It had been a week since his first performance evaluation and training session. The department was empty, as most everyone had either left on time to start the long weekend early, or taken today off entirely. Mike closed the last file on his desk, leaned back in his office chair, and sighed deeply.
Since his first and only training session a couple of weeks ago, he had only seen Jane in passing. Probably a good thing, he thought, shuddering a little. She had never looked happy when he saw her, usually stomping around with a thunderous expression on her face as she glowered at workers who had the nerve to step inadvertently in her way. Mike had been on the receiving end of those glares once or twice, and he had quickly sidestepped her when she was in those moods. The last thing he wanted to do was give her more ammunition for his next training session, whenever that was. So far, he hadn't been summoned to her office, and he mentally crossed his fingers that his performance had so far been satisfactory that he wouldn't be called back. He closed his eyes, hearing again the ominous "zzzzip" noise of the pointer whistling through the air and then the loud crack as it made contact. He shivered. He couldn't forget that noise, or the white hot feeling of the pointer branding his ass.
It had taken all of a week for most of the darker bruises and welts to fade, changing from a deep purple interspersed with fuschia blossoms to a sickly yellow green. He had made excuses to his girlfriend all of that week of why they couldn't have sex. His girlfriend had been immediately suspicious and hurt, wondering why he, who normally couldn't get enough sex, suddenly was feeling celibate. He had tried to appease her fears, but how could he explain that his ass was a welted mess and his boss had put her fingers up his asshole and stroked his cock and made him cum all over her desk, screaming as he did so? How could he possibly explain to his girlfriend that that orgasm had been better than what she could give him? Instead, she had become angry and left. It had been a sexless week since her storming out of his apartment.
His eyes popped open as his email dinged. Only one single sentence: "Come to my office, please." Without even looking at the sender, his stomach dropped. There was only one person who had an office who was still here after six on an evening before a long weekend. He stumbled to his feet and walked down the hallway to Jane's office. The door was shut, and he knocked hesitantly. He waited, but no response came. He stood there awkwardly, wondering if maybe he had gotten the wrong office after all. Just as he was about to leave, a muffled "Enter!" came from behind the door.
Mike wiped his sweaty palms on his pants and opened the door. Jane was behind her desk, her desk lamp on, reading a thick stack of reports. She didn't even look up as he entered her office, and only said, "Shut the door" as he walked over the threshold.
He quietly closed the door, the latch clicking into place. "Lock it," were the only other words she spoke.
He turned to the door, his breath catching. Almost involuntarily, his hand reached up and turned the lock. He heard the bolt slide into place and he turned to face her. He walked up to her desk, standing in front of her as she kept reading. He shifted from foot to foot, wondering why she had summoned him there if she was just going to read.
Suddenly: "Michael. Stop shifting. You're giving me a headache. From now on, when you come to my office, you will close the door, lock it, remove all of your clothing, fold them neatly and put them on the chair, then come stand in front of me with your hands on your head. You are not to shift your weight, but to stand there with good posture and hold your position until told otherwise. Is that clear?"
He nodded, and then realizing she hadn't even looked up at him to issue those commands, he cleared his throat and muttered, "Yes, Miss Jane."
"What?" she barked at him. "I can't hear you."
Again, he said louder and more clearly, "Yes, Miss Jane!"
He stood there, feeling a little foolish about how loud he had raised his voice. At last, she raised her head and stared at him with annoyance.
"Didn't you hear me, Michael? What did I just tell you?"
"I'm sorry, Miss Jane. You said, um, when I come to your office, I should close the door, lock it, and then take off my clothes and stand in front of you with my hands on my head."
She looked at him impatiently, and he realized with a start that she meant for him to do it now.
Feeling foolish, he started removing his clothes with shaking fingers. He unbuttoned his shirt, shrugging off the button-down and lifting the undershirt over his head. His hand reached down to his pants button, and he paused. Why was he even doing this? He could report her. He didn't have to do this, to get naked in front of this tyrannical bitch, to stand there with his cock out while she completely ignored him. Defiantly, he grabbed his undershirt and shrugged it back on, when all of a sudden, the TV mounted on the wall lit up.
He watched in humiliated fascination as a full size video of him on his elbows and knees appeared on the television. He watched himself moaning, no, screaming, "Please. Please Jane. Please, please, I'm cumming. Please give me permission to cum!" His face flushed scarlet as he watched himself buck against her fingers in his ass and her hand on his cock and he howled on the television, "PLEASE! PLEASE!" He saw himself spurt cum all over Jane's desk. He saw his red, sweating face on the screen, panting with his eyes closed.
The video flicked off, and he continued staring at the screen, gaping. The sudden silence after his moans, screams, and groans in the video was deafening.
