The Voice Of My Descent

This night was never going to end, Jules thought miserably as she tried yet again to insert the dry erase marker into her tiny virgin asshole. She had been at this task for almost half an hour and it just seemed so fucking impossible!

"How can he actually expect me to do this EVER!? Much less in 30 minutes!" she muttered in frustration.

But even in the midst of her turmoil, Jules knew she had no one to blame but herself for her humiliating predicament. At first she had tried to blame her poor judgment (understatement of the century) on 20 years of unmet sexual needs in a marriage that otherwise was good. Then she had reasoned it was just a midlife crisis, spurred by years of giving everything she had of herself to everyone but herself. She had been a faithful wife, a loving mother and a dedicated teacher. That last part stung the most, given her current location for these acts of debauchery.

"Ding" she glanced down at her phone message:

"Little slut...times almost up. You don't want to disappoint me again, do you?"

No. She absolutely did not want to disappoint him. She had learned that lesson very quickly.

She wet the end again with her mouth, tasting the bitterness of her own ass but not allowing herself time to dwell on it, and reached behind her, once again placing the end at her hole entrance. She began to push and twist the marker, trying to breathe through her pain and allow the foreign object to slide up inside her. Suddenly she felt a stabbing pop as the marker forced its way past her tight little sphincter. She paused to give herself a moment to adjust to this new sensation.

"Breathe Jules," she whispered as she tried to relax. The pain began to subside and she gently, slowly began pushing the marker up inside her ass.

"Ding" she looked at her phone again. "Times up. Where's my video Jules? I'm ready to see you bent over that desk with your slutty teacher ass all stuffed up with that fat sharpie, fucking yourself really good with it."

Holding the marker still in her ass with one hand, Jules quickly switched her phone to camera video mode, placed it angled up on her office chair behind her as he had instructed, and pressed record. She frantically turned back around and bent over her her desk again, beginning to pull the marker out a little before shoving it back in again. It hurt, but the worry over how much more pain would result from failing at this task spurred her on. She couldn't help but let out a little whimper as she continued to humiliate herself by fucking her own ass in the middle of her empty classroom. Five minutes he had said. After about a minute, her ass was adjusting and she no longer had to focus all her attention on relaxing through the pain. This freed her mind to think about what he was going to see when she sent him this video. God she must look like such a whore. She could almost see the headlines now "Teacher Slut Fucks her Ass raw in Classroom" Jules glanced behind her to see how much time was left. Two minutes to go. As these thoughts continued to run through her head, Jules began to notice a very subtle, yet disturbing change. The initial pain of having something crammed up her ass was beginning to morph into something very different.

"This is not happening! THIS CANNOT BE HAPPENING! Jules thought with dread as she felt a familiar pressure began to build between her legs. As she lay over her desk panting, she could feel her little pussy start to drip. As if her body was under some external control, she began to really fuck her ass deep with that marker- just like he had told her she would do for him.

"Ohhh God Nooo..." She heard herself moan outloud.

She was trying desperately to hold on to her anger and embarrassment so she could avoid producing the conclusive evidence that he was right. But suddenly the truth hit her with a certain clarity. He WAS right. Everything he said about her was true. She was a filthy, slutty little whore who needed to be controlled, used, and degraded.

And it was with that final moment of truth her internal struggle was over and she let go. "Oh my God I am such a SLUT!" She screamed as she gripped the desk tight with both hands and felt her soaking wet pussy spasm over and over again in what had to be the most intense orgasm of her life.

She laid limp across her desk..too spent to even attempt to remove the marker from her ass.

As she began coming back down from that momentary high, the only thought she had left was that she had just lost any and all hope of freedom. She knew she was his now. And once she sent him this video, he would know it too.

"Ding!"

"Times up bitch!"