Chapter 5

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Dare Devil

With Blair's boyfriend Nate helping to close up the family yacht for the season, Blair is free to focus on the most important event of the Fall: her annual sleepover. A tradition since the year 2000, each one more decadent than the last. No expense—or reputation—is spared. With everything from trundle beds to truffles in place, all that's missing is sleepover stars and Waldorf BFFs, Serena van der Woodsen and Anna Hawthorne.

Anna arrived at Blair's home just before 7pm for her annual sleepover. Serena had skipped out due to a date with a certain Dan Humphrey and after cancelling their last one due to Blair's photoshoot Anna could tell Serena was really excited for this one.

Anna took her seat in one of the chairs that occupied Blair's living room and allowed the pedicurist to begin her work. 10 minutes later Jenny Humphrey entered the room.

"What is she doing here?" Anna asked as she turned to Kati, who was sat beside her.

"You didn't hear? Blair invited her because Serena ditched us." Kati explained as her manicure was drying.

After the nails and toes were done everyone got changed and began drinking their martinis.

"Who's ready for a game of truth or dare?" Blair asked the girls in her living room as they all took a seat.

"Oh I love truth or dare. Once I had to eat an entire bag of marshmallows." Jenny replied innocently smiling as she held the untouched martini.

"That's nice, little Humphrey, but that's not how we play." Blair told her.

"Well how do you play?" Jenny asked confused. Blair dared Kati and Is to make out and to say it shocked Jenny was an understatement.

After a couple more rounds Jenny's phone beeped on the table and before she could answer is Blair picked it up and opened it.

"S.O.S, still in prison" Blair read out from Jenny's phone.

"Hey isn't that Eric van der Woodsen. I thought he went home for the weekend." Anna spoke confused as she saw the picture of her best friend's younger brother on the Brooklyn girl's phone.

"Is, why don't you take the girls to Viscounti. Meet you there in an hour." Blair told them and the four girls left leaving Blair, Anna and Jenny alone.

"Let's ramp this up, shall we? Truth or dare." Blair asked Jenny as she stood up next to Anna, who was already on her feet. "Oh and you've already used up your truth."

"So dare?"

"I dare you to jailbreak Eric." Blair spoke casually.

"Blair, she can't." Anna told the other brunette.

"It's perfect. She wants in and he wants out." Blair told her best friend before looking back to Jenny.

"What's it gonna be? Do or die, Little J." Blair spoke to the blonde who was looking back at her.

"Let's do it."

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Anna called Richard who brought the 3 girls to the Ostroff Centre to rescue Eric from his prison.

Royalty // Chuck BassWhere stories live. Discover now