Sharing Cindy Chapter 9 “She Fucks The Owner’s Son”

Over time Cindy and I began to embrace our new lifestyle. While we love each other and enjoy having sex with each other, we realized how turned on we became when there was some extracurricular activity with outside people. We had many encounters through the years with people who we crossed paths with. While the some of these encounters allowed me to experience a little bit of strange pussy now and then, the vast majority were all about Cindy and her encounters with other men and women. She didn’t seem to get the same arousal from me being with another woman as I did when she was with someone else.

These encounters ranged from friends, strangers, celebrities and even included several of Cindy’s bosses. Some of the most exciting times happened by chance while she was at work. I always enjoyed when she came home to me and had a very sexy story to share. In this chapter I want to tell you all about some of the fun Cindy had with the son of one of her bosses.

It was the summertime and Cindy happened to be in between jobs. I was still working with the security firm and Cindy decided to just pick up some extra work nearby our apartment. One day while dropping off some dry cleaning, she noticed a sign saying they needed counter help. Cindy applied and was hired by the couple who owned the cleaners. That is where she met Danny, their teen aged son.

Cindy took the job as the counter person at the dry cleaners and would usually begin work around noon and would work until they closed about 6:00 PM. She was in charge of both the front counter and the drive up window. All of the actual cleaning of the clothes took place in the mornings and by the time she showed up, everyone would be leaving. This meant she was there every day by herself. The owners asked that she dress nicely when working, this lead to Cindy wearing many sundresses, as it was usually hot in the store and the light sundresses would be cool as well as look nice. It was one of these sundresses that caught the attention of Danny one day.

Danny was still finishing school and during the summer months he would help out his parent at the cleaners. Once he saw Cindy he began to hang around after everyone had left and flirt with her. One day he was hanging around as she was working the drive thru. The drive thru was located on the western side of the building and during the afternoon, the sun would stream right through the window. This lead Danny to realize that when she would step up to the window, her entire body was silhouetted through the thin fabric of the sundress for his enjoyment. He made it a point to always place himself so that he got a good look at her. She soon caught on after noticing how he would stutter and be nervous after she had waited on a customer at the window. One day, after she turned around from the window, she happened to look behind him into a wall that had a huge mirror on it. It was then that she realized just how much of her was on display. This began to excite her and she couldn’t wait to tell me about it.

She came home and told me all about Danny and his flirting with “an older woman.” While she was only a couple of years older than him, it was clear he was infatuated with her. She told me how she realized that he could see through her dresses and that it turned her on knowing he was getting hard looking at her. We headed to bed and had a great sex session, talking about teasing Danny and wondering just how far to take it. I began to enjoy each night when she came home and would tell me about teasing him. She began to try to wear things that she could really tease him in, sometimes it was the sundresses, and other times short skirts that would ride up on her ass as she bent over the counter.

It was during one of these times that she remained bent over the counter, shimmying her butt back and forth, that Danny couldn’t take it and finally made a move. He walked up behind her and pressed himself into her. She felt his hard on pressing between the cheeks of her ass and moaned. She pushed her ass back into him and he took that as the green light to continue. She said she turned around and found his lips with hers. She was very excited to be making this boy get so hard. She said that first time they just made out and he was too nervous to really go for it. When she got home she was very horny and climbed on top of me while I was sitting at the dining room table, pulled her panties to the side and had me fuck her right away.

We used her teasing to our advantage and every night she would come home and tell me what had happened. It progressed to the point where she was letting him suck on her tits and even finger her under her dresses. She said he even had his hands under her dress before a customer pulled away from the drive thru one day. This had my mind working and I came up with a plan that I thought would be fun for all three of us. I wanted to stop by the cleaners and go through the drive thru, while he was eating her pussy. We planned it for a Wednesday afternoon when they were usually very slow.

