Author's note: Hello readers. I hope you enjoy another story featuring Pam Beesly from The Office. This idea was suggested by an anonymous comment left on my most recent Office story. That comment ask for a lesbian ass worship story between Pam and Jan. That idea really jumped out at me for some reason and here is the result. I hope it does the subject matter justice as it is something I have never written before.
As always, comments are much appreciated. I am also happy to hear any story ideas for The Office and select other TV shows including Parks and Rec and Modern Family. Either comment on the story through Literotica or send me a PM. I always make sure to check them all. If you want a direct reply, please PM me so it is sent to my email account.
Thanks for reading!
The Office - Jan's Office
Pam Beesly was sitting at her desk at the Dunder Mifflin corporate offices when her phone lit up with a call from her boss. Pam had transferred to the corporate offices to pursue a graphic design internship that was being offered. To make ends meet, Pam had taken a job as the personal assistant to Jan Levinson. Jan was one of the higher ranking executives that Dunder Mifflin had and Pam had been surprised that the position had been open. However, it had only taken Pam about a month to find out why the job had not been filled. Especially with how well paying it was.
"Pam would you come into my office please," Jan said over the intercom system on Pam's phone. "Put the phones on hold."
It was the same thing Jan said every single time she called Pam into her office for the reason why no one kept the assistant job. That reason was because Jan was a dominant lesbian who liked to use her personal assistants sexually. Jan seduced her assistants over a drawn out period of time. Some of them fell into her trap and had simply left for other opportunities and some previous potential assistants had left the job in disgust. Pam happened to be one that fell for the seduction. Her own naivety about sex and her previous sheltered life combined with her submissive nature had led to Pam becoming Jan's full time assistant for all of her boss's needs and desires.
A huge part of Pam hated herself for allowing Jan to use her body like an object for her own pleasures. However, a tiny part of her liked being treated in such a degrading way and that was why she had let it continue for so long. She kept telling herself that she would end it after every embarrassing encounter with her superior, but that time never seemed to come. Plus she really needed the money to make ends meet.
Once Jan finished her message, Pam did as she was told. She hung up the phone, set the system to voicemail, and stood up from her desk. Pam was dressed in smart business attire. Jan was very particular about what Pam was to wear to work every day and had even taken the shy receptionist turned graphic design intern shopping to make sure her clothes were up to Jan's standards.
Today, Pam was dressed in a tight black pencil skirt, stylish heels, a fashionable purple top that displayed her impressive chest while staying modest, and a set of lingerie that Jan had bought for her. Her heels clicked against the marble floors of the corporate offices as she headed to Jan's office. She told herself that she would not let Jan have her way with her again, but there was a voice in Pam's head that knew that was untrue.
Pam knocked on the door of Jan's well-appointed office and waited for Jan to tell her to enter. Once Jan's "come in" was heard, Pam turned the handle of the door, stepped into the office, and closed the door with a soft click behind her.
"You wanted to see me Ms. Levinson?" Pam asked as she had been instructed to do during these situations. The curvy brunette tucked a stray strand of her long hair behind her right ear and looked at the ground while waiting for Jan to answer.
"Ah yes Pam," Jan said without even looking up from the task she was busy with on the computer. "Go ahead and remove your skirt and take your position on the couch. I'll get to you when I'm ready."
Jan used different phrases for all of the different things that she sometimes had Pam do. Jan liked to keep her use of Pam sounding like it was just part of the job and also liked to keep her control over Pam absolute and so she had taught Pam what to do when she said certain things. The phrase she had told Pam today was one of Pam's least favorite. It wasn't that it was unpleasant per say. It was just something that Pam could never really get used to.
Over her several months as Jan's assistant, Jan had Pam do all kinds of sexual things. Pretty much everything had been new to Pam at first since she had never been with a woman sexually before. Some of the things she didn't mind and some she really didn't like at all. At different times, Pam had been told to eat her boss's pussy from underneath her desk during a meeting, had masturbated herself to orgasm while Jan watched, and she had even been fucked by Jan with a strap-on all during work hours. However, on the days that Jan told her to remove her skirt and get on the couch, it meant that Jan was going to play with her assistant's ass that day. Pam had always thought her breasts were her most attractive physical feature, but her boss seemed absolutely obsessed with her butt.
Pam might not have realized how sexy her ass was but anyone who saw it encased in one of her tight skirts would say different. Her ass was plump and round, but also toned and firm. Combined with her curvy hips, Pam's ass really was a work of art. Jan had wanted a piece of Pam's ass since she first met her at the Scranton branch years ago and finally got what she wanted. Jan always got what she wanted.
Pam inwardly sighed and turned away from her boss to face the leather couch on the left side of Jan's large office. She began to work on the clasp of her skirt when Jan cleared her throat. Pam turned her head to look at Jan while still holding onto the now loosened clasp of her skirt.
