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Selena Gomez and Justin Bieber-Selena Gomez lost her virginity to Justin Bieber. Some of his songs are dedicated to her. 
Beyonce and Jay Z -The singer said she only had a boyfriend before her husband Jay Z, but as they were very young were only dating. So it is assumed that Beyonce lost her virginity to Jay Z. 
Kim Kardashian and TJ Jackson -Reality star allegedly lost her virginity to TJ Jackson, nephew of Michael Jackson. 
Taylor Swift and Jake Gyllenhaal -The singer lost her virginity with Jake Gyllenhaal and the Red album is about her experience with him. Apparently Jake Gyllenhaal is quite seductive … 
Kirsten Dunst and Jake Gyllenhaal -Kirsten Dunst lost her virginity in 2001 with Jake Gyllenhaal, when she was in her twenties 
Kristen Stewart and Michael Angarano -Kristen Stewart lost her virginity at age 14 with actor Michael Angarano. They were together 4 years. 
Miley Cyrus and Liam Hemsworth -The couple was together for about four years 
Mila Kunis and Macaulay Culkin-Mila Kunis had lost her virginity to the actor of “Home Alone”. They were in a relationship of seven years when they were adolescents. 
Britney Spears and Justin Timberlake -The singer said she would remain a virgin until marriage, but then her ex-boyfriend Justin Timberlake allegedly confessed that they had had sex while they were together. Later, Spears admitted that she had sex with the leader of N’Sync. 
Vanessa Hudgens and Zac Efron -Vanessa Hudgens lost her virginity to her co-star Zac Efron, who was her partner for five years during the popularity of “High School Musical”.