna has always been very open about her sexuality and even released a book called Sex 

Insider Gil Vazquez told the Daily Mail that Madonna allegedly dated Martinez even while she was already 'hot and heavy' with her Dick Tracy co-star Warren Beatty

Madonna and Penn had met in January 1985 while filming her Material Girl music video 

'By the time I saw Bobby and Madonna together - this is now '88, '89 - and Madonna is hot and heavy with Warren Beatty,' Vazquez told the Daily Mail before sharing that they had all met up for dinner one night with Haring and stylist Maripol also present.

'They were canoodling,' Vazquez recalled of Madonna and Martinez. 'It was the sort of body language two people have when there’s intimacy. They’re close together; they’re acting in a very familiar way as if they’ve had a longstanding relationship.'

Beatty's representative did not return the Daily Mail's request for comment.

In his interview for Andersen's book, Martinez himself described the spontaneous and sexual nature of his relationship with Madonna.

He said, 'We would get together at clubs, or we'd go to hotels. If she wanted to have sex, she'd say, "'Let's go f*ck," and we did.'

Vazquez told the Daily Mail, however, that Martinez no longer looked like the 'cute boy' that had the New York City social scene buzzing at the start of the decade.

'He looked like he had been through a few things. He was a little worse for wear,' the ex-executive director explained. 'I almost feel bad for saying that because I don’t know if he struggled with drugs or alcohol, but that to me is what sort of came across the most. He looked just really ordinary.'

Vazquez continued, 'He wasn’t strikingly beautiful at that point, like, he obviously was in ‘83 and ‘84. He looked almost too ordinary to be hanging out with Madonna. Bobby [was] not going to be the public arm candy.'

Part of the reason Martinez was able to remain an elusive character over the years was because he wasn't photographed with Madonna at award shows or red carpets.

But behind closed doors, Vazquez said they certainly 'acted like a couple.'

Haring's longtime pal said it seemed as though Madonna and Martinez felt comfortable showcasing their affection at the dinner he attended because they were among a 'trusted' group of friends.

'She felt safe. And in New York, she could kind of hide. She could walk down the street and people wouldn’t attack her. It’s a very close circle,' Vazquez said.

That dinner was the last time Vazquez saw Martinez and Madonna together.

Shortly after, their mutual friend Haring died from AIDS-related complications in February 1990 and Martinez's life became somewhat of a mystery.

A New York City local, who often ran into Martinez at parties throughout the '80s, told the Daily Mail that many in Haring's crew were tragically 'getting sick and dying.'

'They were all dropping like flies. Some people disappeared, some people got sick. This Bobby kid, he wasn’t famous. Anything could have happened to him,' they said.

Martinez was a very elusive character and his life was a mystery. A graffiti artist named Cost claimed in a 2012 blog that Madonna's ex-lover allegedly died of an overdose years ago

Madonna initially met Martinez through Keith Haring, seen above. According to Vazquez, the legendary artist claimed the pop star 'stole Bobby' from him

A source told the Daily Mail of the Queen of Pop's May-December romances, 'Believe it or not, from what I hear, they are all totally into her, and they worship her'

Cost disclosed in his 2012 blog interview, though, that Martinez did pass away.

'He ODed [overdosed] and he’s been dead for a long time,' the street artist claimed.

It's unclear whether Madonna shared any heartfelt goodbyes with her former lover.

In more recent years, the Vogue singer has had relationships with men who bear a striking resemblance to Martinez.

Madonna dated Leon, who is eight years younger than her; Jesus Luz, 39, Brahim Zaibat, 29, Ahlamalik Williams, 31; Josh Popper, 32, and most recently, Morris.

'She's just been on this long string of guys that are decades younger than her, gorgeous. They're all, like, supermodels. And believe it or not, from what I hear, they are all totally into her, and they worship her,' a second New York City insider said.

'She wants guys that massage her feet, that wait on her hand and foot, that, like, bring her flowers on a daily basis, even if she pays for it, she doesn't care. They have to bring it to her - and sex on a daily basis.'

Madonna, who penned a book titled Sex and released an album called Erotica, told the Daily News in 2015 that she found men her age to be undatable.

'I’m a very adventurous person and I also have a crazy life,' she said.

'I mean, you have to be pretty open-minded and adventurous to want to step into my world. People who are older, and more set in their ways, are probably not as adventurous as someone younger.'

Vazquez, like many sources we spoke to, defended Madonna's taste in younger men – even though it 'ruffles a lot of feathers.'

'Madonna has always behaved in ways that have been acceptable for men for decades,' he said. 'So the 60-year-old man dating a 24-year-old woman, it’s par for the course for a rich, powerful man, but if she does it, it’s taboo.'

The Daily Mail has contacted Madonna's representatives for comment.

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