My Asshole Boss

by Small Penis


~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

This fictional story is the artistic expression of the author who wrote it. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this story, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~

Stripping the Boss – by jennanips

As Toni walked down the hall, she tried to slow her breathing. Today was the day. She had all her plans in place and, if everything worked perfectly, she would be fired and never have to deal with Phil again.

Phil was Toni’s boss. If you looked up “asshole” in the dictionary, Phil’s picture would be next to it. He was in his early forties, going grey and with a heavily receding hairline, around 5’9″ and at least two hundred pounds. He wore suits that he assured everyone were Italian and high quality, but appeared cheap and ill-tailored. He was completely sexist; Toni, his secretary, was the only female in the whole department. Their department took up half the floor of the building that belonged to their company but, due to Phil’s manipulation of his staff and the workspace, it was literally and figuratively walled off from everyone else. Toni had put up with his belittling, manipulative, bordering-on-sexual harassment for the past two years, since she had graduated from college.

Two months ago, Toni learned that she had been accepted into grad school in the next state. It was her first choice and she was very excited. There was one big problem — Phil. For all his aggressiveness and terrible behavior, the man was completely dependent on and half in love with her. He didn’t even keep a key to his own office; instead, he depended on her to arrive before him to let him in and stay until he was ready to go home. On the days she was on vacation or out sick, she had to find someone willing to go in early to open his door. She knew that if she tried to quit, she would be hounded and endlessly harassed by the man. The only way to truly be rid of him was to do something terrible enough to get fired.

Toni didn’t want to do anything that would hurt the company. She actually liked her coworkers quite a bit. The men, as a whole, were a fun group to be with. She thought a couple of them were downright hot and had entertained fantasies of fucking them in the office after hours, but had always been to scared of the aftermath to do so. At first to get first, she had tried to be rude and annoying to Phil, showed up a few minutes late on multiple occasions (but not late enough to dock her pay,) “forgot” phone calls, made slightly off center copies, etc. But it wasn’t working. One night, after a couple drinks at the bar down the block, she complained to her coworker Ron.

“Ron, I don’t know what I’m going to do. The man is such a prick.” Toni sighed, and took another sip of her drink.

“No he’s not,” Ron replied, laughing.

“What do you mean? Are there worse guys out there that I’m going to work for?” Toni was shocked for a moment.

“No, no, no,” Ron said, laughing harder, “I’m surprised you don’t know.”

“What?” now Toni was truly curious, still not getting his meaning.

Ron started his story, “He’s not a prick. Like, he’s super small. I go to the same gym that he shows up at a few times a year. Last month, I saw him in the locker room. Most guys could care less about being naked in there. I swear, sometimes it feels like a fucking sausage display. But he was being super cautious about wearing his towel and not exposing himself.”

“Don’t tell me you looked?” Toni said, getting interested in this.

“I was trying to stay away from him; I didn’t want him to see me and then make some macho display at my desk the next day about how we were lifting heavy weights together or whatever.” Ron replied.

“So how do you know?” Toni asked.

“He came into the shower area when I was in there. I had to wait until he got out of the shower before I could make my escape. I saw it as he reached out to get his towel. I’d be surprised if the loser is three inches erect.” Ron was laughing as he stated his fact.

“No way! Are you sure he’s not one of those guys who’s a “grower” not a “show-er” or whatever the phrase is?” Toni asked, an idea beginning to form in her head.

“No, that was the worst part. He was erect! I think he was masturbating in there.” Ron grimaced and took a big swallow of his beer, as if trying to get rid of the mental image in his head.

And with that, Toni’s plan clicked into place. She would get fired and make the office better for everyone that she was leaving behind.

If Toni had known that Thursday was National Nude Day, she probably would have liked her plan even more. She picked Thursday as it was payday, and she needed all the money she could save up for school.

