The Boss Plays with Dolls Pt. 02

Joe had been caught by his personal assistant Paula while fucking an inflatable doll in her office. She had also discovered the collection of voyeuristic pictures Joe had taken of her butt and of some other women in the office.

When Paula had left afterwards for the weekend she hadn't decided on whether to report her boss or take another course of action. She wanted to discuss the situation with the other women involved before making a decision.

Joe spent the entire weekend worrying about what was going to happen with his job. Just after lunch on Monday Paula told him "There will be a private meeting tonight after work in the conference room with the other women. We'll let you know at that time what we've decided."

Although Joe begged Paula to give him an indication of what was going to happen all she would say is "You'll know later. Be there and be prepared for anything."

Shortly after 5PM Joe walked into the conference room. Paula was sitting at one end of the table. Julie, Jenny, Teresa, Emily, and Danielle were also there.

This was the entire group of women that Joe had included in the collection of pictures he had taken with his spy cameras. He felt certain that each of the women were now aware of the pictures and what he had been using them for.

Paula had Joe take a seat at the opposite end of the table. She said "Before we discuss our decision with you, we're going to watch a little slide show that I'm sure you will enjoy. Do not talk until you are told."

Julie turned on the power for the large video screen on the wall and Paula started the slide show. The first picture that appeared was Joe sitting at his desk, shirt unbuttoned, pants down, and holding his hard cock. The room was immediately filled with comments and laughter. The next picture was virtually the same except Joe had an expression of ecstasy and cum shooting on his belly.

Joe was already feeling fully embarrassed and the slide show had only just started. Paula had included over fifty pictures taken from the collection that Joe had saved on his flash drive. As each picture was displayed the women continued to make comments and laugh.

With each picture Joe had to remain quiet as his embarrassment increased. Picture after picture showed him playing with his excited cock. In a number of them he was also ejaculating and in some Joe was seen licking his cum from his fingers.

Paula also included a few pictures of Joe wearing panties with an obvious erection. The women especially enjoyed making humiliating and derogatory comments about their boss at seeing him wearing silky women's underpants.

After what seemed like an eternity to Joe, the slideshow ended. Paula instructed Joe to stand up and said "It's obvious to all of us that you are a depraved pervert who needs to be punished for your naughty thoughtless and hurtful actions. While losing your job would be justified, we've agreed to offer you the option of a punishment that will be more appropriate."

"So which would you prefer? Should we report your behavior to the owners of the company or do you agree to accept a punishment that we have in mind?"

Although Joe had no idea what his punishment would be he agreed to accept it rather than lose his job. Paula then informed him "Each Monday after work we are going to have a private meeting with you here in the conference room. You will be required to do whatever we tell you. If you don't follow our instructions without hesitation we will report your deviant actions to the owners of the company. Do you have any questions?"

Joe had no questions. Paula said "In that case Julie will now take over today's meeting."

Julie had a wicked smile as she stood up. She looked at Joe and said "Well boss, we have all become aware that you secretly took pictures of each of us, specifically our rear ends."

After a slight pause Julie turned her butt towards Joe. She looked over her shoulder at her boss, patted her butt cheek and asked "Is this what you like boss? Do you like to look at my butt?"

Joe was embarrassed. When he hesitated Julie said "Tell me. I want to know."

When Joe admitted that he did Julie asked "Have you ever masturbated while either fantasizing about my butt or while looking at it?"

Joe felt even more embarrassed as he admitted to masturbating while doing both. Julie said "Yes, I thought so."

"Since we also know that you like panties so much, I assume you sometimes think about seeing my butt in panties when you're masturbating. To give you something to think about the next time, I want you to know that today I'm wearing Just My Size white cotton full cut briefs. I wear a size 10 to cover my big rump."

When Julie had finished she sat down and nodded towards Danielle. After standing up and turning her butt towards Joe, Danielle did virtually the same thing as Julie including the questions. Before sitting down Danielle also informed Joe on the color, type, and size of panties that she was wearing.

