Megan & Kasey - Job Training Ch. 04

She gave him a big hug and kiss on the lips. "It's so good to see you," she said, bubbly and happy. "Thank you so much for bringing this on such short notice."

"My pleasure," Darrell said. "Mmm, you look better every time I see you, Kasey."

"Thank you, sir," Kasey smiled. She opened the bag and pulled out exactly what she had asked for: A ball gag, a collar and leash, fur-lined handcuffs, and a butt plug. She squealed in delight, then turned to Darrell, "Um, sir, I have about 20 minutes before Mr. Brandt returns. I'm sorry I don't have more time, but I would very much like to thank you for doing this for me. May I please suck your cock, sir?"

"Put the collar and leash on first," Darrell said, unbuttoning his pants.

"Yes, sir," Kasey said. She put on the bright red dog collar with the matching red leash attached to a gold ring on the collar. "It's on sir. May I be your bitch now, sir?"

Darrell pushed her to her knees and grabbed the leash close to her neck as he jerked her toward him. He was half erect and it took only a few licks to get him fully hard. Kasey looked up at him the entire time, sucking and bobbing her head, her pace and depth monitored by Darrell's firm grip on the leash. He gripped her ponytail with his other hand as he worked his cock into her throat. He knew he didn't have a lot of time, so he didn't try to make it last. Normally he would have liked to pull out, rub his cock on her face, slap her cheeks, make her suck his balls. But in this case he just kept pumping into her sweet mouth, staring down at the lovely blonde who seemed to be enjoying this almost as much as he was. Her love of cocksucking seemed genuine and it turned him on.

When Darrell came, as much as he wanted to shoot his white cum all over that little black skirt and boldly mark his territory, he knew she had a big meeting coming up. So, he came in directly in her mouth, letting her suck out every last drop and swallow it all. No mess.

Before he left, Kasey removed the collar and leash and then asked him to put the butt plug in her ass, a task he happily took on. "Where are your panties?" he asked.

"I gave them to Mr. Brandt," Kasey smiled. "Was that bad of me?"

"Very," Darrell laughed. "Call me anytime you need a delivery, Kasey."

"You know I will, sir," Kasey smiled, walking him out, very aware of the butt plug in her ass.

Kasey hurried back into the office, placing the bag of toys under one of the chairs at the small meeting table. She drank some water, rinsing the remnants of Darrell's cum down her throat, then gargled some mouth wash in the bathroom. She checked her hair and clothes, then lifted her skirt and looked over her shoulder, happy to see the shiny diamond-design tip of the butt plug exposed between her cheeks. She went back and ran through the very brief presentation one last time, then awaited Michael's return.

Michael parked the car in the office lot and looked once more at the impossibly small and sexy g-string in his hand. In a rare act of impulsiveness, he hung them on the rearview mirror and walked back into the building, trying to think of anything but the sweet smooth pussy that g-string had held.

"How was your lunch, sir?" Kasey asked when he came back in the office.

"Very good, thank you," he said. "Did you have time to eat?"

Kasey fought back a giggle, thinking of Darrell's cock and the load he had given her, which served as her only lunch. "Yes, sir," she said. "I had a quick lunch. It was yummy."

"Good," he said. "Well, the floor is yours. I promise I will do my best to keep an open mind."

"I appreciate that, sir," she said. "Before lunch, you acknowledged that maybe you need to make some changes, but challenged me to prove that I'm the change you need. I thought about it realized that there's nothing that I can offer that another assistant couldn't. Anyone could help you with your appointments, your emails, your laundry, your errands, and meals. Many would be more qualified than, me, in fact."

Not with a body like that, Michael thought, but he kept his mouth closed, realizing that Kasey wasn't putting herself down, but setting up for a new direction and explanation of why he needed her. It was a good strategy. She had natural presenting and sales skills.

"But I do think you need a hobby, a distraction, if you will, sir," Kasey said. "With Megan now doing her own thing, even though she still lives with you, you have less of her activities to attend. No tennis matches or school events. She is independent in many ways. She needs you as much as ever, but not for as many hours a week. We already discussed your marriage and it's safe to say that you both need time. What you don't need is time to dwell and overthink things. I know you like to analyze things and have a plan. But I urge you to make that plan for something other than your personal life. That needs time to breathe, sir. But the fact remains, you still need an assistant and you still have needs beyond which a normal assistant might be willing to provide - although I must say I know many women who would love to be with you, sir."

