Doing the Boss

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Employee blackmails boss into being his sex toy.
3.6k words
4.38
272.9k
75

Part 1 of the 2 part series

Updated 10/31/2022
Created 01/05/2004
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Robin walked into Christine's office and stood in the doorway watching her. As usual she was on the phone, chatting to her friends whilst surfing the net. At the age of 35 she was still very good looking. Black hair, trim figure good legs and she knew it too. Robin had been working for her for a year and a half and he had spent many a night fantasising about what he would like to do to her. In his hand now was part of that plan to help him make those dreams come alive.

Christine smiled at Robin and continued talking as if he wasn't there. She spoke and laughed to her friend whilst noticing Robin's eyes examining her legs again. She tucked her skirt down a bit more, just so he wouldn't get an eyeful of thigh. Robin closed the door opened the envelope he was holding and placed the photos face down on her desk and lent back against the door. Resting the phone in the crook of her neck she picked them up and examined them. She went silent and almost dropped the phone. Robin grinned.

"I'll call you back Sue, something just come up!"

Two nights before at a works retirement party, Christine had been flirting outrageously with her boss, Jeff. She had sat on his lap, and played shocked when his had cupped her arse. Christine and her boyfriend had been trying for a child for some time now and she had taken fertility drugs to help. All they seemed to do though was make her feel slightly hornier, so when they mixed with the alcohol, it had spelt trouble. As the night wore on he had progressively got bolder and had cupped her breasts and had his hand up her skirt on several occasions. Eventually, they both made an excuse to leave and had departed arm in arm. He had offered to give her a lift home and they had ended up in the car park together. She wouldn't let him fuck her though, no matter how much he begged or how much she wanted.

Chris looked through the photographs slowly. The first one she had hold of showed her and her boss in the staff car park. She was leaning back against the wall, her skirt hitched, as Jeff's hand groped her backside and kissed her neck. Her leg was wrapped round his waist, and a big smile was spread across her face.

She looked at the second picture, and her complexion paled further. It showed her on her knees in front of him, jerking her boss's dick into her mouth as his hands twined through her hair. His trousers round his ankles as she pleasured him. The third showed her hands on his backside as she took his full length into her mouth. She looked up at Rob. His expression was one of amusement. She couldn't stop herself and returned to look at the photos. The fourth and fifth picture showed the boss cumming, she hadn't swallowed and had let him blow over her face and neck. She turned the last picture and showed them both cleaning themselves up.

She looked at Rob's smile "Who else has seen these?"

Rob stretched his arms and cracked his neck to make her wait. "No one. Yet!"

She replaced them back in the envelope so she wouldn't have to look at them. She was his boss and she had to maintain that roll. "These photographs could cause a lot of problems. Just think of the damage it could do the company, let alone to me and to Jeff's families."

"Naturally you'll want me to hand over the originals to you so they can be destroyed."

She didn't like the expression he wore. An expression like that meant that there would be a payment involved. She was prepared to pay what it took, then fire his ass!

"Yes I would Robin." She said as calmly as she could.

He leant down close to her. "Well, I want what Jeff got!"

She swallowed hard. She had only done that with her boss because of the alcohol. "No deal Robin. How dare you try and blackmail me! You little shit! I am not…"

Robin interrupted her little rant. "As you know, they're off my new digital camera. It was simple to download them onto the computer. It'll be even simpler to attach them to an email. Tell me Chris, is our 'all-staff' email address the same? I bet your boyfriend's company email system has a set up very similar to ours!"

She stared at him shocked. Not a word passed between them as each other forced the other to back down first. It was Chris that cracked.

"OK Robin. Lock the door then." She looked at the floor defeated.

"No." he said moving behind her. "Not here." His hands massaged her shoulders. "You know where I live." His hands moved down and cupped her breasts through her white blouse. Her body stiffened against him "Come to my house after work." His thumbs rubbed her nipples and his mouth moved to her neck. "Directly after work! I trust you won't tell anyone about this…" One hand moved slowly down her belly. "…arrangement" his lips kissed her neck.

"You are not fucking me. Understand?" She hissed.

"I'm sure we can come to some other arrangement then!" He moved his mouth up to her ear and licked her earlobe.

"Whatever. Just no fucking!"