That morning, Toni arrived to work dressed immaculately. Her shoulder length dark hair was brushed back from her face and put up in a librarian-style clip. She had spent extra time on her makeup, including cherry-red lipstick, which she knew Phil liked. She was wearing a form-fitting light grey jacket with a white silk camisole underneath. Her matching grey pencil skirt was extremely form-fitting and hugged her curvy hips and behind. You couldn’t tell when the jacket was buttoned, but underneath her outfit was a black bra with cherry-printed ribbon and lace along the top and matching bikini-style underwear. The bra covered her large, heavy breasts well, while at the same time pushing them up and together. She had skipped stockings for the day, as they would just get in the way, and completed her outfit with red, 40’s style peep-toe heels. They brought her normal 5’7″ height up to 5’10”, so that she would be slightly taller than Phil.

The morning started well. She was sweet and extra-attentive with Phil. She kept making sure that his coffee cup was full. She baked muffins for the department that morning, of which he seemed to eat at least half a dozen, the pig. She was even doing the ridiculously obvious flirting moves, like dropping her pen in front of Phil’s desk and making a show to bend over and pick it up.

Phil was completely oblivious to the fact that Toni’s behavior was any different than usual. In fact, he assured himself that she was this wonderful every day and was as attracted to him as he was to her. Rather than his usual micro-managing and harassing the men on the floor, he stayed near his office or Toni’s desk all morning. He was driving her nuts with small requests and demands.

Finally, 10:30 rolled around. Phil was a man of ritual; he always went to the bathroom for a long communion with the toilet at 10:45. Toni wanted him to be as aroused and uncomfortable as possible during this process, so she knew it was time to act.

“Phil, can you come out here and help me with something for a moment, pretty please?” Toni asked, in her what she thought of as her “helpless vixen” voice.

“Just a moment, dear,” Phil replied, slowly getting up from his chair. The helpless little woman, he thought, must need me to move something or fix her computer.

Toni stood up from her chair as soon as she heard Phil behind her. “It’s something on my computer. Could you please take a look at it?” As Phil moved forward, she quietly closed his office door, locking it. She quietly dropped the key into her purse.

Phil sat down in her chair and looked at her monitor. All that was on the screen was a tiny text box, with two words in an Alice in Wonderland-type font. “Do me.” He read the phrase out loud, and then looked at her questioningly.

Toni took a deep breath, and then started the show. “I’ve decided today’s the day.”

“What day?” Phil asked, going through a million fantasies of Toni in his head while wondering what she was talking about.

“The day that I follow my desires. Phil, I need you to make love to me. Now!” And with that, Toni removed her jacket and hung it on the coat rack behind her. She turned to face Phil, so that he could clearly see her bra underneath her camisole.

“Now? I guess in my office…” Phil turned, and realized the door was closed. “Toni?”

Toni bent down and whispered huskily into his ear, “No, right here on my desk. Naked. I want to show everyone in this department how you own me and how wonderful you are.” She moved her head a bit so he could see into her heavily-lidded eyes and then licked her lips.

Phil gulped, both scared and turned on at the prospect. He’d had sex three times, each with a different woman, all of whom said he was wonderful in bed. He knew he was good. Toni must sense it too. If she needed to be naked and taken right there and then, who was he to complain?

“All right,” Phil replied, “I’d be happy to take care of your needs, sweetheart. After all, what are good bosses for?” He looked at her long desk and realized that, other than the monitor, it was completely clear and perfect for fucking her on. He had been completely oblivious to the fact that Toni had taken home every single one of her personal effects over the past two weeks.

Phil quickly undid his tie and threw it on to the desk. He then unbuttoned his shirt and put it on the desk as well. He took off his shoes and socks, leaving them under the desk, and then unzipped his pants. He stood up, taking his shirt with him, and hung his pants and shirt on the coat rack. “Well,” he said, standing proudly in his faded, saggy white briefs and looking at her, “aren’t you going to get naked?”

Toni smiled in reply. “You’re still wearing something. I want to see how excited you get at my body.”

Phil complied with her unsaid request and slowly removed his briefs, half hiding his small, pink penis with his hand, not sure he was ready to expose himself to her. He sat down, quickly, the roll of his belly all but covering his sad little penis and balls.

