Kelly's Tough Spot Ch. 03

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Kelly’s blackmailer makes things difficult for her at work.
3k words
4.41
16.5k
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Part 3 of the 5 part series

Updated 12/10/2023
Created 09/07/2023
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Monday morning rolled around without further drama. Kelly had not heard from either her blackmailer or Matt since Friday night although she figured there was little chance that good luck would continue.

She was still a bit sore from the fucking she got from Matt and then several times later that weekend from Nathan. He seemed reinvigorated by her efforts in the car and although sex with him was not all she would hope for it was better than nothing. She also had to make a trip to Walgreens on Saturday for a plan B pill. Kelly had been off birth control a few months now because her and Nathan wanted to have another child. She couldn't risk the fact that Matt's massive load might have gotten her pregnant when Nathan hadn't been able to.

Around work all was well at least for now and in Nathan's case even better. All the guys in the warehouse had heard about his fun drive to the bar and it seemed to have enhanced his image among them. All morning Nathan felt like he was finally one of the gang and was excited to fit in with the group. Little did they know he was definitely no "hung stud" like Tyrone and Marvin were saying but she was glad Nathan was enjoying it regardless.

Things were always busy around the office on a Monday and this was no exception. Kelly had deliveries to schedule and drivers to dispatch and in typical Monday fashion things weren't going well. No help would be coming though as it was end of month and both Linzee and Marilyn had their own problems.

Their manager Charles stomped thru to his office without a word and slammed the door behind him. All three ladies exchanged looks and went back to what they were doing. Something wasn't right for sure.

Charles was in his early 50's and considered himself quite the ladies man. Short and a bit stocky many women nonetheless seemed to find him attractive. Handsome with a good sense of humor he had managed to use that to his advantage over the years at work. The current group of ladies was no exception. It had been at least a couple years but he had hooked up with them all at one point or another.

He and Marilyn had dated quietly for a while but he broke it off when she wanted it to get serious. He wasn't looking for wife number 2 and she wasn't willing or able to keep a low profile.

His experience with Linzee was a drunken hook up after a work Christmas party. Both instantly regretted it and had never spoken about it again. He would have loved another shot but he sensed it was never going to happen.

Kelly on the other hand had been an on and off things for years. Rumor was that Charles' wife had caught them in bed and that was what caused his divorce. That wasn't exactly the story but she did find some texts between them that ended up being the last nail in the coffin.

After Kelly got serious with Nathan she broke it off with Charles and anyone else she was banging. That didn't sit well with Charles since he blew up his marriage by screwing Kelly. Now he got none of the benefits but still got the alimony and child support bills. That he suspected might just be changing though.

Saturday when he went to his mailbox at home he found plain manilla envelope addressed just to "Charles". No address or postage so it had clearly been put in there by someone other than the postman. He grabbed it and the rest of his mail and walked towards the house opening the envelope as he went. He stopped in his tracks and his jaw dropped as he looked at the handful of pics that were inside.

They all appeared to have been taken from a video time and date stamped Friday night.

Kelly naked in some truck that was clearly not her husbands.

Kelly with a mouthful of dick that was clearly not her husbands.

Kelly getting fucked by the same dick and of course a pic of cum oozing out of her pussy. Both which were clearly not her husbands.

A small hand written note on a 3x5 card was included that simply said "have fun".

He had pondered what to do with them for 36 hours and narrowed it down to two options.

Option 1 He could make sure Nathan saw them. He might dump her and put Kelly back on the market. No guarantee he would not forgive her though. He felt Nathan was a pussy and might not have the guts to leave her.

Option 2 he could blackmail her with the pics. Clearly that's what the sender had in mind. That might work or she might push back. If she said fuck it and went to HR well he might lose his job too.

On the way into work Monday morning he made up his mind. He wanted his pound of flesh, 120 pounds of flesh to be precise. He would be careful, nothing in writing and for sure no text messages again but he was going to use the pics to his advantage.

He kept to himself most of the morning til about 10am when he opened his door and asked Kelly to come in. She shut the door behind her as she sat down.

" I heard you guys had fun at happy hour on Friday" he started.

"Yeah." she replied. " we had a blast."

"From the looks of things though you had an extra good time." As he slid the envelope across his desk to her he added. "Guess now I am sorry I couldn't make it."

She knew what was in there before she even opened it. Her first emotion of course was anger. She did what the blackmailer told her to do so why in fuck did Charles have these pics? As she quickly processed the situation she recalled her long delays in responding. This was probably the payback. Her anger quickly started to fade and be replaced with fear and the more she thought about it the more questions came up.

