Pissed Off Boss

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Rick learns disappointing the Boss has consequences.
4.2k words
4.4
147.4k
36

Part 1 of the 3 part series

Updated 09/22/2022
Created 04/17/2005
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Rick knew that his boss was going to be pissed. He had promised her that the report would be on her desk the first thing in the morning, but there had been no way that he could have known that the train would break down. He was almost an hour late as he briskly made his way to her office. He didn't stop to remove his coat and leave it in his office because he didn't have the time.

Rick knew that he was in trouble as he came around the corner near her office. Ms. Pittman was speaking with her secretary and the look on her face told it all. She spun on her heels as Rick came into sight.

"Where the hell have you been? You assured me that the proposal would be ready by this morning. I just sat through an entire meeting with our new clients and nothing to show them." She said in a very dangerous and measured tone.

"It is ready, but there was a massive power outage on the train. I've been stuck on the train for almost two hours." He tried to explain. He knew she was not going to be placated by any excuse.

"Well, you're lucky that I'm not sending you back on that train. It was all I could do to fake my way through that meeting and your lucky that I came up with a advertising strategy that they liked." She said with a great huff.

"It's no excuse, but I really didn't mean for this to happen." Rick said in apology.

"Well, you're not off the hook. You're going to be putting in a lot of work on this campaign, and you better not disappoint me again." She told him. She was calming down a bit, but Rick knew that she meant every word. Talia Pittman was on top of the advertising game, and she was known to quickly drop anyone who couldn't produce.

"I want you take that coat off and come with me. You can leave the report on my desk." She said as she turned away. Her heels clicked loudly on the tile floor as she strode down the hall.

Rick pulled his coat off and sat it on the visitors' chair in her office and dropped the report on her desk. He quickly caught up with her and followed her into the boardroom.

"Close the door and lock it. I don't want to be interrupted while I lay this campaign out." She told him.

Rick did as he was told. He had prepared the rates package, but as of yet, he still did not know who the client was. He eyed a box on the glass table, and figured that he would soon find out.

"The idea came upon me quickly, and I think it will be a hit. The client offered to help with the work, but I think it will be better if it doesn't have too much of a 'professional' look." Ms. Pittman explained.

Rick was still in the dark as to what she was talking about, but he also knew that he was lucky to even have a job. He watched as she checked the two video cameras that were stationed in the corners of the room. They were often used for video conferencing and even video for promotional work. She was adjusting the angles to make sure that conference table was in clear view, and Rick was somewhat puzzled by her actions. He gave up trying to figure it out, and figured that she wanted to tape the brainstorming session.

"Go ahead an take everything out of that box, so that we know what we have to work with." Ms. Pittman told him as she adjusted the lights in the room. Rick complied, but was shocked as he opened the box. It was filled with all sorts of sex toys! Rick was caught off guard, but did as he was told. He wasn't inexperienced by far, but these were not the standard variety of sex toy. A lot of the items were made out of leather or latex and looked like something out of a science fiction movie. There were items that he knew, but there were also those that he didn't. His face was a deep crimson by the time he emptied the box.

"That's good. Now lets see what we have here." Ms. Pittman said as she examined the items. "Our client wants to branch out into the mainstream, and I think I have just the advertising strategy to do that. We are going to push the everyday aspect of these items. They are a common and useful part of a healthy sex life, and there is nothing to fear. We are going to show that everyone can use these, and that they are not just for the 'sexually perverted' as some people think." She explained.

Rick was still shocked, but his instincts for work were taking over. "I see what you mean. We could have testimonials from people that society would consider 'normal'. We could use housewives, teachers, doctors and possibly ministers. After all, sex between married couples does not have to become routine." He said enthusiastically.

Ms. Pittman smiled. "That's exactly what I had in mind. I knew I would not regret firing you right on the spot this morning." She said as she browsed through the toys on the table.