Toni quickly looked down, confirming what Ron had said. That penis was by far the smallest she had ever seen, with little pink testicles to match. Without betraying her thoughts, she again looked up at Phil and licked her lips. “He looks delicious. I can’t wait for you to have that big guy thrusting into me.”

Toni began her strip show. She removed the clip from her hair, shaking her head in slow motion as her dark, shiny hair cascaded around her shoulders. She unbuttoned her camisole, bending towards Phil, giving him larger and larger looks of her cleavage until each button was opened and her shirt fell to the floor. She then turned, facing away from Phil, and used both hands to unzip her skirt and peel it away from her body. Phil was panting. The sight of Toni in her matching black and cherry underwear and the red fuck-me heels was almost too much. He was as hard as a rock and ready for her.

Phil reacted, reaching forward with his right hand.

“No, no,” she said, lightly slapping his hand away. “No touching until I’m ready.”

Phil thought she was playing hard to get. He was sure that she wanted him to touch her; wanted him to help remove her bra and panties. He couldn’t help himself; while still sitting, he reached out to grab her. “Phil! I guess we’ll have to take care of those wandering hands,” she said, and quickly grabbed his belt from the floor. Before he knew it, she had tied his hands behind him and to the office chair. She hadn’t done it very securely, but knew Phil was the type that wouldn’t try very hard to free himself. She was right. He pushed his hips forward, as if he could try and slide out of the seat. All this did was expose his penis to her. It was now bright red and leaking a bit of precum. Toni now saw that Ron about the three inches. Phil’s penis was more like the size of her ring finger, less than three inches long and rather skinny as well.

Toni looked up and realized that she and Phil were not alone. Toni’s desk was halfway down the hall from the entrance to the office. Unlike everyone else, who had a cubicle, she was out on the floor in front of Phil’s office. Her desk didn’t have a front, so that anyone walking by could practically see up her skirt. For the past two years, she had dealt with having no privacy, no ability to have a quiet phone call or check her e-mail at her desk, as everyone could see everything. Today, however, this would work to her advantage.

Toni looked at the three men, including Ron, who had gathered close to her desk. “If you’re going to watch, you’ll have to get naked, too.” Toni said. Still dressed in her panties, bra, and heels, she wheeled her chair around, so that Phil’s naked back was to his office and his penis waving to his employees. He could now clearly see her desk and out on to the floor. Mark and Jack, two of Toni’s coworkers, quickly complied, removing their clothes and making small piles in the cubes behind them. Ron ran off, as they’d previously discussed to alert the rest of the floor as to what was happening and to leave their clothes behind.

Toni looked at the gathering group. She was glad it was summertime and that a lot of the guys were on vacation. Even still, there were now a dozen men, naked, watching her. She placed both hands on her hips and began to push her panties down, exposing her firm, tight behind to Phil and her neatly trimmed bush to the rest of the men. She pushed the panties slowly down her legs, stepping out of both them and her heels. She turned around and reached behind her to undo the hooks of her bra. She removed each strap in turn, playfully pulling them along each shoulder and arm. She leaned forward, as if giving Phil the chance to remove her bra and see her breasts for the first time. With his hands tied, all he could do was gape at her.

She removed her bra and set it in a bag with her other clothes. She stood up and posed for the men, turning this way and that, making sure Phil was completely and totally erect. The air conditioning quickly hardened her nipples. Being naked in front of the men turned her on and she could feel the cold air cooling the juices forming at the top of her thighs.

Toni gazed at the men. They were slowly growing hard. At this point, though, every single one of them had a penis that was longer and thicker than Phil’s. It was time for Phase Two of her plan.

“Are you ready?” she said, half to herself. Only Phil had heard her.

“Of course I’m ready! Untie me so that I can give you the fucking you need.” Not exactly the most couth words, but Phil wasn’t exactly smooth with the ladies.

She turned, facing him, and placing her butt on the edge of her desk. “Phil, how am I supposed to fuck that?” she frowned, pointing towards his genitals, “your belly is so big I don’t even think you could get that little, teeny, tiny penis inside of me.” She laughed and then turned to face the men. “Have you guys seen this thing? Look! Isn’t it pathetic?”

