Sharing Cindy Chapter 7 “Cindy Fucks Her Boss”

In the last chapter, I told the story of how I finally got the opportunity to see my girlfriend, Cindy get fucked by another guy, our friend David. It was definitely something that had me very emotionally twisted inside. Any guy who goes through this understands the mix of emotions that seem to overwhelm you. Everything from excitement, jealousy, pride, nervousness, guilt and fulfillment is in your head from the start to the finish. Thankfully when everything was over and I had the chance to think more clearly, I understood that what happened was so good that I knew I wanted to experience it again.

Cindy and I had several long talks and while she seemed to be hesitant to admit it, she eventually let me know that she enjoys sex and that having sex with someone else doesn’t mean she has feelings for them. I know a lot of people over the years have questioned us as to how we can do this. It is apparent that most people tend to lump sex and love together and cannot fathom the separation of the two. We have found that while sex with someone that you love is incredible, you can have sex with someone else just for the sake of fulfilling a desire.

Over the next year, both Cindy and I graduated and moved out to our own apartment. It made for a much happier sex life and I swear we wore out our new bed in record time. We also had a couple of more encounters with David and we both got very comfortable with another guy with us. Thankfully David never seemed to get pushy or get out of line in any way. It was always me or Cindy who would initiate anything when it came to sex.

We both got new jobs and were doing fairly well for a couple of kids. I was working for a security firm while getting an engineering degree and Cindy had taken a position at a furniture retail store, working in their office with her friend Sandy. Things were going pretty well for us. We would come home and discuss our days. She would tell me how the guys at her store were pretty flirtatious with her. She was required to wear nice clothes and usually that was a dress or skirt. She said there were a couple of guys who would hit on her constantly, one worked in the warehouse and the other happened to be the store manager.

She said that she and Sandy would always tease the guys and it was a very fun place to work. She would tell me of the offers of lunch with the guys and how the talk always seemed to come back to sex. I began to suggest different outfits for her to wear to work and help her pick out her bras and panties for the day.

One night she came home and told me she wanted to talk to me. We sat down and she went on to tell me that her boss, Bill the store manager, has really been flirting a lot with her lately and had actually asked her out to dinner. He was a guy, about 35 maybe 5’-9” and average build, nothing spectacular. We talked about it and it turned us on to imagine what could happen. He knew she was in a relationship, so I knew his real reasons for asking her out. I told her that he definitely wanted to have sex with her. She laughed and admitted that it kind of turned her on knowing an older guy was interested. I told her to look at herself, what guy with a pulse wasn’t?

Another thing that became apparent to me was that she was turned on by guys with power. Now, looking back, the manager of a furniture store isn’t necessarily a man of power, but to a couple of 18 year old kids, he definitely was. That, plus the fact that he was her boss added to the excitement and we fucked for a couple of hours that night, the whole time talking about what she should do and what could happen. We finally decided to tell Bill that she would go out with him.

We were both excited in the coming days. I was very nervous as well. I knew I wouldn’t be there to watch and keep her safe. What if he got out of line? What if she began to fall for him? What if he was better in bed than me? My head was spinning like crazy, but when all was said and done, I knew this was an incredible turn on for me and I accepted that I wanted it as much as she did.

We found a very sexy dress for her to wear on her date. It was a pale blue wrap around style dress that tied around her waist. Once the ties were undone, it basically could be opened like a coat, exposing her whole body. It was also made out of a silky material that clung to her body’s every curve. Over all it was damn sexy. We found some heels for her to go with it and some sexy little panties. Of course, we had already decided that she wasn’t going to wear a bra, but when she tried the dress on; we saw that even the panties showed because of the material. I suggested she leave them off, but she was unsure.

When Friday rolled around and she came home to get ready, we were both very excited. I watched as she got ready and I have to say, I am not sure if it was how sexy she looked or the situation. But I was hard as I have ever been. The dress came to about mid-thigh and it swayed as she walked in her heels. I desperately wanted to throw her down and fuck her right there, but she held me off. I watched as she walked out the door, on her way to let another man fuck her.