Each woman including Paula took their turn in asking Joe the same group of questions and had him look at their butt as they described the panties they were wearing that day.

Joe admitted to each of the women that he had masturbated with them in mind. As he stood there looking at each of their big butts while listening to each describe the panties they had on, Joe couldn't keep from getting aroused.

After all six women had taken their turn, Julie made a comment about the obvious bulge in the front of Joe's pants. As she looked at her boss she said to the other women "It seems that our boss has enjoyed our little question and answer session. Just look at his pants. It appears that he's already gotten a boner."

Paula chuckled. "Oh my goodness Joe, pull your pants down so we can see what's causing that little bulge."

Joe hesitated for a moment but then undid his pants. As he pulled his underwear down in the front his erect penis popped out. Teresa sarcastically said "My goodness, our boss did get a boner during our little session. He must like thinking about the underpants that we're wearing."

Joe's face was beet red as the women laughed and made humiliating comments about his aroused little penis.

After a short time Teresa asked "Are you already planning to rub your boner after we leave boss?"

Danielle quickly chimed in. "Oh I'm sure he is, but I bet he would enjoy himself even more if we let him rub his boner right now."

As the other women laughed and agreed Emily said "You know, I really don't want to look at his disgusting little pee-pee while he plays with it. I agree that we should let him rub his boner right now but he should do it with his pants on so we don't have to look at it."

The women liked Emily's suggestion. After instructing Joe to pull his pants back up Paula said "Okay boss, start rubbing your boner for us."

When Joe momentarily hesitated Paula reminded him that he must do as he's told or pay the consequences. Joe's face was red with embarrassment as he placed his hand on his pants and started rubbing his cock with the six women watching him.

After about a minute Julie said "Come on boss, you don't seem to be enjoying yourself as much as you should be. Maybe you need to rub yourself faster. And while you're doing it, tell us that you've got a big boner and you like to masturbate it."

Joe started rubbing himself faster and the women laughed when he said "I've got a big boner and I like to masturbate it."

Emily commented "Well it looks like he's starting to enjoy himself now."

Julie agreed. "Yes, it does seem like he's enjoying it more than he was but he would probably enjoy himself even more if he rubbed himself a little bit faster."

Joe was already struggling to control his excitement. When he again increased the pace for rubbing his erection he knew he couldn't last much longer. Joe was trying desperately to avoid the embarrassment of cumming in his pants. He was hoping the women would either tell him to stop rubbing his cock or have him take his pants off.

Danielle replied "You know boss, I agree with Julie. I think you would get more pleasure if you rubbed your boner faster for us."

As Joe rapidly rubbed his excited hard cock through his pants Danielle added "Tell us again about your boner and what you like to do."

At that moment Joe felt the familiar tingling sensation of pleasure in his penis. He knew he could no longer stop the inevitable. With six women from his office watching him, he was going to cum in his pants.

Following Danielle's instructions Joe said "Yes, I've got a big boner and I like to masturbate it."

The excitement from saying those words added to his pleasure and it was more than Joe could handle. He groaned loudly as he felt a warm stream of semen squirt into his underwear.

The women knew immediately by the expression on Joe's face that he was ejaculating. His face seemed to get even redder than it had been as a wet spot appeared in his pants.

As Joe continued moaning and rubbing his cock the spot grew bigger. Within seconds the front of his pants were wet and frothy from the large load of cum Joe had released in them.

Teresa immediately commented "Oh boss, it looks like you've cum in your pants! Can't you control yourself any better than that?"

As the other women laughed and made comments Joe stood quietly feeling embarrassed and humiliated. After each of the women had berated Joe for his lack of self control Paula announced that the meeting was adjourned. She also reminded everyone there would be another meeting the next Monday at the same time.

When the other women were gone Paula told Joe "It certainly looks like you enjoyed our first meeting. I hope you also enjoy explaining to your wife as to how you cum in your pants at work. I only wish I could be around to hear that."

Paula laughed at Joe's predicament and as she turned to walk away she said "Well you have a good night boss!"