I trimmed her pussy close the night before and picked out the dress I wanted her to wear. This one made her tits look incredible and would help to get him in the mood. At the time we had agreed upon, I drove up to the window and there stood my beautiful girlfriend. She had a big smile on her face as we greeted each other. I knew something was up so I mouthed the words “Is he down there?” and pointed below the window. She nodded her head yes and her smile got very big. I could tell she was enjoying this and I began to tell her how hot she looked in that dress and how much I couldn’t wait for her to get home that night so I could fuck her in it. I made sure to talk loud enough for him to hear and she played it up saying she was wet just thinking about having a nice hard dick inside of her. I could tell he was doing a good job on her as she had trouble keeping up the conversation a few times. I told her I would be waiting when she got home and pulled away.

I was very excited and wanted to jack off just to relieve the pressure, but I was patient and waited for her to get home and tell me all the details. When she walked in the door she pulled me into a kiss and told me just how naughty she had been after I left. She told me all about how she had been teasing Danny for the hours before I drove up. Just before our set time, she called Danny over to her and pushed him down onto his knees below the window. She pulled her sundress up and showed him her wet pussy and asked him if he wanted to be naughty. Being a red-blooded kid he jumped at the chance to finally taste this goddess. She was just getting close to her first orgasm as I drove up.

Danny at first started to pull away as he realized it was me at the window, but Cindy grabbed his head and pulled it in tight, making him continue with his tongue. Once he realized she wanted him to eat her while talking to me, he really got into it. After I drove away, she said that Danny had eaten her to a few good orgasms, only slowing down as a customer drove up. They were both so horny after that, that they put the closed sign up and went into the back where they spent the next hour fucking. Cindy liked how enthusiastic he was and how he was able to stay rock hard once he came.

I was so hot hearing all of this that I bent her over the couch and slid right into that freshly fucked pussy. Those who have experienced this feeling know what a pleasure that is. Feeling how warm and wet and silky smooth a pussy is with a couple of loads deep inside is one of the things every man should experience at least once in their lives.

Needless to say, this started a relationship with Danny that continued for a couple of years. Cindy and Danny would have sex about three times a week when the opportunity arose and soon he wanted more. He would have her over to his parent’s house when they were gone under the pretense of swimming in the pool, but what usually ended up with him draining his balls into her several times. It was one of these times at his house that Danny took it to the next level.

He called Cindy and told her that his parents were gone for the weekend and he wanted her to come over and go swimming. I had recently bought a white bikini for her and did a little modification on it to better expose her. Most white suits have a lining in them to help with modesty, but I discovered that if I were careful, I could carefully cut out the lining. When dry, the suit was still opaque and for the most part modest. When it would get wet, it would become see through and showed her off incredibly. I told her I wanted her to wear the suit and see how it works. She was excited about it and with a kiss, was off to tease this young boy and maybe come home with a full pussy.

She came home later with a very good story for me. Apparently Danny had been bragging about banging this incredibly beautiful older woman and he wanted to show her off to some of his friends. When she got there, Danny had three of his friends over to hang out at the pool. She was a little upset because it probably meant she would not get some dick, but it would be fun to tease these boys.

Cindy had on a beach cover up when she walked in and she could see the guys faces light up as she walked out near the pool. She said the guys were a little nervous around her but soon loosened up and began to flirt with her. They all jumped in the pool and asked her to get in. She removed the cover up and she said all of them got very quiet. She stood in front of them in her white bikini, just turning so they could get a good look. When she jumped in and the suit got wet, all of them stood there with their mouths open. She climbed out of the ladder and walked around to the diving board. The guy’s eyes were bugging out as they could see not only her nipples, but her small patch of pubic hair as well as her pussy lips. She dove into the pool and swam over to Danny.

