She doesn't find him

Anna ran outside in her white skirt and blue tanktop. There was just an hour for her to find the nerdy boy with glasses. She headed to the library, which was surprisingly bereft of boys with glasses. The great hall was similarly deprived, as were the benches by the registrar administrative offices.

An hour and a bit later, she wandered into the cafeteria. It was largely empty, except for one table.

"Sit down, Anna," said the boy with glasses.

"Sorry," she said and hurried to sit down across from him.

"We are not impressed, Anna. I wasn't hiding. Being late for the orientation carries a heavy penalty."

"Eek!"

"But first the ground rules. I am the taskmaster of the game. You will call me ‘Sir’. I will call you whatever I choose, however degrading, and I will treat you however I choose, and do with your body what I choose. That's Rule 1."

"Yes, sir," Anna replied in mock gravity. The taskmaster glared at her. "Yes, sir," she repeated in earnest.

"Rule 2:", the taskmaster continued, "You are not to wear any underwear without express permission. No bras, no panties."

Anna squirmed, uncertain.

"Third: If any person, male or female, makes a sexual advance or sexual request of you, for the duration of the game, you are to oblige, so long as it does not violate the orders of myself or another person running the game."

Anna blushed crimson. Even the tops of her breasts, straining against the tank top, turned a certain shade of red.

"Lastly, you may not have an orgasm without permission. Now that that’s settled, follow me,” said the boy, picking up his suitcase and leading Anna to a secluded booth.

When they sat down, he placed the suitcase on the table. “Now, Anna, you chose to wait overnight and you are late to the game orientation. You should know that there are grave consequences to hesitating and worse to incompetence. Most of the tasks of the game involve a choice.” He opened up the suitcase and showed the contents to her. She saw a small ball, a remote control, and a pair of silver hoop earrings.

“The first part of this task is not a choice. Our contestants are required to wear a remote control egg.” He handed her the small ball. “You will place this in your pussy and leave it there until you are told to remove it.” He then picked up the remote and flipped a switch. The ball started to vibrate in Anna’s hand. She flipped out and almost dropped it. This guy could stimulate her whenever he wanted? He could blow her mind in class? This was frightening.

“Now, here is where you get punished for your hesitation. Originally, there were 16 pieces of jewelry in this suitcase, for 16 contestants. You are the LAST to come to me, meaning you only have two left to choose from. Option 16, the nipple rings.” He picked up the silver loops.

'They weren’t earrings, they were nipple rings?' Anna thought. 'Oh jeez, what have I gotten myself into?'

"And, as punishment, your breasts will be photographed as they are pierced."

'PHOTOS!' Anna thought in panic.

"I wouldn't worry about it too much. Your face won't be in them. Still, by hesitating, you chose it." The nerd went on, "You will have to go out and get your nipples pierced. After you insert the egg, of course. So, my sexy little whore, give me your panties.”

Anna stood up in the private cubicle and hiked up her skirt to hook her delicate fingers into her panties. She then demurely wiggled out the undergarment, taking care to not expose herself to the boy, and handed it to him. He frowned. "Come closer."

She did, at which point he took hold of her skirt and crudely flipped it up to reveal Anna's pussy. She tried to protest, but he only glared and handed her the egg. "Anna, hesitating only makes it worse." Reluctantly, she pushed it all the way into her pussy.

"Good girl. Go get yourself pierced," the taskmaster finished and slapped Anna's ass when she turned to go. "I want everyone to see great photos of your tits."