Joe wasn't certain as to what he was going to do but he did call his wife to say he was working late. Afterwards he went to the restroom and washed his pants out as best as he could. It took well over an hour before they dried enough for him to go home.

The remainder of the week was difficult for Joe. Although there was nothing out of the ordinary Joe felt awkward whenever he had to interact with any of the women who had been at the meeting.

On Friday before leaving the office Paula told Joe "Be sure to have your inflatable friend with you on Monday. She will be joining us for our meeting."

It was just before 5PM on Monday when Paula reminded Joe "Our meeting will begin in fifteen minutes. Get your inflatable friend ready and bring her with you. Your favorite employees are all anxious to meet her."

Joe walked into the conference room carrying the inflatable doll. Paula immediately instructed him "Sit your guest on the table and introduce her."

When Joe introduced the doll as Betty, Paula said "Well that isn't her complete name. You need to be more respectful Joe and introduce her by her full name."

Joe hesitated then blushed as he said "Her full name is Big Butt Betty."

As the women at the table snickered and made comments Paula instructed Joe to stand at the head of the table and remove his clothes. Joe slowly took off all his clothes and was soon standing completely naked in front of his female employees.

Joe was red faced with embarrassment having the women see him fully naked. His humiliation increased when some of the women made comments about how small his limp penis was.

Paula laughed then commented "It is small now but I'm certain he knows how to make it get bigger. Show us what you do Joe to make your penis get bigger."

As Joe began to rub his balls and cock Paula said "Come on ladies. Let's encourage our boss while he plays with his penis. Maybe it will get bigger right before our eyes."

Due to his embarrassment it took Joe longer than usual to get aroused but after a few minutes his five and a half inches of cock was standing erect. Teresa chuckled. "Well it is bigger but it's far from being big."

Paula commented "Since he finally got his penis erect I think our boss is ready to have fun with his friend. Does anyone think Joe would enjoy a blow job from Betty to get himself a little more aroused?"

Jenny, the young receptionist giggled. "Oh god yes, I bet he loves getting blow jobs from Betty."

When the other women at the table agreed Paula picked up the doll and placed her on the edge of the table where Joe was standing. She held it slightly forward and said "It looks like she's ready for you Joe. Show us how she sucks your cock."

Joe's face was bright red as he moved directly in front of the doll. After putting his hand on the back of Betty's head he guided his hard cock into her mouth. While holding her head Joe began thrusting his cock in and out of Betty's mouth.

The women laughed and made humiliating comments while Joe slowly face fucked his inflatable doll. As Joe moaned and groaned Paula told him "Don't get too excited yet boss, I'm certain you want your big butt friend to do more than just give you a blow job."

After allowing Joe a few minutes to pleasure himself using Betty's mouth Paula said "Now that Betty has got you worked up with that blow job we have a very special treat for you to enjoy. You can give her a rest while we get things ready and tell you about the fun you get to have with Betty."

Joe removed his cock from Betty's mouth. He looked even more embarrassed as he stood in front of the women with an excited fully erect penis.

As Teresa powered up the large video screen Paula told Joe "Our little tech geek Emily has created a special treat for you to enjoy. She was able to use the pictures that you took of us along with the sound from an instructional video she found online. Emily put it all together including some video excerpts made especially for you."

When Emily acknowledged that everything was set up and ready to go Paula said "Alright Joe, now all you need to do is follow the instructions in the video."

Music began to play in the background of the video as Emily appeared on the screen. She smiled and said "I have a fun game of self control for you to play today boss that I'm sure you will enjoy. Lay your friend on the table on her back with her legs in the air then put your excited cock into her pussy. I will wait a moment for you to get ready."

Joe couldn't believe the women had made a video for him. He had no idea what they had in mind and his face felt warm with embarrassment as the women watched him slide his hard cock into Betty.

After about thirty seconds Emily continued speaking. "Are you ready to play boss? Start fucking your friend's pussy and keep in time with the metronome."