She selected a pair of leather wrist cuffs and approached Rick. "Let's put these on and take a few close up shots of your hands. I think that might be an eye-catching, lead-in image. Rick was feeling a bit uncomfortable about the offer, but knew that he was in no position to refuse. She had already made it clear that she had considered firing him for his earlier issue. He held out his hands and she buckled the first cuff around his wrist, but instead of doing the same with the other, she pulled his hand behind his back.

"It will look better with your arms behind your back. Give me your other hand." She told him. Rick was even more uncomfortable, but complied none the less. He felt her fasten the second cuff and then step away.

She came to stand around in front of him. "Try and pull your hands out. Let's see if these are actually as good as they claim." She instructed.

Rick twisted and pulled his arms. He flexed the muscles in his back and tried to pull the cuffs apart, but the leather and chain held firm. "I can't budge them. These things are pretty strong." He told her finally.

"Good, now lets test these other ones." She said as she retrieved another pair of cuffs from the table. Rick was expecting her to remove the first pair, but instead, she slid down to her knees and began fastening them around his ankles. When she was done, she stood and looked at the total effect.

"See if you can kick out of those." She ordered. Rick tried with all his might, but just as with the first pair, he was not able to break the second.

"Nope, it's just as strong as the others." He said.

"Well, we at least know that we are working with a company that isn't lying about the quality of their merchandise. I hat trying to put a good spin on inferior goods." She said as she perused the table. Rick was hoping that she would get on with taking the pictures and let him out of the restraints. There was something weird about being tied up in front of his boss. It was both strange and exciting all at once, and he didn't want that excitement to show.

"Now this is an interesting piece." Ms. Pittman said. Rick watched as she fingered a leather strap that had a silver ring attached. She picked it up and walked around behind him.

"Lets see how this fits." She said from out of his sight. Rick didn't know what the item was, and was surprised when her hands came over his head and into his line of sight.

"Open up." She said, and he was so surprised that he did so without thinking. He caught a flash of the silver ring before it was placed in his mouth. He found that the ring was had four legs that kept his mouth open, and to his greater shock, he felt the leather strap tightening and being fastened behind his head.

His mouth was held open by the tightly fastened ring, and his eyes were still wide in shock as Ms. Pittman came back into view. She was smiling smugly, and Rick was getting a bad feeling in the pit of his stomach.

"That's just what I had in mind. What is more normal than the corporate male in his natural habitat?" She said. "The manufacturer wants to go mainstream, but not in the way you were thinking. We can never come up with an ad that will play on television for the masses. What they want is to sell to the common adult who already buys the 'vanilla' toys, but has been leery of getting too extreme."

Ms. Pittman touched the intercom on the table and dialed her assistant Sue. "Sue, make sure the phones are set to go directly to voicemail, and come down to the boardroom." She said. Rick was horrified as he watched her walk unlock the door. He didn't want to be tied up and he sure as hell didn't want anyone else knowing about it.

Sue came through the door and Ms. Pittman instructed her to lock it again. She chuckled as she saw Rick and again when she saw how red his face was.

"Now Rick, I hope you realize the situation you put me in this morning. A person in my position cannot enter an important meeting ill prepared. You were to provide me with the information that I needed, but you failed." Ms. Pittman explained. Sue was already browsing through the toys, but Rick's attention was focused on his boss.

"Normally, I would have fired you on the spot, but I like you, and you have always performed above expectation. It's for those reasons that I have decided to keep you on." She explained. Ms. Pittman had come closer to him as she talked, and was now standing so close that he could smell her perfume.

"You come to work everyday in your pressed suits. You work hard, never take a long lunch and put in as much overtime as needed to get the job done. Your attention to detail is really only second to mine, and it shows in everything you do. It is all of these things that makes you the epitome of what the corporate worker should be. It is because of this that you are the perfect person for my ad campaign. We will show that even the straight-laced, corporate executive gets down, dirty and kinky." She explained in a tone that let him know that he did not have another option.

"How do you want to start out Talia?" Sue asked. Rick's attention was drawn to her and for the first time was actually afraid. Sue was a medium built woman in her mid thirties. He would categorize her as being a soccer mom. Her hips and breasts had filled out over the years, but she wasn't large. She had shoulder length blonde hair that she kept in step with whatever the latest fashion was, and she usually dressed in skirts and blouses.

