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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 snogged scantily clad rapper Tokischa Altagracia Peralta, 26, and crawled around on stage as she kicked off NYC Pride weekend with the surprise performance.
The gay icon, 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.
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
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.’
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.
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.
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
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