Had the pics gone to anyone else? Did the blackmailer know about her history with Charles? If he did know how did he and what else did he know?

"What are you planning to do with these" she asked barely making eye contact?

"Guess that's up to you really." he replied. "Now that I know your good girl loving wife act is total bullshit I really want to drop them on your husband. He needs to know what a whore he married"

"It's really not what you think." She stated before being cut off.

"I don't want to hear any more of your lies. Save that shit for Nathan." he sneered. "Things are going to back to the way it was before you got married."

He stood up and walked around behind her and grabbed the envelope from her.

"I'll be keeping these in a really safe place so don't get any ideas." as he locked them in his desk he added. "Hope you don't have lunch plans but if you do cancel. Meet me at my house at 12:30. Park a block down the street and walk up. The door will be unlocked".

Kelly got up without a word and headed to the door. She did indeed have plans but they weren't with Nathan fortunately but instead his mother.

She grabbed her phone and texted her mother in law real fast. A quick apology but she couldn't make it to lunch. A big problem at work that needed her attention. Next week she promised and with that her lunch hour was free.

12:15 rolled around and she headed to the car. It was only about 10 minutes to her destination and she knew it well. Typically she would park at a pizza parlor nearby and he would pick her but apparently she didn't rate that treatment anymore.

She pulled out of the lot and headed for her lunch rendezvous. She was very nervous and focused where she was going and paid no attention to the white pick up truck that pulled out behind her. She also did not notice it follow her turn for turn till she arrived at her destination.

Kelly drove by Charles' house as instructed and parked about a block down the street. The white pick up pulled in just a house down and the driver sunk down in his seat.

Kelly walked quickly up the sidewalk having no idea she was being recorded and even less of an idea that the hole she was in was just getting deeper by the second. A minute later she walked in the front door like she owned the place.

Charles stood in the foyer waiting as she set her purse down and approached him. Just as she was within reach he told her to get down on her knees. She stopped and did as she was told and waited for his next instructions.

"Take my cock out you stupid fucking whore." He demanded. "It's been way too long for this."

She did as she was told and unbuttoned then unzipped his pants before pulling them down. Next followed his boxers and his cock sprung free.

His cock was not unlike Charles himself. Not overly long at about 5 inches but it had impressive girth. It was the fattest cock Kelly has ever been with and over a year away from it made it seem fatter yet.

She didn't need to be told what to do and immediately leaned forward to take his dick in her mouth. He grabbed two handfuls of hair and starting fucking her face and he was anything but gentle. The thickness made it hard to take him all the way but he didn't give her any choice. Every 8 or 10 strokes he would jam it in as far as he could and hold it till she started to gasp for air. The more she struggled the harder his dick seemed to get. The more she resisted the stronger his grip became.

After about ten minutes of this he finally released her and she collapsed in a pile on the floor. She continued to battle to catch her breath as he reached down and grabbed her by the hair and drug her into the living room. He reached down unbuttoned her pants and yanked them down and then her soaked thong after that.

He took note of her soaked panties and laughed "Only a total slut would get wet being treated like this. You can't even argue that you don't enjoy it."

She was ashamed to admit he was right. She liked to be debased and humiliated. She enjoyed being used like a piece of meat. Truth be told she felt something inside that was missing since she got married and it felt good.

Charles pushed Kelly over the arm of his couch and admired her ample ass. It was definitely her best feature and he was excited to have this view again. Without so much as a word he lined his cock up to her wet slit and pushed it in with one stroke.

For Kelly she guessed it was like what getting punched in the gut feels like. She felt her pussy stretch around his cock like it hadn't in over a year. Charles gave her body no time to figure out how to accommodate his cock before he started to pound away. If she thought what she got on Friday night was a hate fucking well Charles was trying fuck her to death then.

She laid face down bent over the coach as he hammered her pussy for what seemed like an eternity. She came twice in the span of a few minutes. Embarrassed her body was betraying her and showing how much she enjoyed being taken like this. She could feel her juices running down her legs and she was grunting and groaning while he fucked away at her pussy like a machine. This continued till she heard his breathing get faster and faster.

Charles was too smart to nut in that pussy he was destroying and risk getting her pregnant plus he had other plans anyway.

A few last deep strokes for good measure and he pulled out. He took a second to admire his work and was shocked at the condition of her pussy. It was gaping wide like she had a speculum in it and was red and raw. Charles grinned and took two steps around to where her head lay on the couch and stroked his cock a couple times till it exploded all over Kelly's face and hair.

Kelly laid there literally unable to move for a minute till a smack on her ass brought her back to her senses.

"Get up whore and get the fuck out of here. You are gonna be late to work if you don't hurry." as he began to gather his clothes.

