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In 2006, Spears guest-starred on the Will & Grace episode "Buy, Buy Baby" as a closeted lesbian. Spears announced her second pregnancy in May 2006 during an appearance on The Late Show with David Letterman.^[89] She also appeared on Dateline the next month to discuss tabloid rumors about an impending divorce, and motherhood. She addressed an incident which occurred in February when photos revealed her driving with her son unrestrained in her lap,^[90] explaining, "I see a bunch of photographers and I’m scared and I want to get out of the situation... They’re coming up on the sides of the car which is a scary situation for me… so I get my baby out of the car and I go home."^[91] The month following the televised interview, Spears posed nude for the August 2006 cover of Harper's Bazaar.^{britney spears porno pics id="cite_ref-91" class="reference">[92]}^[93] Just two days before Sean's first birthday, Spears gave birth to her second son, Jayden James Federline on September 12 in Los Angeles.^[3]

In July 2004, Spears announced her engagement to Kevin Federline, three months after they met. Federline had recently been in a relationship with actress Shar Jackson, who was eight months pregnant with their second child.^[82] These initial stages were chronicled in Spears's first reality show Britney & Kevin: Chaotic, which aired on UPN in May and June 2005.^[83] On the night of September 18, Spears married Federline in a surprise, non-denominational ceremony at a residence in Studio City, California, filing legal papers on October 6.^[84][85] After the marriage, Spears announced via her website that she would be taking another career break to start a family. She gave birth to her first child, Sean Preston Federline, nearly one year later, on September 14, 2005 in Santa Monica, California by a scheduled caesarean section.^[2]

In March 1999, Tamara Conniff of Entertainment News Wire reported: "Only a few years ago, Spears was a Mouseketeer on the Disney Channel's "Mickey Mouse Club." Now, she's a 17-year-old pop superstar with a No. 1 album, a double-platinum single and a provocative video in heavy rotation on MTV. Spears's debut album and its title track, "... Baby One More Time," have taken the music world by storm".^[25] Spears commented, "My main goal is just to make good music...And since I am so young, I can grow as an artist each time and hopefully be britney spears pussy a legend or something, like Madonna".^[25] By April 1999, Spears was described as "the Reigning Princess of Pop" by the Orlando Sentinel.^[26]