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She famously kissed Britney Spears, as well as Christina Aguilera while the trio performed together at the 2003 VMAs.
And on Thursday night, Madonna was at it again as she passionately kissed scantily clad bisexual rapper Tokischa Altagracia Peralta, 26, and crawled around on stage as she kicked off NYC Pride weekend.
Madonna, 63, wore a lace basque teamed with sequin hotpants as she rocked out in typically racy style at the Sandbox show held at Terminal 5 where she was seen simulating a sex act in one of her raciest shows yet.
That’s not Britney, b****! On Thursday, Madonna, 63, snogged a scantily clad Tokischa Altagracia Peralta and crawled around on stage as she kicked off NYC Pride with the surprise performance
Throwback! The moment was reminiscent of Madonna’s famous kiss with Britney Spears, as well as Christina Aguilera, while the trio performed together at the 2003 VMAs (left)
Madonna commanded attention in her skimpy attire, with a cropped safety jacket style over-layer adding a twist, while platform boosts boosted her height.
The icon writhed around in her sexy ensemble, which she completed with fishnets and silver chains.
Madonna later changed into a cleavage baring leather bustier which showcased her pink lace bra.
The singing superstar teamed the busty items with yellow Adidas shorts and a matching cropped sports jacket.
Fabulous: The superstar singer crawled around on all fours during the racy stage show
Sing it! Madonna writhed around while leaning back on the Dominican rapper
Racy! Madonna enjoyed a sexy dance with her on-stage partner Tokischa before kissing with tongues
What she does best: Madonna oozed sex appeal as she performed on stage with Tokischa
Tokischa is a 26-year-old rapper born in Los Frailes, a neighborhood in east Santo Domingo who she met her manager Raymi Paulus of indie Dominican label Paulus Music in 2016.
Of her music, she previously told Billboard: ‘I would say I have a very rock-influenced voice because that’s the type of music I most like. My style is explicit. It [may come off as] morbid but also [it] happiness.’
According to Rolling Stones, Tokischa has become an avator for ‘sexual freedom, queer desire and radical feminism’ while her shows are ‘liberated, raucous spaces, where people let their freakiest freak flag fly.’
The Dominican rapper told the publication last month: ‘I’m very crude with my lyrics, and everything that I’m expressing is very, very, very real. People identify with all of it.’
Madonna has previously teased a collaboration with the rapper, who some commentators have dubbed the Dominican Republic’s Madonna.
Earlier this month Madonna posted a series of photos on Instagram Stories, showing the duo posing with their tongues out at a recording studio, with the caption: ‘A woman’s work is never done’.
Outfit change! Madonna later changed from her all-black ensemble into a cleavage baring leather bustier which showcased her pink lace bra
Sensational: Madonna looked flawless as she crawled across the stage in her fishnet ensemble
Helping hand: The stunning Dominican rapper gave Madonna a hand as she descended the stairs on stage
During 2003’s MTV VMAs, Madonna had a prolonged kiss with Britney during their opening performance for the ceremony.
Britney opened the show by singing Madonna’s Like a Virgin, emerging out of a wedding cake while dressed as a bride, as Madonna did in her 1984 VMAs performance.
Soon after that, Christina joined Britney onstage for the song before Madonna appeared and launched into her single Hollywood. During the performance, Madonna leaned over and kissed Britney.
Teasing a collaboration: Earlier this month Madonna posted a series of photos on Instagram Stories, showing the duo posing with their tongues out at a recording studio, with the caption: ‘A woman’s work is never done’.
Doing her thing: For one section of the show, Madonna slipped into a plunging black blazer
Yas Queen! The singing superstar teamed leather bustier with yellow Adidas shorts and a matching cropped sports jacket
Home time: Following the show, Madonna exited the venue with glamorous black shades shielding her eyes
In 2018 Christina – who was on stage for the kiss – recalled feeling left out of the moment saying her kiss with Madonna just moments later was not shown.
During the broadcast only the image of Britney and Madonna was aired, followed by a reaction shot of Britney’s former flame Justin Timberlake.
‘It was weird. And you know why they cut away for it? Because they cut away to get Justin [Timberlake’s] reaction,’ she said in a radio interview.
Christina went on to elaborate that the manufactured drama was a ‘cheap shot’ as Britney and Justin were no longer an item.
Andy then clarified ‘I don’t think people actually totally realize that she [Madonna] made out with both of you that day.’
She confirmed the sentiment, recalling ‘Yeah, because I definitely saw the newspaper the next day and it was like, ‘Oh, well, I guess I got left out of that’.’
Celebrate: Madonna’s surprise performance kicked off NYC Pride weekend
Work it: The blonde beauty had multiple crosses included in her outfit
Home time: Madonna left in her lace basque teamed with pin stripe shorts and a matching blazer
Who is Tokischa?
Born in Los Frailes, a neighborhood in east Santo Domingo, Tokischa spent her teenage years rebelling against the conservative ideals of her home.
When she was three-years-old Tokischa’s mother left her in Santo Domingo with various relatives to find work in New York. After high school and a childhood immersed in the pursuits of theater and dance, the aspiring star entered what she has called the ‘underworld.’
In between working at a FedEx call center, where she would often showed up high on cocaine or ecstasy, she turned to sex work at the age of 19, entering ‘sugar daddy’ relationships with a string of older men.
She met her manager Raymi Paulus of indie Dominican label Paulus Music in 2016. The photographer and director was looking for a musical artist to represent as a manager and the two began to collaborate in the recording studio.
She has had a string of hits back home, but had never left the Dominican Republic until last year.
As well as her music, the rapper made money during the global pandemic with her explicit OnlyFans content, telling the LA Times in a May 2022 interview: ‘I live off my sexuality right now at this point. I know God doesn’t like it, but he knows I need to hustle and survive.’
In 2021 the rapper and her collaborator J Balvin were widely criticised after the video for their song ‘Perra’ portrayed Black Dominicans from a local neighborhood as dogs. Balvin apologized and took the video down while Tokischa said at the time that she was ‘truly sorry that people felt offended,’ but went on to defend Balvin and said that ‘art is expression.’
Tokischa identifies as bisexual, and her first kiss was with a close friend when she was a teenager. ‘I gave myself liberty,’ she told Rolling Stone. ‘Living with a conservative family, one of the first things they tell you — that the whole world tells you — is that you need to wait, stay a virgin until marriage.’
‘Linda’ and ‘La Combi Versace’, a pair of collaborations with her close friend Rosalia, have become some of her biggest songs.
Earlier this month Madonna teased a collaboration, posting a series of photos on Instagram Stories, showing the duo posing with their tongues out at a recording studio, with the caption: ‘A woman’s work is never done’.
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