Debasement of Carol

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Carol’s fantasies come true at the hands of Sir.
2.4k words
4.49
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Part 1 of the 2 part series

Updated 11/15/2023
Created 08/28/2023
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John was sitting at his desk, fuming. His bitch boss, Carol, had just scolded him for a mistake that she caused.

John, a 36-year-old man, unmarried, not unattractive, with no obligations outside the company, thought, "Is she for real." He was tired of his almost weekly berating. I'm no teenage intern. He pulled up all the files that proved her incompetence on his tablet.

His boss, a 55-year-old married bitch had way more to lose than he did. Way more. A husband, a big house, fancy cars, a retirement account, and her bloated salary.

John was planning on sending the information he had to the higher-ups, hoping to get her fired, until he heard muffled words coming from her direction. He went to investigate and saw her office door cracked open. His friend, Bob, received the same treatment he'd received less than an hour ago.

Bob's job, financial security, and family were threatened for no valid reason.

John started formulating a plan. A plan to show this bitch who the real boss was.

John came to work an hour early for the next few weeks. The first morning, he planted very discrete cameras in her office. One camera looking at her desk, one behind her looking at her computer, and just for fun, one under her desk looking at her crotch.

Worried that a stray signal would be picked up by anyone knowing what to look for, he also hid a storage device with each camera. Every morning after that, he would collect the storage devices, transfer the data to his laptop, and return them before Carol entered the office.

After the first week, he looked at all the footage he'd collected. The camera facing Carol's desk showed little but did record her treatment of the staff, which was good to use in her termination case. The camera looking at her computer revealed that almost every day, Carol would log into a site that revealed her weaknesses, a site dedicated to women being sexually abused, tied, spanked, and humiliated.

The camera under her desk revealed that she used a dildo on herself several times daily. The time stamps showed that she was masturbating while viewing the porn site.

A new plan was working through John's mind, bringing a smile to his face.

After collecting data for three weeks, John invited Bob and his wife to dinner that Saturday.

While at dinner, John explained to Mary, Bob's wife, how their boss had been treating and threatening both his and Bob's employment. Mary was upset. Upset at the prospect of her husband losing his job, worried that he didn't confide in her, concerned that their boss was so cruel.

John and Bob calmed her down. When he revealed everything he'd learned, John said he had a plan.

He reassured them that they didn't need any involvement or knowledge of his plan and that Bob should see an improvement in Carol quickly.

The following Sunday, John compiled all the damning footage onto a single USB drive for safekeeping, transferred it to his tablet, stopped at a local sex shop for his required supplies, and finished the day at a bar near his office.

He spent the night in a hotel nearby to reduce his drive time and arrived at the office two hours early to begin his plan.

When Carol entered the building, he followed her into her office, closed the door behind him, slapping Carol across her face, telling her to get on her knees.

Stunned by the sudden attack, she started to attack John verbally. John told her, "Shut up, get on your knees, and listen to a recording I had for her."

Setting his tablet on the desk so she could see, he played a video of her masturbating while watching a video of a woman being bound and fucked. He showed her the documentation of her incompetence.

In shock from the sudden slap, the tone in John's voice, the video she was watching of her, and the documentation, she slowly sunk to her knees.

"How" was the only word that came from her mouth. John unzipped his pants, pulled out his cock, and told her to start sucking, or her husband and the company would see that video and much more.

Carol started to protest, trying to stand. John pushed her back to her knees, repeating his command to suck.

"But it's too big. I can't fit it in my mouth."

They locked each other's eyes. Carol seeing the rage in John's eyes, opened her mouth and took the head of his cock in her mouth.

While she sucked, he told her he knew how she spent her days at work, what she wanted done to her, and that he would make all her fantasies come true.

Carol worked his cock for ten minutes, sucking, gagging, and making sloppy air-sucking noises. She pulled him into her mouth with her hands on John's ass.

John grabbed her head, forcing his cock into her throat, choking her, yelling, "I'm cumming", cumming in waves. When he released her, she fell back onto her heels gasping for air, cum drooling out of her mouth and down her chin onto her blouse.

John dried his cock with her hair. Put his cock back into his pants and told her that he'd return at the end of the day to continue making her fantasies come true.

Everything was normal for the rest of the day, except Carol was unusually quiet.

At 6 pm, when the office was empty, John walked into her office carrying a large bag, closed her door behind him, dropped the bag with a thud, and told her to remove all her clothes.

She threatened him with the police, attacking her and rapping her. Carol didn't echo the fire of her voice in her eyes. He saw only fear.

He asked her why she hadn't called the police already. He said she wanted what was going to happen. Again John demanded that she remove her clothes.

Carol stood slowly and started removing her blouse, opening one button at a time with trembling hands, taking it off, revealing a light blue bra. Her nipples were hard as stone. She unclasped her skirt, letting it drop to the floor, stepping out of it. She was wearing matching light blue panties. Standing with her arms crossed, looking down in embarrassment.

John reached across her desk, grabbed her arm, pulled her around her desk to the middle of her office, and told her to remove everything.

Carol slowly unclasped her bra, letting it fall to the floor. Covering her breasts with one arm, she put the thumb of her free hand in the waistband of her panties, pulling them down, stepping out of them, covering her sex, now red with embarrassment.

John told her to put her arms at her side, spread her legs, and prepare for inspection.

Carol put her arms down, exposing her large breasts, and opened her legs enough that John could see her pussy, but not far enough for a proper inspection. He told her to spread her legs like the sluts did in the videos she watched.

After she made the adjustments with her legs, John could see moisture glistening from her neatly trimmed pussy.

