The Business Agreement

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Kailey has been watching her married boss for a long time.
5.5k words
4.59
52.6k
32

Part 1 of the 2 part series

Updated 06/08/2023
Created 08/31/2016
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Long time reader here. First time poster. Part two will be coming up shortly. Feedback is always welcomed. Thanks and I hope you enjoy it!

*****

Kailey Masterson was every man's dream come true. She was smart, sexy, and sweet. The whole package. When she applied for an admin position at 23 and fresh out of college, she was hired right on the spot with a big law practice.

Dan Stevens was a hot shot lawyer who was looking for the perfect assistant. He didn't think that he would be so lucky with Kailey. She was a great employee and eye candy for the whole firm. He would go insane without her and needed her help with everything. Even after 7 years he needed her more than ever. Maybe more than just a secretary.

Dan had been struggling with having sexual feelings towards Kailey. He was married and had been for close to 10 years. He felt like he was happy but the sex just wasn't there anymore. His wife wasn't interested anymore and Dan was overly horny all day every day. So lately he had been hornier than ever and having such a hot young employee in the office wearing short skirts and tight blouses was making it harder for him. That and they didn't have the normal boss and secretary relationship.

Dan and Kailey talked about sex on a daily basis. She was a great friend and listener for Dan and his problems. She knew about the lack of sex in his life and she thought with her stories about sex, he would feel better. And it did make him feel better. He got to the point where he couldn't wait to get to work and he delayed going home. His wife didn't seem to mind. The whole office thought Dan and Kailey were fucking, but in reality they had never done anything sexual except for talking. In a lot of cases Dan had asked Kailey to leave his office because he had to jack off and he would have love to have her watch, or better yet join in. But she couldn't. Instead she would just smile and give him a wink before going back to actual work. Dan would never cheat on his wife though even with someone who was so much younger than he was and so much hotter at that.

Kailey enjoyed their talks and tempted him more than she should have with him being a married man. Even though she enjoyed sex she would never hook up with a married man. She knew Dan loved his wife too much to try anything. Everyone needed a little pick me up every once in a while. Plus she did like his wife. They had gone out a few times as a company to dinner and had a great time. Carly Stevens actually didn't mind Kailey. She enjoyed the younger secretary and she wasn't scared of her tempting her husband. She thought she was a nice girl and even though she was beautiful, she didn't feel threatened.

Monday morning came and Dan came into the office with a smile on his faced. He couldn't wait to see what sexy outfit Kailey had on.

"Good morning Mr. Stevens." One of the new interns was extra cherry this morning. Dan didn't mind waking up at 6 every morning to get to the office early especially since he got to see Kailey every day. Dan couldn't remember the young man's name but he smiled and waved with his briefcase in hand before he walked over to his office.

Once inside his office he saw a smoking hot blonde bent over his desk just begging for her to be fucked. She had on a tight black skirt that came to her knees and wedges that made her taller than she already was. Clearing his throat the blonde quickly turned around to see her boss.

"Good morning Mr. Stevens." She teased knowing very well she could call him Dan. She usually did unless she was in a playful mood. He was able to take a good look at her. She had on a white button down blouse that came to her elbows. A hint of cleavage was spilling out of her blouse which made Dan stare slightly. He didn't care about staring because of their relationship. He could look but never touch.

"Good morning Kailey." He stared a little longer at her DD tits before walking over to his desk and sitting down. She put the file she was looking over down on his desk before walking over to the big wooden office door. She shut it lightly which Dan knew meant that she was about to talk about something sexual. He loved this time of the day.

"Can I ask you a personal question?" She said sweetly as she batted her eyes lashes and sat on his desk. That's how this game always started.

"How personal are we talking?" He played along as he eyed her thigh being more exposed. She played with her long blonde hair putting it up in an up do before fanning herself.

"It's so hot in here." She smiled as she noticed his eyes on him. She enjoyed the attention no doubt. She just wish he would do something other than look. Deep down he couldn't but he sure as hell wanted to. He was gorgeous for 50 and she wanted him in any way possible. He had salt and pepper hair. Standing at 6'4 he definitely got looks with his height. He looked about 40 with his lean body which he was proud of. He went to the gym 5 days a week. He knew he got looks but he didn't feel too good when his wife denied him sex almost every time he asked.