Those few hours while she was gone were agonizing for me. I tried to get my mind off of things but no matter what I did thoughts of what she and Bill could be doing at that moment kept creeping back in. Any husband who has experienced this knows what I am saying. You head is swimming and your dick really never seems to get soft. It was only 7:30 pm and would be a long night.

After several hours I heard her heels on the sidewalk out front and then her key in the door. I looked over at the clock and it said 2:43 am. When she walked in with a smile on her face, I knew she had been fucked. She looked happy as she walked over to me and I took her in my arms.

“Well?……Did you?” I asked.

She smiled and held her head down, then looked up at me with her eyes. “Yes,” she whispered to me, possibly judging my reaction.

‘I felt my already hard dick rise to the next level. “Tell me.”

“Let’s go into the bedroom ,” she said as she took my hand. I would have followed her off a cliff right then if she asked.

When we got into the bedroom, she pushed me back on the bed. Then as she slowly untied the tie on her dress and opened it, I saw the love bites on her tits. She opened the dress fully and I saw she did not have her panties on. She told me she had taken them off in the car before she got there.

As she climbed into bed she undid grabbed my dick and began to tell me all about her night.

She said that he had decided to cook for her and invited her in. He lived in a very wealthy neighborhood and had a very nice house. He had been married at one time but had gotten a divorce when she ran off with her lover to another state. He lived alone in the big house. They sat down to dinner at the table. He offered her some wine and she said she had a couple of glasses that seemed to loosen her up and calm her nerves a little.

She began to notice that he would sneak glances at her tits and it began to turn her on. Her nipples always seemed to be hard and since the dress was thin and caressed her tits so well; he could see them perfectly as well as the little bumps of her areola. She said they flirted all through dinner and by the time they were done, there was definitely some sexual tension in the air. She said that it was turning her on knowing that this older man was trying to seduce her with the possibility it could lead to sex. Little did he know that she wouldn’t have accepted the date had she not been planning to get laid. She excused herself to go into the bathroom to freshen up.
She said she touched up her make-up, added another coat of lipstick and then look down and saw her nipples in the mirror. She then slid her hands into her dress and tweaked them to make them stick out more. As she left the bathroom she saw that Bill had moved over to the couch which had a view right down the hallway leading to the bathroom. She said she felt very sexy walking towards him and even added a little sway to her hips as she approached him. He never took his eyes off of her body the whole way.

I can look back now and put myself in his place. Imagine being a 35 year old divorced guy with a super hot 19 year old girl dressed to please and ready for sex. I will bet he had never had something so good ever before.

As she got close to him, he patted the couch next to him letting her know he wanted her to sit beside him. She shook her head and then took his hand and had him stand up. Once he was, she stepped closer, almost touching his body, then reached up and encircled his neck with her arms. She leaned in and kissed him softly. She then pulled back and stared into his eyes for a moment. She said the sexual tension was very high and she was enjoying taking control. As he started to speak, she grabbed his head and pulled him down for another kiss. This time she opened her mouth and slipped her tongue into his. He then put his arms around her waist and pulled her in tight as the kiss got hotter and hotter.

She could feel his hard on pressed up against her and it felt great. He moved his hands to her as and began to rub her butt through the silk of the dress. He soon discovered she was not wearing panties and he moaned into her mouth. His hands traveled down to the hem of the dress, slipped underneath and then moved up until he cupped her cute butt in both hands. When he did this, it was her turn to moan. She said he pulled her hard against him and she felt his cock pressed up against her tummy and knew this was going to happen.

As she was telling me all of this, she had her hand wrapped around my dick and was pumping it up and down. I was so close to the edge that I had to have her slow down or I was going to paint the ceiling with cum. She laughed at that and continued her story.

He pulled back from her and shook his head to clear it. Then he looked at her, down at her tits and back up at her while arching his eyebrows as if he were silently asking for permission to touch. She looked down at her hard nipples then leaned back, arching her back as if inviting him to play. He moved his hands up and slowly ran his palms lightly over her nipples, sending shivers through her body. This made them stick out even more. She said she involuntarily let out a little gasp and a moan.