"Well Chris." He moved away from her "See you tonight. I don't think you'll mind me popping off work early and getting myself ready do you?" He said and sauntered out the door.

As the door closed, Christine realised that she had been holding her breath and panted for air. She put her head in her hand and thought about what was to happen.

Robin left work and headed for home. On the way he visited the local supermarket. He went straight to the chemist counter and explained he needed condoms with out the spermicide on. He had his own ideas about what was going to happen tonight. The only certainty he had was that he was going to fuck her.

Getting home, he quickly opened the pack and pulled out the individual rubbers. From his wardrobe he pulled out a new shirt, still in it's plastic, and removed the pins. Carefully he perforated each condom pack several times and replaced them in their box. He grinned to himself and put them in his dressing gown pocket. He had other things to do before she arrived, and he went through to his computer and grabbed his webcams.

At 5:30, the doorbell rang and Robin, freshly showered and still dressed in his bathrobe opened the door. Christine just looked at him, before pushing past him. He grinned to himself and closed the door. She walked into his front room and stood in the middle of the floor.

"OK let's get this over and done with." She said, hands on her hips. Robin sat down in his favourite chair and took in the view. His eyes worked their way down her body from the thick straight black hair on her head, it moved down to her dark painted lips. He could feel himself getting more turned on as they travelled over her full breasts and he remembered how they had felt in his hands earlier. Moving down further, they went to her hips, down her knee length skirt, to her dark grey nylons and slight high heels.

He looked up at her face. "Jeff had you sat in his lap first!" he said pointing to his.

Christine gritted her teeth. "Do you want this blow job or not?"

"Do you want everyone seeing you and the boss?"

She walked over to him and sat on his lap, as if she was perched on a bar stool.

"No." Rob said calmly, making sure she knew who was in charge and who was doing who a favour. "I want you to hitch your skirt up, and for your knees to be either side of my legs."

Again the expression on her face darkened. If he thought he was going to have a job tomorrow then he thought wrong. Slowly moving her skirt hem up, she knelt across his lap. Robin's hands moved to her waist and he looked into his bosses dark brown eyes. He could tell how much she hated him right at this point, and he loved it. His hands moved to her breasts briefly squeezing them before moving to open her blouse.

"No!" Christine grabbed his hands. "I'm here to give you just a blow job!"

"You said in the office 'just no fucking'. This isn't fucking. If you've gone back on your word then you had better leave." He kept his gaze into her eyes, not moving his hands.

Christine returned his stare then turned her head away from him and released his hands.

Robin's fingers undid the buttons on her blouse, pulling the rest of her blouse from her skirt and sliding it down her arms. He eyed the cream bra she was wearing. It had a silky shine to it, and promoted her breasts to him. Moving his head forward he extended his tongue and slid it down her throat and between her breasts. Christine trembled. His hands travelled to her shoulders and pulled the straps down, before reaching behind and unclipping the bra. He threw it aside and moved his mouth to her uncovered breasts and began to suck and lick at her nipples.

Christine gritted her teeth, her jaw aching. How could she let him do this? She tried to move her mind away from what he was doing to her body, but for some reason her body didn't want her to. She tried to think of her work, but she could feel the way his teeth scraped gently on her erect nipples. She thought of her boyfriend at home, but the stubble from Rob's face quickly removed them from her mind as she felt it graze across her skin. She didn't want to, but her body was getting more turned on by the moment.

Robin's hands moved down to her arse and squeezed. His mouth still working on her breasts, he let his hands wander. They moved down the hiked fabric of her skirt and onto her nylon covered thighs. He could feel the smoothness of the material on her and how thinly it covered. He pushed the skirt up higher and moved past her hips. He prayed to God that the cameras were catching this!

Before taking a shower, he had set up five cameras in this room, all pointing towards this chair from different angles and different zooms. He had plugged them into his computer and set it to record everything. He wanted to treasure this moment forever.


Christine realised that she was biting her lip and that she was secretly enjoying this. Being stripped of her authority and having a man doing as he wished. She grabbed his wrist as it moved between her thighs. "I said no fucking!" She felt him grab her wrist and found her hand guided to his freed cock. She gently stroked it as his hands went back to rubbing the outside of her legs. It had released itself from the bathrobe and stood erect between them. She played with the length of it he groped and played with her.