He walked around her, first tweaking her nipples, then patting her round full ass, also reaching around, grabbing her breasts, and caressing them. He rubbed the outer ring of her anus, hearing little moans, finally finishing before her, fingering her vagina. The sudden invasion caused her to breathe in quickly.

He marveled at how trim and fit she was at her age.

Holding his fingers up to Carol's mouth, he told her, "Suck," she opened her mouth, took John's fingers, and cleaned them.

Their eyes never altered their gaze, looking at each other, John with determination, Carol with resignation.

John retrieved the bag, pulling out a collar, leash, ankle and wrist cuffs. He put them on her, grabbed her shoulders, turning her around.

Next, he pulled a collapsible spreader bar out of the bag, attaching it to her ankle cuffs, preventing her from closing her legs.

He pulled a chair from her desk, one John sat in many times, placing it in front of her. He told her to bend over the chair and tied her wrist to the legs of the chair.

With her legs spread as wide as he wanted, he could see and smell her excitement was building.

With Carol in this position, unable to resist, he pulled a paddle from the bag, showing it to her.

"I'm going to warm up your ass like they do in the videos."

"No, please don't. I don't want a spanking." She protested.

John bent down to look into her eyes. He said, "This is what you fuck yourself to; I'm only giving you what you want."

He walked behind her, settling the paddle on her ass, and told her to get ready. The first swing had her screaming in pain. He reddened her ass with the paddle for the next few minutes reducing Carol to blubbering tears.

"My, your ass looks red. You're going to have a hard time sitting for a few days. Maybe we can reduce the pain a bit."

John grabbed a butt plug from the bag, walked before her, and placed it on her lips.

"Get this wet, and you won't like it going in dry."

Carol complained that it was too big and wouldn't fit. John just chuckled and told her to open her mouth. "I'll make it fit."

Carol opened her mouth, trying to make as much saliva as possible, knowing it was going into her ass soon.

John took it out of her mouth, walked behind her, and shoved it in her rectum without warning, eliciting a squeal of pain.

John retrieved a chain from the bag and walked in front of Carol. Showing it to her asked if she knew what it was. She responded with nipple clamps.

He placed them on her with more squeals of pain. Giving the chain a slight tugs caused Carol to squeal each time.

He retrieved a ball gag from the bag, walked in front of Carol told her to open her mouth. He forced it deep into her mouth when she did and buckled the straps behind her head.

Stepping back, he admired his work. Here was his boss, bent over a chair, tied with her legs spread, butt plug in place, red ass, nipple clamps, and ball gag to finish her ensemble.

Standing before Carol, John removed his clothes, stroked his cock, and told her he would fuck her. She looked at him with drool dripping from the ball gag, lust in her eyes, nodding.

When John placed two fingers inside her, he found a sloppy wet pussy, begging to be fucked. The moans from his boss only added to his arousal.

John placed his cock head at her opening, teasing her with it, rubbing his cock head up and down her slit. Hearing moans coming from her, he plunged in one quick movement. He was slowly pulling back, waiting a bit before diving back in and stroking back and forth, getting into a rhythm. Feeling her inner muscles squeezing on his cock increased his coming release.

John pulled out to rest and prolong her frustration. He plunged into her again, pumping until he was close, pulling the butt plug out, and slipped into her ass to more squealing.

He started his rhythm again fucking Carol's ass. He felt the building release again, then cumming deep inside her.

Carol was a bundle of emotions, having been forcibly taken, made to cum twice, wishing she was forced to suck his cock again.

He pulled out to a popping sound, cum oozing from her anus.

He walked before her, took out the ball gag, and told her she wasn't finished yet. He said he had sold her to the cleaning crew, and four men were waiting to use her as she masturbated in the videos.

She looked at John and said thank you for this. I'm sorry for the way I've treated you.

John opened her office door, ushering in the four men. He watched as they used her mouth, pussy, and ass to their contentment.

Carol was shaking from the onslaught of cock, orgasms, and embarrassment.

When they finished, John saw a slut oozing cum from her gaping anus, down her inner thighs, on her face, and the floor. Cum drooling out of her mouth, the same mouth that had criticized him just a few days ago. He let her out of her restraints, sitting her on the chair she was bent over for the past hour.

Removing the nipple clamps proved to be another painful experience. The tingle added to the heightened sensations as blood rushed back into the sensitive areas.

He knelt, looked her in her eyes, and told her he'd filmed the entire event. If she said anything, her family had friends would receive a copy.

"Thank you, John. I won't say anything if you do this for me again."

John laughed and said, "How about every Friday." Carol just smiled and thanked him for making her fantasies real.

"Carol, I am your master now; that makes you my slave. Call me, Sir, starting now." Looking for a reaction from her, seeing only acceptance. He called her slut, "That is your new name, also starting now."

John asked her how she would explain her bruises and redness to her husband.

"That pussy, he won't dare ask Sir." John smiled at her accepting her position so quickly. Another plan was formulating in his mind.

Carol was absent from work for a couple of days. When she returned, she gave John a small smile touching his shoulder.

Carol whispered, "Sir," as she walked by. She was dressed a little more sexy. Everyone in the office noticed her change of wardrobe style and an improvement in Carol's attitude afterward.

When Carol saw an email from John, she immediately opened it. There was text and a video file. The email read, "Don't worry slut, I sent this email only to you. From now on, this will be your masturbation video. No more browsing the web. Sir"

Smiling, she opened the video file to find the whole hour of her debasement recorded and available for her to relive.

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AnonymousAnonymous8 months ago

Hint: Is she for real... that's a question... so it would have a '?' at the end.

jleetechiejleetechie8 months ago

For your first story, very good. Had you not included the cleaning crew, it would have been quite believable. There is potential for further humiliation, if you continue.

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