"You can turn the A.C. up more." He said as he stared at her while she fanned herself. He couldn't keep his eyes off her most times.

"No that's alright. Thanks though." She pulled her leg and stretched it out along the desk exposing her tan leg along with parts of her thighs. Dan gulped hard and was starting to sweat but not because of the heat. "So back to my question? You don't mind right?" He gave her a look that said yea right and she just giggled and smiled at him. "So you know Rick?"

"The guy you have been seeing for a couple months now?" He remembered Rick. Kailey had invited him out to dinner when the company went over to his house for dinner. Dan had a huge house and had company picnics and dinner a lot. He remembered Rick and Kailey couldn't keep their hands off each other. And he also remembered how jealous and horny he was at the two of them. He had tried desperately to get his wife in the mood that night but it wasn't happening. He did get to eat her out which was a common occurrence. He would eat her out and she would get tired and fall asleep before they could continue. He absolutely loved eating a woman out and making them feel good but he wanted a little something too.

"Yea well we broke up. He said I was getting too serious for him. All I was doing was fucking him." Kailey had the mouth of a sailor and Dan loved it.

"Well I know if I had a young girl fucking me all the time, I wouldn't break up with her." He said as he stared at her thighs again. He had fantasized about what was under that skirt for years but he was a good man and couldn't cheat on his wife.

"So what about you? Get any this weekend?" She chuckled with the look he gave her. She knew very well that his wife wasn't going to give him much. She enjoyed teasing him to no end.

"Actually I got to eat her out. I enjoyed that but she fell asleep before I could do anything else." She could tell he had sadness in his voice and she felt bad for him. She couldn't imagine being married to someone for 10 years and them not wanting her sexually.

"So you like eating pussy?" She changed the subject so he could be more chipper. In an instant that frown turned to a smile and he chuckled.

He stood up from his chair and leaned over so that he was closer to her ear. Every so softly he whispered. "I love it." His voice made a shiver go down her spine and her panties were getting a little wet. He turned her on just as much as she turned him on. He just didn't know it.

He noticed that her calm cool demeanor had changed. She looked like she was at a loss for words. He had never seen her so uncomfortable. He liked it a lot.

"Most men I know don't like to give head unless they get something first." She always would change back in forth to make herself look more presentable. She didn't want to look like a total slut after all. She wouldn't always talk like a sailor.

He was expecting more of a smart sassy comeback but he chuckled when he saw she was trying to compose herself. He liked watching her squirm. He would have to do it more often. He saw the blinking red light on his phone meaning no one was picking up the phones for the day.

"Do I pay you to just sit there and look pretty? Get to work!" He teased as she got up from the desk. Her breasts jiggled as she did and he couldn't keep his eyes off of them.

"Eye eye boss." She winked as she waved him goodbye to head to her office and start the work day. Dan looked down at his black suit pants and noticed the slight bulge in his pants. It would be a long day for sure.

The week had gone by at a faster rate than normal. With the help of Kailey, Dan and the firm got a new client who was going through a nasty divorce. He was very wealthy so that meant more money for them.

Dan was a little sad seeing the weekend approaching because he wouldn't see Kailey for two whole days. He had to think of a way to have more time with her.

"Hey boss I have an idea for you." Just like clockwork at around 3 in the afternoon, Kailey walked into his office. She was wearing a tight red dress that showed her body off along with black heels. Her tits looked fantastic in her dress as always.

"I'm glad you came in. You want to get some drinks tonight?" He had seen her drunk once and tipsy more than a few times. She was even flirtier if that were possible and extra handsy. He had to take an extra cold shower when he got home those nights.

"I would but I'm gonna help you get laid tonight." He raised his eyebrows with question in his eyes.

"And how are you going to do that?" He was intrigued. He didn't think anyone could get his wife in the mood.

