The Boss Plays with Dolls Pt. 01

It had been a little over six months since Joe had taken the job as a controller for a small accounting business. The office location where he worked had ten employees and all were female. It was the perfect job for Joe. He had always been slightly chauvinistic and he enjoyed telling women to do things for him.

Joe was thirty-two. His personal assistant and office manager Paula was fifty-one. She was attractive but motherly with saggy breasts, short brown hair and blue eyes. Paula also had big hips, thick thighs, and a large plump butt. She was a petite five foot three inches tall and her short stature made her large rear end look even bigger than it was.

Joe always liked women with larger butts. Having the opportunity to gaze at Paula's large rear end everyday made Joe's work days even more enjoyable.

Of the other nine women working in the office, five of them also had larger than average rumps for their body size. Joe was pretty much in heaven. He especially enjoyed the days when the women wore tight pants. Many times they would have visible panty lines as well. It was sometimes difficult for Joe to not get caught staring at his employee's big butts.

One of Joe's other pleasures was getting a down the back of the pants peek at a woman's pretty underpants. He was so obsessed by it that he would purposely request items in a lower drawer of a filing cabinet just to watch a woman crouch down, hoping to see her panties. He seemed to get that view often with Paula and truly loved seeing the silky control briefs or panty girdles she often wore.

Despite being happily married with a baby daughter, Joe masturbated often while thinking about the women in his office. He would get so horny during his work day that he pleasured himself in the restroom as he fantasized about his employees.

Joe was also somewhat of a voyeur. For years he had taken pictures of the big butt on an unsuspecting woman in a public place and posted them to a photo sharing website. Joe loved to masturbate as he looked at the pictures and would fantasize about sniffing the women's butts.

Prior to getting married, Joe had a perversion for having sex with inflatable dolls. It was one of his naughty pleasures that he had given up but he fondly remembered it as being some of the best sex he ever had.

It was only a matter of time before Joe was wishing he had some pictures of his employee's large butts to view while he masturbated. In order to get the pictures he desired, Joe purchased two motion activated spy cameras. He knew it was risky to take pictures of his employees without their knowledge but the voyeur in him couldn't resist.

Joe strategically positioned one camera near the filing cabinets where it would capture pictures of the women bending over or squatting down. He put the second camera under his desk in a position to capture pictures of the women walking in and out of his office.

Because of the location of the second camera Joe knew there was also the potential of capturing views up the skirts or dresses of a woman sitting in the chair at the front of his desk. It wasn't his biggest thrill but Joe knew he would enjoy any beaver shots or panty peeks that he may get.

After the first day in operation, Joe was excited to see what his camera's had captured. His twenty-one year old receptionist Jenny had been sitting in his office earlier that day wearing a short skirt with pantyhose. Joe was excited by the prospect of what he may see.

When Joe viewed the pictures from his under desk camera the results were better than he had hoped. His camera had captured some great views up Jenny's skirt. She was not wearing panties under her hose and her young hairy beaver was clearly visible.

Joe's cock was already hard before he even started looking at the pictures captured by his second camera. As he went through those pictures Joe found he'd gotten a number of nice butt pictures along with a few good panty peeks down the back of one woman's pants.

Joe was pleased by the pictures he had captured in just one day. It didn't take long before Joe had taken his hard cock out of his pants and started stroking it. As he sat at his desk looking at the pictures Joe stroked his cock and ejaculated on the carpet protector under his chair.

Over time as his collection of pictures grew, Joe organized them by each employee on a flash drive that he kept in his briefcase. At any time that he desired he could view a slideshow with various pictures of each of his employees.

It became routine for Joe to work late. On many evenings after everyone had left the office Joe would insert the flash drive in his laptop then masturbate and cum while enjoying a slideshow of an employee.

After a number of weeks of Joe's after work hours masturbation sessions he started thinking about the fun he could have if he had an inflatable doll. Joe had the idea of having sex with a doll and fantasizing it was the employee whose pictures he was viewing.

Within a week of searching Joe had found the perfect doll for his needs at an online site for sex toys. Big Butt Betty had forty-six inch hips with three usable orifices.