Ron began to laugh and all of the men followed his lead. Suddenly, instead of seeing a crowd of admirers, Phil saw his employees laughing at him, jeering at him and his body. They insulted his fat body and his small penis. They joked about his miniscule testicles and how he was probably a virgin. He had never felt more humiliated. Tears of shame rolled down his cheeks and jowls. His penis betrayed him, though, standing firmly erect, enjoying the attention.

“Well, since he’s not man enough to fuck me, who’s first?” Toni challenged, looking over all of the men before fixing her eyes on Mark, who at ten inches long and as big around as a coke can, had the largest penis of the group.

“I think I’m the winner here!” Mark said, and began walking toward her.

“No!” Phil cried, straining against his flimsy bonds. “You can’t have her. She’s mine. She loves me!”

Toni looked back at him, pure hatred upon her face now, “No, Phil, I don’t love you. I don’t like you. I don’t want you. You are probably the worst man I have ever met and I don’t want to hear from you anymore.” With that, she reached down to the floor and gingerly picked up Phil’s briefs in two fingers and grabbed his tie in his other hand. She looked into the slightly-grayed, stretched out underwear and grimaced.

“Oh, Phil, gross! Don’t you wipe? You treat us all like shit so it’s time to taste some of your own.” She carefully turned his briefs inside out, not wanting to get her hands dirty, and exposed the brown streak inside. Phil opened his mouth to protest and she quickly shoved his briefs inside. She then tied his tie around his mouth and head, making an efficient gag.

Phil tried to use his tongue to push out the gag. He could easily breathe but wanted his soiled underwear out of his mouth. However, at the first taste of his own shit, he recoiled, wanting his tongue as far away from putrid substance as possible. He was trapped.

Toni looked down. Phil’s penis, if anything, was even redder. She laughed and walked around her desk, moving into Mark’s arms.

Mark kissed her deeply and fondled her large, firm tits before laying her down upon her desk. He pulled her to the end, so that he could stay standing, and opened her long legs. He moved forward, impaling Toni on his giant penis.

Toni screamed in ecstasy. This part of her plan had been exciting her for the past two weeks. The idea of being the center of attention of a group of naked men just got her wet. She knew these men well enough to know she was safe and in for an amazing time, all while humiliating little-dicked Phil.

Mark worked his ten-inch penis into her, at first slowly and then, seeing how much Toni was enjoying it, faster and faster until he was buried balls-deep. She started sliding around on the desk and reached out her arms, looking for something to hang on to. Instead of the sides of her desk, she found two penises. Someone had retrieved a bottle of lotion from his desk (Why do these men own lotion? Toni briefly thought) and poured it over each of her hands, lubricating the two shafts as she began stroking them. She looked to her left. Someone had moved Phil a bit so that he could still see all of the action unfolding around him.

Toni then felt her head being gently turned to the right. Jack was there his penis at mouth level, an expectant look on his face. She opened her mouth and took him in. He wasn’t the largest man of the group, with about a five inch penis, so she could easily suck his length in without gagging.

Behind Jack, she looked at the other men. Most of them were stroking themselves, watching her and the unfolding action. A couple were moving themselves up against her, humping against her thighs and shoulders. Between the sweat and the precum, Toni’s skin was taking on a sexy, glistening sheen.

Toni felt something wet along her breasts. She looked down to see Ron dragging his tongue over her breasts and then on to each nipple. The sensations were delightful. She began moaning along Jack’s penis. As if on cue, Mark changed the angle of his thrusts, pushing harder against her g-spot. Ron began sucking on her left nipple and twisting the right one. Toni began to cum. The orgasm raced through her, tightening every muscle of her body. She arched her back, pushing her breasts further into Ron’s mouth. She sucked Jack furiously and stroked the two men in her hands as if it was her last wish. Her juices began to drip out of her pussy and down the desk. She felt like she could cum forever.

As she began to return to reality, she realized that the penis in her left hard was starting to pulse and that his owner, Brad, looked ready to cum. She lifted her head, losing Jack’s penis for the moment.

“Not on me,” she breathlessly stated, “on Phil. Quick!”

