Durand Bernarr, a trailblazing queer musician, shares his "My First Time" story on work ethic he learned by touring with Earth, Wind & Fire.

'Spider- Man' actor Shameik Moore got honest with us for "My First Time" about the first time he slung his web, if you know what we mean.

Wu-Tang brainchild RZA shared his "My First Time" story on how the "Wu-Tang Financial" skit from 'Chappelle's Show' made for his TV debut.

R&B vet Bobby V has a way with fans, but in his "My First Time" story it was one fan who had it her way by pulling his pants down on stage.

Rap's latest freshman Tia Corine has her foot on the game, but it was her ankle doing the damage as a kid in this funny "My First Time" story.

'Real Housewives' all-star Cynthia Bailey tells us for "My First Time" her story of finding first-time love with actor Leon.

Pop queen Madonna shocked the world on GRAMMYs night by tongue-kissing rising singer/songwriter Jozzy, and now we have the full story!

Issa Rae explained for our latest "My First Time" how YouTube raps, paired with liquid courage from Moscato, led to her Hollywood takeover.

25-year-old burgeoning rap star SleazyWorld Go gives us his "My First Time" story on what debut viral success was like with "Sleazy Flow."

Budding rapper Sukihana is as unfiltered as they come, and she spoke of her love for Jamaican massages in our latest "My First Time" story.

Kaliii is Billboard's latest rap star that has the world watching, and she told us her "My First Time" story of when the viral craze began.

For a quick round of "My First Time," Toosii reflects on learning how to play the room based on a tour experience with Summer Walker fans.