Read Story: SEASON 1 EPISODE 31

That night got tougher yet again. The plug got bigger. It felt twice as heavy and the head measured about two full inches in diameter. Before attempting it, she decided to go back and try the first butt plug again and see how it felt now. Unsurprisingly, it popped in pretty easily. Same with the next two. Reluctantly, she knew she needed to get on with her new torture, she started working the new plug into place.

She took her time to loosen herself up. She got it almost all the way in before it started to hurt. She took a breath, relaxed and eased it the rest of the way. She got the normal hit of pain at the widest point and wondered for the hundredth time how she would possibly be able to take a dick in her ass. His dick in particular made her shudder at the thought.

Determined to not make the same mistake as the night before, she decided on just fingers to tease her pussy and she wouldn't pull on the plug at all. She rubbed and it felt good, hating the act of denying herself. She just didn't know if she could hold it off anymore so didn't take it quite as far. She stopped every time it started to feel good, leaving it to only a tease, while groaning for the camera to make it look good. She sent off her video and continued her cycle with the butt plug. "Only one more day to go." She reminded herself with a sigh of relief.

Finished playing with herself for the night, with the toys away, she focused on finishing her homework. With only a few problems left, her phone sounded, and she checked her texts. Mr. Michaels had sent, "You didn't follow your instructions, did you? You didn't push yourself to an orgasm on your last masturbation."

She had moaned and thrashed her body slamming her fists into the bed in frustration. She had rubbed her clit and it felt great. But he had caught her.

She didn't push herself to the point of no return and had held back. She saw no point in lying. "No sir. Sorry sir." She thought about explaining how hard these two days had been and how her pussy just couldn't take it, but she knew that would be pointless.

She didn't receive a response for about fifteen minutes. She bit her nails waiting and checked her phone obsessively. Finally it came,

"Tell Conner tomorrow that you want him and one of his friends to come over after school tomorrow so that you can blow them both.

Give both boys a blowjob. You are not allowed to fuck them and they are not to touch your pussy. And swallow it all like the good cum guzzling slut you are."

"Fucking hell," she whispered as a cold sweat broke out on her brow. When would she learn her lesson? If she didn't follow instructions, then there were always repercussions. She had failed again. And now she had to be an even bigger slut. Two boys at the same time?? And how would she keep them from fucking her? She paced the room until she decided on an approach to handle it. She sent Conner a text to meet her before the first class.

In the morning, she didn't mess around. She got the dildo out and used it on her pussy. She fucked herself hard and shook when she stopped with her body begging to cum. She gushed onto the sheet. Her clit felt like a grape it had swollen so much. She showed her annoyance for the video, and even muttered how much she hated this challenge. She sent it off and then regretting saying anything, but had other things to worry about.

She got dressed and got to school and found Conner about ten minutes before the first class. "I have something I think would be fun," she started coyly. "Are you up for some fun?"

"After last time, absolutely!"

"I keep thinking about that great dick of yours and I want to blow you again sooo bad. She played it up and Conner loved it. "Buuuut, I want to do something extra naughty. Do you want to do something..extra..naughty with me?" She drew out the 'extra' and leaned into him.

Conner looked like an overexcited puppy dog, "Hell yeah! What did you have in mind?"

"I want you to pick one of your buddies. One that can keep a secret just like you. I want you to both come over and I will blow both of you! What do you think about that?" She gave him her best puppy dog eyes.

"Both of us? Really?" he pondered mystified. Once again, she clearly had surprised him. "Why two of us?" he asked.

"Well, you know I like blowing you, right?" He nodded. "And I'm pretty good at it right?" He nodded again while raising his eyebrows and smiling big. "So just think two would be twice as fun. And it will give me that much more practice to suck you dick perfectly next week as well." He rolled his eyes but she had clearly hooked him.