In addition to the doll Joe also purchased a small plug-in inflating pump. He planned to keep Betty deflated to hide her. Having the pump would make the task of preparing her for pleasure much easier.

On the first day after Big Butt Betty arrived Joe could hardly wait to use her. It seemed to him that it took forever for everyone to leave the office that day.

After getting Betty inflated he bent her over his desk. He turned on a slideshow of his employee Julie, a middle aged divorcee with a very large butt and thick thighs. While still fully dressed Joe began to rub his cock against Betty's big butt while viewing the slideshow of Julie.

It took very little time before Joe was aroused and removed his pants. After sitting down in his chair he picked up the doll and said "I have a special seat ready for you today Julie. I know you've always wanted to sit on this cock."

With Betty facing away from him he lowered the doll's butt onto his erect cock. As he began moving her up and down Joe said "oh yea Julie, ride that cock. I know how much you love it in your big butt."

Joe was fully enjoying the pleasure as he bounced the doll on his lap while viewing the slideshow of Julie's large fat butt. After several minutes he began to rapidly move the doll up and down on his cock.

As Joe neared his point of no return he exclaimed "oh my god yes Julie, you really know how to ride a cock. I love fucking your sexy fat butt!"

It had been a long time since Joe had enjoyed this kind of intense pleasure. He groaned loudly and shoved his cock deep into Betty's butt. As he began filling her with a massive load of cum he said "oh yea Julie take that cock. I know you love it."

When Joe had finished ejaculating he lifted the doll from his cock. He held Betty up over his face and allowed his cum to drain from her butt into his eager waiting mouth.

After taking and swallowing every bit of his cum Joe sighed with pleasure. As he sat there still watching the slide show he said "oh Julie, I have no doubt that you really would love for me to eat my load from your horny hot butt hole. I can just imagine how good your hole smells and tastes."

Over the next several weeks Joe enjoyed a number of after hours sexual encounters in his office with his big butt inflatable doll. Just like that first time Joe would be viewing a slideshow of a big butt employee and fantasize it was her that he was having sex with.

Initially Joe limited his activity to his own office but eventually he started enjoying his pleasure at the desks of the various women. Joe would set the slideshow on his laptop for that particular employee then enjoy the pleasure from one or more of Big Butt Betty's holes.

Joe seemed to find it more arousing to do his decadent deed while being at his employee's desk. For the women who had pictures of husbands on their desks Joe would get turned on imagining them watching as he fucked their wives.

One afternoon while working on a project with his assistant Paula, Joe had a number of opportunities to admire her large butt. She was wearing tight white pants and whenever she walked in front of him Joe's eyes became fixated on her rear end.

As the afternoon went on Joe struggled to resist his desires to masturbate. The visible panty lines from Paula's control brief pinching her big butt cheeks had Joe about as horny as he could be. He held off on his desires and waited anxiously for the day to end. Joe knew he would be fucking his doll and fantasizing about Paula's butt.

By shortly after 5PM, everyone was gone from the office except for Paula. Joe was more than ready to begin his fun but Paula continued working later than usual. After nearly another hour she came into his office and told Joe "I think I've had enough for one day. Have a good night and I'll see you in the morning."

As soon as Paula left the building Joe watched her through a window. When he saw her car leave the parking lot he was ready to get started with his fun.

After quickly inflating Big Butt Betty, Joe took the doll and his laptop into Paula's office. The smell of her perfume was still lingering and Joe was enjoying the sweet fragrance as he started to unbutton his shirt.

In less than a minute Joe was standing completely naked in Paula's office and his cock was getting aroused. He opened the file on the flash drive that contained his pictures of Paula and set the viewing to slide show. Before the first picture of her big butt appeared Joe had a full erection.

Joe put Betty on Paula's desk with her big bottom up and said "I've been waiting all day Paula for you to get your pants down with your sexy big butt ready for me."

As Joe slid his excited cock into his doll's butt hole he exclaimed "oh god yes Paula, your big plump rump is going to get a good butt fucking tonight! I hope your husband likes watching you get your butt fucked!"