"Oh and Pam," Jan said while typing and looking at her computer screen, "don't forget about your mouth."
At hearing that, Pam just nodded and turned back to continue removing her skirt. When Jan told her to not forget her mouth, it meant that Pam was to wear the ball gag that Jan kept in a special cabinet in her office. Pam didn't really know why Jan ever had her wear the stupid thing. Pam hated it and had long ago learned that Jan's office was completely soundproofed so it didn't even serve a purpose except for humiliating Pam even more, but Pam supposed that must have been the point.
Pam finished with the clasp on her skirt and wiggled her curvy hips to get it down. The rest of her clothes remained, but with her skirt gone, Pam's stay-up thigh high stockings and lack of panties was revealed. She wondered if Jan was watching her at that point, but Pam doubted it. After folding her skirt and putting it on a spare chair in the office, Pam went over to the cabinet that doubled as Jan's sex toy chest and kneeled down to reach the lowest drawer. Her sexy ass pressed against her heels and Pam's curves were even further accentuated. She pulled a small key that hung from a chain around her neck out from under her shirt, unlocked the drawer, and pulled out the ball gag.
Once the cabinet was safely closed again, Pam rose to her feet and walked the several steps over to the couch. Before taking the position that Jan had taught her to use in this situation, Pam lifted her manicured hands to her mouth and placed the purple ball gag into between her lips and fastened the strap behind her head. It was starting to become second nature for Pam and that always bothered her.
With everything else done, Pam lowered her luscious body onto the leather couch. She laid down on her stomach and placed her hands at her sides. She faced the back of the couch and settled in to wait. Sometimes Jan made her wait a pretty long time, but others she came over right away. This seemed to be one of the days that Pam would have to wait and her thoughts drifted to previous times that Jan had played with her ass.
Sometimes Jan would spend a long time simply rubbing and massaging Pam's ass before letting Pam get back to work. Other times she really went to work with her tongue and licked and kissed Pam's ass all over. There were even a couple of really strange times when Jan had taken a nap using Pam's ass cheeks as her pillow and another time when Jan had used Pam's ass as a table for her lunch.
Pam continued to lay prone on the couch and her mind drifted to Jim. She wondered what he would think of her if he walked into Jan's office right now. It had been Jim who encouraged her to take the internship and helped her find a place to live in the city. They had remained close and had decided they would take things to the next level as soon as Jim could move closer to the city.
Pam was just chuckling on the inside at the thought of Jim fainting if he could see her right now laying down in Jan's office exposed from the waist down with a ball gag firmly strapped into her mouth when she heard Jan's office door click as the older woman locked it. Pam's thoughts were immediately brought back to the present moment as she heard Jan approaching the couch.
Pam felt the weight of Jan's body subtly shift the couch as she sat down. A blush immediately formed over Pam's face when her older boss placed her cold hands onto Pam's ass cheeks. Pam always blushed during her encounters with Jan. She didn't think she would ever get completely used to being used in the way that Jan used her.
Jan gently ran her hands all over the smooth pale skin of Pam's butt. Pam's thought that Jan was obsessed with her subordinate's ass was completely true. Jan had never seen an ass quite as glorious and perfect as Pam's. She absolutely loved playing with it and couldn't have been happier that Pam had succumbed to her seduction all those months ago. She was proving to be the most willing and submissive personal assistant that she had ever had.
Jan's rubbing increased in speed and soon she was squeezing the soft flesh of Pam's ass between her manicured fingers. Jan's blood red nails contrasted sexily with Pam's white skin as she groped her assistant. The Dunder Mifflin executive alternated between firm pressure on Pam to gently running her fingernails over Pam's skin raising goosebumps on Pam's posterior. Pam just focused on keeping any squirming or movement to a minimum. Jan's hands weren't entirely unpleasant on her skin, but the whole situation still made a part of Pam uncomfortable.
After a minute or two of rubbing everything from Pam's ass to the top of her thighs underneath her stay-up stockings and the curve of her lower back, Jan switched from using her hands on Pam to using her mouth. She began with soft kisses to every inch of Pam's exposed skin before beginning to mix in licks with her long tongue. Jan ran her tongue from the very top of Pam's stockings to the same curve in her lower back and hips that she had groped earlier.
Pam was beginning to get more and more turned on when Jan's hands once again firmly grabbed each of Pam's ass cheeks and spread them roughly apart. Pam's more intimate areas were exposed to the chilly air of the office and if Pam had not been wearing the ball gag, she would have moaned audibly at the sensation. Pam immediately felt Jan's tongue pressing against her asshole and couldn't help but to squirm a little bit. Jan simply gripped Pam's curvy hips to keep the prone employee still.