"Well almost every woman out there enjoys romance. So why don't you surprise her with roses, chocolate, and a nice dinner for starters. Then you can put candles around the bathtub along with rose petals and draw a really nice bubble bath for her. Trust me she'll be in your lap in no time." Dan thought of himself as a romantic. He told his wife how beautiful and sexy she was all the time, but he didn't go out of his way to do those things. Sure he got her flowers and he took her out to nice dinners but he needed to step up his game.

"Do you enjoy those kind of things?" He was curious. She didn't seem like the romantic time.

"If I had it done I think I would. As much of a sex freak as I am, I haven't really found someone to do those things for me. But it's alright. Maybe one day. I'm just having fun now." He felt bad for her. She seemed like the perfect girl and he hoped that she could find someone to treat her right.

"So what are you going to do tonight?" It was Friday so it would probably be something sexual. And he couldn't wait to hear the story.

She put her hands in the air and moved her fingers around. "These." She walked over to his desk and leaned down to his ear. "I have neglected myself for a couple weeks now so I'm going to take a nice long bath, drink a little wine, and then watch some porn to make myself feel good." She giggled when she heard him groan. She noticed his jeans looked a little snug as well. She had fantasized about what his cock looked like. How it would feel in her mouth, her pussy, and even her ass. She liked it everywhere. A fantasy was all it was though. Nothing more. She got by with their little talks.

She stood up straight when they heard a knock on the door. "Come in." Dan said as she walked over closer to the door making sure it didn't look like they were doing anything. Even though they weren't.

The young intern who was in law school open the door. "Hello Mr. Stevens, Kailey."

"Hello Kevin." Kailey pursed her lips together and smiled. Dan was grateful she knew everyone's names because he sometimes forgot.

"Do you need anything Kevin?" Dan said behind his desk. He didn't want to get up and show his uncomfortable boner.

"I was just looking for Kailey." She smiled as she turned her attention to Kevin. "Would you like to have dinner tonight?" Kevin had watched Kailey for the 2 months that he had been interning at the firm and she was beyond gorgeous. She was the whole package. The other employees had warned him that she might be sleeping with the boss but when he meet his wife he quickly figured that they both weren't those kind of people.

"Thanks Kevin but I have plans tonight." Dan chuckled on the inside knowing what she was going to be doing tonight. A mental image popped into his brain of her spread eagle on the bed manipulating her clit as she fingered her hole. Damn this woman made him go crazy. He wished his wife was that open. In 10 years he had never seen her masturbate. She said she was too shy to do anything in front of him.

"Another time then." He said hopeful that she would accept his offer.

"Yes that sounds great." She turned to look at Dan and pointed a finger at him. "Now go home to your wife." She smiled as she walked out of the office to do some work. Dan chuckled as Kevin followed the blonde down the hallway. Checking the clock he decided to do a little bit more work before making a plan to seduce his wife. He hoped Kailey's suggestions would work.

Later that night Kailey sat on her couch with a glass of wine and watched TV. She had on short flannel shorts and a tank top. Her cat and dog were curled up next to her as she heard the rain pour on her roof. The weather channel said that it was supposed to be only 10 or so percent chance of rain but it was falling very hard and very fast. A knock on her front door made her get up from her comfortable position. Her cat and dog weren't too happy with their mommy leaving but they snuggled each other on the end of the couch not knowing if she would be back.

Kailey opened her front door to a very wet Dan on her door step. "Dan what are you doing here?" He looked like a drowned cat. Still wearing the suit that he had on during the day, it was soaked to the core.

"I should have called I'm sorry. I just didn't know where else to go."

"Please come in." He walked into her house as she disappeared for a second to grab some towels. She had about 5 big fully towels in her hands as she handed them to him.

"Sorry I'm getting your floor wet." She went into the kitchen and grabbed a wooden chair and placed it next to her couch so that he could have a seat.

"Are you alright?" She didn't know what was wrong but she wanted to know.

"Carly's cheating on me. Has been for years. That's why she has lost interest in me sexually." Kailey's blue eyes grew wide as she watched Dan dry off with some towels.

"I can't believe she did that. I mean have you see you. You are perfect. Good looking, hardworking, and sweet. The list could go on. Are you sure?" She asked as she handed him another towel. The dog and cat were wide awake and excited to see someone new in the house. Both of them tried to rub up against Dan which he actually enjoyed but Kailey pulled them back.