During her lunch break that day, Paula had bought some items for her family's dinner that night. About fifteen minutes after leaving the office Paula remembered she had left the items in the refrigerator and headed back to get them.

When Paula arrived back at the office she saw that Joe's car was still in the parking lot. As soon as she unlocked the door and let herself in she heard Joe's voice coming from her office saying "oh god yes, I love fucking your big sexy butt. And I know you love it too. My god it feels so good having my big cock in your butt!"

Paula immediately thought "what is going on? Who is he talking too?"

As Paula walked hesitantly towards her office Joe was talking continuously. She heard him say "oh my god yes, I hope you're ready for some cum. I'm going to shoot my load in your big fat butt and then I'm going to eat it."

Paula stopped outside her office thinking Joe was having sex with someone. She didn't know who it could be or why in her office. Regardless, Paula didn't want to walk in on them and decided to leave.

Just as Paula was turning around to walk out she heard Joe loudly exclaim "oh god yes Paula, ride my cock! Ride it faster. Oh my god you're gonna make me shoot my load in your butt!"

When Paula heard what Joe had said she quickly turned back and looked in the open door. She saw Joe standing naked and rapidly thrusting his cock into the inflatable doll on her desk. At that very moment Joe began to ejaculate and shouted out "oh Paula, I'm filling your sexy fat butt with cum!"

Paula immediately screamed "oh my god Joe, what the hell are you doing? I can't believe you're in my office having sex with a doll!"

Joe was startled by the interruption. His slide show of Paula was playing on his laptop and he was standing there with his cock inside the cum filled butt hole of Big Butt Betty.

He was instantly overcome with embarrassment and didn't know what to do or say. Joe's clothes were on the floor and his only means for covering himself was with the doll.

As Joe stammered trying to find words to say his cock popped out of Betty and cum began dripping from the butt hole onto the floor. Paula immediately noticed the cum and said "oh my god, that's so disgusting."

Joe tried to apologize but couldn't get a word in. Paula was livid. She was ranting on about Joe being sick and perverted. Paula then noticed what Joe had been looking at on his laptop and her anger multiplied by ten times what it already was. She said "my god, those are pictures of me. You are a fucking pervert!"

Paula saw the flash drive plugged into Joe's laptop. When Joe admitted that the pictures he was looking at were saved on the flash drive Paula took it. She shook her head with disgust and got quiet for a moment before telling Joe "I need to get home to my family now but we're not done talking. We're going to have a very serious discussion in the morning about how to deal with this situation."

During that entire night Joe worried about the consequences he may face. He realized he could lose his job and he also knew his marriage could be in jeopardy over what had happened. With Paula having the flash drive she not only had evidence of his voyeuristic activities from the hidden spy cameras, she also had pictures of him.

In addition to the pictures Joe had saved on the flash drive of the women in his office there was a file that contained several hundred pictures of himself. Most of them were taken in his office while masturbating. There were also pictures of Joe masturbating while wearing panties.

Joe was hoping that Paula wouldn't look at the pictures but he was certain she would. After a sleepless night, he went to work in the morning fearing what that day would bring.

When Joe arrived at the office that morning Paula was already there and waiting for him. She immediately followed him into his office and shut the door. It was like they had never left as Paula immediately began talking about how disappointed and disgusted she was by what Joe had done.

Paula told Joe "I was so angry last night that my first instinct was to report your actions to the owners of the company. I know that would cost you your job and even though you deserve it I hate to put that hardship on your family. Right now I just don't know what I should do."

Joe cried as he apologized over and over. He begged Paula not to tell anyone. He told Paula he had removed the cameras and promised to never do anything like that again.

After letting Joe plead his case Paula said "as much as I hate to, I feel like I do have to discuss this with the other women that you took pictures of. If I don't and they later find out, my job would be in jeopardy."

Although Joe hated for the others to know he told Paula he understood her predicament. He apologized for putting her in that situation and said "let me know as soon as you can what the ladies decide. I'll accept whatever the decision is."

It was a Friday and by the end of the day Paula told Joe she hadn't got a chance to discuss things with the other women. He would have to wait until Monday to know his fate.