1 comments/ 10867 views/ 5 favorites Mike's Performance Evaluation By: mistressjanem For Mike, who enjoyed every story I ever told him. ***** Mike leaned back in his chair and stretched. He glanced at the clock—almost 4:00 in the afternoon, and on a Friday. The office was nearly empty, everybody having gone home early to get a head start on the weekend. His performance review was coming up in about 10 minutes, with his bitch of a boss, Jane. He grimaced at the pile of work she had left for him a half hour ago, with just a curt instruction to be done before he left for the weekend. He sighed heavily and pulled the first file out to review her instructions and instantly groaned. Research and a memo—on a Friday, an hour before the weekend? He grumbled under his breath, only the words "fucking bitch" audible. As if he had summoned her, she appeared right behind his shoulder. Startled, he dropped the file and stammered a greeting. Jane stood there with a neutral look on her face. She was not very tall, only about 5'2" to his 5'5". She was also very fat, with large legs and a big ass. Everybody in the office was afraid of her, knowing how ruthless she could be. Just last week she had cut the entire marketing department after they had displeased her with a subpar ad. She smiled coolly at him. "Good afternoon, Michael. I see you've finally gotten around to the work I've assigned you. Come to my office, please. We're going to do your performance evaluation now." Mike got up from his chair, still flustered by his boss's sudden appearance in his cubicle. Wiping sweaty palms on his jeans, he followed her to her office. Jane's office was big, with large floor to ceiling windows facing the street, overlooking the city. It was the start of rush hour now, and he could see cars and people rushing by in their haste to get home. "Please close the door and have a seat, Michael." He looked over at Jane, who was sitting in her large executive chair behind her L-desk. She looked at him icy politeness until he sat down in one of the uncomfortable chairs in front of her desk. There was silence as she shuffled papers on her desk and then stared directly at him. He met her gaze, and then looked down and away. "Michael, you've been with our company now for a month. Today is your first performance review. I have to say, your references were excellent when we hired you. Many of your former employers had only good things to say about you—hard-working, dependable, honest. But after a month here, I have to wonder if they were talking about the same person we hired." He looked at her and then dropped his gaze as the silence dragged on. "Frankly, Michael, I'm not sure you're a good fit for our company." He snapped his head up and stared back at her in disbelief. He was being fired? On a Friday? A month into his job? He heard himself start speaking, as if he were listening to another person. "Please. Jane. I really, really need this job. What can I do to improve? I can't lose this job now. I'll do anything. Really." The blubbering went on, and Jane let out a disgusted sigh, muttering under her breath, "I knew I should have let Human Resources handle this. What a mess." "Michael, stop it. Stop whining. If you wanted this job so badly, you should have worked harder and been more disciplined. However, I am willing to work with you to help you keep your job. You are new to the company, so I think it's just a matter of training you to achieve the kind of work ethic we're looking for." Mike couldn't believe it. The ice queen was letting him keep his job? He quieted down, listening intently to her. "Michael, do you want to start this training? It won't be easy." She glanced at him, and he nodded slightly. "Very good then. Take off your clothes." He gaped at her. She sighed again, like a parent with an extremely frustrating toddler. "Take. Off. Your. Clothes." She said it slowly, enunciating each word like he was an idiot incapable of understanding English. He sat there, shocked. What was Jane doing? Didn't she know that there were rules against sexual harassment? She stared disgustedly at him and then told him, "Gather your things. You're done here as of today." With those words, Mike knew he had no choice but to obey. He raised his hands to the first button of his collared shirt and hesitated. He saw her staring intently at him, and he started to unbutton his shirt. He felt the cool air in the office surrounding his body as the shirt came off. He took off his shoes, then his socks. He stared at Jane, still sitting in her large chair. She eyed him coolly as he unbuttoned his jeans and unzipped his fly. He stood up, and pulled down his jeans and stepped out of them. Now he just had his boxers on. He put his fingers on the waist of his boxers, and hesitated again. He let out a soft, "Please" as he looked at her, begging her with his eyes not to make him do this. She cocked her head to the side and held his gaze. Defeated, he pulled down his boxers. With an uncontrolled reflex, his hands immediately came up to cover his cock. He was blushing so hard, he felt his whole body turn warm. "Put down your hands, Michael." The command was soft. He reluctantly put down his hands. "Excellent. Part of being disciplined is following directions. I'm