Who's the "lucky" girl? How much force vs. persuasion does Tim use to make her a nudist?
Sarah, the hottest, most popular cheerleader at the school
(This might as well be the same character as the bet-taker, but without that particular storyline.)
In walked the girl herself, Sarah, the captain of the cheerleading team. Tim groaned as Gene just laughed at his unfortunate friend.
Sarah was blonde and athletic, and all the guys and even some of the girls wanted a piece of her. In some sense, Tim's work was already done - Sarah would flaunt her body with crop tops and short shorts, and in that sense she was already "more of a nudist" than her female classmates. Unfortunately, that also imbued her with a special recognition and modesty of the parts of her body that mattered the most.
"Well, looks like I'll be helping you at Orientation," Tim sighed and conceded defeat.
"Bullshit!" Gene didn't want to win so easily - and he wanted to see Tim flail at even talking to the attractive girl, let alone proposing what he had made a bet on. "Go get 'em, tiger!" he slapped Tim on the back as the high schooler had no choice but to walk up to Sarah.
The blonde, for her part, had her legs confidently crossed as her foot bobbed up and down and she scrolled on her phone. Tim walked up to her peripheral vision, twiddling his thumbs as she turned her gaze up to him.
"Well?" she scoffed with annoyance as he rubbed the back of his neck, "aren't you going to say anything?"
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