"Thank you, Kasey," Michael said.

"But," Kasey said, finally launching the presentation. The first slide was a bubble chart with three intersecting circles. One circle was labeled office assistant. Another was labeled personal assistant and the third was labeled sex partner. For presentation purposes only, each circle had 100 available candidates for each task, but the intersection included just 10. "These are rough estimates, sir, because I did not have time to research. But let's assume you could have your pick of 100 people for each of these roles. But not all could work for you night and day. And not all, despite your attractiveness, would be interested in being your sex partner. So, let's say 10 percent would be willing and able to perform all three tasks. That puts me in a small group, sir. But still, that's a lot of completion. Do you need me, or just someone like me?"

She paused, then went to the next slide which showed four gifs. One gif was her trying to suck on a dildo and gagging as it hit the back of her throat. Another was her trying to dance on a stripper pole and slipping and falling. Another was her trying to insert a dildo in her ass and looking shocked and pained at the camera. He smiled and chuckled.

"Why you need me, sir," she smiled, "is because I need you. I realized I want to be all these things for you, but I do not excel at any of them. So, sir, you need me because I'm the hobby you need. I'm the distraction. You can train me, teach me. I'm your project, sir."

She went to the next slide, which included a gif of her choking on an actual cock while bound and restrained. It wasn't really her, but Jackson had found a clip of a porn star with a similar body and then selected a portion of the clip where the face wasn't identifiable. If Michael studied it long, he would realize it wasn't her, but the intent wasn't so much to deceive as it was to illustrate.

"I had a boyfriend briefly, an older man," Kasey said, telling a story she had made up during his lunch. "He was into rough sex and bondage and role play. He loved talking dirty and calling me names. I didn't mind it, but it was hard to get used to so I think I acted surprised, which he didn't like. He wanted me to play along. I tried hard to learn, to be what he wanted, but I struggled, as you can see. He got frustrated and bored with me and moved on to someone else."

"I'm sorry, Kasey."

"It's OK, sir," she said. "It was a learning experience. But, as you can see, I need to learn these things. You need something fun to do. That, sir, is why you need me."

"But I'm not really into rough sex like that," Michael said.

"Is that because you don't like it or you haven't tried it, sir?" Kasey challenged. "Maybe if you try it you'll find your old self, the man she fell in love with, sir."

It was a bold statement, one she knew could end the meeting abruptly if he was angry or offended. He seemed a bit stunned, but not angry. Like he was thinking. Screw analysis and planning, she thought. She reached in the bag, put on the collar and got on her hands and knees, crawling to him with the leash between her teeth. She sat up at his knees, hands up like a puppy dog's paws, head down, eyes up, looking at him with a pouty mouth and puppy dog eyes. She was begging for it.

Michael could no longer resist. He took the leash from her mouth and pulled her up to her feet. He kissed her hard on the mouth and whispered in her ear, "We have tonight and most of tomorrow until Megan gets back. We'll call it a trial run and see where we stand tomorrow night."

"Yes, sir," Kasey breathed, blown away by his kiss and his partial acceptance of the plan. She wanted to ask him if she could suck his cock, but that would demonstrate some of her training. She needed to act the way should would have just a couple weeks ago. She to be reluctant but willing at first, then enthusiastic but awkward. She had to let him train. She had to ask questions and make mistakes. She knew he probably wouldn't fuck her ass first, but she decided to show him anyway, to plant the seed. "Um, sir, I brought a few other toys. Would you like to see them?"

"Sure, Kasey," he said, still holding the leash. "Show me what you brought."

Kasey walked back to the bag with Michael holding the leash. She pulled out the ball gag and showed him. "Um, in case you needed me to be quiet while you worked, sir," she said.

"Very good idea," he nodded. "Wouldn't want anyone to hear you crying out or anything."

She pulled out the fur-lined cuffs. Having been cuffed himself last night during the massage, he was not surprised that she had these. "If I'm bad or you need me to stay put?" she shrugged innocently.

"Certainly a useful toy," he acknowledged. "Any more?"