Sue wasn't dressed any differently than usual, but her skirt was lifted up and tucked into its waistband. The lifted skirt revealed a series of leather straps, and those leather straps held a very realistic cock shaped dildo pressed to her pussy. Sue was stroking the shaft as if it were real, and grinned at Rick when she realized he was watching.

"You got the right idea, but I think we can get even more of the products into the shot. We'll shoot as much as we want and do the editing later." Talia replied.

Rick thought about trying to get away, but his feet were tied to close together for him to try and move. A hop would be all that he would be able to manage, and that would not be good enough. He could only watch as Ms. Pittman grabbed another leather and item from the table. She stepped in front of him and began unbuckling his pants. He soon felt his pants and then his briefs slide down his legs and pool around his feet, and then what he feared happened.

"Well Rick, I had a feeling you would do your part, and I was right. Sue, come take a look at this." Talia said with a smile.

Sue came around the table and whistled at what she saw. "I told you he would rise to the occasion. I have a talent for spotting the right guy. The cock looks so hard that it must be hurting." She said.

Rick would have blushed more it would have been possible. He turned his head away from them, but groaned aloud when he felt Sue wrap her cool hand around his hard, hot dick.

"Talia, we can't let that go to waste." Sue said excitedly.

"Don't worry about that. I plan on getting a stellar performance out of our boy." She replied.

Rick felt movement and turned his head to see Ms. Pittman kneeling down in front of him. Even though he had not wanted this, he was mentally pleading with her to take his cock into her mouth. It wouldn't take much, as he was ready to explode. Instead, Ms. Pittman produced the toy she was holding. She wrapped the leather straps around the base of his cock and behind his balls, and pulled them tight. Another strap separated his testicles and was pulled tight, making his cock throb even more. He looked down when she was done and saw that his cock and balls were neatly separated and swollen like never before.

Ms. Pittman stepped away and checked the cameras again. When she was satisfied, she returned to the table where Rick and Sue were waiting. She grabbed Rick by his shoulders and guided him so that he was facing the table. For fear of falling, he followed her guidance and was soon bent at the waist with his upper body pressed against the cool surface of the table. His ass was angled upward and he soon felt Sues hand on his hot skin.

The two women were talking and Rick was not paying any attention. He still could not believe how he had been put in this situation. He didn't pay attention until Sue grabbed a few more leather items from the table. He felt her and Ms. Pittman working with the cuffs on his ankles and then heard the vibrations through the table that his face lay on. "Relax so we can get you into the right position." Ms. Pittman told him. He didn't know what she meant, but soon felt his legs being pulled outward. He saw a chance to escape and tried to resist, but the two women were both quick and surprisingly strong. He found his legs spread and his ankle now attached to the legs of the table. He was even more vulnerable than before. He wanted to scream, but feared the embarrassment of someone coming to his aid. It also did not help that his very hard cock was betraying him at every turn.

"This should do the job quickly. Let me get one of the cameras so that we can get a good close-up." Ms. Pittman said.

Rick felt her leave and quickly return. He didn't know what she had in mind, but he was sure it was another one of the client's products. He soon found that he was correct when he felt something cold against his ass. He tried to rise, but his legs were spread too far apart, and a hand quickly pressed into the small of his back.

"Keep still so we can use this correctly." Ms. Pittman instructed. Rick felt wetness along with the cold, as the device parted the tight ring of his ass. His fear was lessened as the item slipped into him, and he found that it was quite thin. He breathed a sigh of relief, but soon felt the coldness slip deep into his bowels. It spread out like a liquid and he realized that he was being filled with some kind of lubricant. There wasn't any time to contemplate what was going on, because the thin tube was quickly removed, causing his cock to throb anew.