He then grabbed them and began to squeeze and really give them a work out. Just as he began to slide his hands into her dress to get his hands on them, she shook her head and stepped back from him. She then looked him in the eye as she grabbed the tie on the dress. She pulled the string and then, grabbing both sides of the dress, opened it up and presented her body to him. She said the situation was so intense, standing there showing her naked body to her boss.

This was enough to push him over the edge and he growled as he picked her up and carried her to his bedroom. She said it was so animalistic having a man just basically take her. He placed her on the bed and stood back and began to rip off all of his clothes. She told me his dick was so hard that it was sticking straight up pointing at the ceiling. I know that as she was relating this story, mine was also as hard as it’s ever been.

Now everyone is expecting me to say he had a huge dick, but she said it was probably about an average size, perfect to fit in her mouth. She scooted to the edge of the bed and pulled him in close. She grabbed his dick and brought it to her mouth. After a few licks she took it fully into her warm wet mouth and he groaned as she did. After only about a minute he was filling her mouth with a big load of cum.

After that he remained hard and pushed her back on the bed. As he positioned himself over top of her, she spread her legs and pulled him into her. And he began to pump her like a madman. Pushing all the way in and slamming her into the bed.

Hearing this I couldn’t take it any longer and rolled her onto her back and slid my hard cock deep inside of her. While it had been a while since he had fucked her, I still believe her pussy felt different. It was extremely wet and it seemed a little swollen. Whatever the reason I knew I needed to be inside of her at that point. She continued her story as I tried to keep from coming.

She said he kept up the assault on her and fucked her like it would be the last piece of ass he would ever get. She wrapped her legs around his waist and held on for dear life as he continued to jackhammer her. She said she had never been fucked so hard, even by me. I asked if she liked it and she said “Oh Yeah.” I would keep that in mind for the future use.

She felt that tingling within her that signaled she was ready to cum and just let it wash over her and send shockwaves throughout her body. As she began to come back down she whispered in his ear, “Cum for me, baby. Fill me up.” That was all it took for him to slam into her one more time and held himself in her as he pumped deep into her. That was all it took for me to also unload my cum into her. I could picture my sperm mixing with his deep within the walls of her pussy. I felt like I was cumming for a full minute.

He pulled back from her and she unhooked her legs from around him. After a few kisses he climbed off and went to the bathroom, bringing back a warm wet towel for her. Then he disappeared and came back with some water and two more glasses of wine.

They sat and had some wine, but she said she began to get horny again and started to tickle his balls with her finger tips. She pushed him back on his back and started to stroke him back to hardness. It looked like he was having trouble getting there so she leaned over toward him and looked him in the eyes as she said “I want you to play with my tits as I ride your hard dick.” That was enough for him to get hard again. She climbed on top of him and slowly slid down onto his dick.

As she began to lift herself up and down on him, she grabbed his hands and placed them onto her breasts. He needed no further encouragement and began to give them a real workout. As she increased her bouncing and began to get close to another orgasm, he leaned up and took her nipples into his mouth. This was when he began to suck hard and leave the love bites on them. She said it triggered her orgasm and she wrapped her arms around her head and held on tight.

As she came down, he laid back and pulled her body down on top of his. This allowed him to grab her hips and pump up into her while pulling her down hard against him. It was only a minute or two before he bellowed out that he was cumming again. She laid there for a few minutes before she looked over at the bedside clock and saw how late it was. She kissed him, thanked him and ran to the bathroom. After washing up, she threw her dress on and headed home to me.

By this time I was lying next to her, stroking her body and tickling her clit as she finished her story. She looked over to me to gauge my reaction. I looked into her eyes and told her I loved her. She leaned over, kissed me and said she loved me too.

While I didn’t get to actually see her with Bill, I felt like I did from her description. I definitely loved the experience and this would become the first of many times she would go out on dates. Several times she even went on vacation with another guy. I will try to go over many of the more memorable times in the coming installments. I believe the next time I will tell you all about the time we met another couple who shared our outlook towards sex. Thanks for joining me on this ride and if you have a moment, I would love to get feedback from some of you.