Robin moved his head from her breasts and got her to her knees. She needed no encouraging as she lent forward and took his manhood into her mouth. He gasped as her mouth engulfed him, feeling her tongue working around the head of his cock. She moved a hand up to his dick and slowly jerked him into her mouth. The sensations she was making him endure were amazing. His hand loosened her grip on his cock and moved it his thigh, before pushing her head gently down, making her deep throat him.

Christine knew she shouldn't be enjoying this but she was. She sucked and teased his dick with vigour. She could feel how wet she was, and squeezing her thighs together didn't make it subside. At any other time she would be asking for a dick to fuck at this point, but she kept on remembering the fertility drugs and her boyfriend waiting for her at home.

There was nothing that would be able to wipe the grin from Robin's face tonight. Non of his former girlfriends or his imagination had blown him like this. She worked the entire length of his dick. Her hand had moved back and was gently fondling his balls, whilst her tongue wrapped around his dick like snake. He could feel his heart pounding. She was good. Very good. He moved his hands to her hair and wound the long lengths around his fingers. She hadn't swallowed her bosses mess, but he was damned if she wasn't going to swallow his.

Christine could feel how close he was and sucked his cock deep, letting the surface of her tongue rub the base of his dick. In her hands she could feel his balls beginning to tighten. She was ready to finish him off by hand when he pushed her fully head down. Gagging, she tried to pull up from him, but his grip was too strong. His hands held her head in place and she felt the wave of his lust rip through him and into her mouth and throat. She didn't want to swallow, but it pumped out of him as he held her to him. Then it was over.

Robin let go of her hair and she sat back wiping at her mouth. "I hate it when guys do that!" She said.

He looked down at her, his lust partly sated. "Now Christine, it's your turn."

She looked up at him. "My turn? I told you I'm not fucking you!"

"I agreed, we won't fuck. I want to eat you out though!"

Christine shook her head. "No, this has gone far enough. It stops now!"

"Get on the chair and spread your legs." He stood up. "Or the deal is off!"

"You said…" She began.

"Chair! Now or your boyfriend sees the pictures!"

She needed a reason. "You don't want to do that." She smiled at him "I'm on!"

Robin stood in front of her, his dick still semi erect. A small amount of unswallowed cum was oozing from the end. "If you are on I'll stop. Chair!"

She stood up and sat down as ordered. "Please Robin!" She tried one last time.

Robin gripped her legs and pushed her knees up and apart. He threw her knees over his shoulders and brought her to the edge of the chair. He stared at his prize, thinly covered by dark nylon, her pantyhose was going to offer no resistance to him. He began by slowly licking his way up her thighs, his hands moving up, keeping pace with his tongue, pushing her further down into the chair. He could hear her still asking him to stop, but the way she was panting and the smell of her sex sounded like she didn't care too much. His fingers ripped at the crotch of her pantyhose and pulled her thin panties aside. There was nothing to show she was on, no pad, no string. His mouth covered her mound in an instant and his tongue explored.

Christine's head was thrown back as she felt his tongue began to assault her. He hadn't believed her lie about being on. She fought for breath as the tongue pounded mercilessly against her clit. She felt it swirling around her clit, drawing it out, and roughly toying with it. She could feel his hands gripping and tearing at her arse as he forced his head deeper. Christine was almost lay flat on the chair, with her legs wrapped around his neck. She grabbed at his head as his tongue pushed into her and bit the knuckles of her other hand as it twisted and writhed inside.

Rob ate her with a vengeance. He was going to make sure that he was going to fuck her before she left tonight. The assault on her continued, bringing her closer to the edge. As her panting grew to fever pitch he suddenly stopped and waited for her to slightly calm down. Each time, he brought within a moment of release before stopping, her body growing more frustrated each time. He stopped completely and stood up.

Christine couldn't believe he would stop now, when she was so close. "What are you doing?"

"I'm going to fuck you!" He held his now erect cock in his hand and smiled.

Enough of her inhibitions remained in place to tell her that this was a bad idea. "No! We agreed no fucking! You said no fucking!"

"You're not leaving here until I've fucked you!"

"Robin, I said no!" She wanted release but not at the cost.

