The Boss' Target

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Caroline realizes she's the object of her boss' desire.
1.6k words
3.2
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Part 1 of the 2 part series

Updated 06/11/2023
Created 10/24/2021
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Her earphones were blasting one of her favourite indie songs as she was clearing her desk. He stood at the opposite end of the room, watching her from the back. He studied the way her work suit fit her small body, how the sleekness of the black contoured her curves and edges.

Either she really liked music or she wanted to avoid talking with him, he could not tell. If it was the latter he had hoped she did not catch his furtive glances. He could not risk her knowing what he wanted to do to her. One wrong move and he could kiss their after work commute arrangement goodbye.

He sometimes wondered if she ever let herself go in the safety of a bedroom, if she ever felt sexual bliss that made her feel alive and free. In the workplace she was always stiff and professional, her voice calm, never a hair out of place. Whenever she started speaking about the documents she drafted there was always a moment where he wanted to push her down, snatch her glasses away and start working on her pussy. He could imagine the wild screaming and the mess he would make out of her hair and makeup.

He was generally a confident man, sometimes too confident. In his youth he would approach women at bars for a one night stand but most of his efforts fell through. He eventually gave up on women until a certain fresh young lawyer entered his firm, and he eventually decided he just had to get his hands on her before it was too late. She made him nervous because she was pretty and he was sure she could have anyone she wanted - soon she would be with a young fool her age and he would be left in the dust.

As they were walking towards his car he tapped on her shoulder to get her attention and then he tapped his ear. She pulled out one earbud and he asked her if she was hungry. Surprised, she said no and pushed it back in.

At some point during the traffic jam she turned off the music and was browsing through her phone with a bored expression on her face. He could not get a glimpse of what she was scrolling through but he knew if he did he would have no idea what he was looking at. Young people and their phones. The interconnectedness of it all.

He was supposed to go north and continue on the main road but he turned right and into a side street. She turned to face him, like he expected. They both said nothing but he could tell she was at least confused. He continued along the road and it was not long until he pulled into his driveway.

"Welcome to my house," he said with a smile.

She opened her mouth to speak but he interrupted by saying "Stay for a while. Have a drink."

He tried not to think about her naked body on his bedsheets while he poured two glasses of whiskey on ice for both of them.

"Did you know that some people drink it hot?" he said. "Could never be me."

She eyed her glass warily and tentatively took a sip. He gulped his down, his eyes never leaving her face. After a few sips she set her glass down. She noticed him staring.

"Is there something you wanted to talk about?" she said.

"Talk? Yes I suppose we could," he replied. "But I think you should take off your clothes first. Get comfortable. And there's no need to be shy."

He saw fear and realization beginning to creep into her eyes. She started to back away from where she was leaning on the kitchen island. The door that led to the garage was on her left and she stared at it as if she was not sure if she should run towards it.

"It's locked," he said. "I have the key in my pocket. Now come here. Let's not turn this into a chase."

She glared at him for a moment and then dashed towards the garage door. It was indeed locked. She gulped and her breathing became shallow. He started walking towards her.

"I'm not going to be rough. But I will do whatever it takes for you to climax."

He hugged her from behind.

"Now you're going to be a good girl and do whatever I tell you to do," he whispered into her ear. "Or I'm going to make you. Understand? Say yes."

She hesitated and then weakly said "Yes."

He dragged her by the arm to the living room. He dropped onto the couch, spread his legs, and undid his belt. He took out his penis and started massaging it. He ordered her to get on the couch and start blowing him. She stared at him in horror, refusing to move. In one swift move he grabbed her and pulled her down. He pulled her head towards his erect penis.

"Start. Come on. Or I'll shove it in your mouth," he said roughly. He had intended to stick to what he told her earlier but he felt like he desperately needed a blowjob.

All he felt was her warm breath on the tip so he pushed her head down and she gagged. She grabbed his jacket and he decided to show mercy. He let her come up for air.

"You see what happens when you don't do what I say? Now do something. Anything."

With a pained expression she closed her mouth around the tip and started moving her tongue around it. He sighed in relief, still holding her head in place.

Tears were starting to fall from her eyes. He felt sorry for her so he told her to stop. He grabbed her face and looked into her red eyes.

"It's too much for you? Alright. I know what will make you feel better," he said gently.

He lit the candles he placed around the jacuzzi while she hugged her naked body, her knees up to her chest. The tears were gone, like he had hoped. His penis was no longer erect. Her glasses and ponytail were off. The bottom half of her long black hair was wet and clung to her soapy fair skin.

After all the candles were lit he switched off the light. He stepped into the jacuzzi and placed a hairy arm around her, pulling her close.

"You're not like other women," he said. "Something about you is different."

She said nothing, but continued to stare at her knees.

"I got too excited earlier. I'm sorry," he said, moving the hair that was closing in on her face.

He unclipped her arms from around her knees. She tried to wrap them back again but he held her left arm back. He could tell from the look on her face that she was angry.

"Don't be like that," he said gently.

She tried to break free of his grip but to no avail. Then she tried kicking him, splashing water and soap in the process. He shielded his eyes but managed to hook her knee with his other hand. She was back to being scared, now that she saw she was out of options.

"Please don't," she said shakily. "Don't do anything more to me."

Her eyes grew wet. He sighed and let go of her, but he was not ready to shake her off.

"Alright," he said. "I can take you home now if you want me to. But not a word of this to anyone, or I'll make sure your job is on the line too."

She stared at him in disbelief, and without a word she raised herself and stepped out of the jacuzzi.

While on the way to her house he said "You must be hungry. I'll get you something to eat."

"No," she responded quickly and through gritted teeth.

She had been in his house for over an hour. The 5pm sun now lit up their faces. The streets were less busy now and he was free to drive a little faster. Her hair soaked her jacket, which made her uncomfortable, but the car's air conditioning was in the process of drying it. She was soapy between her legs but unfortunately the air conditioning could do nothing about that.

He had wanted her in his bed. He could have dragged her there despite her tears and protests but he did not have it in him. He felt weak because he missed out on his chance, but he soon came to the conclusion that he simply cared too much for her.

After dropping her off at her house he went home and saw her hair tie next to the jacuzzi. A piece of her hair was still attached to it. He carefully picked up the hair tie and placed it in an empty drawer in his bedroom where it would sit on its own, uninterrupted and free from contamination. He was extra careful not to pluck the hair.

He undressed and removed the sex doll from the closet. It matched her skin tone and hair colour, just like he wanted however the hair was shorter and the breasts bigger, and the doll was a few inches taller than she was. He knew it was impossible to get a perfect fit so he settled for the closest thing. He had bought it two months after she started at the firm, when he was in the heat of the moment.

He would pretend it was her. He even talked to it. He was always gentle and tender towards it but this time it was different. He pushed it on to the bed and quickly applied the lubricant from his bedside table on to his penis. He positioned himself and the doll into missionary and started thrusting aggressively into its vagina. He sighed as sweat dripped down the side of his face. He eventually climaxed and collapsed onto the doll. He breathily whispered into the doll's ear.

"This isn't over."

End of Part One

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