Her voice broke the silence. "You see, Michael, I don't tell you to do things for my own good. I tell you to do things for your own good. I want to reward you that same way, but it requires you to obey me completely."
Mike hung his head. His cock was throbbing, remembering how the orgasm had grasped him and how his cum had jetted out of his body, harder than even when he had had a particularly pleasurable session of sex with his pretty girlfriend. Jane waited expectantly, as internally he struggled with his desire to experience such an orgasm again war with his desire not to humiliate himself. After a few moments which seemed like much longer to him, his desire to experience an orgasm like that again won out.
He removed his undershirt slowly, then took his shoes off, undid his pants and stepped out of them. The cold air in the office caused his skin to break out in goosebumps as he removed his socks. He folded everything neatly and placed the items on the chair as Jane had ordered. Crooking his thumbs into the waistband of his boxers, Mike closed his eyes briefly and then pulled the boxers down, exposing his cock and ass to the cool air. When his neatly folded boxers joined the stack of clothing on the chair, he stepped over to Jane's desk, placed his hands on his head, and stood there. He closed his eyes, feeling shame creeping over him, with his cock shrinking in the cold air and completely exposed to her.
"Michael." He opened his eyes and found her staring at him intently. "I know this wasn't easy for you to decide to obey me. But it's important you realize what I told you about discipline: it means following my instructions without regard to circumstances. I can reward you if you behave, but if you choose to disobey me, and regress in your lessons, I will have no choice but to punish you to bring you back up to scratch. So far, your work with the company has been marginally better since your last session, but I think more discipline will help make you into a better employee."
He whispered, "Yes, Miss Jane. Thank you for the correction."
She nodded slightly to indicate her approval. "Michael, please move to the chair there," she instructed, gesturing to the same metallic chair she had braced him against previously for his last training session.
He took a deep breath and moved over to the chair, and without being told, he assumed the position, bending over, grabbing the arms, and spreading his legs wide.
"Excellent," she praised him. "I knew you would learn."
Mike closed his eyes, feeling humiliated at being treated like a small dog who had learned to shake hands or drop dead on command. He heard her rise from her office chair, and heard the soft shuffle of her feet against her plush carpet as she came to stand behind him. He felt the tap of the dreaded pointer on his ass, and he swallowed audibly, knowing that what was to come was not going to be pleasant.
"Not to worry yet, Michael. We have one new thing to introduce to your training."
He breathed a small sigh of relief, only to tense when he felt her fingers spreading his ass cheeks apart. The cold air on his ass made him visibly clench, and she tutted and flicked her fingers against his asshole to force him to relax. The stinging sensation reminded him not to tense his ass and he tried to relax, even as the memory of the pointer whipping against his ass made the fear of what was to come loom large in his mind. He felt cold gel around his asshole, and then her fingers smoothed it around and then pushed into his ass to grease his insides. She kept two fingers spreading his asshole, and then he grunted as something firm yet cold pushed into his asshole. The lube helped it slide in without too much pushing from Jane. It grew slightly bigger, and then his ass closed around a thinner notch cut into the object. Mike wondered what it was—it wasn't squishy enough to be silicone, so it wasn't the plug, it wasn't hard enough to be plastic...and then the burning sensation began. He squeezed his asshole around the object in his ass, and the burning sensation only intensified.
"I reminded you, did I not? You do not tense your asshole, but rather keep it relaxed. If you are wondering what is in your ass, it is a finger of ginger. It will stay there this time throughout your initial punishment as a constant reminder to heed my warning not to clench. Should it fall out, Michael, I don't have to tell you that you will definitely regret it. And should you continue to keep your ass clenched around it the way you do now, it will only intensify the burning sensation. Again, Michael—I want you to learn discipline, which is to obey me without regard to other circumstances. Shall we begin?"
With those perfunctory remarks, she tapped the pointer against his ass again, and Mike tried his best to relax before he heard the whipping noise of the pointer zipping through the air and the inevitable crack of the rigid plastic against his ass. He howled, tensed his asshole as he reacted to the pain, and cried out again as the burning grew.
He shook his hips, trying to relieve the burning both inside and out. He relaxed, and then remembering himself, gasped out, "Thank you, Miss Jane."
He felt her hand on his back, almost a gentle caress, and her approval radiated out from that warm palm.
"Very good, Michael," she praised.
Her praise almost startled Mike—would have startled him, had he not been caught up in trying to alleviate the searing pain of the welt now growing on his ass.
He felt the hand lift, and he relaxed his asshole consciously, trying to avoid at least the inner scorching of his ass, and the pointer landed again. Despite the pain, he tried his best to avoid tensing, letting out a loud shriek but keeping his hands firmly grasped on the chair.
"Thank you, Miss Jane!" he cried out.
