Mike's Performance Evaluation Ch. 02

"Relax, Michael. I need you to relax your asshole, or I will bring the ginger back out to remind you not to clench."

At the reminder of his unpleasant experience with the ginger, he tried immediately to relax his asshole.

"Bear down, Michael, like you are expelling."

He groaned at the humiliating image, at his entire situation right now. "Please, Miss Jane. No. Please. Not in my ass. I don't know what that is, but I've never had anything up my ass and I can't do this."

She paused. "Michael. I do not want to do anything you truly do not want to do. This is for your own edification. I do not intend to rape you or force you to accept this. If you truly do not want to, then I will stop here. That means not only this insertion, but the entire training. I cannot have you simply picking and choosing what parts of the training you will and won't accept. It is the entire course or nothing."

Mike expected to feel relief at the prospect of no longer being trained by Jane. No more caning, no more ginger, no more insertions. And he did feel some relief. But the dominant feeling was curiosity at wondering what more Jane could do for him, what more she could teach him about obedience and discipline. He lowered himself back onto his forearms, sinking back and spreading his legs for her, signaling that he was ready to submit to her training again.

There was a pause, and then Jane said, "Michael, you realize that by submitting now, you submit to the entirety of the course. I will take this as agreement that you want to continue with your education and that there will be no further complaints from you."

Michael nodded and said, "Yes, Miss Jane. I understand. Please teach me what discipline means and how I can be a better employee."

"Very well, Michael. Relax."

He relaxed his ass and felt the pressure resume. He let out a high pitched whine as the intruder forced its way deeper, stretching the almost untested ring of his anus. He bore down, trying to help the intruder in, and felt it slip in deeper, sliding against his anal walls until it popped into place, giving one last stretch to his anus. He yelped at the sharp pain of the sudden stretching but held his position.

His breathing rasped out as he adjusted to this new feeling of something being seated in his ass. There was a pause, and then the object was slowly tugged out. The feeling of being stretched in reverse made him groan out loud. He felt it pop out and slide easily out of his anus. He felt his anus open a bit as the end passed through the ring.

She showed him the small metallic plug that had just now been up his ass. "We will be training your anus to take larger things. This is only the beginning, to help you get used to the idea of stretching. Not only stretching, but also depth training. You will learn to obey, despite how much it hurts, despite how much it humiliates you, shames you. I want you to learn that pure discipline. Are we clear?"

He whispered, "Yes, Miss Jane." His mind swirled with the implications of what her training would entail.

"Good, Michael. Now, I want you to reach back and hold yourself open. We are going to start your anal training as of today. On each in stroke, I want you to bear down and hold yourself open. On each out stroke, grip the plug as tightly as you can. Do you understand?"

He nodded, and then cleared his throat and said, "Yes, Miss Jane."

"Excellent. Let us begin."

She brought the intruder back to his anus and began pushing in. Remembering her instructions, he bore down, allowing easier passage to the plug, until it was seated all the way in. His anus continued to burn as it stretched unnaturally. She gripped the base and tugged it out, and he clenched his anus down, gripping it tight.

"Very good, Michael," she praised him warmly, and he gripped it even tighter, anxious to please her. As it was about to exit, she pushed it back in, and he relaxed, trying to open his anus to her again. This continued on until his anus no longer burned and the plug slid in and out easily. The pace quickened, until she was rapidly sawing the plug in and out of his ass. He moaned and gripped his ass cheeks tighter, his cock hard with the feeling of the plug rubbing against his prostate with each stroke. He could no longer keep up with gripping and loosening, and simply tried to enjoy the sensation.

Finally, she pulled the plug out, and traced the tiny gape in his reddened anus with her finger. "Nicely done, Michael," she said gently. She reached down and began to stroke his hard cock, teasing the head and gripping the shaft tight. He gasped as she continued to play with his cock. His cock was swollen and hard, and he ached to release.

She reached over and brought her clock so he could see it right in front of his face. "I want you to hold your cum for two minutes. During this time, I will play with you as I feel fit. You will announce to me when you want to cum. Should you cum before you are granted permission, you will lose the right to cum for the rest of the week. Do you understand?"

He nodded.

"Good, the time starts now."

She reached over and started the stopwatch function on the clock. Her movements quickened, and despite her warning of what would happen if he came too quickly, he began to hump his hips into her hand, trying to draw all the pleasure from her tight fist around his cock. It had been so long, so long since he had cum! The pleasure washed over him as he bounced his hips in a frenzy, his mouth agape. He cracked an eye and realized it had not even been a minute, and groaned desperately. He tried to slow his humping, but Jane simply sped her hand movements, trying to draw out his cum.

He moaned and gritted out, "Please, Miss Jane. I'm about to cum. Please, don't!"

It had not even been a minute and a half and her hand sped up, slicking over the head, gripping the shaft in her lubed hand, jerking him off as he cried out, "I can't hold it, please! Please stop, oh god, please!"

He erupted in her hand, his cum splashing the table underneath him, jetting across the surface and leaving a trail. She removed her hand, and he bent his head, defeated. She stopped the clock: 1:52.

"So close, Michael." She smiled at him benignly, and he teared up. "Get up, Michael. Look at my desk and the mess you made on it. I want you to clean it up."

He nodded and slid off the desk, looking at the milky trail of cum that had jetted out of his cock. He reached for the tissue box, and her voice stopped him. "No, Michael. Not with that. I want you to clean it with your mouth."

He paused, trying to process with his cum-fogged brain what she meant. When he at last realized what she meant, a tear dripped out of his eye. He hesitated, the same feeling of shame that had prevented him from trying his own cum before stopping him from this humiliation. He looked up at Jane and saw her staring at him intently. He could almost hear her telling him about what discipline was. He bent his head, and with his tongue, licked up a bead of cum from her desk. The taste was slightly bitter and he made a face as he continued to lick up the warm cum from her desk. The dripping tears from his eyes mixed with the cum until her desk shone with his saliva.

When at last he was done, he looked up, hating himself for debasing himself like this. She raised a corner of her mouth in a half smile, and then cupped his cheek in her hand. "You did a fine job, Michael. I know it was hard, but you are learning what obedience is. You have pleased me."

His own heart lifted a little at that praise, almost effusive by her standards. He started towards his clothes, but she stopped him. She instructed him to bend over, and then he felt the plug being pushed back into his ass. When at last it was seated, she told him to get dressed. He walked awkwardly over to his clothes, feeling the plug filling him and moving with his own movements. She watched him while he dressed himself, wincing as he slipped his boxers on over his welted and plugged ass, how his hands shook as he tried to button his pants and then his shirt.

As he reached over to open the door, her voice halted him. "Remember, Michael. There will be absolutely no cumming this week. If you cum, I shall find out, and you will regret it. That plug is to stay in your ass this week as a reminder of today's lesson unless you need to remove it to use the bathroom. Are we clear?"

He whispered, "Yes, Miss Jane." He opened the door, stepped out into the office area, and walked in a daze to his desk where he sank into his chair. This was going to be an interesting week.