Question: Who did Chuck Bass lose his virginity to?

Chuck lost his heart to Blair Waldorf but who did he lose his virginity to? In the season one episode Woman on the Verge, Chuck mentions that he lost his virginity to troublemaker Georgina Chapman in the sixth grade.

Did Chuck and Jenny sleep together?

Meanwhile, Jenny goes to Chucks hotel to hang out with Nate but instead finds a sad Chuck drowning his sorrows by getting drunk and Jenny joins him as she is also depressed and has hit rock bottom. Eventually, the two have sex and Jenny finally loses her virginity.

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