Britney Spears' Past Virginity Claims Called Into Question Amid Memoir Reveal

Pop star Britney Spears is finally answering the age-old question of who took her virginity.

Although many fans assumed that she gave her V-Card to Justin Timberlake, whom she dated from 1999 to 2002, the now 41-year-old pop star revealed that she lost her virginity before the two had even started dating.

On Thursday afternoon, a source confirmed to Us Weekly that Britney Spears did not lose her virginity to Justin Timberlake. Instead, an insider told the outlet that Britney wrote in her book that the guy she “lost my virginity to” was a childhood friend of her brother, Bryan Spears. Bryan was a 17-year-old senior in high school at the time Britney was a freshman.

In 2003, Britney told W magazine that she had only slept with “one person my whole life,” when talking about “The Social Network” actor. That led many to believe that she had only slept with Justin, but now it appears that the “Toxic” singer is ready to speak her truth.

“It was two years into my relationship with Justin. And I thought he was The One. But I was wrong. I didn’t think he was gonna go on Barbara Walters and sell me out,” she said at the time, referencing Justin’s famous interview on 20/20 earlier that year. When she asked if Britney had “kept her promise to wait until marriage,” the “Cry Me A River” singer burst out laughing.

Elsewhere in her interview with W Magazine, Britney said, “The most painful thing I’ve ever experienced was that breakup,” adding, “We were together so long, and I had this vision. You think you’re going to spend the rest of your life together. Where I come from, the woman is the homemaker, and that’s how I was brought up — you cook for your kids. But now I realize I need my single time. You have to do your own thing.”

Even though he might not have taken her V-Card, an excerpt of “The Woman In Me” published by People magazine revealed that he might have been her first kiss. The singer first appeared on “The Mickey Mouse Club” in 2003. In her memoir, Britney explained that “Being in the show was boot camp for the entertainment industry: extensive dance rehearsals, singing lessons, acting classes, time in the recording studio, and school in between.”

“The Mouseketeers quickly split into our own cliques, divided by the dressing rooms that we shared: Christina Aguilera and I were the younger kids, and we shared a dressing room,” she continued. “We looked up to the older kids–Keri Russell, Ryan Gosling, and Tony Lucca, who I thought was so handsome. And I quickly connected with a boy named Justin Timberlake.”

“[Once] at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me,” she wrote. “A Janet Jackson song was playing in the background as he leaned in and kissed me.”

Britney later described her work on the show as “unbelievably fun,” although she did confess that it was “exceptionally hard work,” with her and her costars expected to practice choreography and routines “thirty times in a day.”

Fans can understand why she didn't say anything about it at the time, but the two made the difficult decision to terminate an unplanned pregnancy in the year 2000, when Britney was only 19. In another excerpt of “The Woman In Me,” released by People magazine on Tuesday, Britney opened up about the "surprise" pregnancy.

“It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated,” she wrote in her memoir. “But Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young.”

“I don’t know if that was the right decision. If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn’t want to be a father,” she continued, adding, “To this day, it’s one of the most agonizing things I have ever experienced in my life.”

Britney Spears’ memoir “The Woman In Me” will be released on Tuesday, October 24, 2023.