She did the same and was headed to the bathroom when he asked her what the fuck she thought she was doing.

"No time for that. Get dressed and get out of here. You can clean up in the car." as he laughed " Or at work."

Kelly slipped her thong, pants and shoes back on, then shuffled towards the front door. She stopped to look in a mirror by the front door and she was a mess for sure. Hair matted with sweat and cum and her makeup was destroyed from the same also. Her shirt was already stained also.

Just as she opened the door he got her attention one last time.

"Nice to have the old Kelly back. See you back at work. By the way I have some ideas at work to make things more enjoyable." He said ominously. "We can talk about it later."

Kelly stepped out on the porch and looked left and right. For some reason it seemed like Main Street USA at the moment. A couple pushing a stroller walked her way as did a group of teen boys not far behind them. She was also blissfully unaware that she was being photographed from 50 ft away in all her cum covered glory.

She approached the couple first and despite her efforts to remove some of the cum it was obvious to anyone what she had been doing. She walked with her head down but glanced up just enough to see the woman's look of disgust and the man's shit eating grin. As she passed by he could not help but snicker and she heard the lady to tell her husband to shut up.

As she approached the group of teens they were considerably less restrained. They laughed openly and one of them asked her if she had a good time. They all gave him high fives while another replied.

"Well if she didn't it looks like someone sure did."

She got to her car and slid into the drivers seat. She grabbed a pack of wet wipes from the backseat. She cleaned up her face and went to work on fixing her hair and make up. There was no chance she could look as good as she did when she left work but she did her best. She grabbed her sweatshirt from the back seat and threw it on to cover her cum stained shirt. She looked in the mirror, gave herself at least passing approval then started her car and car to head back to work.

She arrived back at work, parked, and hurried in. She was over her hour but just barely. The office girls were not back from lunch yet, so all was quiet and she had a few extra minutes to compose herself.

Not long after Nathan walked in and seeing no one around, gave her a peck on the cheek.

" You're so beautiful babe, I love you." He said as the door opened and in walked Charles, Linzee and Marilyn.

"Hey Nathan, just the man I wanted to see." Charles said loudly. "When you're done with your wife come see me."

Nathan glanced at Kelly and she shrugged as if to say " no idea" and he headed off to speak to Charles.

As she sat there looking at his office door she felt like she could puke. She did everything he asked so what was this conversation about?Minutes seemed like hours till the door opened up and Nathan came out. He had a huge smile on his face as he walked back to her desk.

"I've got great news babe. I just a promotion to operations supervisor. Charles said I'm perfect for the job. Said he made up his mind at lunch today and didn't want to wait to tell me."

"That's awesome, I'm so excited for you. We can celebrate tonight." As she winked at him.

Nathan blushed a bit and said "It's a good raise for us. I have to do some traveling but he didn't seem to think you would mind that at all."

"How much travel?" She asked.

" Just a few days a month. Maybe a weekend here or there." he replied.

Kelly forced a smile on her face and congratulated him one last time as he headed to the warehouse to tell his new buddies. Kelly stole a glance over shoulder and there stood Charles in the door of his office taking the whole thing in with a huge smile on his face.

"Always nice when someone gets what they deserve." he said to the girls as he turned and went back to his desk.

Kelly turned back to her computer and finally got back to work. In a couple weeks she has gone from faithful wife to wanton slut and things seemed like they would only get worse. She would do what she could to protect her family but she wondered how long she could live a double life.

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AmbulAmbul5 months ago

It is fabulous that Charles promoted Nathan but Nathan will have to travel out of town several days a month. For sure Charles, Matt, and the original blackmailer will ensure that Kelly's holes are pretty constantly filled with unwanted but very pleasurable cock. She will be using morning after pills for the next couple of weeks until she can get a birth control prescription. She is going to have to start getting tested regularly for STDs and HIV. Life is getting more and more complicated for the blackmailed slut and almost whore. Love where this may be going.

AmbulAmbul5 months ago

Over the top, as Pappasleaze noted, but still pretty hot. Now that we know that Kelly is really a slut for cock and her sexual relationship with Nathan is a mixed bag - she clearly wants a husband to help her raise her 14-year old daughter. Now the blackmailer has her getting new cock almost regularly, and is watching her closely. Her descent to total depravity is likely to be swift. Love the story.

PappasleazePappasleaze7 months ago

Hated this chapter. 1 person blackmailing is great , 2 could be fun, more than that is ridiculous. I like seeing a blackmail with a lot of humiliations but as much aggressiveness that these guys are using is borderline rape in my opinion. need to reel the story in

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