Brad looked down, realized what Toni had said, and smiled. He quickly complied, putting her hand on to the desk and moving towards Phil. Phil looked up at him, horrified and yelling something against his gag. Brad took himself in hand and, with a few quick jerks, began to cum on Phil’s chest and belly.

Toni watched Phil’s reaction. His yells suddenly grew stronger and he began jerking his hips. Toni looked down, surprised, and realized that Phil was cumming. She called out to the men, “Look, little Phil likes it.”

The men began to laugh. Two of them disengaged from the group and moved towards Phil, making sure not to block his view of Toni. They jerked themselves off, laughing, until their penises spurted over him. The taller of the two men, Ben, came all over Phil’s face and neck. He then called over to Toni, “Look, that little dick of his wants more!” Sure enough, Phil’s tiny prick stood tall again, waving in the air like a teeny, tiny checkered flag.

Toni could no longer concentrate on Phil. Mark had left to cum on Phil, and another man had taken his place. Jack was about ready to pull out and blow. Ron had stopped sucking on nipples, allowing another man to climb on the desk and mount her chest. He used his hands to push her breasts together and began thrusting between them, using Ron’s spit as lube.

Toni closed her eyes and gave over to the sensations sweeping her body. She could no longer count the number of men or whose dick was whose. Orgasm after orgasm swept over her body. As each man became ready to cum, he would withdraw from her and jerk himself off on Phil. New penises kept finding her hands, mouth, chest, and pussy. She had felt at least one set of fingers in her ass, though no one had fucked her there. It seemed like hours until the men from her hands, mouth, and chest withdrew. She felt her body being pushed back along the desk and a single man over her, gently fucking her in missionary style. She opened her eyes.

“Ron?” she whispered. They’d been friends for so long, that somehow she didn’t think he would fuck her.

Ron bent over so he could whisper in her ear. “I wanted to wait until Phil’s ears were mostly plugged with cum. Toni, I’ve liked you since the first time I saw you and the first time I heard you speak. You have no idea how much I’ve enjoyed watching your incredible body go through orgasm after orgasm.”

He gently licked and kissed her ear, then moved up to smile at her. She smiled back, using her arms to bring him back down so that she could whisper a reply. “Ron, I’ve wanted you for a long time. I’m glad I got to save the best for last.”

Ron kissed her and lifted his chest so that he could thrust into her more deeply. Most of the men were now sitting around, looking utterly spent, though a few were still standing next to Phil, masturbating. The man was covered in cum, some of which was his own, as he had now cum three times while being tied to the chair. He had also peed on himself at some point in between erections, as his coffee and breakfast-stuffed bladder could no longer take the pressure. There was cum and urine all over the chair and it appeared a few enterprising men had left their semen on his rumpled clothes. His head was hanging down, though he was still watching Toni through cum-lidded eyes.

Toni felt Ron begin to stiffen. “It’s okay, Ron, you can cum in me.” Ron moaned and began to orgasm. Toni sighed as she felt the first pulse of his seed entering her. Her body orgasmed in reply, as if slaking a deep thirst. When he had finished, Ron climbed off the desk and helped Toni up. She was surprised she could stand, let alone walk, as she had been so thoroughly fucked.

Toni’s mission was complete. She picked up her bag of clothes and her purse and threw them over her shoulder. She pulled a camera from her bag, and then faced Phil and waited until he lifted his head to look up at her.

She gave one of the men a pair of rubber gloves and asked him to remove the gag. She then turned on her camera and took pictures of Phil from every angle. She made sure she had plenty of pictures of his fat, cum-soaked body, his little penis, still half-erect, and his cum-covered face.

“Goodbye, Phil. Remember to always treat your employees with kindness and respect.” She turned off her camera, waved it at him so that he understood, and turned to leave, still completely naked. Head held high, she smiled at the security man at the entrance to their floor. She made a quick stop at the women’s restroom, flushing Phil’s office key down the toilet. She then walked down the three flights of stairs to the garage, got in her car, and drove off, knowing she would never enter that office again.

Authors love your feedback.

%d bloggers like this: