An Office Mommy

This story is complete fiction. It contains themes of pegging, chastity, domination, humiliation and dirty talk, along with alluding to gay sex. Hope you enjoy!

***

Daniel didn’t like to work late. His job was boring, tedious and left him brain dead at the end of every day. But it paid the bills and he knew he would have to work late to move up the corporate ladder and achieve his dreams.

So, instead of going home to his bachelor pad, cracking a beer and zoning out to some TV show or movie, he was working on some decks for presentations next week. He was so focused, he didn’t notice the office get quieter and quieter until there was only the sound of one other person typing away. Then, that noise disappeared. Daniel didn’t notice. Only when he finished his first draft of the deck and leaned back to stretch did he see how empty the office was and how dark the outside had gotten.

He shrugged and got up to use the bathroom before heading out, not seeing any sign of habitation except the glowing light coming out of his boss Jeremy’s office. Daniel had an uneventful bathroom trip, rubbing a hand through his shaggy blonde hair to push it out of his face after washing his hands. He wasn’t a bad looking guy and didn’t mind looking at himself in the mirror, if anything he looked a bit ragged and unkempt. Daniel wasn’t the type to be buttoned up and groomed like most businessmen, instead choosing to keep it casual. He spent a few more seconds putting himself as together as possible in front of the mirror before smiling at himself and leaving, ready to begin his 20-minute commute back to his apartment.

Except, when walking past Jeremy’s office on the way back, he heard something disrupt the suffocating silence an empty office building contains. It was a sharp, smacking noise followed by a whimper.

Daniel paused, tilting his head. Another smack, another whimper. He backpedaled, zeroing in on the source of the noise. This time he heard a muffled voice before the smack and a more distinct whimpering afterward. The noises were definitely coming from Jeremy’s office, and it sounded like Jeremy was at least one of the people making a noise. Daniel just couldn’t tell which.

Now, with his ear pinned to the wood door, he could hear almost perfectly what was being said between each smacking noise.

“This is what you get for being such a bad puppy, hmm,” said a distinctly feminine voice. “Bad boys need to be taught a lesson.”

Smack. Whimper. “Yes mommyyyy,” replied a high-pitched whimper. But Daniel was almost sure it was a man’s voice made falsely high.

“You’re not going to disobey another order, are you?” Daniel thought the voice was starting to sound familiar, at this point.

“No mommy,” the man responded before another smack fell, whimper following.

“So. When I tell you to fuck Jerome during a video call and you don’t, why? What made you disobey your mommy?” Another smack came before the man could respond.

“I was scared I wouldn’t be able to stop moaning, mommy.”

Daniel was now definitely sure he knew the two voices, and knew them well. The man speaking in a high voice sounded kind of like his boss, Jeremy. The woman could still be anyone, though. He only barely felt like he knew that voice. Daniel definitely didn’t know anyone named Jerome and knew that no one in the office was named Jerome. He also couldn’t figure out how someone could get away with being fucked, even on a video call. People in his office were rarely off-camera for meetings.

“Aww poor puppy can’t control his moans?? Not. My. Problem. When I give you an order, you follow it or you’ll be very unhappy. You know this. You remember the team offsite? Disobey me again and you’ll think about that as me going easy. Understood?”

“Yes mommy,” the voice responded. Daniel was now definitely sure it was Jeremy with the high pitch voice. He remembered the 50 year old boss skipping out on a dinner because he was “feeling under the weather” and showing up the next morning with a sore throat, onikişubat escort bloodshot eyes and an odd gait, as if he had a sore ass from lifting. Daniel’s mind was starting to run through very different scenarios than being just “sick.”

“Here’s what we’re going to do instead little boy, because I want you to go back to being the good little boy you are. I’m going to write some encouraging saying on you and then you’ll take Jerome out into that bullpen and we’ll film another video to add to the collection. I want to hear your best whimpers and moans, but no cumming. You lost that privilege. Once I’m happy with our video, then it’ll be my turn to have some fun. How does that sound?”

“Yes mommy.”

“Good, now come here and bring a sharpie. I want you to see this for the rest of the week,” the woman’s voice said, ending the conversation.

Daniel’s head swirled with thoughts, mostly driven by his cock. He’d always loved when women took initiative in the bedroom. One time, drunk, his ex girlfriend had pinned him down and rode him until he came inside her, despite the fact they weren’t on birth control and they always pulled out or wore a condom. He remembered, distinctly, her moaning “Don’t fucking pull out you slut, this dick is mine and I’m going to use it. I want to feel you pulsing inside me, I need to feel it.” About three seconds later, Daniel came.