Jan continued to rim out Pam's ass until her tongue began to tire. The older woman then rose from the couch and walked towards her desk.
"Stay Pam," Jan instructed just as Pam was hoping that they were finished for the day. Jan rarely spoke during their encounters outside of giving commands and the occasional dirty talk to Pam.
Pam heard the door of Jan's mini fridge open and close while she was waiting for whatever else Jan wanted to do with her that day. A moment later, Jan rejoined Pam on the couch. She set down the two items in her arms that she had collected on the table near the couch and took another moment to rub Pam's ass again.
"I'm doing something new today Pam so don't be alarmed when you feel it, ok?" Jan spoke in her sing-song voice.
Pam just nodded in affirmation.
"Good girl," Jan said and punctuated her words with a slap to Pam's ass.
Jan had spent time spanking Pam in the past, both for punishments and for her own enjoyment, so Pam knew that spanking was not the new thing that Jan had in mind for her today. Between the degrading comment of being called a good girl and the anticipation of what was coming next, Pam was on edge and her pussy was getting wetter.
Pam could hear Jan fiddling with something before turning back to the couch. All of a sudden, a burst of heat dripped against the smooth skin of Pam's ass. The former receptionist jumped at the sensation and squeaked through her ball gag. She tried to turn her head to look at Jan with big eyes, but couldn't quite turn her neck enough.
"Relax Pam," Jan said. "It's just a little hot wax."
Pam was aware of hot wax being used by some people during sex but never thought she would be experiencing it on her ass in a brightly lit office in the middle of work by her much older female boss. She didn't have much time to think before another drip of wax impacted her skin. This time it was on the opposite cheek. Pam would later learn that Jan was using one of her Serenity by Jan candles to drip wax on her. Specifically, it was a lavender and cucumber sent.
Jan had chosen that candle as she knew the purple color would look beautiful against Pam's skin. She wasn't wrong about that and was getting very horny herself by this point. She absolutely loved putting Pam through things that she had never experienced before and taking full advantage of the woman who was also her employee.
After the next drip of wax, Pam felt an entirely new sensation that made her groan into the ball gag in her mouth. Jan had quickly applied an ice cube from her mini fridge to Pam's ass right on top of the hot wax. The contrast between hot and cold made Pam whimper in pleasure. It was like nothing she had ever felt before and she hated to admit that she was enjoying it.
Jan continued her wax play with Pam's ass until the entire area was covered in random drips of purple wax. It looked like a work of art to Jan, but she couldn't admire it for long as she was getting desperate to get off. Jan quickly walked over to her drawer of sex toys and pulled another new item that she had recently purchased out. It was a strapless dildo. Instead of using a harness like a traditional strap on, one end of the strapless dildo was inserted into pussy of the woman doing the fucking. It left a seven inch dildo sticking straight out of Jan's waist. The point was that it allowed to Jan to eventually orgasm from fucking Pam without any extra stimulation.
Jan took a moment to take her own skirt off before pulling her pantyhose away from her body, pushing her panties to the side and inserting the smaller end of the strapless dildo into her vagina. She closed her eyes at the pleasure and pulled her pantyhose back up. Jan then tore a hole in her pantyhose and worked the business end of the dildo through it so it was hanging free.
She glanced back at Pam who had not moved from her position and felt another throb rush straight to her cunt. She couldn't wait any longer and walked back over to Pam. She grabbed her assistant by the hips and pulled her onto her hands and knees. Pam's ass was arched perfectly in that position and she knew that Jan was going to fuck her.
Sure enough, Pam felt a drop of cold lube drop onto her ass and Jan's long fingers begin to rub it in. Jan had put enough stuff up Pam's ass by this point that it didn't take long for Pam to be loose enough to be ass fucked. As Jan lined the dildo up with Pam's starfish, Pam dropped one of her stocking and heel clad legs to the marble floor of the office. She was bracing herself to be fucked as hard as Jan desired.
Without any more fanfare, Jan pressed forward with her hips and watched Pam's ass take the entire length of the dildo with ease. She felt a tiny amount of pride that Pam had become such a good submissive slut to her, but didn't focus on that for long. The pressure of Pam's ass pressing back against her hips gave Jan immense pleasure and she was soon grinding into Pam. It only took another minute or so before Jan felt the familiar rush of orgasm beginning in her cunt. She ground into Pam harder and rotated her hips to get the dildo to rub against the perfect spot inside of her before suddenly exploding into the climax that she had been craving as soon as she walked past Pam's desk earlier that morning.
Jan always stayed quiet during her orgasms in the office. Just another way to maintain an air of control over Pam and in her place of work. Jan continued to gently grind on Pam as she came down from her orgasm. Once she was back under control, she was ready to give Pam the ass fucking that would remind the assistant what her place really was.