glad to see you're capable of doing that. Now come here and brace yourself on this chair." She pointed to a chair near a table in the middle of her expansive office. It was a hard, metallic chair, keeping in line with the cold modern lines in Jane's office. "Hold onto the arms, spread your legs and bend over," she commanded. Mike reluctantly grabbed both arms of the chair and bent over. "I said, spread your legs, Michael," she instructed. He moved his legs about 6 inches apart. She made a tsk-ing noise, and curtly commanded him, "I said spread them. More!" He jumped, startled at the change in her voice. He spread his legs wider. She nodded in approval. Mike groaned, imagining how this looked. He could feel the cold air seeping into his ass crack. She got up from her chair and got behind him. He felt her caress his ass cheek, as she told him quietly, "Discipline means following instructions no matter what the circumstances are. You've had trouble with this, but today we're going to correct this." She picked up a pointer from near her display board and told him calmly, "You are not to let go of that chair under any circumstances. Do you understand?" He nodded. She continued, "After every stroke, you are to tell me, 'Thank you, Miss Jane.' Understood?" He nodded again. "Good. Let's begin." He heard her move and reposition herself. There was an alarming amount of silence that seemed to go on for an unbearable amount of time before he felt, rather than saw, her raise her hand back and whip the pointer against his ass. Mike howled, the veins on his neck standing out at he arched his back in pain. He let go of the chair and clutched his reddening backside. And then he remembered Jane, who stood there with her arms crossed and looking extremely displeased with him. He put down his hands and looked down at the ground, already knowing he had messed up. She tapped him on the ass gently with the pointer, and said only, "Again." He moaned quietly and then bent over the chair, spreading his legs without being told. He heard the rustling of her clothes as she again repositioned herself. And then again, a white hot fire against his ass. He screamed and almost let go of the chair, but this time remembered his instructions and gripped the chair tighter as he swung his ass around trying to alleviate the pain. And then he choked out, "Thank you, Miss Jane." He turned his head slightly to look at her, and she lifted one corner of her mouth in a half smile. He bent his head back down, awaiting the next stroke. She swung again, and again, and again. He moaned, shrieked, groaned as his ass was lit on fire. He managed to say "Thank you, Miss Jane" after each stroke, but his mind was clouded with pain and a little fear. She patted him on the backside in approval. Mike could feel the sweat beading on his body from the pain and exertion his body was being put through. There was silence, and then she instructed him to spread his ass cheeks. He reached back without hesitation and spread his ass cheeks, exposing his little anus to her. He heard her move to her desk, and return to her position behind his ass. She instructed him to keep his hands where they were now, opening his ass cheeks up, and not to let go under any circumstances. He nodded his assent. Silence again, and then a stinging pop against his anus that almost made him lose his grip on his ass cheeks. He stifled a little scream as the pain spread. What the hell was that? Mike turned to see her with a thick rubberband, preparing to snap him on the anus again. He groaned, and put his head down, still holding his ass cheeks apart. She snapped him again, and again, and again. He wiggled his ass from side to side, trying to shimmy the pain away. He heard Jane behind him tsk again. She commanded him to stop wriggling his hips like a little whore and hold still. He blushed again, mortified. She snapped his anus until it was swollen and hot to the touch. Mike never let go of his ass cheeks despite his small yelps and whimpers on each strike, and he could tell that Jane was pleased with him. It suddenly felt more important than ever to please this woman, who seemingly was never pleased or satisfied. "Michael, I see the training is starting to work. Perhaps you have potential here after all. One last piece of training, and then you can get back to work." Jane motioned for him to get on the table in her office on his elbows and knees. She instructed him again to spread his legs so that he had easy access to both his cock and his anus. She gently fingered the welts all over his ass, looking at the bruising that was just beginning to turn purple. He shivered in pain as she rubbed each welt. She then quietly told him that the final lesson of the day was not to cum until given permission—he had to learn that he was no longer in control, but she was. He was also instructed to stay in this position no matter what. He groaned quietly and nodded in defeat. He felt her rub cream into his anus, pushing her fingers in to help spread the lube. And then two fingers were suddenly in his anus, and he arched up, trying to escape the intrusion. Jane slapped him on the ass, right on the welts and he screamed. "Did I say to get up? Did I? I specifically told you to stay in