"Just one, sir," she said. She turned around, bent over at the waist and pulled her skirt up to her waist. She spread her ass cheeks and he saw the butt plug. "I've never, well, my ex tried to, but I was too tight. Anyway, I thought you might want to and read that this helps a girl prepare. Um, if you want it, sir."

"That's a very generous offer," he said. He put his hand on her ass cheek and gave it gentle squeeze. Come on, slap it and grope it, Kasey urged in her head. But his touch was gentle, respectful. Maybe it was too soon. Maybe it was being at work. Getting him to take her and own her was going to be a challenge. "Maybe later, though."

"Any time, sir," she said. "Do you want me to call you sir or mister or master or daddy?"

"Daddy?"

"Ew, not like you're my dad but like you're my daddy, you know, you own me, you are in charge," Kasey said, well aware that she seemed like she was teaching him more than he was teaching her. She had to watch that, but she was beginning to think she was going to have to handcuff him again and make him fuck her. He was seriously messed up. She felt it was her mission to fuck him as many times as it took to help him regain his sanity.

"I see," he said. "Well, um, sir sounds good. Or mister. I don't much like master, but you can try daddy if you want. I'm undecided on that one."

Undecided. This man was so wishy-washy. She offered him three holes most men would jump at the chance to fill and he couldn't even decide what dirty talk he would find palatable. Kasey truly cared for him but she could understand Susan's frustrations.

"Yes, mister," she said. "Is there anything I can do to be of, well, use to you currently? Something with your job or, um, other needs? Daddy?"

Most men would have ripped her clothes off and fucked her over the desk or table by now. Michael was not most men. Even though he was clearly aroused, he was still thinking. "Let's think about this," he said. "I am horny right now, which clouds my thinking. Let's fuck so I can cum and recalibrate my brain. Then, we can finish the work day and make our plans for tonight."

Recalibrate? Plans? Kasey was beginning to think she would have to submit paperwork and make calendar appointments with agendas just to get him to finally fuck her. He would probably want someone to take minutes and write a report.

"Of course, sir," she said. "Um, how do you want to fuck me?"

"Holding your panties all through lunch, all I could think about was that little pussy," he said, finally sounding like a man with some balls.

"You want this little pussy?" she teased, holding up her skirt and showing him the bald mound and pink lips. "It belongs to you, sir."

"Yeah, I suppose it does," he said, sounding surprised.

She leaned forward and kissed his neck and whispered in his ear. "Take it, mister," she said. "Any way you want it, sir. Any position. Teach me how to please you, daddy."

"Take off your clothes," he said, stepping back to watch. There was suddenly a depth to his voice, it was guttural, stern.

Without responding, Kasey slowly removed her sweater. She watched him, watching her. He was no longer calm and half-smiling. Now he was looking intently at her, staring at her belly and breasts as they came into view. His gaze was intense. His lips were slightly parted. He looked like a predator studying its prey. The change in his appearance was startling, but also kind of exciting. Maybe there was some animal instinct and desire left in him after all, she thought.

She wriggled her hips as she shimmied out of the tight skirt, leaving only the collar, leash, butt plug, and black pumps as adornments on her body.

"Should I remove the butt plug, sir?" she asked meekly.

"Not until I'm ready to replace it with something else," he said. His tone and demeanor were totally different. It was crazy. The change was so sudden and complete that it was kind of scary. He seemed darker, but more himself, like all this time his sweet but withdrawn demeanor was just a façade.

He took the leash and pulled her to him, kissing her on the mouth, neck and breasts, his hands on her waist and ass. He pulled her to his desk, pushed laptop out of the way, and pushed her on her back. He held the leash in his teeth as he dropped his pants and put her legs up on his shoulders. He looked down at her, analyzing her body. His gaze was different from last night, Kasey thought. Then he had looked at her like he was admiring her beauty. Now he looked at her like she was a delicious piece of meat that he intended to devour. She didn't recognize this man, had never seen this side of him. Had he snapped? Was he in his right mind? It was scary, but, god, it was so exciting too. She was equal parts afraid and excited to see what he would do to her.

He ran his hands down the insides of her thighs, smiling as she trembled. She could see his cock was extremely hard, yet he seemed to be less excited about the moment of entry than she was. She couldn't wait. She needed it. He seemed quite content - indeed intent - on taking his time, despite his earlier indication that he needed to knock out a quickie to clear his head. The reality was, she thought he seemed to be thinking more clearly now. He was in total control of his actions. She thought she might unleash a wild, frantic, horny man long overdue for release. Instead, she had unlocked something else entirely.

He stroked her thighs and pussy lips, then finally pulled her lips apart and took a long, close look at her pussy. It was pussy now. He held her apart while he rubbed his thumbs up and down along her opening. She squirmed, wanting something - his fingers, his cock, anything - to push inside her. But he was taking his time. Her desires were of no consequence to him. She could see that in his face, his actions. He was almost the exact opposite of the caring man he had been 15 minutes ago, with the only exception being that he was still remarkably calm. He should have been tearing into her, fucking her with insane lust and desire. Instead, he was taking his time for no other reason that he wanted to and there was no one who was going to make him do anything differently.

Kasey was like putty in his hands, her thighs quivering, her pussy a wet, juicy mess of desire and need. Her nipples ached, sticking straight up in the air. She felt like one thrust inside her with that big cock would make her cum. Maybe even just the tip. Maybe just a finger. She was so ready.

Finally, he put his index finger inside her like he was poking the middle of a pie. She gasped at his touch. He held his finer inside her, only up to the first knuckle. She wanted the finger. More fingers. The whole fist. But he didn't seem to notice. He was enjoying watching her pussy clamp around his finger, loving the feel of her velvety softness and intense heat.

He put the finger to his lips and tasted her. She watched his expression. It wasn't exactly a smile, but he was pleased, she could tell. He knelt down and put his mouth to her pussy. He kissed the lips, then nibbled them, then licked them. She was on fire as he pulled her lips apart and kissed her hole, then licked inside her, lapping up and down like she was a Popsicle. His tongue covered her entire slit and finished with a slurp across her clit. Kasey bucked her hips off the table, pushing herself toward him, urging his tongue inside her.

He didn't give in to her urgings. He ate her at his pace, but it did the job. He continued to lick and suck on her juicy cunt until she came. She cried out as she came, then fell silent, her body rigid for a moment, then relaxing. He stood up, stepped forward and put the tip of his cock inside her. He had showed her that he could control her pussy with his fingers and mouth. Now he was going to teach her exactly how her pussy was meant to be used

He held the tip inside her as he leaned forward and kissed her neck and sucked on her nipples. She moaned and thrust her hips, trying to get him further inside her. "Patience, little slut," he said. "That's my pussy. I fuck it when I want, how I want. Now hold still or I won't fuck it all. You want me to stop before you cum again?"

"Nooo," she moaned.

"No who?"

"No, daddy," she said. "I need to cum again. Please, mister."

He pulled his cock out and tapped her pussy mound with it. He was so hard and big. It was like he was hitting her with a steel rod. "I'm daddy, sir, mister, right?" he didn't wait for a response. "Well, this, my dear, you can call 'master'," he said, referring to his cock. "You call it master or cock. It's your master because it owns your body know. By the end of the night, it will have marked its territory in every hole. You will bow to it, serve it, and worship it."

"Yes sir," she whimpered. "I love my master. I will worship it and serve it forever."

The second she said "forever", he thrust into her, full force, balls deep, lifting her off the desk with the force of his entry. Kasey absorbed the blow by wrapping her arms around his broad shoulders and holding on. He dropped her legs off his shoulders and she wrapped them around his waist. She embraced him with her arms, legs, and pussy, which clamped on tight to his angry cock. He filled her little pussy with it and he slowed down, raising up momentarily to enjoy the sight of her pussy extending each time he pulled back, those lips so tight around him that it was a like a vacuum seal. He laughed and thrust back into her as she once again embraced him, moaning and gasping as he hammered away at her overmatched pussy.

"You better cum before I do, slut," he said. "You won't like the punishment if you don't." Punished if she didn't cum? That was a new one, Kasey thought. Being brutally fucked, manhandled, dominated and ordered to cum? This was the submissive life she could get used to. His sheer power and dominance overwhelmed her and she came twice more before he finally pulled out and unleashed a massive load. Yes, she had drained him last night, but it had been a long time since he'd had a proper fuck. Last night had been maintenance. This was full on wreck-the-hot-little-pussy fucking and his load demonstrated how overdue he really was. His spray left globs of thick white cum on her belly button, forehead, and all points in between.