Reg Jones
Britney Spears with Reg Jones, the man (boy) who Us Weekly claims (in a November 2007 issue) that popped Britney's cherry (if you know what we mean) at age 14. We mean Reg Jones was the first person to ever have sex with Britney Spears, who was 14 at the time she gave it up. Woo.

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Photo Credit:
Us Weekly
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