position, didn't I?" She punctuated each sentence with an angry slap on his ass. He cried, feeling the tears leak out of his eyes as the pain radiated from his ass. "Now hold still. Do you understand?" Mike nodded, and returned to his hands and elbows position. She wiggled her fingers in deeper, looking for his prostate, and upon finding it, she rubbed her finger over it. Mike let out a deep, low moan, feeling an extraordinary pressure to cum. However, fearing another slap on his already bruised ass, he held his position. And then Jane's hand reached around for his cock and began to stroke it. She stroked his cock slowly, simultaneously milking his prostate. Mike was in agony. He could feel his orgasm coming, and there was nothing he could do about it. He burst out, "Please. Please Jane. Please, please, I'm cumming. Please give me permission to cum!" There was silence and then a curt "no" came from behind him. He sobbed in desperation as she continued to stroke his prostate and his cock. "PLEASE. PLEASE." He almost screamed his pleas, feeling out of control as his orgasm bubbled up. And then she said, "Cum, Michael. Now." And he cried in relief as his cum shot out of his cock, all over the table. The orgasm seemed to go on forever as he tried to pump his cock into her hand. He almost collapsed onto the table in exhaustion when she withdrew her fingers from his ass, but at the last moment, he looked up at her and said quietly, "Thank you, Miss Jane." She half-smiled at him, letting him know that he had done well. And then, without even raising her voice, she instructed him, "Clean your mess up from my table, get dressed, and get back to work. I hope this lesson will hold you until your next performance evaluation and your next training session." He got up, grabbed tissues, and swabbed his cum from her table. He put on his clothes, gingerly, trying to avoid having his boxers rub his sore ass and moaning quietly when sliding his jeans on and feeling the rough material rub the welts through his boxers. He turned to her again, and quietly said, "Thank you, Miss Jane" before opening the door and stepping out into the main area. Mike's Performance Evaluation Ch. 02 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. "Good boy," she murmured, smoothing back the hair on his head. Already his body had broken out into a sweat even with the air conditioning in Jane's office turned down to the maximum cold temperature.She positioned herself behind him, and without any other instruction or reminder, she caned him with the pointer, crisscrossing the marks across his ass, leaving red and white marks. After each strike, he remembered to thank her. By the end, his ass was a map of welts, and he bent his head in deep, long sobs. His fingers gripped the seat so tightly they were white, and his anus still contained the hated ginger root. He felt the ginger being tugged from his ass and he bore down the slightest bit to help the ginger exit all the faster. He felt Jane's fingers trace over the welts and shuddered in pain. Jane tipped her finger under his chin and raised his face so he could look at her. What he saw in her face almost made him cry again—it was kindness and even a little pride. "Michael, you have done much better than our last session. You are learning, and I am proud of you. I will make a disciplined man out of you yet. Stand up, and follow me." She walked over to her black leather couch, and spread her legs. He could see that she was wearing no panties under her skirt, and that her inner thighs were glistening with moisture from her pussy. She leaned back, hitching her skirt up so that her pussy was completely exposed, and propped her legs against the wide arms of the chair. "Kneel, Michael, and see how much pleasure your obedience brought me." He sank to his knees in front of her, her pussy in front of his face, and he breathed in her scent. Funny, he normally hated pleasuring a woman with his tongue. But this fat, mean woman, with her normally angry expressions—somehow, during—after?-the caning, it no longer felt like he needed to obey her. He just wanted to please her. He brought his face forward, and looked at the pussy in front of him. She didn't tame her pussy bush. It grew wild and thick, trapping her scent and her moisture. He could see her big clit straining forward between two fat outer lips, red and swollen with her arousal. He bent his head and gave her clit a little lick and she pressed her head back against the cushion, closed her eyes, and moaned softly. That was all the signal he needed. He gently embraced her fat legs in his arms so she couldn't squirm away, and began licking in earnest. He licked and sucked the clit, making it more engorged, shoving his tongue into her pussy and scooping out the juice inside. She tasted slightly salty, warm, and creamy. He dug deeper with his tongue, and she practically shoved his head back by forcing her hips forward. "Oh yes," she hissed at him. "More!" His cock grew hard at her heated reaction, as she moaned and writhed under his licking and sucking. "Yes, Michael!" she cried, and he nipped at her clit as she reached orgasm. She squeezed his head between her fat thighs as she came, trapping his face near her pussy. He continued licking