"You've got two choices Chris." He reached down and played with her pussy, caressing her clit with his fingers. He could see she was still close to orgasm. Reaching into his pocket he pulled out the packet of condoms. "The two choices are either I fuck you with one of these on." He made sure she was fully aware of her choices. "The second choice is I fuck you without one on. Either way I AM fucking you! What's it to be?"

She could tell by the look on his face that she was not getting out of this. Defeated, she nodded and he quickly opened the condom and rolled it onto himself. He offered his hand and she reluctantly took it. Turning her around he pushed her over the arm of the chair. He ripped at her pantyhose and pulled her panties further aside. Pushing his knee forward, he edged her legs apart and guided his dick forward.

Christine gripped the arm of the chair as she felt him moving behind her. He pushed against her and in one movement entered. She threw her head back and inhaled between clenched teeth. She wanted a good fucking and she hoped this was to be one.

Rob had his own plans. He knew about the fertility drugs, she had mentioned it every day at work for the last month and half. Ramming himself in, he let his mind just focus on his dick. He could feel how warm, wet and tight she was inside. But he was searching for one other feeling. He pulled back and slammed into her again. He heard her moan, and he closed his eyes. He pulled almost out, gripping her hips hard, he forced his way in, hard and deep. She cried out yes to his assault and he felt a snap and the condom sliding down his dick. The pinholes he had put in them had worked. His dick was now totally free to fuck her. He fucked her hard. Holding her by the hips, he pounded against her.

She held onto the arm of the chair, nails digging into the fabric. The attack on her pussy was amazing. She heard herself groaning with pleasure. She lowered her body further, keeping her arse high, allowing him to enter deeper. She could feel the release approaching, what she had been waiting for all evening. Her body began to tense up as she felt the throbbing building between her thighs.

Robin kept fucking. He could feel her muscles gripping him tight and he loved the feeling. He was almost ready himself. She started to moan and whimper as he pounded her tight pussy. He could see her body shaking, then, as he thrust into her she slammed back hard onto him and screamed. Gripping her waist, he rode her through her passion.

Christine's release was a blessing. She felt exhausted by it and collapsed forward onto the chair, her face into the cushion. Robin's hand again gripped her hair, whilst the other playfully slapped her backside. "Christine?"

His pounding against her quickened. One foot now on the chair and the other on the floor. He was fucking her deep. "Christine?"

She began to come back from where she had been "Yes?" She replied.

"I think the condom has broke!"

"Pull out! Pull out!" Christine started to struggle against him. He held her down as he continued fucking. Still holding her face down by the hair, his hammering against her cunt. She begged and screamed at him to pull out, but he wasn't going to.

This is what Rob had been planning. Her struggling just sent him over the edge. He forced her face into the cushion as his body trembled, and with a loud gasp, came. He felt wave after wave of pleasure coursing through his being and erupting into her. The sensations stopping him from making any sound. Even Christine's muffled screams from beneath him didn't register. And then with a final shudder, it ended. He let go of her hair and stumbled back against the wall for support.

Christine got up from the chair and quickly grabbed her blouse. Tears streaking her make up, she pulled her skirt back down into place and left slamming the door.

Rob went into work next day and walked into her office. She watched him without a word.

"I've got you a present." He said reaching into his jacket, and placing a CD in front of her. "On it are all the photos from the party the other night as promised."

Her eyes moved down to examine it. She picked it up and placed it in her drive on the computer. After a few seconds, the pictures began to play in order.

"Before you fire me, there's one extra thing on there." he said as he left the room.

Christine stared as the movie from the night before began to play.

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6 Comments
NightOwl47NightOwl47about 4 years ago
Who's the boss?

I love these blackmail stories. I particularly enjoyed the way he groped her through her clothes in the office and suckled her breasts before getting to the hardcore stuff at his home. Looking forward to Chapter 2.

AnonymousAnonymousover 17 years ago
Not too bad!

Nice start but want to see more.

AnonymousAnonymousabout 18 years ago
Great story

Please continue did she get a baby out of it??? Invite your friends to pleasure the slut also.

AnonymousAnonymousabout 20 years ago
Blackmailing the boss into a total slut

From the start it is a great story that I hope has many chapters

AnonymousAnonymousover 20 years ago
great story

Can hardly wait for more.

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