"I was going to surprise her with tonight and I walked in on them fucking in my bed. I can't believe this is happening. I wasted so much time with that bitch." He rubbed his forehead slightly.

"Strip." He looked up at her not knowing if he heard her right.

"Excuse me?" He didn't know what else to say. He was heartbroken and beside himself but he was turned on by what she had on. He had seen her in skimpy clothes that were on the professional side but never had he seen so much skin on her. She looked so sexy and beautiful with a fresh makeup free face. Her long blonde hair was in a messy bun. She looked so good being casual.

"You're going to get sick. Take your clothes off and I'll go find you something. I'll dry them." She ran upstairs to grab him some clothes as he started to strip out of his work suit. He felt funny as he stripped down to nothing only having a towel wrapped around him. He looked around the house and saw plenty of pictures of friends and family. He stopped dead in his tracks when he saw a picture he was familiar with on her mantel. It was a picture of the two of them at a formal dinner he hosted a couple of years ago. It was just the two of them. She had on a long red dress that hung to her curves perfectly. He remembered that night all too well. He wanted her so bad along with many other nights but that night was special. That was the start of their unusual friendship. He confided in her about his wife and their lack of sex. She was understanding and helped him through his tough time. He couldn't believe she still had the picture.

He heard her come down the stairs and made sure he looked presentable. He didn't want her to see anything even if he wanted to. He didn't want to embarrass her or make her feel uncomfortable in her own house.

"What do you have there?" He asked as she had some clothes in her hands.

"I like to sleep in bigger stuff in the winter. I think it'll fit you." She handed him a t shirt and a pair of boxers as he stood up from the chair with the towel wrapped around his middle. It was her turn to check him out and he noticed. She noticed for the first time how good in shape he was. He had nice muscles for a 50 year old. Her eyes traveled down to his flat stomach down to his towel. He caught her stare as she blushed. He had never seen her blush and he chuckled.

"Thanks." He said as he looked at the t shirt and noticed that it was an extra-large and would probably fit him.

"I won't peak I promise." She teased as she gained her composer. She bent down to grab his wet clothes and went over to the laundry room to put them in the dryer as he put on the t shirt and boxers.

"I feel a lot better. Thanks for the clothes." He said as he made room on the couch. Kailey was nervous for the first time in a long time as she walked over and sat down on the couch. She didn't know how he felt. If it were up to her she would grab him and make him fuck her. But he was technically still married. And she didn't know what he was going to do about his wife. Maybe they would work it out. But Kailey was slowly losing her self-control.

"So what happened?" The cat and dog both got in Dan's lap with the horror of Kailey. He chuckled as she tried to shoo the animals off of him.

"You got some booze? I'm in the mood to get smashed." He smiled as he stared at her behind green eyes. She always loved looking up into his sea foam eyes. They were gorgeous. They had a hint of what looked like yellow in them. It was beautiful.

"Thought you would never ask." She got up from the couch to the kitchen. Dan watched her gorgeous back side as she walked with confidence.

He decided he couldn't take much of this teasing. As she opened the fridge she found a bottle of vodka and orange juice. She hadn't realized that he had moved from his position on the couch.

He was inches from her neck and she stopped what she was going to say as she felt his heat behind her. His hands moved to the jug and bottle in her hand and put them on the granite counter top before wrapping his arms around her waist. She let out a shocked sigh as his lips moved down to her neck. She moaned loudly and pushed her ass into his erection. He felt huge and there was a whimper in her voice as if she couldn't wait to have his cock inside of all of her holes. He smiled into her neck.

He turned her around and her blue eyes had passion in them. They both had wanted this for 7 years now. Kailey moved her hand down to the boxes and rubbed his cock through the thin material. She knew how to work it even through clothes. Her other hand came around to his balls and she cupped them. Dan had his eyes closed and moaned lightly as he was enjoying what she was doing to him.

"Kailey." He whispered as he leaned in and kissed her soft lips. Rubbing his fingertips all over his body, he couldn't wait to devour her. And he had every intention of doing so.

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