Now, caught in the middle of a seemingly extreme version of the femdom videos and stories he sometimes consumed, he wanted to see it through and experience (at least tangentially) as much as possible. So instead of packing his stuff up and running, he hid in the conference room where he could peak his head around just in case.

Only when he heard the pair leave the office did he realize his stuff was still at his desk. The woman noticed almost immediately, but instead of going back into the office a smile spread over her now-familiar face, “Look boy, I think I found where we’re going to film our video.”

Jeremy, because Daniel could now tell it was his boss, just whimpered and followed her on hands and knees.

The whole scene was almost too much for Daniel. Recognizing the woman, taking in her outfit and seeing his boss crawling along naked all in the same moment took a while to process.

The woman was on another team that reported up to Jeremy and someone he’d only talked with occasionally, though each time left him flabbergasted. Her name was Emily, and her dark black hair framed an innocent doe face in a bob. Daniel thought she was about 24, new to the corporate world and fresh out of college. Her pale face was dotted with dark freckles, but it was her eyes that always took Daniel aback. Icy blue and intense, they seemed to hold a hidden power that made you think she knew better than you. And that was just the face.

Daniel had checked her out subtly a couple times before, but that was in business professional dress. Now, with her wearing what can only be described as a domme’s outfit, he was immediately in love. Her 5’2″ frame was bolstered by black stilettos, the heels of which looked to be kneeling naked men. Stockings moved up her thick thighs, all muscle. Around her waist was an empty strap on and some black panties, flowing smoothly into a toned stomach. But Emily’s bust was something magnificent, barely constrained by her black lace bra, the milky skin threatening to burst forward.

From his hiding spot, Daniel could see them walking towards his desk. Or in Jeremy’s case, crawling. There was something in his mouth, like a puppy carrying a stick. It stretched his mouth wide, but definitely wasn’t a stick. Daniel concentrated harder, then realized what it was – a huge, black dildo. Probably 12 or 13 inches long and thick enough that Jeremy looked to be struggling to hold it in his mouth.

After reaching Daniel’s desk, Emily told Jeremy to put Jerome on the chair. He put the dildo on the chair, pointing upwards.

“Deepthroat your boyfriend, puppy.” Emily ordered. Jeremy ordu escort followed orders, slowly working his way down the giant shaft. Jeremy continued, spit leaking out of his mouth and falling down onto the desk chair. Daniel could see his face getting read, his throat opening up every time he went down on the massive cock. It looked like torture, but Jeremy never stopped. Never slowed down.

“Hold for five seconds,” Emily ordered. Jeremy obeyed. No hesitation. “Release.”

Jeremy pulled back up, gasping for air. There was spit running all down his chin, some of it stretching down and only held to his chin by surface tension.

“Let me get a photo for the album boy,” Emily said before taking a photo of Jeremy sitting on his heels.

From this position, Daniel could finally read some of the things written on his boss’ body. On his chest, where his heart is, it read “Emily’s bitch.” On his left side was a graphic and detailed drawing of a cock, shaded as though it was a BBC. On one thigh read “Weak puppy.” The other: “Sissy cuck.” Daniel then saw his cock for the first time. Or, at least, the locked up cock. In a small pink cage, it looked pathetic. But the shaved pubes and the sharpie writing of “Useless Clitty,” rubbed in the humiliation for Jeremy even more.

Poor guy, Daniel thought at the same time as his cock got hard imagining himself in the same situation.

“Ugh, you are a cute puppy when you look pathetic like that,” Emily said. “Now take out your plug and get on your boyfriend.”

Daniel saw Jeremy lean over and pull out a butt plug nearly the thickness of a beer can. Then, he stood up and took the black dildo in one go, letting out a whimper as it worked its way inside him. Emily leaned at the desk across from him, capturing the whole scene with her phone in front of her. She had a wicked gleam in her eye and a coy smile, clearly enjoying watching the other man humiliate himself and follow her orders.

“Tell the camera what you are, slut.”

“I’m a whore.”

“Obviously, give me more whore. What do you love?”

“I’m a cock slut who loves being ordered around.”

“That’s better. Keep fucking yourself, I want to watch your pathetic little clitty bounce. Ooo fuck, you’re making mommy so wet by being so pathetic.”

“I love making you wet mommy,” Jeremy said.

“I know you do, honey. Do you love fucking cock? Do you like fake cock or real cock more?”

“I love mommy’s cock most. Mmm. But other than that I love being railed and controlled by other men.”

Daniel was taken aback by the admission, not realizing Jeremy was bi. Or at least willing to fuck men for Emily.

“That’s good little puppy. Mommy has the best cock. Now remember, no cumming. If you cum I’ll make sure your clitty never gets near me or my holes again. You don’t want that, do you??”