As a metronome began clicking, pictures that Joe had taken of his employees butts appeared on the screen and changed in sync with each click. The pace was slow at first but at fifteen second intervals throughout the first minute the speed increased.

At each interval Emily's voice could be heard. "Does your cock feel good in that pussy boss? Oh I bet it does! Just don't think about it too much. Your friend needs lots of pleasure and she's not ready for you to cum!"

After the first minute the pace slowed to the initial speed then again increased every fifteen seconds for another minute. It was already obvious by his moans and groans that Joe was having a difficult time controlling himself.

At the end of two minutes Emily again appeared in the video. "I bet your cock is starting to feel all tingly isn't it boss? To help you control yourself you may now stop. Relax for a moment before the second round begins."

Emily's instructions continued. "Remove your cock from your friends pussy. Do not touch it and do not say a word. Put your hands on your hips and slowly thrust them. Let everyone have an unobstructed view of your excited cock. Round two will begin momentarily."

As Joe stood there with his very excited cock standing at full attention each of the women made comments to increase his embarrassment and humiliation. After a minute Teresa appeared on the video screen. "Okay boss, I'm sure your excited cock will be happy to know it's time to begin round two."

Teresa instructed Joe to place Betty on the table on her hands and knees. "Your friend now wants the pleasure of being fucked doggy style. Mount her pussy and get ready to make her bark."

Joe's embarrassment continued as he moved behind Betty and guided his cock into her pussy. Just like the first time the metronome started clicking at a slow pace with the speed increasing every fifteen seconds. Again pictures of each of the women's butts flashed in sync on the screen. This time it was Teresa making the comments.

After doing well at controlling himself throughout the first minute of round two Joe thought the pace would decrease like it had the first time. Instead the clicking on the metronome got faster. During the following fifteen second interval the pace increased even more. As the pace increased Joe groaned out loudly exclaiming "Oh my god!"

With a tight grip on Big Butt Betty Joe rapidly thrust his cock in and out of her pussy. He knew he was nearing his point of no return when the pace on the metronome finally decreased.

As his thrusts slowed down Joe was able to maintain control and keep himself from ejaculating. When two minutes were up Teresa announced that round two was complete and Joe could remove his cock from Betty's pussy.

Joe let out a deep sigh of relief. The tip of his excited cock was covered with sticky pre-cum when Joe removed it from the inflatable doll's pussy. Joe was again instructed to not speak and to stand with hands on his hips in order to allow the women to view his cock.

When Paula saw the pre-cum on Joe's cock she immediately commented "It certainly looks like you're enjoying your friend and the video Joe."

After a one minute break, Danielle appeared in the video and began speaking. "Okay boss, your friend is already in position to enjoy the next round of fun. This time she wants your cock in her butt. Stick your excited cock up her poop chute. As you fuck your friends big butt imagine yourself doing this with each of the women in this room. You seem to already know that each of us like getting butt fucked!"

Joe pushed his hard cock into Betty's butt hole as instructed and began fucking her in sync with the clicking metronome. During the first minute the routine was identical to the first two rounds. Joe kept with the pace that was set and had no problem controlling his excitement.

As the second minute in the round began, the pace on the metronome increased significantly. Joe began to rapidly fuck Betty's butt. After ten seconds the pace increased again and Joe had to fuck the doll faster than he had at any previous time during the video.

Joe was relieved when the pace slowed at the next interval but after fifteen seconds the pace of the metronome again increased. Joe knew at the rapid pace he wouldn't be able to control his excitement for much longer. After ten more seconds the pace decreased and Joe was able to feel more under control.

The six women sitting at the table watching their boss humiliate himself as he fucked his inflatable doll were ready for what they knew was coming next. Thus far things had gone exactly as planned. The video had brought their boss to the edge multiple times already. They were feeling certain he would lose control in the manner they had hoped.

Joe assumed he was nearing the end of another round but after one more fifteen second interval at the slower pace the metronome started clicking at a high speed. Ten seconds later it increased again causing Joe to fuck Betty with extremely rapid thrusts. He was breathing heavily and again groaning "Oh my god!".