Jan reached down to grab Pam's hips and began to increase both the speed and power of her thrusts. She loved how Pam's hips made the perfect handles for gripping during a pounding. Jan did a lot of yoga and worked out and was in good enough shape to pound Pam hard. She was thrusting harder and harder and Pam's foot that was on the floor began to slip backwards. Pam strained to keep her balance under the hard fucking she was currently receiving as her hair hung down in her face and her breasts shook while still wrapped in her bra and shirt.
Despite her best efforts, Pam's foot finally slipped all of the way and fell into a prone position onto the couch once again. She let out a breath at the sudden impact and weight of Jan on her back who had fallen along with her. Jan's dildo remained completely lodged in Pam's ass in their new position and her mouth was now right next to Pam's ear. That gave her the perfect opportunity to whisper in Pam's ear while also continuing to fuck her ass.
"Such a good little assistant Pam," Jan whispered into Pam's ear as she thrust another couple of times.
"Your ass is perfect," Jan purred with a lick to Pam's ear. "And it's all mine."
With that, Jan raised herself up on her arms one more time and thrust into Pam a dozen or so more times before finally pulling the dildo free of her ass and rising to her feet again. Pam continued to lie on the couch and worked on catching her breath. Jan would tell her when it was ok to get up anyways.
Jan pulled the strapless dildo from her cunt with a wet sound and worked it out of her pantyhose. She cleaned it and herself off with a wet wipe that she kept in a desk drawer, put the dildo away, and pulled on her skirt. She looked no worse for the wear and could have easily conducted a meeting and make no one the wise to what she had just done to Pam.
"Pam, come with me," Jan told the curvy brunette in a business-like tone once again.
Pam climbed to her feet on shaky legs and took a second to get her balance back from the fucking she had just endured. She then followed her boss into the fancy executive bathroom that was connected to her office. Jan indicated to Pam to stand in front of her at the sink. Pam looked at her reflection in the mirror and blushed again at the site of the ball gag in her mouth. Jan began to gently massage her shoulders.
"You did well today Pam," Jan said as she unbuckled the ball gag and placed it on the sink after Pam spit it out. "Just how I expect you to perform your job. Now let me show you my handiwork."
Jan gently grabbed Pam around her shoulders and turned her around. Pam craned her neck around as Jan told her to and gasped when she her ass. It had dry wax all over it and was red in some spots from Jan's hands and the ice and heat that she had applied. Pam had to admit in her mind that it looked really sexy and that her ass did look pretty damn good. Pam also suddenly realized just how horny she really was after this most recent encounter with Jan.
After letting Pam admire her well-fucked ass for a few seconds, Jan turned her assistant around again and pushed on her back until Pam was bent over the sink. Jan then got a washcloth wet with warm water and crouched down to help Pam clean up. It was more for her own extended pleasure than to actually help Pam, but Jan also still needed Pam to be an effective assistant on the business side of things and Jan knew she wouldn't be comfortable or efficient with her ass in its current state.
Jan rubbed the washcloth all over Pam's plump ass. She enjoyed the show as her rubbing was lifting Pam's ass cheeks and making it jiggle the perfect amount. It wasn't long before Jan had all of the wax off of Pam. She then grabbed a bottle of lotion, squirted some into her hands and began to apply it to Pam's skin. Pam moaned at the contact and that was when Jan realized just how turned on and wet her little assistant's pussy really was.
"Do you need to cum Pam?" Jan asked in a serious tone.
"Yes Ms. Levinson," came Pam's very quick reply.
"Well you have a lot of work to get done before leaving today, so I will allow it," Jan said.
Before Pam could even say anything else, Jan was inserting three manicured fingers straight into her dripping wet cunt. The width of three of Jan's fingers plus the intense session she had just been through had Pam nearly screaming at the penetration. She controlled herself to moaning into her hands as she watched her face in the mirror as she was finger fucked.
It only took a few thrusts of her boss's fingers for Pam to go weak at the knees as a violent and rapid orgasm overcame her curvy and petite body. Jan thrust a few more times with her fingers as Pam came down from her climax. She then slipped her fingers from Pam's slick cunt and brought them up to Pam's face. Pam sucked her superior's fingers into her mouth without even thinking twice and cleaned her own juices from Jan's fingers. Pam continued to recover as Jan washed her hands in the sink right next to Pam.
By the time Pam was starting to stand back up, Jan was drying her hands off on a towel near the door.
"Take a few moments to collect yourself Pam," Jan said over her shoulder. "Then back to work. You have voicemails to catch up on and plenty of filing to do."
With that Jan left the bathroom and settled back in at her desk. When she watched Pam leave her office several minutes later with files in her hands, she was already starting to think about what she was going to do to Pam at their next private meeting.
Jan 13, 2018 in anal