Rick felt a new coldness against his ass, and another soft point pushed past his sphincter. He knew it wasn't the fake cock that Sue was sporting because of how thin the tip was, and he thought it might be more lube until the body began to widen. Sue must have done this before he thought, because she took her time. She would stop just short of him feeling uncomfortable and rest a while before pushing more of the toy inside. After ten minutes of this treatment, Rick felt as if she had lodged a construction cone up his ass. Oddly, it didn't hurt, and deep warmth was spreading through his loins.

"This one worked like a charm. I've got him nice and open and we didn't have any problems. Have you ever taken it up the ass Rick?" Sue asked him. Rick replied by shaking his head from side to side. He had seen such things done in movie but he had never done anything like it.

"The trickiest part is opening that ass. Now that it's nice and ready, we can get on with the show." Sue told him.

Rick had not looked through the table, but the bobbing of his cock caught his eye. It was deep red and he could see the veins standing up along the shaft. His attention was soon drawn back to his ass as Sue slowly pulled the cone-like object free. He gasped at the cool air the flooded into his open bowels, and his muscles contracted, causing a wet trickle of lube to ooze from his hole.

"That's ripe and waiting." Sue said, and he felt her hand grip his ass cheek. He then felt the blunt tip of her fake cock against his hole and prepared himself for what was coming. He gritted his teeth as he felt the pressure of the blunt head, but wasn't prepared for it to slip in so easily. He felt a minor pop as the head slipped past his relaxed ring and gasped from the full feeling and not from any discomfort.

"Let's work this baby deep." Sue told him as she began slowly rocking back and forth. She gained deeper passage with every stroke and Rick found himself sweating as she did so. He was panting and drooling around the ring in his mouth by the time he felt her thighs pressing against the back of his. There was now no doubt that Sue had done this before. She soon picked up speed, but not too fast. She fucked the cock into him with long slow strokes that had his cock bobbing with each tap on his prostate. A steady stream oozed from his cock, even though the straps kept him from fully climaxing.

"Damn, that is going to sell millions." He heard Ms. Pittman say. He felt what could only be her hand rubbing his ass-cheeks light and slow. Her hand disappeared as quickly as it had come, and he felt then saw her move. She had the video camera in her hand and had slid underneath the table. She filmed the cock slowly thrusting into his hole before moving on to his cock. She lastly filmed his face, which was sweaty and flushed against the cool glass.

"Have we got enough footage? I don't think I'm going to last too much longer." Sue asked.

"I've got enough for now. You can finish up." Ms. Pittman said.

Rick didn't know that the dildo had another end that was inserted into Sue's cunt, and she was on the verge of climaxing. He only felt her tempo increase and felt the dildo hitting with a stronger force. His prostate was being pushed like a bulb filled with cream, and his cock leaked even more. His body was shaking, and he watched, limply on the table as Ms. Pittman began to untie the straps that bound his cock. She had only just begun when he felt Sue's movements become erratic. Her hands dug firmly into his hips and she ground her cock deep into him like some horse-dick, hung porno stud.

Rick felt her shiver and quake and knew that she was climaxing. She shook violently for almost a minute before he felt her breasts press heavily against his back. He could feel her sweat running down her breasts and down his back in a small stream. He found that he was the one that was now shaking, and Sue continued to slowly ream his ass with her cock. It was deeper now, and providing constant pressure deep in his ass.

Rick watched Ms. Pittman through the table with sweat stinging his eyes. She was holding the camera in one hand and working on the straps that bound his cock with the other. The work was slow, but he groaned like a bitch in heat as the straps finally came free. He watched as Ms. Pittman dropped the straps and gripped his cock in her tight fist. She stroked him upward toward the table, and to the beat of Sues cock driving into his ass. Her had hand was the extra that he needed, and there were no straps to hold his climax back.

Rick shook on the table as he felt his stomach tighten. He would have sworn that even his ass climaxed. It seemed to open up and take even more of the fake cock and he whimpered a string of gibberish as his seed burst from his cock. His discharge was thick and creamy as it splashed against the glass above and then back down onto his shaft and Ms. Pittman's hand. She milked him like a farmer until he feared he would black out. He could see through the creamy mess that clung to the table, and saw that her hand was coated in his seed.

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