“No mommy I need you…” Jeremy’s moans were getting louder and more frequent. Daniel watched as Emily kept teasing him, talking about the things they’ve done in the past and what he’d miss out on if he came. After a few minutes he slowed down.

“Aww is the poor puppy getting too close to cumming? Why don’t you take a break while I put your boyfriend on.”

“Yes mommy…” he said breathlessly.

Daniel watched as he pulled himself off the monster dildo, seeing the wet patches on his chair that Jeremy left from getting fucked. Then he saw Emily attaching the base of the cock to her strap-on before lubing it up.

“Come bend over the desk and spread your cheeks for me baby. God, I love watching your asshole gape.”

Jeremy was bent over the desk behind Daniel’s giving him a good view of Emily’s ass and back as she prepared to pound the executive.

“What do you want puppy?”

“I want you to fuck me, mommy.”

“Hmm, give me more. What are you?”

“I’m just a hole for you mommy. I only exist to make you happy and I need youuuuuuuuu,” the last word extending as Emily plunged all the way into the man, down to the base balls of the dildo.

Daniel’s örnekköy escort cock, which he’s been slowly stroking for a while, exploded as he watched Emily’s back thrust into Jeremy. He watched as her strong thighs and glutes clenched and unclenched. Her strong, milky white back flex as she spanked the subservient man. From his spot, watching her dominate a man and her body move, Daniel couldn’t help but fall in love. And cum. A lot. With a little moan escaping his lips as the orgasm rushed through him, the strongest he’s had in years, probably.

Once he regained his senses, he looked up to see if the pair at his desk had heard or noticed him, but they were going at it like animals.

Emily was grunting with passion and effort, raining a deluge of spanks onto Jeremy’s ass. Jeremy, for his part, was moaning uncontrollably. Daniel thought he could hear pleas to cum, but it was mumbled and lost amongst his blabbering gibberish and moans.

Even after cumming, Daniel was engrossed in the scene in front of him. The urge to be in the middle of it, dominated by Emily hadn’t left. He was watching his boss get railed, humiliated and used on his desk, but Daniel wanted that.

A few moments passed before Emily had one last powerful thrust into the man’s ass. She leaned over him, drawing her nails along his back and then whispering something into his ear. Daniel watched him shiver before she bit into his shoulder and grabbed his ass cheek roughly, digging her nails into it.

Then the pair separated and Emily said, “Let’s go back to your office, puppy. I want you to give me a treat for being such a good mommy.”

Jeremy merely nodded before crawling back to his office. Emily, with Jerome still on her strap, did a slow turn around the office, looking for something. Daniel ducked away so he wouldn’t be seen, causing him to miss her gaze lingering on the slightly ajar door to the conference room. A couple breaths later, he poked his head back out and caught her walking back to the office with a swagger he immediately found intoxicating. Especially watching the massive black dildo sway side to side, Emily’s hand absentmindedly stroking the top of the lifelike dildo.

Once Jeremy’s office door was closed, Daniel rushed to pack his things. He saw the wet spot on his chair left over by Jeremy riding the cock. He also saw a little pool of precum on his neighbor’s desk where Jeremy had been bent over.

With his stuff all packed up, Daniel worked his way onto the elevator, but not before hearing decidedly feminine moans growing out of Jeremy’s office. Immediately, Daniel was getting hard again imagining himself in Jeremy’s position.

He came twice more that night, picturing Emily doing those things to himself. He was groggy when he showed up to work the next morning, a few minutes late.

“Late night? You look a little tired,” asked a familiar voice as he meandered his way into the building. It was Jeremy.

“Yeah, didn’t get to bed on time,” Daniel replied a little shakily, unprepared to see his boss back to normal after last night’s events.

“Out with a girl??” His boss asked curiously.

“Unfortunately not.”

“There’s always next time,” Jeremy said.

The pair separated as they exited the elevator. Jeremy to his office, Daniel back to his desk. There was no visible stain on the chair from last night, so Daniel sat down, placing his bag down and getting set up for the work day. He pulled open the door to his drawer where he kept his notebook and absently reached a hand in there to grab it when he felt something a little more solid. Plastic.

Daniel looked into the drawer and immediately closed it. There was a purple, plastic chastity device in his drawer.

In. His. Drawer.

He took a deep breath and looked around the cubicles to see if anyone was paying attention. Everyone’s heads were down, focused on their work. Except one, as Daniel moved his eyes to where Emily sat, he saw her staring at him, her eyes exuding power and a small, sly smile on her lips. He looked away and then back down, swallowing.

Slowly this time, he opened the drawer and took in the picture. A purple chastity device, a key and a note.

Have fun last night? Bring me the key and prove you’re wearing it if you want to have more. – Mommy