until she was shuddering and gasping and released his head from between her legs. "I see that part of you needs no training." She smiled at her own joke and Michael managed a smile, still licking her cream off his face. She looked down and saw his cock hard and straining. She reached down and stroked it gently a couple of times and a whining noise came from his throat as his cock grew harder. He was so close! "Not yet, Michael. We still have more training to do." He groaned out his disappointment, and she simply raised an eyebrow at his audible display. He hung his head and muttered, "I'm sorry, Miss Jane." He knew without her telling him that he ought to be grateful for any attention she paid his cock. He felt disappointed in himself for disappointing her, for breaking his streak in obedience. She motioned for him to sit back on his heels. "Michael, you will now answer some questions for me. I expect full answers, without hesitation. Hesitation will be punished. I require more information about you in order to make sure your training progresses correctly, and also to make sure I do not push you too hard, too fast, do you understand?" He nodded, and then said simply, "Yes, Miss Jane." "Good. Put your hands on your head and don't put them down for any reason." She paused, considering, then asked: "Have you had anything up your ass besides my fingers before?" "No, Miss Jane. Just fingers—yours and my doctor's." "How often do you masturbate?" "Not often, Miss Jane. Once every couple of weeks when my girlfriend has to work late." "I see. And how often do you fuck your girlfriend?" He flushed at the crude choice of words, and then said, "Almost everyday. Except for the past two weeks. I couldn't, um...let her see my ass the way it was. And then she got angry when I didn't want to have sex, and then..." He gestured helplessly, trying to communicate his celibacy, and blushed again. She nodded, frowning. The questions continued on, delving into his sex history. What kind of porn did he watch? (Female domination, lesbians, regular vanilla sex.) Had he ever participated in watersports? (No.) Had he tasted his own cum? (No.) Did he want to taste his own cum? Mike hesitated. He hadn't ever tasted it, but after watching a man being dominated in one of his porn videos, he had been tempted to reach down and try a lick. At the last moment, he had decided against it, his shame winning out against his curiosity. All of a sudden, there was a sharp pain in his balls, and he realized Jane was pushing on his balls with her heels. "Didn't I tell you not to hesitate? Didn't I?" With that last question, she kicked a bit harder with her soles into his balls with each word. He yelped and then said, "Yes, Miss Jane! I'm sorry. Yes, I want to taste my own cum!" Her foot eased off his balls, and his hands reached down immediately to cup the throbbing orbs. He immediately realized his mistake and his hands dropped to his sides in defeat. He could see the disappointment in her eyes, as he realized he had failed her again by taking his hands off his head despite her explicit instructions against it. "Michael, I realize this training session has been long and hard on you. But you really must try harder to listen to my instructions and obey them." He nodded, tearing up. Internally, he was surprised at his own submissiveness, at how much he wanted to please her. He dropped his eyes to the floor, and without thinking, he bent and kissed the shoe that had just moments before been crushing his testicle. He felt her hand on his head and knew he had mollified her somewhat. She stood, and walked over to her desk. She reached into her desk and brought out a black leather case that looked almost like briefcase. She unsnapped it and considered the contents. From his position on the floor, still kneeling, Michael could not see what she was looking at. At last, she nodded to herself, and then called for him to come to her. He rose and came to her, and she gestured for him to sit on her desk. "Get on all fours on my desk, Michael. I want you to put your forearms flat on the desk. Spread your legs for me, yes, just like that. A bit wider, if you please." Awkwardly, he readjusted himself so his legs were a bit more splayed. "Good, now stay in that position." He felt her two fingers again spreading his ass cheeks open, and then her two fingers pressing around his anus and then into him, lubing him. They drove in and out, pressing against his prostate on their way out. He gritted his teeth as his cock sprung up, erect. He heard a metallic clink as Jane reached into the case and then he felt something pushing into his anus. It wasn't her fingers. What was that? He turned his head in curiosity and was rewarded with a quick smack to his ass. The tap was a reminder, not a punishment. He brought his face forward again and felt something pushing inexorably into his anus. The burning began almost immediately as his anus stretched to accept the intruder. He reared up to try and escape the pain, and Jane immediately smacked him hard on his welted ass cheek. This hit was definitely more than a reminder, and he sank back down gritting his teeth and hissing out his breaths as the pain intensified. 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.