As she surfaced in front of him, she wrapped her arms around his neck and looked into his eyes. “Did you invite me here to show me off to your friends?” she asked him. He blushed but admitted that he did. She said “Well then, let’s give them something to look at.” With that she leaned forward and kissed him. She said when they broke the kiss; all of his friends were staring at her. She said they all played around in the pool for a while, each one trying to get a feel of her. She didn’t mind and even smiled when she felt a hand on her boob or ass. There was one time when Danny had pulled the tie loose on her bikini top and her tits were in view for all of them. They all cheered. She was just thinking about what it might be like to get fucked by all four of them when Danny told the guys it was time to go. After they left she said he tried to fuck her on top of one of the pool rafts, but it wasn’t working very well. She finally pulled him out of the pool and laid down on one of the big loungers and got what she wanted. Needless to say this story was one of the best things up to this point and we would talk about it in bed for a long time afterwards.

Danny and Cindy had a few more encounters; the most memorable happened at our apartment. As I said, I worked for a security firm and one thing we did was put security systems into banks. I had a big project coming up that required a closed circuit camera system with four cameras and a video monitor and recorder. There was a delay with construction, so I had to keep the system for a few months. I devised a plan to set up the cameras and film us having sex. While that was fun, but I really wanted to have a tape of Cindy and someone else. When Danny called Cindy one day and asked if she wanted to get together, I told her to have him over and we could film it. She said he wouldn’t come over with me there, so I set the system up to capture it all. The four cameras were placed to catch the action from different views. I had set up a mattress in the middle of the room for the best angles and lighting. Cindy asked Danny if he would like to make a movie with her and he was all for it. When I watched the video it was clear her liked to perform.

I had picked out what I wanted Cindy to wear for the video. I had her wearing a white shelf bra that had her nipples peeking over the top. She also had on a white garter belt and thigh high stockings. I was very excited when I left for a couple of hours. But once I saw the video I am glad we did this.

The video began with Cindy walking over to answer the door, hiding behind it as she told him to come in. He walked in with her following and when he turned to look at her, the expression on his face was priceless. She was dressed for one thing, fucking. He looked around and saw the mattress and asked where the camera was. She pointed out the cameras to him and once he knew where they were, he wasted little time in getting into it.

He grabbed her forcefully and pulled her to him. He kissed her hard as his hands roamed over her body. After a short period of time she reached down and felt his dick through his shorts. He was standing right in front of one of the cameras and as she grabbed his dick, it was caught in close up. She sank to her knees and slid his shorts off as she did. His dick sprang up and pointed directly towards her face. She looked over at the camera as she opened her mouth and took his dick inside. The video captured as very good blowjob as she bobbed on his cock. His hands were entangled in her hair as she did it. I could hear him begin to moan and she pulled off and asked if he wanted to cum. He said not yet and pulled her up. He spun her around and he grabbed two handfuls of tits as they both dropped down onto the mattress. He grabbed her hips rather hard and with one more look towards the camera, he sank balls deep into her in one thrust.

Her face was priceless as he did this. She opened her mouth and let out a huge groan as he forcefully began to fuck her. He was really pounding into her and making her tits shake with each thrust. She later told me that he had never been so forceful and had never fucked her so hard before. I watched as his fingers sunk into the flesh around her hips and he pulled her back into him, again and again. She was swept through a couple of nice orgasms, while he continued his assault. He definitely was turned on and a little too soon began to say he was ready to cum. He asked where she wanted it and she looked right at the camera and said “In my mouth.”

He pulled out of her and she spun around and opened her mouth. I didn’t get to see him shoot as she wrapped her lips around him and began to drink down his cum. He came for about thirty seconds, yelling out as he did so. Once he was done they both fell back on the mattress and enjoyed the afterglow for a few minutes. I watched as Cindy walked up to the video controller and winked into the camera before turning it off.

I watched the video as Cindy bounced on my dick. I came twice, once while she was sucking him and again as he was pounding into her like a jack hammer. Unfortunately this would turn out to be the last time Cindy and Danny got together, as he went off to college and they lost touch. I was able to capture another session with my friend David as we both tag teamed Cindy after she put on a sexy strip tease for the cameras.

In the next chapter I will relate some of the things Cindy has done with another of her bosses, his some, co-workers and a couple of his business associates. I hope you have enjoyed this story as much as I have and I hope you will come back for some of the future ones.